# Supplementary Material (ESI) for Perkin Transactions # This journal is © The Royal Society of Chemistry 2002 data_global _journal_coden_Cambridge 207 loop_ _publ_author_name 'Thorfinnur Gunnlaugsson' 'H. Q. Nimal Gunaratne' 'Mark Nieuwenhuyzen' 'Joseph P. Leonard' _publ_contact_author_name 'Dr Thorfinnur Gunnlaugsson' _publ_contact_author_address ; Department of Chemistry Trinity College Dublin Ireland Dublin 2 REPUBLIC OF IRELAND ; _publ_contact_author_email 'GUNNLAUT@TCD.IE' _publ_requested_journal 'Perkin Transactions 1' _publ_section_title ; Syntheses of novel functionalised macrocyclic compounds as Na+ and K+ receptors: a mild and high yielding nitration in water of mono and bis 2-methoxyaniline functionalised crown ethers ; data_2 _database_code_CSD 186701 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C26 H38 N2 O6' _chemical_formula_weight 474.58 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)/c 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 7.218(2) _cell_length_b 7.852(2) _cell_length_c 21.449(6) _cell_angle_alpha 90.00 _cell_angle_beta 93.011(4) _cell_angle_gamma 90.00 _cell_volume 1213.9(6) _cell_formula_units_Z 2 _cell_measurement_temperature 153(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.65 _exptl_crystal_size_mid 0.54 _exptl_crystal_size_min 0.16 _exptl_crystal_density_meas not_measured _exptl_crystal_density_diffrn 1.298 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 512 _exptl_absorpt_coefficient_mu 0.092 _exptl_absorpt_correction_type Empirical _exptl_absorpt_correction_T_min 0.556 _exptl_absorpt_correction_T_max 1.000 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 153(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 13480 _diffrn_reflns_av_R_equivalents 0.0999 _diffrn_reflns_av_sigmaI/netI 0.1157 _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 -28 _diffrn_reflns_limit_l_max 27 _diffrn_reflns_theta_min 1.90 _diffrn_reflns_theta_max 28.53 _reflns_number_total 2810 _reflns_number_gt 1420 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SHELXTL' _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^)+(0.0436P)^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 none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2810 _refine_ls_number_parameters 230 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1098 _refine_ls_R_factor_gt 0.0483 _refine_ls_wR_factor_ref 0.1052 _refine_ls_wR_factor_gt 0.0886 _refine_ls_goodness_of_fit_ref 0.837 _refine_ls_restrained_S_all 0.837 _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 0.7208(3) 0.5805(3) 0.56514(10) 0.0239(5) Uani 1 1 d . . . H1A H 0.652(2) 0.497(2) 0.5383(8) 0.023(5) Uiso 1 1 d . . . H1B H 0.814(2) 0.642(2) 0.5391(8) 0.025(5) Uiso 1 1 d . . . C2 C 0.5808(3) 0.7091(3) 0.58559(10) 0.0258(5) Uani 1 1 d . . . H2A H 0.645(2) 0.806(2) 0.6084(8) 0.019(5) Uiso 1 1 d . . . H2B H 0.493(2) 0.658(3) 0.6173(9) 0.028(5) Uiso 1 1 d . . . O3 O 0.47966(17) 0.76238(17) 0.53044(6) 0.0265(4) Uani 1 1 d . . . C4 C 0.3379(3) 0.8819(3) 0.54142(10) 0.0253(5) Uani 1 1 d . . . H4A H 0.392(3) 1.002(3) 0.5538(9) 0.039(6) Uiso 1 1 d . . . H4B H 0.263(2) 0.844(2) 0.5787(8) 0.019(5) Uiso 1 1 d . . . C5 C 0.2156(3) 0.8978(3) 0.48303(10) 0.0246(5) Uani 1 1 d . . . H5A H 0.136(2) 1.009(3) 0.4853(8) 0.027(5) Uiso 1 1 d . . . H5B H 0.293(3) 0.905(2) 0.4458(9) 0.030(6) Uiso 1 1 d . . . O6 O 0.09952(17) 0.75171(17) 0.47822(6) 0.0252(4) Uani 1 1 d . . . C7 C -0.0118(3) 0.7398(3) 0.42155(10) 0.0256(5) Uani 1 1 d . . . H7B H -0.142(3) 0.774(2) 0.4285(8) 0.024(5) Uiso 1 1 d . . . H7A H 0.038(2) 0.819(2) 0.3880(9) 0.024(5) Uiso 1 1 d . . . C8 C -0.0115(3) 0.5587(3) 0.39747(10) 0.0245(5) Uani 1 1 d . . . H8A H -0.058(2) 0.484(2) 0.4291(7) 0.007(4) Uiso 1 1 d . . . H8B H -0.102(2) 0.553(2) 0.3593(8) 0.014(5) Uiso 1 1 d . . . N9 N 0.1727(2) 0.4952(2) 0.38186(7) 0.0214(4) Uani 1 1 d . . . C10 C 0.2709(3) 0.6028(2) 0.34187(9) 0.0201(5) Uani 1 1 d . . . C11 C 0.4441(3) 0.6718(3) 0.35941(10) 0.0237(5) Uani 1 1 d . . . H11 H 0.501(2) 0.649(2) 0.4009(8) 0.020(5) Uiso 1 1 d . . . C12 C 0.5396(3) 0.7735(3) 0.31864(10) 0.0287(5) Uani 1 1 d . . . H12 H 0.667(3) 0.820(3) 0.3312(9) 0.037(6) Uiso 1 1 d . . . C13 C 0.4623(3) 0.8117(3) 0.26092(11) 0.0303(6) Uani 1 1 d . . . H13 H 0.526(2) 0.882(3) 0.2320(9) 0.031(6) Uiso 1 1 d . . . C14 C 0.2908(3) 0.7455(3) 0.24211(10) 0.0251(5) Uani 1 1 d . . . H14 H 0.231(2) 0.774(2) 0.2019(9) 0.027(6) Uiso 1 1 d . . . C15 C 0.1958(3) 0.6417(2) 0.28160(9) 0.0223(5) Uani 1 1 d . . . O16 O 0.02797(18) 0.56894(18) 0.26521(6) 0.0291(4) Uani 1 1 d . . . C17 C -0.0621(4) 0.6191(3) 0.20708(11) 0.0347(6) Uani 1 1 d . . . H17A H -0.078(3) 0.749(3) 0.2035(9) 0.049(7) Uiso 1 1 d . . . H17B H 0.015(3) 0.585(3) 0.1720(9) 0.035(6) Uiso 1 1 d . . . H17C H -0.186(3) 0.558(3) 0.2065(9) 0.039(6) Uiso 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 0.0271(11) 0.0226(12) 0.0215(12) 0.0038(10) -0.0021(10) 0.0009(10) C2 0.0312(12) 0.0231(12) 0.0224(12) 0.0005(10) -0.0050(10) 0.0052(10) O3 0.0281(8) 0.0262(8) 0.0246(8) 0.0007(6) -0.0049(6) 0.0095(7) C4 0.0216(11) 0.0224(13) 0.0318(14) -0.0024(10) 0.0008(10) 0.0044(10) C5 0.0213(10) 0.0192(12) 0.0330(14) 0.0017(10) -0.0003(10) 0.0014(10) O6 0.0262(8) 0.0239(8) 0.0249(8) 0.0018(7) -0.0048(6) -0.0039(7) C7 0.0223(11) 0.0294(13) 0.0245(12) 0.0016(10) -0.0040(10) 0.0061(10) C8 0.0234(11) 0.0266(12) 0.0234(13) 0.0012(10) -0.0010(10) -0.0007(10) N9 0.0215(9) 0.0217(9) 0.0206(9) 0.0036(8) -0.0017(7) 0.0046(8) C10 0.0222(10) 0.0177(11) 0.0203(12) -0.0004(9) 0.0005(9) 0.0041(9) C11 0.0266(11) 0.0244(12) 0.0195(12) -0.0014(10) -0.0021(10) 0.0018(10) C12 0.0249(11) 0.0287(13) 0.0323(14) -0.0010(11) -0.0019(10) -0.0009(11) C13 0.0336(13) 0.0278(13) 0.0298(14) 0.0063(11) 0.0042(11) -0.0027(10) C14 0.0297(11) 0.0230(12) 0.0224(12) 0.0036(10) -0.0010(10) 0.0009(10) C15 0.0218(10) 0.0200(11) 0.0244(12) -0.0015(9) -0.0037(9) 0.0028(9) O16 0.0306(8) 0.0292(9) 0.0263(9) 0.0063(7) -0.0108(7) -0.0065(7) C17 0.0409(15) 0.0331(15) 0.0286(15) 0.0091(11) -0.0127(12) -0.0039(12) _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 C1 N9 1.465(2) 3_666 ? C1 C2 1.509(3) . ? C2 O3 1.420(2) . ? O3 C4 1.417(2) . ? C4 C5 1.499(3) . ? C5 O6 1.421(2) . ? O6 C7 1.425(2) . ? C7 C8 1.513(3) . ? C8 N9 1.475(2) . ? N9 C10 1.420(2) . ? N9 C1 1.465(2) 3_666 ? C10 C11 1.396(3) . ? C10 C15 1.409(3) . ? C11 C12 1.393(3) . ? C12 C13 1.365(3) . ? C13 C14 1.383(3) . ? C14 C15 1.382(3) . ? C15 O16 1.369(2) . ? O16 C17 1.431(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 N9 C1 C2 112.23(17) 3_666 . ? O3 C2 C1 106.12(16) . . ? C4 O3 C2 113.62(15) . . ? O3 C4 C5 108.36(17) . . ? O6 C5 C4 108.18(17) . . ? C5 O6 C7 114.77(15) . . ? O6 C7 C8 110.00(16) . . ? N9 C8 C7 114.40(17) . . ? C10 N9 C1 116.86(16) . 3_666 ? C10 N9 C8 114.87(16) . . ? C1 N9 C8 113.83(16) 3_666 . ? C11 C10 C15 117.30(18) . . ? C11 C10 N9 122.46(17) . . ? C15 C10 N9 120.24(17) . . ? C12 C11 C10 121.3(2) . . ? C13 C12 C11 120.2(2) . . ? C12 C13 C14 119.9(2) . . ? C15 C14 C13 120.5(2) . . ? O16 C15 C14 123.31(18) . . ? O16 C15 C10 115.94(17) . . ? C14 C15 C10 120.74(18) . . ? C15 O16 C17 117.68(17) . . ? _diffrn_measured_fraction_theta_max 0.910 _diffrn_reflns_theta_full 28.53 _diffrn_measured_fraction_theta_full 0.910 _refine_diff_density_max 0.262 _refine_diff_density_min -0.234 _refine_diff_density_rms 0.052 #===END data_2k _database_code_CSD 186702 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C26 H38 F6 K N2 O6 P' _chemical_formula_weight 658.65 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' 'P' 'P' 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'K' 'K' 0.2009 0.2494 '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 11.908(3) _cell_length_b 12.219(3) _cell_length_c 12.268(3) _cell_angle_alpha 86.206(3) _cell_angle_beta 70.910(3) _cell_angle_gamma 64.190(3) _cell_volume 1512.5(6) _cell_formula_units_Z 2 _cell_measurement_temperature 153(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.28 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.16 _exptl_crystal_density_meas not_measured _exptl_crystal_density_diffrn 1.446 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 688 _exptl_absorpt_coefficient_mu 0.308 _exptl_absorpt_correction_type Empirical _exptl_absorpt_correction_T_min 0.794 _exptl_absorpt_correction_T_max 1.000 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 153(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 17315 _diffrn_reflns_av_R_equivalents 0.0565 _diffrn_reflns_av_sigmaI/netI 0.1000 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 1.76 _diffrn_reflns_theta_max 28.60 _reflns_number_total 6681 _reflns_number_gt 3364 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SHELXTL' _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^)+(0.0981P)^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 none _refine_ls_extinction_coef ? _refine_ls_number_reflns 6681 _refine_ls_number_parameters 429 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1238 _refine_ls_R_factor_gt 0.0593 _refine_ls_wR_factor_ref 0.1924 _refine_ls_wR_factor_gt 0.1488 _refine_ls_goodness_of_fit_ref 0.921 _refine_ls_restrained_S_all 0.921 _refine_ls_shift/su_max 0.198 _refine_ls_shift/su_mean 0.005 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 K1A K -0.5000 0.5000 1.0000 0.0581(4) Uani 1 2 d S . . C1A C -0.7234(13) 0.3651(12) 1.1223(12) 0.036(3) Uani 0.50 1 d P . 1 H1A1 H -0.7672 0.3166 1.1690 0.044 Uiso 0.50 1 calc PR . 1 H1A2 H -0.6997 0.3417 1.0393 0.044 Uiso 0.50 1 calc PR . 1 C2A C -0.8161(7) 0.5039(7) 1.1519(7) 0.0289(16) Uani 0.50 1 d P A 1 H2AA H -0.9086 0.5225 1.1614 0.035 Uiso 0.50 1 calc PR A 1 H2AB H -0.8132 0.5354 1.2228 0.035 Uiso 0.50 1 calc PR A 1 C1' C -0.7576(13) 0.4059(13) 1.1683(12) 0.045(3) Uani 0.50 1 d P . 2 H1'1 H -0.7952 0.3474 1.1976 0.054 Uiso 0.50 1 calc PR . 2 H1'2 H -0.8033 0.4775 1.2261 0.054 Uiso 0.50 1 calc PR . 2 C2' C -0.7765(10) 0.4434(10) 1.0603(10) 0.063(3) Uani 0.50 1 d P A 2 H2'A H -0.8674 0.4624 1.0637 0.076 Uiso 0.50 1 calc PR A 2 H2'B H -0.7127 0.3788 0.9968 0.076 Uiso 0.50 1 calc PR A 2 O3A O -0.7533(3) 0.5550(3) 1.0425(3) 0.0751(11) Uani 1 1 d . A . C4A C -0.8391(4) 0.6774(5) 1.0751(4) 0.0662(15) Uani 1 1 d . A . H4AA H -0.8434 0.6999 1.1529 0.079 Uiso 1 1 calc R . . H4AB H -0.9291 0.6925 1.0787 0.079 Uiso 1 1 calc R . . C5A C -0.7922(4) 0.7522(4) 0.9901(3) 0.0453(10) Uani 1 1 d . . . H5AA H -0.7796 0.7244 0.9112 0.054 Uiso 1 1 calc R B . H5AB H -0.8586 0.8387 1.0073 0.054 Uiso 1 1 calc R . . O6A O -0.6709(3) 0.7408(2) 0.9961(2) 0.0415(7) Uani 1 1 d . B . C7A C -0.6220(4) 0.8150(4) 0.9189(4) 0.0488(11) Uani 1 1 d . . . H7AA H -0.6765 0.9020 0.9485 0.059 Uiso 1 1 calc R B . H7AB H -0.6272 0.8046 0.8416 0.059 Uiso 1 1 calc R . . C8A C -0.4826(5) 0.7784(4) 0.9094(4) 0.0591(13) Uani 1 1 d . B . H8AA H -0.4534 0.8379 0.8663 0.071 Uiso 1 1 calc R . . H8AB H -0.4772 0.7804 0.9880 0.071 Uiso 1 1 calc R . . N9A N -0.3934(3) 0.6557(3) 0.8502(3) 0.0518(10) Uani 1 1 d . . . C10A C -0.3903(4) 0.6463(4) 0.7319(4) 0.0488(11) Uani 1 1 d . . . C11A C -0.3706(5) 0.7273(5) 0.6544(5) 0.0746(15) Uani 1 1 d . B . H11A H -0.3574 0.7919 0.6784 0.089 Uiso 1 1 calc R . . C12A C -0.3692(6) 0.7178(6) 0.5416(5) 0.0857(18) Uani 1 1 d . . . H12A H -0.3529 0.7743 0.4893 0.103 Uiso 1 1 calc R B . C13A C -0.3906(5) 0.6302(5) 0.5068(5) 0.0708(15) Uani 1 1 d . B . H13A H -0.3907 0.6240 0.4301 0.085 Uiso 1 1 calc R . . C14A C -0.4126(5) 0.5482(6) 0.5837(5) 0.0790(16) Uani 1 1 d . . . H14A H -0.4274 0.4850 0.5593 0.095 Uiso 1 1 calc R B . C15A C -0.4132(5) 0.5569(5) 0.6955(5) 0.0650(14) Uani 1 1 d . B . O16A O -0.4628(10) 0.4951(12) 0.7851(12) 0.065(4) Uani 0.50 1 d P B 1 C17A C -0.5150(11) 0.4179(10) 0.7553(9) 0.069(3) Uiso 0.50 1 d P B 1 H17A H -0.6001 0.4692 0.7445 0.103 Uiso 0.50 1 calc PR B 1 H17B H -0.5274 0.3657 0.8178 0.103 Uiso 0.50 1 calc PR B 1 H17C H -0.4526 0.3668 0.6834 0.103 Uiso 0.50 1 calc PR B 1 O16' O -0.3936(14) 0.4569(13) 0.7572(13) 0.099(5) Uani 0.50 1 d P B 2 C17' C -0.4145(19) 0.3579(17) 0.7249(16) 0.152(7) Uiso 0.50 1 d P B 2 H17D H -0.4843 0.3897 0.6897 0.228 Uiso 0.50 1 calc PR B 2 H17E H -0.4410 0.3179 0.7940 0.228 Uiso 0.50 1 calc PR B 2 H17F H -0.3324 0.2986 0.6691 0.228 Uiso 0.50 1 calc PR B 2 K1B K 0.0000 0.0000 0.5000 0.0372(3) Uani 1 2 d S . . C1B C -0.0144(6) -0.0317(4) 0.7895(4) 0.0658(15) Uani 1 1 d . . . H1B1 H -0.0343 -0.0512 0.8712 0.079 Uiso 1 1 calc R . . H1B2 H -0.0573 0.0582 0.7892 0.079 Uiso 1 1 calc R . . C2B C 0.1332(5) -0.0775(4) 0.7343(4) 0.0579(13) Uani 1 1 d . . . H2BA H 0.1674 -0.0451 0.7813 0.070 Uiso 1 1 calc R . . H2BB H 0.1773 -0.1678 0.7301 0.070 Uiso 1 1 calc R . . O3B O 0.1602(3) -0.0378(2) 0.6204(2) 0.0456(7) Uani 1 1 d . . . C4B C 0.2998(5) -0.0888(4) 0.5571(4) 0.0611(13) Uani 1 1 d . . . H4BA H 0.3363 -0.1786 0.5445 0.073 Uiso 1 1 calc R . . H4BB H 0.3459 -0.0701 0.6020 0.073 Uiso 1 1 calc R . . C5B C 0.3211(5) -0.0363(5) 0.4446(5) 0.0804(18) Uani 1 1 d . C . H5BA H 0.2796 0.0539 0.4569 0.096 Uiso 1 1 calc R . . H5BB H 0.4169 -0.0652 0.4031 0.096 Uiso 1 1 calc R . . O6B O 0.2642(3) -0.0730(4) 0.3782(3) 0.0929(14) Uani 1 1 d . . . C7B C 0.2816(8) 0.0219(9) 0.2852(7) 0.046(2) Uani 0.50 1 d P C 1 H7BA H 0.2433 0.1053 0.3228 0.055 Uiso 0.50 1 calc PR C 1 H7BB H 0.3758 -0.0035 0.2389 0.055 Uiso 0.50 1 calc PR C 1 C8B C 0.2053(16) 0.0143(16) 0.2127(14) 0.043(3) Uani 0.50 1 d P C 1 H8BA H 0.2331 0.0448 0.1365 0.051 Uiso 0.50 1 calc PR C 1 H8BB H 0.2235 -0.0717 0.1995 0.051 Uiso 0.50 1 calc PR C 1 C7# C 0.3022(8) -0.0845(7) 0.2498(7) 0.0423(19) Uani 0.50 1 d P C 2 H7#A H 0.2735 -0.1399 0.2236 0.051 Uiso 0.50 1 calc PR C 2 H7#B H 0.3989 -0.1146 0.2124 0.051 Uiso 0.50 1 calc PR C 2 C8# C 0.2293(17) 0.0436(15) 0.2251(17) 0.041(3) Uani 0.50 1 d P C 2 H8#A H 0.2608 0.0506 0.1408 0.050 Uiso 0.50 1 calc PR C 2 H8#B H 0.2474 0.0990 0.2648 0.050 Uiso 0.50 1 calc PR C 2 N9B N 0.0707(3) 0.0843(3) 0.2692(3) 0.0434(9) Uani 1 1 d . . . C10B C 0.0151(3) 0.2154(3) 0.2728(3) 0.0345(9) Uani 1 1 d . C . C11B C -0.0117(4) 0.2790(4) 0.1794(3) 0.0419(10) Uani 1 1 d . . . H11B H 0.0111 0.2347 0.1085 0.050 Uiso 1 1 calc R C . C12B C -0.0705(4) 0.4045(4) 0.1868(4) 0.0483(11) Uani 1 1 d . C . H12B H -0.0901 0.4461 0.1224 0.058 Uiso 1 1 calc R . . C13B C -0.1005(4) 0.4689(4) 0.2875(4) 0.0477(11) Uani 1 1 d . . . H13B H -0.1410 0.5556 0.2929 0.057 Uiso 1 1 calc R C . C14B C -0.0723(4) 0.4085(4) 0.3818(4) 0.0501(11) Uani 1 1 d . C . H14B H -0.0925 0.4538 0.4512 0.060 Uiso 1 1 calc R . . C15B C -0.0149(4) 0.2826(4) 0.3749(3) 0.0421(10) Uani 1 1 d . . . O16B O 0.0164(3) 0.2159(2) 0.4645(2) 0.0592(9) Uani 1 1 d . C . C17B C -0.0028(7) 0.2830(4) 0.5662(4) 0.089(2) Uani 1 1 d . . . H17G H 0.0449 0.3336 0.5441 0.134 Uiso 1 1 calc R C . H17H H 0.0310 0.2258 0.6203 0.134 Uiso 1 1 calc R . . H17I H -0.0973 0.3354 0.6034 0.134 Uiso 1 1 calc R . . P1 P -0.73270(10) 1.17357(9) 0.82810(8) 0.0330(3) Uani 1 1 d . . . F11 F -0.6380(2) 1.2335(2) 0.7576(2) 0.0644(7) Uani 1 1 d . . . F12 F -0.6634(2) 1.1420(2) 0.9239(2) 0.0606(7) Uani 1 1 d . . . F13 F -0.8015(3) 1.2035(2) 0.7317(2) 0.0620(7) Uani 1 1 d . . . F14 F -0.8375(2) 1.30315(19) 0.8961(2) 0.0540(7) Uani 1 1 d . . . F15 F -0.6277(2) 1.04386(19) 0.7595(2) 0.0521(6) Uani 1 1 d . . . F16 F -0.8276(2) 1.11398(19) 0.8981(2) 0.0480(6) 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 K1A 0.0283(7) 0.0392(8) 0.1009(12) 0.0376(8) -0.0176(7) -0.0166(6) C1A 0.031(7) 0.033(7) 0.049(8) 0.004(5) -0.011(6) -0.019(6) C2A 0.026(4) 0.039(5) 0.032(4) 0.004(4) -0.012(3) -0.022(4) C1' 0.030(7) 0.047(10) 0.066(10) 0.027(6) -0.023(7) -0.023(7) C2' 0.054(6) 0.080(7) 0.087(8) 0.033(7) -0.040(6) -0.047(6) O3A 0.0458(18) 0.060(2) 0.145(3) 0.064(2) -0.055(2) -0.0367(17) C4A 0.037(2) 0.109(4) 0.046(3) 0.029(3) -0.016(2) -0.027(3) C5A 0.042(2) 0.036(2) 0.041(2) 0.0035(19) -0.019(2) 0.0006(19) O6A 0.0555(17) 0.0303(15) 0.0470(16) 0.0138(12) -0.0296(14) -0.0184(13) C7A 0.074(3) 0.031(2) 0.048(3) 0.0154(19) -0.030(2) -0.023(2) C8A 0.095(4) 0.052(3) 0.077(3) 0.038(3) -0.056(3) -0.058(3) N9A 0.053(2) 0.050(2) 0.082(3) 0.035(2) -0.043(2) -0.0382(19) C10A 0.033(2) 0.049(3) 0.072(3) 0.023(2) -0.024(2) -0.023(2) C11A 0.086(4) 0.065(4) 0.074(4) 0.023(3) -0.014(3) -0.045(3) C12A 0.086(4) 0.085(4) 0.063(4) 0.035(3) -0.007(3) -0.034(4) C13A 0.043(3) 0.081(4) 0.066(4) 0.005(3) -0.011(3) -0.012(3) C14A 0.089(4) 0.092(4) 0.082(4) 0.020(4) -0.044(3) -0.052(4) C15A 0.075(4) 0.067(3) 0.078(4) 0.027(3) -0.042(3) -0.044(3) O16A 0.077(7) 0.067(8) 0.062(5) -0.009(5) 0.006(5) -0.060(6) O16' 0.184(15) 0.082(10) 0.111(12) 0.048(8) -0.104(11) -0.097(11) K1B 0.0326(6) 0.0480(7) 0.0323(6) 0.0128(5) -0.0145(5) -0.0174(6) C1B 0.120(5) 0.037(3) 0.027(2) 0.0043(19) -0.033(3) -0.018(3) C2B 0.107(4) 0.048(3) 0.054(3) 0.022(2) -0.060(3) -0.044(3) O3B 0.064(2) 0.0390(16) 0.0544(18) 0.0186(13) -0.0409(16) -0.0276(15) C4B 0.060(3) 0.057(3) 0.088(4) 0.013(3) -0.051(3) -0.027(3) C5B 0.042(3) 0.093(4) 0.119(5) 0.061(4) -0.038(3) -0.039(3) O6B 0.0374(18) 0.184(4) 0.048(2) 0.046(2) -0.0186(16) -0.043(2) C7B 0.026(4) 0.061(6) 0.039(5) 0.008(4) -0.003(4) -0.015(4) C8B 0.038(8) 0.051(9) 0.026(5) 0.006(6) -0.005(5) -0.012(6) C7# 0.040(4) 0.026(4) 0.049(5) -0.002(4) -0.008(4) -0.008(4) C8# 0.032(7) 0.044(8) 0.046(8) 0.001(6) -0.006(5) -0.018(5) N9B 0.045(2) 0.039(2) 0.0255(17) 0.0033(15) -0.0095(15) -0.0015(16) C10B 0.0295(19) 0.038(2) 0.032(2) 0.0111(17) -0.0090(16) -0.0129(17) C11B 0.041(2) 0.056(3) 0.039(2) 0.018(2) -0.0155(19) -0.029(2) C12B 0.049(3) 0.052(3) 0.059(3) 0.033(2) -0.030(2) -0.030(2) C13B 0.039(2) 0.033(2) 0.061(3) 0.019(2) -0.012(2) -0.0121(19) C14B 0.052(3) 0.037(2) 0.042(2) 0.0063(19) -0.004(2) -0.012(2) C15B 0.044(2) 0.036(2) 0.030(2) 0.0098(17) -0.0080(18) -0.0072(19) O16B 0.091(2) 0.0338(16) 0.0289(15) 0.0027(12) -0.0213(16) -0.0053(16) C17B 0.157(6) 0.050(3) 0.035(3) 0.001(2) -0.037(3) -0.019(3) P1 0.0373(5) 0.0304(5) 0.0360(6) 0.0083(4) -0.0160(4) -0.0171(4) F11 0.0650(17) 0.0582(17) 0.0781(18) 0.0163(14) -0.0111(14) -0.0444(14) F12 0.0762(18) 0.0610(16) 0.0673(17) 0.0168(13) -0.0518(15) -0.0314(14) F13 0.0796(19) 0.0691(18) 0.0538(15) 0.0184(13) -0.0441(14) -0.0331(15) F14 0.0600(16) 0.0287(13) 0.0595(15) -0.0015(11) -0.0113(12) -0.0127(11) F15 0.0477(14) 0.0372(13) 0.0597(15) -0.0039(11) -0.0057(12) -0.0160(11) F16 0.0467(13) 0.0374(13) 0.0573(15) 0.0084(11) -0.0083(11) -0.0232(11) _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 K1A O16A 2.527(15) . ? K1A O16A 2.527(15) 2_467 ? K1A O3A 2.659(3) 2_467 ? K1A O3A 2.659(3) . ? K1A O6A 2.763(2) . ? K1A O6A 2.763(2) 2_467 ? K1A O16' 2.813(14) . ? K1A O16' 2.813(14) 2_467 ? K1A N9A 2.953(3) . ? K1A N9A 2.953(3) 2_467 ? K1A C17A 3.310(10) 2_467 ? K1A C4A 3.474(5) . ? C1A N9A 1.449(15) 2_467 ? C1A C2A 1.554(14) . ? C2A O3A 1.547(8) . ? C1' C2' 1.429(18) . ? C1' N9A 1.559(14) 2_467 ? C2' O3A 1.494(10) . ? O3A C4A 1.386(6) . ? C4A C5A 1.474(6) . ? C5A O6A 1.416(5) . ? O6A C7A 1.429(5) . ? C7A C8A 1.484(6) . ? C8A N9A 1.468(6) . ? N9A C1A 1.449(15) 2_467 ? N9A C10A 1.451(6) . ? N9A C1' 1.559(14) 2_467 ? C10A C15A 1.368(6) . ? C10A C11A 1.368(6) . ? C11A C12A 1.391(7) . ? C12A C13A 1.328(8) . ? C13A C14A 1.379(7) . ? C14A C15A 1.380(7) . ? C15A O16' 1.365(15) . ? C15A O16A 1.407(14) . ? O16A C17A 1.454(17) . ? O16' C17' 1.44(2) . ? K1B O3B 2.650(2) 2_556 ? K1B O3B 2.650(2) . ? K1B O16B 2.725(3) 2_556 ? K1B O16B 2.725(3) . ? K1B O6B 2.754(3) 2_556 ? K1B O6B 2.754(3) . ? K1B N9B 2.932(3) . ? K1B N9B 2.932(3) 2_556 ? K1B C5B 3.484(5) 2_556 ? K1B C5B 3.484(5) . ? K1B C1B 3.502(4) 2_556 ? K1B C1B 3.502(4) . ? C1B N9B 1.460(6) 2_556 ? C1B C2B 1.508(7) . ? C2B O3B 1.429(5) . ? O3B C4B 1.439(5) . ? C4B C5B 1.475(7) . ? C5B O6B 1.413(6) . ? O6B C7# 1.487(8) . ? O6B C7B 1.603(9) . ? C7B C8B 1.496(15) . ? C8B N9B 1.393(17) . ? C7# C8# 1.49(2) . ? C8# N9B 1.631(16) . ? N9B C10B 1.441(5) . ? N9B C1B 1.460(6) 2_556 ? C10B C11B 1.387(5) . ? C10B C15B 1.400(5) . ? C11B C12B 1.376(6) . ? C12B C13B 1.367(6) . ? C13B C14B 1.386(6) . ? C14B C15B 1.380(5) . ? C15B O16B 1.377(4) . ? O16B C17B 1.437(5) . ? P1 F12 1.584(2) . ? P1 F13 1.587(2) . ? P1 F14 1.592(2) . ? P1 F16 1.595(2) . ? P1 F15 1.596(2) . ? P1 F11 1.597(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 O16A K1A O16A 180.000(2) . 2_467 ? O16A K1A O3A 90.1(3) . 2_467 ? O16A K1A O3A 89.9(3) 2_467 2_467 ? O16A K1A O3A 89.9(3) . . ? O16A K1A O3A 90.1(3) 2_467 . ? O3A K1A O3A 180.0 2_467 . ? O16A K1A O6A 82.6(3) . . ? O16A K1A O6A 97.4(3) 2_467 . ? O3A K1A O6A 117.85(9) 2_467 . ? O3A K1A O6A 62.15(9) . . ? O16A K1A O6A 97.4(3) . 2_467 ? O16A K1A O6A 82.6(3) 2_467 2_467 ? O3A K1A O6A 62.15(9) 2_467 2_467 ? O3A K1A O6A 117.85(9) . 2_467 ? O6A K1A O6A 180.0 . 2_467 ? O16A K1A O16' 14.2(4) . . ? O16A K1A O16' 165.8(4) 2_467 . ? O3A K1A O16' 77.2(3) 2_467 . ? O3A K1A O16' 102.8(3) . . ? O6A K1A O16' 93.8(3) . . ? O6A K1A O16' 86.2(3) 2_467 . ? O16A K1A O16' 165.8(4) . 2_467 ? O16A K1A O16' 14.2(4) 2_467 2_467 ? O3A K1A O16' 102.8(3) 2_467 2_467 ? O3A K1A O16' 77.2(3) . 2_467 ? O6A K1A O16' 86.2(3) . 2_467 ? O6A K1A O16' 93.8(3) 2_467 2_467 ? O16' K1A O16' 180.000(2) . 2_467 ? O16A K1A N9A 58.1(3) . . ? O16A K1A N9A 121.9(3) 2_467 . ? O3A K1A N9A 62.55(9) 2_467 . ? O3A K1A N9A 117.45(9) . . ? O6A K1A N9A 61.59(9) . . ? O6A K1A N9A 118.41(9) 2_467 . ? O16' K1A N9A 57.0(3) . . ? O16' K1A N9A 123.0(3) 2_467 . ? O16A K1A N9A 121.9(3) . 2_467 ? O16A K1A N9A 58.1(3) 2_467 2_467 ? O3A K1A N9A 117.45(9) 2_467 2_467 ? O3A K1A N9A 62.55(9) . 2_467 ? O6A K1A N9A 118.41(9) . 2_467 ? O6A K1A N9A 61.59(9) 2_467 2_467 ? O16' K1A N9A 123.0(3) . 2_467 ? O16' K1A N9A 57.0(3) 2_467 2_467 ? N9A K1A N9A 180.00(9) . 2_467 ? O16A K1A C17A 155.5(3) . 2_467 ? O16A K1A C17A 24.5(3) 2_467 2_467 ? O3A K1A C17A 74.7(2) 2_467 2_467 ? O3A K1A C17A 105.3(2) . 2_467 ? O6A K1A C17A 87.7(2) . 2_467 ? O6A K1A C17A 92.3(2) 2_467 2_467 ? O16' K1A C17A 148.8(3) . 2_467 ? O16' K1A C17A 31.2(3) 2_467 2_467 ? N9A K1A C17A 97.6(2) . 2_467 ? N9A K1A C17A 82.4(2) 2_467 2_467 ? O16A K1A C4A 93.9(3) . . ? O16A K1A C4A 86.1(3) 2_467 . ? O3A K1A C4A 158.74(11) 2_467 . ? O3A K1A C4A 21.26(11) . . ? O6A K1A C4A 42.45(11) . . ? O6A K1A C4A 137.55(11) 2_467 . ? O16' K1A C4A 108.0(3) . . ? O16' K1A C4A 72.0(3) 2_467 . ? N9A K1A C4A 102.28(11) . . ? N9A K1A C4A 77.72(11) 2_467 . ? C17A K1A C4A 94.0(2) 2_467 . ? N9A C1A C2A 106.0(8) 2_467 . ? O3A C2A C1A 100.5(7) . . ? C2' C1' N9A 108.8(10) . 2_467 ? C1' C2' O3A 104.8(9) . . ? C1' C2' K1A 86.5(6) . . ? O3A C2' K1A 45.2(3) . . ? C4A O3A C2' 131.2(5) . . ? C4A O3A C2A 97.3(4) . . ? C2' O3A C2A 47.3(5) . . ? C4A O3A K1A 114.6(3) . . ? C2' O3A K1A 111.2(4) . . ? C2A O3A K1A 114.8(3) . . ? O3A C4A C5A 109.4(4) . . ? O3A C4A K1A 44.10(18) . . ? C5A C4A K1A 80.3(2) . . ? O6A C5A C4A 109.0(3) . . ? O6A C5A K1A 46.60(15) . . ? C4A C5A K1A 75.5(2) . . ? C5A O6A C7A 112.1(3) . . ? C5A O6A K1A 111.5(2) . . ? C7A O6A K1A 118.8(2) . . ? O6A C7A C8A 109.2(3) . . ? N9A C8A C7A 112.3(3) . . ? C1A N9A C10A 122.1(6) 2_467 . ? C1A N9A C8A 99.6(5) 2_467 . ? C10A N9A C8A 112.8(3) . . ? C1A N9A C1' 25.2(5) 2_467 2_467 ? C10A N9A C1' 100.2(6) . 2_467 ? C8A N9A C1' 122.6(6) . 2_467 ? C1A N9A K1A 104.3(7) 2_467 . ? C10A N9A K1A 112.9(2) . . ? C8A N9A K1A 102.9(2) . . ? C1' N9A K1A 105.5(6) 2_467 . ? C15A C10A C11A 117.4(5) . . ? C15A C10A N9A 120.0(4) . . ? C11A C10A N9A 122.6(4) . . ? C10A C11A C12A 121.9(5) . . ? C13A C12A C11A 120.3(5) . . ? C12A C13A C14A 119.0(6) . . ? C13A C14A C15A 120.9(6) . . ? O16' C15A C10A 117.0(7) . . ? O16' C15A C14A 119.2(8) . . ? C10A C15A C14A 120.5(5) . . ? O16' C15A O16A 29.9(7) . . ? C10A C15A O16A 114.4(7) . . ? C14A C15A O16A 123.8(7) . . ? C15A O16A C17A 116.7(12) . . ? C15A O16A K1A 133.5(8) . . ? C17A O16A K1A 109.5(8) . . ? C15A O16' C17' 120.9(13) . . ? C15A O16' K1A 117.0(8) . . ? C17' O16' K1A 107.5(11) . . ? O3B K1B O3B 180.0 2_556 . ? O3B K1B O16B 83.98(8) 2_556 2_556 ? O3B K1B O16B 96.02(8) . 2_556 ? O3B K1B O16B 96.02(8) 2_556 . ? O3B K1B O16B 83.98(8) . . ? O16B K1B O16B 180.000(19) 2_556 . ? O3B K1B O6B 62.41(10) 2_556 2_556 ? O3B K1B O6B 117.59(10) . 2_556 ? O16B K1B O6B 77.13(12) 2_556 2_556 ? O16B K1B O6B 102.87(12) . 2_556 ? O3B K1B O6B 117.59(10) 2_556 . ? O3B K1B O6B 62.41(10) . . ? O16B K1B O6B 102.87(12) 2_556 . ? O16B K1B O6B 77.13(12) . . ? O6B K1B O6B 180.0 2_556 . ? O3B K1B N9B 62.90(9) 2_556 . ? O3B K1B N9B 117.10(9) . . ? O16B K1B N9B 122.93(9) 2_556 . ? O16B K1B N9B 57.07(9) . . ? O6B K1B N9B 117.96(9) 2_556 . ? O6B K1B N9B 62.04(9) . . ? O3B K1B N9B 117.10(9) 2_556 2_556 ? O3B K1B N9B 62.90(9) . 2_556 ? O16B K1B N9B 57.07(9) 2_556 2_556 ? O16B K1B N9B 122.93(9) . 2_556 ? O6B K1B N9B 62.04(9) 2_556 2_556 ? O6B K1B N9B 117.96(9) . 2_556 ? N9B K1B N9B 180.0 . 2_556 ? O3B K1B C5B 42.94(11) 2_556 2_556 ? O3B K1B C5B 137.06(11) . 2_556 ? O16B K1B C5B 68.16(11) 2_556 2_556 ? O16B K1B C5B 111.84(11) . 2_556 ? O6B K1B C5B 22.52(12) 2_556 2_556 ? O6B K1B C5B 157.48(12) . 2_556 ? N9B K1B C5B 104.44(11) . 2_556 ? N9B K1B C5B 75.56(11) 2_556 2_556 ? O3B K1B C5B 137.06(11) 2_556 . ? O3B K1B C5B 42.94(11) . . ? O16B K1B C5B 111.84(11) 2_556 . ? O16B K1B C5B 68.16(11) . . ? O6B K1B C5B 157.48(12) 2_556 . ? O6B K1B C5B 22.52(12) . . ? N9B K1B C5B 75.56(11) . . ? N9B K1B C5B 104.44(11) 2_556 . ? C5B K1B C5B 180.0 2_556 . ? O3B K1B C1B 42.92(12) 2_556 2_556 ? O3B K1B C1B 137.08(12) . 2_556 ? O16B K1B C1B 101.78(10) 2_556 2_556 ? O16B K1B C1B 78.22(10) . 2_556 ? O6B K1B C1B 104.39(12) 2_556 2_556 ? O6B K1B C1B 75.61(12) . 2_556 ? N9B K1B C1B 24.21(11) . 2_556 ? N9B K1B C1B 155.79(11) 2_556 2_556 ? C5B K1B C1B 85.85(14) 2_556 2_556 ? C5B K1B C1B 94.15(14) . 2_556 ? O3B K1B C1B 137.09(12) 2_556 . ? O3B K1B C1B 42.92(12) . . ? O16B K1B C1B 78.22(10) 2_556 . ? O16B K1B C1B 101.78(10) . . ? O6B K1B C1B 75.61(12) 2_556 . ? O6B K1B C1B 104.39(12) . . ? N9B K1B C1B 155.79(11) . . ? N9B K1B C1B 24.21(11) 2_556 . ? C5B K1B C1B 94.15(14) 2_556 . ? C5B K1B C1B 85.85(14) . . ? C1B K1B C1B 180.0 2_556 . ? N9B C1B C2B 113.2(3) 2_556 . ? N9B C1B K1B 55.42(19) 2_556 . ? C2B C1B K1B 81.5(2) . . ? O3B C2B C1B 108.6(3) . . ? C2B O3B C4B 112.1(3) . . ? C2B O3B K1B 121.2(2) . . ? C4B O3B K1B 117.1(2) . . ? O3B C4B C5B 109.2(3) . . ? O6B C5B C4B 108.8(4) . . ? O6B C5B K1B 48.3(2) . . ? C4B C5B K1B 80.2(2) . . ? C5B O6B C7# 127.3(5) . . ? C5B O6B C7B 91.4(5) . . ? C7# O6B C7B 49.2(4) . . ? C5B O6B K1B 109.2(3) . . ? C7# O6B K1B 116.1(4) . . ? C7B O6B K1B 110.0(3) . . ? C8B C7B O6B 101.3(8) . . ? N9B C8B C7B 109.4(11) . . ? O6B C7# C8# 102.2(9) . . ? C7# C8# N9B 110.7(10) . . ? C8B N9B C10B 119.9(7) . . ? C8B N9B C1B 100.8(6) . 2_556 ? C10B N9B C1B 113.3(3) . 2_556 ? C8B N9B C8# 21.0(7) . . ? C10B N9B C8# 102.9(6) . . ? C1B N9B C8# 120.9(6) 2_556 . ? C8B N9B K1B 108.2(8) . . ? C10B N9B K1B 112.1(2) . . ? C1B N9B K1B 100.4(2) 2_556 . ? C8# N9B K1B 107.5(7) . . ? C11B C10B C15B 118.1(4) . . ? C11B C10B N9B 122.8(3) . . ? C15B C10B N9B 119.1(3) . . ? C12B C11B C10B 121.7(4) . . ? C13B C12B C11B 119.6(4) . . ? C12B C13B C14B 120.4(4) . . ? C15B C14B C13B 120.1(4) . . ? O16B C15B C14B 123.7(4) . . ? O16B C15B C10B 116.2(3) . . ? C14B C15B C10B 120.1(4) . . ? C15B O16B C17B 116.8(3) . . ? C15B O16B K1B 121.6(2) . . ? C17B O16B K1B 115.6(3) . . ? F12 P1 F13 179.28(14) . . ? F12 P1 F14 90.82(14) . . ? F13 P1 F14 89.84(14) . . ? F12 P1 F16 89.89(14) . . ? F13 P1 F16 89.81(14) . . ? F14 P1 F16 90.42(13) . . ? F12 P1 F15 89.40(14) . . ? F13 P1 F15 89.94(14) . . ? F14 P1 F15 179.77(15) . . ? F16 P1 F15 89.66(12) . . ? F12 P1 F11 90.38(15) . . ? F13 P1 F11 89.93(15) . . ? F14 P1 F11 89.55(14) . . ? F16 P1 F11 179.73(15) . . ? F15 P1 F11 90.37(14) . . ? _diffrn_measured_fraction_theta_max 0.864 _diffrn_reflns_theta_full 28.60 _diffrn_measured_fraction_theta_full 0.864 _refine_diff_density_max 0.713 _refine_diff_density_min -0.351 _refine_diff_density_rms 0.075 #===END data_11 _database_code_CSD 186703 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C26 H36 N4 O10' _chemical_formula_weight 564.59 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 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.4201(17) _cell_length_b 8.1588(19) _cell_length_c 11.055(3) _cell_angle_alpha 99.130(3) _cell_angle_beta 100.381(3) _cell_angle_gamma 93.595(3) _cell_volume 647.1(3) _cell_formula_units_Z 1 _cell_measurement_temperature 153(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_max 0.66 _exptl_crystal_size_mid 0.60 _exptl_crystal_size_min 0.42 _exptl_crystal_density_meas not_measured _exptl_crystal_density_diffrn 1.449 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 300 _exptl_absorpt_coefficient_mu 0.112 _exptl_absorpt_correction_type Empirical _exptl_absorpt_correction_T_min 0.760 _exptl_absorpt_correction_T_max 1.000 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 153(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 7478 _diffrn_reflns_av_R_equivalents 0.0330 _diffrn_reflns_av_sigmaI/netI 0.0390 _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 -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 1.90 _diffrn_reflns_theta_max 28.57 _reflns_number_total 2884 _reflns_number_gt 2232 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SHELXTL' _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^)+(0.0821P)^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 none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2884 _refine_ls_number_parameters 253 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0595 _refine_ls_R_factor_gt 0.0460 _refine_ls_wR_factor_ref 0.1317 _refine_ls_wR_factor_gt 0.1181 _refine_ls_goodness_of_fit_ref 1.027 _refine_ls_restrained_S_all 1.027 _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 -0.2726(2) -0.38498(19) -0.17160(15) 0.0206(3) Uani 1 1 d . . . H1A H -0.232(2) -0.444(2) -0.0983(16) 0.024(4) Uiso 1 1 d . . . H1B H -0.361(2) -0.463(2) -0.2286(16) 0.021(4) Uiso 1 1 d . . . C2 C -0.3627(2) -0.2334(2) -0.12392(15) 0.0222(4) Uani 1 1 d . . . H2A H -0.282(2) -0.159(2) -0.0573(16) 0.023(4) Uiso 1 1 d . . . H2B H -0.474(2) -0.275(2) -0.0929(17) 0.029(5) Uiso 1 1 d . . . O3 O -0.42003(15) -0.15015(13) -0.22633(10) 0.0254(3) Uani 1 1 d . . . C4 C -0.4887(2) 0.0065(2) -0.19193(16) 0.0238(4) Uani 1 1 d . . . H4A H -0.565(2) -0.003(2) -0.1277(17) 0.024(4) Uiso 1 1 d . . . H4B H -0.566(2) 0.028(2) -0.2632(16) 0.023(4) Uiso 1 1 d . . . C5 C -0.3412(2) 0.1486(2) -0.14488(15) 0.0254(4) Uani 1 1 d . . . H5A H -0.257(2) 0.151(2) -0.1976(15) 0.021(4) Uiso 1 1 d . . . H5B H -0.401(2) 0.258(2) -0.1384(15) 0.028(5) Uiso 1 1 d . . . O6 O -0.24819(15) 0.13322(13) -0.02424(10) 0.0240(3) Uani 1 1 d . . . C7 C -0.1002(2) 0.2577(2) 0.02707(15) 0.0220(3) Uani 1 1 d . . . H7A H -0.008(2) 0.252(2) -0.0313(16) 0.021(4) Uiso 1 1 d . . . H7B H -0.144(2) 0.369(2) 0.0366(16) 0.025(4) Uiso 1 1 d . . . C8 C -0.0230(2) 0.21693(19) 0.15438(15) 0.0216(3) Uani 1 1 d . . . H8A H 0.025(2) 0.105(2) 0.1395(15) 0.022(4) Uiso 1 1 d . . . H8B H -0.122(2) 0.211(2) 0.1981(15) 0.021(4) Uiso 1 1 d . . . N9 N 0.11493(17) 0.34590(15) 0.22996(12) 0.0194(3) Uani 1 1 d . . . C10 C 0.1509(2) 0.34511(18) 0.35755(14) 0.0189(3) Uani 1 1 d . . . C11 C 0.0958(2) 0.2065(2) 0.40682(16) 0.0227(4) Uani 1 1 d . . . H11 H 0.042(2) 0.105(2) 0.3442(17) 0.030(5) Uiso 1 1 d . . . C12 C 0.1196(2) 0.2083(2) 0.53353(15) 0.0232(4) Uani 1 1 d . . . H12 H 0.089(3) 0.113(2) 0.5671(18) 0.032(5) Uiso 1 1 d . . . C13 C 0.2010(2) 0.34969(19) 0.61391(14) 0.0206(3) Uani 1 1 d . . . C14 C 0.2611(2) 0.49098(19) 0.57123(15) 0.0199(3) Uani 1 1 d . . . H14 H 0.315(2) 0.584(2) 0.6295(17) 0.027(5) Uiso 1 1 d . . . C15 C 0.2345(2) 0.48988(18) 0.44427(14) 0.0184(3) Uani 1 1 d . . . O16 O 0.27808(15) 0.62565(13) 0.39366(10) 0.0226(3) Uani 1 1 d . . . C17 C 0.3615(2) 0.7731(2) 0.47796(16) 0.0241(4) Uani 1 1 d . . . H17A H 0.280(2) 0.810(2) 0.5360(16) 0.027(5) Uiso 1 1 d . . . H17B H 0.374(2) 0.857(2) 0.4271(17) 0.027(5) Uiso 1 1 d . . . H17C H 0.484(3) 0.756(2) 0.5294(18) 0.037(5) Uiso 1 1 d . . . N18 N 0.22403(18) 0.35068(17) 0.74732(13) 0.0237(3) Uani 1 1 d . . . O19 O 0.15584(18) 0.23022(15) 0.78320(11) 0.0340(3) Uani 1 1 d . . . O20 O 0.31268(17) 0.47082(15) 0.81951(11) 0.0320(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 0.0224(8) 0.0176(8) 0.0209(8) 0.0027(6) 0.0043(6) -0.0034(6) C2 0.0249(8) 0.0221(8) 0.0190(8) 0.0022(7) 0.0045(7) 0.0007(7) O3 0.0315(7) 0.0239(6) 0.0194(6) 0.0004(5) 0.0033(5) 0.0062(5) C4 0.0230(8) 0.0242(8) 0.0212(9) 0.0007(7) -0.0011(7) 0.0040(6) C5 0.0274(9) 0.0260(9) 0.0212(9) 0.0051(7) 0.0002(7) 0.0014(7) O6 0.0257(6) 0.0226(6) 0.0201(6) 0.0026(5) -0.0016(5) -0.0053(5) C7 0.0229(8) 0.0210(8) 0.0197(8) 0.0009(6) 0.0016(7) -0.0024(6) C8 0.0220(8) 0.0200(8) 0.0210(8) 0.0017(6) 0.0027(7) -0.0038(6) N9 0.0201(6) 0.0183(6) 0.0186(7) 0.0018(5) 0.0033(5) -0.0023(5) C10 0.0164(7) 0.0199(8) 0.0198(8) 0.0024(6) 0.0029(6) 0.0016(6) C11 0.0245(8) 0.0189(8) 0.0228(8) 0.0012(6) 0.0036(7) -0.0033(6) C12 0.0240(8) 0.0204(8) 0.0260(9) 0.0061(7) 0.0061(7) -0.0019(6) C13 0.0190(8) 0.0257(8) 0.0177(8) 0.0041(6) 0.0045(6) 0.0038(6) C14 0.0171(7) 0.0192(8) 0.0213(8) -0.0004(6) 0.0021(6) 0.0010(6) C15 0.0169(7) 0.0170(7) 0.0215(8) 0.0032(6) 0.0046(6) 0.0008(6) O16 0.0306(6) 0.0157(5) 0.0193(6) 0.0017(4) 0.0022(5) -0.0031(4) C17 0.0299(9) 0.0178(8) 0.0223(9) -0.0004(7) 0.0038(7) -0.0035(7) N18 0.0222(7) 0.0276(7) 0.0229(7) 0.0050(6) 0.0068(6) 0.0052(6) O19 0.0452(8) 0.0337(7) 0.0264(7) 0.0115(5) 0.0117(6) -0.0009(6) O20 0.0344(7) 0.0369(7) 0.0204(6) -0.0020(5) 0.0027(5) -0.0043(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 C1 N9 1.476(2) 2 ? C1 C2 1.509(2) . ? C2 O3 1.4251(19) . ? O3 C4 1.4265(19) . ? C4 C5 1.502(2) . ? C5 O6 1.4152(19) . ? O6 C7 1.4185(18) . ? C7 C8 1.517(2) . ? C8 N9 1.4598(19) . ? N9 C10 1.3886(19) . ? N9 C1 1.476(2) 2 ? C10 C11 1.400(2) . ? C10 C15 1.426(2) . ? C11 C12 1.377(2) . ? C12 C13 1.370(2) . ? C13 C14 1.391(2) . ? C13 N18 1.452(2) . ? C14 C15 1.380(2) . ? C15 O16 1.3643(17) . ? O16 C17 1.4288(19) . ? N18 O20 1.2297(17) . ? N18 O19 1.2300(17) . ? 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 N9 C1 C2 113.66(12) 2 . ? O3 C2 C1 107.84(13) . . ? C2 O3 C4 113.91(12) . . ? O3 C4 C5 113.91(14) . . ? O6 C5 C4 109.20(13) . . ? C5 O6 C7 113.90(11) . . ? O6 C7 C8 104.57(12) . . ? N9 C8 C7 112.82(12) . . ? C10 N9 C8 116.13(12) . . ? C10 N9 C1 117.40(12) . 2 ? C8 N9 C1 114.84(12) . 2 ? N9 C10 C11 121.53(14) . . ? N9 C10 C15 121.12(13) . . ? C11 C10 C15 117.22(14) . . ? C12 C11 C10 122.04(15) . . ? C13 C12 C11 119.02(14) . . ? C12 C13 C14 121.90(14) . . ? C12 C13 N18 118.56(13) . . ? C14 C13 N18 119.54(14) . . ? C15 C14 C13 119.00(15) . . ? O16 C15 C14 123.27(14) . . ? O16 C15 C10 115.86(13) . . ? C14 C15 C10 120.81(14) . . ? C15 O16 C17 117.33(12) . . ? O20 N18 O19 122.81(13) . . ? O20 N18 C13 118.66(13) . . ? O19 N18 C13 118.52(13) . . ? _diffrn_measured_fraction_theta_max 0.876 _diffrn_reflns_theta_full 28.57 _diffrn_measured_fraction_theta_full 0.876 _refine_diff_density_max 0.284 _refine_diff_density_min -0.315 _refine_diff_density_rms 0.064 #===END data_13 _database_code_CSD 186704 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C17 H26 N2 O7' _chemical_formula_weight 370.40 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 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.696(3) _cell_length_b 8.943(4) _cell_length_c 12.098(5) _cell_angle_alpha 83.932(6) _cell_angle_beta 71.217(6) _cell_angle_gamma 76.937(6) _cell_volume 867.1(6) _cell_formula_units_Z 2 _cell_measurement_temperature 153(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description plate _exptl_crystal_colour yellow _exptl_crystal_size_max 0.52 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas not_measured _exptl_crystal_density_diffrn 1.419 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 396 _exptl_absorpt_coefficient_mu 0.110 _exptl_absorpt_correction_type Empirical _exptl_absorpt_correction_T_min 0.747 _exptl_absorpt_correction_T_max 1.000 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 153(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 6975 _diffrn_reflns_av_R_equivalents 0.0565 _diffrn_reflns_av_sigmaI/netI 0.1665 _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 -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 1.78 _diffrn_reflns_theta_max 28.67 _reflns_number_total 3838 _reflns_number_gt 1474 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SHELXTL' _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^)+(0.0898P)^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 none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3838 _refine_ls_number_parameters 339 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1572 _refine_ls_R_factor_gt 0.0640 _refine_ls_wR_factor_ref 0.1939 _refine_ls_wR_factor_gt 0.1458 _refine_ls_goodness_of_fit_ref 0.814 _refine_ls_restrained_S_all 0.814 _refine_ls_shift/su_max 0.008 _refine_ls_shift/su_mean 0.001 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 -0.3049(5) 0.4305(5) 0.3536(4) 0.0279(10) Uani 1 1 d . . . H1A H -0.420(5) 0.387(4) 0.382(3) 0.046(12) Uiso 1 1 d . . . H1B H -0.332(4) 0.523(4) 0.333(3) 0.023(11) Uiso 1 1 d . . . C2 C -0.2644(5) 0.4320(5) 0.4653(4) 0.0296(10) Uani 1 1 d . . . H2A H -0.316(4) 0.531(4) 0.504(3) 0.030(11) Uiso 1 1 d . . . H2B H -0.143(5) 0.424(4) 0.451(3) 0.030(11) Uiso 1 1 d . . . O3 O -0.3251(3) 0.3121(3) 0.5423(2) 0.0289(7) Uani 1 1 d . . . C4 C -0.2901(6) 0.3067(5) 0.6493(4) 0.0283(10) Uani 1 1 d . . . H4A H -0.322(5) 0.408(5) 0.671(4) 0.048(14) Uiso 1 1 d . . . H4B H -0.161(6) 0.276(5) 0.625(4) 0.053(14) Uiso 1 1 d . . . C5 C -0.3820(6) 0.2002(5) 0.7331(4) 0.0308(10) Uani 1 1 d . . . H5A H -0.505(5) 0.225(4) 0.728(3) 0.038(12) Uiso 1 1 d . . . H5B H -0.372(5) 0.202(4) 0.800(3) 0.025(11) Uiso 1 1 d . . . O6 O -0.3128(3) 0.0477(3) 0.6962(2) 0.0307(7) Uani 1 1 d . . . C7 C -0.4012(6) -0.0603(5) 0.7672(4) 0.0311(11) Uani 1 1 d . . . H7A H -0.402(5) -0.059(5) 0.837(3) 0.039(13) Uiso 1 1 d . . . H7B H -0.527(5) -0.020(4) 0.758(3) 0.024(10) Uiso 1 1 d . . . C8 C -0.3272(6) -0.2159(5) 0.7171(4) 0.0311(11) Uani 1 1 d . . . H8A H -0.195(5) -0.241(4) 0.699(3) 0.036(11) Uiso 1 1 d . . . H8B H -0.383(6) -0.284(5) 0.751(4) 0.062(16) Uiso 1 1 d . . . O9 O -0.3493(3) -0.2219(3) 0.6064(2) 0.0306(7) Uani 1 1 d . . . C10 C -0.2145(5) -0.1872(5) 0.5116(4) 0.0300(10) Uani 1 1 d . . . H10A H -0.164(4) -0.118(4) 0.536(3) 0.012(9) Uiso 1 1 d . . . H10B H -0.150(5) -0.280(5) 0.484(4) 0.049(14) Uiso 1 1 d . . . C11 C -0.2806(5) -0.1129(5) 0.4160(4) 0.0323(11) Uani 1 1 d . . . H11A H -0.345(5) -0.175(5) 0.403(4) 0.050(14) Uiso 1 1 d . . . H11B H -0.363(5) -0.009(5) 0.444(3) 0.049(13) Uiso 1 1 d . . . O12 O -0.1484(3) -0.0860(3) 0.3153(2) 0.0334(7) Uani 1 1 d . . . C13 C -0.1058(6) 0.0594(5) 0.3166(4) 0.0281(10) Uani 1 1 d . . . H13A H -0.129(5) 0.086(4) 0.413(4) 0.044(12) Uiso 1 1 d . . . H13B H 0.001(4) 0.051(4) 0.282(3) 0.016(10) Uiso 1 1 d . . . C14 C -0.2112(6) 0.1812(5) 0.2614(4) 0.0280(11) Uani 1 1 d . . . H14A H -0.342(5) 0.178(5) 0.325(4) 0.055(13) Uiso 1 1 d . . . H14B H -0.197(5) 0.161(5) 0.206(3) 0.029(15) Uiso 1 1 d . . . N15 N -0.1810(4) 0.3351(3) 0.2638(3) 0.0243(8) Uani 1 1 d . . . C16 C -0.0472(5) 0.3936(4) 0.1924(3) 0.0237(9) Uani 1 1 d . . . C17 C -0.0263(5) 0.5386(4) 0.2147(3) 0.0236(9) Uani 1 1 d . . . H17 H -0.116(5) 0.597(4) 0.303(3) 0.043(12) Uiso 1 1 d . . . C18 C 0.0993(5) 0.6075(5) 0.1414(3) 0.0268(10) Uani 1 1 d . . . H18 H 0.107(5) 0.708(5) 0.172(3) 0.045(12) Uiso 1 1 d . . . C19 C 0.2096(4) 0.5311(4) 0.0468(3) 0.0239(9) Uani 1 1 d . . . C20 C 0.1989(5) 0.3869(4) 0.0226(3) 0.0236(9) Uani 1 1 d . . . H20 H 0.271(5) 0.334(5) -0.044(4) 0.049(13) Uiso 1 1 d . . . C21 C 0.0732(5) 0.3183(4) 0.0925(3) 0.0236(9) Uani 1 1 d . . . O22 O 0.0573(3) 0.1766(3) 0.0709(2) 0.0316(7) Uani 1 1 d . . . C23 C 0.1819(6) 0.0971(5) -0.0251(4) 0.0342(11) Uani 1 1 d . . . H23A H 0.157(5) -0.008(5) -0.019(3) 0.036(11) Uiso 1 1 d . . . H23B H 0.294(5) 0.082(4) -0.012(3) 0.037(12) Uiso 1 1 d . . . H23C H 0.192(5) 0.149(5) -0.113(4) 0.061(14) Uiso 1 1 d . . . N24 N 0.3397(4) 0.6017(4) -0.0325(3) 0.0275(8) Uani 1 1 d . . . O25 O 0.3477(3) 0.7324(3) -0.0129(2) 0.0358(8) Uani 1 1 d . . . O26 O 0.4390(3) 0.5280(3) -0.1166(2) 0.0345(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 0.024(2) 0.025(2) 0.030(2) -0.001(2) -0.004(2) -0.001(2) C2 0.028(2) 0.028(2) 0.027(2) -0.008(2) 0.002(2) -0.007(2) O3 0.0402(17) 0.0271(16) 0.0205(14) -0.0028(12) -0.0063(13) -0.0125(13) C4 0.031(3) 0.032(3) 0.024(2) -0.004(2) -0.008(2) -0.009(2) C5 0.031(3) 0.032(3) 0.029(3) -0.009(2) -0.008(2) -0.005(2) O6 0.0269(16) 0.0276(16) 0.0334(16) -0.0040(13) -0.0019(13) -0.0065(13) C7 0.032(3) 0.036(3) 0.025(2) 0.001(2) -0.005(2) -0.013(2) C8 0.033(3) 0.031(3) 0.029(2) 0.002(2) -0.007(2) -0.011(2) O9 0.0272(16) 0.0381(17) 0.0252(15) -0.0040(13) 0.0001(13) -0.0148(13) C10 0.025(2) 0.028(3) 0.032(2) -0.005(2) 0.000(2) -0.008(2) C11 0.030(3) 0.029(3) 0.035(3) 0.003(2) -0.004(2) -0.013(2) O12 0.0391(17) 0.0235(15) 0.0300(16) -0.0031(12) 0.0007(14) -0.0068(13) C13 0.028(3) 0.024(2) 0.029(2) 0.0012(19) -0.003(2) -0.0085(19) C14 0.029(3) 0.028(3) 0.027(3) -0.004(2) -0.007(2) -0.0067(19) N15 0.0219(18) 0.0229(18) 0.0215(17) -0.0057(14) 0.0023(15) -0.0022(14) C16 0.022(2) 0.023(2) 0.025(2) -0.0028(17) -0.0064(18) -0.0016(17) C17 0.021(2) 0.023(2) 0.024(2) -0.0052(17) -0.0046(18) -0.0011(17) C18 0.029(2) 0.028(2) 0.027(2) -0.0046(19) -0.0128(19) -0.0047(19) C19 0.019(2) 0.025(2) 0.025(2) 0.0041(18) -0.0061(18) -0.0039(17) C20 0.021(2) 0.026(2) 0.020(2) -0.0043(18) -0.0017(18) -0.0006(18) C21 0.024(2) 0.023(2) 0.023(2) -0.0043(17) -0.0079(18) -0.0007(17) O22 0.0360(17) 0.0252(15) 0.0268(15) -0.0111(12) 0.0041(13) -0.0083(13) C23 0.036(3) 0.027(3) 0.029(2) -0.014(2) 0.005(2) -0.003(2) N24 0.0246(19) 0.0266(19) 0.032(2) 0.0016(16) -0.0105(17) -0.0049(15) O25 0.0378(18) 0.0306(17) 0.0397(18) -0.0004(14) -0.0085(15) -0.0135(14) O26 0.0292(16) 0.0377(18) 0.0297(17) -0.0052(14) 0.0014(14) -0.0064(14) _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 C1 N15 1.447(5) . ? C1 C2 1.505(6) . ? C2 O3 1.422(5) . ? O3 C4 1.416(5) . ? C4 C5 1.481(6) . ? C5 O6 1.417(5) . ? O6 C7 1.413(5) . ? C7 C8 1.497(6) . ? C8 O9 1.422(5) . ? O9 C10 1.417(5) . ? C10 C11 1.483(6) . ? C11 O12 1.423(5) . ? O12 C13 1.433(4) . ? C13 C14 1.503(6) . ? C14 N15 1.463(5) . ? N15 C16 1.380(4) . ? C16 C17 1.415(5) . ? C16 C21 1.432(5) . ? C17 C18 1.386(5) . ? C18 C19 1.364(5) . ? C19 C20 1.381(5) . ? C19 N24 1.448(5) . ? C20 C21 1.373(5) . ? C21 O22 1.366(4) . ? O22 C23 1.430(4) . ? N24 O25 1.238(4) . ? N24 O26 1.239(4) . ? 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 N15 C1 C2 115.7(4) . . ? O3 C2 C1 108.9(3) . . ? C4 O3 C2 111.8(3) . . ? O3 C4 C5 109.2(4) . . ? O6 C5 C4 109.3(4) . . ? C7 O6 C5 112.8(3) . . ? O6 C7 C8 109.1(4) . . ? O9 C8 C7 111.4(4) . . ? C10 O9 C8 113.3(3) . . ? O9 C10 C11 108.1(3) . . ? O12 C11 C10 110.3(4) . . ? C11 O12 C13 112.2(3) . . ? O12 C13 C14 109.4(4) . . ? N15 C14 C13 113.1(4) . . ? C16 N15 C1 118.7(3) . . ? C16 N15 C14 126.7(3) . . ? C1 N15 C14 114.6(3) . . ? N15 C16 C17 119.7(3) . . ? N15 C16 C21 124.1(3) . . ? C17 C16 C21 116.2(3) . . ? C18 C17 C16 122.1(4) . . ? C19 C18 C17 119.1(4) . . ? C18 C19 C20 121.5(4) . . ? C18 C19 N24 120.2(4) . . ? C20 C19 N24 118.3(3) . . ? C21 C20 C19 120.4(3) . . ? O22 C21 C20 122.2(3) . . ? O22 C21 C16 117.1(3) . . ? C20 C21 C16 120.7(3) . . ? C21 O22 C23 117.5(3) . . ? O25 N24 O26 122.9(3) . . ? O25 N24 C19 118.7(3) . . ? O26 N24 C19 118.4(3) . . ? _diffrn_measured_fraction_theta_max 0.859 _diffrn_reflns_theta_full 28.67 _diffrn_measured_fraction_theta_full 0.859 _refine_diff_density_max 0.317 _refine_diff_density_min -0.332 _refine_diff_density_rms 0.076 #===END