#------------------------------------------------------------------------------ #$Date: 2024-04-23 04:13:16 +0300 (Tue, 23 Apr 2024) $ #$Revision: 291331 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/15/99/7159914.cif $ #------------------------------------------------------------------------------ # # This file is available in the Crystallography Open Database (COD), # http://www.crystallography.net/ # # All data on this site have been placed in the public domain by the # contributors. # data_7159914 loop_ _publ_author_name 'Alexeev, Michael S.' 'Strelkova, Tatyana V.' 'Ilyin, Jr., Michail M.' 'Nelyubina, Yulia V.' 'Bespalov, Ivan A.' 'Medvedev, Michael' 'Khrustalev, Victor N.' 'Kuznetsov, Nikolai' _publ_section_title ; New Generation of Highly Reactive Allylborating Agents For Cu(I)-Catalyzed Allylation of Chiral Sulfinylimines ; _journal_name_full 'Organic & Biomolecular Chemistry' _journal_paper_doi 10.1039/D4OB00291A _journal_year 2024 _chemical_absolute_configuration ad _chemical_formula_moiety 'C14 H22 N2 O S' _chemical_formula_sum 'C14 H22 N2 O S' _chemical_formula_weight 266.39 _space_group_crystal_system monoclinic _space_group_IT_number 4 _space_group_name_Hall 'P 2yb' _space_group_name_H-M_alt 'P 1 21 1' _atom_sites_solution_hydrogens mixed _atom_sites_solution_primary dual _audit_creation_date 2023-08-14 _audit_creation_method ; Olex2 1.3 (compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408) ; _audit_update_record ; 2023-08-16 deposited with the CCDC. 2024-04-17 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 108.897(2) _cell_angle_gamma 90 _cell_formula_units_Z 2 _cell_length_a 10.7916(4) _cell_length_b 6.2242(2) _cell_length_c 11.7768(4) _cell_measurement_reflns_used 5319 _cell_measurement_temperature 100 _cell_measurement_theta_max 30.60 _cell_measurement_theta_min 3.11 _cell_volume 748.40(5) _computing_molecular_graphics 'Olex2 1.3 (Dolomanov et al., 2009)' _computing_publication_material 'Olex2 1.3 (Dolomanov et al., 2009)' _computing_structure_refinement 'XL (Sheldrick, 2008)' _computing_structure_solution 'SHELXT 2014/4 (Sheldrick, 2014)' _diffrn_ambient_temperature 100 _diffrn_measured_fraction_theta_full 0.999 _diffrn_measured_fraction_theta_max 0.999 _diffrn_measurement_device_type 'Bruker Quest D8' _diffrn_measurement_method '\f and \w scans' _diffrn_radiation_monochromator graphite _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0347 _diffrn_reflns_av_unetI/netI 0.0446 _diffrn_reflns_Laue_measured_fraction_full 0.999 _diffrn_reflns_Laue_measured_fraction_max 0.999 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_number 9895 _diffrn_reflns_point_group_measured_fraction_full 0.993 _diffrn_reflns_point_group_measured_fraction_max 0.990 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 28.997 _diffrn_reflns_theta_min 1.995 _diffrn_source_current 1.4 _diffrn_source_power 0.07 _diffrn_source_voltage 50.0 _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 0.208 _exptl_absorpt_correction_T_max 0.7461 _exptl_absorpt_correction_T_min 0.6473 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1129 before and 0.0536 after correction. The Ratio of minimum to maximum transmission is 0.8676. The \l/2 correction factor is Not present. ; _exptl_crystal_colour colourless _exptl_crystal_colour_primary colourless _exptl_crystal_density_diffrn 1.182 _exptl_crystal_description needle _exptl_crystal_F_000 288 _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.05 _exptl_crystal_size_min 0.05 _refine_diff_density_max 0.288 _refine_diff_density_min -0.195 _refine_diff_density_rms 0.040 _refine_ls_abs_structure_details ; Flack x determined using 1589 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). ; _refine_ls_abs_structure_Flack 0.03(3) _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.039 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 167 _refine_ls_number_reflns 3943 _refine_ls_number_restraints 1 _refine_ls_restrained_S_all 1.039 _refine_ls_R_factor_all 0.0347 _refine_ls_R_factor_gt 0.0316 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0358P)^2^+0.0575P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0750 _refine_ls_wR_factor_ref 0.0767 _reflns_Friedel_coverage 0.823 _reflns_Friedel_fraction_full 0.987 _reflns_Friedel_fraction_max 0.980 _reflns_number_gt 3721 _reflns_number_total 3943 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d4ob00291a3.cif _cod_data_source_block Org _cod_database_code 7159914 _shelxl_version_number 2014/6 _shelx_space_group_comment ; The symmetry employed for this shelxl refinement is uniquely defined by the following loop, which should always be used as a source of symmetry information in preference to the above space-group names. They are only intended as comments. ; _shelx_estimated_absorpt_t_max 0.990 _shelx_estimated_absorpt_t_min 0.950 _olex2_refinement_description ; 1. Fixed Uiso At 1.2 times of: All C(H) groups, All C(H,H) groups, All N(H) groups At 1.5 times of: All C(H,H,H) groups 2.a Riding coordinates: N1(H1) 2.b Ternary CH refined with riding coordinates: C1(H1A) 2.c Secondary CH2 refined with riding coordinates: C8(H8A,H8B) 2.d Aromatic/amide H refined with riding coordinates: C3(H3), C4(H4), C5(H5), C9(H9) 2.e X=CH2 refined with riding coordinates: C10(H10A,H10B) 2.f Idealised Me refined as rotating group: C7(H7A,H7B,H7C), C12(H12A,H12B,H12C), C13(H13A,H13B,H13C), C14(H14A,H14B,H14C) ; _shelx_res_file ; TITL a_a.res in P2(1) REM Old TITL a in P2(1) REM SHELXT solution in P2(1) REM R1 0.082, Rweak 0.030, Alpha 0.006, Orientation as input REM Flack x = -0.010 ( 0.034 ) from Parsons' quotients REM Formula found by SHELXT: C13 N2 O2 S CELL 0.71073 10.7916 6.2242 11.7768 90 108.897 90 ZERR 2 0.0004 0.0002 0.0004 0 0.002 0 LATT -1 SYMM -X,0.5+Y,-Z SFAC C H N O S UNIT 28 44 4 2 2 L.S. 10 PLAN 7 SIZE 0.05 0.05 0.25 TEMP -173.15 CONF BOND $H MORE -1 fmap 2 acta OMIT -4 58 REM REM REM WGHT 0.035800 0.057500 FVAR 1.00360 S1 5 0.856347 0.520780 0.517511 11.00000 0.01609 0.01169 = 0.01660 0.00102 0.00242 0.00030 O1 4 0.998217 0.546779 0.589860 11.00000 0.01527 0.01844 = 0.01881 -0.00087 0.00061 0.00297 N1 3 0.823393 0.658777 0.389959 11.00000 0.01986 0.01214 = 0.01493 -0.00058 0.00200 -0.00164 AFIX 3 H1 2 0.868113 0.780917 0.396119 11.00000 -1.20000 AFIX 0 N2 3 0.590787 0.521979 0.187243 11.00000 0.01473 0.01430 = 0.01876 -0.00173 0.00179 0.00043 C1 1 0.826898 0.523281 0.286921 11.00000 0.01542 0.01193 = 0.01665 -0.00020 0.00241 0.00016 AFIX 13 H1A 2 0.899865 0.416940 0.315628 11.00000 -1.20000 AFIX 0 C2 1 0.698229 0.402697 0.237416 11.00000 0.01552 0.01168 = 0.01522 -0.00071 0.00295 -0.00050 C3 1 0.695225 0.181258 0.244972 11.00000 0.01889 0.01278 = 0.02117 -0.00060 0.00415 0.00101 AFIX 43 H3 2 0.773141 0.102540 0.282701 11.00000 -1.20000 AFIX 0 C4 1 0.575907 0.075492 0.196281 11.00000 0.02310 0.01533 = 0.02940 -0.00415 0.00808 -0.00393 AFIX 43 H4 2 0.570748 -0.076635 0.199527 11.00000 -1.20000 AFIX 0 C5 1 0.465426 0.197344 0.143224 11.00000 0.01780 0.01969 = 0.02464 -0.00608 0.00686 -0.00519 AFIX 43 H5 2 0.382943 0.129623 0.108129 11.00000 -1.20000 AFIX 0 C6 1 0.475693 0.420235 0.141489 11.00000 0.01541 0.01950 = 0.01652 -0.00292 0.00361 0.00058 C7 1 0.358397 0.562812 0.089502 11.00000 0.01606 0.02876 = 0.02908 -0.00369 0.00162 0.00459 AFIX 137 H7A 2 0.340523 0.642436 0.154294 11.00000 -1.50000 H7B 2 0.282162 0.474582 0.047332 11.00000 -1.50000 H7C 2 0.376088 0.664307 0.033011 11.00000 -1.50000 AFIX 0 C8 1 0.853603 0.669004 0.192611 11.00000 0.01788 0.01541 = 0.01975 -0.00011 0.00516 -0.00113 AFIX 23 H8A 2 0.775534 0.759131 0.154718 11.00000 -1.20000 H8B 2 0.927746 0.765806 0.232432 11.00000 -1.20000 AFIX 0 C9 1 0.885349 0.542008 0.097703 11.00000 0.02488 0.01782 = 0.01854 -0.00069 0.00423 -0.00110 AFIX 43 H9 2 0.820903 0.445560 0.050521 11.00000 -1.20000 AFIX 0 C10 1 0.997049 0.555733 0.075592 11.00000 0.03019 0.02777 = 0.02769 -0.00045 0.01206 0.00234 AFIX 93 H10A 2 1.063458 0.650717 0.121232 11.00000 -1.20000 H10B 2 1.011284 0.470658 0.013990 11.00000 -1.20000 AFIX 0 C11 1 0.763595 0.685178 0.592503 11.00000 0.01902 0.01822 = 0.02468 0.00116 0.00965 0.00201 C12 1 0.789666 0.923611 0.586235 11.00000 0.02465 0.01857 = 0.02783 -0.00375 0.00961 0.00268 AFIX 137 H12A 2 0.884140 0.950319 0.618385 11.00000 -1.50000 H12B 2 0.745298 1.003064 0.633746 11.00000 -1.50000 H12C 2 0.756403 0.971508 0.502524 11.00000 -1.50000 AFIX 0 C13 1 0.809687 0.606143 0.722545 11.00000 0.04070 0.03468 = 0.02754 0.00704 0.01945 0.00937 AFIX 137 H13A 2 0.793890 0.451298 0.724154 11.00000 -1.50000 H13B 2 0.761154 0.681527 0.767865 11.00000 -1.50000 H13C 2 0.903536 0.634985 0.758901 11.00000 -1.50000 AFIX 0 C14 1 0.620146 0.630210 0.529899 11.00000 0.01801 0.03288 = 0.05324 -0.00212 0.01207 -0.00181 AFIX 137 H14A 2 0.593909 0.679623 0.446448 11.00000 -1.50000 H14B 2 0.566066 0.701312 0.571420 11.00000 -1.50000 H14C 2 0.608123 0.474310 0.531532 11.00000 -1.50000 AFIX 0 HKLF 4 REM a_a.res in P2(1) REM R1 = 0.0316 for 3721 Fo > 4sig(Fo) and 0.0347 for all 3943 data REM 167 parameters refined using 1 restraints END WGHT 0.0358 0.0575 REM Highest difference peak 0.288, deepest hole -0.195, 1-sigma level 0.040 Q1 1 0.9335 0.5382 0.5551 11.00000 0.05 0.29 Q2 1 0.8406 0.5917 0.2375 11.00000 0.05 0.23 Q3 1 0.8556 0.6143 0.4623 11.00000 0.05 0.22 Q4 1 0.8224 0.5723 0.3435 11.00000 0.05 0.21 Q5 1 0.6294 0.1493 0.2179 11.00000 0.05 0.20 Q6 1 0.7626 0.4725 0.2593 11.00000 0.05 0.20 Q7 1 0.8592 0.5981 0.1494 11.00000 0.05 0.20 ; _shelx_res_checksum 36759 _olex2_submission_special_instructions 'No special instructions were received' loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, y+1/2, -z' 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_site_symmetry_order _atom_site_calc_flag _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group S1 S 0.85635(4) 0.52078(8) 0.51751(4) 0.01549(11) Uani 1 1 d . . . . . O1 O 0.99822(12) 0.5468(2) 0.58986(11) 0.0187(3) Uani 1 1 d . . . . . N1 N 0.82339(15) 0.6588(3) 0.38996(13) 0.0165(3) Uani 1 1 d . . . . . H1 H 0.8681 0.7809 0.3961 0.020 Uiso 1 1 d R U . . . N2 N 0.59079(13) 0.5220(3) 0.18724(12) 0.0168(3) Uani 1 1 d . . . . . C1 C 0.82690(16) 0.5233(4) 0.28692(14) 0.0153(3) Uani 1 1 d . . . . . H1A H 0.8999 0.4169 0.3156 0.018 Uiso 1 1 calc R U . . . C2 C 0.69823(18) 0.4027(3) 0.23742(16) 0.0146(4) Uani 1 1 d . . . . . C3 C 0.69522(19) 0.1813(3) 0.24497(17) 0.0182(4) Uani 1 1 d . . . . . H3 H 0.7731 0.1025 0.2827 0.022 Uiso 1 1 calc R U . . . C4 C 0.5759(2) 0.0755(3) 0.19628(18) 0.0227(5) Uani 1 1 d . . . . . H4 H 0.5707 -0.0766 0.1995 0.027 Uiso 1 1 calc R U . . . C5 C 0.46543(19) 0.1973(3) 0.14322(18) 0.0207(4) Uani 1 1 d . . . . . H5 H 0.3829 0.1296 0.1081 0.025 Uiso 1 1 calc R U . . . C6 C 0.47569(18) 0.4202(3) 0.14149(17) 0.0175(4) Uani 1 1 d . . . . . C7 C 0.35840(19) 0.5628(4) 0.08950(19) 0.0260(5) Uani 1 1 d . . . . . H7A H 0.3405 0.6424 0.1543 0.039 Uiso 1 1 calc R U . . . H7B H 0.2822 0.4746 0.0473 0.039 Uiso 1 1 calc R U . . . H7C H 0.3761 0.6643 0.0330 0.039 Uiso 1 1 calc R U . . . C8 C 0.85360(19) 0.6690(3) 0.19261(17) 0.0179(4) Uani 1 1 d . . . . . H8A H 0.7755 0.7591 0.1547 0.021 Uiso 1 1 calc R U . . . H8B H 0.9277 0.7658 0.2324 0.021 Uiso 1 1 calc R U . . . C9 C 0.88535(19) 0.5420(4) 0.09770(16) 0.0211(4) Uani 1 1 d . . . . . H9 H 0.8209 0.4456 0.0505 0.025 Uiso 1 1 calc R U . . . C10 C 0.9970(2) 0.5557(4) 0.07559(19) 0.0279(5) Uani 1 1 d . . . . . H10A H 1.0635 0.6507 0.1212 0.033 Uiso 1 1 calc R U . . . H10B H 1.0113 0.4707 0.0140 0.033 Uiso 1 1 calc R U . . . C11 C 0.76360(19) 0.6852(4) 0.59250(18) 0.0200(4) Uani 1 1 d . . . . . C12 C 0.7897(2) 0.9236(3) 0.5862(2) 0.0234(4) Uani 1 1 d . . . . . H12A H 0.8841 0.9503 0.6184 0.035 Uiso 1 1 calc R U . . . H12B H 0.7453 1.0031 0.6337 0.035 Uiso 1 1 calc R U . . . H12C H 0.7564 0.9715 0.5025 0.035 Uiso 1 1 calc R U . . . C13 C 0.8097(3) 0.6061(4) 0.72255(19) 0.0323(5) Uani 1 1 d . . . . . H13A H 0.7939 0.4513 0.7242 0.048 Uiso 1 1 calc R U . . . H13B H 0.7612 0.6815 0.7679 0.048 Uiso 1 1 calc R U . . . H13C H 0.9035 0.6350 0.7589 0.048 Uiso 1 1 calc R U . . . C14 C 0.6201(2) 0.6302(4) 0.5299(2) 0.0346(6) Uani 1 1 d . . . . . H14A H 0.5939 0.6796 0.4464 0.052 Uiso 1 1 calc R U . . . H14B H 0.5661 0.7013 0.5714 0.052 Uiso 1 1 calc R U . . . H14C H 0.6081 0.4743 0.5315 0.052 Uiso 1 1 calc R U . . . 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 0.01609(19) 0.01169(19) 0.01660(19) 0.00102(19) 0.00242(15) 0.0003(2) O1 0.0153(6) 0.0184(8) 0.0188(6) -0.0009(6) 0.0006(5) 0.0030(6) N1 0.0199(8) 0.0121(8) 0.0149(7) -0.0006(6) 0.0020(6) -0.0016(6) N2 0.0147(6) 0.0143(7) 0.0188(7) -0.0017(8) 0.0018(5) 0.0004(8) C1 0.0154(7) 0.0119(7) 0.0167(7) -0.0002(9) 0.0024(6) 0.0002(9) C2 0.0155(8) 0.0117(9) 0.0152(8) -0.0007(7) 0.0030(7) -0.0005(7) C3 0.0189(9) 0.0128(9) 0.0212(9) -0.0006(7) 0.0041(7) 0.0010(8) C4 0.0231(10) 0.0153(11) 0.0294(10) -0.0042(8) 0.0081(8) -0.0039(8) C5 0.0178(9) 0.0197(10) 0.0246(10) -0.0061(8) 0.0069(8) -0.0052(8) C6 0.0154(8) 0.0195(10) 0.0165(9) -0.0029(7) 0.0036(7) 0.0006(8) C7 0.0161(8) 0.0288(15) 0.0291(10) -0.0037(9) 0.0016(8) 0.0046(8) C8 0.0179(8) 0.0154(9) 0.0198(9) -0.0001(7) 0.0052(7) -0.0011(8) C9 0.0249(9) 0.0178(11) 0.0185(8) -0.0007(8) 0.0042(7) -0.0011(9) C10 0.0302(10) 0.0278(15) 0.0277(10) -0.0004(9) 0.0121(8) 0.0023(10) C11 0.0190(9) 0.0182(10) 0.0247(10) 0.0012(8) 0.0097(8) 0.0020(8) C12 0.0246(10) 0.0186(10) 0.0278(10) -0.0037(8) 0.0096(9) 0.0027(8) C13 0.0407(13) 0.0347(13) 0.0275(11) 0.0070(10) 0.0195(10) 0.0094(10) C14 0.0180(10) 0.0329(14) 0.0532(15) -0.0021(11) 0.0121(10) -0.0018(9) 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' 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 N1 109.70(8) . . ? O1 S1 C11 106.29(9) . . ? N1 S1 C11 98.93(9) . . ? S1 N1 H1 114.5 . . ? C1 N1 S1 112.87(13) . . ? C1 N1 H1 113.2 . . ? C6 N2 C2 118.10(19) . . ? N1 C1 H1A 108.9 . . ? N1 C1 C2 109.36(14) . . ? N1 C1 C8 108.43(18) . . ? C2 C1 H1A 108.9 . . ? C2 C1 C8 112.18(14) . . ? C8 C1 H1A 108.9 . . ? N2 C2 C1 116.60(18) . . ? N2 C2 C3 123.03(18) . . ? C3 C2 C1 120.37(18) . . ? C2 C3 H3 120.6 . . ? C2 C3 C4 118.84(19) . . ? C4 C3 H3 120.6 . . ? C3 C4 H4 120.8 . . ? C5 C4 C3 118.32(19) . . ? C5 C4 H4 120.8 . . ? C4 C5 H5 120.2 . . ? C4 C5 C6 119.54(19) . . ? C6 C5 H5 120.2 . . ? N2 C6 C5 122.14(19) . . ? N2 C6 C7 115.62(19) . . ? C5 C6 C7 122.23(18) . . ? C6 C7 H7A 109.5 . . ? C6 C7 H7B 109.5 . . ? C6 C7 H7C 109.5 . . ? H7A C7 H7B 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? C1 C8 H8A 109.3 . . ? C1 C8 H8B 109.3 . . ? H8A C8 H8B 107.9 . . ? C9 C8 C1 111.78(17) . . ? C9 C8 H8A 109.3 . . ? C9 C8 H8B 109.3 . . ? C8 C9 H9 118.0 . . ? C10 C9 C8 124.0(2) . . ? C10 C9 H9 118.0 . . ? C9 C10 H10A 120.0 . . ? C9 C10 H10B 120.0 . . ? H10A C10 H10B 120.0 . . ? C12 C11 S1 112.43(14) . . ? C12 C11 C13 111.0(2) . . ? C12 C11 C14 111.83(19) . . ? C13 C11 S1 104.48(15) . . ? C14 C11 S1 105.54(15) . . ? C14 C11 C13 111.25(19) . . ? C11 C12 H12A 109.5 . . ? C11 C12 H12B 109.5 . . ? C11 C12 H12C 109.5 . . ? H12A C12 H12B 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? C11 C13 H13A 109.5 . . ? C11 C13 H13B 109.5 . . ? C11 C13 H13C 109.5 . . ? H13A C13 H13B 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? C11 C14 H14A 109.5 . . ? C11 C14 H14B 109.5 . . ? C11 C14 H14C 109.5 . . ? H14A C14 H14B 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? 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 1.5004(13) . ? S1 N1 1.6657(16) . ? S1 C11 1.844(2) . ? N1 H1 0.8907 . ? N1 C1 1.488(2) . ? N2 C2 1.342(2) . ? N2 C6 1.342(2) . ? C1 H1A 1.0000 . ? C1 C2 1.519(3) . ? C1 C8 1.532(3) . ? C2 C3 1.382(3) . ? C3 H3 0.9500 . ? C3 C4 1.394(3) . ? C4 H4 0.9500 . ? C4 C5 1.380(3) . ? C5 H5 0.9500 . ? C5 C6 1.392(3) . ? C6 C7 1.504(3) . ? C7 H7A 0.9800 . ? C7 H7B 0.9800 . ? C7 H7C 0.9800 . ? C8 H8A 0.9900 . ? C8 H8B 0.9900 . ? C8 C9 1.496(3) . ? C9 H9 0.9500 . ? C9 C10 1.316(3) . ? C10 H10A 0.9500 . ? C10 H10B 0.9500 . ? C11 C12 1.517(3) . ? C11 C13 1.530(3) . ? C11 C14 1.522(3) . ? C12 H12A 0.9800 . ? C12 H12B 0.9800 . ? C12 H12C 0.9800 . ? C13 H13A 0.9800 . ? C13 H13B 0.9800 . ? C13 H13C 0.9800 . ? C14 H14A 0.9800 . ? C14 H14B 0.9800 . ? C14 H14C 0.9800 . ? 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 C1 C2 81.01(17) . . . . ? S1 N1 C1 C8 -156.39(12) . . . . ? O1 S1 N1 C1 96.78(13) . . . . ? O1 S1 C11 C12 66.33(17) . . . . ? O1 S1 C11 C13 -54.10(17) . . . . ? O1 S1 C11 C14 -171.50(15) . . . . ? N1 S1 C11 C12 -47.33(16) . . . . ? N1 S1 C11 C13 -167.77(15) . . . . ? N1 S1 C11 C14 74.83(16) . . . . ? N1 C1 C2 N2 65.5(2) . . . . ? N1 C1 C2 C3 -114.5(2) . . . . ? N1 C1 C8 C9 168.54(15) . . . . ? N2 C2 C3 C4 1.3(3) . . . . ? C1 C2 C3 C4 -178.61(16) . . . . ? C1 C8 C9 C10 -119.1(2) . . . . ? C2 N2 C6 C5 -0.9(3) . . . . ? C2 N2 C6 C7 178.42(16) . . . . ? C2 C1 C8 C9 -70.6(2) . . . . ? C2 C3 C4 C5 -0.5(3) . . . . ? C3 C4 C5 C6 -1.0(3) . . . . ? C4 C5 C6 N2 1.8(3) . . . . ? C4 C5 C6 C7 -177.54(18) . . . . ? C6 N2 C2 C1 179.31(15) . . . . ? C6 N2 C2 C3 -0.7(3) . . . . ? C8 C1 C2 N2 -54.8(2) . . . . ? C8 C1 C2 C3 125.2(2) . . . . ? C11 S1 N1 C1 -152.25(13) . . . . ?