# Electronic Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2012 ####################################################################### # # 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_cd211553 _database_code_depnum_ccdc_archive 'CCDC 880541' #TrackingRef '3j.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C12 H14 Cl N O2 S' _chemical_formula_weight 271.75 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 7.7348(5) _cell_length_b 8.2950(5) _cell_length_c 20.1342(13) _cell_angle_alpha 90.00 _cell_angle_beta 98.5980(10) _cell_angle_gamma 90.00 _cell_volume 1277.30(14) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 4111 _cell_measurement_theta_min 4.911 _cell_measurement_theta_max 56.345 _exptl_crystal_description prismatic _exptl_crystal_colour colorless _exptl_crystal_size_max 0.323 _exptl_crystal_size_mid 0.211 _exptl_crystal_size_min 0.145 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.413 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 568 _exptl_absorpt_coefficient_mu 0.451 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.80037 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_process_details sadabs _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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 7493 _diffrn_reflns_av_R_equivalents 0.0285 _diffrn_reflns_av_sigmaI/netI 0.0301 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_theta_min 2.05 _diffrn_reflns_theta_max 26.00 _reflns_number_total 2511 _reflns_number_gt 2253 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _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^)+(0.0587P)^2^+0.2902P] 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 SHELXL _refine_ls_extinction_coef 0.053(4) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 2511 _refine_ls_number_parameters 156 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0439 _refine_ls_R_factor_gt 0.0401 _refine_ls_wR_factor_ref 0.1062 _refine_ls_wR_factor_gt 0.1023 _refine_ls_goodness_of_fit_ref 1.065 _refine_ls_restrained_S_all 1.065 _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 0.47469(5) 0.79568(5) 0.14486(2) 0.04647(18) Uani 1 1 d . . . Cl1 Cl 0.00507(9) 0.76105(9) 0.36293(3) 0.0837(2) Uani 1 1 d . . . N1 N 0.34728(18) 0.78971(15) 0.20294(7) 0.0427(3) Uani 1 1 d . . . O1 O 0.64675(16) 0.82891(17) 0.17875(7) 0.0616(4) Uani 1 1 d . . . O2 O 0.4424(2) 0.65080(15) 0.10714(7) 0.0644(4) Uani 1 1 d . . . C1 C 0.1629(2) 0.7490(2) 0.18055(9) 0.0536(4) Uani 1 1 d . . . H1A H 0.1544 0.6691 0.1450 0.064 Uiso 1 1 calc R . . H1B H 0.0995 0.8444 0.1630 0.064 Uiso 1 1 calc R . . C2 C 0.0839(3) 0.6832(2) 0.23918(10) 0.0588(5) Uani 1 1 d . . . H2A H -0.0422 0.6777 0.2275 0.071 Uiso 1 1 calc R . . H2B H 0.1273 0.5749 0.2496 0.071 Uiso 1 1 calc R . . C3 C 0.1304(2) 0.7888(2) 0.29888(9) 0.0493(4) Uani 1 1 d . . . C4 C 0.2551(2) 0.8967(2) 0.30473(8) 0.0479(4) Uani 1 1 d . . . H4 H 0.2734 0.9600 0.3433 0.058 Uiso 1 1 calc R . . C5 C 0.3689(2) 0.9223(2) 0.25219(8) 0.0477(4) Uani 1 1 d . . . H5A H 0.3388 1.0238 0.2294 0.057 Uiso 1 1 calc R . . H5B H 0.4901 0.9281 0.2731 0.057 Uiso 1 1 calc R . . C6 C 0.4039(2) 0.95894(18) 0.09222(8) 0.0407(4) Uani 1 1 d . . . C7 C 0.4615(2) 1.1122(2) 0.11061(9) 0.0481(4) Uani 1 1 d . . . H7 H 0.5439 1.1278 0.1487 0.058 Uiso 1 1 calc R . . C8 C 0.3958(3) 1.2420(2) 0.07209(9) 0.0519(4) Uani 1 1 d . . . H8 H 0.4337 1.3455 0.0848 0.062 Uiso 1 1 calc R . . C9 C 0.2755(2) 1.2212(2) 0.01530(9) 0.0497(4) Uani 1 1 d . . . C10 C 0.2226(2) 1.0661(2) -0.00332(9) 0.0554(4) Uani 1 1 d . . . H10 H 0.1431 1.0503 -0.0422 0.067 Uiso 1 1 calc R . . C11 C 0.2854(2) 0.9350(2) 0.03465(9) 0.0511(4) Uani 1 1 d . . . H11 H 0.2484 0.8315 0.0217 0.061 Uiso 1 1 calc R . . C12 C 0.2006(3) 1.3654(3) -0.02546(11) 0.0731(6) Uani 1 1 d . . . H12A H 0.0879 1.3913 -0.0139 0.110 Uiso 1 1 calc R . . H12B H 0.1888 1.3401 -0.0724 0.110 Uiso 1 1 calc R . . H12C H 0.2775 1.4559 -0.0159 0.110 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 S1 0.0465(3) 0.0331(2) 0.0598(3) 0.00009(16) 0.00772(19) 0.00717(15) Cl1 0.0840(4) 0.0913(5) 0.0834(4) 0.0078(3) 0.0378(3) -0.0081(3) N1 0.0422(7) 0.0333(7) 0.0508(8) -0.0019(5) 0.0013(6) -0.0030(5) O1 0.0419(7) 0.0613(8) 0.0801(9) 0.0089(7) 0.0043(6) 0.0106(6) O2 0.0843(10) 0.0346(6) 0.0764(9) -0.0082(6) 0.0191(7) 0.0101(6) C1 0.0467(10) 0.0547(10) 0.0560(10) -0.0069(8) -0.0034(8) -0.0084(8) C2 0.0489(10) 0.0542(10) 0.0721(12) -0.0015(9) 0.0051(8) -0.0135(8) C3 0.0470(9) 0.0448(9) 0.0563(10) 0.0077(7) 0.0083(7) 0.0049(7) C4 0.0525(10) 0.0405(8) 0.0494(9) -0.0012(7) 0.0030(7) 0.0041(7) C5 0.0504(9) 0.0374(8) 0.0541(9) -0.0045(7) 0.0034(7) -0.0070(7) C6 0.0402(8) 0.0346(8) 0.0481(8) -0.0014(6) 0.0096(6) 0.0017(6) C7 0.0482(9) 0.0393(8) 0.0546(9) -0.0017(7) 0.0002(7) -0.0049(7) C8 0.0611(11) 0.0351(8) 0.0604(11) 0.0003(7) 0.0122(8) -0.0016(7) C9 0.0502(10) 0.0515(10) 0.0505(9) 0.0087(8) 0.0175(7) 0.0099(8) C10 0.0553(10) 0.0641(11) 0.0450(9) 0.0013(8) 0.0010(7) -0.0012(8) C11 0.0576(10) 0.0439(9) 0.0513(9) -0.0084(7) 0.0065(8) -0.0064(7) C12 0.0819(15) 0.0684(13) 0.0715(13) 0.0234(11) 0.0200(11) 0.0239(11) _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 O2 1.4235(13) . ? S1 O1 1.4287(14) . ? S1 N1 1.6389(15) . ? S1 C6 1.7560(16) . ? Cl1 C3 1.7405(19) . ? N1 C1 1.469(2) . ? N1 C5 1.474(2) . ? C1 C2 1.510(3) . ? C1 H1A 0.9700 . ? C1 H1B 0.9700 . ? C2 C3 1.487(3) . ? C2 H2A 0.9700 . ? C2 H2B 0.9700 . ? C3 C4 1.308(2) . ? C4 C5 1.489(2) . ? C4 H4 0.9300 . ? C5 H5A 0.9700 . ? C5 H5B 0.9700 . ? C6 C7 1.379(2) . ? C6 C11 1.381(2) . ? C7 C8 1.379(2) . ? C7 H7 0.9300 . ? C8 C9 1.373(3) . ? C8 H8 0.9300 . ? C9 C10 1.385(3) . ? C9 C12 1.516(3) . ? C10 C11 1.375(3) . ? C10 H10 0.9300 . ? C11 H11 0.9300 . ? C12 H12A 0.9600 . ? C12 H12B 0.9600 . ? C12 H12C 0.9600 . ? 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 O2 S1 O1 119.61(8) . . ? O2 S1 N1 106.20(8) . . ? O1 S1 N1 106.35(8) . . ? O2 S1 C6 108.37(8) . . ? O1 S1 C6 108.88(8) . . ? N1 S1 C6 106.71(7) . . ? C1 N1 C5 112.66(13) . . ? C1 N1 S1 116.58(11) . . ? C5 N1 S1 115.97(10) . . ? N1 C1 C2 109.31(15) . . ? N1 C1 H1A 109.8 . . ? C2 C1 H1A 109.8 . . ? N1 C1 H1B 109.8 . . ? C2 C1 H1B 109.8 . . ? H1A C1 H1B 108.3 . . ? C3 C2 C1 109.98(15) . . ? C3 C2 H2A 109.7 . . ? C1 C2 H2A 109.7 . . ? C3 C2 H2B 109.7 . . ? C1 C2 H2B 109.7 . . ? H2A C2 H2B 108.2 . . ? C4 C3 C2 124.16(17) . . ? C4 C3 Cl1 120.56(15) . . ? C2 C3 Cl1 115.28(13) . . ? C3 C4 C5 122.68(16) . . ? C3 C4 H4 118.7 . . ? C5 C4 H4 118.7 . . ? N1 C5 C4 110.60(13) . . ? N1 C5 H5A 109.5 . . ? C4 C5 H5A 109.5 . . ? N1 C5 H5B 109.5 . . ? C4 C5 H5B 109.5 . . ? H5A C5 H5B 108.1 . . ? C7 C6 C11 120.33(15) . . ? C7 C6 S1 119.33(12) . . ? C11 C6 S1 120.27(12) . . ? C8 C7 C6 119.47(16) . . ? C8 C7 H7 120.3 . . ? C6 C7 H7 120.3 . . ? C9 C8 C7 121.12(16) . . ? C9 C8 H8 119.4 . . ? C7 C8 H8 119.4 . . ? C8 C9 C10 118.59(16) . . ? C8 C9 C12 120.57(18) . . ? C10 C9 C12 120.84(19) . . ? C11 C10 C9 121.22(16) . . ? C11 C10 H10 119.4 . . ? C9 C10 H10 119.4 . . ? C10 C11 C6 119.23(16) . . ? C10 C11 H11 120.4 . . ? C6 C11 H11 120.4 . . ? C9 C12 H12A 109.5 . . ? C9 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? C9 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? 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 O2 S1 N1 C1 -48.65(13) . . . . ? O1 S1 N1 C1 -177.08(12) . . . . ? C6 S1 N1 C1 66.81(13) . . . . ? O2 S1 N1 C5 175.05(12) . . . . ? O1 S1 N1 C5 46.63(13) . . . . ? C6 S1 N1 C5 -69.49(13) . . . . ? C5 N1 C1 C2 -65.22(19) . . . . ? S1 N1 C1 C2 157.09(13) . . . . ? N1 C1 C2 C3 47.2(2) . . . . ? C1 C2 C3 C4 -15.9(3) . . . . ? C1 C2 C3 Cl1 163.85(13) . . . . ? C2 C3 C4 C5 -1.8(3) . . . . ? Cl1 C3 C4 C5 178.42(13) . . . . ? C1 N1 C5 C4 46.00(18) . . . . ? S1 N1 C5 C4 -176.04(11) . . . . ? C3 C4 C5 N1 -12.5(2) . . . . ? O2 S1 C6 C7 -162.90(13) . . . . ? O1 S1 C6 C7 -31.30(16) . . . . ? N1 S1 C6 C7 83.11(14) . . . . ? O2 S1 C6 C11 20.17(16) . . . . ? O1 S1 C6 C11 151.77(14) . . . . ? N1 S1 C6 C11 -93.82(14) . . . . ? C11 C6 C7 C8 1.9(3) . . . . ? S1 C6 C7 C8 -175.05(13) . . . . ? C6 C7 C8 C9 -0.7(3) . . . . ? C7 C8 C9 C10 -0.9(3) . . . . ? C7 C8 C9 C12 178.22(17) . . . . ? C8 C9 C10 C11 1.4(3) . . . . ? C12 C9 C10 C11 -177.72(17) . . . . ? C9 C10 C11 C6 -0.3(3) . . . . ? C7 C6 C11 C10 -1.4(3) . . . . ? S1 C6 C11 C10 175.52(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 C8 H8 O2 0.93 2.57 3.471(2) 162.9 1_565 _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.271 _refine_diff_density_min -0.381 _refine_diff_density_rms 0.085 data_z _database_code_depnum_ccdc_archive 'CCDC 880542' #TrackingRef '4a.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C24 H21 Cl2 N O2 S' _chemical_formula_weight 458.38 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' 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' N N 0.0061 0.0033 '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)/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 17.918(2) _cell_length_b 5.8464(8) _cell_length_c 21.295(3) _cell_angle_alpha 90.00 _cell_angle_beta 99.577(4) _cell_angle_gamma 90.00 _cell_volume 2199.7(5) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description needle _exptl_crystal_colour block _exptl_crystal_size_max 0.57 _exptl_crystal_size_mid 0.09 _exptl_crystal_size_min 0.02 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.384 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 952 _exptl_absorpt_coefficient_mu 0.411 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7994 _exptl_absorpt_correction_T_max 0.9918 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(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 ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 24225 _diffrn_reflns_av_R_equivalents 0.0603 _diffrn_reflns_av_sigmaI/netI 0.0397 _diffrn_reflns_limit_h_min -21 _diffrn_reflns_limit_h_max 21 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_limit_l_max 25 _diffrn_reflns_theta_min 1.38 _diffrn_reflns_theta_max 25.01 _reflns_number_total 3857 _reflns_number_gt 2849 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _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^)+(0.0387P)^2^+3.5105P] 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 3857 _refine_ls_number_parameters 271 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0759 _refine_ls_R_factor_gt 0.0536 _refine_ls_wR_factor_ref 0.1405 _refine_ls_wR_factor_gt 0.1300 _refine_ls_goodness_of_fit_ref 1.077 _refine_ls_restrained_S_all 1.077 _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 0.02846(5) 0.42052(17) 0.13019(4) 0.0459(3) Uani 1 1 d . . . Cl2 Cl -0.29530(6) 0.4742(2) 0.15701(6) 0.0774(4) Uani 1 1 d . . . Cl1 Cl 0.01064(8) 0.7883(3) 0.44377(5) 0.0829(4) Uani 1 1 d . . . O2 O 0.05910(15) 0.4769(5) 0.07457(12) 0.0642(8) Uani 1 1 d . . . O1 O 0.01012(16) 0.1880(4) 0.14251(14) 0.0629(8) Uani 1 1 d . . . N1 N -0.04629(16) 0.5745(6) 0.12776(13) 0.0463(8) Uani 1 1 d . . . C1 C -0.07243(18) 0.5945(6) 0.23968(16) 0.0401(8) Uani 1 1 d . . . C2 C -0.0822(2) 0.4469(7) 0.28855(17) 0.0492(9) Uani 1 1 d . . . H2A H -0.1061 0.3070 0.2788 0.059 Uiso 1 1 calc R . . C3 C -0.0572(2) 0.5039(8) 0.35133(18) 0.0552(10) Uani 1 1 d . . . H3A H -0.0643 0.4042 0.3839 0.066 Uiso 1 1 calc R . . C4 C -0.0216(2) 0.7108(7) 0.36498(17) 0.0507(10) Uani 1 1 d . . . C5 C -0.0107(2) 0.8600(7) 0.31776(18) 0.0501(10) Uani 1 1 d . . . H5A H 0.0141 0.9982 0.3277 0.060 Uiso 1 1 calc R . . C6 C -0.0373(2) 0.8018(7) 0.25492(17) 0.0464(9) Uani 1 1 d . . . H6A H -0.0313 0.9039 0.2226 0.056 Uiso 1 1 calc R . . C7 C 0.09200(18) 0.5115(6) 0.19742(17) 0.0399(8) Uani 1 1 d . . . C8 C 0.1037(2) 0.3785(6) 0.25162(17) 0.0464(9) Uani 1 1 d . . . H8A H 0.0794 0.2382 0.2521 0.056 Uiso 1 1 calc R . . C9 C 0.1514(2) 0.4536(7) 0.30494(18) 0.0525(10) Uani 1 1 d . . . H9A H 0.1589 0.3629 0.3413 0.063 Uiso 1 1 calc R . . C10 C 0.1882(2) 0.6595(7) 0.30555(19) 0.0495(10) Uani 1 1 d . . . C11 C 0.1759(2) 0.7915(7) 0.2509(2) 0.0532(10) Uani 1 1 d . . . H11A H 0.2003 0.9318 0.2506 0.064 Uiso 1 1 calc R . . C12 C 0.1282(2) 0.7195(6) 0.19691(19) 0.0481(9) Uani 1 1 d . . . H12A H 0.1205 0.8103 0.1605 0.058 Uiso 1 1 calc R . . C13 C -0.07330(19) 0.7363(6) 0.07611(16) 0.0404(8) Uani 1 1 d . . . H13A H -0.0765 0.6645 0.0347 0.049 Uiso 1 1 calc R . . H13B H -0.0407 0.8695 0.0780 0.049 Uiso 1 1 calc R . . C14 C -0.15019(18) 0.7981(6) 0.08986(16) 0.0397(8) Uani 1 1 d . . . C15 C -0.16540(19) 0.6902(6) 0.14116(16) 0.0416(8) Uani 1 1 d . . . C16 C -0.10215(19) 0.5346(6) 0.17059(15) 0.0411(8) Uani 1 1 d . . . H16A H -0.1192 0.3751 0.1674 0.049 Uiso 1 1 calc R . . C17 C -0.19838(19) 0.9642(6) 0.04938(16) 0.0419(8) Uani 1 1 d . . . C18 C -0.1670(2) 1.1524(7) 0.02358(18) 0.0521(10) Uani 1 1 d . . . H18A H -0.1147 1.1698 0.0301 0.062 Uiso 1 1 calc R . . C19 C -0.2118(2) 1.3128(8) -0.01133(19) 0.0610(11) Uani 1 1 d . . . H19A H -0.1897 1.4373 -0.0283 0.073 Uiso 1 1 calc R . . C20 C -0.2895(2) 1.2906(8) -0.0214(2) 0.0614(11) Uani 1 1 d . . . H20A H -0.3199 1.4029 -0.0436 0.074 Uiso 1 1 calc R . . C21 C -0.3216(2) 1.1025(8) 0.0014(2) 0.0603(11) Uani 1 1 d . . . H21A H -0.3739 1.0845 -0.0064 0.072 Uiso 1 1 calc R . . C22 C -0.2768(2) 0.9393(7) 0.03602(18) 0.0518(10) Uani 1 1 d . . . H22A H -0.2992 0.8107 0.0507 0.062 Uiso 1 1 calc R . . C23 C 0.2422(3) 0.7385(9) 0.3634(2) 0.0784(15) Uani 1 1 d . . . H23A H 0.2440 0.6270 0.3967 0.118 Uiso 1 1 calc R . . H23B H 0.2253 0.8822 0.3777 0.118 Uiso 1 1 calc R . . H23C H 0.2918 0.7567 0.3526 0.118 Uiso 1 1 calc R . . C24 C -0.2326(2) 0.7157(7) 0.17304(18) 0.0522(10) Uani 1 1 d . . . H24A H -0.2596 0.8544 0.1581 0.063 Uiso 1 1 calc R . . H24B H -0.2162 0.7298 0.2186 0.063 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 S1 0.0473(5) 0.0487(6) 0.0417(5) -0.0097(4) 0.0071(4) 0.0055(4) Cl2 0.0622(7) 0.0888(9) 0.0857(9) 0.0079(7) 0.0261(6) -0.0187(6) Cl1 0.0958(9) 0.1086(11) 0.0412(6) -0.0106(6) 0.0030(6) 0.0045(8) O2 0.0586(16) 0.095(2) 0.0420(15) -0.0072(15) 0.0177(13) 0.0160(16) O1 0.0682(18) 0.0371(15) 0.078(2) -0.0171(14) -0.0033(15) -0.0003(13) N1 0.0443(16) 0.059(2) 0.0377(16) 0.0063(15) 0.0130(13) 0.0095(15) C1 0.0403(18) 0.043(2) 0.039(2) 0.0030(17) 0.0121(15) 0.0030(16) C2 0.054(2) 0.049(2) 0.048(2) 0.0057(19) 0.0153(18) -0.0012(18) C3 0.066(2) 0.063(3) 0.040(2) 0.013(2) 0.0180(19) 0.003(2) C4 0.054(2) 0.063(3) 0.035(2) -0.001(2) 0.0084(17) 0.010(2) C5 0.053(2) 0.047(2) 0.051(2) -0.0069(19) 0.0132(18) 0.0031(18) C6 0.056(2) 0.047(2) 0.038(2) 0.0065(18) 0.0125(17) 0.0049(19) C7 0.0375(18) 0.036(2) 0.047(2) -0.0015(17) 0.0119(15) 0.0016(16) C8 0.049(2) 0.037(2) 0.052(2) 0.0006(18) 0.0063(17) -0.0073(17) C9 0.053(2) 0.057(3) 0.046(2) 0.0044(19) 0.0045(18) -0.005(2) C10 0.046(2) 0.054(2) 0.051(2) -0.012(2) 0.0154(17) -0.0047(19) C11 0.052(2) 0.039(2) 0.072(3) -0.011(2) 0.020(2) -0.0086(18) C12 0.050(2) 0.040(2) 0.055(2) 0.0028(18) 0.0126(18) -0.0016(18) C13 0.0456(19) 0.041(2) 0.0348(19) -0.0021(16) 0.0071(15) -0.0039(16) C14 0.0402(18) 0.042(2) 0.0365(19) -0.0056(16) 0.0041(15) -0.0034(16) C15 0.0411(18) 0.047(2) 0.0369(19) -0.0048(17) 0.0067(15) -0.0004(17) C16 0.0458(19) 0.045(2) 0.0352(19) -0.0010(16) 0.0137(15) 0.0000(16) C17 0.0458(19) 0.044(2) 0.0354(19) -0.0042(16) 0.0042(15) -0.0021(17) C18 0.048(2) 0.056(3) 0.050(2) 0.004(2) -0.0015(17) -0.0074(19) C19 0.065(3) 0.057(3) 0.056(3) 0.014(2) -0.003(2) -0.011(2) C20 0.064(3) 0.053(3) 0.062(3) 0.008(2) -0.006(2) 0.007(2) C21 0.046(2) 0.072(3) 0.061(3) 0.004(2) 0.0027(19) 0.003(2) C22 0.047(2) 0.055(2) 0.054(2) 0.002(2) 0.0077(17) -0.0052(19) C23 0.075(3) 0.095(4) 0.063(3) -0.026(3) 0.007(2) -0.025(3) C24 0.047(2) 0.067(3) 0.044(2) -0.002(2) 0.0124(17) 0.005(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 S1 O2 1.425(3) . ? S1 O1 1.433(3) . ? S1 N1 1.607(3) . ? S1 C7 1.757(4) . ? Cl2 C24 1.801(4) . ? Cl1 C4 1.741(4) . ? N1 C13 1.470(4) . ? N1 C16 1.480(4) . ? C1 C6 1.379(5) . ? C1 C2 1.386(5) . ? C1 C16 1.520(5) . ? C2 C3 1.378(5) . ? C2 H2A 0.9300 . ? C3 C4 1.376(6) . ? C3 H3A 0.9300 . ? C4 C5 1.369(5) . ? C5 C6 1.386(5) . ? C5 H5A 0.9300 . ? C6 H6A 0.9300 . ? C7 C8 1.378(5) . ? C7 C12 1.379(5) . ? C8 C9 1.374(5) . ? C8 H8A 0.9300 . ? C9 C10 1.371(5) . ? C9 H9A 0.9300 . ? C10 C11 1.383(6) . ? C10 C23 1.507(5) . ? C11 C12 1.380(5) . ? C11 H11A 0.9300 . ? C12 H12A 0.9300 . ? C13 C14 1.500(5) . ? C13 H13A 0.9700 . ? C13 H13B 0.9700 . ? C14 C15 1.328(5) . ? C14 C17 1.478(5) . ? C15 C24 1.485(5) . ? C15 C16 1.506(5) . ? C16 H16A 0.9800 . ? C17 C18 1.389(5) . ? C17 C22 1.394(5) . ? C18 C19 1.370(5) . ? C18 H18A 0.9300 . ? C19 C20 1.379(6) . ? C19 H19A 0.9300 . ? C20 C21 1.367(6) . ? C20 H20A 0.9300 . ? C21 C22 1.379(6) . ? C21 H21A 0.9300 . ? C22 H22A 0.9300 . ? C23 H23A 0.9600 . ? C23 H23B 0.9600 . ? C23 H23C 0.9600 . ? C24 H24A 0.9700 . ? C24 H24B 0.9700 . ? 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 O2 S1 O1 120.23(19) . . ? O2 S1 N1 106.15(16) . . ? O1 S1 N1 108.77(17) . . ? O2 S1 C7 108.68(17) . . ? O1 S1 C7 105.99(17) . . ? N1 S1 C7 106.27(16) . . ? C13 N1 C16 113.0(3) . . ? C13 N1 S1 123.6(2) . . ? C16 N1 S1 122.5(2) . . ? C6 C1 C2 118.7(3) . . ? C6 C1 C16 120.2(3) . . ? C2 C1 C16 121.1(3) . . ? C3 C2 C1 121.1(4) . . ? C3 C2 H2A 119.4 . . ? C1 C2 H2A 119.4 . . ? C4 C3 C2 118.8(4) . . ? C4 C3 H3A 120.6 . . ? C2 C3 H3A 120.6 . . ? C5 C4 C3 121.5(4) . . ? C5 C4 Cl1 118.5(3) . . ? C3 C4 Cl1 120.0(3) . . ? C4 C5 C6 119.0(4) . . ? C4 C5 H5A 120.5 . . ? C6 C5 H5A 120.5 . . ? C1 C6 C5 120.8(4) . . ? C1 C6 H6A 119.6 . . ? C5 C6 H6A 119.6 . . ? C8 C7 C12 119.8(3) . . ? C8 C7 S1 120.0(3) . . ? C12 C7 S1 120.2(3) . . ? C9 C8 C7 119.9(3) . . ? C9 C8 H8A 120.0 . . ? C7 C8 H8A 120.0 . . ? C10 C9 C8 121.3(4) . . ? C10 C9 H9A 119.3 . . ? C8 C9 H9A 119.3 . . ? C9 C10 C11 118.2(4) . . ? C9 C10 C23 121.3(4) . . ? C11 C10 C23 120.5(4) . . ? C12 C11 C10 121.4(4) . . ? C12 C11 H11A 119.3 . . ? C10 C11 H11A 119.3 . . ? C7 C12 C11 119.3(4) . . ? C7 C12 H12A 120.4 . . ? C11 C12 H12A 120.4 . . ? N1 C13 C14 102.0(3) . . ? N1 C13 H13A 111.4 . . ? C14 C13 H13A 111.4 . . ? N1 C13 H13B 111.4 . . ? C14 C13 H13B 111.4 . . ? H13A C13 H13B 109.2 . . ? C15 C14 C17 127.7(3) . . ? C15 C14 C13 111.5(3) . . ? C17 C14 C13 120.7(3) . . ? C14 C15 C24 128.4(3) . . ? C14 C15 C16 112.7(3) . . ? C24 C15 C16 118.8(3) . . ? N1 C16 C15 100.8(3) . . ? N1 C16 C1 113.3(3) . . ? C15 C16 C1 112.4(3) . . ? N1 C16 H16A 110.0 . . ? C15 C16 H16A 110.0 . . ? C1 C16 H16A 110.0 . . ? C18 C17 C22 117.5(3) . . ? C18 C17 C14 121.0(3) . . ? C22 C17 C14 121.4(3) . . ? C19 C18 C17 121.2(4) . . ? C19 C18 H18A 119.4 . . ? C17 C18 H18A 119.4 . . ? C18 C19 C20 120.3(4) . . ? C18 C19 H19A 119.8 . . ? C20 C19 H19A 119.8 . . ? C21 C20 C19 119.6(4) . . ? C21 C20 H20A 120.2 . . ? C19 C20 H20A 120.2 . . ? C20 C21 C22 120.3(4) . . ? C20 C21 H21A 119.8 . . ? C22 C21 H21A 119.8 . . ? C21 C22 C17 120.9(4) . . ? C21 C22 H22A 119.5 . . ? C17 C22 H22A 119.5 . . ? C10 C23 H23A 109.5 . . ? C10 C23 H23B 109.5 . . ? H23A C23 H23B 109.5 . . ? C10 C23 H23C 109.5 . . ? H23A C23 H23C 109.5 . . ? H23B C23 H23C 109.5 . . ? C15 C24 Cl2 111.2(3) . . ? C15 C24 H24A 109.4 . . ? Cl2 C24 H24A 109.4 . . ? C15 C24 H24B 109.4 . . ? Cl2 C24 H24B 109.4 . . ? H24A C24 H24B 108.0 . . ? 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 O2 S1 N1 C13 0.2(3) . . . . ? O1 S1 N1 C13 -130.5(3) . . . . ? C7 S1 N1 C13 115.8(3) . . . . ? O2 S1 N1 C16 168.1(3) . . . . ? O1 S1 N1 C16 37.4(3) . . . . ? C7 S1 N1 C16 -76.3(3) . . . . ? C6 C1 C2 C3 -0.3(5) . . . . ? C16 C1 C2 C3 -178.1(3) . . . . ? C1 C2 C3 C4 -0.4(6) . . . . ? C2 C3 C4 C5 0.0(6) . . . . ? C2 C3 C4 Cl1 180.0(3) . . . . ? C3 C4 C5 C6 1.0(6) . . . . ? Cl1 C4 C5 C6 -179.0(3) . . . . ? C2 C1 C6 C5 1.4(5) . . . . ? C16 C1 C6 C5 179.2(3) . . . . ? C4 C5 C6 C1 -1.7(5) . . . . ? O2 S1 C7 C8 -141.3(3) . . . . ? O1 S1 C7 C8 -10.8(3) . . . . ? N1 S1 C7 C8 104.9(3) . . . . ? O2 S1 C7 C12 41.0(3) . . . . ? O1 S1 C7 C12 171.5(3) . . . . ? N1 S1 C7 C12 -72.9(3) . . . . ? C12 C7 C8 C9 0.0(5) . . . . ? S1 C7 C8 C9 -177.7(3) . . . . ? C7 C8 C9 C10 -0.1(6) . . . . ? C8 C9 C10 C11 0.2(6) . . . . ? C8 C9 C10 C23 -178.2(4) . . . . ? C9 C10 C11 C12 -0.1(6) . . . . ? C23 C10 C11 C12 178.3(4) . . . . ? C8 C7 C12 C11 0.1(5) . . . . ? S1 C7 C12 C11 177.8(3) . . . . ? C10 C11 C12 C7 0.0(6) . . . . ? C16 N1 C13 C14 0.6(4) . . . . ? S1 N1 C13 C14 169.6(2) . . . . ? N1 C13 C14 C15 0.1(4) . . . . ? N1 C13 C14 C17 178.9(3) . . . . ? C17 C14 C15 C24 -3.2(6) . . . . ? C13 C14 C15 C24 175.5(3) . . . . ? C17 C14 C15 C16 -179.4(3) . . . . ? C13 C14 C15 C16 -0.7(4) . . . . ? C13 N1 C16 C15 -1.0(4) . . . . ? S1 N1 C16 C15 -170.1(2) . . . . ? C13 N1 C16 C1 -121.4(3) . . . . ? S1 N1 C16 C1 69.5(4) . . . . ? C14 C15 C16 N1 1.0(4) . . . . ? C24 C15 C16 N1 -175.6(3) . . . . ? C14 C15 C16 C1 122.1(3) . . . . ? C24 C15 C16 C1 -54.6(4) . . . . ? C6 C1 C16 N1 48.9(4) . . . . ? C2 C1 C16 N1 -133.3(3) . . . . ? C6 C1 C16 C15 -64.6(4) . . . . ? C2 C1 C16 C15 113.1(4) . . . . ? C15 C14 C17 C18 142.5(4) . . . . ? C13 C14 C17 C18 -36.1(5) . . . . ? C15 C14 C17 C22 -37.1(6) . . . . ? C13 C14 C17 C22 144.3(4) . . . . ? C22 C17 C18 C19 2.8(6) . . . . ? C14 C17 C18 C19 -176.7(4) . . . . ? C17 C18 C19 C20 0.2(6) . . . . ? C18 C19 C20 C21 -2.7(7) . . . . ? C19 C20 C21 C22 2.0(7) . . . . ? C20 C21 C22 C17 1.1(6) . . . . ? C18 C17 C22 C21 -3.5(6) . . . . ? C14 C17 C22 C21 176.0(4) . . . . ? C14 C15 C24 Cl2 105.7(4) . . . . ? C16 C15 C24 Cl2 -78.2(4) . . . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 25.01 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.302 _refine_diff_density_min -0.270 _refine_diff_density_rms 0.053