#------------------------------------------------------------------------------ #$Date: 2017-12-07 07:08:07 +0200 (Thu, 07 Dec 2017) $ #$Revision: 204036 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/15/60/7156021.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_7156021 loop_ _publ_author_name 'Swamy, K. C. Kumara' 'Anitha, Mandala' _publ_section_title ; Synthesis of thiazolidine-thiones, iminothiazolidines and oxazolidines via base promoted cyclisation of epoxy-sulfonamides and heterocumulenes ; _journal_name_full 'Organic & Biomolecular Chemistry' _journal_paper_doi 10.1039/C7OB02915B _journal_year 2017 _chemical_formula_sum 'C18 H19 Cl N2 O2 S2' _chemical_formula_weight 394.92 _space_group_crystal_system monoclinic _space_group_IT_number 14 _space_group_name_Hall '-P 2ybc' _space_group_name_H-M_alt 'P 1 21/c 1' _symmetry_space_group_name_Hall '-P 2ybc' _symmetry_space_group_name_H-M 'P 1 21/c 1' _atom_sites_solution_hydrogens geom _audit_creation_method SHELXL-2014/7 _audit_update_record ; 2017-09-20 deposited with the CCDC. 2017-12-05 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 103.225(12) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 17.218(7) _cell_length_b 7.657(3) _cell_length_c 14.611(6) _cell_measurement_reflns_used 3462 _cell_measurement_temperature 292(2) _cell_measurement_theta_max 21.99 _cell_measurement_theta_min 2.43 _cell_volume 1875.2(13) _computing_cell_refinement 'Bruker SAINT' _computing_data_collection 'Bruker APEX2' _computing_data_reduction 'Bruker SAINT' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _computing_structure_refinement 'SHELXL-2014/7 (Sheldrick, 2014)' _computing_structure_solution 'SHELXL-2014/7 (Sheldrick, 2014)' _diffrn_ambient_temperature 292(2) _diffrn_measured_fraction_theta_full 0.991 _diffrn_measured_fraction_theta_max 0.991 _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.1759 _diffrn_reflns_av_unetI/netI 0.0937 _diffrn_reflns_Laue_measured_fraction_full 0.991 _diffrn_reflns_Laue_measured_fraction_max 0.991 _diffrn_reflns_limit_h_max 20 _diffrn_reflns_limit_h_min -20 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_number 25407 _diffrn_reflns_point_group_measured_fraction_full 0.991 _diffrn_reflns_point_group_measured_fraction_max 0.991 _diffrn_reflns_theta_full 25.000 _diffrn_reflns_theta_max 25.000 _diffrn_reflns_theta_min 2.430 _diffrn_source 'fine-focus sealed tube' _exptl_absorpt_coefficient_mu 0.440 _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.399 _exptl_crystal_description blocks _exptl_crystal_F_000 824 _exptl_crystal_recrystallization_method 'Re-crystallisation from solvent' _exptl_crystal_size_max 0.060 _exptl_crystal_size_mid 0.050 _exptl_crystal_size_min 0.050 _refine_diff_density_max 0.299 _refine_diff_density_min -0.334 _refine_diff_density_rms 0.061 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.009 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 229 _refine_ls_number_reflns 3274 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.009 _refine_ls_R_factor_all 0.1276 _refine_ls_R_factor_gt 0.0547 _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^)+(0.0528P)^2^+0.1817P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1079 _refine_ls_wR_factor_ref 0.1277 _reflns_Friedel_coverage 0.000 _reflns_number_gt 1899 _reflns_number_total 3274 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file c7ob02915b2.cif _cod_data_source_block Compound40 _cod_database_code 7156021 _shelx_shelxl_version_number 2014/7 _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_min 0.974 _shelx_estimated_absorpt_t_max 0.978 _shelx_res_file ; shelx.res created by SHELXL-2014/7 TITL kck53_a.res in P2(1)/c CELL 0.71073 17.2184 7.6570 14.6110 90.000 103.225 90.000 ZERR 4.00 0.0068 0.0030 0.0056 0.000 0.012 0.000 LATT 1 SYMM - X, 1/2 + Y, 1/2 - Z SFAC C H N O S CL UNIT 72 76 8 8 8 4 MERG 2 SIZE 0.050 0.050 0.060 OMIT -1.00 50.00 FMAP 2 PLAN 20 ACTA BOND $H LIST 6 L.S. 10 TEMP 18.80 WGHT 0.052800 0.181700 FVAR 0.41922 S1 5 0.393926 0.699081 0.351411 11.00000 0.04073 0.03421 = 0.03515 0.00415 0.01490 -0.00082 S2 5 0.384742 0.191843 0.456346 11.00000 0.05359 0.03504 = 0.05478 0.00990 0.02402 0.00975 CL1 6 0.038723 0.826936 0.148810 11.00000 0.04733 0.13309 = 0.08470 0.01605 -0.00888 -0.00775 O1 4 0.405641 0.792689 0.437799 11.00000 0.05094 0.03893 = 0.03766 -0.00924 0.00464 0.00284 O2 4 0.448596 0.727862 0.292815 11.00000 0.05436 0.05727 = 0.05496 0.01362 0.03082 -0.00671 N1 3 0.398005 0.485559 0.372063 11.00000 0.03899 0.03211 = 0.03818 0.00458 0.02277 0.00750 N2 3 0.303862 0.493259 0.464929 11.00000 0.05796 0.04049 = 0.04412 0.01025 0.03233 0.01168 C9 1 0.355820 0.408636 0.433963 11.00000 0.03644 0.03685 = 0.02365 0.00172 0.00746 -0.00204 C10 1 0.262784 0.410123 0.525673 11.00000 0.04639 0.03255 = 0.03544 0.00271 0.02042 0.00685 C6 1 0.269223 0.694258 0.193578 11.00000 0.05813 0.03648 = 0.03409 0.00381 0.01629 -0.00298 C1 1 0.294892 0.734120 0.289547 11.00000 0.03785 0.03255 = 0.02692 0.00528 0.00982 -0.00200 C13 1 0.176529 0.266515 0.648855 11.00000 0.05417 0.05136 = 0.04303 -0.00071 0.02814 -0.00206 C2 1 0.243191 0.803033 0.338922 11.00000 0.05140 0.03808 = 0.03125 0.00375 0.01211 0.00101 AFIX 43 H2 2 0.263035 0.831188 0.401851 11.00000 -1.20000 AFIX 0 C11 1 0.299004 0.377039 0.618289 11.00000 0.03660 0.05862 = 0.05025 0.01409 0.01580 -0.00157 AFIX 43 H11 2 0.352846 0.402397 0.640524 11.00000 -1.20000 AFIX 0 C7 1 0.467306 0.383353 0.360117 11.00000 0.05109 0.04824 = 0.05753 0.00263 0.02614 0.01218 AFIX 23 H7A 2 0.514901 0.419294 0.405680 11.00000 -1.20000 H7B 2 0.476175 0.400122 0.297495 11.00000 -1.20000 AFIX 0 C4 1 0.138414 0.795913 0.205109 11.00000 0.04246 0.05992 = 0.05501 0.01025 0.00530 -0.00536 C8 1 0.448580 0.195765 0.374937 11.00000 0.03847 0.04603 = 0.03923 -0.00283 0.01429 0.01127 AFIX 23 H8A 2 0.497278 0.131362 0.400201 11.00000 -1.20000 H8B 2 0.421914 0.142701 0.315803 11.00000 -1.20000 AFIX 0 C3 1 0.163169 0.832866 0.300137 11.00000 0.04407 0.04577 = 0.04819 0.01087 0.01340 0.00550 C12 1 0.256280 0.306951 0.678033 11.00000 0.05258 0.06032 = 0.03435 0.01440 0.00934 0.00568 AFIX 43 H12 2 0.282066 0.286100 0.740274 11.00000 -1.20000 AFIX 0 C16 1 0.319975 0.619230 0.132361 11.00000 0.08242 0.06670 = 0.03166 -0.00683 0.02374 0.00015 AFIX 137 H16A 2 0.349558 0.711263 0.111370 11.00000 -1.50000 H16B 2 0.286491 0.562978 0.078921 11.00000 -1.50000 H16C 2 0.356347 0.535445 0.167623 11.00000 -1.50000 AFIX 0 C5 1 0.188573 0.729399 0.153867 11.00000 0.06730 0.05876 = 0.03015 0.00684 0.00014 -0.01313 AFIX 43 H5 2 0.168584 0.706528 0.090323 11.00000 -1.20000 AFIX 0 C15 1 0.182397 0.374587 0.496372 11.00000 0.05206 0.10015 = 0.02573 -0.00190 0.00933 -0.00451 AFIX 43 H15 2 0.155774 0.399876 0.434945 11.00000 -1.20000 AFIX 0 C14 1 0.141458 0.302226 0.557191 11.00000 0.04265 0.10903 = 0.04951 -0.00512 0.01327 -0.02266 AFIX 43 H14 2 0.087643 0.276446 0.535103 11.00000 -1.20000 AFIX 0 C17 1 0.108546 0.897931 0.359701 11.00000 0.05732 0.10607 = 0.07364 0.00926 0.02305 0.02017 AFIX 137 H17A 2 0.070602 0.978097 0.323836 11.00000 -1.50000 H17B 2 0.139379 0.956261 0.414182 11.00000 -1.50000 H17C 2 0.080814 0.800941 0.379083 11.00000 -1.50000 AFIX 0 C18 1 0.130183 0.192053 0.715785 11.00000 0.08779 0.08118 = 0.07658 0.00759 0.05008 -0.00575 AFIX 137 H18A 2 0.166309 0.162204 0.774050 11.00000 -1.50000 H18B 2 0.102133 0.089294 0.688691 11.00000 -1.50000 H18C 2 0.092611 0.277273 0.727210 11.00000 -1.50000 AFIX 0 HKLF 4 REM kck53_a.res in P2(1)/c REM R1 = 0.0547 for 1899 Fo > 4sig(Fo) and 0.1276 for all 3274 data REM 229 parameters refined using 0 restraints END WGHT 0.0528 0.1817 REM Highest difference peak 0.299, deepest hole -0.334, 1-sigma level 0.061 Q1 1 0.1484 0.0564 0.7743 11.00000 0.05 0.30 Q2 1 0.3874 0.3437 0.4606 11.00000 0.05 0.29 Q3 1 0.3983 0.5632 0.3528 11.00000 0.05 0.26 Q4 1 0.3960 0.0255 0.3415 11.00000 0.05 0.25 Q5 1 0.0000 0.5000 0.5000 10.50000 0.05 0.24 Q6 1 0.4159 0.4170 0.3597 11.00000 0.05 0.24 Q7 1 0.2864 0.5908 0.4591 11.00000 0.05 0.24 Q8 1 0.0408 0.7208 0.0811 11.00000 0.05 0.24 Q9 1 0.1532 0.3183 0.7821 11.00000 0.05 0.23 Q10 1 0.3951 0.9445 0.4334 11.00000 0.05 0.22 Q11 1 0.3526 0.0155 0.5048 11.00000 0.05 0.22 Q12 1 0.0294 0.6315 0.1456 11.00000 0.05 0.21 Q13 1 0.2974 0.4484 0.4228 11.00000 0.05 0.21 Q14 1 0.2944 0.1806 0.6796 11.00000 0.05 0.20 Q15 1 0.3995 0.8814 0.3599 11.00000 0.05 0.20 Q16 1 0.4092 0.8423 0.4779 11.00000 0.05 0.20 Q17 1 0.3715 0.0491 0.3262 11.00000 0.05 0.20 Q18 1 0.3131 0.4651 0.1380 11.00000 0.05 0.20 Q19 1 0.4102 0.2813 0.4998 11.00000 0.05 0.19 Q20 1 0.0309 1.0067 0.1246 11.00000 0.05 0.19 ; _shelx_res_checksum 47890 loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' 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 S1 S 0.39393(5) 0.69908(11) 0.35141(6) 0.0357(3) Uani 1 1 d . . S2 S 0.38474(6) 0.19184(11) 0.45635(7) 0.0459(3) Uani 1 1 d . . Cl1 Cl 0.03872(6) 0.82694(18) 0.14881(10) 0.0922(5) Uani 1 1 d . . O1 O 0.40564(13) 0.7927(3) 0.43780(17) 0.0434(7) Uani 1 1 d . . O2 O 0.44860(15) 0.7279(3) 0.29282(18) 0.0526(7) Uani 1 1 d . . N1 N 0.39801(15) 0.4856(3) 0.3721(2) 0.0342(7) Uani 1 1 d . . N2 N 0.30386(18) 0.4933(4) 0.4649(2) 0.0442(8) Uani 1 1 d . . C9 C 0.3558(2) 0.4086(4) 0.4340(2) 0.0322(8) Uani 1 1 d . . C10 C 0.2628(2) 0.4101(4) 0.5257(3) 0.0363(9) Uani 1 1 d . . C6 C 0.2692(2) 0.6943(4) 0.1936(3) 0.0420(10) Uani 1 1 d . . C1 C 0.2949(2) 0.7341(4) 0.2895(2) 0.0321(8) Uani 1 1 d . . C13 C 0.1765(2) 0.2665(4) 0.6489(3) 0.0468(10) Uani 1 1 d . . C2 C 0.2432(2) 0.8030(4) 0.3389(3) 0.0398(9) Uani 1 1 d . . H2 H 0.2630 0.8312 0.4019 0.048 Uiso 1 1 calc R U C11 C 0.2990(2) 0.3770(5) 0.6183(3) 0.0475(10) Uani 1 1 d . . H11 H 0.3528 0.4024 0.6405 0.057 Uiso 1 1 calc R U C7 C 0.4673(2) 0.3834(4) 0.3601(3) 0.0501(11) Uani 1 1 d . . H7A H 0.5149 0.4193 0.4057 0.060 Uiso 1 1 calc R U H7B H 0.4762 0.4001 0.2975 0.060 Uiso 1 1 calc R U C4 C 0.1384(2) 0.7959(5) 0.2051(3) 0.0534(11) Uani 1 1 d . . C8 C 0.4486(2) 0.1958(4) 0.3749(3) 0.0404(9) Uani 1 1 d . . H8A H 0.4973 0.1314 0.4002 0.048 Uiso 1 1 calc R U H8B H 0.4219 0.1427 0.3158 0.048 Uiso 1 1 calc R U C3 C 0.1632(2) 0.8329(4) 0.3001(3) 0.0456(10) Uani 1 1 d . . C12 C 0.2563(2) 0.3070(5) 0.6780(3) 0.0492(10) Uani 1 1 d . . H12 H 0.2821 0.2861 0.7403 0.059 Uiso 1 1 calc R U C16 C 0.3200(3) 0.6192(5) 0.1324(3) 0.0585(11) Uani 1 1 d . . H16A H 0.3496 0.7113 0.1114 0.088 Uiso 1 1 calc R U H16B H 0.2865 0.5630 0.0789 0.088 Uiso 1 1 calc R U H16C H 0.3563 0.5354 0.1676 0.088 Uiso 1 1 calc R U C5 C 0.1886(3) 0.7294(5) 0.1539(3) 0.0538(11) Uani 1 1 d . . H5 H 0.1686 0.7065 0.0903 0.065 Uiso 1 1 calc R U C15 C 0.1824(2) 0.3746(6) 0.4964(3) 0.0592(12) Uani 1 1 d . . H15 H 0.1558 0.3999 0.4349 0.071 Uiso 1 1 calc R U C14 C 0.1415(2) 0.3022(6) 0.5572(3) 0.0666(13) Uani 1 1 d . . H14 H 0.0876 0.2764 0.5351 0.080 Uiso 1 1 calc R U C17 C 0.1085(2) 0.8979(6) 0.3597(3) 0.0777(14) Uani 1 1 d . . H17A H 0.0706 0.9781 0.3238 0.117 Uiso 1 1 calc R U H17B H 0.1394 0.9563 0.4142 0.117 Uiso 1 1 calc R U H17C H 0.0808 0.8009 0.3791 0.117 Uiso 1 1 calc R U C18 C 0.1302(3) 0.1921(5) 0.7158(3) 0.0768(14) Uani 1 1 d . . H18A H 0.1663 0.1622 0.7740 0.115 Uiso 1 1 calc R U H18B H 0.1021 0.0893 0.6887 0.115 Uiso 1 1 calc R U H18C H 0.0926 0.2773 0.7272 0.115 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 0.0407(5) 0.0342(5) 0.0351(6) 0.0041(4) 0.0149(5) -0.0008(4) S2 0.0536(6) 0.0350(5) 0.0548(7) 0.0099(5) 0.0240(5) 0.0098(4) Cl1 0.0473(7) 0.1331(12) 0.0847(11) 0.0160(8) -0.0089(7) -0.0077(7) O1 0.0509(15) 0.0389(13) 0.0377(16) -0.0092(12) 0.0046(13) 0.0028(11) O2 0.0544(16) 0.0573(16) 0.0550(19) 0.0136(13) 0.0308(15) -0.0067(12) N1 0.0390(16) 0.0321(15) 0.0382(19) 0.0046(13) 0.0228(16) 0.0075(13) N2 0.0580(19) 0.0405(17) 0.044(2) 0.0102(15) 0.0323(18) 0.0117(15) C9 0.036(2) 0.0369(19) 0.024(2) 0.0017(16) 0.0075(18) -0.0020(16) C10 0.046(2) 0.0325(19) 0.035(3) 0.0027(17) 0.020(2) 0.0069(16) C6 0.058(3) 0.036(2) 0.034(2) 0.0038(18) 0.016(2) -0.0030(18) C1 0.038(2) 0.0326(18) 0.027(2) 0.0053(15) 0.0098(18) -0.0020(15) C13 0.054(3) 0.051(2) 0.043(3) -0.0007(19) 0.028(2) -0.0021(19) C2 0.051(2) 0.038(2) 0.031(2) 0.0038(17) 0.012(2) 0.0010(18) C11 0.037(2) 0.059(2) 0.050(3) 0.014(2) 0.016(2) -0.0016(18) C7 0.051(2) 0.048(2) 0.058(3) 0.003(2) 0.026(2) 0.0122(19) C4 0.042(2) 0.060(3) 0.055(3) 0.010(2) 0.005(2) -0.005(2) C8 0.038(2) 0.046(2) 0.039(2) -0.0028(18) 0.0143(19) 0.0113(17) C3 0.044(2) 0.046(2) 0.048(3) 0.0109(19) 0.013(2) 0.0055(18) C12 0.053(3) 0.060(2) 0.034(2) 0.014(2) 0.009(2) 0.006(2) C16 0.082(3) 0.067(3) 0.032(3) -0.007(2) 0.024(2) 0.000(2) C5 0.067(3) 0.059(3) 0.030(3) 0.0068(19) 0.000(2) -0.013(2) C15 0.052(3) 0.100(3) 0.026(3) -0.002(2) 0.009(2) -0.005(2) C14 0.043(2) 0.109(4) 0.050(3) -0.005(3) 0.013(2) -0.023(2) C17 0.057(3) 0.106(4) 0.074(4) 0.009(3) 0.023(3) 0.020(3) C18 0.088(3) 0.081(3) 0.077(4) 0.008(3) 0.050(3) -0.006(3) 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' Cl Cl 0.1484 0.1585 '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 O1 S1 O2 118.33(15) O1 S1 N1 110.03(14) O2 S1 N1 104.76(14) O1 S1 C1 107.62(15) O2 S1 C1 111.30(16) N1 S1 C1 103.85(14) C9 S2 C8 92.97(16) C9 N1 C7 113.9(3) C9 N1 S1 121.4(2) C7 N1 S1 120.3(2) C9 N2 C10 119.4(3) N2 C9 N1 121.6(3) N2 C9 S2 127.9(3) N1 C9 S2 110.5(2) C11 C10 C15 117.7(4) C11 C10 N2 121.5(3) C15 C10 N2 120.5(4) C5 C6 C1 115.3(4) C5 C6 C16 118.9(4) C1 C6 C16 125.8(3) C2 C1 C6 121.0(3) C2 C1 S1 117.2(3) C6 C1 S1 121.8(3) C14 C13 C12 116.4(4) C14 C13 C18 122.1(4) C12 C13 C18 121.5(4) C1 C2 C3 123.6(4) C1 C2 H2 118.2 C3 C2 H2 118.2 C12 C11 C10 120.6(4) C12 C11 H11 119.7 C10 C11 H11 119.7 N1 C7 C8 106.6(3) N1 C7 H7A 110.4 C8 C7 H7A 110.4 N1 C7 H7B 110.4 C8 C7 H7B 110.4 H7A C7 H7B 108.6 C5 C4 C3 122.5(4) C5 C4 Cl1 118.1(3) C3 C4 Cl1 119.3(4) C7 C8 S2 107.2(2) C7 C8 H8A 110.3 S2 C8 H8A 110.3 C7 C8 H8B 110.3 S2 C8 H8B 110.3 H8A C8 H8B 108.5 C2 C3 C4 115.2(4) C2 C3 C17 120.9(4) C4 C3 C17 123.9(4) C11 C12 C13 122.2(4) C11 C12 H12 118.9 C13 C12 H12 118.9 C6 C16 H16A 109.5 C6 C16 H16B 109.5 H16A C16 H16B 109.5 C6 C16 H16C 109.5 H16A C16 H16C 109.5 H16B C16 H16C 109.5 C4 C5 C6 122.4(4) C4 C5 H5 118.8 C6 C5 H5 118.8 C14 C15 C10 120.4(4) C14 C15 H15 119.8 C10 C15 H15 119.8 C13 C14 C15 122.6(4) C13 C14 H14 118.7 C15 C14 H14 118.7 C3 C17 H17A 109.5 C3 C17 H17B 109.5 H17A C17 H17B 109.5 C3 C17 H17C 109.5 H17A C17 H17C 109.5 H17B C17 H17C 109.5 C13 C18 H18A 109.5 C13 C18 H18B 109.5 H18A C18 H18B 109.5 C13 C18 H18C 109.5 H18A C18 H18C 109.5 H18B C18 H18C 109.5 loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance S1 O1 1.425(2) S1 O2 1.427(3) S1 N1 1.661(3) S1 C1 1.758(3) S2 C9 1.742(3) S2 C8 1.795(4) Cl1 C4 1.742(4) N1 C9 1.412(4) N1 C7 1.470(4) N2 C9 1.269(4) N2 C10 1.407(4) C10 C11 1.378(5) C10 C15 1.379(5) C6 C5 1.403(5) C6 C1 1.404(5) C6 C16 1.500(5) C1 C2 1.373(5) C13 C14 1.365(5) C13 C12 1.377(5) C13 C18 1.508(5) C2 C3 1.384(5) C2 H2 0.9300 C11 C12 1.373(5) C11 H11 0.9300 C7 C8 1.499(4) C7 H7A 0.9700 C7 H7B 0.9700 C4 C5 1.364(6) C4 C3 1.385(6) C8 H8A 0.9700 C8 H8B 0.9700 C3 C17 1.505(5) C12 H12 0.9300 C16 H16A 0.9600 C16 H16B 0.9600 C16 H16C 0.9600 C5 H5 0.9300 C15 C14 1.371(5) C15 H15 0.9300 C14 H14 0.9300 C17 H17A 0.9600 C17 H17B 0.9600 C17 H17C 0.9600 C18 H18A 0.9600 C18 H18B 0.9600 C18 H18C 0.9600