Electronic Supplementary Material for CrystEngComm This Journal is © The Royal Society of Chemistry 2004 data_global _journal_coden_Cambridge 1350 loop_ _publ_author_name 'Paul Kelly' 'Mark Robert James Elsegood' 'Liam M. Gilby' 'Kathryn E. Holmes' 'Julia M. Stonehouse' _publ_contact_author_name 'Dr Paul Kelly' _publ_contact_author_address ; Department of Chemistry Loughborough University Loughborough Leics LE11 3TU UNITED KINGDOM ; _publ_contact_author_email P.F.KELLY@LBORO.AC.UK _publ_requested_journal 'Cryst Eng. Comm.' _publ_section_title ; The preparation and crystal structures of derivatised sulfimidium salts ; data_2 _database_code_depnum_ccdc_archive 'CCDC 226731' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C18 H18 Cl2 N2 S2' _chemical_formula_weight 397.36 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' 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 orthorhombic _symmetry_space_group_name_H-M Pbca loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' '-x, -y, -z' 'x-1/2, y, -z-1/2' 'x, -y-1/2, z-1/2' '-x-1/2, y-1/2, z' _cell_length_a 9.1712(6) _cell_length_b 18.3898(12) _cell_length_c 21.6441(14) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 3650.4(4) _cell_formula_units_Z 8 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 8395 _cell_measurement_theta_min 2.407 _cell_measurement_theta_max 28.084 _exptl_crystal_description needle _exptl_crystal_colour colourless _exptl_crystal_size_max 0.69 _exptl_crystal_size_mid 0.09 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.446 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1648 _exptl_absorpt_coefficient_mu 0.587 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.688 _exptl_absorpt_correction_T_max 0.966 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker SMART 1000 CCD diffractometer' _diffrn_measurement_method '\w rotation with narrow frames' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 24708 _diffrn_reflns_av_R_equivalents 0.0326 _diffrn_reflns_av_sigmaI/netI 0.0190 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -21 _diffrn_reflns_limit_k_max 21 _diffrn_reflns_limit_l_min -25 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_theta_min 2.21 _diffrn_reflns_theta_max 25.00 _reflns_number_total 3203 _reflns_number_gt 2640 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'Bruker SHELXTL' _computing_structure_refinement 'Bruker SHELXTL' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL and local programs' _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^)+(0.1090P)^2^+16.4193P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens 'geom except NH coords freely refined' _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0002(5) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 3203 _refine_ls_number_parameters 230 _refine_ls_number_restraints 7 _refine_ls_R_factor_all 0.0761 _refine_ls_R_factor_gt 0.0629 _refine_ls_wR_factor_ref 0.2014 _refine_ls_wR_factor_gt 0.1838 _refine_ls_goodness_of_fit_ref 1.054 _refine_ls_restrained_S_all 1.053 _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 C1 C 0.1377(6) 0.4429(3) 0.6050(2) 0.0333(11) Uani 1 1 d . . . C2 C 0.2517(6) 0.4658(3) 0.5684(2) 0.0362(12) Uani 1 1 d . . . H2 H 0.3350 0.4884 0.5862 0.043 Uiso 1 1 calc R . . C3 C 0.2424(7) 0.4552(3) 0.5048(3) 0.0399(13) Uani 1 1 d . . . H3 H 0.3194 0.4704 0.4784 0.048 Uiso 1 1 calc R . . C4 C 0.1183(7) 0.4221(3) 0.4805(3) 0.0447(14) Uani 1 1 d . . . H4 H 0.1110 0.4151 0.4371 0.054 Uiso 1 1 calc R . . C5 C 0.0064(6) 0.3992(3) 0.5181(3) 0.0426(13) Uani 1 1 d . . . H5 H -0.0765 0.3763 0.5004 0.051 Uiso 1 1 calc R . . C6 C 0.0135(6) 0.4094(3) 0.5815(3) 0.0387(12) Uani 1 1 d . . . H6 H -0.0635 0.3942 0.6079 0.046 Uiso 1 1 calc R . . S1 S 0.14055(16) 0.45995(7) 0.68719(6) 0.0367(4) Uani 1 1 d . . . N1 N 0.3039(5) 0.4564(3) 0.7123(2) 0.0451(12) Uani 1 1 d D . . H1A H 0.327(7) 0.404(3) 0.735(3) 0.068 Uiso 1 1 d D . . H1B H 0.390(6) 0.478(3) 0.681(3) 0.068 Uiso 1 1 d D . . C7 C 0.0969(5) 0.5553(3) 0.6830(2) 0.0278(10) Uani 1 1 d . . . C8 C -0.0472(5) 0.5758(3) 0.6906(2) 0.0313(11) Uani 1 1 d . . . H8 H -0.1212 0.5414 0.7001 0.038 Uiso 1 1 calc R . . C9 C -0.0776(6) 0.6494(3) 0.6837(2) 0.0367(12) Uani 1 1 d . . . H9 H -0.1747 0.6664 0.6883 0.044 Uiso 1 1 calc R . . C10 C 0.0328(6) 0.6976(3) 0.6702(2) 0.0352(12) Uani 1 1 d . . . H10 H 0.0147 0.7482 0.6660 0.042 Uiso 1 1 calc R . . C11 C 0.1714(6) 0.6689(3) 0.6630(2) 0.0315(11) Uani 1 1 d . . . C12 C 0.2063(5) 0.5995(2) 0.66897(18) 0.0187(9) Uani 1 1 d . . . H12 H 0.3032 0.5824 0.6636 0.022 Uiso 1 1 calc R . . S2 S 0.31934(16) 0.72864(7) 0.64105(6) 0.0360(4) Uani 1 1 d . . . N2 N 0.4603(6) 0.6922(3) 0.6719(2) 0.0432(12) Uani 1 1 d D . . H2A H 0.550(6) 0.726(3) 0.691(3) 0.065 Uiso 1 1 d D . . H2B H 0.481(7) 0.633(2) 0.669(3) 0.065 Uiso 1 1 d D . . C13 C 0.3236(6) 0.7088(3) 0.5598(2) 0.0345(12) Uani 1 1 d . . . C14 C 0.2497(7) 0.7564(3) 0.5218(3) 0.0447(14) Uani 1 1 d . . . H14 H 0.1993 0.7970 0.5385 0.054 Uiso 1 1 calc R . . C15 C 0.2508(7) 0.7438(4) 0.4585(3) 0.0519(16) Uani 1 1 d . . . H15 H 0.2015 0.7763 0.4316 0.062 Uiso 1 1 calc R . . C16 C 0.3230(6) 0.6843(4) 0.4346(3) 0.0487(16) Uani 1 1 d . . . H16 H 0.3219 0.6754 0.3914 0.058 Uiso 1 1 calc R . . C17 C 0.3967(6) 0.6377(4) 0.4734(3) 0.0463(14) Uani 1 1 d . . . H17 H 0.4467 0.5970 0.4566 0.056 Uiso 1 1 calc R . . C18 C 0.3989(6) 0.6494(3) 0.5372(2) 0.0403(13) Uani 1 1 d . . . H18 H 0.4504 0.6177 0.5641 0.048 Uiso 1 1 calc R . . Cl1 Cl 0.30721(13) 0.30438(6) 0.77951(5) 0.0321(4) Uani 1 1 d . . . Cl2 Cl 0.59075(11) 0.52916(6) 0.65155(5) 0.0243(3) Uani 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 0.041(3) 0.024(2) 0.035(3) -0.004(2) -0.004(2) 0.000(2) C2 0.041(3) 0.031(3) 0.036(3) -0.002(2) -0.003(2) 0.000(2) C3 0.050(3) 0.034(3) 0.036(3) 0.000(2) 0.001(2) 0.005(2) C4 0.062(4) 0.035(3) 0.037(3) -0.008(2) -0.018(3) 0.011(3) C5 0.047(3) 0.036(3) 0.045(3) -0.008(2) -0.012(3) 0.001(2) C6 0.038(3) 0.033(3) 0.045(3) -0.006(2) -0.010(2) 0.001(2) S1 0.0485(8) 0.0283(7) 0.0333(7) -0.0006(5) -0.0054(6) -0.0023(6) N1 0.044(3) 0.046(3) 0.045(3) 0.004(2) -0.002(2) 0.002(2) C7 0.031(3) 0.026(2) 0.026(2) -0.0014(18) 0.0004(19) -0.004(2) C8 0.027(2) 0.041(3) 0.026(2) -0.004(2) 0.0028(19) -0.004(2) C9 0.028(3) 0.050(3) 0.032(3) -0.009(2) -0.001(2) 0.009(2) C10 0.045(3) 0.030(3) 0.030(3) -0.006(2) -0.009(2) 0.011(2) C11 0.038(3) 0.031(3) 0.026(2) -0.002(2) -0.004(2) -0.004(2) C12 0.019(2) 0.018(2) 0.019(2) -0.0029(16) 0.0015(16) -0.0015(16) S2 0.0464(8) 0.0268(7) 0.0346(7) 0.0017(5) -0.0054(6) -0.0095(5) N2 0.046(3) 0.039(3) 0.045(3) 0.003(2) -0.014(2) -0.015(2) C13 0.040(3) 0.031(3) 0.033(3) 0.007(2) -0.005(2) -0.015(2) C14 0.048(3) 0.036(3) 0.050(3) 0.012(3) -0.008(3) -0.010(3) C15 0.053(4) 0.059(4) 0.043(3) 0.025(3) -0.017(3) -0.018(3) C16 0.044(3) 0.071(4) 0.031(3) 0.010(3) -0.007(2) -0.018(3) C17 0.038(3) 0.063(4) 0.038(3) -0.001(3) 0.005(2) -0.007(3) C18 0.038(3) 0.050(3) 0.033(3) 0.007(2) -0.002(2) -0.005(2) Cl1 0.0389(7) 0.0258(6) 0.0314(6) 0.0056(4) 0.0042(5) 0.0085(5) Cl2 0.0151(5) 0.0369(6) 0.0208(5) 0.0037(4) -0.0013(4) -0.0027(4) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C2 1.378(8) . ? C1 C6 1.391(7) . ? C1 S1 1.806(5) . ? C2 C3 1.392(8) . ? C3 C4 1.394(8) . ? C4 C5 1.375(9) . ? C5 C6 1.388(8) . ? S1 N1 1.595(5) . ? S1 C7 1.802(5) . ? C7 C12 1.326(6) . ? C7 C8 1.383(7) . ? C8 C9 1.390(8) . ? C9 C10 1.377(8) . ? C10 C11 1.385(8) . ? C11 C12 1.322(7) . ? C11 S2 1.809(5) . ? S2 N2 1.602(5) . ? S2 C13 1.797(5) . ? C13 C14 1.380(8) . ? C13 C18 1.381(8) . ? C14 C15 1.388(8) . ? C15 C16 1.380(10) . ? C16 C17 1.377(9) . ? C17 C18 1.396(8) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 C1 C6 123.1(5) . . ? C2 C1 S1 120.2(4) . . ? C6 C1 S1 116.7(4) . . ? C1 C2 C3 118.6(5) . . ? C2 C3 C4 119.0(6) . . ? C5 C4 C3 121.3(5) . . ? C4 C5 C6 120.6(5) . . ? C5 C6 C1 117.4(5) . . ? N1 S1 C7 105.4(3) . . ? N1 S1 C1 110.0(3) . . ? C7 S1 C1 96.7(2) . . ? C12 C7 C8 125.7(5) . . ? C12 C7 S1 116.1(4) . . ? C8 C7 S1 118.1(4) . . ? C7 C8 C9 116.3(5) . . ? C10 C9 C8 120.2(5) . . ? C9 C10 C11 116.9(5) . . ? C12 C11 C10 125.3(5) . . ? C12 C11 S2 115.5(4) . . ? C10 C11 S2 119.1(4) . . ? C11 C12 C7 115.5(4) . . ? N2 S2 C13 107.8(3) . . ? N2 S2 C11 104.0(2) . . ? C13 S2 C11 98.6(2) . . ? C14 C13 C18 122.4(5) . . ? C14 C13 S2 116.4(4) . . ? C18 C13 S2 121.2(4) . . ? C13 C14 C15 118.6(6) . . ? C16 C15 C14 120.4(6) . . ? C17 C16 C15 120.0(6) . . ? C16 C17 C18 121.0(6) . . ? C13 C18 C17 117.7(5) . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N1 H1A Cl1 1.10(4) 2.08(4) 3.151(5) 164(5) . N1 H1B Cl2 1.11(4) 2.17(4) 3.231(5) 160(6) . N2 H2A Cl1 1.10(4) 2.06(4) 3.148(5) 169(5) 3_656 N2 H2B Cl2 1.10(4) 2.19(4) 3.258(5) 161(5) . _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 1.457 _refine_diff_density_min -0.874 _refine_diff_density_rms 0.114 #===END data_3 _database_code_depnum_ccdc_archive 'CCDC 226732' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C12 H12 Cl N O S' _chemical_formula_weight 253.74 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 orthorhombic _symmetry_space_group_name_H-M Pbca loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' '-x, -y, -z' 'x-1/2, y, -z-1/2' 'x, -y-1/2, z-1/2' '-x-1/2, y-1/2, z' _cell_length_a 9.0907(4) _cell_length_b 9.8349(4) _cell_length_c 27.2937(14) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2440.22(19) _cell_formula_units_Z 8 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 19733 _cell_measurement_theta_min 1 _cell_measurement_theta_max 27.48 _exptl_crystal_description needle _exptl_crystal_colour colourless _exptl_crystal_size_max 0.08 _exptl_crystal_size_mid 0.04 _exptl_crystal_size_min 0.01 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.381 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1056 _exptl_absorpt_coefficient_mu 0.461 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.964 _exptl_absorpt_correction_T_max 0.995 _exptl_absorpt_process_details ; Using multiple and symmetry-related data measurements via the program SORTAV See R.H.Blessing, Acta Cryst, (1995), A51, 33-38 ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Enraf Nonius FR591 rotating anode' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Enraf Nonius KappaCCD area detector' _diffrn_measurement_method 'Phi and Omega scans to fill Ewald sphere' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 10411 _diffrn_reflns_av_R_equivalents 0.0915 _diffrn_reflns_av_sigmaI/netI 0.0923 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_limit_l_max 32 _diffrn_reflns_theta_min 2.69 _diffrn_reflns_theta_max 25.00 _reflns_number_total 2140 _reflns_number_gt 1399 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'COLLECT, (Hooft, 1998)' _computing_cell_refinement 'DENZO (Otwinowski and Minor, 1997) and COLLECT (Hooft, 1998)' _computing_data_reduction 'DENZO (Otwinowski and Minor, 1997) and COLLECT (Hooft, 1998)' _computing_structure_solution 'Bruker SHELXTL' _computing_structure_refinement 'Bruker SHELXTL' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL and local programs' _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^)+(0.0105P)^2^+5.7459P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens 'geom except NH & OH coords freely refined' _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0013(5) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 2140 _refine_ls_number_parameters 155 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1142 _refine_ls_R_factor_gt 0.0649 _refine_ls_wR_factor_ref 0.1168 _refine_ls_wR_factor_gt 0.1031 _refine_ls_goodness_of_fit_ref 1.041 _refine_ls_restrained_S_all 1.041 _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 S1 S 0.10092(11) 0.39978(9) 0.11822(4) 0.0240(3) Uani 1 1 d . . . N1 N -0.0564(4) 0.3543(4) 0.09492(15) 0.0293(10) Uani 1 1 d . . . H1A H -0.091(5) 0.277(4) 0.1036(17) 0.035 Uiso 1 1 d . . . H1B H -0.120(5) 0.416(4) 0.0992(17) 0.035 Uiso 1 1 d . . . O1 O 0.4028(3) 0.4352(3) 0.12525(12) 0.0290(8) Uani 1 1 d . . . H1 H 0.487(5) 0.458(4) 0.1217(18) 0.035 Uiso 1 1 d . . . C1 C 0.2299(4) 0.2983(4) 0.08603(16) 0.0225(10) Uani 1 1 d . . . C2 C 0.3760(5) 0.3346(4) 0.09219(16) 0.0253(10) Uani 1 1 d . . . C3 C 0.4830(5) 0.2665(4) 0.06547(16) 0.0260(11) Uani 1 1 d . . . H3 H 0.5839 0.2889 0.0695 0.031 Uiso 1 1 calc R . . C4 C 0.4415(5) 0.1664(4) 0.03306(17) 0.0303(11) Uani 1 1 d . . . H4 H 0.5151 0.1208 0.0146 0.036 Uiso 1 1 calc R . . C5 C 0.2947(5) 0.1301(4) 0.02665(16) 0.0282(11) Uani 1 1 d . . . H5 H 0.2686 0.0603 0.0042 0.034 Uiso 1 1 calc R . . C6 C 0.1868(5) 0.1971(4) 0.05339(16) 0.0245(10) Uani 1 1 d . . . H6 H 0.0860 0.1743 0.0495 0.029 Uiso 1 1 calc R . . C7 C 0.1120(5) 0.3410(4) 0.18016(15) 0.0236(10) Uani 1 1 d . . . C8 C 0.1912(5) 0.2299(5) 0.1950(2) 0.0460(14) Uani 1 1 d . . . H8 H 0.2409 0.1745 0.1718 0.055 Uiso 1 1 calc R . . C9 C 0.1972(6) 0.2002(6) 0.2444(2) 0.0551(16) Uani 1 1 d . . . H9 H 0.2516 0.1235 0.2553 0.066 Uiso 1 1 calc R . . C10 C 0.1257(6) 0.2800(6) 0.27798(19) 0.0460(14) Uani 1 1 d . . . H10 H 0.1332 0.2606 0.3120 0.055 Uiso 1 1 calc R . . C11 C 0.0433(8) 0.3878(5) 0.2621(2) 0.0651(18) Uani 1 1 d . . . H11 H -0.0105 0.4406 0.2851 0.078 Uiso 1 1 calc R . . C12 C 0.0379(6) 0.4202(5) 0.2133(2) 0.0536(16) Uani 1 1 d . . . H12 H -0.0167 0.4968 0.2025 0.064 Uiso 1 1 calc R . . Cl1 Cl 0.69591(12) 0.56738(11) 0.11775(6) 0.0466(4) Uani 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 S1 0.0230(6) 0.0238(5) 0.0252(6) 0.0000(5) 0.0018(5) 0.0017(4) N1 0.022(2) 0.031(2) 0.035(3) 0.001(2) -0.0012(18) 0.0045(17) O1 0.0212(15) 0.0341(16) 0.032(2) -0.0039(15) 0.0025(16) -0.0054(14) C1 0.025(3) 0.023(2) 0.020(2) 0.004(2) 0.004(2) 0.0058(18) C2 0.031(3) 0.024(2) 0.021(3) 0.004(2) -0.003(2) -0.001(2) C3 0.018(2) 0.028(2) 0.032(3) 0.006(2) 0.003(2) 0.0026(19) C4 0.035(3) 0.026(2) 0.030(3) 0.001(2) 0.010(2) 0.006(2) C5 0.042(3) 0.022(2) 0.021(3) -0.001(2) -0.002(2) 0.003(2) C6 0.029(2) 0.022(2) 0.023(3) 0.005(2) -0.002(2) 0.001(2) C7 0.024(2) 0.027(2) 0.020(3) -0.001(2) 0.003(2) -0.006(2) C8 0.043(3) 0.058(3) 0.037(3) 0.016(3) 0.008(3) 0.019(3) C9 0.043(3) 0.082(4) 0.040(4) 0.029(3) 0.006(3) 0.015(3) C10 0.049(3) 0.067(4) 0.022(3) 0.007(3) 0.005(3) -0.023(3) C11 0.122(5) 0.041(3) 0.032(4) -0.001(3) 0.026(4) 0.002(4) C12 0.084(4) 0.036(3) 0.041(4) 0.004(3) 0.019(3) 0.010(3) Cl1 0.0254(6) 0.0291(6) 0.0853(12) -0.0029(7) 0.0071(7) 0.0004(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 S1 N1 1.628(4) . ? S1 C1 1.773(4) . ? S1 C7 1.790(4) . ? O1 C2 1.361(5) . ? C1 C2 1.385(6) . ? C1 C6 1.392(6) . ? C2 C3 1.388(6) . ? C3 C4 1.376(6) . ? C4 C5 1.393(6) . ? C5 C6 1.388(6) . ? C7 C8 1.369(6) . ? C7 C12 1.369(6) . ? C8 C9 1.381(7) . ? C9 C10 1.370(7) . ? C10 C11 1.368(7) . ? C11 C12 1.372(7) . ? 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 N1 S1 C1 103.5(2) . . ? N1 S1 C7 109.2(2) . . ? C1 S1 C7 104.4(2) . . ? C2 C1 C6 122.1(4) . . ? C2 C1 S1 115.4(3) . . ? C6 C1 S1 122.2(3) . . ? O1 C2 C1 116.1(4) . . ? O1 C2 C3 125.0(4) . . ? C1 C2 C3 119.0(4) . . ? C4 C3 C2 119.4(4) . . ? C3 C4 C5 121.8(4) . . ? C6 C5 C4 119.3(4) . . ? C5 C6 C1 118.5(4) . . ? C8 C7 C12 121.1(5) . . ? C8 C7 S1 124.6(4) . . ? C12 C7 S1 114.3(4) . . ? C7 C8 C9 118.6(5) . . ? C10 C9 C8 120.8(5) . . ? C11 C10 C9 119.5(5) . . ? C10 C11 C12 120.4(5) . . ? C7 C12 C11 119.5(5) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N1 S1 C1 C2 168.4(3) . . . . ? C7 S1 C1 C2 -77.3(3) . . . . ? N1 S1 C1 C6 -6.1(4) . . . . ? C7 S1 C1 C6 108.2(4) . . . . ? C6 C1 C2 O1 180.0(4) . . . . ? S1 C1 C2 O1 5.5(5) . . . . ? C6 C1 C2 C3 -0.9(6) . . . . ? S1 C1 C2 C3 -175.4(3) . . . . ? O1 C2 C3 C4 -180.0(4) . . . . ? C1 C2 C3 C4 1.0(6) . . . . ? C2 C3 C4 C5 -0.7(6) . . . . ? C3 C4 C5 C6 0.4(6) . . . . ? C4 C5 C6 C1 -0.3(6) . . . . ? C2 C1 C6 C5 0.6(6) . . . . ? S1 C1 C6 C5 174.7(3) . . . . ? N1 S1 C7 C8 102.7(4) . . . . ? C1 S1 C7 C8 -7.4(4) . . . . ? N1 S1 C7 C12 -79.7(4) . . . . ? C1 S1 C7 C12 170.1(4) . . . . ? C12 C7 C8 C9 -1.1(7) . . . . ? S1 C7 C8 C9 176.3(4) . . . . ? C7 C8 C9 C10 0.0(8) . . . . ? C8 C9 C10 C11 2.2(8) . . . . ? C9 C10 C11 C12 -3.2(9) . . . . ? C8 C7 C12 C11 0.1(8) . . . . ? S1 C7 C12 C11 -177.6(5) . . . . ? C10 C11 C12 C7 2.1(9) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N1 H1A Cl1 0.85(4) 2.31(4) 3.155(4) 173(4) 8_655 N1 H1B Cl1 0.84(4) 2.30(4) 3.138(4) 173(4) 1_455 O1 H1 Cl1 0.80(4) 2.19(4) 2.972(3) 166(4) . _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.379 _refine_diff_density_min -0.304 _refine_diff_density_rms 0.069 #===END data_4 _database_code_depnum_ccdc_archive 'CCDC 226733' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C12 H12 Cl N O S' _chemical_formula_weight 253.74 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 13.5552(19) _cell_length_b 5.6845(8) _cell_length_c 15.508(2) _cell_angle_alpha 90.00 _cell_angle_beta 91.335(2) _cell_angle_gamma 90.00 _cell_volume 1194.6(3) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 5352 _cell_measurement_theta_min 2.63 _cell_measurement_theta_max 28.43 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.66 _exptl_crystal_size_mid 0.29 _exptl_crystal_size_min 0.18 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.411 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 528 _exptl_absorpt_coefficient_mu 0.471 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.746 _exptl_absorpt_correction_T_max 0.920 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker SMART 1000 CCD diffractometer' _diffrn_measurement_method '\w rotation with narrow frames' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 9507 _diffrn_reflns_av_R_equivalents 0.0233 _diffrn_reflns_av_sigmaI/netI 0.0239 _diffrn_reflns_limit_h_min -18 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 1.50 _diffrn_reflns_theta_max 28.93 _reflns_number_total 2825 _reflns_number_gt 2373 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'Bruker SHELXTL' _computing_structure_refinement 'Bruker SHELXTL' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL and local programs' _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^)+(0.0545P)^2^+0.3183P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens 'geom except NH & OH coords freely refined' _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2825 _refine_ls_number_parameters 154 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0416 _refine_ls_R_factor_gt 0.0325 _refine_ls_wR_factor_ref 0.0939 _refine_ls_wR_factor_gt 0.0873 _refine_ls_goodness_of_fit_ref 1.042 _refine_ls_restrained_S_all 1.042 _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 S1 S 0.21476(3) -0.04028(7) 0.07754(3) 0.02717(12) Uani 1 1 d . . . N1 N 0.18540(11) -0.0082(3) -0.02488(9) 0.0310(3) Uani 1 1 d . . . H1A H 0.2105(15) 0.115(4) -0.0514(13) 0.046 Uiso 1 1 d . . . H1B H 0.1988(15) -0.129(4) -0.0499(13) 0.046 Uiso 1 1 d . . . O1 O 0.63534(8) 0.0786(2) 0.16270(7) 0.0323(3) Uani 1 1 d . . . H1 H 0.6604(15) 0.213(4) 0.1454(13) 0.048 Uiso 1 1 d . . . C1 C 0.34155(11) 0.0077(3) 0.09841(10) 0.0258(3) Uani 1 1 d . . . C2 C 0.39115(11) 0.2082(3) 0.07031(10) 0.0283(3) Uani 1 1 d . . . H2 H 0.3571 0.3260 0.0380 0.034 Uiso 1 1 calc R . . C3 C 0.49041(11) 0.2322(3) 0.09033(10) 0.0270(3) Uani 1 1 d . . . H3 H 0.5252 0.3670 0.0714 0.032 Uiso 1 1 calc R . . C4 C 0.53984(11) 0.0584(3) 0.13847(9) 0.0253(3) Uani 1 1 d . . . C5 C 0.49024(12) -0.1427(3) 0.16419(10) 0.0298(3) Uani 1 1 d . . . H5 H 0.5246 -0.2625 0.1953 0.036 Uiso 1 1 calc R . . C6 C 0.39064(11) -0.1683(3) 0.14440(10) 0.0293(3) Uani 1 1 d . . . H6 H 0.3562 -0.3050 0.1621 0.035 Uiso 1 1 calc R . . C7 C 0.15637(10) 0.2114(3) 0.12257(9) 0.0254(3) Uani 1 1 d . . . C8 C 0.19629(11) 0.3190(3) 0.19576(10) 0.0293(3) Uani 1 1 d . . . H8 H 0.2568 0.2652 0.2209 0.035 Uiso 1 1 calc R . . C9 C 0.14609(12) 0.5065(3) 0.23156(11) 0.0332(4) Uani 1 1 d . . . H9 H 0.1728 0.5833 0.2813 0.040 Uiso 1 1 calc R . . C10 C 0.05733(12) 0.5826(3) 0.19535(11) 0.0342(4) Uani 1 1 d . . . H10 H 0.0239 0.7126 0.2198 0.041 Uiso 1 1 calc R . . C11 C 0.01726(12) 0.4700(3) 0.12375(11) 0.0350(4) Uani 1 1 d . . . H11 H -0.0442 0.5213 0.0998 0.042 Uiso 1 1 calc R . . C12 C 0.06601(11) 0.2836(3) 0.08682(10) 0.0322(4) Uani 1 1 d . . . H12 H 0.0384 0.2055 0.0378 0.039 Uiso 1 1 calc R . . Cl1 Cl 0.74523(3) 0.50280(7) 0.10231(3) 0.03371(13) Uani 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 S1 0.0223(2) 0.02450(19) 0.0348(2) 0.00150(14) 0.00234(14) -0.00406(14) N1 0.0298(7) 0.0295(7) 0.0336(7) -0.0063(6) 0.0014(6) -0.0055(6) O1 0.0220(5) 0.0323(6) 0.0424(7) 0.0040(5) -0.0029(4) 0.0016(5) C1 0.0221(7) 0.0236(7) 0.0318(8) 0.0006(6) 0.0021(6) -0.0009(5) C2 0.0236(7) 0.0239(7) 0.0373(8) 0.0060(6) 0.0002(6) 0.0008(6) C3 0.0236(7) 0.0228(7) 0.0348(8) 0.0040(6) 0.0025(6) -0.0015(6) C4 0.0218(7) 0.0270(7) 0.0272(7) -0.0020(6) 0.0018(5) 0.0027(6) C5 0.0311(8) 0.0246(7) 0.0335(8) 0.0052(6) 0.0006(6) 0.0049(6) C6 0.0299(8) 0.0227(7) 0.0353(8) 0.0038(6) 0.0039(6) -0.0010(6) C7 0.0189(7) 0.0294(7) 0.0281(7) 0.0019(6) 0.0030(5) -0.0019(6) C8 0.0212(7) 0.0379(9) 0.0287(7) 0.0015(6) -0.0005(5) -0.0020(6) C9 0.0301(8) 0.0407(9) 0.0291(8) -0.0053(6) 0.0035(6) -0.0054(7) C10 0.0302(8) 0.0352(9) 0.0375(8) -0.0001(7) 0.0109(7) 0.0018(7) C11 0.0226(8) 0.0449(10) 0.0375(9) 0.0028(7) 0.0006(6) 0.0054(7) C12 0.0238(8) 0.0400(9) 0.0325(8) -0.0024(7) -0.0041(6) -0.0020(6) Cl1 0.0283(2) 0.0245(2) 0.0481(3) 0.00072(15) -0.00446(16) -0.00126(14) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag S1 N1 1.6386(15) . ? S1 C1 1.7626(16) . ? S1 C7 1.7850(16) . ? O1 C4 1.3444(18) . ? C1 C6 1.389(2) . ? C1 C2 1.398(2) . ? C2 C3 1.380(2) . ? C3 C4 1.400(2) . ? C4 C5 1.389(2) . ? C5 C6 1.385(2) . ? C7 C8 1.388(2) . ? C7 C12 1.394(2) . ? C8 C9 1.388(2) . ? C9 C10 1.385(2) . ? C10 C11 1.382(3) . ? C11 C12 1.381(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 N1 S1 C1 111.99(7) . . ? N1 S1 C7 100.96(7) . . ? C1 S1 C7 104.10(7) . . ? C6 C1 C2 121.26(14) . . ? C6 C1 S1 115.85(11) . . ? C2 C1 S1 122.88(12) . . ? C3 C2 C1 118.94(14) . . ? C2 C3 C4 120.14(14) . . ? O1 C4 C5 117.35(14) . . ? O1 C4 C3 122.31(14) . . ? C5 C4 C3 120.33(14) . . ? C6 C5 C4 119.91(14) . . ? C5 C6 C1 119.39(14) . . ? C8 C7 C12 121.17(14) . . ? C8 C7 S1 120.33(11) . . ? C12 C7 S1 118.28(12) . . ? C9 C8 C7 118.70(14) . . ? C10 C9 C8 120.48(15) . . ? C11 C10 C9 120.17(16) . . ? C12 C11 C10 120.40(15) . . ? C11 C12 C7 119.05(15) . . ? 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 N1 S1 C1 C6 -128.28(12) . . . . ? C7 S1 C1 C6 123.49(12) . . . . ? N1 S1 C1 C2 51.16(15) . . . . ? C7 S1 C1 C2 -57.07(15) . . . . ? C6 C1 C2 C3 -1.2(2) . . . . ? S1 C1 C2 C3 179.37(12) . . . . ? C1 C2 C3 C4 -0.4(2) . . . . ? C2 C3 C4 O1 -177.08(14) . . . . ? C2 C3 C4 C5 2.0(2) . . . . ? O1 C4 C5 C6 177.13(14) . . . . ? C3 C4 C5 C6 -2.0(2) . . . . ? C4 C5 C6 C1 0.4(2) . . . . ? C2 C1 C6 C5 1.2(2) . . . . ? S1 C1 C6 C5 -179.34(12) . . . . ? N1 S1 C7 C8 -149.34(13) . . . . ? C1 S1 C7 C8 -33.12(14) . . . . ? N1 S1 C7 C12 36.01(14) . . . . ? C1 S1 C7 C12 152.23(12) . . . . ? C12 C7 C8 C9 -2.2(2) . . . . ? S1 C7 C8 C9 -176.65(12) . . . . ? C7 C8 C9 C10 0.7(2) . . . . ? C8 C9 C10 C11 0.9(3) . . . . ? C9 C10 C11 C12 -1.1(3) . . . . ? C10 C11 C12 C7 -0.3(3) . . . . ? C8 C7 C12 C11 1.9(2) . . . . ? S1 C7 C12 C11 176.55(13) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N1 H1A Cl1 0.88(2) 2.39(2) 3.2608(16) 166.9(18) 3_665 N1 H1B Cl1 0.81(2) 2.40(2) 3.2067(15) 170(2) 3_655 O1 H1 Cl1 0.88(2) 2.12(2) 2.9958(13) 169.5(19) . _diffrn_measured_fraction_theta_max 0.895 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.544 _refine_diff_density_min -0.260 _refine_diff_density_rms 0.054 #===END