# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry A # This journal is © The Royal Society of Chemistry 2014 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_2a _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C12 H16 I N' _chemical_formula_sum 'C12 H16 I N' _chemical_formula_weight 301.16 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M P212121 _symmetry_space_group_name_Hall 'P 2ac 2ab ' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' _cell_length_a 6.944(2) _cell_length_b 11.434(4) _cell_length_c 15.743(6) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1249.9(8) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 5439 _cell_measurement_theta_min 2.2 _cell_measurement_theta_max 31.2 _exptl_crystal_description lath _exptl_crystal_colour yellow _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.600 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 592 _exptl_absorpt_coefficient_mu 2.527 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.3647 _exptl_absorpt_correction_T_max 0.8631 _exptl_absorpt_process_details 'CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_source_power 2.5 _diffrn_source_voltage 45.0 _diffrn_source_current 55.0 _diffrn_radiation_wavelength 0.71075 _diffrn_radiation_type 'Mo K\a' _diffrn_source 'Rotating Anode' _diffrn_radiation_monochromator Confocal _diffrn_measurement_specimen_support Mitegen _diffrn_detector CCD _diffrn_measurement_device ; AFC12 (Right): Kappa 3 circle ; _diffrn_measurement_device_type ; Rigaku Saturn724+ (2x2 bin mode) ; _diffrn_detector_area_resol_mean 28.5714 _diffrn_measurement_method 'profile data from \w-scans' _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 8462 _diffrn_reflns_av_R_equivalents 0.0230 _diffrn_reflns_av_sigmaI/netI 0.0297 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 3.14 _diffrn_reflns_theta_max 27.48 _reflns_number_total 2810 _reflns_number_gt 2696 _reflns_threshold_expression >2\s(I) _computing_data_collection ; CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011) ; _computing_cell_refinement ; CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011) ; _computing_data_reduction ; CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011) ; _computing_structure_solution 'SHELXL-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2\s(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0447P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.011(18) _refine_ls_number_reflns 2810 _refine_ls_number_parameters 131 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0164 _refine_ls_R_factor_gt 0.0151 _refine_ls_wR_factor_ref 0.0385 _refine_ls_wR_factor_gt 0.0378 _refine_ls_goodness_of_fit_ref 0.623 _refine_ls_restrained_S_all 0.623 _refine_ls_shift/su_max 0.002 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.3966(3) 0.94580(18) 0.10236(13) 0.0145(4) Uani 1 1 d . . . C1A C 0.3380(4) 0.96476(17) 0.26132(12) 0.0189(4) Uani 1 1 d . . . H1A1 H 0.4152 0.9095 0.2946 0.028 Uiso 1 1 calc R . . H1A2 H 0.2144 0.9286 0.2467 0.028 Uiso 1 1 calc R . . H1A3 H 0.3151 1.0356 0.2948 0.028 Uiso 1 1 calc R . . C2 C 0.2631(3) 0.86004(18) 0.08313(15) 0.0181(4) Uani 1 1 d . . . H2 H 0.1824 0.8264 0.1253 0.022 Uiso 1 1 calc R . . C3 C 0.2540(4) 0.82584(18) -0.00170(15) 0.0214(5) Uani 1 1 d . . . H3 H 0.1650 0.7670 -0.0182 0.026 Uiso 1 1 calc R . . C4 C 0.3730(4) 0.87635(19) -0.06286(14) 0.0227(5) Uani 1 1 d . . . H4 H 0.3642 0.8512 -0.1202 0.027 Uiso 1 1 calc R . . C5 C 0.5044(3) 0.96299(18) -0.04114(13) 0.0208(5) Uani 1 1 d . . . H5 H 0.5831 0.9985 -0.0833 0.025 Uiso 1 1 calc R . . C6 C 0.5183(3) 0.99659(17) 0.04318(13) 0.0158(4) Uani 1 1 d . . . C7 C 0.6520(3) 1.08011(16) 0.08759(12) 0.0150(4) Uani 1 1 d . . . C8 C 0.5841(3) 1.06870(17) 0.17819(13) 0.0142(4) Uani 1 1 d . . . C9 C 0.6298(3) 1.20793(19) 0.05756(13) 0.0196(4) Uani 1 1 d . . . H9A H 0.6535 1.2123 -0.0037 0.029 Uiso 1 1 calc R . . H9B H 0.7228 1.2574 0.0875 0.029 Uiso 1 1 calc R . . H9C H 0.4989 1.2352 0.0698 0.029 Uiso 1 1 calc R . . C10 C 0.8637(3) 1.0403(2) 0.07987(15) 0.0227(5) Uani 1 1 d . . . H10A H 0.8765 0.9604 0.1017 0.034 Uiso 1 1 calc R . . H10B H 0.9461 1.0930 0.1129 0.034 Uiso 1 1 calc R . . H10C H 0.9029 1.0423 0.0201 0.034 Uiso 1 1 calc R . . C11 C 0.6645(4) 1.13082(18) 0.25223(13) 0.0196(4) Uani 1 1 d . . . H11A H 0.5663 1.1829 0.2762 0.029 Uiso 1 1 calc R . . H11B H 0.7763 1.1770 0.2344 0.029 Uiso 1 1 calc R . . H11C H 0.7042 1.0738 0.2953 0.029 Uiso 1 1 calc R . . N1 N 0.4412(3) 0.99522(15) 0.18369(11) 0.0141(3) Uani 1 1 d . . . I1 I 0.825993(17) 0.799080(10) 0.282141(8) 0.01644(4) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0137(11) 0.0158(9) 0.0141(9) -0.0003(7) -0.0010(8) 0.0027(8) C1A 0.0183(12) 0.0197(9) 0.0186(10) 0.0015(7) 0.0089(9) 0.0007(9) C2 0.0129(11) 0.0170(10) 0.0245(11) 0.0023(8) 0.0003(8) 0.0018(8) C3 0.0205(12) 0.0175(10) 0.0263(12) -0.0015(9) -0.0074(9) 0.0006(8) C4 0.0297(14) 0.0211(10) 0.0172(10) -0.0019(8) -0.0077(9) 0.0037(9) C5 0.0262(13) 0.0203(10) 0.0160(9) 0.0012(8) 0.0012(9) 0.0018(9) C6 0.0165(11) 0.0135(9) 0.0175(9) 0.0015(8) -0.0004(8) 0.0001(9) C7 0.0142(11) 0.0145(8) 0.0163(9) 0.0001(7) 0.0018(8) 0.0003(8) C8 0.0113(11) 0.0139(9) 0.0175(10) 0.0014(7) -0.0007(7) 0.0036(7) C9 0.0217(12) 0.0161(9) 0.0209(10) 0.0033(8) 0.0037(8) 0.0001(9) C10 0.0169(13) 0.0235(10) 0.0275(11) 0.0001(9) 0.0051(9) 0.0028(9) C11 0.0205(12) 0.0187(9) 0.0196(9) -0.0028(7) -0.0035(9) -0.0009(10) N1 0.0120(9) 0.0146(8) 0.0156(8) 0.0018(6) 0.0010(6) 0.0022(7) I1 0.01497(7) 0.01624(6) 0.01812(6) -0.00183(5) 0.00011(5) 0.00024(5) _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C6 1.386(3) . ? C1 C2 1.383(3) . ? C1 N1 1.434(3) . ? C1A N1 1.459(3) . ? C1A H1A1 0.9800 . ? C1A H1A2 0.9800 . ? C1A H1A3 0.9800 . ? C2 C3 1.393(3) . ? C2 H2 0.9500 . ? C3 C4 1.394(3) . ? C3 H3 0.9500 . ? C4 C5 1.389(3) . ? C4 H4 0.9500 . ? C5 C6 1.385(3) . ? C5 H5 0.9500 . ? C6 C7 1.504(3) . ? C7 C8 1.508(3) . ? C7 C10 1.544(3) . ? C7 C9 1.544(3) . ? C8 N1 1.303(3) . ? C8 C11 1.475(3) . ? C9 H9A 0.9800 . ? C9 H9B 0.9800 . ? C9 H9C 0.9800 . ? C10 H10A 0.9800 . ? C10 H10B 0.9800 . ? C10 H10C 0.9800 . ? C11 H11A 0.9800 . ? C11 H11B 0.9800 . ? C11 H11C 0.9800 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C6 C1 C2 123.98(19) . . ? C6 C1 N1 107.66(17) . . ? C2 C1 N1 128.32(19) . . ? N1 C1A H1A1 109.5 . . ? N1 C1A H1A2 109.5 . . ? H1A1 C1A H1A2 109.5 . . ? N1 C1A H1A3 109.5 . . ? H1A1 C1A H1A3 109.5 . . ? H1A2 C1A H1A3 109.5 . . ? C1 C2 C3 116.1(2) . . ? C1 C2 H2 122.0 . . ? C3 C2 H2 122.0 . . ? C2 C3 C4 121.3(2) . . ? C2 C3 H3 119.4 . . ? C4 C3 H3 119.4 . . ? C5 C4 C3 121.0(2) . . ? C5 C4 H4 119.5 . . ? C3 C4 H4 119.5 . . ? C6 C5 C4 118.7(2) . . ? C6 C5 H5 120.7 . . ? C4 C5 H5 120.7 . . ? C1 C6 C5 119.04(19) . . ? C1 C6 C7 109.27(17) . . ? C5 C6 C7 131.7(2) . . ? C6 C7 C8 101.06(17) . . ? C6 C7 C10 111.34(17) . . ? C8 C7 C10 110.29(17) . . ? C6 C7 C9 113.40(18) . . ? C8 C7 C9 109.90(16) . . ? C10 C7 C9 110.48(17) . . ? N1 C8 C11 123.11(19) . . ? N1 C8 C7 110.90(18) . . ? C11 C8 C7 125.98(19) . . ? C7 C9 H9A 109.5 . . ? C7 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? C7 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? C7 C10 H10A 109.5 . . ? C7 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? C7 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? C8 C11 H11A 109.5 . . ? C8 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? C8 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? C8 N1 C1 111.07(17) . . ? C8 N1 C1A 125.71(18) . . ? C1 N1 C1A 123.22(17) . . ? _diffrn_measured_fraction_theta_max 0.992 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.992 _refine_diff_density_max 0.370 _refine_diff_density_min -0.230 _refine_diff_density_rms 0.059 _database_code_depnum_ccdc_archive 'CCDC 977417' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_2b _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C14 H18 N O2, I' _chemical_formula_sum 'C14 H18 I N O2' _chemical_formula_weight 359.19 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _space_group_crystal_system orthorhombic _space_group_IT_number 61 _space_group_name_H-M_alt 'P b c a' _space_group_name_Hall '-P 2ac 2ab' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, y, -z-1/2' '-x-1/2, y-1/2, z' 'x, -y-1/2, z-1/2' _cell_length_a 7.4137(5) _cell_length_b 13.6430(12) _cell_length_c 29.756(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 3009.7(5) _cell_formula_units_Z 8 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 6349 _cell_measurement_theta_min 3.0 _cell_measurement_theta_max 25.1 _exptl_crystal_description Chip _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.01 _exptl_crystal_size_mid 0.01 _exptl_crystal_size_min 0.01 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.585 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1424 _exptl_absorpt_coefficient_mu 2.123 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.9791 _exptl_absorpt_correction_T_max 0.9895 _exptl_absorpt_process_details 'CrystalClear-SM Expert 2.0 r11 (Rigaku, 2011)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100 _diffrn_source_power 2.5 _diffrn_source_voltage 45.0 _diffrn_source_current 55.0 _diffrn_radiation_wavelength 0.71075 _diffrn_radiation_type 'Mo K\a' _diffrn_source 'Rotating Anode' _diffrn_radiation_monochromator Confocal _diffrn_measurement_specimen_support Mitegen _diffrn_detector CCD _diffrn_measurement_device ; AFC12 (Right): Kappa 3 circle ; _diffrn_measurement_device_type ; Rigaku Saturn724+ (2x2 bin mode) ; _diffrn_detector_area_resol_mean 28.5714 _diffrn_measurement_method 'profile data from \w-scans' _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 12057 _diffrn_reflns_av_R_equivalents 0.1625 _diffrn_reflns_av_sigmaI/netI 0.1572 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -35 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 2.99 _diffrn_reflns_theta_max 25.02 _reflns_number_total 2644 _reflns_number_gt 1333 _reflns_threshold_expression >2\s(I) _computing_data_collection 'CrystalClear-SM Expert 2.0 r11 (Rigaku, 2011)' _computing_cell_refinement 'CrystalClear-SM Expert 2.0 r11 (Rigaku, 2011)' _computing_data_reduction 'CrystalClear-SM Expert 2.0 r11 (Rigaku, 2011)' _computing_structure_solution 'SHELXL-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2\s(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0046P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2644 _refine_ls_number_parameters 167 _refine_ls_number_restraints 6 _refine_ls_R_factor_all 0.1289 _refine_ls_R_factor_gt 0.0486 _refine_ls_wR_factor_ref 0.0845 _refine_ls_wR_factor_gt 0.0690 _refine_ls_goodness_of_fit_ref 0.858 _refine_ls_restrained_S_all 0.857 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.0938(11) 0.1194(6) 0.5900(2) 0.022(2) Uani 1 1 d . . . C1A C 0.0594(10) 0.1210(7) 0.6751(3) 0.033(3) Uani 1 1 d . . . H1A1 H 0.0961 0.0767 0.6998 0.040 Uiso 1 1 calc R . . H1A2 H -0.0723 0.1139 0.6707 0.040 Uiso 1 1 calc R . . C2 C -0.0533(10) 0.1744(6) 0.5784(3) 0.025(2) Uani 1 1 d . . . H2 H -0.1320 0.2014 0.6004 0.030 Uiso 1 1 calc R . . C2A C 0.1014(11) 0.2252(6) 0.6880(2) 0.024(2) Uani 1 1 d . . . H2A1 H 0.2311 0.2384 0.6829 0.029 Uiso 1 1 calc R . . H2A2 H 0.0310 0.2705 0.6688 0.029 Uiso 1 1 calc R . . C3 C -0.0811(10) 0.1886(6) 0.5328(3) 0.027(2) Uani 1 1 d . . . H3 H -0.1782 0.2288 0.5232 0.032 Uiso 1 1 calc R . . C3A C 0.0564(11) 0.2434(8) 0.7366(3) 0.030(2) Uani 1 1 d . . . C4 C 0.0309(10) 0.1449(7) 0.5008(2) 0.025(2) Uani 1 1 d . . . H4 H 0.0053 0.1534 0.4698 0.030 Uiso 1 1 calc R . . C5 C 0.1791(10) 0.0893(6) 0.5137(3) 0.022(2) Uani 1 1 d . . . H5 H 0.2576 0.0614 0.4919 0.027 Uiso 1 1 calc R . . C6 C 0.2093(9) 0.0755(6) 0.5596(3) 0.017(2) Uani 1 1 d . . . C7 C 0.3569(9) 0.0242(6) 0.5839(2) 0.0161(19) Uani 1 1 d U . . C8 C 0.2996(10) 0.0408(6) 0.6320(3) 0.026(2) Uani 1 1 d . . . C9 C 0.3754(9) -0.0841(6) 0.5728(2) 0.023(2) Uani 1 1 d . . . H9A H 0.2639 -0.1183 0.5809 0.035 Uiso 1 1 calc R . . H9B H 0.4764 -0.1119 0.5898 0.035 Uiso 1 1 calc R . . H9C H 0.3980 -0.0918 0.5405 0.035 Uiso 1 1 calc R . . C10 C 0.5377(9) 0.0781(7) 0.5768(3) 0.029(2) Uani 1 1 d . . . H10A H 0.5748 0.0720 0.5453 0.044 Uiso 1 1 calc R . . H10B H 0.6301 0.0490 0.5962 0.044 Uiso 1 1 calc R . . H10C H 0.5231 0.1476 0.5844 0.044 Uiso 1 1 calc R . . C11 C 0.3945(11) 0.0020(6) 0.6718(3) 0.032(2) Uani 1 1 d . . . H11A H 0.4377 0.0566 0.6903 0.047 Uiso 1 1 calc R . . H11B H 0.4973 -0.0379 0.6621 0.047 Uiso 1 1 calc R . . H11C H 0.3115 -0.0386 0.6894 0.047 Uiso 1 1 calc R . . N1 N 0.1538(7) 0.0920(4) 0.6333(2) 0.0237(16) Uani 1 1 d . . . O1A O 0.1124(9) 0.3303(4) 0.75032(17) 0.0393(16) Uani 1 1 d . . . H1A H 0.1054 0.3334 0.7785 0.059 Uiso 1 1 calc R . . O2A O -0.0223(8) 0.1844(5) 0.7596(2) 0.0405(18) Uani 1 1 d . . . I1 I -0.10483(6) -0.13859(4) 0.635617(16) 0.02767(16) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.030(4) 0.010(6) 0.024(4) -0.004(4) 0.008(4) -0.001(5) C1A 0.043(6) 0.029(8) 0.028(4) -0.008(4) 0.011(4) -0.003(4) C2 0.027(5) 0.010(6) 0.038(5) -0.003(4) -0.003(4) 0.003(4) C2A 0.036(4) 0.012(6) 0.025(4) 0.001(4) 0.002(5) 0.001(5) C3 0.014(4) 0.023(6) 0.044(5) 0.004(4) -0.014(4) -0.006(4) C3A 0.031(5) 0.031(7) 0.026(5) -0.007(5) -0.001(4) -0.007(5) C4 0.036(4) 0.018(6) 0.022(4) 0.002(5) -0.005(4) -0.014(5) C5 0.022(4) 0.016(6) 0.028(5) 0.004(4) 0.002(4) 0.000(4) C6 0.014(4) 0.004(5) 0.033(5) 0.000(4) 0.002(4) 0.001(3) C7 0.018(4) 0.007(5) 0.023(4) -0.009(3) -0.005(3) -0.001(3) C8 0.030(4) 0.015(6) 0.033(5) -0.001(5) 0.008(5) -0.002(4) C9 0.021(4) 0.021(6) 0.029(4) -0.004(4) -0.004(4) -0.001(4) C10 0.029(4) 0.024(7) 0.036(5) 0.002(5) -0.007(4) 0.003(4) C11 0.037(5) 0.028(6) 0.029(5) -0.008(4) -0.014(5) 0.008(5) N1 0.029(4) 0.016(4) 0.025(3) -0.006(4) 0.005(4) -0.001(3) O1A 0.062(4) 0.031(5) 0.025(3) -0.008(3) 0.003(3) -0.007(4) O2A 0.069(4) 0.021(5) 0.032(3) 0.000(3) 0.022(3) -0.006(3) I1 0.0328(2) 0.0256(3) 0.0246(2) 0.0000(3) -0.0002(3) -0.0053(3) _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C2 1.368(10) . ? C1 C6 1.383(10) . ? C1 N1 1.412(9) . ? C1A N1 1.480(9) . ? C1A C2A 1.505(10) . ? C1A H1A1 0.9900 . ? C1A H1A2 0.9900 . ? C2 C3 1.385(10) . ? C2 H2 0.9500 . ? C2A C3A 1.505(10) . ? C2A H2A1 0.9900 . ? C2A H2A2 0.9900 . ? C3 C4 1.398(10) . ? C3 H3 0.9500 . ? C3A O2A 1.207(10) . ? C3A O1A 1.322(10) . ? C4 C5 1.389(10) . ? C4 H4 0.9500 . ? C5 C6 1.397(10) . ? C5 H5 0.9500 . ? C6 C7 1.487(10) . ? C7 C8 1.511(11) . ? C7 C9 1.520(10) . ? C7 C10 1.544(10) . ? C8 N1 1.287(8) . ? C8 C11 1.475(11) . ? C9 H9A 0.9800 . ? C9 H9B 0.9800 . ? C9 H9C 0.9800 . ? C10 H10A 0.9800 . ? C10 H10B 0.9800 . ? C10 H10C 0.9800 . ? C11 H11A 0.9800 . ? C11 H11B 0.9800 . ? C11 H11C 0.9800 . ? O1A H1A 0.8400 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 C1 C6 124.5(7) . . ? C2 C1 N1 128.8(7) . . ? C6 C1 N1 106.7(7) . . ? N1 C1A C2A 111.7(6) . . ? N1 C1A H1A1 109.3 . . ? C2A C1A H1A1 109.3 . . ? N1 C1A H1A2 109.3 . . ? C2A C1A H1A2 109.3 . . ? H1A1 C1A H1A2 107.9 . . ? C1 C2 C3 116.2(8) . . ? C1 C2 H2 121.9 . . ? C3 C2 H2 121.9 . . ? C3A C2A C1A 110.9(7) . . ? C3A C2A H2A1 109.5 . . ? C1A C2A H2A1 109.5 . . ? C3A C2A H2A2 109.5 . . ? C1A C2A H2A2 109.5 . . ? H2A1 C2A H2A2 108.1 . . ? C2 C3 C4 121.4(7) . . ? C2 C3 H3 119.3 . . ? C4 C3 H3 119.3 . . ? O2A C3A O1A 125.1(8) . . ? O2A C3A C2A 122.9(9) . . ? O1A C3A C2A 112.0(7) . . ? C5 C4 C3 121.0(7) . . ? C5 C4 H4 119.5 . . ? C3 C4 H4 119.5 . . ? C4 C5 C6 118.0(7) . . ? C4 C5 H5 121.0 . . ? C6 C5 H5 121.0 . . ? C1 C6 C5 118.9(7) . . ? C1 C6 C7 110.0(7) . . ? C5 C6 C7 131.0(7) . . ? C6 C7 C8 100.6(6) . . ? C6 C7 C9 114.7(6) . . ? C8 C7 C9 112.2(6) . . ? C6 C7 C10 110.4(6) . . ? C8 C7 C10 107.6(6) . . ? C9 C7 C10 110.8(6) . . ? N1 C8 C11 124.9(8) . . ? N1 C8 C7 110.2(7) . . ? C11 C8 C7 124.9(7) . . ? C7 C9 H9A 109.5 . . ? C7 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? C7 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? C7 C10 H10A 109.5 . . ? C7 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? C7 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? C8 C11 H11A 109.5 . . ? C8 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? C8 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? C8 N1 C1 112.5(7) . . ? C8 N1 C1A 124.5(7) . . ? C1 N1 C1A 123.0(6) . . ? C3A O1A H1A 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C6 C1 C2 C3 -2.3(12) . . . . ? N1 C1 C2 C3 -179.0(7) . . . . ? N1 C1A C2A C3A -161.7(7) . . . . ? C1 C2 C3 C4 2.9(12) . . . . ? C1A C2A C3A O2A -8.1(12) . . . . ? C1A C2A C3A O1A 172.2(7) . . . . ? C2 C3 C4 C5 -2.9(12) . . . . ? C3 C4 C5 C6 2.1(12) . . . . ? C2 C1 C6 C5 1.7(13) . . . . ? N1 C1 C6 C5 179.0(7) . . . . ? C2 C1 C6 C7 178.3(8) . . . . ? N1 C1 C6 C7 -4.4(9) . . . . ? C4 C5 C6 C1 -1.5(12) . . . . ? C4 C5 C6 C7 -177.3(8) . . . . ? C1 C6 C7 C8 3.3(8) . . . . ? C5 C6 C7 C8 179.4(8) . . . . ? C1 C6 C7 C9 124.0(7) . . . . ? C5 C6 C7 C9 -60.0(11) . . . . ? C1 C6 C7 C10 -110.0(7) . . . . ? C5 C6 C7 C10 66.0(11) . . . . ? C6 C7 C8 N1 -1.0(8) . . . . ? C9 C7 C8 N1 -123.4(7) . . . . ? C10 C7 C8 N1 114.5(7) . . . . ? C6 C7 C8 C11 177.5(7) . . . . ? C9 C7 C8 C11 55.1(9) . . . . ? C10 C7 C8 C11 -66.9(10) . . . . ? C11 C8 N1 C1 179.8(7) . . . . ? C7 C8 N1 C1 -1.6(9) . . . . ? C11 C8 N1 C1A 0.9(12) . . . . ? C7 C8 N1 C1A 179.4(6) . . . . ? C2 C1 N1 C8 -179.0(8) . . . . ? C6 C1 N1 C8 3.8(9) . . . . ? C2 C1 N1 C1A -0.1(12) . . . . ? C6 C1 N1 C1A -177.2(7) . . . . ? C2A C1A N1 C8 100.2(9) . . . . ? C2A C1A N1 C1 -78.6(9) . . . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 25.02 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.974 _refine_diff_density_min -0.595 _refine_diff_density_rms 0.149 _database_code_depnum_ccdc_archive 'CCDC 977418' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_3a _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C18 H19 N O3' _chemical_formula_sum 'C18 H19 N O3' _chemical_formula_weight 297.34 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M P-1 _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.2314(2) _cell_length_b 9.4760(3) _cell_length_c 11.6165(4) _cell_angle_alpha 82.094(2) _cell_angle_beta 82.082(2) _cell_angle_gamma 78.631(2) _cell_volume 767.95(4) _cell_formula_units_Z 2 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 3455 _cell_measurement_theta_min 2.910 _cell_measurement_theta_max 27.485 _exptl_crystal_description Slab _exptl_crystal_colour Orange _exptl_crystal_size_max 0.16 _exptl_crystal_size_mid 0.11 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.286 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 316 _exptl_absorpt_coefficient_mu 0.087 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9861 _exptl_absorpt_correction_T_max 0.9956 _exptl_absorpt_process_details 'SADABS 2007/2 (Sheldrick, G.M., 2007)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Bruker-Nonius FR591 rotating anode' _diffrn_radiation_monochromator '10cm confocal mirrors' _diffrn_measurement_device_type 'Bruker-Nonius APEX II CCD camera on \k-goniostat' _diffrn_measurement_method '\f & \w scans' _diffrn_detector_area_resol_mean '4096x4096pixels / 62x62mm' _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 13277 _diffrn_reflns_av_R_equivalents 0.0435 _diffrn_reflns_av_sigmaI/netI 0.0423 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 2.99 _diffrn_reflns_theta_max 27.48 _reflns_number_total 3509 _reflns_number_gt 2951 _reflns_threshold_expression >2\s(I) _computing_data_collection 'COLLECT (Hooft, R.W.W., 1998)' _computing_cell_refinement 'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)' #Although determined using DirAx, the cell is refined in the HKL #package during data reduction _computing_data_reduction 'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2\s(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0345P)^2^+0.6433P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3509 _refine_ls_number_parameters 203 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0673 _refine_ls_R_factor_gt 0.0542 _refine_ls_wR_factor_ref 0.1243 _refine_ls_wR_factor_gt 0.1154 _refine_ls_goodness_of_fit_ref 1.049 _refine_ls_restrained_S_all 1.049 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.3019(2) 0.30222(17) 1.25716(14) 0.0182(3) Uani 1 1 d . . . C1A C 0.2739(2) 0.28546(18) 1.04519(14) 0.0214(3) Uani 1 1 d . . . H1A1 H 0.1516 0.3212 1.0143 0.032 Uiso 1 1 calc R . . H1A2 H 0.2840 0.1823 1.0738 0.032 Uiso 1 1 calc R . . H1A3 H 0.3772 0.2986 0.9829 0.032 Uiso 1 1 calc R . . C1S C 0.2325(2) 0.74692(17) 0.99354(14) 0.0192(3) Uani 1 1 d . . . C2 C 0.3270(2) 0.15692(18) 1.30037(14) 0.0203(3) Uani 1 1 d . . . H2 H 0.3391 0.0833 1.2505 0.024 Uiso 1 1 calc R . . C2S C 0.2375(2) 0.88755(18) 1.03678(15) 0.0227(4) Uani 1 1 d . . . C3 C 0.3336(2) 0.12386(19) 1.42045(15) 0.0229(4) Uani 1 1 d . . . H3 H 0.3498 0.0253 1.4531 0.027 Uiso 1 1 calc R . . C3S C 0.2230(2) 0.96197(18) 0.91174(15) 0.0233(4) Uani 1 1 d . . . C4 C 0.3172(2) 0.23061(19) 1.49387(15) 0.0233(4) Uani 1 1 d . . . H4 H 0.3214 0.2047 1.5756 0.028 Uiso 1 1 calc R . . C4S C 0.2115(2) 0.81939(17) 0.88167(14) 0.0197(3) Uani 1 1 d . . . C5 C 0.2945(2) 0.37681(19) 1.44729(14) 0.0221(3) Uani 1 1 d . . . H5 H 0.2833 0.4507 1.4967 0.026 Uiso 1 1 calc R . . C5S C 0.1582(3) 0.86781(19) 0.68328(14) 0.0236(4) Uani 1 1 d . . . H5S1 H 0.2585 0.9278 0.6663 0.028 Uiso 1 1 calc R . . H5S2 H 0.0335 0.9325 0.6953 0.028 Uiso 1 1 calc R . . C6 C 0.2888(2) 0.41137(17) 1.32833(14) 0.0186(3) Uani 1 1 d . . . C7 C 0.2697(2) 0.55740(17) 1.25429(13) 0.0185(3) Uani 1 1 d . . . C8 C 0.2689(2) 0.51310(17) 1.13227(14) 0.0178(3) Uani 1 1 d . . . C9 C 0.4413(2) 0.62760(19) 1.26268(15) 0.0234(4) Uani 1 1 d . . . H9A H 0.4422 0.6453 1.3437 0.035 Uiso 1 1 calc R . . H9B H 0.4323 0.7197 1.2119 0.035 Uiso 1 1 calc R . . H9C H 0.5587 0.5625 1.2378 0.035 Uiso 1 1 calc R . . C10 C 0.0801(2) 0.65542(19) 1.29103(15) 0.0243(4) Uani 1 1 d . . . H10A H -0.0254 0.6094 1.2803 0.036 Uiso 1 1 calc R . . H10B H 0.0715 0.7492 1.2427 0.036 Uiso 1 1 calc R . . H10C H 0.0736 0.6700 1.3735 0.036 Uiso 1 1 calc R . . C11 C 0.2473(2) 0.59631(17) 1.02665(14) 0.0193(3) Uani 1 1 d . . . H11 H 0.2412 0.5426 0.9644 0.023 Uiso 1 1 calc R . . C6S C 0.1630(3) 0.7798(2) 0.58424(15) 0.0271(4) Uani 1 1 d . . . H6S1 H 0.2893 0.7200 0.5708 0.041 Uiso 1 1 calc R . . H6S2 H 0.1351 0.8450 0.5131 0.041 Uiso 1 1 calc R . . H6S3 H 0.0677 0.7172 0.6042 0.041 Uiso 1 1 calc R . . N1 N 0.28686(19) 0.36639(14) 1.14131(11) 0.0185(3) Uani 1 1 d . . . O1S O 0.2463(2) 0.92998(13) 1.12949(11) 0.0316(3) Uani 1 1 d . . . O2S O 0.2258(2) 1.08360(13) 0.86227(11) 0.0311(3) Uani 1 1 d . . . O3S O 0.19075(18) 0.76367(13) 0.78705(10) 0.0241(3) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0175(7) 0.0206(8) 0.0167(7) -0.0010(6) -0.0024(6) -0.0042(6) C1A 0.0285(9) 0.0188(8) 0.0183(8) -0.0046(6) -0.0033(6) -0.0059(6) C1S 0.0196(8) 0.0197(8) 0.0182(8) -0.0027(6) -0.0026(6) -0.0027(6) C2 0.0209(8) 0.0186(8) 0.0216(8) -0.0019(6) -0.0027(6) -0.0042(6) C2S 0.0284(9) 0.0172(8) 0.0234(8) -0.0021(6) -0.0055(7) -0.0045(6) C3 0.0219(8) 0.0203(8) 0.0253(9) 0.0045(7) -0.0050(6) -0.0043(6) C3S 0.0246(9) 0.0194(8) 0.0259(9) -0.0028(7) -0.0058(7) -0.0019(6) C4 0.0235(8) 0.0278(9) 0.0183(8) 0.0026(7) -0.0042(6) -0.0062(7) C4S 0.0222(8) 0.0182(8) 0.0188(8) -0.0027(6) -0.0030(6) -0.0030(6) C5 0.0221(8) 0.0244(9) 0.0199(8) -0.0028(6) -0.0034(6) -0.0039(6) C5S 0.0297(9) 0.0242(9) 0.0175(8) 0.0035(6) -0.0057(6) -0.0085(7) C6 0.0185(8) 0.0184(8) 0.0184(8) -0.0012(6) -0.0020(6) -0.0031(6) C7 0.0234(8) 0.0181(8) 0.0146(7) -0.0024(6) -0.0028(6) -0.0041(6) C8 0.0173(7) 0.0163(8) 0.0205(8) -0.0039(6) -0.0014(6) -0.0037(6) C9 0.0300(9) 0.0230(9) 0.0195(8) -0.0014(6) -0.0048(7) -0.0100(7) C10 0.0281(9) 0.0225(9) 0.0202(8) -0.0037(7) -0.0002(7) -0.0003(7) C11 0.0231(8) 0.0173(8) 0.0183(8) -0.0035(6) -0.0041(6) -0.0037(6) C6S 0.0282(9) 0.0361(10) 0.0187(8) -0.0024(7) -0.0025(7) -0.0107(8) N1 0.0246(7) 0.0161(7) 0.0153(6) -0.0022(5) -0.0021(5) -0.0044(5) O1S 0.0536(9) 0.0205(6) 0.0234(7) -0.0050(5) -0.0096(6) -0.0077(6) O2S 0.0467(8) 0.0180(6) 0.0297(7) 0.0022(5) -0.0110(6) -0.0073(5) O3S 0.0356(7) 0.0212(6) 0.0166(6) -0.0008(5) -0.0064(5) -0.0065(5) _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C2 1.385(2) . ? C1 C6 1.392(2) . ? C1 N1 1.408(2) . ? C1A N1 1.462(2) . ? C1A H1A1 0.9800 . ? C1A H1A2 0.9800 . ? C1A H1A3 0.9800 . ? C1S C4S 1.397(2) . ? C1S C11 1.413(2) . ? C1S C2S 1.496(2) . ? C2 C3 1.392(2) . ? C2 H2 0.9500 . ? C2S O1S 1.214(2) . ? C2S C3S 1.533(2) . ? C3 C4 1.388(2) . ? C3 H3 0.9500 . ? C3S O2S 1.218(2) . ? C3S C4S 1.462(2) . ? C4 C5 1.403(2) . ? C4 H4 0.9500 . ? C4S O3S 1.3212(19) . ? C5 C6 1.380(2) . ? C5 H5 0.9500 . ? C5S O3S 1.4635(19) . ? C5S C6S 1.504(2) . ? C5S H5S1 0.9900 . ? C5S H5S2 0.9900 . ? C6 C7 1.518(2) . ? C7 C8 1.534(2) . ? C7 C10 1.539(2) . ? C7 C9 1.539(2) . ? C8 N1 1.361(2) . ? C8 C11 1.375(2) . ? C9 H9A 0.9800 . ? C9 H9B 0.9800 . ? C9 H9C 0.9800 . ? C10 H10A 0.9800 . ? C10 H10B 0.9800 . ? C10 H10C 0.9800 . ? C11 H11 0.9500 . ? C6S H6S1 0.9800 . ? C6S H6S2 0.9800 . ? C6S H6S3 0.9800 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 C1 C6 122.47(15) . . ? C2 C1 N1 128.96(15) . . ? C6 C1 N1 108.57(14) . . ? N1 C1A H1A1 109.5 . . ? N1 C1A H1A2 109.5 . . ? H1A1 C1A H1A2 109.5 . . ? N1 C1A H1A3 109.5 . . ? H1A1 C1A H1A3 109.5 . . ? H1A2 C1A H1A3 109.5 . . ? C4S C1S C11 126.52(15) . . ? C4S C1S C2S 89.61(13) . . ? C11 C1S C2S 143.81(15) . . ? C1 C2 C3 116.77(15) . . ? C1 C2 H2 121.6 . . ? C3 C2 H2 121.6 . . ? O1S C2S C1S 137.26(16) . . ? O1S C2S C3S 133.93(16) . . ? C1S C2S C3S 88.81(12) . . ? C4 C3 C2 122.00(16) . . ? C4 C3 H3 119.0 . . ? C2 C3 H3 119.0 . . ? O2S C3S C4S 138.12(17) . . ? O2S C3S C2S 136.02(16) . . ? C4S C3S C2S 85.83(13) . . ? C3 C4 C5 119.92(15) . . ? C3 C4 H4 120.0 . . ? C5 C4 H4 120.0 . . ? O3S C4S C1S 127.54(15) . . ? O3S C4S C3S 136.80(15) . . ? C1S C4S C3S 95.65(13) . . ? C6 C5 C4 118.81(16) . . ? C6 C5 H5 120.6 . . ? C4 C5 H5 120.6 . . ? O3S C5S C6S 106.23(14) . . ? O3S C5S H5S1 110.5 . . ? C6S C5S H5S1 110.5 . . ? O3S C5S H5S2 110.5 . . ? C6S C5S H5S2 110.5 . . ? H5S1 C5S H5S2 108.7 . . ? C5 C6 C1 120.01(15) . . ? C5 C6 C7 130.37(15) . . ? C1 C6 C7 109.63(13) . . ? C6 C7 C8 101.31(12) . . ? C6 C7 C10 110.91(13) . . ? C8 C7 C10 110.17(13) . . ? C6 C7 C9 109.41(13) . . ? C8 C7 C9 112.54(13) . . ? C10 C7 C9 112.01(14) . . ? N1 C8 C11 120.88(14) . . ? N1 C8 C7 108.56(13) . . ? C11 C8 C7 130.51(14) . . ? C7 C9 H9A 109.5 . . ? C7 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? C7 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? C7 C10 H10A 109.5 . . ? C7 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? C7 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? C8 C11 C1S 131.90(15) . . ? C8 C11 H11 114.1 . . ? C1S C11 H11 114.1 . . ? C5S C6S H6S1 109.5 . . ? C5S C6S H6S2 109.5 . . ? H6S1 C6S H6S2 109.5 . . ? C5S C6S H6S3 109.5 . . ? H6S1 C6S H6S3 109.5 . . ? H6S2 C6S H6S3 109.5 . . ? C8 N1 C1 111.90(13) . . ? C8 N1 C1A 124.40(13) . . ? C1 N1 C1A 123.46(13) . . ? C4S O3S C5S 115.54(13) . . ? _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.261 _refine_diff_density_min -0.212 _refine_diff_density_rms 0.050 _database_code_depnum_ccdc_archive 'CCDC 977419' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_4bsalt _audit_creation_method SHELXL-2013 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C34 H36 N2 Na2 O9' _chemical_formula_weight 662.63 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Na Na 0.0362 0.0249 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _space_group_crystal_system triclinic _space_group_IT_number 2 _space_group_name_H-M_alt 'P -1' _space_group_name_Hall '-P 1' _shelx_space_group_comment ; The symmetry employed for this shelxl refinement is uniquely defined by the following loop, which should always be used as a source of symmetry information in preference to the above space-group names. They are only intended as comments. ; loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.810(4) _cell_length_b 12.003(5) _cell_length_c 17.977(8) _cell_angle_alpha 82.678(14) _cell_angle_beta 86.660(17) _cell_angle_gamma 74.635(14) _cell_volume 1817.5(14) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 4381 _cell_measurement_theta_min 2.2 _cell_measurement_theta_max 25.0 _exptl_crystal_description Block _exptl_crystal_colour orange _exptl_crystal_density_meas ? _exptl_crystal_density_method ? _exptl_crystal_density_diffrn 1.211 _exptl_crystal_F_000 696 _exptl_transmission_factor_min ? _exptl_transmission_factor_max ? _exptl_crystal_size_max 0.100 _exptl_crystal_size_mid 0.060 _exptl_crystal_size_min 0.040 _exptl_absorpt_coefficient_mu 0.108 _shelx_estimated_absorpt_T_min 0.989 _shelx_estimated_absorpt_T_max 0.996 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_max 1.000 _exptl_absorpt_correction_T_min 0.719 _exptl_absorpt_process_details 'CrystalClear-SM Expert 2.0 r11 (Rigaku, 2011)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100 _diffrn_source_power 2.5 _diffrn_source_voltage 45.0 _diffrn_source_current 55.0 _diffrn_radiation_wavelength 0.71075 _diffrn_radiation_type 'Mo K\a' _diffrn_source 'Rotating Anode' _diffrn_radiation_monochromator Confocal _diffrn_measurement_specimen_support Mitegen _diffrn_detector CCD _diffrn_measurement_device ; AFC12 (Right): Kappa 3 circle ; _diffrn_measurement_device_type ; Rigaku Saturn724+ (2x2 bin mode) ; _diffrn_detector_area_resol_mean 28.5714 _diffrn_measurement_method 'profile data from \w-scans' _diffrn_reflns_number 26587 _diffrn_reflns_av_unetI/netI 0.0581 _diffrn_reflns_av_R_equivalents 0.0518 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 2.933 _diffrn_reflns_theta_max 25.057 _diffrn_reflns_theta_full 25.242 _diffrn_measured_fraction_theta_max 0.995 _diffrn_measured_fraction_theta_full 0.977 _diffrn_reflns_Laue_measured_fraction_max 0.995 _diffrn_reflns_Laue_measured_fraction_full 0.977 _diffrn_reflns_point_group_measured_fraction_max 0.995 _diffrn_reflns_point_group_measured_fraction_full 0.977 _reflns_number_total 6434 _reflns_number_gt 4237 _reflns_threshold_expression 'I > 2\s(I)' _reflns_Friedel_coverage 0.000 _reflns_Friedel_fraction_max . _reflns_Friedel_fraction_full . _reflns_special_details ; Reflections were merged by SHELXL according to the crystal class for the calculation of statistics and refinement. Structure factors included contributions from the .fab file. _reflns_Friedel_fraction is defined as the number of unique Friedel pairs measured divided by the number that would be possible theoretically, ignoring centric projections and systematic absences. ; _computing_data_collection 'CrystalClear-SM Expert 2.0 r11 (Rigaku, 2011)' _computing_cell_refinement 'CrystalClear-SM Expert 2.0 r11 (Rigaku, 2011)' _computing_data_reduction 'CrystalClear-SM Expert 2.0 r11 (Rigaku, 2011)' _computing_structure_solution 'SHELXL-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-2013 (Sheldrick, 2013)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Crystal structure of 4b_salt exhibits positional disorder which has been modelled over two sites with 60:40 ratio. Additionaly, in 4b_salt highly diffused solvent electron density has been removed with PLATON/SQUEEZE routine. The hydrogen atoms on O3 and O6 have been succesfuly found and refined. However, finding hydrogen atoms on 05 was difficult possibly due to presence of highly diffused electron density from solvent molecules located in the voids. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.1381P)^2^+0.1063P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary ? _atom_sites_solution_secondary ? _atom_sites_solution_hydrogens mixed _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.028(5) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 6434 _refine_ls_number_parameters 510 _refine_ls_number_restraints 791 _refine_ls_R_factor_all 0.0986 _refine_ls_R_factor_gt 0.0751 _refine_ls_wR_factor_ref 0.2457 _refine_ls_wR_factor_gt 0.2271 _refine_ls_goodness_of_fit_ref 1.085 _refine_ls_restrained_S_all 1.030 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_site_symmetry_order _atom_site_calc_flag _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group C101 C -0.0440(6) 0.6454(8) 0.5406(4) 0.051(2) Uani 0.625(7) 1 d G U P A 1 C102 C -0.0818(6) 0.6657(7) 0.4652(4) 0.055(2) Uani 0.625(7) 1 d G U P A 1 H102 H -0.0073 0.6834 0.4283 0.066 Uiso 0.625(7) 1 calc R U P A 1 C103 C -0.2284(7) 0.6602(6) 0.4438(2) 0.0556(19) Uani 0.625(7) 1 d G U P A 1 H103 H -0.2542 0.6741 0.3923 0.067 Uiso 0.625(7) 1 calc R U P A 1 C104 C -0.3374(5) 0.6343(6) 0.4978(2) 0.0608(19) Uani 0.625(7) 1 d G U P A 1 H104 H -0.4376 0.6305 0.4832 0.073 Uiso 0.625(7) 1 calc R U P A 1 C105 C -0.2996(5) 0.6140(6) 0.5732(2) 0.0556(17) Uani 0.625(7) 1 d G U P A 1 H105 H -0.3741 0.5963 0.6101 0.067 Uiso 0.625(7) 1 calc R U P A 1 C106 C -0.1530(6) 0.6195(7) 0.5946(3) 0.047(2) Uani 0.625(7) 1 d G U P A 1 C107 C -0.0866(16) 0.6027(8) 0.6708(7) 0.040(2) Uani 0.625(7) 1 d D U P A 1 C108 C -0.0762(16) 0.4816(7) 0.7121(7) 0.047(2) Uani 0.625(7) 1 d D U P A 1 H10A H -0.0324 0.4757 0.7617 0.071 Uiso 0.625(7) 1 calc R U P A 1 H10B H -0.0079 0.4228 0.6832 0.071 Uiso 0.625(7) 1 calc R U P A 1 H10C H -0.1817 0.4686 0.7177 0.071 Uiso 0.625(7) 1 calc R U P A 1 C109 C -0.1713(15) 0.6968(7) 0.7203(6) 0.048(2) Uani 0.625(7) 1 d D U P A 1 H10D H -0.1227 0.6804 0.7695 0.072 Uiso 0.625(7) 1 calc R U P A 1 H10E H -0.2827 0.6970 0.7266 0.072 Uiso 0.625(7) 1 calc R U P A 1 H10F H -0.1628 0.7731 0.6965 0.072 Uiso 0.625(7) 1 calc R U P A 1 C110 C 0.089(3) 0.624(4) 0.6493(18) 0.042(3) Uani 0.625(7) 1 d . U P A 1 C1C C 0.2439(14) 0.6497(9) 0.5284(9) 0.050(2) Uani 0.625(7) 1 d . U P A 1 H1C1 H 0.3308 0.5942 0.5569 0.059 Uiso 0.625(7) 1 calc R U P A 1 H1C2 H 0.2436 0.6261 0.4776 0.059 Uiso 0.625(7) 1 calc R U P A 1 C2C C 0.2597(7) 0.7731(6) 0.5242(4) 0.0572(18) Uani 0.625(7) 1 d . U P A 1 H2C1 H 0.3546 0.7797 0.4947 0.086 Uiso 0.625(7) 1 calc R U P A 1 H2C2 H 0.2677 0.7923 0.5750 0.086 Uiso 0.625(7) 1 calc R U P A 1 H2C3 H 0.1671 0.8271 0.5003 0.086 Uiso 0.625(7) 1 calc R U P A 1 N101 N 0.084(2) 0.6553(13) 0.5699(10) 0.044(2) Uani 0.625(7) 1 d . U P A 1 C201 C -0.0509(8) 0.6655(13) 0.5370(7) 0.048(3) Uani 0.375(7) 1 d G U P A 2 C202 C -0.0932(10) 0.6950(11) 0.4624(6) 0.052(3) Uani 0.375(7) 1 d G U P A 2 H202 H -0.0146 0.6975 0.4242 0.062 Uiso 0.375(7) 1 calc R U P A 2 C203 C -0.2506(11) 0.7210(8) 0.4436(4) 0.051(3) Uani 0.375(7) 1 d G U P A 2 H203 H -0.2796 0.7412 0.3926 0.062 Uiso 0.375(7) 1 calc R U P A 2 C204 C -0.3656(8) 0.7174(9) 0.4995(4) 0.053(3) Uani 0.375(7) 1 d G U P A 2 H204 H -0.4732 0.7352 0.4867 0.064 Uiso 0.375(7) 1 calc R U P A 2 C205 C -0.3233(10) 0.6879(8) 0.5742(3) 0.046(2) Uani 0.375(7) 1 d G U P A 2 H205 H -0.4019 0.6854 0.6124 0.056 Uiso 0.375(7) 1 calc R U P A 2 C206 C -0.1659(11) 0.6619(10) 0.5929(5) 0.047(3) Uani 0.375(7) 1 d G U P A 2 C207 C -0.081(3) 0.6379(14) 0.6697(12) 0.038(3) Uani 0.375(7) 1 d D U P A 2 C208 C -0.104(3) 0.5215(14) 0.7068(13) 0.047(2) Uani 0.375(7) 1 d D U P A 2 H20A H -0.2150 0.5302 0.7211 0.071 Uiso 0.375(7) 1 calc R U P A 2 H20B H -0.0396 0.4962 0.7516 0.071 Uiso 0.375(7) 1 calc R U P A 2 H20C H -0.0711 0.4633 0.6714 0.071 Uiso 0.375(7) 1 calc R U P A 2 C209 C -0.162(3) 0.7388(13) 0.7149(12) 0.048(2) Uani 0.375(7) 1 d D U P A 2 H20D H -0.2725 0.7396 0.7244 0.072 Uiso 0.375(7) 1 calc R U P A 2 H20E H -0.1546 0.8125 0.6863 0.072 Uiso 0.375(7) 1 calc R U P A 2 H20F H -0.1090 0.7286 0.7628 0.072 Uiso 0.375(7) 1 calc R U P A 2 C210 C 0.073(6) 0.621(7) 0.647(3) 0.041(4) Uani 0.375(7) 1 d . U P A 2 C1B C 0.210(3) 0.6879(17) 0.5267(16) 0.050(2) Uani 0.375(7) 1 d . U P A 2 H1B1 H 0.1501 0.7498 0.4897 0.059 Uiso 0.375(7) 1 calc R U P A 2 H1B2 H 0.2758 0.7200 0.5565 0.059 Uiso 0.375(7) 1 calc R U P A 2 C2B C 0.3014(14) 0.5857(10) 0.4918(7) 0.065(3) Uani 0.375(7) 1 d . U P A 2 H2B1 H 0.3907 0.6050 0.4629 0.097 Uiso 0.375(7) 1 calc R U P A 2 H2B2 H 0.2341 0.5627 0.4583 0.097 Uiso 0.375(7) 1 calc R U P A 2 H2B3 H 0.3405 0.5212 0.5310 0.097 Uiso 0.375(7) 1 calc R U P A 2 N102 N 0.107(4) 0.628(3) 0.5744(18) 0.044(2) Uani 0.375(7) 1 d . U P A 2 C111 C 0.2084(4) 0.6105(3) 0.69180(18) 0.0434(8) Uani 1 1 d . U . . . H111 H 0.3027 0.6150 0.6646 0.052 Uiso 1 1 calc R U . A 1 C21S C 0.2266(4) 0.5903(3) 0.77108(18) 0.0384(7) Uani 1 1 d . U . . . C24S C 0.3708(4) 0.5779(3) 0.80880(17) 0.0397(8) Uani 1 1 d . U . . . C23S C 0.2922(4) 0.5595(3) 0.88305(17) 0.0371(7) Uani 1 1 d . U . . . C22S C 0.1428(4) 0.5771(3) 0.84234(18) 0.0430(8) Uani 1 1 d . U . . . C1 C 0.5895(4) 0.0299(3) 0.63930(19) 0.0443(8) Uani 1 1 d . U . . . C2 C 0.6534(4) -0.0343(3) 0.58083(19) 0.0520(9) Uani 1 1 d . U . . . H2 H 0.5907 -0.0679 0.5539 0.062 Uiso 1 1 calc R U . . . C3 C 0.8116(5) -0.0477(4) 0.5631(2) 0.0660(12) Uani 1 1 d . U . . . H3 H 0.8585 -0.0927 0.5239 0.079 Uiso 1 1 calc R U . . . C4 C 0.9028(5) 0.0026(5) 0.6009(2) 0.0753(14) Uani 1 1 d . U . . . H4 H 1.0112 -0.0075 0.5876 0.090 Uiso 1 1 calc R U . . . C5 C 0.8356(5) 0.0687(4) 0.6591(2) 0.0651(12) Uani 1 1 d . U . . . H5 H 0.8980 0.1031 0.6857 0.078 Uiso 1 1 calc R U . . . C6 C 0.6779(4) 0.0833(3) 0.67723(19) 0.0455(8) Uani 1 1 d . U . . . C7 C 0.5777(4) 0.1450(3) 0.73850(19) 0.0425(8) Uani 1 1 d . U . . . C9 C 0.5661(5) 0.2768(3) 0.7266(2) 0.0569(10) Uani 1 1 d . U . . . H9A H 0.6712 0.2891 0.7291 0.085 Uiso 1 1 calc R U . . . H9B H 0.4974 0.3151 0.7658 0.085 Uiso 1 1 calc R U . . . H9C H 0.5223 0.3099 0.6773 0.085 Uiso 1 1 calc R U . . . C10 C 0.6457(4) 0.0902(3) 0.8154(2) 0.0503(9) Uani 1 1 d . U . . . H10G H 0.6522 0.0068 0.8217 0.075 Uiso 1 1 calc R U . . . H10H H 0.5772 0.1274 0.8551 0.075 Uiso 1 1 calc R U . . . H10I H 0.7512 0.1015 0.8186 0.075 Uiso 1 1 calc R U . . . C1A C 0.3179(4) -0.0001(3) 0.6493(2) 0.0516(9) Uani 1 1 d . U . . . H1A1 H 0.3400 -0.0201 0.5973 0.062 Uiso 1 1 calc R U . . . H1A2 H 0.2134 0.0565 0.6507 0.062 Uiso 1 1 calc R U . . . C2A C 0.3142(5) -0.1089(4) 0.7015(2) 0.0674(11) Uani 1 1 d . U . . . H2A1 H 0.4147 -0.1675 0.6972 0.101 Uiso 1 1 calc R U . . . H2A2 H 0.2285 -0.1396 0.6877 0.101 Uiso 1 1 calc R U . . . H2A3 H 0.2970 -0.0900 0.7533 0.101 Uiso 1 1 calc R U . . . N1 N 0.4369(3) 0.0530(3) 0.67016(16) 0.0470(7) Uani 1 1 d . U . . . C8 C 0.4211(4) 0.1187(3) 0.72895(19) 0.0439(8) Uani 1 1 d . U . . . C11 C 0.2832(4) 0.1506(3) 0.7672(2) 0.0538(10) Uani 1 1 d . U . . . H11 H 0.2010 0.1248 0.7489 0.065 Uiso 1 1 calc R U . . . C1S C 0.2361(4) 0.2155(3) 0.8297(2) 0.0523(9) Uani 1 1 d . U . . . C4S C 0.0803(4) 0.2442(4) 0.8628(3) 0.0727(14) Uani 1 1 d . U . . . C3S C 0.1318(4) 0.3061(3) 0.9188(2) 0.0536(10) Uani 1 1 d . U . . . C2S C 0.2933(4) 0.2734(3) 0.8839(2) 0.0450(8) Uani 1 1 d . U . . . O23S O 0.5071(3) 0.5816(2) 0.78760(13) 0.0528(7) Uani 1 1 d . U . . . O22S O 0.3300(2) 0.53858(19) 0.94911(11) 0.0388(5) Uani 1 1 d . U . . . O21S O 0.0068(3) 0.5780(3) 0.86413(14) 0.0638(8) Uani 1 1 d . U . . . O1S O 0.4197(3) 0.2897(2) 0.89903(14) 0.0493(6) Uani 1 1 d . U . . . O2S O 0.0702(3) 0.3609(2) 0.97132(14) 0.0519(7) Uani 1 1 d . U . . . O3S O -0.0448(3) 0.2207(4) 0.8505(3) 0.1201(18) Uani 1 1 d . U . . . O6 O 0.3933(3) 0.3245(2) 1.09073(13) 0.0448(6) Uani 1 1 d D U . . . O5 O 0.7760(4) 0.1791(3) 0.9932(2) 0.0954(11) Uani 1 1 d . U . . . O4 O 0.7174(3) 0.4132(2) 0.88307(12) 0.0440(6) Uani 1 1 d D U . . . Na1 Na 0.55307(14) 0.35276(12) 0.98084(7) 0.0441(4) Uani 1 1 d . U . . . Na2 Na -0.16426(14) 0.52232(11) 0.95252(7) 0.0402(4) Uani 1 1 d . U . . . H30 H 0.386(5) 0.2543(14) 1.0991(19) 0.060 Uiso 1 1 d D U . . . H1O H 0.668(4) 0.460(2) 0.8486(14) 0.060 Uiso 1 1 d D U . . . H4O H 0.401(5) 0.351(3) 1.1296(12) 0.060 Uiso 1 1 d D U . . . H2O H 0.772(4) 0.355(2) 0.8642(18) 0.060 Uiso 1 1 d D U . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C101 0.059(4) 0.073(5) 0.033(4) -0.011(4) 0.000(3) -0.034(4) C102 0.063(4) 0.069(5) 0.030(4) -0.007(3) 0.003(3) -0.014(3) C103 0.062(4) 0.065(5) 0.032(3) -0.005(3) -0.008(3) -0.002(4) C104 0.043(3) 0.090(5) 0.044(3) -0.021(3) -0.004(3) -0.002(3) C105 0.047(3) 0.083(5) 0.038(3) -0.012(3) 0.001(3) -0.016(4) C106 0.039(3) 0.068(6) 0.034(3) -0.004(3) 0.001(2) -0.013(3) C107 0.044(3) 0.058(6) 0.028(3) -0.009(4) 0.002(2) -0.031(4) C108 0.048(5) 0.065(6) 0.033(3) 0.001(4) -0.004(3) -0.025(5) C109 0.048(3) 0.062(6) 0.029(3) 0.000(5) 0.001(2) -0.008(5) C110 0.046(6) 0.060(6) 0.027(4) -0.007(5) 0.004(4) -0.028(6) C1C 0.055(6) 0.069(7) 0.031(2) -0.016(5) 0.009(4) -0.025(5) C2C 0.051(4) 0.068(4) 0.053(4) -0.009(3) 0.015(3) -0.019(3) N101 0.048(5) 0.061(7) 0.024(2) -0.002(4) 0.001(3) -0.020(4) C201 0.043(5) 0.061(7) 0.033(5) -0.002(6) -0.014(4) -0.002(5) C202 0.070(6) 0.054(7) 0.034(5) 0.003(5) -0.013(5) -0.021(5) C203 0.067(6) 0.047(6) 0.039(5) -0.003(5) -0.024(4) -0.009(6) C204 0.056(5) 0.057(6) 0.046(5) -0.006(5) -0.029(4) -0.008(5) C205 0.050(5) 0.055(6) 0.040(4) -0.008(5) -0.013(4) -0.018(5) C206 0.048(5) 0.057(8) 0.036(5) -0.006(4) -0.017(4) -0.009(5) C207 0.049(5) 0.052(8) 0.026(4) -0.001(6) -0.008(4) -0.037(6) C208 0.048(5) 0.065(6) 0.033(3) 0.001(4) -0.004(3) -0.025(5) C209 0.048(3) 0.062(6) 0.029(3) 0.000(5) 0.001(2) -0.008(5) C210 0.041(7) 0.058(11) 0.025(5) -0.005(7) -0.003(4) -0.017(7) C1B 0.055(6) 0.069(7) 0.031(2) -0.016(5) 0.009(4) -0.025(5) C2B 0.068(7) 0.062(7) 0.067(8) -0.017(5) 0.015(5) -0.021(5) N102 0.048(5) 0.061(7) 0.024(2) -0.002(4) 0.001(3) -0.020(4) C111 0.0407(19) 0.067(2) 0.0282(16) -0.0075(15) 0.0048(14) -0.0242(16) C21S 0.0365(17) 0.0539(19) 0.0299(16) -0.0101(13) 0.0012(13) -0.0187(14) C24S 0.0363(18) 0.058(2) 0.0284(16) -0.0084(14) 0.0025(13) -0.0185(14) C23S 0.0355(17) 0.0503(18) 0.0303(17) -0.0119(13) 0.0046(13) -0.0175(13) C22S 0.0358(18) 0.067(2) 0.0287(17) -0.0098(15) 0.0027(14) -0.0170(15) C1 0.0391(18) 0.061(2) 0.0332(18) -0.0104(15) 0.0011(14) -0.0120(15) C2 0.044(2) 0.079(3) 0.0330(19) -0.0161(17) 0.0000(15) -0.0123(18) C3 0.051(2) 0.113(4) 0.038(2) -0.028(2) 0.0099(18) -0.021(2) C4 0.042(2) 0.139(4) 0.049(2) -0.033(3) 0.0124(19) -0.023(2) C5 0.047(2) 0.119(4) 0.038(2) -0.023(2) 0.0064(17) -0.033(2) C6 0.0371(18) 0.071(2) 0.0307(17) -0.0114(15) 0.0013(14) -0.0163(16) C7 0.0372(18) 0.058(2) 0.0354(18) -0.0094(14) -0.0039(14) -0.0148(15) C9 0.063(2) 0.067(2) 0.048(2) -0.0139(18) -0.0042(18) -0.0259(19) C10 0.042(2) 0.068(2) 0.040(2) -0.0143(16) -0.0010(16) -0.0081(16) C1A 0.043(2) 0.070(2) 0.052(2) -0.0307(18) 0.0009(17) -0.0198(17) C2A 0.077(3) 0.078(3) 0.058(3) -0.020(2) 0.001(2) -0.036(2) N1 0.0393(16) 0.0641(18) 0.0426(17) -0.0219(14) -0.0036(13) -0.0141(13) C8 0.0385(18) 0.054(2) 0.0423(19) -0.0198(15) -0.0048(15) -0.0099(14) C11 0.0334(18) 0.073(2) 0.064(2) -0.040(2) -0.0006(16) -0.0143(16) C1S 0.0360(18) 0.069(2) 0.060(2) -0.0391(19) 0.0005(16) -0.0124(16) C4S 0.033(2) 0.102(3) 0.097(3) -0.069(3) 0.003(2) -0.016(2) C3S 0.0337(18) 0.060(2) 0.073(3) -0.0366(19) -0.0007(17) -0.0099(15) C2S 0.0326(18) 0.062(2) 0.044(2) -0.0212(16) -0.0021(15) -0.0112(15) O23S 0.0374(13) 0.0931(19) 0.0334(13) -0.0087(12) 0.0045(10) -0.0271(12) O22S 0.0363(12) 0.0599(14) 0.0243(12) -0.0086(9) -0.0015(9) -0.0178(10) O21S 0.0357(14) 0.125(2) 0.0337(14) 0.0001(14) 0.0024(11) -0.0305(14) O1S 0.0359(13) 0.0696(16) 0.0495(15) -0.0281(12) 0.0001(11) -0.0164(11) O2S 0.0374(13) 0.0687(16) 0.0529(15) -0.0326(12) -0.0017(11) -0.0071(11) O3S 0.0335(15) 0.176(4) 0.183(4) -0.149(3) 0.017(2) -0.0275(19) O6 0.0430(13) 0.0595(15) 0.0350(13) -0.0097(11) -0.0002(11) -0.0170(11) O5 0.085(2) 0.088(2) 0.104(3) -0.026(2) -0.023(2) 0.0055(17) O4 0.0364(13) 0.0681(16) 0.0328(13) -0.0183(11) 0.0060(10) -0.0184(11) Na1 0.0377(7) 0.0686(9) 0.0330(7) -0.0167(6) 0.0027(6) -0.0216(6) Na2 0.0305(7) 0.0629(8) 0.0314(7) -0.0150(6) 0.0037(5) -0.0158(6) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C101 N101 1.308(19) . ? C101 C102 1.3900 . ? C101 C106 1.3900 . ? C102 C103 1.3900 . ? C102 H102 0.9500 . ? C103 C104 1.3900 . ? C103 H103 0.9500 . ? C104 C105 1.3900 . ? C104 H104 0.9500 . ? C105 C106 1.3900 . ? C105 H105 0.9500 . ? C106 C107 1.490(15) . ? C107 C108 1.528(7) . ? C107 C109 1.535(7) . ? C107 C110 1.65(3) . ? C108 H10A 0.9800 . ? C108 H10B 0.9800 . ? C108 H10C 0.9800 . ? C109 H10D 0.9800 . ? C109 H10E 0.9800 . ? C109 H10F 0.9800 . ? C110 C111 1.30(2) . ? C110 N101 1.43(4) . ? C1C C2C 1.517(13) . ? C1C N101 1.55(3) . ? C1C H1C1 0.9900 . ? C1C H1C2 0.9900 . ? C2C H2C1 0.9800 . ? C2C H2C2 0.9800 . ? C2C H2C3 0.9800 . ? C201 C202 1.3900 . ? C201 C206 1.3900 . ? C201 N102 1.51(3) . ? C202 C203 1.3900 . ? C202 H202 0.9500 . ? C203 C204 1.3900 . ? C203 H203 0.9500 . ? C204 C205 1.3900 . ? C204 H204 0.9500 . ? C205 C206 1.3900 . ? C205 H205 0.9500 . ? C206 C207 1.57(2) . ? C207 C210 1.37(6) . ? C207 C208 1.527(9) . ? C207 C209 1.534(9) . ? C208 H20A 0.9800 . ? C208 H20B 0.9800 . ? C208 H20C 0.9800 . ? C209 H20D 0.9800 . ? C209 H20E 0.9800 . ? C209 H20F 0.9800 . ? C210 N102 1.33(7) . ? C210 C111 1.44(4) . ? C1B C2B 1.47(2) . ? C1B N102 1.48(5) . ? C1B H1B1 0.9900 . ? C1B H1B2 0.9900 . ? C2B H2B1 0.9800 . ? C2B H2B2 0.9800 . ? C2B H2B3 0.9800 . ? C111 C21S 1.426(5) . ? C111 H111 0.9500 . ? C21S C24S 1.439(5) . ? C21S C22S 1.453(4) . ? C24S O23S 1.250(4) . ? C24S C23S 1.486(4) . ? C23S O22S 1.229(4) . ? C23S C22S 1.495(5) . ? C22S O21S 1.237(4) . ? C1 C6 1.386(5) . ? C1 C2 1.387(5) . ? C1 N1 1.396(4) . ? C2 C3 1.383(5) . ? C2 H2 0.9500 . ? C3 C4 1.378(6) . ? C3 H3 0.9500 . ? C4 C5 1.402(6) . ? C4 H4 0.9500 . ? C5 C6 1.378(5) . ? C5 H5 0.9500 . ? C6 C7 1.513(5) . ? C7 C8 1.518(5) . ? C7 C10 1.536(5) . ? C7 C9 1.546(5) . ? C9 H9A 0.9800 . ? C9 H9B 0.9800 . ? C9 H9C 0.9800 . ? C10 H10G 0.9800 . ? C10 H10H 0.9800 . ? C10 H10I 0.9800 . ? C1A N1 1.451(4) . ? C1A C2A 1.514(6) . ? C1A H1A1 0.9900 . ? C1A H1A2 0.9900 . ? C2A H2A1 0.9800 . ? C2A H2A2 0.9800 . ? C2A H2A3 0.9800 . ? N1 C8 1.377(4) . ? C8 C11 1.349(5) . ? C11 C1S 1.427(5) . ? C11 H11 0.9500 . ? C1S C4S 1.437(5) . ? C1S C2S 1.451(5) . ? C4S O3S 1.245(5) . ? C4S C3S 1.481(5) . ? C3S O2S 1.235(4) . ? C3S C2S 1.495(5) . ? C2S O1S 1.231(4) . ? O22S Na1 2.373(2) 2_667 ? O22S Na2 2.394(2) 2_567 ? O22S Na1 2.578(3) . ? O21S Na2 2.286(3) . ? O1S Na1 2.252(3) . ? O2S Na2 2.401(3) 2_567 ? O2S Na2 2.435(3) . ? O6 Na1 2.400(3) . ? O6 Na2 2.431(3) 2_567 ? O6 H30 0.856(10) . ? O6 H4O 0.821(10) . ? O5 Na1 2.453(4) . ? O4 Na1 2.376(3) . ? O4 Na2 2.378(3) 1_655 ? O4 H1O 0.835(10) . ? O4 H2O 0.834(10) . ? Na1 O22S 2.373(2) 2_667 ? Na1 Na1 3.555(3) 2_667 ? Na1 Na2 3.560(2) 2_567 ? Na1 Na2 3.588(2) 1_655 ? Na2 O4 2.378(3) 1_455 ? Na2 O22S 2.394(2) 2_567 ? Na2 O2S 2.401(3) 2_567 ? Na2 O6 2.431(3) 2_567 ? Na2 Na2 3.331(3) 2_567 ? Na2 Na1 3.560(2) 2_567 ? Na2 Na1 3.588(2) 1_455 ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N101 C101 C102 127.2(10) . . ? N101 C101 C106 112.6(10) . . ? C102 C101 C106 120.0 . . ? C101 C102 C103 120.0 . . ? C101 C102 H102 120.0 . . ? C103 C102 H102 120.0 . . ? C104 C103 C102 120.0 . . ? C104 C103 H103 120.0 . . ? C102 C103 H103 120.0 . . ? C103 C104 C105 120.0 . . ? C103 C104 H104 120.0 . . ? C105 C104 H104 120.0 . . ? C106 C105 C104 120.0 . . ? C106 C105 H105 120.0 . . ? C104 C105 H105 120.0 . . ? C105 C106 C101 120.0 . . ? C105 C106 C107 129.9(6) . . ? C101 C106 C107 110.1(6) . . ? C106 C107 C108 113.1(8) . . ? C106 C107 C109 113.6(10) . . ? C108 C107 C109 110.4(7) . . ? C106 C107 C110 100.5(13) . . ? C108 C107 C110 112.1(19) . . ? C109 C107 C110 106.7(18) . . ? C107 C108 H10A 109.5 . . ? C107 C108 H10B 109.5 . . ? H10A C108 H10B 109.5 . . ? C107 C108 H10C 109.5 . . ? H10A C108 H10C 109.5 . . ? H10B C108 H10C 109.5 . . ? C107 C109 H10D 109.5 . . ? C107 C109 H10E 109.5 . . ? H10D C109 H10E 109.5 . . ? C107 C109 H10F 109.5 . . ? H10D C109 H10F 109.5 . . ? H10E C109 H10F 109.5 . . ? C111 C110 N101 127(2) . . ? C111 C110 C107 130(2) . . ? N101 C110 C107 102.8(17) . . ? C2C C1C N101 103.6(9) . . ? C2C C1C H1C1 111.0 . . ? N101 C1C H1C1 111.0 . . ? C2C C1C H1C2 111.0 . . ? N101 C1C H1C2 111.0 . . ? H1C1 C1C H1C2 109.0 . . ? C1C C2C H2C1 109.5 . . ? C1C C2C H2C2 109.5 . . ? H2C1 C2C H2C2 109.5 . . ? C1C C2C H2C3 109.5 . . ? H2C1 C2C H2C3 109.5 . . ? H2C2 C2C H2C3 109.5 . . ? C101 N101 C110 113.5(18) . . ? C101 N101 C1C 126.0(16) . . ? C110 N101 C1C 116.0(16) . . ? C202 C201 C206 120.0 . . ? C202 C201 N102 132.5(15) . . ? C206 C201 N102 107.4(15) . . ? C201 C202 C203 120.0 . . ? C201 C202 H202 120.0 . . ? C203 C202 H202 120.0 . . ? C204 C203 C202 120.0 . . ? C204 C203 H203 120.0 . . ? C202 C203 H203 120.0 . . ? C203 C204 C205 120.0 . . ? C203 C204 H204 120.0 . . ? C205 C204 H204 120.0 . . ? C206 C205 C204 120.0 . . ? C206 C205 H205 120.0 . . ? C204 C205 H205 120.0 . . ? C205 C206 C201 120.0 . . ? C205 C206 C207 132.9(10) . . ? C201 C206 C207 106.8(10) . . ? C210 C207 C208 108(4) . . ? C210 C207 C209 120(4) . . ? C208 C207 C209 112.3(13) . . ? C210 C207 C206 102(2) . . ? C208 C207 C206 105.9(14) . . ? C209 C207 C206 106.9(17) . . ? C207 C208 H20A 109.5 . . ? C207 C208 H20B 109.5 . . ? H20A C208 H20B 109.5 . . ? C207 C208 H20C 109.5 . . ? H20A C208 H20C 109.5 . . ? H20B C208 H20C 109.5 . . ? C207 C209 H20D 109.5 . . ? C207 C209 H20E 109.5 . . ? H20D C209 H20E 109.5 . . ? C207 C209 H20F 109.5 . . ? H20D C209 H20F 109.5 . . ? H20E C209 H20F 109.5 . . ? N102 C210 C207 118(3) . . ? N102 C210 C111 113(4) . . ? C207 C210 C111 129(5) . . ? C2B C1B N102 96.5(18) . . ? C2B C1B H1B1 112.5 . . ? N102 C1B H1B1 112.5 . . ? C2B C1B H1B2 112.5 . . ? N102 C1B H1B2 112.5 . . ? H1B1 C1B H1B2 110.0 . . ? C1B C2B H2B1 109.5 . . ? C1B C2B H2B2 109.5 . . ? H2B1 C2B H2B2 109.5 . . ? C1B C2B H2B3 109.5 . . ? H2B1 C2B H2B3 109.5 . . ? H2B2 C2B H2B3 109.5 . . ? C210 N102 C1B 132(4) . . ? C210 N102 C201 105(3) . . ? C1B N102 C201 105(2) . . ? C110 C111 C21S 133.1(14) . . ? C21S C111 C210 131(2) . . ? C110 C111 H111 113.5 . . ? C21S C111 H111 113.5 . . ? C111 C21S C24S 125.2(3) . . ? C111 C21S C22S 143.7(3) . . ? C24S C21S C22S 91.1(3) . . ? O23S C24S C21S 134.5(3) . . ? O23S C24S C23S 134.5(3) . . ? C21S C24S C23S 91.0(2) . . ? O22S C23S C24S 137.1(3) . . ? O22S C23S C22S 135.2(3) . . ? C24S C23S C22S 87.7(2) . . ? O21S C22S C21S 137.3(3) . . ? O21S C22S C23S 132.6(3) . . ? C21S C22S C23S 90.1(2) . . ? C6 C1 C2 121.8(3) . . ? C6 C1 N1 108.8(3) . . ? C2 C1 N1 129.4(3) . . ? C3 C2 C1 117.7(4) . . ? C3 C2 H2 121.1 . . ? C1 C2 H2 121.1 . . ? C4 C3 C2 121.5(4) . . ? C4 C3 H3 119.2 . . ? C2 C3 H3 119.2 . . ? C3 C4 C5 119.9(4) . . ? C3 C4 H4 120.0 . . ? C5 C4 H4 120.0 . . ? C6 C5 C4 119.2(4) . . ? C6 C5 H5 120.4 . . ? C4 C5 H5 120.4 . . ? C5 C6 C1 119.7(3) . . ? C5 C6 C7 130.4(3) . . ? C1 C6 C7 109.8(3) . . ? C6 C7 C8 101.5(3) . . ? C6 C7 C10 109.7(3) . . ? C8 C7 C10 110.7(3) . . ? C6 C7 C9 111.1(3) . . ? C8 C7 C9 112.5(3) . . ? C10 C7 C9 110.9(3) . . ? C7 C9 H9A 109.5 . . ? C7 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? C7 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? C7 C10 H10G 109.5 . . ? C7 C10 H10H 109.5 . . ? H10G C10 H10H 109.5 . . ? C7 C10 H10I 109.5 . . ? H10G C10 H10I 109.5 . . ? H10H C10 H10I 109.5 . . ? N1 C1A C2A 111.7(3) . . ? N1 C1A H1A1 109.3 . . ? C2A C1A H1A1 109.3 . . ? N1 C1A H1A2 109.3 . . ? C2A C1A H1A2 109.3 . . ? H1A1 C1A H1A2 107.9 . . ? C1A C2A H2A1 109.5 . . ? C1A C2A H2A2 109.5 . . ? H2A1 C2A H2A2 109.5 . . ? C1A C2A H2A3 109.5 . . ? H2A1 C2A H2A3 109.5 . . ? H2A2 C2A H2A3 109.5 . . ? C8 N1 C1 111.5(3) . . ? C8 N1 C1A 124.6(3) . . ? C1 N1 C1A 123.3(3) . . ? C11 C8 N1 121.5(3) . . ? C11 C8 C7 130.1(3) . . ? N1 C8 C7 108.4(3) . . ? C8 C11 C1S 132.9(3) . . ? C8 C11 H11 113.5 . . ? C1S C11 H11 113.5 . . ? C11 C1S C4S 125.5(3) . . ? C11 C1S C2S 143.3(3) . . ? C4S C1S C2S 91.2(3) . . ? O3S C4S C1S 133.6(4) . . ? O3S C4S C3S 135.3(4) . . ? C1S C4S C3S 91.1(3) . . ? O2S C3S C4S 136.7(3) . . ? O2S C3S C2S 135.6(3) . . ? C4S C3S C2S 87.7(3) . . ? O1S C2S C1S 137.3(3) . . ? O1S C2S C3S 132.7(3) . . ? C1S C2S C3S 90.0(3) . . ? C23S O22S Na1 128.4(2) . 2_667 ? C23S O22S Na2 122.84(19) . 2_567 ? Na1 O22S Na2 97.68(9) 2_667 2_567 ? C23S O22S Na1 115.3(2) . . ? Na1 O22S Na1 91.69(9) 2_667 . ? Na2 O22S Na1 91.39(9) 2_567 . ? C22S O21S Na2 150.2(2) . . ? C2S O1S Na1 146.7(2) . . ? C3S O2S Na2 132.2(2) . 2_567 ? C3S O2S Na2 120.8(2) . . ? Na2 O2S Na2 87.08(9) 2_567 . ? Na1 O6 Na2 94.95(9) . 2_567 ? Na1 O6 H30 112(2) . . ? Na2 O6 H30 119(3) 2_567 . ? Na1 O6 H4O 122(3) . . ? Na2 O6 H4O 95(3) 2_567 . ? H30 O6 H4O 112(2) . . ? Na1 O4 Na2 98.03(9) . 1_655 ? Na1 O4 H1O 114(3) . . ? Na2 O4 H1O 107(3) 1_655 . ? Na1 O4 H2O 109(3) . . ? Na2 O4 H2O 121(3) 1_655 . ? H1O O4 H2O 108(2) . . ? O1S Na1 O22S 166.79(11) . 2_667 ? O1S Na1 O4 91.62(10) . . ? O22S Na1 O4 82.39(9) 2_667 . ? O1S Na1 O6 97.95(10) . . ? O22S Na1 O6 86.93(9) 2_667 . ? O4 Na1 O6 168.52(10) . . ? O1S Na1 O5 96.39(12) . . ? O22S Na1 O5 94.41(12) 2_667 . ? O4 Na1 O5 81.88(13) . . ? O6 Na1 O5 103.20(13) . . ? O1S Na1 O22S 80.04(9) . . ? O22S Na1 O22S 88.31(9) 2_667 . ? O4 Na1 O22S 91.36(9) . . ? O6 Na1 O22S 84.12(9) . . ? O5 Na1 O22S 172.30(12) . . ? O1S Na1 Na1 121.63(9) . 2_667 ? O22S Na1 Na1 46.46(6) 2_667 2_667 ? O4 Na1 Na1 85.92(8) . 2_667 ? O6 Na1 Na1 83.68(8) . 2_667 ? O5 Na1 Na1 140.35(11) . 2_667 ? O22S Na1 Na1 41.85(6) . 2_667 ? O1S Na1 Na2 81.66(8) . 2_567 ? O22S Na1 Na2 93.93(7) 2_667 2_567 ? O4 Na1 Na2 133.59(8) . 2_567 ? O6 Na1 Na2 42.87(7) . 2_567 ? O5 Na1 Na2 144.38(11) . 2_567 ? O22S Na1 Na2 42.23(5) . 2_567 ? Na1 Na1 Na2 60.57(4) 2_667 2_567 ? O1S Na1 Na2 131.56(9) . 1_655 ? O22S Na1 Na2 41.38(6) 2_667 1_655 ? O4 Na1 Na2 41.01(6) . 1_655 ? O6 Na1 Na2 128.18(8) . 1_655 ? O5 Na1 Na2 87.49(11) . 1_655 ? O22S Na1 Na2 89.81(7) . 1_655 ? Na1 Na1 Na2 59.79(5) 2_667 1_655 ? Na2 Na1 Na2 120.36(5) 2_567 1_655 ? O21S Na2 O4 100.87(10) . 1_455 ? O21S Na2 O22S 176.26(9) . 2_567 ? O4 Na2 O22S 81.91(9) 1_455 2_567 ? O21S Na2 O2S 83.79(11) . 2_567 ? O4 Na2 O2S 174.23(10) 1_455 2_567 ? O22S Na2 O2S 93.59(9) 2_567 2_567 ? O21S Na2 O6 95.35(10) . 2_567 ? O4 Na2 O6 81.14(10) 1_455 2_567 ? O22S Na2 O6 87.52(9) 2_567 2_567 ? O2S Na2 O6 95.12(10) 2_567 2_567 ? O21S Na2 O2S 78.28(11) . . ? O4 Na2 O2S 91.37(10) 1_455 . ? O22S Na2 O2S 99.24(10) 2_567 . ? O2S Na2 O2S 92.92(9) 2_567 . ? O6 Na2 O2S 169.16(10) 2_567 . ? O21S Na2 Na2 76.91(8) . 2_567 ? O4 Na2 Na2 137.27(9) 1_455 2_567 ? O22S Na2 Na2 99.35(8) 2_567 2_567 ? O2S Na2 Na2 46.88(7) 2_567 2_567 ? O6 Na2 Na2 141.45(9) 2_567 2_567 ? O2S Na2 Na2 46.04(6) . 2_567 ? O21S Na2 Na1 135.95(9) . 2_567 ? O4 Na2 Na1 85.76(7) 1_455 2_567 ? O22S Na2 Na1 46.37(6) 2_567 2_567 ? O2S Na2 Na1 88.52(7) 2_567 2_567 ? O6 Na2 Na1 42.18(6) 2_567 2_567 ? O2S Na2 Na1 145.57(8) . 2_567 ? Na2 Na2 Na1 125.75(6) 2_567 2_567 ? O21S Na2 Na1 141.78(9) . 1_455 ? O4 Na2 Na1 40.97(6) 1_455 1_455 ? O22S Na2 Na1 40.94(6) 2_567 1_455 ? O2S Na2 Na1 134.43(8) 2_567 1_455 ? O6 Na2 Na1 82.53(8) 2_567 1_455 ? O2S Na2 Na1 96.99(8) . 1_455 ? Na2 Na2 Na1 126.40(7) 2_567 1_455 ? Na1 Na2 Na1 59.64(5) 2_567 1_455 ? _refine_diff_density_max 0.747 _refine_diff_density_min -0.525 _refine_diff_density_rms 0.073 # SQUEEZE RESULTS (APPEND TO CIF) # Note: Data are Listed for all Voids in the P1 Unit Cell # i.e. Centre of Gravity, Solvent Accessible Volume, # Recovered number of Electrons in the Void and # Details about the Squeezed Material loop_ _platon_squeeze_void_nr _platon_squeeze_void_average_x _platon_squeeze_void_average_y _platon_squeeze_void_average_z _platon_squeeze_void_volume _platon_squeeze_void_count_electrons _platon_squeeze_void_content 1 0.487 0.000 0.000 219 30 ' ' _platon_squeeze_details ? _database_code_depnum_ccdc_archive 'CCDC 977420' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_4csalt _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C64 H98 N2 Na2 O9' _chemical_formula_weight 1085.42 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Na Na 0.0362 0.0249 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 _symmetry_space_group_name_Hall '-P 1 ' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.6755(7) _cell_length_b 10.3795(8) _cell_length_c 35.240(3) _cell_angle_alpha 92.172(2) _cell_angle_beta 91.370(2) _cell_angle_gamma 99.956(3) _cell_volume 3121.7(4) _cell_formula_units_Z 2 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 76046 _cell_measurement_theta_min 2.91 _cell_measurement_theta_max 27.4 _exptl_crystal_description plate _exptl_crystal_colour yellow _exptl_crystal_size_max 0.18 _exptl_crystal_size_mid 0.13 _exptl_crystal_size_min 0.03 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.155 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1180 _exptl_absorpt_coefficient_mu 0.087 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9845 _exptl_absorpt_correction_T_max 0.9974 _exptl_absorpt_process_details 'SADABS 2007/2 (Sheldrick, G.M., 2007)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Bruker-Nonius FR591 rotating anode' _diffrn_radiation_monochromator '10cm confocal mirrors' _diffrn_measurement_device_type 'Bruker-Nonius APEX II CCD camera on \k-goniostat' _diffrn_measurement_method '\f & \w scans' _diffrn_detector_area_resol_mean '4096x4096pixels / 62x62mm' _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 10081 _diffrn_reflns_av_R_equivalents 0.0000 _diffrn_reflns_av_sigmaI/netI 0.0330 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 41 _diffrn_reflns_theta_min 3.05 _diffrn_reflns_theta_max 24.71 _reflns_number_total 10081 _reflns_number_gt 8831 _reflns_threshold_expression >2\s(I) _computing_data_collection 'COLLECT (Hooft, R.W.W., 1998)' _computing_cell_refinement 'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)' #Although determined using DirAx, the cell is refined in the HKL #package during data reduction _computing_data_reduction 'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; The crystal structure of 4c is non-merohedraly twinned (180 rotation around 001 reciprocal vector) EvalCCD was used to integrate the domains and the structure was refined using the HKLF 5 instruction in Shelxl. The refined percentage ratio of the twin domains was 25:75 (refined BASF = 0.25714). Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2\s(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0633P)^2^+12.7776P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 10081 _refine_ls_number_parameters 715 _refine_ls_number_restraints 5 _refine_ls_R_factor_all 0.1133 _refine_ls_R_factor_gt 0.0958 _refine_ls_wR_factor_ref 0.2473 _refine_ls_wR_factor_gt 0.2295 _refine_ls_goodness_of_fit_ref 1.171 _refine_ls_restrained_S_all 1.171 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C -0.2144(6) 1.0528(6) 0.70588(15) 0.0240(12) Uani 1 1 d . . . C1A C 0.0723(6) 1.0358(6) 0.70826(15) 0.0254(12) Uani 1 1 d . . . H1A1 H 0.0800 1.1168 0.7245 0.031 Uiso 1 1 calc R . . H1A2 H 0.1478 1.0541 0.6877 0.031 Uiso 1 1 calc R . . C1B C -0.2470(6) 0.4923(6) 0.73711(15) 0.0250(12) Uani 1 1 d . . . H1B1 H -0.2438 0.4739 0.7644 0.030 Uiso 1 1 calc R . . H1B2 H -0.3477 0.4455 0.7258 0.030 Uiso 1 1 calc R . . C1M C 0.2026(9) 0.1732(8) 0.5461(2) 0.054(2) Uani 1 1 d . . . H1M1 H 0.1654 0.1303 0.5215 0.081 Uiso 1 1 calc R . . H1M2 H 0.1127 0.1838 0.5614 0.081 Uiso 1 1 calc R . . H1M3 H 0.2671 0.1193 0.5593 0.081 Uiso 1 1 calc R . . C1S C -0.0229(7) 0.8330(6) 0.59841(16) 0.0274(13) Uani 1 1 d . . . C2 C -0.2256(7) 1.1217(6) 0.74045(16) 0.0284(13) Uani 1 1 d . . . H2 H -0.1390 1.1424 0.7579 0.034 Uiso 1 1 calc R . . C2A C 0.1193(7) 0.9278(6) 0.73227(15) 0.0264(13) Uani 1 1 d . . . H2A1 H 0.0914 0.8427 0.7179 0.032 Uiso 1 1 calc R . . H2A2 H 0.2343 0.9453 0.7367 0.032 Uiso 1 1 calc R . . C2B C -0.2348(7) 0.6384(6) 0.73246(16) 0.0292(13) Uani 1 1 d . . . H2B1 H -0.2296 0.6555 0.7050 0.035 Uiso 1 1 calc R . . H2B2 H -0.1353 0.6835 0.7448 0.035 Uiso 1 1 calc R . . C2M C 0.6745(12) 0.1273(8) 0.5164(2) 0.066(3) Uani 1 1 d . . . H2M1 H 0.7753 0.1870 0.5167 0.099 Uiso 1 1 calc R . . H2M2 H 0.6920 0.0367 0.5137 0.099 Uiso 1 1 calc R . . H2M3 H 0.6218 0.1395 0.5402 0.099 Uiso 1 1 calc R . . C2S C -0.1284(7) 0.7743(6) 0.56722(17) 0.0315(14) Uani 1 1 d . . . C3 C -0.3665(7) 1.1577(6) 0.74786(18) 0.0346(14) Uani 1 1 d . . . H3 H -0.3778 1.2046 0.7710 0.042 Uiso 1 1 calc R . . C3A C 0.0396(7) 0.9182(6) 0.77065(15) 0.0292(13) Uani 1 1 d . . . H3A1 H -0.0748 0.9089 0.7659 0.035 Uiso 1 1 calc R . . H3A2 H 0.0595 0.8373 0.7825 0.035 Uiso 1 1 calc R . . C3B C -0.3694(7) 0.6985(6) 0.74897(16) 0.0297(13) Uani 1 1 d . . . H3B1 H -0.4696 0.6463 0.7390 0.036 Uiso 1 1 calc R . . H3B2 H -0.3628 0.7880 0.7397 0.036 Uiso 1 1 calc R . . C3S C 0.0041(7) 0.7304(6) 0.54725(16) 0.0300(13) Uani 1 1 d . . . C4 C -0.4945(8) 1.1272(7) 0.7222(2) 0.0412(16) Uani 1 1 d . . . H4 H -0.5906 1.1545 0.7280 0.049 Uiso 1 1 calc R . . C4A C 0.0909(7) 1.0330(6) 0.79899(15) 0.0281(13) Uani 1 1 d . . . H4A1 H 0.0881 1.1158 0.7862 0.034 Uiso 1 1 calc R . . H4A2 H 0.2003 1.0332 0.8077 0.034 Uiso 1 1 calc R . . C4B C -0.3729(7) 0.7063(6) 0.79258(16) 0.0297(13) Uani 1 1 d . . . H4B1 H -0.3998 0.6166 0.8019 0.036 Uiso 1 1 calc R . . H4B2 H -0.2671 0.7447 0.8029 0.036 Uiso 1 1 calc R . . C4S C 0.1091(7) 0.7993(6) 0.57853(16) 0.0291(13) Uani 1 1 d . . . C5 C -0.4819(7) 1.0583(6) 0.68882(18) 0.0311(14) Uani 1 1 d . . . H5 H -0.5693 1.0370 0.6716 0.037 Uiso 1 1 calc R . . C5A C -0.0134(7) 1.0265(6) 0.83330(16) 0.0303(13) Uani 1 1 d . . . H5A1 H 0.0103 0.9559 0.8494 0.036 Uiso 1 1 calc R . . H5A2 H -0.1239 1.0022 0.8243 0.036 Uiso 1 1 calc R . . C5B C -0.4890(8) 0.7874(7) 0.80739(16) 0.0330(14) Uani 1 1 d . . . H5B1 H -0.5962 0.7417 0.8003 0.040 Uiso 1 1 calc R . . H5B2 H -0.4723 0.8723 0.7949 0.040 Uiso 1 1 calc R . . C6 C -0.3412(7) 1.0201(6) 0.68039(16) 0.0277(13) Uani 1 1 d . . . C6A C 0.0042(7) 1.1534(6) 0.85776(16) 0.0277(13) Uani 1 1 d . . . H6A1 H 0.1146 1.1787 0.8668 0.033 Uiso 1 1 calc R . . H6A2 H -0.0218 1.2241 0.8420 0.033 Uiso 1 1 calc R . . C6B C -0.4770(7) 0.8134(6) 0.85060(16) 0.0302(13) Uani 1 1 d . . . H6B1 H -0.4965 0.7285 0.8631 0.036 Uiso 1 1 calc R . . H6B2 H -0.3691 0.8570 0.8578 0.036 Uiso 1 1 calc R . . C7 C -0.2947(6) 0.9444(6) 0.64645(16) 0.0271(13) Uani 1 1 d . . . C7A C -0.1005(7) 1.1404(6) 0.89175(16) 0.0287(13) Uani 1 1 d . . . H7A1 H -0.0669 1.0759 0.9087 0.034 Uiso 1 1 calc R . . H7A2 H -0.2092 1.1055 0.8827 0.034 Uiso 1 1 calc R . . C7B C -0.5906(7) 0.8973(6) 0.86523(16) 0.0307(14) Uani 1 1 d . . . H7B1 H -0.6987 0.8519 0.8589 0.037 Uiso 1 1 calc R . . H7B2 H -0.5741 0.9807 0.8519 0.037 Uiso 1 1 calc R . . C8 C -0.1220(6) 0.9419(5) 0.65594(14) 0.0217(12) Uani 1 1 d . . . C8A C -0.0993(7) 1.2680(6) 0.91461(16) 0.0287(13) Uani 1 1 d . . . H8A1 H -0.1338 1.3324 0.8978 0.034 Uiso 1 1 calc R . . H8A2 H 0.0094 1.3033 0.9235 0.034 Uiso 1 1 calc R . . C8B C -0.5745(7) 0.9280(6) 0.90806(16) 0.0291(13) Uani 1 1 d . . . H8B1 H -0.5877 0.8445 0.9213 0.035 Uiso 1 1 calc R . . H8B2 H -0.4673 0.9756 0.9142 0.035 Uiso 1 1 calc R . . C9 C -0.3107(7) 1.0206(7) 0.60997(17) 0.0345(14) Uani 1 1 d . . . H9A H -0.4211 1.0260 0.6051 0.052 Uiso 1 1 calc R . . H9B H -0.2717 0.9749 0.5884 0.052 Uiso 1 1 calc R . . H9C H -0.2495 1.1092 0.6134 0.052 Uiso 1 1 calc R . . C9A C -0.2046(7) 1.2531(6) 0.94894(16) 0.0290(13) Uani 1 1 d . . . H9A1 H -0.3128 1.2162 0.9399 0.035 Uiso 1 1 calc R . . H9A2 H -0.1691 1.1894 0.9658 0.035 Uiso 1 1 calc R . . C9B C -0.6916(7) 1.0092(6) 0.92327(16) 0.0292(13) Uani 1 1 d . . . H9B1 H -0.6788 1.0923 0.9098 0.035 Uiso 1 1 calc R . . H9B2 H -0.7987 0.9611 0.9172 0.035 Uiso 1 1 calc R . . C10 C -0.3933(7) 0.8070(6) 0.64251(17) 0.0286(13) Uani 1 1 d . . . H10A H -0.3831 0.7611 0.6660 0.043 Uiso 1 1 calc R . . H10B H -0.3565 0.7582 0.6212 0.043 Uiso 1 1 calc R . . H10C H -0.5033 0.8137 0.6378 0.043 Uiso 1 1 calc R . . C10A C -0.2076(7) 1.3786(6) 0.97186(16) 0.0272(13) Uani 1 1 d . . . H10D H -0.2468 1.4415 0.9552 0.033 Uiso 1 1 calc R . . H10E H -0.0991 1.4172 0.9802 0.033 Uiso 1 1 calc R . . C10B C -0.6760(7) 1.0410(6) 0.96567(16) 0.0287(13) Uani 1 1 d . . . H10F H -0.5701 1.0916 0.9717 0.034 Uiso 1 1 calc R . . H10G H -0.6859 0.9582 0.9792 0.034 Uiso 1 1 calc R . . C11 C -0.0125(7) 0.8954(6) 0.63486(15) 0.0265(13) Uani 1 1 d . . . H11 H 0.0886 0.9070 0.6468 0.032 Uiso 1 1 calc R . . C11A C -0.3085(7) 1.3616(6) 1.00663(17) 0.0301(13) Uani 1 1 d . . . H11A H -0.4169 1.3227 0.9983 0.036 Uiso 1 1 calc R . . H11B H -0.2690 1.2991 1.0233 0.036 Uiso 1 1 calc R . . C11B C -0.7969(7) 1.1189(6) 0.98053(16) 0.0280(13) Uani 1 1 d . . . H11C H -0.9028 1.0681 0.9747 0.034 Uiso 1 1 calc R . . H11D H -0.7874 1.2015 0.9669 0.034 Uiso 1 1 calc R . . C12A C -0.3120(6) 1.4879(6) 1.02954(16) 0.0264(13) Uani 1 1 d . . . H12A H -0.3542 1.5496 1.0131 0.032 Uiso 1 1 calc R . . H12B H -0.2034 1.5280 1.0373 0.032 Uiso 1 1 calc R . . C12B C -0.7806(7) 1.1518(6) 1.02331(16) 0.0264(13) Uani 1 1 d . . . H12C H -0.7883 1.0694 1.0370 0.032 Uiso 1 1 calc R . . H12D H -0.6757 1.2043 1.0292 0.032 Uiso 1 1 calc R . . C13A C -0.4099(7) 1.4699(6) 1.06486(17) 0.0301(13) Uani 1 1 d . . . H13A H -0.5182 1.4290 1.0570 0.036 Uiso 1 1 calc R . . H13B H -0.3673 1.4083 1.0813 0.036 Uiso 1 1 calc R . . C13B C -0.9042(7) 1.2271(6) 1.03757(16) 0.0288(13) Uani 1 1 d . . . H13C H -1.0088 1.1734 1.0321 0.035 Uiso 1 1 calc R . . H13D H -0.8982 1.3080 1.0233 0.035 Uiso 1 1 calc R . . C14A C -0.4156(7) 1.5948(6) 1.08803(16) 0.0288(13) Uani 1 1 d . . . H14A H -0.4552 1.6576 1.0715 0.035 Uiso 1 1 calc R . . H14B H -0.3079 1.6342 1.0968 0.035 Uiso 1 1 calc R . . C14B C -0.8884(7) 1.2644(6) 1.07990(16) 0.0288(13) Uani 1 1 d . . . H14C H -0.8932 1.1838 1.0943 0.035 Uiso 1 1 calc R . . H14D H -0.7845 1.3194 1.0854 0.035 Uiso 1 1 calc R . . C15A C -0.5181(8) 1.5747(6) 1.12230(16) 0.0348(15) Uani 1 1 d . . . H15A H -0.4776 1.5127 1.1390 0.042 Uiso 1 1 calc R . . H15B H -0.6254 1.5340 1.1135 0.042 Uiso 1 1 calc R . . C15B C -1.0142(7) 1.3380(6) 1.09362(16) 0.0308(14) Uani 1 1 d . . . H15C H -1.1178 1.2823 1.0885 0.037 Uiso 1 1 calc R . . H15D H -1.0105 1.4176 1.0788 0.037 Uiso 1 1 calc R . . C16A C -0.5266(8) 1.6996(7) 1.14548(17) 0.0400(16) Uani 1 1 d . . . H16A H -0.4217 1.7386 1.1553 0.060 Uiso 1 1 calc R . . H16B H -0.5962 1.6791 1.1667 0.060 Uiso 1 1 calc R . . H16C H -0.5675 1.7615 1.1293 0.060 Uiso 1 1 calc R . . C16B C -0.9989(8) 1.3782(7) 1.13556(17) 0.0412(16) Uani 1 1 d . . . H16D H -1.0018 1.3001 1.1505 0.062 Uiso 1 1 calc R . . H16E H -1.0857 1.4226 1.1425 0.062 Uiso 1 1 calc R . . H16F H -0.8993 1.4377 1.1407 0.062 Uiso 1 1 calc R . . C21S C -0.2460(7) 0.4271(6) 0.61528(15) 0.0259(13) Uani 1 1 d . . . C22S C -0.1581(6) 0.4364(6) 0.58029(15) 0.0257(13) Uani 1 1 d . . . C23S C -0.3069(6) 0.4410(6) 0.55823(15) 0.0259(13) Uani 1 1 d . . . C24S C -0.3906(7) 0.4224(7) 0.59474(16) 0.0309(14) Uani 1 1 d . . . C101 C 0.0237(6) 0.4355(6) 0.73746(14) 0.0231(12) Uani 1 1 d . . . C102 C 0.0569(7) 0.4388(6) 0.77587(15) 0.0271(13) Uani 1 1 d . . . H102 H -0.0190 0.4526 0.7939 0.032 Uiso 1 1 calc R . . C103 C 0.2056(7) 0.4214(6) 0.78728(17) 0.0319(14) Uani 1 1 d . . . H103 H 0.2315 0.4230 0.8137 0.038 Uiso 1 1 calc R . . C104 C 0.3183(7) 0.4015(6) 0.76118(16) 0.0302(14) Uani 1 1 d . . . H104 H 0.4191 0.3893 0.7698 0.036 Uiso 1 1 calc R . . C105 C 0.2822(7) 0.3997(6) 0.72238(16) 0.0278(13) Uani 1 1 d . . . H105 H 0.3582 0.3863 0.7044 0.033 Uiso 1 1 calc R . . C106 C 0.1351(6) 0.4175(5) 0.71040(15) 0.0228(12) Uani 1 1 d . . . C107 C 0.0653(6) 0.4249(6) 0.67099(15) 0.0234(12) Uani 1 1 d . . . C108 C -0.1052(6) 0.4332(5) 0.67956(14) 0.0223(12) Uani 1 1 d . . . C109 C 0.0803(7) 0.3041(6) 0.64557(16) 0.0294(13) Uani 1 1 d . . . H10H H 0.1912 0.2980 0.6432 0.044 Uiso 1 1 calc R . . H10I H 0.0339 0.3123 0.6203 0.044 Uiso 1 1 calc R . . H10J H 0.0253 0.2250 0.6569 0.044 Uiso 1 1 calc R . . C110 C 0.1452(7) 0.5520(6) 0.65328(15) 0.0270(13) Uani 1 1 d . . . H11E H 0.1335 0.6274 0.6699 0.041 Uiso 1 1 calc R . . H11F H 0.0962 0.5600 0.6283 0.041 Uiso 1 1 calc R . . H11G H 0.2567 0.5495 0.6504 0.041 Uiso 1 1 calc R . . C111 C -0.2304(6) 0.4295(6) 0.65553(16) 0.0265(13) Uani 1 1 d . . . H111 H -0.3263 0.4283 0.6680 0.032 Uiso 1 1 calc R . . N1 N -0.0854(5) 1.0037(5) 0.69133(13) 0.0264(11) Uani 1 1 d . . . N101 N -0.1164(5) 0.4464(5) 0.71819(12) 0.0215(10) Uani 1 1 d . . . O1H O 0.3612(5) 0.6000(5) 0.56200(11) 0.0346(10) Uani 1 1 d D . . O1M O 0.2942(5) 0.2992(5) 0.54011(11) 0.0346(10) Uani 1 1 d D . . O1S O -0.2700(5) 0.7620(5) 0.55862(12) 0.0447(12) Uani 1 1 d . . . O2M O 0.5799(7) 0.1544(6) 0.48551(16) 0.0627(15) Uani 1 1 d D . . O2S O 0.0179(5) 0.6623(4) 0.51878(11) 0.0322(10) Uani 1 1 d . . . O3S O 0.2541(5) 0.8210(5) 0.58563(12) 0.0392(11) Uani 1 1 d . . . O21S O -0.0209(4) 0.4405(4) 0.57098(10) 0.0302(10) Uani 1 1 d . . . O23S O -0.5313(5) 0.4106(5) 0.60354(11) 0.0395(12) Uani 1 1 d . . . Na1 Na 0.1572(2) 0.4764(2) 0.52391(6) 0.0272(5) Uani 1 1 d . . . Na2 Na 0.4560(3) 0.3303(3) 0.48504(6) 0.0357(6) Uani 1 1 d . . . O22S O -0.3415(4) 0.4606(4) 0.52501(10) 0.0313(10) Uani 1 1 d . . . H1O H 0.326(8) 0.665(4) 0.5703(15) 0.047 Uiso 1 1 d D . . H2O H 0.400(8) 0.562(6) 0.5792(12) 0.047 Uiso 1 1 d D . . H2M H 0.637(7) 0.143(7) 0.4666(13) 0.047 Uiso 1 1 d D . . H1M H 0.325(8) 0.320(7) 0.5630(7) 0.047 Uiso 1 1 d D . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.023(3) 0.028(3) 0.020(3) 0.002(2) 0.006(2) 0.000(2) C1A 0.023(3) 0.036(3) 0.017(3) -0.006(2) 0.002(2) 0.003(3) C1B 0.021(3) 0.038(3) 0.017(3) -0.005(2) 0.005(2) 0.008(3) C1M 0.055(5) 0.051(5) 0.053(5) -0.003(4) 0.014(4) -0.001(4) C1S 0.024(3) 0.034(3) 0.024(3) -0.001(2) 0.002(2) 0.003(3) C2 0.028(3) 0.031(3) 0.027(3) -0.002(2) 0.004(2) 0.007(3) C2A 0.026(3) 0.033(3) 0.020(3) -0.001(2) 0.006(2) 0.004(3) C2B 0.031(3) 0.034(3) 0.024(3) 0.002(2) 0.012(2) 0.004(3) C2M 0.122(8) 0.044(4) 0.025(4) 0.009(3) -0.017(4) -0.005(5) C2S 0.023(3) 0.042(4) 0.028(3) -0.006(3) 0.001(2) 0.004(3) C3 0.035(4) 0.033(3) 0.036(3) -0.004(3) 0.012(3) 0.003(3) C3A 0.033(3) 0.033(3) 0.021(3) 0.002(2) 0.009(2) 0.003(3) C3B 0.031(3) 0.035(3) 0.025(3) 0.000(3) 0.008(2) 0.010(3) C3S 0.025(3) 0.037(3) 0.027(3) -0.001(3) 0.003(2) 0.001(3) C4 0.028(4) 0.043(4) 0.053(4) -0.009(3) 0.007(3) 0.009(3) C4A 0.032(3) 0.030(3) 0.022(3) 0.002(2) 0.008(2) 0.004(3) C4B 0.032(3) 0.032(3) 0.023(3) -0.001(2) 0.011(2) 0.001(3) C4S 0.029(3) 0.037(3) 0.021(3) -0.005(2) -0.002(2) 0.006(3) C5 0.023(3) 0.034(3) 0.038(3) -0.004(3) 0.004(3) 0.009(3) C5A 0.038(4) 0.029(3) 0.023(3) 0.003(2) 0.009(3) 0.003(3) C5B 0.036(4) 0.040(4) 0.025(3) -0.005(3) 0.005(3) 0.013(3) C6 0.028(3) 0.026(3) 0.027(3) 0.002(2) 0.004(2) 0.000(3) C6A 0.030(3) 0.028(3) 0.024(3) -0.002(2) 0.008(2) 0.000(3) C6B 0.033(3) 0.029(3) 0.030(3) 0.001(3) 0.007(3) 0.010(3) C7 0.016(3) 0.039(3) 0.026(3) 0.001(3) 0.003(2) 0.005(3) C7A 0.030(3) 0.029(3) 0.026(3) -0.003(2) 0.007(2) 0.003(3) C7B 0.030(3) 0.036(4) 0.027(3) -0.003(3) 0.006(2) 0.006(3) C8 0.027(3) 0.023(3) 0.014(2) 0.004(2) 0.003(2) 0.000(2) C8A 0.029(3) 0.028(3) 0.027(3) -0.001(2) 0.008(2) -0.001(3) C8B 0.027(3) 0.030(3) 0.029(3) 0.002(3) 0.008(2) 0.001(3) C9 0.030(3) 0.045(4) 0.029(3) 0.008(3) -0.002(3) 0.004(3) C9A 0.031(3) 0.032(3) 0.023(3) -0.001(2) 0.005(2) 0.002(3) C9B 0.036(3) 0.029(3) 0.024(3) 0.000(2) 0.012(3) 0.008(3) C10 0.023(3) 0.032(3) 0.029(3) -0.003(3) 0.001(2) 0.000(3) C10A 0.027(3) 0.031(3) 0.023(3) -0.001(2) 0.007(2) 0.001(3) C10B 0.024(3) 0.031(3) 0.030(3) -0.004(3) 0.008(2) 0.000(3) C11 0.020(3) 0.036(3) 0.022(3) -0.003(2) -0.001(2) 0.001(3) C11A 0.030(3) 0.029(3) 0.030(3) -0.001(2) 0.013(3) 0.000(3) C11B 0.029(3) 0.030(3) 0.024(3) -0.003(2) 0.008(2) 0.003(3) C12A 0.019(3) 0.029(3) 0.029(3) -0.006(2) 0.009(2) -0.004(2) C12B 0.024(3) 0.028(3) 0.026(3) 0.001(2) 0.009(2) 0.002(3) C13A 0.033(3) 0.026(3) 0.032(3) 0.000(2) 0.012(3) 0.003(3) C13B 0.032(3) 0.031(3) 0.024(3) 0.009(2) 0.012(2) 0.005(3) C14A 0.028(3) 0.032(3) 0.026(3) -0.004(2) 0.008(2) 0.001(3) C14B 0.027(3) 0.028(3) 0.030(3) -0.003(2) 0.006(2) 0.000(3) C15A 0.039(4) 0.040(4) 0.024(3) -0.005(3) 0.013(3) 0.002(3) C15B 0.033(3) 0.031(3) 0.027(3) -0.002(3) 0.012(3) 0.003(3) C16A 0.042(4) 0.053(4) 0.026(3) -0.008(3) 0.006(3) 0.015(3) C16B 0.048(4) 0.046(4) 0.029(3) -0.003(3) 0.014(3) 0.006(3) C21S 0.022(3) 0.035(3) 0.020(3) -0.002(2) 0.004(2) 0.004(3) C22S 0.020(3) 0.039(3) 0.021(3) -0.002(2) 0.006(2) 0.012(3) C23S 0.017(3) 0.041(4) 0.019(3) -0.007(2) 0.003(2) 0.005(3) C24S 0.022(3) 0.050(4) 0.022(3) -0.001(3) 0.004(2) 0.007(3) C101 0.021(3) 0.032(3) 0.016(3) -0.002(2) 0.005(2) 0.002(2) C102 0.025(3) 0.035(3) 0.021(3) 0.001(2) 0.006(2) 0.004(3) C103 0.032(3) 0.036(4) 0.027(3) 0.002(3) -0.004(3) 0.005(3) C104 0.019(3) 0.044(4) 0.027(3) 0.000(3) -0.001(2) 0.003(3) C105 0.022(3) 0.036(3) 0.024(3) -0.001(2) 0.009(2) 0.002(3) C106 0.021(3) 0.026(3) 0.020(3) 0.000(2) 0.003(2) 0.001(2) C107 0.019(3) 0.032(3) 0.019(3) -0.001(2) 0.009(2) 0.002(2) C108 0.022(3) 0.027(3) 0.017(3) -0.001(2) 0.006(2) 0.003(2) C109 0.029(3) 0.034(3) 0.024(3) -0.001(2) 0.005(2) 0.001(3) C110 0.026(3) 0.034(3) 0.020(3) 0.004(2) 0.003(2) -0.001(3) C111 0.016(3) 0.037(3) 0.026(3) 0.000(2) 0.008(2) 0.001(2) N1 0.019(2) 0.037(3) 0.022(2) -0.004(2) -0.0007(19) 0.001(2) N101 0.017(2) 0.029(3) 0.019(2) 0.0000(19) 0.0050(18) 0.005(2) O1H 0.022(2) 0.057(3) 0.025(2) -0.010(2) 0.0002(17) 0.010(2) O1M 0.028(2) 0.051(3) 0.025(2) -0.005(2) 0.0004(18) 0.008(2) O1S 0.021(2) 0.075(4) 0.034(2) -0.018(2) -0.0039(19) 0.003(2) O2M 0.051(3) 0.089(4) 0.049(3) 0.007(3) 0.014(3) 0.009(3) O2S 0.031(2) 0.044(3) 0.020(2) -0.0054(19) 0.0013(17) 0.003(2) O3S 0.023(2) 0.054(3) 0.039(2) -0.018(2) -0.0042(19) 0.008(2) O21S 0.021(2) 0.051(3) 0.0195(19) 0.0033(18) 0.0063(16) 0.0081(19) O23S 0.018(2) 0.079(4) 0.021(2) -0.001(2) 0.0057(17) 0.009(2) Na1 0.0156(11) 0.0469(14) 0.0184(10) -0.0061(10) 0.0046(9) 0.0042(10) Na2 0.0183(12) 0.0608(17) 0.0258(12) -0.0129(11) 0.0035(9) 0.0035(11) O22S 0.020(2) 0.055(3) 0.018(2) -0.0024(18) 0.0024(16) 0.004(2) _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C6 1.390(8) . ? C1 C2 1.403(8) . ? C1 N1 1.406(7) . ? C1A N1 1.458(7) . ? C1A C2A 1.534(8) . ? C1A H1A1 0.9900 . ? C1A H1A2 0.9900 . ? C1B N101 1.468(7) . ? C1B C2B 1.517(8) . ? C1B H1B1 0.9900 . ? C1B H1B2 0.9900 . ? C1M O1M 1.434(9) . ? C1M H1M1 0.9800 . ? C1M H1M2 0.9800 . ? C1M H1M3 0.9800 . ? C1S C11 1.410(8) . ? C1S C4S 1.444(8) . ? C1S C2S 1.458(8) . ? C2 C3 1.367(8) . ? C2 H2 0.9500 . ? C2A C3A 1.532(7) . ? C2A H2A1 0.9900 . ? C2A H2A2 0.9900 . ? C2B C3B 1.533(8) . ? C2B H2B1 0.9900 . ? C2B H2B2 0.9900 . ? C2M O2M 1.413(10) . ? C2M H2M1 0.9800 . ? C2M H2M2 0.9800 . ? C2M H2M3 0.9800 . ? C2S O1S 1.242(7) . ? C2S C3S 1.490(8) . ? C3 C4 1.399(9) . ? C3 H3 0.9500 . ? C3A C4A 1.523(8) . ? C3A H3A1 0.9900 . ? C3A H3A2 0.9900 . ? C3B C4B 1.537(7) . ? C3B H3B1 0.9900 . ? C3B H3B2 0.9900 . ? C3S O2S 1.225(7) . ? C3S C4S 1.491(8) . ? C4 C5 1.370(9) . ? C4 H4 0.9500 . ? C4A C5A 1.524(8) . ? C4A H4A1 0.9900 . ? C4A H4A2 0.9900 . ? C4B C5B 1.510(8) . ? C4B H4B1 0.9900 . ? C4B H4B2 0.9900 . ? C4S O3S 1.256(7) . ? C5 C6 1.383(8) . ? C5 H5 0.9500 . ? C5A C6A 1.530(8) . ? C5A H5A1 0.9900 . ? C5A H5A2 0.9900 . ? C5B C6B 1.534(8) . ? C5B H5B1 0.9900 . ? C5B H5B2 0.9900 . ? C6 C7 1.507(8) . ? C6A C7A 1.516(8) . ? C6A H6A1 0.9900 . ? C6A H6A2 0.9900 . ? C6B C7B 1.511(8) . ? C6B H6B1 0.9900 . ? C6B H6B2 0.9900 . ? C7 C10 1.531(8) . ? C7 C8 1.532(8) . ? C7 C9 1.551(8) . ? C7A C8A 1.522(8) . ? C7A H7A1 0.9900 . ? C7A H7A2 0.9900 . ? C7B C8B 1.528(8) . ? C7B H7B1 0.9900 . ? C7B H7B2 0.9900 . ? C8 C11 1.360(8) . ? C8 N1 1.385(7) . ? C8A C9A 1.530(8) . ? C8A H8A1 0.9900 . ? C8A H8A2 0.9900 . ? C8B C9B 1.522(8) . ? C8B H8B1 0.9900 . ? C8B H8B2 0.9900 . ? C9 H9A 0.9800 . ? C9 H9B 0.9800 . ? C9 H9C 0.9800 . ? C9A C10A 1.511(8) . ? C9A H9A1 0.9900 . ? C9A H9A2 0.9900 . ? C9B C10B 1.516(8) . ? C9B H9B1 0.9900 . ? C9B H9B2 0.9900 . ? C10 H10A 0.9800 . ? C10 H10B 0.9800 . ? C10 H10C 0.9800 . ? C10A C11A 1.521(8) . ? C10A H10D 0.9900 . ? C10A H10E 0.9900 . ? C10B C11B 1.521(8) . ? C10B H10F 0.9900 . ? C10B H10G 0.9900 . ? C11 H11 0.9500 . ? C11A C12A 1.518(8) . ? C11A H11A 0.9900 . ? C11A H11B 0.9900 . ? C11B C12B 1.531(7) . ? C11B H11C 0.9900 . ? C11B H11D 0.9900 . ? C12A C13A 1.523(8) . ? C12A H12A 0.9900 . ? C12A H12B 0.9900 . ? C12B C13B 1.516(8) . ? C12B H12C 0.9900 . ? C12B H12D 0.9900 . ? C13A C14A 1.515(8) . ? C13A H13A 0.9900 . ? C13A H13B 0.9900 . ? C13B C14B 1.524(8) . ? C13B H13C 0.9900 . ? C13B H13D 0.9900 . ? C14A C15A 1.516(8) . ? C14A H14A 0.9900 . ? C14A H14B 0.9900 . ? C14B C15B 1.515(8) . ? C14B H14C 0.9900 . ? C14B H14D 0.9900 . ? C15A C16A 1.519(9) . ? C15A H15A 0.9900 . ? C15A H15B 0.9900 . ? C15B C16B 1.517(8) . ? C15B H15C 0.9900 . ? C15B H15D 0.9900 . ? C16A H16A 0.9800 . ? C16A H16B 0.9800 . ? C16A H16C 0.9800 . ? C16B H16D 0.9800 . ? C16B H16E 0.9800 . ? C16B H16F 0.9800 . ? C21S C111 1.421(8) . ? C21S C24S 1.426(8) . ? C21S C22S 1.463(7) . ? C22S O21S 1.236(7) . ? C22S C23S 1.500(8) . ? C23S O22S 1.235(7) . ? C23S C24S 1.495(8) . ? C24S O23S 1.253(7) . ? C101 C102 1.375(7) . ? C101 N101 1.402(7) . ? C101 C106 1.403(7) . ? C102 C103 1.385(8) . ? C102 H102 0.9500 . ? C103 C104 1.393(8) . ? C103 H103 0.9500 . ? C104 C105 1.394(8) . ? C104 H104 0.9500 . ? C105 C106 1.379(8) . ? C105 H105 0.9500 . ? C106 C107 1.512(7) . ? C107 C108 1.532(7) . ? C107 C109 1.539(8) . ? C107 C110 1.542(8) . ? C108 C111 1.355(8) . ? C108 N101 1.370(7) . ? C109 H10H 0.9800 . ? C109 H10I 0.9800 . ? C109 H10J 0.9800 . ? C110 H11E 0.9800 . ? C110 H11F 0.9800 . ? C110 H11G 0.9800 . ? C111 H111 0.9500 . ? O1H Na1 2.356(5) . ? O1H Na2 2.368(5) 2_666 ? O1H H1O 0.832(10) . ? O1H H2O 0.829(10) . ? O1M Na2 2.421(5) . ? O1M Na1 2.434(5) . ? O1M H1M 0.850(10) . ? O1S Na2 2.263(5) 2_566 ? O2M Na2 2.274(7) . ? O2M H2M 0.857(10) . ? O2S Na1 2.370(4) 2_566 ? O2S Na1 2.457(5) . ? O21S Na1 2.291(4) . ? Na1 O2S 2.370(4) 2_566 ? Na1 O22S 2.411(4) 2_566 ? Na1 Na1 3.290(4) 2_566 ? Na1 Na2 3.502(3) . ? Na1 Na2 3.627(3) 2_666 ? Na2 O1S 2.263(5) 2_566 ? Na2 O1H 2.368(5) 2_666 ? Na2 O22S 2.412(5) 1_655 ? Na2 O22S 2.571(5) 2_566 ? Na2 Na2 3.586(5) 2_666 ? Na2 Na1 3.627(3) 2_666 ? O22S Na1 2.411(4) 2_566 ? O22S Na2 2.412(5) 1_455 ? O22S Na2 2.571(5) 2_566 ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C6 C1 C2 121.9(5) . . ? C6 C1 N1 109.2(5) . . ? C2 C1 N1 129.0(5) . . ? N1 C1A C2A 114.1(5) . . ? N1 C1A H1A1 108.7 . . ? C2A C1A H1A1 108.7 . . ? N1 C1A H1A2 108.7 . . ? C2A C1A H1A2 108.7 . . ? H1A1 C1A H1A2 107.6 . . ? N101 C1B C2B 109.4(5) . . ? N101 C1B H1B1 109.8 . . ? C2B C1B H1B1 109.8 . . ? N101 C1B H1B2 109.8 . . ? C2B C1B H1B2 109.8 . . ? H1B1 C1B H1B2 108.2 . . ? O1M C1M H1M1 109.5 . . ? O1M C1M H1M2 109.5 . . ? H1M1 C1M H1M2 109.5 . . ? O1M C1M H1M3 109.5 . . ? H1M1 C1M H1M3 109.5 . . ? H1M2 C1M H1M3 109.5 . . ? C11 C1S C4S 124.3(5) . . ? C11 C1S C2S 145.3(6) . . ? C4S C1S C2S 90.4(4) . . ? C3 C2 C1 117.1(6) . . ? C3 C2 H2 121.4 . . ? C1 C2 H2 121.4 . . ? C3A C2A C1A 112.7(5) . . ? C3A C2A H2A1 109.0 . . ? C1A C2A H2A1 109.0 . . ? C3A C2A H2A2 109.0 . . ? C1A C2A H2A2 109.0 . . ? H2A1 C2A H2A2 107.8 . . ? C1B C2B C3B 115.1(5) . . ? C1B C2B H2B1 108.5 . . ? C3B C2B H2B1 108.5 . . ? C1B C2B H2B2 108.5 . . ? C3B C2B H2B2 108.5 . . ? H2B1 C2B H2B2 107.5 . . ? O2M C2M H2M1 109.5 . . ? O2M C2M H2M2 109.5 . . ? H2M1 C2M H2M2 109.5 . . ? O2M C2M H2M3 109.5 . . ? H2M1 C2M H2M3 109.5 . . ? H2M2 C2M H2M3 109.5 . . ? O1S C2S C1S 137.5(6) . . ? O1S C2S C3S 131.8(5) . . ? C1S C2S C3S 90.8(5) . . ? C2 C3 C4 121.7(6) . . ? C2 C3 H3 119.2 . . ? C4 C3 H3 119.2 . . ? C4A C3A C2A 115.9(5) . . ? C4A C3A H3A1 108.3 . . ? C2A C3A H3A1 108.3 . . ? C4A C3A H3A2 108.3 . . ? C2A C3A H3A2 108.3 . . ? H3A1 C3A H3A2 107.4 . . ? C2B C3B C4B 115.2(5) . . ? C2B C3B H3B1 108.5 . . ? C4B C3B H3B1 108.5 . . ? C2B C3B H3B2 108.5 . . ? C4B C3B H3B2 108.5 . . ? H3B1 C3B H3B2 107.5 . . ? O2S C3S C2S 135.8(6) . . ? O2S C3S C4S 136.7(6) . . ? C2S C3S C4S 87.4(4) . . ? C5 C4 C3 120.4(6) . . ? C5 C4 H4 119.8 . . ? C3 C4 H4 119.8 . . ? C3A C4A C5A 112.1(5) . . ? C3A C4A H4A1 109.2 . . ? C5A C4A H4A1 109.2 . . ? C3A C4A H4A2 109.2 . . ? C5A C4A H4A2 109.2 . . ? H4A1 C4A H4A2 107.9 . . ? C5B C4B C3B 113.0(5) . . ? C5B C4B H4B1 109.0 . . ? C3B C4B H4B1 109.0 . . ? C5B C4B H4B2 109.0 . . ? C3B C4B H4B2 109.0 . . ? H4B1 C4B H4B2 107.8 . . ? O3S C4S C1S 133.2(5) . . ? O3S C4S C3S 135.5(5) . . ? C1S C4S C3S 91.3(5) . . ? C4 C5 C6 119.5(6) . . ? C4 C5 H5 120.2 . . ? C6 C5 H5 120.2 . . ? C4A C5A C6A 114.8(5) . . ? C4A C5A H5A1 108.6 . . ? C6A C5A H5A1 108.6 . . ? C4A C5A H5A2 108.6 . . ? C6A C5A H5A2 108.6 . . ? H5A1 C5A H5A2 107.5 . . ? C4B C5B C6B 113.7(5) . . ? C4B C5B H5B1 108.8 . . ? C6B C5B H5B1 108.8 . . ? C4B C5B H5B2 108.8 . . ? C6B C5B H5B2 108.8 . . ? H5B1 C5B H5B2 107.7 . . ? C5 C6 C1 119.4(5) . . ? C5 C6 C7 130.9(5) . . ? C1 C6 C7 109.7(5) . . ? C7A C6A C5A 112.4(5) . . ? C7A C6A H6A1 109.1 . . ? C5A C6A H6A1 109.1 . . ? C7A C6A H6A2 109.1 . . ? C5A C6A H6A2 109.1 . . ? H6A1 C6A H6A2 107.8 . . ? C7B C6B C5B 113.6(5) . . ? C7B C6B H6B1 108.9 . . ? C5B C6B H6B1 108.9 . . ? C7B C6B H6B2 108.9 . . ? C5B C6B H6B2 108.9 . . ? H6B1 C6B H6B2 107.7 . . ? C6 C7 C10 111.1(5) . . ? C6 C7 C8 102.0(4) . . ? C10 C7 C8 112.4(5) . . ? C6 C7 C9 109.8(5) . . ? C10 C7 C9 110.7(5) . . ? C8 C7 C9 110.4(5) . . ? C6A C7A C8A 114.2(5) . . ? C6A C7A H7A1 108.7 . . ? C8A C7A H7A1 108.7 . . ? C6A C7A H7A2 108.7 . . ? C8A C7A H7A2 108.7 . . ? H7A1 C7A H7A2 107.6 . . ? C6B C7B C8B 113.7(5) . . ? C6B C7B H7B1 108.8 . . ? C8B C7B H7B1 108.8 . . ? C6B C7B H7B2 108.8 . . ? C8B C7B H7B2 108.8 . . ? H7B1 C7B H7B2 107.7 . . ? C11 C8 N1 121.9(5) . . ? C11 C8 C7 130.0(5) . . ? N1 C8 C7 108.0(5) . . ? C7A C8A C9A 113.6(5) . . ? C7A C8A H8A1 108.8 . . ? C9A C8A H8A1 108.8 . . ? C7A C8A H8A2 108.8 . . ? C9A C8A H8A2 108.8 . . ? H8A1 C8A H8A2 107.7 . . ? C9B C8B C7B 114.1(5) . . ? C9B C8B H8B1 108.7 . . ? C7B C8B H8B1 108.7 . . ? C9B C8B H8B2 108.7 . . ? C7B C8B H8B2 108.7 . . ? H8B1 C8B H8B2 107.6 . . ? C7 C9 H9A 109.5 . . ? C7 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? C7 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? C10A C9A C8A 114.8(5) . . ? C10A C9A H9A1 108.6 . . ? C8A C9A H9A1 108.6 . . ? C10A C9A H9A2 108.6 . . ? C8A C9A H9A2 108.6 . . ? H9A1 C9A H9A2 107.6 . . ? C10B C9B C8B 114.6(5) . . ? C10B C9B H9B1 108.6 . . ? C8B C9B H9B1 108.6 . . ? C10B C9B H9B2 108.6 . . ? C8B C9B H9B2 108.6 . . ? H9B1 C9B H9B2 107.6 . . ? C7 C10 H10A 109.5 . . ? C7 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? C7 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? C9A C10A C11A 114.2(5) . . ? C9A C10A H10D 108.7 . . ? C11A C10A H10D 108.7 . . ? C9A C10A H10E 108.7 . . ? C11A C10A H10E 108.7 . . ? H10D C10A H10E 107.6 . . ? C9B C10B C11B 113.9(5) . . ? C9B C10B H10F 108.8 . . ? C11B C10B H10F 108.8 . . ? C9B C10B H10G 108.8 . . ? C11B C10B H10G 108.8 . . ? H10F C10B H10G 107.7 . . ? C8 C11 C1S 131.3(5) . . ? C8 C11 H11 114.4 . . ? C1S C11 H11 114.4 . . ? C12A C11A C10A 114.1(5) . . ? C12A C11A H11A 108.7 . . ? C10A C11A H11A 108.7 . . ? C12A C11A H11B 108.7 . . ? C10A C11A H11B 108.7 . . ? H11A C11A H11B 107.6 . . ? C10B C11B C12B 113.9(5) . . ? C10B C11B H11C 108.8 . . ? C12B C11B H11C 108.8 . . ? C10B C11B H11D 108.8 . . ? C12B C11B H11D 108.8 . . ? H11C C11B H11D 107.7 . . ? C11A C12A C13A 113.9(5) . . ? C11A C12A H12A 108.8 . . ? C13A C12A H12A 108.8 . . ? C11A C12A H12B 108.8 . . ? C13A C12A H12B 108.8 . . ? H12A C12A H12B 107.7 . . ? C13B C12B C11B 112.9(5) . . ? C13B C12B H12C 109.0 . . ? C11B C12B H12C 109.0 . . ? C13B C12B H12D 109.0 . . ? C11B C12B H12D 109.0 . . ? H12C C12B H12D 107.8 . . ? C14A C13A C12A 114.8(5) . . ? C14A C13A H13A 108.6 . . ? C12A C13A H13A 108.6 . . ? C14A C13A H13B 108.6 . . ? C12A C13A H13B 108.6 . . ? H13A C13A H13B 107.5 . . ? C12B C13B C14B 114.1(5) . . ? C12B C13B H13C 108.7 . . ? C14B C13B H13C 108.7 . . ? C12B C13B H13D 108.7 . . ? C14B C13B H13D 108.7 . . ? H13C C13B H13D 107.6 . . ? C13A C14A C15A 113.7(5) . . ? C13A C14A H14A 108.8 . . ? C15A C14A H14A 108.8 . . ? C13A C14A H14B 108.8 . . ? C15A C14A H14B 108.8 . . ? H14A C14A H14B 107.7 . . ? C15B C14B C13B 113.2(5) . . ? C15B C14B H14C 108.9 . . ? C13B C14B H14C 108.9 . . ? C15B C14B H14D 108.9 . . ? C13B C14B H14D 108.9 . . ? H14C C14B H14D 107.8 . . ? C14A C15A C16A 114.2(5) . . ? C14A C15A H15A 108.7 . . ? C16A C15A H15A 108.7 . . ? C14A C15A H15B 108.7 . . ? C16A C15A H15B 108.7 . . ? H15A C15A H15B 107.6 . . ? C14B C15B C16B 114.0(5) . . ? C14B C15B H15C 108.7 . . ? C16B C15B H15C 108.7 . . ? C14B C15B H15D 108.7 . . ? C16B C15B H15D 108.7 . . ? H15C C15B H15D 107.6 . . ? C15A C16A H16A 109.5 . . ? C15A C16A H16B 109.5 . . ? H16A C16A H16B 109.5 . . ? C15A C16A H16C 109.5 . . ? H16A C16A H16C 109.5 . . ? H16B C16A H16C 109.5 . . ? C15B C16B H16D 109.5 . . ? C15B C16B H16E 109.5 . . ? H16D C16B H16E 109.5 . . ? C15B C16B H16F 109.5 . . ? H16D C16B H16F 109.5 . . ? H16E C16B H16F 109.5 . . ? C111 C21S C24S 124.4(5) . . ? C111 C21S C22S 143.7(5) . . ? C24S C21S C22S 91.8(4) . . ? O21S C22S C21S 137.6(5) . . ? O21S C22S C23S 133.1(5) . . ? C21S C22S C23S 89.3(4) . . ? O22S C23S C24S 136.6(5) . . ? O22S C23S C22S 135.5(5) . . ? C24S C23S C22S 87.7(4) . . ? O23S C24S C21S 134.9(5) . . ? O23S C24S C23S 134.1(5) . . ? C21S C24S C23S 90.9(4) . . ? C102 C101 N101 129.4(5) . . ? C102 C101 C106 122.2(5) . . ? N101 C101 C106 108.3(4) . . ? C101 C102 C103 117.3(5) . . ? C101 C102 H102 121.3 . . ? C103 C102 H102 121.3 . . ? C102 C103 C104 121.9(5) . . ? C102 C103 H103 119.0 . . ? C104 C103 H103 119.0 . . ? C103 C104 C105 119.7(5) . . ? C103 C104 H104 120.2 . . ? C105 C104 H104 120.2 . . ? C106 C105 C104 119.4(5) . . ? C106 C105 H105 120.3 . . ? C104 C105 H105 120.3 . . ? C105 C106 C101 119.5(5) . . ? C105 C106 C107 131.1(5) . . ? C101 C106 C107 109.4(5) . . ? C106 C107 C108 101.7(4) . . ? C106 C107 C109 111.8(5) . . ? C108 C107 C109 112.7(5) . . ? C106 C107 C110 109.1(5) . . ? C108 C107 C110 110.1(5) . . ? C109 C107 C110 111.1(4) . . ? C111 C108 N101 122.1(5) . . ? C111 C108 C107 130.0(5) . . ? N101 C108 C107 107.9(4) . . ? C107 C109 H10H 109.5 . . ? C107 C109 H10I 109.5 . . ? H10H C109 H10I 109.5 . . ? C107 C109 H10J 109.5 . . ? H10H C109 H10J 109.5 . . ? H10I C109 H10J 109.5 . . ? C107 C110 H11E 109.5 . . ? C107 C110 H11F 109.5 . . ? H11E C110 H11F 109.5 . . ? C107 C110 H11G 109.5 . . ? H11E C110 H11G 109.5 . . ? H11F C110 H11G 109.5 . . ? C108 C111 C21S 132.5(5) . . ? C108 C111 H111 113.7 . . ? C21S C111 H111 113.7 . . ? C8 N1 C1 111.1(5) . . ? C8 N1 C1A 124.6(5) . . ? C1 N1 C1A 123.4(5) . . ? C108 N101 C101 112.1(4) . . ? C108 N101 C1B 124.1(4) . . ? C101 N101 C1B 122.7(4) . . ? Na1 O1H Na2 100.33(16) . 2_666 ? Na1 O1H H1O 105(5) . . ? Na2 O1H H1O 108(5) 2_666 . ? Na1 O1H H2O 118(5) . . ? Na2 O1H H2O 112(5) 2_666 . ? H1O O1H H2O 112(3) . . ? C1M O1M Na2 119.8(4) . . ? C1M O1M Na1 118.1(4) . . ? Na2 O1M Na1 92.35(17) . . ? C1M O1M H1M 99(5) . . ? Na2 O1M H1M 126(5) . . ? Na1 O1M H1M 102(5) . . ? C2S O1S Na2 143.4(4) . 2_566 ? C2M O2M Na2 123.5(5) . . ? C2M O2M H2M 102(5) . . ? Na2 O2M H2M 117(5) . . ? C3S O2S Na1 135.2(4) . 2_566 ? C3S O2S Na1 119.3(4) . . ? Na1 O2S Na1 85.91(15) 2_566 . ? C22S O21S Na1 147.1(4) . . ? O21S Na1 O1H 96.51(16) . . ? O21S Na1 O2S 90.21(16) . 2_566 ? O1H Na1 O2S 171.33(17) . 2_566 ? O21S Na1 O22S 173.66(19) . 2_566 ? O1H Na1 O22S 81.18(16) . 2_566 ? O2S Na1 O22S 92.69(15) 2_566 2_566 ? O21S Na1 O1M 95.36(17) . . ? O1H Na1 O1M 81.83(17) . . ? O2S Na1 O1M 92.12(17) 2_566 . ? O22S Na1 O1M 90.17(16) 2_566 . ? O21S Na1 O2S 77.67(16) . . ? O1H Na1 O2S 92.70(17) . . ? O2S Na1 O2S 94.09(16) 2_566 . ? O22S Na1 O2S 96.49(16) 2_566 . ? O1M Na1 O2S 170.66(16) . . ? O21S Na1 Na1 80.97(13) . 2_566 ? O1H Na1 Na1 138.36(18) . 2_566 ? O2S Na1 Na1 48.16(12) 2_566 2_566 ? O22S Na1 Na1 96.79(13) 2_566 2_566 ? O1M Na1 Na1 139.78(16) . 2_566 ? O2S Na1 Na1 45.93(11) . 2_566 ? O21S Na1 Na2 138.68(15) . . ? O1H Na1 Na2 84.35(12) . . ? O2S Na1 Na2 86.98(12) 2_566 . ? O22S Na1 Na2 47.22(12) 2_566 . ? O1M Na1 Na2 43.67(11) . . ? O2S Na1 Na2 143.65(13) . . ? Na1 Na1 Na2 124.30(10) 2_566 . ? O21S Na1 Na2 136.02(14) . 2_666 ? O1H Na1 Na2 39.96(11) . 2_666 ? O2S Na1 Na2 133.75(13) 2_566 2_666 ? O22S Na1 Na2 41.24(10) 2_566 2_666 ? O1M Na1 Na2 85.63(13) . 2_666 ? O2S Na1 Na2 95.06(13) . 2_666 ? Na1 Na1 Na2 124.34(12) 2_566 2_666 ? Na2 Na1 Na2 60.36(8) . 2_666 ? O1S Na2 O2M 94.6(2) 2_566 . ? O1S Na2 O1H 92.79(17) 2_566 2_666 ? O2M Na2 O1H 83.08(19) . 2_666 ? O1S Na2 O22S 170.3(2) 2_566 1_655 ? O2M Na2 O22S 92.0(2) . 1_655 ? O1H Na2 O22S 80.90(15) 2_666 1_655 ? O1S Na2 O1M 96.93(17) 2_566 . ? O2M Na2 O1M 102.4(2) . . ? O1H Na2 O1M 168.36(19) 2_666 . ? O22S Na2 O1M 88.61(15) 1_655 . ? O1S Na2 O22S 84.34(18) 2_566 2_566 ? O2M Na2 O22S 170.76(19) . 2_566 ? O1H Na2 O22S 87.81(17) 2_666 2_566 ? O22S Na2 O22S 88.01(15) 1_655 2_566 ? O1M Na2 O22S 86.79(15) . 2_566 ? O1S Na2 Na1 84.85(13) 2_566 . ? O2M Na2 Na1 145.64(17) . . ? O1H Na2 Na1 131.28(16) 2_666 . ? O22S Na2 Na1 93.73(12) 1_655 . ? O1M Na2 Na1 43.98(12) . . ? O22S Na2 Na1 43.49(10) 2_566 . ? O1S Na2 Na2 126.32(19) 2_566 2_666 ? O2M Na2 Na2 137.01(19) . 2_666 ? O1H Na2 Na2 82.31(15) 2_666 2_666 ? O22S Na2 Na2 45.77(12) 1_655 2_666 ? O1M Na2 Na2 86.77(14) . 2_666 ? O22S Na2 Na2 42.25(10) 2_566 2_666 ? Na1 Na2 Na2 61.55(7) . 2_666 ? O1S Na2 Na1 132.23(15) 2_566 2_666 ? O2M Na2 Na1 85.75(16) . 2_666 ? O1H Na2 Na1 39.71(11) 2_666 2_666 ? O22S Na2 Na1 41.21(10) 1_655 2_666 ? O1M Na2 Na1 129.72(13) . 2_666 ? O22S Na2 Na1 88.21(12) 2_566 2_666 ? Na1 Na2 Na1 119.64(8) . 2_666 ? Na2 Na2 Na1 58.10(7) 2_666 2_666 ? C23S O22S Na1 125.4(4) . 2_566 ? C23S O22S Na2 126.8(4) . 1_455 ? Na1 O22S Na2 97.55(15) 2_566 1_455 ? C23S O22S Na2 115.6(4) . 2_566 ? Na1 O22S Na2 89.30(16) 2_566 2_566 ? Na2 O22S Na2 91.99(15) 1_455 2_566 ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O1H H1O O3S 0.832(10) 1.899(13) 2.729(6) 175(7) . O1H H2O O23S 0.829(10) 1.99(3) 2.768(7) 155(6) 1_655 O2M H2M O3S 0.857(10) 2.10(3) 2.918(7) 158(7) 2_666 O1M H1M O23S 0.850(10) 1.97(3) 2.768(6) 155(7) 1_655 _diffrn_measured_fraction_theta_max 0.945 _diffrn_reflns_theta_full 24.71 _diffrn_measured_fraction_theta_full 0.945 _refine_diff_density_max 0.926 _refine_diff_density_min -0.404 _refine_diff_density_rms 0.083 _database_code_depnum_ccdc_archive 'CCDC 977421' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_5a _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C17 H20 N, I' _chemical_formula_sum 'C17 H20 I N' _chemical_formula_weight 365.24 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _space_group_crystal_system monoclinic _space_group_IT_number 14 _space_group_name_H-M_alt 'P 21/c' _space_group_name_Hall '-P 2ybc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 15.3349(3) _cell_length_b 7.5158(2) _cell_length_c 13.7564(2) _cell_angle_alpha 90.00 _cell_angle_beta 92.5450(10) _cell_angle_gamma 90.00 _cell_volume 1583.92(6) _cell_formula_units_Z 4 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 16070 _cell_measurement_theta_min 2.91 _cell_measurement_theta_max 27.48 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.08 _exptl_crystal_size_mid 0.08 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.532 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 728 _exptl_absorpt_coefficient_mu 2.010 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8558 _exptl_absorpt_correction_T_max 0.8889 _exptl_absorpt_process_details 'SADABS 2007/2 (Sheldrick, G.M., 2007)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Bruker-Nonius FR591 rotating anode' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker-Nonius Roper CCD camera on \k-goniostat' _diffrn_measurement_method '\f & \w scans' _diffrn_detector_area_resol_mean 9.091 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 14035 _diffrn_reflns_av_R_equivalents 0.0390 _diffrn_reflns_av_sigmaI/netI 0.0285 _diffrn_reflns_limit_h_min -18 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 2.96 _diffrn_reflns_theta_max 25.02 _reflns_number_total 2792 _reflns_number_gt 2592 _reflns_threshold_expression >2\s(I) _computing_data_collection 'COLLECT (Hooft, R.W.W., 1998)' _computing_cell_refinement 'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)' _computing_data_reduction 'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)' _computing_structure_solution 'SHELXL-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2\s(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0107P)^2^+2.1960P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2792 _refine_ls_number_parameters 176 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0243 _refine_ls_R_factor_gt 0.0217 _refine_ls_wR_factor_ref 0.0528 _refine_ls_wR_factor_gt 0.0507 _refine_ls_goodness_of_fit_ref 1.070 _refine_ls_restrained_S_all 1.070 _refine_ls_shift/su_max 0.002 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.75090(16) 0.9217(3) 0.35881(16) 0.0161(5) Uani 1 1 d . . . C1A C 0.58538(16) 0.9471(4) 0.34527(17) 0.0232(5) Uani 1 1 d . . . H1A1 H 0.5933 1.0777 0.3492 0.028 Uiso 1 1 calc R . . H1A2 H 0.5371 0.9140 0.3871 0.028 Uiso 1 1 calc R . . C2 C 0.76974(16) 1.0682(3) 0.30159(17) 0.0188(5) Uani 1 1 d . . . H2 H 0.7248 1.1392 0.2717 0.023 Uiso 1 1 calc R . . C2A C 0.56206(18) 0.8940(4) 0.24063(18) 0.0279(6) Uani 1 1 d . . . H2A1 H 0.6036 0.9485 0.1974 0.042 Uiso 1 1 calc R . . H2A2 H 0.5029 0.9351 0.2226 0.042 Uiso 1 1 calc R . . H2A3 H 0.5647 0.7642 0.2345 0.042 Uiso 1 1 calc R . . C3 C 0.85588(17) 1.1050(3) 0.29046(17) 0.0200(5) Uani 1 1 d . . . H3 H 0.8712 1.2036 0.2515 0.024 Uiso 1 1 calc R . . C4 C 0.92326(16) 1.0001(3) 0.33555(16) 0.0180(5) Uani 1 1 d . . . C5 C 0.90238(17) 0.8493(3) 0.39343(16) 0.0183(5) Uani 1 1 d . . . C6 C 0.81282(16) 0.8130(3) 0.40351(15) 0.0160(5) Uani 1 1 d . . . C7 C 0.76571(16) 0.6635(3) 0.45356(16) 0.0175(5) Uani 1 1 d . . . C8 C 0.67193(16) 0.7164(3) 0.43475(16) 0.0186(5) Uani 1 1 d . . . C9 C 0.78545(17) 0.6451(3) 0.56418(17) 0.0205(5) Uani 1 1 d . . . H9A H 0.7695 0.7556 0.5968 0.031 Uiso 1 1 calc R . . H9B H 0.8479 0.6220 0.5765 0.031 Uiso 1 1 calc R . . H9C H 0.7516 0.5462 0.5894 0.031 Uiso 1 1 calc R . . C10 C 0.77991(18) 0.4843(3) 0.40057(18) 0.0237(5) Uani 1 1 d . . . H10A H 0.7486 0.3895 0.4333 0.036 Uiso 1 1 calc R . . H10B H 0.8424 0.4564 0.4021 0.036 Uiso 1 1 calc R . . H10C H 0.7578 0.4938 0.3328 0.036 Uiso 1 1 calc R . . C11 C 0.59508(18) 0.6229(4) 0.47234(19) 0.0278(6) Uani 1 1 d . . . H11A H 0.5740 0.6878 0.5285 0.042 Uiso 1 1 calc R . . H11B H 0.6118 0.5020 0.4922 0.042 Uiso 1 1 calc R . . H11C H 0.5486 0.6173 0.4212 0.042 Uiso 1 1 calc R . . C12 C 1.01220(17) 1.0456(3) 0.32459(18) 0.0244(6) Uani 1 1 d . . . H12 H 1.0264 1.1442 0.2851 0.029 Uiso 1 1 calc R . . C13 C 1.07767(17) 0.9488(4) 0.37034(19) 0.0266(6) Uani 1 1 d . . . H13 H 1.1369 0.9817 0.3636 0.032 Uiso 1 1 calc R . . C14 C 1.05705(17) 0.8003(4) 0.42745(19) 0.0272(6) Uani 1 1 d . . . H14 H 1.1028 0.7336 0.4588 0.033 Uiso 1 1 calc R . . C15 C 0.97216(16) 0.7507(3) 0.43849(17) 0.0226(5) Uani 1 1 d . . . H15 H 0.9598 0.6493 0.4767 0.027 Uiso 1 1 calc R . . N1 N 0.66637(13) 0.8578(3) 0.38064(14) 0.0167(4) Uani 1 1 d . . . I1 I 0.656569(10) 1.12549(2) 0.603800(11) 0.02231(7) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0193(12) 0.0162(11) 0.0128(11) -0.0038(9) 0.0007(9) 0.0007(10) C1A 0.0198(13) 0.0282(14) 0.0213(13) 0.0009(11) -0.0016(10) 0.0051(11) C2 0.0241(13) 0.0163(12) 0.0160(11) 0.0010(9) -0.0005(9) 0.0035(10) C2A 0.0270(15) 0.0351(16) 0.0211(13) 0.0012(11) -0.0059(11) -0.0016(12) C3 0.0295(14) 0.0143(12) 0.0165(12) 0.0004(9) 0.0041(10) -0.0002(10) C4 0.0219(13) 0.0186(12) 0.0139(11) -0.0056(9) 0.0045(9) -0.0027(10) C5 0.0253(13) 0.0174(12) 0.0123(11) -0.0041(9) 0.0023(9) 0.0022(10) C6 0.0227(13) 0.0133(11) 0.0120(11) -0.0014(9) 0.0011(9) 0.0003(10) C7 0.0221(13) 0.0158(12) 0.0144(11) 0.0016(9) 0.0002(9) -0.0016(10) C8 0.0238(13) 0.0189(12) 0.0132(11) -0.0033(9) 0.0005(9) -0.0038(10) C9 0.0254(14) 0.0207(13) 0.0155(12) 0.0030(9) 0.0011(10) -0.0014(10) C10 0.0344(15) 0.0164(12) 0.0204(12) -0.0001(10) 0.0020(11) -0.0009(11) C11 0.0259(15) 0.0328(16) 0.0246(13) 0.0047(11) 0.0007(11) -0.0074(11) C12 0.0282(14) 0.0243(14) 0.0212(13) -0.0078(10) 0.0073(10) -0.0055(11) C13 0.0178(13) 0.0332(15) 0.0294(14) -0.0149(12) 0.0069(10) -0.0042(11) C14 0.0240(14) 0.0306(15) 0.0268(13) -0.0083(12) -0.0004(11) 0.0073(12) C15 0.0259(14) 0.0236(13) 0.0184(12) -0.0017(10) 0.0010(10) 0.0064(11) N1 0.0152(10) 0.0198(11) 0.0150(9) -0.0027(8) 0.0006(8) -0.0002(8) I1 0.01945(11) 0.02284(11) 0.02448(11) -0.00636(6) -0.00082(7) -0.00090(6) _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C6 1.377(3) . ? C1 C2 1.392(3) . ? C1 N1 1.427(3) . ? C1A N1 1.475(3) . ? C1A C2A 1.521(3) . ? C1A H1A1 0.9900 . ? C1A H1A2 0.9900 . ? C2 C3 1.365(4) . ? C2 H2 0.9500 . ? C2A H2A1 0.9800 . ? C2A H2A2 0.9800 . ? C2A H2A3 0.9800 . ? C3 C4 1.421(3) . ? C3 H3 0.9500 . ? C4 C12 1.421(4) . ? C4 C5 1.430(3) . ? C5 C6 1.413(4) . ? C5 C15 1.421(3) . ? C6 C7 1.517(3) . ? C7 C8 1.503(3) . ? C7 C9 1.544(3) . ? C7 C10 1.551(3) . ? C8 N1 1.298(3) . ? C8 C11 1.485(4) . ? C9 H9A 0.9800 . ? C9 H9B 0.9800 . ? C9 H9C 0.9800 . ? C10 H10A 0.9800 . ? C10 H10B 0.9800 . ? C10 H10C 0.9800 . ? C11 H11A 0.9800 . ? C11 H11B 0.9800 . ? C11 H11C 0.9800 . ? C12 C13 1.370(4) . ? C12 H12 0.9500 . ? C13 C14 1.408(4) . ? C13 H13 0.9500 . ? C14 C15 1.369(4) . ? C14 H14 0.9500 . ? C15 H15 0.9500 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C6 C1 C2 124.5(2) . . ? C6 C1 N1 108.7(2) . . ? C2 C1 N1 126.8(2) . . ? N1 C1A C2A 110.6(2) . . ? N1 C1A H1A1 109.5 . . ? C2A C1A H1A1 109.5 . . ? N1 C1A H1A2 109.5 . . ? C2A C1A H1A2 109.5 . . ? H1A1 C1A H1A2 108.1 . . ? C3 C2 C1 116.8(2) . . ? C3 C2 H2 121.6 . . ? C1 C2 H2 121.6 . . ? C1A C2A H2A1 109.5 . . ? C1A C2A H2A2 109.5 . . ? H2A1 C2A H2A2 109.5 . . ? C1A C2A H2A3 109.5 . . ? H2A1 C2A H2A3 109.5 . . ? H2A2 C2A H2A3 109.5 . . ? C2 C3 C4 121.8(2) . . ? C2 C3 H3 119.1 . . ? C4 C3 H3 119.1 . . ? C12 C4 C3 120.2(2) . . ? C12 C4 C5 119.3(2) . . ? C3 C4 C5 120.5(2) . . ? C6 C5 C15 125.0(2) . . ? C6 C5 C4 116.8(2) . . ? C15 C5 C4 118.2(2) . . ? C1 C6 C5 119.7(2) . . ? C1 C6 C7 108.0(2) . . ? C5 C6 C7 132.2(2) . . ? C8 C7 C6 101.36(19) . . ? C8 C7 C9 109.7(2) . . ? C6 C7 C9 115.90(19) . . ? C8 C7 C10 107.6(2) . . ? C6 C7 C10 110.48(19) . . ? C9 C7 C10 111.10(19) . . ? N1 C8 C11 123.7(2) . . ? N1 C8 C7 110.7(2) . . ? C11 C8 C7 125.6(2) . . ? C7 C9 H9A 109.5 . . ? C7 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? C7 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? C7 C10 H10A 109.5 . . ? C7 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? C7 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? C8 C11 H11A 109.5 . . ? C8 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? C8 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? C13 C12 C4 120.7(2) . . ? C13 C12 H12 119.6 . . ? C4 C12 H12 119.6 . . ? C12 C13 C14 119.9(2) . . ? C12 C13 H13 120.0 . . ? C14 C13 H13 120.0 . . ? C15 C14 C13 121.1(2) . . ? C15 C14 H14 119.5 . . ? C13 C14 H14 119.5 . . ? C14 C15 C5 120.7(2) . . ? C14 C15 H15 119.6 . . ? C5 C15 H15 119.6 . . ? C8 N1 C1 111.0(2) . . ? C8 N1 C1A 126.5(2) . . ? C1 N1 C1A 122.5(2) . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 25.02 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.366 _refine_diff_density_min -0.367 _refine_diff_density_rms 0.072 _database_code_depnum_ccdc_archive 'CCDC 977422' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_6b _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C33 H43 N O3' _chemical_formula_sum 'C33 H43 N O3' _chemical_formula_weight 501.68 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M C2/c _symmetry_space_group_name_Hall '-C 2yc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 19.2363(14) _cell_length_b 10.2830(7) _cell_length_c 29.048(2) _cell_angle_alpha 90.00 _cell_angle_beta 92.704(2) _cell_angle_gamma 90.00 _cell_volume 5739.5(7) _cell_formula_units_Z 8 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min 2.8 _cell_measurement_theta_max 27.5 _exptl_crystal_description tablet _exptl_crystal_colour orange _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.161 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2176 _exptl_absorpt_coefficient_mu 0.073 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9714 _exptl_absorpt_correction_T_max 0.9971 _exptl_absorpt_process_details 'CrystalClear-SM Expert 3.1 b27 (Rigaku, 20112)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_source_power 2.5 _diffrn_source_voltage 45.0 _diffrn_source_current 55.0 _diffrn_radiation_wavelength 0.71075 _diffrn_radiation_type 'Mo K\a' _diffrn_source 'Rotating Anode' _diffrn_radiation_monochromator Confocal _diffrn_measurement_specimen_support MiTeGen _diffrn_detector CCD _diffrn_measurement_device ; AFC12 (Right): Kappa 3 circle ; _diffrn_measurement_device_type ; Rigaku Saturn724+ (2x2 bin mode) ; _diffrn_detector_area_resol_mean 28.5714 _diffrn_measurement_method 'profile data from \w-scans' _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 15920 _diffrn_reflns_av_R_equivalents 0.0461 _diffrn_reflns_av_sigmaI/netI 0.0357 _diffrn_reflns_limit_h_min -22 _diffrn_reflns_limit_h_max 21 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -34 _diffrn_reflns_limit_l_max 34 _diffrn_reflns_theta_min 3.05 _diffrn_reflns_theta_max 25.02 _reflns_number_total 5046 _reflns_number_gt 4129 _reflns_threshold_expression >2\s(I) _computing_data_collection 'CrystalClear-SM Expert 3.1 b27 (Rigaku, 20112)' _computing_cell_refinement 'CrystalClear-SM Expert 3.1 b27 (Rigaku, 20112)' _computing_data_reduction 'CrystalClear-SM Expert 3.1 b27 (Rigaku, 20112)' _computing_structure_solution 'SHELXL-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2\s(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0582P)^2^+1.5580P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 5046 _refine_ls_number_parameters 338 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0505 _refine_ls_R_factor_gt 0.0401 _refine_ls_wR_factor_ref 0.1077 _refine_ls_wR_factor_gt 0.1025 _refine_ls_goodness_of_fit_ref 1.033 _refine_ls_restrained_S_all 1.033 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.22242(6) -0.00775(13) 0.16605(4) 0.0188(3) Uani 1 1 d . . . C1A C 0.26889(7) 0.19525(14) 0.12824(5) 0.0217(3) Uani 1 1 d . . . H1A1 H 0.2485 0.2444 0.1016 0.026 Uiso 1 1 calc R . . H1A2 H 0.3040 0.1347 0.1166 0.026 Uiso 1 1 calc R . . C1S C 0.06607(6) 0.36010(14) 0.14717(4) 0.0214(3) Uani 1 1 d . . . C2 C 0.28300(6) -0.08418(13) 0.16471(4) 0.0207(3) Uani 1 1 d . . . H2 H 0.3245 -0.0511 0.1527 0.025 Uiso 1 1 calc R . . C2A C 0.30449(7) 0.28998(14) 0.16219(5) 0.0244(3) Uani 1 1 d . . . H2A1 H 0.3312 0.2400 0.1862 0.029 Uiso 1 1 calc R . . H2A2 H 0.2685 0.3405 0.1776 0.029 Uiso 1 1 calc R . . C2S C -0.00631(7) 0.35775(14) 0.16500(5) 0.0230(3) Uani 1 1 d . . . C3 C 0.27945(7) -0.20829(13) 0.18149(4) 0.0221(3) Uani 1 1 d . . . H3 H 0.3196 -0.2620 0.1810 0.026 Uiso 1 1 calc R . . C3A C 0.35358(7) 0.38413(14) 0.13911(5) 0.0270(3) Uani 1 1 d . . . H3A1 H 0.3872 0.3330 0.1218 0.032 Uiso 1 1 calc R . . H3A2 H 0.3803 0.4329 0.1634 0.032 Uiso 1 1 calc R . . C3S C -0.01695(7) 0.49587(14) 0.14641(5) 0.0228(3) Uani 1 1 d . . . C4 C 0.21801(7) -0.25945(14) 0.19962(4) 0.0214(3) Uani 1 1 d . . . C4A C 0.31731(7) 0.48188(14) 0.10613(5) 0.0253(3) Uani 1 1 d . . . H4A1 H 0.2976 0.4347 0.0788 0.030 Uiso 1 1 calc R . . H4A2 H 0.2782 0.5228 0.1217 0.030 Uiso 1 1 calc R . . C4S C 0.05409(6) 0.48589(14) 0.13078(5) 0.0217(3) Uani 1 1 d . . . C5 C 0.15738(6) -0.17834(14) 0.20191(4) 0.0206(3) Uani 1 1 d . . . C5A C 0.36606(7) 0.58820(14) 0.09024(5) 0.0252(3) Uani 1 1 d . . . H5A1 H 0.3905 0.6270 0.1177 0.030 Uiso 1 1 calc R . . H5A2 H 0.4017 0.5480 0.0712 0.030 Uiso 1 1 calc R . . C5S C 0.07072(7) 0.68873(14) 0.09474(5) 0.0295(3) Uani 1 1 d . . . H5S1 H 0.0500 0.7329 0.1211 0.035 Uiso 1 1 calc R . . H5S2 H 0.0345 0.6800 0.0695 0.035 Uiso 1 1 calc R . . C6 C 0.16157(6) -0.05001(13) 0.18428(4) 0.0192(3) Uani 1 1 d . . . C6A C 0.32974(7) 0.69622(14) 0.06246(5) 0.0253(3) Uani 1 1 d . . . H6A1 H 0.2906 0.7299 0.0800 0.030 Uiso 1 1 calc R . . H6A2 H 0.3100 0.6594 0.0332 0.030 Uiso 1 1 calc R . . C6S C 0.13149(8) 0.76525(15) 0.07866(5) 0.0299(3) Uani 1 1 d . . . H6S1 H 0.1660 0.7760 0.1043 0.045 Uiso 1 1 calc R . . H6S2 H 0.1155 0.8509 0.0678 0.045 Uiso 1 1 calc R . . H6S3 H 0.1526 0.7187 0.0534 0.045 Uiso 1 1 calc R . . C7 C 0.10840(6) 0.05976(13) 0.18124(4) 0.0198(3) Uani 1 1 d . . . C7A C 0.37774(7) 0.80881(14) 0.05155(5) 0.0274(3) Uani 1 1 d . . . H7A1 H 0.4046 0.8336 0.0801 0.033 Uiso 1 1 calc R . . H7A2 H 0.4114 0.7785 0.0291 0.033 Uiso 1 1 calc R . . C8 C 0.14864(6) 0.16626(13) 0.15699(4) 0.0190(3) Uani 1 1 d . . . C8A C 0.34088(7) 0.92921(14) 0.03204(5) 0.0269(3) Uani 1 1 d . . . H8A1 H 0.3144 0.9053 0.0032 0.032 Uiso 1 1 calc R . . H8A2 H 0.3072 0.9601 0.0543 0.032 Uiso 1 1 calc R . . C9 C 0.09086(7) 0.10834(15) 0.22964(4) 0.0252(3) Uani 1 1 d . . . H9A H 0.0699 0.0374 0.2467 0.038 Uiso 1 1 calc R . . H9B H 0.0580 0.1810 0.2266 0.038 Uiso 1 1 calc R . . H9C H 0.1336 0.1375 0.2463 0.038 Uiso 1 1 calc R . . C9A C 0.39052(8) 1.03936(16) 0.02191(6) 0.0351(4) Uani 1 1 d . . . H9A1 H 0.4248 1.0068 0.0003 0.042 Uiso 1 1 calc R . . H9A2 H 0.4164 1.0632 0.0509 0.042 Uiso 1 1 calc R . . C10 C 0.04223(7) 0.02351(15) 0.15192(5) 0.0245(3) Uani 1 1 d . . . H10A H 0.0552 -0.0032 0.1211 0.037 Uiso 1 1 calc R . . H10B H 0.0112 0.0990 0.1494 0.037 Uiso 1 1 calc R . . H10C H 0.0183 -0.0483 0.1667 0.037 Uiso 1 1 calc R . . C10A C 0.35702(8) 1.16155(15) 0.00147(5) 0.0323(4) Uani 1 1 d . . . H10D H 0.3348 1.1402 -0.0290 0.039 Uiso 1 1 calc R . . H10E H 0.3200 1.1907 0.0216 0.039 Uiso 1 1 calc R . . C11 C 0.12877(7) 0.28979(14) 0.14362(5) 0.0217(3) Uani 1 1 d . . . H11 H 0.1641 0.3371 0.1292 0.026 Uiso 1 1 calc R . . C11A C 0.40786(10) 1.27215(18) -0.00415(7) 0.0507(5) Uani 1 1 d . . . H11A H 0.4304 1.2922 0.0264 0.061 Uiso 1 1 calc R . . H11B H 0.4447 1.2427 -0.0245 0.061 Uiso 1 1 calc R . . C12 C 0.21529(7) -0.38980(14) 0.21548(5) 0.0244(3) Uani 1 1 d . . . H12 H 0.2554 -0.4432 0.2140 0.029 Uiso 1 1 calc R . . C12A C 0.37608(11) 1.39591(17) -0.02398(6) 0.0474(5) Uani 1 1 d . . . H12A H 0.3579 1.3798 -0.0555 0.071 Uiso 1 1 calc R . . H12B H 0.4117 1.4640 -0.0242 0.071 Uiso 1 1 calc R . . H12C H 0.3381 1.4241 -0.0050 0.071 Uiso 1 1 calc R . . C13 C 0.15620(7) -0.44008(15) 0.23282(5) 0.0282(3) Uani 1 1 d . . . H13 H 0.1551 -0.5280 0.2428 0.034 Uiso 1 1 calc R . . C14 C 0.09706(7) -0.36062(15) 0.23580(5) 0.0301(3) Uani 1 1 d . . . H14 H 0.0563 -0.3954 0.2483 0.036 Uiso 1 1 calc R . . C15 C 0.09697(7) -0.23433(15) 0.22100(5) 0.0255(3) Uani 1 1 d . . . H15 H 0.0562 -0.1830 0.2234 0.031 Uiso 1 1 calc R . . N1 N 0.21392(5) 0.12020(11) 0.14938(4) 0.0198(3) Uani 1 1 d . . . O1S O -0.04238(5) 0.28234(10) 0.18515(4) 0.0307(3) Uani 1 1 d . . . O2S O -0.06415(5) 0.57569(10) 0.14537(4) 0.0307(3) Uani 1 1 d . . . O3S O 0.09717(5) 0.56135(10) 0.10860(3) 0.0275(2) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0145(6) 0.0219(7) 0.0198(6) -0.0017(5) -0.0002(5) 0.0001(5) C1A 0.0152(6) 0.0238(7) 0.0264(7) 0.0023(6) 0.0056(5) -0.0001(6) C1S 0.0148(6) 0.0254(8) 0.0237(7) -0.0020(6) -0.0009(5) 0.0000(6) C2 0.0130(6) 0.0265(8) 0.0228(7) -0.0027(6) 0.0028(5) 0.0004(6) C2A 0.0177(7) 0.0276(8) 0.0279(7) 0.0022(6) -0.0008(5) -0.0002(6) C2S 0.0148(6) 0.0296(8) 0.0246(7) -0.0005(6) 0.0003(5) 0.0029(6) C3 0.0163(6) 0.0253(8) 0.0243(7) -0.0027(6) -0.0006(5) 0.0045(6) C3A 0.0177(7) 0.0270(8) 0.0359(8) 0.0024(6) -0.0013(6) -0.0038(6) C3S 0.0160(6) 0.0257(8) 0.0266(7) -0.0020(6) -0.0009(5) 0.0011(6) C4 0.0199(6) 0.0248(8) 0.0192(6) -0.0021(5) -0.0033(5) 0.0003(6) C4A 0.0176(6) 0.0268(8) 0.0316(7) 0.0008(6) 0.0005(5) -0.0025(6) C4S 0.0151(6) 0.0241(7) 0.0257(7) -0.0004(6) 0.0006(5) -0.0001(6) C5 0.0163(6) 0.0255(8) 0.0197(6) -0.0009(5) -0.0013(5) -0.0017(6) C5A 0.0187(7) 0.0262(8) 0.0306(7) 0.0004(6) 0.0009(5) -0.0023(6) C5S 0.0252(7) 0.0229(8) 0.0401(8) 0.0066(6) -0.0014(6) 0.0053(6) C6 0.0130(6) 0.0249(7) 0.0198(6) -0.0022(5) 0.0002(5) -0.0002(6) C6A 0.0198(7) 0.0280(8) 0.0282(7) -0.0009(6) 0.0013(5) -0.0027(6) C6S 0.0336(8) 0.0273(8) 0.0290(8) 0.0011(6) 0.0051(6) 0.0000(7) C7 0.0127(6) 0.0232(7) 0.0233(7) 0.0003(6) 0.0010(5) 0.0013(5) C7A 0.0230(7) 0.0284(8) 0.0305(7) 0.0027(6) -0.0023(6) -0.0039(6) C8 0.0113(6) 0.0250(7) 0.0208(6) -0.0025(5) 0.0002(5) 0.0009(5) C8A 0.0254(7) 0.0281(8) 0.0271(7) -0.0014(6) 0.0006(6) -0.0008(6) C9 0.0188(7) 0.0319(8) 0.0249(7) -0.0010(6) 0.0029(5) 0.0057(6) C9A 0.0319(8) 0.0322(9) 0.0406(9) 0.0076(7) -0.0050(7) -0.0050(7) C10 0.0147(6) 0.0283(8) 0.0303(7) 0.0018(6) -0.0007(5) -0.0001(6) C10A 0.0358(8) 0.0305(9) 0.0305(8) 0.0041(7) 0.0016(6) 0.0009(7) C11 0.0133(6) 0.0246(7) 0.0275(7) 0.0001(6) 0.0024(5) -0.0015(6) C11A 0.0516(11) 0.0385(10) 0.0604(12) 0.0185(9) -0.0138(9) -0.0095(9) C12 0.0232(7) 0.0253(8) 0.0243(7) 0.0001(6) -0.0043(5) 0.0009(6) C12A 0.0719(13) 0.0337(10) 0.0360(9) 0.0067(7) -0.0050(9) -0.0061(9) C13 0.0301(8) 0.0262(8) 0.0276(7) 0.0055(6) -0.0072(6) -0.0056(6) C14 0.0219(7) 0.0375(9) 0.0306(8) 0.0079(7) -0.0014(6) -0.0077(7) C15 0.0165(6) 0.0317(8) 0.0282(7) 0.0033(6) 0.0003(5) -0.0014(6) N1 0.0123(5) 0.0221(6) 0.0252(6) 0.0002(5) 0.0038(4) 0.0006(5) O1S 0.0187(5) 0.0348(6) 0.0391(6) 0.0087(5) 0.0072(4) 0.0019(4) O2S 0.0184(5) 0.0316(6) 0.0424(6) 0.0020(5) 0.0039(4) 0.0085(5) O3S 0.0188(5) 0.0244(6) 0.0394(6) 0.0064(4) 0.0043(4) 0.0028(4) _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C6 1.3777(17) . ? C1 C2 1.4075(18) . ? C1 N1 1.4088(17) . ? C1A N1 1.4670(16) . ? C1A C2A 1.5253(19) . ? C1A H1A1 0.9900 . ? C1A H1A2 0.9900 . ? C1S C4S 1.394(2) . ? C1S C11 1.4142(18) . ? C1S C2S 1.5084(18) . ? C2 C3 1.3690(19) . ? C2 H2 0.9500 . ? C2A C3A 1.5292(19) . ? C2A H2A1 0.9900 . ? C2A H2A2 0.9900 . ? C2S O1S 1.2098(17) . ? C2S C3S 1.530(2) . ? C3 C4 1.4176(19) . ? C3 H3 0.9500 . ? C3A C4A 1.5335(19) . ? C3A H3A1 0.9900 . ? C3A H3A2 0.9900 . ? C3S O2S 1.2231(16) . ? C3S C4S 1.4640(18) . ? C4 C12 1.419(2) . ? C4 C5 1.4379(18) . ? C4A C5A 1.5261(19) . ? C4A H4A1 0.9900 . ? C4A H4A2 0.9900 . ? C4S O3S 1.3244(16) . ? C5 C6 1.4191(19) . ? C5 C15 1.4318(18) . ? C5A C6A 1.523(2) . ? C5A H5A1 0.9900 . ? C5A H5A2 0.9900 . ? C5S O3S 1.4551(17) . ? C5S C6S 1.502(2) . ? C5S H5S1 0.9900 . ? C5S H5S2 0.9900 . ? C6 C7 1.5230(18) . ? C6A C7A 1.5236(19) . ? C6A H6A1 0.9900 . ? C6A H6A2 0.9900 . ? C6S H6S1 0.9800 . ? C6S H6S2 0.9800 . ? C6S H6S3 0.9800 . ? C7 C8 1.5318(18) . ? C7 C10 1.5435(17) . ? C7 C9 1.5442(18) . ? C7A C8A 1.523(2) . ? C7A H7A1 0.9900 . ? C7A H7A2 0.9900 . ? C8 N1 1.3697(16) . ? C8 C11 1.3772(19) . ? C8A C9A 1.519(2) . ? C8A H8A1 0.9900 . ? C8A H8A2 0.9900 . ? C9 H9A 0.9800 . ? C9 H9B 0.9800 . ? C9 H9C 0.9800 . ? C9A C10A 1.520(2) . ? C9A H9A1 0.9900 . ? C9A H9A2 0.9900 . ? C10 H10A 0.9800 . ? C10 H10B 0.9800 . ? C10 H10C 0.9800 . ? C10A C11A 1.514(2) . ? C10A H10D 0.9900 . ? C10A H10E 0.9900 . ? C11 H11 0.9500 . ? C11A C12A 1.514(2) . ? C11A H11A 0.9900 . ? C11A H11B 0.9900 . ? C12 C13 1.366(2) . ? C12 H12 0.9500 . ? C12A H12A 0.9800 . ? C12A H12B 0.9800 . ? C12A H12C 0.9800 . ? C13 C14 1.407(2) . ? C13 H13 0.9500 . ? C14 C15 1.368(2) . ? C14 H14 0.9500 . ? C15 H15 0.9500 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C6 C1 C2 123.64(13) . . ? C6 C1 N1 109.86(11) . . ? C2 C1 N1 126.50(12) . . ? N1 C1A C2A 112.07(11) . . ? N1 C1A H1A1 109.2 . . ? C2A C1A H1A1 109.2 . . ? N1 C1A H1A2 109.2 . . ? C2A C1A H1A2 109.2 . . ? H1A1 C1A H1A2 107.9 . . ? C4S C1S C11 125.26(13) . . ? C4S C1S C2S 89.53(11) . . ? C11 C1S C2S 145.19(13) . . ? C3 C2 C1 117.10(12) . . ? C3 C2 H2 121.5 . . ? C1 C2 H2 121.5 . . ? C1A C2A C3A 112.86(11) . . ? C1A C2A H2A1 109.0 . . ? C3A C2A H2A1 109.0 . . ? C1A C2A H2A2 109.0 . . ? C3A C2A H2A2 109.0 . . ? H2A1 C2A H2A2 107.8 . . ? O1S C2S C1S 137.40(13) . . ? O1S C2S C3S 134.07(12) . . ? C1S C2S C3S 88.52(11) . . ? C2 C3 C4 122.32(12) . . ? C2 C3 H3 118.8 . . ? C4 C3 H3 118.8 . . ? C2A C3A C4A 114.63(11) . . ? C2A C3A H3A1 108.6 . . ? C4A C3A H3A1 108.6 . . ? C2A C3A H3A2 108.6 . . ? C4A C3A H3A2 108.6 . . ? H3A1 C3A H3A2 107.6 . . ? O2S C3S C4S 137.90(14) . . ? O2S C3S C2S 135.94(13) . . ? C4S C3S C2S 86.16(10) . . ? C3 C4 C12 121.02(12) . . ? C3 C4 C5 119.62(12) . . ? C12 C4 C5 119.37(12) . . ? C5A C4A C3A 112.99(11) . . ? C5A C4A H4A1 109.0 . . ? C3A C4A H4A1 109.0 . . ? C5A C4A H4A2 109.0 . . ? C3A C4A H4A2 109.0 . . ? H4A1 C4A H4A2 107.8 . . ? O3S C4S C1S 127.80(12) . . ? O3S C4S C3S 136.42(13) . . ? C1S C4S C3S 95.78(11) . . ? C6 C5 C15 125.07(12) . . ? C6 C5 C4 117.56(12) . . ? C15 C5 C4 117.36(12) . . ? C6A C5A C4A 114.18(11) . . ? C6A C5A H5A1 108.7 . . ? C4A C5A H5A1 108.7 . . ? C6A C5A H5A2 108.7 . . ? C4A C5A H5A2 108.7 . . ? H5A1 C5A H5A2 107.6 . . ? O3S C5S C6S 106.89(11) . . ? O3S C5S H5S1 110.3 . . ? C6S C5S H5S1 110.3 . . ? O3S C5S H5S2 110.3 . . ? C6S C5S H5S2 110.3 . . ? H5S1 C5S H5S2 108.6 . . ? C1 C6 C5 119.72(12) . . ? C1 C6 C7 108.93(12) . . ? C5 C6 C7 131.35(12) . . ? C5A C6A C7A 113.39(11) . . ? C5A C6A H6A1 108.9 . . ? C7A C6A H6A1 108.9 . . ? C5A C6A H6A2 108.9 . . ? C7A C6A H6A2 108.9 . . ? H6A1 C6A H6A2 107.7 . . ? C5S C6S H6S1 109.5 . . ? C5S C6S H6S2 109.5 . . ? H6S1 C6S H6S2 109.5 . . ? C5S C6S H6S3 109.5 . . ? H6S1 C6S H6S3 109.5 . . ? H6S2 C6S H6S3 109.5 . . ? C6 C7 C8 101.77(10) . . ? C6 C7 C10 112.78(11) . . ? C8 C7 C10 109.90(11) . . ? C6 C7 C9 111.22(10) . . ? C8 C7 C9 108.92(11) . . ? C10 C7 C9 111.75(10) . . ? C8A C7A C6A 114.78(11) . . ? C8A C7A H7A1 108.6 . . ? C6A C7A H7A1 108.6 . . ? C8A C7A H7A2 108.6 . . ? C6A C7A H7A2 108.6 . . ? H7A1 C7A H7A2 107.5 . . ? N1 C8 C11 121.19(12) . . ? N1 C8 C7 108.30(11) . . ? C11 C8 C7 130.51(11) . . ? C9A C8A C7A 113.10(11) . . ? C9A C8A H8A1 109.0 . . ? C7A C8A H8A1 109.0 . . ? C9A C8A H8A2 109.0 . . ? C7A C8A H8A2 109.0 . . ? H8A1 C8A H8A2 107.8 . . ? C7 C9 H9A 109.5 . . ? C7 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? C7 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? C8A C9A C10A 115.67(12) . . ? C8A C9A H9A1 108.4 . . ? C10A C9A H9A1 108.4 . . ? C8A C9A H9A2 108.4 . . ? C10A C9A H9A2 108.4 . . ? H9A1 C9A H9A2 107.4 . . ? C7 C10 H10A 109.5 . . ? C7 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? C7 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? C11A C10A C9A 113.52(13) . . ? C11A C10A H10D 108.9 . . ? C9A C10A H10D 108.9 . . ? C11A C10A H10E 108.9 . . ? C9A C10A H10E 108.9 . . ? H10D C10A H10E 107.7 . . ? C8 C11 C1S 132.64(13) . . ? C8 C11 H11 113.7 . . ? C1S C11 H11 113.7 . . ? C12A C11A C10A 114.92(15) . . ? C12A C11A H11A 108.5 . . ? C10A C11A H11A 108.5 . . ? C12A C11A H11B 108.5 . . ? C10A C11A H11B 108.5 . . ? H11A C11A H11B 107.5 . . ? C13 C12 C4 121.41(13) . . ? C13 C12 H12 119.3 . . ? C4 C12 H12 119.3 . . ? C11A C12A H12A 109.5 . . ? C11A C12A H12B 109.5 . . ? H12A C12A H12B 109.5 . . ? C11A C12A H12C 109.5 . . ? H12A C12A H12C 109.5 . . ? H12B C12A H12C 109.5 . . ? C12 C13 C14 119.48(14) . . ? C12 C13 H13 120.3 . . ? C14 C13 H13 120.3 . . ? C15 C14 C13 121.41(13) . . ? C15 C14 H14 119.3 . . ? C13 C14 H14 119.3 . . ? C14 C15 C5 120.96(13) . . ? C14 C15 H15 119.5 . . ? C5 C15 H15 119.5 . . ? C8 N1 C1 111.10(11) . . ? C8 N1 C1A 124.75(11) . . ? C1 N1 C1A 124.12(10) . . ? C4S O3S C5S 116.32(10) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C6 C1 C2 C3 1.85(19) . . . . ? N1 C1 C2 C3 -177.86(12) . . . . ? N1 C1A C2A C3A -170.77(11) . . . . ? C4S C1S C2S O1S 179.79(17) . . . . ? C11 C1S C2S O1S -1.7(3) . . . . ? C4S C1S C2S C3S -0.01(10) . . . . ? C11 C1S C2S C3S 178.54(19) . . . . ? C1 C2 C3 C4 -0.07(19) . . . . ? C1A C2A C3A C4A 67.22(16) . . . . ? O1S C2S C3S O2S -0.2(3) . . . . ? C1S C2S C3S O2S 179.65(16) . . . . ? O1S C2S C3S C4S -179.80(16) . . . . ? C1S C2S C3S C4S 0.01(10) . . . . ? C2 C3 C4 C12 178.06(12) . . . . ? C2 C3 C4 C5 -1.78(19) . . . . ? C2A C3A C4A C5A 170.15(12) . . . . ? C11 C1S C4S O3S 1.3(2) . . . . ? C2S C1S C4S O3S -179.72(13) . . . . ? C11 C1S C4S C3S -178.98(13) . . . . ? C2S C1S C4S C3S 0.01(11) . . . . ? O2S C3S C4S O3S 0.1(3) . . . . ? C2S C3S C4S O3S 179.68(16) . . . . ? O2S C3S C4S C1S -179.64(17) . . . . ? C2S C3S C4S C1S -0.01(10) . . . . ? C3 C4 C5 C6 1.89(18) . . . . ? C12 C4 C5 C6 -177.95(11) . . . . ? C3 C4 C5 C15 -179.30(12) . . . . ? C12 C4 C5 C15 0.86(18) . . . . ? C3A C4A C5A C6A -172.58(12) . . . . ? C2 C1 C6 C5 -1.70(19) . . . . ? N1 C1 C6 C5 178.06(11) . . . . ? C2 C1 C6 C7 178.13(11) . . . . ? N1 C1 C6 C7 -2.12(14) . . . . ? C15 C5 C6 C1 -178.94(12) . . . . ? C4 C5 C6 C1 -0.23(18) . . . . ? C15 C5 C6 C7 1.3(2) . . . . ? C4 C5 C6 C7 179.99(12) . . . . ? C4A C5A C6A C7A 173.50(12) . . . . ? C1 C6 C7 C8 2.00(13) . . . . ? C5 C6 C7 C8 -178.20(13) . . . . ? C1 C6 C7 C10 119.69(12) . . . . ? C5 C6 C7 C10 -60.51(18) . . . . ? C1 C6 C7 C9 -113.86(12) . . . . ? C5 C6 C7 C9 65.94(17) . . . . ? C5A C6A C7A C8A -168.85(12) . . . . ? C6 C7 C8 N1 -1.21(13) . . . . ? C10 C7 C8 N1 -120.94(11) . . . . ? C9 C7 C8 N1 116.32(11) . . . . ? C6 C7 C8 C11 179.06(13) . . . . ? C10 C7 C8 C11 59.32(18) . . . . ? C9 C7 C8 C11 -63.41(17) . . . . ? C6A C7A C8A C9A 179.66(12) . . . . ? C7A C8A C9A C10A 178.87(13) . . . . ? C8A C9A C10A C11A 175.05(14) . . . . ? N1 C8 C11 C1S 179.96(13) . . . . ? C7 C8 C11 C1S -0.3(2) . . . . ? C4S C1S C11 C8 -178.74(14) . . . . ? C2S C1S C11 C8 3.0(3) . . . . ? C9A C10A C11A C12A -179.41(15) . . . . ? C3 C4 C12 C13 -179.72(12) . . . . ? C5 C4 C12 C13 0.12(19) . . . . ? C4 C12 C13 C14 -1.1(2) . . . . ? C12 C13 C14 C15 1.1(2) . . . . ? C13 C14 C15 C5 0.0(2) . . . . ? C6 C5 C15 C14 177.80(13) . . . . ? C4 C5 C15 C14 -0.91(19) . . . . ? C11 C8 N1 C1 179.79(11) . . . . ? C7 C8 N1 C1 0.03(14) . . . . ? C11 C8 N1 C1A 1.90(19) . . . . ? C7 C8 N1 C1A -177.86(11) . . . . ? C6 C1 N1 C8 1.34(14) . . . . ? C2 C1 N1 C8 -178.92(12) . . . . ? C6 C1 N1 C1A 179.25(11) . . . . ? C2 C1 N1 C1A -1.0(2) . . . . ? C2A C1A N1 C8 78.46(15) . . . . ? C2A C1A N1 C1 -99.17(14) . . . . ? C1S C4S O3S C5S 179.15(13) . . . . ? C3S C4S O3S C5S -0.5(2) . . . . ? C6S C5S O3S C4S 169.57(11) . . . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 25.02 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.194 _refine_diff_density_min -0.182 _refine_diff_density_rms 0.039 _database_code_depnum_ccdc_archive 'CCDC 977423' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_6c _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C32 H41 N O3' _chemical_formula_weight 487.66 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 9.802(13) _cell_length_b 9.8259(10) _cell_length_c 15.69(2) _cell_angle_alpha 83.509(10) _cell_angle_beta 89.40(9) _cell_angle_gamma 66.40(6) _cell_volume 1375(3) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 250 _cell_measurement_theta_min 3.7 _cell_measurement_theta_max 27.2 _exptl_crystal_description Needle _exptl_crystal_colour Orange _exptl_crystal_size_max 0.14 _exptl_crystal_size_mid 0.02 _exptl_crystal_size_min 0.01 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.178 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 528 _exptl_absorpt_coefficient_mu 0.074 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.9897 _exptl_absorpt_correction_T_max 0.9993 _exptl_absorpt_process_details 'CrystalClear-SM Expert 3.1ba16 (Rigaku, 2012)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100 _diffrn_source_power 2.5 _diffrn_source_voltage 45.0 _diffrn_source_current 55.0 _diffrn_radiation_wavelength 0.71075 _diffrn_radiation_type 'Mo K\a' _diffrn_source 'Rotating Anode' _diffrn_radiation_monochromator Confocal _diffrn_measurement_specimen_support Mitegen _diffrn_detector CCD _diffrn_measurement_device ; AFC12 (Right): Kappa 3 circle ; _diffrn_measurement_device_type ; Rigaku Saturn724+ (2x2 bin mode) ; _diffrn_detector_area_resol_mean 28.5714 _diffrn_measurement_method 'profile data from \w-scans' _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 15659 _diffrn_reflns_av_R_equivalents 0.0554 _diffrn_reflns_av_sigmaI/netI 0.0601 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 3.26 _diffrn_reflns_theta_max 25.03 _reflns_number_total 4847 _reflns_number_gt 3510 _reflns_threshold_expression >2\s(I) _computing_data_collection 'CrystalClear-SM Expert 3.1ba16 (Rigaku, 2012)' _computing_cell_refinement 'CrystalClear-SM Expert 3.1ba16 (Rigaku, 2012)' _computing_data_reduction 'CrystalClear-SM Expert 3.1ba16 (Rigaku, 2012)' _computing_structure_solution 'SHELXL-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2\s(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0782P)^2^+1.1003P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4847 _refine_ls_number_parameters 329 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1169 _refine_ls_R_factor_gt 0.0848 _refine_ls_wR_factor_ref 0.2128 _refine_ls_wR_factor_gt 0.1943 _refine_ls_goodness_of_fit_ref 1.113 _refine_ls_restrained_S_all 1.113 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.6769(3) -0.0171(3) 0.1631(2) 0.0364(8) Uani 1 1 d . . . C1A C 0.5315(4) -0.1446(3) 0.0982(2) 0.0394(8) Uani 1 1 d . . . H1A1 H 0.6325 -0.2183 0.0879 0.047 Uiso 1 1 calc R . . H1A2 H 0.4745 -0.1116 0.0426 0.047 Uiso 1 1 calc R . . C1S C 0.1503(4) 0.2766(4) 0.1011(2) 0.0418(9) Uani 1 1 d . . . C2 C 0.8207(4) -0.1347(4) 0.1662(2) 0.0425(9) Uani 1 1 d . . . H2 H 0.8363 -0.2274 0.1462 0.051 Uiso 1 1 calc R . . C2A C 0.4551(4) -0.2208(4) 0.1600(2) 0.0437(9) Uani 1 1 d . . . H2A1 H 0.3496 -0.1516 0.1636 0.052 Uiso 1 1 calc R . . H2A2 H 0.4565 -0.3104 0.1361 0.052 Uiso 1 1 calc R . . C2S C 0.0738(4) 0.4314(4) 0.1231(2) 0.0531(11) Uani 1 1 d . . . C3 C 0.9355(4) -0.1100(4) 0.1990(2) 0.0447(9) Uani 1 1 d . . . H3 H 1.0327 -0.1873 0.2012 0.054 Uiso 1 1 calc R . . C3A C 0.5253(4) -0.2679(4) 0.2497(2) 0.0460(9) Uani 1 1 d . . . H3A1 H 0.5279 -0.1796 0.2732 0.055 Uiso 1 1 calc R . . H3A2 H 0.6293 -0.3416 0.2471 0.055 Uiso 1 1 calc R . . C3S C -0.0724(4) 0.4386(4) 0.0878(2) 0.0571(11) Uani 1 1 d . . . C4 C 0.9162(4) 0.0267(4) 0.2301(2) 0.0409(8) Uani 1 1 d . . . C4A C 0.4404(4) -0.3369(4) 0.3097(2) 0.0461(9) Uani 1 1 d . . . H4A1 H 0.3357 -0.2637 0.3102 0.055 Uiso 1 1 calc R . . H4A2 H 0.4397 -0.4257 0.2859 0.055 Uiso 1 1 calc R . . C4S C 0.0141(4) 0.2866(4) 0.0666(2) 0.0478(10) Uani 1 1 d . . . C5 C 0.7687(4) 0.1436(4) 0.2281(2) 0.0409(8) Uani 1 1 d . . . C5A C 0.5019(4) -0.3838(4) 0.4018(2) 0.0499(9) Uani 1 1 d . . . H5A1 H 0.6089 -0.4505 0.4012 0.060 Uiso 1 1 calc R . . H5A2 H 0.4503 -0.4424 0.4321 0.060 Uiso 1 1 calc R . . C5S C -0.1655(4) 0.2157(6) -0.0020(3) 0.093(2) Uani 1 1 d . . . H5S1 H -0.2380 0.2694 0.0389 0.140 Uiso 1 1 calc R . . H5S2 H -0.1739 0.1211 -0.0081 0.140 Uiso 1 1 calc R . . H5S3 H -0.1857 0.2771 -0.0579 0.140 Uiso 1 1 calc R . . C6 C 0.6505(3) 0.1181(3) 0.1927(2) 0.0381(8) Uani 1 1 d . . . C6A C 0.4859(4) -0.2547(4) 0.4525(2) 0.0478(9) Uani 1 1 d . . . H6A1 H 0.5471 -0.2961 0.5064 0.057 Uiso 1 1 calc R . . H6A2 H 0.5265 -0.1890 0.4187 0.057 Uiso 1 1 calc R . . C7 C 0.4853(3) 0.2193(3) 0.1779(2) 0.0359(8) Uani 1 1 d . . . C7A C 0.3271(4) -0.1603(4) 0.4745(2) 0.0476(9) Uani 1 1 d . . . H7A1 H 0.2902 -0.2238 0.5133 0.057 Uiso 1 1 calc R . . H7A2 H 0.2638 -0.1280 0.4212 0.057 Uiso 1 1 calc R . . C8 C 0.4269(4) 0.1197(3) 0.13485(19) 0.0358(8) Uani 1 1 d . . . C8A C 0.3078(4) -0.0216(4) 0.5173(2) 0.0446(9) Uani 1 1 d . . . H8A1 H 0.3683 -0.0537 0.5717 0.054 Uiso 1 1 calc R . . H8A2 H 0.3470 0.0409 0.4793 0.054 Uiso 1 1 calc R . . C9 C 0.4620(4) 0.3617(3) 0.1158(2) 0.0439(9) Uani 1 1 d . . . H9A H 0.4996 0.3331 0.0595 0.066 Uiso 1 1 calc R . . H9B H 0.5161 0.4153 0.1388 0.066 Uiso 1 1 calc R . . H9C H 0.3555 0.4266 0.1097 0.066 Uiso 1 1 calc R . . C9A C 0.1485(4) 0.0728(4) 0.5363(2) 0.0419(8) Uani 1 1 d . . . H9A1 H 0.1113 0.0117 0.5767 0.050 Uiso 1 1 calc R . . H9A2 H 0.0871 0.0999 0.4823 0.050 Uiso 1 1 calc R . . C10 C 0.4073(4) 0.2565(4) 0.2635(2) 0.0433(9) Uani 1 1 d . . . H10A H 0.3018 0.3214 0.2518 0.065 Uiso 1 1 calc R . . H10B H 0.4546 0.3079 0.2949 0.065 Uiso 1 1 calc R . . H10C H 0.4162 0.1637 0.2982 0.065 Uiso 1 1 calc R . . C10A C 0.1264(4) 0.2157(4) 0.5744(2) 0.0412(8) Uani 1 1 d . . . H10D H 0.1791 0.1887 0.6313 0.049 Uiso 1 1 calc R . . H10E H 0.1723 0.2725 0.5370 0.049 Uiso 1 1 calc R . . C11 C 0.2871(4) 0.1493(3) 0.1040(2) 0.0381(8) Uani 1 1 d . . . H11 H 0.2799 0.0682 0.0795 0.046 Uiso 1 1 calc R . . C11A C -0.0363(4) 0.3161(4) 0.5848(2) 0.0461(9) Uani 1 1 d . . . H11A H -0.0889 0.3434 0.5279 0.055 Uiso 1 1 calc R . . H11B H -0.0823 0.2591 0.6220 0.055 Uiso 1 1 calc R . . C12 C 1.0368(4) 0.0511(4) 0.2630(2) 0.0495(10) Uani 1 1 d . . . H12 H 1.1343 -0.0254 0.2634 0.059 Uiso 1 1 calc R . . C13 C 1.0170(4) 0.1815(4) 0.2942(2) 0.0493(9) Uani 1 1 d . . . H13 H 1.0999 0.1952 0.3161 0.059 Uiso 1 1 calc R . . C13A C -0.0587(5) 0.4580(4) 0.6230(3) 0.0594(11) Uani 1 1 d . . . H13A H -0.0099 0.4321 0.6803 0.089 Uiso 1 1 calc R . . H13B H -0.1655 0.5175 0.6275 0.089 Uiso 1 1 calc R . . H13C H -0.0152 0.5162 0.5861 0.089 Uiso 1 1 calc R . . C14 C 0.8728(4) 0.2957(4) 0.2938(2) 0.0511(9) Uani 1 1 d . . . H14 H 0.8591 0.3857 0.3165 0.061 Uiso 1 1 calc R . . C15 C 0.7522(4) 0.2790(4) 0.2614(2) 0.0467(9) Uani 1 1 d . . . H15 H 0.6563 0.3581 0.2609 0.056 Uiso 1 1 calc R . . N1 N 0.5441(3) -0.0151(3) 0.12988(16) 0.0356(6) Uani 1 1 d . . . O1S O 0.1095(3) 0.5204(3) 0.15617(17) 0.0613(8) Uani 1 1 d . . . O2S O -0.2020(3) 0.5296(3) 0.08135(17) 0.0711(9) Uani 1 1 d . . . O3S O -0.0108(3) 0.1842(3) 0.03045(17) 0.0541(7) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0343(18) 0.0295(16) 0.0295(17) 0.0021(13) 0.0087(14) 0.0023(14) C1A 0.0414(19) 0.0290(16) 0.0302(17) -0.0027(13) 0.0095(14) 0.0037(14) C1S 0.0389(19) 0.0352(18) 0.0301(17) 0.0058(14) 0.0124(15) 0.0044(15) C2 0.0383(19) 0.0358(18) 0.0326(18) 0.0012(14) 0.0096(15) 0.0053(15) C2A 0.052(2) 0.0295(17) 0.0369(19) -0.0040(14) 0.0075(16) -0.0029(16) C2S 0.060(2) 0.035(2) 0.034(2) 0.0007(16) 0.0178(18) 0.0103(18) C3 0.0352(19) 0.041(2) 0.0368(19) 0.0045(15) 0.0091(16) 0.0034(15) C3A 0.047(2) 0.0386(19) 0.041(2) 0.0005(15) 0.0068(16) -0.0062(16) C3S 0.042(2) 0.054(2) 0.038(2) 0.0159(17) 0.0147(17) 0.0142(18) C4 0.0340(18) 0.043(2) 0.0301(18) 0.0059(15) 0.0089(15) -0.0027(15) C4A 0.057(2) 0.0340(18) 0.0373(19) -0.0021(15) 0.0086(17) -0.0091(17) C4S 0.0334(19) 0.045(2) 0.0345(19) 0.0121(16) 0.0126(16) 0.0107(16) C5 0.0391(19) 0.0371(18) 0.0297(17) 0.0073(14) 0.0124(15) -0.0009(15) C5A 0.055(2) 0.045(2) 0.041(2) 0.0019(16) 0.0044(18) -0.0121(18) C5S 0.0179(18) 0.155(5) 0.046(2) 0.045(3) 0.0002(17) 0.015(2) C6 0.0329(18) 0.0334(17) 0.0333(18) 0.0038(14) 0.0079(14) -0.0003(14) C6A 0.047(2) 0.051(2) 0.038(2) 0.0019(17) 0.0045(16) -0.0140(18) C7 0.0331(17) 0.0305(16) 0.0287(17) 0.0003(13) 0.0061(14) 0.0021(14) C7A 0.049(2) 0.054(2) 0.041(2) -0.0071(17) 0.0062(17) -0.0228(18) C8 0.0380(18) 0.0259(15) 0.0278(16) 0.0008(13) 0.0117(14) 0.0022(14) C8A 0.042(2) 0.058(2) 0.0368(19) -0.0067(17) 0.0053(16) -0.0227(18) C9 0.0400(19) 0.0317(17) 0.042(2) 0.0036(15) 0.0062(16) 0.0018(15) C9A 0.0422(19) 0.053(2) 0.0341(18) -0.0064(16) 0.0061(15) -0.0223(17) C10 0.0420(19) 0.0357(18) 0.0357(19) -0.0034(15) 0.0098(15) 0.0012(15) C10A 0.0429(19) 0.055(2) 0.0301(18) -0.0044(16) 0.0035(15) -0.0241(17) C11 0.0374(19) 0.0274(16) 0.0326(18) -0.0008(13) 0.0109(15) 0.0035(14) C11A 0.046(2) 0.053(2) 0.038(2) -0.0055(17) 0.0082(16) -0.0195(18) C12 0.039(2) 0.052(2) 0.039(2) 0.0084(17) 0.0127(16) -0.0029(17) C13 0.043(2) 0.056(2) 0.043(2) 0.0092(18) 0.0059(17) -0.0169(18) C13A 0.067(3) 0.059(2) 0.051(2) -0.012(2) 0.016(2) -0.022(2) C14 0.049(2) 0.048(2) 0.047(2) 0.0025(17) 0.0071(18) -0.0115(18) C15 0.042(2) 0.044(2) 0.044(2) 0.0017(16) 0.0070(17) -0.0076(17) N1 0.0309(14) 0.0264(13) 0.0317(14) 0.0000(11) 0.0079(12) 0.0059(11) O1S 0.0626(18) 0.0427(15) 0.0466(16) -0.0024(13) 0.0127(13) 0.0110(13) O2S 0.0473(16) 0.0601(17) 0.0559(17) 0.0156(14) 0.0161(13) 0.0244(13) O3S 0.0327(13) 0.0597(17) 0.0500(16) 0.0063(13) 0.0018(12) -0.0013(12) _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C6 1.381(4) . ? C1 N1 1.400(5) . ? C1 C2 1.418(5) . ? C1A N1 1.466(4) . ? C1A C2A 1.527(5) . ? C1A H1A1 0.9900 . ? C1A H1A2 0.9900 . ? C1S C4S 1.408(5) . ? C1S C11 1.417(4) . ? C1S C2S 1.481(5) . ? C2 C3 1.359(5) . ? C2 H2 0.9500 . ? C2A C3A 1.512(5) . ? C2A H2A1 0.9900 . ? C2A H2A2 0.9900 . ? C2S O1S 1.229(5) . ? C2S C3S 1.513(6) . ? C2S C4S 2.027(7) . ? C3 C4 1.421(5) . ? C3 H3 0.9500 . ? C3A C4A 1.527(5) . ? C3A H3A1 0.9900 . ? C3A H3A2 0.9900 . ? C3S O2S 1.223(4) . ? C3S C4S 1.467(5) . ? C4 C12 1.410(5) . ? C4 C5 1.440(5) . ? C4A C5A 1.519(5) . ? C4A H4A1 0.9900 . ? C4A H4A2 0.9900 . ? C4S O3S 1.313(5) . ? C5 C6 1.412(5) . ? C5 C15 1.432(5) . ? C5A C6A 1.527(5) . ? C5A H5A1 0.9900 . ? C5A H5A2 0.9900 . ? C5S O3S 1.503(5) . ? C5S H5S1 0.9800 . ? C5S H5S2 0.9800 . ? C5S H5S3 0.9800 . ? C6 C7 1.527(5) . ? C6A C7A 1.519(5) . ? C6A H6A1 0.9900 . ? C6A H6A2 0.9900 . ? C7 C8 1.532(5) . ? C7 C10 1.546(4) . ? C7 C9 1.549(4) . ? C7A C8A 1.530(5) . ? C7A H7A1 0.9900 . ? C7A H7A2 0.9900 . ? C8 C11 1.365(5) . ? C8 N1 1.372(4) . ? C8A C9A 1.510(5) . ? C8A H8A1 0.9900 . ? C8A H8A2 0.9900 . ? C9 H9A 0.9800 . ? C9 H9B 0.9800 . ? C9 H9C 0.9800 . ? C9A C10A 1.524(5) . ? C9A H9A1 0.9900 . ? C9A H9A2 0.9900 . ? C10 H10A 0.9800 . ? C10 H10B 0.9800 . ? C10 H10C 0.9800 . ? C10A C11A 1.521(5) . ? C10A H10D 0.9900 . ? C10A H10E 0.9900 . ? C11 H11 0.9500 . ? C11A C13A 1.515(5) . ? C11A H11A 0.9900 . ? C11A H11B 0.9900 . ? C12 C13 1.364(5) . ? C12 H12 0.9500 . ? C13 C14 1.409(5) . ? C13 H13 0.9500 . ? C13A H13A 0.9800 . ? C13A H13B 0.9800 . ? C13A H13C 0.9800 . ? C14 C15 1.368(5) . ? C14 H14 0.9500 . ? C15 H15 0.9500 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C6 C1 N1 109.8(3) . . ? C6 C1 C2 122.6(3) . . ? N1 C1 C2 127.6(3) . . ? N1 C1A C2A 113.4(2) . . ? N1 C1A H1A1 108.9 . . ? C2A C1A H1A1 108.9 . . ? N1 C1A H1A2 108.9 . . ? C2A C1A H1A2 108.9 . . ? H1A1 C1A H1A2 107.7 . . ? C4S C1S C11 125.1(3) . . ? C4S C1S C2S 89.1(3) . . ? C11 C1S C2S 145.8(4) . . ? C3 C2 C1 117.5(3) . . ? C3 C2 H2 121.3 . . ? C1 C2 H2 121.3 . . ? C3A C2A C1A 114.4(3) . . ? C3A C2A H2A1 108.7 . . ? C1A C2A H2A1 108.7 . . ? C3A C2A H2A2 108.7 . . ? C1A C2A H2A2 108.7 . . ? H2A1 C2A H2A2 107.6 . . ? O1S C2S C1S 136.4(4) . . ? O1S C2S C3S 133.5(3) . . ? C1S C2S C3S 90.1(3) . . ? O1S C2S C4S 179.1(3) . . ? C1S C2S C4S 44.0(2) . . ? C3S C2S C4S 46.2(2) . . ? C2 C3 C4 122.8(3) . . ? C2 C3 H3 118.6 . . ? C4 C3 H3 118.6 . . ? C2A C3A C4A 112.2(3) . . ? C2A C3A H3A1 109.2 . . ? C4A C3A H3A1 109.2 . . ? C2A C3A H3A2 109.2 . . ? C4A C3A H3A2 109.2 . . ? H3A1 C3A H3A2 107.9 . . ? O2S C3S C4S 137.8(4) . . ? O2S C3S C2S 136.5(4) . . ? C4S C3S C2S 85.7(3) . . ? C12 C4 C3 122.1(3) . . ? C12 C4 C5 119.0(3) . . ? C3 C4 C5 118.9(3) . . ? C5A C4A C3A 115.4(3) . . ? C5A C4A H4A1 108.4 . . ? C3A C4A H4A1 108.4 . . ? C5A C4A H4A2 108.4 . . ? C3A C4A H4A2 108.4 . . ? H4A1 C4A H4A2 107.5 . . ? O3S C4S C1S 127.6(3) . . ? O3S C4S C3S 137.4(4) . . ? C1S C4S C3S 95.0(3) . . ? O3S C4S C2S 174.5(3) . . ? C1S C4S C2S 46.9(2) . . ? C3S C4S C2S 48.1(2) . . ? C6 C5 C15 124.3(3) . . ? C6 C5 C4 118.0(3) . . ? C15 C5 C4 117.7(3) . . ? C4A C5A C6A 114.8(3) . . ? C4A C5A H5A1 108.6 . . ? C6A C5A H5A1 108.6 . . ? C4A C5A H5A2 108.6 . . ? C6A C5A H5A2 108.6 . . ? H5A1 C5A H5A2 107.5 . . ? O3S C5S H5S1 109.5 . . ? O3S C5S H5S2 109.5 . . ? H5S1 C5S H5S2 109.5 . . ? O3S C5S H5S3 109.5 . . ? H5S1 C5S H5S3 109.5 . . ? H5S2 C5S H5S3 109.5 . . ? C1 C6 C5 120.2(3) . . ? C1 C6 C7 108.7(3) . . ? C5 C6 C7 131.0(3) . . ? C7A C6A C5A 114.6(3) . . ? C7A C6A H6A1 108.6 . . ? C5A C6A H6A1 108.6 . . ? C7A C6A H6A2 108.6 . . ? C5A C6A H6A2 108.6 . . ? H6A1 C6A H6A2 107.6 . . ? C6 C7 C8 101.8(3) . . ? C6 C7 C10 111.6(3) . . ? C8 C7 C10 109.5(3) . . ? C6 C7 C9 111.3(3) . . ? C8 C7 C9 109.8(3) . . ? C10 C7 C9 112.3(3) . . ? C6A C7A C8A 115.0(3) . . ? C6A C7A H7A1 108.5 . . ? C8A C7A H7A1 108.5 . . ? C6A C7A H7A2 108.5 . . ? C8A C7A H7A2 108.5 . . ? H7A1 C7A H7A2 107.5 . . ? C11 C8 N1 122.1(3) . . ? C11 C8 C7 129.9(3) . . ? N1 C8 C7 108.0(3) . . ? C9A C8A C7A 114.0(3) . . ? C9A C8A H8A1 108.7 . . ? C7A C8A H8A1 108.7 . . ? C9A C8A H8A2 108.7 . . ? C7A C8A H8A2 108.7 . . ? H8A1 C8A H8A2 107.6 . . ? C7 C9 H9A 109.5 . . ? C7 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? C7 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? C8A C9A C10A 114.7(3) . . ? C8A C9A H9A1 108.6 . . ? C10A C9A H9A1 108.6 . . ? C8A C9A H9A2 108.6 . . ? C10A C9A H9A2 108.6 . . ? H9A1 C9A H9A2 107.6 . . ? C7 C10 H10A 109.5 . . ? C7 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? C7 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? C11A C10A C9A 113.6(3) . . ? C11A C10A H10D 108.8 . . ? C9A C10A H10D 108.8 . . ? C11A C10A H10E 108.8 . . ? C9A C10A H10E 108.8 . . ? H10D C10A H10E 107.7 . . ? C8 C11 C1S 133.0(3) . . ? C8 C11 H11 113.5 . . ? C1S C11 H11 113.5 . . ? C13A C11A C10A 113.7(3) . . ? C13A C11A H11A 108.8 . . ? C10A C11A H11A 108.8 . . ? C13A C11A H11B 108.8 . . ? C10A C11A H11B 108.8 . . ? H11A C11A H11B 107.7 . . ? C13 C12 C4 121.7(3) . . ? C13 C12 H12 119.1 . . ? C4 C12 H12 119.1 . . ? C12 C13 C14 119.7(4) . . ? C12 C13 H13 120.2 . . ? C14 C13 H13 120.2 . . ? C11A C13A H13A 109.5 . . ? C11A C13A H13B 109.5 . . ? H13A C13A H13B 109.5 . . ? C11A C13A H13C 109.5 . . ? H13A C13A H13C 109.5 . . ? H13B C13A H13C 109.5 . . ? C15 C14 C13 121.1(4) . . ? C15 C14 H14 119.5 . . ? C13 C14 H14 119.5 . . ? C14 C15 C5 120.8(3) . . ? C14 C15 H15 119.6 . . ? C5 C15 H15 119.6 . . ? C8 N1 C1 111.6(3) . . ? C8 N1 C1A 124.6(3) . . ? C1 N1 C1A 123.7(2) . . ? C4S O3S C5S 119.7(3) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C6 C1 C2 C3 -0.8(5) . . . . ? N1 C1 C2 C3 177.8(3) . . . . ? N1 C1A C2A C3A -54.8(4) . . . . ? C4S C1S C2S O1S -178.8(4) . . . . ? C11 C1S C2S O1S 2.1(8) . . . . ? C4S C1S C2S C3S 1.4(2) . . . . ? C11 C1S C2S C3S -177.8(5) . . . . ? C11 C1S C2S C4S -179.1(6) . . . . ? C1 C2 C3 C4 0.4(5) . . . . ? C1A C2A C3A C4A 177.4(3) . . . . ? O1S C2S C3S O2S -1.7(7) . . . . ? C1S C2S C3S O2S 178.1(4) . . . . ? C4S C2S C3S O2S 179.5(5) . . . . ? O1S C2S C3S C4S 178.8(4) . . . . ? C1S C2S C3S C4S -1.3(2) . . . . ? C2 C3 C4 C12 -179.3(3) . . . . ? C2 C3 C4 C5 1.0(5) . . . . ? C2A C3A C4A C5A -178.6(3) . . . . ? C11 C1S C4S O3S -1.3(5) . . . . ? C2S C1S C4S O3S 179.3(3) . . . . ? C11 C1S C4S C3S 178.0(3) . . . . ? C2S C1S C4S C3S -1.4(3) . . . . ? C11 C1S C4S C2S 179.4(4) . . . . ? O2S C3S C4S O3S 1.1(8) . . . . ? C2S C3S C4S O3S -179.4(4) . . . . ? O2S C3S C4S C1S -178.0(4) . . . . ? C2S C3S C4S C1S 1.4(3) . . . . ? O2S C3S C4S C2S -179.4(6) . . . . ? O1S C2S C4S O3S 106(19) . . . . ? C1S C2S C4S O3S -6(3) . . . . ? C3S C2S C4S O3S 176(3) . . . . ? O1S C2S C4S C1S 112(20) . . . . ? C3S C2S C4S C1S -178.1(3) . . . . ? O1S C2S C4S C3S -70(20) . . . . ? C1S C2S C4S C3S 178.1(3) . . . . ? C12 C4 C5 C6 178.3(3) . . . . ? C3 C4 C5 C6 -2.0(4) . . . . ? C12 C4 C5 C15 -0.9(4) . . . . ? C3 C4 C5 C15 178.8(3) . . . . ? C3A C4A C5A C6A 68.1(4) . . . . ? N1 C1 C6 C5 -179.1(3) . . . . ? C2 C1 C6 C5 -0.3(5) . . . . ? N1 C1 C6 C7 0.0(3) . . . . ? C2 C1 C6 C7 178.8(3) . . . . ? C15 C5 C6 C1 -179.2(3) . . . . ? C4 C5 C6 C1 1.6(4) . . . . ? C15 C5 C6 C7 2.0(5) . . . . ? C4 C5 C6 C7 -177.2(3) . . . . ? C4A C5A C6A C7A 70.2(4) . . . . ? C1 C6 C7 C8 -0.8(3) . . . . ? C5 C6 C7 C8 178.2(3) . . . . ? C1 C6 C7 C10 116.0(3) . . . . ? C5 C6 C7 C10 -65.1(4) . . . . ? C1 C6 C7 C9 -117.7(3) . . . . ? C5 C6 C7 C9 61.2(4) . . . . ? C5A C6A C7A C8A -174.1(3) . . . . ? C6 C7 C8 C11 -178.0(3) . . . . ? C10 C7 C8 C11 63.7(4) . . . . ? C9 C7 C8 C11 -60.0(4) . . . . ? C6 C7 C8 N1 1.3(3) . . . . ? C10 C7 C8 N1 -117.0(3) . . . . ? C9 C7 C8 N1 119.3(3) . . . . ? C6A C7A C8A C9A 178.3(3) . . . . ? C7A C8A C9A C10A -176.9(3) . . . . ? C8A C9A C10A C11A 174.3(3) . . . . ? N1 C8 C11 C1S -179.8(3) . . . . ? C7 C8 C11 C1S -0.6(6) . . . . ? C4S C1S C11 C8 -179.4(3) . . . . ? C2S C1S C11 C8 -0.5(8) . . . . ? C9A C10A C11A C13A 179.8(3) . . . . ? C3 C4 C12 C13 -178.7(3) . . . . ? C5 C4 C12 C13 1.0(5) . . . . ? C4 C12 C13 C14 -0.1(5) . . . . ? C12 C13 C14 C15 -1.0(5) . . . . ? C13 C14 C15 C5 1.1(5) . . . . ? C6 C5 C15 C14 -179.3(3) . . . . ? C4 C5 C15 C14 -0.1(5) . . . . ? C11 C8 N1 C1 178.0(3) . . . . ? C7 C8 N1 C1 -1.4(3) . . . . ? C11 C8 N1 C1A -5.2(5) . . . . ? C7 C8 N1 C1A 175.5(2) . . . . ? C6 C1 N1 C8 0.9(3) . . . . ? C2 C1 N1 C8 -177.8(3) . . . . ? C6 C1 N1 C1A -176.0(3) . . . . ? C2 C1 N1 C1A 5.3(5) . . . . ? C2A C1A N1 C8 -72.0(4) . . . . ? C2A C1A N1 C1 104.4(3) . . . . ? C1S C4S O3S C5S 179.5(3) . . . . ? C3S C4S O3S C5S 0.5(6) . . . . ? C2S C4S O3S C5S -175(3) . . . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 25.03 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.593 _refine_diff_density_min -0.330 _refine_diff_density_rms 0.049 _database_code_depnum_ccdc_archive 'CCDC 977424' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_8salt _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C68 H76 N6 Na2 O7' _chemical_formula_weight 1135.33 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0032 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0032 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0058 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Na Na 0.0348 0.0240 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 11.9454(11) _cell_length_b 12.4652(11) _cell_length_c 24.378(2) _cell_angle_alpha 90.54(2) _cell_angle_beta 101.50(2) _cell_angle_gamma 118.10(3) _cell_volume 3115.3(5) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 14357 _cell_measurement_theta_min 1.9 _cell_measurement_theta_max 26.6 _exptl_crystal_description fragment _exptl_crystal_colour Orange _exptl_crystal_size_max 0.05 _exptl_crystal_size_mid 0.05 _exptl_crystal_size_min 0.03 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.210 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1208 _exptl_absorpt_coefficient_mu 0.084 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9958 _exptl_absorpt_correction_T_max 0.9975 _exptl_absorpt_process_details 'CrystalClear-SM Expert 3.1 b27 (Rigaku, 2012)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_source_type 'DLS beamline I19' _diffrn_source synchrotron _diffrn_radiation_type synchrotron _diffrn_radiation_wavelength 0.68890 _diffrn_radiation_collimation 'Confocal mirrors' _diffrn_radiation_monochromator 'double crystal silicon' _diffrn_detector 'CCD plate' _diffrn_detector_type 'Rigaku Saturn724+ (2x2 bin mode)' _diffrn_detector_area_resol_mean 28.5714 _diffrn_measurement_device 'four-circle \k goniometer' _diffrn_measurement_device_type CrystalLogic _diffrn_measurement_method 'profile data from \w-scans' _diffrn_measurement_specimen_support 'MiTeGen MicroLoop' _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 22317 _diffrn_reflns_av_R_equivalents 0.2525 _diffrn_reflns_av_sigmaI/netI 0.2681 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -29 _diffrn_reflns_limit_l_max 28 _diffrn_reflns_theta_min 2.90 _diffrn_reflns_theta_max 24.21 _reflns_number_total 10395 _reflns_number_gt 2921 _reflns_threshold_expression >2\s(I) _computing_data_collection 'CrystalClear-SM Expert 3.1 b27 (Rigaku, 2012)' _computing_cell_refinement 'CrystalClear-SM Expert 3.1 b27 (Rigaku, 2012)' _computing_data_reduction 'CrystalClear-SM Expert 3.1 b27 (Rigaku, 2012)' _computing_structure_solution 'SHELXL-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; In the crystal structure long aliphatic chain is disordered and was modelled over two sites with 50:50 ratio. For disordered components vibrational restraints (SIMU/DELU) and distance/angle restraints DFIX/DANG used to maintain sensible geometries and atomic displacement ellipsoids. Due to poor quality of the weakly diffracting crystals of 8_salt the X-ray data were collected with the use of synchrotron radiation at Diamond Light Source UK, beamline I19 (wavelength=0.6889 Ang) Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2\s(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.2000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.050(8) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 10395 _refine_ls_number_parameters 863 _refine_ls_number_restraints 1005 _refine_ls_R_factor_all 0.3242 _refine_ls_R_factor_gt 0.1277 _refine_ls_wR_factor_ref 0.4276 _refine_ls_wR_factor_gt 0.3028 _refine_ls_goodness_of_fit_ref 0.993 _refine_ls_restrained_S_all 0.963 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.1468(9) 0.8633(10) -0.1486(4) 0.073(2) Uani 1 1 d U . . C2 C 0.1128(11) 0.9418(10) -0.1774(4) 0.088(3) Uani 1 1 d U . . H2 H 0.0242 0.9238 -0.1871 0.106 Uiso 1 1 calc R . . C3 C 0.2071(11) 1.0461(11) -0.1922(4) 0.091(3) Uani 1 1 d U . . H3 H 0.1838 1.1008 -0.2118 0.109 Uiso 1 1 calc R . . C4 C 0.3394(11) 1.0726(10) -0.1782(4) 0.082(3) Uani 1 1 d U . . C12 C 0.4386(12) 1.1833(11) -0.1926(5) 0.096(3) Uani 1 1 d U . . H12 H 0.4164 1.2401 -0.2106 0.115 Uiso 1 1 calc R . . C13 C 0.5649(12) 1.2060(11) -0.1800(5) 0.097(3) Uani 1 1 d U . . H13 H 0.6307 1.2786 -0.1898 0.117 Uiso 1 1 calc R . . C14 C 0.5973(11) 1.1243(10) -0.1533(4) 0.087(3) Uani 1 1 d U . . H14 H 0.6862 1.1431 -0.1448 0.105 Uiso 1 1 calc R . . C15 C 0.5091(9) 1.0188(9) -0.1384(4) 0.075(2) Uani 1 1 d U . . H15 H 0.5354 0.9643 -0.1205 0.090 Uiso 1 1 calc R . . C5 C 0.3739(10) 0.9903(9) -0.1504(4) 0.077(2) Uani 1 1 d U . . C6 C 0.2745(9) 0.8836(9) -0.1367(4) 0.070(2) Uani 1 1 d U . . C7 C 0.2790(8) 0.7744(9) -0.1102(4) 0.067(2) Uani 1 1 d U . . C9 C 0.3637(9) 0.8066(9) -0.0515(4) 0.076(3) Uani 1 1 d U . . H9A H 0.4553 0.8566 -0.0530 0.113 Uiso 1 1 calc R . . H9B H 0.3518 0.7313 -0.0353 0.113 Uiso 1 1 calc R . . H9C H 0.3394 0.8527 -0.0281 0.113 Uiso 1 1 calc R . . C10 C 0.3105(9) 0.7065(9) -0.1532(4) 0.073(3) Uani 1 1 d U . . H10A H 0.3996 0.7587 -0.1575 0.110 Uiso 1 1 calc R . . H10B H 0.2489 0.6878 -0.1897 0.110 Uiso 1 1 calc R . . H10C H 0.3030 0.6302 -0.1396 0.110 Uiso 1 1 calc R . . C8 C 0.1318(8) 0.6925(9) -0.1092(4) 0.066(2) Uani 1 1 d U . . C11 C 0.0736(8) 0.5832(9) -0.0913(4) 0.067(2) Uani 1 1 d U . . H11 H -0.0170 0.5537 -0.0948 0.081 Uiso 1 1 calc R . . C1S C 0.1156(7) 0.5001(9) -0.0680(3) 0.063(2) Uani 1 1 d U . . C2S C 0.2343(8) 0.4859(9) -0.0549(4) 0.072(3) Uani 1 1 d U . . C3S C 0.1581(8) 0.3717(9) -0.0322(4) 0.063(2) Uani 1 1 d U . . C4S C 0.0435(7) 0.3867(8) -0.0485(4) 0.063(2) Uani 1 1 d U . . C5S C -0.0880(8) 0.3148(9) -0.0462(4) 0.064(2) Uani 1 1 d U . . C6S C -0.1791(8) 0.3593(9) -0.0584(4) 0.070(3) Uani 1 1 d U . . C7S C -0.1324(8) 0.1972(10) -0.0266(4) 0.059(2) Uani 1 1 d U . . C1A C -0.0758(9) 0.7032(10) -0.1382(4) 0.085(3) Uani 1 1 d U . . H1A1 H -0.0951 0.7723 -0.1390 0.102 Uiso 1 1 calc R . . H1A2 H -0.1036 0.6596 -0.1056 0.102 Uiso 1 1 calc R . . C2A C -0.1524(12) 0.6150(12) -0.1930(6) 0.128(4) Uani 1 1 d U . . H2A1 H -0.1057 0.6525 -0.2229 0.154 Uiso 1 1 calc R . . H2A2 H -0.1470 0.5390 -0.1873 0.154 Uiso 1 1 calc R . . C3A C -0.2825(15) 0.5812(16) -0.2141(7) 0.160(6) Uani 1 1 d U . . H3A1 H -0.2907 0.6565 -0.2163 0.192 Uiso 1 1 calc R . . H3A2 H -0.3324 0.5340 -0.1868 0.192 Uiso 1 1 calc R . . C4A C -0.3468(19) 0.5035(15) -0.2731(7) 0.183(7) Uani 1 1 d U . . H4A1 H -0.2960 0.5506 -0.3001 0.220 Uiso 1 1 calc R . . H4A2 H -0.3386 0.4282 -0.2706 0.220 Uiso 1 1 calc R . . C5A C -0.479(2) 0.4686(18) -0.2955(7) 0.188(7) Uani 1 1 d U . . H5A1 H -0.4878 0.5435 -0.2996 0.226 Uiso 1 1 calc R . . H5A2 H -0.5305 0.4230 -0.2683 0.226 Uiso 1 1 calc R . . C6A C -0.536(2) 0.3920(18) -0.3506(8) 0.187(7) Uani 1 1 d U . . H6A1 H -0.4816 0.4367 -0.3769 0.224 Uiso 1 1 calc R . . H6A2 H -0.5293 0.3165 -0.3458 0.224 Uiso 1 1 calc R . . C7A C -0.671(2) 0.356(2) -0.3774(8) 0.222(8) Uani 1 1 d U . . H7A1 H -0.7264 0.3037 -0.3529 0.267 Uiso 1 1 calc R . . H7A2 H -0.6799 0.4310 -0.3785 0.267 Uiso 1 1 calc R . . C8A C -0.720(2) 0.293(2) -0.4323(9) 0.260(10) Uani 1 1 d U . . H8A1 H -0.7207 0.2138 -0.4310 0.312 Uiso 1 1 calc R . . H8A2 H -0.6612 0.3415 -0.4564 0.312 Uiso 1 1 calc R . . C9A C -0.870(3) 0.267(3) -0.4619(12) 0.275(11) Uani 1 1 d U . . H9A1 H -0.8746 0.3423 -0.4526 0.330 Uiso 1 1 calc R . . H9A2 H -0.8807 0.2568 -0.5033 0.330 Uiso 1 1 calc R . . C10A C -0.975(3) 0.171(3) -0.4492(10) 0.244(9) Uani 1 1 d U . . H10D H -0.9675 0.1825 -0.4082 0.293 Uiso 1 1 calc R . . H10E H -0.9702 0.0956 -0.4574 0.293 Uiso 1 1 calc R . . C11A C -1.103(2) 0.153(3) -0.4788(11) 0.241(10) Uani 1 1 d U . . H11A H -1.1090 0.2266 -0.4689 0.290 Uiso 1 1 calc R . . H11B H -1.1079 0.1461 -0.5198 0.290 Uiso 1 1 calc R . . C12A C -1.199(3) 0.062(3) -0.4694(17) 0.37(2) Uani 1 1 d U . . H12A H -1.2757 0.0423 -0.4999 0.556 Uiso 1 1 calc R . . H12B H -1.2154 0.0804 -0.4335 0.556 Uiso 1 1 calc R . . H12C H -1.1828 -0.0078 -0.4675 0.556 Uiso 1 1 calc R . . C101 C -0.1739(10) 0.3065(13) -0.3484(5) 0.118(4) Uani 1 1 d U A . C102 C -0.2351(11) 0.3401(15) -0.3970(5) 0.145(6) Uani 1 1 d U . . H102 H -0.3271 0.2995 -0.4110 0.174 Uiso 1 1 calc R . . C103 C -0.1540(12) 0.4330(13) -0.4218(5) 0.125(5) Uani 1 1 d U . . H103 H -0.1907 0.4566 -0.4545 0.151 Uiso 1 1 calc R . . C104 C -0.0195(11) 0.4955(11) -0.4014(5) 0.098(3) Uani 1 1 d U . . C112 C 0.0602(12) 0.5867(11) -0.4308(5) 0.112(4) Uani 1 1 d U . . H112 H 0.0226 0.6062 -0.4647 0.134 Uiso 1 1 calc R . . C113 C 0.1910(13) 0.6463(13) -0.4104(5) 0.128(5) Uani 1 1 d U . . H113 H 0.2451 0.7058 -0.4309 0.154 Uiso 1 1 calc R . . C114 C 0.2482(13) 0.6217(14) -0.3595(6) 0.139(5) Uani 1 1 d U . . H114 H 0.3399 0.6677 -0.3450 0.167 Uiso 1 1 calc R . . C115 C 0.1741(11) 0.5333(11) -0.3308(5) 0.106(4) Uani 1 1 d U . . H115 H 0.2146 0.5175 -0.2965 0.127 Uiso 1 1 calc R . . C105 C 0.0387(10) 0.4647(10) -0.3507(4) 0.087(3) Uani 1 1 d U . . C106 C -0.0466(10) 0.3638(10) -0.3248(4) 0.084(3) Uani 1 1 d U . . C107 C -0.0166(9) 0.3093(10) -0.2732(4) 0.076(2) Uani 1 1 d U . . C110 C 0.0800(9) 0.2616(10) -0.2765(4) 0.082(3) Uani 1 1 d U . . H11C H 0.0524 0.2113 -0.3128 0.123 Uiso 1 1 calc R . . H11D H 0.0817 0.2120 -0.2457 0.123 Uiso 1 1 calc R . . H11E H 0.1674 0.3311 -0.2732 0.123 Uiso 1 1 calc R . . C109 C 0.0280(12) 0.3966(11) -0.2197(4) 0.100(3) Uani 1 1 d U . . H10F H 0.1132 0.4671 -0.2191 0.150 Uiso 1 1 calc R . . H10G H 0.0350 0.3540 -0.1867 0.150 Uiso 1 1 calc R . . H10H H -0.0356 0.4250 -0.2189 0.150 Uiso 1 1 calc R . . C108 C -0.1501(9) 0.2030(11) -0.2743(4) 0.097(3) Uani 1 1 d U A . C111 C -0.1885(9) 0.1103(11) -0.2403(4) 0.097(4) Uani 1 1 d U . . H111 H -0.2772 0.0489 -0.2526 0.117 Uiso 1 1 calc R . . C21S C -0.1196(8) 0.0890(9) -0.1898(4) 0.070(2) Uani 1 1 d U . . C22S C 0.0037(9) 0.1373(9) -0.1486(4) 0.066(2) Uani 1 1 d U . . C23S C -0.0614(8) 0.0341(8) -0.1148(4) 0.062(2) Uani 1 1 d U . . C24S C -0.1778(8) -0.0120(9) -0.1593(4) 0.069(2) Uani 1 1 d U . . C25S C -0.2978(9) -0.1172(9) -0.1680(4) 0.075(2) Uani 1 1 d U . . C26S C -0.3922(9) -0.1570(10) -0.2201(5) 0.083(3) Uani 1 1 d U . . C27S C -0.3309(8) -0.1885(10) -0.1229(4) 0.073(3) Uani 1 1 d U . . C1B C -0.3582(13) 0.0910(17) -0.3459(8) 0.113(7) Uani 0.473(10) 1 d PDU A 1 H1B1 H -0.3459 0.0190 -0.3381 0.136 Uiso 0.473(10) 1 calc PR A 1 H1B2 H -0.3774 0.0928 -0.3872 0.136 Uiso 0.473(10) 1 calc PR A 1 C2B C -0.4684(15) 0.086(3) -0.3215(12) 0.136(8) Uani 0.473(10) 1 d PDU A 1 H2B1 H -0.4674 0.1653 -0.3231 0.163 Uiso 0.473(10) 1 calc PR A 1 H2B2 H -0.4532 0.0719 -0.2814 0.163 Uiso 0.473(10) 1 calc PR A 1 C3B C -0.6035(14) -0.017(3) -0.3532(12) 0.125(8) Uani 0.473(10) 1 d PDU A 1 H3B1 H -0.6263 0.0010 -0.3921 0.150 Uiso 0.473(10) 1 calc PR A 1 H3B2 H -0.6048 -0.0967 -0.3549 0.150 Uiso 0.473(10) 1 calc PR A 1 C4B C -0.6997(17) -0.018(4) -0.3191(14) 0.194(11) Uani 0.473(10) 1 d PDU A 1 H4B1 H -0.6851 -0.0494 -0.2826 0.233 Uiso 0.473(10) 1 calc PR A 1 H4B2 H -0.6856 0.0657 -0.3114 0.233 Uiso 0.473(10) 1 calc PR A 1 C5B C -0.8397(17) -0.102(4) -0.3532(18) 0.222(11) Uani 0.473(10) 1 d PDU A 1 H5B1 H -0.8674 -0.1878 -0.3465 0.266 Uiso 0.473(10) 1 calc PR A 1 H5B2 H -0.8438 -0.0962 -0.3939 0.266 Uiso 0.473(10) 1 calc PR A 1 C6B C -0.931(2) -0.061(3) -0.3348(19) 0.225(11) Uani 0.473(10) 1 d PDU A 1 H6B1 H -0.9115 0.0212 -0.3461 0.270 Uiso 0.473(10) 1 calc PR A 1 H6B2 H -0.9193 -0.0560 -0.2933 0.270 Uiso 0.473(10) 1 calc PR A 1 C7B C -1.0723(19) -0.156(4) -0.3638(18) 0.218(10) Uani 0.473(10) 1 d PDU A 1 H7B1 H -1.0945 -0.1376 -0.4026 0.262 Uiso 0.473(10) 1 calc PR A 1 H7B2 H -1.0803 -0.2387 -0.3661 0.262 Uiso 0.473(10) 1 calc PR A 1 C8B C -1.168(2) -0.153(5) -0.3303(13) 0.230(11) Uani 0.473(10) 1 d PDU A 1 H8B1 H -1.1501 -0.0683 -0.3222 0.276 Uiso 0.473(10) 1 calc PR A 1 H8B2 H -1.1573 -0.1867 -0.2941 0.276 Uiso 0.473(10) 1 calc PR A 1 C9B C -1.307(2) -0.233(4) -0.3666(17) 0.222(11) Uani 0.473(10) 1 d PDU A 1 H9B1 H -1.3178 -0.3113 -0.3821 0.267 Uiso 0.473(10) 1 calc PR A 1 H9B2 H -1.3716 -0.2505 -0.3432 0.267 Uiso 0.473(10) 1 calc PR A 1 C10B C -1.331(2) -0.162(4) -0.4149(15) 0.217(12) Uani 0.473(10) 1 d PDU A 1 H10I H -1.2770 -0.1563 -0.4418 0.260 Uiso 0.473(10) 1 calc PR A 1 H10J H -1.3060 -0.0779 -0.3996 0.260 Uiso 0.473(10) 1 calc PR A 1 C11B C -1.477(2) -0.230(4) -0.4452(17) 0.221(13) Uani 0.473(10) 1 d PDU A 1 H11F H -1.5008 -0.3122 -0.4623 0.265 Uiso 0.473(10) 1 calc PR A 1 H11G H -1.5311 -0.2390 -0.4180 0.265 Uiso 0.473(10) 1 calc PR A 1 C12B C -1.498(4) -0.153(4) -0.4911(16) 0.25(2) Uani 0.473(10) 1 d PDU A 1 H12D H -1.5906 -0.1932 -0.5105 0.372 Uiso 0.473(10) 1 calc PR A 1 H12E H -1.4456 -0.1468 -0.5184 0.372 Uiso 0.473(10) 1 calc PR A 1 H12F H -1.4718 -0.0712 -0.4738 0.372 Uiso 0.473(10) 1 calc PR A 1 C1C C -0.3780(11) 0.1659(16) -0.3174(7) 0.082(5) Uani 0.527(10) 1 d PDU A 2 H1C1 H -0.4035 0.2288 -0.3289 0.099 Uiso 0.527(10) 1 calc PR A 2 H1C2 H -0.3967 0.1438 -0.2801 0.099 Uiso 0.527(10) 1 calc PR A 2 C2C C -0.4467(15) 0.0531(17) -0.3617(8) 0.108(6) Uani 0.527(10) 1 d PDU A 2 H2C1 H -0.4338 -0.0142 -0.3459 0.130 Uiso 0.527(10) 1 calc PR A 2 H2C2 H -0.4080 0.0731 -0.3950 0.130 Uiso 0.527(10) 1 calc PR A 2 C3C C -0.5933(15) 0.011(3) -0.3797(10) 0.152(10) Uani 0.527(10) 1 d PDU A 2 H3C1 H -0.6060 0.0807 -0.3924 0.183 Uiso 0.527(10) 1 calc PR A 2 H3C2 H -0.6342 -0.0546 -0.4118 0.183 Uiso 0.527(10) 1 calc PR A 2 C4C C -0.6595(18) -0.036(4) -0.3308(11) 0.170(10) Uani 0.527(10) 1 d PDU A 2 H4C1 H -0.6179 0.0277 -0.2980 0.204 Uiso 0.527(10) 1 calc PR A 2 H4C2 H -0.6521 -0.1091 -0.3192 0.204 Uiso 0.527(10) 1 calc PR A 2 C5C C -0.8052(19) -0.071(4) -0.3522(16) 0.221(11) Uani 0.527(10) 1 d PDU A 2 H5C1 H -0.8155 0.0030 -0.3486 0.266 Uiso 0.527(10) 1 calc PR A 2 H5C2 H -0.8360 -0.1053 -0.3924 0.266 Uiso 0.527(10) 1 calc PR A 2 C6C C -0.885(2) -0.166(4) -0.3167(15) 0.232(11) Uani 0.527(10) 1 d PDU A 2 H6C1 H -0.8667 -0.1253 -0.2784 0.278 Uiso 0.527(10) 1 calc PR A 2 H6C2 H -0.8588 -0.2299 -0.3133 0.278 Uiso 0.527(10) 1 calc PR A 2 C7C C -1.0322(19) -0.225(3) -0.3431(18) 0.238(11) Uani 0.527(10) 1 d PDU A 2 H7C1 H -1.0541 -0.2803 -0.3774 0.286 Uiso 0.527(10) 1 calc PR A 2 H7C2 H -1.0815 -0.2742 -0.3161 0.286 Uiso 0.527(10) 1 calc PR A 2 C8C C -1.073(2) -0.127(3) -0.3584(19) 0.238(10) Uani 0.527(10) 1 d PDU A 2 H8C1 H -1.0598 -0.1048 -0.3965 0.286 Uiso 0.527(10) 1 calc PR A 2 H8C2 H -1.0179 -0.0521 -0.3311 0.286 Uiso 0.527(10) 1 calc PR A 2 C9C C -1.217(2) -0.177(4) -0.3574(14) 0.224(10) Uani 0.527(10) 1 d PDU A 2 H9C1 H -1.2367 -0.2265 -0.3256 0.269 Uiso 0.527(10) 1 calc PR A 2 H9C2 H -1.2349 -0.1084 -0.3518 0.269 Uiso 0.527(10) 1 calc PR A 2 C10C C -1.305(2) -0.257(4) -0.4130(13) 0.199(11) Uani 0.527(10) 1 d PDU A 2 H10K H -1.2952 -0.3313 -0.4166 0.239 Uiso 0.527(10) 1 calc PR A 2 H10L H -1.2795 -0.2111 -0.4452 0.239 Uiso 0.527(10) 1 calc PR A 2 C11C C -1.449(2) -0.295(4) -0.4142(13) 0.212(11) Uani 0.527(10) 1 d PDU A 2 H11H H -1.4591 -0.2217 -0.4100 0.254 Uiso 0.527(10) 1 calc PR A 2 H11I H -1.4757 -0.3436 -0.3827 0.254 Uiso 0.527(10) 1 calc PR A 2 C12C C -1.534(3) -0.373(4) -0.4710(14) 0.27(2) Uani 0.527(10) 1 d PDU A 2 H12G H -1.6248 -0.3944 -0.4734 0.403 Uiso 0.527(10) 1 calc PR A 2 H12H H -1.5270 -0.4483 -0.4738 0.403 Uiso 0.527(10) 1 calc PR A 2 H12I H -1.5035 -0.3262 -0.5020 0.403 Uiso 0.527(10) 1 calc PR A 2 N1 N 0.0654(7) 0.7508(8) -0.1314(3) 0.075(2) Uani 1 1 d U . . N1S N -0.2529(7) 0.3945(7) -0.0686(3) 0.079(2) Uani 1 1 d U . . N2S N -0.1692(7) 0.1005(8) -0.0133(3) 0.074(2) Uani 1 1 d U . . N101 N -0.2370(7) 0.2086(11) -0.3170(4) 0.141(4) Uani 1 1 d DU . . N21S N -0.4694(9) -0.1930(10) -0.2622(4) 0.119(4) Uani 1 1 d U . . N22S N -0.3573(6) -0.2410(7) -0.0847(4) 0.077(2) Uani 1 1 d U . . O1S O 0.3489(5) 0.5422(6) -0.0572(3) 0.0757(18) Uani 1 1 d U . . O2S O 0.1823(5) 0.2942(6) -0.0083(2) 0.0715(17) Uani 1 1 d U . . O21S O 0.1164(5) 0.2243(6) -0.1412(2) 0.0741(18) Uani 1 1 d U . . O22S O -0.0286(5) -0.0009(5) -0.0701(2) 0.0656(16) Uani 1 1 d U . . O3H O 0.3524(7) 0.4160(9) -0.1640(3) 0.121(3) Uani 1 1 d . . . O1H O 0.3013(5) 0.1813(6) -0.0592(2) 0.0751(18) Uani 1 1 d U . . O2H O -0.4594(5) -0.5477(5) -0.0634(2) 0.0706(17) Uani 1 1 d U . . Na1 Na 0.1593(3) 0.0940(3) 0.00244(14) 0.0713(11) Uani 1 1 d U . . Na2 Na -0.4245(3) -0.3661(3) -0.01033(15) 0.0724(11) Uani 1 1 d U . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.083(5) 0.096(7) 0.077(6) 0.029(5) 0.029(5) 0.069(5) C2 0.110(6) 0.107(8) 0.099(7) 0.036(6) 0.043(6) 0.085(6) C3 0.123(6) 0.100(8) 0.094(7) 0.041(6) 0.041(6) 0.081(6) C4 0.110(5) 0.089(7) 0.083(6) 0.027(6) 0.038(6) 0.071(5) C12 0.125(7) 0.089(7) 0.100(7) 0.037(6) 0.037(7) 0.066(6) C13 0.120(6) 0.084(8) 0.090(7) 0.027(6) 0.037(7) 0.046(6) C14 0.089(6) 0.081(8) 0.095(7) 0.026(6) 0.028(6) 0.040(5) C15 0.087(5) 0.077(7) 0.080(6) 0.022(5) 0.030(5) 0.050(5) C5 0.093(5) 0.073(6) 0.082(6) 0.021(5) 0.032(5) 0.050(5) C6 0.081(4) 0.085(6) 0.069(5) 0.021(5) 0.026(5) 0.057(4) C7 0.059(4) 0.089(6) 0.074(5) 0.026(5) 0.026(4) 0.049(4) C9 0.078(5) 0.090(8) 0.079(5) 0.025(5) 0.024(4) 0.054(5) C10 0.078(6) 0.083(7) 0.083(6) 0.022(5) 0.037(5) 0.051(6) C8 0.068(4) 0.085(6) 0.073(6) 0.017(5) 0.021(4) 0.057(4) C11 0.056(4) 0.085(6) 0.081(6) 0.025(5) 0.020(4) 0.048(5) C1S 0.053(4) 0.089(6) 0.068(5) 0.025(5) 0.022(4) 0.047(4) C2S 0.051(4) 0.082(6) 0.093(6) 0.028(5) 0.011(5) 0.042(4) C3S 0.056(4) 0.082(6) 0.070(5) 0.014(5) 0.018(4) 0.046(4) C4S 0.049(4) 0.075(6) 0.071(5) 0.015(5) 0.007(4) 0.037(4) C5S 0.051(4) 0.075(6) 0.075(6) 0.020(5) 0.017(4) 0.037(4) C6S 0.058(5) 0.087(7) 0.074(6) 0.021(5) 0.014(5) 0.043(5) C7S 0.053(5) 0.074(6) 0.067(5) 0.011(5) 0.022(4) 0.042(5) C1A 0.070(5) 0.105(8) 0.112(7) 0.027(5) 0.024(5) 0.066(5) C2A 0.111(7) 0.121(10) 0.155(10) -0.003(7) -0.022(7) 0.077(8) C3A 0.135(9) 0.166(13) 0.169(11) 0.013(9) -0.018(8) 0.086(10) C4A 0.215(14) 0.115(12) 0.164(12) 0.016(9) -0.045(10) 0.068(11) C5A 0.225(14) 0.178(15) 0.129(11) 0.018(9) -0.021(10) 0.095(13) C6A 0.232(15) 0.174(15) 0.136(11) -0.011(10) -0.021(10) 0.108(13) C7A 0.204(14) 0.29(2) 0.124(12) -0.022(13) 0.028(9) 0.086(16) C8A 0.244(15) 0.32(2) 0.180(15) -0.096(16) -0.028(12) 0.140(17) C9A 0.207(15) 0.36(3) 0.205(19) -0.038(19) 0.005(13) 0.115(17) C10A 0.255(16) 0.34(3) 0.159(15) 0.063(17) 0.024(16) 0.174(18) C11A 0.209(16) 0.30(3) 0.24(2) 0.15(2) 0.074(17) 0.132(18) C12A 0.279(18) 0.34(4) 0.37(4) 0.17(3) 0.06(3) 0.06(3) C101 0.077(5) 0.181(10) 0.101(8) 0.073(7) 0.014(5) 0.068(6) C102 0.084(6) 0.216(13) 0.124(9) 0.101(9) 0.014(6) 0.065(7) C103 0.096(6) 0.174(12) 0.104(8) 0.073(8) 0.016(6) 0.065(7) C104 0.099(5) 0.099(8) 0.092(7) 0.035(6) 0.011(5) 0.049(6) C112 0.105(6) 0.109(10) 0.114(8) 0.046(7) 0.015(6) 0.050(7) C113 0.112(7) 0.144(11) 0.106(9) 0.052(8) 0.019(7) 0.045(8) C114 0.103(7) 0.145(12) 0.106(9) 0.046(8) -0.005(7) 0.019(7) C115 0.094(6) 0.104(9) 0.080(7) 0.018(6) -0.007(5) 0.028(6) C105 0.084(5) 0.098(8) 0.075(6) 0.017(5) 0.004(5) 0.046(5) C106 0.083(5) 0.107(8) 0.071(5) 0.025(5) 0.009(5) 0.057(5) C107 0.072(4) 0.103(7) 0.071(5) 0.032(5) 0.018(4) 0.055(5) C110 0.080(6) 0.100(8) 0.086(7) 0.030(6) 0.027(5) 0.056(6) C109 0.135(9) 0.122(9) 0.070(6) 0.023(5) 0.023(6) 0.085(7) C108 0.065(5) 0.133(8) 0.094(7) 0.046(5) 0.011(4) 0.050(5) C111 0.055(5) 0.137(9) 0.100(7) 0.056(6) 0.017(5) 0.046(6) C21S 0.055(4) 0.088(7) 0.076(5) 0.021(5) 0.017(4) 0.039(4) C22S 0.064(4) 0.086(7) 0.065(5) 0.021(5) 0.027(4) 0.045(4) C23S 0.055(4) 0.077(6) 0.073(5) 0.019(4) 0.025(4) 0.043(4) C24S 0.059(4) 0.087(6) 0.074(5) 0.023(5) 0.017(4) 0.044(4) C25S 0.070(5) 0.082(7) 0.069(5) 0.013(5) 0.017(4) 0.033(4) C26S 0.062(5) 0.104(8) 0.076(6) 0.025(6) 0.021(4) 0.031(5) C27S 0.052(5) 0.090(7) 0.079(6) 0.021(5) 0.016(4) 0.037(5) C1B 0.089(8) 0.178(14) 0.056(12) 0.032(11) 0.007(7) 0.054(9) C2B 0.088(8) 0.187(18) 0.118(16) -0.007(15) 0.008(11) 0.061(10) C3B 0.077(8) 0.187(17) 0.126(19) -0.009(17) -0.002(10) 0.087(11) C4B 0.116(9) 0.25(2) 0.170(19) -0.050(18) 0.050(12) 0.046(15) C5B 0.091(9) 0.29(2) 0.22(2) 0.01(2) 0.057(15) 0.033(14) C6B 0.157(11) 0.30(2) 0.23(2) 0.05(2) 0.028(16) 0.117(15) C7B 0.141(10) 0.30(2) 0.26(2) 0.064(19) 0.027(13) 0.145(15) C8B 0.169(13) 0.30(2) 0.24(2) 0.08(2) 0.062(13) 0.117(18) C9B 0.157(12) 0.30(2) 0.24(2) 0.068(19) 0.071(15) 0.124(17) C10B 0.154(15) 0.31(3) 0.23(2) 0.06(2) 0.066(16) 0.136(19) C11B 0.147(16) 0.33(3) 0.23(3) 0.05(2) 0.072(17) 0.14(2) C12B 0.19(3) 0.36(5) 0.15(3) 0.02(3) 0.01(2) 0.10(4) C1C 0.080(6) 0.134(13) 0.066(10) 0.036(8) 0.016(7) 0.078(8) C2C 0.096(8) 0.124(13) 0.088(13) 0.029(9) -0.007(9) 0.050(9) C3C 0.099(10) 0.191(19) 0.149(19) 0.000(16) -0.021(10) 0.075(12) C4C 0.116(11) 0.211(19) 0.174(19) -0.042(17) 0.020(12) 0.078(15) C5C 0.111(12) 0.27(2) 0.22(2) -0.021(17) 0.009(14) 0.055(16) C6C 0.130(12) 0.30(2) 0.25(2) 0.018(18) 0.038(15) 0.095(15) C7C 0.131(12) 0.32(2) 0.26(2) 0.07(2) 0.047(16) 0.106(14) C8C 0.151(12) 0.32(2) 0.26(2) 0.059(19) 0.066(14) 0.119(14) C9C 0.142(13) 0.30(2) 0.25(2) 0.074(19) 0.066(15) 0.111(15) C10C 0.150(12) 0.29(2) 0.22(2) 0.103(19) 0.060(14) 0.141(16) C11C 0.146(13) 0.30(3) 0.22(2) 0.09(2) 0.056(15) 0.132(18) C12C 0.158(19) 0.45(5) 0.20(3) 0.09(3) 0.049(18) 0.14(3) N1 0.071(4) 0.102(6) 0.082(5) 0.030(4) 0.019(4) 0.066(4) N1S 0.060(4) 0.089(6) 0.091(6) 0.008(5) 0.006(4) 0.044(4) N2S 0.066(5) 0.079(6) 0.094(6) 0.025(5) 0.028(4) 0.047(5) N101 0.061(4) 0.196(10) 0.123(7) 0.083(6) -0.008(4) 0.039(5) N21S 0.073(6) 0.154(10) 0.085(6) 0.027(6) 0.002(4) 0.026(6) N22S 0.048(4) 0.086(6) 0.101(6) 0.028(5) 0.015(4) 0.036(4) O1S 0.050(3) 0.088(5) 0.098(5) 0.024(4) 0.020(3) 0.040(3) O2S 0.063(3) 0.092(4) 0.081(4) 0.025(3) 0.020(3) 0.053(3) O21S 0.058(3) 0.089(5) 0.085(4) 0.030(4) 0.023(3) 0.041(3) O22S 0.054(3) 0.087(4) 0.076(4) 0.027(3) 0.020(3) 0.048(3) O3H 0.103(5) 0.166(8) 0.115(6) 0.033(6) 0.021(5) 0.083(6) O1H 0.063(3) 0.089(5) 0.080(4) 0.012(3) 0.022(3) 0.040(3) O2H 0.050(3) 0.083(4) 0.092(4) 0.020(3) 0.018(3) 0.042(3) Na1 0.0577(19) 0.088(3) 0.079(2) 0.029(2) 0.0183(17) 0.0426(19) Na2 0.0512(18) 0.088(3) 0.090(2) 0.024(2) 0.0232(17) 0.0409(19) _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C2 1.374(12) . ? C1 C6 1.391(11) . ? C1 N1 1.406(11) . ? C2 C3 1.371(14) . ? C2 H2 0.9500 . ? C3 C4 1.420(14) . ? C3 H3 0.9500 . ? C4 C5 1.407(13) . ? C4 C12 1.436(14) . ? C12 C13 1.364(15) . ? C12 H12 0.9500 . ? C13 C14 1.377(14) . ? C13 H13 0.9500 . ? C14 C15 1.351(12) . ? C14 H14 0.9500 . ? C15 C5 1.446(12) . ? C15 H15 0.9500 . ? C5 C6 1.404(12) . ? C6 C7 1.531(12) . ? C7 C9 1.503(12) . ? C7 C10 1.548(12) . ? C7 C8 1.568(12) . ? C9 H9A 0.9800 . ? C9 H9B 0.9800 . ? C9 H9C 0.9800 . ? C10 H10A 0.9800 . ? C10 H10B 0.9800 . ? C10 H10C 0.9800 . ? C8 C11 1.330(11) . ? C8 N1 1.353(10) . ? C11 C1S 1.426(11) . ? C11 H11 0.9500 . ? C1S C4S 1.413(11) . ? C1S C2S 1.484(10) . ? C2S O1S 1.223(9) . ? C2S C3S 1.469(12) . ? C3S O2S 1.250(9) . ? C3S C4S 1.447(10) . ? C4S C5S 1.409(11) . ? C5S C6S 1.422(11) . ? C5S C7S 1.429(13) . ? C6S N1S 1.145(10) . ? C7S N2S 1.147(10) . ? C1A N1 1.472(11) . ? C1A C2A 1.540(16) . ? C1A H1A1 0.9900 . ? C1A H1A2 0.9900 . ? C2A C3A 1.384(16) . ? C2A H2A1 0.9900 . ? C2A H2A2 0.9900 . ? C3A C4A 1.56(2) . ? C3A H3A1 0.9900 . ? C3A H3A2 0.9900 . ? C4A C5A 1.41(2) . ? C4A H4A1 0.9900 . ? C4A H4A2 0.9900 . ? C5A C6A 1.47(2) . ? C5A H5A1 0.9900 . ? C5A H5A2 0.9900 . ? C6A C7A 1.45(2) . ? C6A H6A1 0.9900 . ? C6A H6A2 0.9900 . ? C7A C8A 1.41(2) . ? C7A H7A1 0.9900 . ? C7A H7A2 0.9900 . ? C8A C9A 1.66(3) . ? C8A H8A1 0.9900 . ? C8A H8A2 0.9900 . ? C9A C10A 1.36(3) . ? C9A H9A1 0.9900 . ? C9A H9A2 0.9900 . ? C10A C11A 1.46(3) . ? C10A H10D 0.9900 . ? C10A H10E 0.9900 . ? C11A C12A 1.24(3) . ? C11A H11A 0.9900 . ? C11A H11B 0.9900 . ? C12A H12A 0.9800 . ? C12A H12B 0.9800 . ? C12A H12C 0.9800 . ? C101 C106 1.331(13) . ? C101 N101 1.422(13) . ? C101 C102 1.439(13) . ? C102 C103 1.354(15) . ? C102 H102 0.9500 . ? C103 C104 1.389(15) . ? C103 H103 0.9500 . ? C104 C112 1.407(15) . ? C104 C105 1.442(13) . ? C112 C113 1.352(15) . ? C112 H112 0.9500 . ? C113 C114 1.402(16) . ? C113 H113 0.9500 . ? C114 C115 1.354(15) . ? C114 H114 0.9500 . ? C115 C105 1.399(14) . ? C115 H115 0.9500 . ? C105 C106 1.443(13) . ? C106 C107 1.497(12) . ? C107 C108 1.513(14) . ? C107 C109 1.523(14) . ? C107 C110 1.542(12) . ? C110 H11C 0.9800 . ? C110 H11D 0.9800 . ? C110 H11E 0.9800 . ? C109 H10F 0.9800 . ? C109 H10G 0.9800 . ? C109 H10H 0.9800 . ? C108 N101 1.344(11) . ? C108 C111 1.378(13) . ? C111 C21S 1.440(12) . ? C111 H111 0.9500 . ? C21S C24S 1.422(12) . ? C21S C22S 1.451(12) . ? C22S O21S 1.243(10) . ? C22S C23S 1.507(12) . ? C23S O22S 1.239(9) . ? C23S C24S 1.440(12) . ? C24S C25S 1.386(12) . ? C25S C27S 1.419(13) . ? C25S C26S 1.421(13) . ? C26S N21S 1.153(11) . ? C27S N22S 1.153(10) . ? C27S Na1 3.078(10) 2 ? C1B N101 1.522(9) . ? C1B C2B 1.524(10) . ? C1B H1B1 0.9900 . ? C1B H1B2 0.9900 . ? C2B C3B 1.541(10) . ? C2B H2B1 0.9900 . ? C2B H2B2 0.9900 . ? C3B C4B 1.539(10) . ? C3B H3B1 0.9900 . ? C3B H3B2 0.9900 . ? C4B C5B 1.536(10) . ? C4B H4B1 0.9900 . ? C4B H4B2 0.9900 . ? C5B C6B 1.539(10) . ? C5B H5B1 0.9900 . ? C5B H5B2 0.9900 . ? C6B C7B 1.541(10) . ? C6B H6B1 0.9900 . ? C6B H6B2 0.9900 . ? C7B C8B 1.539(10) . ? C7B H7B1 0.9900 . ? C7B H7B2 0.9900 . ? C8B C9B 1.544(10) . ? C8B H8B1 0.9900 . ? C8B H8B2 0.9900 . ? C9B C10B 1.536(10) . ? C9B H9B1 0.9900 . ? C9B H9B2 0.9900 . ? C10B C11B 1.541(10) . ? C10B H10I 0.9900 . ? C10B H10J 0.9900 . ? C11B C12B 1.537(10) . ? C11B H11F 0.9900 . ? C11B H11G 0.9900 . ? C12B H12D 0.9800 . ? C12B H12E 0.9800 . ? C12B H12F 0.9800 . ? C1C N101 1.506(9) . ? C1C C2C 1.533(10) . ? C1C H1C1 0.9900 . ? C1C H1C2 0.9900 . ? C2C C3C 1.536(9) . ? C2C H2C1 0.9900 . ? C2C H2C2 0.9900 . ? C3C C4C 1.533(10) . ? C3C H3C1 0.9900 . ? C3C H3C2 0.9900 . ? C4C C5C 1.554(10) . ? C4C H4C1 0.9900 . ? C4C H4C2 0.9900 . ? C5C C6C 1.529(10) . ? C5C H5C1 0.9900 . ? C5C H5C2 0.9900 . ? C6C C7C 1.537(10) . ? C6C H6C1 0.9900 . ? C6C H6C2 0.9900 . ? C7C C8C 1.535(10) . ? C7C H7C1 0.9900 . ? C7C H7C2 0.9900 . ? C8C C9C 1.541(10) . ? C8C H8C1 0.9900 . ? C8C H8C2 0.9900 . ? C9C C10C 1.534(10) . ? C9C H9C1 0.9900 . ? C9C H9C2 0.9900 . ? C10C C11C 1.540(10) . ? C10C H10K 0.9900 . ? C10C H10L 0.9900 . ? C11C C12C 1.542(10) . ? C11C H11H 0.9900 . ? C11C H11I 0.9900 . ? C12C H12G 0.9800 . ? C12C H12H 0.9800 . ? C12C H12I 0.9800 . ? N2S Na1 2.497(9) 2 ? N22S Na2 2.412(9) . ? N22S Na1 2.632(8) 2 ? O1S Na2 2.402(6) 1_665 ? O2S Na1 2.401(7) . ? O2S Na2 2.530(6) 2 ? O22S Na1 2.332(6) . ? O22S Na1 2.421(6) 2 ? O1H Na1 2.372(6) . ? O1H Na2 2.466(8) 2 ? O2H Na2 2.411(7) . ? O2H Na2 2.437(6) 2_445 ? Na1 O22S 2.421(6) 2 ? Na1 N2S 2.497(9) 2 ? Na1 N22S 2.632(8) 2 ? Na1 C27S 3.078(10) 2 ? Na1 Na2 3.346(5) 2 ? Na1 Na1 3.378(6) 2 ? Na2 O1S 2.402(6) 1_445 ? Na2 O2H 2.437(6) 2_445 ? Na2 O1H 2.466(8) 2 ? Na2 O2S 2.530(6) 2 ? Na2 Na2 3.062(7) 2_445 ? Na2 Na1 3.346(5) 2 ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 C1 C6 121.4(10) . . ? C2 C1 N1 128.7(9) . . ? C6 C1 N1 109.8(7) . . ? C3 C2 C1 119.8(10) . . ? C3 C2 H2 120.1 . . ? C1 C2 H2 120.1 . . ? C2 C3 C4 120.1(9) . . ? C2 C3 H3 119.9 . . ? C4 C3 H3 119.9 . . ? C5 C4 C3 120.1(10) . . ? C5 C4 C12 119.8(10) . . ? C3 C4 C12 120.1(9) . . ? C13 C12 C4 119.4(10) . . ? C13 C12 H12 120.3 . . ? C4 C12 H12 120.3 . . ? C12 C13 C14 120.3(11) . . ? C12 C13 H13 119.9 . . ? C14 C13 H13 119.9 . . ? C15 C14 C13 123.3(10) . . ? C15 C14 H14 118.3 . . ? C13 C14 H14 118.3 . . ? C14 C15 C5 118.7(9) . . ? C14 C15 H15 120.7 . . ? C5 C15 H15 120.7 . . ? C6 C5 C4 118.1(9) . . ? C6 C5 C15 123.4(8) . . ? C4 C5 C15 118.4(9) . . ? C1 C6 C5 120.2(8) . . ? C1 C6 C7 109.2(8) . . ? C5 C6 C7 130.5(8) . . ? C9 C7 C6 114.2(8) . . ? C9 C7 C10 115.6(7) . . ? C6 C7 C10 107.4(7) . . ? C9 C7 C8 110.6(7) . . ? C6 C7 C8 100.6(6) . . ? C10 C7 C8 107.3(8) . . ? C7 C9 H9A 109.5 . . ? C7 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? C7 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? C7 C10 H10A 109.5 . . ? C7 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? C7 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? C11 C8 N1 122.3(8) . . ? C11 C8 C7 129.3(7) . . ? N1 C8 C7 108.4(8) . . ? C8 C11 C1S 134.9(8) . . ? C8 C11 H11 112.5 . . ? C1S C11 H11 112.5 . . ? C4S C1S C11 129.4(7) . . ? C4S C1S C2S 90.6(6) . . ? C11 C1S C2S 140.0(8) . . ? O1S C2S C3S 132.9(7) . . ? O1S C2S C1S 139.0(8) . . ? C3S C2S C1S 87.9(6) . . ? O2S C3S C4S 135.0(8) . . ? O2S C3S C2S 135.2(7) . . ? C4S C3S C2S 89.8(6) . . ? C5S C4S C1S 134.7(7) . . ? C5S C4S C3S 133.8(8) . . ? C1S C4S C3S 91.6(6) . . ? C4S C5S C6S 122.1(8) . . ? C4S C5S C7S 120.6(7) . . ? C6S C5S C7S 117.1(7) . . ? N1S C6S C5S 179.5(12) . . ? N2S C7S C5S 176.8(10) . . ? N1 C1A C2A 110.6(9) . . ? N1 C1A H1A1 109.5 . . ? C2A C1A H1A1 109.5 . . ? N1 C1A H1A2 109.5 . . ? C2A C1A H1A2 109.5 . . ? H1A1 C1A H1A2 108.1 . . ? C3A C2A C1A 120.0(13) . . ? C3A C2A H2A1 107.3 . . ? C1A C2A H2A1 107.3 . . ? C3A C2A H2A2 107.3 . . ? C1A C2A H2A2 107.3 . . ? H2A1 C2A H2A2 106.9 . . ? C2A C3A C4A 116.0(16) . . ? C2A C3A H3A1 108.3 . . ? C4A C3A H3A1 108.3 . . ? C2A C3A H3A2 108.3 . . ? C4A C3A H3A2 108.3 . . ? H3A1 C3A H3A2 107.4 . . ? C5A C4A C3A 117.0(19) . . ? C5A C4A H4A1 108.1 . . ? C3A C4A H4A1 108.1 . . ? C5A C4A H4A2 108.1 . . ? C3A C4A H4A2 108.1 . . ? H4A1 C4A H4A2 107.3 . . ? C4A C5A C6A 115(2) . . ? C4A C5A H5A1 108.6 . . ? C6A C5A H5A1 108.6 . . ? C4A C5A H5A2 108.6 . . ? C6A C5A H5A2 108.6 . . ? H5A1 C5A H5A2 107.6 . . ? C7A C6A C5A 118(2) . . ? C7A C6A H6A1 107.8 . . ? C5A C6A H6A1 107.8 . . ? C7A C6A H6A2 107.8 . . ? C5A C6A H6A2 107.8 . . ? H6A1 C6A H6A2 107.2 . . ? C8A C7A C6A 118(2) . . ? C8A C7A H7A1 107.9 . . ? C6A C7A H7A1 107.9 . . ? C8A C7A H7A2 107.9 . . ? C6A C7A H7A2 107.9 . . ? H7A1 C7A H7A2 107.2 . . ? C7A C8A C9A 114(2) . . ? C7A C8A H8A1 108.7 . . ? C9A C8A H8A1 108.7 . . ? C7A C8A H8A2 108.7 . . ? C9A C8A H8A2 108.7 . . ? H8A1 C8A H8A2 107.6 . . ? C10A C9A C8A 120(3) . . ? C10A C9A H9A1 107.3 . . ? C8A C9A H9A1 107.3 . . ? C10A C9A H9A2 107.3 . . ? C8A C9A H9A2 107.3 . . ? H9A1 C9A H9A2 106.9 . . ? C9A C10A C11A 116(3) . . ? C9A C10A H10D 108.2 . . ? C11A C10A H10D 108.2 . . ? C9A C10A H10E 108.2 . . ? C11A C10A H10E 108.2 . . ? H10D C10A H10E 107.4 . . ? C12A C11A C10A 117(3) . . ? C12A C11A H11A 108.1 . . ? C10A C11A H11A 108.1 . . ? C12A C11A H11B 108.1 . . ? C10A C11A H11B 108.1 . . ? H11A C11A H11B 107.3 . . ? C11A C12A H12A 109.5 . . ? C11A C12A H12B 109.5 . . ? H12A C12A H12B 109.5 . . ? C11A C12A H12C 109.5 . . ? H12A C12A H12C 109.5 . . ? H12B C12A H12C 109.5 . . ? C106 C101 N101 108.3(8) . . ? C106 C101 C102 125.0(11) . . ? N101 C101 C102 126.7(10) . . ? C103 C102 C101 116.1(11) . . ? C103 C102 H102 122.0 . . ? C101 C102 H102 122.0 . . ? C102 C103 C104 123.0(10) . . ? C102 C103 H103 118.5 . . ? C104 C103 H103 118.5 . . ? C103 C104 C112 120.3(10) . . ? C103 C104 C105 119.8(10) . . ? C112 C104 C105 119.9(11) . . ? C113 C112 C104 119.4(10) . . ? C113 C112 H112 120.3 . . ? C104 C112 H112 120.3 . . ? C112 C113 C114 121.2(12) . . ? C112 C113 H113 119.4 . . ? C114 C113 H113 119.4 . . ? C115 C114 C113 120.6(12) . . ? C115 C114 H114 119.7 . . ? C113 C114 H114 119.7 . . ? C114 C115 C105 121.1(10) . . ? C114 C115 H115 119.5 . . ? C105 C115 H115 119.5 . . ? C115 C105 C104 117.6(10) . . ? C115 C105 C106 124.8(9) . . ? C104 C105 C106 117.6(9) . . ? C101 C106 C105 118.4(8) . . ? C101 C106 C107 111.2(9) . . ? C105 C106 C107 130.4(9) . . ? C106 C107 C108 100.9(8) . . ? C106 C107 C109 111.8(9) . . ? C108 C107 C109 108.8(9) . . ? C106 C107 C110 113.2(8) . . ? C108 C107 C110 110.0(9) . . ? C109 C107 C110 111.6(8) . . ? C107 C110 H11C 109.5 . . ? C107 C110 H11D 109.5 . . ? H11C C110 H11D 109.5 . . ? C107 C110 H11E 109.5 . . ? H11C C110 H11E 109.5 . . ? H11D C110 H11E 109.5 . . ? C107 C109 H10F 109.5 . . ? C107 C109 H10G 109.5 . . ? H10F C109 H10G 109.5 . . ? C107 C109 H10H 109.5 . . ? H10F C109 H10H 109.5 . . ? H10G C109 H10H 109.5 . . ? N101 C108 C111 120.9(9) . . ? N101 C108 C107 108.5(8) . . ? C111 C108 C107 130.6(8) . . ? C108 C111 C21S 132.1(9) . . ? C108 C111 H111 114.0 . . ? C21S C111 H111 114.0 . . ? C24S C21S C111 124.0(8) . . ? C24S C21S C22S 91.0(7) . . ? C111 C21S C22S 144.9(9) . . ? O21S C22S C21S 138.5(8) . . ? O21S C22S C23S 133.1(8) . . ? C21S C22S C23S 88.5(7) . . ? O22S C23S C24S 135.3(8) . . ? O22S C23S C22S 136.5(8) . . ? C24S C23S C22S 88.1(7) . . ? C25S C24S C21S 135.3(8) . . ? C25S C24S C23S 132.4(8) . . ? C21S C24S C23S 92.3(7) . . ? C24S C25S C27S 119.4(8) . . ? C24S C25S C26S 123.2(9) . . ? C27S C25S C26S 117.5(8) . . ? N21S C26S C25S 177.8(12) . . ? N22S C27S C25S 176.3(11) . . ? N22S C27S Na1 56.9(6) . 2 ? C25S C27S Na1 120.9(6) . 2 ? N101 C1B C2B 105.6(12) . . ? N101 C1B H1B1 110.6 . . ? C2B C1B H1B1 110.6 . . ? N101 C1B H1B2 110.6 . . ? C2B C1B H1B2 110.6 . . ? H1B1 C1B H1B2 108.8 . . ? C1B C2B C3B 112.7(12) . . ? C1B C2B H2B1 109.1 . . ? C3B C2B H2B1 109.1 . . ? C1B C2B H2B2 109.1 . . ? C3B C2B H2B2 109.1 . . ? H2B1 C2B H2B2 107.8 . . ? C4B C3B C2B 105.5(12) . . ? C4B C3B H3B1 110.6 . . ? C2B C3B H3B1 110.6 . . ? C4B C3B H3B2 110.6 . . ? C2B C3B H3B2 110.6 . . ? H3B1 C3B H3B2 108.8 . . ? C5B C4B C3B 109.0(12) . . ? C5B C4B H4B1 109.9 . . ? C3B C4B H4B1 109.9 . . ? C5B C4B H4B2 109.9 . . ? C3B C4B H4B2 109.9 . . ? H4B1 C4B H4B2 108.3 . . ? C4B C5B C6B 109.0(13) . . ? C4B C5B H5B1 109.9 . . ? C6B C5B H5B1 109.9 . . ? C4B C5B H5B2 109.9 . . ? C6B C5B H5B2 109.9 . . ? H5B1 C5B H5B2 108.3 . . ? C5B C6B C7B 107.7(13) . . ? C5B C6B H6B1 110.2 . . ? C7B C6B H6B1 110.2 . . ? C5B C6B H6B2 110.2 . . ? C7B C6B H6B2 110.2 . . ? H6B1 C6B H6B2 108.5 . . ? C8B C7B C6B 110.2(14) . . ? C8B C7B H7B1 109.6 . . ? C6B C7B H7B1 109.6 . . ? C8B C7B H7B2 109.6 . . ? C6B C7B H7B2 109.6 . . ? H7B1 C7B H7B2 108.1 . . ? C7B C8B C9B 107.7(13) . . ? C7B C8B H8B1 110.2 . . ? C9B C8B H8B1 110.2 . . ? C7B C8B H8B2 110.2 . . ? C9B C8B H8B2 110.2 . . ? H8B1 C8B H8B2 108.5 . . ? C10B C9B C8B 108.7(14) . . ? C10B C9B H9B1 110.0 . . ? C8B C9B H9B1 110.0 . . ? C10B C9B H9B2 110.0 . . ? C8B C9B H9B2 110.0 . . ? H9B1 C9B H9B2 108.3 . . ? C9B C10B C11B 109.1(13) . . ? C9B C10B H10I 109.9 . . ? C11B C10B H10I 109.9 . . ? C9B C10B H10J 109.9 . . ? C11B C10B H10J 109.9 . . ? H10I C10B H10J 108.3 . . ? C12B C11B C10B 107.7(14) . . ? C12B C11B H11F 110.2 . . ? C10B C11B H11F 110.2 . . ? C12B C11B H11G 110.2 . . ? C10B C11B H11G 110.2 . . ? H11F C11B H11G 108.5 . . ? C11B C12B H12D 109.5 . . ? C11B C12B H12E 109.5 . . ? H12D C12B H12E 109.5 . . ? C11B C12B H12F 109.5 . . ? H12D C12B H12F 109.5 . . ? H12E C12B H12F 109.5 . . ? N101 C1C C2C 101.3(11) . . ? N101 C1C H1C1 111.5 . . ? C2C C1C H1C1 111.5 . . ? N101 C1C H1C2 111.5 . . ? C2C C1C H1C2 111.5 . . ? H1C1 C1C H1C2 109.3 . . ? C1C C2C C3C 110.5(13) . . ? C1C C2C H2C1 109.6 . . ? C3C C2C H2C1 109.6 . . ? C1C C2C H2C2 109.6 . . ? C3C C2C H2C2 109.6 . . ? H2C1 C2C H2C2 108.1 . . ? C4C C3C C2C 110.8(12) . . ? C4C C3C H3C1 109.5 . . ? C2C C3C H3C1 109.5 . . ? C4C C3C H3C2 109.5 . . ? C2C C3C H3C2 109.5 . . ? H3C1 C3C H3C2 108.1 . . ? C3C C4C C5C 107.0(12) . . ? C3C C4C H4C1 110.3 . . ? C5C C4C H4C1 110.3 . . ? C3C C4C H4C2 110.3 . . ? C5C C4C H4C2 110.3 . . ? H4C1 C4C H4C2 108.6 . . ? C6C C5C C4C 108.6(13) . . ? C6C C5C H5C1 110.0 . . ? C4C C5C H5C1 110.0 . . ? C6C C5C H5C2 110.0 . . ? C4C C5C H5C2 110.0 . . ? H5C1 C5C H5C2 108.4 . . ? C5C C6C C7C 111.6(13) . . ? C5C C6C H6C1 109.3 . . ? C7C C6C H6C1 109.3 . . ? C5C C6C H6C2 109.3 . . ? C7C C6C H6C2 109.3 . . ? H6C1 C6C H6C2 108.0 . . ? C8C C7C C6C 110.9(14) . . ? C8C C7C H7C1 109.5 . . ? C6C C7C H7C1 109.5 . . ? C8C C7C H7C2 109.5 . . ? C6C C7C H7C2 109.5 . . ? H7C1 C7C H7C2 108.1 . . ? C7C C8C C9C 109.2(14) . . ? C7C C8C H8C1 109.8 . . ? C9C C8C H8C1 109.8 . . ? C7C C8C H8C2 109.8 . . ? C9C C8C H8C2 109.8 . . ? H8C1 C8C H8C2 108.3 . . ? C10C C9C C8C 110.3(14) . . ? C10C C9C H9C1 109.6 . . ? C8C C9C H9C1 109.6 . . ? C10C C9C H9C2 109.6 . . ? C8C C9C H9C2 109.6 . . ? H9C1 C9C H9C2 108.1 . . ? C9C C10C C11C 109.8(13) . . ? C9C C10C H10K 109.7 . . ? C11C C10C H10K 109.7 . . ? C9C C10C H10L 109.7 . . ? C11C C10C H10L 109.7 . . ? H10K C10C H10L 108.2 . . ? C10C C11C C12C 108.3(13) . . ? C10C C11C H11H 110.0 . . ? C12C C11C H11H 110.0 . . ? C10C C11C H11I 110.0 . . ? C12C C11C H11I 110.0 . . ? H11H C11C H11I 108.4 . . ? C11C C12C H12G 109.5 . . ? C11C C12C H12H 109.5 . . ? H12G C12C H12H 109.5 . . ? C11C C12C H12I 109.5 . . ? H12G C12C H12I 109.5 . . ? H12H C12C H12I 109.5 . . ? C8 N1 C1 112.0(7) . . ? C8 N1 C1A 125.0(8) . . ? C1 N1 C1A 123.0(7) . . ? C7S N2S Na1 152.9(7) . 2 ? C108 N101 C101 110.9(8) . . ? C108 N101 C1C 125.0(10) . . ? C101 N101 C1C 118.2(10) . . ? C108 N101 C1B 119.4(12) . . ? C101 N101 C1B 120.7(11) . . ? C1C N101 C1B 50.6(10) . . ? C27S N22S Na2 175.2(8) . . ? C27S N22S Na1 101.6(7) . 2 ? Na2 N22S Na1 83.0(3) . 2 ? C2S O1S Na2 149.2(6) . 1_665 ? C3S O2S Na1 155.5(6) . . ? C3S O2S Na2 109.7(5) . 2 ? Na1 O2S Na2 85.4(2) . 2 ? C23S O22S Na1 131.2(6) . . ? C23S O22S Na1 127.3(5) . 2 ? Na1 O22S Na1 90.6(2) . 2 ? Na1 O1H Na2 87.5(2) . 2 ? Na2 O2H Na2 78.3(2) . 2_445 ? O22S Na1 O1H 94.3(2) . . ? O22S Na1 O2S 93.0(2) . . ? O1H Na1 O2S 73.2(2) . . ? O22S Na1 O22S 89.4(2) . 2 ? O1H Na1 O22S 175.0(2) . 2 ? O2S Na1 O22S 110.0(2) . 2 ? O22S Na1 N2S 92.4(3) . 2 ? O1H Na1 N2S 100.2(3) . 2 ? O2S Na1 N2S 171.8(2) . 2 ? O22S Na1 N2S 76.3(2) 2 2 ? O22S Na1 N22S 167.0(3) . 2 ? O1H Na1 N22S 86.8(3) . 2 ? O2S Na1 N22S 74.9(2) . 2 ? O22S Na1 N22S 90.3(3) 2 2 ? N2S Na1 N22S 100.2(3) 2 2 ? O22S Na1 C27S 159.1(2) . 2 ? O1H Na1 C27S 106.2(3) . 2 ? O2S Na1 C27S 89.6(3) . 2 ? O22S Na1 C27S 70.3(2) 2 2 ? N2S Na1 C27S 87.5(3) 2 2 ? N22S Na1 C27S 21.5(2) 2 2 ? O22S Na1 Na2 128.43(18) . 2 ? O1H Na1 Na2 47.42(18) . 2 ? O2S Na1 Na2 48.93(15) . 2 ? O22S Na1 Na2 131.6(2) 2 2 ? N2S Na1 Na2 123.0(2) 2 2 ? N22S Na1 Na2 45.7(2) 2 2 ? C27S Na1 Na2 67.2(2) 2 2 ? O22S Na1 Na1 45.78(15) . 2 ? O1H Na1 Na1 140.0(2) . 2 ? O2S Na1 Na1 106.34(19) . 2 ? O22S Na1 Na1 43.67(15) 2 2 ? N2S Na1 Na1 81.9(2) 2 2 ? N22S Na1 Na1 132.6(2) 2 2 ? C27S Na1 Na1 113.8(2) 2 2 ? Na2 Na1 Na1 154.77(18) 2 2 ? O1S Na2 O2H 77.5(2) 1_445 . ? O1S Na2 N22S 92.6(2) 1_445 . ? O2H Na2 N22S 93.2(3) . . ? O1S Na2 O2H 75.4(2) 1_445 2_445 ? O2H Na2 O2H 101.7(2) . 2_445 ? N22S Na2 O2H 158.2(3) . 2_445 ? O1S Na2 O1H 126.6(2) 1_445 2 ? O2H Na2 O1H 155.6(2) . 2 ? N22S Na2 O1H 89.8(3) . 2 ? O2H Na2 O1H 83.3(2) 2_445 2 ? O1S Na2 O2S 161.3(3) 1_445 2 ? O2H Na2 O2S 87.7(2) . 2 ? N22S Na2 O2S 76.6(2) . 2 ? O2H Na2 O2S 119.5(2) 2_445 2 ? O1H Na2 O2S 69.4(2) 2 2 ? O1S Na2 Na2 68.23(18) 1_445 2_445 ? O2H Na2 Na2 51.20(17) . 2_445 ? N22S Na2 Na2 141.5(3) . 2_445 ? O2H Na2 Na2 50.46(17) 2_445 2_445 ? O1H Na2 Na2 128.6(2) 2 2_445 ? O2S Na2 Na2 111.1(2) 2 2_445 ? O1S Na2 Na1 136.0(2) 1_445 2 ? O2H Na2 Na1 122.44(17) . 2 ? N22S Na2 Na1 51.3(2) . 2 ? O2H Na2 Na1 127.9(2) 2_445 2 ? O1H Na2 Na1 45.09(16) 2 2 ? O2S Na2 Na1 45.67(16) 2 2 ? Na2 Na2 Na1 155.69(16) 2_445 2 ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C6 C1 C2 C3 -3.7(16) . . . . ? N1 C1 C2 C3 -177.7(10) . . . . ? C1 C2 C3 C4 0.5(16) . . . . ? C2 C3 C4 C5 1.6(16) . . . . ? C2 C3 C4 C12 -178.6(10) . . . . ? C5 C4 C12 C13 1.3(17) . . . . ? C3 C4 C12 C13 -178.5(11) . . . . ? C4 C12 C13 C14 -0.7(18) . . . . ? C12 C13 C14 C15 0.5(18) . . . . ? C13 C14 C15 C5 -0.9(16) . . . . ? C3 C4 C5 C6 -0.6(15) . . . . ? C12 C4 C5 C6 179.6(9) . . . . ? C3 C4 C5 C15 178.1(9) . . . . ? C12 C4 C5 C15 -1.6(15) . . . . ? C14 C15 C5 C6 -179.8(10) . . . . ? C14 C15 C5 C4 1.4(15) . . . . ? C2 C1 C6 C5 4.6(15) . . . . ? N1 C1 C6 C5 179.7(9) . . . . ? C2 C1 C6 C7 -174.0(9) . . . . ? N1 C1 C6 C7 1.1(11) . . . . ? C4 C5 C6 C1 -2.4(14) . . . . ? C15 C5 C6 C1 178.9(9) . . . . ? C4 C5 C6 C7 175.9(9) . . . . ? C15 C5 C6 C7 -2.9(17) . . . . ? C1 C6 C7 C9 -119.0(8) . . . . ? C5 C6 C7 C9 62.6(13) . . . . ? C1 C6 C7 C10 111.4(8) . . . . ? C5 C6 C7 C10 -67.0(13) . . . . ? C1 C6 C7 C8 -0.6(10) . . . . ? C5 C6 C7 C8 -179.0(10) . . . . ? C9 C7 C8 C11 -59.9(13) . . . . ? C6 C7 C8 C11 179.2(10) . . . . ? C10 C7 C8 C11 67.0(12) . . . . ? C9 C7 C8 N1 120.9(8) . . . . ? C6 C7 C8 N1 -0.1(9) . . . . ? C10 C7 C8 N1 -112.3(8) . . . . ? N1 C8 C11 C1S 178.2(10) . . . . ? C7 C8 C11 C1S -1.0(18) . . . . ? C8 C11 C1S C4S 177.5(11) . . . . ? C8 C11 C1S C2S -4(2) . . . . ? C4S C1S C2S O1S -178.8(13) . . . . ? C11 C1S C2S O1S 3(2) . . . . ? C4S C1S C2S C3S -2.9(7) . . . . ? C11 C1S C2S C3S 178.6(12) . . . . ? O1S C2S C3S O2S 0(2) . . . . ? C1S C2S C3S O2S -176.7(11) . . . . ? O1S C2S C3S C4S 179.2(12) . . . . ? C1S C2S C3S C4S 2.8(7) . . . . ? C11 C1S C4S C5S 2.3(18) . . . . ? C2S C1S C4S C5S -176.5(11) . . . . ? C11 C1S C4S C3S -178.3(10) . . . . ? C2S C1S C4S C3S 2.9(7) . . . . ? O2S C3S C4S C5S -4.0(19) . . . . ? C2S C3S C4S C5S 176.5(11) . . . . ? O2S C3S C4S C1S 176.6(11) . . . . ? C2S C3S C4S C1S -2.9(8) . . . . ? C1S C4S C5S C6S -9.6(17) . . . . ? C3S C4S C5S C6S 171.3(10) . . . . ? C1S C4S C5S C7S 175.9(10) . . . . ? C3S C4S C5S C7S -3.3(16) . . . . ? C4S C5S C6S N1S 116(100) . . . . ? C7S C5S C6S N1S -69(100) . . . . ? C4S C5S C7S N2S -89(14) . . . . ? C6S C5S C7S N2S 96(14) . . . . ? N1 C1A C2A C3A -165.6(12) . . . . ? C1A C2A C3A C4A 173.5(12) . . . . ? C2A C3A C4A C5A -179.6(15) . . . . ? C3A C4A C5A C6A -178.2(15) . . . . ? C4A C5A C6A C7A -177.8(18) . . . . ? C5A C6A C7A C8A 174(2) . . . . ? C6A C7A C8A C9A -175(2) . . . . ? C7A C8A C9A C10A -81(4) . . . . ? C8A C9A C10A C11A -178(2) . . . . ? C9A C10A C11A C12A 177(4) . . . . ? C106 C101 C102 C103 4(2) . . . . ? N101 C101 C102 C103 -176.7(15) . . . . ? C101 C102 C103 C104 -1(2) . . . . ? C102 C103 C104 C112 176.4(15) . . . . ? C102 C103 C104 C105 -2(2) . . . . ? C103 C104 C112 C113 -179.8(14) . . . . ? C105 C104 C112 C113 -1(2) . . . . ? C104 C112 C113 C114 -2(2) . . . . ? C112 C113 C114 C115 3(2) . . . . ? C113 C114 C115 C105 -1(2) . . . . ? C114 C115 C105 C104 -2.8(19) . . . . ? C114 C115 C105 C106 175.8(13) . . . . ? C103 C104 C105 C115 -177.7(13) . . . . ? C112 C104 C105 C115 3.7(18) . . . . ? C103 C104 C105 C106 3.6(18) . . . . ? C112 C104 C105 C106 -175.0(11) . . . . ? N101 C101 C106 C105 178.0(11) . . . . ? C102 C101 C106 C105 -2(2) . . . . ? N101 C101 C106 C107 -2.4(16) . . . . ? C102 C101 C106 C107 177.1(14) . . . . ? C115 C105 C106 C101 -180.0(13) . . . . ? C104 C105 C106 C101 -1.3(17) . . . . ? C115 C105 C106 C107 1(2) . . . . ? C104 C105 C106 C107 179.2(11) . . . . ? C101 C106 C107 C108 4.3(13) . . . . ? C105 C106 C107 C108 -176.2(11) . . . . ? C101 C106 C107 C109 -111.2(12) . . . . ? C105 C106 C107 C109 68.3(14) . . . . ? C101 C106 C107 C110 121.7(11) . . . . ? C105 C106 C107 C110 -58.8(16) . . . . ? C106 C107 C108 N101 -4.7(13) . . . . ? C109 C107 C108 N101 113.1(11) . . . . ? C110 C107 C108 N101 -124.4(10) . . . . ? C106 C107 C108 C111 174.8(13) . . . . ? C109 C107 C108 C111 -67.4(16) . . . . ? C110 C107 C108 C111 55.1(16) . . . . ? N101 C108 C111 C21S -173.6(13) . . . . ? C107 C108 C111 C21S 7(2) . . . . ? C108 C111 C21S C24S 178.2(12) . . . . ? C108 C111 C21S C22S 2(3) . . . . ? C24S C21S C22S O21S 177.1(12) . . . . ? C111 C21S C22S O21S -6(2) . . . . ? C24S C21S C22S C23S -3.3(7) . . . . ? C111 C21S C22S C23S 173.3(15) . . . . ? O21S C22S C23S O22S -0.6(18) . . . . ? C21S C22S C23S O22S 179.7(11) . . . . ? O21S C22S C23S C24S -177.1(11) . . . . ? C21S C22S C23S C24S 3.2(7) . . . . ? C111 C21S C24S C25S 7.3(18) . . . . ? C22S C21S C24S C25S -175.1(11) . . . . ? C111 C21S C24S C23S -174.2(10) . . . . ? C22S C21S C24S C23S 3.4(7) . . . . ? O22S C23S C24S C25S -1.3(19) . . . . ? C22S C23S C24S C25S 175.3(11) . . . . ? O22S C23S C24S C21S -179.8(10) . . . . ? C22S C23S C24S C21S -3.3(7) . . . . ? C21S C24S C25S C27S -168.6(10) . . . . ? C23S C24S C25S C27S 13.4(16) . . . . ? C21S C24S C25S C26S 10.0(18) . . . . ? C23S C24S C25S C26S -167.9(10) . . . . ? C24S C25S C26S N21S 135(28) . . . . ? C27S C25S C26S N21S -46(28) . . . . ? C24S C25S C27S N22S 62(14) . . . . ? C26S C25S C27S N22S -117(13) . . . . ? C24S C25S C27S Na1 9.1(12) . . . 2 ? C26S C25S C27S Na1 -169.7(7) . . . 2 ? N101 C1B C2B C3B 170(2) . . . . ? C1B C2B C3B C4B 174(3) . . . . ? C2B C3B C4B C5B 170(3) . . . . ? C3B C4B C5B C6B -154(4) . . . . ? C4B C5B C6B C7B -173(3) . . . . ? C5B C6B C7B C8B 156(4) . . . . ? C6B C7B C8B C9B 170(3) . . . . ? C7B C8B C9B C10B -74(4) . . . . ? C8B C9B C10B C11B -170(3) . . . . ? C9B C10B C11B C12B 177(4) . . . . ? N101 C1C C2C C3C -166.5(14) . . . . ? C1C C2C C3C C4C -67(3) . . . . ? C2C C3C C4C C5C 178(2) . . . . ? C3C C4C C5C C6C 156(3) . . . . ? C4C C5C C6C C7C -168(3) . . . . ? C5C C6C C7C C8C -49(4) . . . . ? C6C C7C C8C C9C -153(2) . . . . ? C7C C8C C9C C10C -82(4) . . . . ? C8C C9C C10C C11C -174(3) . . . . ? C9C C10C C11C C12C 179(4) . . . . ? C11 C8 N1 C1 -178.5(9) . . . . ? C7 C8 N1 C1 0.8(11) . . . . ? C11 C8 N1 C1A 0.3(15) . . . . ? C7 C8 N1 C1A 179.6(8) . . . . ? C2 C1 N1 C8 173.4(10) . . . . ? C6 C1 N1 C8 -1.2(11) . . . . ? C2 C1 N1 C1A -5.5(16) . . . . ? C6 C1 N1 C1A 179.9(9) . . . . ? C2A C1A N1 C8 -83.7(11) . . . . ? C2A C1A N1 C1 95.1(11) . . . . ? C5S C7S N2S Na1 62(15) . . . 2 ? C111 C108 N101 C101 -175.9(12) . . . . ? C107 C108 N101 C101 3.6(15) . . . . ? C111 C108 N101 C1C 32(2) . . . . ? C107 C108 N101 C1C -148.7(13) . . . . ? C111 C108 N101 C1B -28.6(18) . . . . ? C107 C108 N101 C1B 151.0(11) . . . . ? C106 C101 N101 C108 -0.8(17) . . . . ? C102 C101 N101 C108 179.7(15) . . . . ? C106 C101 N101 C1C 153.6(12) . . . . ? C102 C101 N101 C1C -26(2) . . . . ? C106 C101 N101 C1B -147.7(13) . . . . ? C102 C101 N101 C1B 33(2) . . . . ? C2C C1C N101 C108 -110.5(16) . . . . ? C2C C1C N101 C101 99.0(16) . . . . ? C2C C1C N101 C1B -8.9(14) . . . . ? C2B C1B N101 C108 101(2) . . . . ? C2B C1B N101 C101 -115(2) . . . . ? C2B C1B N101 C1C -11.8(18) . . . . ? C25S C27S N22S Na2 146(11) . . . . ? Na1 C27S N22S Na2 -160(8) 2 . . . ? C25S C27S N22S Na1 -54(14) . . . 2 ? C3S C2S O1S Na2 -51(2) . . . 1_665 ? C1S C2S O1S Na2 123.3(12) . . . 1_665 ? C4S C3S O2S Na1 60.9(19) . . . . ? C2S C3S O2S Na1 -119.8(13) . . . . ? C4S C3S O2S Na2 -173.7(9) . . . 2 ? C2S C3S O2S Na2 5.6(13) . . . 2 ? C24S C23S O22S Na1 -173.4(8) . . . . ? C22S C23S O22S Na1 11.6(15) . . . . ? C24S C23S O22S Na1 -40.2(15) . . . 2 ? C22S C23S O22S Na1 144.8(8) . . . 2 ? C23S O22S Na1 O1H -38.8(7) . . . . ? Na1 O22S Na1 O1H 176.7(3) 2 . . . ? C23S O22S Na1 O2S 34.6(7) . . . . ? Na1 O22S Na1 O2S -110.0(2) 2 . . . ? C23S O22S Na1 O22S 144.5(8) . . . 2 ? Na1 O22S Na1 O22S 0.0 2 . . 2 ? C23S O22S Na1 N2S -139.2(7) . . . 2 ? Na1 O22S Na1 N2S 76.2(2) 2 . . 2 ? C23S O22S Na1 N22S 55.7(14) . . . 2 ? Na1 O22S Na1 N22S -88.9(12) 2 . . 2 ? C23S O22S Na1 C27S 131.4(9) . . . 2 ? Na1 O22S Na1 C27S -13.1(8) 2 . . 2 ? C23S O22S Na1 Na2 -2.5(8) . . . 2 ? Na1 O22S Na1 Na2 -147.1(2) 2 . . 2 ? C23S O22S Na1 Na1 144.5(8) . . . 2 ? Na2 O1H Na1 O22S 141.0(2) 2 . . . ? Na2 O1H Na1 O2S 49.1(2) 2 . . . ? Na2 O1H Na1 O22S -81(3) 2 . . 2 ? Na2 O1H Na1 N2S -125.8(2) 2 . . 2 ? Na2 O1H Na1 N22S -26.0(2) 2 . . 2 ? Na2 O1H Na1 C27S -35.4(3) 2 . . 2 ? Na2 O1H Na1 Na1 144.7(3) 2 . . 2 ? C3S O2S Na1 O22S -11.6(13) . . . . ? Na2 O2S Na1 O22S -141.2(2) 2 . . . ? C3S O2S Na1 O1H 82.0(13) . . . . ? Na2 O2S Na1 O1H -47.6(2) 2 . . . ? C3S O2S Na1 O22S -102.1(13) . . . 2 ? Na2 O2S Na1 O22S 128.3(2) 2 . . 2 ? C3S O2S Na1 N2S 120(2) . . . 2 ? Na2 O2S Na1 N2S -10(2) 2 . . 2 ? C3S O2S Na1 N22S 173.2(13) . . . 2 ? Na2 O2S Na1 N22S 43.6(2) 2 . . 2 ? C3S O2S Na1 C27S -170.9(13) . . . 2 ? Na2 O2S Na1 C27S 59.5(2) 2 . . 2 ? C3S O2S Na1 Na2 129.6(14) . . . 2 ? C3S O2S Na1 Na1 -56.2(13) . . . 2 ? Na2 O2S Na1 Na1 174.22(19) 2 . . 2 ? Na2 O2H Na2 O1S -71.99(19) 2_445 . . 1_445 ? Na2 O2H Na2 N22S -163.9(2) 2_445 . . . ? Na2 O2H Na2 O2H 0.0 2_445 . . 2_445 ? Na2 O2H Na2 O1H 99.6(6) 2_445 . . 2 ? Na2 O2H Na2 O2S 119.6(2) 2_445 . . 2 ? Na2 O2H Na2 Na1 151.0(2) 2_445 . . 2 ? C27S N22S Na2 O1S -47(8) . . . 1_445 ? Na1 N22S Na2 O1S 152.3(2) 2 . . 1_445 ? C27S N22S Na2 O2H 30(8) . . . . ? Na1 N22S Na2 O2H -130.1(2) 2 . . . ? C27S N22S Na2 O2H -103(8) . . . 2_445 ? Na1 N22S Na2 O2H 96.8(7) 2 . . 2_445 ? C27S N22S Na2 O1H -174(8) . . . 2 ? Na1 N22S Na2 O1H 25.7(2) 2 . . 2 ? C27S N22S Na2 O2S 117(8) . . . 2 ? Na1 N22S Na2 O2S -43.2(2) 2 . . 2 ? C27S N22S Na2 Na2 10(8) . . . 2_445 ? Na1 N22S Na2 Na2 -150.3(3) 2 . . 2_445 ? C27S N22S Na2 Na1 160(8) . . . 2 ? _diffrn_measured_fraction_theta_max 0.945 _diffrn_reflns_theta_full 24.21 _diffrn_measured_fraction_theta_full 0.945 _refine_diff_density_max 0.459 _refine_diff_density_min -0.422 _refine_diff_density_rms 0.071 _database_code_depnum_ccdc_archive 'CCDC 977425' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_9 _audit_creation_method SHELXL-2013 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C18 H20 N O2, I' _chemical_formula_sum 'C18 H20 I N O2' _chemical_formula_weight 409.25 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _space_group_crystal_system orthorhombic _space_group_IT_number 61 _space_group_name_H-M_alt 'P b c a' _space_group_name_Hall '-P 2ac 2ab' _shelx_space_group_comment ; The symmetry employed for this shelxl refinement is uniquely defined by the following loop, which should always be used as a source of symmetry information in preference to the above space-group names. They are only intended as comments. ; loop_ _space_group_symop_operation_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' '-x, -y, -z' 'x-1/2, y, -z-1/2' 'x, -y-1/2, z-1/2' '-x-1/2, y-1/2, z' _cell_length_a 7.530(2) _cell_length_b 13.635(3) _cell_length_c 34.164(8) _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_volume 3507.9(15) _cell_formula_units_Z 8 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 12464 _cell_measurement_theta_min 2.3 _cell_measurement_theta_max 34.6 _exptl_crystal_description Platelet _exptl_crystal_colour Colourless _exptl_crystal_density_meas ? _exptl_crystal_density_method ? _exptl_crystal_density_diffrn 1.550 _exptl_crystal_F_000 1632 _exptl_transmission_factor_min ? _exptl_transmission_factor_max ? _exptl_crystal_size_max 0.200 _exptl_crystal_size_mid 0.150 _exptl_crystal_size_min 0.010 _exptl_absorpt_coefficient_mu 1.832 _shelx_estimated_absorpt_T_min 0.711 _shelx_estimated_absorpt_T_max 0.982 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_max 1.000 _exptl_absorpt_correction_T_min 0.698 _exptl_absorpt_process_details 'CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_source_power 2.5 _diffrn_source_voltage 45.0 _diffrn_source_current 55.0 _diffrn_radiation_wavelength 0.71075 _diffrn_radiation_type 'Mo K\a' _diffrn_source 'Rotating Anode' _diffrn_radiation_monochromator Confocal _diffrn_measurement_specimen_support MiTeGen _diffrn_detector CCD _diffrn_measurement_device ; AFC12 (Right): Kappa 3 circle ; _diffrn_measurement_device_type ; Rigaku Saturn724+ (2x2 bin mode) ; _diffrn_detector_area_resol_mean 28.5714 _diffrn_measurement_method 'profile data from \w-scans' _diffrn_reflns_number 21886 _diffrn_reflns_av_unetI/netI 0.0572 _diffrn_reflns_av_R_equivalents 0.0666 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -44 _diffrn_reflns_limit_l_max 39 _diffrn_reflns_theta_min 2.956 _diffrn_reflns_theta_max 27.482 _diffrn_reflns_theta_full 25.242 _diffrn_measured_fraction_theta_max 0.993 _diffrn_measured_fraction_theta_full 0.991 _diffrn_reflns_Laue_measured_fraction_max 0.993 _diffrn_reflns_Laue_measured_fraction_full 0.991 _diffrn_reflns_point_group_measured_fraction_max 0.993 _diffrn_reflns_point_group_measured_fraction_full 0.991 _reflns_number_total 3992 _reflns_number_gt 3503 _reflns_threshold_expression 'I > 2\s(I)' _reflns_Friedel_coverage 0.000 _reflns_Friedel_fraction_max . _reflns_Friedel_fraction_full . _reflns_special_details ; Reflections were merged by SHELXL according to the crystal class for the calculation of statistics and refinement. _reflns_Friedel_fraction is defined as the number of unique Friedel pairs measured divided by the number that would be possible theoretically, ignoring centric projections and systematic absences. ; _computing_data_collection 'CrystalClear-SM Expert 2.0 r11 (Rigaku, 2011)' _computing_cell_refinement 'CrystalClear-SM Expert 2.0 r11 (Rigaku, 2011)' _computing_data_reduction 'CrystalClear-SM Expert 2.0 r11 (Rigaku, 2011)' _computing_structure_solution 'SHELXL-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-2013 (Sheldrick, 2013)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; ? ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0081P)^2^+10.2099P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary ? _atom_sites_solution_secondary ? _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef . _refine_ls_number_reflns 3992 _refine_ls_number_parameters 203 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0717 _refine_ls_R_factor_gt 0.0595 _refine_ls_wR_factor_ref 0.0896 _refine_ls_wR_factor_gt 0.0856 _refine_ls_goodness_of_fit_ref 1.233 _refine_ls_restrained_S_all 1.233 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_site_symmetry_order _atom_site_calc_flag _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group C11 C 0.5663(7) 0.4930(4) 0.17751(14) 0.0263(12) Uani 1 1 d . . . . . H11A H 0.5284 0.4391 0.1945 0.039 Uiso 1 1 calc R U . . . H11B H 0.4616 0.5253 0.1664 0.039 Uiso 1 1 calc R U . . . H11C H 0.6349 0.5406 0.1928 0.039 Uiso 1 1 calc R U . . . I1 I 0.40340(4) 0.12735(2) 0.14830(2) 0.02040(10) Uani 1 1 d . . . . . C1 C 0.9001(6) 0.3751(3) 0.11391(13) 0.0148(9) Uani 1 1 d . . . . . C1A C 0.9014(7) 0.3767(4) 0.18864(13) 0.0228(11) Uani 1 1 d . . . . . H1A1 H 0.8514 0.4195 0.2093 0.027 Uiso 1 1 calc R U . . . H1A2 H 1.0312 0.3881 0.1876 0.027 Uiso 1 1 calc R U . . . C2 C 1.0522(6) 0.3169(3) 0.10885(14) 0.0175(10) Uani 1 1 d . . . . . H2 H 1.1182 0.2928 0.1305 0.021 Uiso 1 1 calc R U . . . C2A C 0.8659(7) 0.2700(4) 0.19895(14) 0.0230(11) Uani 1 1 d . . . . . H2A1 H 0.7398 0.2543 0.1937 0.028 Uiso 1 1 calc R U . . . H2A2 H 0.9402 0.2270 0.1823 0.028 Uiso 1 1 calc R U . . . C3 C 1.0999(6) 0.2971(3) 0.07134(13) 0.0177(10) Uani 1 1 d . . . . . H3 H 1.1996 0.2561 0.0667 0.021 Uiso 1 1 calc R U . . . C3A C 0.9069(8) 0.2510(4) 0.24114(16) 0.0296(12) Uani 1 1 d . . . . . C4 C 1.0047(6) 0.3362(3) 0.03870(14) 0.0161(10) Uani 1 1 d . . . . . C6 C 0.8003(6) 0.4136(3) 0.08409(13) 0.0127(9) Uani 1 1 d . . . . . C7 C 0.6428(6) 0.4670(3) 0.10224(13) 0.0155(10) Uani 1 1 d . . . . . C8 C 0.6783(6) 0.4537(3) 0.14545(14) 0.0186(10) Uani 1 1 d . . . . . C9 C 0.4680(6) 0.4117(4) 0.09275(15) 0.0206(11) Uani 1 1 d . . . . . H9A H 0.4782 0.3433 0.1013 0.031 Uiso 1 1 calc R U . . . H9B H 0.4463 0.4138 0.0645 0.031 Uiso 1 1 calc R U . . . H9C H 0.3690 0.4432 0.1065 0.031 Uiso 1 1 calc R U . . . C10 C 0.6261(6) 0.5766(3) 0.09224(14) 0.0170(10) Uani 1 1 d . . . . . H10A H 0.5197 0.6035 0.1048 0.026 Uiso 1 1 calc R U . . . H10B H 0.6168 0.5845 0.0638 0.026 Uiso 1 1 calc R U . . . H10C H 0.7313 0.6116 0.1018 0.026 Uiso 1 1 calc R U . . . C12 C 1.0615(6) 0.3161(3) -0.00023(14) 0.0204(11) Uani 1 1 d . . . . . H12 H 1.1612 0.2747 -0.0045 0.024 Uiso 1 1 calc R U . . . C13 C 0.9739(6) 0.3557(3) -0.03136(14) 0.0196(10) Uani 1 1 d . . . . . H13 H 1.0136 0.3427 -0.0572 0.024 Uiso 1 1 calc R U . . . C14 C 0.8245(6) 0.4161(4) -0.02528(14) 0.0199(11) Uani 1 1 d . . . . . H14 H 0.7653 0.4437 -0.0472 0.024 Uiso 1 1 calc R U . . . C15 C 0.7630(6) 0.4359(3) 0.01132(14) 0.0172(10) Uani 1 1 d . . . . . H15 H 0.6610 0.4761 0.0146 0.021 Uiso 1 1 calc R U . . . C16 C 0.8516(6) 0.3963(3) 0.04484(13) 0.0145(10) Uani 1 1 d . . . . . N1 N 0.8224(5) 0.4026(3) 0.15090(11) 0.0169(8) Uani 1 1 d . . . . . O1A O 0.8583(6) 0.1624(3) 0.25296(11) 0.0355(10) Uani 1 1 d . . . . . H1A H 0.8530 0.1613 0.2775 0.053 Uiso 1 1 calc R U . . . O2A O 0.9839(6) 0.3103(3) 0.26173(12) 0.0470(12) Uani 1 1 d . . . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C11 0.034(3) 0.021(3) 0.024(3) -0.002(2) 0.005(2) 0.010(2) I1 0.02335(17) 0.02087(17) 0.01697(17) -0.00017(14) 0.00005(13) 0.00451(14) C1 0.017(2) 0.009(2) 0.018(2) 0.0005(19) 0.0008(18) -0.0022(19) C1A 0.028(3) 0.021(3) 0.020(3) 0.006(2) -0.005(2) 0.001(2) C2 0.014(2) 0.014(2) 0.025(3) 0.0044(19) -0.0039(18) -0.0003(19) C2A 0.030(3) 0.020(3) 0.019(3) 0.000(2) -0.005(2) -0.002(2) C3 0.016(2) 0.015(2) 0.022(3) -0.0020(19) -0.0012(19) 0.000(2) C3A 0.046(3) 0.021(3) 0.021(3) 0.003(2) -0.005(2) 0.000(3) C4 0.016(2) 0.009(2) 0.023(3) 0.0007(19) -0.0014(19) -0.0020(19) C6 0.013(2) 0.008(2) 0.016(2) -0.0002(18) -0.0046(18) -0.0024(18) C7 0.014(2) 0.014(2) 0.018(3) 0.0012(19) -0.0007(18) -0.0010(19) C8 0.022(2) 0.013(2) 0.021(3) -0.001(2) 0.002(2) -0.0043(19) C9 0.018(2) 0.016(3) 0.028(3) 0.002(2) -0.0023(19) -0.003(2) C10 0.018(2) 0.011(2) 0.023(3) 0.0011(19) -0.0041(19) -0.0003(19) C12 0.024(3) 0.013(2) 0.024(3) -0.006(2) 0.001(2) -0.004(2) C13 0.027(3) 0.014(3) 0.018(3) -0.0033(19) 0.0012(19) -0.009(2) C14 0.026(3) 0.015(3) 0.019(3) 0.003(2) -0.007(2) -0.005(2) C15 0.020(2) 0.009(2) 0.022(3) 0.000(2) -0.0052(19) 0.0008(18) C16 0.015(2) 0.009(2) 0.019(3) 0.0016(18) -0.0006(17) -0.0024(18) N1 0.021(2) 0.015(2) 0.015(2) 0.0021(16) -0.0023(16) -0.0015(16) O1A 0.064(3) 0.023(2) 0.020(2) 0.0076(17) -0.0026(19) -0.0093(19) O2A 0.080(3) 0.032(3) 0.029(2) 0.0037(19) -0.024(2) -0.015(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C11 C8 1.483(6) . ? C11 H11A 0.9800 . ? C11 H11B 0.9800 . ? C11 H11C 0.9800 . ? C1 C6 1.370(6) . ? C1 C2 1.404(6) . ? C1 N1 1.442(6) . ? C1A N1 1.463(5) . ? C1A C2A 1.521(7) . ? C1A H1A1 0.9900 . ? C1A H1A2 0.9900 . ? C2 C3 1.358(6) . ? C2 H2 0.9500 . ? C2A C3A 1.497(7) . ? C2A H2A1 0.9900 . ? C2A H2A2 0.9900 . ? C3 C4 1.429(6) . ? C3 H3 0.9500 . ? C3A O2A 1.218(6) . ? C3A O1A 1.325(6) . ? C4 C12 1.424(6) . ? C4 C16 1.430(6) . ? C6 C16 1.416(6) . ? C6 C7 1.523(6) . ? C7 C8 1.511(6) . ? C7 C10 1.539(6) . ? C7 C9 1.551(6) . ? C8 N1 1.303(6) . ? C9 H9A 0.9800 . ? C9 H9B 0.9800 . ? C9 H9C 0.9800 . ? C10 H10A 0.9800 . ? C10 H10B 0.9800 . ? C10 H10C 0.9800 . ? C12 C13 1.364(7) . ? C12 H12 0.9500 . ? C13 C14 1.410(7) . ? C13 H13 0.9500 . ? C14 C15 1.360(7) . ? C14 H14 0.9500 . ? C15 C16 1.431(6) . ? C15 H15 0.9500 . ? O1A H1A 0.8400 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C8 C11 H11A 109.5 . . ? C8 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? C8 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? C6 C1 C2 124.9(4) . . ? C6 C1 N1 109.2(4) . . ? C2 C1 N1 125.8(4) . . ? N1 C1A C2A 111.3(4) . . ? N1 C1A H1A1 109.4 . . ? C2A C1A H1A1 109.4 . . ? N1 C1A H1A2 109.4 . . ? C2A C1A H1A2 109.4 . . ? H1A1 C1A H1A2 108.0 . . ? C3 C2 C1 116.4(4) . . ? C3 C2 H2 121.8 . . ? C1 C2 H2 121.8 . . ? C3A C2A C1A 110.6(4) . . ? C3A C2A H2A1 109.5 . . ? C1A C2A H2A1 109.5 . . ? C3A C2A H2A2 109.5 . . ? C1A C2A H2A2 109.5 . . ? H2A1 C2A H2A2 108.1 . . ? C2 C3 C4 122.0(4) . . ? C2 C3 H3 119.0 . . ? C4 C3 H3 119.0 . . ? O2A C3A O1A 124.1(5) . . ? O2A C3A C2A 122.6(5) . . ? O1A C3A C2A 113.2(5) . . ? C12 C4 C16 119.3(4) . . ? C12 C4 C3 120.4(4) . . ? C16 C4 C3 120.2(4) . . ? C1 C6 C16 119.4(4) . . ? C1 C6 C7 107.9(4) . . ? C16 C6 C7 132.7(4) . . ? C8 C7 C6 101.7(4) . . ? C8 C7 C10 110.3(4) . . ? C6 C7 C10 115.9(4) . . ? C8 C7 C9 107.2(4) . . ? C6 C7 C9 110.1(4) . . ? C10 C7 C9 110.9(4) . . ? N1 C8 C11 124.2(5) . . ? N1 C8 C7 110.5(4) . . ? C11 C8 C7 125.3(4) . . ? C7 C9 H9A 109.5 . . ? C7 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? C7 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? C7 C10 H10A 109.5 . . ? C7 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? C7 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? C13 C12 C4 120.5(4) . . ? C13 C12 H12 119.8 . . ? C4 C12 H12 119.8 . . ? C12 C13 C14 120.2(5) . . ? C12 C13 H13 119.9 . . ? C14 C13 H13 119.9 . . ? C15 C14 C13 121.5(4) . . ? C15 C14 H14 119.2 . . ? C13 C14 H14 119.2 . . ? C14 C15 C16 120.1(4) . . ? C14 C15 H15 119.9 . . ? C16 C15 H15 119.9 . . ? C6 C16 C4 117.1(4) . . ? C6 C16 C15 124.6(4) . . ? C4 C16 C15 118.4(4) . . ? C8 N1 C1 110.6(4) . . ? C8 N1 C1A 126.4(4) . . ? C1 N1 C1A 123.0(4) . . ? C3A O1A H1A 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C6 C1 C2 C3 -1.0(7) . . . . ? N1 C1 C2 C3 177.9(4) . . . . ? N1 C1A C2A C3A -166.1(4) . . . . ? C1 C2 C3 C4 2.2(7) . . . . ? C1A C2A C3A O2A -10.5(8) . . . . ? C1A C2A C3A O1A 172.3(5) . . . . ? C2 C3 C4 C12 178.2(4) . . . . ? C2 C3 C4 C16 -1.5(7) . . . . ? C2 C1 C6 C16 -1.0(7) . . . . ? N1 C1 C6 C16 179.9(4) . . . . ? C2 C1 C6 C7 177.0(4) . . . . ? N1 C1 C6 C7 -2.1(5) . . . . ? C1 C6 C7 C8 1.8(5) . . . . ? C16 C6 C7 C8 179.5(5) . . . . ? C1 C6 C7 C10 121.5(4) . . . . ? C16 C6 C7 C10 -60.8(6) . . . . ? C1 C6 C7 C9 -111.6(4) . . . . ? C16 C6 C7 C9 66.0(6) . . . . ? C6 C7 C8 N1 -1.0(5) . . . . ? C10 C7 C8 N1 -124.5(4) . . . . ? C9 C7 C8 N1 114.6(4) . . . . ? C6 C7 C8 C11 179.0(4) . . . . ? C10 C7 C8 C11 55.4(6) . . . . ? C9 C7 C8 C11 -65.4(6) . . . . ? C16 C4 C12 C13 1.7(7) . . . . ? C3 C4 C12 C13 -178.0(4) . . . . ? C4 C12 C13 C14 -0.8(7) . . . . ? C12 C13 C14 C15 -0.5(7) . . . . ? C13 C14 C15 C16 0.9(7) . . . . ? C1 C6 C16 C4 1.7(6) . . . . ? C7 C6 C16 C4 -175.7(4) . . . . ? C1 C6 C16 C15 -177.2(4) . . . . ? C7 C6 C16 C15 5.4(8) . . . . ? C12 C4 C16 C6 179.7(4) . . . . ? C3 C4 C16 C6 -0.6(6) . . . . ? C12 C4 C16 C15 -1.3(6) . . . . ? C3 C4 C16 C15 178.4(4) . . . . ? C14 C15 C16 C6 178.9(4) . . . . ? C14 C15 C16 C4 0.1(7) . . . . ? C11 C8 N1 C1 179.8(4) . . . . ? C7 C8 N1 C1 -0.2(5) . . . . ? C11 C8 N1 C1A -1.5(7) . . . . ? C7 C8 N1 C1A 178.5(4) . . . . ? C6 C1 N1 C8 1.5(5) . . . . ? C2 C1 N1 C8 -177.6(4) . . . . ? C6 C1 N1 C1A -177.3(4) . . . . ? C2 C1 N1 C1A 3.6(7) . . . . ? C2A C1A N1 C8 104.2(5) . . . . ? C2A C1A N1 C1 -77.3(5) . . . . ? _refine_diff_density_max 0.908 _refine_diff_density_min -0.631 _refine_diff_density_rms 0.113 # END _database_code_depnum_ccdc_archive 'CCDC 977426' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_12a _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C26 H33 N O5' _chemical_formula_sum 'C26 H33 N O5' _chemical_formula_weight 439.53 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P21/c _symmetry_space_group_name_Hall '-P 2ybc ' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 12.7035(9) _cell_length_b 18.2291(13) _cell_length_c 11.1693(8) _cell_angle_alpha 90.00 _cell_angle_beta 111.529(2) _cell_angle_gamma 90.00 _cell_volume 2406.1(3) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min 2.1 _cell_measurement_theta_max 27.5 _exptl_crystal_description column _exptl_crystal_colour Orange _exptl_crystal_size_max 0.43 _exptl_crystal_size_mid 0.09 _exptl_crystal_size_min 0.07 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.213 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 944 _exptl_absorpt_coefficient_mu 0.083 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9650 _exptl_absorpt_correction_T_max 0.9942 _exptl_absorpt_process_details 'CrystalClear-SM Expert 3.1 b27 (Rigaku, 2012)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_source_power 2.5 _diffrn_source_voltage 45.0 _diffrn_source_current 55.0 _diffrn_radiation_wavelength 0.71075 _diffrn_radiation_type 'Mo K\a' _diffrn_source 'Rotating Anode' _diffrn_radiation_monochromator Confocal _diffrn_measurement_specimen_support Mitegen _diffrn_detector CCD _diffrn_measurement_device ; AFC12 (Right): Kappa 3 circle ; _diffrn_measurement_device_type ; Rigaku Saturn724+ (2x2 bin mode) ; _diffrn_detector_area_resol_mean 28.5714 _diffrn_measurement_method 'profile data from \w-scans' _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 30172 _diffrn_reflns_av_R_equivalents 0.0562 _diffrn_reflns_av_sigmaI/netI 0.0353 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -23 _diffrn_reflns_limit_k_max 22 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 2.97 _diffrn_reflns_theta_max 27.48 _reflns_number_total 5504 _reflns_number_gt 4195 _reflns_threshold_expression >2\s(I) _computing_data_collection 'CrystalClear-SM Expert 3.1 b27 (Rigaku, 2012)' _computing_cell_refinement 'CrystalClear-SM Expert 3.1 b27 (Rigaku, 2012)' _computing_data_reduction 'CrystalClear-SM Expert 3.1 b27 (Rigaku, 2012)' _computing_structure_solution 'SHELXL-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2\s(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0683P)^2^+0.2530P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 5504 _refine_ls_number_parameters 294 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0593 _refine_ls_R_factor_gt 0.0406 _refine_ls_wR_factor_ref 0.1137 _refine_ls_wR_factor_gt 0.1051 _refine_ls_goodness_of_fit_ref 0.975 _refine_ls_restrained_S_all 0.975 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.62144(10) 0.45045(6) 0.21088(11) 0.0185(2) Uani 1 1 d . . . C1A C 0.46619(10) 0.38895(6) 0.26195(11) 0.0200(3) Uani 1 1 d . . . H1A1 H 0.4427 0.3918 0.3371 0.024 Uiso 1 1 calc R . . H1A2 H 0.5114 0.3437 0.2703 0.024 Uiso 1 1 calc R . . C1S C 0.40031(10) 0.60459(7) 0.38345(11) 0.0210(3) Uani 1 1 d . . . C2 C 0.65989(10) 0.39062(7) 0.16154(11) 0.0208(3) Uani 1 1 d . . . H2 H 0.6281 0.3432 0.1590 0.025 Uiso 1 1 calc R . . C2A C 0.36079(10) 0.38493(7) 0.13847(11) 0.0230(3) Uani 1 1 d . . . H2A1 H 0.3200 0.4323 0.1256 0.028 Uiso 1 1 calc R . . H2A2 H 0.3844 0.3771 0.0643 0.028 Uiso 1 1 calc R . . C2S C 0.42763(11) 0.68462(7) 0.40920(12) 0.0227(3) Uani 1 1 d . . . C3 C 0.74634(10) 0.40274(7) 0.11615(11) 0.0214(3) Uani 1 1 d . . . H3 H 0.7744 0.3629 0.0819 0.026 Uiso 1 1 calc R . . C3A C 0.28051(11) 0.32327(7) 0.14206(12) 0.0255(3) Uani 1 1 d . . . H3A1 H 0.2257 0.3148 0.0536 0.031 Uiso 1 1 calc R . . H3A2 H 0.3249 0.2777 0.1710 0.031 Uiso 1 1 calc R . . C3S C 0.33081(11) 0.69060(7) 0.45876(12) 0.0224(3) Uani 1 1 d . . . C4 C 0.79318(10) 0.47288(7) 0.11983(11) 0.0203(3) Uani 1 1 d . . . C4A C 0.21518(11) 0.33827(7) 0.22970(13) 0.0260(3) Uani 1 1 d . . . H4A1 H 0.2696 0.3466 0.3184 0.031 Uiso 1 1 calc R . . H4A2 H 0.1702 0.3836 0.2007 0.031 Uiso 1 1 calc R . . C4S C 0.31147(10) 0.61187(7) 0.42724(11) 0.0213(3) Uani 1 1 d . . . C5 C 0.75227(10) 0.53278(6) 0.16973(11) 0.0190(3) Uani 1 1 d . . . H5 H 0.7834 0.5804 0.1719 0.023 Uiso 1 1 calc R . . C5A C 0.13627(11) 0.27566(8) 0.23107(13) 0.0287(3) Uani 1 1 d . . . H5A1 H 0.0903 0.2626 0.1409 0.034 Uiso 1 1 calc R . . H5A2 H 0.1829 0.2324 0.2711 0.034 Uiso 1 1 calc R . . C5S C 0.15177(11) 0.58230(7) 0.48189(13) 0.0250(3) Uani 1 1 d . . . H5S1 H 0.1475 0.6364 0.4857 0.030 Uiso 1 1 calc R . . H5S2 H 0.1686 0.5625 0.5695 0.030 Uiso 1 1 calc R . . C6 C 0.66655(10) 0.52128(6) 0.21529(11) 0.0182(2) Uani 1 1 d . . . C6A C 0.05666(11) 0.29106(7) 0.30154(12) 0.0252(3) Uani 1 1 d . . . H6A1 H 0.0114 0.3353 0.2642 0.030 Uiso 1 1 calc R . . H6A2 H 0.1018 0.3014 0.3931 0.030 Uiso 1 1 calc R . . C6S C 0.04161(13) 0.55185(9) 0.39063(15) 0.0383(4) Uani 1 1 d . . . H6S1 H 0.0250 0.5727 0.3048 0.058 Uiso 1 1 calc R . . H6S2 H -0.0192 0.5646 0.4211 0.058 Uiso 1 1 calc R . . H6S3 H 0.0473 0.4984 0.3865 0.058 Uiso 1 1 calc R . . C7 C 0.60475(10) 0.57429(6) 0.27147(11) 0.0186(2) Uani 1 1 d . . . C7A C -0.02311(12) 0.22723(8) 0.29355(14) 0.0297(3) Uani 1 1 d . . . H7A1 H -0.0642 0.2150 0.2018 0.036 Uiso 1 1 calc R . . H7A2 H 0.0226 0.1839 0.3351 0.036 Uiso 1 1 calc R . . C8 C 0.51829(10) 0.52330(6) 0.29569(11) 0.0191(3) Uani 1 1 d . . . C8A C -0.10894(12) 0.24145(8) 0.35582(14) 0.0309(3) Uani 1 1 d . . . H8A1 H -0.0694 0.2515 0.4477 0.046 Uiso 1 1 calc R . . H8A2 H -0.1574 0.1982 0.3453 0.046 Uiso 1 1 calc R . . H8A3 H -0.1556 0.2839 0.3147 0.046 Uiso 1 1 calc R . . C9 C 0.54431(11) 0.63438(7) 0.17270(12) 0.0227(3) Uani 1 1 d . . . H9A H 0.6007 0.6635 0.1529 0.034 Uiso 1 1 calc R . . H9B H 0.5014 0.6663 0.2088 0.034 Uiso 1 1 calc R . . H9C H 0.4925 0.6114 0.0937 0.034 Uiso 1 1 calc R . . C10 C 0.68726(10) 0.60773(7) 0.39832(11) 0.0217(3) Uani 1 1 d . . . H10A H 0.7198 0.5685 0.4610 0.032 Uiso 1 1 calc R . . H10B H 0.6463 0.6422 0.4327 0.032 Uiso 1 1 calc R . . H10C H 0.7481 0.6337 0.3817 0.032 Uiso 1 1 calc R . . C11 C 0.43360(11) 0.53844(7) 0.33982(11) 0.0213(3) Uani 1 1 d . . . H11 H 0.3886 0.4971 0.3417 0.026 Uiso 1 1 calc R . . C12 C 0.88280(11) 0.48520(7) 0.06736(12) 0.0217(3) Uani 1 1 d . . . N1 N 0.53631(8) 0.45270(5) 0.26204(9) 0.0193(2) Uani 1 1 d . . . O1 O 0.91961(8) 0.54701(5) 0.05986(9) 0.0276(2) Uani 1 1 d . . . O1S O 0.49603(8) 0.72818(5) 0.39880(10) 0.0308(2) Uani 1 1 d . . . O2 O 0.91928(8) 0.42547(5) 0.02926(10) 0.0314(2) Uani 1 1 d . . . H2A H 0.9681 0.4367 -0.0018 0.047 Uiso 1 1 calc R . . O2S O 0.29100(8) 0.73833(5) 0.50507(10) 0.0313(2) Uani 1 1 d . . . O3S O 0.24032(8) 0.56063(5) 0.43411(9) 0.0281(2) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0181(6) 0.0189(6) 0.0179(6) 0.0000(4) 0.0057(4) 0.0002(4) C1A 0.0221(6) 0.0148(6) 0.0246(6) 0.0005(4) 0.0105(5) -0.0015(4) C1S 0.0240(6) 0.0188(6) 0.0209(6) 0.0018(4) 0.0091(5) -0.0007(5) C2 0.0217(6) 0.0161(6) 0.0235(6) -0.0019(4) 0.0069(5) -0.0015(5) C2A 0.0234(6) 0.0249(6) 0.0215(6) -0.0013(5) 0.0092(5) -0.0026(5) C2S 0.0274(6) 0.0172(6) 0.0260(6) 0.0027(4) 0.0129(5) 0.0029(5) C3 0.0217(6) 0.0189(6) 0.0228(6) -0.0019(4) 0.0073(5) 0.0020(5) C3A 0.0248(6) 0.0256(7) 0.0262(6) -0.0063(5) 0.0095(5) -0.0059(5) C3S 0.0254(6) 0.0180(6) 0.0257(6) 0.0034(5) 0.0115(5) 0.0026(5) C4 0.0203(6) 0.0190(6) 0.0215(6) -0.0003(4) 0.0075(5) 0.0006(5) C4A 0.0243(6) 0.0260(7) 0.0296(7) -0.0041(5) 0.0119(5) -0.0048(5) C4S 0.0245(6) 0.0181(6) 0.0226(6) 0.0027(4) 0.0101(5) 0.0013(5) C5 0.0195(6) 0.0157(6) 0.0216(6) 0.0004(4) 0.0071(5) -0.0009(4) C5A 0.0269(7) 0.0267(7) 0.0357(7) -0.0069(5) 0.0154(6) -0.0057(5) C5S 0.0245(6) 0.0252(7) 0.0291(7) 0.0028(5) 0.0145(5) 0.0019(5) C6 0.0193(6) 0.0168(6) 0.0177(6) 0.0002(4) 0.0058(4) 0.0006(4) C6A 0.0247(6) 0.0241(7) 0.0282(6) -0.0018(5) 0.0112(5) -0.0013(5) C6S 0.0334(8) 0.0372(9) 0.0416(8) 0.0048(6) 0.0105(6) -0.0047(6) C7 0.0203(6) 0.0156(6) 0.0216(6) 0.0003(4) 0.0096(5) 0.0002(4) C7A 0.0294(7) 0.0256(7) 0.0369(8) -0.0050(5) 0.0153(6) -0.0041(5) C8 0.0214(6) 0.0163(6) 0.0190(6) 0.0007(4) 0.0065(5) 0.0001(4) C8A 0.0285(7) 0.0326(8) 0.0341(7) 0.0024(6) 0.0144(6) -0.0005(6) C9 0.0251(6) 0.0207(6) 0.0238(6) 0.0041(5) 0.0109(5) 0.0038(5) C10 0.0248(6) 0.0171(6) 0.0227(6) -0.0010(4) 0.0082(5) -0.0001(5) C11 0.0253(6) 0.0165(6) 0.0243(6) -0.0001(4) 0.0117(5) -0.0016(5) C12 0.0229(6) 0.0189(6) 0.0236(6) -0.0006(4) 0.0089(5) 0.0017(5) N1 0.0211(5) 0.0150(5) 0.0236(5) -0.0012(4) 0.0103(4) -0.0009(4) O1 0.0308(5) 0.0196(5) 0.0396(5) -0.0011(4) 0.0213(4) -0.0009(4) O1S 0.0350(5) 0.0185(5) 0.0473(6) -0.0008(4) 0.0251(5) -0.0019(4) O2 0.0345(5) 0.0206(5) 0.0514(6) -0.0045(4) 0.0305(5) -0.0015(4) O2S 0.0386(5) 0.0195(5) 0.0442(6) -0.0007(4) 0.0253(5) 0.0035(4) O3S 0.0296(5) 0.0204(5) 0.0420(5) -0.0025(4) 0.0223(4) -0.0039(4) _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C2 1.3889(17) . ? C1 N1 1.3969(16) . ? C1 C6 1.4061(16) . ? C1A N1 1.4641(15) . ? C1A C2A 1.5313(16) . ? C1A H1A1 0.9900 . ? C1A H1A2 0.9900 . ? C1S C4S 1.3913(18) . ? C1S C11 1.4218(17) . ? C1S C2S 1.5027(17) . ? C2 C3 1.3858(18) . ? C2 H2 0.9500 . ? C2A C3A 1.5280(18) . ? C2A H2A1 0.9900 . ? C2A H2A2 0.9900 . ? C2S O1S 1.2136(16) . ? C2S C3S 1.5268(18) . ? C3 C4 1.4045(17) . ? C3 H3 0.9500 . ? C3A C4A 1.5225(19) . ? C3A H3A1 0.9900 . ? C3A H3A2 0.9900 . ? C3S O2S 1.2132(16) . ? C3S C4S 1.4767(17) . ? C4 C5 1.4090(17) . ? C4 C12 1.4765(18) . ? C4A C5A 1.5229(18) . ? C4A H4A1 0.9900 . ? C4A H4A2 0.9900 . ? C4S O3S 1.3214(15) . ? C5 C6 1.3768(18) . ? C5 H5 0.9500 . ? C5A C6A 1.5183(19) . ? C5A H5A1 0.9900 . ? C5A H5A2 0.9900 . ? C5S O3S 1.4653(16) . ? C5S C6S 1.5028(19) . ? C5S H5S1 0.9900 . ? C5S H5S2 0.9900 . ? C6 C7 1.5184(16) . ? C6A C7A 1.5240(18) . ? C6A H6A1 0.9900 . ? C6A H6A2 0.9900 . ? C6S H6S1 0.9800 . ? C6S H6S2 0.9800 . ? C6S H6S3 0.9800 . ? C7 C8 1.5368(17) . ? C7 C10 1.5452(16) . ? C7 C9 1.5443(16) . ? C7A C8A 1.515(2) . ? C7A H7A1 0.9900 . ? C7A H7A2 0.9900 . ? C8 C11 1.3660(18) . ? C8 N1 1.3832(15) . ? C8A H8A1 0.9800 . ? C8A H8A2 0.9800 . ? C8A H8A3 0.9800 . ? C9 H9A 0.9800 . ? C9 H9B 0.9800 . ? C9 H9C 0.9800 . ? C10 H10A 0.9800 . ? C10 H10B 0.9800 . ? C10 H10C 0.9800 . ? C11 H11 0.9500 . ? C12 O1 1.2346(15) . ? C12 O2 1.3137(15) . ? O2 H2A 0.8400 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 C1 N1 128.54(11) . . ? C2 C1 C6 122.47(12) . . ? N1 C1 C6 108.99(10) . . ? N1 C1A C2A 111.67(10) . . ? N1 C1A H1A1 109.3 . . ? C2A C1A H1A1 109.3 . . ? N1 C1A H1A2 109.3 . . ? C2A C1A H1A2 109.3 . . ? H1A1 C1A H1A2 107.9 . . ? C4S C1S C11 125.66(12) . . ? C4S C1S C2S 90.02(10) . . ? C11 C1S C2S 144.30(12) . . ? C3 C2 C1 117.47(11) . . ? C3 C2 H2 121.3 . . ? C1 C2 H2 121.3 . . ? C3A C2A C1A 112.52(10) . . ? C3A C2A H2A1 109.1 . . ? C1A C2A H2A1 109.1 . . ? C3A C2A H2A2 109.1 . . ? C1A C2A H2A2 109.1 . . ? H2A1 C2A H2A2 107.8 . . ? O1S C2S C1S 137.73(12) . . ? O1S C2S C3S 133.49(12) . . ? C1S C2S C3S 88.77(10) . . ? C2 C3 C4 121.22(11) . . ? C2 C3 H3 119.4 . . ? C4 C3 H3 119.4 . . ? C4A C3A C2A 114.28(11) . . ? C4A C3A H3A1 108.7 . . ? C2A C3A H3A1 108.7 . . ? C4A C3A H3A2 108.7 . . ? C2A C3A H3A2 108.7 . . ? H3A1 C3A H3A2 107.6 . . ? O2S C3S C4S 137.70(13) . . ? O2S C3S C2S 136.31(12) . . ? C4S C3S C2S 85.97(10) . . ? C3 C4 C5 120.22(12) . . ? C3 C4 C12 120.46(11) . . ? C5 C4 C12 119.29(11) . . ? C5A C4A C3A 112.83(11) . . ? C5A C4A H4A1 109.0 . . ? C3A C4A H4A1 109.0 . . ? C5A C4A H4A2 109.0 . . ? C3A C4A H4A2 109.0 . . ? H4A1 C4A H4A2 107.8 . . ? O3S C4S C1S 127.83(11) . . ? O3S C4S C3S 136.94(12) . . ? C1S C4S C3S 95.23(10) . . ? C6 C5 C4 119.00(11) . . ? C6 C5 H5 120.5 . . ? C4 C5 H5 120.5 . . ? C6A C5A C4A 115.64(11) . . ? C6A C5A H5A1 108.4 . . ? C4A C5A H5A1 108.4 . . ? C6A C5A H5A2 108.4 . . ? C4A C5A H5A2 108.4 . . ? H5A1 C5A H5A2 107.4 . . ? O3S C5S C6S 107.55(11) . . ? O3S C5S H5S1 110.2 . . ? C6S C5S H5S1 110.2 . . ? O3S C5S H5S2 110.2 . . ? C6S C5S H5S2 110.2 . . ? H5S1 C5S H5S2 108.5 . . ? C5 C6 C1 119.62(11) . . ? C5 C6 C7 130.91(11) . . ? C1 C6 C7 109.45(11) . . ? C5A C6A C7A 112.56(11) . . ? C5A C6A H6A1 109.1 . . ? C7A C6A H6A1 109.1 . . ? C5A C6A H6A2 109.1 . . ? C7A C6A H6A2 109.1 . . ? H6A1 C6A H6A2 107.8 . . ? C5S C6S H6S1 109.5 . . ? C5S C6S H6S2 109.5 . . ? H6S1 C6S H6S2 109.5 . . ? C5S C6S H6S3 109.5 . . ? H6S1 C6S H6S3 109.5 . . ? H6S2 C6S H6S3 109.5 . . ? C6 C7 C8 101.49(9) . . ? C6 C7 C10 110.51(9) . . ? C8 C7 C10 111.43(10) . . ? C6 C7 C9 110.68(10) . . ? C8 C7 C9 110.78(10) . . ? C10 C7 C9 111.55(10) . . ? C8A C7A C6A 114.68(11) . . ? C8A C7A H7A1 108.6 . . ? C6A C7A H7A1 108.6 . . ? C8A C7A H7A2 108.6 . . ? C6A C7A H7A2 108.6 . . ? H7A1 C7A H7A2 107.6 . . ? C11 C8 N1 121.12(11) . . ? C11 C8 C7 130.53(11) . . ? N1 C8 C7 108.34(10) . . ? C7A C8A H8A1 109.5 . . ? C7A C8A H8A2 109.5 . . ? H8A1 C8A H8A2 109.5 . . ? C7A C8A H8A3 109.5 . . ? H8A1 C8A H8A3 109.5 . . ? H8A2 C8A H8A3 109.5 . . ? C7 C9 H9A 109.5 . . ? C7 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? C7 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? C7 C10 H10A 109.5 . . ? C7 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? C7 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? C8 C11 C1S 131.89(12) . . ? C8 C11 H11 114.1 . . ? C1S C11 H11 114.1 . . ? O1 C12 O2 123.17(12) . . ? O1 C12 C4 122.16(11) . . ? O2 C12 C4 114.68(11) . . ? C8 N1 C1 111.64(10) . . ? C8 N1 C1A 125.27(10) . . ? C1 N1 C1A 122.59(10) . . ? C12 O2 H2A 109.5 . . ? C4S O3S C5S 117.61(10) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N1 C1 C2 C3 -179.95(11) . . . . ? C6 C1 C2 C3 0.28(17) . . . . ? N1 C1A C2A C3A -174.28(10) . . . . ? C4S C1S C2S O1S -179.94(16) . . . . ? C11 C1S C2S O1S 1.8(3) . . . . ? C4S C1S C2S C3S 0.87(9) . . . . ? C11 C1S C2S C3S -177.38(17) . . . . ? C1 C2 C3 C4 -0.05(17) . . . . ? C1A C2A C3A C4A 73.27(14) . . . . ? O1S C2S C3S O2S -1.5(3) . . . . ? C1S C2S C3S O2S 177.77(15) . . . . ? O1S C2S C3S C4S 179.92(15) . . . . ? C1S C2S C3S C4S -0.82(9) . . . . ? C2 C3 C4 C5 -0.29(17) . . . . ? C2 C3 C4 C12 -178.10(10) . . . . ? C2A C3A C4A C5A -179.89(11) . . . . ? C11 C1S C4S O3S -1.7(2) . . . . ? C2S C1S C4S O3S 179.53(12) . . . . ? C11 C1S C4S C3S 177.84(12) . . . . ? C2S C1S C4S C3S -0.91(9) . . . . ? O2S C3S C4S O3S 1.8(3) . . . . ? C2S C3S C4S O3S -179.61(15) . . . . ? O2S C3S C4S C1S -177.66(16) . . . . ? C2S C3S C4S C1S 0.89(9) . . . . ? C3 C4 C5 C6 0.41(17) . . . . ? C12 C4 C5 C6 178.25(10) . . . . ? C3A C4A C5A C6A -171.87(11) . . . . ? C4 C5 C6 C1 -0.19(16) . . . . ? C4 C5 C6 C7 -178.78(11) . . . . ? C2 C1 C6 C5 -0.17(17) . . . . ? N1 C1 C6 C5 -179.97(10) . . . . ? C2 C1 C6 C7 178.71(10) . . . . ? N1 C1 C6 C7 -1.09(12) . . . . ? C4A C5A C6A C7A 177.41(11) . . . . ? C5 C6 C7 C8 177.95(11) . . . . ? C1 C6 C7 C8 -0.76(11) . . . . ? C5 C6 C7 C10 -63.76(16) . . . . ? C1 C6 C7 C10 117.54(11) . . . . ? C5 C6 C7 C9 60.33(16) . . . . ? C1 C6 C7 C9 -118.38(11) . . . . ? C5A C6A C7A C8A -176.65(11) . . . . ? C6 C7 C8 C11 -176.46(12) . . . . ? C10 C7 C8 C11 65.91(16) . . . . ? C9 C7 C8 C11 -58.91(16) . . . . ? C6 C7 C8 N1 2.37(11) . . . . ? C10 C7 C8 N1 -115.26(11) . . . . ? C9 C7 C8 N1 119.92(10) . . . . ? N1 C8 C11 C1S 177.88(12) . . . . ? C7 C8 C11 C1S -3.4(2) . . . . ? C4S C1S C11 C8 -179.46(12) . . . . ? C2S C1S C11 C8 -1.6(3) . . . . ? C3 C4 C12 O1 174.23(11) . . . . ? C5 C4 C12 O1 -3.60(17) . . . . ? C3 C4 C12 O2 -5.49(16) . . . . ? C5 C4 C12 O2 176.68(11) . . . . ? C11 C8 N1 C1 175.70(10) . . . . ? C7 C8 N1 C1 -3.27(12) . . . . ? C11 C8 N1 C1A 3.73(17) . . . . ? C7 C8 N1 C1A -175.24(10) . . . . ? C2 C1 N1 C8 -177.01(11) . . . . ? C6 C1 N1 C8 2.78(13) . . . . ? C2 C1 N1 C1A -4.78(18) . . . . ? C6 C1 N1 C1A 175.01(10) . . . . ? C2A C1A N1 C8 82.34(14) . . . . ? C2A C1A N1 C1 -88.80(13) . . . . ? C1S C4S O3S C5S -178.89(11) . . . . ? C3S C4S O3S C5S 1.7(2) . . . . ? C6S C5S O3S C4S 132.29(12) . . . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.305 _refine_diff_density_min -0.199 _refine_diff_density_rms 0.042 _database_code_depnum_ccdc_archive 'CCDC 977427' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_12b _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C104 H130 N4 O20' _chemical_formula_weight 1756.12 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _space_group_crystal_system triclinic _space_group_IT_number 2 _space_group_name_H-M_alt 'P -1' _space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 10.8885(8) _cell_length_b 17.3070(11) _cell_length_c 27.892(2) _cell_angle_alpha 78.372(3) _cell_angle_beta 80.234(3) _cell_angle_gamma 77.874(3) _cell_volume 4988.8(6) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min 2.3 _cell_measurement_theta_max 27.5 _exptl_crystal_description shard _exptl_crystal_colour yellow _exptl_crystal_size_max 0.38 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.03 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.169 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1884 _exptl_absorpt_coefficient_mu 0.080 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9701 _exptl_absorpt_correction_T_max 0.9976 _exptl_absorpt_process_details 'CrystalClear-SM Expert 3.1 b27 (Rigaku, 2012)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_source_power 2.5 _diffrn_source_voltage 45.0 _diffrn_source_current 55.0 _diffrn_radiation_wavelength 0.71075 _diffrn_radiation_type 'Mo K\a' _diffrn_source 'Rotating Anode' _diffrn_radiation_monochromator Confocal _diffrn_measurement_specimen_support Mitegen _diffrn_detector CCD _diffrn_measurement_device ; AFC12 (Right): Kappa 3 circle ; _diffrn_measurement_device_type ; Rigaku Saturn724+ (2x2 bin mode) ; _diffrn_detector_area_resol_mean 28.5714 _diffrn_measurement_method 'profile data from \w-scans' _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 47382 _diffrn_reflns_av_R_equivalents 0.0964 _diffrn_reflns_av_sigmaI/netI 0.1016 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -20 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min -33 _diffrn_reflns_limit_l_max 33 _diffrn_reflns_theta_min 3.03 _diffrn_reflns_theta_max 25.03 _reflns_number_total 17294 _reflns_number_gt 9296 _reflns_threshold_expression >2\s(I) _computing_data_collection 'CrystalClear-SM Expert 3.1 b27 (Rigaku, 2012)' _computing_cell_refinement 'CrystalClear-SM Expert 3.1 b27 (Rigaku, 2012)' _computing_data_reduction 'CrystalClear-SM Expert 3.1 b27 (Rigaku, 2012)' _computing_structure_solution 'SHELXL-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Asymmetric part of the unit cell contains 4 indemendent molecules (Z'=4) Two of them exhibit positional disored on long aliphatic chain, which has been modelled over two sites. For disordered components vibrational restraints (SIMU/DELU), similar displacement restraints (EADP), ISOR and distance/angle restraints DFIX/DANG had to be used to maintain sensible geometries and atomic displacement ellipsoids. Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2\s(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.2000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 17294 _refine_ls_number_parameters 1259 _refine_ls_number_restraints 1444 _refine_ls_R_factor_all 0.1697 _refine_ls_R_factor_gt 0.1066 _refine_ls_wR_factor_ref 0.3071 _refine_ls_wR_factor_gt 0.2603 _refine_ls_goodness_of_fit_ref 0.965 _refine_ls_restrained_S_all 0.978 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C -0.6679(4) 0.2473(2) 0.37752(14) 0.0167(8) Uani 1 1 d U . . C2 C -0.7962(4) 0.2568(2) 0.37400(14) 0.0197(9) Uani 1 1 d U . . H2 H -0.8527 0.2322 0.3994 0.024 Uiso 1 1 calc R . . C3 C -0.8372(4) 0.3042(3) 0.33128(15) 0.0247(10) Uani 1 1 d U . . H3 H -0.9245 0.3127 0.3276 0.030 Uiso 1 1 calc R . . C4 C -0.7548(4) 0.3396(3) 0.29366(15) 0.0233(9) Uani 1 1 d U . . C5 C -0.6239(4) 0.3253(2) 0.29733(15) 0.0215(9) Uani 1 1 d U . . H5 H -0.5665 0.3476 0.2712 0.026 Uiso 1 1 calc R . . C6 C -0.5808(4) 0.2783(2) 0.33971(14) 0.0174(8) Uani 1 1 d U . . C7 C -0.4504(4) 0.2569(2) 0.35543(14) 0.0163(8) Uani 1 1 d U . . C8 C -0.4783(4) 0.2167(2) 0.40938(13) 0.0137(8) Uani 1 1 d U . . C9 C -0.3913(4) 0.3321(2) 0.34964(15) 0.0191(9) Uani 1 1 d U . . H9A H -0.3764 0.3553 0.3145 0.029 Uiso 1 1 calc R . . H9B H -0.3107 0.3174 0.3633 0.029 Uiso 1 1 calc R . . H9C H -0.4494 0.3716 0.3674 0.029 Uiso 1 1 calc R . . C10 C -0.3621(4) 0.1962(3) 0.32534(14) 0.0232(9) Uani 1 1 d U . . H10A H -0.4004 0.1487 0.3287 0.035 Uiso 1 1 calc R . . H10B H -0.2799 0.1805 0.3378 0.035 Uiso 1 1 calc R . . H10C H -0.3500 0.2211 0.2905 0.035 Uiso 1 1 calc R . . C12 C -0.8071(4) 0.3949(3) 0.25104(16) 0.0292(11) Uani 1 1 d U . . C1A C -0.6683(4) 0.1733(2) 0.46527(14) 0.0161(8) Uani 1 1 d U . . H1A1 H -0.7609 0.1924 0.4662 0.019 Uiso 1 1 calc R . . H1A2 H -0.6409 0.1914 0.4926 0.019 Uiso 1 1 calc R . . C2A C -0.6407(4) 0.0812(2) 0.47341(15) 0.0220(9) Uani 1 1 d U . . H2A1 H -0.6632 0.0632 0.4451 0.026 Uiso 1 1 calc R . . H2A2 H -0.5487 0.0620 0.4745 0.026 Uiso 1 1 calc R . . C3A C -0.7134(4) 0.0438(3) 0.52074(16) 0.0248(10) Uani 1 1 d U . . H3A1 H -0.7043 -0.0142 0.5204 0.030 Uiso 1 1 calc R . . H3A2 H -0.8044 0.0676 0.5206 0.030 Uiso 1 1 calc R . . C4A C -0.6741(5) 0.0534(3) 0.56899(15) 0.0289(10) Uani 1 1 d U . . H4A1 H -0.6707 0.1105 0.5678 0.035 Uiso 1 1 calc R . . H4A2 H -0.5881 0.0217 0.5724 0.035 Uiso 1 1 calc R . . C5A C -0.7662(5) 0.0255(3) 0.61419(16) 0.0323(11) Uani 1 1 d U . . H5A1 H -0.8525 0.0559 0.6098 0.039 Uiso 1 1 calc R . . H5A2 H -0.7676 -0.0319 0.6154 0.039 Uiso 1 1 calc R . . C6A C -0.7352(6) 0.0355(3) 0.66324(18) 0.0445(13) Uani 1 1 d U . . H6A1 H -0.7238 0.0916 0.6607 0.053 Uiso 1 1 calc R . . H6A2 H -0.6533 0.0002 0.6695 0.053 Uiso 1 1 calc R . . C7A C -0.8336(7) 0.0169(4) 0.7073(2) 0.0645(18) Uani 1 1 d U . . H7A1 H -0.8502 -0.0376 0.7085 0.077 Uiso 1 1 calc R . . H7A2 H -0.7989 0.0168 0.7379 0.077 Uiso 1 1 calc R . . C8A C -0.9560(8) 0.0750(6) 0.7060(3) 0.092(3) Uani 1 1 d U . . H8A1 H -0.9423 0.1280 0.7089 0.139 Uiso 1 1 calc R . . H8A2 H -1.0178 0.0568 0.7336 0.139 Uiso 1 1 calc R . . H8A3 H -0.9881 0.0784 0.6748 0.139 Uiso 1 1 calc R . . C11 C -0.4022(4) 0.1894(2) 0.44593(14) 0.0174(8) Uani 1 1 d U . . H11 H -0.4449 0.1668 0.4765 0.021 Uiso 1 1 calc R . . C1S C -0.2726(4) 0.1883(2) 0.44703(14) 0.0163(8) Uani 1 1 d U . . C2S C -0.1510(4) 0.2070(2) 0.41604(14) 0.0187(9) Uani 1 1 d U . . C3S C -0.0860(4) 0.1753(2) 0.46241(14) 0.0160(8) Uani 1 1 d U . . C4S C -0.2079(4) 0.1606(2) 0.48864(14) 0.0147(8) Uani 1 1 d U . . C5S C -0.1737(4) 0.1087(3) 0.57200(16) 0.0275(10) Uani 1 1 d U . . H5S1 H -0.2243 0.1071 0.6051 0.033 Uiso 1 1 calc R . . H5S2 H -0.1178 0.1486 0.5680 0.033 Uiso 1 1 calc R . . C6S C -0.0943(5) 0.0273(3) 0.56790(18) 0.0390(12) Uani 1 1 d U . . H6S1 H -0.1494 -0.0103 0.5669 0.059 Uiso 1 1 calc R . . H6S2 H -0.0480 0.0081 0.5965 0.059 Uiso 1 1 calc R . . H6S3 H -0.0338 0.0311 0.5376 0.059 Uiso 1 1 calc R . . C301 C 0.6578(4) 0.6726(2) 0.45759(14) 0.0149(8) Uani 1 1 d U B . C302 C 0.5302(4) 0.6806(2) 0.45378(14) 0.0180(9) Uani 1 1 d U . . H302 H 0.4727 0.6599 0.4805 0.022 Uiso 1 1 calc R . . C303 C 0.4905(4) 0.7203(2) 0.40873(14) 0.0191(9) Uani 1 1 d U . . H303 H 0.4041 0.7269 0.4043 0.023 Uiso 1 1 calc R . . C304 C 0.5764(4) 0.7505(2) 0.37012(14) 0.0195(9) Uani 1 1 d U . . C305 C 0.7043(4) 0.7393(2) 0.37500(15) 0.0181(9) Uani 1 1 d U . . H305 H 0.7632 0.7577 0.3481 0.022 Uiso 1 1 calc R . . C306 C 0.7441(4) 0.7012(2) 0.41941(14) 0.0158(8) Uani 1 1 d U . . C307 C 0.8752(4) 0.6852(2) 0.43644(13) 0.0138(8) Uani 1 1 d U . . C308 C 0.8439(4) 0.6475(2) 0.49108(14) 0.0147(8) Uani 1 1 d U B . C309 C 0.9240(4) 0.7638(2) 0.43085(14) 0.0168(8) Uani 1 1 d U . . H30A H 1.0063 0.7527 0.4430 0.025 Uiso 1 1 calc R . . H30B H 0.8634 0.8003 0.4500 0.025 Uiso 1 1 calc R . . H30C H 0.9333 0.7888 0.3960 0.025 Uiso 1 1 calc R . . C310 C 0.9719(4) 0.6250(2) 0.40951(14) 0.0193(9) Uani 1 1 d U . . H31A H 0.9426 0.5736 0.4159 0.029 Uiso 1 1 calc R . . H31B H 1.0539 0.6173 0.4214 0.029 Uiso 1 1 calc R . . H31C H 0.9809 0.6455 0.3739 0.029 Uiso 1 1 calc R . . C312 C 0.5266(4) 0.7960(3) 0.32446(15) 0.0239(10) Uani 1 1 d U . . C1E C 0.6542(4) 0.6037(2) 0.54647(13) 0.0147(8) Uani 1 1 d U B . H1E1 H 0.5621 0.6249 0.5482 0.018 Uiso 1 1 calc R . . H1E2 H 0.6849 0.6181 0.5743 0.018 Uiso 1 1 calc R . . C2E C 0.6771(4) 0.5126(2) 0.55148(14) 0.0205(9) Uani 1 1 d DU . . H2E1 H 0.7688 0.4925 0.5433 0.025 Uiso 1 1 calc R A 1 H2E2 H 0.6323 0.4982 0.5274 0.025 Uiso 1 1 calc R A 1 C3E C 0.6316(8) 0.4712(7) 0.6037(3) 0.0212(17) Uani 0.743(9) 1 d PDU B 1 H3E1 H 0.5402 0.4923 0.6119 0.025 Uiso 0.743(9) 1 calc PR B 1 H3E2 H 0.6411 0.4131 0.6036 0.025 Uiso 0.743(9) 1 calc PR B 1 C4E C 0.7019(10) 0.4822(7) 0.6442(3) 0.032(2) Uani 0.743(9) 1 d PDU B 1 H4E1 H 0.7938 0.4746 0.6321 0.039 Uiso 0.743(9) 1 calc PR B 1 H4E2 H 0.6746 0.5381 0.6502 0.039 Uiso 0.743(9) 1 calc PR B 1 C5E C 0.6817(10) 0.4262(6) 0.6927(3) 0.067(3) Uani 0.743(9) 1 d PDU B 1 H5E1 H 0.7072 0.3703 0.6865 0.081 Uiso 0.743(9) 1 calc PR B 1 H5E2 H 0.7388 0.4337 0.7148 0.081 Uiso 0.743(9) 1 calc PR B 1 C6E C 0.5525(12) 0.4361(7) 0.7184(5) 0.107(4) Uani 0.743(9) 1 d PDU B 1 H6E1 H 0.4954 0.4249 0.6976 0.129 Uiso 0.743(9) 1 calc PR B 1 H6E2 H 0.5245 0.4925 0.7235 0.129 Uiso 0.743(9) 1 calc PR B 1 C7E C 0.5421(13) 0.3792(11) 0.7695(4) 0.122(5) Uani 0.743(9) 1 d PDU B 1 H7E1 H 0.5611 0.3224 0.7649 0.147 Uiso 0.743(9) 1 calc PR B 1 H7E2 H 0.6022 0.3872 0.7901 0.147 Uiso 0.743(9) 1 calc PR B 1 C8E C 0.4075(14) 0.4008(11) 0.7933(5) 0.144(5) Uani 0.743(9) 1 d PDU B 1 H8E1 H 0.3952 0.3661 0.8255 0.216 Uiso 0.743(9) 1 calc PR B 1 H8E2 H 0.3492 0.3934 0.7721 0.216 Uiso 0.743(9) 1 calc PR B 1 H8E3 H 0.3906 0.4570 0.7978 0.216 Uiso 0.743(9) 1 calc PR B 1 C3F C 0.601(3) 0.472(2) 0.5988(8) 0.0212(17) Uani 0.257(9) 1 d PDU B 2 H3F1 H 0.5119 0.5010 0.6020 0.025 Uiso 0.257(9) 1 calc PR B 2 H3F2 H 0.6014 0.4160 0.5966 0.025 Uiso 0.257(9) 1 calc PR B 2 C4F C 0.662(3) 0.476(3) 0.6439(9) 0.041(6) Uani 0.257(9) 1 d PDU B 2 H4F1 H 0.6771 0.5311 0.6406 0.049 Uiso 0.257(9) 1 calc PR B 2 H4F2 H 0.7461 0.4403 0.6415 0.049 Uiso 0.257(9) 1 calc PR B 2 C5F C 0.594(3) 0.4530(15) 0.6967(9) 0.068(5) Uani 0.257(9) 1 d PDU B 2 H5F1 H 0.6401 0.4667 0.7208 0.082 Uiso 0.257(9) 1 calc PR B 2 H5F2 H 0.5071 0.4845 0.6997 0.082 Uiso 0.257(9) 1 calc PR B 2 C6F C 0.589(3) 0.3662(16) 0.7086(10) 0.094(7) Uani 0.257(9) 1 d PDU B 2 H6F1 H 0.6727 0.3333 0.7149 0.113 Uiso 0.257(9) 1 calc PR B 2 H6F2 H 0.5586 0.3483 0.6819 0.113 Uiso 0.257(9) 1 calc PR B 2 C7F C 0.491(4) 0.363(3) 0.7569(12) 0.144(5) Uani 0.257(9) 1 d PDU B 2 H7F1 H 0.4060 0.3903 0.7482 0.172 Uiso 0.257(9) 1 calc PR B 2 H7F2 H 0.4859 0.3063 0.7709 0.172 Uiso 0.257(9) 1 calc PR B 2 C8F C 0.525(4) 0.403(3) 0.7964(14) 0.131(12) Uani 0.257(9) 1 d PDU B 2 H8F1 H 0.5099 0.3694 0.8289 0.197 Uiso 0.257(9) 1 calc PR B 2 H8F2 H 0.4712 0.4559 0.7963 0.197 Uiso 0.257(9) 1 calc PR B 2 H8F3 H 0.6139 0.4081 0.7890 0.197 Uiso 0.257(9) 1 calc PR B 2 C311 C 0.9206(4) 0.6202(2) 0.52793(14) 0.0149(8) Uani 1 1 d U . . H311 H 0.8795 0.5951 0.5581 0.018 Uiso 1 1 calc R . . C41S C 1.0494(4) 0.6225(2) 0.52910(13) 0.0142(8) Uani 1 1 d U . . C42S C 1.1679(4) 0.6471(2) 0.49967(14) 0.0154(8) Uani 1 1 d U . . C43S C 1.2366(4) 0.6115(2) 0.54465(14) 0.0158(8) Uani 1 1 d U . . C44S C 1.1139(4) 0.5930(2) 0.57029(14) 0.0145(8) Uani 1 1 d U . . C45 C 1.1556(4) 0.5421(3) 0.65339(15) 0.0248(10) Uani 1 1 d DU . . H45A H 1.2080 0.5841 0.6482 0.030 Uiso 1 1 calc R C 1 H45B H 1.1055 0.5404 0.6866 0.030 Uiso 1 1 calc R C 1 C46A C 1.2290(10) 0.4708(6) 0.6494(4) 0.047(3) Uani 0.515(12) 1 d PDU D 1 H46A H 1.2872 0.4569 0.6743 0.071 Uiso 0.515(12) 1 calc PR D 1 H46B H 1.2779 0.4734 0.6164 0.071 Uiso 0.515(12) 1 calc PR D 1 H46C H 1.1759 0.4299 0.6545 0.071 Uiso 0.515(12) 1 calc PR D 1 C46B C 1.1395(11) 0.4630(6) 0.6861(4) 0.039(3) Uani 0.485(12) 1 d PDU D 2 H46D H 1.1955 0.4513 0.7117 0.059 Uiso 0.485(12) 1 calc PR D 2 H46E H 1.1613 0.4203 0.6661 0.059 Uiso 0.485(12) 1 calc PR D 2 H46F H 1.0513 0.4661 0.7016 0.059 Uiso 0.485(12) 1 calc PR D 2 C201 C 1.2522(4) 0.0705(2) 0.08313(13) 0.0151(8) Uani 1 1 d U . . C202 C 1.3779(4) 0.0664(2) 0.08849(14) 0.0172(8) Uani 1 1 d U . . H202 H 1.4333 0.0927 0.0635 0.021 Uiso 1 1 calc R . . C203 C 1.4190(4) 0.0222(3) 0.13195(14) 0.0208(9) Uani 1 1 d U . . H203 H 1.5044 0.0181 0.1369 0.025 Uiso 1 1 calc R . . C204 C 1.3377(4) -0.0163(2) 0.16842(14) 0.0202(9) Uani 1 1 d U . . C205 C 1.2104(4) -0.0105(2) 0.16268(14) 0.0189(9) Uani 1 1 d U . . H205 H 1.1546 -0.0363 0.1878 0.023 Uiso 1 1 calc R . . C206 C 1.1679(4) 0.0336(2) 0.11955(13) 0.0155(8) Uani 1 1 d U . . C207 C 1.0383(4) 0.0508(2) 0.10221(13) 0.0145(8) Uani 1 1 d U . . C208 C 1.0630(3) 0.1028(2) 0.05139(13) 0.0139(8) Uani 1 1 d U . . C209 C 0.9388(4) 0.0964(2) 0.13801(14) 0.0189(9) Uani 1 1 d U . . H20A H 0.9262 0.0611 0.1700 0.028 Uiso 1 1 calc R . . H20B H 0.8584 0.1132 0.1243 0.028 Uiso 1 1 calc R . . H20C H 0.9686 0.1437 0.1425 0.028 Uiso 1 1 calc R . . C210 C 0.9991(4) -0.0276(2) 0.09735(15) 0.0193(9) Uani 1 1 d U . . H21A H 1.0601 -0.0534 0.0726 0.029 Uiso 1 1 calc R . . H21B H 0.9145 -0.0153 0.0870 0.029 Uiso 1 1 calc R . . H21C H 0.9979 -0.0638 0.1293 0.029 Uiso 1 1 calc R . . C212 C 1.3884(4) -0.0674(3) 0.21303(15) 0.0248(10) Uani 1 1 d U . . C1C C 1.2515(4) 0.1503(2) -0.00332(13) 0.0151(8) Uani 1 1 d U . . H1C1 H 1.3281 0.1667 0.0032 0.018 Uiso 1 1 calc R . . H1C2 H 1.1939 0.1992 -0.0168 0.018 Uiso 1 1 calc R . . C2C C 1.2894(4) 0.0943(2) -0.04137(14) 0.0203(9) Uani 1 1 d U F . H2C1 H 1.3644 0.0539 -0.0323 0.024 Uiso 1 1 calc R . . H2C2 H 1.2193 0.0655 -0.0403 0.024 Uiso 1 1 calc R . . C3C C 1.3204(4) 0.1378(3) -0.09403(15) 0.0289(10) Uani 1 1 d DU . . H3C1 H 1.3916 0.1655 -0.0944 0.035 Uiso 1 1 calc R E 1 H3C2 H 1.3517 0.0966 -0.1154 0.035 Uiso 1 1 calc R E 1 C4C C 1.2169(19) 0.1989(16) -0.1179(7) 0.0281(18) Uani 0.408(9) 1 d PDU F 1 H4C1 H 1.2006 0.2490 -0.1040 0.034 Uiso 0.408(9) 1 calc PR F 1 H4C2 H 1.1373 0.1775 -0.1123 0.034 Uiso 0.408(9) 1 calc PR F 1 C5C C 1.2655(15) 0.2152(11) -0.1733(5) 0.040(4) Uani 0.408(9) 1 d PDU F 1 H5C1 H 1.3419 0.2399 -0.1789 0.049 Uiso 0.408(9) 1 calc PR F 1 H5C2 H 1.2880 0.1643 -0.1865 0.049 Uiso 0.408(9) 1 calc PR F 1 C6C C 1.1612(15) 0.2711(9) -0.1988(5) 0.046(4) Uani 0.408(9) 1 d PDU F 1 H6C1 H 1.0930 0.2407 -0.1831 0.055 Uiso 0.408(9) 1 calc PR F 1 H6C2 H 1.1500 0.3137 -0.1787 0.055 Uiso 0.408(9) 1 calc PR F 1 C7C C 1.0925(14) 0.3209(11) -0.2393(5) 0.066(4) Uani 0.408(9) 1 d PDU F 1 H7C1 H 1.1233 0.2880 -0.2655 0.079 Uiso 0.408(9) 1 calc PR F 1 H7C2 H 1.1403 0.3656 -0.2489 0.079 Uiso 0.408(9) 1 calc PR F 1 C8C C 0.9625(13) 0.3639(11) -0.2545(5) 0.058(5) Uani 0.408(9) 1 d PDU F 1 H8C1 H 0.9731 0.3891 -0.2893 0.087 Uiso 0.408(9) 1 calc PR F 1 H8C2 H 0.9254 0.4052 -0.2341 0.087 Uiso 0.408(9) 1 calc PR F 1 H8C3 H 0.9062 0.3249 -0.2497 0.087 Uiso 0.408(9) 1 calc PR F 1 C4D C 1.2008(13) 0.1925(11) -0.1129(5) 0.0281(18) Uani 0.592(9) 1 d PDU F 2 H4D1 H 1.1327 0.1603 -0.1065 0.034 Uiso 0.592(9) 1 calc PR F 2 H4D2 H 1.1732 0.2357 -0.0929 0.034 Uiso 0.592(9) 1 calc PR F 2 C5D C 1.2116(13) 0.2312(9) -0.1669(4) 0.060(4) Uani 0.592(9) 1 d PDU F 2 H5D1 H 1.2811 0.2623 -0.1731 0.072 Uiso 0.592(9) 1 calc PR F 2 H5D2 H 1.2388 0.1875 -0.1866 0.072 Uiso 0.592(9) 1 calc PR F 2 C6D C 1.0996(15) 0.2855(7) -0.1873(4) 0.073(4) Uani 0.592(9) 1 d PDU F 2 H6D1 H 1.0485 0.3164 -0.1621 0.088 Uiso 0.592(9) 1 calc PR F 2 H6D2 H 1.1274 0.3237 -0.2166 0.088 Uiso 0.592(9) 1 calc PR F 2 C7D C 1.0355(11) 0.2409(7) -0.1989(5) 0.073(4) Uani 0.592(9) 1 d PDU F 2 H7D1 H 0.9880 0.2133 -0.1693 0.088 Uiso 0.592(9) 1 calc PR F 2 H7D2 H 1.0907 0.2003 -0.2172 0.088 Uiso 0.592(9) 1 calc PR F 2 C8D C 0.9452(13) 0.2996(9) -0.2318(5) 0.086(4) Uani 0.592(9) 1 d PDU F 2 H8D1 H 0.8987 0.2694 -0.2464 0.129 Uiso 0.592(9) 1 calc PR F 2 H8D2 H 0.9941 0.3317 -0.2582 0.129 Uiso 0.592(9) 1 calc PR F 2 H8D3 H 0.8851 0.3351 -0.2119 0.129 Uiso 0.592(9) 1 calc PR F 2 C211 C 0.9837(4) 0.1373(2) 0.01642(14) 0.0163(8) Uani 1 1 d U . . H211 H 1.0242 0.1653 -0.0128 0.020 Uiso 1 1 calc R . . C31S C 0.8542(4) 0.1392(2) 0.01547(14) 0.0160(8) Uani 1 1 d U . . C32S C 0.7364(4) 0.1123(2) 0.04460(14) 0.0158(8) Uani 1 1 d U . . C33S C 0.6654(4) 0.1527(2) 0.00073(14) 0.0163(8) Uani 1 1 d U . . C34S C 0.7856(4) 0.1781(2) -0.02426(14) 0.0157(8) Uani 1 1 d U . . C35S C 0.7342(4) 0.2608(3) -0.09995(15) 0.0251(10) Uani 1 1 d U . . C36S C 0.7046(5) 0.2021(3) -0.12755(18) 0.0368(12) Uani 1 1 d U . . H36A H 0.7825 0.1782 -0.1465 0.055 Uiso 1 1 calc R . . H36B H 0.6433 0.2301 -0.1501 0.055 Uiso 1 1 calc R . . H36C H 0.6687 0.1598 -0.1040 0.055 Uiso 1 1 calc R . . C101 C 0.9292(4) 0.6378(2) 0.00249(14) 0.0165(8) Uani 1 1 d U . . C102 C 1.0537(4) 0.6378(2) 0.00866(15) 0.0188(9) Uani 1 1 d U . . H102 H 1.1104 0.6608 -0.0174 0.023 Uiso 1 1 calc R . . C103 C 1.0913(4) 0.6026(2) 0.05453(14) 0.0188(9) Uani 1 1 d U . . H103 H 1.1750 0.6020 0.0604 0.023 Uiso 1 1 calc R . . C104 C 1.0068(4) 0.5682(3) 0.09207(15) 0.0223(9) Uani 1 1 d U . . C105 C 0.8824(4) 0.5689(3) 0.08460(15) 0.0212(9) Uani 1 1 d U . . H105 H 0.8252 0.5459 0.1105 0.025 Uiso 1 1 calc R . . C106 C 0.8445(4) 0.6030(2) 0.03970(14) 0.0177(8) Uani 1 1 d U . . C107 C 0.7168(4) 0.6145(2) 0.02188(14) 0.0180(8) Uani 1 1 d U . . C108 C 0.7430(4) 0.6631(2) -0.03032(14) 0.0175(8) Uani 1 1 d U . . C110 C 0.6812(4) 0.5347(2) 0.01903(17) 0.0257(10) Uani 1 1 d U . . H11A H 0.7459 0.5066 -0.0036 0.039 Uiso 1 1 calc R . . H11B H 0.5989 0.5450 0.0069 0.039 Uiso 1 1 calc R . . H11C H 0.6760 0.5015 0.0520 0.039 Uiso 1 1 calc R . . C109 C 0.6131(4) 0.6617(2) 0.05490(14) 0.0186(9) Uani 1 1 d U . . H10D H 0.6004 0.6291 0.0878 0.028 Uiso 1 1 calc R . . H10E H 0.5338 0.6746 0.0404 0.028 Uiso 1 1 calc R . . H10F H 0.6389 0.7114 0.0576 0.028 Uiso 1 1 calc R . . C112 C 1.0537(4) 0.5300(3) 0.13972(16) 0.0258(10) Uani 1 1 d U . . C1B C 0.9288(4) 0.7133(2) -0.08516(14) 0.0181(9) Uani 1 1 d U . . H1B1 H 1.0059 0.7290 -0.0786 0.022 Uiso 1 1 calc R . . H1B2 H 0.8706 0.7630 -0.0972 0.022 Uiso 1 1 calc R . . C2B C 0.9655(4) 0.6615(3) -0.12554(15) 0.0235(9) Uani 1 1 d U . . H2B1 H 0.8955 0.6332 -0.1257 0.028 Uiso 1 1 calc R . . H2B2 H 1.0413 0.6205 -0.1181 0.028 Uiso 1 1 calc R . . C3B C 0.9942(4) 0.7116(3) -0.17696(15) 0.0260(10) Uani 1 1 d U . . H3B1 H 1.0568 0.7449 -0.1756 0.031 Uiso 1 1 calc R . . H3B2 H 1.0327 0.6750 -0.2007 0.031 Uiso 1 1 calc R . . C4B C 0.8764(5) 0.7661(3) -0.19548(15) 0.0286(10) Uani 1 1 d U . . H4B1 H 0.8382 0.8019 -0.1712 0.034 Uiso 1 1 calc R . . H4B2 H 0.8143 0.7322 -0.1964 0.034 Uiso 1 1 calc R . . C5B C 0.8971(5) 0.8178(3) -0.24622(16) 0.0362(12) Uani 1 1 d U . . H5B1 H 0.9425 0.7833 -0.2703 0.043 Uiso 1 1 calc R . . H5B2 H 0.9509 0.8567 -0.2448 0.043 Uiso 1 1 calc R . . C6B C 0.7719(5) 0.8635(3) -0.26367(17) 0.0357(11) Uani 1 1 d U . . H6B1 H 0.7204 0.8238 -0.2660 0.043 Uiso 1 1 calc R . . H6B2 H 0.7251 0.8950 -0.2382 0.043 Uiso 1 1 calc R . . C7B C 0.7827(5) 0.9200(3) -0.31299(19) 0.0397(12) Uani 1 1 d U . . H7B1 H 0.8256 0.9636 -0.3101 0.048 Uiso 1 1 calc R . . H7B2 H 0.8354 0.8902 -0.3383 0.048 Uiso 1 1 calc R . . C8B C 0.6549(5) 0.9560(3) -0.32936(19) 0.0436(13) Uani 1 1 d U . . H8B1 H 0.6152 0.9134 -0.3351 0.065 Uiso 1 1 calc R . . H8B2 H 0.6653 0.9947 -0.3600 0.065 Uiso 1 1 calc R . . H8B3 H 0.6009 0.9833 -0.3036 0.065 Uiso 1 1 calc R . . C111 C 0.6646(4) 0.6948(2) -0.06618(14) 0.0198(9) Uani 1 1 d U . . H111 H 0.7052 0.7217 -0.0958 0.024 Uiso 1 1 calc R . . C21S C 0.5340(4) 0.6949(2) -0.06721(14) 0.0199(9) Uani 1 1 d U . . C22S C 0.4165(4) 0.6712(3) -0.03828(15) 0.0224(9) Uani 1 1 d U . . C23S C 0.3481(4) 0.7076(3) -0.08397(16) 0.0257(10) Uani 1 1 d U . . C24S C 0.4696(4) 0.7274(3) -0.10831(15) 0.0270(10) Uani 1 1 d U . . C25S C 0.4275(6) 0.7892(4) -0.1893(2) 0.0593(17) Uani 1 1 d DU . . H25A H 0.4638 0.7638 -0.2186 0.071 Uiso 1 1 calc R . . H25B H 0.3456 0.7719 -0.1757 0.071 Uiso 1 1 calc R . . C26S C 0.4079(6) 0.8758(4) -0.2034(2) 0.0525(15) Uani 1 1 d DU . . H26A H 0.3765 0.9005 -0.1739 0.079 Uiso 1 1 calc R . . H26B H 0.3456 0.8932 -0.2267 0.079 Uiso 1 1 calc R . . H26C H 0.4883 0.8921 -0.2189 0.079 Uiso 1 1 calc R . . O1 O -0.9230(3) 0.4127(2) 0.24959(12) 0.0369(8) Uani 1 1 d U . . O2 O -0.7231(3) 0.4238(2) 0.21645(12) 0.0399(9) Uani 1 1 d U . . H2A H -0.7602 0.4543 0.1937 0.060 Uiso 1 1 calc R . . O1S O -0.1141(3) 0.2337(2) 0.37368(10) 0.0307(8) Uani 1 1 d U . . O2S O 0.0233(3) 0.16588(17) 0.47198(11) 0.0244(7) Uani 1 1 d U . . O3S O -0.2589(3) 0.13293(17) 0.53381(10) 0.0225(7) Uani 1 1 d U . . O301 O 0.4100(3) 0.8093(2) 0.32161(11) 0.0390(9) Uani 1 1 d U . . O302 O 0.6067(3) 0.8251(2) 0.28947(11) 0.0331(8) Uani 1 1 d U . . H30D H 0.5689 0.8497 0.2654 0.050 Uiso 1 1 calc R . . O8 O 1.1996(3) 0.68095(17) 0.45817(10) 0.0201(6) Uani 1 1 d U . . O9 O 1.3448(3) 0.60234(17) 0.55368(10) 0.0225(7) Uani 1 1 d U . . O10 O 1.0715(3) 0.55902(16) 0.61528(9) 0.0198(6) Uani 1 1 d DU D . O201 O 1.5024(3) -0.0731(2) 0.21798(11) 0.0354(8) Uani 1 1 d U . . O202 O 1.3095(3) -0.1040(2) 0.24512(11) 0.0380(9) Uani 1 1 d U . . H20D H 1.3468 -0.1309 0.2688 0.057 Uiso 1 1 calc R . . O31S O 0.7044(3) 0.07596(16) 0.08490(10) 0.0206(6) Uani 1 1 d U . . O32S O 0.5585(3) 0.16066(18) -0.00971(10) 0.0239(7) Uani 1 1 d U . . O33S O 0.8288(3) 0.21964(17) -0.06610(10) 0.0206(6) Uani 1 1 d U . . O101 O 1.1659(3) 0.5228(2) 0.14586(12) 0.0387(9) Uani 1 1 d U . . O102 O 0.9697(3) 0.5013(2) 0.17451(11) 0.0359(8) Uani 1 1 d U . . H10G H 1.0039 0.4808 0.2001 0.054 Uiso 1 1 calc R . . O21S O 0.3823(3) 0.63821(18) 0.00304(10) 0.0274(7) Uani 1 1 d U . . O22S O 0.2413(3) 0.7144(2) -0.09421(12) 0.0352(8) Uani 1 1 d U . . O23S O 0.5150(3) 0.7647(2) -0.15179(11) 0.0462(10) Uani 1 1 d U . . N1 N -0.6043(3) 0.20929(19) 0.41838(11) 0.0162(7) Uani 1 1 d U . . N201 N 1.1881(3) 0.11134(19) 0.04313(11) 0.0151(7) Uani 1 1 d U . . N301 N 0.7186(3) 0.64075(18) 0.50006(11) 0.0133(7) Uani 1 1 d U . . N101 N 0.8673(3) 0.6727(2) -0.03892(11) 0.0176(7) Uani 1 1 d U . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.016(2) 0.0201(19) 0.0158(18) -0.0029(16) -0.0075(16) -0.0031(16) C2 0.016(2) 0.027(2) 0.0148(19) -0.0002(17) -0.0031(16) -0.0048(17) C3 0.015(2) 0.035(2) 0.024(2) 0.0010(18) -0.0122(17) -0.0022(18) C4 0.020(2) 0.030(2) 0.021(2) -0.0009(18) -0.0114(17) -0.0032(17) C5 0.019(2) 0.030(2) 0.0153(19) 0.0015(17) -0.0064(17) -0.0066(17) C6 0.014(2) 0.026(2) 0.0139(18) -0.0003(16) -0.0061(15) -0.0063(16) C7 0.012(2) 0.025(2) 0.0136(18) -0.0007(16) -0.0069(15) -0.0067(16) C8 0.0084(19) 0.0188(19) 0.0153(18) -0.0044(15) -0.0039(15) -0.0022(15) C9 0.010(2) 0.023(2) 0.026(2) 0.0026(17) -0.0115(17) -0.0051(16) C10 0.021(2) 0.034(2) 0.016(2) -0.0040(18) -0.0067(17) -0.0055(18) C12 0.022(3) 0.047(3) 0.019(2) 0.002(2) -0.0101(18) -0.009(2) C1A 0.012(2) 0.0227(19) 0.0142(18) 0.0002(16) -0.0050(15) -0.0045(16) C2A 0.019(2) 0.025(2) 0.023(2) -0.0060(17) -0.0066(17) 0.0005(17) C3A 0.023(2) 0.023(2) 0.030(2) -0.0017(18) -0.0093(19) -0.0052(17) C4A 0.040(3) 0.027(2) 0.021(2) -0.0008(19) -0.014(2) -0.004(2) C5A 0.038(3) 0.034(3) 0.025(2) -0.004(2) -0.007(2) -0.007(2) C6A 0.054(3) 0.052(3) 0.027(2) -0.004(2) -0.009(2) -0.007(3) C7A 0.088(5) 0.072(4) 0.029(3) 0.001(3) 0.000(3) -0.020(4) C8A 0.085(5) 0.122(7) 0.056(4) -0.016(4) 0.022(4) -0.010(5) C11 0.016(2) 0.023(2) 0.0148(18) 0.0006(16) -0.0056(16) -0.0078(16) C1S 0.014(2) 0.0181(19) 0.0184(19) -0.0040(16) -0.0069(16) -0.0013(15) C2S 0.012(2) 0.029(2) 0.019(2) -0.0085(17) -0.0058(16) -0.0041(16) C3S 0.013(2) 0.0185(19) 0.0181(19) -0.0032(16) -0.0049(16) -0.0029(15) C4S 0.017(2) 0.0129(18) 0.0159(18) 0.0005(15) -0.0087(16) -0.0041(15) C5S 0.030(3) 0.039(2) 0.019(2) 0.0058(19) -0.0187(19) -0.017(2) C6S 0.029(3) 0.053(3) 0.033(3) 0.007(2) -0.014(2) -0.011(2) C301 0.013(2) 0.0184(19) 0.0127(18) 0.0004(15) -0.0065(15) -0.0018(15) C302 0.013(2) 0.026(2) 0.0155(19) 0.0003(16) -0.0067(16) -0.0035(16) C303 0.012(2) 0.029(2) 0.0185(19) -0.0029(17) -0.0074(16) -0.0059(17) C304 0.016(2) 0.027(2) 0.0166(19) 0.0013(17) -0.0084(16) -0.0056(17) C305 0.011(2) 0.023(2) 0.0190(19) 0.0000(17) -0.0038(16) -0.0038(16) C306 0.012(2) 0.022(2) 0.0152(18) -0.0039(16) -0.0073(15) -0.0034(15) C307 0.0095(19) 0.0196(19) 0.0129(18) -0.0017(15) -0.0037(15) -0.0031(15) C308 0.0110(19) 0.0183(19) 0.0158(18) -0.0021(15) -0.0050(15) -0.0033(15) C309 0.015(2) 0.0210(19) 0.0141(18) 0.0021(16) -0.0047(16) -0.0049(16) C310 0.013(2) 0.026(2) 0.019(2) -0.0068(17) -0.0046(16) 0.0000(16) C312 0.015(2) 0.038(2) 0.019(2) -0.0005(18) -0.0079(17) -0.0058(18) C1E 0.009(2) 0.0220(19) 0.0125(18) -0.0010(15) -0.0025(15) -0.0021(15) C2E 0.021(2) 0.025(2) 0.0175(19) -0.0046(17) -0.0035(17) -0.0065(17) C3E 0.020(5) 0.020(2) 0.022(2) 0.001(2) -0.005(3) -0.003(3) C4E 0.044(6) 0.033(4) 0.018(3) -0.005(3) -0.013(3) 0.002(4) C5E 0.088(6) 0.062(5) 0.040(4) 0.009(4) -0.016(4) 0.001(4) C6E 0.113(8) 0.081(7) 0.092(7) 0.032(6) 0.030(6) -0.020(6) C7E 0.126(9) 0.192(13) 0.046(6) 0.035(7) -0.021(6) -0.068(10) C8E 0.121(9) 0.241(13) 0.063(7) 0.029(8) -0.008(6) -0.077(10) C3F 0.020(5) 0.020(2) 0.022(2) 0.001(2) -0.005(3) -0.003(3) C4F 0.048(14) 0.045(12) 0.029(6) 0.000(8) -0.020(8) -0.001(11) C5F 0.072(10) 0.073(8) 0.043(6) 0.005(7) -0.008(7) 0.007(7) C6F 0.116(16) 0.096(11) 0.063(11) 0.011(11) -0.003(10) -0.035(14) C7F 0.121(9) 0.241(13) 0.063(7) 0.029(8) -0.008(6) -0.077(10) C8F 0.09(3) 0.22(3) 0.059(17) -0.010(18) 0.011(18) 0.00(2) C311 0.0101(19) 0.025(2) 0.0106(17) -0.0012(16) -0.0053(15) -0.0037(15) C41S 0.0129(19) 0.0179(19) 0.0130(18) -0.0015(15) -0.0041(15) -0.0041(15) C42S 0.013(2) 0.0191(19) 0.0163(19) -0.0030(16) -0.0058(15) -0.0038(15) C43S 0.012(2) 0.021(2) 0.0159(19) -0.0034(16) -0.0049(16) -0.0048(16) C44S 0.013(2) 0.0187(19) 0.0145(18) -0.0045(15) -0.0060(15) -0.0048(15) C45 0.024(2) 0.036(2) 0.0175(19) 0.0045(17) -0.0167(17) -0.0116(17) C46A 0.036(7) 0.071(7) 0.034(6) -0.013(5) -0.004(5) -0.006(5) C46B 0.053(8) 0.044(6) 0.027(6) 0.008(4) -0.028(5) -0.019(5) C201 0.015(2) 0.0189(19) 0.0131(18) -0.0023(15) -0.0088(15) -0.0022(15) C202 0.012(2) 0.023(2) 0.0158(19) 0.0006(16) -0.0054(16) -0.0029(16) C203 0.013(2) 0.034(2) 0.019(2) -0.0049(17) -0.0082(16) -0.0044(17) C204 0.018(2) 0.027(2) 0.0165(19) 0.0022(17) -0.0106(17) -0.0037(17) C205 0.018(2) 0.025(2) 0.0145(19) 0.0005(16) -0.0063(16) -0.0062(17) C206 0.013(2) 0.023(2) 0.0122(18) -0.0037(15) -0.0050(15) -0.0031(15) C207 0.013(2) 0.0193(19) 0.0125(18) 0.0023(15) -0.0083(15) -0.0050(15) C208 0.0064(19) 0.0217(19) 0.0142(18) -0.0023(16) -0.0032(14) -0.0033(15) C209 0.014(2) 0.028(2) 0.0150(19) -0.0036(17) -0.0046(16) -0.0030(17) C210 0.017(2) 0.023(2) 0.019(2) -0.0011(17) -0.0085(17) -0.0052(16) C212 0.017(2) 0.039(2) 0.017(2) -0.0001(18) -0.0083(17) -0.0016(18) C1C 0.011(2) 0.022(2) 0.0123(18) 0.0002(15) -0.0041(15) -0.0057(16) C2C 0.021(2) 0.022(2) 0.0174(19) -0.0039(16) -0.0053(17) -0.0016(17) C3C 0.031(3) 0.041(3) 0.015(2) -0.0087(19) -0.0009(18) -0.006(2) C4C 0.043(4) 0.027(3) 0.015(3) -0.002(2) -0.005(2) -0.009(3) C5C 0.032(9) 0.053(8) 0.022(5) -0.004(6) 0.001(6) 0.021(7) C6C 0.046(9) 0.033(7) 0.044(7) -0.010(6) -0.011(6) 0.031(6) C7C 0.060(7) 0.097(8) 0.031(6) 0.006(6) -0.023(5) 0.006(6) C8C 0.051(9) 0.087(12) 0.025(7) 0.010(7) -0.021(6) 0.006(8) C4D 0.043(4) 0.027(3) 0.015(3) -0.002(2) -0.005(2) -0.009(3) C5D 0.056(8) 0.084(8) 0.016(4) 0.011(5) -0.005(5) 0.021(7) C6D 0.118(10) 0.055(7) 0.034(6) -0.019(5) -0.048(7) 0.055(6) C7D 0.058(7) 0.073(7) 0.069(8) 0.027(6) -0.017(5) 0.004(5) C8D 0.074(9) 0.106(10) 0.074(9) 0.012(8) -0.037(7) -0.012(7) C211 0.013(2) 0.023(2) 0.0128(18) -0.0002(16) -0.0045(15) -0.0021(16) C31S 0.013(2) 0.023(2) 0.0141(18) -0.0041(16) -0.0071(15) -0.0021(15) C32S 0.014(2) 0.0188(19) 0.0187(19) -0.0073(16) -0.0076(16) -0.0032(15) C33S 0.009(2) 0.025(2) 0.0152(18) -0.0049(16) -0.0015(15) -0.0031(16) C34S 0.010(2) 0.024(2) 0.0139(18) -0.0031(16) -0.0062(15) 0.0000(15) C35S 0.018(2) 0.037(2) 0.021(2) -0.0013(19) -0.0154(18) 0.0003(18) C36S 0.039(3) 0.047(3) 0.029(2) -0.006(2) -0.021(2) -0.007(2) C101 0.014(2) 0.0189(19) 0.0167(19) -0.0017(16) -0.0061(16) -0.0021(16) C102 0.014(2) 0.024(2) 0.0178(19) -0.0023(17) -0.0028(16) -0.0040(16) C103 0.010(2) 0.027(2) 0.020(2) -0.0041(17) -0.0049(16) -0.0020(16) C104 0.018(2) 0.031(2) 0.020(2) -0.0019(18) -0.0070(17) -0.0085(18) C105 0.014(2) 0.033(2) 0.0179(19) -0.0058(18) -0.0043(16) -0.0056(17) C106 0.013(2) 0.0188(19) 0.0189(19) 0.0010(16) -0.0044(16) 0.0004(15) C107 0.014(2) 0.021(2) 0.0184(19) 0.0004(16) -0.0047(16) -0.0032(16) C108 0.012(2) 0.025(2) 0.0160(19) -0.0047(16) -0.0035(15) -0.0026(16) C110 0.029(3) 0.020(2) 0.030(2) -0.0034(18) -0.012(2) -0.0034(18) C109 0.014(2) 0.027(2) 0.0139(19) -0.0010(16) -0.0055(16) -0.0019(16) C112 0.016(2) 0.035(2) 0.029(2) -0.0021(19) -0.0147(18) -0.0044(18) C1B 0.014(2) 0.024(2) 0.0160(19) 0.0013(16) -0.0043(16) -0.0038(16) C2B 0.019(2) 0.032(2) 0.021(2) -0.0066(18) -0.0029(17) -0.0053(18) C3B 0.024(2) 0.037(2) 0.019(2) -0.0095(18) -0.0003(18) -0.0060(19) C4B 0.035(3) 0.034(2) 0.018(2) -0.0047(18) -0.0040(19) -0.008(2) C5B 0.048(3) 0.044(3) 0.019(2) -0.002(2) -0.008(2) -0.014(2) C6B 0.045(3) 0.040(3) 0.026(2) -0.007(2) -0.010(2) -0.010(2) C7B 0.047(3) 0.038(3) 0.035(3) -0.001(2) -0.011(2) -0.012(2) C8B 0.050(3) 0.048(3) 0.033(3) -0.001(2) -0.013(2) -0.011(3) C111 0.014(2) 0.030(2) 0.0147(19) -0.0013(17) -0.0044(16) -0.0040(17) C21S 0.016(2) 0.028(2) 0.0156(19) -0.0022(17) -0.0058(16) -0.0024(17) C22S 0.018(2) 0.030(2) 0.022(2) -0.0072(18) -0.0081(17) -0.0024(17) C23S 0.017(2) 0.035(2) 0.027(2) -0.0071(19) -0.0088(18) -0.0028(18) C24S 0.017(2) 0.046(3) 0.019(2) -0.0015(19) -0.0103(17) -0.0063(19) C25S 0.046(4) 0.093(4) 0.037(3) 0.024(3) -0.025(3) -0.025(3) C26S 0.041(3) 0.073(4) 0.049(3) -0.016(3) -0.015(3) -0.011(3) O1 0.0222(18) 0.055(2) 0.0297(17) 0.0081(16) -0.0118(14) -0.0064(15) O2 0.0209(18) 0.064(2) 0.0280(17) 0.0186(16) -0.0109(14) -0.0119(16) O1S 0.0193(17) 0.053(2) 0.0168(15) 0.0038(14) -0.0074(12) -0.0053(14) O2S 0.0156(16) 0.0310(16) 0.0292(16) -0.0003(13) -0.0118(13) -0.0076(12) O3S 0.0188(16) 0.0342(16) 0.0170(14) 0.0019(12) -0.0093(12) -0.0106(13) O301 0.0148(17) 0.070(2) 0.0264(17) 0.0134(17) -0.0129(13) -0.0073(15) O302 0.0190(17) 0.056(2) 0.0172(15) 0.0103(14) -0.0089(13) -0.0021(15) O8 0.0124(15) 0.0309(15) 0.0163(14) 0.0017(12) -0.0023(11) -0.0075(12) O9 0.0120(15) 0.0377(16) 0.0199(14) -0.0027(13) -0.0074(12) -0.0074(12) O10 0.0172(15) 0.0306(15) 0.0131(13) 0.0025(12) -0.0079(11) -0.0091(12) O201 0.0177(17) 0.058(2) 0.0292(17) 0.0081(16) -0.0165(14) -0.0081(15) O202 0.0303(19) 0.057(2) 0.0254(16) 0.0194(15) -0.0191(14) -0.0179(16) O31S 0.0192(16) 0.0269(15) 0.0169(14) -0.0006(12) -0.0071(12) -0.0063(12) O32S 0.0109(15) 0.0373(17) 0.0239(15) -0.0004(13) -0.0092(12) -0.0044(12) O33S 0.0129(15) 0.0326(16) 0.0144(13) 0.0026(12) -0.0069(11) -0.0021(12) O101 0.0275(19) 0.057(2) 0.0303(17) 0.0156(16) -0.0184(14) -0.0154(16) O102 0.0325(19) 0.051(2) 0.0208(16) 0.0111(15) -0.0149(14) -0.0083(16) O21S 0.0219(17) 0.0401(18) 0.0206(15) -0.0020(14) -0.0035(13) -0.0086(14) O22S 0.0159(17) 0.059(2) 0.0331(18) -0.0075(16) -0.0111(14) -0.0062(15) O23S 0.028(2) 0.090(3) 0.0208(16) 0.0144(17) -0.0154(14) -0.0223(18) N1 0.0137(18) 0.0233(17) 0.0122(15) 0.0004(13) -0.0067(13) -0.0041(13) N201 0.0116(17) 0.0202(16) 0.0135(15) 0.0021(13) -0.0066(13) -0.0035(13) N301 0.0088(17) 0.0206(16) 0.0111(15) -0.0007(13) -0.0055(12) -0.0028(13) N101 0.0139(18) 0.0257(17) 0.0129(15) 0.0004(14) -0.0049(13) -0.0037(14) _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C2 1.389(6) . ? C1 C6 1.395(5) . ? C1 N1 1.409(5) . ? C2 C3 1.387(5) . ? C2 H2 0.9500 . ? C3 C4 1.391(6) . ? C3 H3 0.9500 . ? C4 C5 1.412(6) . ? C4 C12 1.482(6) . ? C5 C6 1.386(5) . ? C5 H5 0.9500 . ? C6 C7 1.507(5) . ? C7 C8 1.533(5) . ? C7 C9 1.539(5) . ? C7 C10 1.545(6) . ? C8 C11 1.370(5) . ? C8 N1 1.380(5) . ? C9 H9A 0.9800 . ? C9 H9B 0.9800 . ? C9 H9C 0.9800 . ? C10 H10A 0.9800 . ? C10 H10B 0.9800 . ? C10 H10C 0.9800 . ? C12 O1 1.240(5) . ? C12 O2 1.310(5) . ? C1A N1 1.459(5) . ? C1A C2A 1.536(5) . ? C1A H1A1 0.9900 . ? C1A H1A2 0.9900 . ? C2A C3A 1.518(6) . ? C2A H2A1 0.9900 . ? C2A H2A2 0.9900 . ? C3A C4A 1.529(6) . ? C3A H3A1 0.9900 . ? C3A H3A2 0.9900 . ? C4A C5A 1.535(6) . ? C4A H4A1 0.9900 . ? C4A H4A2 0.9900 . ? C5A C6A 1.515(7) . ? C5A H5A1 0.9900 . ? C5A H5A2 0.9900 . ? C6A C7A 1.517(8) . ? C6A H6A1 0.9900 . ? C6A H6A2 0.9900 . ? C7A C8A 1.492(11) . ? C7A H7A1 0.9900 . ? C7A H7A2 0.9900 . ? C8A H8A1 0.9800 . ? C8A H8A2 0.9800 . ? C8A H8A3 0.9800 . ? C11 C1S 1.413(5) . ? C11 H11 0.9500 . ? C1S C4S 1.409(5) . ? C1S C2S 1.512(6) . ? C2S O1S 1.212(5) . ? C2S C3S 1.528(5) . ? C3S O2S 1.234(5) . ? C3S C4S 1.449(6) . ? C4S O3S 1.325(5) . ? C5S O3S 1.470(5) . ? C5S C6S 1.505(7) . ? C5S H5S1 0.9900 . ? C5S H5S2 0.9900 . ? C6S H6S1 0.9800 . ? C6S H6S2 0.9800 . ? C6S H6S3 0.9800 . ? C301 C306 1.380(5) . ? C301 C302 1.387(5) . ? C301 N301 1.413(5) . ? C302 C303 1.396(5) . ? C302 H302 0.9500 . ? C303 C304 1.394(6) . ? C303 H303 0.9500 . ? C304 C305 1.392(6) . ? C304 C312 1.479(5) . ? C305 C306 1.374(5) . ? C305 H305 0.9500 . ? C306 C307 1.533(5) . ? C307 C310 1.531(6) . ? C307 C309 1.533(5) . ? C307 C308 1.543(5) . ? C308 N301 1.370(5) . ? C308 C311 1.381(5) . ? C309 H30A 0.9800 . ? C309 H30B 0.9800 . ? C309 H30C 0.9800 . ? C310 H31A 0.9800 . ? C310 H31B 0.9800 . ? C310 H31C 0.9800 . ? C312 O301 1.255(5) . ? C312 O302 1.290(5) . ? C1E N301 1.457(5) . ? C1E C2E 1.525(5) . ? C1E H1E1 0.9900 . ? C1E H1E2 0.9900 . ? C2E C3E 1.537(8) . ? C2E C3F 1.553(18) . ? C2E H2E1 0.9900 . ? C2E H2E2 0.9900 . ? C3E C4E 1.532(9) . ? C3E H3E1 0.9900 . ? C3E H3E2 0.9900 . ? C4E C5E 1.509(10) . ? C4E H4E1 0.9900 . ? C4E H4E2 0.9900 . ? C5E C6E 1.459(13) . ? C5E H5E1 0.9900 . ? C5E H5E2 0.9900 . ? C6E C7E 1.561(12) . ? C6E H6E1 0.9900 . ? C6E H6E2 0.9900 . ? C7E C8E 1.506(15) . ? C7E H7E1 0.9900 . ? C7E H7E2 0.9900 . ? C8E H8E1 0.9800 . ? C8E H8E2 0.9800 . ? C8E H8E3 0.9800 . ? C3F C4F 1.535(18) . ? C3F H3F1 0.9900 . ? C3F H3F2 0.9900 . ? C4F C5F 1.545(19) . ? C4F H4F1 0.9900 . ? C4F H4F2 0.9900 . ? C5F C6F 1.483(19) . ? C5F H5F1 0.9900 . ? C5F H5F2 0.9900 . ? C6F C7F 1.57(2) . ? C6F H6F1 0.9900 . ? C6F H6F2 0.9900 . ? C7F C8F 1.54(2) . ? C7F H7F1 0.9900 . ? C7F H7F2 0.9900 . ? C8F H8F1 0.9800 . ? C8F H8F2 0.9800 . ? C8F H8F3 0.9800 . ? C311 C41S 1.417(5) . ? C311 H311 0.9500 . ? C41S C44S 1.400(5) . ? C41S C42S 1.500(5) . ? C42S O8 1.216(5) . ? C42S C43S 1.525(5) . ? C43S O9 1.217(5) . ? C43S C44S 1.470(5) . ? C44S O10 1.324(4) . ? C45 C46A 1.336(10) . ? C45 O10 1.465(4) . ? C45 C46B 1.509(9) . ? C45 H45A 0.9900 . ? C45 H45B 0.9900 . ? C46A H46A 0.9800 . ? C46A H46B 0.9800 . ? C46A H46C 0.9800 . ? C46B H46D 0.9800 . ? C46B H46E 0.9800 . ? C46B H46F 0.9800 . ? C201 C202 1.387(5) . ? C201 C206 1.396(5) . ? C201 N201 1.404(5) . ? C202 C203 1.386(5) . ? C202 H202 0.9500 . ? C203 C204 1.389(6) . ? C203 H203 0.9500 . ? C204 C205 1.403(6) . ? C204 C212 1.490(5) . ? C205 C206 1.384(5) . ? C205 H205 0.9500 . ? C206 C207 1.520(5) . ? C207 C208 1.533(5) . ? C207 C210 1.541(5) . ? C207 C209 1.545(6) . ? C208 C211 1.374(5) . ? C208 N201 1.377(5) . ? C209 H20A 0.9800 . ? C209 H20B 0.9800 . ? C209 H20C 0.9800 . ? C210 H21A 0.9800 . ? C210 H21B 0.9800 . ? C210 H21C 0.9800 . ? C212 O201 1.252(5) . ? C212 O202 1.297(5) . ? C1C N201 1.466(5) . ? C1C C2C 1.528(6) . ? C1C H1C1 0.9900 . ? C1C H1C2 0.9900 . ? C2C C3C 1.527(5) . ? C2C H2C1 0.9900 . ? C2C H2C2 0.9900 . ? C3C C4C 1.517(15) . ? C3C C4D 1.543(12) . ? C3C H3C1 0.9900 . ? C3C H3C2 0.9900 . ? C4C C5C 1.535(16) . ? C4C H4C1 0.9900 . ? C4C H4C2 0.9900 . ? C5C C6C 1.506(14) . ? C5C H5C1 0.9900 . ? C5C H5C2 0.9900 . ? C6C C7C 1.483(14) . ? C6C H6C1 0.9900 . ? C6C H6C2 0.9900 . ? C7C C8C 1.540(14) . ? C7C H7C1 0.9900 . ? C7C H7C2 0.9900 . ? C8C H8C1 0.9800 . ? C8C H8C2 0.9800 . ? C8C H8C3 0.9800 . ? C4D C5D 1.516(12) . ? C4D H4D1 0.9900 . ? C4D H4D2 0.9900 . ? C5D C6D 1.493(12) . ? C5D H5D1 0.9900 . ? C5D H5D2 0.9900 . ? C6D C7D 1.261(14) . ? C6D H6D1 0.9900 . ? C6D H6D2 0.9900 . ? C7D C8D 1.533(12) . ? C7D H7D1 0.9900 . ? C7D H7D2 0.9900 . ? C8D H8D1 0.9800 . ? C8D H8D2 0.9800 . ? C8D H8D3 0.9800 . ? C211 C31S 1.408(5) . ? C211 H211 0.9500 . ? C31S C34S 1.417(5) . ? C31S C32S 1.506(6) . ? C32S O31S 1.206(5) . ? C32S C33S 1.527(5) . ? C33S O32S 1.220(5) . ? C33S C34S 1.484(5) . ? C34S O33S 1.310(5) . ? C35S O33S 1.486(4) . ? C35S C36S 1.506(6) . ? C36S H36A 0.9800 . ? C36S H36B 0.9800 . ? C36S H36C 0.9800 . ? C101 C102 1.395(6) . ? C101 C106 1.396(5) . ? C101 N101 1.402(5) . ? C102 C103 1.391(5) . ? C102 H102 0.9500 . ? C103 C104 1.396(6) . ? C103 H103 0.9500 . ? C104 C105 1.402(6) . ? C104 C112 1.483(6) . ? C105 C106 1.364(5) . ? C105 H105 0.9500 . ? C106 C107 1.515(5) . ? C107 C110 1.531(6) . ? C107 C109 1.534(6) . ? C107 C108 1.541(5) . ? C108 N101 1.373(5) . ? C108 C111 1.379(5) . ? C110 H11A 0.9800 . ? C110 H11B 0.9800 . ? C110 H11C 0.9800 . ? C109 H10D 0.9800 . ? C109 H10E 0.9800 . ? C109 H10F 0.9800 . ? C112 O101 1.239(5) . ? C112 O102 1.311(5) . ? C1B N101 1.464(5) . ? C1B C2B 1.529(6) . ? C1B H1B1 0.9900 . ? C1B H1B2 0.9900 . ? C2B C3B 1.539(6) . ? C2B H2B1 0.9900 . ? C2B H2B2 0.9900 . ? C3B C4B 1.523(6) . ? C3B H3B1 0.9900 . ? C3B H3B2 0.9900 . ? C4B C5B 1.524(6) . ? C4B H4B1 0.9900 . ? C4B H4B2 0.9900 . ? C5B C6B 1.529(7) . ? C5B H5B1 0.9900 . ? C5B H5B2 0.9900 . ? C6B C7B 1.522(6) . ? C6B H6B1 0.9900 . ? C6B H6B2 0.9900 . ? C7B C8B 1.506(7) . ? C7B H7B1 0.9900 . ? C7B H7B2 0.9900 . ? C8B H8B1 0.9800 . ? C8B H8B2 0.9800 . ? C8B H8B3 0.9800 . ? C111 C21S 1.426(6) . ? C111 H111 0.9500 . ? C21S C24S 1.404(5) . ? C21S C22S 1.481(6) . ? C22S O21S 1.213(5) . ? C22S C23S 1.542(6) . ? C23S O22S 1.220(5) . ? C23S C24S 1.457(6) . ? C24S O23S 1.321(5) . ? C25S C26S 1.449(8) . ? C25S O23S 1.474(6) . ? C25S H25A 0.9900 . ? C25S H25B 0.9900 . ? C26S H26A 0.9800 . ? C26S H26B 0.9800 . ? C26S H26C 0.9800 . ? O2 H2A 0.8400 . ? O302 H30D 0.8400 . ? O202 H20D 0.8400 . ? O102 H10G 0.8400 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 C1 C6 123.5(3) . . ? C2 C1 N1 127.9(4) . . ? C6 C1 N1 108.6(3) . . ? C3 C2 C1 116.3(4) . . ? C3 C2 H2 121.8 . . ? C1 C2 H2 121.8 . . ? C2 C3 C4 122.1(4) . . ? C2 C3 H3 118.9 . . ? C4 C3 H3 118.9 . . ? C3 C4 C5 120.1(4) . . ? C3 C4 C12 119.0(4) . . ? C5 C4 C12 120.8(4) . . ? C6 C5 C4 118.7(4) . . ? C6 C5 H5 120.6 . . ? C4 C5 H5 120.6 . . ? C5 C6 C1 119.1(4) . . ? C5 C6 C7 130.9(4) . . ? C1 C6 C7 109.9(3) . . ? C6 C7 C8 101.7(3) . . ? C6 C7 C9 111.1(3) . . ? C8 C7 C9 113.2(3) . . ? C6 C7 C10 111.1(3) . . ? C8 C7 C10 110.0(3) . . ? C9 C7 C10 109.6(3) . . ? C11 C8 N1 120.4(3) . . ? C11 C8 C7 131.5(3) . . ? N1 C8 C7 108.0(3) . . ? C7 C9 H9A 109.5 . . ? C7 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? C7 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? C7 C10 H10A 109.5 . . ? C7 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? C7 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? O1 C12 O2 123.6(4) . . ? O1 C12 C4 121.1(4) . . ? O2 C12 C4 115.3(4) . . ? N1 C1A C2A 112.7(3) . . ? N1 C1A H1A1 109.1 . . ? C2A C1A H1A1 109.1 . . ? N1 C1A H1A2 109.1 . . ? C2A C1A H1A2 109.1 . . ? H1A1 C1A H1A2 107.8 . . ? C3A C2A C1A 112.7(3) . . ? C3A C2A H2A1 109.1 . . ? C1A C2A H2A1 109.1 . . ? C3A C2A H2A2 109.1 . . ? C1A C2A H2A2 109.1 . . ? H2A1 C2A H2A2 107.8 . . ? C2A C3A C4A 116.3(4) . . ? C2A C3A H3A1 108.2 . . ? C4A C3A H3A1 108.2 . . ? C2A C3A H3A2 108.2 . . ? C4A C3A H3A2 108.2 . . ? H3A1 C3A H3A2 107.4 . . ? C3A C4A C5A 112.1(4) . . ? C3A C4A H4A1 109.2 . . ? C5A C4A H4A1 109.2 . . ? C3A C4A H4A2 109.2 . . ? C5A C4A H4A2 109.2 . . ? H4A1 C4A H4A2 107.9 . . ? C6A C5A C4A 115.0(4) . . ? C6A C5A H5A1 108.5 . . ? C4A C5A H5A1 108.5 . . ? C6A C5A H5A2 108.5 . . ? C4A C5A H5A2 108.5 . . ? H5A1 C5A H5A2 107.5 . . ? C5A C6A C7A 115.1(5) . . ? C5A C6A H6A1 108.5 . . ? C7A C6A H6A1 108.5 . . ? C5A C6A H6A2 108.5 . . ? C7A C6A H6A2 108.5 . . ? H6A1 C6A H6A2 107.5 . . ? C8A C7A C6A 113.6(5) . . ? C8A C7A H7A1 108.8 . . ? C6A C7A H7A1 108.8 . . ? C8A C7A H7A2 108.8 . . ? C6A C7A H7A2 108.8 . . ? H7A1 C7A H7A2 107.7 . . ? C7A C8A H8A1 109.5 . . ? C7A C8A H8A2 109.5 . . ? H8A1 C8A H8A2 109.5 . . ? C7A C8A H8A3 109.5 . . ? H8A1 C8A H8A3 109.5 . . ? H8A2 C8A H8A3 109.5 . . ? C8 C11 C1S 132.5(4) . . ? C8 C11 H11 113.8 . . ? C1S C11 H11 113.8 . . ? C4S C1S C11 125.9(4) . . ? C4S C1S C2S 89.8(3) . . ? C11 C1S C2S 144.2(4) . . ? O1S C2S C1S 138.7(4) . . ? O1S C2S C3S 133.6(4) . . ? C1S C2S C3S 87.6(3) . . ? O2S C3S C4S 137.1(4) . . ? O2S C3S C2S 135.1(4) . . ? C4S C3S C2S 87.7(3) . . ? O3S C4S C1S 125.8(4) . . ? O3S C4S C3S 139.3(3) . . ? C1S C4S C3S 94.8(3) . . ? O3S C5S C6S 110.2(4) . . ? O3S C5S H5S1 109.6 . . ? C6S C5S H5S1 109.6 . . ? O3S C5S H5S2 109.6 . . ? C6S C5S H5S2 109.6 . . ? H5S1 C5S H5S2 108.1 . . ? C5S C6S H6S1 109.5 . . ? C5S C6S H6S2 109.5 . . ? H6S1 C6S H6S2 109.5 . . ? C5S C6S H6S3 109.5 . . ? H6S1 C6S H6S3 109.5 . . ? H6S2 C6S H6S3 109.5 . . ? C306 C301 C302 123.2(3) . . ? C306 C301 N301 109.4(3) . . ? C302 C301 N301 127.3(3) . . ? C301 C302 C303 116.6(4) . . ? C301 C302 H302 121.7 . . ? C303 C302 H302 121.7 . . ? C304 C303 C302 120.8(4) . . ? C304 C303 H303 119.6 . . ? C302 C303 H303 119.6 . . ? C305 C304 C303 120.8(3) . . ? C305 C304 C312 121.3(4) . . ? C303 C304 C312 117.9(4) . . ? C306 C305 C304 118.9(4) . . ? C306 C305 H305 120.5 . . ? C304 C305 H305 120.5 . . ? C305 C306 C301 119.7(4) . . ? C305 C306 C307 130.5(4) . . ? C301 C306 C307 109.8(3) . . ? C310 C307 C309 110.7(3) . . ? C310 C307 C306 112.7(3) . . ? C309 C307 C306 110.6(3) . . ? C310 C307 C308 109.7(3) . . ? C309 C307 C308 112.2(3) . . ? C306 C307 C308 100.6(3) . . ? N301 C308 C311 120.6(3) . . ? N301 C308 C307 108.8(3) . . ? C311 C308 C307 130.6(3) . . ? C307 C309 H30A 109.5 . . ? C307 C309 H30B 109.5 . . ? H30A C309 H30B 109.5 . . ? C307 C309 H30C 109.5 . . ? H30A C309 H30C 109.5 . . ? H30B C309 H30C 109.5 . . ? C307 C310 H31A 109.5 . . ? C307 C310 H31B 109.5 . . ? H31A C310 H31B 109.5 . . ? C307 C310 H31C 109.5 . . ? H31A C310 H31C 109.5 . . ? H31B C310 H31C 109.5 . . ? O301 C312 O302 122.2(4) . . ? O301 C312 C304 120.6(4) . . ? O302 C312 C304 117.2(4) . . ? N301 C1E C2E 111.8(3) . . ? N301 C1E H1E1 109.3 . . ? C2E C1E H1E1 109.3 . . ? N301 C1E H1E2 109.3 . . ? C2E C1E H1E2 109.3 . . ? H1E1 C1E H1E2 107.9 . . ? C1E C2E C3E 112.7(5) . . ? C1E C2E C3F 112.6(15) . . ? C3E C2E C3F 14.0(11) . . ? C1E C2E H2E1 109.1 . . ? C3E C2E H2E1 109.1 . . ? C3F C2E H2E1 120.4 . . ? C1E C2E H2E2 109.1 . . ? C3E C2E H2E2 109.1 . . ? C3F C2E H2E2 96.7 . . ? H2E1 C2E H2E2 107.8 . . ? C4E C3E C2E 114.6(6) . . ? C4E C3E H3E1 108.6 . . ? C2E C3E H3E1 108.6 . . ? C4E C3E H3E2 108.6 . . ? C2E C3E H3E2 108.6 . . ? H3E1 C3E H3E2 107.6 . . ? C5E C4E C3E 114.9(8) . . ? C5E C4E H4E1 108.5 . . ? C3E C4E H4E1 108.5 . . ? C5E C4E H4E2 108.5 . . ? C3E C4E H4E2 108.5 . . ? H4E1 C4E H4E2 107.5 . . ? C6E C5E C4E 115.5(9) . . ? C6E C5E H5E1 108.4 . . ? C4E C5E H5E1 108.4 . . ? C6E C5E H5E2 108.4 . . ? C4E C5E H5E2 108.4 . . ? H5E1 C5E H5E2 107.5 . . ? C5E C6E C7E 112.0(10) . . ? C5E C6E H6E1 109.2 . . ? C7E C6E H6E1 109.2 . . ? C5E C6E H6E2 109.2 . . ? C7E C6E H6E2 109.2 . . ? H6E1 C6E H6E2 107.9 . . ? C8E C7E C6E 106.0(11) . . ? C8E C7E H7E1 110.5 . . ? C6E C7E H7E1 110.5 . . ? C8E C7E H7E2 110.5 . . ? C6E C7E H7E2 110.5 . . ? H7E1 C7E H7E2 108.7 . . ? C7E C8E H8E1 109.5 . . ? C7E C8E H8E2 109.5 . . ? H8E1 C8E H8E2 109.5 . . ? C7E C8E H8E3 109.5 . . ? H8E1 C8E H8E3 109.5 . . ? H8E2 C8E H8E3 109.5 . . ? C4F C3F C2E 109.0(18) . . ? C4F C3F H3F1 109.9 . . ? C2E C3F H3F1 109.9 . . ? C4F C3F H3F2 109.9 . . ? C2E C3F H3F2 109.9 . . ? H3F1 C3F H3F2 108.3 . . ? C3F C4F C5F 121(2) . . ? C3F C4F H4F1 107.2 . . ? C5F C4F H4F1 107.2 . . ? C3F C4F H4F2 107.2 . . ? C5F C4F H4F2 107.2 . . ? H4F1 C4F H4F2 106.8 . . ? C6F C5F C4F 111(3) . . ? C6F C5F H5F1 109.4 . . ? C4F C5F H5F1 109.4 . . ? C6F C5F H5F2 109.4 . . ? C4F C5F H5F2 109.4 . . ? H5F1 C5F H5F2 108.0 . . ? C5F C6F C7F 101(3) . . ? C5F C6F H6F1 111.6 . . ? C7F C6F H6F1 111.6 . . ? C5F C6F H6F2 111.6 . . ? C7F C6F H6F2 111.6 . . ? H6F1 C6F H6F2 109.4 . . ? C8F C7F C6F 113(3) . . ? C8F C7F H7F1 108.9 . . ? C6F C7F H7F1 108.9 . . ? C8F C7F H7F2 108.9 . . ? C6F C7F H7F2 108.9 . . ? H7F1 C7F H7F2 107.8 . . ? C7F C8F H8F1 109.5 . . ? C7F C8F H8F2 109.5 . . ? H8F1 C8F H8F2 109.5 . . ? C7F C8F H8F3 109.5 . . ? H8F1 C8F H8F3 109.5 . . ? H8F2 C8F H8F3 109.5 . . ? C308 C311 C41S 131.9(4) . . ? C308 C311 H311 114.0 . . ? C41S C311 H311 114.0 . . ? C44S C41S C311 125.1(3) . . ? C44S C41S C42S 89.8(3) . . ? C311 C41S C42S 145.1(3) . . ? O8 C42S C41S 137.1(4) . . ? O8 C42S C43S 134.0(4) . . ? C41S C42S C43S 88.8(3) . . ? O9 C43S C44S 138.0(4) . . ? O9 C43S C42S 135.7(4) . . ? C44S C43S C42S 86.3(3) . . ? O10 C44S C41S 129.3(3) . . ? O10 C44S C43S 135.7(3) . . ? C41S C44S C43S 95.0(3) . . ? C46A C45 O10 106.5(5) . . ? C46A C45 C46B 53.7(7) . . ? O10 C45 C46B 109.0(4) . . ? C46A C45 H45A 110.4 . . ? O10 C45 H45A 110.4 . . ? C46B C45 H45A 140.4 . . ? C46A C45 H45B 110.4 . . ? O10 C45 H45B 110.4 . . ? C46B C45 H45B 59.3 . . ? H45A C45 H45B 108.6 . . ? C45 C46A H46A 109.5 . . ? C45 C46A H46B 109.5 . . ? H46A C46A H46B 109.5 . . ? C45 C46A H46C 109.5 . . ? H46A C46A H46C 109.5 . . ? H46B C46A H46C 109.5 . . ? C45 C46B H46D 109.5 . . ? C45 C46B H46E 109.5 . . ? H46D C46B H46E 109.5 . . ? C45 C46B H46F 109.5 . . ? H46D C46B H46F 109.5 . . ? H46E C46B H46F 109.5 . . ? C202 C201 C206 122.8(3) . . ? C202 C201 N201 127.9(3) . . ? C206 C201 N201 109.2(3) . . ? C203 C202 C201 117.0(4) . . ? C203 C202 H202 121.5 . . ? C201 C202 H202 121.5 . . ? C202 C203 C204 121.4(4) . . ? C202 C203 H203 119.3 . . ? C204 C203 H203 119.3 . . ? C203 C204 C205 120.8(3) . . ? C203 C204 C212 119.3(4) . . ? C205 C204 C212 119.8(4) . . ? C206 C205 C204 118.5(4) . . ? C206 C205 H205 120.8 . . ? C204 C205 H205 120.8 . . ? C205 C206 C201 119.5(4) . . ? C205 C206 C207 131.2(4) . . ? C201 C206 C207 109.3(3) . . ? C206 C207 C208 101.6(3) . . ? C206 C207 C210 110.8(3) . . ? C208 C207 C210 110.8(3) . . ? C206 C207 C209 110.2(3) . . ? C208 C207 C209 112.2(3) . . ? C210 C207 C209 110.8(3) . . ? C211 C208 N201 120.8(3) . . ? C211 C208 C207 130.8(3) . . ? N201 C208 C207 108.5(3) . . ? C207 C209 H20A 109.5 . . ? C207 C209 H20B 109.5 . . ? H20A C209 H20B 109.5 . . ? C207 C209 H20C 109.5 . . ? H20A C209 H20C 109.5 . . ? H20B C209 H20C 109.5 . . ? C207 C210 H21A 109.5 . . ? C207 C210 H21B 109.5 . . ? H21A C210 H21B 109.5 . . ? C207 C210 H21C 109.5 . . ? H21A C210 H21C 109.5 . . ? H21B C210 H21C 109.5 . . ? O201 C212 O202 123.5(4) . . ? O201 C212 C204 119.8(4) . . ? O202 C212 C204 116.7(4) . . ? N201 C1C C2C 111.4(3) . . ? N201 C1C H1C1 109.3 . . ? C2C C1C H1C1 109.3 . . ? N201 C1C H1C2 109.3 . . ? C2C C1C H1C2 109.3 . . ? H1C1 C1C H1C2 108.0 . . ? C3C C2C C1C 113.4(3) . . ? C3C C2C H2C1 108.9 . . ? C1C C2C H2C1 108.9 . . ? C3C C2C H2C2 108.9 . . ? C1C C2C H2C2 108.9 . . ? H2C1 C2C H2C2 107.7 . . ? C4C C3C C2C 118.9(8) . . ? C4C C3C C4D 8.8(15) . . ? C2C C3C C4D 111.0(6) . . ? C4C C3C H3C1 107.6 . . ? C2C C3C H3C1 107.6 . . ? C4D C3C H3C1 115.1 . . ? C4C C3C H3C2 107.6 . . ? C2C C3C H3C2 107.6 . . ? C4D C3C H3C2 108.3 . . ? H3C1 C3C H3C2 107.0 . . ? C3C C4C C5C 106.2(12) . . ? C3C C4C H4C1 110.5 . . ? C5C C4C H4C1 110.5 . . ? C3C C4C H4C2 110.5 . . ? C5C C4C H4C2 110.5 . . ? H4C1 C4C H4C2 108.7 . . ? C6C C5C C4C 107.7(12) . . ? C6C C5C H5C1 110.2 . . ? C4C C5C H5C1 110.2 . . ? C6C C5C H5C2 110.2 . . ? C4C C5C H5C2 110.2 . . ? H5C1 C5C H5C2 108.5 . . ? C7C C6C C5C 159.6(14) . . ? C7C C6C H6C1 96.3 . . ? C5C C6C H6C1 96.3 . . ? C7C C6C H6C2 96.3 . . ? C5C C6C H6C2 96.3 . . ? H6C1 C6C H6C2 103.4 . . ? C6C C7C C8C 145.8(14) . . ? C6C C7C H7C1 100.4 . . ? C8C C7C H7C1 100.4 . . ? C6C C7C H7C2 100.4 . . ? C8C C7C H7C2 100.4 . . ? H7C1 C7C H7C2 104.3 . . ? C7C C8C H8C1 109.5 . . ? C7C C8C H8C2 109.5 . . ? H8C1 C8C H8C2 109.5 . . ? C7C C8C H8C3 109.5 . . ? H8C1 C8C H8C3 109.5 . . ? H8C2 C8C H8C3 109.5 . . ? C5D C4D C3C 117.5(10) . . ? C5D C4D H4D1 107.9 . . ? C3C C4D H4D1 107.9 . . ? C5D C4D H4D2 107.9 . . ? C3C C4D H4D2 107.9 . . ? H4D1 C4D H4D2 107.2 . . ? C6D C5D C4D 120.0(10) . . ? C6D C5D H5D1 107.3 . . ? C4D C5D H5D1 107.3 . . ? C6D C5D H5D2 107.3 . . ? C4D C5D H5D2 107.3 . . ? H5D1 C5D H5D2 106.9 . . ? C7D C6D C5D 106.4(11) . . ? C7D C6D H6D1 110.5 . . ? C5D C6D H6D1 110.5 . . ? C7D C6D H6D2 110.5 . . ? C5D C6D H6D2 110.5 . . ? H6D1 C6D H6D2 108.6 . . ? C6D C7D C8D 103.5(10) . . ? C6D C7D H7D1 111.1 . . ? C8D C7D H7D1 111.1 . . ? C6D C7D H7D2 111.1 . . ? C8D C7D H7D2 111.1 . . ? H7D1 C7D H7D2 109.0 . . ? C7D C8D H8D1 109.5 . . ? C7D C8D H8D2 109.5 . . ? H8D1 C8D H8D2 109.5 . . ? C7D C8D H8D3 109.5 . . ? H8D1 C8D H8D3 109.5 . . ? H8D2 C8D H8D3 109.5 . . ? C208 C211 C31S 132.5(4) . . ? C208 C211 H211 113.7 . . ? C31S C211 H211 113.7 . . ? C211 C31S C34S 125.5(4) . . ? C211 C31S C32S 144.2(3) . . ? C34S C31S C32S 90.3(3) . . ? O31S C32S C31S 138.2(4) . . ? O31S C32S C33S 133.0(4) . . ? C31S C32S C33S 88.7(3) . . ? O32S C33S C34S 135.9(4) . . ? O32S C33S C32S 137.0(4) . . ? C34S C33S C32S 87.0(3) . . ? O33S C34S C31S 127.1(3) . . ? O33S C34S C33S 139.0(3) . . ? C31S C34S C33S 93.9(3) . . ? O33S C35S C36S 110.3(3) . . ? C35S C36S H36A 109.5 . . ? C35S C36S H36B 109.5 . . ? H36A C36S H36B 109.5 . . ? C35S C36S H36C 109.5 . . ? H36A C36S H36C 109.5 . . ? H36B C36S H36C 109.5 . . ? C102 C101 C106 122.7(4) . . ? C102 C101 N101 128.0(4) . . ? C106 C101 N101 109.2(3) . . ? C103 C102 C101 117.2(4) . . ? C103 C102 H102 121.4 . . ? C101 C102 H102 121.4 . . ? C102 C103 C104 120.4(4) . . ? C102 C103 H103 119.8 . . ? C104 C103 H103 119.8 . . ? C103 C104 C105 121.0(4) . . ? C103 C104 C112 117.7(4) . . ? C105 C104 C112 121.3(4) . . ? C106 C105 C104 119.2(4) . . ? C106 C105 H105 120.4 . . ? C104 C105 H105 120.4 . . ? C105 C106 C101 119.5(4) . . ? C105 C106 C107 130.6(4) . . ? C101 C106 C107 109.8(3) . . ? C106 C107 C110 112.2(3) . . ? C106 C107 C109 110.7(3) . . ? C110 C107 C109 110.3(3) . . ? C106 C107 C108 100.8(3) . . ? C110 C107 C108 110.4(3) . . ? C109 C107 C108 112.0(3) . . ? N101 C108 C111 120.2(3) . . ? N101 C108 C107 109.0(3) . . ? C111 C108 C107 130.8(4) . . ? C107 C110 H11A 109.5 . . ? C107 C110 H11B 109.5 . . ? H11A C110 H11B 109.5 . . ? C107 C110 H11C 109.5 . . ? H11A C110 H11C 109.5 . . ? H11B C110 H11C 109.5 . . ? C107 C109 H10D 109.5 . . ? C107 C109 H10E 109.5 . . ? H10D C109 H10E 109.5 . . ? C107 C109 H10F 109.5 . . ? H10D C109 H10F 109.5 . . ? H10E C109 H10F 109.5 . . ? O101 C112 O102 121.9(4) . . ? O101 C112 C104 122.4(4) . . ? O102 C112 C104 115.6(4) . . ? N101 C1B C2B 113.2(3) . . ? N101 C1B H1B1 108.9 . . ? C2B C1B H1B1 108.9 . . ? N101 C1B H1B2 108.9 . . ? C2B C1B H1B2 108.9 . . ? H1B1 C1B H1B2 107.8 . . ? C1B C2B C3B 112.0(3) . . ? C1B C2B H2B1 109.2 . . ? C3B C2B H2B1 109.2 . . ? C1B C2B H2B2 109.2 . . ? C3B C2B H2B2 109.2 . . ? H2B1 C2B H2B2 107.9 . . ? C4B C3B C2B 112.8(4) . . ? C4B C3B H3B1 109.0 . . ? C2B C3B H3B1 109.0 . . ? C4B C3B H3B2 109.0 . . ? C2B C3B H3B2 109.0 . . ? H3B1 C3B H3B2 107.8 . . ? C3B C4B C5B 116.0(4) . . ? C3B C4B H4B1 108.3 . . ? C5B C4B H4B1 108.3 . . ? C3B C4B H4B2 108.3 . . ? C5B C4B H4B2 108.3 . . ? H4B1 C4B H4B2 107.4 . . ? C4B C5B C6B 111.8(4) . . ? C4B C5B H5B1 109.3 . . ? C6B C5B H5B1 109.3 . . ? C4B C5B H5B2 109.3 . . ? C6B C5B H5B2 109.3 . . ? H5B1 C5B H5B2 107.9 . . ? C7B C6B C5B 115.9(4) . . ? C7B C6B H6B1 108.3 . . ? C5B C6B H6B1 108.3 . . ? C7B C6B H6B2 108.3 . . ? C5B C6B H6B2 108.3 . . ? H6B1 C6B H6B2 107.4 . . ? C8B C7B C6B 111.9(4) . . ? C8B C7B H7B1 109.2 . . ? C6B C7B H7B1 109.2 . . ? C8B C7B H7B2 109.2 . . ? C6B C7B H7B2 109.2 . . ? H7B1 C7B H7B2 107.9 . . ? C7B C8B H8B1 109.5 . . ? C7B C8B H8B2 109.5 . . ? H8B1 C8B H8B2 109.5 . . ? C7B C8B H8B3 109.5 . . ? H8B1 C8B H8B3 109.5 . . ? H8B2 C8B H8B3 109.5 . . ? C108 C111 C21S 132.2(4) . . ? C108 C111 H111 113.9 . . ? C21S C111 H111 113.9 . . ? C24S C21S C111 124.7(4) . . ? C24S C21S C22S 90.2(3) . . ? C111 C21S C22S 145.1(4) . . ? O21S C22S C21S 138.0(4) . . ? O21S C22S C23S 133.4(4) . . ? C21S C22S C23S 88.6(3) . . ? O22S C23S C24S 138.0(4) . . ? O22S C23S C22S 136.0(4) . . ? C24S C23S C22S 86.0(3) . . ? O23S C24S C21S 127.6(4) . . ? O23S C24S C23S 137.2(4) . . ? C21S C24S C23S 95.2(3) . . ? C26S C25S O23S 108.6(5) . . ? C26S C25S H25A 110.0 . . ? O23S C25S H25A 110.0 . . ? C26S C25S H25B 110.0 . . ? O23S C25S H25B 110.0 . . ? H25A C25S H25B 108.3 . . ? C25S C26S H26A 109.5 . . ? C25S C26S H26B 109.5 . . ? H26A C26S H26B 109.5 . . ? C25S C26S H26C 109.5 . . ? H26A C26S H26C 109.5 . . ? H26B C26S H26C 109.5 . . ? C12 O2 H2A 109.5 . . ? C4S O3S C5S 116.6(3) . . ? C312 O302 H30D 109.5 . . ? C44S O10 C45 118.0(3) . . ? C212 O202 H20D 109.5 . . ? C34S O33S C35S 116.5(3) . . ? C112 O102 H10G 109.5 . . ? C24S O23S C25S 116.1(4) . . ? C8 N1 C1 111.3(3) . . ? C8 N1 C1A 125.3(3) . . ? C1 N1 C1A 123.1(3) . . ? C208 N201 C201 111.4(3) . . ? C208 N201 C1C 125.0(3) . . ? C201 N201 C1C 123.3(3) . . ? C308 N301 C301 111.3(3) . . ? C308 N301 C1E 125.7(3) . . ? C301 N301 C1E 123.0(3) . . ? C108 N101 C101 111.1(3) . . ? C108 N101 C1B 125.0(3) . . ? C101 N101 C1B 123.9(3) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C6 C1 C2 C3 -4.1(6) . . . . ? N1 C1 C2 C3 173.3(4) . . . . ? C1 C2 C3 C4 0.7(6) . . . . ? C2 C3 C4 C5 2.4(7) . . . . ? C2 C3 C4 C12 -174.9(4) . . . . ? C3 C4 C5 C6 -2.4(6) . . . . ? C12 C4 C5 C6 174.9(4) . . . . ? C4 C5 C6 C1 -0.7(6) . . . . ? C4 C5 C6 C7 -175.9(4) . . . . ? C2 C1 C6 C5 4.1(6) . . . . ? N1 C1 C6 C5 -173.7(4) . . . . ? C2 C1 C6 C7 -179.8(4) . . . . ? N1 C1 C6 C7 2.5(4) . . . . ? C5 C6 C7 C8 170.1(4) . . . . ? C1 C6 C7 C8 -5.5(4) . . . . ? C5 C6 C7 C9 49.3(6) . . . . ? C1 C6 C7 C9 -126.2(4) . . . . ? C5 C6 C7 C10 -72.9(5) . . . . ? C1 C6 C7 C10 111.6(4) . . . . ? C6 C7 C8 C11 -174.0(4) . . . . ? C9 C7 C8 C11 -54.7(6) . . . . ? C10 C7 C8 C11 68.3(5) . . . . ? C6 C7 C8 N1 6.6(4) . . . . ? C9 C7 C8 N1 125.9(3) . . . . ? C10 C7 C8 N1 -111.1(3) . . . . ? C3 C4 C12 O1 3.3(7) . . . . ? C5 C4 C12 O1 -174.0(4) . . . . ? C3 C4 C12 O2 -178.0(4) . . . . ? C5 C4 C12 O2 4.7(6) . . . . ? N1 C1A C2A C3A -176.6(3) . . . . ? C1A C2A C3A C4A -68.8(5) . . . . ? C2A C3A C4A C5A 171.0(4) . . . . ? C3A C4A C5A C6A -178.3(4) . . . . ? C4A C5A C6A C7A 173.4(5) . . . . ? C5A C6A C7A C8A -67.4(8) . . . . ? N1 C8 C11 C1S 179.2(4) . . . . ? C7 C8 C11 C1S -0.1(7) . . . . ? C8 C11 C1S C4S 177.3(4) . . . . ? C8 C11 C1S C2S -4.3(9) . . . . ? C4S C1S C2S O1S 179.6(5) . . . . ? C11 C1S C2S O1S 0.9(10) . . . . ? C4S C1S C2S C3S 0.5(3) . . . . ? C11 C1S C2S C3S -178.2(6) . . . . ? O1S C2S C3S O2S -0.8(8) . . . . ? C1S C2S C3S O2S 178.4(5) . . . . ? O1S C2S C3S C4S -179.7(5) . . . . ? C1S C2S C3S C4S -0.5(3) . . . . ? C11 C1S C4S O3S -1.9(6) . . . . ? C2S C1S C4S O3S 179.1(4) . . . . ? C11 C1S C4S C3S 178.5(4) . . . . ? C2S C1S C4S C3S -0.5(3) . . . . ? O2S C3S C4S O3S 2.2(9) . . . . ? C2S C3S C4S O3S -179.0(5) . . . . ? O2S C3S C4S C1S -178.3(5) . . . . ? C2S C3S C4S C1S 0.5(3) . . . . ? C306 C301 C302 C303 -0.6(6) . . . . ? N301 C301 C302 C303 174.7(4) . . . . ? C301 C302 C303 C304 -0.3(6) . . . . ? C302 C303 C304 C305 2.1(6) . . . . ? C302 C303 C304 C312 -176.5(4) . . . . ? C303 C304 C305 C306 -3.0(6) . . . . ? C312 C304 C305 C306 175.6(4) . . . . ? C304 C305 C306 C301 2.0(6) . . . . ? C304 C305 C306 C307 -175.9(4) . . . . ? C302 C301 C306 C305 -0.3(6) . . . . ? N301 C301 C306 C305 -176.3(3) . . . . ? C302 C301 C306 C307 178.1(4) . . . . ? N301 C301 C306 C307 2.1(4) . . . . ? C305 C306 C307 C310 -68.1(5) . . . . ? C301 C306 C307 C310 113.8(4) . . . . ? C305 C306 C307 C309 56.3(5) . . . . ? C301 C306 C307 C309 -121.8(4) . . . . ? C305 C306 C307 C308 175.0(4) . . . . ? C301 C306 C307 C308 -3.1(4) . . . . ? C310 C307 C308 N301 -116.0(3) . . . . ? C309 C307 C308 N301 120.6(3) . . . . ? C306 C307 C308 N301 3.0(4) . . . . ? C310 C307 C308 C311 62.0(5) . . . . ? C309 C307 C308 C311 -61.4(5) . . . . ? C306 C307 C308 C311 -179.0(4) . . . . ? C305 C304 C312 O301 -176.1(4) . . . . ? C303 C304 C312 O301 2.5(6) . . . . ? C305 C304 C312 O302 -0.2(6) . . . . ? C303 C304 C312 O302 178.5(4) . . . . ? N301 C1E C2E C3E 169.3(4) . . . . ? N301 C1E C2E C3F -175.6(11) . . . . ? C1E C2E C3E C4E -64.0(9) . . . . ? C3F C2E C3E C4E -156(8) . . . . ? C2E C3E C4E C5E -165.5(8) . . . . ? C3E C4E C5E C6E -64.9(13) . . . . ? C4E C5E C6E C7E -176.7(11) . . . . ? C5E C6E C7E C8E 175.4(14) . . . . ? C1E C2E C3F C4F -73(3) . . . . ? C3E C2E C3F C4F 20(6) . . . . ? C2E C3F C4F C5F 170(3) . . . . ? C3F C4F C5F C6F 68(4) . . . . ? C4F C5F C6F C7F -167(3) . . . . ? C5F C6F C7F C8F -52(5) . . . . ? N301 C308 C311 C41S -177.2(4) . . . . ? C307 C308 C311 C41S 5.1(7) . . . . ? C308 C311 C41S C44S 178.8(4) . . . . ? C308 C311 C41S C42S -2.0(9) . . . . ? C44S C41S C42S O8 -177.7(5) . . . . ? C311 C41S C42S O8 3.0(10) . . . . ? C44S C41S C42S C43S 2.0(3) . . . . ? C311 C41S C42S C43S -177.4(6) . . . . ? O8 C42S C43S O9 -3.3(8) . . . . ? C41S C42S C43S O9 177.0(5) . . . . ? O8 C42S C43S C44S 177.8(5) . . . . ? C41S C42S C43S C44S -1.9(3) . . . . ? C311 C41S C44S O10 -1.1(7) . . . . ? C42S C41S C44S O10 179.4(4) . . . . ? C311 C41S C44S C43S 177.5(4) . . . . ? C42S C41S C44S C43S -2.1(3) . . . . ? O9 C43S C44S O10 1.6(8) . . . . ? C42S C43S C44S O10 -179.6(4) . . . . ? O9 C43S C44S C41S -176.8(5) . . . . ? C42S C43S C44S C41S 2.0(3) . . . . ? C206 C201 C202 C203 1.2(6) . . . . ? N201 C201 C202 C203 179.6(4) . . . . ? C201 C202 C203 C204 0.1(6) . . . . ? C202 C203 C204 C205 -1.0(6) . . . . ? C202 C203 C204 C212 176.1(4) . . . . ? C203 C204 C205 C206 0.8(6) . . . . ? C212 C204 C205 C206 -176.3(4) . . . . ? C204 C205 C206 C201 0.4(6) . . . . ? C204 C205 C206 C207 179.6(4) . . . . ? C202 C201 C206 C205 -1.4(6) . . . . ? N201 C201 C206 C205 179.9(3) . . . . ? C202 C201 C206 C207 179.3(4) . . . . ? N201 C201 C206 C207 0.5(4) . . . . ? C205 C206 C207 C208 -179.7(4) . . . . ? C201 C206 C207 C208 -0.5(4) . . . . ? C205 C206 C207 C210 -61.9(5) . . . . ? C201 C206 C207 C210 117.3(4) . . . . ? C205 C206 C207 C209 61.1(5) . . . . ? C201 C206 C207 C209 -119.6(3) . . . . ? C206 C207 C208 C211 179.3(4) . . . . ? C210 C207 C208 C211 61.5(5) . . . . ? C209 C207 C208 C211 -63.0(5) . . . . ? C206 C207 C208 N201 0.3(4) . . . . ? C210 C207 C208 N201 -117.5(3) . . . . ? C209 C207 C208 N201 118.0(3) . . . . ? C203 C204 C212 O201 2.2(7) . . . . ? C205 C204 C212 O201 179.4(4) . . . . ? C203 C204 C212 O202 -177.8(4) . . . . ? C205 C204 C212 O202 -0.6(6) . . . . ? N201 C1C C2C C3C 163.5(3) . . . . ? C1C C2C C3C C4C -62.9(15) . . . . ? C1C C2C C3C C4D -67.2(10) . . . . ? C2C C3C C4C C5C -165.7(13) . . . . ? C4D C3C C4C C5C -139(14) . . . . ? C3C C4C C5C C6C 175.9(17) . . . . ? C4C C5C C6C C7C -177(5) . . . . ? C5C C6C C7C C8C 161(4) . . . . ? C4C C3C C4D C5D 33(11) . . . . ? C2C C3C C4D C5D -171.9(13) . . . . ? C3C C4D C5D C6D -179.3(14) . . . . ? C4D C5D C6D C7D -85.1(19) . . . . ? C5D C6D C7D C8D -165.0(10) . . . . ? N201 C208 C211 C31S -178.8(4) . . . . ? C207 C208 C211 C31S 2.3(8) . . . . ? C208 C211 C31S C34S -180.0(4) . . . . ? C208 C211 C31S C32S 0.4(9) . . . . ? C211 C31S C32S O31S 2.1(10) . . . . ? C34S C31S C32S O31S -177.6(5) . . . . ? C211 C31S C32S C33S -178.8(6) . . . . ? C34S C31S C32S C33S 1.5(3) . . . . ? O31S C32S C33S O32S -2.5(8) . . . . ? C31S C32S C33S O32S 178.3(5) . . . . ? O31S C32S C33S C34S 177.7(4) . . . . ? C31S C32S C33S C34S -1.5(3) . . . . ? C211 C31S C34S O33S -1.2(7) . . . . ? C32S C31S C34S O33S 178.6(4) . . . . ? C211 C31S C34S C33S 178.6(4) . . . . ? C32S C31S C34S C33S -1.6(3) . . . . ? O32S C33S C34S O33S 1.6(9) . . . . ? C32S C33S C34S O33S -178.7(5) . . . . ? O32S C33S C34S C31S -178.2(5) . . . . ? C32S C33S C34S C31S 1.6(3) . . . . ? C106 C101 C102 C103 -1.3(6) . . . . ? N101 C101 C102 C103 176.5(4) . . . . ? C101 C102 C103 C104 0.8(6) . . . . ? C102 C103 C104 C105 -0.5(6) . . . . ? C102 C103 C104 C112 178.6(4) . . . . ? C103 C104 C105 C106 0.7(6) . . . . ? C112 C104 C105 C106 -178.4(4) . . . . ? C104 C105 C106 C101 -1.2(6) . . . . ? C104 C105 C106 C107 -177.8(4) . . . . ? C102 C101 C106 C105 1.6(6) . . . . ? N101 C101 C106 C105 -176.6(4) . . . . ? C102 C101 C106 C107 178.8(4) . . . . ? N101 C101 C106 C107 0.6(4) . . . . ? C105 C106 C107 C110 -67.2(6) . . . . ? C101 C106 C107 C110 116.0(4) . . . . ? C105 C106 C107 C109 56.5(5) . . . . ? C101 C106 C107 C109 -120.3(4) . . . . ? C105 C106 C107 C108 175.3(4) . . . . ? C101 C106 C107 C108 -1.5(4) . . . . ? C106 C107 C108 N101 2.0(4) . . . . ? C110 C107 C108 N101 -116.8(4) . . . . ? C109 C107 C108 N101 119.8(4) . . . . ? C106 C107 C108 C111 -178.5(4) . . . . ? C110 C107 C108 C111 62.8(6) . . . . ? C109 C107 C108 C111 -60.7(6) . . . . ? C103 C104 C112 O101 -5.3(7) . . . . ? C105 C104 C112 O101 173.8(4) . . . . ? C103 C104 C112 O102 177.4(4) . . . . ? C105 C104 C112 O102 -3.5(6) . . . . ? N101 C1B C2B C3B 163.8(3) . . . . ? C1B C2B C3B C4B -69.2(5) . . . . ? C2B C3B C4B C5B 179.9(4) . . . . ? C3B C4B C5B C6B 174.0(4) . . . . ? C4B C5B C6B C7B 177.2(4) . . . . ? C5B C6B C7B C8B 174.5(4) . . . . ? N101 C108 C111 C21S -179.2(4) . . . . ? C107 C108 C111 C21S 1.2(8) . . . . ? C108 C111 C21S C24S -176.9(5) . . . . ? C108 C111 C21S C22S 3.3(10) . . . . ? C24S C21S C22S O21S -179.8(6) . . . . ? C111 C21S C22S O21S 0.0(11) . . . . ? C24S C21S C22S C23S -0.1(3) . . . . ? C111 C21S C22S C23S 179.7(6) . . . . ? O21S C22S C23S O22S -1.3(9) . . . . ? C21S C22S C23S O22S 178.9(6) . . . . ? O21S C22S C23S C24S 179.9(5) . . . . ? C21S C22S C23S C24S 0.1(3) . . . . ? C111 C21S C24S O23S -1.9(8) . . . . ? C22S C21S C24S O23S 177.9(5) . . . . ? C111 C21S C24S C23S -179.7(4) . . . . ? C22S C21S C24S C23S 0.1(4) . . . . ? O22S C23S C24S O23S 3.6(11) . . . . ? C22S C23S C24S O23S -177.6(6) . . . . ? O22S C23S C24S C21S -178.9(6) . . . . ? C22S C23S C24S C21S -0.1(3) . . . . ? C1S C4S O3S C5S -178.7(4) . . . . ? C3S C4S O3S C5S 0.7(7) . . . . ? C6S C5S O3S C4S -78.5(4) . . . . ? C41S C44S O10 C45 -172.8(4) . . . . ? C43S C44S O10 C45 9.3(6) . . . . ? C46A C45 O10 C44S -85.4(6) . . . . ? C46B C45 O10 C44S -142.0(6) . . . . ? C31S C34S O33S C35S -174.6(4) . . . . ? C33S C34S O33S C35S 5.7(7) . . . . ? C36S C35S O33S C34S -79.3(5) . . . . ? C21S C24S O23S C25S 177.0(5) . . . . ? C23S C24S O23S C25S -6.2(9) . . . . ? C26S C25S O23S C24S 118.9(5) . . . . ? C11 C8 N1 C1 174.8(3) . . . . ? C7 C8 N1 C1 -5.7(4) . . . . ? C11 C8 N1 C1A -0.1(6) . . . . ? C7 C8 N1 C1A 179.4(3) . . . . ? C2 C1 N1 C8 -175.5(4) . . . . ? C6 C1 N1 C8 2.1(4) . . . . ? C2 C1 N1 C1A -0.5(6) . . . . ? C6 C1 N1 C1A 177.2(3) . . . . ? C2A C1A N1 C8 -79.2(5) . . . . ? C2A C1A N1 C1 106.5(4) . . . . ? C211 C208 N201 C201 -179.1(3) . . . . ? C207 C208 N201 C201 0.0(4) . . . . ? C211 C208 N201 C1C -5.4(6) . . . . ? C207 C208 N201 C1C 173.7(3) . . . . ? C202 C201 N201 C208 -179.0(4) . . . . ? C206 C201 N201 C208 -0.3(4) . . . . ? C202 C201 N201 C1C 7.2(6) . . . . ? C206 C201 N201 C1C -174.1(3) . . . . ? C2C C1C N201 C208 -79.6(5) . . . . ? C2C C1C N201 C201 93.4(4) . . . . ? C311 C308 N301 C301 179.7(3) . . . . ? C307 C308 N301 C301 -2.1(4) . . . . ? C311 C308 N301 C1E -2.1(6) . . . . ? C307 C308 N301 C1E 176.2(3) . . . . ? C306 C301 N301 C308 0.0(4) . . . . ? C302 C301 N301 C308 -175.7(4) . . . . ? C306 C301 N301 C1E -178.3(3) . . . . ? C302 C301 N301 C1E 6.0(6) . . . . ? C2E C1E N301 C308 -81.5(4) . . . . ? C2E C1E N301 C301 96.5(4) . . . . ? C111 C108 N101 C101 178.6(4) . . . . ? C107 C108 N101 C101 -1.8(4) . . . . ? C111 C108 N101 C1B -1.8(6) . . . . ? C107 C108 N101 C1B 177.8(3) . . . . ? C102 C101 N101 C108 -177.3(4) . . . . ? C106 C101 N101 C108 0.7(5) . . . . ? C102 C101 N101 C1B 3.1(6) . . . . ? C106 C101 N101 C1B -178.8(3) . . . . ? C2B C1B N101 C108 -78.3(5) . . . . ? C2B C1B N101 C101 101.2(4) . . . . ? _diffrn_measured_fraction_theta_max 0.981 _diffrn_reflns_theta_full 25.03 _diffrn_measured_fraction_theta_full 0.981 _refine_diff_density_max 1.222 _refine_diff_density_min -0.468 _refine_diff_density_rms 0.122 _database_code_depnum_ccdc_archive 'CCDC 977428'