# Copyright The Royal Society of Chemistry, 1998 # CCDC Number: 207/275 data_ch1 _audit_creation_method SHELXL _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_formula_sum 'C18 H12 N2 O2' _chemical_formula_weight 288.30 _chemical_melting_point ? _chemical_compound_source synthesis 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 Orthorhombic _symmetry_space_group_name_H-M 'Pbca' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' '-x, -y, -z' 'x-1/2, y, -z-1/2' 'x, -y-1/2, z-1/2' '-x-1/2, y-1/2, z' _cell_length_a 14.487(2) _cell_length_b 8.605(2) _cell_length_c 22.048(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2748.5(8) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 40 _cell_measurement_theta_min 1.85 _cell_measurement_theta_max 24.99 _exptl_crystal_description needle _exptl_crystal_colour transparent _exptl_crystal_size_max 0.80 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 0.697 _exptl_crystal_density_method ? _exptl_crystal_F_000 600 _exptl_absorpt_coefficient_mu 0.046 _exptl_absorpt_correction_type 'none' _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(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 'Siemens P4' _diffrn_measurement_method '2\q/\w scans' _diffrn_standards_number 3 _diffrn_standards_interval_count 100 _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 3144 _diffrn_reflns_av_R_equivalents 0.0365 _diffrn_reflns_av_sigmaI/netI 0.0452 _diffrn_reflns_limit_h_min -1 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -1 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -26 _diffrn_reflns_limit_l_max 1 _diffrn_reflns_theta_min 1.85 _diffrn_reflns_theta_max 24.99 _reflns_number_total 2417 _reflns_number_observed 1693 _reflns_observed_criterion >2sigma(I) _computing_data_collection 'Siemens XSCAN' _computing_cell_refinement 'Siemens XSCAN' _computing_data_reduction 'Siemens SHELXTL' _computing_structure_solution 'SHELXS-86 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-93 (Sheldrick, 1993)' _computing_molecular_graphics 'Siemens SHELXTL' _computing_publication_material 'Siemens SHELXTL' _refine_special_details ; Refinement on F^2^ for ALL reflections except for 0 with very negative F^2^ or flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses 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 observed criterion of F^2^ > 2sigma(F^2^) is used only for calculating _R_factor_obs 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 w=1/[\s^2^(Fo^2^)+(0.0773P)^2^+1.0486P] 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 'see text' _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0224(21) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_number_reflns 2417 _refine_ls_number_parameters 248 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0846 _refine_ls_R_factor_obs 0.0573 _refine_ls_wR_factor_all 0.1644 _refine_ls_wR_factor_obs 0.1435 _refine_ls_goodness_of_fit_all 1.060 _refine_ls_goodness_of_fit_obs 1.130 _refine_ls_restrained_S_all 1.060 _refine_ls_restrained_S_obs 1.130 _refine_ls_shift/esd_max 0.000 _refine_ls_shift/esd_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_thermal_displace_type _atom_site_occupancy _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_group O1 O 0.65665(13) 0.2136(3) 0.21423(10) 0.0752(7) Uani 1 d . . O2 O 0.93915(12) 0.1254(2) 0.27875(8) 0.0543(6) Uani 1 d . . N1 N 0.80908(14) 0.2174(3) 0.23332(10) 0.0510(6) Uani 1 d . . N2 N 1.0181(2) 0.2337(4) 0.03543(14) 0.0931(11) Uani 1 d . . C1 C 0.8074(2) 0.2635(3) 0.29459(12) 0.0496(7) Uani 1 d . . C2 C 0.7439(2) 0.3456(4) 0.32825(14) 0.0645(9) Uani 1 d . . C3 C 0.7641(2) 0.3698(5) 0.38903(14) 0.0722(10) Uani 1 d . . C4 C 0.8434(2) 0.3124(4) 0.41439(15) 0.0682(9) Uani 1 d . . C5 C 0.9076(2) 0.2290(4) 0.38086(13) 0.0586(8) Uani 1 d . . C6 C 0.8874(2) 0.2080(3) 0.32069(11) 0.0483(7) Uani 1 d . . C7 C 0.9036(2) 0.1715(3) 0.22048(11) 0.0467(7) Uani 1 d . . C8 C 0.9213(2) 0.0522(4) 0.17015(12) 0.0474(7) Uani 1 d . . C9 C 0.9665(2) 0.2895(4) 0.18958(15) 0.0593(8) Uani 1 d . . C10 C 1.0034(2) 0.1583(4) 0.14887(13) 0.0558(8) Uani 1 d . . C11 C 1.0122(2) 0.1961(4) 0.0846(2) 0.0666(9) Uani 1 d . . C12 C 0.8416(2) 0.0343(3) 0.12712(11) 0.0476(7) Uani 1 d . . C13 C 0.8534(2) -0.0484(4) 0.07366(13) 0.0585(8) Uani 1 d . . C14 C 0.7799(2) -0.0725(4) 0.03501(15) 0.0655(9) Uani 1 d . . C15 C 0.6942(2) -0.0148(4) 0.04879(14) 0.0682(9) Uani 1 d . . C16 C 0.6814(2) 0.0686(4) 0.10145(14) 0.0613(9) Uani 1 d . . C17 C 0.7546(2) 0.0936(3) 0.14138(11) 0.0493(7) Uani 1 d . . C18 C 0.7347(2) 0.1790(4) 0.19817(13) 0.0532(7) Uani 1 d . . H2 H 0.6902(20) 0.3872(35) 0.3089(13) 0.059(8) Uiso 1 d . . H3 H 0.7243(22) 0.4244(40) 0.4121(15) 0.078(10) Uiso 1 d . . H4 H 0.8563(20) 0.3303(36) 0.4580(14) 0.069(9) Uiso 1 d . . H5 H 0.9648(22) 0.1860(36) 0.3983(13) 0.071(9) Uiso 1 d . . H8 H 0.9417(17) -0.0447(34) 0.1859(12) 0.050(7) Uiso 1 d . . H9A H 1.0090(24) 0.3518(42) 0.2144(14) 0.077(10) Uiso 1 d . . H9B H 0.9288(21) 0.3610(37) 0.1678(13) 0.065(9) Uiso 1 d . . H10 H 1.0629(20) 0.1114(34) 0.1619(12) 0.060(8) Uiso 1 d . . H14 H 0.7903(21) -0.1294(40) -0.0012(14) 0.072(9) Uiso 1 d . . H13 H 0.9152(19) -0.0913(33) 0.0624(12) 0.060(8) Uiso 1 d . . H15 H 0.6425(22) -0.0314(41) 0.0212(15) 0.089(11) Uiso 1 d . . H16 H 0.6231(23) 0.1088(41) 0.1140(13) 0.078(10) Uiso 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 0.0403(11) 0.109(2) 0.0766(14) -0.0029(13) 0.0009(10) 0.0164(11) O2 0.0442(10) 0.0696(14) 0.0490(10) -0.0028(9) -0.0054(8) 0.0126(9) N1 0.0386(12) 0.065(2) 0.0500(13) -0.0038(11) -0.0016(9) 0.0091(11) N2 0.088(2) 0.123(3) 0.068(2) 0.001(2) 0.023(2) -0.016(2) C1 0.0440(14) 0.055(2) 0.049(2) 0.0008(13) 0.0025(12) 0.0029(13) C2 0.053(2) 0.073(2) 0.067(2) -0.005(2) 0.004(2) 0.017(2) C3 0.071(2) 0.084(3) 0.062(2) -0.017(2) 0.014(2) 0.016(2) C4 0.072(2) 0.080(2) 0.052(2) -0.006(2) 0.007(2) 0.003(2) C5 0.056(2) 0.068(2) 0.052(2) 0.0021(15) -0.0043(14) 0.002(2) C6 0.0452(15) 0.050(2) 0.0495(15) -0.0001(13) 0.0047(12) 0.0006(12) C7 0.0368(13) 0.058(2) 0.0455(14) 0.0004(12) -0.0008(11) 0.0028(12) C8 0.0402(14) 0.053(2) 0.050(2) 0.0012(13) -0.0014(11) 0.0049(13) C9 0.057(2) 0.061(2) 0.060(2) -0.005(2) 0.0056(15) -0.007(2) C10 0.0379(14) 0.073(2) 0.056(2) -0.0027(15) 0.0014(13) 0.0013(15) C11 0.051(2) 0.086(2) 0.063(2) -0.006(2) 0.0132(15) -0.011(2) C12 0.0435(14) 0.051(2) 0.0485(15) 0.0067(13) -0.0036(12) -0.0031(12) C13 0.060(2) 0.066(2) 0.050(2) 0.0013(14) -0.0026(14) -0.001(2) C14 0.079(2) 0.066(2) 0.052(2) 0.002(2) -0.010(2) -0.013(2) C15 0.066(2) 0.077(2) 0.061(2) 0.011(2) -0.021(2) -0.017(2) C16 0.047(2) 0.073(2) 0.064(2) 0.013(2) -0.0107(14) -0.008(2) C17 0.0418(13) 0.057(2) 0.0492(14) 0.0109(13) -0.0048(12) -0.0040(12) C18 0.0369(14) 0.066(2) 0.057(2) 0.0090(14) -0.0020(12) 0.0054(13) _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 C18 1.222(3) . ? O2 C6 1.386(3) . ? O2 C7 1.439(3) . ? N1 C18 1.368(3) . ? N1 C1 1.408(3) . ? N1 C7 1.454(3) . ? N2 C11 1.136(4) . ? C1 C2 1.377(4) . ? C1 C6 1.380(4) . ? C2 C3 1.388(4) . ? C3 C4 1.369(5) . ? C4 C5 1.387(4) . ? C5 C6 1.371(4) . ? C7 C9 1.525(4) . ? C7 C8 1.533(4) . ? C8 C12 1.502(3) . ? C8 C10 1.572(4) . ? C9 C10 1.538(4) . ? C10 C11 1.459(4) . ? C12 C13 1.388(4) . ? C12 C17 1.395(4) . ? C13 C14 1.379(4) . ? C14 C15 1.372(5) . ? C15 C16 1.377(5) . ? C16 C17 1.395(4) . ? C17 C18 1.480(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 C6 O2 C7 105.1(2) . . ? C18 N1 C1 126.7(2) . . ? C18 N1 C7 124.5(2) . . ? C1 N1 C7 106.3(2) . . ? C2 C1 C6 121.0(3) . . ? C2 C1 N1 132.3(3) . . ? C6 C1 N1 106.7(2) . . ? C1 C2 C3 117.1(3) . . ? C4 C3 C2 121.2(3) . . ? C3 C4 C5 122.1(3) . . ? C6 C5 C4 116.2(3) . . ? C5 C6 C1 122.5(3) . . ? C5 C6 O2 126.8(2) . . ? C1 C6 O2 110.7(2) . . ? O2 C7 N1 103.8(2) . . ? O2 C7 C9 111.6(2) . . ? N1 C7 C9 117.9(3) . . ? O2 C7 C8 113.7(2) . . ? N1 C7 C8 118.7(2) . . ? C9 C7 C8 91.3(2) . . ? C12 C8 C7 113.4(2) . . ? C12 C8 C10 116.9(2) . . ? C7 C8 C10 87.3(2) . . ? C7 C9 C10 88.8(2) . . ? C11 C10 C9 115.7(3) . . ? C11 C10 C8 119.1(2) . . ? C9 C10 C8 89.4(2) . . ? N2 C11 C10 176.3(4) . . ? C13 C12 C17 119.4(2) . . ? C13 C12 C8 119.6(2) . . ? C17 C12 C8 121.0(2) . . ? C14 C13 C12 120.4(3) . . ? C15 C14 C13 120.5(3) . . ? C14 C15 C16 119.8(3) . . ? C15 C16 C17 120.7(3) . . ? C16 C17 C12 119.2(3) . . ? C16 C17 C18 117.6(3) . . ? C12 C17 C18 123.2(2) . . ? O1 C18 N1 120.4(3) . . ? O1 C18 C17 123.1(3) . . ? N1 C18 C17 116.5(2) . . ? _refine_diff_density_max 0.205 _refine_diff_density_min -0.194 _refine_diff_density_rms 0.055 #===END data_cha5 _audit_creation_method SHELXL _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_formula_sum 'C21 H17 N O5 S' _chemical_formula_weight 395.42 _chemical_melting_point ? _chemical_compound_source ? 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 'Monoclinic' _symmetry_space_group_name_H-M 'P2(1)/c (#14)' 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 9.280(2) _cell_length_b 11.797(2) _cell_length_c 16.781(3) _cell_angle_alpha 90.00 _cell_angle_beta 95.03(3) _cell_angle_gamma 90.00 _cell_volume 1830.0(6) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 25 _cell_measurement_theta_min 13.5 _cell_measurement_theta_max 17.0 _exptl_crystal_description ? _exptl_crystal_colour 'Colorless' _exptl_crystal_size_max 1.50 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.18 _exptl_crystal_density_meas 'none' _exptl_crystal_density_diffrn 1.435 _exptl_crystal_density_method 'none' _exptl_crystal_F_000 824 _exptl_absorpt_coefficient_mu 0.211 _exptl_absorpt_correction_type 'Empirical_\y' _exptl_absorpt_correction_T_min 0.9492 _exptl_absorpt_correction_T_max 0.9967 _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(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 'Enraf-Nonius CAD4' _diffrn_measurement_method '\w/2\q' _diffrn_standards_number 3 _diffrn_standards_interval_count 97 _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 3806 _diffrn_reflns_av_R_equivalents 0.0185 _diffrn_reflns_av_sigmaI/netI 0.0295 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 2.11 _diffrn_reflns_theta_max 25.97 _reflns_number_total 3587 _reflns_number_observed 2837 _reflns_observed_criterion >2sigma(I) _computing_data_collection 'Enraf-Nonius CAD4' _computing_cell_refinement 'Enraf-Nonius CAD4' _computing_data_reduction 'Lorentz-Polarization (MolEN)' _computing_structure_solution 'SHELXS-86 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-93 (Sheldrick, 1993)' _computing_molecular_graphics 'SHELXTL Version 5' _computing_publication_material 'SHELXTL Version 5' _refine_special_details ; Refinement on F^2^ for ALL reflections except for 5 with very negative F^2^ or flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses 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 observed criterion of F^2^ > 2sigma(F^2^) is used only for calculating _R_factor_obs 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 w=1/[\s^2^(Fo^2^)+(0.0784P)^2^+0.2513P] 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 'not refine' _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0078(15) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_number_reflns 3582 _refine_ls_number_parameters 254 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0652 _refine_ls_R_factor_obs 0.0478 _refine_ls_wR_factor_all 0.1323 _refine_ls_wR_factor_obs 0.1235 _refine_ls_goodness_of_fit_all 1.032 _refine_ls_goodness_of_fit_obs 1.098 _refine_ls_restrained_S_all 1.039 _refine_ls_restrained_S_obs 1.098 _refine_ls_shift/esd_max 0.000 _refine_ls_shift/esd_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_thermal_displace_type _atom_site_occupancy _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_group S1 S 0.50364(5) 0.47689(5) 0.12643(3) 0.0429(2) Uani 1 d . . N1 N 0.2639(2) 0.46948(14) 0.03133(10) 0.0331(4) Uani 1 d . . O1 O 0.1170(2) 0.45087(14) -0.08278(9) 0.0499(4) Uani 1 d . . O2 O 0.0713(2) 0.7742(2) 0.18819(15) 0.0807(7) Uani 1 d . . O3 O 0.2754(2) 0.87506(14) 0.20293(11) 0.0637(5) Uani 1 d . . O4 O 0.3061(2) 0.5279(2) 0.30527(10) 0.0699(6) Uani 1 d . . O5 O 0.2311(2) 0.38565(14) 0.22515(9) 0.0481(4) Uani 1 d . . C1 C 0.4412(2) 0.3457(2) 0.08818(12) 0.0384(5) Uani 1 d . . C2 C 0.5064(3) 0.2420(2) 0.10278(14) 0.0478(6) Uani 1 d . . H2A H 0.5891(3) 0.2357(2) 0.13800(14) 0.057 Uiso 1 calc R . C3 C 0.4463(3) 0.1474(2) 0.0640(2) 0.0561(6) Uani 1 d . . H3A H 0.4894(3) 0.0768(2) 0.0725(2) 0.067 Uiso 1 calc R . C4 C 0.3219(3) 0.1583(2) 0.0126(2) 0.0566(6) Uani 1 d . . H4A H 0.2832(3) 0.0941(2) -0.0133(2) 0.068 Uiso 1 calc R . C5 C 0.2532(3) 0.2619(2) -0.00137(14) 0.0453(5) Uani 1 d . . H5A H 0.1688(3) 0.2675(2) -0.03538(14) 0.054 Uiso 1 calc R . C6 C 0.3139(2) 0.3564(2) 0.03674(12) 0.0354(5) Uani 1 d . . C7 C 0.1745(2) 0.5125(2) -0.03134(12) 0.0353(5) Uani 1 d . . C8 C 0.1543(2) 0.6370(2) -0.03415(13) 0.0369(5) Uani 1 d . . C9 C 0.0603(2) 0.6799(2) -0.09645(14) 0.0476(6) Uani 1 d . . H9A H 0.0107(2) 0.6299(2) -0.13193(14) 0.057 Uiso 1 calc R . C10 C 0.0400(3) 0.7933(2) -0.1061(2) 0.0571(7) Uani 1 d . . H10A H -0.0235(3) 0.8204(2) -0.1477(2) 0.069 Uiso 1 calc R . C11 C 0.1134(3) 0.8683(2) -0.0542(2) 0.0548(6) Uani 1 d . . H11A H 0.0991(3) 0.9460(2) -0.0605(2) 0.066 Uiso 1 calc R . C12 C 0.2084(3) 0.8277(2) 0.00740(14) 0.0469(5) Uani 1 d . . H12A H 0.2588(3) 0.8785(2) 0.04178(14) 0.056 Uiso 1 calc R . C13 C 0.2295(2) 0.7125(2) 0.01858(12) 0.0373(5) Uani 1 d . . C14 C 0.3388(2) 0.6694(2) 0.08263(12) 0.0366(5) Uani 1 d . . H14A H 0.4376(2) 0.6941(2) 0.07518(12) 0.044 Uiso 1 calc R . C15 C 0.3272(2) 0.5411(2) 0.09583(12) 0.0340(5) Uani 1 d . . C16 C 0.2357(2) 0.5649(2) 0.16787(12) 0.0359(5) Uani 1 d . . H16A H 0.1324(2) 0.5667(2) 0.14991(12) 0.043 Uiso 1 calc R . C17 C 0.2984(2) 0.6849(2) 0.17082(13) 0.0404(5) Uani 1 d . . H17A H 0.3863(2) 0.6876(2) 0.20764(13) 0.049 Uiso 1 calc R . C18 C 0.1990(3) 0.7806(2) 0.18840(14) 0.0493(6) Uani 1 d . . C19 C 0.1939(4) 0.9770(2) 0.2139(2) 0.0831(10) Uani 1 d . . H19A H 0.2591(4) 1.0395(2) 0.2240(2) 0.125 Uiso 1 calc R . H19B H 0.1371(4) 0.9675(2) 0.2586(2) 0.125 Uiso 1 calc R . H19C H 0.1310(4) 0.9918(2) 0.1666(2) 0.125 Uiso 1 calc R . C20 C 0.2620(2) 0.4932(2) 0.24117(13) 0.0405(5) Uani 1 d . . C21 C 0.2689(3) 0.3052(2) 0.2879(2) 0.0656(8) Uani 1 d . . H21A H 0.2418(3) 0.2304(2) 0.2697(2) 0.098 Uiso 1 calc R . H21B H 0.2189(3) 0.3238(2) 0.3339(2) 0.098 Uiso 1 calc R . H21C H 0.3714(3) 0.3077(2) 0.3020(2) 0.098 Uiso 1 calc R . 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 S1 0.0260(3) 0.0552(4) 0.0458(3) -0.0022(3) -0.0061(2) 0.0025(2) N1 0.0290(8) 0.0387(9) 0.0307(8) -0.0022(7) -0.0024(6) 0.0007(7) O1 0.0485(9) 0.0501(9) 0.0470(9) -0.0045(7) -0.0197(7) -0.0038(7) O2 0.0495(12) 0.0768(14) 0.117(2) -0.0220(13) 0.0150(11) 0.0103(10) O3 0.0747(12) 0.0428(10) 0.0698(12) -0.0120(8) -0.0146(10) 0.0043(9) O4 0.103(2) 0.0682(12) 0.0352(10) -0.0082(8) -0.0114(9) -0.0064(11) O5 0.0523(9) 0.0509(10) 0.0395(8) 0.0036(7) -0.0047(7) -0.0094(8) C1 0.0328(10) 0.0494(13) 0.0336(10) 0.0021(9) 0.0053(8) 0.0044(9) C2 0.0444(13) 0.0555(15) 0.0433(12) 0.0080(11) 0.0029(10) 0.0123(11) C3 0.063(2) 0.0469(14) 0.058(2) 0.0066(12) 0.0059(13) 0.0122(12) C4 0.068(2) 0.0427(14) 0.058(2) -0.0019(11) 0.0003(13) 0.0008(12) C5 0.0465(13) 0.0454(13) 0.0430(12) -0.0019(10) -0.0015(10) -0.0015(10) C6 0.0328(10) 0.0435(12) 0.0300(10) 0.0016(8) 0.0028(8) 0.0027(8) C7 0.0253(9) 0.0439(12) 0.0358(10) 0.0014(9) -0.0022(8) -0.0027(8) C8 0.0269(10) 0.0454(12) 0.0378(11) 0.0023(9) -0.0001(8) -0.0017(8) C9 0.0387(12) 0.0522(14) 0.0494(13) 0.0039(11) -0.0102(10) 0.0002(10) C10 0.0528(15) 0.057(2) 0.058(2) 0.0147(13) -0.0102(12) 0.0097(12) C11 0.059(2) 0.0457(14) 0.059(2) 0.0091(12) -0.0002(12) 0.0035(11) C12 0.0502(13) 0.0423(13) 0.0475(13) 0.0023(10) 0.0006(10) -0.0038(10) C13 0.0318(10) 0.0428(12) 0.0374(11) 0.0021(9) 0.0032(8) -0.0039(9) C14 0.0268(10) 0.0421(11) 0.0402(11) -0.0021(9) -0.0015(8) -0.0051(9) C15 0.0251(9) 0.0439(12) 0.0320(10) -0.0013(8) -0.0046(8) -0.0001(8) C16 0.0273(9) 0.0452(12) 0.0344(10) -0.0061(9) -0.0014(8) -0.0011(9) C17 0.0358(11) 0.0450(12) 0.0387(11) -0.0050(9) -0.0070(9) -0.0028(9) C18 0.057(2) 0.0500(14) 0.0394(12) -0.0075(10) -0.0035(11) 0.0043(12) C19 0.117(3) 0.048(2) 0.081(2) -0.0123(15) -0.014(2) 0.021(2) C20 0.0357(11) 0.0512(13) 0.0345(11) -0.0046(10) 0.0027(9) -0.0012(9) C21 0.070(2) 0.062(2) 0.063(2) 0.0208(14) -0.0048(14) -0.0022(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 S1 C1 1.755(2) . ? S1 C15 1.836(2) . ? N1 C7 1.378(3) . ? N1 C6 1.412(3) . ? N1 C15 1.456(2) . ? O1 C7 1.216(3) . ? O2 C18 1.187(3) . ? O3 C18 1.332(3) . ? O3 C19 1.441(3) . ? O4 C20 1.189(3) . ? O5 C20 1.323(3) . ? O5 C21 1.438(3) . ? C1 C2 1.377(3) . ? C1 C6 1.406(3) . ? C2 C3 1.384(4) . ? C3 C4 1.385(4) . ? C4 C5 1.390(3) . ? C5 C6 1.381(3) . ? C7 C8 1.481(3) . ? C8 C9 1.397(3) . ? C8 C13 1.398(3) . ? C9 C10 1.359(4) . ? C10 C11 1.379(4) . ? C11 C12 1.384(3) . ? C12 C13 1.383(3) . ? C13 C14 1.500(3) . ? C14 C15 1.535(3) . ? C14 C17 1.569(3) . ? C15 C16 1.562(3) . ? C16 C20 1.495(3) . ? C16 C17 1.529(3) . ? C17 C18 1.503(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 C1 S1 C15 90.21(10) . . ? C7 N1 C6 124.7(2) . . ? C7 N1 C15 122.0(2) . . ? C6 N1 C15 113.1(2) . . ? C18 O3 C19 116.4(2) . . ? C20 O5 C21 116.7(2) . . ? C2 C1 C6 121.4(2) . . ? C2 C1 S1 126.3(2) . . ? C6 C1 S1 112.2(2) . . ? C1 C2 C3 118.7(2) . . ? C2 C3 C4 119.8(2) . . ? C3 C4 C5 122.1(2) . . ? C6 C5 C4 118.0(2) . . ? C5 C6 C1 119.9(2) . . ? C5 C6 N1 127.9(2) . . ? C1 C6 N1 112.2(2) . . ? O1 C7 N1 121.3(2) . . ? O1 C7 C8 121.6(2) . . ? N1 C7 C8 117.1(2) . . ? C9 C8 C13 119.2(2) . . ? C9 C8 C7 116.9(2) . . ? C13 C8 C7 123.8(2) . . ? C10 C9 C8 121.1(2) . . ? C9 C10 C11 120.1(2) . . ? C10 C11 C12 119.7(2) . . ? C13 C12 C11 121.0(2) . . ? C12 C13 C8 118.9(2) . . ? C12 C13 C14 120.6(2) . . ? C8 C13 C14 120.4(2) . . ? C13 C14 C15 112.7(2) . . ? C13 C14 C17 115.7(2) . . ? C15 C14 C17 87.3(2) . . ? N1 C15 C14 119.6(2) . . ? N1 C15 C16 118.0(2) . . ? C14 C15 C16 89.1(2) . . ? N1 C15 S1 105.06(13) . . ? C14 C15 S1 112.01(13) . . ? C16 C15 S1 112.92(13) . . ? C20 C16 C17 117.6(2) . . ? C20 C16 C15 118.3(2) . . ? C17 C16 C15 87.8(2) . . ? C18 C17 C16 117.6(2) . . ? C18 C17 C14 118.3(2) . . ? C16 C17 C14 89.0(2) . . ? O2 C18 O3 124.7(2) . . ? O2 C18 C17 125.5(2) . . ? O3 C18 C17 109.8(2) . . ? O4 C20 O5 124.4(2) . . ? O4 C20 C16 124.6(2) . . ? O5 C20 C16 111.0(2) . . ? _refine_diff_density_max 0.366 _refine_diff_density_min -0.249 _refine_diff_density_rms 0.050 #===END