data_150520_cc_1538 _audit_creation_date 2015-05-20 _audit_creation_method ; Olex2 1.2 (compiled 2014.03.20 svn.r2914 for OlexSys, GUI svn.r4816) ; _publ_contact_author_address ? _publ_contact_author_email ? _publ_contact_author_name '' _publ_contact_author_phone ? _publ_section_references ; Dolomanov, O.V., Bourhis, L.J., Gildea, R.J, Howard, J.A.K. & Puschmann, H. (2009), J. Appl. Cryst. 42, 339-341. Sheldrick, G.M. (2008). Acta Cryst. A64, 112-122. ; _chemical_name_common ? _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C22 H22 N2 O3 S' _chemical_formula_sum 'C22 H22 N2 O3 S' _chemical_formula_weight 394.48 _chemical_melting_point ? _chemical_oxdiff_formula 'c10 h10 n2 o8 S1' 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' _space_group_crystal_system 'monoclinic' _space_group_IT_number 14 _space_group_name_H-M_alt 'P 1 21/n 1' _space_group_name_Hall '-P 2yn' loop_ _space_group_symop_id _space_group_symop_operation_xyz 1 'x, y, z' 2 '-x+1/2, y+1/2, -z+1/2' 3 '-x, -y, -z' 4 'x-1/2, -y-1/2, z-1/2' _cell_length_a 13.4257(11) _cell_length_b 10.9838(7) _cell_length_c 14.5635(11) _cell_angle_alpha 90.00 _cell_angle_beta 109.954(9) _cell_angle_gamma 90.00 _cell_volume 2018.7(3) _cell_formula_units_Z 4 _cell_measurement_reflns_used 2008 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 29.5801 _cell_measurement_theta_min 2.9701 _exptl_absorpt_coefficient_mu 0.185 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.84822 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro, Agilent Technologies, Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET) (compiled May 16 2011,17:55:39) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_crystal_colour yellow _exptl_crystal_colour_primary yellow _exptl_crystal_density_diffrn 1.298 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_description block _exptl_crystal_F_000 832 _exptl_crystal_size_max 0.39 _exptl_crystal_size_mid 0.33 _exptl_crystal_size_min 0.2 _exptl_special_details ; ? ; _diffrn_reflns_av_R_equivalents 0.0296 _diffrn_reflns_av_unetI/netI 0.0384 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_number 8311 _diffrn_reflns_theta_full 25.35 _diffrn_reflns_theta_max 25.35 _diffrn_reflns_theta_min 2.98 _diffrn_ambient_temperature 293.15 _diffrn_detector_area_resol_mean 10.3592 _diffrn_measured_fraction_theta_full 0.996 _diffrn_measured_fraction_theta_max 0.996 _diffrn_measurement_device_type 'Xcalibur, Atlas, Gemini ultra' _diffrn_measurement_method '\w scans' _diffrn_orient_matrix_UB_11 0.0248910000 _diffrn_orient_matrix_UB_12 0.0465411000 _diffrn_orient_matrix_UB_13 -0.0181429000 _diffrn_orient_matrix_UB_21 0.0216577000 _diffrn_orient_matrix_UB_22 0.0248143000 _diffrn_orient_matrix_UB_23 0.0476924000 _diffrn_orient_matrix_UB_31 0.0454974000 _diffrn_orient_matrix_UB_32 -0.0372403000 _diffrn_orient_matrix_UB_33 0.0090621000 _diffrn_radiation_monochromator graphite _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_source 'Enhance (Mo) X-ray Source' _diffrn_standards_decay_% ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_number ? _reflns_number_gt 2598 _reflns_number_total 3681 _reflns_odcompleteness_completeness 99.56 _reflns_odcompleteness_iscentric 1 _reflns_odcompleteness_theta 26.32 _reflns_threshold_expression >2sigma(I) _computing_cell_refinement ; CrysAlisPro, Agilent Technologies, Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET) (compiled May 16 2011,17:55:39) ; _computing_data_collection ; CrysAlisPro, Agilent Technologies, Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET) (compiled May 16 2011,17:55:39) ; _computing_data_reduction ; CrysAlisPro, Agilent Technologies, Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET) (compiled May 16 2011,17:55:39) ; _computing_molecular_graphics 'Olex2 (Dolomanov et al., 2009)' _computing_publication_material 'Olex2 (Dolomanov et al., 2009)' _computing_structure_refinement 'ShelXL (Sheldrick, 2008)' _computing_structure_solution 'ShelXS (Sheldrick, 2008)' _refine_diff_density_max 0.503 _refine_diff_density_min -0.237 _refine_diff_density_rms 0.044 _refine_ls_extinction_coef ? _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.037 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 254 _refine_ls_number_reflns 3681 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0772 _refine_ls_R_factor_gt 0.0506 _refine_ls_restrained_S_all 1.037 _refine_ls_shift/su_max 0.003 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0764P)^2^+0.5292P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1324 _refine_ls_wR_factor_ref 0.1543 _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. ; _olex2_refinement_description ; 1. Fixed Uiso At 1.2 times of: All C(H) groups, All C(H,H) groups At 1.5 times of: All C(H,H,H) groups 2.a Ternary CH refined with riding coordinates: C9(H9), C10(H10) 2.b Secondary CH2 refined with riding coordinates: C11(H11A,H11B), C12(H12A,H12B), C13(H13A,H13B) 2.c Aromatic/amide H refined with riding coordinates: C1(H1), C2(H2), C3(H3), C4(H4), C14(H14), C17(H17), C18(H18), C20(H20), C21(H21) 2.d X=CH2 refined with riding coordinates: C15(H15A,H15B) 2.e Idealised Me refined as rotating group: C22(H22A,H22B,H22C) ; _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap 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_disorder_assembly _atom_site_disorder_group _atom_site_refinement_flags_posn S1 S 0.18686(5) 0.60155(6) 0.18718(5) 0.0536(2) Uani 1 d . . . O1 O 0.14634(16) 0.49114(17) 0.13751(16) 0.0735(6) Uani 1 d . . . O2 O 0.22116(17) 0.60461(19) 0.29122(13) 0.0734(6) Uani 1 d . . . O3 O 0.45724(15) 0.70363(18) 0.27676(13) 0.0675(6) Uani 1 d . . . N1 N 0.29365(15) 0.63805(18) 0.15955(14) 0.0477(5) Uani 1 d . . . N2 N 0.26103(16) 0.58520(19) -0.02012(15) 0.0531(6) Uani 1 d . . . C1 C 0.2843(2) 0.6136(3) -0.1828(2) 0.0752(9) Uani 1 d . . . H1 H 0.2560 0.5388 -0.2087 0.090 Uiso 1 calc . . R C2 C 0.3224(3) 0.6956(5) -0.2353(2) 0.0923(13) Uani 1 d . . . H2 H 0.3190 0.6745 -0.2981 0.111 Uiso 1 calc . . R C3 C 0.3649(3) 0.8069(4) -0.1986(3) 0.0887(11) Uani 1 d . . . H3 H 0.3895 0.8587 -0.2366 0.106 Uiso 1 calc . . R C4 C 0.3712(3) 0.8422(3) -0.1057(2) 0.0743(9) Uani 1 d . . . H4 H 0.3991 0.9177 -0.0811 0.089 Uiso 1 calc . . R C5 C 0.3349(2) 0.7625(3) -0.04916(18) 0.0549(7) Uani 1 d . . . C6 C 0.29074(19) 0.6494(3) -0.08898(18) 0.0549(7) Uani 1 d . . . C7 C 0.28877(18) 0.6578(2) 0.06156(16) 0.0459(6) Uani 1 d . . . C8 C 0.33219(19) 0.7640(2) 0.04793(17) 0.0496(6) Uani 1 d . . . C9 C 0.3762(2) 0.8336(2) 0.14117(18) 0.0583(7) Uani 1 d . . . H9 H 0.3404 0.9118 0.1392 0.070 Uiso 1 calc . . R C10 C 0.3579(2) 0.7438(2) 0.21628(18) 0.0538(7) Uani 1 d . . . H10 H 0.3203 0.7843 0.2547 0.065 Uiso 1 calc . . R C11 C 0.5331(2) 0.7272(3) 0.2304(2) 0.0792(10) Uani 1 d . . . H11A H 0.5331 0.6626 0.1850 0.095 Uiso 1 calc . . R H11B H 0.6037 0.7348 0.2782 0.095 Uiso 1 calc . . R C12 C 0.4971(3) 0.8459(3) 0.1773(2) 0.0831(10) Uani 1 d . . . H12A H 0.5232 0.8549 0.1232 0.100 Uiso 1 calc . . R H12B H 0.5206 0.9148 0.2211 0.100 Uiso 1 calc . . R C13 C 0.2303(2) 0.4576(3) -0.0298(2) 0.0722(9) Uani 1 d . . . H13A H 0.1914 0.4405 -0.0981 0.087 Uiso 1 calc . . R H13B H 0.1829 0.4431 0.0065 0.087 Uiso 1 calc . . R C14 C 0.3201(4) 0.3735(4) 0.0050(3) 0.0983(12) Uani 1 d . . . H14 H 0.3030 0.2912 -0.0029 0.118 Uiso 1 calc . . R C15 C 0.4110(5) 0.3958(5) 0.0416(4) 0.142(2) Uani 1 d . . . H15A H 0.4335 0.4763 0.0517 0.170 Uiso 1 calc . . R H15B H 0.4602 0.3329 0.0605 0.170 Uiso 1 calc . . R C16 C 0.09253(18) 0.7162(2) 0.14067(16) 0.0451(6) Uani 1 d . . . C17 C 0.0899(2) 0.8150(3) 0.19844(18) 0.0572(7) Uani 1 d . . . H17 H 0.1386 0.8208 0.2615 0.069 Uiso 1 calc . . R C18 C 0.0151(2) 0.9049(3) 0.1627(2) 0.0607(7) Uani 1 d . . . H18 H 0.0141 0.9714 0.2019 0.073 Uiso 1 calc . . R C19 C -0.05878(19) 0.8977(2) 0.06886(18) 0.0523(6) Uani 1 d . . . C20 C -0.0529(2) 0.7996(3) 0.01198(18) 0.0604(7) Uani 1 d . . . H20 H -0.1005 0.7947 -0.0516 0.072 Uiso 1 calc . . R C21 C 0.0207(2) 0.7088(2) 0.04595(18) 0.0547(7) Uani 1 d . . . H21 H 0.0226 0.6432 0.0061 0.066 Uiso 1 calc . . R C22 C -0.1418(2) 0.9946(3) 0.0324(2) 0.0770(9) Uani 1 d . . . H22A H -0.2041 0.9714 0.0462 0.115 Uiso 1 calc . . GR H22B H -0.1591 1.0042 -0.0368 0.115 Uiso 1 calc . . GR H22C H -0.1152 1.0702 0.0645 0.115 Uiso 1 calc . . GR 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 0.0580(4) 0.0484(4) 0.0529(4) 0.0100(3) 0.0170(3) -0.0025(3) O1 0.0796(13) 0.0458(11) 0.0941(15) 0.0043(10) 0.0285(11) -0.0121(10) O2 0.0861(14) 0.0832(14) 0.0488(10) 0.0239(10) 0.0204(10) 0.0074(11) O3 0.0535(11) 0.0771(13) 0.0566(11) 0.0121(10) -0.0011(9) -0.0094(10) N1 0.0457(11) 0.0477(11) 0.0444(11) -0.0003(9) 0.0087(9) 0.0003(9) N2 0.0443(11) 0.0562(13) 0.0520(12) -0.0130(10) 0.0075(9) 0.0024(10) C1 0.0596(17) 0.104(3) 0.0547(17) -0.0116(17) 0.0101(14) 0.0242(17) C2 0.087(2) 0.141(4) 0.0514(17) 0.012(2) 0.0273(17) 0.047(3) C3 0.094(2) 0.110(3) 0.069(2) 0.038(2) 0.0367(19) 0.042(2) C4 0.081(2) 0.073(2) 0.0719(19) 0.0280(17) 0.0309(16) 0.0267(17) C5 0.0506(14) 0.0607(17) 0.0500(14) 0.0113(13) 0.0126(11) 0.0225(13) C6 0.0424(13) 0.0715(18) 0.0455(13) -0.0006(13) 0.0080(11) 0.0201(13) C7 0.0415(12) 0.0478(14) 0.0438(13) -0.0018(11) 0.0085(10) 0.0076(11) C8 0.0505(14) 0.0449(14) 0.0472(13) 0.0026(11) 0.0085(11) 0.0090(11) C9 0.0690(17) 0.0409(14) 0.0572(15) 0.0002(12) 0.0116(13) 0.0020(12) C10 0.0538(14) 0.0538(15) 0.0468(13) -0.0061(12) 0.0081(12) -0.0008(12) C11 0.0504(16) 0.086(2) 0.087(2) 0.0122(18) 0.0037(15) -0.0133(16) C12 0.084(2) 0.071(2) 0.081(2) 0.0038(17) 0.0106(17) -0.0332(18) C13 0.0695(18) 0.0674(19) 0.0751(19) -0.0282(16) 0.0188(15) -0.0171(15) C14 0.108(3) 0.066(2) 0.120(3) -0.010(2) 0.038(3) 0.009(2) C15 0.138(5) 0.131(4) 0.162(5) 0.034(4) 0.059(4) 0.063(4) C16 0.0437(12) 0.0487(14) 0.0424(12) 0.0007(11) 0.0140(10) -0.0091(11) C17 0.0509(14) 0.0710(18) 0.0423(13) -0.0090(13) 0.0064(11) 0.0009(13) C18 0.0581(16) 0.0610(17) 0.0609(16) -0.0142(13) 0.0176(13) -0.0013(14) C19 0.0449(13) 0.0603(16) 0.0538(14) 0.0048(13) 0.0197(11) -0.0013(12) C20 0.0499(15) 0.082(2) 0.0418(13) 0.0027(14) 0.0066(11) -0.0009(14) C21 0.0520(14) 0.0605(16) 0.0474(13) -0.0104(12) 0.0115(11) -0.0047(13) C22 0.0640(18) 0.087(2) 0.078(2) 0.0184(17) 0.0220(15) 0.0168(17) _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 O1 1.422(2) . ? S1 O2 1.4258(19) . ? S1 N1 1.665(2) . ? S1 C16 1.750(2) . ? O3 C10 1.395(3) . ? O3 C11 1.424(4) . ? N1 C7 1.423(3) . ? N1 C10 1.513(3) . ? N2 C6 1.391(4) . ? N2 C7 1.373(3) . ? N2 C13 1.454(4) . ? C1 H1 0.9300 . ? C1 C2 1.387(5) . ? C1 C6 1.396(4) . ? C2 H2 0.9300 . ? C2 C3 1.377(5) . ? C3 H3 0.9300 . ? C3 C4 1.383(5) . ? C4 H4 0.9300 . ? C4 C5 1.398(4) . ? C5 C6 1.413(4) . ? C5 C8 1.427(4) . ? C7 C8 1.349(4) . ? C8 C9 1.493(3) . ? C9 H9 0.9800 . ? C9 C10 1.553(4) . ? C9 C12 1.533(4) . ? C10 H10 0.9800 . ? C11 H11A 0.9700 . ? C11 H11B 0.9700 . ? C11 C12 1.509(4) . ? C12 H12A 0.9700 . ? C12 H12B 0.9700 . ? C13 H13A 0.9700 . ? C13 H13B 0.9700 . ? C13 C14 1.466(5) . ? C14 H14 0.9300 . ? C14 C15 1.179(6) . ? C15 H15A 0.9300 . ? C15 H15B 0.9300 . ? C16 C17 1.381(4) . ? C16 C21 1.390(3) . ? C17 H17 0.9300 . ? C17 C18 1.377(4) . ? C18 H18 0.9300 . ? C18 C19 1.390(4) . ? C19 C20 1.378(4) . ? C19 C22 1.500(4) . ? C20 H20 0.9300 . ? C20 C21 1.372(4) . ? C21 H21 0.9300 . ? C22 H22A 0.9600 . ? C22 H22B 0.9600 . ? C22 H22C 0.9600 . ? 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 O1 S1 O2 119.31(12) . . ? O1 S1 N1 107.10(12) . . ? O1 S1 C16 108.44(12) . . ? O2 S1 N1 104.99(11) . . ? O2 S1 C16 108.84(12) . . ? N1 S1 C16 107.60(11) . . ? C10 O3 C11 109.1(2) . . ? C7 N1 S1 122.03(15) . . ? C7 N1 C10 104.67(19) . . ? C10 N1 S1 115.50(16) . . ? C6 N2 C13 124.1(2) . . ? C7 N2 C6 105.7(2) . . ? C7 N2 C13 128.9(2) . . ? C2 C1 H1 121.8 . . ? C2 C1 C6 116.5(3) . . ? C6 C1 H1 121.8 . . ? C1 C2 H2 118.5 . . ? C3 C2 C1 123.0(3) . . ? C3 C2 H2 118.5 . . ? C2 C3 H3 119.8 . . ? C2 C3 C4 120.5(4) . . ? C4 C3 H3 119.8 . . ? C3 C4 H4 120.5 . . ? C3 C4 C5 118.9(3) . . ? C5 C4 H4 120.5 . . ? C4 C5 C6 119.4(3) . . ? C4 C5 C8 135.1(3) . . ? C6 C5 C8 105.5(2) . . ? N2 C6 C1 128.7(3) . . ? N2 C6 C5 109.5(2) . . ? C1 C6 C5 121.8(3) . . ? N2 C7 N1 133.4(2) . . ? C8 C7 N1 113.9(2) . . ? C8 C7 N2 112.2(2) . . ? C5 C8 C9 140.5(3) . . ? C7 C8 C5 107.1(2) . . ? C7 C8 C9 111.5(2) . . ? C8 C9 H9 112.6 . . ? C8 C9 C10 101.9(2) . . ? C8 C9 C12 113.7(3) . . ? C10 C9 H9 112.6 . . ? C12 C9 H9 112.6 . . ? C12 C9 C10 102.6(2) . . ? O3 C10 N1 110.2(2) . . ? O3 C10 C9 107.4(2) . . ? O3 C10 H10 110.5 . . ? N1 C10 C9 107.49(19) . . ? N1 C10 H10 110.5 . . ? C9 C10 H10 110.5 . . ? O3 C11 H11A 110.9 . . ? O3 C11 H11B 110.9 . . ? O3 C11 C12 104.2(3) . . ? H11A C11 H11B 108.9 . . ? C12 C11 H11A 110.9 . . ? C12 C11 H11B 110.9 . . ? C9 C12 H12A 111.3 . . ? C9 C12 H12B 111.3 . . ? C11 C12 C9 102.5(2) . . ? C11 C12 H12A 111.3 . . ? C11 C12 H12B 111.3 . . ? H12A C12 H12B 109.2 . . ? N2 C13 H13A 108.8 . . ? N2 C13 H13B 108.8 . . ? N2 C13 C14 113.7(3) . . ? H13A C13 H13B 107.7 . . ? C14 C13 H13A 108.8 . . ? C14 C13 H13B 108.8 . . ? C13 C14 H14 115.6 . . ? C15 C14 C13 128.9(5) . . ? C15 C14 H14 115.6 . . ? C14 C15 H15A 120.0 . . ? C14 C15 H15B 120.0 . . ? H15A C15 H15B 120.0 . . ? C17 C16 S1 119.69(18) . . ? C17 C16 C21 119.8(2) . . ? C21 C16 S1 120.5(2) . . ? C16 C17 H17 120.0 . . ? C18 C17 C16 120.0(2) . . ? C18 C17 H17 120.0 . . ? C17 C18 H18 119.5 . . ? C17 C18 C19 121.0(3) . . ? C19 C18 H18 119.5 . . ? C18 C19 C22 120.2(3) . . ? C20 C19 C18 117.8(2) . . ? C20 C19 C22 122.0(2) . . ? C19 C20 H20 118.9 . . ? C21 C20 C19 122.3(2) . . ? C21 C20 H20 118.9 . . ? C16 C21 H21 120.5 . . ? C20 C21 C16 119.1(2) . . ? C20 C21 H21 120.5 . . ? C19 C22 H22A 109.5 . . ? C19 C22 H22B 109.5 . . ? C19 C22 H22C 109.5 . . ? H22A C22 H22B 109.5 . . ? H22A C22 H22C 109.5 . . ? H22B C22 H22C 109.5 . . ? 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 S1 N1 C7 N2 -61.3(3) . . . . ? S1 N1 C7 C8 128.3(2) . . . . ? S1 N1 C10 O3 113.6(2) . . . . ? S1 N1 C10 C9 -129.68(19) . . . . ? S1 C16 C17 C18 -179.3(2) . . . . ? S1 C16 C21 C20 179.4(2) . . . . ? O1 S1 N1 C7 59.2(2) . . . . ? O1 S1 N1 C10 -171.81(16) . . . . ? O1 S1 C16 C17 153.7(2) . . . . ? O1 S1 C16 C21 -26.7(3) . . . . ? O2 S1 N1 C7 -173.05(18) . . . . ? O2 S1 N1 C10 -44.03(18) . . . . ? O2 S1 C16 C17 22.5(2) . . . . ? O2 S1 C16 C21 -157.9(2) . . . . ? O3 C11 C12 C9 -37.5(3) . . . . ? N1 S1 C16 C17 -90.8(2) . . . . ? N1 S1 C16 C21 88.9(2) . . . . ? N1 C7 C8 C5 171.88(19) . . . . ? N1 C7 C8 C9 0.8(3) . . . . ? N2 C7 C8 C5 -0.6(3) . . . . ? N2 C7 C8 C9 -171.7(2) . . . . ? N2 C13 C14 C15 2.6(7) . . . . ? C1 C2 C3 C4 -0.2(5) . . . . ? C2 C1 C6 N2 -178.5(3) . . . . ? C2 C1 C6 C5 -0.8(4) . . . . ? C2 C3 C4 C5 0.8(5) . . . . ? C3 C4 C5 C6 -1.4(4) . . . . ? C3 C4 C5 C8 177.0(3) . . . . ? C4 C5 C6 N2 179.5(2) . . . . ? C4 C5 C6 C1 1.4(4) . . . . ? C4 C5 C8 C7 -178.6(3) . . . . ? C4 C5 C8 C9 -11.7(5) . . . . ? C5 C8 C9 C10 -162.7(3) . . . . ? C5 C8 C9 C12 -53.1(4) . . . . ? C6 N2 C7 N1 -169.5(2) . . . . ? C6 N2 C7 C8 1.1(3) . . . . ? C6 N2 C13 C14 85.5(3) . . . . ? C6 C1 C2 C3 0.2(5) . . . . ? C6 C5 C8 C7 -0.1(3) . . . . ? C6 C5 C8 C9 166.8(3) . . . . ? C7 N1 C10 O3 -109.3(2) . . . . ? C7 N1 C10 C9 7.4(2) . . . . ? C7 N2 C6 C1 176.9(2) . . . . ? C7 N2 C6 C5 -1.1(3) . . . . ? C7 N2 C13 C14 -79.2(4) . . . . ? C7 C8 C9 C10 3.9(3) . . . . ? C7 C8 C9 C12 113.5(3) . . . . ? C8 C5 C6 N2 0.7(3) . . . . ? C8 C5 C6 C1 -177.4(2) . . . . ? C8 C9 C10 O3 111.8(2) . . . . ? C8 C9 C10 N1 -6.8(3) . . . . ? C8 C9 C12 C11 -83.2(3) . . . . ? C10 O3 C11 C12 35.5(3) . . . . ? C10 N1 C7 N2 165.2(2) . . . . ? C10 N1 C7 C8 -5.3(3) . . . . ? C10 C9 C12 C11 26.0(3) . . . . ? C11 O3 C10 N1 98.7(3) . . . . ? C11 O3 C10 C9 -18.1(3) . . . . ? C12 C9 C10 O3 -6.1(3) . . . . ? C12 C9 C10 N1 -124.7(2) . . . . ? C13 N2 C6 C1 9.2(4) . . . . ? C13 N2 C6 C5 -168.8(2) . . . . ? C13 N2 C7 N1 -2.6(4) . . . . ? C13 N2 C7 C8 167.9(2) . . . . ? C16 S1 N1 C7 -57.2(2) . . . . ? C16 S1 N1 C10 71.79(17) . . . . ? C16 C17 C18 C19 0.4(4) . . . . ? C17 C16 C21 C20 -1.0(4) . . . . ? C17 C18 C19 C20 -1.7(4) . . . . ? C17 C18 C19 C22 178.0(3) . . . . ? C18 C19 C20 C21 1.8(4) . . . . ? C19 C20 C21 C16 -0.5(4) . . . . ? C21 C16 C17 C18 1.0(4) . . . . ? C22 C19 C20 C21 -178.0(3) . . . . ?