# Electronic Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2013 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_cm44_0m _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common 'Potassium (4-nitrophenylcarbamothioyl)(tosyl)amide' _chemical_melting_point ? _chemical_formula_moiety '2(C14 H12 N3 O4 S2), 2.5(C3 H6 O1), K2' _chemical_formula_sum 'C35.50 H39 K2 N6 O10.50 S4' _chemical_formula_weight 924.17 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' K K 0.2009 0.2494 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.3664(12) _cell_length_b 16.466(3) _cell_length_c 18.699(3) _cell_angle_alpha 107.650(2) _cell_angle_beta 93.736(2) _cell_angle_gamma 96.762(2) _cell_volume 2134.1(6) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 2340 _cell_measurement_theta_min 2.30 _cell_measurement_theta_max 21.26 _exptl_crystal_description Needles _exptl_crystal_colour Yellow _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.438 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 960 _exptl_absorpt_coefficient_mu 0.480 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.802 _exptl_absorpt_correction_T_max 0.949 _exptl_absorpt_process_details 'SADABS (Sheldrick, 1996)' _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 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 21256 _diffrn_reflns_av_R_equivalents 0.0669 _diffrn_reflns_av_sigmaI/netI 0.0973 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -20 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 1.15 _diffrn_reflns_theta_max 25.60 _reflns_number_total 7955 _reflns_number_gt 3987 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _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. ; _vrf_PLAT220_cm44_0m ; PROBLEM: Large Non-Solvent C Ueq(max)/Ueq(min) ... 5.0 Ratio Large Non-Solvent O Ueq(max)/Ueq(min) ... 4.7 Ratio RESPONSE: A large difference in Ueq between carbon and oxygen atoms is caused by the presence of a highly disordered acetone molecule. ; _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^)+(0.0741P)^2^+0.0107P] 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_number_reflns 7955 _refine_ls_number_parameters 540 _refine_ls_number_restraints 27 _refine_ls_R_factor_all 0.1361 _refine_ls_R_factor_gt 0.0582 _refine_ls_wR_factor_ref 0.1656 _refine_ls_wR_factor_gt 0.1269 _refine_ls_goodness_of_fit_ref 0.965 _refine_ls_restrained_S_all 0.968 _refine_ls_shift/su_max 0.018 _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 O1 O 1.0433(4) 0.99159(18) 0.27155(16) 0.0445(8) Uani 1 1 d . . . O2 O 0.7167(4) 0.98865(19) 0.24673(18) 0.0524(9) Uani 1 1 d . . . N1 N 0.8798(5) 0.8872(2) 0.14846(19) 0.0408(9) Uani 1 1 d . . . N2 N 0.9284(5) 0.8773(2) 0.0263(2) 0.0469(10) Uani 1 1 d . . . H1N H 0.9463 0.9057 -0.0049 0.056 Uiso 1 1 calc R . . C8 C 0.9214(6) 0.9283(3) 0.0987(3) 0.0414(11) Uani 1 1 d . . . C9 C 0.9120(6) 0.7878(3) -0.0070(2) 0.0409(11) Uani 1 1 d . . . C14 C 0.9032(7) 0.7573(3) -0.0850(3) 0.0531(13) Uani 1 1 d . . . H14 H 0.9026 0.7960 -0.1123 0.064 Uiso 1 1 calc R . . C11 C 0.8961(7) 0.6427(3) -0.0055(3) 0.0592(14) Uani 1 1 d . . . H11 H 0.8917 0.6031 0.0210 0.071 Uiso 1 1 calc R . . C12 C 0.8920(6) 0.6149(3) -0.0825(3) 0.0431(11) Uani 1 1 d . . . C13 C 0.8953(7) 0.6714(3) -0.1226(3) 0.0545(13) Uani 1 1 d . . . H13 H 0.8923 0.6520 -0.1749 0.065 Uiso 1 1 calc R . . C10 C 0.9068(7) 0.7293(3) 0.0327(3) 0.0588(14) Uani 1 1 d . . . H10 H 0.9105 0.7484 0.0850 0.071 Uiso 1 1 calc R . . N3 N 0.8864(6) 0.5229(3) -0.1209(3) 0.0599(12) Uani 1 1 d . . . O4 O 0.9046(6) 0.5004(2) -0.1884(2) 0.0802(12) Uani 1 1 d . . . O3 O 0.8642(6) 0.4727(2) -0.0849(2) 0.0858(13) Uani 1 1 d . . . N4 N 1.4667(5) 1.7045(2) 0.6419(2) 0.0435(9) Uani 1 1 d . . . N5 N 1.4074(5) 1.6984(2) 0.5181(2) 0.0529(11) Uani 1 1 d . . . H2N H 1.4177 1.7267 0.4864 0.063 Uiso 1 1 calc R . . C15 C 1.4662(6) 1.6722(3) 0.7695(3) 0.0410(11) Uani 1 1 d . . . C17 C 1.3171(6) 1.6149(3) 0.4867(2) 0.0410(11) Uani 1 1 d . . . C16 C 1.4846(7) 1.7450(3) 0.5910(3) 0.0494(12) Uani 1 1 d . . . C18 C 1.3039(6) 1.5522(3) 0.5230(3) 0.0497(12) Uani 1 1 d . . . H18 H 1.3548 1.5657 0.5727 0.060 Uiso 1 1 calc R . . C20 C 1.1403(6) 1.4503(3) 0.4118(3) 0.0397(11) Uani 1 1 d . . . C22 C 1.2380(7) 1.5920(3) 0.4113(3) 0.0493(12) Uani 1 1 d . . . H22 H 1.2458 1.6331 0.3863 0.059 Uiso 1 1 calc R . . C19 C 1.2159(6) 1.4708(3) 0.4853(3) 0.0482(12) Uani 1 1 d . . . H19 H 1.2073 1.4291 0.5096 0.058 Uiso 1 1 calc R . . C21 C 1.1498(6) 1.5105(3) 0.3743(3) 0.0496(12) Uani 1 1 d . . . H21 H 1.0973 1.4961 0.3246 0.059 Uiso 1 1 calc R . . O6 O 0.9827(5) 1.3454(2) 0.3069(2) 0.0655(10) Uani 1 1 d . . . O5 O 1.0335(5) 1.3115(2) 0.40855(19) 0.0660(10) Uani 1 1 d . . . N6 N 1.0464(5) 1.3637(2) 0.3731(2) 0.0486(10) Uani 1 1 d . . . C24 C 1.4687(7) 1.5300(3) 0.7755(3) 0.0633(15) Uani 1 1 d . . . H24 H 1.4935 1.4742 0.7538 0.076 Uiso 1 1 calc R . . C27 C 1.3931(7) 1.6936(3) 0.8368(3) 0.0594(14) Uani 1 1 d . . . H27 H 1.3645 1.7488 0.8579 0.071 Uiso 1 1 calc R . . C23 C 1.5031(7) 1.5895(3) 0.7377(3) 0.0538(13) Uani 1 1 d . . . H23 H 1.5506 1.5740 0.6913 0.065 Uiso 1 1 calc R . . C25 C 1.3998(7) 1.5503(4) 0.8432(3) 0.0631(15) Uani 1 1 d . . . C26 C 1.3618(8) 1.6325(4) 0.8735(3) 0.0695(16) Uani 1 1 d . . . H26 H 1.3139 1.6477 0.9198 0.083 Uiso 1 1 calc R . . C28 C 1.3662(9) 1.4851(4) 0.8852(4) 0.095(2) Uani 1 1 d . . . H28A H 1.4042 1.4318 0.8571 0.142 Uiso 1 1 calc R . . H28B H 1.2376 1.4756 0.8909 0.142 Uiso 1 1 calc R . . H28C H 1.4355 1.5067 0.9340 0.142 Uiso 1 1 calc R . . O7 O 1.7195(4) 1.7818(2) 0.74734(18) 0.0572(9) Uani 1 1 d . . . O8 O 1.4125(4) 1.82049(19) 0.75833(18) 0.0553(9) Uani 1 1 d . . . O9 O 1.2766(6) 1.8029(3) 0.4229(2) 0.0845(13) Uani 1 1 d . . . O10 O 1.6666(6) 2.1517(3) 0.8123(3) 0.129(2) Uani 1 1 d . . . C30 C 1.2189(8) 1.8681(4) 0.4556(3) 0.0673(16) Uani 1 1 d . . . C33 C 1.6288(8) 2.2238(4) 0.8332(5) 0.088(2) Uani 1 1 d . . . C31 C 1.1210(9) 1.8735(4) 0.5236(4) 0.103(2) Uani 1 1 d . . . H31A H 1.1123 1.8192 0.5333 0.155 Uiso 1 1 calc R . . H31B H 0.9998 1.8870 0.5152 0.155 Uiso 1 1 calc R . . H31C H 1.1879 1.9177 0.5663 0.155 Uiso 1 1 calc R . . C29 C 1.2482(10) 1.9435(4) 0.4285(4) 0.113(3) Uani 1 1 d . . . H29A H 1.3133 1.9296 0.3845 0.170 Uiso 1 1 calc R . . H29B H 1.3189 1.9910 0.4674 0.170 Uiso 1 1 calc R . . H29C H 1.1315 1.9591 0.4160 0.170 Uiso 1 1 calc R . . K1 K 2.05615(15) 1.84157(6) 0.71379(6) 0.0534(3) Uani 1 1 d . . . K2 K 0.37265(14) 1.02189(7) 0.22068(7) 0.0562(3) Uani 1 1 d . . . C1A C 1.6357(9) 2.2781(4) 0.7817(4) 0.104(2) Uani 1 1 d . . . H1A1 H 1.6652 2.2449 0.7332 0.155 Uiso 1 1 calc R . . H1A2 H 1.7282 2.3275 0.8027 0.155 Uiso 1 1 calc R . . H1A3 H 1.5183 2.2966 0.7762 0.155 Uiso 1 1 calc R . . C2A C 1.5775(11) 2.2633(5) 0.9089(5) 0.140(3) Uani 1 1 d . . . H2A1 H 1.6017 2.2280 0.9399 0.210 Uiso 1 1 calc R . . H2A2 H 1.4490 2.2685 0.9058 0.210 Uiso 1 1 calc R . . H2A3 H 1.6482 2.3194 0.9307 0.210 Uiso 1 1 calc R . . S1 S 0.87046(15) 0.94104(7) 0.23480(6) 0.0371(3) Uani 1 1 d . . . S3 S 1.52487(16) 1.75425(7) 0.72843(6) 0.0412(3) Uani 1 1 d . . . S5 S 0.9708(2) 1.03573(8) 0.11446(7) 0.0643(4) Uani 1 1 d . . . S6 S 1.5897(2) 1.84571(8) 0.60148(8) 0.0737(5) Uani 1 1 d . . . C5 C 0.8306(6) 0.8575(3) 0.2748(2) 0.0363(10) Uani 1 1 d . . . C3 C 0.7158(7) 0.8118(4) 0.3753(3) 0.0641(15) Uani 1 1 d . . . H3 H 0.6518 0.8224 0.4177 0.077 Uiso 1 1 calc R . . C7 C 0.8926(7) 0.7250(3) 0.2908(3) 0.0583(14) Uani 1 1 d . . . H7 H 0.9482 0.6756 0.2749 0.070 Uiso 1 1 calc R . . C6 C 0.9106(6) 0.7838(3) 0.2522(3) 0.0528(13) Uani 1 1 d . . . H6 H 0.9771 0.7737 0.2106 0.063 Uiso 1 1 calc R . . C2 C 0.7953(7) 0.7371(3) 0.3521(3) 0.0553(14) Uani 1 1 d . . . C4 C 0.7315(7) 0.8712(3) 0.3354(3) 0.0568(14) Uani 1 1 d . . . H4 H 0.6742 0.9202 0.3502 0.068 Uiso 1 1 calc R . . C1 C 0.7766(8) 0.6726(4) 0.3953(3) 0.0849(19) Uani 1 1 d . . . H1A H 0.7039 0.6924 0.4362 0.127 Uiso 1 1 calc R . . H1B H 0.8964 0.6668 0.4150 0.127 Uiso 1 1 calc R . . H1C H 0.7178 0.6178 0.3621 0.127 Uiso 1 1 calc R . . C1S C 0.5000 1.0000 0.0000 0.181(8) Uani 1 2 d SDU . . C2S C 0.444(3) 0.934(2) 0.034(2) 0.179(10) Uani 0.50 1 d PDU . . H2S1 H 0.4471 0.8780 -0.0020 0.269 Uiso 0.50 1 calc PR . . H2S2 H 0.3219 0.9378 0.0477 0.269 Uiso 0.50 1 calc PR . . H2S3 H 0.5272 0.9411 0.0778 0.269 Uiso 0.50 1 calc PR . . O1S O 0.506(4) 1.0783(7) 0.0351(19) 0.209(8) Uani 0.50 1 d PDU . . C3S C 0.569(3) 0.965(3) -0.0722(7) 0.167(10) Uani 0.50 1 d PDU . . H3S1 H 0.5465 0.9031 -0.0875 0.250 Uiso 0.50 1 calc PR . . H3S2 H 0.6994 0.9836 -0.0676 0.250 Uiso 0.50 1 calc PR . . H3S3 H 0.5085 0.9847 -0.1094 0.250 Uiso 0.50 1 calc PR . . 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 O1 0.0467(19) 0.0392(18) 0.0445(19) 0.0136(15) 0.0004(15) -0.0052(14) O2 0.048(2) 0.052(2) 0.066(2) 0.0239(18) 0.0175(17) 0.0174(16) N1 0.059(2) 0.030(2) 0.032(2) 0.0094(17) 0.0036(18) 0.0025(17) N2 0.075(3) 0.031(2) 0.034(2) 0.0115(18) 0.006(2) 0.0012(19) C8 0.055(3) 0.032(3) 0.037(3) 0.013(2) 0.000(2) 0.006(2) C9 0.050(3) 0.034(3) 0.037(3) 0.010(2) 0.003(2) 0.002(2) C14 0.086(4) 0.036(3) 0.039(3) 0.017(2) 0.001(3) 0.004(3) C11 0.101(4) 0.037(3) 0.044(3) 0.019(3) 0.009(3) 0.009(3) C12 0.055(3) 0.023(2) 0.045(3) 0.006(2) -0.001(2) 0.000(2) C13 0.081(4) 0.041(3) 0.036(3) 0.007(2) 0.004(3) 0.003(3) C10 0.103(4) 0.038(3) 0.038(3) 0.015(2) 0.009(3) 0.013(3) N3 0.076(3) 0.039(3) 0.058(3) 0.009(2) -0.003(3) 0.003(2) O4 0.128(4) 0.046(2) 0.058(3) 0.003(2) 0.002(2) 0.017(2) O3 0.146(4) 0.031(2) 0.076(3) 0.018(2) -0.003(3) 0.001(2) N4 0.059(3) 0.035(2) 0.031(2) 0.0085(18) 0.0002(18) -0.0042(18) N5 0.080(3) 0.034(2) 0.042(2) 0.0145(19) 0.006(2) -0.007(2) C15 0.039(3) 0.039(3) 0.046(3) 0.017(2) 0.004(2) 0.001(2) C17 0.051(3) 0.033(3) 0.036(3) 0.007(2) 0.009(2) 0.002(2) C16 0.062(3) 0.038(3) 0.044(3) 0.009(2) 0.004(3) -0.001(2) C18 0.068(3) 0.038(3) 0.042(3) 0.015(2) 0.000(2) -0.003(2) C20 0.046(3) 0.029(2) 0.038(3) 0.002(2) 0.007(2) 0.001(2) C22 0.074(3) 0.034(3) 0.040(3) 0.015(2) 0.005(3) 0.001(2) C19 0.067(3) 0.035(3) 0.043(3) 0.016(2) 0.007(3) -0.001(2) C21 0.064(3) 0.039(3) 0.041(3) 0.009(2) 0.002(2) 0.003(2) O6 0.087(3) 0.048(2) 0.045(2) -0.0007(18) -0.010(2) -0.0047(19) O5 0.096(3) 0.036(2) 0.060(2) 0.0117(18) 0.007(2) -0.0055(18) N6 0.054(3) 0.037(2) 0.049(3) 0.005(2) 0.010(2) 0.0049(19) C24 0.073(4) 0.041(3) 0.077(4) 0.020(3) 0.003(3) 0.009(3) C27 0.071(4) 0.057(3) 0.052(3) 0.015(3) 0.020(3) 0.018(3) C23 0.072(4) 0.044(3) 0.047(3) 0.015(3) 0.013(3) 0.012(3) C25 0.057(4) 0.075(4) 0.069(4) 0.041(4) 0.010(3) 0.005(3) C26 0.087(4) 0.082(5) 0.048(4) 0.028(3) 0.021(3) 0.017(3) C28 0.104(5) 0.093(5) 0.115(6) 0.074(5) 0.017(4) 0.011(4) O7 0.043(2) 0.069(2) 0.058(2) 0.0249(19) -0.0037(16) -0.0116(16) O8 0.067(2) 0.0366(19) 0.060(2) 0.0068(16) 0.0165(18) 0.0130(16) O9 0.123(4) 0.062(3) 0.074(3) 0.025(2) 0.011(3) 0.023(3) O10 0.094(4) 0.049(3) 0.230(6) 0.021(3) 0.020(4) 0.011(3) C30 0.075(4) 0.055(4) 0.065(4) 0.017(3) -0.015(3) 0.001(3) C33 0.052(4) 0.053(4) 0.144(7) 0.018(5) -0.005(4) -0.007(3) C31 0.117(6) 0.105(6) 0.084(5) 0.021(4) 0.024(5) 0.017(5) C29 0.122(6) 0.076(5) 0.158(7) 0.064(5) -0.002(5) 0.011(4) K1 0.0605(7) 0.0332(6) 0.0583(7) 0.0036(5) 0.0108(6) 0.0004(5) K2 0.0494(7) 0.0382(6) 0.0748(9) 0.0092(6) 0.0098(6) 0.0032(5) C1A 0.095(5) 0.073(5) 0.123(6) 0.010(5) -0.013(4) 0.006(4) C2A 0.158(8) 0.137(8) 0.119(7) 0.025(6) 0.052(6) 0.013(6) S1 0.0419(7) 0.0309(6) 0.0383(7) 0.0119(5) 0.0064(5) 0.0008(5) S3 0.0464(7) 0.0335(7) 0.0392(7) 0.0075(5) 0.0040(6) -0.0008(5) S5 0.1192(13) 0.0298(7) 0.0427(8) 0.0133(6) 0.0134(8) -0.0008(7) S6 0.1161(13) 0.0398(8) 0.0544(9) 0.0144(7) -0.0010(8) -0.0244(8) C5 0.040(3) 0.033(3) 0.036(3) 0.012(2) 0.008(2) 0.001(2) C3 0.072(4) 0.077(4) 0.058(4) 0.038(3) 0.027(3) 0.010(3) C7 0.074(4) 0.051(3) 0.066(4) 0.033(3) 0.023(3) 0.024(3) C6 0.060(3) 0.057(3) 0.054(3) 0.031(3) 0.020(3) 0.015(3) C2 0.056(3) 0.058(3) 0.061(4) 0.035(3) 0.006(3) 0.001(3) C4 0.073(4) 0.049(3) 0.055(3) 0.021(3) 0.020(3) 0.014(3) C1 0.099(5) 0.082(4) 0.098(5) 0.066(4) 0.019(4) 0.005(4) C1S 0.145(13) 0.152(14) 0.195(18) -0.014(13) -0.076(12) 0.049(12) C2S 0.133(15) 0.170(19) 0.27(2) 0.135(18) -0.003(17) 0.013(14) O1S 0.214(18) 0.186(15) 0.187(17) -0.006(13) -0.018(14) 0.064(14) C3S 0.129(15) 0.27(2) 0.080(13) 0.014(15) 0.030(11) 0.027(16) _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 O1 S1 1.441(3) . ? O1 K2 2.710(3) 1_655 ? O1 K1 2.864(3) 2_886 ? O2 S1 1.443(3) . ? O2 K2 2.699(3) . ? O2 K1 2.941(3) 2_886 ? N1 C8 1.337(5) . ? N1 S1 1.599(3) . ? N2 C8 1.367(5) . ? N2 C9 1.403(5) . ? C8 S5 1.693(4) . ? C9 C10 1.380(6) . ? C9 C14 1.385(6) . ? C14 C13 1.367(6) . ? C11 C12 1.368(6) . ? C11 C10 1.379(6) . ? C12 C13 1.361(6) . ? C12 N3 1.460(6) . ? N3 O3 1.219(5) . ? N3 O4 1.223(5) . ? N4 C16 1.322(5) . ? N4 S3 1.580(4) . ? N5 C17 1.386(5) . ? N5 C16 1.390(6) . ? C15 C27 1.364(6) . ? C15 C23 1.378(6) . ? C15 S3 1.772(4) . ? C17 C18 1.393(6) . ? C17 C22 1.411(6) . ? C16 S6 1.694(5) . ? C18 C19 1.371(6) . ? C20 C21 1.375(6) . ? C20 C19 1.374(6) . ? C20 N6 1.454(5) . ? C22 C21 1.370(6) . ? O6 N6 1.227(5) . ? O6 K1 2.961(3) 2_886 ? O5 N6 1.234(5) . ? O5 K1 2.817(3) 2_886 ? N6 K1 3.246(4) 2_886 ? C24 C25 1.357(7) . ? C24 C23 1.382(6) . ? C27 C26 1.386(7) . ? C25 C26 1.370(7) . ? C25 C28 1.517(7) . ? O7 S3 1.439(3) . ? O7 K1 2.741(3) . ? O7 K2 3.266(3) 2_786 ? O8 S3 1.446(3) . ? O8 K2 2.780(3) 2_786 ? O8 K1 2.794(3) 1_455 ? O9 C30 1.204(6) . ? O10 C33 1.203(7) . ? O10 K2 2.711(5) 2_786 ? C30 C29 1.476(7) . ? C30 C31 1.488(8) . ? C33 C2A 1.464(9) . ? C33 C1A 1.499(9) . ? K1 O8 2.794(3) 1_655 ? K1 O5 2.817(3) 2_886 ? K1 O1 2.864(3) 2_886 ? K1 O2 2.941(3) 2_886 ? K1 O6 2.961(3) 2_886 ? K1 N6 3.246(4) 2_886 ? K1 S5 3.2677(17) 2_886 ? K1 S1 3.3794(15) 2_886 ? K1 K2 4.1280(15) 2_786 ? K1 K2 4.4374(16) 2_886 ? K2 O1 2.710(3) 1_455 ? K2 O10 2.711(5) 2_786 ? K2 O8 2.780(3) 2_786 ? K2 C3S 2.90(2) 2_675 ? K2 O7 3.266(3) 2_786 ? K2 S6 3.3509(18) 2_786 ? K2 C2S 3.46(5) . ? K2 S3 3.4909(16) 2_786 ? K2 S5 3.525(2) 1_455 ? K2 K1 4.1280(15) 2_786 ? K2 K1 4.4374(16) 2_886 ? S1 C5 1.759(4) . ? S1 K1 3.3794(15) 2_886 ? S3 K2 3.4909(16) 2_786 ? S5 K1 3.2677(17) 2_886 ? S5 K2 3.525(2) 1_655 ? S6 K2 3.3509(18) 2_786 ? C5 C4 1.363(6) . ? C5 C6 1.375(6) . ? C3 C2 1.387(7) . ? C3 C4 1.399(6) . ? C7 C2 1.366(6) . ? C7 C6 1.372(6) . ? C2 C1 1.517(6) . ? C1S O1S 1.2503(11) 2_675 ? C1S O1S 1.2503(11) . ? C1S C3S 1.452(3) 2_675 ? C1S C3S 1.452(3) . ? C1S C2S 1.452(3) 2_675 ? C1S C2S 1.452(3) . ? 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 S1 O1 K2 132.63(17) . 1_655 ? S1 O1 K1 97.95(15) . 2_886 ? K2 O1 K1 95.52(9) 1_655 2_886 ? S1 O2 K2 156.7(2) . . ? S1 O2 K1 94.66(15) . 2_886 ? K2 O2 K1 103.69(10) . 2_886 ? C8 N1 S1 120.0(3) . . ? C8 N2 C9 132.7(4) . . ? N1 C8 N2 116.1(4) . . ? N1 C8 S5 128.0(3) . . ? N2 C8 S5 115.9(3) . . ? C10 C9 C14 118.7(4) . . ? C10 C9 N2 124.4(4) . . ? C14 C9 N2 116.9(4) . . ? C13 C14 C9 121.4(4) . . ? C12 C11 C10 120.0(4) . . ? C13 C12 C11 121.1(4) . . ? C13 C12 N3 120.4(4) . . ? C11 C12 N3 118.5(4) . . ? C12 C13 C14 119.0(5) . . ? C11 C10 C9 119.8(5) . . ? O3 N3 O4 123.3(4) . . ? O3 N3 C12 119.1(5) . . ? O4 N3 C12 117.6(4) . . ? C16 N4 S3 120.5(3) . . ? C17 N5 C16 132.3(4) . . ? C27 C15 C23 119.8(4) . . ? C27 C15 S3 118.5(4) . . ? C23 C15 S3 121.7(4) . . ? N5 C17 C18 125.2(4) . . ? N5 C17 C22 116.4(4) . . ? C18 C17 C22 118.3(4) . . ? N4 C16 N5 115.7(4) . . ? N4 C16 S6 129.4(4) . . ? N5 C16 S6 114.9(3) . . ? C19 C18 C17 120.0(4) . . ? C21 C20 C19 121.3(4) . . ? C21 C20 N6 119.3(4) . . ? C19 C20 N6 119.4(4) . . ? C21 C22 C17 121.2(4) . . ? C18 C19 C20 120.4(4) . . ? C22 C21 C20 118.8(4) . . ? N6 O6 K1 92.1(3) . 2_886 ? N6 O5 K1 99.0(3) . 2_886 ? O6 N6 O5 122.7(4) . . ? O6 N6 C20 119.0(4) . . ? O5 N6 C20 118.3(4) . . ? O6 N6 K1 65.7(2) . 2_886 ? O5 N6 K1 59.0(2) . 2_886 ? C20 N6 K1 165.3(3) . 2_886 ? C25 C24 C23 122.1(5) . . ? C15 C27 C26 119.6(5) . . ? C24 C23 C15 119.2(5) . . ? C24 C25 C26 117.9(5) . . ? C24 C25 C28 121.8(6) . . ? C26 C25 C28 120.3(6) . . ? C25 C26 C27 121.5(5) . . ? S3 O7 K1 151.43(19) . . ? S3 O7 K2 86.65(15) . 2_786 ? K1 O7 K2 86.35(9) . 2_786 ? S3 O8 K2 107.12(16) . 2_786 ? S3 O8 K1 132.39(19) . 1_455 ? K2 O8 K1 105.50(10) 2_786 1_455 ? C33 O10 K2 159.2(4) . 2_786 ? O9 C30 C29 119.7(6) . . ? O9 C30 C31 120.5(6) . . ? C29 C30 C31 119.9(6) . . ? O10 C33 C2A 122.8(8) . . ? O10 C33 C1A 120.5(8) . . ? C2A C33 C1A 116.7(6) . . ? O7 K1 O8 131.75(10) . 1_655 ? O7 K1 O5 80.13(10) . 2_886 ? O8 K1 O5 98.69(10) 1_655 2_886 ? O7 K1 O1 92.66(9) . 2_886 ? O8 K1 O1 121.64(9) 1_655 2_886 ? O5 K1 O1 128.77(10) 2_886 2_886 ? O7 K1 O2 134.89(10) . 2_886 ? O8 K1 O2 73.05(9) 1_655 2_886 ? O5 K1 O2 139.94(10) 2_886 2_886 ? O1 K1 O2 49.09(8) 2_886 2_886 ? O7 K1 O6 68.42(10) . 2_886 ? O8 K1 O6 77.77(10) 1_655 2_886 ? O5 K1 O6 43.81(10) 2_886 2_886 ? O1 K1 O6 159.89(10) 2_886 2_886 ? O2 K1 O6 150.78(10) 2_886 2_886 ? O7 K1 N6 70.08(10) . 2_886 ? O8 K1 N6 90.94(10) 1_655 2_886 ? O5 K1 N6 22.05(9) 2_886 2_886 ? O1 K1 N6 145.39(11) 2_886 2_886 ? O2 K1 N6 154.97(10) 2_886 2_886 ? O6 K1 N6 22.19(9) 2_886 2_886 ? O7 K1 S5 75.87(8) . 2_886 ? O8 K1 S5 89.32(8) 1_655 2_886 ? O5 K1 S5 153.61(8) 2_886 2_886 ? O1 K1 S5 63.82(6) 2_886 2_886 ? O2 K1 S5 66.45(7) 2_886 2_886 ? O6 K1 S5 115.22(8) 2_886 2_886 ? N6 K1 S5 134.01(9) 2_886 2_886 ? O7 K1 S1 111.62(8) . 2_886 ? O8 K1 S1 96.71(7) 1_655 2_886 ? O5 K1 S1 145.01(8) 2_886 2_886 ? O1 K1 S1 24.97(6) 2_886 2_886 ? O2 K1 S1 25.20(6) 2_886 2_886 ? O6 K1 S1 171.01(8) 2_886 2_886 ? N6 K1 S1 166.79(9) 2_886 2_886 ? S5 K1 S1 57.14(3) 2_886 2_886 ? O7 K1 K2 52.14(7) . 2_786 ? O8 K1 K2 144.17(7) 1_655 2_786 ? O5 K1 K2 115.84(8) 2_886 2_786 ? O1 K1 K2 40.80(6) 2_886 2_786 ? O2 K1 K2 85.38(6) 2_886 2_786 ? O6 K1 K2 120.54(8) 2_886 2_786 ? N6 K1 K2 117.41(7) 2_886 2_786 ? S5 K1 K2 55.47(4) 2_886 2_786 ? S1 K1 K2 60.47(3) 2_886 2_786 ? O7 K1 K2 152.30(8) . 2_886 ? O8 K1 K2 37.14(6) 1_655 2_886 ? O5 K1 K2 122.13(8) 2_886 2_886 ? O1 K1 K2 85.31(6) 2_886 2_886 ? O2 K1 K2 36.23(6) 2_886 2_886 ? O6 K1 K2 114.58(8) 2_886 2_886 ? N6 K1 K2 123.85(8) 2_886 2_886 ? S5 K1 K2 78.51(4) 2_886 2_886 ? S1 K1 K2 60.90(3) 2_886 2_886 ? K2 K1 K2 118.59(3) 2_786 2_886 ? O2 K2 O1 136.07(10) . 1_455 ? O2 K2 O10 75.78(12) . 2_786 ? O1 K2 O10 79.34(12) 1_455 2_786 ? O2 K2 O8 77.10(10) . 2_786 ? O1 K2 O8 128.14(9) 1_455 2_786 ? O10 K2 O8 151.15(12) 2_786 2_786 ? O2 K2 C3S 93.5(5) . 2_675 ? O1 K2 C3S 126.2(5) 1_455 2_675 ? O10 K2 C3S 99.4(8) 2_786 2_675 ? O8 K2 C3S 72.6(8) 2_786 2_675 ? O2 K2 O7 121.93(9) . 2_786 ? O1 K2 O7 84.94(8) 1_455 2_786 ? O10 K2 O7 162.11(12) 2_786 2_786 ? O8 K2 O7 46.45(8) 2_786 2_786 ? C3S K2 O7 83.0(8) 2_675 2_786 ? O2 K2 S6 88.93(8) . 2_786 ? O1 K2 S6 74.52(7) 1_455 2_786 ? O10 K2 S6 122.13(14) 2_786 2_786 ? O8 K2 S6 66.70(7) 2_786 2_786 ? C3S K2 S6 137.5(8) 2_675 2_786 ? O7 K2 S6 60.45(6) 2_786 2_786 ? O2 K2 C2S 83.3(4) . . ? O1 K2 C2S 122.0(4) 1_455 . ? O10 K2 C2S 71.7(3) 2_786 . ? O8 K2 C2S 95.5(3) 2_786 . ? C3S K2 C2S 27.9(6) 2_675 . ? O7 K2 C2S 110.5(3) 2_786 . ? S6 K2 C2S 161.9(3) 2_786 . ? O2 K2 S3 97.68(7) . 2_786 ? O1 K2 S3 105.22(7) 1_455 2_786 ? O10 K2 S3 173.38(11) 2_786 2_786 ? O8 K2 S3 23.32(6) 2_786 2_786 ? C3S K2 S3 81.9(8) 2_675 2_786 ? O7 K2 S3 24.29(5) 2_786 2_786 ? S6 K2 S3 55.84(3) 2_786 2_786 ? C2S K2 S3 109.0(3) . 2_786 ? O2 K2 S5 157.54(8) . 1_455 ? O1 K2 S5 61.40(7) 1_455 1_455 ? O10 K2 S5 98.40(12) 2_786 1_455 ? O8 K2 S5 102.94(8) 2_786 1_455 ? C3S K2 S5 65.7(4) 2_675 1_455 ? O7 K2 S5 66.25(6) 2_786 1_455 ? S6 K2 S5 111.96(5) 2_786 1_455 ? C2S K2 S5 74.4(4) . 1_455 ? S3 K2 S5 88.07(4) 2_786 1_455 ? O2 K2 K1 150.98(8) . 2_786 ? O1 K2 K1 43.68(6) 1_455 2_786 ? O10 K2 K1 121.69(10) 2_786 2_786 ? O8 K2 K1 87.07(7) 2_786 2_786 ? C3S K2 K1 104.9(6) 2_675 2_786 ? O7 K2 K1 41.51(5) 2_786 2_786 ? S6 K2 K1 62.34(4) 2_786 2_786 ? C2S K2 K1 122.8(4) . 2_786 ? S3 K2 K1 63.82(3) 2_786 2_786 ? S5 K2 K1 49.79(3) 1_455 2_786 ? O2 K2 K1 40.08(7) . 2_886 ? O1 K2 K1 144.63(7) 1_455 2_886 ? O10 K2 K1 115.78(10) 2_786 2_886 ? O8 K2 K1 37.36(7) 2_786 2_886 ? C3S K2 K1 84.7(5) 2_675 2_886 ? O7 K2 K1 82.05(6) 2_786 2_886 ? S6 K2 K1 70.43(4) 2_786 2_886 ? C2S K2 K1 93.4(4) . 2_886 ? S3 K2 K1 57.76(3) 2_786 2_886 ? S5 K2 K1 138.17(4) 1_455 2_886 ? K1 K2 K1 118.59(3) 2_786 2_886 ? O1 S1 O2 113.54(19) . . ? O1 S1 N1 113.28(18) . . ? O2 S1 N1 113.9(2) . . ? O1 S1 C5 106.52(19) . . ? O2 S1 C5 107.41(19) . . ? N1 S1 C5 100.98(19) . . ? O1 S1 K1 57.07(12) . 2_886 ? O2 S1 K1 60.14(13) . 2_886 ? N1 S1 K1 118.71(13) . 2_886 ? C5 S1 K1 140.23(15) . 2_886 ? O7 S3 O8 114.5(2) . . ? O7 S3 N4 114.04(19) . . ? O8 S3 N4 112.3(2) . . ? O7 S3 C15 106.7(2) . . ? O8 S3 C15 106.6(2) . . ? N4 S3 C15 101.5(2) . . ? O7 S3 K2 69.05(14) . 2_786 ? O8 S3 K2 49.56(13) . 2_786 ? N4 S3 K2 116.64(14) . 2_786 ? C15 S3 K2 140.15(16) . 2_786 ? C8 S5 K1 116.04(16) . 2_886 ? C8 S5 K2 85.22(16) . 1_655 ? K1 S5 K2 74.74(4) 2_886 1_655 ? C16 S6 K2 113.40(17) . 2_786 ? C4 C5 C6 119.4(4) . . ? C4 C5 S1 117.9(3) . . ? C6 C5 S1 122.4(3) . . ? C2 C3 C4 120.4(5) . . ? C2 C7 C6 121.8(5) . . ? C7 C6 C5 120.3(4) . . ? C7 C2 C3 118.0(4) . . ? C7 C2 C1 121.9(5) . . ? C3 C2 C1 120.1(5) . . ? C5 C4 C3 120.1(5) . . ? O1S C1S O1S 180(3) 2_675 . ? O1S C1S C3S 125.7(11) 2_675 2_675 ? O1S C1S C3S 54.3(11) . 2_675 ? O1S C1S C3S 54.3(11) 2_675 . ? O1S C1S C3S 125.7(11) . . ? C3S C1S C3S 180.0(6) 2_675 . ? O1S C1S C2S 121.9(12) 2_675 2_675 ? O1S C1S C2S 58.1(12) . 2_675 ? C3S C1S C2S 111.9(12) 2_675 2_675 ? C3S C1S C2S 68.1(12) . 2_675 ? O1S C1S C2S 58.1(12) 2_675 . ? O1S C1S C2S 121.9(12) . . ? C3S C1S C2S 68.1(12) 2_675 . ? C3S C1S C2S 111.9(12) . . ? C2S C1S C2S 180(3) 2_675 . ? C1S C2S K2 111(2) . . ? _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 25.60 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 0.409 _refine_diff_density_min -0.342 _refine_diff_density_rms 0.067 _database_code_depnum_ccdc_archive 'CCDC 965656' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_cm47_0m _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common 4-methyl-N-(phenylcarbamothioyl)benzenesulfonamide _chemical_melting_point ? _chemical_formula_moiety 'C14 H14 N2 O2 S2' _chemical_formula_sum 'C14 H14 N2 O2 S2' _chemical_formula_weight 306.39 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 Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.557(4) _cell_length_b 9.922(5) _cell_length_c 11.266(6) _cell_angle_alpha 106.421(6) _cell_angle_beta 103.828(6) _cell_angle_gamma 98.312(6) _cell_volume 766.0(7) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 1649 _cell_measurement_theta_min 2.20 _cell_measurement_theta_max 22.10 _exptl_crystal_description Rhombohedral _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.40 _exptl_crystal_size_min 0.30 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.328 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 320 _exptl_absorpt_coefficient_mu 0.349 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.702 _exptl_absorpt_correction_T_max 0.949 _exptl_absorpt_process_details 'SADABS (Sheldrick, 1996)' _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 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 7852 _diffrn_reflns_av_R_equivalents 0.0461 _diffrn_reflns_av_sigmaI/netI 0.0590 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 1.97 _diffrn_reflns_theta_max 26.17 _reflns_number_total 3021 _reflns_number_gt 1719 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _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^)+(0.0826P)^2^+0.0153P] 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_number_reflns 3021 _refine_ls_number_parameters 182 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1013 _refine_ls_R_factor_gt 0.0533 _refine_ls_wR_factor_ref 0.1566 _refine_ls_wR_factor_gt 0.1281 _refine_ls_goodness_of_fit_ref 0.973 _refine_ls_restrained_S_all 0.973 _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_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C -0.1443(6) -0.2304(4) 0.0726(3) 0.0714(10) Uani 1 1 d . . . C2 C 0.0319(6) -0.2538(4) 0.0732(4) 0.0771(10) Uani 1 1 d . . . H2 H 0.0451 -0.3477 0.0398 0.093 Uiso 1 1 calc R . . C3 C 0.1881(5) -0.1419(4) 0.1220(3) 0.0689(9) Uani 1 1 d . . . H3 H 0.3055 -0.1594 0.1211 0.083 Uiso 1 1 calc R . . C4 C 0.1672(5) -0.0026(3) 0.1725(3) 0.0548(8) Uani 1 1 d . . . C5 C -0.0082(5) 0.0236(4) 0.1704(3) 0.0674(9) Uani 1 1 d . . . H5 H -0.0220 0.1175 0.2024 0.081 Uiso 1 1 calc R . . C6 C -0.1622(5) -0.0901(4) 0.1206(4) 0.0766(10) Uani 1 1 d . . . H6 H -0.2801 -0.0723 0.1191 0.092 Uiso 1 1 calc R . . C7 C -0.3148(6) -0.3552(5) 0.0239(4) 0.1085(15) Uani 1 1 d . . . H7A H -0.3342 -0.3839 0.0951 0.163 Uiso 1 1 calc R . . H7B H -0.2950 -0.4351 -0.0391 0.163 Uiso 1 1 calc R . . H7C H -0.4230 -0.3253 -0.0152 0.163 Uiso 1 1 calc R . . C8 C 0.3396(4) 0.1936(3) 0.4940(3) 0.0551(8) Uani 1 1 d . . . C9 C 0.1456(4) 0.3588(3) 0.5669(3) 0.0552(8) Uani 1 1 d . . . C10 C -0.0241(5) 0.2844(4) 0.5634(4) 0.0800(11) Uani 1 1 d . . . H10 H -0.0738 0.1899 0.5081 0.096 Uiso 1 1 calc R . . C11 C -0.1202(6) 0.3525(7) 0.6436(5) 0.1014(15) Uani 1 1 d . . . H11 H -0.2351 0.3030 0.6427 0.122 Uiso 1 1 calc R . . C12 C -0.0484(8) 0.4919(6) 0.7242(4) 0.0976(15) Uani 1 1 d . . . H12 H -0.1146 0.5369 0.7773 0.117 Uiso 1 1 calc R . . C13 C 0.1196(8) 0.5643(5) 0.7266(4) 0.1012(14) Uani 1 1 d . . . H13 H 0.1682 0.6592 0.7812 0.121 Uiso 1 1 calc R . . C14 C 0.2183(6) 0.4982(4) 0.6488(4) 0.0775(10) Uani 1 1 d . . . H14 H 0.3343 0.5479 0.6516 0.093 Uiso 1 1 calc R . . N1 N 0.4298(4) 0.1446(3) 0.4013(2) 0.0583(7) Uani 1 1 d . . . N2 N 0.2463(4) 0.2954(3) 0.4813(2) 0.0607(7) Uani 1 1 d . . . H2N H 0.2466 0.3253 0.4168 0.073 Uiso 1 1 calc R . . O1 O 0.5176(3) 0.0982(3) 0.2005(2) 0.0751(7) Uani 1 1 d . . . O2 O 0.3164(3) 0.2722(2) 0.2465(2) 0.0690(6) Uani 1 1 d . . . S1 S 0.36717(12) 0.13806(9) 0.24735(8) 0.0603(3) Uani 1 1 d . . . S2 S 0.36120(14) 0.12998(10) 0.61764(9) 0.0729(3) Uani 1 1 d . . . H1N H 0.5009 0.0675 0.4151 0.090 Uiso 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 C1 0.083(3) 0.075(2) 0.058(2) 0.0325(18) 0.0209(19) 0.000(2) C2 0.097(3) 0.061(2) 0.075(2) 0.0257(18) 0.021(2) 0.021(2) C3 0.072(2) 0.062(2) 0.074(2) 0.0212(17) 0.0213(19) 0.0227(19) C4 0.067(2) 0.0548(18) 0.0510(18) 0.0227(14) 0.0240(16) 0.0178(16) C5 0.072(2) 0.067(2) 0.071(2) 0.0232(17) 0.0297(19) 0.025(2) C6 0.065(2) 0.092(3) 0.076(2) 0.027(2) 0.031(2) 0.015(2) C7 0.108(3) 0.106(3) 0.094(3) 0.039(2) 0.023(3) -0.028(3) C8 0.0515(18) 0.0543(18) 0.0553(19) 0.0170(15) 0.0123(15) 0.0072(15) C9 0.060(2) 0.0559(19) 0.0564(18) 0.0250(15) 0.0184(16) 0.0186(16) C10 0.066(2) 0.089(3) 0.078(3) 0.024(2) 0.020(2) 0.001(2) C11 0.071(3) 0.164(5) 0.092(3) 0.062(3) 0.039(3) 0.031(3) C12 0.124(4) 0.131(4) 0.077(3) 0.050(3) 0.052(3) 0.080(4) C13 0.148(4) 0.078(3) 0.096(3) 0.026(2) 0.058(3) 0.046(3) C14 0.090(3) 0.057(2) 0.090(3) 0.0227(19) 0.037(2) 0.014(2) N1 0.0631(16) 0.0619(16) 0.0560(16) 0.0230(13) 0.0205(13) 0.0205(13) N2 0.0742(18) 0.0580(16) 0.0610(16) 0.0259(13) 0.0290(14) 0.0208(14) O1 0.0766(16) 0.0838(16) 0.0803(16) 0.0307(13) 0.0433(13) 0.0239(13) O2 0.0907(17) 0.0574(13) 0.0750(15) 0.0341(11) 0.0345(13) 0.0243(12) S1 0.0686(6) 0.0609(5) 0.0620(5) 0.0277(4) 0.0278(4) 0.0180(4) S2 0.0845(7) 0.0880(7) 0.0661(6) 0.0399(5) 0.0306(5) 0.0373(5) _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 C6 1.383(5) . ? C1 C2 1.383(5) . ? C1 C7 1.520(5) . ? C2 C3 1.377(5) . ? C3 C4 1.385(4) . ? C4 C5 1.384(4) . ? C4 S1 1.749(3) . ? C5 C6 1.375(5) . ? C8 N2 1.333(4) . ? C8 N1 1.393(4) . ? C8 S2 1.668(3) . ? C9 C10 1.370(5) . ? C9 C14 1.373(4) . ? C9 N2 1.432(4) . ? C10 C11 1.382(6) . ? C11 C12 1.367(6) . ? C12 C13 1.355(7) . ? C13 C14 1.372(5) . ? N1 S1 1.664(3) . ? O1 S1 1.423(2) . ? O2 S1 1.439(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 C6 C1 C2 118.5(3) . . ? C6 C1 C7 120.1(4) . . ? C2 C1 C7 121.3(4) . . ? C3 C2 C1 121.7(3) . . ? C2 C3 C4 118.7(3) . . ? C3 C4 C5 120.5(3) . . ? C3 C4 S1 118.9(3) . . ? C5 C4 S1 120.5(2) . . ? C6 C5 C4 119.6(3) . . ? C5 C6 C1 120.9(3) . . ? N2 C8 N1 117.0(3) . . ? N2 C8 S2 123.4(2) . . ? N1 C8 S2 119.5(2) . . ? C10 C9 C14 120.3(3) . . ? C10 C9 N2 120.9(3) . . ? C14 C9 N2 118.7(3) . . ? C9 C10 C11 118.8(4) . . ? C12 C11 C10 120.8(4) . . ? C13 C12 C11 119.9(4) . . ? C12 C13 C14 120.3(4) . . ? C9 C14 C13 119.9(4) . . ? C8 N1 S1 127.2(2) . . ? C8 N2 C9 125.0(3) . . ? O1 S1 O2 120.70(14) . . ? O1 S1 N1 104.54(14) . . ? O2 S1 N1 106.79(13) . . ? O1 S1 C4 109.75(15) . . ? O2 S1 C4 109.11(15) . . ? N1 S1 C4 104.67(14) . . ? _diffrn_measured_fraction_theta_max 0.983 _diffrn_reflns_theta_full 26.17 _diffrn_measured_fraction_theta_full 0.983 _refine_diff_density_max 0.247 _refine_diff_density_min -0.378 _refine_diff_density_rms 0.052 _database_code_depnum_ccdc_archive 'CCDC 965657' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_vs10_0ma _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common 5-chloro-2-methoxy-N-(4-sulfamoylphenethyl_benzamide _chemical_melting_point ? _chemical_formula_moiety 'C16 H17 Cl1 N2 O4 S1' _chemical_formula_sum 'C16 H17 Cl N2 O4 S' _chemical_formula_weight 368.83 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' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 9.634(2) _cell_length_b 10.046(2) _cell_length_c 10.667(2) _cell_angle_alpha 64.209(3) _cell_angle_beta 69.198(2) _cell_angle_gamma 72.313(2) _cell_volume 855.1(3) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 2376 _cell_measurement_theta_min 2.196 _cell_measurement_theta_max 23.250 _exptl_crystal_description Prismatic _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.40 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.432 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 384 _exptl_absorpt_coefficient_mu 0.368 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.891 _exptl_absorpt_correction_T_max 0.964 _exptl_absorpt_process_details 'SADABS (Sheldrick, 1996)' _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 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 8013 _diffrn_reflns_av_R_equivalents 0.0209 _diffrn_reflns_av_sigmaI/netI 0.0246 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 2.20 _diffrn_reflns_theta_max 24.42 _reflns_number_total 2829 _reflns_number_gt 2120 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _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^)+(0.0457P)^2^+0.3248P] 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_number_reflns 2829 _refine_ls_number_parameters 219 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0541 _refine_ls_R_factor_gt 0.0388 _refine_ls_wR_factor_ref 0.1022 _refine_ls_wR_factor_gt 0.0922 _refine_ls_goodness_of_fit_ref 0.989 _refine_ls_restrained_S_all 0.989 _refine_ls_shift/su_max 0.008 _refine_ls_shift/su_mean 0.002 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 C1 C 0.0249(3) 0.5860(3) 0.6899(3) 0.0697(8) Uani 1 1 d . . . H1 H 0.0243 0.5013 0.7741 0.084 Uiso 1 1 calc R . . C2 C -0.0705(3) 0.6137(3) 0.6066(4) 0.0813(9) Uani 1 1 d . . . H2 H -0.1341 0.5465 0.6350 0.098 Uiso 1 1 calc R . . C3 C -0.0723(3) 0.7408(4) 0.4809(3) 0.0750(8) Uani 1 1 d . . . C4 C 0.0219(3) 0.8382(4) 0.4440(3) 0.0780(9) Uani 1 1 d . . . H4 H 0.0203 0.9251 0.3620 0.094 Uiso 1 1 calc R . . C5 C 0.1187(3) 0.8112(3) 0.5250(3) 0.0665(7) Uani 1 1 d . . . H5 H 0.1824 0.8782 0.4969 0.080 Uiso 1 1 calc R . . C6 C 0.1201(3) 0.6837(3) 0.6478(2) 0.0521(6) Uani 1 1 d . . . C7 C -0.1767(3) 0.7777(4) 0.3878(4) 0.1009(12) Uani 1 1 d . . . H7A H -0.1313 0.8368 0.2890 0.121 Uiso 1 1 calc R . . H7B H -0.1908 0.6854 0.3894 0.121 Uiso 1 1 calc R . . C8 C -0.3259(3) 0.8633(3) 0.4412(3) 0.0565(6) Uani 1 1 d . . . H8A H -0.3816 0.7957 0.5293 0.068 Uiso 1 1 calc R . . H8B H -0.3098 0.9401 0.4640 0.068 Uiso 1 1 calc R . . C9 C -0.5874(2) 0.9419(3) 0.2107(2) 0.0475(5) Uani 1 1 d . . . C10 C -0.6298(3) 1.0981(3) 0.1513(2) 0.0528(6) Uani 1 1 d . . . C11 C -0.7323(3) 1.1612(3) 0.0670(3) 0.0647(7) Uani 1 1 d . . . H11 H -0.7618 1.2649 0.0294 0.078 Uiso 1 1 calc R . . C12 C -0.7900(3) 1.0700(4) 0.0393(3) 0.0700(8) Uani 1 1 d . . . H12 H -0.8585 1.1122 -0.0169 0.084 Uiso 1 1 calc R . . C13 C -0.7463(3) 0.9170(3) 0.0945(3) 0.0631(7) Uani 1 1 d . . . C14 C -0.6480(3) 0.8530(3) 0.1804(2) 0.0560(6) Uani 1 1 d . . . H14 H -0.6214 0.7490 0.2189 0.067 Uiso 1 1 calc R . . C15 C -0.5860(4) 1.3406(3) 0.1044(3) 0.0786(9) Uani 1 1 d . . . H15A H -0.5324 1.3834 0.1341 0.118 Uiso 1 1 calc R . . H15B H -0.6913 1.3838 0.1246 0.118 Uiso 1 1 calc R . . H15C H -0.5468 1.3613 0.0028 0.118 Uiso 1 1 calc R . . C16 C -0.4871(3) 0.8588(3) 0.3113(2) 0.0505(6) Uani 1 1 d . . . N1 N 0.4043(2) 0.5536(2) 0.6806(2) 0.0630(6) Uani 1 1 d . . . N2 N -0.4160(2) 0.9346(2) 0.3359(2) 0.0564(5) Uani 1 1 d . . . H3N H -0.4228 1.0297 0.2881 0.068 Uiso 1 1 calc R . . O1 O -0.5677(2) 1.18234(17) 0.18099(18) 0.0647(5) Uani 1 1 d . . . O2 O 0.2844(2) 0.78815(18) 0.7169(2) 0.0753(6) Uani 1 1 d . . . O3 O 0.1909(2) 0.5536(2) 0.89080(19) 0.0828(6) Uani 1 1 d . . . O4 O -0.4745(2) 0.72037(18) 0.37199(19) 0.0675(5) Uani 1 1 d . . . S1 S 0.24940(8) 0.64763(7) 0.74612(7) 0.0583(2) Uani 1 1 d . . . Cl1 Cl -0.81689(9) 0.80160(11) 0.05743(10) 0.0951(3) Uani 1 1 d . . . H1N H 0.4528 0.6068 0.5776 0.074(8) Uiso 1 1 d . . . H2N H 0.3876 0.4546 0.6926 0.105(10) Uiso 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 C1 0.0802(19) 0.0552(15) 0.0830(19) -0.0166(14) -0.0500(16) -0.0036(14) C2 0.076(2) 0.0776(19) 0.114(2) -0.0404(19) -0.0555(19) -0.0007(15) C3 0.0628(18) 0.098(2) 0.081(2) -0.0517(18) -0.0447(16) 0.0221(16) C4 0.0660(18) 0.097(2) 0.0544(16) -0.0131(15) -0.0332(14) 0.0070(16) C5 0.0586(16) 0.0749(17) 0.0574(16) -0.0105(13) -0.0288(13) -0.0049(13) C6 0.0542(14) 0.0515(13) 0.0554(14) -0.0192(12) -0.0310(12) 0.0036(11) C7 0.073(2) 0.152(3) 0.110(3) -0.087(2) -0.0574(19) 0.036(2) C8 0.0624(15) 0.0543(14) 0.0637(15) -0.0229(12) -0.0363(13) 0.0008(12) C9 0.0421(12) 0.0592(14) 0.0460(13) -0.0214(11) -0.0187(10) -0.0037(10) C10 0.0500(14) 0.0633(15) 0.0478(13) -0.0157(11) -0.0238(11) -0.0073(12) C11 0.0574(16) 0.0760(17) 0.0581(15) -0.0117(13) -0.0327(13) -0.0070(13) C12 0.0520(15) 0.105(2) 0.0582(16) -0.0254(16) -0.0312(13) -0.0086(15) C13 0.0471(14) 0.097(2) 0.0613(16) -0.0386(15) -0.0189(12) -0.0143(14) C14 0.0488(14) 0.0717(16) 0.0590(15) -0.0315(13) -0.0202(12) -0.0076(12) C15 0.097(2) 0.0501(15) 0.092(2) -0.0070(14) -0.0592(18) -0.0058(14) C16 0.0519(14) 0.0511(14) 0.0558(14) -0.0214(12) -0.0268(12) -0.0011(11) N1 0.0642(13) 0.0523(12) 0.0829(16) -0.0203(11) -0.0441(12) -0.0012(10) N2 0.0645(13) 0.0458(11) 0.0702(13) -0.0150(10) -0.0460(11) -0.0006(9) O1 0.0811(12) 0.0486(9) 0.0730(11) -0.0071(8) -0.0522(10) -0.0077(8) O2 0.1062(15) 0.0528(10) 0.0922(14) -0.0285(10) -0.0578(12) -0.0070(10) O3 0.0973(15) 0.0886(14) 0.0565(11) 0.0000(10) -0.0441(11) -0.0202(11) O4 0.0851(13) 0.0488(10) 0.0824(12) -0.0187(9) -0.0505(10) -0.0044(9) S1 0.0726(4) 0.0512(4) 0.0609(4) -0.0140(3) -0.0436(3) -0.0030(3) Cl1 0.0786(5) 0.1409(8) 0.1120(7) -0.0717(6) -0.0412(5) -0.0236(5) _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 C6 1.371(3) . ? C1 C2 1.386(4) . ? C2 C3 1.394(4) . ? C3 C4 1.374(4) . ? C3 C7 1.516(3) . ? C4 C5 1.379(4) . ? C5 C6 1.378(3) . ? C6 S1 1.763(2) . ? C7 C8 1.492(4) . ? C8 N2 1.464(3) . ? C9 C14 1.394(3) . ? C9 C10 1.400(3) . ? C9 C16 1.500(3) . ? C10 O1 1.360(3) . ? C10 C11 1.393(3) . ? C11 C12 1.376(4) . ? C12 C13 1.372(4) . ? C13 C14 1.373(3) . ? C13 Cl1 1.741(3) . ? C15 O1 1.424(3) . ? C16 O4 1.240(3) . ? C16 N2 1.317(3) . ? N1 S1 1.607(2) . ? O2 S1 1.4267(18) . ? O3 S1 1.4245(19) . ? 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 C6 C1 C2 119.8(3) . . ? C3 C2 C1 120.9(3) . . ? C4 C3 C2 117.7(2) . . ? C4 C3 C7 119.4(3) . . ? C2 C3 C7 122.9(3) . . ? C3 C4 C5 122.0(3) . . ? C6 C5 C4 119.3(3) . . ? C1 C6 C5 120.3(2) . . ? C1 C6 S1 121.09(18) . . ? C5 C6 S1 118.62(19) . . ? C8 C7 C3 110.7(2) . . ? N2 C8 C7 112.6(2) . . ? C14 C9 C10 118.2(2) . . ? C14 C9 C16 115.9(2) . . ? C10 C9 C16 125.9(2) . . ? O1 C10 C11 122.7(2) . . ? O1 C10 C9 117.06(18) . . ? C11 C10 C9 120.2(2) . . ? C12 C11 C10 120.0(3) . . ? C13 C12 C11 120.0(2) . . ? C12 C13 C14 120.6(2) . . ? C12 C13 Cl1 120.12(19) . . ? C14 C13 Cl1 119.3(2) . . ? C13 C14 C9 120.9(2) . . ? O4 C16 N2 121.0(2) . . ? O4 C16 C9 119.6(2) . . ? N2 C16 C9 119.4(2) . . ? C16 N2 C8 122.7(2) . . ? C10 O1 C15 119.35(18) . . ? O3 S1 O2 120.11(12) . . ? O3 S1 N1 107.36(12) . . ? O2 S1 N1 105.67(12) . . ? O3 S1 C6 107.68(12) . . ? O2 S1 C6 107.58(11) . . ? N1 S1 C6 107.92(11) . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 24.42 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.206 _refine_diff_density_min -0.251 _refine_diff_density_rms 0.037 _database_code_depnum_ccdc_archive 'CCDC 965658' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_davin1_0m _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common 4-chloro-N-(cyclohexylcarbamoyl)benzenesulfonamide _chemical_melting_point ? _chemical_formula_moiety 'C13 H17 Cl N2 O3 S' _chemical_formula_sum 'C13 H17 Cl N2 O3 S' _chemical_formula_weight 316.80 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' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 9.3333(8) _cell_length_b 16.0646(14) _cell_length_c 19.6441(17) _cell_angle_alpha 90.00 _cell_angle_beta 97.5800(10) _cell_angle_gamma 90.00 _cell_volume 2919.6(4) _cell_formula_units_Z 8 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 9898 _cell_measurement_theta_min 2.45 _cell_measurement_theta_max 27.45 _exptl_crystal_description Needles _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.15 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.441 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1328 _exptl_absorpt_coefficient_mu 0.413 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.941 _exptl_absorpt_correction_T_max 0.980 _exptl_absorpt_process_details 'SADABS (Sheldrick, 1996)' _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 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 32712 _diffrn_reflns_av_R_equivalents 0.0339 _diffrn_reflns_av_sigmaI/netI 0.0279 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -20 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_l_min -25 _diffrn_reflns_limit_l_max 25 _diffrn_reflns_theta_min 1.64 _diffrn_reflns_theta_max 27.73 _reflns_number_total 6633 _reflns_number_gt 5453 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _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^)+(0.0432P)^2^+1.4890P] 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_number_reflns 6633 _refine_ls_number_parameters 361 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0449 _refine_ls_R_factor_gt 0.0336 _refine_ls_wR_factor_ref 0.0897 _refine_ls_wR_factor_gt 0.0836 _refine_ls_goodness_of_fit_ref 1.026 _refine_ls_restrained_S_all 1.026 _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 O1 O 0.84708(11) 0.17696(7) 0.14644(6) 0.0211(2) Uani 1 1 d . . . O2 O 0.81540(12) 0.35290(7) 0.13562(6) 0.0227(3) Uani 1 1 d . . . O3 O 0.56729(12) 0.38564(7) 0.15980(6) 0.0231(3) Uani 1 1 d . . . N1 N 0.64408(14) 0.09963(8) 0.11946(7) 0.0174(3) Uani 1 1 d . . . H1N H 0.5512 0.0988 0.1151 0.021 Uiso 1 1 calc R . . N2 N 0.62686(14) 0.24172(8) 0.13635(7) 0.0177(3) Uani 1 1 d . . . H2N H 0.5365 0.2378 0.1210 0.021 Uiso 1 1 calc R . . C13 C 0.71458(16) 0.17130(10) 0.13444(8) 0.0163(3) Uani 1 1 d . . . C17 C 0.28682(17) 0.07652(10) 0.26061(8) 0.0176(3) Uani 1 1 d . . . C16 C 0.42909(17) 0.10324(10) 0.27356(9) 0.0215(3) Uani 1 1 d . . . H16 H 0.4865 0.1049 0.2383 0.026 Uiso 1 1 calc R . . C15 C 0.48507(18) 0.12742(11) 0.33943(9) 0.0240(4) Uani 1 1 d . . . H15 H 0.5801 0.1459 0.3486 0.029 Uiso 1 1 calc R . . C18 C 0.2006(2) 0.07295(13) 0.31285(9) 0.0297(4) Uani 1 1 d . . . H18 H 0.1054 0.0547 0.3037 0.036 Uiso 1 1 calc R . . C14 C 0.39899(19) 0.12396(11) 0.39121(9) 0.0260(4) Uani 1 1 d . . . C19 C 0.2572(2) 0.09667(14) 0.37861(10) 0.0361(5) Uani 1 1 d . . . H19 H 0.2005 0.0943 0.4141 0.043 Uiso 1 1 calc R . . O5 O 0.32671(12) 0.02800(8) 0.13847(6) 0.0239(3) Uani 1 1 d . . . N3 N 0.13162(14) 0.13436(8) 0.14489(7) 0.0169(3) Uani 1 1 d . . . H3N H 0.0403 0.1335 0.1310 0.020 Uiso 1 1 calc R . . O4 O 0.09499(12) -0.00793(7) 0.18041(6) 0.0229(3) Uani 1 1 d . . . C20 C 0.20850(16) 0.20844(10) 0.13992(8) 0.0170(3) Uani 1 1 d . . . O6 O 0.34093(12) 0.20753(8) 0.14321(7) 0.0260(3) Uani 1 1 d . . . N4 N 0.12646(14) 0.27681(8) 0.13291(7) 0.0201(3) Uani 1 1 d . . . H4N H 0.0345 0.2718 0.1320 0.024 Uiso 1 1 calc R . . C21 C 0.18798(17) 0.36016(10) 0.12676(9) 0.0202(3) Uani 1 1 d . . . H21 H 0.2932 0.3547 0.1295 0.024 Uiso 1 1 calc R . . C22 C 0.1311(2) 0.39813(10) 0.05753(9) 0.0233(4) Uani 1 1 d . . . H22A H 0.0265 0.4014 0.0528 0.028 Uiso 1 1 calc R . . H22B H 0.1575 0.3630 0.0210 0.028 Uiso 1 1 calc R . . C24 C 0.1573(2) 0.54090(11) 0.10882(10) 0.0267(4) Uani 1 1 d . . . H24A H 0.0533 0.5478 0.1051 0.032 Uiso 1 1 calc R . . H24B H 0.2002 0.5954 0.1047 0.032 Uiso 1 1 calc R . . C23 C 0.1941(2) 0.48523(11) 0.05129(10) 0.0281(4) Uani 1 1 d . . . H23A H 0.2983 0.4815 0.0531 0.034 Uiso 1 1 calc R . . H23B H 0.1555 0.5093 0.0074 0.034 Uiso 1 1 calc R . . C26 C 0.1544(2) 0.41543(11) 0.18587(9) 0.0268(4) Uani 1 1 d . . . H26A H 0.1974 0.3916 0.2291 0.032 Uiso 1 1 calc R . . H26B H 0.0506 0.4180 0.1861 0.032 Uiso 1 1 calc R . . C25 C 0.2135(2) 0.50338(12) 0.17867(10) 0.0304(4) Uani 1 1 d . . . H25A H 0.1849 0.5385 0.2147 0.037 Uiso 1 1 calc R . . H25B H 0.3183 0.5015 0.1840 0.037 Uiso 1 1 calc R . . S1N S 0.21148(4) 0.04898(2) 0.17665(2) 0.01715(9) Uani 1 1 d . . . S2N S 0.69077(4) 0.33196(2) 0.16710(2) 0.01772(10) Uani 1 1 d . . . Cl1N Cl 0.86461(5) 0.26101(3) 0.48003(2) 0.02949(11) Uani 1 1 d . . . Cl2N Cl 0.47133(5) 0.15383(4) 0.47354(2) 0.03937(13) Uani 1 1 d . . . C4 C 0.74429(17) 0.31411(10) 0.25561(8) 0.0183(3) Uani 1 1 d . . . C1 C 0.81981(19) 0.28315(10) 0.39337(8) 0.0211(3) Uani 1 1 d . . . C7 C 0.72401(16) 0.02217(10) 0.11041(8) 0.0165(3) Uani 1 1 d . . . H7 H 0.8113 0.0220 0.1441 0.020 Uiso 1 1 calc R . . C3 C 0.88207(18) 0.28418(10) 0.27911(9) 0.0215(3) Uani 1 1 d . . . H3 H 0.9484 0.2752 0.2485 0.026 Uiso 1 1 calc R . . C2 C 0.91943(18) 0.26792(10) 0.34830(9) 0.0225(4) Uani 1 1 d . . . H2 H 1.0105 0.2470 0.3645 0.027 Uiso 1 1 calc R . . C5 C 0.64500(18) 0.32958(10) 0.30104(9) 0.0226(3) Uani 1 1 d . . . H5 H 0.5534 0.3498 0.2849 0.027 Uiso 1 1 calc R . . C8 C 0.7706(2) 0.01721(11) 0.03873(9) 0.0240(4) Uani 1 1 d . . . H8A H 0.6861 0.0209 0.0044 0.029 Uiso 1 1 calc R . . H8B H 0.8334 0.0638 0.0321 0.029 Uiso 1 1 calc R . . C6 C 0.68368(19) 0.31454(11) 0.37057(9) 0.0250(4) Uani 1 1 d . . . H6 H 0.6189 0.3254 0.4016 0.030 Uiso 1 1 calc R . . C9 C 0.8501(2) -0.06430(11) 0.02963(9) 0.0259(4) Uani 1 1 d . . . H9A H 0.8752 -0.0672 -0.0167 0.031 Uiso 1 1 calc R . . H9B H 0.9389 -0.0658 0.0614 0.031 Uiso 1 1 calc R . . C11 C 0.71236(19) -0.13373(11) 0.11441(10) 0.0256(4) Uani 1 1 d . . . H11A H 0.7978 -0.1373 0.1482 0.031 Uiso 1 1 calc R . . H11B H 0.6504 -0.1806 0.1215 0.031 Uiso 1 1 calc R . . C10 C 0.7569(2) -0.13884(11) 0.04254(9) 0.0277(4) Uani 1 1 d . . . H10A H 0.8107 -0.1898 0.0381 0.033 Uiso 1 1 calc R . . H10B H 0.6714 -0.1399 0.0086 0.033 Uiso 1 1 calc R . . C12 C 0.63235(18) -0.05270(10) 0.12476(9) 0.0232(4) Uani 1 1 d . . . H12A H 0.5419 -0.0516 0.0941 0.028 Uiso 1 1 calc R . . H12B H 0.6102 -0.0499 0.1716 0.028 Uiso 1 1 calc R . . 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 O1 0.0113(5) 0.0212(6) 0.0308(6) -0.0044(5) 0.0023(5) -0.0001(4) O2 0.0164(6) 0.0231(6) 0.0287(6) 0.0029(5) 0.0034(5) -0.0035(5) O3 0.0171(6) 0.0187(6) 0.0328(7) 0.0007(5) 0.0008(5) 0.0033(5) N1 0.0100(6) 0.0183(7) 0.0239(7) -0.0024(5) 0.0020(5) -0.0004(5) N2 0.0099(6) 0.0180(7) 0.0248(7) -0.0034(5) 0.0008(5) -0.0014(5) C13 0.0144(7) 0.0192(8) 0.0156(7) -0.0010(6) 0.0034(6) 0.0003(6) C17 0.0167(8) 0.0162(8) 0.0194(8) 0.0000(6) 0.0010(6) 0.0016(6) C16 0.0159(8) 0.0248(9) 0.0243(9) 0.0015(7) 0.0041(6) 0.0013(6) C15 0.0167(8) 0.0234(9) 0.0306(9) -0.0009(7) -0.0013(7) 0.0001(6) C18 0.0206(9) 0.0438(11) 0.0251(9) -0.0010(8) 0.0051(7) -0.0091(8) C14 0.0256(9) 0.0293(9) 0.0216(9) -0.0030(7) -0.0022(7) -0.0002(7) C19 0.0280(10) 0.0596(14) 0.0215(9) -0.0034(9) 0.0064(8) -0.0101(9) O5 0.0194(6) 0.0280(7) 0.0245(6) -0.0046(5) 0.0036(5) 0.0083(5) N3 0.0106(6) 0.0180(7) 0.0218(7) 0.0020(5) 0.0015(5) 0.0014(5) O4 0.0207(6) 0.0166(6) 0.0303(7) -0.0012(5) -0.0005(5) -0.0016(5) C20 0.0139(7) 0.0216(8) 0.0156(8) 0.0035(6) 0.0020(6) 0.0002(6) O6 0.0113(6) 0.0267(7) 0.0401(7) 0.0102(5) 0.0042(5) 0.0004(5) N4 0.0101(6) 0.0198(7) 0.0302(8) 0.0058(6) 0.0016(5) -0.0011(5) C21 0.0127(7) 0.0194(8) 0.0283(9) 0.0063(7) 0.0023(6) -0.0018(6) C22 0.0288(9) 0.0216(9) 0.0200(8) 0.0030(6) 0.0054(7) 0.0012(7) C24 0.0243(9) 0.0191(9) 0.0360(10) 0.0023(7) 0.0015(7) -0.0011(7) C23 0.0306(10) 0.0248(9) 0.0291(10) 0.0100(7) 0.0048(8) 0.0003(7) C26 0.0298(10) 0.0288(10) 0.0208(9) 0.0017(7) -0.0007(7) -0.0107(8) C25 0.0336(10) 0.0268(10) 0.0295(10) -0.0018(8) -0.0011(8) -0.0097(8) S1N 0.01462(19) 0.01608(19) 0.0205(2) -0.00133(14) 0.00128(14) 0.00248(14) S2N 0.01329(18) 0.01581(19) 0.0238(2) -0.00002(15) 0.00161(15) -0.00055(14) Cl1N 0.0372(3) 0.0281(2) 0.0223(2) -0.00098(17) 0.00087(18) -0.00005(18) Cl2N 0.0356(3) 0.0565(3) 0.0240(2) -0.0101(2) -0.00384(19) -0.0043(2) C4 0.0173(8) 0.0147(8) 0.0225(8) -0.0025(6) 0.0014(6) -0.0022(6) C1 0.0267(9) 0.0152(8) 0.0208(8) -0.0023(6) 0.0007(7) -0.0029(6) C7 0.0131(7) 0.0182(8) 0.0180(8) -0.0018(6) 0.0010(6) 0.0012(6) C3 0.0176(8) 0.0213(8) 0.0258(9) -0.0040(7) 0.0037(6) -0.0011(6) C2 0.0177(8) 0.0204(8) 0.0285(9) -0.0026(7) -0.0009(7) -0.0002(6) C5 0.0186(8) 0.0198(8) 0.0296(9) -0.0019(7) 0.0037(7) 0.0040(6) C8 0.0300(9) 0.0242(9) 0.0184(8) -0.0009(6) 0.0057(7) 0.0031(7) C6 0.0257(9) 0.0230(9) 0.0277(9) -0.0033(7) 0.0093(7) 0.0029(7) C9 0.0303(9) 0.0304(10) 0.0175(8) -0.0049(7) 0.0058(7) 0.0052(8) C11 0.0210(8) 0.0187(8) 0.0375(10) 0.0012(7) 0.0050(7) 0.0014(7) C10 0.0266(9) 0.0238(9) 0.0303(10) -0.0095(7) -0.0054(7) 0.0060(7) C12 0.0174(8) 0.0195(8) 0.0335(10) 0.0006(7) 0.0057(7) -0.0003(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 O1 C13 1.2314(19) . ? O2 S2N 1.4277(12) . ? O3 S2N 1.4313(12) . ? N1 C13 1.339(2) . ? N1 C7 1.4736(19) . ? N2 C13 1.400(2) . ? N2 S2N 1.6516(13) . ? C17 C18 1.386(2) . ? C17 C16 1.387(2) . ? C17 S1N 1.7621(16) . ? C16 C15 1.386(2) . ? C15 C14 1.378(3) . ? C18 C19 1.383(3) . ? C14 C19 1.385(3) . ? C14 Cl2N 1.7361(18) . ? O5 S1N 1.4302(12) . ? N3 C20 1.400(2) . ? N3 S1N 1.6441(13) . ? O4 S1N 1.4299(12) . ? C20 O6 1.2292(19) . ? C20 N4 1.336(2) . ? N4 C21 1.468(2) . ? C21 C22 1.521(2) . ? C21 C26 1.527(2) . ? C22 C23 1.529(2) . ? C24 C23 1.516(3) . ? C24 C25 1.527(3) . ? C26 C25 1.530(2) . ? S2N C4 1.7679(17) . ? Cl1N C1 1.7353(17) . ? C4 C5 1.391(2) . ? C4 C3 1.393(2) . ? C1 C6 1.385(2) . ? C1 C2 1.388(2) . ? C7 C12 1.524(2) . ? C7 C8 1.530(2) . ? C3 C2 1.383(2) . ? C5 C6 1.387(2) . ? C8 C9 1.527(2) . ? C9 C10 1.520(3) . ? C11 C10 1.526(3) . ? C11 C12 1.527(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 C13 N1 C7 120.70(13) . . ? C13 N2 S2N 122.34(11) . . ? O1 C13 N1 123.87(14) . . ? O1 C13 N2 120.76(14) . . ? N1 C13 N2 115.37(13) . . ? C18 C17 C16 120.83(15) . . ? C18 C17 S1N 118.91(13) . . ? C16 C17 S1N 120.24(13) . . ? C15 C16 C17 119.47(16) . . ? C14 C15 C16 119.56(16) . . ? C19 C18 C17 119.47(17) . . ? C15 C14 C19 121.14(16) . . ? C15 C14 Cl2N 118.92(14) . . ? C19 C14 Cl2N 119.94(14) . . ? C18 C19 C14 119.52(17) . . ? C20 N3 S1N 121.65(11) . . ? O6 C20 N4 125.03(15) . . ? O6 C20 N3 120.49(14) . . ? N4 C20 N3 114.46(13) . . ? C20 N4 C21 122.23(13) . . ? N4 C21 C22 110.19(13) . . ? N4 C21 C26 110.25(13) . . ? C22 C21 C26 111.38(14) . . ? C21 C22 C23 110.25(14) . . ? C23 C24 C25 110.62(15) . . ? C24 C23 C22 110.67(15) . . ? C21 C26 C25 110.72(14) . . ? C24 C25 C26 111.24(14) . . ? O4 S1N O5 120.39(7) . . ? O4 S1N N3 104.07(7) . . ? O5 S1N N3 109.41(7) . . ? O4 S1N C17 108.93(7) . . ? O5 S1N C17 108.38(7) . . ? N3 S1N C17 104.52(7) . . ? O2 S2N O3 120.39(7) . . ? O2 S2N N2 108.90(7) . . ? O3 S2N N2 104.18(7) . . ? O2 S2N C4 108.88(7) . . ? O3 S2N C4 108.40(7) . . ? N2 S2N C4 105.01(7) . . ? C5 C4 C3 120.86(15) . . ? C5 C4 S2N 118.44(12) . . ? C3 C4 S2N 120.70(13) . . ? C6 C1 C2 121.41(16) . . ? C6 C1 Cl1N 118.93(13) . . ? C2 C1 Cl1N 119.65(13) . . ? N1 C7 C12 109.81(12) . . ? N1 C7 C8 111.40(13) . . ? C12 C7 C8 111.33(14) . . ? C2 C3 C4 119.53(16) . . ? C3 C2 C1 119.38(15) . . ? C6 C5 C4 119.46(16) . . ? C9 C8 C7 110.73(14) . . ? C1 C6 C5 119.35(16) . . ? C10 C9 C8 111.02(15) . . ? C10 C11 C12 111.51(15) . . ? C9 C10 C11 110.10(14) . . ? C7 C12 C11 110.60(13) . . ? _diffrn_measured_fraction_theta_max 0.967 _diffrn_reflns_theta_full 27.73 _diffrn_measured_fraction_theta_full 0.967 _refine_diff_density_max 0.469 _refine_diff_density_min -0.464 _refine_diff_density_rms 0.053 _database_code_depnum_ccdc_archive 'CCDC 965659'