# Electronic Supplementary Material (ESI) for CrystEngComm # This journal is © The Royal Society of Chemistry 2012 ####################################################################### # # 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_a446 _database_code_depnum_ccdc_archive 'CCDC 888316' #TrackingRef 'GK10CEC2012.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C16 H12 F3 N O4' _chemical_formula_weight 339.27 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' F F 0.0171 0.0103 '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 7.2580(9) _cell_length_b 8.4271(10) _cell_length_c 12.6094(15) _cell_angle_alpha 77.860(2) _cell_angle_beta 75.529(2) _cell_angle_gamma 72.829(3) _cell_volume 705.67(15) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 993 _cell_measurement_theta_min 3.00 _cell_measurement_theta_max 27.47 _exptl_crystal_description BLOCK _exptl_crystal_colour COLOURLESS _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.14 _exptl_crystal_density_meas 'Not Measured' _exptl_crystal_density_diffrn 1.597 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 348 _exptl_absorpt_coefficient_mu 0.140 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.9331 _exptl_absorpt_correction_T_max 0.9806 _exptl_absorpt_process_details 'SADABS (Sheldrick, 2004)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 9191 _diffrn_reflns_av_R_equivalents 0.0299 _diffrn_reflns_av_sigmaI/netI 0.0339 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 2.56 _diffrn_reflns_theta_max 27.49 _reflns_number_total 3233 _reflns_number_gt 2895 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^ > 2sigma(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^)+(0.0587P)^2^+0.6288P] 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 3233 _refine_ls_number_parameters 225 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0643 _refine_ls_R_factor_gt 0.0578 _refine_ls_wR_factor_ref 0.1432 _refine_ls_wR_factor_gt 0.1395 _refine_ls_goodness_of_fit_ref 1.091 _refine_ls_restrained_S_all 1.091 _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 O1 O 0.4350(2) 0.8024(2) -0.44719(12) 0.0255(3) Uani 1 1 d . . . H1O H 0.429(4) 0.851(4) -0.512(3) 0.044(8) Uiso 1 1 d . . . O2 O 0.1818(2) 1.0206(2) -0.40140(12) 0.0299(4) Uani 1 1 d . . . O3 O 0.2773(3) 0.7539(2) 0.31321(13) 0.0311(4) Uani 1 1 d . . . O4 O 0.4212(2) 0.9366(2) 0.34571(12) 0.0293(4) Uani 1 1 d . . . F1 F 0.3992(2) 1.08718(15) 0.13529(10) 0.0314(3) Uani 1 1 d . . . F2 F 0.62181(18) 0.85359(17) 0.12764(10) 0.0302(3) Uani 1 1 d . . . F3 F 0.33572(19) 0.87320(17) 0.09994(10) 0.0287(3) Uani 1 1 d . . . N1 N -0.1038(3) 0.3473(2) 0.47767(15) 0.0249(4) Uani 1 1 d . . . H1N H -0.144(5) 0.295(4) 0.542(3) 0.052(9) Uiso 1 1 d . . . C1 C 0.2925(3) 0.8858(3) -0.37533(16) 0.0215(4) Uani 1 1 d . . . C2 C 0.2726(3) 0.7970(2) -0.25919(16) 0.0198(4) Uani 1 1 d . . . C3 C 0.3879(3) 0.6371(2) -0.22922(16) 0.0200(4) Uani 1 1 d . . . H3 H 0.4904 0.5822 -0.2829 0.024 Uiso 1 1 calc R . . C4 C 0.3527(3) 0.5581(2) -0.12064(16) 0.0201(4) Uani 1 1 d . . . H4 H 0.4316 0.4488 -0.1006 0.024 Uiso 1 1 calc R . . C5 C 0.2031(3) 0.6363(2) -0.04033(16) 0.0194(4) Uani 1 1 d . . . C6 C 0.0878(3) 0.7976(3) -0.07174(17) 0.0223(4) Uani 1 1 d . . . H6 H -0.0149 0.8530 -0.0183 0.027 Uiso 1 1 calc R . . C7 C 0.1228(3) 0.8760(3) -0.17957(17) 0.0224(4) Uani 1 1 d . . . H7 H 0.0439 0.9852 -0.1999 0.027 Uiso 1 1 calc R . . C8 C 0.1669(3) 0.5455(2) 0.07238(16) 0.0199(4) Uani 1 1 d . . . H8 H 0.2334 0.4297 0.0838 0.024 Uiso 1 1 calc R . . C9 C 0.0487(3) 0.6115(3) 0.16008(17) 0.0209(4) Uani 1 1 d . . . H9 H -0.0107 0.7288 0.1500 0.025 Uiso 1 1 calc R . . C10 C -0.2077(3) 0.5047(3) 0.45057(17) 0.0245(4) Uani 1 1 d . . . H10 H -0.3177 0.5551 0.5026 0.029 Uiso 1 1 calc R . . C11 C -0.1566(3) 0.5939(3) 0.34843(17) 0.0220(4) Uani 1 1 d . . . H11 H -0.2289 0.7065 0.3305 0.026 Uiso 1 1 calc R . . C12 C 0.0029(3) 0.5184(2) 0.27042(16) 0.0185(4) Uani 1 1 d . . . C13 C 0.1087(3) 0.3537(3) 0.30297(17) 0.0212(4) Uani 1 1 d . . . H13 H 0.2189 0.2991 0.2529 0.025 Uiso 1 1 calc R . . C14 C 0.0527(3) 0.2716(3) 0.40705(17) 0.0237(4) Uani 1 1 d . . . H14 H 0.1252 0.1606 0.4291 0.028 Uiso 1 1 calc R . . C15 C 0.3662(3) 0.8649(3) 0.28738(16) 0.0209(4) Uani 1 1 d . . . C16 C 0.4283(3) 0.9214(2) 0.16103(16) 0.0204(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 O1 0.0302(8) 0.0277(8) 0.0157(7) 0.0006(6) -0.0022(6) -0.0076(6) O2 0.0360(9) 0.0270(8) 0.0196(7) 0.0045(6) -0.0067(6) -0.0021(7) O3 0.0403(9) 0.0341(9) 0.0212(7) -0.0014(6) 0.0001(7) -0.0202(7) O4 0.0394(9) 0.0323(9) 0.0187(7) -0.0006(6) -0.0055(6) -0.0156(7) F1 0.0472(8) 0.0205(6) 0.0202(6) 0.0017(5) -0.0016(6) -0.0071(6) F2 0.0227(6) 0.0375(8) 0.0230(6) -0.0010(5) 0.0014(5) -0.0038(5) F3 0.0338(7) 0.0364(7) 0.0187(6) -0.0023(5) -0.0066(5) -0.0133(6) N1 0.0306(10) 0.0298(10) 0.0163(8) 0.0018(7) -0.0033(7) -0.0159(8) C1 0.0236(10) 0.0239(10) 0.0182(9) -0.0004(8) -0.0044(8) -0.0096(8) C2 0.0212(9) 0.0214(10) 0.0177(9) 0.0004(7) -0.0050(7) -0.0082(8) C3 0.0192(9) 0.0209(10) 0.0200(9) -0.0045(7) -0.0023(7) -0.0055(8) C4 0.0214(10) 0.0163(9) 0.0218(10) 0.0000(7) -0.0067(8) -0.0037(7) C5 0.0208(9) 0.0202(10) 0.0178(9) -0.0002(7) -0.0046(7) -0.0075(8) C6 0.0215(10) 0.0222(10) 0.0205(10) -0.0026(8) -0.0021(8) -0.0035(8) C7 0.0249(10) 0.0181(9) 0.0212(10) 0.0009(8) -0.0063(8) -0.0024(8) C8 0.0210(10) 0.0174(9) 0.0202(9) 0.0022(7) -0.0062(8) -0.0051(7) C9 0.0231(10) 0.0184(9) 0.0201(9) 0.0016(7) -0.0068(8) -0.0050(8) C10 0.0229(10) 0.0332(11) 0.0191(10) -0.0062(8) -0.0012(8) -0.0107(9) C11 0.0226(10) 0.0218(10) 0.0216(10) -0.0032(8) -0.0052(8) -0.0051(8) C12 0.0193(9) 0.0202(9) 0.0183(9) -0.0014(7) -0.0063(7) -0.0072(7) C13 0.0214(10) 0.0207(10) 0.0210(10) -0.0026(8) -0.0039(8) -0.0054(8) C14 0.0296(11) 0.0215(10) 0.0213(10) 0.0017(8) -0.0087(8) -0.0088(8) C15 0.0206(9) 0.0204(9) 0.0181(9) -0.0011(7) -0.0021(7) -0.0028(8) C16 0.0204(9) 0.0187(9) 0.0197(10) -0.0026(7) -0.0012(7) -0.0040(7) _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 O1 C1 1.325(3) . ? O2 C1 1.217(3) . ? O3 C15 1.233(3) . ? O4 C15 1.241(3) . ? F1 C16 1.331(2) . ? F2 C16 1.344(2) . ? F3 C16 1.327(2) . ? N1 C10 1.339(3) . ? N1 C14 1.340(3) . ? C1 C2 1.491(3) . ? C2 C3 1.392(3) . ? C2 C7 1.393(3) . ? C3 C4 1.388(3) . ? C4 C5 1.395(3) . ? C5 C6 1.405(3) . ? C5 C8 1.466(3) . ? C6 C7 1.378(3) . ? C8 C9 1.331(3) . ? C9 C12 1.458(3) . ? C10 C11 1.371(3) . ? C11 C12 1.404(3) . ? C12 C13 1.405(3) . ? C13 C14 1.372(3) . ? C15 C16 1.555(3) . ? 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 C10 N1 C14 121.71(18) . . ? O2 C1 O1 123.48(18) . . ? O2 C1 C2 122.21(19) . . ? O1 C1 C2 114.25(18) . . ? C3 C2 C7 119.51(18) . . ? C3 C2 C1 123.04(18) . . ? C7 C2 C1 117.33(18) . . ? C4 C3 C2 119.76(18) . . ? C3 C4 C5 121.13(18) . . ? C4 C5 C6 118.51(18) . . ? C4 C5 C8 119.13(18) . . ? C6 C5 C8 122.32(18) . . ? C7 C6 C5 120.36(19) . . ? C6 C7 C2 120.73(18) . . ? C9 C8 C5 125.50(18) . . ? C8 C9 C12 125.34(19) . . ? N1 C10 C11 120.6(2) . . ? C10 C11 C12 119.87(19) . . ? C11 C12 C13 117.52(18) . . ? C11 C12 C9 119.25(18) . . ? C13 C12 C9 123.21(18) . . ? C14 C13 C12 120.01(19) . . ? N1 C14 C13 120.30(19) . . ? O3 C15 O4 130.66(19) . . ? O3 C15 C16 115.66(18) . . ? O4 C15 C16 113.63(17) . . ? F3 C16 F1 107.47(16) . . ? F3 C16 F2 106.74(16) . . ? F1 C16 F2 106.90(16) . . ? F3 C16 C15 113.49(16) . . ? F1 C16 C15 112.43(16) . . ? F2 C16 C15 109.46(16) . . ? 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 N1 H1N O3 0.87(3) 1.86(3) 2.701(2) 163(3) 2_566 O1 H1O O4 0.84(3) 1.79(3) 2.633(2) 175(3) 1_554 _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 27.49 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.530 _refine_diff_density_min -0.220 _refine_diff_density_rms 0.067 data_a449jj _database_code_depnum_ccdc_archive 'CCDC 888317' #TrackingRef 'GK10CEC2012.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C15 H16 Cl N O7' _chemical_formula_weight 357.74 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' Cl Cl 0.1484 0.1585 '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 8.6037(11) _cell_length_b 9.5432(12) _cell_length_c 10.2702(13) _cell_angle_alpha 93.248(2) _cell_angle_beta 101.615(2) _cell_angle_gamma 107.129(2) _cell_volume 783.27(17) _cell_formula_units_Z 2 _cell_measurement_temperature 223(2) _cell_measurement_reflns_used 3468 _cell_measurement_theta_min 2.54 _cell_measurement_theta_max 26.08 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.34 _exptl_crystal_size_min 0.34 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.517 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 372 _exptl_absorpt_coefficient_mu 0.283 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8715 _exptl_absorpt_correction_T_max 0.9100 _exptl_absorpt_process_details 'SADABS (Sheldrick 2001)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 223(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 10107 _diffrn_reflns_av_R_equivalents 0.0357 _diffrn_reflns_av_sigmaI/netI 0.0360 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 2.04 _diffrn_reflns_theta_max 27.50 _reflns_number_total 3589 _reflns_number_gt 3008 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _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^ > 2sigma(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^)+(0.1051P)^2^+0.5929P] 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 3589 _refine_ls_number_parameters 347 _refine_ls_number_restraints 496 _refine_ls_R_factor_all 0.0893 _refine_ls_R_factor_gt 0.0784 _refine_ls_wR_factor_ref 0.2274 _refine_ls_wR_factor_gt 0.2203 _refine_ls_goodness_of_fit_ref 1.221 _refine_ls_restrained_S_all 1.279 _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 C2 C 0.1495(12) 0.8323(7) 0.7012(5) 0.0403(14) Uani 0.712(10) 1 d PGDU A 1 C3 C 0.1291(10) 0.8431(6) 0.5648(6) 0.0434(14) Uani 0.712(10) 1 d PGU A 1 H3 H 0.0951 0.9207 0.5291 0.052 Uiso 0.712(10) 1 calc PR A 1 C4 C 0.1589(7) 0.7391(6) 0.4811(4) 0.0426(13) Uani 0.712(10) 1 d PGU A 1 H4 H 0.1451 0.7464 0.3889 0.051 Uiso 0.712(10) 1 calc PR A 1 C5 C 0.2092(5) 0.6243(4) 0.5338(5) 0.0359(11) Uani 0.712(10) 1 d PGU A 1 C6 C 0.2297(6) 0.6136(4) 0.6702(5) 0.0421(12) Uani 0.712(10) 1 d PGU A 1 H6 H 0.2637 0.5359 0.7059 0.051 Uiso 0.712(10) 1 calc PR A 1 C7 C 0.1998(10) 0.7175(7) 0.7539(4) 0.0449(15) Uani 0.712(10) 1 d PGDU A 1 H7 H 0.2136 0.7102 0.8462 0.054 Uiso 0.712(10) 1 calc PR A 1 C2A C 0.149(4) 0.822(2) 0.7168(18) 0.043(2) Uani 0.288(10) 1 d PDU A 2 C3A C 0.145(3) 0.812(2) 0.5777(19) 0.043(2) Uani 0.288(10) 1 d PU A 2 H3A H 0.1144 0.8830 0.5277 0.051 Uiso 0.288(10) 1 calc PR A 2 C4A C 0.1833(19) 0.7021(18) 0.5147(15) 0.039(2) Uani 0.288(10) 1 d PU A 2 H4A H 0.1834 0.7010 0.4231 0.047 Uiso 0.288(10) 1 calc PR A 2 C5A C 0.2225(16) 0.5910(16) 0.5838(17) 0.038(2) Uani 0.288(10) 1 d PU A 2 C6A C 0.231(2) 0.5997(17) 0.7243(16) 0.046(2) Uani 0.288(10) 1 d PU A 2 H6A H 0.2640 0.5297 0.7743 0.055 Uiso 0.288(10) 1 calc PR A 2 C7A C 0.191(3) 0.707(2) 0.7844(19) 0.046(2) Uani 0.288(10) 1 d PDU A 2 H7A H 0.1897 0.7070 0.8758 0.056 Uiso 0.288(10) 1 calc PR A 2 C10 C 0.3271(13) 0.2259(10) 0.1384(10) 0.0522(18) Uani 0.712(10) 1 d PU A 1 H10 H 0.3138 0.2419 0.0480 0.063 Uiso 0.712(10) 1 calc PR A 1 C11 C 0.3028(13) 0.3223(10) 0.2329(7) 0.0471(14) Uani 0.712(10) 1 d PDU A 1 H11 H 0.2780 0.4071 0.2052 0.056 Uiso 0.712(10) 1 calc PR A 1 C12 C 0.3133(10) 0.2994(7) 0.3679(5) 0.0364(14) Uani 0.712(10) 1 d PDU A 1 C13 C 0.3551(12) 0.1721(9) 0.4017(9) 0.0505(17) Uani 0.712(10) 1 d PDU A 1 H13 H 0.3633 0.1492 0.4901 0.061 Uiso 0.712(10) 1 calc PR A 1 C14 C 0.3837(11) 0.0816(9) 0.3085(9) 0.0543(17) Uani 0.712(10) 1 d PU A 1 H14 H 0.4134 -0.0017 0.3342 0.065 Uiso 0.712(10) 1 calc PR A 1 N1 N 0.3705(10) 0.1086(9) 0.1808(6) 0.0473(16) Uani 0.712(10) 1 d PU A 1 H1 H 0.3905 0.0489 0.1237 0.057 Uiso 0.712(10) 1 calc PR A 1 C10A C 0.348(3) 0.195(3) 0.153(3) 0.051(3) Uani 0.288(10) 1 d PU A 2 H10A H 0.3611 0.1901 0.0643 0.061 Uiso 0.288(10) 1 calc PR A 2 C11A C 0.300(4) 0.307(3) 0.1960(18) 0.051(3) Uani 0.288(10) 1 d PDU A 2 H11A H 0.2675 0.3710 0.1381 0.061 Uiso 0.288(10) 1 calc PR A 2 C12A C 0.303(3) 0.3231(19) 0.3333(17) 0.041(3) Uani 0.288(10) 1 d PDU A 2 C13A C 0.337(3) 0.210(2) 0.404(2) 0.047(3) Uani 0.288(10) 1 d PDU A 2 H13A H 0.3356 0.2155 0.4959 0.056 Uiso 0.288(10) 1 calc PR A 2 C14A C 0.371(3) 0.097(3) 0.351(2) 0.050(3) Uani 0.288(10) 1 d PU A 2 H14A H 0.3898 0.0223 0.4019 0.060 Uiso 0.288(10) 1 calc PR A 2 N1A N 0.377(3) 0.092(2) 0.223(2) 0.049(3) Uani 0.288(10) 1 d PU A 2 H1A H 0.4006 0.0195 0.1850 0.059 Uiso 0.288(10) 1 calc PR A 2 C8 C 0.2392(6) 0.5149(6) 0.4390(5) 0.0393(13) Uani 0.712(10) 1 d P A 1 H8 H 0.2240 0.5325 0.3489 0.047 Uiso 0.712(10) 1 calc PR A 1 C9 C 0.2847(6) 0.3958(6) 0.4664(5) 0.0395(13) Uani 0.712(10) 1 d PD A 1 H9 H 0.2987 0.3738 0.5552 0.047 Uiso 0.712(10) 1 calc PR A 1 C8A C 0.2616(15) 0.4680(14) 0.5241(14) 0.045(3) Uani 0.288(10) 1 d P A 2 H8A H 0.2886 0.4012 0.5816 0.054 Uiso 0.288(10) 1 calc PR A 2 C9A C 0.2632(16) 0.4406(14) 0.3981(16) 0.044(3) Uani 0.288(10) 1 d PD A 2 H9A H 0.2341 0.5078 0.3421 0.052 Uiso 0.288(10) 1 calc PR A 2 O3 O 0.4887(4) 0.8688(2) 0.0911(2) 0.0583(7) Uani 1 1 d D B 1 O4 O 0.3102(5) 0.6348(4) 0.0918(4) 0.136(3) Uani 0.902(5) 1 d PDU B 1 O5 O 0.5941(5) 0.6804(4) 0.1589(4) 0.1064(18) Uani 0.902(5) 1 d PDU B 1 O6 O 0.4559(5) 0.7783(4) 0.2917(3) 0.0940(15) Uani 0.902(5) 1 d PDU B 1 O4A O 0.3123(5) 0.7155(7) 0.2023(5) 0.1064(18) Uani 0.098(5) 1 d PDU B 2 O5A O 0.4510(7) 0.6180(6) 0.0689(5) 0.0940(15) Uani 0.098(5) 1 d PDU B 2 O6A O 0.5973(6) 0.7624(7) 0.2692(5) 0.136(3) Uani 0.098(5) 1 d PDU B 2 Cl1 Cl 0.46231(11) 0.74046(9) 0.15800(8) 0.0455(3) Uani 1 1 d D . . O1 O 0.0650(4) 1.0383(3) 0.7250(3) 0.0658(8) Uani 1 1 d . A . H1O H 0.0517 1.0993 0.7792 0.099 Uiso 1 1 calc R . . O2 O 0.1245(4) 0.9378(3) 0.9109(3) 0.0635(8) Uani 1 1 d . A . C1 C 0.1134(4) 0.9368(4) 0.7900(3) 0.0467(8) Uani 1 1 d D . . C1S C 0.9569(11) 0.6469(9) 0.0998(10) 0.137(3) Uani 1 1 d . . . H1S1 H 0.9233 0.6108 0.1795 0.206 Uiso 1 1 calc R . . H1S2 H 1.0367 0.6013 0.0775 0.206 Uiso 1 1 calc R . . H1S3 H 0.8596 0.6223 0.0258 0.206 Uiso 1 1 calc R . . O1S O 1.0278(5) 0.7943(4) 0.1227(4) 0.0863(11) Uani 1 1 d D . . H1S H 1.074(5) 0.861(4) 0.077(4) 0.050 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 C2 0.038(2) 0.042(2) 0.036(3) -0.004(2) 0.009(2) 0.006(2) C3 0.053(3) 0.042(3) 0.038(2) 0.004(2) 0.012(2) 0.019(2) C4 0.053(3) 0.048(3) 0.031(2) 0.0093(19) 0.009(2) 0.021(2) C5 0.039(2) 0.038(3) 0.029(3) 0.007(2) 0.0060(19) 0.0096(19) C6 0.051(2) 0.042(2) 0.032(3) 0.011(2) 0.008(3) 0.0138(18) C7 0.050(3) 0.052(3) 0.030(3) 0.004(2) 0.009(2) 0.011(2) C2A 0.044(4) 0.045(4) 0.035(4) -0.002(4) 0.009(4) 0.010(4) C3A 0.051(4) 0.040(4) 0.040(4) 0.005(4) 0.009(4) 0.020(4) C4A 0.050(4) 0.042(5) 0.029(4) 0.007(4) 0.005(4) 0.023(4) C5A 0.044(4) 0.038(4) 0.035(5) 0.008(4) 0.007(4) 0.019(3) C6A 0.054(4) 0.049(4) 0.035(5) 0.007(4) 0.006(5) 0.019(4) C7A 0.049(4) 0.048(4) 0.042(4) 0.000(4) 0.005(4) 0.019(4) C10 0.065(3) 0.054(4) 0.045(3) 0.004(3) 0.018(2) 0.025(3) C11 0.062(3) 0.042(3) 0.038(3) -0.001(3) 0.016(3) 0.017(2) C12 0.036(2) 0.036(3) 0.033(3) 0.001(2) 0.005(2) 0.0072(19) C13 0.063(3) 0.046(4) 0.042(3) -0.001(3) 0.004(2) 0.023(3) C14 0.066(3) 0.053(3) 0.046(4) -0.003(3) 0.008(3) 0.027(2) N1 0.055(2) 0.049(3) 0.042(3) -0.009(3) 0.015(3) 0.022(2) C10A 0.062(5) 0.050(5) 0.044(4) 0.000(4) 0.020(4) 0.019(4) C11A 0.063(5) 0.048(5) 0.042(5) 0.002(5) 0.018(5) 0.015(4) C12A 0.048(5) 0.041(5) 0.035(5) -0.003(4) 0.014(5) 0.011(4) C13A 0.057(5) 0.046(6) 0.037(4) -0.009(4) 0.009(4) 0.018(5) C14A 0.064(5) 0.050(5) 0.041(5) -0.004(5) 0.011(5) 0.027(4) N1A 0.059(4) 0.048(4) 0.044(5) -0.005(5) 0.017(5) 0.022(4) C8 0.043(2) 0.044(3) 0.029(2) 0.004(2) 0.0103(18) 0.010(2) C9 0.045(3) 0.042(3) 0.029(2) 0.002(2) 0.0060(19) 0.013(2) C8A 0.046(7) 0.045(7) 0.049(8) 0.004(6) 0.011(5) 0.021(5) C9A 0.052(7) 0.035(6) 0.047(8) -0.003(6) 0.014(6) 0.018(5) O3 0.094(2) 0.0446(14) 0.0535(15) 0.0176(12) 0.0375(14) 0.0314(14) O4 0.135(4) 0.068(3) 0.134(4) 0.041(3) -0.062(3) -0.020(3) O5 0.139(4) 0.105(3) 0.134(4) 0.061(3) 0.075(3) 0.089(3) O6 0.154(4) 0.097(3) 0.0467(19) 0.0233(19) 0.038(2) 0.050(3) O4A 0.139(4) 0.105(3) 0.134(4) 0.061(3) 0.075(3) 0.089(3) O5A 0.154(4) 0.097(3) 0.0467(19) 0.0233(19) 0.038(2) 0.050(3) O6A 0.135(4) 0.068(3) 0.134(4) 0.041(3) -0.062(3) -0.020(3) Cl1 0.0628(6) 0.0403(5) 0.0356(4) 0.0115(3) 0.0110(3) 0.0184(4) O1 0.088(2) 0.0636(18) 0.0501(16) -0.0056(13) 0.0072(15) 0.0387(16) O2 0.081(2) 0.0691(18) 0.0436(14) -0.0022(13) 0.0213(13) 0.0253(15) C1 0.0417(17) 0.0517(19) 0.0421(18) -0.0051(14) 0.0085(14) 0.0105(15) C1S 0.132(7) 0.115(6) 0.164(8) 0.035(6) 0.027(6) 0.039(5) O1S 0.118(3) 0.066(2) 0.091(3) 0.0218(19) 0.040(2) 0.041(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 C2 C3 1.3900 . ? C2 C7 1.3900 . ? C2 C1 1.454(3) . ? C3 C4 1.3900 . ? C4 C5 1.3900 . ? C5 C6 1.3900 . ? C5 C8 1.501(6) . ? C6 C7 1.3900 . ? C2A C3A 1.418(19) . ? C2A C7A 1.428(5) . ? C2A C1 1.433(5) . ? C3A C4A 1.36(2) . ? C4A C5A 1.394(16) . ? C5A C6A 1.427(18) . ? C5A C8A 1.450(19) . ? C6A C7A 1.33(2) . ? C10 N1 1.349(9) . ? C10 C11 1.387(11) . ? C11 C12 1.405(5) . ? C12 C13 1.407(5) . ? C12 C9 1.434(4) . ? C13 C14 1.360(10) . ? C14 N1 1.340(9) . ? C10A N1A 1.30(3) . ? C10A C11A 1.33(3) . ? C11A C12A 1.405(6) . ? C12A C13A 1.406(6) . ? C12A C9A 1.430(5) . ? C13A C14A 1.32(2) . ? C14A N1A 1.33(2) . ? C8 C9 1.333(8) . ? C8A C9A 1.31(2) . ? O3 Cl1 1.421(2) . ? O4 Cl1 1.407(3) . ? O5 Cl1 1.412(3) . ? O6 Cl1 1.416(3) . ? O4A Cl1 1.413(4) . ? O5A Cl1 1.410(4) . ? O6A Cl1 1.412(4) . ? O1 C1 1.325(4) . ? O2 C1 1.226(4) . ? C1S O1S 1.344(9) . ? 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 C3 C2 C7 120.0 . . ? C3 C2 C1 121.0(4) . . ? C7 C2 C1 119.0(4) . . ? C2 C3 C4 120.0 . . ? C5 C4 C3 120.0 . . ? C4 C5 C6 120.0 . . ? C4 C5 C8 117.8(4) . . ? C6 C5 C8 122.2(4) . . ? C7 C6 C5 120.0 . . ? C6 C7 C2 120.0 . . ? C3A C2A C7A 115.6(11) . . ? C3A C2A C1 124.8(14) . . ? C7A C2A C1 119.6(14) . . ? C4A C3A C2A 121.9(14) . . ? C3A C4A C5A 120.9(13) . . ? C4A C5A C6A 118.5(12) . . ? C4A C5A C8A 124.6(14) . . ? C6A C5A C8A 116.8(13) . . ? C7A C6A C5A 119.8(13) . . ? C6A C7A C2A 123.1(15) . . ? N1 C10 C11 117.8(9) . . ? C10 C11 C12 123.2(8) . . ? C11 C12 C13 114.7(6) . . ? C11 C12 C9 124.0(6) . . ? C13 C12 C9 121.2(6) . . ? C14 C13 C12 121.1(8) . . ? N1 C14 C13 121.5(8) . . ? C14 N1 C10 121.6(8) . . ? N1A C10A C11A 126(3) . . ? C10A C11A C12A 116(2) . . ? C11A C12A C13A 115.7(17) . . ? C11A C12A C9A 123.6(17) . . ? C13A C12A C9A 120.6(16) . . ? C14A C13A C12A 124.1(19) . . ? C13A C14A N1A 118(2) . . ? C10A N1A C14A 121(2) . . ? C9 C8 C5 128.2(5) . . ? C8 C9 C12 123.7(5) . . ? C9A C8A C5A 126.5(14) . . ? C8A C9A C12A 129.3(16) . . ? O4 Cl1 O5A 56.43(15) . . ? O4 Cl1 O6A 141.3(3) . . ? O5A Cl1 O6A 109.8(2) . . ? O4 Cl1 O5 109.43(19) . . ? O5A Cl1 O5 56.30(15) . . ? O6A Cl1 O5 56.24(15) . . ? O4 Cl1 O4A 56.23(15) . . ? O5A Cl1 O4A 109.8(2) . . ? O6A Cl1 O4A 109.6(2) . . ? O5 Cl1 O4A 140.9(3) . . ? O4 Cl1 O6 109.24(19) . . ? O5A Cl1 O6 141.2(3) . . ? O6A Cl1 O6 56.22(15) . . ? O5 Cl1 O6 109.16(18) . . ? O4A Cl1 O6 56.15(15) . . ? O4 Cl1 O3 109.51(17) . . ? O5A Cl1 O3 109.4(3) . . ? O6A Cl1 O3 109.2(3) . . ? O5 Cl1 O3 110.04(17) . . ? O4A Cl1 O3 109.1(3) . . ? O6 Cl1 O3 109.44(16) . . ? O2 C1 O1 121.0(3) . . ? O2 C1 C2A 119.7(9) . . ? O1 C1 C2A 119.3(8) . . ? O2 C1 C2 127.1(4) . . ? O1 C1 C2 112.0(4) . . ? C2A C1 C2 7.5(10) . . ? 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 N1 H1 O3 0.87 2.16 2.937(8) 147.7 1_545 N1A H1A Cl1 0.87 2.87 3.69(2) 157.7 1_545 O1 H1 O1S 0.83 1.76 2.569(5) 166.1 2_676 O1S H1S O2 0.87(2) 1.97(3) 2.773(5) 154(4) 1_654 _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.764 _refine_diff_density_min -0.729 _refine_diff_density_rms 0.087 data_a276 _database_code_depnum_ccdc_archive 'CCDC 888318' #TrackingRef 'GK10CEC2012.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C56 H52 N4 O21 S3' _chemical_formula_weight 1213.20 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' S S 0.1246 0.1234 '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 11.1151(9) _cell_length_b 11.8964(9) _cell_length_c 22.1546(18) _cell_angle_alpha 91.414(2) _cell_angle_beta 98.911(2) _cell_angle_gamma 110.246(2) _cell_volume 2705.6(4) _cell_formula_units_Z 2 _cell_measurement_temperature 223(2) _cell_measurement_reflns_used 3367 _cell_measurement_theta_min 2.29 _cell_measurement_theta_max 23.00 _exptl_crystal_description Block _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.28 _exptl_crystal_size_mid 0.22 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas 'Not Measured' _exptl_crystal_density_diffrn 1.489 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1264 _exptl_absorpt_coefficient_mu 0.224 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.9399 _exptl_absorpt_correction_T_max 0.9823 _exptl_absorpt_process_details 'Sadabs, (Sheldrick 2001)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 223(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 35723 _diffrn_reflns_av_R_equivalents 0.0613 _diffrn_reflns_av_sigmaI/netI 0.0748 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -28 _diffrn_reflns_limit_l_max 28 _diffrn_reflns_theta_min 1.83 _diffrn_reflns_theta_max 27.50 _reflns_number_total 12429 _reflns_number_gt 8465 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^ > 2sigma(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^)+(0.0614P)^2^+0.3409P] 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 12429 _refine_ls_number_parameters 796 _refine_ls_number_restraints 6 _refine_ls_R_factor_all 0.0998 _refine_ls_R_factor_gt 0.0652 _refine_ls_wR_factor_ref 0.1503 _refine_ls_wR_factor_gt 0.1352 _refine_ls_goodness_of_fit_ref 1.035 _refine_ls_restrained_S_all 1.035 _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_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.9509(2) 0.8109(2) 0.64605(9) 0.0427(6) Uani 1 1 d . . . H1 H 0.9229 0.8293 0.6760 0.064 Uiso 1 1 calc R . . O2 O 0.7400(2) 0.7448(2) 0.60496(9) 0.0473(6) Uani 1 1 d . . . O3 O 0.4962(2) 0.58822(18) 0.40895(9) 0.0373(5) Uani 1 1 d . . . H3 H 0.5165 0.5728 0.3761 0.056 Uiso 1 1 calc R . . O4 O 0.4950(2) 0.7551(2) 0.36581(10) 0.0522(6) Uani 1 1 d . . . O5 O 0.1276(2) 0.9966(2) 0.47006(10) 0.0482(6) Uani 1 1 d . . . O6 O -0.0827(2) 0.9269(2) 0.42715(10) 0.0499(6) Uani 1 1 d . . . H6O H -0.109(5) 0.962(5) 0.476(3) 0.17(2) Uiso 1 1 d . . . O7 O 0.3356(2) 1.1726(2) 0.30149(9) 0.0416(5) Uani 1 1 d . . . H7 H 0.3082 1.1955 0.3305 0.062 Uiso 1 1 calc R . . O8 O 0.1276(2) 1.1250(2) 0.25610(9) 0.0425(6) Uani 1 1 d . . . N1 N 1.1263(2) 0.4079(2) 0.20958(10) 0.0260(5) Uani 1 1 d D . . H1N H 1.137(3) 0.377(2) 0.1743(7) 0.032(8) Uiso 1 1 d D . . N2 N 0.2128(2) 1.0051(2) 0.81211(10) 0.0311(6) Uani 1 1 d D . . H2N H 0.185(3) 1.021(3) 0.8471(9) 0.058(10) Uiso 1 1 d D . . N3 N 0.3175(2) 0.56361(19) 0.04740(10) 0.0257(5) Uani 1 1 d D . . H3N H 0.328(3) 0.526(2) 0.0136(9) 0.047(9) Uiso 1 1 d D . . N4 N 0.5064(2) 0.7000(2) -0.11230(10) 0.0279(5) Uani 1 1 d D . . H4N H 0.516(3) 0.659(2) -0.1450(9) 0.043(9) Uiso 1 1 d D . . C1 C 0.8544(3) 0.7582(3) 0.60213(12) 0.0304(6) Uani 1 1 d . . . C2 C 0.8872(3) 0.7101(2) 0.54667(12) 0.0293(6) Uani 1 1 d . . . C3 C 1.0117(3) 0.7137(3) 0.54377(13) 0.0358(7) Uani 1 1 d . . . H3A H 1.0792 0.7487 0.5773 0.043 Uiso 1 1 calc R . . C4 C 1.0375(3) 0.6662(3) 0.49180(13) 0.0363(7) Uani 1 1 d . . . H4 H 1.1224 0.6685 0.4905 0.044 Uiso 1 1 calc R . . C5 C 0.9397(3) 0.6152(2) 0.44164(12) 0.0296(6) Uani 1 1 d . . . C6 C 0.8153(3) 0.6136(3) 0.44517(14) 0.0462(9) Uani 1 1 d . . . H6 H 0.7479 0.5803 0.4114 0.055 Uiso 1 1 calc R . . C7 C 0.7891(3) 0.6597(3) 0.49711(14) 0.0451(9) Uani 1 1 d . . . H7A H 0.7041 0.6569 0.4988 0.054 Uiso 1 1 calc R . . C8 C 0.9598(3) 0.5639(3) 0.38473(13) 0.0332(7) Uani 1 1 d . . . H8 H 0.8885 0.5387 0.3523 0.040 Uiso 1 1 calc R . . C9 C 1.0672(3) 0.5494(3) 0.37435(12) 0.0321(7) Uani 1 1 d . . . H9 H 1.1390 0.5732 0.4066 0.038 Uiso 1 1 calc R . . C10 C 1.0838(3) 0.4989(2) 0.31638(12) 0.0248(6) Uani 1 1 d . . . C11 C 1.1978(3) 0.4764(2) 0.31337(12) 0.0291(6) Uani 1 1 d . . . H11 H 1.2624 0.4928 0.3486 0.035 Uiso 1 1 calc R . . C12 C 1.2168(3) 0.4308(2) 0.25978(13) 0.0285(6) Uani 1 1 d . . . H12 H 1.2939 0.4155 0.2584 0.034 Uiso 1 1 calc R . . C13 C 1.0153(3) 0.4296(2) 0.21000(12) 0.0256(6) Uani 1 1 d . . . H13 H 0.9535 0.4139 0.1738 0.031 Uiso 1 1 calc R . . C14 C 0.9916(3) 0.4743(2) 0.26248(12) 0.0262(6) Uani 1 1 d . . . H14 H 0.9134 0.4884 0.2624 0.031 Uiso 1 1 calc R . . C15 C 0.4833(3) 0.6947(3) 0.40891(13) 0.0315(7) Uani 1 1 d . . . C16 C 0.4485(3) 0.7287(2) 0.46729(12) 0.0277(6) Uani 1 1 d . . . C17 C 0.4459(3) 0.6615(3) 0.51717(13) 0.0360(7) Uani 1 1 d . . . H17 H 0.4654 0.5908 0.5148 0.043 Uiso 1 1 calc R . . C18 C 0.4147(3) 0.6974(3) 0.57064(13) 0.0368(7) Uani 1 1 d . . . H18 H 0.4141 0.6510 0.6044 0.044 Uiso 1 1 calc R . . C19 C 0.3844(3) 0.8003(2) 0.57556(12) 0.0282(6) Uani 1 1 d . . . C20 C 0.3858(3) 0.8668(3) 0.52484(13) 0.0394(8) Uani 1 1 d . . . H20 H 0.3636 0.9361 0.5266 0.047 Uiso 1 1 calc R . . C21 C 0.4192(3) 0.8322(3) 0.47197(13) 0.0392(8) Uani 1 1 d . . . H21 H 0.4222 0.8797 0.4385 0.047 Uiso 1 1 calc R . . C22 C 0.3496(3) 0.8312(3) 0.63315(12) 0.0300(6) Uani 1 1 d . . . H22 H 0.3367 0.7730 0.6618 0.036 Uiso 1 1 calc R . . C23 C 0.3342(3) 0.9334(3) 0.64919(12) 0.0325(7) Uani 1 1 d . . . H23 H 0.3507 0.9944 0.6221 0.039 Uiso 1 1 calc R . . C24 C 0.2931(3) 0.9565(2) 0.70633(12) 0.0271(6) Uani 1 1 d . . . C25 C 0.2362(3) 0.8656(3) 0.74278(13) 0.0350(7) Uani 1 1 d . . . H25 H 0.2251 0.7856 0.7313 0.042 Uiso 1 1 calc R . . C26 C 0.1967(3) 0.8916(3) 0.79474(13) 0.0349(7) Uani 1 1 d . . . H26 H 0.1578 0.8294 0.8187 0.042 Uiso 1 1 calc R . . C27 C 0.2682(3) 1.0956(3) 0.77926(13) 0.0365(7) Uani 1 1 d . . . H27 H 0.2791 1.1747 0.7925 0.044 Uiso 1 1 calc R . . C28 C 0.3093(3) 1.0740(3) 0.72645(13) 0.0369(7) Uani 1 1 d . . . H28 H 0.3484 1.1382 0.7037 0.044 Uiso 1 1 calc R . . C29 C 0.0387(3) 0.9437(3) 0.42708(13) 0.0340(7) Uani 1 1 d . . . C30 C 0.0680(3) 0.8942(3) 0.37122(12) 0.0315(7) Uani 1 1 d . . . C31 C 0.1967(3) 0.9126(3) 0.36696(13) 0.0356(7) Uani 1 1 d . . . H31 H 0.2639 0.9590 0.3985 0.043 Uiso 1 1 calc R . . C32 C 0.2266(3) 0.8632(3) 0.31680(12) 0.0326(7) Uani 1 1 d . . . H32 H 0.3138 0.8742 0.3150 0.039 Uiso 1 1 calc R . . C33 C 0.1288(3) 0.7976(2) 0.26913(11) 0.0257(6) Uani 1 1 d . . . C34 C -0.0007(3) 0.7824(3) 0.27301(13) 0.0332(7) Uani 1 1 d . . . H34 H -0.0678 0.7404 0.2405 0.040 Uiso 1 1 calc R . . C35 C -0.0304(3) 0.8285(3) 0.32408(13) 0.0363(7) Uani 1 1 d . . . H35 H -0.1177 0.8152 0.3269 0.044 Uiso 1 1 calc R . . C36 C 0.1528(3) 0.7425(2) 0.21424(11) 0.0245(6) Uani 1 1 d . . . H36 H 0.0842 0.7179 0.1805 0.029 Uiso 1 1 calc R . . C37 C 0.2615(3) 0.7237(2) 0.20731(11) 0.0242(6) Uani 1 1 d . . . H37 H 0.3316 0.7485 0.2404 0.029 Uiso 1 1 calc R . . C38 C 0.2788(2) 0.6674(2) 0.15181(11) 0.0209(5) Uani 1 1 d . . . C39 C 0.3930(3) 0.6441(2) 0.14965(12) 0.0259(6) Uani 1 1 d . . . H39 H 0.4589 0.6646 0.1845 0.031 Uiso 1 1 calc R . . C40 C 0.4102(3) 0.5918(2) 0.09744(12) 0.0274(6) Uani 1 1 d . . . H40 H 0.4871 0.5757 0.0968 0.033 Uiso 1 1 calc R . . C41 C 0.2063(3) 0.5844(2) 0.04704(12) 0.0248(6) Uani 1 1 d . . . H41 H 0.1431 0.5643 0.0111 0.030 Uiso 1 1 calc R . . C42 C 0.1837(3) 0.6348(2) 0.09853(11) 0.0246(6) Uani 1 1 d . . . H42 H 0.1047 0.6475 0.0981 0.029 Uiso 1 1 calc R . . C43 C 0.2399(3) 1.1255(2) 0.25603(12) 0.0270(6) Uani 1 1 d . . . C44 C 0.2714(3) 1.0692(2) 0.20331(12) 0.0255(6) Uani 1 1 d . . . C45 C 0.3944(3) 1.0616(2) 0.20432(12) 0.0278(6) Uani 1 1 d . . . H45 H 0.4601 1.0946 0.2387 0.033 Uiso 1 1 calc R . . C46 C 0.4194(3) 1.0059(2) 0.15499(12) 0.0274(6) Uani 1 1 d . . . H46 H 0.5020 1.0003 0.1562 0.033 Uiso 1 1 calc R . . C47 C 0.3233(3) 0.9577(2) 0.10313(11) 0.0231(6) Uani 1 1 d . . . C48 C 0.2010(3) 0.9663(3) 0.10273(12) 0.0292(6) Uani 1 1 d . . . H48 H 0.1354 0.9349 0.0681 0.035 Uiso 1 1 calc R . . C49 C 0.1756(3) 1.0204(3) 0.15257(12) 0.0295(6) Uani 1 1 d . . . H49 H 0.0923 1.0241 0.1520 0.035 Uiso 1 1 calc R . . C50 C 0.3443(3) 0.8981(2) 0.04963(12) 0.0248(6) Uani 1 1 d . . . H50 H 0.2736 0.8708 0.0169 0.030 Uiso 1 1 calc R . . C51 C 0.4511(3) 0.8774(2) 0.04138(12) 0.0256(6) Uani 1 1 d . . . H51 H 0.5230 0.9051 0.0735 0.031 Uiso 1 1 calc R . . C52 C 0.4671(3) 0.8159(2) -0.01288(11) 0.0224(6) Uani 1 1 d . . . C53 C 0.5855(3) 0.8001(3) -0.01444(13) 0.0319(7) Uani 1 1 d . . . H53 H 0.6539 0.8297 0.0192 0.038 Uiso 1 1 calc R . . C54 C 0.6024(3) 0.7417(3) -0.06470(13) 0.0352(7) Uani 1 1 d . . . H54 H 0.6822 0.7312 -0.0654 0.042 Uiso 1 1 calc R . . C55 C 0.3908(3) 0.7121(2) -0.11292(12) 0.0285(6) Uani 1 1 d . . . H55 H 0.3242 0.6805 -0.1472 0.034 Uiso 1 1 calc R . . C56 C 0.3690(3) 0.7699(2) -0.06418(12) 0.0274(6) Uani 1 1 d . . . H56 H 0.2880 0.7789 -0.0651 0.033 Uiso 1 1 calc R . . S1 S 0.96753(6) 0.75565(6) 0.93635(3) 0.02038(15) Uani 1 1 d . . . O9 O 0.9836(2) 0.68294(17) 0.99214(9) 0.0318(5) Uani 1 1 d . . . H9O H 0.938(4) 0.698(3) 1.0218(17) 0.079(13) Uiso 1 1 d . . . O10 O 1.07660(17) 0.76441(18) 0.90630(8) 0.0328(5) Uani 1 1 d . . . O11 O 0.84411(17) 0.68574(17) 0.89745(8) 0.0288(4) Uani 1 1 d . . . O12 O 0.96755(19) 0.86947(16) 0.96034(8) 0.0324(5) Uani 1 1 d . . . S2 S 0.59006(7) 0.46892(6) 0.26135(3) 0.02338(16) Uani 1 1 d . . . O13 O 0.6699(2) 0.39640(19) 0.26146(9) 0.0420(5) Uani 1 1 d . . . O14 O 0.6740(2) 0.60026(19) 0.25291(10) 0.0460(6) Uani 1 1 d . . . H14O H 0.694(4) 0.606(3) 0.2164(16) 0.069(12) Uiso 1 1 d . . . O15 O 0.48081(18) 0.43176(17) 0.21077(8) 0.0314(5) Uani 1 1 d . . . O16 O 0.5486(2) 0.47894(17) 0.31926(8) 0.0355(5) Uani 1 1 d . . . S3 S 0.77543(7) 0.61316(6) 0.10115(3) 0.02364(16) Uani 1 1 d . . . O17 O 0.8448(2) 0.5373(2) 0.12459(11) 0.0525(6) Uani 1 1 d . . . O18 O 0.8650(2) 0.71602(18) 0.07439(10) 0.0464(6) Uani 1 1 d . . . O19 O 0.66314(19) 0.54672(19) 0.05449(8) 0.0385(5) Uani 1 1 d . . . O20 O 0.7288(2) 0.66512(17) 0.14988(8) 0.0359(5) Uani 1 1 d . . . O1W O 0.1466(2) 0.06032(19) 0.91475(9) 0.0328(5) Uani 1 1 d D . . H1WA H 0.098(3) 0.008(2) 0.9342(14) 0.065(12) Uiso 1 1 d D . . H1WB H 0.142(4) 0.1288(17) 0.9213(17) 0.074(13) 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 O1 0.0398(13) 0.0581(14) 0.0267(11) -0.0170(10) 0.0079(10) 0.0135(11) O2 0.0387(13) 0.0718(16) 0.0352(12) -0.0163(11) 0.0105(10) 0.0239(12) O3 0.0499(14) 0.0439(13) 0.0272(11) -0.0041(9) 0.0122(10) 0.0259(11) O4 0.0833(19) 0.0537(15) 0.0347(12) 0.0144(11) 0.0311(13) 0.0334(14) O5 0.0540(15) 0.0619(15) 0.0318(12) -0.0128(11) 0.0117(11) 0.0240(13) O6 0.0522(15) 0.0685(16) 0.0394(13) -0.0085(11) 0.0179(11) 0.0311(13) O7 0.0425(13) 0.0538(14) 0.0270(11) -0.0173(10) 0.0074(10) 0.0160(11) O8 0.0437(13) 0.0677(16) 0.0285(11) -0.0078(10) 0.0096(10) 0.0344(12) N1 0.0301(13) 0.0280(12) 0.0234(12) -0.0022(10) 0.0133(10) 0.0112(10) N2 0.0301(14) 0.0429(15) 0.0237(13) -0.0042(11) 0.0060(11) 0.0169(12) N3 0.0322(13) 0.0231(12) 0.0251(12) -0.0010(10) 0.0109(10) 0.0115(10) N4 0.0360(14) 0.0256(12) 0.0266(13) -0.0026(10) 0.0138(11) 0.0132(11) C1 0.0360(17) 0.0330(16) 0.0218(14) -0.0053(12) 0.0071(13) 0.0113(14) C2 0.0332(16) 0.0297(15) 0.0270(15) -0.0009(12) 0.0121(13) 0.0108(13) C3 0.0318(17) 0.0504(19) 0.0227(15) -0.0102(13) 0.0035(13) 0.0129(15) C4 0.0275(16) 0.0511(19) 0.0313(16) -0.0085(14) 0.0067(13) 0.0154(15) C5 0.0345(17) 0.0303(15) 0.0253(14) -0.0024(12) 0.0105(13) 0.0110(13) C6 0.0347(18) 0.067(2) 0.0327(17) -0.0205(16) 0.0018(14) 0.0170(17) C7 0.0319(18) 0.068(2) 0.0346(17) -0.0203(16) 0.0063(14) 0.0189(17) C8 0.0361(17) 0.0367(17) 0.0267(15) -0.0044(12) 0.0091(13) 0.0117(14) C9 0.0360(17) 0.0381(17) 0.0219(14) -0.0029(12) 0.0046(13) 0.0133(14) C10 0.0288(15) 0.0234(14) 0.0237(14) 0.0010(11) 0.0097(12) 0.0088(12) C11 0.0275(15) 0.0340(16) 0.0260(15) -0.0032(12) 0.0025(12) 0.0128(13) C12 0.0245(15) 0.0297(15) 0.0357(16) 0.0002(12) 0.0095(13) 0.0132(12) C13 0.0281(15) 0.0233(14) 0.0229(14) -0.0039(11) 0.0008(11) 0.0080(12) C14 0.0235(14) 0.0288(15) 0.0297(15) 0.0004(12) 0.0080(12) 0.0124(12) C15 0.0309(16) 0.0365(17) 0.0290(16) -0.0029(13) 0.0059(13) 0.0143(14) C16 0.0271(15) 0.0326(16) 0.0243(14) -0.0002(12) 0.0062(12) 0.0111(13) C17 0.053(2) 0.0344(17) 0.0333(16) 0.0067(13) 0.0170(15) 0.0273(16) C18 0.057(2) 0.0420(18) 0.0247(15) 0.0110(13) 0.0182(14) 0.0292(16) C19 0.0304(16) 0.0311(15) 0.0244(14) -0.0011(12) 0.0042(12) 0.0131(13) C20 0.062(2) 0.0376(18) 0.0301(16) 0.0064(13) 0.0140(15) 0.0299(17) C21 0.062(2) 0.0419(18) 0.0258(15) 0.0091(13) 0.0144(15) 0.0295(17) C22 0.0333(16) 0.0370(16) 0.0226(14) 0.0037(12) 0.0083(12) 0.0144(14) C23 0.0408(18) 0.0391(17) 0.0227(14) 0.0039(12) 0.0126(13) 0.0175(14) C24 0.0258(15) 0.0325(15) 0.0236(14) -0.0001(12) 0.0035(12) 0.0116(13) C25 0.0464(19) 0.0252(15) 0.0344(16) -0.0010(12) 0.0151(14) 0.0106(14) C26 0.0376(18) 0.0373(17) 0.0312(16) 0.0043(13) 0.0131(14) 0.0119(14) C27 0.0452(19) 0.0313(16) 0.0404(17) 0.0015(14) 0.0132(15) 0.0205(15) C28 0.049(2) 0.0324(16) 0.0386(17) 0.0070(13) 0.0199(15) 0.0211(15) C29 0.047(2) 0.0384(17) 0.0249(15) 0.0002(13) 0.0132(14) 0.0234(16) C30 0.0448(18) 0.0323(16) 0.0271(15) 0.0041(12) 0.0135(14) 0.0227(14) C31 0.0380(18) 0.0454(18) 0.0238(15) -0.0060(13) 0.0050(13) 0.0162(15) C32 0.0306(16) 0.0413(17) 0.0281(15) -0.0036(13) 0.0078(13) 0.0148(14) C33 0.0366(16) 0.0269(14) 0.0192(13) 0.0034(11) 0.0092(12) 0.0163(13) C34 0.0304(16) 0.0460(18) 0.0263(15) -0.0060(13) 0.0048(13) 0.0180(14) C35 0.0366(17) 0.0510(19) 0.0306(16) -0.0015(14) 0.0129(14) 0.0243(16) C36 0.0303(15) 0.0266(14) 0.0178(13) -0.0025(11) 0.0060(11) 0.0112(12) C37 0.0279(15) 0.0259(14) 0.0184(13) -0.0029(11) 0.0034(11) 0.0098(12) C38 0.0258(14) 0.0181(13) 0.0210(13) 0.0033(10) 0.0079(11) 0.0089(11) C39 0.0245(15) 0.0283(15) 0.0260(14) -0.0005(11) 0.0024(11) 0.0116(12) C40 0.0253(15) 0.0317(15) 0.0304(15) 0.0017(12) 0.0099(12) 0.0147(13) C41 0.0241(14) 0.0251(14) 0.0252(14) -0.0023(11) 0.0042(11) 0.0091(12) C42 0.0235(14) 0.0281(14) 0.0266(14) 0.0002(11) 0.0079(11) 0.0135(12) C43 0.0333(16) 0.0294(15) 0.0205(14) -0.0034(11) 0.0069(12) 0.0134(13) C44 0.0300(15) 0.0277(15) 0.0218(13) -0.0002(11) 0.0082(12) 0.0124(12) C45 0.0236(14) 0.0349(16) 0.0222(14) -0.0055(12) 0.0007(11) 0.0091(13) C46 0.0240(14) 0.0335(16) 0.0281(15) -0.0019(12) 0.0096(12) 0.0124(13) C47 0.0289(15) 0.0224(13) 0.0200(13) -0.0006(10) 0.0096(11) 0.0097(12) C48 0.0303(16) 0.0394(17) 0.0200(14) -0.0034(12) 0.0015(12) 0.0167(14) C49 0.0282(15) 0.0410(17) 0.0238(14) -0.0040(12) 0.0053(12) 0.0178(14) C50 0.0275(15) 0.0259(14) 0.0222(13) 0.0006(11) 0.0079(11) 0.0096(12) C51 0.0268(15) 0.0269(14) 0.0213(13) -0.0034(11) 0.0040(11) 0.0076(12) C52 0.0269(14) 0.0185(13) 0.0235(13) 0.0006(10) 0.0079(11) 0.0085(11) C53 0.0236(15) 0.0397(17) 0.0315(16) -0.0068(13) 0.0018(12) 0.0121(13) C54 0.0284(16) 0.0440(18) 0.0399(17) -0.0030(14) 0.0127(14) 0.0186(14) C55 0.0297(16) 0.0307(15) 0.0233(14) -0.0029(12) 0.0063(12) 0.0080(13) C56 0.0235(15) 0.0350(16) 0.0277(14) 0.0001(12) 0.0084(12) 0.0138(13) S1 0.0200(3) 0.0267(3) 0.0179(3) -0.0001(3) 0.0058(3) 0.0117(3) O9 0.0454(13) 0.0369(12) 0.0255(10) 0.0071(9) 0.0118(9) 0.0274(10) O10 0.0233(10) 0.0470(12) 0.0296(11) 0.0011(9) 0.0120(9) 0.0111(9) O11 0.0219(10) 0.0407(11) 0.0237(10) -0.0057(8) 0.0040(8) 0.0113(9) O12 0.0430(12) 0.0252(10) 0.0328(11) 0.0003(8) 0.0087(9) 0.0163(9) S2 0.0274(4) 0.0290(4) 0.0158(3) -0.0001(3) 0.0067(3) 0.0115(3) O13 0.0396(13) 0.0557(14) 0.0431(13) 0.0046(11) 0.0096(10) 0.0314(11) O14 0.0633(16) 0.0376(13) 0.0250(12) -0.0037(9) 0.0201(11) -0.0019(11) O15 0.0293(11) 0.0427(12) 0.0250(10) -0.0073(9) 0.0012(8) 0.0183(9) O16 0.0527(13) 0.0351(11) 0.0215(10) 0.0018(8) 0.0173(9) 0.0147(10) S3 0.0272(4) 0.0235(3) 0.0225(3) 0.0022(3) 0.0079(3) 0.0102(3) O17 0.0440(14) 0.0475(14) 0.0714(16) 0.0175(12) 0.0020(12) 0.0256(12) O18 0.0661(16) 0.0293(11) 0.0543(14) 0.0094(10) 0.0431(12) 0.0159(11) O19 0.0329(12) 0.0561(14) 0.0282(11) -0.0163(10) 0.0017(9) 0.0206(11) O20 0.0461(13) 0.0357(12) 0.0233(10) -0.0034(9) 0.0153(9) 0.0077(10) O1W 0.0353(12) 0.0279(12) 0.0336(12) -0.0059(10) 0.0128(10) 0.0068(10) _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 O1 C1 1.293(3) . ? O2 C1 1.236(3) . ? O3 C15 1.324(3) . ? O4 C15 1.205(3) . ? O5 C29 1.237(3) . ? O6 C29 1.293(4) . ? O7 C43 1.299(3) . ? O8 C43 1.246(3) . ? N1 C12 1.332(3) . ? N1 C13 1.346(3) . ? N2 C27 1.337(4) . ? N2 C26 1.337(4) . ? N3 C40 1.338(3) . ? N3 C41 1.342(3) . ? N4 C54 1.325(4) . ? N4 C55 1.341(3) . ? C1 C2 1.489(4) . ? C2 C7 1.378(4) . ? C2 C3 1.381(4) . ? C3 C4 1.382(4) . ? C4 C5 1.386(4) . ? C5 C6 1.390(4) . ? C5 C8 1.469(4) . ? C6 C7 1.377(4) . ? C8 C9 1.317(4) . ? C9 C10 1.468(4) . ? C10 C11 1.394(4) . ? C10 C14 1.399(4) . ? C11 C12 1.369(4) . ? C13 C14 1.366(3) . ? C15 C16 1.491(4) . ? C16 C17 1.378(4) . ? C16 C21 1.384(4) . ? C17 C18 1.382(4) . ? C18 C19 1.383(4) . ? C19 C20 1.389(4) . ? C19 C22 1.464(4) . ? C20 C21 1.377(4) . ? C22 C23 1.333(4) . ? C23 C24 1.461(4) . ? C24 C25 1.396(4) . ? C24 C28 1.398(4) . ? C25 C26 1.359(4) . ? C27 C28 1.369(4) . ? C29 C30 1.486(4) . ? C30 C35 1.383(4) . ? C30 C31 1.388(4) . ? C31 C32 1.381(4) . ? C32 C33 1.387(4) . ? C33 C34 1.404(4) . ? C33 C36 1.470(3) . ? C34 C35 1.378(4) . ? C36 C37 1.333(4) . ? C37 C38 1.456(3) . ? C38 C39 1.397(3) . ? C38 C42 1.403(3) . ? C39 C40 1.370(4) . ? C41 C42 1.372(3) . ? C43 C44 1.479(3) . ? C44 C49 1.380(4) . ? C44 C45 1.397(4) . ? C45 C46 1.377(3) . ? C46 C47 1.398(4) . ? C47 C48 1.396(4) . ? C47 C50 1.456(3) . ? C48 C49 1.379(3) . ? C50 C51 1.331(4) . ? C51 C52 1.458(3) . ? C52 C56 1.397(3) . ? C52 C53 1.397(4) . ? C53 C54 1.369(4) . ? C55 C56 1.362(3) . ? S1 O12 1.4423(19) . ? S1 O10 1.4456(18) . ? S1 O11 1.4578(19) . ? S1 O9 1.5490(19) . ? S2 O13 1.436(2) . ? S2 O16 1.4444(18) . ? S2 O15 1.4520(18) . ? S2 O14 1.551(2) . ? S3 O17 1.435(2) . ? S3 O19 1.459(2) . ? S3 O20 1.4761(19) . ? S3 O18 1.488(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 C12 N1 C13 121.3(2) . . ? C27 N2 C26 121.2(2) . . ? C40 N3 C41 121.5(2) . . ? C54 N4 C55 121.9(2) . . ? O2 C1 O1 123.5(2) . . ? O2 C1 C2 120.3(3) . . ? O1 C1 C2 116.1(3) . . ? C7 C2 C3 119.5(3) . . ? C7 C2 C1 118.4(3) . . ? C3 C2 C1 122.1(3) . . ? C2 C3 C4 120.3(3) . . ? C3 C4 C5 120.8(3) . . ? C4 C5 C6 118.0(3) . . ? C4 C5 C8 123.9(3) . . ? C6 C5 C8 118.0(3) . . ? C7 C6 C5 121.3(3) . . ? C6 C7 C2 120.1(3) . . ? C9 C8 C5 126.9(3) . . ? C8 C9 C10 125.2(3) . . ? C11 C10 C14 117.2(2) . . ? C11 C10 C9 119.4(2) . . ? C14 C10 C9 123.4(2) . . ? C12 C11 C10 120.8(3) . . ? N1 C12 C11 120.1(2) . . ? N1 C13 C14 120.7(2) . . ? C13 C14 C10 119.9(2) . . ? O4 C15 O3 123.5(3) . . ? O4 C15 C16 124.4(3) . . ? O3 C15 C16 112.1(2) . . ? C17 C16 C21 118.6(3) . . ? C17 C16 C15 122.4(3) . . ? C21 C16 C15 118.9(2) . . ? C16 C17 C18 120.3(3) . . ? C17 C18 C19 121.4(3) . . ? C18 C19 C20 117.9(3) . . ? C18 C19 C22 118.3(2) . . ? C20 C19 C22 123.7(3) . . ? C21 C20 C19 120.7(3) . . ? C20 C21 C16 121.0(3) . . ? C23 C22 C19 126.7(3) . . ? C22 C23 C24 124.0(3) . . ? C25 C24 C28 117.0(3) . . ? C25 C24 C23 123.0(3) . . ? C28 C24 C23 119.9(3) . . ? C26 C25 C24 120.7(3) . . ? N2 C26 C25 120.5(3) . . ? N2 C27 C28 120.6(3) . . ? C27 C28 C24 120.1(3) . . ? O5 C29 O6 123.9(3) . . ? O5 C29 C30 120.1(3) . . ? O6 C29 C30 116.0(3) . . ? C35 C30 C31 119.6(3) . . ? C35 C30 C29 121.2(3) . . ? C31 C30 C29 119.2(3) . . ? C32 C31 C30 120.5(3) . . ? C31 C32 C33 120.4(3) . . ? C32 C33 C34 118.7(2) . . ? C32 C33 C36 123.7(3) . . ? C34 C33 C36 117.7(2) . . ? C35 C34 C33 120.6(3) . . ? C34 C35 C30 120.1(3) . . ? C37 C36 C33 126.8(3) . . ? C36 C37 C38 124.2(2) . . ? C39 C38 C42 117.1(2) . . ? C39 C38 C37 120.6(2) . . ? C42 C38 C37 122.3(2) . . ? C40 C39 C38 120.9(2) . . ? N3 C40 C39 120.0(2) . . ? N3 C41 C42 120.7(2) . . ? C41 C42 C38 119.9(2) . . ? O8 C43 O7 123.4(2) . . ? O8 C43 C44 121.0(2) . . ? O7 C43 C44 115.6(2) . . ? C49 C44 C45 119.4(2) . . ? C49 C44 C43 118.9(2) . . ? C45 C44 C43 121.7(2) . . ? C46 C45 C44 120.1(2) . . ? C45 C46 C47 120.7(2) . . ? C48 C47 C46 118.5(2) . . ? C48 C47 C50 118.4(2) . . ? C46 C47 C50 123.1(2) . . ? C49 C48 C47 120.7(3) . . ? C48 C49 C44 120.6(3) . . ? C51 C50 C47 128.0(3) . . ? C50 C51 C52 126.1(3) . . ? C56 C52 C53 117.3(2) . . ? C56 C52 C51 123.4(2) . . ? C53 C52 C51 119.3(2) . . ? C54 C53 C52 120.4(3) . . ? N4 C54 C53 120.1(3) . . ? N4 C55 C56 120.4(3) . . ? C55 C56 C52 120.0(2) . . ? O12 S1 O10 114.35(12) . . ? O12 S1 O11 112.04(11) . . ? O10 S1 O11 111.39(11) . . ? O12 S1 O9 106.72(11) . . ? O10 S1 O9 104.76(11) . . ? O11 S1 O9 106.91(11) . . ? O13 S2 O16 113.65(12) . . ? O13 S2 O15 112.43(12) . . ? O16 S2 O15 111.61(12) . . ? O13 S2 O14 108.34(13) . . ? O16 S2 O14 103.43(12) . . ? O15 S2 O14 106.69(12) . . ? O17 S3 O19 111.10(13) . . ? O17 S3 O20 112.05(13) . . ? O19 S3 O20 108.12(11) . . ? O17 S3 O18 109.10(14) . . ? O19 S3 O18 109.68(13) . . ? O20 S3 O18 106.68(11) . . ? 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 O1W H1WB O18 0.843(10) 1.876(11) 2.715(3) 173(4) 2_666 O1W H1WA O12 0.849(10) 1.950(13) 2.783(3) 167(3) 1_445 O14 H14O O20 0.87(4) 1.69(4) 2.524(3) 159(4) . O9 H9O O18 0.94(4) 1.57(4) 2.507(3) 176(4) 1_556 N4 H4N O15 0.901(10) 1.807(11) 2.705(3) 175(3) 2_665 N3 H3N O19 0.905(10) 1.754(11) 2.658(3) 176(3) 2_665 N2 H2N O1W 0.913(10) 1.720(11) 2.631(3) 175(3) 1_565 N1 H1N O11 0.899(10) 1.810(10) 2.709(3) 179(3) 2_766 O7 H7 O2 0.83 1.81 2.642(3) 175.6 2_676 O6 H6O O5 1.26(6) 1.35(6) 2.613(3) 176(5) 2_576 O3 H3 O16 0.83 1.82 2.595(3) 155.4 . O1 H1 O8 0.83 1.82 2.647(3) 176.4 2_676 _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.444 _refine_diff_density_min -0.333 _refine_diff_density_rms 0.068 data_A571jj _database_code_depnum_ccdc_archive 'CCDC 888319' #TrackingRef 'GK10CEC2012.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C40.75 H39 N4 O6.75' _chemical_formula_weight 692.76 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 P2(1)/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 10.1643(11) _cell_length_b 10.1819(10) _cell_length_c 34.305(4) _cell_angle_alpha 90.00 _cell_angle_beta 95.067(3) _cell_angle_gamma 90.00 _cell_volume 3536.4(6) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 668 _cell_measurement_theta_min 2.68 _cell_measurement_theta_max 20.24 _exptl_crystal_description Block _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.46 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas 'Not Measured' _exptl_crystal_density_diffrn 1.301 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1462 _exptl_absorpt_coefficient_mu 0.089 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.9600 _exptl_absorpt_correction_T_max 0.9911 _exptl_absorpt_process_details 'Sadabs, (Sheldrick 2001)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 20322 _diffrn_reflns_av_R_equivalents 0.0839 _diffrn_reflns_av_sigmaI/netI 0.0889 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -35 _diffrn_reflns_limit_l_max 40 _diffrn_reflns_theta_min 2.05 _diffrn_reflns_theta_max 25.00 _reflns_number_total 6205 _reflns_number_gt 3999 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^ > 2sigma(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^)+(0.1029P)^2^+3.7133P] 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 6205 _refine_ls_number_parameters 489 _refine_ls_number_restraints 4 _refine_ls_R_factor_all 0.1337 _refine_ls_R_factor_gt 0.0861 _refine_ls_wR_factor_ref 0.2338 _refine_ls_wR_factor_gt 0.2053 _refine_ls_goodness_of_fit_ref 1.072 _refine_ls_restrained_S_all 1.073 _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 O1 O 0.4986(3) 0.5983(3) 0.36365(9) 0.0312(7) Uani 1 1 d . . . H1 H 0.4403 0.5986 0.3796 0.047 Uiso 1 1 calc R . . O2 O 0.3698(3) 0.4397(3) 0.33470(9) 0.0316(7) Uani 1 1 d . . . O3 O 1.5028(3) 0.1176(3) 0.13482(9) 0.0306(7) Uani 1 1 d . . . H3 H 1.5592 0.1033 0.1188 0.046 Uiso 1 1 calc R . . O4 O 1.5663(4) 0.3239(3) 0.12717(13) 0.0668(12) Uani 1 1 d . . . N1 N 0.9962(4) 0.5666(4) 0.09614(11) 0.0401(10) Uani 1 1 d . . . N2 N 0.9680(4) 0.1828(4) 0.37219(11) 0.0399(10) Uani 1 1 d . . . N3 N 0.6801(3) 0.0611(4) 0.08856(10) 0.0318(9) Uani 1 1 d . . . N4 N 0.1850(3) 0.1079(4) 0.08722(11) 0.0336(9) Uani 1 1 d . . . C1 C 0.9842(4) 0.2983(4) 0.25166(12) 0.0247(9) Uani 1 1 d . . . H1A H 0.9922 0.2176 0.2354 0.030 Uiso 1 1 calc R . . C2 C 0.8691(4) 0.3880(4) 0.23165(12) 0.0244(9) Uani 1 1 d . . . H2 H 0.8261 0.3427 0.2080 0.029 Uiso 1 1 calc R . . C3 C 0.9727(4) 0.4882(4) 0.21909(12) 0.0256(9) Uani 1 1 d . . . H3A H 0.9650 0.5728 0.2335 0.031 Uiso 1 1 calc R . . C4 C 1.0867(4) 0.4007(4) 0.24033(12) 0.0255(9) Uani 1 1 d . . . H4 H 1.1255 0.4468 0.2644 0.031 Uiso 1 1 calc R . . C5 C 1.0732(5) 0.2435(5) 0.35978(14) 0.0404(12) Uani 1 1 d . . . H5 H 1.1457 0.2610 0.3785 0.048 Uiso 1 1 calc R . . C6 C 1.0838(4) 0.2825(4) 0.32160(13) 0.0279(10) Uani 1 1 d . . . H6 H 1.1616 0.3251 0.3147 0.033 Uiso 1 1 calc R . . C7 C 0.9807(4) 0.2591(4) 0.29342(12) 0.0228(9) Uani 1 1 d . . . C8 C 0.8723(4) 0.1935(4) 0.30610(13) 0.0289(10) Uani 1 1 d . . . H8 H 0.7993 0.1731 0.2879 0.035 Uiso 1 1 calc R . . C9 C 0.8692(4) 0.1580(4) 0.34440(14) 0.0331(11) Uani 1 1 d . . . H9 H 0.7932 0.1133 0.3518 0.040 Uiso 1 1 calc R . . C10 C 0.7654(4) 0.4339(4) 0.25709(12) 0.0241(9) Uani 1 1 d . . . C11 C 0.6363(4) 0.3886(4) 0.24976(12) 0.0249(9) Uani 1 1 d . . . H11 H 0.6134 0.3375 0.2270 0.030 Uiso 1 1 calc R . . C12 C 0.5409(4) 0.4160(4) 0.27474(12) 0.0243(9) Uani 1 1 d . . . H12 H 0.4537 0.3833 0.2692 0.029 Uiso 1 1 calc R . . C13 C 0.5720(4) 0.4917(4) 0.30818(12) 0.0228(9) Uani 1 1 d . . . C14 C 0.6993(4) 0.5436(4) 0.31500(12) 0.0230(9) Uani 1 1 d . . . H14 H 0.7206 0.5989 0.3369 0.028 Uiso 1 1 calc R . . C15 C 0.7942(4) 0.5144(4) 0.28983(11) 0.0233(9) Uani 1 1 d . . . H15 H 0.8806 0.5497 0.2948 0.028 Uiso 1 1 calc R . . C16 C 0.4696(4) 0.5082(4) 0.33663(12) 0.0257(10) Uani 1 1 d . . . C17 C 1.0177(4) 0.6576(4) 0.12402(13) 0.0352(11) Uani 1 1 d . . . H17 H 1.0408 0.7434 0.1161 0.042 Uiso 1 1 calc R . . C18 C 1.0090(4) 0.6366(4) 0.16296(13) 0.0285(10) Uani 1 1 d . . . H18 H 1.0252 0.7067 0.1810 0.034 Uiso 1 1 calc R . . C19 C 0.9768(4) 0.5139(4) 0.17623(12) 0.0245(9) Uani 1 1 d . . . C20 C 0.9538(4) 0.4169(4) 0.14776(13) 0.0322(10) Uani 1 1 d . . . H20 H 0.9310 0.3303 0.1550 0.039 Uiso 1 1 calc R . . C21 C 0.9644(4) 0.4474(5) 0.10886(13) 0.0360(11) Uani 1 1 d . . . H21 H 0.9481 0.3796 0.0900 0.043 Uiso 1 1 calc R . . C22 C 1.1966(4) 0.3566(4) 0.21628(12) 0.0244(9) Uani 1 1 d . . . C23 C 1.2732(4) 0.4508(4) 0.19922(13) 0.0300(10) Uani 1 1 d . . . H23 H 1.2584 0.5413 0.2040 0.036 Uiso 1 1 calc R . . C24 C 1.3698(4) 0.4144(4) 0.17564(13) 0.0287(10) Uani 1 1 d . . . H24 H 1.4204 0.4800 0.1641 0.034 Uiso 1 1 calc R . . C25 C 1.3943(4) 0.2818(4) 0.16849(11) 0.0237(9) Uani 1 1 d . . . C26 C 1.3220(4) 0.1879(4) 0.18625(11) 0.0236(9) Uani 1 1 d . . . H26 H 1.3384 0.0974 0.1821 0.028 Uiso 1 1 calc R . . C27 C 1.2253(4) 0.2255(4) 0.21017(12) 0.0248(9) Uani 1 1 d . . . H27 H 1.1777 0.1597 0.2227 0.030 Uiso 1 1 calc R . . C28 C 1.4968(4) 0.2445(4) 0.14170(13) 0.0334(11) Uani 1 1 d . . . C29 C 0.7187(4) -0.0625(5) 0.08419(13) 0.0340(11) Uani 1 1 d . . . H29 H 0.6802 -0.1296 0.0987 0.041 Uiso 1 1 calc R . . C30 C 0.8122(4) -0.0967(5) 0.05940(13) 0.0344(11) Uani 1 1 d . . . H30 H 0.8366 -0.1862 0.0571 0.041 Uiso 1 1 calc R . . C31 C 0.8709(4) -0.0027(5) 0.03788(12) 0.0332(11) Uani 1 1 d . . . C32 C 0.8288(4) 0.1271(5) 0.04221(13) 0.0365(11) Uani 1 1 d . . . H32 H 0.8647 0.1956 0.0276 0.044 Uiso 1 1 calc R . . C33 C 0.7353(4) 0.1549(5) 0.06764(13) 0.0360(11) Uani 1 1 d . . . H33 H 0.7087 0.2435 0.0706 0.043 Uiso 1 1 calc R . . C34 C 0.9707(4) -0.0410(5) 0.01150(13) 0.0359(11) Uani 1 1 d . . . H34 H 0.9949 -0.1310 0.0109 0.043 Uiso 1 1 calc R . . C35 C 0.2329(4) -0.0102(5) 0.08019(14) 0.0371(11) Uani 1 1 d . . . H35 H 0.2017 -0.0833 0.0939 0.044 Uiso 1 1 calc R . . C36 C 0.3259(4) -0.0323(5) 0.05391(13) 0.0356(11) Uani 1 1 d . . . H36 H 0.3564 -0.1189 0.0497 0.043 Uiso 1 1 calc R . . C37 C 0.3748(4) 0.0723(5) 0.03354(12) 0.0347(11) Uani 1 1 d . . . C38 C 0.3238(5) 0.1952(5) 0.04131(14) 0.0415(12) Uani 1 1 d . . . H38 H 0.3534 0.2703 0.0281 0.050 Uiso 1 1 calc R . . C39 C 0.2310(4) 0.2094(5) 0.06788(14) 0.0392(12) Uani 1 1 d . . . H39 H 0.1984 0.2948 0.0727 0.047 Uiso 1 1 calc R . . C40 C 0.4727(4) 0.0567(5) 0.00495(13) 0.0362(11) Uani 1 1 d . . . H40 H 0.4997 0.1339 -0.0077 0.043 Uiso 1 1 calc R . . O1W O 1.0656(5) 0.6125(5) 0.01827(16) 0.0906(16) Uani 1 1 d D . . H1WA H 0.9819(8) 0.603(6) 0.016(2) 0.109 Uiso 1 1 d D . . H1WB H 1.107(5) 0.540(3) 0.020(2) 0.109 Uiso 1 1 d D . . C1S C 0.5176(11) 0.6497(8) 0.0444(3) 0.100(4) Uani 0.75 1 d PD A 1 H1SA H 0.4340 0.6421 0.0280 0.149 Uiso 0.75 1 calc PR A 1 H1SB H 0.5881 0.6741 0.0281 0.149 Uiso 0.75 1 calc PR A 1 H1SC H 0.5093 0.7173 0.0644 0.149 Uiso 0.75 1 calc PR A 1 O1S O 0.5502(10) 0.5204(7) 0.0639(2) 0.114(3) Uani 0.75 1 d PD A 1 H1S H 0.5546 0.5300 0.0883 0.171 Uiso 0.75 1 calc PR A 1 O2W O 0.3261(7) 0.5611(10) 0.0029(2) 0.144(4) Uani 0.75 1 d P B 2 O3W O 0.6620(16) 0.4522(18) 0.0600(6) 0.078(6) Uani 0.25 1 d P C 2 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 O1 0.0254(16) 0.0384(18) 0.0313(18) -0.0003(14) 0.0118(13) -0.0011(14) O2 0.0211(16) 0.0311(16) 0.0440(19) -0.0001(14) 0.0109(13) -0.0030(14) O3 0.0261(17) 0.0385(19) 0.0289(18) -0.0004(13) 0.0113(13) 0.0012(13) O4 0.064(2) 0.040(2) 0.106(3) -0.003(2) 0.063(2) -0.0112(19) N1 0.042(2) 0.044(2) 0.036(2) -0.0008(19) 0.0107(19) -0.0040(19) N2 0.050(3) 0.033(2) 0.038(2) -0.0020(18) 0.014(2) 0.0025(19) N3 0.0236(19) 0.044(2) 0.028(2) -0.0050(17) 0.0080(16) 0.0010(17) N4 0.0245(19) 0.044(2) 0.032(2) 0.0032(18) 0.0036(16) -0.0021(18) C1 0.019(2) 0.024(2) 0.031(2) -0.0077(18) 0.0051(17) -0.0006(17) C2 0.024(2) 0.027(2) 0.023(2) -0.0019(17) 0.0058(17) -0.0029(18) C3 0.023(2) 0.025(2) 0.030(2) -0.0049(18) 0.0073(18) 0.0001(18) C4 0.023(2) 0.028(2) 0.026(2) -0.0026(18) 0.0066(18) -0.0028(18) C5 0.044(3) 0.037(3) 0.039(3) -0.008(2) -0.003(2) -0.002(2) C6 0.026(2) 0.023(2) 0.034(3) -0.0006(18) 0.0020(19) -0.0014(18) C7 0.020(2) 0.017(2) 0.031(2) -0.0061(17) 0.0073(18) 0.0033(17) C8 0.024(2) 0.025(2) 0.039(3) -0.0032(19) 0.0091(19) -0.0001(18) C9 0.030(2) 0.024(2) 0.047(3) -0.002(2) 0.015(2) 0.0049(19) C10 0.023(2) 0.025(2) 0.025(2) 0.0057(18) 0.0029(17) 0.0018(18) C11 0.021(2) 0.027(2) 0.026(2) -0.0005(17) -0.0023(18) -0.0009(18) C12 0.019(2) 0.023(2) 0.031(2) 0.0069(18) 0.0000(18) 0.0000(17) C13 0.019(2) 0.022(2) 0.028(2) 0.0076(17) 0.0058(17) 0.0069(17) C14 0.023(2) 0.022(2) 0.024(2) 0.0023(17) 0.0023(17) 0.0020(17) C15 0.018(2) 0.027(2) 0.026(2) 0.0027(18) 0.0058(17) 0.0016(17) C16 0.020(2) 0.024(2) 0.034(3) 0.0075(19) 0.0060(18) 0.0063(19) C17 0.040(3) 0.029(2) 0.037(3) 0.000(2) 0.005(2) -0.006(2) C18 0.029(2) 0.028(2) 0.030(3) -0.0064(19) 0.0061(19) 0.0004(19) C19 0.016(2) 0.031(2) 0.027(2) -0.0074(18) 0.0093(17) 0.0036(18) C20 0.030(2) 0.029(2) 0.039(3) -0.003(2) 0.010(2) -0.0047(19) C21 0.036(3) 0.043(3) 0.030(3) -0.014(2) 0.008(2) -0.004(2) C22 0.016(2) 0.033(2) 0.024(2) -0.0014(18) 0.0016(17) -0.0006(18) C23 0.022(2) 0.024(2) 0.045(3) -0.0044(19) 0.007(2) -0.0023(18) C24 0.021(2) 0.024(2) 0.042(3) 0.0065(19) 0.007(2) -0.0025(18) C25 0.016(2) 0.032(2) 0.024(2) 0.0046(18) 0.0029(17) -0.0001(17) C26 0.023(2) 0.025(2) 0.024(2) 0.0014(17) 0.0055(17) 0.0008(18) C27 0.022(2) 0.028(2) 0.025(2) 0.0065(17) 0.0055(17) -0.0034(18) C28 0.026(2) 0.034(3) 0.042(3) 0.000(2) 0.011(2) -0.001(2) C29 0.025(2) 0.049(3) 0.028(3) 0.003(2) 0.0067(19) -0.003(2) C30 0.028(2) 0.048(3) 0.027(3) 0.000(2) 0.006(2) 0.006(2) C31 0.022(2) 0.055(3) 0.024(2) -0.007(2) 0.0068(18) 0.001(2) C32 0.033(3) 0.046(3) 0.032(3) -0.005(2) 0.011(2) -0.010(2) C33 0.032(2) 0.045(3) 0.032(3) -0.003(2) 0.012(2) -0.004(2) C34 0.026(2) 0.053(3) 0.029(3) -0.004(2) 0.0044(19) -0.003(2) C35 0.030(2) 0.044(3) 0.039(3) 0.009(2) 0.012(2) 0.002(2) C36 0.032(3) 0.049(3) 0.027(3) 0.008(2) 0.010(2) 0.007(2) C37 0.024(2) 0.058(3) 0.022(2) 0.006(2) 0.0043(19) 0.002(2) C38 0.037(3) 0.050(3) 0.038(3) 0.005(2) 0.009(2) -0.008(2) C39 0.035(3) 0.048(3) 0.037(3) 0.002(2) 0.013(2) -0.003(2) C40 0.021(2) 0.064(3) 0.024(2) 0.006(2) 0.0064(19) -0.001(2) O1W 0.093(4) 0.107(4) 0.077(3) 0.031(3) 0.037(3) 0.022(3) C1S 0.158(10) 0.087(7) 0.051(6) 0.014(5) -0.008(6) -0.063(7) O1S 0.152(8) 0.109(6) 0.079(5) -0.011(4) 0.008(5) -0.003(5) O2W 0.077(5) 0.275(11) 0.086(5) 0.082(6) 0.048(4) 0.089(6) O3W 0.049(10) 0.087(13) 0.103(15) 0.012(10) 0.030(9) 0.042(9) _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 O1 C16 1.319(5) . ? O2 C16 1.228(5) . ? O3 C28 1.315(5) . ? O4 C28 1.210(5) . ? N1 C17 1.336(6) . ? N1 C21 1.339(6) . ? N2 C5 1.337(6) . ? N2 C9 1.346(6) . ? N3 C29 1.331(6) . ? N3 C33 1.346(6) . ? N4 C35 1.328(6) . ? N4 C39 1.335(6) . ? C1 C7 1.491(6) . ? C1 C4 1.548(5) . ? C1 C2 1.592(6) . ? C2 C10 1.501(6) . ? C2 C3 1.554(6) . ? C3 C19 1.497(6) . ? C3 C4 1.587(6) . ? C4 C22 1.514(6) . ? C5 C6 1.382(6) . ? C6 C7 1.383(6) . ? C7 C8 1.390(6) . ? C8 C9 1.366(6) . ? C10 C11 1.393(6) . ? C10 C15 1.401(6) . ? C11 C12 1.378(6) . ? C12 C13 1.395(6) . ? C13 C14 1.398(6) . ? C13 C16 1.498(5) . ? C14 C15 1.382(5) . ? C17 C18 1.364(6) . ? C18 C19 1.379(6) . ? C19 C20 1.394(6) . ? C20 C21 1.384(6) . ? C22 C27 1.386(6) . ? C22 C23 1.396(6) . ? C23 C24 1.378(6) . ? C24 C25 1.398(6) . ? C25 C26 1.380(5) . ? C25 C28 1.498(6) . ? C26 C27 1.388(6) . ? C29 C30 1.375(6) . ? C30 C31 1.377(6) . ? C31 C32 1.401(6) . ? C31 C34 1.470(6) . ? C32 C33 1.375(6) . ? C34 C34 1.326(9) 3_755 ? C35 C36 1.381(6) . ? C36 C37 1.390(6) . ? C37 C38 1.389(7) . ? C37 C40 1.466(6) . ? C38 C39 1.376(6) . ? C40 C40 1.337(9) 3_655 ? C1S O1S 1.500(8) . ? 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 C17 N1 C21 115.1(4) . . ? C5 N2 C9 115.4(4) . . ? C29 N3 C33 118.0(4) . . ? C35 N4 C39 117.4(4) . . ? C7 C1 C4 119.7(3) . . ? C7 C1 C2 119.3(3) . . ? C4 C1 C2 89.5(3) . . ? C10 C2 C3 119.1(3) . . ? C10 C2 C1 117.1(3) . . ? C3 C2 C1 90.3(3) . . ? C19 C3 C2 117.7(3) . . ? C19 C3 C4 117.8(3) . . ? C2 C3 C4 89.4(3) . . ? C22 C4 C1 118.9(3) . . ? C22 C4 C3 117.4(3) . . ? C1 C4 C3 90.7(3) . . ? N2 C5 C6 124.5(4) . . ? C5 C6 C7 119.7(4) . . ? C6 C7 C8 115.9(4) . . ? C6 C7 C1 123.0(4) . . ? C8 C7 C1 121.1(4) . . ? C9 C8 C7 120.9(4) . . ? N2 C9 C8 123.6(4) . . ? C11 C10 C15 117.8(4) . . ? C11 C10 C2 119.4(4) . . ? C15 C10 C2 122.7(4) . . ? C12 C11 C10 121.6(4) . . ? C11 C12 C13 120.1(4) . . ? C12 C13 C14 119.1(4) . . ? C12 C13 C16 118.5(4) . . ? C14 C13 C16 122.3(4) . . ? C15 C14 C13 120.1(4) . . ? C14 C15 C10 121.2(4) . . ? O2 C16 O1 124.4(4) . . ? O2 C16 C13 121.3(4) . . ? O1 C16 C13 114.3(4) . . ? N1 C17 C18 124.9(4) . . ? C17 C18 C19 120.3(4) . . ? C18 C19 C20 116.1(4) . . ? C18 C19 C3 120.7(4) . . ? C20 C19 C3 123.1(4) . . ? C21 C20 C19 119.6(4) . . ? N1 C21 C20 124.0(4) . . ? C27 C22 C23 117.8(4) . . ? C27 C22 C4 122.9(4) . . ? C23 C22 C4 119.3(4) . . ? C24 C23 C22 121.0(4) . . ? C23 C24 C25 120.6(4) . . ? C26 C25 C24 118.8(4) . . ? C26 C25 C28 121.4(4) . . ? C24 C25 C28 119.8(4) . . ? C25 C26 C27 120.2(4) . . ? C22 C27 C26 121.6(4) . . ? O4 C28 O3 123.0(4) . . ? O4 C28 C25 123.1(4) . . ? O3 C28 C25 113.9(4) . . ? N3 C29 C30 122.4(4) . . ? C29 C30 C31 120.8(4) . . ? C30 C31 C32 116.6(4) . . ? C30 C31 C34 120.1(4) . . ? C32 C31 C34 123.3(4) . . ? C33 C32 C31 119.7(4) . . ? N3 C33 C32 122.4(4) . . ? C34 C34 C31 124.8(6) 3_755 . ? N4 C35 C36 123.3(4) . . ? C35 C36 C37 120.0(4) . . ? C38 C37 C36 116.0(4) . . ? C38 C37 C40 120.8(4) . . ? C36 C37 C40 123.2(4) . . ? C39 C38 C37 120.7(4) . . ? N4 C39 C38 122.6(5) . . ? C40 C40 C37 125.8(6) 3_655 . ? 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 O1 H1 N4 0.84 1.79 2.625(5) 177.1 2 O3 H3 N3 0.84 1.73 2.569(4) 174.6 1_655 O1W H1WB O2W 0.851(5) 2.36(6) 2.794(8) 112(5) 1_655 O1S H1S N2 0.84 2.09 2.764(8) 137.1 2_655 O1S H1S O4 0.84 2.48 2.945(8) 115.6 1_455 _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 1.076 _refine_diff_density_min -0.478 _refine_diff_density_rms 0.081 #===#END