data_pyrrolidine_2_(CCDC#696031) _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C24 H40 N2 O4 S' _chemical_formula_sum 'C24 H40 N2 O4 S' _chemical_formula_weight 452.64 _chemical_absolute_configuration ad 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 'Orthorhombic' _symmetry_space_group_name_H-M 'P 21 21 21' _symmetry_space_group_name_Hall 'P 2ac 2ab' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' _cell_length_a 8.1083(5) _cell_length_b 10.8440(6) _cell_length_c 27.2736(16) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2398.1(2) _cell_formula_units_Z 4 _cell_measurement_temperature 90(1) _cell_measurement_reflns_used 9978 _cell_measurement_theta_min 2.40 _cell_measurement_theta_max 28.16 _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.254 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 984 _exptl_absorpt_coefficient_mu 0.167 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9594 _exptl_absorpt_correction_T_max 0.9981 _exptl_absorpt_process_details '(SADABS 2004/1 Bruker 2004)' _exptl_special_details ; Data collection was performed with four runs at \f = 0.00 \%, at \f = 70.00 \%, at \f = 140 \%,at \f = 210 \% and at \f = 280 \% (360 frames each). Frame width = 0.50 \% in \w. Data were merged, corrected for decay, and treated with multi-scan absorption corrections, Bruker (2004). ; _diffrn_ambient_temperature 90(1) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'rotating anode' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker SMART APEX2' _diffrn_source_type 'RIGAKU RU-2000BEH' _diffrn_detector_area_resol_mean 8.33 _diffrn_measurement_method '\f and \w scans' _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 46282 _diffrn_reflns_av_R_equivalents 0.0359 _diffrn_reflns_av_sigmaI/netI 0.0196 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -36 _diffrn_reflns_limit_l_max 36 _diffrn_reflns_theta_min 1.49 _diffrn_reflns_theta_max 28.19 _reflns_number_total 5894 _reflns_number_gt 5509 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEX2 (Bruker, 2004)' _computing_cell_refinement 'Bruker Saint v7.23A (Bruker, 2005)' _computing_data_reduction 'Bruker Saint v7.23A (Bruker, 2005)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _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^)+(0.0318P)^2^+0.4649P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.02(4) _refine_ls_number_reflns 5894 _refine_ls_number_parameters 286 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0305 _refine_ls_R_factor_gt 0.0255 _refine_ls_wR_factor_ref 0.0649 _refine_ls_wR_factor_gt 0.0618 _refine_ls_goodness_of_fit_ref 1.084 _refine_ls_restrained_S_all 1.084 _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 C21 C 0.45690(15) 0.55598(11) 0.70453(4) 0.0159(2) Uani 1 1 d . . . C22 C 0.30901(15) 0.62119(11) 0.70915(5) 0.0180(2) Uani 1 1 d . . . H22 H 0.2971 0.6992 0.6937 0.022 Uiso 1 1 calc R . . C23 C 0.18059(15) 0.57295(11) 0.73601(4) 0.0166(2) Uani 1 1 d . . . H23 H 0.0792 0.6164 0.7385 0.020 Uiso 1 1 calc R . . C18 C 0.20037(14) 0.45949(11) 0.75965(4) 0.0133(2) Uani 1 1 d . . . C19 C 0.34856(14) 0.39603(12) 0.75626(4) 0.0159(2) Uani 1 1 d . . . H19 H 0.3621 0.3200 0.7731 0.019 Uiso 1 1 calc R . . C20 C 0.47745(16) 0.44337(11) 0.72830(4) 0.0165(2) Uani 1 1 d . . . H20 H 0.5783 0.3994 0.7255 0.020 Uiso 1 1 calc R . . C5 C -0.13595(13) 0.59712(11) 0.82786(4) 0.0127(2) Uani 1 1 d . . . H5 H -0.1710 0.5978 0.7927 0.015 Uiso 1 1 calc R . . C4 C -0.03727(17) 0.71409(11) 0.83950(4) 0.0151(2) Uani 1 1 d . . . H4B H -0.1110 0.7814 0.8505 0.018 Uiso 1 1 calc R . . H4A H 0.0256 0.7422 0.8105 0.018 Uiso 1 1 calc R . . C2 C 0.11875(14) 0.53760(10) 0.87080(4) 0.0126(2) Uani 1 1 d . . . H2 H 0.2293 0.5303 0.8548 0.015 Uiso 1 1 calc R . . C3 C 0.07928(15) 0.67418(11) 0.88086(4) 0.0155(2) Uani 1 1 d . . . H3B H 0.0252 0.6838 0.9132 0.019 Uiso 1 1 calc R . . H3A H 0.1813 0.7243 0.8805 0.019 Uiso 1 1 calc R . . C6 C -0.28694(14) 0.57780(11) 0.86119(4) 0.0151(2) Uani 1 1 d . . . H6 H -0.2529 0.5942 0.8958 0.018 Uiso 1 1 calc R . . C7 C -0.35263(16) 0.44596(12) 0.85813(5) 0.0186(2) Uani 1 1 d . . . H7B H -0.3735 0.4246 0.8238 0.028 Uiso 1 1 calc R . . H7C H -0.4556 0.4397 0.8768 0.028 Uiso 1 1 calc R . . H7A H -0.2709 0.3890 0.8719 0.028 Uiso 1 1 calc R . . C8 C -0.42401(16) 0.66882(12) 0.84765(5) 0.0214(3) Uani 1 1 d . . . H8B H -0.5146 0.6616 0.8713 0.032 Uiso 1 1 calc R . . H8C H -0.4649 0.6501 0.8147 0.032 Uiso 1 1 calc R . . H8A H -0.3803 0.7530 0.8483 0.032 Uiso 1 1 calc R . . C1 C 0.11391(15) 0.45909(11) 0.91708(4) 0.0154(2) Uani 1 1 d . . . H1A H 0.0027 0.4606 0.9321 0.018 Uiso 1 1 calc R . . H1B H 0.1440 0.3726 0.9098 0.018 Uiso 1 1 calc R . . C9 C 0.18252(15) 0.54710(12) 1.03324(4) 0.0157(2) Uani 1 1 d . . . C15 C -0.00348(15) 0.56595(12) 1.02619(5) 0.0195(3) Uani 1 1 d . . . H15A H -0.0593 0.4858 1.0268 0.029 Uiso 1 1 calc R . . H15B H -0.0236 0.6062 0.9946 0.029 Uiso 1 1 calc R . . H15C H -0.0464 0.6179 1.0527 0.029 Uiso 1 1 calc R . . C14 C 0.26712(18) 0.67304(12) 1.02907(5) 0.0217(3) Uani 1 1 d . . . H14B H 0.2637 0.7010 0.9949 0.033 Uiso 1 1 calc R . . H14A H 0.3822 0.6659 1.0397 0.033 Uiso 1 1 calc R . . H14C H 0.2096 0.7328 1.0499 0.033 Uiso 1 1 calc R . . C10 C 0.20843(16) 0.49062(12) 1.08441(4) 0.0188(3) Uani 1 1 d . . . H10B H 0.1815 0.5533 1.1096 0.023 Uiso 1 1 calc R . . H10A H 0.1312 0.4207 1.0887 0.023 Uiso 1 1 calc R . . C11 C 0.38367(16) 0.44520(13) 1.09272(5) 0.0230(3) Uani 1 1 d . . . H11B H 0.4619 0.5151 1.0907 0.028 Uiso 1 1 calc R . . H11A H 0.3933 0.4077 1.1257 0.028 Uiso 1 1 calc R . . C12 C 0.42378(17) 0.35029(12) 1.05367(5) 0.0210(3) Uani 1 1 d . . . H12A H 0.3492 0.2787 1.0577 0.025 Uiso 1 1 calc R . . H12B H 0.5382 0.3209 1.0586 0.025 Uiso 1 1 calc R . . C13 C 0.40670(15) 0.40033(12) 1.00117(4) 0.0156(2) Uani 1 1 d . . . C17 C 0.54976(16) 0.48938(12) 0.98951(5) 0.0192(2) Uani 1 1 d . . . H17B H 0.5695 0.5432 1.0178 0.029 Uiso 1 1 calc R . . H17A H 0.5209 0.5397 0.9609 0.029 Uiso 1 1 calc R . . H17C H 0.6497 0.4418 0.9824 0.029 Uiso 1 1 calc R . . C16 C 0.41552(17) 0.29103(12) 0.96593(5) 0.0203(3) Uani 1 1 d . . . H13A H 0.4111 0.3211 0.9321 0.031 Uiso 1 1 calc R . . H13B H 0.3221 0.2357 0.9720 0.031 Uiso 1 1 calc R . . H13C H 0.5190 0.2462 0.9712 0.031 Uiso 1 1 calc R . . C24 C 0.71496(16) 0.54053(13) 0.66275(5) 0.0228(3) Uani 1 1 d . . . H24C H 0.7879 0.5907 0.6422 0.034 Uiso 1 1 calc R . . H24B H 0.6804 0.4670 0.6445 0.034 Uiso 1 1 calc R . . H24A H 0.7740 0.5154 0.6925 0.034 Uiso 1 1 calc R . . N1 N -0.01204(12) 0.49797(9) 0.83609(3) 0.01218(19) Uani 1 1 d . . . N2 N 0.23719(13) 0.45348(10) 0.99638(3) 0.01343(19) Uani 1 1 d . . . O4 O 0.57298(11) 0.61111(9) 0.67596(3) 0.02052(18) Uani 1 1 d . . . O2 O 0.09482(11) 0.28914(8) 0.81764(3) 0.01802(18) Uani 1 1 d . . . O3 O -0.10695(10) 0.38930(8) 0.76228(3) 0.01722(17) Uani 1 1 d . . . O1 O 0.23278(11) 0.51473(8) 0.94892(3) 0.01449(17) Uani 1 1 d . . . S1 S 0.03474(3) 0.39841(3) 0.793845(10) 0.01257(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 C21 0.0152(5) 0.0184(5) 0.0139(5) -0.0038(5) 0.0005(5) -0.0033(5) C22 0.0210(6) 0.0164(6) 0.0167(5) 0.0015(5) 0.0015(5) 0.0013(4) C23 0.0172(6) 0.0167(6) 0.0160(5) -0.0009(4) 0.0009(4) 0.0041(5) C18 0.0132(5) 0.0151(5) 0.0115(5) -0.0019(4) 0.0009(4) -0.0012(4) C19 0.0154(5) 0.0159(5) 0.0165(5) -0.0006(5) -0.0014(4) 0.0012(5) C20 0.0133(5) 0.0191(5) 0.0171(5) -0.0031(5) -0.0007(5) 0.0018(5) C5 0.0120(5) 0.0141(5) 0.0120(5) -0.0003(4) -0.0002(4) 0.0021(5) C4 0.0163(5) 0.0142(5) 0.0150(5) 0.0017(4) 0.0006(5) -0.0006(5) C2 0.0113(5) 0.0143(5) 0.0122(5) -0.0008(4) -0.0016(4) -0.0002(4) C3 0.0153(6) 0.0149(5) 0.0163(5) -0.0006(4) -0.0012(4) -0.0007(4) C6 0.0127(5) 0.0185(6) 0.0142(5) -0.0013(4) 0.0012(4) 0.0006(4) C7 0.0159(6) 0.0212(6) 0.0187(6) -0.0014(5) 0.0027(5) -0.0035(5) C8 0.0151(6) 0.0231(6) 0.0260(7) -0.0033(5) -0.0006(5) 0.0048(5) C1 0.0169(6) 0.0155(5) 0.0136(5) 0.0002(4) -0.0039(4) -0.0034(5) C9 0.0168(6) 0.0161(5) 0.0141(5) -0.0017(5) -0.0009(4) 0.0001(5) C15 0.0181(6) 0.0201(6) 0.0203(6) -0.0005(5) -0.0002(5) 0.0044(5) C14 0.0284(7) 0.0162(6) 0.0206(6) -0.0031(5) -0.0012(5) -0.0029(5) C10 0.0195(6) 0.0226(6) 0.0144(6) 0.0000(5) 0.0001(5) -0.0002(5) C11 0.0206(6) 0.0331(7) 0.0153(6) 0.0047(5) -0.0035(5) 0.0001(6) C12 0.0173(6) 0.0247(6) 0.0209(6) 0.0085(5) -0.0011(5) 0.0033(5) C13 0.0128(5) 0.0168(5) 0.0173(5) 0.0030(5) -0.0012(4) 0.0005(5) C17 0.0142(6) 0.0227(6) 0.0206(6) 0.0012(5) -0.0007(5) -0.0025(5) C16 0.0175(6) 0.0186(6) 0.0249(6) 0.0007(5) 0.0022(5) 0.0020(5) C24 0.0164(6) 0.0272(7) 0.0246(6) -0.0039(5) 0.0061(5) -0.0023(5) N1 0.0122(5) 0.0133(4) 0.0110(4) -0.0020(3) -0.0015(4) 0.0020(4) N2 0.0153(5) 0.0146(5) 0.0105(4) 0.0025(4) -0.0011(4) 0.0013(4) O4 0.0169(4) 0.0221(4) 0.0225(4) 0.0002(4) 0.0057(3) -0.0017(4) O2 0.0200(4) 0.0129(4) 0.0212(4) 0.0012(3) 0.0031(4) 0.0011(3) O3 0.0149(4) 0.0203(4) 0.0164(4) -0.0057(4) -0.0006(3) -0.0014(4) O1 0.0165(4) 0.0156(4) 0.0114(4) 0.0023(3) -0.0038(3) -0.0029(3) S1 0.01227(12) 0.01206(12) 0.01340(12) -0.00208(11) 0.00063(10) -0.00010(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 C21 O4 1.3603(15) . ? C21 C20 1.3926(17) . ? C21 C22 1.3977(17) . ? C22 C23 1.3765(17) . ? C22 H22 0.9500 . ? C23 C18 1.3983(17) . ? C23 H23 0.9500 . ? C18 C19 1.3878(16) . ? C18 S1 1.7640(12) . ? C19 C20 1.3919(17) . ? C19 H19 0.9500 . ? C20 H20 0.9500 . ? C5 N1 1.4887(15) . ? C5 C4 1.5330(17) . ? C5 C6 1.5392(16) . ? C5 H5 1.0000 . ? C4 C3 1.5338(17) . ? C4 H4B 0.9900 . ? C4 H4A 0.9900 . ? C2 N1 1.4850(14) . ? C2 C1 1.5231(16) . ? C2 C3 1.5399(16) . ? C2 H2 1.0000 . ? C3 H3B 0.9900 . ? C3 H3A 0.9900 . ? C6 C7 1.5280(17) . ? C6 C8 1.5316(17) . ? C6 H6 1.0000 . ? C7 H7B 0.9800 . ? C7 H7C 0.9800 . ? C7 H7A 0.9800 . ? C8 H8B 0.9800 . ? C8 H8C 0.9800 . ? C8 H8A 0.9800 . ? C1 O1 1.4308(14) . ? C1 H1A 0.9900 . ? C1 H1B 0.9900 . ? C9 N2 1.4959(15) . ? C9 C14 1.5326(17) . ? C9 C15 1.5341(17) . ? C9 C10 1.5386(17) . ? C15 H15A 0.9800 . ? C15 H15B 0.9800 . ? C15 H15C 0.9800 . ? C14 H14B 0.9800 . ? C14 H14A 0.9800 . ? C14 H14C 0.9800 . ? C10 C11 1.5209(18) . ? C10 H10B 0.9900 . ? C10 H10A 0.9900 . ? C11 C12 1.516(2) . ? C11 H11B 0.9900 . ? C11 H11A 0.9900 . ? C12 C13 1.5374(17) . ? C12 H12A 0.9900 . ? C12 H12B 0.9900 . ? C13 N2 1.4961(15) . ? C13 C16 1.5278(18) . ? C13 C17 1.5425(18) . ? C17 H17B 0.9800 . ? C17 H17A 0.9800 . ? C17 H17C 0.9800 . ? C16 H13A 0.9800 . ? C16 H13B 0.9800 . ? C16 H13C 0.9800 . ? C24 O4 1.4286(16) . ? C24 H24C 0.9800 . ? C24 H24B 0.9800 . ? C24 H24A 0.9800 . ? N1 S1 1.6239(10) . ? N2 O1 1.4553(12) . ? O2 S1 1.4361(9) . ? O3 S1 1.4390(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 O4 C21 C20 124.69(11) . . ? O4 C21 C22 115.02(11) . . ? C20 C21 C22 120.29(11) . . ? C23 C22 C21 120.31(11) . . ? C23 C22 H22 119.8 . . ? C21 C22 H22 119.8 . . ? C22 C23 C18 119.54(11) . . ? C22 C23 H23 120.2 . . ? C18 C23 H23 120.2 . . ? C19 C18 C23 120.32(11) . . ? C19 C18 S1 120.55(9) . . ? C23 C18 S1 119.13(9) . . ? C18 C19 C20 120.25(11) . . ? C18 C19 H19 119.9 . . ? C20 C19 H19 119.9 . . ? C19 C20 C21 119.25(11) . . ? C19 C20 H20 120.4 . . ? C21 C20 H20 120.4 . . ? N1 C5 C4 102.36(9) . . ? N1 C5 C6 110.45(9) . . ? C4 C5 C6 113.92(10) . . ? N1 C5 H5 110.0 . . ? C4 C5 H5 110.0 . . ? C6 C5 H5 110.0 . . ? C5 C4 C3 103.92(9) . . ? C5 C4 H4B 111.0 . . ? C3 C4 H4B 111.0 . . ? C5 C4 H4A 111.0 . . ? C3 C4 H4A 111.0 . . ? H4B C4 H4A 109.0 . . ? N1 C2 C1 110.37(9) . . ? N1 C2 C3 104.09(9) . . ? C1 C2 C3 112.62(10) . . ? N1 C2 H2 109.9 . . ? C1 C2 H2 109.9 . . ? C3 C2 H2 109.9 . . ? C4 C3 C2 105.57(9) . . ? C4 C3 H3B 110.6 . . ? C2 C3 H3B 110.6 . . ? C4 C3 H3A 110.6 . . ? C2 C3 H3A 110.6 . . ? H3B C3 H3A 108.8 . . ? C7 C6 C8 109.69(10) . . ? C7 C6 C5 111.86(10) . . ? C8 C6 C5 110.30(10) . . ? C7 C6 H6 108.3 . . ? C8 C6 H6 108.3 . . ? C5 C6 H6 108.3 . . ? C6 C7 H7B 109.5 . . ? C6 C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? C6 C7 H7A 109.5 . . ? H7B C7 H7A 109.5 . . ? H7C C7 H7A 109.5 . . ? C6 C8 H8B 109.5 . . ? C6 C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? C6 C8 H8A 109.5 . . ? H8B C8 H8A 109.5 . . ? H8C C8 H8A 109.5 . . ? O1 C1 C2 104.47(9) . . ? O1 C1 H1A 110.9 . . ? C2 C1 H1A 110.9 . . ? O1 C1 H1B 110.9 . . ? C2 C1 H1B 110.9 . . ? H1A C1 H1B 108.9 . . ? N2 C9 C14 114.98(10) . . ? N2 C9 C15 107.31(10) . . ? C14 C9 C15 108.18(11) . . ? N2 C9 C10 107.40(10) . . ? C14 C9 C10 111.15(10) . . ? C15 C9 C10 107.52(10) . . ? C9 C15 H15A 109.5 . . ? C9 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? C9 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? C9 C14 H14B 109.5 . . ? C9 C14 H14A 109.5 . . ? H14B C14 H14A 109.5 . . ? C9 C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? C11 C10 C9 113.06(11) . . ? C11 C10 H10B 109.0 . . ? C9 C10 H10B 109.0 . . ? C11 C10 H10A 109.0 . . ? C9 C10 H10A 109.0 . . ? H10B C10 H10A 107.8 . . ? C12 C11 C10 108.39(11) . . ? C12 C11 H11B 110.0 . . ? C10 C11 H11B 110.0 . . ? C12 C11 H11A 110.0 . . ? C10 C11 H11A 110.0 . . ? H11B C11 H11A 108.4 . . ? C11 C12 C13 113.28(11) . . ? C11 C12 H12A 108.9 . . ? C13 C12 H12A 108.9 . . ? C11 C12 H12B 108.9 . . ? C13 C12 H12B 108.9 . . ? H12A C12 H12B 107.7 . . ? N2 C13 C16 106.67(10) . . ? N2 C13 C12 107.47(10) . . ? C16 C13 C12 107.94(11) . . ? N2 C13 C17 115.57(10) . . ? C16 C13 C17 108.70(10) . . ? C12 C13 C17 110.20(10) . . ? C13 C17 H17B 109.5 . . ? C13 C17 H17A 109.5 . . ? H17B C17 H17A 109.5 . . ? C13 C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? C13 C16 H13A 109.5 . . ? C13 C16 H13B 109.5 . . ? H13A C16 H13B 109.5 . . ? C13 C16 H13C 109.5 . . ? H13A C16 H13C 109.5 . . ? H13B C16 H13C 109.5 . . ? O4 C24 H24C 109.5 . . ? O4 C24 H24B 109.5 . . ? H24C C24 H24B 109.5 . . ? O4 C24 H24A 109.5 . . ? H24C C24 H24A 109.5 . . ? H24B C24 H24A 109.5 . . ? C2 N1 C5 111.66(9) . . ? C2 N1 S1 118.55(8) . . ? C5 N1 S1 122.06(8) . . ? O1 N2 C9 106.30(9) . . ? O1 N2 C13 106.03(9) . . ? C9 N2 C13 118.35(9) . . ? C21 O4 C24 117.82(10) . . ? C1 O1 N2 111.34(8) . . ? O2 S1 O3 118.97(6) . . ? O2 S1 N1 107.89(5) . . ? O3 S1 N1 106.48(5) . . ? O2 S1 C18 106.88(6) . . ? O3 S1 C18 108.51(5) . . ? N1 S1 C18 107.66(5) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O4 C21 C22 C23 178.15(11) . . . . ? C20 C21 C22 C23 -1.98(18) . . . . ? C21 C22 C23 C18 1.52(18) . . . . ? C22 C23 C18 C19 0.24(18) . . . . ? C22 C23 C18 S1 -179.84(10) . . . . ? C23 C18 C19 C20 -1.56(17) . . . . ? S1 C18 C19 C20 178.52(9) . . . . ? C18 C19 C20 C21 1.11(17) . . . . ? O4 C21 C20 C19 -179.49(11) . . . . ? C22 C21 C20 C19 0.65(17) . . . . ? N1 C5 C4 C3 -34.42(11) . . . . ? C6 C5 C4 C3 84.81(12) . . . . ? C5 C4 C3 C2 32.47(12) . . . . ? N1 C2 C3 C4 -17.22(12) . . . . ? C1 C2 C3 C4 -136.79(10) . . . . ? N1 C5 C6 C7 -49.71(13) . . . . ? C4 C5 C6 C7 -164.24(10) . . . . ? N1 C5 C6 C8 -172.08(9) . . . . ? C4 C5 C6 C8 73.38(12) . . . . ? N1 C2 C1 O1 -174.14(9) . . . . ? C3 C2 C1 O1 -58.29(12) . . . . ? N2 C9 C10 C11 54.20(14) . . . . ? C14 C9 C10 C11 -72.37(14) . . . . ? C15 C9 C10 C11 169.40(11) . . . . ? C9 C10 C11 C12 -58.11(14) . . . . ? C10 C11 C12 C13 57.99(14) . . . . ? C11 C12 C13 N2 -53.95(14) . . . . ? C11 C12 C13 C16 -168.65(11) . . . . ? C11 C12 C13 C17 72.78(14) . . . . ? C1 C2 N1 C5 116.07(10) . . . . ? C3 C2 N1 C5 -5.01(12) . . . . ? C1 C2 N1 S1 -93.91(10) . . . . ? C3 C2 N1 S1 145.01(8) . . . . ? C4 C5 N1 C2 24.92(11) . . . . ? C6 C5 N1 C2 -96.72(11) . . . . ? C4 C5 N1 S1 -123.88(9) . . . . ? C6 C5 N1 S1 114.47(10) . . . . ? C14 C9 N2 O1 -48.17(13) . . . . ? C15 C9 N2 O1 72.21(11) . . . . ? C10 C9 N2 O1 -172.44(9) . . . . ? C14 C9 N2 C13 70.83(13) . . . . ? C15 C9 N2 C13 -168.80(10) . . . . ? C10 C9 N2 C13 -53.45(13) . . . . ? C16 C13 N2 O1 -72.06(11) . . . . ? C12 C13 N2 O1 172.40(10) . . . . ? C17 C13 N2 O1 48.90(12) . . . . ? C16 C13 N2 C9 168.80(10) . . . . ? C12 C13 N2 C9 53.26(13) . . . . ? C17 C13 N2 C9 -70.24(13) . . . . ? C20 C21 O4 C24 10.76(17) . . . . ? C22 C21 O4 C24 -169.37(11) . . . . ? C2 C1 O1 N2 177.05(9) . . . . ? C9 N2 O1 C1 -116.03(10) . . . . ? C13 N2 O1 C1 117.19(10) . . . . ? C2 N1 S1 O2 58.38(10) . . . . ? C5 N1 S1 O2 -154.84(9) . . . . ? C2 N1 S1 O3 -172.84(8) . . . . ? C5 N1 S1 O3 -26.07(10) . . . . ? C2 N1 S1 C18 -56.64(10) . . . . ? C5 N1 S1 C18 90.13(10) . . . . ? C19 C18 S1 O2 5.51(11) . . . . ? C23 C18 S1 O2 -174.40(9) . . . . ? C19 C18 S1 O3 -123.94(10) . . . . ? C23 C18 S1 O3 56.14(11) . . . . ? C19 C18 S1 N1 121.20(10) . . . . ? C23 C18 S1 N1 -58.72(10) . . . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 28.19 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.279 _refine_diff_density_min -0.232 _refine_diff_density_rms 0.038