# Copyright The Royal Society of Chemistry, 1999 # CCDC Number: 207/327 data_global _publ-contact_author_name ; T. L. Gilchrist ; _publ_contact_author_name ; Chemistry Department, The University of Liverpool Liverpool L69 7ZD, U.K. ; _publ_section_journal ' Perkin Trans. 1' _publ_section_title ; Diastereoselectivity in the Addition and Cycloaddition Reactions of a Chiral Ester of 2H-Azirine-3-carboxylic Acid ; data_za107 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_sum 'C22 H34 N2 O4 S' _chemical_formula_weight 422.64 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0020 0.0020 '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' 0.0040 0.0030 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'S' 'S' 0.1100 0.1240 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'O' 'O' 0.0080 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 ' P 21 ' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 7.4889(12) _cell_length_b 8.9188(12) _cell_length_c 16.948(2) _cell_angle_alpha 90.00 _cell_angle_beta 101.972(17) _cell_angle_gamma 90.00 _cell_volume 1107.4(3) _cell_formula_units_Z 2 _cell_measurement_temperature 213(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ' needle' _exptl_crystal_colour ' Colourless' _exptl_crystal_size_max .8 _exptl_crystal_size_mid .3 _exptl_crystal_size_min .2 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.268 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 456 _exptl_absorpt_coefficient_mu 0.135 _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_type ' STOE IPDS' _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 5572 _diffrn_reflns_av_R_equivalents 0.0861 _diffrn_reflns_av_sigmaI/netI 0.0785 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 2.46 _diffrn_reflns_theta_max 22.48 _reflns_number_total 2891 _reflns_number_gt 2418 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'IPDS (STOE, 1997)' _computing_cell_refinement ? _computing_data_reduction 'X-RED (STOE, 1996)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme 'calc w=1/[\s^2^(Fo^2^)+(0.0835P)^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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.15(13) _refine_ls_number_reflns 2891 _refine_ls_number_parameters 314 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0616 _refine_ls_R_factor_gt 0.0524 _refine_ls_wR_factor_ref 0.1289 _refine_ls_wR_factor_gt 0.1246 _refine_ls_goodness_of_fit_ref 0.978 _refine_ls_restrained_S_all 0.978 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.6178(6) 0.2082(5) 0.4494(3) 0.0367(10) Uani 1 d . . . H1 H 0.523(8) 0.160(6) 0.419(3) 0.053(14) Uiso 1 d . . . C2 C 0.5981(6) 0.2987(5) 0.5221(3) 0.0420(11) Uani 1 d . . . H2 H 0.4894 0.3293 0.5355 0.050 Uiso 1 calc R . . C3 C 0.7655(6) 0.3264(6) 0.5635(3) 0.0427(11) Uani 1 d . . . H3 H 0.7962 0.3810 0.6112 0.051 Uiso 1 calc R . . C4 C 0.8964(7) 0.2531(5) 0.5190(3) 0.0369(10) Uani 1 d . . . H4 H 0.994(6) 0.243(4) 0.548(2) 0.026(11) Uiso 1 d . . . C5 C 0.7840(6) 0.1150(5) 0.4853(3) 0.0385(11) Uani 1 d . . . H5A H 0.830(6) 0.064(6) 0.447(3) 0.047(12) Uiso 1 d . . . H5B H 0.774(7) 0.035(6) 0.530(3) 0.061(14) Uiso 1 d . . . C6 C 0.8884(5) 0.3357(5) 0.4389(2) 0.0297(9) Uani 1 d . . . C7 C 0.7545(6) 0.4591(5) 0.4133(3) 0.0371(10) Uani 1 d . . . H7A H 0.729(7) 0.504(6) 0.456(3) 0.049(13) Uiso 1 d . . . H7B H 0.762(5) 0.529(5) 0.368(2) 0.028(10) Uiso 1 d . . . C8 C 1.0433(5) 0.3083(5) 0.3973(2) 0.0311(9) Uani 1 d . . . C9 C 1.1532(5) 0.3542(5) 0.2761(2) 0.0384(10) Uani 1 d . . . H9 H 1.2238 0.2623 0.2909 0.046 Uiso 1 calc R . . C10 C 1.2796(7) 0.4930(7) 0.2825(3) 0.0534(13) Uani 1 d . . . H10A H 1.421(7) 0.462(5) 0.306(3) 0.043(12) Uiso 1 d . . . H10B H 1.249(7) 0.569(7) 0.326(3) 0.075(17) Uiso 1 d . . . C11 C 1.2441(7) 0.5508(7) 0.1953(3) 0.0559(13) Uani 1 d . . . H11 H 1.258(7) 0.658(7) 0.200(3) 0.060(16) Uiso 1 d . . . C12 C 1.3311(8) 0.4402(8) 0.1465(4) 0.0767(19) Uani 1 d . . . H12A H 1.4548 0.4160 0.1739 0.092 Uiso 1 calc R . . H12B H 1.3332 0.4797 0.0934 0.092 Uiso 1 calc R . . C13 C 1.2060(8) 0.3020(7) 0.1409(4) 0.0612(15) Uani 1 d . . . H13A H 1.122(9) 0.271(7) 0.086(4) 0.09(2) Uiso 1 d . . . H13B H 1.264(10) 0.216(8) 0.166(4) 0.08(2) Uiso 1 d . . . C14 C 0.9714(9) 0.5518(7) 0.0743(3) 0.0660(15) Uani 1 d . . . H14B H 0.9633 0.6579 0.0649 0.079 Uiso 1 calc R . . H14A H 0.8535 0.5071 0.0560 0.079 Uiso 1 calc R . . H5C H 1.0565 0.5089 0.0455 0.079 Uiso 1 calc R . . C15 C 1.0363(6) 0.5223(5) 0.1643(2) 0.0419(11) Uani 1 d . . . C16 C 0.9145(7) 0.6141(5) 0.2087(3) 0.0516(13) Uani 1 d . . . H16A H 0.9118 0.7166 0.1912 0.062 Uiso 1 calc R . . H16B H 0.9626 0.6092 0.2657 0.062 Uiso 1 calc R . . H16C H 0.7930 0.5739 0.1969 0.062 Uiso 1 calc R . . C17 C 1.0548(6) 0.3514(5) 0.1873(3) 0.0369(10) Uani 1 d . . . C18 C 0.8782(7) 0.2630(5) 0.1684(3) 0.0384(10) Uani 1 d . . . H18A H 0.794(6) 0.290(5) 0.197(3) 0.036(12) Uiso 1 d . . . H18B H 0.813(6) 0.275(5) 0.106(3) 0.036(11) Uiso 1 d . . . C19 C 0.5795(9) -0.0036(7) 0.0905(3) 0.0689(16) Uani 1 d . . . H19A H 0.4809 0.0679 0.0881 0.083 Uiso 1 calc R . . H19B H 0.6516 0.0283 0.0522 0.083 Uiso 1 calc R . . C20 C 0.5013(10) -0.1512(8) 0.0665(4) 0.086(2) Uani 1 d . . . H20A H 0.4280 -0.1455 0.0129 0.104 Uiso 1 calc R . . H20B H 0.4268 -0.1824 0.1032 0.104 Uiso 1 calc R . . H20C H 0.5980 -0.2223 0.0675 0.104 Uiso 1 calc R . . C21 C 0.6043(8) 0.0137(7) 0.2409(3) 0.0588(14) Uani 1 d . . . H21A H 0.4773 0.0407 0.2213 0.071 Uiso 1 calc R . . H21B H 0.6620 0.0938 0.2757 0.071 Uiso 1 calc R . . C22 C 0.6140(11) -0.1300(8) 0.2892(4) 0.0817(19) Uani 1 d . . . H22A H 0.5549 -0.1155 0.3338 0.098 Uiso 1 calc R . . H22B H 0.7394 -0.1566 0.3091 0.098 Uiso 1 calc R . . H22C H 0.5537 -0.2090 0.2553 0.098 Uiso 1 calc R . . N1 N 0.6998(4) 0.3052(4) 0.3897(2) 0.0324(8) Uani 1 d . . . N2 N 0.6947(6) -0.0010(4) 0.1717(2) 0.0480(10) Uani 1 d . . . S1 S 0.90201(19) 0.06480(11) 0.18255(7) 0.0500(4) Uani 1 d . . . O1 O 1.1781(4) 0.2390(4) 0.42705(18) 0.0460(8) Uani 1 d . . . O2 O 1.0139(4) 0.3732(3) 0.32481(16) 0.0359(7) Uani 1 d . . . O3 O 0.9923(5) 0.0374(4) 0.2636(2) 0.0595(9) Uani 1 d . . . O4 O 0.9771(7) 0.0043(4) 0.1173(3) 0.0842(14) Uani 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 0.032(2) 0.045(3) 0.034(2) -0.0003(19) 0.008(2) -0.006(2) C2 0.040(3) 0.049(3) 0.042(3) 0.004(2) 0.020(2) 0.010(2) C3 0.044(3) 0.055(3) 0.032(2) -0.001(2) 0.013(2) 0.002(2) C4 0.027(2) 0.054(3) 0.026(2) -0.001(2) -0.0017(19) 0.007(2) C5 0.040(3) 0.037(2) 0.041(3) 0.006(2) 0.014(2) 0.0023(18) C6 0.024(2) 0.033(2) 0.032(2) -0.0029(18) 0.0065(17) -0.0009(18) C7 0.039(3) 0.037(3) 0.038(3) 0.003(2) 0.013(2) 0.0075(19) C8 0.024(2) 0.037(2) 0.032(2) -0.0009(19) 0.0037(17) -0.0041(19) C9 0.034(2) 0.051(3) 0.034(2) 0.006(2) 0.0155(18) 0.008(2) C10 0.035(3) 0.076(4) 0.048(3) 0.006(3) 0.006(2) -0.014(2) C11 0.057(3) 0.066(4) 0.050(3) 0.006(3) 0.022(2) -0.020(3) C12 0.061(4) 0.111(5) 0.070(4) 0.005(3) 0.040(3) -0.013(3) C13 0.060(3) 0.082(4) 0.052(3) 0.004(3) 0.036(3) 0.013(3) C14 0.095(4) 0.051(3) 0.049(3) 0.018(3) 0.008(3) -0.014(3) C15 0.048(3) 0.038(3) 0.040(2) 0.009(2) 0.010(2) -0.0067(19) C16 0.060(3) 0.025(2) 0.068(3) 0.009(2) 0.010(3) 0.000(2) C17 0.044(2) 0.036(2) 0.035(2) 0.0006(18) 0.0186(19) 0.004(2) C18 0.046(3) 0.034(2) 0.035(2) -0.0005(19) 0.009(2) 0.004(2) C19 0.105(5) 0.051(3) 0.047(3) -0.002(2) 0.006(3) -0.003(3) C20 0.102(5) 0.069(4) 0.073(4) -0.001(3) -0.015(4) -0.017(4) C21 0.067(3) 0.063(3) 0.048(3) 0.001(2) 0.017(3) 0.002(3) C22 0.117(5) 0.081(5) 0.061(4) -0.001(3) 0.050(4) -0.018(4) N1 0.0260(17) 0.036(2) 0.0343(18) -0.0005(15) 0.0047(14) 0.0028(15) N2 0.074(3) 0.040(2) 0.0284(19) -0.0029(16) 0.0073(18) -0.012(2) S1 0.0732(9) 0.0306(6) 0.0503(7) -0.0001(5) 0.0223(6) 0.0012(6) O1 0.0295(17) 0.069(2) 0.0403(17) 0.0150(15) 0.0090(13) 0.0096(16) O2 0.0337(15) 0.046(2) 0.0310(16) 0.0077(13) 0.0145(12) 0.0071(13) O3 0.073(2) 0.038(2) 0.062(2) 0.0138(16) 0.0033(17) 0.0001(17) O4 0.139(4) 0.0451(19) 0.089(3) -0.013(2) 0.073(3) -0.003(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C2 1.505(6) . ? C1 C5 1.516(6) . ? C1 N1 1.552(5) . ? C2 C3 1.327(7) . ? C3 C4 1.505(6) . ? C4 C5 1.534(7) . ? C4 C6 1.535(6) . ? C6 C7 1.492(6) . ? C6 C8 1.497(5) . ? C6 N1 1.509(5) . ? C7 N1 1.464(6) . ? C8 O1 1.202(5) . ? C8 O2 1.335(5) . ? C9 O2 1.468(5) . ? C9 C17 1.532(6) . ? C9 C10 1.548(7) . ? C10 C11 1.536(7) . ? C11 C12 1.518(9) . ? C11 C15 1.557(7) . ? C12 C13 1.539(9) . ? C13 C17 1.570(6) . ? C14 C15 1.524(6) . ? C15 C16 1.534(7) . ? C15 C17 1.572(6) . ? C17 C18 1.516(7) . ? C18 S1 1.788(4) . ? C19 C20 1.464(9) . ? C19 N2 1.465(6) . ? C21 N2 1.476(6) . ? C21 C22 1.514(8) . ? N2 S1 1.634(4) . ? S1 O3 1.421(4) . ? S1 O4 1.444(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 C2 C1 C5 100.2(4) . . ? C2 C1 N1 110.8(4) . . ? C5 C1 N1 99.5(3) . . ? C3 C2 C1 106.9(4) . . ? C2 C3 C4 107.2(4) . . ? C3 C4 C5 99.9(4) . . ? C3 C4 C6 109.0(4) . . ? C5 C4 C6 97.9(3) . . ? C1 C5 C4 92.9(4) . . ? C7 C6 C8 121.5(4) . . ? C7 C6 N1 58.4(3) . . ? C8 C6 N1 116.0(3) . . ? C7 C6 C4 120.8(3) . . ? C8 C6 C4 116.5(3) . . ? N1 C6 C4 105.2(3) . . ? N1 C7 C6 61.4(3) . . ? O1 C8 O2 124.9(3) . . ? O1 C8 C6 123.5(4) . . ? O2 C8 C6 111.6(3) . . ? O2 C9 C17 107.5(3) . . ? O2 C9 C10 111.3(4) . . ? C17 C9 C10 104.1(3) . . ? C11 C10 C9 102.7(4) . . ? C12 C11 C10 107.3(5) . . ? C12 C11 C15 102.8(4) . . ? C10 C11 C15 103.4(3) . . ? C11 C12 C13 103.3(4) . . ? C12 C13 C17 103.7(4) . . ? C14 C15 C16 107.5(4) . . ? C14 C15 C11 113.5(4) . . ? C16 C15 C11 113.7(4) . . ? C14 C15 C17 114.2(4) . . ? C16 C15 C17 115.2(3) . . ? C11 C15 C17 92.5(4) . . ? C18 C17 C9 115.9(3) . . ? C18 C17 C13 115.9(4) . . ? C9 C17 C13 104.3(4) . . ? C18 C17 C15 115.0(4) . . ? C9 C17 C15 103.2(4) . . ? C13 C17 C15 100.5(4) . . ? C17 C18 S1 115.3(3) . . ? C20 C19 N2 113.5(5) . . ? N2 C21 C22 112.1(5) . . ? C7 N1 C6 60.2(3) . . ? C7 N1 C1 118.0(3) . . ? C6 N1 C1 101.0(3) . . ? C19 N2 C21 118.0(5) . . ? C19 N2 S1 118.2(3) . . ? C21 N2 S1 117.4(3) . . ? O3 S1 O4 119.5(3) . . ? O3 S1 N2 107.3(2) . . ? O4 S1 N2 107.0(2) . . ? O3 S1 C18 108.3(2) . . ? O4 S1 C18 108.1(2) . . ? N2 S1 C18 105.9(2) . . ? C8 O2 C9 117.9(3) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C5 C1 C2 C3 35.3(5) . . . . ? N1 C1 C2 C3 -69.0(5) . . . . ? C1 C2 C3 C4 -0.6(5) . . . . ? C2 C3 C4 C5 -33.7(5) . . . . ? C2 C3 C4 C6 68.3(5) . . . . ? C2 C1 C5 C4 -52.0(4) . . . . ? N1 C1 C5 C4 61.3(4) . . . . ? C3 C4 C5 C1 51.5(4) . . . . ? C6 C4 C5 C1 -59.4(3) . . . . ? C3 C4 C6 C7 -4.6(6) . . . . ? C5 C4 C6 C7 98.7(4) . . . . ? C3 C4 C6 C8 163.3(4) . . . . ? C5 C4 C6 C8 -93.3(4) . . . . ? C3 C4 C6 N1 -66.6(4) . . . . ? C5 C4 C6 N1 36.8(4) . . . . ? C8 C6 C7 N1 103.1(4) . . . . ? C4 C6 C7 N1 -89.6(4) . . . . ? C7 C6 C8 O1 160.2(4) . . . . ? N1 C6 C8 O1 -132.5(4) . . . . ? C4 C6 C8 O1 -7.7(6) . . . . ? C7 C6 C8 O2 -18.4(5) . . . . ? N1 C6 C8 O2 49.0(5) . . . . ? C4 C6 C8 O2 173.8(3) . . . . ? O2 C9 C10 C11 -117.6(4) . . . . ? C17 C9 C10 C11 -2.0(5) . . . . ? C9 C10 C11 C12 -71.4(5) . . . . ? C9 C10 C11 C15 36.9(5) . . . . ? C10 C11 C12 C13 71.5(6) . . . . ? C15 C11 C12 C13 -37.2(6) . . . . ? C11 C12 C13 C17 0.9(6) . . . . ? C12 C11 C15 C14 -60.8(6) . . . . ? C10 C11 C15 C14 -172.3(5) . . . . ? C12 C11 C15 C16 176.0(4) . . . . ? C10 C11 C15 C16 64.5(5) . . . . ? C12 C11 C15 C17 57.0(4) . . . . ? C10 C11 C15 C17 -54.5(5) . . . . ? O2 C9 C17 C18 -41.4(5) . . . . ? C10 C9 C17 C18 -159.7(4) . . . . ? O2 C9 C17 C13 -170.1(4) . . . . ? C10 C9 C17 C13 71.7(5) . . . . ? O2 C9 C17 C15 85.2(4) . . . . ? C10 C9 C17 C15 -33.0(4) . . . . ? C12 C13 C17 C18 159.6(4) . . . . ? C12 C13 C17 C9 -71.7(5) . . . . ? C12 C13 C17 C15 35.0(5) . . . . ? C14 C15 C17 C18 -62.7(5) . . . . ? C16 C15 C17 C18 62.4(5) . . . . ? C11 C15 C17 C18 -179.9(4) . . . . ? C14 C15 C17 C9 170.0(4) . . . . ? C16 C15 C17 C9 -64.9(5) . . . . ? C11 C15 C17 C9 52.8(4) . . . . ? C14 C15 C17 C13 62.5(5) . . . . ? C16 C15 C17 C13 -172.4(4) . . . . ? C11 C15 C17 C13 -54.7(4) . . . . ? C9 C17 C18 S1 -67.1(4) . . . . ? C13 C17 C18 S1 55.7(5) . . . . ? C15 C17 C18 S1 172.5(3) . . . . ? C6 C7 N1 C1 86.9(3) . . . . ? C8 C6 N1 C7 -112.5(4) . . . . ? C4 C6 N1 C7 117.1(4) . . . . ? C7 C6 N1 C1 -116.1(3) . . . . ? C8 C6 N1 C1 131.3(4) . . . . ? C4 C6 N1 C1 1.0(4) . . . . ? C2 C1 N1 C7 3.7(5) . . . . ? C5 C1 N1 C7 -101.1(4) . . . . ? C2 C1 N1 C6 65.7(4) . . . . ? C5 C1 N1 C6 -39.1(4) . . . . ? C20 C19 N2 C21 -82.2(7) . . . . ? C20 C19 N2 S1 126.5(5) . . . . ? C22 C21 N2 C19 109.3(6) . . . . ? C22 C21 N2 S1 -99.2(5) . . . . ? C19 N2 S1 O3 -172.5(4) . . . . ? C21 N2 S1 O3 36.1(4) . . . . ? C19 N2 S1 O4 -43.1(4) . . . . ? C21 N2 S1 O4 165.5(4) . . . . ? C19 N2 S1 C18 72.0(4) . . . . ? C21 N2 S1 C18 -79.4(4) . . . . ? C17 C18 S1 O3 56.9(4) . . . . ? C17 C18 S1 O4 -73.9(4) . . . . ? C17 C18 S1 N2 171.7(3) . . . . ? O1 C8 O2 C9 2.4(6) . . . . ? C6 C8 O2 C9 -179.1(3) . . . . ? C17 C9 O2 C8 147.4(3) . . . . ? C10 C9 O2 C8 -99.2(4) . . . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 22.48 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.257 _refine_diff_density_min -0.233 _refine_diff_density_rms 0.055 data_za116 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_sum 'C23 H34 N2 O4 S2' _chemical_formula_weight 466.71 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0020 0.0020 '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' 0.0040 0.0030 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'O' 'O' 0.0080 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'S' 'S' 0.1100 0.1240 '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' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' '-x+1/2, -y, z+1/2' _cell_length_a 10.5115(12) _cell_length_b 11.468(3) _cell_length_c 20.141(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2427.9(7) _cell_formula_units_Z 4 _cell_measurement_temperature 213(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ' needle' _exptl_crystal_colour ' colourless ' _exptl_crystal_size_max .7 _exptl_crystal_size_mid .25 _exptl_crystal_size_min .2 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.277 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1000 _exptl_absorpt_coefficient_mu 0.206 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 213(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 ' STOE IPDS' _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 13051 _diffrn_reflns_av_R_equivalents 0.0643 _diffrn_reflns_av_sigmaI/netI 0.0495 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 2.02 _diffrn_reflns_theta_max 22.48 _reflns_number_total 3150 _reflns_number_gt 2645 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'IPDS (STOE, 1997)' _computing_cell_refinement ? _computing_data_reduction 'X-RED (STOE, 1996)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme 'calc w=1/[\s^2^(Fo^2^)+(0.0480P)^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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.05(8) _refine_ls_number_reflns 3150 _refine_ls_number_parameters 308 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0440 _refine_ls_R_factor_gt 0.0344 _refine_ls_wR_factor_ref 0.0812 _refine_ls_wR_factor_gt 0.0779 _refine_ls_goodness_of_fit_ref 0.974 _refine_ls_restrained_S_all 0.974 _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_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C21 C 0.3163(4) 0.4591(3) 1.04356(18) 0.0492(8) Uani 1 d . . . H21A H 0.3619 0.4476 1.0849 0.059 Uiso 1 calc R . . H21B H 0.3588 0.4168 1.0083 0.059 Uiso 1 calc R . . H21C H 0.2299 0.4306 1.0482 0.059 Uiso 1 calc R . . C20 C 0.3136(3) 0.5884(2) 1.02675(13) 0.0333(7) Uani 1 d . . . H20A H 0.2703 0.6309 1.0624 0.040 Uiso 1 calc R . . H20B H 0.4010 0.6178 1.0238 0.040 Uiso 1 calc R . . C22 C 0.3099(4) 0.5667(3) 0.90201(14) 0.0434(9) Uani 1 d . . . H22A H 0.3915 0.5309 0.9138 0.052 Uiso 1 calc R . . H22B H 0.3274 0.6327 0.8724 0.052 Uiso 1 calc R . . C19 C 0.2969(3) 0.8423(2) 0.95376(15) 0.0277(7) Uani 1 d . . . H19A H 0.3498 0.8337 0.9935 0.033 Uiso 1 calc R . . H19B H 0.3508 0.8254 0.9153 0.033 Uiso 1 calc R . . C17 C 0.1788(4) 1.0154(2) 1.00990(13) 0.0332(7) Uani 1 d . . . H17A H 0.0890 0.9929 1.0070 0.040 Uiso 1 calc R . . H17B H 0.2142 0.9855 1.0516 0.040 Uiso 1 calc R . . C10 C 0.1714(3) 1.0028(2) 0.88971(12) 0.0289(7) Uani 1 d . . . H10 H 0.0811 0.9843 0.8989 0.035 Uiso 1 calc R . . C6 C 0.3103(4) 1.0506(3) 0.69367(14) 0.0447(9) Uani 1 d . . . C16 C 0.2546(3) 0.9689(2) 0.94929(14) 0.0257(6) Uani 1 d . . . C9 C 0.1227(4) 0.9171(3) 0.78551(14) 0.0408(9) Uani 1 d . . . C2 C 0.1874(4) 1.2244(3) 0.67574(14) 0.0479(9) Uani 1 d . . . H2 H 0.1096 1.2598 0.6647 0.057 Uiso 1 calc R . . C1 C 0.1972(3) 1.1038(3) 0.67633(14) 0.0411(8) Uani 1 d . . . H1 H 0.1264 1.0580 0.6648 0.049 Uiso 1 calc R . . C4 C 0.4036(5) 1.2405(5) 0.70659(18) 0.0787(16) Uani 1 d . . . H4 H 0.4748 1.2873 0.7159 0.094 Uiso 1 calc R . . C5 C 0.4146(4) 1.1202(4) 0.70858(16) 0.0632(12) Uani 1 d . . . H5 H 0.4926 1.0857 0.7200 0.076 Uiso 1 calc R . . C3 C 0.2897(5) 1.2915(4) 0.69110(17) 0.0685(13) Uani 1 d . . . H3 H 0.2823 1.3732 0.6911 0.082 Uiso 1 calc R . . C11 C 0.1899(4) 1.1356(3) 0.88370(18) 0.0374(8) Uani 1 d . . . H11B H 0.110(3) 1.177(3) 0.8848(13) 0.031(8) Uiso 1 d . . . H11A H 0.215(3) 1.151(3) 0.8465(18) 0.039(10) Uiso 1 d . . . C14 C 0.3667(3) 1.0594(2) 0.94646(14) 0.0307(7) Uani 1 d . . . C18 C 0.1940(4) 1.1498(3) 1.00540(17) 0.0424(9) Uani 1 d . . . H18A H 0.117(4) 1.189(3) 1.0014(17) 0.054(11) Uiso 1 d . . . H18B H 0.242(4) 1.181(3) 1.044(2) 0.067(11) Uiso 1 d . . . C12 C 0.2758(3) 1.1647(3) 0.94298(16) 0.0373(8) Uani 1 d . . . H12 H 0.322(3) 1.240(2) 0.9381(12) 0.029(7) Uiso 1 d . . . C15 C 0.4503(3) 1.0589(3) 1.00852(14) 0.0374(8) Uani 1 d . . . H15C H 0.5178 1.1159 1.0035 0.045 Uiso 1 calc R . . H15B H 0.4871 0.9821 1.0144 0.045 Uiso 1 calc R . . H15A H 0.3990 1.0785 1.0470 0.045 Uiso 1 calc R . . C7 C 0.1771(4) 0.8531(3) 0.72666(15) 0.0499(10) Uani 1 d . . . C13 C 0.4540(3) 1.0471(3) 0.88636(15) 0.0412(9) Uani 1 d . . . H13C H 0.5204 1.1057 0.8885 0.049 Uiso 1 calc R . . H13B H 0.4050 1.0576 0.8460 0.049 Uiso 1 calc R . . H13A H 0.4921 0.9700 0.8864 0.049 Uiso 1 calc R . . C23 C 0.2288(4) 0.4781(3) 0.86554(18) 0.0622(12) Uani 1 d . . . H23A H 0.2734 0.4516 0.8262 0.075 Uiso 1 calc R . . H23B H 0.1488 0.5138 0.8527 0.075 Uiso 1 calc R . . H23C H 0.2121 0.4122 0.8944 0.075 Uiso 1 calc R . . C8 C 0.1391(8) 0.7286(4) 0.7201(3) 0.0821(17) Uani 1 d . . . H8A H 0.204(4) 0.691(4) 0.705(2) 0.070(16) Uiso 1 d . . . H8B H 0.082(4) 0.701(4) 0.755(2) 0.068(13) Uiso 1 d . . . N2 N 0.2474(2) 0.61026(18) 0.96314(11) 0.0294(6) Uani 1 d . . . N1 N 0.0802(4) 0.8168(3) 0.67794(14) 0.0749(12) Uani 1 d . . . H1N H 0.0267 0.8348 0.6467 0.090 Uiso 1 calc R . . O3 O 0.1083(2) 0.73452(18) 0.89445(11) 0.0482(6) Uani 1 d . . . O4 O 0.1019(2) 0.75238(18) 1.01640(11) 0.0457(6) Uani 1 d . . . O2 O 0.21382(19) 0.94289(16) 0.82970(9) 0.0329(5) Uani 1 d . . . O1 O 0.0123(3) 0.9408(2) 0.79080(11) 0.0508(6) Uani 1 d . . . S2 S 0.17454(8) 0.73531(6) 0.95695(4) 0.0326(2) Uani 1 d . . . S1 S 0.32893(12) 0.89717(9) 0.69686(4) 0.0614(3) Uani 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 0.041(2) 0.0415(18) 0.065(2) 0.0160(16) -0.009(2) -0.0043(17) C20 0.0359(19) 0.0292(15) 0.0347(15) 0.0017(13) -0.0074(14) 0.0008(15) C22 0.053(2) 0.0355(18) 0.0416(18) -0.0062(14) 0.0083(17) 0.0042(18) C19 0.0271(19) 0.0253(15) 0.0305(15) -0.0001(12) -0.0003(14) 0.0017(12) C17 0.037(2) 0.0310(16) 0.0316(15) 0.0024(12) 0.0010(15) 0.0033(16) C10 0.038(2) 0.0246(15) 0.0242(14) -0.0003(12) -0.0074(15) 0.0062(15) C6 0.040(2) 0.071(2) 0.0228(15) 0.0015(15) 0.0024(16) 0.004(2) C16 0.0285(17) 0.0235(14) 0.0252(16) 0.0009(12) -0.0034(14) 0.0022(13) C9 0.061(3) 0.0294(17) 0.0317(18) 0.0015(14) -0.0147(17) -0.0071(18) C2 0.055(2) 0.050(2) 0.0384(18) 0.0070(15) 0.0003(18) -0.006(2) C1 0.037(2) 0.051(2) 0.0349(17) 0.0020(15) -0.0014(15) -0.0029(18) C4 0.078(4) 0.115(5) 0.043(2) 0.022(3) -0.017(2) -0.055(3) C5 0.045(3) 0.110(4) 0.035(2) 0.021(2) -0.0011(17) -0.011(3) C3 0.107(4) 0.060(3) 0.039(2) 0.0097(18) -0.009(2) -0.024(3) C11 0.051(3) 0.0289(17) 0.0325(19) 0.0048(15) -0.0071(18) 0.0065(18) C14 0.037(2) 0.0241(15) 0.0314(15) 0.0047(13) -0.0039(13) -0.0038(13) C18 0.059(3) 0.0286(17) 0.039(2) -0.0050(14) -0.0014(19) 0.0118(19) C12 0.051(3) 0.0230(16) 0.0378(19) 0.0013(14) -0.0049(16) -0.0015(15) C15 0.039(2) 0.0321(18) 0.0413(17) 0.0008(14) -0.0097(15) -0.0103(15) C7 0.078(3) 0.0394(19) 0.0328(17) -0.0041(14) -0.013(2) 0.005(2) C13 0.047(2) 0.0367(19) 0.0404(18) 0.0016(15) 0.0041(16) -0.0119(16) C23 0.097(4) 0.041(2) 0.049(2) -0.0190(16) -0.009(2) 0.000(2) C8 0.141(6) 0.047(3) 0.058(3) -0.016(2) -0.013(3) -0.002(3) N2 0.0332(15) 0.0218(11) 0.0334(14) 0.0007(11) -0.0026(11) 0.0029(11) N1 0.121(3) 0.058(2) 0.0463(19) -0.0067(15) -0.046(2) -0.012(2) O3 0.0461(15) 0.0382(13) 0.0604(14) 0.0139(11) -0.0279(11) -0.0128(12) O4 0.0393(15) 0.0327(12) 0.0651(14) 0.0049(11) 0.0211(11) 0.0012(11) O2 0.0411(15) 0.0333(11) 0.0243(10) -0.0017(8) -0.0054(9) -0.0022(9) O1 0.0459(18) 0.0569(16) 0.0497(15) 0.0045(11) -0.0197(12) -0.0024(14) S2 0.0284(4) 0.0240(4) 0.0454(4) 0.0050(3) -0.0053(4) -0.0007(3) S1 0.0731(7) 0.0731(7) 0.0381(4) -0.0071(5) -0.0027(5) 0.0316(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 C21 C20 1.521(4) . ? C20 N2 1.479(3) . ? C22 N2 1.482(4) . ? C22 C23 1.517(5) . ? C19 C16 1.520(3) . ? C19 S2 1.779(3) . ? C17 C18 1.552(4) . ? C17 C16 1.553(4) . ? C10 O2 1.460(3) . ? C10 C16 1.535(4) . ? C10 C11 1.540(4) . ? C6 C1 1.381(5) . ? C6 C5 1.389(5) . ? C6 S1 1.772(4) . ? C16 C14 1.571(4) . ? C9 O1 1.197(4) . ? C9 O2 1.340(4) . ? C9 C7 1.507(5) . ? C2 C3 1.359(6) . ? C2 C1 1.386(5) . ? C4 C3 1.368(6) . ? C4 C5 1.384(6) . ? C11 C12 1.534(5) . ? C14 C13 1.526(4) . ? C14 C15 1.528(4) . ? C14 C12 1.542(4) . ? C18 C12 1.533(5) . ? C7 N1 1.474(5) . ? C7 C8 1.489(6) . ? C7 S1 1.778(5) . ? C8 N1 1.457(6) . ? N2 S2 1.631(2) . ? O3 S2 1.438(2) . ? O4 S2 1.434(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 N2 C20 C21 111.5(2) . . ? N2 C22 C23 112.3(3) . . ? C16 C19 S2 116.7(2) . . ? C18 C17 C16 104.0(3) . . ? O2 C10 C16 110.7(2) . . ? O2 C10 C11 111.2(3) . . ? C16 C10 C11 103.9(2) . . ? C1 C6 C5 118.7(4) . . ? C1 C6 S1 122.9(3) . . ? C5 C6 S1 118.4(3) . . ? C19 C16 C10 117.0(2) . . ? C19 C16 C17 115.6(2) . . ? C10 C16 C17 103.6(2) . . ? C19 C16 C14 114.5(2) . . ? C10 C16 C14 103.4(2) . . ? C17 C16 C14 100.7(2) . . ? O1 C9 O2 125.7(3) . . ? O1 C9 C7 123.3(3) . . ? O2 C9 C7 111.0(4) . . ? C3 C2 C1 120.3(4) . . ? C6 C1 C2 120.4(3) . . ? C3 C4 C5 120.4(4) . . ? C4 C5 C6 120.0(4) . . ? C2 C3 C4 120.1(4) . . ? C12 C11 C10 103.2(2) . . ? C13 C14 C15 107.6(3) . . ? C13 C14 C12 114.2(2) . . ? C15 C14 C12 113.4(2) . . ? C13 C14 C16 114.7(2) . . ? C15 C14 C16 113.5(2) . . ? C12 C14 C16 93.2(2) . . ? C12 C18 C17 102.5(3) . . ? C18 C12 C11 106.5(3) . . ? C18 C12 C14 102.9(2) . . ? C11 C12 C14 103.2(3) . . ? N1 C7 C8 58.9(3) . . ? N1 C7 C9 113.5(4) . . ? C8 C7 C9 115.8(4) . . ? N1 C7 S1 118.4(3) . . ? C8 C7 S1 118.9(4) . . ? C9 C7 S1 117.9(3) . . ? N1 C8 C7 60.1(3) . . ? C20 N2 C22 117.0(2) . . ? C20 N2 S2 115.86(18) . . ? C22 N2 S2 116.16(19) . . ? C8 N1 C7 61.0(3) . . ? C9 O2 C10 115.8(3) . . ? O4 S2 O3 118.29(15) . . ? O4 S2 N2 107.85(12) . . ? O3 S2 N2 106.77(13) . . ? O4 S2 C19 108.74(14) . . ? O3 S2 C19 108.81(14) . . ? N2 S2 C19 105.66(13) . . ? C6 S1 C7 101.25(17) . . ? 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 S2 C19 C16 C10 -58.7(3) . . . . ? S2 C19 C16 C17 63.7(3) . . . . ? S2 C19 C16 C14 -179.87(19) . . . . ? O2 C10 C16 C19 -38.7(4) . . . . ? C11 C10 C16 C19 -158.2(3) . . . . ? O2 C10 C16 C17 -167.2(2) . . . . ? C11 C10 C16 C17 73.4(3) . . . . ? O2 C10 C16 C14 88.1(3) . . . . ? C11 C10 C16 C14 -31.3(3) . . . . ? C18 C17 C16 C19 158.9(3) . . . . ? C18 C17 C16 C10 -71.8(3) . . . . ? C18 C17 C16 C14 35.0(3) . . . . ? C5 C6 C1 C2 -1.8(4) . . . . ? S1 C6 C1 C2 178.9(2) . . . . ? C3 C2 C1 C6 1.2(4) . . . . ? C3 C4 C5 C6 1.2(6) . . . . ? C1 C6 C5 C4 0.7(5) . . . . ? S1 C6 C5 C4 180.0(3) . . . . ? C1 C2 C3 C4 0.7(5) . . . . ? C5 C4 C3 C2 -1.8(6) . . . . ? O2 C10 C11 C12 -122.3(3) . . . . ? C16 C10 C11 C12 -3.2(4) . . . . ? C19 C16 C14 C13 61.8(3) . . . . ? C10 C16 C14 C13 -66.6(3) . . . . ? C17 C16 C14 C13 -173.5(2) . . . . ? C19 C16 C14 C15 -62.5(3) . . . . ? C10 C16 C14 C15 169.1(2) . . . . ? C17 C16 C14 C15 62.2(3) . . . . ? C19 C16 C14 C12 -179.7(2) . . . . ? C10 C16 C14 C12 51.9(2) . . . . ? C17 C16 C14 C12 -55.0(2) . . . . ? C16 C17 C18 C12 0.3(4) . . . . ? C17 C18 C12 C11 71.7(3) . . . . ? C17 C18 C12 C14 -36.5(4) . . . . ? C10 C11 C12 C18 -70.5(3) . . . . ? C10 C11 C12 C14 37.4(4) . . . . ? C13 C14 C12 C18 175.5(3) . . . . ? C15 C14 C12 C18 -60.8(3) . . . . ? C16 C14 C12 C18 56.6(3) . . . . ? C13 C14 C12 C11 64.8(3) . . . . ? C15 C14 C12 C11 -171.5(3) . . . . ? C16 C14 C12 C11 -54.1(3) . . . . ? O1 C9 C7 N1 -3.2(4) . . . . ? O2 C9 C7 N1 176.9(3) . . . . ? O1 C9 C7 C8 -68.7(5) . . . . ? O2 C9 C7 C8 111.4(4) . . . . ? O1 C9 C7 S1 141.6(3) . . . . ? O2 C9 C7 S1 -38.3(3) . . . . ? C9 C7 C8 N1 103.1(4) . . . . ? S1 C7 C8 N1 -107.6(3) . . . . ? C21 C20 N2 C22 -67.4(4) . . . . ? C21 C20 N2 S2 149.7(2) . . . . ? C23 C22 N2 C20 118.9(3) . . . . ? C23 C22 N2 S2 -98.4(3) . . . . ? C9 C7 N1 C8 -106.9(4) . . . . ? S1 C7 N1 C8 108.4(4) . . . . ? O1 C9 O2 C10 1.5(4) . . . . ? C7 C9 O2 C10 -178.6(2) . . . . ? C16 C10 O2 C9 148.3(3) . . . . ? C11 C10 O2 C9 -96.8(3) . . . . ? C20 N2 S2 O4 -47.1(3) . . . . ? C22 N2 S2 O4 169.8(2) . . . . ? C20 N2 S2 O3 -175.2(2) . . . . ? C22 N2 S2 O3 41.7(3) . . . . ? C20 N2 S2 C19 69.1(2) . . . . ? C22 N2 S2 C19 -74.1(2) . . . . ? C16 C19 S2 O4 -63.2(3) . . . . ? C16 C19 S2 O3 66.9(3) . . . . ? C16 C19 S2 N2 -178.8(2) . . . . ? C1 C6 S1 C7 -35.8(3) . . . . ? C5 C6 S1 C7 144.9(3) . . . . ? N1 C7 S1 C6 95.8(3) . . . . ? C8 C7 S1 C6 164.0(3) . . . . ? C9 C7 S1 C6 -47.3(3) . . . . ? _diffrn_measured_fraction_theta_max 0.986 _diffrn_reflns_theta_full 22.48 _diffrn_measured_fraction_theta_full 0.986 _refine_diff_density_max 0.144 _refine_diff_density_min -0.234 _refine_diff_density_rms 0.042