# Electronic Supplementary Material (ESI) for CrystEngComm # This journal is © The Royal Society of Chemistry 2014 ####################################################################### # # 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_CMSH-I _audit_creation_method SHELXL-97 _chemical_name_systematic ; chlorodimethyl sulfonylhydrazone ; _chemical_name_common 'chlorodimethyl sulfonylhydrazone' _chemical_melting_point 434(2) _chemical_formula_moiety 'C21 H19 Cl N2 O2 S' _chemical_formula_sum 'C21 H19 Cl N2 O2 S' _chemical_formula_weight 398.89 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 'C2/c ' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 22.305(2) _cell_length_b 12.0112(12) _cell_length_c 15.3336(15) _cell_angle_alpha 90.00 _cell_angle_beta 100.953(2) _cell_angle_gamma 90.00 _cell_volume 4033.1(7) _cell_formula_units_Z 8 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 7175 _cell_measurement_theta_min 2.26 _cell_measurement_theta_max 26.06 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.42 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.314 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1664 _exptl_absorpt_coefficient_mu 0.311 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8805 _exptl_absorpt_correction_T_max 0.9696 _exptl_absorpt_process_details 'Bruker AXS SADABS program' _exptl_special_details ; Sheldrick,G.M.,(2003),University of gottingen,Germany ; _diffrn_ambient_temperature 298(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 20658 _diffrn_reflns_av_R_equivalents 0.0412 _diffrn_reflns_av_sigmaI/netI 0.0300 _diffrn_reflns_limit_h_min -27 _diffrn_reflns_limit_h_max 27 _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 1.86 _diffrn_reflns_theta_max 26.06 _reflns_number_total 3992 _reflns_number_gt 3164 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _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^)+(0.0686P)^2^+2.2428P] 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 3992 _refine_ls_number_parameters 250 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0663 _refine_ls_R_factor_gt 0.0514 _refine_ls_wR_factor_ref 0.1360 _refine_ls_wR_factor_gt 0.1270 _refine_ls_goodness_of_fit_ref 1.039 _refine_ls_restrained_S_all 1.039 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.05474(12) 0.3981(3) 0.11332(18) 0.0645(7) Uani 1 1 d . . . C2 C 0.04634(12) 0.2901(3) 0.13560(19) 0.0706(8) Uani 1 1 d . . . H2 H 0.0122 0.2703 0.1587 0.085 Uiso 1 1 calc R . . C3 C 0.08830(11) 0.2107(2) 0.12391(17) 0.0592(6) Uani 1 1 d . . . H3 H 0.0831 0.1370 0.1397 0.071 Uiso 1 1 calc R . . C4 C 0.13836(10) 0.24117(18) 0.08851(14) 0.0446(5) Uani 1 1 d . . . C5 C 0.14651(12) 0.3507(2) 0.06631(19) 0.0628(7) Uani 1 1 d . . . H5 H 0.1805 0.3711 0.0429 0.075 Uiso 1 1 calc R . . C6 C 0.10441(13) 0.4294(2) 0.0788(2) 0.0714(8) Uani 1 1 d . . . H6 H 0.1096 0.5034 0.0640 0.086 Uiso 1 1 calc R . . C7 C 0.30628(9) 0.20755(17) 0.27228(14) 0.0419(5) Uani 1 1 d . . . C8 C 0.35145(10) 0.27488(18) 0.23448(13) 0.0428(5) Uani 1 1 d . . . C9 C 0.39671(11) 0.2241(2) 0.19911(17) 0.0584(6) Uani 1 1 d . . . H9 H 0.4007 0.1470 0.2016 0.070 Uiso 1 1 calc R . . C10 C 0.43645(12) 0.2868(3) 0.15980(19) 0.0686(7) Uani 1 1 d . . . H10 H 0.4668 0.2513 0.1360 0.082 Uiso 1 1 calc R . . C11 C 0.43160(12) 0.4016(3) 0.15549(17) 0.0639(7) Uani 1 1 d . . . C12 C 0.38669(13) 0.4512(2) 0.19173(17) 0.0637(7) Uani 1 1 d . . . H12 H 0.3830 0.5283 0.1898 0.076 Uiso 1 1 calc R . . C13 C 0.34678(12) 0.3897(2) 0.23100(15) 0.0530(6) Uani 1 1 d . . . H13 H 0.3167 0.4255 0.2551 0.064 Uiso 1 1 calc R . . C14 C 0.31346(10) 0.19359(18) 0.36955(14) 0.0426(5) Uani 1 1 d . . . C15 C 0.27331(11) 0.1278(2) 0.40669(15) 0.0509(6) Uani 1 1 d . . . H15 H 0.2407 0.0935 0.3697 0.061 Uiso 1 1 calc R . . C16 C 0.28121(12) 0.1129(2) 0.49722(15) 0.0561(6) Uani 1 1 d . . . H16 H 0.2536 0.0689 0.5202 0.067 Uiso 1 1 calc R . . C17 C 0.32918(12) 0.1619(2) 0.55484(16) 0.0566(6) Uani 1 1 d . . . C18 C 0.36837(13) 0.2274(2) 0.51821(16) 0.0658(7) Uani 1 1 d . . . H18 H 0.4007 0.2620 0.5556 0.079 Uiso 1 1 calc R . . C19 C 0.36123(11) 0.2436(2) 0.42724(15) 0.0577(6) Uani 1 1 d . . . H19 H 0.3887 0.2884 0.4048 0.069 Uiso 1 1 calc R . . C20 C 0.47374(15) 0.4689(3) 0.1097(2) 0.1022(12) Uani 1 1 d . . . H20A H 0.4504 0.5051 0.0585 0.153 Uiso 1 1 calc R . . H20B H 0.5033 0.4204 0.0915 0.153 Uiso 1 1 calc R . . H20C H 0.4944 0.5238 0.1500 0.153 Uiso 1 1 calc R . . C21 C 0.33785(16) 0.1428(3) 0.65364(17) 0.0838(9) Uani 1 1 d . . . H21A H 0.3780 0.1133 0.6751 0.126 Uiso 1 1 calc R . . H21B H 0.3078 0.0908 0.6658 0.126 Uiso 1 1 calc R . . H21C H 0.3333 0.2121 0.6829 0.126 Uiso 1 1 calc R . . Cl1 Cl 0.00136(4) 0.49775(9) 0.12831(7) 0.1063(4) Uani 1 1 d . . . H1A H 0.2757(11) 0.2205(19) 0.1149(16) 0.047(7) Uiso 1 1 d . . . N1 N 0.25688(9) 0.16902(17) 0.13187(12) 0.0469(5) Uani 1 1 d . . . N2 N 0.26065(8) 0.15887(15) 0.22324(11) 0.0451(4) Uani 1 1 d . . . O1 O 0.17095(8) 0.03523(13) 0.09527(11) 0.0577(4) Uani 1 1 d . . . O2 O 0.20262(7) 0.15490(13) -0.01850(9) 0.0509(4) Uani 1 1 d . . . S1 S 0.19130(2) 0.13989(4) 0.06919(3) 0.04319(18) 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 0.0543(15) 0.0765(19) 0.0618(16) -0.0115(14) 0.0090(12) 0.0074(14) C2 0.0499(15) 0.096(2) 0.0704(18) 0.0005(16) 0.0229(13) -0.0050(15) C3 0.0549(14) 0.0613(16) 0.0639(16) 0.0057(12) 0.0172(12) -0.0115(12) C4 0.0432(12) 0.0514(13) 0.0386(11) -0.0008(9) 0.0065(9) -0.0100(10) C5 0.0589(15) 0.0534(15) 0.0820(19) 0.0036(13) 0.0288(14) -0.0075(12) C6 0.0684(17) 0.0532(16) 0.095(2) -0.0009(15) 0.0228(16) -0.0004(13) C7 0.0427(11) 0.0421(12) 0.0409(11) 0.0025(9) 0.0076(9) 0.0031(9) C8 0.0450(12) 0.0456(12) 0.0370(11) 0.0041(9) 0.0061(9) -0.0027(9) C9 0.0524(14) 0.0526(14) 0.0722(17) 0.0091(12) 0.0166(12) 0.0059(11) C10 0.0469(14) 0.086(2) 0.0775(19) 0.0110(15) 0.0236(13) 0.0024(13) C11 0.0524(14) 0.081(2) 0.0561(15) 0.0136(14) 0.0046(12) -0.0222(14) C12 0.0793(18) 0.0511(15) 0.0578(15) 0.0029(12) 0.0056(13) -0.0177(14) C13 0.0653(15) 0.0487(14) 0.0464(13) -0.0039(10) 0.0145(11) -0.0070(11) C14 0.0461(12) 0.0431(12) 0.0376(11) 0.0027(9) 0.0055(9) 0.0011(10) C15 0.0542(14) 0.0542(14) 0.0446(13) -0.0005(10) 0.0101(11) -0.0039(11) C16 0.0667(16) 0.0578(15) 0.0475(14) 0.0077(11) 0.0205(12) 0.0005(12) C17 0.0714(16) 0.0597(15) 0.0380(12) 0.0030(11) 0.0088(11) 0.0117(13) C18 0.0684(17) 0.0766(18) 0.0460(14) -0.0031(13) -0.0056(12) -0.0089(14) C19 0.0589(15) 0.0657(16) 0.0464(13) 0.0040(11) 0.0042(11) -0.0145(12) C20 0.083(2) 0.127(3) 0.098(3) 0.030(2) 0.0205(19) -0.045(2) C21 0.105(2) 0.103(2) 0.0427(15) 0.0060(15) 0.0123(15) 0.0164(19) Cl1 0.0860(6) 0.1160(8) 0.1214(8) -0.0188(6) 0.0310(5) 0.0341(5) N1 0.0483(11) 0.0572(12) 0.0358(10) 0.0063(9) 0.0095(8) -0.0082(9) N2 0.0471(10) 0.0538(11) 0.0341(9) 0.0054(8) 0.0071(8) -0.0022(9) O1 0.0715(11) 0.0469(9) 0.0551(10) 0.0033(7) 0.0131(8) -0.0134(8) O2 0.0607(10) 0.0565(10) 0.0361(8) -0.0019(7) 0.0107(7) -0.0071(8) S1 0.0494(3) 0.0439(3) 0.0362(3) 0.0011(2) 0.0079(2) -0.0085(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 C1 C2 1.364(4) . ? C1 C6 1.368(4) . ? C1 Cl1 1.734(3) . ? C2 C3 1.372(4) . ? C3 C4 1.380(3) . ? C4 C5 1.380(3) . ? C4 S1 1.759(2) . ? C5 C6 1.371(4) . ? C7 N2 1.285(3) . ? C7 C14 1.479(3) . ? C7 C8 1.492(3) . ? C8 C9 1.376(3) . ? C8 C13 1.384(3) . ? C9 C10 1.386(3) . ? C10 C11 1.383(4) . ? C11 C12 1.371(4) . ? C11 C20 1.510(3) . ? C12 C13 1.380(3) . ? C14 C19 1.386(3) . ? C14 C15 1.394(3) . ? C15 C16 1.377(3) . ? C16 C17 1.383(4) . ? C17 C18 1.373(4) . ? C17 C21 1.508(3) . ? C18 C19 1.387(3) . ? N1 N2 1.393(2) . ? N1 S1 1.628(2) . ? O1 S1 1.4197(16) . ? O2 S1 1.4259(15) . ? 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 121.2(3) . . ? C2 C1 Cl1 119.5(2) . . ? C6 C1 Cl1 119.2(2) . . ? C1 C2 C3 119.9(2) . . ? C2 C3 C4 119.3(2) . . ? C5 C4 C3 120.3(2) . . ? C5 C4 S1 119.58(17) . . ? C3 C4 S1 120.11(19) . . ? C6 C5 C4 119.8(2) . . ? C1 C6 C5 119.4(3) . . ? N2 C7 C14 117.41(19) . . ? N2 C7 C8 122.50(19) . . ? C14 C7 C8 120.09(18) . . ? C9 C8 C13 118.8(2) . . ? C9 C8 C7 120.9(2) . . ? C13 C8 C7 120.3(2) . . ? C8 C9 C10 120.6(2) . . ? C11 C10 C9 120.8(2) . . ? C12 C11 C10 118.1(2) . . ? C12 C11 C20 121.6(3) . . ? C10 C11 C20 120.4(3) . . ? C11 C12 C13 121.7(3) . . ? C12 C13 C8 120.0(2) . . ? C19 C14 C15 117.4(2) . . ? C19 C14 C7 121.2(2) . . ? C15 C14 C7 121.41(19) . . ? C16 C15 C14 121.1(2) . . ? C15 C16 C17 121.6(2) . . ? C18 C17 C16 117.2(2) . . ? C18 C17 C21 121.9(3) . . ? C16 C17 C21 120.9(3) . . ? C17 C18 C19 122.1(2) . . ? C14 C19 C18 120.6(2) . . ? N2 N1 S1 116.79(15) . . ? C7 N2 N1 116.00(18) . . ? O1 S1 O2 120.07(10) . . ? O1 S1 N1 108.87(11) . . ? O2 S1 N1 103.25(9) . . ? O1 S1 C4 107.70(10) . . ? O2 S1 C4 108.43(10) . . ? N1 S1 C4 107.97(10) . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 26.06 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.230 _refine_diff_density_min -0.295 _refine_diff_density_rms 0.045 _database_code_depnum_ccdc_archive 'CCDC 971250' ####################################################################### # # 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_CMSH-II _audit_creation_method SHELXL-97 _chemical_name_systematic ; chlorodimethyl sulfonylhydrazone ; _chemical_name_common 'chlorodimethyl sulfonylhydrazone' _chemical_melting_point 434(2) _chemical_formula_moiety 'C21 H19 Cl N2 O2 S' _chemical_formula_sum 'C21 H19 Cl N2 O2 S' _chemical_formula_weight 398.89 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 11.726(5) _cell_length_b 15.488(7) _cell_length_c 22.317(10) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 4053(3) _cell_formula_units_Z 8 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 6059 _cell_measurement_theta_min ? _cell_measurement_theta_max 26.25 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.24 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.18 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.307 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1664 _exptl_absorpt_coefficient_mu 0.309 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9294 _exptl_absorpt_correction_T_max 0.9464 _exptl_absorpt_process_details 'Bruker AXS SADABS program' _exptl_special_details ; Sheldrick,G.M.,(2003),University of gottingen,Germany ; _diffrn_ambient_temperature 298(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 40435 _diffrn_reflns_av_R_equivalents 0.0429 _diffrn_reflns_av_sigmaI/netI 0.0232 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min -27 _diffrn_reflns_limit_l_max 27 _diffrn_reflns_theta_min 1.82 _diffrn_reflns_theta_max 26.25 _reflns_number_total 4096 _reflns_number_gt 3097 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _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^)+(0.0649P)^2^+0.9428P] 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 4096 _refine_ls_number_parameters 250 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0631 _refine_ls_R_factor_gt 0.0451 _refine_ls_wR_factor_ref 0.1268 _refine_ls_wR_factor_gt 0.1141 _refine_ls_goodness_of_fit_ref 1.050 _refine_ls_restrained_S_all 1.050 _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 0.3747(2) 0.17630(14) 0.31224(10) 0.0596(6) Uani 1 1 d . . . C2 C 0.3357(2) 0.12829(17) 0.35927(11) 0.0722(7) Uani 1 1 d . . . H2 H 0.2587 0.1144 0.3624 0.087 Uiso 1 1 calc R . . C3 C 0.4121(2) 0.10076(17) 0.40191(11) 0.0669(7) Uani 1 1 d . . . H3 H 0.3871 0.0680 0.4342 0.080 Uiso 1 1 calc R . . C4 C 0.52489(17) 0.12169(12) 0.39668(9) 0.0447(4) Uani 1 1 d . . . C5 C 0.56274(19) 0.16951(15) 0.34914(10) 0.0583(6) Uani 1 1 d . . . H5 H 0.6396 0.1834 0.3459 0.070 Uiso 1 1 calc R . . C6 C 0.4870(2) 0.19697(16) 0.30622(11) 0.0699(7) Uani 1 1 d . . . H6 H 0.5120 0.2291 0.2736 0.084 Uiso 1 1 calc R . . C7 C 0.53958(16) 0.24787(13) 0.56457(9) 0.0467(5) Uani 1 1 d . . . C8 C 0.55125(17) 0.34244(13) 0.57252(9) 0.0490(5) Uani 1 1 d . . . C9 C 0.5067(2) 0.38352(15) 0.62206(11) 0.0626(6) Uani 1 1 d . . . H9 H 0.4656 0.3521 0.6503 0.075 Uiso 1 1 calc R . . C10 C 0.5229(2) 0.47153(16) 0.62998(13) 0.0736(7) Uani 1 1 d . . . H10 H 0.4928 0.4981 0.6638 0.088 Uiso 1 1 calc R . . C11 C 0.5820(2) 0.52045(15) 0.58929(13) 0.0685(7) Uani 1 1 d . . . C12 C 0.6241(2) 0.47935(15) 0.53941(12) 0.0685(7) Uani 1 1 d . . . H12 H 0.6631 0.5114 0.5107 0.082 Uiso 1 1 calc R . . C13 C 0.6102(2) 0.39214(14) 0.53082(11) 0.0583(6) Uani 1 1 d . . . H13 H 0.6404 0.3661 0.4968 0.070 Uiso 1 1 calc R . . C14 C 0.46990(17) 0.19638(12) 0.60739(9) 0.0469(5) Uani 1 1 d . . . C15 C 0.35220(18) 0.19334(13) 0.60228(10) 0.0546(5) Uani 1 1 d . . . H15 H 0.3156 0.2267 0.5735 0.066 Uiso 1 1 calc R . . C16 C 0.28943(19) 0.14126(15) 0.63954(11) 0.0619(6) Uani 1 1 d . . . H16 H 0.2105 0.1403 0.6355 0.074 Uiso 1 1 calc R . . C17 C 0.3396(2) 0.09051(14) 0.68271(11) 0.0629(6) Uani 1 1 d . . . C18 C 0.4567(2) 0.09393(17) 0.68764(11) 0.0697(7) Uani 1 1 d . . . H18 H 0.4931 0.0604 0.7165 0.084 Uiso 1 1 calc R . . C19 C 0.5207(2) 0.14592(16) 0.65076(10) 0.0616(6) Uani 1 1 d . . . H19 H 0.5995 0.1471 0.6551 0.074 Uiso 1 1 calc R . . C20 C 0.5994(3) 0.61672(17) 0.59795(18) 0.1044(11) Uani 1 1 d . . . H20A H 0.5442 0.6478 0.5746 0.157 Uiso 1 1 calc R . . H20B H 0.6748 0.6323 0.5852 0.157 Uiso 1 1 calc R . . H20C H 0.5901 0.6309 0.6395 0.157 Uiso 1 1 calc R . . C21 C 0.2698(3) 0.0325(2) 0.72288(15) 0.0995(10) Uani 1 1 d . . . H21A H 0.2111 0.0657 0.7420 0.149 Uiso 1 1 calc R . . H21B H 0.3183 0.0073 0.7528 0.149 Uiso 1 1 calc R . . H21C H 0.2355 -0.0125 0.6993 0.149 Uiso 1 1 calc R . . Cl1 Cl 0.27836(8) 0.21295(6) 0.25942(4) 0.1010(3) Uani 1 1 d . . . H1A H 0.5322(19) 0.1012(14) 0.5285(10) 0.050(7) Uiso 1 1 d . . . N1 N 0.58516(17) 0.12509(11) 0.51504(8) 0.0499(4) Uani 1 1 d . . . N2 N 0.59318(14) 0.21392(10) 0.52033(8) 0.0489(4) Uani 1 1 d . . . O1 O 0.60627(12) -0.00602(9) 0.45847(6) 0.0522(4) Uani 1 1 d . . . O2 O 0.73192(12) 0.11702(10) 0.43528(7) 0.0594(4) Uani 1 1 d . . . S1 S 0.62284(4) 0.08471(3) 0.45063(2) 0.04509(16) 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 0.0752(16) 0.0547(13) 0.0489(12) 0.0048(10) -0.0088(11) 0.0014(11) C2 0.0567(14) 0.0899(19) 0.0700(16) 0.0219(14) -0.0041(12) -0.0041(13) C3 0.0563(13) 0.0811(17) 0.0634(14) 0.0290(13) 0.0059(11) -0.0057(12) C4 0.0522(11) 0.0377(10) 0.0441(10) 0.0007(8) 0.0064(9) 0.0008(8) C5 0.0597(13) 0.0611(14) 0.0540(13) 0.0080(11) 0.0084(11) -0.0094(11) C6 0.0844(18) 0.0719(16) 0.0534(13) 0.0178(12) 0.0048(12) -0.0114(13) C7 0.0470(11) 0.0451(11) 0.0481(11) -0.0001(9) -0.0039(9) -0.0025(9) C8 0.0481(11) 0.0435(11) 0.0554(12) -0.0035(9) -0.0024(9) -0.0001(9) C9 0.0626(14) 0.0564(13) 0.0688(15) -0.0121(12) 0.0103(12) -0.0063(11) C10 0.0744(16) 0.0606(15) 0.0858(18) -0.0270(13) 0.0093(14) -0.0009(13) C11 0.0628(14) 0.0440(12) 0.0988(19) -0.0116(13) -0.0068(14) -0.0003(11) C12 0.0721(16) 0.0485(13) 0.0848(18) 0.0049(12) 0.0031(13) -0.0055(11) C13 0.0676(15) 0.0452(12) 0.0622(13) -0.0019(10) 0.0063(11) 0.0006(10) C14 0.0549(12) 0.0409(11) 0.0448(11) -0.0036(8) 0.0006(9) -0.0018(9) C15 0.0549(12) 0.0456(12) 0.0634(13) -0.0031(10) -0.0016(10) 0.0055(9) C16 0.0502(12) 0.0596(14) 0.0760(16) -0.0108(12) 0.0092(11) -0.0022(11) C17 0.0731(16) 0.0547(13) 0.0607(14) -0.0058(11) 0.0156(12) -0.0065(12) C18 0.0763(17) 0.0780(17) 0.0546(14) 0.0154(12) 0.0011(12) 0.0009(13) C19 0.0533(12) 0.0758(16) 0.0556(13) 0.0079(12) -0.0039(10) -0.0013(11) C20 0.112(2) 0.0514(16) 0.150(3) -0.0229(18) -0.008(2) -0.0069(16) C21 0.106(2) 0.093(2) 0.099(2) 0.0169(17) 0.0324(19) -0.0182(18) Cl1 0.1130(6) 0.1073(6) 0.0827(5) 0.0282(4) -0.0396(4) -0.0014(5) N1 0.0607(11) 0.0389(9) 0.0501(10) -0.0006(8) 0.0070(9) -0.0063(8) N2 0.0577(10) 0.0387(9) 0.0504(10) -0.0020(7) 0.0009(8) -0.0038(7) O1 0.0612(9) 0.0388(8) 0.0567(8) 0.0020(6) 0.0071(7) 0.0029(6) O2 0.0489(8) 0.0572(9) 0.0721(10) 0.0070(8) 0.0090(7) -0.0018(7) S1 0.0487(3) 0.0370(3) 0.0496(3) 0.0024(2) 0.0066(2) 0.0005(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 C1 C6 1.362(3) . ? C1 C2 1.365(3) . ? C1 Cl1 1.728(2) . ? C2 C3 1.375(3) . ? C3 C4 1.366(3) . ? C4 C5 1.368(3) . ? C4 S1 1.760(2) . ? C5 C6 1.374(3) . ? C7 N2 1.283(3) . ? C7 C8 1.482(3) . ? C7 C14 1.489(3) . ? C8 C9 1.378(3) . ? C8 C13 1.391(3) . ? C9 C10 1.388(3) . ? C10 C11 1.371(4) . ? C11 C12 1.374(4) . ? C11 C20 1.517(3) . ? C12 C13 1.374(3) . ? C14 C19 1.379(3) . ? C14 C15 1.386(3) . ? C15 C16 1.372(3) . ? C16 C17 1.376(3) . ? C17 C18 1.379(4) . ? C17 C21 1.511(3) . ? C18 C19 1.374(3) . ? N1 N2 1.384(2) . ? N1 S1 1.6287(19) . ? O1 S1 1.4293(15) . ? O2 S1 1.4156(16) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C6 C1 C2 121.9(2) . . ? C6 C1 Cl1 119.16(18) . . ? C2 C1 Cl1 119.0(2) . . ? C1 C2 C3 118.8(2) . . ? C4 C3 C2 119.9(2) . . ? C3 C4 C5 120.6(2) . . ? C3 C4 S1 119.73(16) . . ? C5 C4 S1 119.68(16) . . ? C4 C5 C6 119.9(2) . . ? C1 C6 C5 118.9(2) . . ? N2 C7 C8 116.87(18) . . ? N2 C7 C14 122.90(18) . . ? C8 C7 C14 120.22(18) . . ? C9 C8 C13 118.0(2) . . ? C9 C8 C7 121.15(19) . . ? C13 C8 C7 120.84(19) . . ? C8 C9 C10 120.2(2) . . ? C11 C10 C9 121.9(2) . . ? C10 C11 C12 117.5(2) . . ? C10 C11 C20 121.8(3) . . ? C12 C11 C20 120.7(3) . . ? C13 C12 C11 121.7(2) . . ? C12 C13 C8 120.6(2) . . ? C19 C14 C15 117.9(2) . . ? C19 C14 C7 121.14(19) . . ? C15 C14 C7 120.80(18) . . ? C16 C15 C14 120.3(2) . . ? C15 C16 C17 122.0(2) . . ? C16 C17 C18 117.4(2) . . ? C16 C17 C21 121.6(3) . . ? C18 C17 C21 121.0(3) . . ? C19 C18 C17 121.2(2) . . ? C18 C19 C14 121.1(2) . . ? N2 N1 S1 116.02(14) . . ? C7 N2 N1 116.09(17) . . ? O2 S1 O1 120.00(9) . . ? O2 S1 N1 108.84(10) . . ? O1 S1 N1 103.45(9) . . ? O2 S1 C4 108.00(10) . . ? O1 S1 C4 108.36(9) . . ? N1 S1 C4 107.57(10) . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 26.25 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.281 _refine_diff_density_min -0.194 _refine_diff_density_rms 0.045 _database_code_depnum_ccdc_archive 'CCDC 971251' ####################################################################### # # 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_FMSH _audit_creation_method SHELXL-97 _chemical_name_systematic ; fluorodimethyl sulfonylhydrazone ; _chemical_name_common 'fluorodimethyl sulfonylhydrazone' _chemical_melting_point 412(2) _chemical_formula_moiety 'C21 H19 F N2 O2 S' _chemical_formula_sum 'C21 H19 F N2 O2 S' _chemical_formula_weight 382.44 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' F F 0.0171 0.0103 '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 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 11.939(2) _cell_length_b 15.261(3) _cell_length_c 21.322(4) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 3884.9(12) _cell_formula_units_Z 8 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 6645 _cell_measurement_theta_min 2.37 _cell_measurement_theta_max 26.02 _exptl_crystal_description BLock _exptl_crystal_colour yellow _exptl_crystal_size_max 0.28 _exptl_crystal_size_mid 0.24 _exptl_crystal_size_min 0.17 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.308 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1600 _exptl_absorpt_coefficient_mu 0.194 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9477 _exptl_absorpt_correction_T_max 0.9678 _exptl_absorpt_process_details 'Bruker AXS SADABS program' _exptl_special_details ; Sheldrick,G.M.,(2003),University of gottingen,Germany ; _diffrn_ambient_temperature 298(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 33011 _diffrn_reflns_av_R_equivalents 0.0396 _diffrn_reflns_av_sigmaI/netI 0.0218 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -26 _diffrn_reflns_limit_l_max 26 _diffrn_reflns_theta_min 1.91 _diffrn_reflns_theta_max 26.05 _reflns_number_total 3843 _reflns_number_gt 3047 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _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^)+(0.0705P)^2^+0.8332P] 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 3843 _refine_ls_number_parameters 250 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0550 _refine_ls_R_factor_gt 0.0428 _refine_ls_wR_factor_ref 0.1233 _refine_ls_wR_factor_gt 0.1138 _refine_ls_goodness_of_fit_ref 1.048 _refine_ls_restrained_S_all 1.048 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.3548(2) 0.16768(15) 0.29927(11) 0.0703(6) Uani 1 1 d . . . C2 C 0.3206(2) 0.12263(16) 0.35101(11) 0.0693(6) Uani 1 1 d . . . H2 H 0.2454 0.1090 0.3568 0.083 Uiso 1 1 calc R . . C3 C 0.39924(17) 0.09782(14) 0.39439(10) 0.0565(5) Uani 1 1 d . . . H3 H 0.3779 0.0668 0.4300 0.068 Uiso 1 1 calc R . . C4 C 0.51064(15) 0.11924(11) 0.38490(8) 0.0426(4) Uani 1 1 d . . . C5 C 0.5432(2) 0.16464(13) 0.33220(9) 0.0565(5) Uani 1 1 d . . . H5 H 0.6182 0.1789 0.3262 0.068 Uiso 1 1 calc R . . C6 C 0.4641(2) 0.18886(15) 0.28843(10) 0.0720(7) Uani 1 1 d . . . H6 H 0.4847 0.2190 0.2523 0.086 Uiso 1 1 calc R . . C7 C 0.54049(14) 0.25546(11) 0.55850(8) 0.0415(4) Uani 1 1 d . . . C8 C 0.47376(15) 0.20424(11) 0.60527(8) 0.0425(4) Uani 1 1 d . . . C9 C 0.35800(17) 0.20461(12) 0.60343(10) 0.0529(5) Uani 1 1 d . . . H9 H 0.3208 0.2393 0.5743 0.063 Uiso 1 1 calc R . . C10 C 0.29751(17) 0.15367(13) 0.64471(11) 0.0595(5) Uani 1 1 d . . . H10 H 0.2197 0.1547 0.6428 0.071 Uiso 1 1 calc R . . C11 C 0.34900(19) 0.10111(13) 0.68883(10) 0.0575(5) Uani 1 1 d . . . C12 C 0.46483(19) 0.10122(14) 0.69058(10) 0.0578(5) Uani 1 1 d . . . H12 H 0.5018 0.0664 0.7198 0.069 Uiso 1 1 calc R . . C13 C 0.52653(17) 0.15230(12) 0.64955(9) 0.0512(5) Uani 1 1 d . . . H13 H 0.6043 0.1517 0.6518 0.061 Uiso 1 1 calc R . . C14 C 0.55306(15) 0.35196(11) 0.56580(8) 0.0427(4) Uani 1 1 d . . . C15 C 0.62139(16) 0.39988(12) 0.52569(10) 0.0504(5) Uani 1 1 d . . . H15 H 0.6579 0.3717 0.4929 0.061 Uiso 1 1 calc R . . C16 C 0.63568(17) 0.48887(13) 0.53401(10) 0.0561(5) Uani 1 1 d . . . H16 H 0.6811 0.5197 0.5063 0.067 Uiso 1 1 calc R . . C17 C 0.58400(18) 0.53313(12) 0.58259(11) 0.0558(5) Uani 1 1 d . . . C18 C 0.51537(19) 0.48603(13) 0.62170(10) 0.0597(5) Uani 1 1 d . . . H18 H 0.4790 0.5148 0.6543 0.072 Uiso 1 1 calc R . . C19 C 0.49885(17) 0.39660(12) 0.61385(9) 0.0525(5) Uani 1 1 d . . . H19 H 0.4513 0.3665 0.6409 0.063 Uiso 1 1 calc R . . C20 C 0.2817(3) 0.04349(19) 0.73222(13) 0.0896(8) Uani 1 1 d . . . H20A H 0.2205 0.0765 0.7494 0.134 Uiso 1 1 calc R . . H20B H 0.3287 0.0230 0.7656 0.134 Uiso 1 1 calc R . . H20C H 0.2529 -0.0057 0.7092 0.134 Uiso 1 1 calc R . . C21 C 0.6020(2) 0.63099(14) 0.59133(14) 0.0823(8) Uani 1 1 d . . . H21A H 0.6665 0.6492 0.5678 0.123 Uiso 1 1 calc R . . H21B H 0.6137 0.6434 0.6350 0.123 Uiso 1 1 calc R . . H21C H 0.5372 0.6622 0.5767 0.123 Uiso 1 1 calc R . . F1 F 0.27680(17) 0.19196(12) 0.25702(8) 0.1168(7) Uani 1 1 d . . . H1A H 0.5289(17) 0.1044(13) 0.5255(10) 0.050(6) Uiso 1 1 d . . . N1 N 0.58069(15) 0.12898(9) 0.50729(7) 0.0451(4) Uani 1 1 d . . . N2 N 0.58976(13) 0.21980(9) 0.51153(7) 0.0440(4) Uani 1 1 d . . . O1 O 0.59685(11) -0.00704(8) 0.45143(6) 0.0488(3) Uani 1 1 d . . . O2 O 0.71722(11) 0.11638(9) 0.41969(7) 0.0567(4) Uani 1 1 d . . . S1 S 0.61154(4) 0.08482(3) 0.43987(2) 0.04113(15) 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 0.0934(17) 0.0621(14) 0.0555(13) 0.0078(11) -0.0237(13) -0.0074(12) C2 0.0642(13) 0.0772(16) 0.0666(14) 0.0099(12) -0.0090(11) -0.0072(11) C3 0.0571(12) 0.0638(13) 0.0487(11) 0.0116(9) 0.0038(9) -0.0050(9) C4 0.0560(10) 0.0318(8) 0.0401(9) -0.0028(7) 0.0067(8) -0.0015(7) C5 0.0733(13) 0.0480(11) 0.0482(11) 0.0034(9) 0.0110(10) -0.0100(9) C6 0.109(2) 0.0602(14) 0.0470(12) 0.0145(10) -0.0014(12) -0.0171(13) C7 0.0479(10) 0.0316(8) 0.0449(10) -0.0005(7) -0.0044(8) -0.0023(7) C8 0.0521(10) 0.0309(8) 0.0445(9) -0.0046(7) 0.0017(8) -0.0009(7) C9 0.0550(11) 0.0370(9) 0.0667(13) 0.0012(9) 0.0020(10) 0.0071(8) C10 0.0499(11) 0.0481(11) 0.0804(15) -0.0070(10) 0.0119(10) 0.0005(9) C11 0.0722(13) 0.0483(11) 0.0519(11) -0.0061(9) 0.0163(10) -0.0077(10) C12 0.0723(14) 0.0574(12) 0.0438(11) 0.0063(9) -0.0010(10) -0.0013(10) C13 0.0527(11) 0.0528(11) 0.0481(11) 0.0032(9) -0.0024(8) -0.0015(9) C14 0.0495(10) 0.0312(8) 0.0475(10) -0.0013(7) -0.0033(8) -0.0015(7) C15 0.0605(12) 0.0368(10) 0.0540(11) -0.0036(8) 0.0055(9) -0.0019(8) C16 0.0630(12) 0.0382(10) 0.0671(13) 0.0055(9) -0.0014(10) -0.0092(9) C17 0.0652(12) 0.0320(9) 0.0702(13) -0.0058(9) -0.0148(11) -0.0006(8) C18 0.0732(13) 0.0423(11) 0.0637(13) -0.0154(9) 0.0006(11) 0.0044(10) C19 0.0628(12) 0.0408(10) 0.0540(11) -0.0060(8) 0.0059(10) -0.0028(8) C20 0.098(2) 0.0886(19) 0.0818(18) 0.0098(15) 0.0285(15) -0.0226(15) C21 0.108(2) 0.0340(11) 0.105(2) -0.0087(12) -0.0178(15) -0.0061(11) F1 0.1323(15) 0.1230(14) 0.0950(12) 0.0392(11) -0.0582(11) -0.0183(11) N1 0.0602(10) 0.0284(7) 0.0466(9) -0.0011(6) 0.0049(7) -0.0054(7) N2 0.0569(9) 0.0273(7) 0.0477(8) -0.0019(6) -0.0012(7) -0.0032(6) O1 0.0608(8) 0.0269(6) 0.0586(8) -0.0006(5) 0.0083(6) -0.0003(5) O2 0.0505(8) 0.0468(7) 0.0729(9) 0.0011(7) 0.0139(7) -0.0051(6) S1 0.0470(3) 0.0281(2) 0.0483(3) -0.00085(17) 0.00748(19) -0.00175(17) _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 F1 1.348(3) . ? C1 C2 1.363(3) . ? C1 C6 1.363(4) . ? C2 C3 1.371(3) . ? C3 C4 1.384(3) . ? C4 C5 1.376(2) . ? C4 S1 1.7609(19) . ? C5 C6 1.379(3) . ? C7 N2 1.283(2) . ? C7 C14 1.488(2) . ? C7 C8 1.497(2) . ? C8 C9 1.383(3) . ? C8 C13 1.384(3) . ? C9 C10 1.379(3) . ? C10 C11 1.381(3) . ? C11 C12 1.384(3) . ? C11 C20 1.508(3) . ? C12 C13 1.384(3) . ? C14 C15 1.390(3) . ? C14 C19 1.390(3) . ? C15 C16 1.380(3) . ? C16 C17 1.382(3) . ? C17 C18 1.372(3) . ? C17 C21 1.520(3) . ? C18 C19 1.389(3) . ? N1 N2 1.3931(19) . ? N1 S1 1.6298(16) . ? O1 S1 1.4342(12) . ? O2 S1 1.4174(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 F1 C1 C2 118.2(2) . . ? F1 C1 C6 118.9(2) . . ? C2 C1 C6 123.0(2) . . ? C1 C2 C3 118.7(2) . . ? C2 C3 C4 119.62(19) . . ? C5 C4 C3 120.64(19) . . ? C5 C4 S1 120.02(15) . . ? C3 C4 S1 119.31(14) . . ? C4 C5 C6 119.6(2) . . ? C1 C6 C5 118.5(2) . . ? N2 C7 C14 117.08(15) . . ? N2 C7 C8 122.87(15) . . ? C14 C7 C8 120.05(15) . . ? C9 C8 C13 118.46(17) . . ? C9 C8 C7 120.74(16) . . ? C13 C8 C7 120.74(17) . . ? C10 C9 C8 120.22(19) . . ? C9 C10 C11 121.97(19) . . ? C10 C11 C12 117.56(18) . . ? C10 C11 C20 121.3(2) . . ? C12 C11 C20 121.1(2) . . ? C11 C12 C13 121.05(19) . . ? C12 C13 C8 120.75(19) . . ? C15 C14 C19 117.97(17) . . ? C15 C14 C7 121.02(16) . . ? C19 C14 C7 120.99(16) . . ? C16 C15 C14 120.75(18) . . ? C15 C16 C17 121.47(19) . . ? C18 C17 C16 117.77(18) . . ? C18 C17 C21 121.6(2) . . ? C16 C17 C21 120.6(2) . . ? C17 C18 C19 121.75(19) . . ? C18 C19 C14 120.27(19) . . ? N2 N1 S1 116.81(12) . . ? C7 N2 N1 115.92(15) . . ? O2 S1 O1 119.55(8) . . ? O2 S1 N1 109.18(9) . . ? O1 S1 N1 103.00(8) . . ? O2 S1 C4 107.79(9) . . ? O1 S1 C4 108.80(8) . . ? N1 S1 C4 108.01(8) . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 26.05 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.472 _refine_diff_density_min -0.277 _refine_diff_density_rms 0.054 _database_code_depnum_ccdc_archive 'CCDC 971252' ####################################################################### # # 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_MISH _audit_creation_method SHELXL-97 _chemical_name_systematic ; methyldiiodo sulfonylhydrazone ; _chemical_name_common 'methyldiiodo sulfonylhydrazone' _chemical_melting_point 522(2) _chemical_formula_moiety 'C20 H16 I2 N2 O2 S' _chemical_formula_sum 'C20 H16 I2 N2 O2 S' _chemical_formula_weight 602.21 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' 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' I I -0.4742 1.8119 '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' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P21/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 11.6335(16) _cell_length_b 11.6089(16) _cell_length_c 15.843(2) _cell_angle_alpha 90.00 _cell_angle_beta 96.670(2) _cell_angle_gamma 90.00 _cell_volume 2125.1(5) _cell_formula_units_Z 4 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 6494 _cell_measurement_theta_min 2.49 _cell_measurement_theta_max 26.01 _exptl_crystal_description plate _exptl_crystal_colour brown _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.40 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.882 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1152 _exptl_absorpt_coefficient_mu 3.075 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.3086 _exptl_absorpt_correction_T_max 0.7485 _exptl_absorpt_process_details 'Bruker AXS SADABS program' _exptl_special_details ; Sheldrick,G.M.,(2003),University of gottingen,Germany ; _diffrn_ambient_temperature 298(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 21633 _diffrn_reflns_av_R_equivalents 0.0280 _diffrn_reflns_av_sigmaI/netI 0.0206 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 1.76 _diffrn_reflns_theta_max 26.16 _reflns_number_total 4235 _reflns_number_gt 3678 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _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^)+(0.0498P)^2^+3.1330P] 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 4235 _refine_ls_number_parameters 249 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0447 _refine_ls_R_factor_gt 0.0390 _refine_ls_wR_factor_ref 0.1047 _refine_ls_wR_factor_gt 0.1003 _refine_ls_goodness_of_fit_ref 1.064 _refine_ls_restrained_S_all 1.064 _refine_ls_shift/su_max 0.002 _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 0.6204(4) 0.3751(4) 0.2961(3) 0.0589(11) Uani 1 1 d . . . C2 C 0.6071(4) 0.4916(5) 0.2839(3) 0.0704(13) Uani 1 1 d . . . H2 H 0.5408 0.5193 0.2518 0.084 Uiso 1 1 calc R . . C3 C 0.6903(4) 0.5687(4) 0.3184(3) 0.0614(11) Uani 1 1 d . . . H3 H 0.6803 0.6474 0.3093 0.074 Uiso 1 1 calc R . . C4 C 0.7876(3) 0.5281(3) 0.3661(2) 0.0443(8) Uani 1 1 d . . . C5 C 0.8029(4) 0.4118(4) 0.3796(3) 0.0651(12) Uani 1 1 d . . . H5 H 0.8691 0.3843 0.4119 0.078 Uiso 1 1 calc R . . C6 C 0.7190(4) 0.3368(4) 0.3447(3) 0.0695(12) Uani 1 1 d . . . H6 H 0.7290 0.2582 0.3542 0.083 Uiso 1 1 calc R . . C7 C 1.1109(3) 0.5378(3) 0.2654(2) 0.0424(8) Uani 1 1 d . . . C8 C 1.1934(3) 0.4642(3) 0.3210(2) 0.0436(8) Uani 1 1 d . . . C9 C 1.2756(4) 0.5164(4) 0.3797(3) 0.0588(10) Uani 1 1 d . . . H9 H 1.2784 0.5962 0.3842 0.071 Uiso 1 1 calc R . . C10 C 1.3530(4) 0.4496(4) 0.4315(3) 0.0662(12) Uani 1 1 d . . . H10 H 1.4082 0.4844 0.4705 0.079 Uiso 1 1 calc R . . C11 C 1.3480(3) 0.3315(4) 0.4250(3) 0.0543(10) Uani 1 1 d . . . C12 C 1.2647(4) 0.2787(4) 0.3687(3) 0.0547(10) Uani 1 1 d . . . H12 H 1.2603 0.1988 0.3660 0.066 Uiso 1 1 calc R . . C13 C 1.1880(4) 0.3455(3) 0.3164(2) 0.0493(9) Uani 1 1 d . . . H13 H 1.1325 0.3103 0.2779 0.059 Uiso 1 1 calc R . . C14 C 1.1282(3) 0.5517(3) 0.1748(2) 0.0441(8) Uani 1 1 d . . . C15 C 1.0492(4) 0.6124(3) 0.1184(3) 0.0511(9) Uani 1 1 d . . . H15 H 0.9829 0.6430 0.1373 0.061 Uiso 1 1 calc R . . C16 C 1.0687(4) 0.6277(4) 0.0347(3) 0.0556(10) Uani 1 1 d . . . H16 H 1.0152 0.6674 -0.0027 0.067 Uiso 1 1 calc R . . C17 C 1.1674(4) 0.5839(4) 0.0069(2) 0.0533(9) Uani 1 1 d . . . C18 C 1.2459(4) 0.5228(4) 0.0606(3) 0.0638(11) Uani 1 1 d . . . H18 H 1.3119 0.4924 0.0410 0.077 Uiso 1 1 calc R . . C19 C 1.2260(4) 0.5068(4) 0.1445(3) 0.0580(10) Uani 1 1 d . . . H19 H 1.2791 0.4652 0.1810 0.070 Uiso 1 1 calc R . . C20 C 0.5324(5) 0.2911(6) 0.2558(4) 0.0859(17) Uani 1 1 d . . . H20A H 0.5626 0.2531 0.2092 0.129 Uiso 1 1 calc R . . H20B H 0.4628 0.3315 0.2354 0.129 Uiso 1 1 calc R . . H20C H 0.5158 0.2349 0.2972 0.129 Uiso 1 1 calc R . . H1A H 1.040(4) 0.538(4) 0.400(3) 0.039(12) Uiso 1 1 d . . . I1 I 1.47179(3) 0.23244(4) 0.49995(2) 0.08088(15) Uani 1 1 d . . . I2 I 1.20019(4) 0.60982(3) -0.11925(2) 0.08052(15) Uani 1 1 d . . . N1 N 1.0169(3) 0.5838(3) 0.3782(2) 0.0476(8) Uani 1 1 d . . . N2 N 1.0268(3) 0.5930(3) 0.29255(19) 0.0450(7) Uani 1 1 d . . . O1 O 0.8667(3) 0.7365(2) 0.37800(19) 0.0574(7) Uani 1 1 d . . . O2 O 0.9141(3) 0.6065(2) 0.50049(16) 0.0517(6) Uani 1 1 d . . . S1 S 0.89469(8) 0.62430(8) 0.41040(5) 0.0431(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 C1 0.052(2) 0.077(3) 0.049(2) -0.010(2) 0.0128(18) -0.010(2) C2 0.050(2) 0.086(4) 0.071(3) 0.001(3) -0.011(2) 0.008(2) C3 0.056(2) 0.060(3) 0.066(3) 0.005(2) -0.003(2) 0.011(2) C4 0.0452(19) 0.050(2) 0.0375(17) -0.0011(15) 0.0048(14) 0.0047(16) C5 0.061(3) 0.053(2) 0.077(3) 0.006(2) -0.013(2) 0.003(2) C6 0.074(3) 0.050(2) 0.082(3) 0.002(2) -0.002(2) -0.002(2) C7 0.0447(18) 0.0430(18) 0.0395(18) 0.0021(15) 0.0045(14) -0.0046(15) C8 0.0417(18) 0.049(2) 0.0405(18) -0.0005(15) 0.0060(14) -0.0012(15) C9 0.052(2) 0.049(2) 0.071(3) 0.003(2) -0.007(2) -0.0075(18) C10 0.048(2) 0.070(3) 0.076(3) 0.000(2) -0.015(2) -0.008(2) C11 0.047(2) 0.065(3) 0.051(2) 0.0111(19) 0.0044(17) 0.0060(19) C12 0.063(3) 0.051(2) 0.050(2) 0.0025(18) 0.0081(19) 0.0025(19) C13 0.054(2) 0.053(2) 0.0400(18) -0.0036(16) 0.0015(16) -0.0029(17) C14 0.049(2) 0.0430(19) 0.0416(18) -0.0001(15) 0.0089(15) -0.0034(15) C15 0.051(2) 0.059(2) 0.044(2) 0.0017(17) 0.0092(16) 0.0063(18) C16 0.069(3) 0.056(2) 0.042(2) 0.0038(17) 0.0046(18) 0.002(2) C17 0.071(3) 0.049(2) 0.042(2) -0.0011(16) 0.0176(18) -0.0077(19) C18 0.074(3) 0.062(3) 0.061(3) 0.005(2) 0.030(2) 0.013(2) C19 0.062(2) 0.059(2) 0.054(2) 0.0114(19) 0.0160(19) 0.013(2) C20 0.072(3) 0.107(4) 0.078(4) -0.022(3) 0.008(3) -0.024(3) I1 0.0699(2) 0.0919(3) 0.0775(2) 0.02783(18) -0.00541(17) 0.01418(17) I2 0.1160(3) 0.0823(3) 0.04877(19) -0.00129(14) 0.03263(18) -0.0166(2) N1 0.0502(19) 0.057(2) 0.0356(16) 0.0068(15) 0.0058(14) 0.0075(16) N2 0.0481(17) 0.0515(17) 0.0356(15) 0.0033(13) 0.0058(12) 0.0010(14) O1 0.076(2) 0.0448(15) 0.0510(16) 0.0034(12) 0.0048(14) 0.0079(13) O2 0.0631(17) 0.0582(16) 0.0340(13) 0.0002(11) 0.0065(11) 0.0067(13) S1 0.0510(5) 0.0443(5) 0.0341(4) 0.0015(3) 0.0050(4) 0.0059(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 1.373(7) . ? C1 C6 1.378(7) . ? C1 C20 1.501(7) . ? C2 C3 1.384(7) . ? C2 H2 0.9300 . ? C3 C4 1.370(6) . ? C3 H3 0.9300 . ? C4 C5 1.375(6) . ? C4 S1 1.757(4) . ? C5 C6 1.375(7) . ? C5 H5 0.9300 . ? C6 H6 0.9300 . ? C7 N2 1.284(5) . ? C7 C14 1.482(5) . ? C7 C8 1.493(5) . ? C8 C13 1.381(6) . ? C8 C9 1.393(6) . ? C9 C10 1.383(6) . ? C9 H9 0.9300 . ? C10 C11 1.376(7) . ? C10 H10 0.9300 . ? C11 C12 1.381(6) . ? C11 I1 2.100(4) . ? C12 C13 1.383(6) . ? C12 H12 0.9300 . ? C13 H13 0.9300 . ? C14 C19 1.387(6) . ? C14 C15 1.396(5) . ? C15 C16 1.382(6) . ? C15 H15 0.9300 . ? C16 C17 1.374(6) . ? C16 H16 0.9300 . ? C17 C18 1.372(7) . ? C17 I2 2.099(4) . ? C18 C19 1.388(6) . ? C18 H18 0.9300 . ? C19 H19 0.9300 . ? C20 H20A 0.9600 . ? C20 H20B 0.9600 . ? C20 H20C 0.9600 . ? N1 N2 1.379(4) . ? N1 S1 1.635(4) . ? N1 H1A 0.67(4) . ? O1 S1 1.424(3) . ? O2 S1 1.434(3) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 C1 C6 118.0(4) . . ? C2 C1 C20 121.3(5) . . ? C6 C1 C20 120.6(5) . . ? C1 C2 C3 121.3(4) . . ? C1 C2 H2 119.4 . . ? C3 C2 H2 119.4 . . ? C4 C3 C2 119.4(4) . . ? C4 C3 H3 120.3 . . ? C2 C3 H3 120.3 . . ? C3 C4 C5 120.5(4) . . ? C3 C4 S1 120.3(3) . . ? C5 C4 S1 119.2(3) . . ? C6 C5 C4 119.0(4) . . ? C6 C5 H5 120.5 . . ? C4 C5 H5 120.5 . . ? C5 C6 C1 121.8(4) . . ? C5 C6 H6 119.1 . . ? C1 C6 H6 119.1 . . ? N2 C7 C14 117.7(3) . . ? N2 C7 C8 123.4(3) . . ? C14 C7 C8 118.9(3) . . ? C13 C8 C9 119.5(4) . . ? C13 C8 C7 121.2(3) . . ? C9 C8 C7 119.3(4) . . ? C10 C9 C8 120.1(4) . . ? C10 C9 H9 119.9 . . ? C8 C9 H9 119.9 . . ? C11 C10 C9 119.7(4) . . ? C11 C10 H10 120.2 . . ? C9 C10 H10 120.2 . . ? C10 C11 C12 120.7(4) . . ? C10 C11 I1 118.9(3) . . ? C12 C11 I1 120.4(3) . . ? C11 C12 C13 119.6(4) . . ? C11 C12 H12 120.2 . . ? C13 C12 H12 120.2 . . ? C8 C13 C12 120.4(4) . . ? C8 C13 H13 119.8 . . ? C12 C13 H13 119.8 . . ? C19 C14 C15 118.3(4) . . ? C19 C14 C7 120.2(3) . . ? C15 C14 C7 121.5(3) . . ? C16 C15 C14 120.6(4) . . ? C16 C15 H15 119.7 . . ? C14 C15 H15 119.7 . . ? C17 C16 C15 119.8(4) . . ? C17 C16 H16 120.1 . . ? C15 C16 H16 120.1 . . ? C18 C17 C16 120.9(4) . . ? C18 C17 I2 118.9(3) . . ? C16 C17 I2 120.3(3) . . ? C17 C18 C19 119.4(4) . . ? C17 C18 H18 120.3 . . ? C19 C18 H18 120.3 . . ? C14 C19 C18 121.0(4) . . ? C14 C19 H19 119.5 . . ? C18 C19 H19 119.5 . . ? C1 C20 H20A 109.5 . . ? C1 C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? C1 C20 H20C 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? N2 N1 S1 117.4(3) . . ? N2 N1 H1A 119(4) . . ? S1 N1 H1A 113(4) . . ? C7 N2 N1 116.4(3) . . ? O1 S1 O2 119.56(17) . . ? O1 S1 N1 108.8(2) . . ? O2 S1 N1 103.15(17) . . ? O1 S1 C4 108.38(19) . . ? O2 S1 C4 109.18(17) . . ? N1 S1 C4 107.13(18) . . ? _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 26.16 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 1.798 _refine_diff_density_min -1.257 _refine_diff_density_rms 0.097 _database_code_depnum_ccdc_archive 'CCDC 971253' ####################################################################### # # 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_TBSH _audit_creation_method SHELXL-97 _chemical_name_systematic ; tribromo sulfonylhydrazone ; _chemical_name_common 'tribromo sulfonylhydrazone' _chemical_melting_point 509(2) _chemical_formula_moiety 'C19 H13 Br3 N2 O2 S' _chemical_formula_sum 'C19 H13 Br3 N2 O2 S' _chemical_formula_weight 573.10 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' Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'C2/c ' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 23.334(8) _cell_length_b 11.594(4) _cell_length_c 15.600(5) _cell_angle_alpha 90.00 _cell_angle_beta 103.035(5) _cell_angle_gamma 90.00 _cell_volume 4112(2) _cell_formula_units_Z 8 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 6293 _cell_measurement_theta_min 2.27 _cell_measurement_theta_max 25.60 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.42 _exptl_crystal_size_mid 0.38 _exptl_crystal_size_min 0.24 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.852 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2224 _exptl_absorpt_coefficient_mu 6.005 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.1870 _exptl_absorpt_correction_T_max 0.3267 _exptl_absorpt_process_details 'Bruker AXS SADABS program' _exptl_special_details ; Sheldrick,G.M.,(2003),University of gottingen,Germany ; _diffrn_ambient_temperature 298(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 20670 _diffrn_reflns_av_R_equivalents 0.0427 _diffrn_reflns_av_sigmaI/netI 0.0361 _diffrn_reflns_limit_h_min -28 _diffrn_reflns_limit_h_max 28 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 1.79 _diffrn_reflns_theta_max 26.09 _reflns_number_total 4031 _reflns_number_gt 2569 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _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^)+(0.0319P)^2^+14.0441P] 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 4031 _refine_ls_number_parameters 248 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0793 _refine_ls_R_factor_gt 0.0399 _refine_ls_wR_factor_ref 0.1011 _refine_ls_wR_factor_gt 0.0836 _refine_ls_goodness_of_fit_ref 1.003 _refine_ls_restrained_S_all 1.003 _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 Br1 Br 0.00471(3) 0.00690(6) 0.62726(4) 0.0955(2) Uani 1 1 d . . . Br2 Br 0.34503(3) 0.35008(6) 1.16885(3) 0.0937(3) Uani 1 1 d . . . Br3 Br 0.47873(3) 0.01589(6) 0.60312(4) 0.0906(2) Uani 1 1 d . . . C1 C 0.0612(2) 0.1150(4) 0.6089(3) 0.0561(12) Uani 1 1 d . . . C2 C 0.1073(2) 0.0779(4) 0.5757(3) 0.0677(14) Uani 1 1 d . . . H2 H 0.1106 0.0004 0.5621 0.081 Uiso 1 1 calc R . . C3 C 0.1487(2) 0.1562(4) 0.5627(3) 0.0595(13) Uani 1 1 d . . . H3 H 0.1801 0.1320 0.5396 0.071 Uiso 1 1 calc R . . C4 C 0.14369(17) 0.2702(4) 0.5837(3) 0.0424(10) Uani 1 1 d . . . C5 C 0.09692(19) 0.3059(4) 0.6177(3) 0.0535(12) Uani 1 1 d . . . H5 H 0.0935 0.3830 0.6323 0.064 Uiso 1 1 calc R . . C6 C 0.0555(2) 0.2277(5) 0.6299(3) 0.0623(13) Uani 1 1 d . . . H6 H 0.0237 0.2514 0.6524 0.075 Uiso 1 1 calc R . . C7 C 0.30762(17) 0.2904(3) 0.7693(3) 0.0398(9) Uani 1 1 d . . . C8 C 0.31567(18) 0.3024(3) 0.8658(2) 0.0406(9) Uani 1 1 d . . . C9 C 0.3637(2) 0.2530(4) 0.9219(3) 0.0542(12) Uani 1 1 d . . . H9 H 0.3902 0.2097 0.8990 0.065 Uiso 1 1 calc R . . C10 C 0.3726(2) 0.2673(4) 1.0123(3) 0.0621(13) Uani 1 1 d . . . H10 H 0.4053 0.2348 1.0499 0.074 Uiso 1 1 calc R . . C11 C 0.3331(2) 0.3296(4) 1.0452(3) 0.0540(12) Uani 1 1 d . . . C12 C 0.2844(2) 0.3780(4) 0.9914(3) 0.0545(12) Uani 1 1 d . . . H12 H 0.2575 0.4193 1.0152 0.065 Uiso 1 1 calc R . . C13 C 0.27581(19) 0.3644(4) 0.9015(3) 0.0478(10) Uani 1 1 d . . . H13 H 0.2430 0.3972 0.8645 0.057 Uiso 1 1 calc R . . C14 C 0.35121(17) 0.2228(4) 0.7336(2) 0.0402(9) Uani 1 1 d . . . C15 C 0.3481(2) 0.1041(4) 0.7295(3) 0.0501(11) Uani 1 1 d . . . H15 H 0.3199 0.0658 0.7524 0.060 Uiso 1 1 calc R . . C16 C 0.3862(2) 0.0416(4) 0.6920(3) 0.0544(12) Uani 1 1 d . . . H16 H 0.3842 -0.0385 0.6897 0.065 Uiso 1 1 calc R . . C17 C 0.4271(2) 0.0999(4) 0.6583(3) 0.0536(12) Uani 1 1 d . . . C18 C 0.4315(2) 0.2161(5) 0.6615(3) 0.0620(13) Uani 1 1 d . . . H18 H 0.4599 0.2535 0.6384 0.074 Uiso 1 1 calc R . . C19 C 0.39336(19) 0.2786(4) 0.6994(3) 0.0566(12) Uani 1 1 d . . . H19 H 0.3960 0.3586 0.7020 0.068 Uiso 1 1 calc R . . H1A H 0.2728(18) 0.280(4) 0.613(3) 0.043(13) Uiso 1 1 d . . . N1 N 0.25889(16) 0.3333(3) 0.6299(2) 0.0446(9) Uani 1 1 d . . . N2 N 0.26367(15) 0.3424(3) 0.7201(2) 0.0425(8) Uani 1 1 d . . . O1 O 0.20572(13) 0.3529(2) 0.47991(16) 0.0486(7) Uani 1 1 d . . . O2 O 0.18032(13) 0.4801(2) 0.59246(19) 0.0525(8) Uani 1 1 d . . . S1 S 0.19631(5) 0.36984(9) 0.56660(6) 0.0413(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 Br1 0.0800(4) 0.1121(6) 0.0984(5) 0.0205(4) 0.0287(4) -0.0293(4) Br2 0.1200(5) 0.1242(6) 0.0332(3) -0.0048(3) 0.0095(3) -0.0236(4) Br3 0.0757(4) 0.1138(5) 0.0870(4) -0.0203(4) 0.0285(3) 0.0376(4) C1 0.043(3) 0.074(4) 0.050(3) 0.010(2) 0.007(2) -0.005(2) C2 0.066(3) 0.051(3) 0.091(4) 0.000(3) 0.027(3) -0.002(3) C3 0.058(3) 0.052(3) 0.076(3) -0.001(2) 0.031(3) 0.011(2) C4 0.041(2) 0.048(3) 0.036(2) -0.0004(18) 0.0035(18) 0.009(2) C5 0.045(3) 0.061(3) 0.056(3) -0.009(2) 0.015(2) 0.012(2) C6 0.044(3) 0.088(4) 0.059(3) -0.003(3) 0.019(2) 0.006(3) C7 0.036(2) 0.043(2) 0.041(2) -0.0027(19) 0.0091(18) -0.0013(19) C8 0.046(2) 0.039(2) 0.034(2) 0.0006(17) 0.0054(18) -0.0016(19) C9 0.055(3) 0.057(3) 0.047(2) -0.005(2) 0.004(2) 0.009(2) C10 0.068(3) 0.066(3) 0.044(3) 0.005(2) -0.007(2) 0.003(3) C11 0.076(3) 0.054(3) 0.030(2) -0.001(2) 0.007(2) -0.017(3) C12 0.067(3) 0.058(3) 0.042(2) -0.005(2) 0.020(2) -0.001(2) C13 0.048(3) 0.057(3) 0.038(2) 0.002(2) 0.0085(19) 0.009(2) C14 0.039(2) 0.048(3) 0.033(2) 0.0001(18) 0.0062(17) 0.004(2) C15 0.058(3) 0.053(3) 0.041(2) 0.006(2) 0.015(2) 0.003(2) C16 0.071(3) 0.045(3) 0.046(3) 0.002(2) 0.011(2) 0.013(2) C17 0.048(3) 0.067(3) 0.044(2) -0.006(2) 0.006(2) 0.021(2) C18 0.043(3) 0.074(4) 0.075(3) -0.006(3) 0.026(2) -0.004(3) C19 0.050(3) 0.051(3) 0.072(3) -0.008(2) 0.021(2) -0.007(2) N1 0.045(2) 0.056(2) 0.0336(18) -0.0055(17) 0.0107(16) 0.0101(18) N2 0.044(2) 0.053(2) 0.0311(16) -0.0052(15) 0.0087(15) 0.0019(17) O1 0.0577(18) 0.0579(19) 0.0305(14) 0.0001(13) 0.0108(13) 0.0075(15) O2 0.063(2) 0.0438(17) 0.0523(18) 0.0011(14) 0.0167(15) 0.0125(15) S1 0.0453(6) 0.0451(6) 0.0334(5) 0.0000(4) 0.0087(4) 0.0079(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 Br1 C1 1.888(5) . ? Br2 C11 1.900(4) . ? Br3 C17 1.899(4) . ? C1 C6 1.361(7) . ? C1 C2 1.364(6) . ? C2 C3 1.374(6) . ? C3 C4 1.374(6) . ? C4 C5 1.380(5) . ? C4 S1 1.749(4) . ? C5 C6 1.370(6) . ? C7 N2 1.284(5) . ? C7 C8 1.481(5) . ? C7 C14 1.489(5) . ? C8 C9 1.381(6) . ? C8 C13 1.388(5) . ? C9 C10 1.388(6) . ? C10 C11 1.361(7) . ? C11 C12 1.371(6) . ? C12 C13 1.381(5) . ? C14 C15 1.378(6) . ? C14 C19 1.380(6) . ? C15 C16 1.375(6) . ? C16 C17 1.368(6) . ? C17 C18 1.351(7) . ? C18 C19 1.381(6) . ? N1 N2 1.391(4) . ? N1 S1 1.624(4) . ? O1 S1 1.432(3) . ? O2 S1 1.416(3) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C6 C1 C2 121.6(4) . . ? C6 C1 Br1 119.4(4) . . ? C2 C1 Br1 119.0(4) . . ? C1 C2 C3 119.2(5) . . ? C4 C3 C2 120.0(4) . . ? C3 C4 C5 119.9(4) . . ? C3 C4 S1 119.9(3) . . ? C5 C4 S1 120.2(3) . . ? C6 C5 C4 119.9(4) . . ? C1 C6 C5 119.4(4) . . ? N2 C7 C8 117.7(3) . . ? N2 C7 C14 123.0(3) . . ? C8 C7 C14 119.3(3) . . ? C9 C8 C13 118.8(4) . . ? C9 C8 C7 120.3(4) . . ? C13 C8 C7 120.9(4) . . ? C8 C9 C10 120.7(4) . . ? C11 C10 C9 119.1(4) . . ? C10 C11 C12 121.7(4) . . ? C10 C11 Br2 119.5(4) . . ? C12 C11 Br2 118.8(4) . . ? C11 C12 C13 119.0(4) . . ? C12 C13 C8 120.7(4) . . ? C15 C14 C19 119.0(4) . . ? C15 C14 C7 120.7(4) . . ? C19 C14 C7 120.2(4) . . ? C16 C15 C14 120.9(4) . . ? C17 C16 C15 118.5(4) . . ? C18 C17 C16 122.2(4) . . ? C18 C17 Br3 118.5(4) . . ? C16 C17 Br3 119.3(4) . . ? C17 C18 C19 119.2(4) . . ? C14 C19 C18 120.2(4) . . ? N2 N1 S1 116.8(3) . . ? C7 N2 N1 116.1(3) . . ? O2 S1 O1 119.98(17) . . ? O2 S1 N1 108.7(2) . . ? O1 S1 N1 103.27(18) . . ? O2 S1 C4 108.29(19) . . ? O1 S1 C4 108.39(18) . . ? N1 S1 C4 107.53(19) . . ? _diffrn_measured_fraction_theta_max 0.986 _diffrn_reflns_theta_full 26.09 _diffrn_measured_fraction_theta_full 0.986 _refine_diff_density_max 0.886 _refine_diff_density_min -0.682 _refine_diff_density_rms 0.073 _database_code_depnum_ccdc_archive 'CCDC 971254' ####################################################################### # # 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_TCSH _audit_creation_method SHELXL-97 _chemical_name_systematic ; trichloro sulfonylhydrazone ; _chemical_name_common 'trichloro sulfonylhydrazone' _chemical_melting_point 476(2) _chemical_formula_moiety 'C19 H13 Cl3 N2 O2 S' _chemical_formula_sum 'C19 H13 Cl3 N2 O2 S' _chemical_formula_weight 439.72 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 'C2/c ' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 22.655(4) _cell_length_b 11.6004(18) _cell_length_c 15.428(3) _cell_angle_alpha 90.00 _cell_angle_beta 101.926(3) _cell_angle_gamma 90.00 _cell_volume 3967.2(11) _cell_formula_units_Z 8 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 3778 _cell_measurement_theta_min 2.29 _cell_measurement_theta_max 24.89 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.26 _exptl_crystal_size_mid 0.21 _exptl_crystal_size_min 0.17 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.472 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1792 _exptl_absorpt_coefficient_mu 0.584 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8629 _exptl_absorpt_correction_T_max 0.9072 _exptl_absorpt_process_details 'Bruker AXS SADABS program' _exptl_special_details ; Sheldrick,G.M.,(2003),University of gottingen,Germany ; _diffrn_ambient_temperature 298(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 15441 _diffrn_reflns_av_R_equivalents 0.0460 _diffrn_reflns_av_sigmaI/netI 0.0480 _diffrn_reflns_limit_h_min -28 _diffrn_reflns_limit_h_max 27 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 1.84 _diffrn_reflns_theta_max 26.07 _reflns_number_total 3923 _reflns_number_gt 2454 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _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^)+(0.0567P)^2^+1.3652P] 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 3923 _refine_ls_number_parameters 248 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0920 _refine_ls_R_factor_gt 0.0516 _refine_ls_wR_factor_ref 0.1297 _refine_ls_wR_factor_gt 0.1124 _refine_ls_goodness_of_fit_ref 1.016 _refine_ls_restrained_S_all 1.016 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.05538(15) 0.3888(3) 0.1127(2) 0.0688(9) Uani 1 1 d . . . C2 C 0.04957(15) 0.2770(4) 0.1356(2) 0.0726(10) Uani 1 1 d . . . H2 H 0.0168 0.2540 0.1592 0.087 Uiso 1 1 calc R . . C3 C 0.09224(14) 0.1980(3) 0.1237(2) 0.0627(9) Uani 1 1 d . . . H3 H 0.0888 0.1215 0.1399 0.075 Uiso 1 1 calc R . . C4 C 0.14031(12) 0.2324(2) 0.08738(17) 0.0474(7) Uani 1 1 d . . . C5 C 0.14555(15) 0.3460(3) 0.0646(2) 0.0680(9) Uani 1 1 d . . . H5 H 0.1780 0.3696 0.0406 0.082 Uiso 1 1 calc R . . C6 C 0.10272(17) 0.4246(3) 0.0773(3) 0.0793(10) Uani 1 1 d . . . H6 H 0.1060 0.5015 0.0619 0.095 Uiso 1 1 calc R . . C7 C 0.30913(12) 0.2101(2) 0.27039(17) 0.0429(6) Uani 1 1 d . . . C8 C 0.35338(12) 0.2768(2) 0.23197(17) 0.0455(7) Uani 1 1 d . . . C9 C 0.39698(13) 0.2210(3) 0.1970(2) 0.0610(8) Uani 1 1 d . . . H9 H 0.3998 0.1411 0.2001 0.073 Uiso 1 1 calc R . . C10 C 0.43655(14) 0.2824(3) 0.1573(2) 0.0709(10) Uani 1 1 d . . . H10 H 0.4656 0.2443 0.1335 0.085 Uiso 1 1 calc R . . C11 C 0.43232(14) 0.3998(3) 0.1536(2) 0.0636(9) Uani 1 1 d . . . C12 C 0.38951(16) 0.4577(3) 0.18817(19) 0.0651(9) Uani 1 1 d . . . H12 H 0.3872 0.5377 0.1852 0.078 Uiso 1 1 calc R . . C13 C 0.35008(14) 0.3960(3) 0.22721(18) 0.0556(8) Uani 1 1 d . . . H13 H 0.3210 0.4347 0.2506 0.067 Uiso 1 1 calc R . . C14 C 0.31763(12) 0.1982(2) 0.36786(17) 0.0447(7) Uani 1 1 d . . . C15 C 0.27793(14) 0.1341(2) 0.40645(18) 0.0530(7) Uani 1 1 d . . . H15 H 0.2450 0.0985 0.3705 0.064 Uiso 1 1 calc R . . C16 C 0.28677(15) 0.1228(3) 0.49701(19) 0.0619(8) Uani 1 1 d . . . H16 H 0.2598 0.0803 0.5221 0.074 Uiso 1 1 calc R . . C17 C 0.33548(16) 0.1743(3) 0.54995(19) 0.0637(9) Uani 1 1 d . . . C18 C 0.37499(16) 0.2388(3) 0.5144(2) 0.0682(9) Uani 1 1 d . . . H18 H 0.4076 0.2743 0.5512 0.082 Uiso 1 1 calc R . . C19 C 0.36625(14) 0.2511(3) 0.4234(2) 0.0574(8) Uani 1 1 d . . . H19 H 0.3931 0.2952 0.3992 0.069 Uiso 1 1 calc R . . Cl1 Cl 0.00144(5) 0.48801(11) 0.12842(8) 0.1145(4) Uani 1 1 d . . . Cl2 Cl 0.48102(5) 0.47626(11) 0.10173(7) 0.1067(4) Uani 1 1 d . . . Cl3 Cl 0.34672(6) 0.15889(11) 0.66421(6) 0.1086(4) Uani 1 1 d . . . H1A H 0.2753(12) 0.224(2) 0.1121(17) 0.044(8) Uiso 1 1 d . . . N1 N 0.25876(11) 0.1674(2) 0.13147(15) 0.0498(6) Uani 1 1 d . . . N2 N 0.26355(10) 0.15876(19) 0.22243(14) 0.0470(6) Uani 1 1 d . . . O1 O 0.17709(9) 0.02207(16) 0.09580(13) 0.0605(6) Uani 1 1 d . . . O2 O 0.20421(9) 0.14824(16) -0.01876(11) 0.0551(5) Uani 1 1 d . . . S1 S 0.19415(3) 0.13212(6) 0.06902(4) 0.0476(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 C1 0.062(2) 0.078(3) 0.065(2) -0.0136(19) 0.0093(18) 0.0009(19) C2 0.049(2) 0.102(3) 0.070(2) 0.003(2) 0.0183(17) -0.009(2) C3 0.057(2) 0.071(2) 0.059(2) 0.0113(16) 0.0097(16) -0.0128(18) C4 0.0500(17) 0.0522(18) 0.0387(15) -0.0006(13) 0.0062(13) -0.0112(14) C5 0.069(2) 0.056(2) 0.086(3) -0.0005(18) 0.0320(19) -0.0104(17) C6 0.082(3) 0.056(2) 0.103(3) -0.004(2) 0.027(2) -0.004(2) C7 0.0447(16) 0.0459(17) 0.0371(14) -0.0003(12) 0.0063(13) 0.0004(14) C8 0.0477(16) 0.0479(18) 0.0391(15) 0.0009(13) 0.0049(12) -0.0037(14) C9 0.0524(19) 0.059(2) 0.074(2) 0.0071(17) 0.0175(17) 0.0047(16) C10 0.052(2) 0.085(3) 0.080(2) 0.006(2) 0.0241(18) 0.0010(19) C11 0.056(2) 0.080(3) 0.0522(19) 0.0075(17) 0.0061(16) -0.0251(18) C12 0.091(3) 0.053(2) 0.0490(18) 0.0002(15) 0.0082(18) -0.0193(19) C13 0.071(2) 0.053(2) 0.0439(17) -0.0039(14) 0.0147(15) -0.0028(16) C14 0.0531(17) 0.0421(16) 0.0374(14) 0.0008(12) 0.0063(13) 0.0051(14) C15 0.0620(19) 0.0564(19) 0.0406(16) -0.0024(14) 0.0106(14) -0.0018(16) C16 0.078(2) 0.066(2) 0.0441(17) 0.0066(16) 0.0178(17) 0.0036(19) C17 0.084(2) 0.070(2) 0.0347(16) 0.0029(15) 0.0074(17) 0.0194(19) C18 0.078(2) 0.069(2) 0.0471(19) -0.0079(17) -0.0102(17) -0.0006(19) C19 0.062(2) 0.058(2) 0.0485(17) 0.0013(15) 0.0022(15) -0.0072(16) Cl1 0.0921(8) 0.1236(10) 0.1321(10) -0.0245(7) 0.0329(7) 0.0306(7) Cl2 0.0889(7) 0.1334(10) 0.1005(8) 0.0261(7) 0.0261(6) -0.0478(7) Cl3 0.1367(10) 0.1469(11) 0.0375(5) 0.0046(5) 0.0070(5) 0.0267(8) N1 0.0551(15) 0.0588(17) 0.0353(13) 0.0060(11) 0.0091(11) -0.0121(13) N2 0.0526(14) 0.0525(15) 0.0362(12) 0.0057(11) 0.0100(11) -0.0025(12) O1 0.0781(14) 0.0471(12) 0.0572(12) 0.0034(10) 0.0160(11) -0.0152(11) O2 0.0669(13) 0.0635(13) 0.0353(10) -0.0016(9) 0.0113(9) -0.0122(11) S1 0.0564(5) 0.0489(4) 0.0369(4) 0.0005(3) 0.0084(3) -0.0117(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 1.358(5) . ? C1 C6 1.366(5) . ? C1 Cl1 1.731(3) . ? C2 C3 1.372(4) . ? C3 C4 1.382(4) . ? C4 C5 1.375(4) . ? C4 S1 1.751(3) . ? C5 C6 1.375(4) . ? C7 N2 1.286(3) . ? C7 C14 1.482(4) . ? C7 C8 1.484(4) . ? C8 C9 1.381(4) . ? C8 C13 1.386(4) . ? C9 C10 1.383(4) . ? C10 C11 1.366(5) . ? C11 C12 1.374(4) . ? C11 Cl2 1.735(3) . ? C12 C13 1.377(4) . ? C14 C19 1.391(4) . ? C14 C15 1.392(4) . ? C15 C16 1.376(4) . ? C16 C17 1.367(4) . ? C17 C18 1.365(5) . ? C17 Cl3 1.738(3) . ? C18 C19 1.385(4) . ? N1 N2 1.389(3) . ? N1 S1 1.630(3) . ? O1 S1 1.4198(19) . ? O2 S1 1.4313(18) . ? 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 121.4(3) . . ? C2 C1 Cl1 119.3(3) . . ? C6 C1 Cl1 119.3(3) . . ? C1 C2 C3 119.7(3) . . ? C2 C3 C4 119.8(3) . . ? C5 C4 C3 119.8(3) . . ? C5 C4 S1 119.7(2) . . ? C3 C4 S1 120.5(2) . . ? C6 C5 C4 119.9(3) . . ? C1 C6 C5 119.5(3) . . ? N2 C7 C14 117.5(2) . . ? N2 C7 C8 122.7(2) . . ? C14 C7 C8 119.8(2) . . ? C9 C8 C13 118.8(3) . . ? C9 C8 C7 120.6(3) . . ? C13 C8 C7 120.5(3) . . ? C8 C9 C10 120.8(3) . . ? C11 C10 C9 119.1(3) . . ? C10 C11 C12 121.3(3) . . ? C10 C11 Cl2 118.9(3) . . ? C12 C11 Cl2 119.8(3) . . ? C11 C12 C13 119.3(3) . . ? C12 C13 C8 120.6(3) . . ? C19 C14 C15 118.2(3) . . ? C19 C14 C7 120.3(3) . . ? C15 C14 C7 121.6(2) . . ? C16 C15 C14 120.9(3) . . ? C17 C16 C15 119.6(3) . . ? C18 C17 C16 121.0(3) . . ? C18 C17 Cl3 119.5(3) . . ? C16 C17 Cl3 119.5(3) . . ? C17 C18 C19 119.7(3) . . ? C18 C19 C14 120.5(3) . . ? N2 N1 S1 116.89(19) . . ? C7 N2 N1 115.7(2) . . ? O1 S1 O2 119.94(12) . . ? O1 S1 N1 108.61(13) . . ? O2 S1 N1 103.13(12) . . ? O1 S1 C4 108.05(13) . . ? O2 S1 C4 108.59(12) . . ? N1 S1 C4 107.95(13) . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 26.07 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.345 _refine_diff_density_min -0.266 _refine_diff_density_rms 0.048 _database_code_depnum_ccdc_archive 'CCDC 971255'