# Electronic Supplementary Material (ESI) for CrystEngComm # 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_sh3155 #TrackingRef 'sh3155.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C26 H23 Cl N2 O S2' _chemical_formula_weight 479.03 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 16.2099(6) _cell_length_b 11.0498(4) _cell_length_c 12.7896(5) _cell_angle_alpha 90.00 _cell_angle_beta 103.183(2) _cell_angle_gamma 90.00 _cell_volume 2230.45(14) _cell_formula_units_Z 4 _cell_measurement_temperature 153(2) _cell_measurement_reflns_used 8672 _cell_measurement_theta_min 2.25 _cell_measurement_theta_max 27.07 _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_max 0.23 _exptl_crystal_size_mid 0.23 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.427 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1000 _exptl_absorpt_coefficient_mu 0.381 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9184 _exptl_absorpt_correction_T_max 0.9716 _exptl_absorpt_process_details 'sadabs Brukeraxs 2010' _exptl_special_details ; ? ; _diffrn_ambient_temperature 153(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_reflns_number 40877 _diffrn_reflns_av_R_equivalents 0.0450 _diffrn_reflns_av_sigmaI/netI 0.0293 _diffrn_reflns_limit_h_min -20 _diffrn_reflns_limit_h_max 20 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 1.29 _diffrn_reflns_theta_max 27.15 _reflns_number_total 4953 _reflns_number_gt 3920 _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, 2008)' _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^)+(0.0406P)^2^+1.0175P] 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 mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4953 _refine_ls_number_parameters 381 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0495 _refine_ls_R_factor_gt 0.0350 _refine_ls_wR_factor_ref 0.0916 _refine_ls_wR_factor_gt 0.0836 _refine_ls_goodness_of_fit_ref 1.048 _refine_ls_restrained_S_all 1.048 _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 Cl1 Cl 0.40573(3) 1.28727(4) 0.60322(4) 0.03416(13) Uani 1 1 d . . . O1 O 0.30022(7) 0.95524(12) 0.31055(10) 0.0268(3) Uani 1 1 d . . . N1 N 0.22720(10) 0.58916(14) 0.38830(13) 0.0295(4) Uani 1 1 d . . . N2 N 0.13237(11) 0.74957(17) 0.68808(14) 0.0376(4) Uani 1 1 d . . . S1 S 0.45500(3) 0.72713(4) 0.59445(4) 0.02802(12) Uani 1 1 d . . . S2 S 0.05027(3) 1.02228(4) 0.38630(4) 0.02896(12) Uani 1 1 d . . . C1 C 0.28297(11) 0.73711(16) 0.52543(14) 0.0224(4) Uani 1 1 d . . . C2 C 0.35231(11) 0.67878(18) 0.60924(15) 0.0263(4) Uani 1 1 d . . . C3 C 0.43670(11) 0.88351(16) 0.59635(13) 0.0230(4) Uani 1 1 d . . . C4 C 0.50590(11) 0.95775(18) 0.63547(14) 0.0264(4) Uani 1 1 d . . . C5 C 0.49775(11) 1.08150(18) 0.63662(14) 0.0271(4) Uani 1 1 d . . . C6 C 0.41853(11) 1.13156(16) 0.59773(13) 0.0245(4) Uani 1 1 d . . . C7 C 0.34923(11) 1.05979(16) 0.55530(14) 0.0235(4) Uani 1 1 d . . . C8 C 0.35572(10) 0.93377(16) 0.55348(13) 0.0212(3) Uani 1 1 d . . . C9 C 0.28270(10) 0.85548(16) 0.50313(13) 0.0213(3) Uani 1 1 d . . . C10 C 0.20728(10) 0.90972(16) 0.42387(14) 0.0223(4) Uani 1 1 d . . . C11 C 0.23255(10) 0.97672(15) 0.33260(13) 0.0205(3) Uani 1 1 d . . . C12 C 0.17147(10) 1.06205(15) 0.26567(14) 0.0223(4) Uani 1 1 d . . . C13 C 0.19611(12) 1.11720(17) 0.17931(15) 0.0279(4) Uani 1 1 d . . . C14 C 0.14203(13) 1.19369(18) 0.11045(16) 0.0339(4) Uani 1 1 d . . . C15 C 0.06218(13) 1.21681(18) 0.12730(17) 0.0347(5) Uani 1 1 d . . . C16 C 0.03654(13) 1.16507(18) 0.21277(16) 0.0321(4) Uani 1 1 d . . . C17 C 0.09068(11) 1.08720(16) 0.28275(14) 0.0242(4) Uani 1 1 d . . . C18 C 0.14632(11) 0.97653(19) 0.47789(16) 0.0280(4) Uani 1 1 d . . . C19 C 0.21431(11) 0.65103(16) 0.47369(14) 0.0242(4) Uani 1 1 d . . . C20 C 0.29979(12) 0.60571(18) 0.33933(16) 0.0297(4) Uani 1 1 d . . . C21 C 0.35477(13) 0.49329(18) 0.35299(18) 0.0336(4) Uani 1 1 d . . . C22 C 0.30312(14) 0.3807(2) 0.31290(19) 0.0387(5) Uani 1 1 d . . . C23 C 0.22604(14) 0.37139(19) 0.36149(18) 0.0350(5) Uani 1 1 d . . . C24 C 0.17416(13) 0.48635(19) 0.34184(19) 0.0357(5) Uani 1 1 d . . . C25 C 0.14711(12) 0.63424(18) 0.51955(15) 0.0296(4) Uani 1 1 d . . . C26 C 0.14010(11) 0.69870(18) 0.61203(16) 0.0301(4) Uani 1 1 d . . . H1 H 0.3520(12) 0.5913(19) 0.6000(15) 0.027(5) Uiso 1 1 d . . . H2 H 0.3468(13) 0.6978(18) 0.6805(17) 0.032(5) Uiso 1 1 d . . . H3 H 0.5607(13) 0.9225(19) 0.6633(16) 0.035(5) Uiso 1 1 d . . . H4 H 0.5415(14) 1.129(2) 0.6596(17) 0.040(6) Uiso 1 1 d . . . H5 H 0.2975(13) 1.0969(18) 0.5260(15) 0.030(5) Uiso 1 1 d . . . H6 H 0.1722(13) 0.8434(19) 0.3874(16) 0.032(5) Uiso 1 1 d . . . H7 H 0.1309(12) 0.9266(19) 0.5306(16) 0.032(5) Uiso 1 1 d . . . H8 H 0.1722(13) 1.052(2) 0.5164(17) 0.039(6) Uiso 1 1 d . . . H9 H -0.0163(15) 1.184(2) 0.2245(17) 0.042(6) Uiso 1 1 d . . . H10 H 0.0264(13) 1.2685(19) 0.0801(17) 0.035(6) Uiso 1 1 d . . . H11 H 0.1610(14) 1.231(2) 0.0511(18) 0.040(6) Uiso 1 1 d . . . H12 H 0.2503(13) 1.1000(18) 0.1696(16) 0.032(5) Uiso 1 1 d . . . H13 H 0.3343(12) 0.6793(18) 0.3734(15) 0.029(5) Uiso 1 1 d . . . H14 H 0.2767(12) 0.6187(18) 0.2613(17) 0.032(5) Uiso 1 1 d . . . H15 H 0.3849(14) 0.4865(19) 0.4296(19) 0.040(6) Uiso 1 1 d . . . H16 H 0.3990(13) 0.5066(18) 0.3152(17) 0.035(6) Uiso 1 1 d . . . H17 H 0.3387(14) 0.308(2) 0.3311(18) 0.044(6) Uiso 1 1 d . . . H18 H 0.2836(14) 0.387(2) 0.2330(19) 0.049(7) Uiso 1 1 d . . . H19 H 0.2437(13) 0.360(2) 0.4380(18) 0.038(6) Uiso 1 1 d . . . H20 H 0.1920(15) 0.304(2) 0.3349(19) 0.051(7) Uiso 1 1 d . . . H21 H 0.1567(14) 0.5017(19) 0.265(2) 0.042(6) Uiso 1 1 d . . . H22 H 0.1241(14) 0.4807(19) 0.3742(17) 0.038(6) Uiso 1 1 d . . . H23 H 0.1014(14) 0.578(2) 0.4949(17) 0.041(6) 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 Cl1 0.0356(3) 0.0255(2) 0.0421(3) -0.0032(2) 0.0103(2) -0.00461(19) O1 0.0201(6) 0.0346(7) 0.0274(6) -0.0004(6) 0.0084(5) 0.0032(5) N1 0.0276(8) 0.0279(8) 0.0353(9) -0.0067(7) 0.0119(7) -0.0049(6) N2 0.0339(9) 0.0450(10) 0.0371(10) -0.0021(8) 0.0145(8) 0.0006(8) S1 0.0201(2) 0.0289(2) 0.0349(3) 0.00322(19) 0.00588(18) 0.00548(17) S2 0.0184(2) 0.0349(3) 0.0354(3) 0.0102(2) 0.00987(18) 0.00449(18) C1 0.0203(8) 0.0256(9) 0.0225(8) 0.0013(7) 0.0074(7) 0.0017(7) C2 0.0228(9) 0.0286(10) 0.0271(10) 0.0052(8) 0.0047(7) 0.0018(7) C3 0.0217(8) 0.0279(9) 0.0199(8) 0.0019(7) 0.0058(7) 0.0021(7) C4 0.0194(9) 0.0358(10) 0.0232(9) 0.0013(8) 0.0032(7) 0.0009(7) C5 0.0223(9) 0.0371(11) 0.0215(9) -0.0030(8) 0.0043(7) -0.0069(8) C6 0.0264(9) 0.0266(9) 0.0218(8) -0.0016(7) 0.0084(7) -0.0028(7) C7 0.0194(8) 0.0275(9) 0.0238(9) 0.0000(7) 0.0054(7) 0.0007(7) C8 0.0189(8) 0.0274(9) 0.0183(8) 0.0011(7) 0.0063(6) 0.0010(7) C9 0.0174(8) 0.0258(9) 0.0215(8) -0.0008(7) 0.0062(7) 0.0018(7) C10 0.0190(8) 0.0231(9) 0.0247(9) 0.0007(7) 0.0049(7) 0.0018(7) C11 0.0190(8) 0.0209(8) 0.0214(8) -0.0043(7) 0.0040(6) -0.0022(7) C12 0.0209(8) 0.0188(8) 0.0277(9) -0.0011(7) 0.0070(7) -0.0012(7) C13 0.0296(10) 0.0249(9) 0.0321(10) 0.0009(8) 0.0128(8) 0.0015(8) C14 0.0433(12) 0.0288(10) 0.0329(10) 0.0069(8) 0.0154(9) 0.0044(9) C15 0.0368(11) 0.0300(10) 0.0365(11) 0.0100(9) 0.0068(9) 0.0098(9) C16 0.0266(10) 0.0319(10) 0.0384(11) 0.0059(9) 0.0086(8) 0.0070(8) C17 0.0220(9) 0.0219(9) 0.0293(9) 0.0022(7) 0.0070(7) 0.0004(7) C18 0.0218(9) 0.0337(10) 0.0303(10) 0.0064(9) 0.0096(8) 0.0042(8) C19 0.0232(9) 0.0210(8) 0.0275(9) 0.0043(7) 0.0041(7) 0.0025(7) C20 0.0330(10) 0.0301(10) 0.0288(10) -0.0005(8) 0.0127(8) -0.0023(8) C21 0.0334(11) 0.0349(11) 0.0364(11) 0.0008(9) 0.0161(9) 0.0006(9) C22 0.0437(12) 0.0303(11) 0.0467(13) -0.0040(10) 0.0200(10) 0.0025(9) C23 0.0424(12) 0.0281(10) 0.0370(12) -0.0047(9) 0.0144(9) -0.0067(9) C24 0.0323(11) 0.0335(11) 0.0418(12) -0.0107(9) 0.0096(9) -0.0073(9) C25 0.0243(9) 0.0315(10) 0.0337(10) -0.0009(8) 0.0079(8) -0.0028(8) C26 0.0228(9) 0.0331(10) 0.0355(11) 0.0062(9) 0.0091(8) -0.0016(8) _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 Cl1 C6 1.7364(19) . ? O1 C11 1.217(2) . ? N1 C19 1.345(2) . ? N1 C20 1.465(2) . ? N1 C24 1.466(2) . ? N2 C26 1.155(3) . ? S1 C3 1.7543(18) . ? S1 C2 1.7987(19) . ? S2 C17 1.7587(18) . ? S2 C18 1.7945(19) . ? C1 C9 1.338(2) . ? C1 C19 1.498(2) . ? C1 C2 1.509(2) . ? C2 H1 0.97(2) . ? C2 H2 0.96(2) . ? C3 C4 1.388(2) . ? C3 C8 1.416(2) . ? C4 C5 1.374(3) . ? C4 H3 0.96(2) . ? C5 C6 1.382(3) . ? C5 H4 0.88(2) . ? C6 C7 1.381(2) . ? C7 C8 1.397(3) . ? C7 H5 0.93(2) . ? C8 C9 1.489(2) . ? C9 C10 1.522(2) . ? C10 C11 1.515(2) . ? C10 C18 1.520(2) . ? C10 H6 0.98(2) . ? C11 C12 1.488(2) . ? C12 C13 1.397(2) . ? C12 C17 1.404(2) . ? C13 C14 1.381(3) . ? C13 H12 0.93(2) . ? C14 C15 1.384(3) . ? C14 H11 0.97(2) . ? C15 C16 1.379(3) . ? C15 H10 0.93(2) . ? C16 C17 1.398(3) . ? C16 H9 0.93(2) . ? C18 H7 0.95(2) . ? C18 H8 1.01(2) . ? C19 C25 1.362(3) . ? C20 C21 1.516(3) . ? C20 H13 1.03(2) . ? C20 H14 0.99(2) . ? C21 C22 1.522(3) . ? C21 H15 0.99(2) . ? C21 H16 0.96(2) . ? C22 C23 1.521(3) . ? C22 H17 0.99(2) . ? C22 H18 1.00(2) . ? C23 C24 1.512(3) . ? C23 H19 0.96(2) . ? C23 H20 0.94(2) . ? C24 H21 0.98(2) . ? C24 H22 0.99(2) . ? C25 C26 1.407(3) . ? C25 H23 0.96(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 C19 N1 C20 124.92(15) . . ? C19 N1 C24 122.53(16) . . ? C20 N1 C24 112.17(15) . . ? C3 S1 C2 97.34(9) . . ? C17 S2 C18 100.94(9) . . ? C9 C1 C19 124.06(15) . . ? C9 C1 C2 122.30(16) . . ? C19 C1 C2 113.60(15) . . ? C1 C2 S1 110.83(13) . . ? C1 C2 H1 110.8(11) . . ? S1 C2 H1 105.1(11) . . ? C1 C2 H2 111.4(12) . . ? S1 C2 H2 108.9(12) . . ? H1 C2 H2 109.5(16) . . ? C4 C3 C8 120.64(17) . . ? C4 C3 S1 117.51(13) . . ? C8 C3 S1 121.72(13) . . ? C5 C4 C3 121.36(17) . . ? C5 C4 H3 118.8(13) . . ? C3 C4 H3 119.8(13) . . ? C4 C5 C6 118.55(17) . . ? C4 C5 H4 122.0(14) . . ? C6 C5 H4 119.4(14) . . ? C7 C6 C5 121.15(17) . . ? C7 C6 Cl1 119.40(14) . . ? C5 C6 Cl1 119.45(14) . . ? C6 C7 C8 121.42(17) . . ? C6 C7 H5 118.8(12) . . ? C8 C7 H5 119.7(12) . . ? C7 C8 C3 116.83(16) . . ? C7 C8 C9 122.07(15) . . ? C3 C8 C9 121.01(15) . . ? C1 C9 C8 120.79(15) . . ? C1 C9 C10 119.33(15) . . ? C8 C9 C10 119.86(15) . . ? C11 C10 C18 115.52(15) . . ? C11 C10 C9 112.85(14) . . ? C18 C10 C9 113.29(14) . . ? C11 C10 H6 103.2(11) . . ? C18 C10 H6 102.3(12) . . ? C9 C10 H6 108.3(12) . . ? O1 C11 C12 120.46(15) . . ? O1 C11 C10 119.97(15) . . ? C12 C11 C10 119.43(14) . . ? C13 C12 C17 118.80(16) . . ? C13 C12 C11 117.28(15) . . ? C17 C12 C11 123.90(15) . . ? C14 C13 C12 121.12(18) . . ? C14 C13 H12 121.3(12) . . ? C12 C13 H12 117.6(12) . . ? C13 C14 C15 119.62(18) . . ? C13 C14 H11 119.4(13) . . ? C15 C14 H11 121.0(13) . . ? C16 C15 C14 120.57(18) . . ? C16 C15 H10 120.9(13) . . ? C14 C15 H10 118.6(13) . . ? C15 C16 C17 120.28(18) . . ? C15 C16 H9 119.6(14) . . ? C17 C16 H9 120.1(14) . . ? C16 C17 C12 119.60(17) . . ? C16 C17 S2 116.49(14) . . ? C12 C17 S2 123.88(13) . . ? C10 C18 S2 113.41(13) . . ? C10 C18 H7 110.2(12) . . ? S2 C18 H7 107.3(12) . . ? C10 C18 H8 112.4(12) . . ? S2 C18 H8 106.8(12) . . ? H7 C18 H8 106.3(17) . . ? N1 C19 C25 124.61(17) . . ? N1 C19 C1 116.36(15) . . ? C25 C19 C1 118.85(16) . . ? N1 C20 C21 110.91(16) . . ? N1 C20 H13 109.3(11) . . ? C21 C20 H13 110.6(11) . . ? N1 C20 H14 107.0(11) . . ? C21 C20 H14 108.1(12) . . ? H13 C20 H14 110.8(16) . . ? C20 C21 C22 111.55(17) . . ? C20 C21 H15 108.6(12) . . ? C22 C21 H15 112.3(12) . . ? C20 C21 H16 107.6(12) . . ? C22 C21 H16 111.8(12) . . ? H15 C21 H16 104.6(18) . . ? C23 C22 C21 110.97(17) . . ? C23 C22 H17 109.7(13) . . ? C21 C22 H17 110.0(13) . . ? C23 C22 H18 109.0(13) . . ? C21 C22 H18 107.8(14) . . ? H17 C22 H18 109.3(19) . . ? C24 C23 C22 110.65(18) . . ? C24 C23 H19 107.5(13) . . ? C22 C23 H19 110.0(13) . . ? C24 C23 H20 110.3(14) . . ? C22 C23 H20 111.9(14) . . ? H19 C23 H20 106.2(19) . . ? N1 C24 C23 109.33(17) . . ? N1 C24 H21 106.4(13) . . ? C23 C24 H21 109.6(13) . . ? N1 C24 H22 109.8(12) . . ? C23 C24 H22 110.7(12) . . ? H21 C24 H22 110.8(18) . . ? C19 C25 C26 121.24(18) . . ? C19 C25 H23 125.4(13) . . ? C26 C25 H23 113.4(13) . . ? N2 C26 C25 178.0(2) . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 27.15 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.349 _refine_diff_density_min -0.263 _refine_diff_density_rms 0.052 _database_code_depnum_ccdc_archive 'CCDC 892391' ####################################################################### # # 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_sh3157 #TrackingRef 'sh3157.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C18 H16 N2 O2 S' _chemical_formula_weight 324.39 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 7.6912(5) _cell_length_b 9.0394(6) _cell_length_c 11.8022(8) _cell_angle_alpha 105.136(3) _cell_angle_beta 107.797(3) _cell_angle_gamma 94.983(3) _cell_volume 741.66(9) _cell_formula_units_Z 2 _cell_measurement_temperature 153(2) _cell_measurement_reflns_used 9258 _cell_measurement_theta_min 2.37 _cell_measurement_theta_max 34.13 _exptl_crystal_description ? _exptl_crystal_colour yellow _exptl_crystal_size_max 0.34 _exptl_crystal_size_mid 0.32 _exptl_crystal_size_min 0.16 _exptl_crystal_density_meas 0 _exptl_crystal_density_diffrn 1.453 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 340 _exptl_absorpt_coefficient_mu 0.230 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min 0.9265 _exptl_absorpt_correction_T_max 0.9632 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 153(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_reflns_number 23027 _diffrn_reflns_av_R_equivalents 0.0265 _diffrn_reflns_av_sigmaI/netI 0.0284 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 1.90 _diffrn_reflns_theta_max 34.79 _reflns_number_total 6145 _reflns_number_gt 5061 _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, 2008)' _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^)+(0.0607P)^2^+0.0878P] 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 mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 6145 _refine_ls_number_parameters 272 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0467 _refine_ls_R_factor_gt 0.0364 _refine_ls_wR_factor_ref 0.1081 _refine_ls_wR_factor_gt 0.1006 _refine_ls_goodness_of_fit_ref 1.063 _refine_ls_restrained_S_all 1.063 _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 N1 N 0.35560(10) 0.24318(9) 0.14552(7) 0.01758(14) Uani 1 1 d . . . N2 N 0.33361(13) 0.00886(11) -0.17800(8) 0.02743(18) Uani 1 1 d . . . O2 O 0.11792(11) -0.28646(8) -0.11148(6) 0.02675(15) Uani 1 1 d . . . S1 S 0.30713(3) 0.11202(3) 0.46510(2) 0.02198(7) Uani 1 1 d . . . C1 C 0.15530(11) -0.10535(10) 0.19409(7) 0.01600(14) Uani 1 1 d . . . O1 O 0.12907(9) -0.21729(7) 0.08460(6) 0.01913(13) Uani 1 1 d . . . C5 C 0.15397(12) -0.17936(10) -0.01628(8) 0.01803(15) Uani 1 1 d . . . C4 C 0.22982(11) -0.01995(10) 0.00409(8) 0.01611(14) Uani 1 1 d . . . C3 C 0.27269(11) 0.09409(9) 0.11958(7) 0.01506(14) Uani 1 1 d . . . C2 C 0.21633(12) 0.04782(10) 0.21338(8) 0.01590(14) Uani 1 1 d . . . C6 C 0.19287(13) 0.16007(10) 0.32486(8) 0.01941(16) Uani 1 1 d . . . C7 C 0.18997(12) -0.08122(10) 0.41484(8) 0.01802(15) Uani 1 1 d . . . C8 C 0.17631(14) -0.15023(12) 0.50532(9) 0.02297(17) Uani 1 1 d . . . C9 C 0.08971(14) -0.30414(12) 0.47027(9) 0.02418(18) Uani 1 1 d . . . C10 C 0.01388(14) -0.39099(11) 0.34471(9) 0.02259(17) Uani 1 1 d . . . C11 C 0.02765(12) -0.32377(10) 0.25441(8) 0.01913(16) Uani 1 1 d . . . C12 C 0.11779(12) -0.16912(10) 0.28745(8) 0.01632(14) Uani 1 1 d . . . C13 C 0.28765(12) -0.00021(10) -0.09566(8) 0.01873(16) Uani 1 1 d . . . C14 C 0.50819(13) 0.32250(11) 0.26385(8) 0.02054(16) Uani 1 1 d . . . C15 C 0.49654(15) 0.49318(11) 0.31408(10) 0.02584(19) Uani 1 1 d . . . C16 C 0.48680(16) 0.57579(12) 0.21555(10) 0.0274(2) Uani 1 1 d . . . C17 C 0.33149(14) 0.48610(11) 0.09440(9) 0.02355(18) Uani 1 1 d . . . C18 C 0.35243(13) 0.31721(11) 0.04835(9) 0.02006(16) Uani 1 1 d . . . H1 H 0.2448(18) 0.2692(15) 0.3395(12) 0.023(3) Uiso 1 1 d . . . H2 H 0.063(2) 0.1545(16) 0.3134(13) 0.027(3) Uiso 1 1 d . . . H3 H 0.230(2) -0.0876(18) 0.5921(15) 0.036(4) Uiso 1 1 d . . . H4 H 0.085(2) -0.3471(17) 0.5373(14) 0.031(3) Uiso 1 1 d . . . H5 H -0.047(2) -0.4973(18) 0.3197(14) 0.035(4) Uiso 1 1 d . . . H6 H -0.0247(18) -0.3830(15) 0.1676(12) 0.024(3) Uiso 1 1 d . . . H7 H 0.6212(19) 0.3133(15) 0.2436(12) 0.023(3) Uiso 1 1 d . . . H8 H 0.5107(17) 0.2649(15) 0.3215(12) 0.019(3) Uiso 1 1 d . . . H9 H 0.605(2) 0.5381(17) 0.3877(14) 0.033(4) Uiso 1 1 d . . . H10 H 0.385(2) 0.5005(16) 0.3406(13) 0.028(3) Uiso 1 1 d . . . H11 H 0.601(2) 0.5807(17) 0.1980(14) 0.037(4) Uiso 1 1 d . . . H12 H 0.4639(19) 0.6836(17) 0.2454(13) 0.030(3) Uiso 1 1 d . . . H13 H 0.327(2) 0.5341(17) 0.0305(14) 0.033(4) Uiso 1 1 d . . . H14 H 0.213(2) 0.4848(16) 0.1059(13) 0.030(3) Uiso 1 1 d . . . H15 H 0.4658(17) 0.3110(14) 0.0269(12) 0.018(3) Uiso 1 1 d . . . H16 H 0.2494(18) 0.2623(15) -0.0254(12) 0.021(3) 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 N1 0.0205(3) 0.0144(3) 0.0156(3) 0.0043(2) 0.0041(3) 0.0002(2) N2 0.0331(4) 0.0307(4) 0.0197(4) 0.0063(3) 0.0120(3) 0.0055(3) O2 0.0412(4) 0.0182(3) 0.0162(3) -0.0003(2) 0.0097(3) -0.0007(3) S1 0.02806(12) 0.01808(11) 0.01402(10) 0.00157(7) 0.00357(8) -0.00184(8) C1 0.0184(3) 0.0151(3) 0.0127(3) 0.0026(3) 0.0045(3) 0.0021(3) O1 0.0271(3) 0.0143(3) 0.0136(3) 0.0016(2) 0.0067(2) 0.0006(2) C5 0.0221(4) 0.0169(4) 0.0142(3) 0.0033(3) 0.0061(3) 0.0029(3) C4 0.0177(3) 0.0158(3) 0.0135(3) 0.0034(3) 0.0046(3) 0.0022(3) C3 0.0156(3) 0.0139(3) 0.0147(3) 0.0040(3) 0.0041(3) 0.0029(3) C2 0.0189(3) 0.0145(3) 0.0135(3) 0.0032(3) 0.0055(3) 0.0026(3) C6 0.0257(4) 0.0161(4) 0.0162(4) 0.0029(3) 0.0084(3) 0.0038(3) C7 0.0196(3) 0.0177(4) 0.0150(3) 0.0037(3) 0.0050(3) 0.0016(3) C8 0.0276(4) 0.0251(4) 0.0152(4) 0.0059(3) 0.0070(3) 0.0012(3) C9 0.0300(4) 0.0243(4) 0.0200(4) 0.0095(3) 0.0097(3) 0.0012(4) C10 0.0256(4) 0.0197(4) 0.0230(4) 0.0077(3) 0.0092(3) -0.0001(3) C11 0.0213(4) 0.0172(4) 0.0172(4) 0.0047(3) 0.0057(3) 0.0000(3) C12 0.0181(3) 0.0156(3) 0.0145(3) 0.0041(3) 0.0053(3) 0.0014(3) C13 0.0196(4) 0.0186(4) 0.0156(3) 0.0031(3) 0.0046(3) 0.0030(3) C14 0.0202(4) 0.0168(4) 0.0189(4) 0.0029(3) 0.0018(3) 0.0000(3) C15 0.0315(5) 0.0163(4) 0.0232(4) 0.0010(3) 0.0055(4) 0.0004(3) C16 0.0311(5) 0.0166(4) 0.0315(5) 0.0065(4) 0.0083(4) -0.0001(3) C17 0.0279(4) 0.0180(4) 0.0265(4) 0.0095(3) 0.0094(4) 0.0043(3) C18 0.0247(4) 0.0180(4) 0.0194(4) 0.0078(3) 0.0088(3) 0.0024(3) _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 N1 C3 1.3537(11) . ? N1 C18 1.4662(11) . ? N1 C14 1.4733(11) . ? N2 C13 1.1500(12) . ? O2 C5 1.2130(10) . ? S1 C7 1.7532(9) . ? S1 C6 1.8036(9) . ? C1 C2 1.3588(12) . ? C1 O1 1.3626(10) . ? C1 C12 1.4583(12) . ? O1 C5 1.3831(11) . ? C5 C4 1.4359(12) . ? C4 C3 1.4007(12) . ? C4 C13 1.4254(12) . ? C3 C2 1.4464(12) . ? C2 C6 1.5076(12) . ? C6 H1 0.982(13) . ? C6 H2 0.963(14) . ? C7 C8 1.3948(13) . ? C7 C12 1.4104(12) . ? C8 C9 1.3858(14) . ? C8 H3 0.968(16) . ? C9 C10 1.3917(14) . ? C9 H4 0.976(14) . ? C10 C11 1.3829(13) . ? C10 H5 0.959(16) . ? C11 C12 1.4031(12) . ? C11 H6 0.960(13) . ? C14 C15 1.5228(14) . ? C14 H7 0.974(13) . ? C14 H8 0.956(12) . ? C15 C16 1.5249(15) . ? C15 H9 0.962(15) . ? C15 H10 1.000(14) . ? C16 C17 1.5202(15) . ? C16 H11 0.960(16) . ? C16 H12 0.997(14) . ? C17 C18 1.5215(13) . ? C17 H13 0.957(15) . ? C17 H14 0.959(14) . ? C18 H15 0.981(12) . ? C18 H16 0.957(13) . ? 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 C3 N1 C18 122.86(7) . . ? C3 N1 C14 121.24(7) . . ? C18 N1 C14 112.44(7) . . ? C7 S1 C6 97.03(4) . . ? C2 C1 O1 122.61(8) . . ? C2 C1 C12 124.64(8) . . ? O1 C1 C12 112.71(7) . . ? C1 O1 C5 121.30(7) . . ? O2 C5 O1 116.23(8) . . ? O2 C5 C4 126.61(8) . . ? O1 C5 C4 117.04(7) . . ? C3 C4 C13 124.55(8) . . ? C3 C4 C5 122.04(8) . . ? C13 C4 C5 112.34(7) . . ? N1 C3 C4 124.08(8) . . ? N1 C3 C2 119.32(7) . . ? C4 C3 C2 116.55(7) . . ? C1 C2 C3 119.42(7) . . ? C1 C2 C6 115.69(8) . . ? C3 C2 C6 124.27(7) . . ? C2 C6 S1 110.28(6) . . ? C2 C6 H1 114.0(8) . . ? S1 C6 H1 106.6(8) . . ? C2 C6 H2 109.6(8) . . ? S1 C6 H2 109.1(8) . . ? H1 C6 H2 107.1(11) . . ? C8 C7 C12 119.86(8) . . ? C8 C7 S1 118.09(7) . . ? C12 C7 S1 121.99(7) . . ? C9 C8 C7 120.19(9) . . ? C9 C8 H3 122.0(9) . . ? C7 C8 H3 117.8(9) . . ? C8 C9 C10 120.51(9) . . ? C8 C9 H4 116.9(9) . . ? C10 C9 H4 122.6(9) . . ? C11 C10 C9 119.68(9) . . ? C11 C10 H5 119.3(9) . . ? C9 C10 H5 121.0(9) . . ? C10 C11 C12 120.96(8) . . ? C10 C11 H6 120.1(8) . . ? C12 C11 H6 119.0(8) . . ? C11 C12 C7 118.76(8) . . ? C11 C12 C1 120.84(7) . . ? C7 C12 C1 120.03(8) . . ? N2 C13 C4 177.04(10) . . ? N1 C14 C15 111.69(8) . . ? N1 C14 H7 105.0(8) . . ? C15 C14 H7 110.5(8) . . ? N1 C14 H8 109.2(8) . . ? C15 C14 H8 113.7(7) . . ? H7 C14 H8 106.3(11) . . ? C14 C15 C16 110.68(9) . . ? C14 C15 H9 106.6(9) . . ? C16 C15 H9 112.0(9) . . ? C14 C15 H10 109.5(8) . . ? C16 C15 H10 110.5(8) . . ? H9 C15 H10 107.4(11) . . ? C17 C16 C15 110.04(8) . . ? C17 C16 H11 107.5(9) . . ? C15 C16 H11 110.5(9) . . ? C17 C16 H12 109.5(8) . . ? C15 C16 H12 110.1(8) . . ? H11 C16 H12 109.2(12) . . ? C16 C17 C18 111.89(8) . . ? C16 C17 H13 111.1(9) . . ? C18 C17 H13 109.1(9) . . ? C16 C17 H14 110.6(8) . . ? C18 C17 H14 107.1(8) . . ? H13 C17 H14 106.9(12) . . ? N1 C18 C17 108.96(7) . . ? N1 C18 H15 110.8(7) . . ? C17 C18 H15 110.7(7) . . ? N1 C18 H16 108.7(8) . . ? C17 C18 H16 110.0(8) . . ? H15 C18 H16 107.6(10) . . ? _diffrn_measured_fraction_theta_max 0.955 _diffrn_reflns_theta_full 34.79 _diffrn_measured_fraction_theta_full 0.955 _refine_diff_density_max 0.509 _refine_diff_density_min -0.267 _refine_diff_density_rms 0.062 _database_code_depnum_ccdc_archive 'CCDC 892392' ####################################################################### # # 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_sh3158 #TrackingRef 'sh3158.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C21 H13 N O S2' _chemical_formula_weight 359.44 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 7.354(7) _cell_length_b 10.160(9) _cell_length_c 11.440(11) _cell_angle_alpha 106.88(3) _cell_angle_beta 98.32(4) _cell_angle_gamma 93.54(4) _cell_volume 804.4(13) _cell_formula_units_Z 2 _cell_measurement_temperature 152(2) _cell_measurement_reflns_used 803 _cell_measurement_theta_min 2.37 _cell_measurement_theta_max 19.01 _exptl_crystal_description ? _exptl_crystal_colour 'dark orange' _exptl_crystal_size_max 0.31 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas 0 _exptl_crystal_density_diffrn 1.484 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 372 _exptl_absorpt_coefficient_mu 0.340 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min 0.9023 _exptl_absorpt_correction_T_max 0.9859 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 152(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_reflns_number 20068 _diffrn_reflns_av_R_equivalents 0.0342 _diffrn_reflns_av_sigmaI/netI 0.0367 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 1.89 _diffrn_reflns_theta_max 32.53 _reflns_number_total 5404 _reflns_number_gt 4420 _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, 2008)' _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^)+(0.0500P)^2^+0.1998P] 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 mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 5404 _refine_ls_number_parameters 278 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0484 _refine_ls_R_factor_gt 0.0371 _refine_ls_wR_factor_ref 0.0998 _refine_ls_wR_factor_gt 0.0932 _refine_ls_goodness_of_fit_ref 1.035 _refine_ls_restrained_S_all 1.035 _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 1.15823(4) 0.61040(3) 0.90775(3) 0.02133(8) Uani 1 1 d . . . S2 S 0.75885(5) 0.93169(3) 0.52714(3) 0.02083(8) Uani 1 1 d . . . O1 O 0.74076(13) 0.49310(9) 0.49235(8) 0.01809(18) Uani 1 1 d . . . N1 N 0.75054(18) 0.17019(12) 0.31515(11) 0.0267(2) Uani 1 1 d . . . C1 C 1.02674(19) 0.82125(14) 1.07199(12) 0.0220(3) Uani 1 1 d . . . H1 H 1.135(3) 0.8131(18) 1.1301(17) 0.032(5) Uiso 1 1 d . . . C2 C 0.9010(2) 0.91679(15) 1.10860(13) 0.0243(3) Uani 1 1 d . . . H2 H 0.915(2) 0.9729(18) 1.1912(16) 0.029(4) Uiso 1 1 d . . . C3 C 0.74375(19) 0.92330(14) 1.02651(12) 0.0231(3) Uani 1 1 d . . . H3 H 0.658(2) 0.9863(17) 1.0536(15) 0.025(4) Uiso 1 1 d . . . C4 C 0.71576(18) 0.83831(13) 0.90528(12) 0.0202(2) Uani 1 1 d . . . H4 H 0.610(2) 0.8429(17) 0.8518(15) 0.025(4) Uiso 1 1 d . . . C5 C 0.84738(17) 0.74656(12) 0.86352(11) 0.0174(2) Uani 1 1 d . . . C6 C 0.99977(18) 0.73447(13) 0.95075(12) 0.0186(2) Uani 1 1 d . . . C7 C 0.99439(19) 0.47870(13) 0.80271(12) 0.0196(2) Uani 1 1 d . . . H7A H 1.065(2) 0.4038(18) 0.7671(15) 0.025(4) Uiso 1 1 d . . . H7B H 0.915(2) 0.4451(17) 0.8504(16) 0.026(4) Uiso 1 1 d . . . C8 C 0.88820(16) 0.53310(12) 0.70424(11) 0.0163(2) Uani 1 1 d . . . C9 C 0.82640(16) 0.66331(12) 0.73276(11) 0.0157(2) Uani 1 1 d . . . C10 C 0.74183(16) 0.71643(12) 0.63218(11) 0.0159(2) Uani 1 1 d . . . C11 C 0.69885(19) 0.86513(13) 0.64867(12) 0.0190(2) Uani 1 1 d . . . H11A H 0.771(2) 0.9274(17) 0.7250(15) 0.024(4) Uiso 1 1 d . . . H11B H 0.567(2) 0.8780(17) 0.6505(15) 0.023(4) Uiso 1 1 d . . . C12 C 0.65012(17) 0.80046(13) 0.39726(12) 0.0178(2) Uani 1 1 d . . . C13 C 0.59529(19) 0.83012(14) 0.28492(13) 0.0221(3) Uani 1 1 d . . . H13 H 0.609(2) 0.9201(18) 0.2797(15) 0.026(4) Uiso 1 1 d . . . C14 C 0.51976(19) 0.72611(15) 0.17971(13) 0.0231(3) Uani 1 1 d . . . H14 H 0.486(2) 0.7473(17) 0.1013(16) 0.027(4) Uiso 1 1 d . . . C15 C 0.49615(18) 0.59154(14) 0.18486(12) 0.0211(2) Uani 1 1 d . . . H15 H 0.438(2) 0.5185(18) 0.1110(16) 0.030(5) Uiso 1 1 d . . . C16 C 0.55423(17) 0.56043(13) 0.29549(12) 0.0183(2) Uani 1 1 d . . . H16 H 0.545(2) 0.4692(17) 0.3033(14) 0.023(4) Uiso 1 1 d . . . C17 C 0.63202(17) 0.66361(12) 0.40257(11) 0.0168(2) Uani 1 1 d . . . C18 C 0.70544(16) 0.62929(12) 0.51635(11) 0.0163(2) Uani 1 1 d . . . C19 C 0.83971(16) 0.44283(12) 0.58070(11) 0.0160(2) Uani 1 1 d . . . C20 C 0.87328(18) 0.30744(13) 0.54104(12) 0.0197(2) Uani 1 1 d . . . H20 H 0.936(2) 0.2569(18) 0.5938(16) 0.028(4) Uiso 1 1 d . . . C21 C 0.80778(18) 0.23093(13) 0.41612(12) 0.0204(2) 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 0.01935(15) 0.02219(16) 0.01829(15) 0.00085(11) -0.00011(11) 0.00445(11) S2 0.02509(17) 0.01382(14) 0.02228(16) 0.00442(11) 0.00313(12) -0.00036(11) O1 0.0240(4) 0.0119(4) 0.0163(4) 0.0020(3) 0.0011(3) 0.0021(3) N1 0.0300(6) 0.0199(5) 0.0256(6) 0.0001(4) 0.0048(5) 0.0002(4) C1 0.0232(6) 0.0228(6) 0.0160(6) 0.0014(5) 0.0019(5) -0.0006(5) C2 0.0271(7) 0.0235(6) 0.0182(6) -0.0009(5) 0.0064(5) 0.0002(5) C3 0.0254(7) 0.0221(6) 0.0198(6) 0.0005(5) 0.0088(5) 0.0042(5) C4 0.0202(6) 0.0210(6) 0.0187(6) 0.0036(5) 0.0054(5) 0.0032(5) C5 0.0191(6) 0.0158(5) 0.0153(5) 0.0014(4) 0.0044(4) 0.0006(4) C6 0.0191(6) 0.0178(5) 0.0173(6) 0.0025(4) 0.0039(4) 0.0010(4) C7 0.0226(6) 0.0169(6) 0.0172(6) 0.0028(4) 0.0014(5) 0.0030(5) C8 0.0158(5) 0.0157(5) 0.0162(5) 0.0034(4) 0.0026(4) 0.0006(4) C9 0.0149(5) 0.0149(5) 0.0154(5) 0.0019(4) 0.0031(4) -0.0003(4) C10 0.0164(5) 0.0132(5) 0.0170(5) 0.0025(4) 0.0042(4) 0.0015(4) C11 0.0222(6) 0.0143(5) 0.0186(6) 0.0020(4) 0.0036(5) 0.0020(4) C12 0.0175(5) 0.0166(5) 0.0190(6) 0.0044(4) 0.0041(4) 0.0029(4) C13 0.0246(6) 0.0201(6) 0.0239(6) 0.0098(5) 0.0042(5) 0.0039(5) C14 0.0233(6) 0.0267(7) 0.0207(6) 0.0098(5) 0.0023(5) 0.0037(5) C15 0.0189(6) 0.0240(6) 0.0177(6) 0.0034(5) 0.0014(5) 0.0006(5) C16 0.0179(5) 0.0178(6) 0.0180(6) 0.0037(4) 0.0030(4) 0.0004(4) C17 0.0160(5) 0.0161(5) 0.0177(5) 0.0039(4) 0.0036(4) 0.0019(4) C18 0.0161(5) 0.0130(5) 0.0189(6) 0.0034(4) 0.0035(4) 0.0011(4) C19 0.0164(5) 0.0156(5) 0.0154(5) 0.0039(4) 0.0030(4) 0.0006(4) C20 0.0212(6) 0.0154(5) 0.0202(6) 0.0022(4) 0.0029(5) 0.0021(4) C21 0.0218(6) 0.0139(5) 0.0240(6) 0.0029(4) 0.0053(5) 0.0029(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 S1 C7 1.7703(19) . ? S1 C6 1.7821(18) . ? S2 C12 1.7317(19) . ? S2 C11 1.8087(19) . ? O1 C18 1.3790(19) . ? O1 C19 1.3944(17) . ? N1 C21 1.143(2) . ? C1 C6 1.389(2) . ? C1 C2 1.400(2) . ? C1 H1 0.983(19) . ? C2 C3 1.398(2) . ? C2 H2 0.938(18) . ? C3 C4 1.382(2) . ? C3 H3 0.945(17) . ? C4 C5 1.421(2) . ? C4 H4 0.929(17) . ? C5 C6 1.425(2) . ? C5 C9 1.469(2) . ? C7 C8 1.531(2) . ? C7 H7A 0.970(17) . ? C7 H7B 0.965(17) . ? C8 C9 1.389(2) . ? C8 C19 1.424(2) . ? C9 C10 1.482(2) . ? C10 C18 1.341(2) . ? C10 C11 1.526(2) . ? C11 H11A 0.974(17) . ? C11 H11B 0.991(17) . ? C12 C17 1.408(2) . ? C12 C13 1.412(2) . ? C13 C14 1.367(2) . ? C13 H13 0.934(17) . ? C14 C15 1.387(2) . ? C14 H14 0.984(17) . ? C15 C16 1.406(2) . ? C15 H15 0.970(18) . ? C16 C17 1.380(2) . ? C16 H16 0.955(16) . ? C17 C18 1.480(2) . ? C19 C20 1.368(2) . ? C20 C21 1.410(2) . ? C20 H20 0.986(17) . ? 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 C7 S1 C6 96.60(9) . . ? C12 S2 C11 100.46(9) . . ? C18 O1 C19 122.91(10) . . ? C6 C1 C2 119.85(13) . . ? C6 C1 H1 118.4(11) . . ? C2 C1 H1 121.7(11) . . ? C3 C2 C1 121.21(13) . . ? C3 C2 H2 118.2(11) . . ? C1 C2 H2 120.4(11) . . ? C4 C3 C2 119.56(14) . . ? C4 C3 H3 120.3(10) . . ? C2 C3 H3 120.1(10) . . ? C3 C4 C5 120.35(13) . . ? C3 C4 H4 118.8(10) . . ? C5 C4 H4 120.9(10) . . ? C4 C5 C6 119.09(12) . . ? C4 C5 C9 120.89(12) . . ? C6 C5 C9 120.02(12) . . ? C1 C6 C5 119.63(13) . . ? C1 C6 S1 118.92(11) . . ? C5 C6 S1 121.45(11) . . ? C8 C7 S1 110.62(11) . . ? C8 C7 H7A 112.4(10) . . ? S1 C7 H7A 105.7(10) . . ? C8 C7 H7B 113.0(10) . . ? S1 C7 H7B 107.6(10) . . ? H7A C7 H7B 107.1(14) . . ? C9 C8 C19 118.89(11) . . ? C9 C8 C7 122.44(12) . . ? C19 C8 C7 118.51(12) . . ? C8 C9 C5 118.84(11) . . ? C8 C9 C10 120.07(12) . . ? C5 C9 C10 121.09(12) . . ? C18 C10 C9 118.10(12) . . ? C18 C10 C11 116.69(12) . . ? C9 C10 C11 125.17(11) . . ? C10 C11 S2 113.24(10) . . ? C10 C11 H11A 110.6(10) . . ? S2 C11 H11A 105.0(10) . . ? C10 C11 H11B 113.9(10) . . ? S2 C11 H11B 105.6(10) . . ? H11A C11 H11B 107.9(14) . . ? C17 C12 C13 120.88(12) . . ? C17 C12 S2 119.28(11) . . ? C13 C12 S2 119.62(12) . . ? C14 C13 C12 120.28(14) . . ? C14 C13 H13 118.0(10) . . ? C12 C13 H13 121.8(10) . . ? C13 C14 C15 119.27(14) . . ? C13 C14 H14 119.7(10) . . ? C15 C14 H14 121.0(10) . . ? C14 C15 C16 120.89(13) . . ? C14 C15 H15 119.1(10) . . ? C16 C15 H15 120.0(10) . . ? C17 C16 C15 120.80(13) . . ? C17 C16 H16 115.0(9) . . ? C15 C16 H16 124.2(9) . . ? C16 C17 C12 117.83(13) . . ? C16 C17 C18 120.59(13) . . ? C12 C17 C18 121.45(11) . . ? C10 C18 O1 120.81(11) . . ? C10 C18 C17 126.56(12) . . ? O1 C18 C17 112.61(11) . . ? C20 C19 O1 116.17(12) . . ? C20 C19 C8 125.85(12) . . ? O1 C19 C8 117.89(12) . . ? C19 C20 C21 118.36(12) . . ? C19 C20 H20 125.2(10) . . ? C21 C20 H20 116.4(10) . . ? N1 C21 C20 178.29(15) . . ? _diffrn_measured_fraction_theta_max 0.925 _diffrn_reflns_theta_full 32.53 _diffrn_measured_fraction_theta_full 0.925 _refine_diff_density_max 0.443 _refine_diff_density_min -0.282 _refine_diff_density_rms 0.062 _database_code_depnum_ccdc_archive 'CCDC 892393' ####################################################################### # # 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_sh3167 #TrackingRef 'sh3167.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C21 H12 Cl N O S' _chemical_formula_weight 361.83 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 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 16.6265(17) _cell_length_b 5.0888(4) _cell_length_c 20.3020(15) _cell_angle_alpha 90.00 _cell_angle_beta 103.401(8) _cell_angle_gamma 90.00 _cell_volume 1671.0(2) _cell_formula_units_Z 4 _cell_measurement_temperature 153(2) _cell_measurement_reflns_used 510 _cell_measurement_theta_min 2.86 _cell_measurement_theta_max 18.61 _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.22 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.02 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.438 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 744 _exptl_absorpt_coefficient_mu 0.362 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min 0.9250 _exptl_absorpt_correction_T_max 0.9935 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 153(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_reflns_number 23378 _diffrn_reflns_av_R_equivalents 0.1507 _diffrn_reflns_av_sigmaI/netI 0.1752 _diffrn_reflns_limit_h_min -21 _diffrn_reflns_limit_h_max 19 _diffrn_reflns_limit_k_min -5 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_l_min -26 _diffrn_reflns_limit_l_max 26 _diffrn_reflns_theta_min 1.26 _diffrn_reflns_theta_max 27.15 _reflns_number_total 3710 _reflns_number_gt 1589 _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, 2008)' _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^)+(0.0500P)^2^+0.0000P] 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 mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3710 _refine_ls_number_parameters 266 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1899 _refine_ls_R_factor_gt 0.0589 _refine_ls_wR_factor_ref 0.1357 _refine_ls_wR_factor_gt 0.1003 _refine_ls_goodness_of_fit_ref 0.966 _refine_ls_restrained_S_all 0.966 _refine_ls_shift/su_max 0.003 _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 S S 0.44778(6) 0.7332(2) 0.44635(5) 0.0325(3) Uani 1 1 d . . . Cl Cl 0.09452(7) 0.4539(3) 0.48193(5) 0.0653(5) Uani 1 1 d . . . O O 0.30045(15) 0.9754(5) 0.20848(12) 0.0301(7) Uani 1 1 d . . . N N 0.3980(2) 1.4627(8) 0.1417(2) 0.0526(11) Uani 1 1 d . . . C1 C 0.2460(2) 0.7806(8) 0.21241(18) 0.0255(9) Uani 1 1 d . . . C2 C 0.1891(3) 0.6810(9) 0.1508(2) 0.0308(11) Uani 1 1 d . . . C3 C 0.1430(2) 0.4755(8) 0.17990(18) 0.0257(9) Uani 1 1 d . . . C4 C 0.0799(2) 0.3144(8) 0.1472(2) 0.0319(11) Uani 1 1 d . . . C5 C 0.0492(3) 0.1272(9) 0.1842(2) 0.0345(11) Uani 1 1 d . . . C6 C 0.0819(2) 0.1010(8) 0.2525(2) 0.0308(10) Uani 1 1 d . . . C7 C 0.1450(2) 0.2644(9) 0.28681(19) 0.0300(10) Uani 1 1 d . . . C8 C 0.1747(2) 0.4607(7) 0.25094(17) 0.0239(9) Uani 1 1 d . . . C9 C 0.2388(2) 0.6656(7) 0.27040(18) 0.0253(9) Uani 1 1 d . . . C10 C 0.2913(2) 0.7573(7) 0.33344(17) 0.0227(9) Uani 1 1 d . . . C11 C 0.2803(2) 0.6700(7) 0.40018(17) 0.0253(10) Uani 1 1 d . . . C12 C 0.2021(2) 0.6240(8) 0.41063(19) 0.0294(10) Uani 1 1 d . . . C13 C 0.1934(2) 0.5201(9) 0.47106(19) 0.0377(11) Uani 1 1 d . . . C14 C 0.2618(3) 0.4647(9) 0.5237(2) 0.0388(11) Uani 1 1 d . . . C15 C 0.3386(2) 0.5297(8) 0.51526(19) 0.0314(10) Uani 1 1 d . . . C16 C 0.3491(2) 0.6375(7) 0.45504(18) 0.0255(9) Uani 1 1 d . . . C17 C 0.4134(2) 1.0143(7) 0.39295(18) 0.0297(10) Uani 1 1 d . . . H10 H 0.3871 1.1435 0.4178 0.036 Uiso 1 1 calc R . . H11 H 0.4615 1.1000 0.3809 0.036 Uiso 1 1 calc R . . C18 C 0.3526(2) 0.9304(7) 0.32962(18) 0.0257(9) Uani 1 1 d . . . C19 C 0.3572(2) 1.0515(8) 0.26665(19) 0.0281(10) Uani 1 1 d . . . C20 C 0.4097(3) 1.2454(9) 0.2576(2) 0.0333(10) Uani 1 1 d . . . C21 C 0.4032(2) 1.3624(9) 0.1937(2) 0.0381(11) Uani 1 1 d . . . H1 H 0.222(2) 0.616(7) 0.1180(18) 0.042(12) Uiso 1 1 d . . . H2 H 0.154(2) 0.813(7) 0.1256(17) 0.034(11) Uiso 1 1 d . . . H3 H 0.062(2) 0.331(7) 0.0973(17) 0.032(10) Uiso 1 1 d . . . H4 H 0.010(2) -0.003(8) 0.1632(19) 0.048(13) Uiso 1 1 d . . . H5 H 0.0650(19) -0.031(7) 0.2786(16) 0.019(10) Uiso 1 1 d . . . H6 H 0.1677(19) 0.240(6) 0.3373(15) 0.021(9) Uiso 1 1 d . . . H7 H 0.151(2) 0.660(7) 0.3744(17) 0.035(11) Uiso 1 1 d . . . H8 H 0.253(2) 0.374(7) 0.5645(19) 0.045(12) Uiso 1 1 d . . . H9 H 0.388(2) 0.508(6) 0.5510(16) 0.023(9) Uiso 1 1 d . . . H12 H 0.446(2) 1.316(7) 0.2904(18) 0.037(13) 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 S 0.0190(5) 0.0332(7) 0.0390(6) -0.0009(5) -0.0063(4) 0.0007(5) Cl 0.0275(6) 0.1305(13) 0.0375(7) 0.0206(7) 0.0070(5) -0.0039(7) O 0.0240(15) 0.0353(18) 0.0291(15) 0.0016(13) 0.0021(12) -0.0047(14) N 0.038(2) 0.064(3) 0.055(3) 0.009(2) 0.009(2) -0.004(2) C1 0.017(2) 0.027(2) 0.031(2) -0.004(2) 0.0026(17) 0.002(2) C2 0.024(2) 0.041(3) 0.025(2) -0.004(2) 0.0008(19) 0.001(2) C3 0.020(2) 0.033(3) 0.023(2) -0.0019(19) 0.0033(17) 0.008(2) C4 0.023(2) 0.041(3) 0.028(2) -0.005(2) -0.0011(19) 0.002(2) C5 0.023(2) 0.035(3) 0.041(3) -0.009(2) -0.002(2) -0.003(2) C6 0.020(2) 0.030(3) 0.043(3) 0.001(2) 0.007(2) 0.000(2) C7 0.021(2) 0.037(3) 0.028(2) 0.001(2) -0.0016(18) 0.006(2) C8 0.019(2) 0.024(2) 0.027(2) -0.0017(19) 0.0038(17) 0.0049(18) C9 0.016(2) 0.027(3) 0.030(2) -0.0032(19) -0.0014(17) 0.0023(18) C10 0.0137(19) 0.025(2) 0.028(2) -0.0009(19) 0.0001(16) 0.0063(19) C11 0.024(2) 0.024(3) 0.026(2) -0.0016(18) 0.0004(18) 0.0044(18) C12 0.020(2) 0.042(3) 0.024(2) -0.002(2) 0.0016(19) 0.003(2) C13 0.018(2) 0.068(3) 0.027(2) -0.003(2) 0.0039(18) -0.001(2) C14 0.034(3) 0.058(3) 0.024(2) 0.002(2) 0.006(2) 0.006(2) C15 0.021(2) 0.041(3) 0.028(2) -0.004(2) -0.003(2) 0.007(2) C16 0.018(2) 0.027(2) 0.028(2) -0.0059(19) -0.0009(17) 0.0022(18) C17 0.027(2) 0.023(2) 0.035(2) -0.0024(19) -0.0017(19) -0.0056(19) C18 0.018(2) 0.028(3) 0.029(2) -0.0017(19) 0.0006(17) 0.0049(19) C19 0.019(2) 0.028(3) 0.035(2) -0.006(2) 0.0025(19) 0.003(2) C20 0.026(2) 0.033(3) 0.038(3) 0.004(2) 0.003(2) 0.000(2) C21 0.021(2) 0.041(3) 0.051(3) -0.001(2) 0.006(2) -0.008(2) _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 S C16 1.760(4) . ? S C17 1.806(4) . ? Cl C13 1.741(4) . ? O C1 1.357(4) . ? O C19 1.385(4) . ? N C21 1.158(5) . ? C1 C9 1.345(5) . ? C1 C2 1.473(5) . ? C2 C3 1.497(5) . ? C2 H1 1.01(4) . ? C2 H2 0.95(4) . ? C3 C4 1.375(5) . ? C3 C8 1.418(5) . ? C4 C5 1.382(5) . ? C4 H3 0.99(3) . ? C5 C6 1.374(6) . ? C5 H4 0.96(4) . ? C6 C7 1.392(5) . ? C6 H5 0.94(3) . ? C7 C8 1.392(5) . ? C7 H6 1.01(3) . ? C8 C9 1.478(5) . ? C9 C10 1.449(5) . ? C10 C18 1.363(5) . ? C10 C11 1.477(5) . ? C11 C12 1.385(5) . ? C11 C16 1.408(5) . ? C12 C13 1.374(5) . ? C12 H7 1.00(4) . ? C13 C14 1.397(5) . ? C14 C15 1.369(5) . ? C14 H8 0.99(4) . ? C15 C16 1.387(5) . ? C15 H9 0.97(3) . ? C17 C18 1.502(5) . ? C17 H10 0.9900 . ? C17 H11 0.9900 . ? C18 C19 1.437(5) . ? C19 C20 1.358(5) . ? C20 C21 1.409(6) . ? C20 H12 0.87(4) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C16 S C17 96.12(18) . . ? C1 O C19 119.1(3) . . ? C9 C1 O 124.4(3) . . ? C9 C1 C2 115.1(4) . . ? O C1 C2 120.5(3) . . ? C1 C2 C3 101.1(3) . . ? C1 C2 H1 110(2) . . ? C3 C2 H1 116(2) . . ? C1 C2 H2 114(2) . . ? C3 C2 H2 114(2) . . ? H1 C2 H2 103(3) . . ? C4 C3 C8 121.4(4) . . ? C4 C3 C2 129.0(3) . . ? C8 C3 C2 109.6(3) . . ? C3 C4 C5 119.0(4) . . ? C3 C4 H3 117(2) . . ? C5 C4 H3 124(2) . . ? C6 C5 C4 120.4(4) . . ? C6 C5 H4 117(2) . . ? C4 C5 H4 122(2) . . ? C5 C6 C7 121.5(4) . . ? C5 C6 H5 123(2) . . ? C7 C6 H5 116(2) . . ? C6 C7 C8 119.0(4) . . ? C6 C7 H6 119.5(18) . . ? C8 C7 H6 121.5(18) . . ? C7 C8 C3 118.5(4) . . ? C7 C8 C9 133.4(3) . . ? C3 C8 C9 108.0(3) . . ? C1 C9 C10 118.4(3) . . ? C1 C9 C8 106.1(3) . . ? C10 C9 C8 135.4(3) . . ? C18 C10 C9 117.6(3) . . ? C18 C10 C11 120.0(3) . . ? C9 C10 C11 122.5(3) . . ? C12 C11 C16 118.5(3) . . ? C12 C11 C10 120.7(3) . . ? C16 C11 C10 120.7(3) . . ? C13 C12 C11 119.9(4) . . ? C13 C12 H7 118.7(19) . . ? C11 C12 H7 121.4(19) . . ? C12 C13 C14 121.7(4) . . ? C12 C13 Cl 119.1(3) . . ? C14 C13 Cl 119.3(3) . . ? C15 C14 C13 118.2(4) . . ? C15 C14 H8 122(2) . . ? C13 C14 H8 119(2) . . ? C14 C15 C16 121.1(4) . . ? C14 C15 H9 122.3(19) . . ? C16 C15 H9 116.5(19) . . ? C15 C16 C11 119.9(3) . . ? C15 C16 S 120.5(3) . . ? C11 C16 S 119.5(3) . . ? C18 C17 S 110.2(3) . . ? C18 C17 H10 109.6 . . ? S C17 H10 109.6 . . ? C18 C17 H11 109.6 . . ? S C17 H11 109.6 . . ? H10 C17 H11 108.1 . . ? C10 C18 C19 121.5(3) . . ? C10 C18 C17 119.9(3) . . ? C19 C18 C17 118.4(3) . . ? C20 C19 O 114.9(4) . . ? C20 C19 C18 126.9(4) . . ? O C19 C18 118.2(3) . . ? C19 C20 C21 121.1(4) . . ? C19 C20 H12 124(2) . . ? C21 C20 H12 115(3) . . ? N C21 C20 178.8(5) . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 27.15 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.339 _refine_diff_density_min -0.364 _refine_diff_density_rms 0.075 _database_code_depnum_ccdc_archive 'CCDC 900876'