# Supplementary Material (ESI) for Dalton Transactions # This journal is (c) The Royal Society of Chemistry 2010 data_global _journal_name_full 'Dalton Trans.' _journal_coden_Cambridge 0222 loop_ _publ_author_address ; Departamento de Quimica Inorganica Facultad de Quimica, UNAM, CU; CP 04510 Mexico DF, Mexico ; ; Departamento de Quimica Inorganica Facultad de Quimica, UNAM, CU; CP 04510 Mexico DF, Mexico ; ; Departamento de Quimica Cinvestav, Mexico A.P. 14-740; CP 07360 Mexico DF, Mexico ; ; Departamento de Quimica Cinvestav, Mexico A.P. 14-740; CP 07360 Mexico DF, Mexico ; ; Departamento de Quimica Inorganica Facultad de Quimica, UNAM, CU; CP 04510 Mexico DF, Mexico ; ; Departamento de Quimica Cinvestav, Mexico A.P. 14-740; CP 07360 Mexico DF, Mexico ; ; Departamento de Quimica Cinvestav, Mexico A.P. 14-740; CP 07360 Mexico DF, Mexico ; ; Departamento de Quimica Inorganica Facultad de Quimica, UNAM, CU; CP 04510 Mexico DF, Mexico ; _publ_contact_author_name 'Barba-Behrens, Norah' _publ_contact_author_email norah@servidor.unam.mx _publ_section_title ; Eleven membered chelate ring in cobalt(II), zinc(II), and cadmium(II) compounds containing a disulfide benzimidazole derivative. Nickel(II) thiolate and sulfonate chelates. ; _publ_contact_author_address ; Departamento de Quimica Inorganica Facultad de Quimica, UNAM, CU; CP 04510 Mexico DF, Mexico ; _publ_contact_author_fax 52(55)5622-3810 _publ_contact_author_phone 52(55)5622-3810 _publ_requested_category FM _publ_author_name N.Barba-Behrens # Attachment '- CCDC 758097.cif' #\#CIF_1.1 # CIF produced by WinGX routine CIF_UPDATE # Created on 2009-12-03 at 16:45:12 # Using CIFtbx version 2.6.2 16 Jun 1998 # Dictionary name : cif_core.dic # Dictionary vers : 2.3 # Request file : c:\wingx\files\archive.dat # CIF files read : publish dreduc struct data_1 _database_code_depnum_ccdc_archive 'CCDC 758097' #TrackingRef '- CCDC 758097.cif' _audit_creation_date 2009-12-03T16:45:12-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' _audit_conform_dict_name cif_core.dic _audit_conform_dict_version 2.3 _audit_conform_dict_location ftp://ftp.iucr.org/pub/cif_core.dic _publ_section_abstract ; Herein we report the synthesis, structural and spectroscopic characterization of coordination compounds with bis[2-(1H-benzimidazol-2-yl)phenyl]disulfide [bis-(2phSbz)] (1) and cobalt(II), zinc(II) and cadmium halides (2-7). Their X-ray diffraction analyses showed that the metal ions present similar distorted tetrahedral structure, with the disulfide ligand coordinated through the imidazolic nitrogen atoms, forming a twisted eleven membered chelate. Structures of nickel(II) compounds 8 and 9, showed that the disulfide bond in the ligand was broken and the two halves were coordinated to the nickel(II) through the sulfur and one imidazole nitrogen atom forming six membered rings. In 8, the two ligands were sulfides, however in 9 one of them was oxidized to a sulfone. In both compounds the nickel(II) has a distorted square planar geometry and the sulfur atoms are in cis positions. The oxidation reaction of bis-(2phSbz) was performed in KMnO4/NaOH, giving the 2-(1H,3H-benzimidazolium-2-yl)-benzene sulfonate (10). The solid state structure of compounds 2-5 and 7-10 was determined by X-ray diffraction analyses. ; #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_formula_moiety 'C26 H18 Cl2 Co N4 S2, 2(C2 H6 O)' _chemical_formula_sum 'C30 H30 Cl2 Co1 N4 O2 S2' _chemical_formula_weight 672.56 _chemical_compound_source 'synthesis as described' _chemical_absolute_configuration . #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P 1 21/n 1' _symmetry_space_group_name_Hall '-P 2yn' _symmetry_Int_Tables_number 14 loop_ _symmetry_equiv_pos_as_xyz x,y,z -x,-y,-z -x+1/2,y+1/2,-z+1/2 x+1/2,-y+1/2,z+1/2 _cell_length_a 12.2196(4) _cell_length_b 15.9043(7) _cell_length_c 16.7766(10) _cell_angle_alpha 90 _cell_angle_beta 108.868(2) _cell_angle_gamma 90 _cell_volume 3085.2(3) _cell_formula_units_Z 4 _cell_measurement_temperature 293 _cell_measurement_reflns_used 13393 _cell_measurement_theta_min 1 _cell_measurement_theta_max 27 _cell_measurement_wavelength 0.71073 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description prism _exptl_crystal_colour blue _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.1 _exptl_crystal_size_min 0.08 _exptl_crystal_density_diffrn 1.448 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1388 #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.899 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SADABS (Siemens, 1996)' _exptl_absorpt_correction_T_min 0.14 _exptl_absorpt_correction_T_max 0.93 #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_source 'Enraf Nonius FR590' _diffrn_ambient_temperature 298 _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_detector 'CCD plate' _diffrn_detector_area_resol_mean 9 _diffrn_orient_matrix_type 'by Bruker AXS Collect from scalepack cell' _diffrn_orient_matrix_ub_11 -0.862798E-1 _diffrn_orient_matrix_ub_12 0.4341E-3 _diffrn_orient_matrix_ub_13 -0.24386E-1 _diffrn_orient_matrix_ub_21 -0.59185E-2 _diffrn_orient_matrix_ub_22 -0.34489E-2 _diffrn_orient_matrix_ub_23 0.57983E-1 _diffrn_orient_matrix_ub_31 0.2714E-3 _diffrn_orient_matrix_ub_32 0.627799E-1 _diffrn_orient_matrix_ub_33 0.3354E-2 _diffrn_measurement_device '95mm CCD camera on \k-goniostat' _diffrn_measurement_device_type 'Nonius KappaCCD' _diffrn_measurement_method '\f & \w scans' _diffrn_standards_number 0 _diffrn_reflns_av_R_equivalents 0.126 _diffrn_reflns_number 16218 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -20 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 2.899 _diffrn_reflns_theta_max 27.562 _diffrn_reflns_theta_full 25.081 _diffrn_measured_fraction_theta_full 0.857 _diffrn_measured_fraction_theta_max 0.813 _reflns_number_total 5797 _reflns_number_gt 2313 _reflns_threshold_expression I>3.0\s(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection 'COLLECT (Nonius, 1997-2001).' _computing_cell_refinement 'DENZO/SCALEPACK (Otwinowski & Minor, 1997)' _computing_data_reduction 'DENZO/SCALEPACK (Otwinowski & Minor, 1997)' _computing_structure_solution 'SHELXS 97 (Sheldrick, 1997)' _computing_structure_refinement 'CRYSTALS (Betteridge et al., 2003)' _computing_molecular_graphics 'CAMERON (Watkin et al., 1996)' _computing_publication_material 'CRYSTALS (Betteridge et al., 2003)' #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _refine_ls_structure_factor_coef F _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details ; Method= Modified Sheldrick w=1/[\s^2^(F^2^) + ( 0.00P)^2^ + 0.12P] ,where P=(max(Fo^2^,0) + 2Fc^2^)/3 ; _atom_sites_solution_primary direct _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method None _refine_ls_number_reflns 2313 _refine_ls_number_parameters 388 _refine_ls_number_restraints 48 _refine_ls_R_factor_all 0.1716 _refine_ls_R_factor_gt 0.0617 _refine_ls_wR_factor_ref 0.0828 _refine_ls_wR_factor_gt 0.0828 _refine_ls_wR_factor_all 0.1681 _refine_ls_goodness_of_fit_ref 1.0383 _refine_ls_shift/su_max 0.000232 _refine_diff_density_max 0.59 _refine_diff_density_min -0.45 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# loop_ _atom_type_symbol _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C 0.0033 0.0016 'International Tables Vol C 4.2.6.8 and 6.1.1.4' H 0 0 'International Tables Vol C 4.2.6.8 and 6.1.1.4' Cl 0.1484 0.1585 'International Tables Vol C 4.2.6.8 and 6.1.1.4' N 0.0061 0.0033 'International Tables Vol C 4.2.6.8 and 6.1.1.4' Co 0.3494 0.9721 'International Tables Vol C 4.2.6.8 and 6.1.1.4' O 0.0106 0.006 'International Tables Vol C 4.2.6.8 and 6.1.1.4' S 0.1246 0.1234 'International Tables Vol C 4.2.6.8 and 6.1.1.4' 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_disorder_assembly _atom_site_disorder_group C2 C 0.1614(7) 0.7666(5) 0.1012(7) 0.0562 Uani 1 . . C4 C 0.0978(9) 0.6302(7) 0.2469(9) 0.0801 Uani 1 . . C5 C 0.1577(9) 0.5580(7) 0.2791(8) 0.0809 Uani 1 . . C6 C 0.2515(9) 0.5317(6) 0.2554(9) 0.0841 Uani 1 . . C7 C 0.2892(8) 0.5787(6) 0.1993(8) 0.0719 Uani 1 . . C8 C 0.2301(7) 0.6516(5) 0.1685(7) 0.0525 Uani 1 . . C9 C 0.1384(7) 0.6755(6) 0.1928(7) 0.0602 Uani 1 . . C10 C 0.1399(7) 0.8396(5) 0.0431(7) 0.0587 Uani 1 . . C11 C 0.0409(8) 0.8440(6) -0.0259(8) 0.0709 Uani 1 . . C12 C 0.0237(11) 0.9122(8) -0.0806(9) 0.0952 Uani 1 . . C13 C 0.1029(12) 0.9762(7) -0.0622(10) 0.092 Uani 1 . . C14 C 0.2016(11) 0.9730(6) 0.0044(9) 0.0793 Uani 1 . . C15 C 0.2190(8) 0.9037(5) 0.0587(8) 0.0666 Uani 1 . . C17 C 0.2212(7) 0.7216(5) -0.1147(7) 0.0534 Uani 1 . . C19 C 0.2624(8) 0.9060(5) -0.2243(7) 0.0642 Uani 1 . . C20 C 0.3486(9) 0.9634(6) -0.1926(8) 0.0714 Uani 1 . . C21 C 0.4298(8) 0.9544(5) -0.1144(7) 0.0645 Uani 1 . . C22 C 0.4290(7) 0.8869(5) -0.0631(7) 0.0617 Uani 1 . . C23 C 0.3392(6) 0.8283(5) -0.0943(6) 0.0475 Uani 1 . . C24 C 0.2590(6) 0.8380(5) -0.1728(7) 0.0558 Uani 1 . . C25 C 0.1710(7) 0.6400(5) -0.1037(7) 0.0566 Uani 1 . . C26 C 0.0515(7) 0.6284(6) -0.1197(8) 0.0676 Uani 1 . . C27 C 0.0148(10) 0.5486(9) -0.1043(9) 0.0879 Uani 1 . . C28 C 0.0890(13) 0.4842(8) -0.0781(10) 0.0974 Uani 1 . . C29 C 0.2030(10) 0.4944(6) -0.0625(8) 0.0782 Uani 1 . . C30 C 0.2453(9) 0.5723(5) -0.0754(8) 0.0721 Uani 1 . . C36 C -0.1896(16) 0.8020(18) 0.166(2) 0.1323 Uani 0.5 . 1 C37 C -0.269(3) 0.787(2) 0.075(2) 0.1371 Uani 0.5 . 1 C38 C -0.2047(9) 0.8365(15) 0.145(2) 0.1277 Uani 0.5 . 2 C39 C -0.226(3) 0.7462(14) 0.109(3) 0.1279 Uani 0.5 . 2 C41 C 0.466(2) 0.3659(19) 0.1153(16) 0.2425 Uani 1 . . C42 C 0.355(2) 0.3468(16) 0.137(2) 0.2445 Uani 1 . . H3 H 0.0363 0.7781 0.1497 0.0865 Uiso 1 . . H4 H 0.0339 0.6468 0.261 0.098 Uiso 1 . . H5 H 0.1353 0.5268 0.3179 0.0991 Uiso 1 . . H6 H 0.2895 0.4818 0.2765 0.1041 Uiso 1 . . H7 H 0.3513 0.5607 0.1827 0.0869 Uiso 1 . . H12 H -0.0408 0.9134 -0.1287 0.112 Uiso 1 . . H13 H 0.0884 1.0232 -0.0973 0.1108 Uiso 1 . . H14 H 0.2574 1.0149 0.0143 0.0949 Uiso 1 . . H15 H 0.2846 0.9011 0.1062 0.0819 Uiso 1 . . H18 H 0.1278 0.7581 -0.2293 0.0712 Uiso 1 . . H19 H 0.2105 0.9112 -0.2774 0.0762 Uiso 1 . . H20 H 0.3527 1.0102 -0.2251 0.084 Uiso 1 . . H21 H 0.487 0.9946 -0.0946 0.0812 Uiso 1 . . H22 H 0.4852 0.8798 -0.0108 0.0751 Uiso 1 . . H27 H -0.0633 0.5403 -0.1128 0.109 Uiso 1 . . H28 H 0.0611 0.4321 -0.0699 0.114 Uiso 1 . . H29 H 0.2528 0.4501 -0.0437 0.0939 Uiso 1 . . H30 H 0.3243 0.5797 -0.0649 0.0858 Uiso 1 . . H35 H -0.048 0.8479 0.2232 0.1715 Uiso 1 . . H40 H 0.5075 0.4636 0.1565 0.2867 Uiso 1 . . H361 H -0.2299 0.8403 0.1899 0.1776 Uiso 0.5 . 1 H362 H -0.1771 0.7508 0.1969 0.1776 Uiso 0.5 . 1 H371 H -0.3399 0.7638 0.0771 0.1822 Uiso 0.5 . 1 H372 H -0.2848 0.8373 0.0427 0.1822 Uiso 0.5 . 1 H373 H -0.232 0.7478 0.0497 0.1822 Uiso 0.5 . 1 H381 H -0.2349 0.8765 0.1009 0.1726 Uiso 0.5 . 2 H382 H -0.2373 0.8456 0.188 0.1726 Uiso 0.5 . 2 H391 H -0.3071 0.7364 0.0861 0.1724 Uiso 0.5 . 2 H392 H -0.1912 0.7387 0.0669 0.1724 Uiso 0.5 . 2 H393 H -0.1936 0.7077 0.154 0.1724 Uiso 0.5 . 2 H411 H 0.4484 0.3955 0.0635 0.2888 Uiso 1 . . H412 H 0.5093 0.317 0.113 0.2888 Uiso 1 . . H421 H 0.3047 0.3114 0.0952 0.2913 Uiso 1 . . H422 H 0.3168 0.3978 0.1401 0.2913 Uiso 1 . . H423 H 0.3778 0.3193 0.1896 0.2913 Uiso 1 . . N1 N 0.2449(5) 0.7100(4) 0.1098(5) 0.051 Uani 1 . . N3 N 0.0961(7) 0.7486(5) 0.1475(6) 0.0725 Uani 1 . . N16 N 0.3150(5) 0.7541(4) -0.0561(5) 0.0484 Uani 1 . . N18 N 0.1869(6) 0.7690(4) -0.1839(6) 0.0598 Uani 1 . . O35 O -0.0826(8) 0.8400(5) 0.1731(8) 0.1258 Uani 1 . . O40 O 0.5162(17) 0.4165(11) 0.1867(15) 0.2398 Uani 1 . . S31 S -0.0659(2) 0.7622(2) -0.0498(2) 0.0906 Uani 1 . . S32 S -0.05317(19) 0.70999(19) -0.1584(2) 0.0829 Uani 1 . . Cl33 Cl 0.49858(17) 0.81922(13) 0.15059(16) 0.0642 Uani 1 . . Cl34 Cl 0.4980(2) 0.60558(15) 0.0876(2) 0.0815 Uani 1 . . Co1 Co 0.38217(9) 0.71998(7) 0.06663(9) 0.0521 Uani 1 . . 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 C2 0.059(5) 0.056(5) 0.052(8) -0.003(4) 0.016(5) -0.002(4) C4 0.074(6) 0.086(7) 0.085(11) 0.000(6) 0.034(7) -0.005(6) C5 0.075(6) 0.098(7) 0.071(10) 0.024(6) 0.026(6) -0.003(6) C6 0.084(7) 0.070(6) 0.087(11) 0.025(6) 0.012(7) -0.001(5) C7 0.062(5) 0.079(6) 0.068(9) 0.024(6) 0.013(5) -0.002(5) C8 0.050(4) 0.056(5) 0.047(7) 0.003(4) 0.010(4) -0.010(4) C9 0.063(5) 0.068(5) 0.052(8) 0.006(5) 0.021(5) 0.000(5) C10 0.059(5) 0.068(5) 0.052(8) -0.008(5) 0.023(5) 0.004(5) C11 0.066(6) 0.081(6) 0.067(9) -0.003(6) 0.023(6) 0.010(5) C12 0.094(8) 0.104(8) 0.075(12) 0.022(7) 0.009(7) 0.035(7) C13 0.126(10) 0.071(7) 0.082(12) 0.026(7) 0.037(9) 0.035(7) C14 0.106(8) 0.054(5) 0.086(11) 0.012(6) 0.043(8) 0.007(5) C15 0.067(5) 0.059(5) 0.070(9) -0.007(5) 0.016(5) 0.006(5) C17 0.048(4) 0.059(5) 0.045(7) -0.007(5) 0.003(4) 0.001(4) C19 0.066(5) 0.074(6) 0.040(7) 0.010(5) -0.001(5) 0.002(5) C20 0.099(7) 0.061(5) 0.052(8) 0.014(5) 0.022(6) 0.004(5) C21 0.070(5) 0.062(5) 0.057(8) 0.000(5) 0.015(5) -0.014(4) C22 0.062(5) 0.058(5) 0.055(8) -0.007(5) 0.005(5) -0.012(4) C23 0.043(4) 0.062(5) 0.037(6) -0.001(4) 0.013(4) 0.003(4) C24 0.040(4) 0.064(5) 0.059(8) -0.005(5) 0.009(4) 0.001(4) C25 0.061(5) 0.067(5) 0.037(7) -0.014(4) 0.010(4) -0.020(5) C26 0.050(5) 0.080(6) 0.068(9) -0.013(5) 0.012(5) -0.018(5) C27 0.072(6) 0.120(9) 0.074(11) -0.024(7) 0.026(6) -0.037(7) C28 0.123(10) 0.079(7) 0.086(13) -0.011(7) 0.029(9) -0.029(8) C29 0.098(8) 0.075(6) 0.056(9) 0.000(5) 0.017(6) -0.011(6) C30 0.079(6) 0.058(5) 0.077(10) -0.012(5) 0.023(6) -0.006(5) C36 0.127(6) 0.127(7) 0.165(13) 0.010(7) 0.077(8) 0.007(6) C37 0.130(8) 0.131(9) 0.168(13) 0.010(8) 0.073(9) 0.006(7) C38 0.121(6) 0.121(7) 0.164(12) 0.007(7) 0.079(8) 0.018(6) C39 0.122(7) 0.120(8) 0.165(13) 0.007(8) 0.078(9) 0.022(8) C41 0.286(16) 0.260(15) 0.18(2) 0.010(11) 0.073(16) -0.037(11) C42 0.287(16) 0.263(15) 0.18(2) 0.013(11) 0.072(16) -0.040(12) N1 0.047(3) 0.058(4) 0.045(6) -0.006(4) 0.011(3) -0.006(3) N3 0.076(5) 0.079(5) 0.079(9) 0.005(5) 0.047(5) 0.008(4) N16 0.046(3) 0.054(3) 0.036(5) -0.002(3) 0.000(3) -0.001(3) N18 0.053(4) 0.068(4) 0.052(6) -0.002(4) 0.006(4) -0.002(4) O35 0.121(6) 0.123(6) 0.161(12) 0.008(5) 0.084(7) 0.016(5) O40 0.285(15) 0.253(15) 0.18(2) 0.011(10) 0.074(15) -0.037(11) S31 0.0630(14) 0.128(2) 0.085(3) -0.0219(19) 0.0296(16) -0.0094(15) S32 0.0492(12) 0.127(2) 0.063(2) -0.0181(17) 0.0048(12) -0.0066(13) Cl33 0.0611(12) 0.0703(12) 0.0458(17) 0.0057(11) -0.0042(10) -0.0101(11) Cl34 0.0621(13) 0.0782(15) 0.094(3) 0.0111(14) 0.0106(14) 0.0159(12) Co1 0.0436(6) 0.0611(7) 0.0440(9) 0.0041(6) 0.0038(5) -0.0040(5) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 _geom_bond_publ_flag C2 C10 1.485(14) . . yes C2 N1 1.333(10) . . yes C2 N3 1.313(12) . . yes C4 C5 1.376(14) . . yes C4 C9 1.372(14) . . yes C4 H4 0.924 . . no C5 C6 1.394(14) . . yes C5 H5 0.927 . . no C6 C7 1.391(15) . . yes C6 H6 0.929 . . no C7 C8 1.376(12) . . yes C7 H7 0.935 . . no C8 C9 1.364(12) . . yes C8 N1 1.407(11) . . yes C9 N3 1.393(12) . . yes C10 C11 1.380(15) . . yes C10 C15 1.370(11) . . yes C11 C12 1.392(17) . . yes C11 S31 1.793(10) . . yes C12 C13 1.368(16) . . yes C12 H12 0.929 . . no C13 C14 1.355(19) . . yes C13 H13 0.932 . . no C14 C15 1.402(15) . . yes C14 H14 0.928 . . no C15 H15 0.93 . . no C17 C25 1.473(12) . . yes C17 N16 1.348(11) . . yes C17 N18 1.334(12) . . yes C19 C20 1.364(13) . . yes C19 C24 1.394(13) . . yes C19 H19 0.915 . . no C20 C21 1.372(15) . . yes C20 H20 0.934 . . no C21 C22 1.378(14) . . yes C21 H21 0.926 . . no C22 C23 1.405(11) . . yes C22 H22 0.929 . . no C23 C24 1.372(13) . . yes C23 N16 1.420(11) . . yes C24 N18 1.382(10) . . yes C25 C26 1.409(11) . . yes C25 C30 1.389(13) . . yes C26 C27 1.399(15) . . yes C26 S32 1.790(10) . . yes C27 C28 1.344(16) . . yes C27 H27 0.927 . . no C28 C29 1.341(16) . . yes C28 H28 0.923 . . no C29 C30 1.388(13) . . yes C29 H29 0.918 . . no C30 H30 0.931 . . no C36 C37 1.541(5) . . yes C36 H361 0.95 . . no C36 H362 0.95 . . no C36 O35 1.410(5) . . yes C37 H371 0.95 . . no C37 H372 0.95 . . no C37 H373 0.95 . . no C38 C39 1.542(5) . . yes C38 H381 0.95 . . no C38 H382 0.95 . . no C38 O35 1.413(5) . . yes C39 H391 0.95 . . no C39 H392 0.95 . . no C39 H393 0.95 . . no C41 C42 1.54(4) . . yes C41 H411 0.95 . . no C41 H412 0.95 . . no C41 O40 1.41(3) . . yes C42 H421 0.95 . . no C42 H422 0.95 . . no C42 H423 0.95 . . no H3 N3 0.879 . . no H18 N18 0.881 . . no H35 O35 0.82 . . no H40 O40 0.891 . . no N1 Co1 2.037(6) . . yes N16 Co1 2.028(8) . . yes S31 S32 2.054(5) . . yes Cl33 Co1 2.281(2) . . yes Cl34 Co1 2.262(2) . . yes 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_2 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C10 C2 N1 124.4(8) . . . yes C10 C2 N3 123.2(8) . . . yes N1 C2 N3 112.3(8) . . . yes C5 C4 C9 116.0(9) . . . yes C5 C4 H4 121.5 . . . no C9 C4 H4 122.5 . . . no C4 C5 C6 121.4(10) . . . yes C4 C5 H5 118.9 . . . no C6 C5 H5 119.8 . . . no C5 C6 C7 121.0(9) . . . yes C5 C6 H6 120.2 . . . no C7 C6 H6 118.8 . . . no C6 C7 C8 117.3(9) . . . yes C6 C7 H7 121 . . . no C8 C7 H7 121.6 . . . no C7 C8 C9 120.3(9) . . . yes C7 C8 N1 130.5(8) . . . yes C9 C8 N1 109.3(7) . . . yes C4 C9 C8 124.1(9) . . . yes C4 C9 N3 130.5(8) . . . yes C8 C9 N3 105.4(8) . . . yes C2 C10 C11 120.7(8) . . . yes C2 C10 C15 119.5(9) . . . yes C11 C10 C15 119.8(9) . . . yes C10 C11 C12 119.7(10) . . . yes C10 C11 S31 121.9(8) . . . yes C12 C11 S31 118.3(10) . . . yes C11 C12 C13 119.0(12) . . . yes C11 C12 H12 119.5 . . . no C13 C12 H12 121.4 . . . no C12 C13 C14 122.4(10) . . . yes C12 C13 H13 118.5 . . . no C14 C13 H13 119.1 . . . no C13 C14 C15 118.2(10) . . . yes C13 C14 H14 121.9 . . . no C15 C14 H14 120 . . . no C14 C15 C10 120.7(10) . . . yes C14 C15 H15 119.9 . . . no C10 C15 H15 119.4 . . . no C25 C17 N16 122.4(9) . . . yes C25 C17 N18 125.5(8) . . . yes N16 C17 N18 111.9(7) . . . yes C20 C19 C24 116.8(10) . . . yes C20 C19 H19 121.7 . . . no C24 C19 H19 121.5 . . . no C19 C20 C21 122.1(9) . . . yes C19 C20 H20 119 . . . no C21 C20 H20 118.9 . . . no C20 C21 C22 122.0(9) . . . yes C20 C21 H21 119.9 . . . no C22 C21 H21 118.1 . . . no C21 C22 C23 116.5(10) . . . yes C21 C22 H22 122 . . . no C23 C22 H22 121.5 . . . no C22 C23 C24 120.8(8) . . . yes C22 C23 N16 129.4(8) . . . yes C24 C23 N16 109.8(7) . . . yes C19 C24 C23 121.8(7) . . . yes C19 C24 N18 132.7(9) . . . yes C23 C24 N18 105.5(8) . . . yes C17 C25 C26 122.6(8) . . . yes C17 C25 C30 118.2(7) . . . yes C26 C25 C30 119.2(8) . . . yes C25 C26 C27 117.3(9) . . . yes C25 C26 S32 123.3(7) . . . yes C27 C26 S32 119.4(7) . . . yes C26 C27 C28 121.9(9) . . . yes C26 C27 H27 118.4 . . . no C28 C27 H27 119.7 . . . no C27 C28 C29 121.4(10) . . . yes C27 C28 H28 119.3 . . . no C29 C28 H28 119.3 . . . no C28 C29 C30 119.6(11) . . . yes C28 C29 H29 120.4 . . . no C30 C29 H29 120 . . . no C25 C30 C29 120.6(9) . . . yes C25 C30 H30 119.4 . . . no C29 C30 H30 120 . . . no C37 C36 H361 105.6 . . . no C37 C36 H362 110.3 . . . no H361 C36 H362 109.5 . . . no C37 C36 O35 115(2) . . . yes H361 C36 O35 106.4 . . . no H362 C36 O35 109.9 . . . no C36 C37 H371 108.3 . . . no C36 C37 H372 112.4 . . . no H371 C37 H372 109.5 . . . no C36 C37 H373 107.7 . . . no H371 C37 H373 109.5 . . . no H372 C37 H373 109.5 . . . no C39 C38 H381 110.7 . . . no C39 C38 H382 111.9 . . . no H381 C38 H382 109.5 . . . no C39 C38 O35 101.5(18) . . . yes H381 C38 O35 109.9 . . . no H382 C38 O35 113.2 . . . no C38 C39 H391 109.8 . . . no C38 C39 H392 111 . . . no H391 C39 H392 109.5 . . . no C38 C39 H393 108.7 . . . no H391 C39 H393 109.5 . . . no H392 C39 H393 109.5 . . . no C42 C41 H411 110.9 . . . no C42 C41 H412 113.1 . . . no H411 C41 H412 109.5 . . . no C42 C41 O40 95.2(18) . . . yes H411 C41 O40 113.7 . . . no H412 C41 O40 113.9 . . . no C41 C42 H421 110 . . . no C41 C42 H422 109.6 . . . no H421 C42 H422 109.5 . . . no C41 C42 H423 107.5 . . . no H421 C42 H423 109.5 . . . no H422 C42 H423 109.5 . . . no C8 N1 C2 104.7(6) . . . yes C8 N1 Co1 127.4(5) . . . yes C2 N1 Co1 126.8(6) . . . yes C9 N3 H3 126.1 . . . no C9 N3 C2 108.3(7) . . . yes H3 N3 C2 125.5 . . . no C23 N16 C17 103.9(8) . . . yes C23 N16 Co1 127.3(5) . . . yes C17 N16 Co1 127.4(6) . . . yes C24 N18 C17 108.9(8) . . . yes C24 N18 H18 125.6 . . . no C17 N18 H18 125.4 . . . no C36 O35 H35 107.9 . . . no C41 O40 H40 93.2 . . . no C11 S31 S32 103.5(4) . . . yes C26 S32 S31 102.8(4) . . . yes N1 Co1 N16 105.8(3) . . . yes N1 Co1 Cl33 104.8(2) . . . yes N16 Co1 Cl33 114.13(19) . . . yes N1 Co1 Cl34 115.3(2) . . . yes N16 Co1 Cl34 113.6(2) . . . yes Cl33 Co1 Cl34 103.11(10) . . . yes # Attachment '- CCDC 758098.cif' #\#CIF_1.1 # CIF produced by WinGX routine CIF_UPDATE # Created on 2009-12-07 at 16:31:31 # Using CIFtbx version 2.6.2 16 Jun 1998 # Dictionary name : cif_core.dic # Dictionary vers : 2.3 # Request file : c:\wingx\files\archive.dat # CIF files read : publish dreduc struct data_2 _database_code_depnum_ccdc_archive 'CCDC 758098' #TrackingRef '- CCDC 758098.cif' _audit_creation_date 2009-12-07T16:31:31-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' _audit_conform_dict_name cif_core.dic _audit_conform_dict_version 2.3 _audit_conform_dict_location ftp://ftp.iucr.org/pub/cif_core.dic _publ_section_abstract ; Herein we report the synthesis, structural and spectroscopic characterization of coordination compounds with bis[2-(1H-benzimidazol-2-yl)phenyl]disulfide [bis-(2phSbz)] (1) and cobalt(II), zinc(II) and cadmium halides (2-7). Their X-ray diffraction analyses showed that the metal ions present similar distorted tetrahedral structure, with the disulfide ligand coordinated through the imidazolic nitrogen atoms, forming a twisted eleven membered chelate. Structures of nickel(II) compounds 8 and 9, showed that the disulfide bond in the ligand was broken and the two halves were coordinated to the nickel(II) through the sulfur and one imidazole nitrogen atom forming six membered rings. In 8, the two ligands were sulfides, however in 9 one of them was oxidized to a sulfone. In both compounds the nickel(II) has a distorted square planar geometry and the sulfur atoms are in cis positions. The oxidation reaction of bis-(2phSbz) was performed in KMnO4/NaOH, giving the 2-(1H,3H-benzimidazolium-2-yl)-benzene sulfonate (10). The solid state structure of compounds 2-5 and 7-10 was determined by X-ray diffraction analyses. ; #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_formula_moiety 'C26 H18 Br2 Co N4 S2, 2(C2 H6 O)' _chemical_formula_sum 'C30 H30 Br2 Co1 N4 O2 S2' _chemical_formula_weight 761.47 _chemical_compound_source 'synthesis as described' _chemical_absolute_configuration . #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P 1 21/n 1' _symmetry_space_group_name_Hall '-P 2yn ' _symmetry_Int_Tables_number 14 loop_ _symmetry_equiv_pos_as_xyz x,y,z -x,-y,-z -x+1/2,y+1/2,-z+1/2 x+1/2,-y+1/2,z+1/2 _cell_length_a 12.3673(2) _cell_length_b 15.8818(3) _cell_length_c 17.1902(4) _cell_angle_alpha 90 _cell_angle_beta 108.1130(10) _cell_angle_gamma 90 _cell_volume 3209.10(11) _cell_formula_units_Z 4 _cell_measurement_temperature 293 _cell_measurement_reflns_used 18282 _cell_measurement_theta_min 3 _cell_measurement_theta_max 27 _cell_measurement_wavelength 0.71073 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description prism _exptl_crystal_colour blue _exptl_crystal_size_max 0.2 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.08 _exptl_crystal_density_diffrn 1.576 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1532 #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 3.189 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SADABS (Siemens, 1996)' _exptl_absorpt_correction_T_min 0.5 _exptl_absorpt_correction_T_max 0.77 #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_source 'Enraf Nonius FR590' _diffrn_ambient_temperature 293 _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_detector 'CCD plate' _diffrn_detector_area_resol_mean 9 _diffrn_orient_matrix_type 'by Bruker AXS Collect from scalepack cell' _diffrn_orient_matrix_ub_11 0.406032E-1 _diffrn_orient_matrix_ub_12 0.335932E-1 _diffrn_orient_matrix_ub_13 0.497012E-1 _diffrn_orient_matrix_ub_21 0.482307E-1 _diffrn_orient_matrix_ub_22 -0.499983E-1 _diffrn_orient_matrix_ub_23 0.02354 _diffrn_orient_matrix_ub_31 0.571206E-1 _diffrn_orient_matrix_ub_32 0.183378E-1 _diffrn_orient_matrix_ub_33 -0.26866E-1 _diffrn_measurement_device '95mm CCD camera on \k-goniostat' _diffrn_measurement_device_type 'Nonius KappaCCD' _diffrn_measurement_method '\f & \w scans' _diffrn_standards_number 0 _diffrn_reflns_av_R_equivalents 0.063 _diffrn_reflns_number 31351 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -20 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 3.697 _diffrn_reflns_theta_max 27.497 _diffrn_reflns_theta_full 26.947 _diffrn_measured_fraction_theta_full 0.995 _diffrn_measured_fraction_theta_max 0.992 _reflns_number_total 7297 _reflns_number_gt 3407 _reflns_threshold_expression I>2.5\s(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection 'COLLECT (Nonius, 1997-2001).' _computing_cell_refinement 'DENZO/SCALEPACK (Otwinowski & Minor, 1997)' _computing_data_reduction 'DENZO/SCALEPACK (Otwinowski & Minor, 1997)' _computing_structure_solution 'SHELXS 86 (Sheldrick, 1986)' _computing_structure_refinement 'CRYSTALS (Betteridge et al., 2003)' _computing_molecular_graphics 'CAMERON (Watkin et al., 1996)' _computing_publication_material 'CRYSTALS (Betteridge et al., 2003)' #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _refine_ls_structure_factor_coef F _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details ; Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982) [weight] = 1.0/[A~0~*T~0~(x)+A~1~*T~1~(x) ... +A~n-1~]*T~n-1~(x)] where A~i~ are the Chebychev coefficients listed below and x= Fcalc/Fmax Method = Robust Weighting (Prince, 1982) W = [weight] * [1-(deltaF/6*sigmaF)^2^]^2^ A~i~ are: 3.01 -0.414 2.52 ; _atom_sites_solution_primary direct _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method None _refine_ls_number_reflns 3407 _refine_ls_number_parameters 388 _refine_ls_number_restraints 47 _refine_ls_R_factor_all 0.1004 _refine_ls_R_factor_gt 0.0393 _refine_ls_wR_factor_ref 0.0495 _refine_ls_wR_factor_gt 0.0495 _refine_ls_wR_factor_all 0.0692 _refine_ls_goodness_of_fit_ref 1.0242 _refine_ls_shift/su_max 0.000633 _refine_diff_density_max 0.96 _refine_diff_density_min -0.54 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# loop_ _atom_type_symbol _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C 0.0033 0.0016 'International Tables Vol C 4.2.6.8 and 6.1.1.4' H 0 0 'International Tables Vol C 4.2.6.8 and 6.1.1.4' Br -0.2901 2.4595 'International Tables Vol C 4.2.6.8 and 6.1.1.4' Co 0.3494 0.9721 'International Tables Vol C 4.2.6.8 and 6.1.1.4' N 0.0061 0.0033 'International Tables Vol C 4.2.6.8 and 6.1.1.4' O 0.0106 0.006 'International Tables Vol C 4.2.6.8 and 6.1.1.4' S 0.1246 0.1234 'International Tables Vol C 4.2.6.8 and 6.1.1.4' 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_disorder_assembly _atom_site_disorder_group C2 C 0.6538(4) 0.7652(3) 0.1004(3) 0.0489 Uani 1 . . C4 C 0.5944(6) 0.6305(5) 0.2483(4) 0.0716 Uani 1 . . C5 C 0.6562(6) 0.5605(5) 0.2809(4) 0.0774 Uani 1 . . C6 C 0.7494(6) 0.5345(4) 0.2568(4) 0.0738 Uani 1 . . C7 C 0.7852(5) 0.5808(4) 0.2014(4) 0.0645 Uani 1 . . C8 C 0.7239(4) 0.6525(3) 0.1688(3) 0.05 Uani 1 . . C9 C 0.6301(5) 0.6752(4) 0.1917(3) 0.0564 Uani 1 . . C10 C 0.6310(4) 0.8373(3) 0.0431(3) 0.0506 Uani 1 . . C11 C 0.5357(5) 0.8404(4) -0.0258(3) 0.0581 Uani 1 . . C12 C 0.5213(7) 0.9081(5) -0.0781(4) 0.0816 Uani 1 . . C13 C 0.5975(8) 0.9722(5) -0.0615(4) 0.0891 Uani 1 . . C14 C 0.6911(6) 0.9717(4) 0.0058(4) 0.0728 Uani 1 . . C15 C 0.7081(5) 0.9042(3) 0.0587(4) 0.0597 Uani 1 . . C17 C 0.7177(4) 0.7190(3) -0.1090(3) 0.0481 Uani 1 . . C19 C 0.7626(5) 0.9023(4) -0.2187(3) 0.0656 Uani 1 . . C20 C 0.8479(6) 0.9589(4) -0.1881(3) 0.0639 Uani 1 . . C21 C 0.9262(5) 0.9503(4) -0.1106(3) 0.0612 Uani 1 . . C22 C 0.9215(4) 0.8844(3) -0.0604(3) 0.0491 Uani 1 . . C23 C 0.8355(4) 0.8259(3) -0.0891(3) 0.0439 Uani 1 . . C24 C 0.7569(4) 0.8352(3) -0.1671(3) 0.047 Uani 1 . . C25 C 0.6666(4) 0.6378(4) -0.1001(3) 0.0541 Uani 1 . . C26 C 0.5492(5) 0.6260(4) -0.1168(3) 0.0621 Uani 1 . . C27 C 0.5124(6) 0.5431(5) -0.1024(4) 0.085 Uani 1 . . C28 C 0.5865(8) 0.4788(5) -0.0765(5) 0.0959 Uani 1 . . C29 C 0.7011(7) 0.4913(5) -0.0630(4) 0.082 Uani 1 . . C30 C 0.7407(6) 0.5696(4) -0.0753(4) 0.0646 Uani 1 . . C36 C 0.3085(10) 0.8040(13) 0.1651(11) 0.1102 Uani 0.5 . 1 C37 C 0.2358(16) 0.7864(15) 0.0762(11) 0.116 Uani 0.5 . 1 C38 C 0.2937(6) 0.8342(10) 0.1446(13) 0.1078 Uani 0.5 . 2 C39 C 0.2744(16) 0.7426(10) 0.1145(13) 0.107 Uani 0.5 . 2 C41 C 0.5278(14) 0.8482(11) 0.3703(10) 0.205 Uani 1 . . C42 C 0.6485(13) 0.8504(11) 0.3640(9) 0.2067 Uani 1 . . H3 H 0.5284 0.7749 0.1485 0.0718 Uiso 1 . . H4 H 0.5316 0.6474 0.2635 0.0884 Uiso 1 . . H5 H 0.6343 0.5281 0.3193 0.0882 Uiso 1 . . H6 H 0.789 0.4857 0.2793 0.0863 Uiso 1 . . H7 H 0.8486 0.5643 0.1856 0.0733 Uiso 1 . . H12 H 0.4586 0.9095 -0.1255 0.0953 Uiso 1 . . H13 H 0.5857 1.0177 -0.0967 0.1053 Uiso 1 . . H14 H 0.7434 1.016 0.0161 0.0912 Uiso 1 . . H15 H 0.7719 0.9028 0.1055 0.0734 Uiso 1 . . H18 H 0.6281 0.7566 -0.2218 0.0593 Uiso 1 . . H19 H 0.7086 0.9077 -0.2709 0.0732 Uiso 1 . . H20 H 0.855 1.0045 -0.2204 0.0762 Uiso 1 . . H21 H 0.983 0.9907 -0.0923 0.0705 Uiso 1 . . H22 H 0.9739 0.8796 -0.0082 0.0605 Uiso 1 . . H27 H 0.4341 0.5353 -0.1117 0.1042 Uiso 1 . . H28 H 0.5589 0.4259 -0.0674 0.1144 Uiso 1 . . H29 H 0.7517 0.4463 -0.0458 0.0975 Uiso 1 . . H30 H 0.8189 0.5786 -0.0665 0.0763 Uiso 1 . . H35 H 0.4374 0.8583 0.2164 0.1671 Uiso 1 . . H411 H 0.5301 0.866 0.4255 0.2384 Uiso 1 . . H412 H 0.4928 0.7928 0.3553 0.2382 Uiso 1 . . H421 H 0.6874 0.8026 0.3946 0.2981 Uiso 1 . . H422 H 0.6831 0.9031 0.386 0.2981 Uiso 1 . . H423 H 0.6397 0.8454 0.3063 0.298 Uiso 1 . . N1 N 0.7383(3) 0.7100(3) 0.1099(2) 0.0469 Uani 1 . . N3 N 0.5867(4) 0.7467(3) 0.1464(3) 0.0595 Uani 1 . . N16 N 0.8082(3) 0.7530(3) -0.0531(2) 0.0433 Uani 1 . . N18 N 0.6851(3) 0.7672(3) -0.1776(2) 0.0522 Uani 1 . . O35 O 0.4134(4) 0.8412(4) 0.1683(4) 0.1038 Uani 1 . . O40 O 0.4778(10) 0.9117(7) 0.3133(7) 0.2057 Uani 1 . . S31 S 0.43322(14) 0.75751(14) -0.04699(10) 0.0789 Uani 1 . . S32 S 0.44635(12) 0.70604(13) -0.15323(9) 0.0742 Uani 1 . . Co1 Co 0.87272(5) 0.71980(4) 0.06739(4) 0.0446 Uani 1 . . Br33 Br 0.99281(5) 0.82487(3) 0.15561(3) 0.0553 Uani 1 . . Br34 Br 0.99822(5) 0.60008(4) 0.08761(4) 0.0675 Uani 1 . . H381 H 0.2558 0.8746 0.1037 0.1347 Uiso 0.5 . 2 H382 H 0.2652 0.8391 0.1926 0.1347 Uiso 0.5 . 2 H371 H 0.1616 0.7612 0.0733 0.1462 Uiso 0.5 . 1 H372 H 0.2173 0.846 0.048 0.1462 Uiso 0.5 . 1 H373 H 0.2758 0.7544 0.045 0.1462 Uiso 0.5 . 1 H391 H 0.1907 0.7301 0.0918 0.1332 Uiso 0.5 . 2 H392 H 0.3046 0.7382 0.0635 0.1332 Uiso 0.5 . 2 H393 H 0.3142 0.7019 0.1543 0.1332 Uiso 0.5 . 2 H361 H 0.2679 0.8351 0.1933 0.1411 Uiso 0.5 . 1 H362 H 0.3252 0.7453 0.1905 0.1411 Uiso 0.5 . 1 H40 H 0.5141 0.9593 0.3236 0.2428 Uiso 1 . . 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 C2 0.053(3) 0.051(3) 0.043(2) -0.004(2) 0.016(2) -0.004(2) C4 0.068(4) 0.089(5) 0.066(4) 0.007(3) 0.034(3) -0.008(3) C5 0.076(4) 0.088(5) 0.071(4) 0.026(4) 0.026(3) -0.007(4) C6 0.069(4) 0.072(4) 0.075(4) 0.028(3) 0.016(3) 0.000(3) C7 0.061(3) 0.068(4) 0.062(3) 0.014(3) 0.015(3) 0.004(3) C8 0.046(3) 0.057(3) 0.046(3) 0.001(2) 0.013(2) -0.007(2) C9 0.058(3) 0.060(3) 0.052(3) 0.001(3) 0.018(2) -0.006(3) C10 0.051(3) 0.050(3) 0.054(3) -0.002(2) 0.021(2) 0.006(2) C11 0.050(3) 0.079(4) 0.046(3) 0.002(3) 0.016(2) 0.014(3) C12 0.084(5) 0.092(5) 0.063(4) 0.012(4) 0.015(3) 0.021(4) C13 0.138(7) 0.063(4) 0.069(4) 0.025(3) 0.038(5) 0.034(5) C14 0.091(5) 0.052(3) 0.079(4) 0.004(3) 0.032(4) 0.005(3) C15 0.067(3) 0.051(3) 0.059(3) 0.002(3) 0.016(3) 0.010(3) C17 0.040(2) 0.059(3) 0.043(2) -0.016(2) 0.0098(19) -0.003(2) C19 0.069(4) 0.072(4) 0.048(3) 0.014(3) 0.006(3) 0.008(3) C20 0.085(4) 0.054(3) 0.051(3) 0.007(3) 0.019(3) -0.006(3) C21 0.067(3) 0.055(3) 0.058(3) -0.003(3) 0.015(3) -0.013(3) C22 0.053(3) 0.050(3) 0.041(2) -0.003(2) 0.011(2) -0.007(2) C23 0.045(2) 0.051(3) 0.036(2) -0.003(2) 0.0133(19) 0.004(2) C24 0.043(2) 0.053(3) 0.041(2) -0.010(2) 0.0064(19) 0.001(2) C25 0.053(3) 0.064(3) 0.040(2) -0.015(2) 0.008(2) -0.022(3) C26 0.059(3) 0.077(4) 0.049(3) -0.014(3) 0.015(3) -0.014(3) C27 0.081(5) 0.102(6) 0.077(4) -0.025(4) 0.033(4) -0.049(5) C28 0.128(7) 0.071(5) 0.089(5) -0.005(4) 0.034(5) -0.033(5) C29 0.087(5) 0.066(4) 0.083(4) -0.005(3) 0.010(4) -0.018(4) C30 0.069(4) 0.056(3) 0.063(3) -0.003(3) 0.011(3) -0.013(3) C36 0.091(4) 0.116(6) 0.134(6) 0.004(5) 0.050(5) 0.003(4) C37 0.096(6) 0.124(7) 0.136(6) -0.003(6) 0.049(5) 0.004(6) C38 0.086(3) 0.112(6) 0.132(6) 0.003(5) 0.043(5) 0.008(5) C39 0.085(5) 0.112(6) 0.131(7) 0.003(6) 0.043(6) 0.008(6) C41 0.212(9) 0.211(8) 0.164(7) -0.043(6) 0.017(7) 0.059(7) C42 0.211(9) 0.215(9) 0.165(8) -0.044(7) 0.016(8) 0.058(8) N1 0.044(2) 0.051(2) 0.044(2) 0.0018(18) 0.0114(17) -0.001(2) N3 0.059(3) 0.068(3) 0.058(3) 0.005(2) 0.028(2) 0.007(2) N16 0.042(2) 0.050(2) 0.0364(19) -0.0029(17) 0.0104(16) -0.0069(18) N18 0.045(2) 0.069(3) 0.035(2) -0.0041(19) 0.0027(17) -0.002(2) O35 0.086(3) 0.110(4) 0.127(4) 0.002(3) 0.051(3) 0.009(3) O40 0.214(8) 0.204(8) 0.166(7) -0.049(6) 0.012(6) 0.062(7) S31 0.0560(8) 0.1184(14) 0.0660(9) -0.0199(9) 0.0242(7) -0.0100(9) S32 0.0456(7) 0.1163(14) 0.0559(8) -0.0205(9) 0.0089(6) -0.0070(8) Co1 0.0413(3) 0.0510(4) 0.0383(3) 0.0036(3) 0.0078(2) -0.0034(3) Br33 0.0557(3) 0.0570(3) 0.0422(3) 0.0044(2) -0.0008(2) -0.0088(2) Br34 0.0566(3) 0.0663(4) 0.0752(4) 0.0070(3) 0.0139(3) 0.0116(3) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 _geom_bond_publ_flag C2 C10 1.479(7) . . yes C2 N1 1.333(7) . . yes C2 N3 1.346(7) . . yes C4 C5 1.368(10) . . yes C4 C9 1.383(8) . . yes C4 H4 0.931 . . no C5 C6 1.401(10) . . yes C5 H5 0.942 . . no C6 C7 1.380(9) . . yes C6 H6 0.934 . . no C7 C8 1.386(8) . . yes C7 H7 0.944 . . no C8 C9 1.384(8) . . yes C8 N1 1.415(6) . . yes C9 N3 1.386(8) . . yes C10 C11 1.388(7) . . yes C10 C15 1.397(8) . . yes C11 C12 1.377(9) . . yes C11 S31 1.785(6) . . yes C12 C13 1.356(11) . . yes C12 H12 0.934 . . no C13 C14 1.359(11) . . yes C13 H13 0.925 . . no C14 C15 1.378(8) . . yes C14 H14 0.934 . . no C15 H15 0.935 . . no C17 C25 1.465(8) . . yes C17 N16 1.341(6) . . yes C17 N18 1.358(7) . . yes C19 C20 1.362(8) . . yes C19 C24 1.402(8) . . yes C19 H19 0.941 . . no C20 C21 1.388(8) . . yes C20 H20 0.933 . . no C21 C22 1.370(8) . . yes C21 H21 0.931 . . no C22 C23 1.382(7) . . yes C22 H22 0.932 . . no C23 C24 1.397(6) . . yes C23 N16 1.403(6) . . yes C24 N18 1.374(7) . . yes C25 C26 1.402(8) . . yes C25 C30 1.398(9) . . yes C26 C27 1.439(10) . . yes C26 S32 1.769(7) . . yes C27 C28 1.353(11) . . yes C27 H27 0.939 . . no C28 C29 1.377(11) . . yes C28 H28 0.938 . . no C29 C30 1.376(9) . . yes C29 H29 0.935 . . no C30 H30 0.942 . . no C36 C37 1.538(5) . . yes C36 O35 1.412(5) . . yes C36 H361 0.939 . . no C36 H362 1.022 . . no C37 H371 0.987 . . no C37 H372 1.057 . . no C37 H373 0.978 . . no C38 C39 1.537(5) . . yes C38 O35 1.413(5) . . yes C38 H381 0.96 . . no C38 H382 0.997 . . no C39 H391 1.006 . . no C39 H392 1.058 . . no C39 H393 0.958 . . no C41 C42 1.53(2) . . yes C41 H411 0.982 . . no C41 H412 0.979 . . no C41 O40 1.408(19) . . yes C42 H421 0.963 . . no C42 H422 0.961 . . no C42 H423 0.968 . . no H3 N3 0.86 . . no H18 N18 0.878 . . no H35 O35 0.832 . . no N1 Co1 2.020(4) . . yes N16 Co1 2.044(4) . . yes O40 H40 0.869 . . no S31 S32 2.053(2) . . yes Co1 Br33 2.4269(8) . . yes Co1 Br34 2.4102(9) . . yes 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_2 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C10 C2 N1 124.8(4) . . . yes C10 C2 N3 122.4(5) . . . yes N1 C2 N3 112.8(4) . . . yes C5 C4 C9 116.4(6) . . . yes C5 C4 H4 121.9 . . . no C9 C4 H4 121.7 . . . no C4 C5 C6 121.6(6) . . . yes C4 C5 H5 119 . . . no C6 C5 H5 119.3 . . . no C5 C6 C7 121.1(6) . . . yes C5 C6 H6 119.7 . . . no C7 C6 H6 119.2 . . . no C6 C7 C8 117.7(6) . . . yes C6 C7 H7 121.6 . . . no C8 C7 H7 120.7 . . . no C7 C8 C9 120.0(5) . . . yes C7 C8 N1 130.2(5) . . . yes C9 C8 N1 109.7(5) . . . yes C8 C9 C4 123.1(6) . . . yes C8 C9 N3 105.4(5) . . . yes C4 C9 N3 131.5(6) . . . yes C2 C10 C11 122.1(5) . . . yes C2 C10 C15 118.9(5) . . . yes C11 C10 C15 119.0(5) . . . yes C10 C11 C12 119.2(6) . . . yes C10 C11 S31 120.6(4) . . . yes C12 C11 S31 120.2(5) . . . yes C11 C12 C13 120.5(6) . . . yes C11 C12 H12 119.4 . . . no C13 C12 H12 120.1 . . . no C12 C13 C14 121.8(6) . . . yes C12 C13 H13 119.4 . . . no C14 C13 H13 118.8 . . . no C13 C14 C15 118.8(7) . . . yes C13 C14 H14 120.8 . . . no C15 C14 H14 120.4 . . . no C10 C15 C14 120.6(6) . . . yes C10 C15 H15 119.3 . . . no C14 C15 H15 120 . . . no C25 C17 N16 124.8(5) . . . yes C25 C17 N18 124.5(4) . . . yes N16 C17 N18 110.6(4) . . . yes C20 C19 C24 116.2(5) . . . yes C20 C19 H19 122.9 . . . no C24 C19 H19 120.8 . . . no C19 C20 C21 122.1(5) . . . yes C19 C20 H20 119.1 . . . no C21 C20 H20 118.8 . . . no C20 C21 C22 121.8(5) . . . yes C20 C21 H21 119 . . . no C22 C21 H21 119.2 . . . no C21 C22 C23 117.8(5) . . . yes C21 C22 H22 121 . . . no C23 C22 H22 121.1 . . . no C22 C23 C24 120.0(5) . . . yes C22 C23 N16 131.4(4) . . . yes C24 C23 N16 108.6(4) . . . yes C19 C24 C23 122.0(5) . . . yes C19 C24 N18 132.2(4) . . . yes C23 C24 N18 105.8(4) . . . yes C17 C25 C26 123.4(5) . . . yes C17 C25 C30 116.8(5) . . . yes C26 C25 C30 119.8(5) . . . yes C25 C26 C27 116.7(6) . . . yes C25 C26 S32 124.1(5) . . . yes C27 C26 S32 119.2(5) . . . yes C26 C27 C28 122.0(6) . . . yes C26 C27 H27 117.1 . . . no C28 C27 H27 120.9 . . . no C27 C28 C29 120.2(7) . . . yes C27 C28 H28 119.2 . . . no C29 C28 H28 120.7 . . . no C28 C29 C30 120.1(7) . . . yes C28 C29 H29 119.6 . . . no C30 C29 H29 120.3 . . . no C25 C30 C29 121.1(6) . . . yes C25 C30 H30 118.3 . . . no C29 C30 H30 120.6 . . . no C37 C36 O35 111.2(13) . . . yes C37 C36 H361 111.6 . . . no O35 C36 H361 113 . . . no C37 C36 H362 103.7 . . . no O35 C36 H362 107.7 . . . no H361 C36 H362 109.3 . . . no C36 C37 H371 111.9 . . . no C36 C37 H372 105.7 . . . no H371 C37 H372 106 . . . no C36 C37 H373 113.6 . . . no H371 C37 H373 112.4 . . . no H372 C37 H373 106.7 . . . no C39 C38 O35 102.2(11) . . . yes C39 C38 H381 113.4 . . . no O35 C38 H381 112.8 . . . no C39 C38 H382 107.1 . . . no O35 C38 H382 111.3 . . . no H381 C38 H382 109.7 . . . no C38 C39 H391 110.5 . . . no C38 C39 H392 106.5 . . . no H391 C39 H392 104.6 . . . no C38 C39 H393 114 . . . no H391 C39 H393 112.5 . . . no H392 C39 H393 108.2 . . . no C42 C41 H411 108.9 . . . no C42 C41 H412 111.3 . . . no H411 C41 H412 113.1 . . . no C42 C41 O40 99.3(14) . . . yes H411 C41 O40 109.9 . . . no H412 C41 O40 113.4 . . . no C41 C42 H421 106 . . . no C41 C42 H422 108.5 . . . no H421 C42 H422 112.8 . . . no C41 C42 H423 105.6 . . . no H421 C42 H423 111.8 . . . no H422 C42 H423 111.5 . . . no C8 N1 C2 104.2(4) . . . yes C8 N1 Co1 127.5(3) . . . yes C2 N1 Co1 127.3(3) . . . yes C9 N3 C2 107.9(5) . . . yes C9 N3 H3 125.9 . . . no C2 N3 H3 126.2 . . . no C23 N16 C17 106.2(4) . . . yes C23 N16 Co1 126.0(3) . . . yes C17 N16 Co1 126.7(3) . . . yes C24 N18 C17 108.9(4) . . . yes C24 N18 H18 125.2 . . . no C17 N18 H18 125.9 . . . no C36 O35 H35 102.4 . . . no C41 O40 H40 113.2 . . . no C11 S31 S32 103.1(2) . . . yes C26 S32 S31 102.61(19) . . . yes N16 Co1 N1 106.28(15) . . . yes N16 Co1 Br33 115.23(11) . . . yes N1 Co1 Br33 103.86(12) . . . yes N16 Co1 Br34 112.38(12) . . . yes N1 Co1 Br34 116.93(12) . . . yes Br33 Co1 Br34 102.17(3) . . . yes 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_D _geom_hbond_site_symmetry_H _geom_hbond_site_symmetry_A _geom_hbond_publ_flag N3 H3 O35 0.86 1.88 2.737(8) 172 . . . yes O35 H35 O40 0.83 1.8 2.620(13) 170 . . . yes # Attachment '- CCDC 758099.cif' #\#CIF_1.1 # CIF produced by WinGX routine CIF_UPDATE # Created on 2009-12-03 at 18:11:49 # Using CIFtbx version 2.6.2 16 Jun 1998 # Dictionary name : cif_core.dic # Dictionary vers : 2.3 # Request file : c:\wingx\files\archive.dat # CIF files read : publish dreduc struct data_3 _database_code_depnum_ccdc_archive 'CCDC 758099' #TrackingRef '- CCDC 758099.cif' _audit_creation_date 2009-12-03T18:11:49-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' _audit_conform_dict_name cif_core.dic _audit_conform_dict_version 2.3 _audit_conform_dict_location ftp://ftp.iucr.org/pub/cif_core.dic _publ_section_abstract ; Herein we report the synthesis, structural and spectroscopic characterization of coordination compounds with bis[2-(1H-benzimidazol-2-yl)phenyl]disulfide [bis-(2phSbz)] (1) and cobalt(II), zinc(II) and cadmium halides (2-7). Their X-ray diffraction analyses showed that the metal ions present similar distorted tetrahedral structure, with the disulfide ligand coordinated through the imidazolic nitrogen atoms, forming a twisted eleven membered chelate. Structures of nickel(II) compounds 8 and 9, showed that the disulfide bond in the ligand was broken and the two halves were coordinated to the nickel(II) through the sulfur and one imidazole nitrogen atom forming six membered rings. In 8, the two ligands were sulfides, however in 9 one of them was oxidized to a sulfone. In both compounds the nickel(II) has a distorted square planar geometry and the sulfur atoms are in cis positions. The oxidation reaction of bis-(2phSbz) was performed in KMnO4/NaOH, giving the 2-(1H,3H-benzimidazolium-2-yl)-benzene sulfonate (10). The solid state structure of compounds 2-5 and 7-10 was determined by X-ray diffraction analyses. ; #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_formula_moiety 'C26 H18 Cl2 N4 S2 Zn, 2(C2 H6 O)' _chemical_formula_sum 'C30 H30 Cl2 N4 O2 S2 Zn1' _chemical_formula_weight 679.01 _chemical_compound_source 'synthesis as described' _chemical_absolute_configuration . #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P 1 21/n 1' _symmetry_space_group_name_Hall '-P 2yn ' _symmetry_Int_Tables_number 14 loop_ _symmetry_equiv_pos_as_xyz x,y,z -x,-y,-z -x+1/2,y+1/2,-z+1/2 x+1/2,-y+1/2,z+1/2 _cell_length_a 12.1415(3) _cell_length_b 15.7394(4) _cell_length_c 16.8483(3) _cell_angle_alpha 90 _cell_angle_beta 108.652(2) _cell_angle_gamma 90 _cell_volume 3050.61(13) _cell_formula_units_Z 4 _cell_measurement_temperature 173 _cell_measurement_reflns_used 35900 _cell_measurement_theta_min 2 _cell_measurement_theta_max 27 _cell_measurement_wavelength 0.71073 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.35 _exptl_crystal_size_min 0.1 _exptl_crystal_density_diffrn 1.478 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1400 #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 1.152 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SADABS (Siemens, 1996)' _exptl_absorpt_correction_T_min 0.74 _exptl_absorpt_correction_T_max 0.89 #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_source 'Enraf Nonius FR590' _diffrn_ambient_temperature 173 _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_detector 'CCD plate' _diffrn_detector_area_resol_mean 9 _diffrn_orient_matrix_type 'by Bruker AXS Collect from scalepack cell' _diffrn_orient_matrix_ub_11 -0.761057E-1 _diffrn_orient_matrix_ub_12 -0.82135E-2 _diffrn_orient_matrix_ub_13 -0.45175E-1 _diffrn_orient_matrix_ub_21 0.412672E-1 _diffrn_orient_matrix_ub_22 -0.32025E-2 _diffrn_orient_matrix_ub_23 -0.426418E-1 _diffrn_orient_matrix_ub_31 0.78342E-2 _diffrn_orient_matrix_ub_32 -0.629202E-1 _diffrn_orient_matrix_ub_33 0.80674E-2 _diffrn_measurement_device '95mm CCD camera on \k-goniostat' _diffrn_measurement_device_type 'Nonius KappaCCD' _diffrn_measurement_method '\f & \w scans' _diffrn_standards_number 0 _diffrn_reflns_av_R_equivalents 0.049 _diffrn_reflns_number 30682 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -20 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 4.089 _diffrn_reflns_theta_max 27.473 _diffrn_reflns_theta_full 25.001 _diffrn_measured_fraction_theta_full 0.938 _diffrn_measured_fraction_theta_max 0.928 _reflns_number_total 6487 _reflns_number_gt 4628 _reflns_threshold_expression I>3.0\s(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection 'COLLECT (Nonius, 1997-2001).' _computing_cell_refinement 'DENZO/SCALEPACK (Otwinowski & Minor, 1997)' _computing_data_reduction 'DENZO/SCALEPACK (Otwinowski & Minor, 1997)' _computing_structure_solution 'SHELXS 86 (Sheldrick, 1986)' _computing_structure_refinement 'CRYSTALS (Betteridge et al., 2003)' _computing_molecular_graphics 'CAMERON (Watkin et al., 1996)' _computing_publication_material 'CRYSTALS (Betteridge et al., 2003)' #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _refine_ls_structure_factor_coef F _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details ; Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982) [weight] = 1.0/[A~0~*T~0~(x)+A~1~*T~1~(x) ... +A~n-1~]*T~n-1~(x)] where A~i~ are the Chebychev coefficients listed below and x= Fcalc/Fmax Method = Robust Weighting (Prince, 1982) W = [weight] * [1-(deltaF/6*sigmaF)^2^]^2^ A~i~ are: 1.97 -0.523 1.71 -0.298 0.457 ; _atom_sites_solution_primary direct _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method None _refine_ls_number_reflns 4628 _refine_ls_number_parameters 388 _refine_ls_number_restraints 47 _refine_ls_R_factor_all 0.0785 _refine_ls_R_factor_gt 0.0383 _refine_ls_wR_factor_ref 0.0442 _refine_ls_wR_factor_gt 0.0442 _refine_ls_wR_factor_all 0.0646 _refine_ls_goodness_of_fit_ref 1.0112 _refine_ls_shift/su_max 0.000512 _refine_diff_density_max 0.59 _refine_diff_density_min -0.65 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# loop_ _atom_type_symbol _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C 0.0033 0.0016 'International Tables Vol C 4.2.6.8 and 6.1.1.4' H 0 0 'International Tables Vol C 4.2.6.8 and 6.1.1.4' Cl 0.1484 0.1585 'International Tables Vol C 4.2.6.8 and 6.1.1.4' N 0.0061 0.0033 'International Tables Vol C 4.2.6.8 and 6.1.1.4' S 0.1246 0.1234 'International Tables Vol C 4.2.6.8 and 6.1.1.4' Zn 0.2839 1.4301 'International Tables Vol C 4.2.6.8 and 6.1.1.4' O 0.0106 0.006 'International Tables Vol C 4.2.6.8 and 6.1.1.4' 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_disorder_assembly _atom_site_disorder_group C2 C 0.1615(2) 0.76395(16) 0.10075(18) 0.0279 Uani 1 . . C4 C 0.0977(3) 0.6292(2) 0.2509(2) 0.0396 Uani 1 . . C5 C 0.1571(3) 0.5559(2) 0.2823(2) 0.0431 Uani 1 . . C6 C 0.2515(3) 0.5287(2) 0.2582(2) 0.0393 Uani 1 . . C7 C 0.2906(2) 0.57472(19) 0.20228(19) 0.0347 Uani 1 . . C8 C 0.2306(2) 0.64863(17) 0.16965(17) 0.0283 Uani 1 . . C9 C 0.1355(2) 0.67463(18) 0.19391(19) 0.0318 Uani 1 . . C10 C 0.1401(2) 0.83747(17) 0.04231(17) 0.0286 Uani 1 . . C11 C 0.0399(3) 0.8419(2) -0.02691(19) 0.0357 Uani 1 . . C12 C 0.0226(3) 0.9116(2) -0.0795(2) 0.0472 Uani 1 . . C13 C 0.1026(3) 0.9765(2) -0.0640(2) 0.0494 Uani 1 . . C14 C 0.2027(3) 0.97325(19) 0.0055(2) 0.0416 Uani 1 . . C15 C 0.2200(2) 0.90333(18) 0.05805(19) 0.0329 Uani 1 . . C17 C 0.2242(2) 0.71787(17) -0.11255(17) 0.0254 Uani 1 . . C19 C 0.2627(3) 0.90513(19) -0.22170(19) 0.0355 Uani 1 . . C20 C 0.3500(3) 0.96408(19) -0.1898(2) 0.0364 Uani 1 . . C21 C 0.4335(3) 0.95410(17) -0.11034(18) 0.0318 Uani 1 . . C22 C 0.4316(2) 0.88505(17) -0.05961(18) 0.0297 Uani 1 . . C23 C 0.3428(2) 0.82578(16) -0.09071(17) 0.0246 Uani 1 . . C24 C 0.2612(2) 0.83599(17) -0.16997(18) 0.0287 Uani 1 . . C25 C 0.1723(2) 0.63524(17) -0.10284(17) 0.029 Uani 1 . . C26 C 0.0519(2) 0.6234(2) -0.11800(19) 0.0364 Uani 1 . . C27 C 0.0119(3) 0.5436(2) -0.1036(2) 0.0495 Uani 1 . . C28 C 0.0893(3) 0.4762(2) -0.0762(2) 0.0515 Uani 1 . . C29 C 0.2054(3) 0.4872(2) -0.0644(2) 0.0441 Uani 1 . . C30 C 0.2466(3) 0.56660(19) -0.07754(19) 0.0349 Uani 1 . . C36 C -0.1935(5) 0.8098(6) 0.1676(6) 0.065 Uani 0.5 . 1 C37 C -0.2472(9) 0.7697(7) 0.0812(6) 0.0729 Uani 0.5 . 1 C38 C -0.2052(4) 0.8302(5) 0.1459(6) 0.0589 Uani 0.5 . 2 C39 C -0.2234(8) 0.7384(5) 0.1155(6) 0.0609 Uani 0.5 . 2 C41 C 0.0362(5) 0.8556(4) 0.3777(4) 0.0945 Uani 1 . . C42 C 0.1566(5) 0.8496(4) 0.3700(4) 0.0969 Uani 1 . . H3 H 0.0353 0.779 0.1503 0.0428 Uiso 1 . . H4 H 0.0353 0.6472 0.2658 0.0503 Uiso 1 . . H5 H 0.1332 0.5227 0.3209 0.0523 Uiso 1 . . H6 H 0.2903 0.4777 0.2802 0.0477 Uiso 1 . . H7 H 0.356 0.5571 0.1875 0.0418 Uiso 1 . . H12 H -0.0454 0.9135 -0.1265 0.0565 Uiso 1 . . H13 H 0.0883 1.0224 -0.1002 0.0612 Uiso 1 . . H14 H 0.2563 1.0186 0.016 0.0527 Uiso 1 . . H15 H 0.2876 0.8996 0.1055 0.0413 Uiso 1 . . H18 H 0.1292 0.7556 -0.2252 0.0381 Uiso 1 . . H19 H 0.207 0.9111 -0.2738 0.0437 Uiso 1 . . H20 H 0.3547 1.0119 -0.2219 0.0449 Uiso 1 . . H21 H 0.492 0.9948 -0.0913 0.0403 Uiso 1 . . H22 H 0.4879 0.8782 -0.0062 0.0369 Uiso 1 . . H27 H -0.0672 0.535 -0.1119 0.0603 Uiso 1 . . H28 H 0.0617 0.4234 -0.0662 0.0624 Uiso 1 . . H29 H 0.2576 0.4413 -0.0462 0.0525 Uiso 1 . . H30 H 0.3266 0.5743 -0.0701 0.0416 Uiso 1 . . H35 H -0.0555 0.8724 0.2136 0.0845 Uiso 1 . . H40 H -0.0234 0.96 0.3485 0.1453 Uiso 1 . . H361 H -0.2434 0.8564 0.176 0.0826 Uiso 0.5 . 1 H362 H -0.1859 0.7655 0.2108 0.0826 Uiso 0.5 . 1 H371 H -0.3242 0.7473 0.0767 0.0929 Uiso 0.5 . 1 H372 H -0.2549 0.8135 0.0384 0.0929 Uiso 0.5 . 1 H373 H -0.1979 0.7236 0.0728 0.0929 Uiso 0.5 . 1 H381 H -0.2443 0.871 0.101 0.0752 Uiso 0.5 . 2 H382 H -0.235 0.8377 0.1937 0.0752 Uiso 0.5 . 2 H391 H -0.3068 0.7254 0.0961 0.0774 Uiso 0.5 . 2 H392 H -0.1924 0.7321 0.0688 0.0774 Uiso 0.5 . 2 H393 H -0.1831 0.6991 0.1606 0.0774 Uiso 0.5 . 2 H411 H 0.042 0.8721 0.4357 0.1166 Uiso 1 . . H412 H 0.0003 0.7974 0.363 0.1167 Uiso 1 . . H421 H 0.19 0.7978 0.4009 0.1464 Uiso 1 . . H422 H 0.1978 0.9022 0.3943 0.1463 Uiso 1 . . H423 H 0.1471 0.8439 0.3101 0.1464 Uiso 1 . . N1 N 0.24546(18) 0.70695(14) 0.11102(14) 0.0263 Uani 1 . . N3 N 0.0941(2) 0.74783(15) 0.14826(16) 0.0328 Uani 1 . . N16 N 0.31731(18) 0.75092(14) -0.05452(14) 0.0241 Uani 1 . . N18 N 0.1881(2) 0.76666(15) -0.18148(15) 0.0307 Uani 1 . . O35 O -0.0829(2) 0.84162(16) 0.17210(17) 0.0519 Uani 1 . . O40 O -0.0246(4) 0.9162(2) 0.3213(3) 0.0993 Uani 1 . . S31 S -0.06624(7) 0.75895(6) -0.04897(6) 0.0444 Uani 1 . . S32 S -0.05326(6) 0.70552(6) -0.15705(5) 0.0423 Uani 1 . . Cl33 Cl 0.49999(6) 0.81699(4) 0.15150(4) 0.0305 Uani 1 . . Cl34 Cl 0.49707(6) 0.59841(5) 0.08853(5) 0.0363 Uani 1 . . Zn1 Zn 0.38369(2) 0.715908(19) 0.068193(19) 0.025 Uani 1 . . 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 C2 0.0265(12) 0.0298(13) 0.0274(16) -0.0034(10) 0.0088(11) -0.0025(10) C4 0.0334(15) 0.0534(18) 0.0375(19) 0.0042(13) 0.0191(14) -0.0004(13) C5 0.0419(16) 0.0515(18) 0.038(2) 0.0125(14) 0.0156(14) -0.0029(14) C6 0.0358(15) 0.0428(16) 0.0376(19) 0.0119(13) 0.0095(13) -0.0002(12) C7 0.0260(13) 0.0433(16) 0.0335(18) 0.0049(12) 0.0076(12) -0.0002(11) C8 0.0273(12) 0.0342(13) 0.0214(15) -0.0001(10) 0.0051(10) -0.0025(10) C9 0.0266(13) 0.0376(14) 0.0315(16) 0.0001(11) 0.0098(11) -0.0019(11) C10 0.0317(13) 0.0331(13) 0.0231(15) -0.0024(10) 0.0118(11) 0.0067(10) C11 0.0337(14) 0.0467(16) 0.0274(17) -0.0035(12) 0.0105(12) 0.0074(12) C12 0.0498(19) 0.054(2) 0.033(2) 0.0054(14) 0.0061(15) 0.0140(15) C13 0.066(2) 0.0428(18) 0.041(2) 0.0112(14) 0.0195(17) 0.0148(16) C14 0.0510(18) 0.0330(15) 0.045(2) 0.0005(12) 0.0203(15) 0.0050(13) C15 0.0332(14) 0.0329(14) 0.0311(17) -0.0010(11) 0.0083(12) 0.0027(11) C17 0.0217(11) 0.0343(13) 0.0209(14) -0.0058(10) 0.0079(10) -0.0010(10) C19 0.0351(15) 0.0442(16) 0.0229(16) 0.0042(11) 0.0033(11) 0.0041(12) C20 0.0439(16) 0.0336(14) 0.0328(18) 0.0055(11) 0.0136(13) 0.0038(12) C21 0.0370(14) 0.0313(13) 0.0277(16) -0.0025(11) 0.0111(12) -0.0047(11) C22 0.0307(13) 0.0350(14) 0.0216(15) -0.0032(10) 0.0057(11) -0.0007(11) C23 0.0232(11) 0.0286(12) 0.0226(14) -0.0008(10) 0.0081(10) 0.0003(9) C24 0.0243(12) 0.0365(14) 0.0237(15) -0.0027(10) 0.0051(10) 0.0007(10) C25 0.0275(13) 0.0378(14) 0.0210(15) -0.0070(10) 0.0067(11) -0.0083(10) C26 0.0268(14) 0.0539(18) 0.0277(17) -0.0087(12) 0.0075(11) -0.0104(12) C27 0.0368(17) 0.064(2) 0.049(2) -0.0126(16) 0.0152(15) -0.0246(16) C28 0.061(2) 0.0473(19) 0.047(2) -0.0060(15) 0.0179(17) -0.0248(17) C29 0.0521(19) 0.0391(16) 0.0369(19) -0.0023(13) 0.0085(14) -0.0105(14) C30 0.0332(14) 0.0389(15) 0.0287(17) -0.0071(11) 0.0044(12) -0.0067(12) C36 0.055(3) 0.069(4) 0.083(4) 0.014(3) 0.038(3) 0.000(3) C37 0.060(4) 0.081(5) 0.090(5) 0.003(4) 0.040(4) -0.005(4) C38 0.048(2) 0.064(3) 0.070(4) 0.015(3) 0.026(3) 0.002(3) C39 0.052(4) 0.069(4) 0.067(4) 0.008(3) 0.026(3) 0.005(3) C41 0.108(3) 0.104(3) 0.081(3) -0.004(2) 0.044(2) 0.015(2) C42 0.101(3) 0.108(4) 0.086(4) -0.005(3) 0.036(3) 0.015(3) N1 0.0232(10) 0.0332(11) 0.0217(13) -0.0007(8) 0.0059(8) -0.0002(8) N3 0.0327(12) 0.0354(12) 0.0337(15) 0.0017(10) 0.0155(10) 0.0035(10) N16 0.0211(10) 0.0300(10) 0.0209(12) -0.0018(8) 0.0062(8) -0.0015(8) N18 0.0250(11) 0.0414(13) 0.0217(13) -0.0033(9) 0.0017(9) -0.0033(9) O35 0.0447(12) 0.0539(14) 0.0648(17) 0.0087(11) 0.0283(12) 0.0102(10) O40 0.124(3) 0.084(2) 0.086(3) -0.0222(17) 0.029(2) 0.027(2) S31 0.0310(4) 0.0675(5) 0.0361(5) -0.0111(4) 0.0127(3) -0.0057(3) S32 0.0233(3) 0.0678(5) 0.0320(5) -0.0116(3) 0.0035(3) -0.0022(3) Cl33 0.0288(3) 0.0343(3) 0.0233(4) 0.0017(2) 0.0010(2) -0.0042(2) Cl34 0.0299(3) 0.0384(4) 0.0388(4) 0.0035(3) 0.0083(3) 0.0058(3) Zn1 0.02115(14) 0.03111(16) 0.02123(18) 0.00130(11) 0.00462(11) -0.00133(11) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 _geom_bond_publ_flag C2 C10 1.487(4) . . yes C2 N1 1.327(3) . . yes C2 N3 1.340(4) . . yes C4 C5 1.373(5) . . yes C4 C9 1.389(4) . . yes C4 H4 0.916 . . no C5 C6 1.400(5) . . yes C5 H5 0.95 . . no C6 C7 1.387(4) . . yes C6 H6 0.945 . . no C7 C8 1.389(4) . . yes C7 H7 0.947 . . no C8 C9 1.403(4) . . yes C8 N1 1.402(3) . . yes C9 N3 1.387(4) . . yes C10 C11 1.391(4) . . yes C10 C15 1.386(4) . . yes C11 C12 1.383(5) . . yes C11 S31 1.788(3) . . yes C12 C13 1.376(5) . . yes C12 H12 0.944 . . no C13 C14 1.393(5) . . yes C13 H13 0.925 . . no C14 C15 1.386(4) . . yes C14 H14 0.943 . . no C15 H15 0.947 . . no C17 C25 1.477(4) . . yes C17 N16 1.341(3) . . yes C17 N18 1.344(4) . . yes C19 C20 1.382(4) . . yes C19 C24 1.398(4) . . yes C19 H19 0.926 . . no C20 C21 1.406(4) . . yes C20 H20 0.938 . . no C21 C22 1.387(4) . . yes C21 H21 0.934 . . no C22 C23 1.395(4) . . yes C22 H22 0.946 . . no C23 C24 1.394(4) . . yes C23 N16 1.406(3) . . yes C24 N18 1.381(4) . . yes C25 C26 1.414(4) . . yes C25 C30 1.385(4) . . yes C26 C27 1.396(5) . . yes C26 S32 1.787(3) . . yes C27 C28 1.394(6) . . yes C27 H27 0.935 . . no C28 C29 1.369(5) . . yes C28 H28 0.933 . . no C29 C30 1.390(4) . . yes C29 H29 0.945 . . no C30 H30 0.946 . . no C36 C37 1.529(5) . . yes C36 H361 0.99 . . no C36 H362 0.99 . . no C36 O35 1.412(5) . . yes C37 H371 0.98 . . no C37 H372 0.98 . . no C37 H373 0.98 . . no C38 C39 1.525(5) . . yes C38 H381 0.99 . . no C38 H382 0.99 . . no C38 O35 1.419(4) . . yes C39 H391 0.98 . . no C39 H392 0.98 . . no C39 H393 0.98 . . no C41 C42 1.511(9) . . yes C41 H411 0.991 . . no C41 H412 1.011 . . no C41 O40 1.383(7) . . yes C42 H421 0.982 . . no C42 H422 0.987 . . no C42 H423 0.983 . . no H3 N3 0.875 . . no H18 N18 0.864 . . no H35 O35 0.829 . . no H40 O40 0.825 . . no N1 Zn1 2.033(2) . . yes N16 Zn1 2.040(2) . . yes S31 S32 2.0570(12) . . yes Cl33 Zn1 2.2863(7) . . yes Cl34 Zn1 2.2651(7) . . yes 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_2 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C10 C2 N1 125.2(2) . . . yes C10 C2 N3 122.1(2) . . . yes N1 C2 N3 112.6(2) . . . yes C5 C4 C9 116.7(3) . . . yes C5 C4 H4 122.2 . . . no C9 C4 H4 121 . . . no C4 C5 C6 121.6(3) . . . yes C4 C5 H5 119.2 . . . no C6 C5 H5 119.3 . . . no C5 C6 C7 121.8(3) . . . yes C5 C6 H6 119.8 . . . no C7 C6 H6 118.3 . . . no C6 C7 C8 117.1(3) . . . yes C6 C7 H7 121.6 . . . no C8 C7 H7 121.3 . . . no C7 C8 C9 120.3(3) . . . yes C7 C8 N1 131.1(3) . . . yes C9 C8 N1 108.5(2) . . . yes C8 C9 C4 122.4(3) . . . yes C8 C9 N3 105.5(2) . . . yes C4 C9 N3 132.1(3) . . . yes C2 C10 C11 121.0(3) . . . yes C2 C10 C15 119.4(3) . . . yes C11 C10 C15 119.6(3) . . . yes C10 C11 C12 119.3(3) . . . yes C10 C11 S31 121.1(2) . . . yes C12 C11 S31 119.6(3) . . . yes C11 C12 C13 120.9(3) . . . yes C11 C12 H12 118.4 . . . no C13 C12 H12 120.7 . . . no C12 C13 C14 120.4(3) . . . yes C12 C13 H13 118.8 . . . no C14 C13 H13 120.8 . . . no C13 C14 C15 118.6(3) . . . yes C13 C14 H14 119.6 . . . no C15 C14 H14 121.7 . . . no C10 C15 C14 121.2(3) . . . yes C10 C15 H15 118.7 . . . no C14 C15 H15 120.1 . . . no C25 C17 N16 123.4(2) . . . yes C25 C17 N18 124.5(2) . . . yes N16 C17 N18 112.0(2) . . . yes C20 C19 C24 116.2(3) . . . yes C20 C19 H19 122.5 . . . no C24 C19 H19 121.3 . . . no C19 C20 C21 121.7(3) . . . yes C19 C20 H20 119.7 . . . no C21 C20 H20 118.7 . . . no C20 C21 C22 121.7(3) . . . yes C20 C21 H21 119.2 . . . no C22 C21 H21 119.1 . . . no C21 C22 C23 117.1(3) . . . yes C21 C22 H22 121.8 . . . no C23 C22 H22 121.1 . . . no C22 C23 C24 120.6(2) . . . yes C22 C23 N16 130.4(3) . . . yes C24 C23 N16 108.9(2) . . . yes C19 C24 C23 122.7(3) . . . yes C19 C24 N18 131.6(3) . . . yes C23 C24 N18 105.8(2) . . . yes C17 C25 C26 123.3(3) . . . yes C17 C25 C30 117.5(2) . . . yes C26 C25 C30 119.2(3) . . . yes C25 C26 C27 119.0(3) . . . yes C25 C26 S32 123.2(2) . . . yes C27 C26 S32 117.8(2) . . . yes C26 C27 C28 120.4(3) . . . yes C26 C27 H27 120.2 . . . no C28 C27 H27 119.4 . . . no C27 C28 C29 120.4(3) . . . yes C27 C28 H28 119.7 . . . no C29 C28 H28 119.9 . . . no C28 C29 C30 119.8(3) . . . yes C28 C29 H29 120.2 . . . no C30 C29 H29 120 . . . no C29 C30 C25 121.2(3) . . . yes C29 C30 H30 120 . . . no C25 C30 H30 118.8 . . . no C37 C36 H361 110.3 . . . no C37 C36 H362 108.7 . . . no H361 C36 H362 109.5 . . . no C37 C36 O35 107.8(7) . . . yes H361 C36 O35 110.2 . . . no H362 C36 O35 110.3 . . . no C36 C37 H371 109.1 . . . no C36 C37 H372 108.8 . . . no H371 C37 H372 109.5 . . . no C36 C37 H373 110.4 . . . no H371 C37 H373 109.5 . . . no H372 C37 H373 109.5 . . . no C39 C38 H381 112 . . . no C39 C38 H382 109.6 . . . no H381 C38 H382 109.5 . . . no C39 C38 O35 104.5(6) . . . yes H381 C38 O35 110.7 . . . no H382 C38 O35 110.5 . . . no C38 C39 H391 109.4 . . . no C38 C39 H392 108.3 . . . no H391 C39 H392 109.5 . . . no C38 C39 H393 110.7 . . . no H391 C39 H393 109.5 . . . no H392 C39 H393 109.5 . . . no C42 C41 H411 109.6 . . . no C42 C41 H412 106 . . . no H411 C41 H412 111.7 . . . no C42 C41 O40 107.6(5) . . . yes H411 C41 O40 110.5 . . . no H412 C41 O40 111.3 . . . no C41 C42 H421 104.6 . . . no C41 C42 H422 106.7 . . . no H421 C42 H422 114.1 . . . no C41 C42 H423 107.1 . . . no H421 C42 H423 111.2 . . . no H422 C42 H423 112.4 . . . no C8 N1 C2 105.6(2) . . . yes C8 N1 Zn1 127.04(17) . . . yes C2 N1 Zn1 126.42(18) . . . yes C9 N3 C2 107.8(2) . . . yes C9 N3 H3 126.8 . . . no C2 N3 H3 125.4 . . . no C23 N16 C17 105.1(2) . . . yes C23 N16 Zn1 126.55(17) . . . yes C17 N16 Zn1 127.01(18) . . . yes C24 N18 C17 108.2(2) . . . yes C24 N18 H18 126.8 . . . no C17 N18 H18 125 . . . no C36 O35 H35 111.8 . . . no C41 O40 H40 106.5 . . . no C11 S31 S32 103.20(10) . . . yes C26 S32 S31 102.57(11) . . . yes N16 Zn1 N1 105.96(9) . . . yes N16 Zn1 Cl33 113.61(6) . . . yes N1 Zn1 Cl33 104.38(7) . . . yes N16 Zn1 Cl34 113.44(6) . . . yes N1 Zn1 Cl34 114.86(7) . . . yes Cl33 Zn1 Cl34 104.43(3) . . . yes # Attachment '- CCDC 758100.cif' #\#CIF_1.1 # CIF produced by WinGX routine CIF_UPDATE # Created on 2009-12-03 at 13:49:55 # Using CIFtbx version 2.6.2 16 Jun 1998 # Dictionary name : cif_core.dic # Dictionary vers : 2.3 # Request file : c:\wingx\files\archive.dat # CIF files read : publish dreduc struct data_4 _database_code_depnum_ccdc_archive 'CCDC 758100' #TrackingRef '- CCDC 758100.cif' _audit_creation_date 2009-12-03T13:49:55-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' _audit_conform_dict_name cif_core.dic _audit_conform_dict_version 2.3 _audit_conform_dict_location ftp://ftp.iucr.org/pub/cif_core.dic _publ_section_abstract ; Herein we report the synthesis, structural and spectroscopic characterization of coordination compounds with bis[2-(1H-benzimidazol-2-yl)phenyl]disulfide [bis-(2phSbz)] (1) and cobalt(II), zinc(II) and cadmium halides (2-7). Their X-ray diffraction analyses showed that the metal ions present similar distorted tetrahedral structure, with the disulfide ligand coordinated through the imidazolic nitrogen atoms, forming a twisted eleven membered chelate. Structures of nickel(II) compounds 8 and 9, showed that the disulfide bond in the ligand was broken and the two halves were coordinated to the nickel(II) through the sulfur and one imidazole nitrogen atom forming six membered rings. In 8, the two ligands were sulfides, however in 9 one of them was oxidized to a sulfone. In both compounds the nickel(II) has a distorted square planar geometry and the sulfur atoms are in cis positions. The oxidation reaction of bis-(2phSbz) was performed in KMnO4/NaOH, giving the 2-(1H,3H-benzimidazolium-2-yl)-benzene sulfonate (10). The solid state structure of compounds 2-5 and 7-10 was determined by X-ray diffraction analyses. ; #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_formula_moiety 'C26 H18 Br2 N4 S2 Zn, 2(C2 H6 O)' _chemical_formula_sum 'C30 H30 Br2 N4 O2 S2 Zn1' _chemical_formula_weight 767.91 _chemical_compound_source 'synthesis as described' _chemical_absolute_configuration . #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P 1 21/n 1' _symmetry_space_group_name_Hall '-P 2yn' _symmetry_Int_Tables_number 14 loop_ _symmetry_equiv_pos_as_xyz x,y,z -x,-y,-z -x+1/2,y+1/2,-z+1/2 x+1/2,-y+1/2,z+1/2 _cell_length_a 12.2875(1) _cell_length_b 15.7146(2) _cell_length_c 17.1248(2) _cell_angle_alpha 90 _cell_angle_beta 107.828(1) _cell_angle_gamma 90 _cell_volume 3147.89(6) _cell_formula_units_Z 4 _cell_measurement_temperature 173 _cell_measurement_reflns_used 25430 _cell_measurement_theta_min 3 _cell_measurement_theta_max 27 _cell_measurement_wavelength 0.71073 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.15 _exptl_crystal_density_diffrn 1.62 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1544 #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 3.486 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SADABS (Siemens, 1996)' _exptl_absorpt_correction_T_min 0.45 _exptl_absorpt_correction_T_max 0.59 #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_source 'Enraf Nonius FR590' _diffrn_ambient_temperature 173 _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_detector 'CCD plate' _diffrn_detector_area_resol_mean 9 _diffrn_orient_matrix_type 'by Bruker AXS Collect from scalepack cell' _diffrn_orient_matrix_ub_11 0.41929E-2 _diffrn_orient_matrix_ub_12 0.431829E-1 _diffrn_orient_matrix_ub_13 -0.418746E-1 _diffrn_orient_matrix_ub_21 0.73489E-1 _diffrn_orient_matrix_ub_22 -0.255991E-1 _diffrn_orient_matrix_ub_23 -0.22482E-2 _diffrn_orient_matrix_ub_31 -0.434755E-1 _diffrn_orient_matrix_ub_32 -0.391069E-1 _diffrn_orient_matrix_ub_33 -0.447674E-1 _diffrn_measurement_device '95mm CCD camera on \k-goniostat' _diffrn_measurement_device_type 'Nonius KappaCCD' _diffrn_measurement_method '\f & \w scans' _diffrn_standards_number 0 _diffrn_reflns_av_R_equivalents 0.077 _diffrn_reflns_number 43854 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -20 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 3.123 _diffrn_reflns_theta_max 27.482 _diffrn_reflns_theta_full 26.932 _diffrn_measured_fraction_theta_full 0.996 _diffrn_measured_fraction_theta_max 0.994 _reflns_number_total 7172 _reflns_number_gt 4858 _reflns_threshold_expression I>3.0\s(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection 'COLLECT (Nonius, 1997-2001).' _computing_cell_refinement 'DENZO/SCALEPACK (Otwinowski & Minor, 1997)' _computing_data_reduction 'DENZO/SCALEPACK (Otwinowski & Minor, 1997)' _computing_structure_solution 'SHELXS 86 (Sheldrick, 1986)' _computing_structure_refinement 'CRYSTALS (Betteridge et al., 2003)' _computing_molecular_graphics 'CAMERON (Watkin et al., 1996)' _computing_publication_material 'CRYSTALS (Betteridge et al., 2003)' #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _refine_ls_structure_factor_coef F _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details ; Method= Modified Sheldrick w=1/[\s^2^(F^2^) + ( 0.00P)^2^ + 0.07P] ,where P=(max(Fo^2^,0) + 2Fc^2^)/3 ; _atom_sites_solution_primary direct _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method None _refine_ls_number_reflns 4858 _refine_ls_number_parameters 388 _refine_ls_number_restraints 47 _refine_ls_R_factor_all 0.0689 _refine_ls_R_factor_gt 0.0377 _refine_ls_wR_factor_ref 0.047 _refine_ls_wR_factor_gt 0.047 _refine_ls_wR_factor_all 0.0646 _refine_ls_goodness_of_fit_ref 1.0336 _refine_ls_shift/su_max 0.000788 _refine_diff_density_max 0.85 _refine_diff_density_min -0.67 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# loop_ _atom_type_symbol _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C 0.0033 0.0016 'International Tables Vol C 4.2.6.8 and 6.1.1.4' H 0 0 'International Tables Vol C 4.2.6.8 and 6.1.1.4' Br -0.2901 2.4595 'International Tables Vol C 4.2.6.8 and 6.1.1.4' N 0.0061 0.0033 'International Tables Vol C 4.2.6.8 and 6.1.1.4' O 0.0106 0.006 'International Tables Vol C 4.2.6.8 and 6.1.1.4' S 0.1246 0.1234 'International Tables Vol C 4.2.6.8 and 6.1.1.4' Zn 0.2839 1.4301 'International Tables Vol C 4.2.6.8 and 6.1.1.4' 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_disorder_assembly _atom_site_disorder_group C2 C 0.6543(3) 0.2361(3) 0.1000(2) 0.027 Uani 1 . . C4 C 0.5940(4) 0.3708(3) 0.2503(3) 0.0375 Uani 1 . . C5 C 0.6554(4) 0.4423(3) 0.2829(3) 0.0403 Uani 1 . . C6 C 0.7509(4) 0.4687(3) 0.2597(3) 0.0378 Uani 1 . . C7 C 0.7867(4) 0.4231(3) 0.2037(3) 0.0321 Uani 1 . . C8 C 0.7252(3) 0.3502(3) 0.1695(2) 0.0272 Uani 1 . . C9 C 0.6304(3) 0.3254(3) 0.1934(3) 0.0294 Uani 1 . . C10 C 0.6324(3) 0.1637(3) 0.0427(3) 0.0266 Uani 1 . . C11 C 0.5350(4) 0.1607(3) -0.0257(3) 0.0332 Uani 1 . . C12 C 0.5189(4) 0.0913(3) -0.0785(3) 0.0457 Uani 1 . . C13 C 0.5967(5) 0.0253(3) -0.0636(3) 0.0482 Uani 1 . . C14 C 0.6917(4) 0.0276(3) 0.0044(3) 0.0405 Uani 1 . . C16 C 0.7088(4) 0.0962(3) 0.0576(3) 0.0324 Uani 1 . . C17 C 0.7196(3) 0.2837(3) -0.1083(2) 0.0245 Uani 1 . . C19 C 0.7625(4) 0.0977(3) -0.2177(3) 0.0364 Uani 1 . . C20 C 0.8488(4) 0.0395(3) -0.1876(3) 0.0372 Uani 1 . . C21 C 0.9281(4) 0.0486(3) -0.1098(3) 0.0321 Uani 1 . . C22 C 0.9249(3) 0.1159(3) -0.0594(2) 0.0271 Uani 1 . . C23 C 0.8379(3) 0.1753(3) -0.0881(2) 0.0227 Uani 1 . . C24 C 0.7585(3) 0.1659(3) -0.1660(2) 0.0261 Uani 1 . . C25 C 0.6684(3) 0.3659(3) -0.0995(2) 0.0286 Uani 1 . . C26 C 0.5503(4) 0.3791(3) -0.1151(3) 0.0344 Uani 1 . . C27 C 0.5110(4) 0.4601(4) -0.1024(3) 0.0456 Uani 1 . . C28 C 0.5857(5) 0.5264(3) -0.0761(3) 0.0493 Uani 1 . . C29 C 0.7020(4) 0.5144(3) -0.0627(3) 0.0411 Uani 1 . . C30 C 0.7420(4) 0.4354(3) -0.0747(3) 0.0347 Uani 1 . . C36 C 0.2949(5) 0.1717(6) 0.1559(7) 0.0678 Uani 0.65 . 1 C37 C 0.2674(9) 0.2529(6) 0.1051(7) 0.0723 Uani 0.65 . 1 C38 C 0.3115(10) 0.2079(11) 0.1545(11) 0.0649 Uani 0.35 . 2 C39 C 0.2320(14) 0.2029(13) 0.0659(10) 0.0676 Uani 0.35 . 2 C41 C 0.5309(7) 0.1577(6) 0.3744(5) 0.1033 Uani 1 . . C42 C 0.6488(6) 0.1497(6) 0.3654(5) 0.0998 Uani 1 . . H3 H 0.5306 0.2251 0.1496 0.035 Uiso 1 . . H4 H 0.5308 0.354 0.2649 0.0454 Uiso 1 . . H5 H 0.634 0.4753 0.3214 0.049 Uiso 1 . . H6 H 0.7906 0.5179 0.2826 0.045 Uiso 1 . . H7 H 0.8489 0.439 0.1877 0.0386 Uiso 1 . . H12 H 0.4552 0.0893 -0.1235 0.0543 Uiso 1 . . H13 H 0.5833 -0.0208 -0.0984 0.0577 Uiso 1 . . H14 H 0.7444 -0.0166 0.0147 0.0478 Uiso 1 . . H15 H 0.7734 0.0968 0.1031 0.0386 Uiso 1 . . H18 H 0.6279 0.2435 -0.2178 0.0338 Uiso 1 . . H19 H 0.7104 0.0925 -0.2689 0.0438 Uiso 1 . . H20 H 0.854 -0.0066 -0.2201 0.0451 Uiso 1 . . H21 H 0.9844 0.0084 -0.0924 0.0378 Uiso 1 . . H22 H 0.9781 0.1224 -0.0075 0.0319 Uiso 1 . . H27 H 0.4326 0.4689 -0.1134 0.0551 Uiso 1 . . H28 H 0.5585 0.5784 -0.0661 0.0592 Uiso 1 . . H29 H 0.7535 0.5589 -0.0457 0.049 Uiso 1 . . H30 H 0.8193 0.4275 -0.0675 0.042 Uiso 1 . . H35 H 0.4302 0.1366 0.2178 0.0679 Uiso 1 . . H40 H 0.4965 0.0449 0.3325 0.1425 Uiso 1 . . H361 H 0.2784 0.1786 0.2063 0.0833 Uiso 0.65 . 1 H362 H 0.2523 0.1251 0.1265 0.0833 Uiso 0.65 . 1 H371 H 0.1885 0.2661 0.0927 0.0891 Uiso 0.65 . 1 H372 H 0.3117 0.2983 0.1353 0.0891 Uiso 0.65 . 1 H373 H 0.2857 0.2449 0.0555 0.0891 Uiso 0.65 . 1 H381 H 0.3304 0.2653 0.1705 0.0792 Uiso 0.35 . 2 H382 H 0.2691 0.1842 0.1872 0.0792 Uiso 0.35 . 2 H391 H 0.1651 0.2354 0.0611 0.0835 Uiso 0.35 . 2 H392 H 0.2726 0.2271 0.0322 0.0835 Uiso 0.35 . 2 H393 H 0.2112 0.146 0.0489 0.0835 Uiso 0.35 . 2 H411 H 0.5316 0.1466 0.4291 0.1201 Uiso 1 . . H412 H 0.5008 0.213 0.3587 0.1201 Uiso 1 . . H421 H 0.6996 0.1894 0.4 0.1151 Uiso 1 . . H422 H 0.6759 0.0935 0.3804 0.1151 Uiso 1 . . H423 H 0.645 0.16 0.31 0.1151 Uiso 1 . . N1 N 0.7396(3) 0.2926(2) 0.1110(2) 0.025 Uani 1 . . N3 N 0.5885(3) 0.2536(2) 0.1482(2) 0.0293 Uani 1 . . N16 N 0.8106(3) 0.2497(2) -0.05250(19) 0.024 Uani 1 . . N18 N 0.6861(3) 0.2350(2) -0.1765(2) 0.0282 Uani 1 . . O35 O 0.4130(3) 0.1595(2) 0.1692(3) 0.0563 Uani 1 . . O40 O 0.4665(6) 0.0941(4) 0.3175(4) 0.1227 Uani 1 . . S31 S 0.43262(10) 0.24450(9) -0.04608(7) 0.0417 Uani 1 . . S32 S 0.44610(9) 0.29688(9) -0.15257(7) 0.04 Uani 1 . . Zn1 Zn 0.87548(4) 0.28323(3) 0.06823(3) 0.0231 Uani 1 . . Br33 Br 0.99409(3) 0.17588(3) 0.15613(2) 0.0284 Uani 1 . . Br34 Br 0.99949(4) 0.40488(3) 0.08761(3) 0.035 Uani 1 . . 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 C2 0.025(2) 0.030(2) 0.025(2) 0.0006(17) 0.0056(17) 0.0019(17) C4 0.038(3) 0.043(3) 0.038(3) -0.003(2) 0.021(2) 0.000(2) C5 0.037(3) 0.050(3) 0.038(3) -0.013(2) 0.017(2) 0.005(2) C6 0.036(2) 0.037(3) 0.038(3) -0.015(2) 0.009(2) -0.001(2) C7 0.029(2) 0.032(3) 0.035(2) -0.0030(19) 0.0084(19) -0.0001(18) C8 0.023(2) 0.032(2) 0.025(2) -0.0011(18) 0.0052(17) 0.0066(17) C9 0.024(2) 0.035(2) 0.029(2) 0.0001(19) 0.0078(18) 0.0019(18) C10 0.026(2) 0.027(2) 0.028(2) 0.0000(17) 0.0102(18) -0.0046(17) C11 0.034(2) 0.039(3) 0.028(2) 0.0021(19) 0.0111(19) -0.006(2) C12 0.047(3) 0.054(3) 0.030(2) -0.005(2) 0.002(2) -0.013(3) C13 0.069(4) 0.040(3) 0.040(3) -0.011(2) 0.024(3) -0.015(3) C14 0.051(3) 0.027(3) 0.048(3) -0.001(2) 0.021(2) -0.005(2) C16 0.033(2) 0.032(2) 0.034(2) 0.0000(19) 0.013(2) -0.0052(19) C17 0.0210(19) 0.029(2) 0.023(2) 0.0046(17) 0.0073(16) -0.0006(16) C19 0.039(2) 0.040(3) 0.025(2) -0.003(2) 0.0010(19) -0.002(2) C20 0.051(3) 0.031(3) 0.032(2) -0.006(2) 0.015(2) 0.000(2) C21 0.040(2) 0.029(2) 0.029(2) 0.0052(18) 0.013(2) 0.0108(19) C22 0.029(2) 0.033(2) 0.0187(19) 0.0023(17) 0.0060(17) 0.0018(18) C23 0.0223(19) 0.028(2) 0.0195(19) -0.0004(16) 0.0084(16) -0.0043(16) C24 0.024(2) 0.032(2) 0.0212(19) 0.0069(17) 0.0053(16) -0.0020(17) C25 0.028(2) 0.034(2) 0.022(2) 0.0062(18) 0.0041(17) 0.0049(18) C26 0.026(2) 0.051(3) 0.025(2) 0.008(2) 0.0058(18) 0.010(2) C27 0.038(3) 0.056(4) 0.042(3) 0.015(2) 0.013(2) 0.025(2) C28 0.059(3) 0.038(3) 0.051(3) 0.006(2) 0.018(3) 0.019(3) C29 0.047(3) 0.032(3) 0.041(3) 0.003(2) 0.008(2) 0.009(2) C30 0.033(2) 0.035(3) 0.034(2) 0.009(2) 0.006(2) 0.010(2) C36 0.049(2) 0.065(4) 0.097(4) -0.001(4) 0.034(3) -0.009(3) C37 0.057(4) 0.074(5) 0.098(5) 0.006(4) 0.040(4) -0.004(4) C38 0.053(4) 0.062(5) 0.089(5) -0.004(5) 0.035(4) -0.007(3) C39 0.059(5) 0.068(6) 0.086(5) 0.000(6) 0.038(5) -0.007(5) C41 0.124(4) 0.109(4) 0.086(4) 0.011(3) 0.047(4) -0.014(4) C42 0.114(5) 0.105(5) 0.084(4) 0.013(4) 0.035(4) -0.010(4) N1 0.0227(16) 0.0272(19) 0.0236(17) -0.0010(14) 0.0049(14) 0.0002(14) N3 0.0275(18) 0.032(2) 0.0315(19) -0.0028(16) 0.0140(16) -0.0060(16) N16 0.0201(16) 0.0273(18) 0.0233(17) 0.0000(14) 0.0047(14) 0.0014(14) N18 0.0211(17) 0.038(2) 0.0209(17) 0.0016(15) -0.0003(14) 0.0050(15) O35 0.0482(19) 0.056(2) 0.076(2) -0.0091(19) 0.0350(19) -0.0133(17) O40 0.159(5) 0.100(4) 0.099(4) 0.028(3) 0.024(4) -0.032(3) S31 0.0294(6) 0.0620(8) 0.0353(6) 0.0114(6) 0.0122(5) 0.0058(6) S32 0.0239(5) 0.0629(9) 0.0303(6) 0.0126(6) 0.0043(5) 0.0026(5) Zn1 0.0206(2) 0.0272(3) 0.0208(2) -0.00109(19) 0.00519(18) 0.00107(19) Br33 0.0281(2) 0.0295(2) 0.0225(2) -0.00159(17) 0.00037(16) 0.00388(17) Br34 0.0292(2) 0.0345(3) 0.0396(3) -0.0021(2) 0.00821(19) -0.00655(19) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 _geom_bond_publ_flag C2 C10 1.473(6) . . yes C2 N1 1.342(5) . . yes C2 N3 1.349(5) . . yes C4 C5 1.373(7) . . yes C4 C9 1.389(6) . . yes C4 H4 0.923 . . no C5 C6 1.412(7) . . yes C5 H5 0.936 . . no C6 C7 1.373(6) . . yes C6 H6 0.934 . . no C7 C8 1.399(6) . . yes C7 H7 0.922 . . no C8 C9 1.402(6) . . yes C8 N1 1.400(5) . . yes C9 N3 1.376(5) . . yes C10 C11 1.396(6) . . yes C10 C16 1.387(6) . . yes C11 C12 1.392(7) . . yes C11 S31 1.780(5) . . yes C12 C13 1.381(8) . . yes C12 H12 0.915 . . no C13 C14 1.374(7) . . yes C13 H13 0.921 . . no C14 C16 1.385(6) . . yes C14 H14 0.928 . . no C16 H15 0.927 . . no C17 C25 1.465(6) . . yes C17 N16 1.340(5) . . yes C17 N18 1.350(5) . . yes C19 C20 1.376(6) . . yes C19 C24 1.400(6) . . yes C19 H19 0.918 . . no C20 C21 1.396(6) . . yes C20 H20 0.928 . . no C21 C22 1.374(6) . . yes C21 H21 0.917 . . no C22 C23 1.390(6) . . yes C22 H22 0.934 . . no C23 C24 1.399(5) . . yes C23 N16 1.406(5) . . yes C24 N18 1.380(5) . . yes C25 C26 1.408(6) . . yes C25 C30 1.398(6) . . yes C26 C27 1.402(7) . . yes C26 S32 1.793(5) . . yes C27 C28 1.370(8) . . yes C27 H27 0.933 . . no C28 C29 1.389(7) . . yes C28 H28 0.92 . . no C29 C30 1.374(6) . . yes C29 H29 0.928 . . no C30 H30 0.928 . . no C36 C37 1.523(5) . . yes C36 H361 0.95 . . no C36 H362 0.95 . . no C36 O35 1.411(5) . . yes C37 H371 0.95 . . no C37 H372 0.95 . . no C37 H373 0.95 . . no C38 C39 1.535(5) . . yes C38 H381 0.95 . . no C38 H382 0.95 . . no C38 O35 1.415(5) . . yes C39 H391 0.95 . . no C39 H392 0.95 . . no C39 H393 0.95 . . no C41 C42 1.509(5) . . yes C41 H411 0.95 . . no C41 H412 0.95 . . no C41 O40 1.451(10) . . yes C42 H421 0.95 . . no C42 H422 0.95 . . no C42 H423 0.95 . . no H3 N3 0.847 . . no H18 N18 0.849 . . no H35 O35 0.871 . . no H40 O40 0.86 . . no N1 Zn1 2.024(3) . . yes N16 Zn1 2.044(3) . . yes S31 S32 2.0532(16) . . yes Zn1 Br33 2.4274(6) . . yes Zn1 Br34 2.4035(6) . . yes 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_2 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C10 C2 N1 125.5(4) . . . yes C10 C2 N3 122.9(4) . . . yes N1 C2 N3 111.6(4) . . . yes C5 C4 C9 116.8(4) . . . yes C5 C4 H4 121.8 . . . no C9 C4 H4 121.4 . . . no C4 C5 C6 121.8(4) . . . yes C4 C5 H5 120.1 . . . no C6 C5 H5 118.1 . . . no C5 C6 C7 121.0(4) . . . yes C5 C6 H6 119.8 . . . no C7 C6 H6 119.2 . . . no C6 C7 C8 118.2(4) . . . yes C6 C7 H7 122.6 . . . no C8 C7 H7 119.3 . . . no C7 C8 C9 119.8(4) . . . yes C7 C8 N1 131.1(4) . . . yes C9 C8 N1 109.1(4) . . . yes C8 C9 C4 122.5(4) . . . yes C8 C9 N3 105.4(3) . . . yes C4 C9 N3 132.1(4) . . . yes C2 C10 C11 121.3(4) . . . yes C2 C10 C16 119.6(4) . . . yes C11 C10 C16 119.1(4) . . . yes C10 C11 C12 119.1(4) . . . yes C10 C11 S31 120.9(3) . . . yes C12 C11 S31 120.0(4) . . . yes C11 C12 C13 121.0(5) . . . yes C11 C12 H12 119.3 . . . no C13 C12 H12 119.7 . . . no C12 C13 C14 119.9(5) . . . yes C12 C13 H13 119.7 . . . no C14 C13 H13 120.4 . . . no C13 C14 C16 119.7(5) . . . yes C13 C14 H14 120.3 . . . no C16 C14 H14 120 . . . no C10 C16 C14 121.1(4) . . . yes C10 C16 H15 120.2 . . . no C14 C16 H15 118.7 . . . no C25 C17 N16 124.7(4) . . . yes C25 C17 N18 124.2(4) . . . yes N16 C17 N18 111.0(4) . . . yes C20 C19 C24 116.4(4) . . . yes C20 C19 H19 122.1 . . . no C24 C19 H19 121.5 . . . no C19 C20 C21 121.5(4) . . . yes C19 C20 H20 118.8 . . . no C21 C20 H20 119.8 . . . no C20 C21 C22 122.2(4) . . . yes C20 C21 H21 118.5 . . . no C22 C21 H21 119.3 . . . no C21 C22 C23 117.5(4) . . . yes C21 C22 H22 122.4 . . . no C23 C22 H22 120.1 . . . no C22 C23 C24 120.2(4) . . . yes C22 C23 N16 131.6(4) . . . yes C24 C23 N16 108.2(3) . . . yes C19 C24 C23 122.3(4) . . . yes C19 C24 N18 131.8(4) . . . yes C23 C24 N18 105.9(4) . . . yes C17 C25 C26 124.1(4) . . . yes C17 C25 C30 117.5(4) . . . yes C26 C25 C30 118.4(4) . . . yes C25 C26 C27 119.2(5) . . . yes C25 C26 S32 122.9(4) . . . yes C27 C26 S32 117.9(3) . . . yes C26 C27 C28 120.9(4) . . . yes C26 C27 H27 119.1 . . . no C28 C27 H27 120 . . . no C27 C28 C29 120.3(5) . . . yes C27 C28 H28 119.4 . . . no C29 C28 H28 120.3 . . . no C28 C29 C30 119.6(5) . . . yes C28 C29 H29 121.2 . . . no C30 C29 H29 119.2 . . . no C25 C30 C29 121.6(4) . . . yes C25 C30 H30 118.5 . . . no C29 C30 H30 119.9 . . . no C37 C36 H361 110.6 . . . no C37 C36 H362 110.6 . . . no H361 C36 H362 109.5 . . . no C37 C36 O35 104.1(6) . . . yes H361 C36 O35 111.3 . . . no H362 C36 O35 110.7 . . . no C36 C37 H371 110.1 . . . no C36 C37 H372 109.2 . . . no H371 C37 H372 109.5 . . . no C36 C37 H373 109.2 . . . no H371 C37 H373 109.5 . . . no H372 C37 H373 109.5 . . . no C39 C38 H381 111 . . . no C39 C38 H382 105.4 . . . no H381 C38 H382 109.5 . . . no C39 C38 O35 114.1(12) . . . yes H381 C38 O35 109.5 . . . no H382 C38 O35 107.3 . . . no C38 C39 H391 109.3 . . . no C38 C39 H392 106.7 . . . no H391 C39 H392 109.5 . . . no C38 C39 H393 112.4 . . . no H391 C39 H393 109.5 . . . no H392 C39 H393 109.5 . . . no C42 C41 H411 111.4 . . . no C42 C41 H412 110.5 . . . no H411 C41 H412 109.5 . . . no C42 C41 O40 102.5(7) . . . yes H411 C41 O40 112 . . . no H412 C41 O40 110.8 . . . no C41 C42 H421 110.4 . . . no C41 C42 H422 108.5 . . . no H421 C42 H422 109.5 . . . no C41 C42 H423 109.4 . . . no H421 C42 H423 109.5 . . . no H422 C42 H423 109.5 . . . no C8 N1 C2 105.3(3) . . . yes C8 N1 Zn1 127.3(3) . . . yes C2 N1 Zn1 126.6(3) . . . yes C9 N3 C2 108.6(3) . . . yes C9 N3 H3 126.1 . . . no C2 N3 H3 125.2 . . . no C23 N16 C17 106.3(3) . . . yes C23 N16 Zn1 125.6(3) . . . yes C17 N16 Zn1 126.9(3) . . . yes C24 N18 C17 108.7(3) . . . yes C24 N18 H18 125.2 . . . no C17 N18 H18 126.1 . . . no C36 O35 H35 98.5 . . . no C41 O40 H40 108.9 . . . no C11 S31 S32 103.07(15) . . . yes C26 S32 S31 102.35(15) . . . yes N16 Zn1 N1 106.00(13) . . . yes N16 Zn1 Br33 114.98(10) . . . yes N1 Zn1 Br33 103.38(10) . . . yes N16 Zn1 Br34 112.28(10) . . . yes N1 Zn1 Br34 116.76(10) . . . yes Br33 Zn1 Br34 103.43(2) . . . yes # Attachment '- CCDC 758101.cif' #\#CIF_1.1 # CIF produced by WinGX routine CIF_UPDATE # Created on 2009-12-03 at 21:28:35 # Using CIFtbx version 2.6.2 16 Jun 1998 # Dictionary name : cif_core.dic # Dictionary vers : 2.3 # Request file : c:\wingx\files\archive.dat # CIF files read : publish dreduc struct data_5 _database_code_depnum_ccdc_archive 'CCDC 758101' #TrackingRef '- CCDC 758101.cif' _audit_creation_date 2009-12-03T21:28:35-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' _audit_conform_dict_name cif_core.dic _audit_conform_dict_version 2.3 _audit_conform_dict_location ftp://ftp.iucr.org/pub/cif_core.dic _publ_section_abstract ; Herein we report the synthesis, structural and spectroscopic characterization of coordination compounds with bis[2-(1H-benzimidazol-2-yl)phenyl]disulfide [bis-(2phSbz)] (1) and cobalt(II), zinc(II) and cadmium halides (2-7). Their X-ray diffraction analyses showed that the metal ions present similar distorted tetrahedral structure, with the disulfide ligand coordinated through the imidazolic nitrogen atoms, forming a twisted eleven membered chelate. Structures of nickel(II) compounds 8 and 9, showed that the disulfide bond in the ligand was broken and the two halves were coordinated to the nickel(II) through the sulfur and one imidazole nitrogen atom forming six membered rings. In 8, the two ligands were sulfides, however in 9 one of them was oxidized to a sulfone. In both compounds the nickel(II) has a distorted square planar geometry and the sulfur atoms are in cis positions. The oxidation reaction of bis-(2phSbz) was performed in KMnO4/NaOH, giving the 2-(1H,3H-benzimidazolium-2-yl)-benzene sulfonate (10). The solid state structure of compounds 2-5 and 7-10 was determined by X-ray diffraction analyses. ; #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_formula_moiety 'C26 H18 Br2 Cd N4 S2, 2(C2 H6 O)' _chemical_formula_sum 'C30 H30 Br2 Cd1 N4 O2 S2' _chemical_formula_weight 814.93 _chemical_compound_source 'synthesis as described' _chemical_absolute_configuration . #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P 1 21/n 1' _symmetry_space_group_name_Hall '-P 2yn' _symmetry_Int_Tables_number 14 loop_ _symmetry_equiv_pos_as_xyz x,y,z -x,-y,-z -x+1/2,y+1/2,-z+1/2 x+1/2,-y+1/2,z+1/2 _cell_length_a 12.5344(3) _cell_length_b 15.8964(4) _cell_length_c 17.4744(4) _cell_angle_alpha 90 _cell_angle_beta 107.9850(10) _cell_angle_gamma 90 _cell_volume 3311.68(14) _cell_formula_units_Z 4 _cell_measurement_temperature 293 _cell_measurement_reflns_used 13797 _cell_measurement_theta_min 3 _cell_measurement_theta_max 27 _cell_measurement_wavelength 0.71073 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.45 _exptl_crystal_size_mid 0.13 _exptl_crystal_size_min 0.05 _exptl_crystal_density_diffrn 1.634 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1616 #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 3.231 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SADABS (Siemens, 1996)' _exptl_absorpt_correction_T_min 0.52 _exptl_absorpt_correction_T_max 0.85 #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_source 'Enraf Nonius FR590' _diffrn_ambient_temperature 293 _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_detector 'CCD plate' _diffrn_detector_area_resol_mean 9 _diffrn_orient_matrix_type 'by Bruker AXS Collect from scalepack cell' _diffrn_orient_matrix_ub_11 0.81277E-1 _diffrn_orient_matrix_ub_12 0.118653E-1 _diffrn_orient_matrix_ub_13 0.271407E-1 _diffrn_orient_matrix_ub_21 -0.195038E-1 _diffrn_orient_matrix_ub_22 0.299921E-1 _diffrn_orient_matrix_ub_23 0.441923E-1 _diffrn_orient_matrix_ub_31 0.7025E-2 _diffrn_orient_matrix_ub_32 -0.540094E-1 _diffrn_orient_matrix_ub_33 0.305031E-1 _diffrn_measurement_device '95mm CCD camera on \k-goniostat' _diffrn_measurement_device_type 'Nonius KappaCCD' _diffrn_measurement_method '\f & \w scans' _diffrn_standards_number 0 _diffrn_reflns_av_R_equivalents 0.052 _diffrn_reflns_number 23385 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 3.08 _diffrn_reflns_theta_max 27.471 _diffrn_reflns_theta_full 26.372 _diffrn_measured_fraction_theta_full 0.995 _diffrn_measured_fraction_theta_max 0.991 _reflns_number_total 7521 _reflns_number_gt 4215 _reflns_threshold_expression I>3.0\s(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection 'COLLECT (Nonius, 1997-2001).' _computing_cell_refinement 'DENZO/SCALEPACK (Otwinowski & Minor, 1997)' _computing_data_reduction 'DENZO/SCALEPACK (Otwinowski & Minor, 1997)' _computing_structure_solution 'SHELXS 87 (Sheldrick, 1987)' _computing_structure_refinement 'CRYSTALS (Betteridge et al., 2003)' _computing_molecular_graphics 'CAMERON (Watkin et al., 1996)' _computing_publication_material 'CRYSTALS (Betteridge et al., 2003)' #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _refine_ls_structure_factor_coef F _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details ; Method= Modified Sheldrick w=1/[\s^2^(F^2^) + ( 0.00P)^2^ + 0.06P] ,where P=(max(Fo^2^,0) + 2Fc^2^)/3 ; _atom_sites_solution_primary direct _atom_sites_solution_hydrogens difmap _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method None _refine_ls_number_reflns 4215 _refine_ls_number_parameters 388 _refine_ls_number_restraints 47 _refine_ls_R_factor_all 0.0946 _refine_ls_R_factor_gt 0.0378 _refine_ls_wR_factor_ref 0.0449 _refine_ls_wR_factor_gt 0.0449 _refine_ls_wR_factor_all 0.0768 _refine_ls_goodness_of_fit_ref 1.0009 _refine_ls_shift/su_max 0.000954 _refine_diff_density_max 0.56 _refine_diff_density_min -0.7 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# loop_ _atom_type_symbol _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C 0.0033 0.0016 'International Tables Vol C 4.2.6.8 and 6.1.1.4' H 0 0 'International Tables Vol C 4.2.6.8 and 6.1.1.4' Br -0.2901 2.4595 'International Tables Vol C 4.2.6.8 and 6.1.1.4' Cd -0.8075 1.2024 'International Tables Vol C 4.2.6.8 and 6.1.1.4' N 0.0061 0.0033 'International Tables Vol C 4.2.6.8 and 6.1.1.4' O 0.0106 0.006 'International Tables Vol C 4.2.6.8 and 6.1.1.4' S 0.1246 0.1234 'International Tables Vol C 4.2.6.8 and 6.1.1.4' 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_disorder_assembly _atom_site_disorder_group C2 C 0.6405(4) 0.2592(4) 0.1004(3) 0.0448 Uani 1 . . C4 C 0.5812(6) 0.1262(5) 0.2473(4) 0.0701 Uani 1 . . C5 C 0.6463(6) 0.0585(5) 0.2813(4) 0.0748 Uani 1 . . C6 C 0.7416(6) 0.0354(5) 0.2619(4) 0.0731 Uani 1 . . C7 C 0.7760(5) 0.0808(4) 0.2060(4) 0.062 Uani 1 . . C8 C 0.7126(4) 0.1496(4) 0.1718(3) 0.0446 Uani 1 . . C9 C 0.6184(5) 0.1717(4) 0.1917(3) 0.0512 Uani 1 . . C10 C 0.6224(4) 0.3319(4) 0.0440(3) 0.0448 Uani 1 . . C11 C 0.5306(5) 0.3344(4) -0.0256(3) 0.0534 Uani 1 . . C12 C 0.5193(6) 0.4034(5) -0.0760(4) 0.0742 Uani 1 . . C13 C 0.5967(7) 0.4667(5) -0.0591(4) 0.0792 Uani 1 . . C14 C 0.6876(6) 0.4650(4) 0.0099(4) 0.0669 Uani 1 . . C15 C 0.6984(5) 0.3972(4) 0.0608(3) 0.0539 Uani 1 . . C17 C 0.7146(4) 0.2176(4) -0.1143(3) 0.0409 Uani 1 . . C19 C 0.7564(5) 0.4023(4) -0.2218(3) 0.0599 Uani 1 . . C20 C 0.8382(5) 0.4601(4) -0.1912(4) 0.062 Uani 1 . . C21 C 0.9145(5) 0.4521(4) -0.1138(3) 0.0573 Uani 1 . . C22 C 0.9104(5) 0.3853(4) -0.0650(3) 0.0489 Uani 1 . . C23 C 0.8267(4) 0.3255(3) -0.0949(3) 0.038 Uani 1 . . C24 C 0.7515(4) 0.3349(4) -0.1715(3) 0.0461 Uani 1 . . C25 C 0.6658(4) 0.1366(4) -0.1036(3) 0.0464 Uani 1 . . C26 C 0.5500(5) 0.1231(4) -0.1176(3) 0.0537 Uani 1 . . C27 C 0.5144(6) 0.0437(5) -0.1023(4) 0.0737 Uani 1 . . C28 C 0.5891(7) -0.0204(5) -0.0745(4) 0.0855 Uani 1 . . C29 C 0.7021(6) -0.0081(4) -0.0628(4) 0.0721 Uani 1 . . C30 C 0.7389(5) 0.0698(4) -0.0776(3) 0.0565 Uani 1 . . C36 C 0.3004(9) 0.3029(12) 0.1588(9) 0.1017 Uani 0.5 . 1 C37 C 0.2338(14) 0.2940(14) 0.0689(9) 0.1053 Uani 0.5 . 1 C38 C 0.2849(6) 0.3357(9) 0.1354(12) 0.0983 Uani 0.5 . 2 C39 C 0.2650(14) 0.2436(9) 0.1077(12) 0.0949 Uani 0.5 . 2 C41 C 0.5257(12) 0.3413(10) 0.3704(9) 0.2066 Uani 1 . . C42 C 0.6412(12) 0.3519(10) 0.3603(8) 0.2079 Uani 1 . . H3 H 0.5137 0.2702 0.147 0.0659 Uiso 1 . . H4 H 0.5155 0.1416 0.2601 0.0872 Uiso 1 . . H5 H 0.6251 0.0258 0.3197 0.0913 Uiso 1 . . H6 H 0.7849 -0.0136 0.2862 0.0864 Uiso 1 . . H7 H 0.8433 0.0654 0.1924 0.0734 Uiso 1 . . H12 H 0.4571 0.4068 -0.1227 0.0864 Uiso 1 . . H13 H 0.5881 0.5116 -0.0955 0.0961 Uiso 1 . . H14 H 0.7424 0.5101 0.0225 0.0814 Uiso 1 . . H15 H 0.7603 0.3951 0.1088 0.0675 Uiso 1 . . H18 H 0.6263 0.2542 -0.2241 0.0585 Uiso 1 . . H19 H 0.7038 0.4074 -0.2741 0.0713 Uiso 1 . . H20 H 0.8451 0.5072 -0.2237 0.0755 Uiso 1 . . H21 H 0.9719 0.4949 -0.0945 0.0694 Uiso 1 . . H22 H 0.9615 0.3799 -0.0124 0.0612 Uiso 1 . . H27 H 0.4364 0.0344 -0.1108 0.087 Uiso 1 . . H28 H 0.5639 -0.0737 -0.0629 0.1003 Uiso 1 . . H29 H 0.7548 -0.0539 -0.0452 0.0845 Uiso 1 . . H30 H 0.8179 0.0784 -0.0692 0.0664 Uiso 1 . . H35 H 0.4317 0.3677 0.2057 0.1175 Uiso 1 . . H40 H 0.5076 0.4537 0.3204 0.2331 Uiso 1 . . H361 H 0.2581 0.3356 0.188 0.1278 Uiso 0.5 . 1 H362 H 0.3163 0.246 0.1827 0.1278 Uiso 0.5 . 1 H371 H 0.1626 0.2655 0.0634 0.1328 Uiso 0.5 . 1 H372 H 0.219 0.3506 0.0457 0.1328 Uiso 0.5 . 1 H373 H 0.2766 0.2619 0.0404 0.1328 Uiso 0.5 . 1 H381 H 0.2488 0.3784 0.0928 0.1236 Uiso 0.5 . 2 H382 H 0.2566 0.3438 0.1813 0.1236 Uiso 0.5 . 2 H391 H 0.184 0.2327 0.0896 0.1186 Uiso 0.5 . 2 H392 H 0.2946 0.2367 0.0623 0.1186 Uiso 0.5 . 2 H393 H 0.3022 0.2038 0.1504 0.1186 Uiso 0.5 . 2 H411 H 0.5317 0.3529 0.4277 0.2203 Uiso 1 . . H412 H 0.502 0.2803 0.3585 0.2202 Uiso 1 . . H421 H 0.6937 0.3119 0.3977 0.2313 Uiso 1 . . H422 H 0.6689 0.4108 0.3735 0.2313 Uiso 1 . . H423 H 0.6375 0.3387 0.3036 0.2313 Uiso 1 . . N1 N 0.7262(3) 0.2065(3) 0.1138(2) 0.0443 Uani 1 . . N3 N 0.5736(4) 0.2414(3) 0.1454(3) 0.0535 Uani 1 . . N16 N 0.8021(3) 0.2529(3) -0.0601(2) 0.0402 Uani 1 . . N18 N 0.6822(4) 0.2656(3) -0.1815(2) 0.0513 Uani 1 . . O35 O 0.4030(4) 0.3410(4) 0.1607(3) 0.0943 Uani 1 . . O40 O 0.4746(8) 0.4091(6) 0.3062(6) 0.2136 Uani 1 . . S31 S 0.42955(13) 0.25188(14) -0.04938(10) 0.0686 Uani 1 . . S32 S 0.44715(12) 0.20318(13) -0.15384(9) 0.0657 Uani 1 . . Cd1 Cd 0.87499(3) 0.21587(3) 0.06954(2) 0.0422 Uani 1 . . Br33 Br 0.99492(5) 0.33257(4) 0.15914(3) 0.0498 Uani 1 . . Br34 Br 1.00159(5) 0.08624(4) 0.08923(4) 0.0663 Uani 1 . . 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 C2 0.044(3) 0.049(3) 0.041(3) -0.005(2) 0.012(2) -0.002(3) C4 0.064(4) 0.091(6) 0.062(4) 0.009(4) 0.030(3) -0.011(4) C5 0.078(5) 0.087(6) 0.063(4) 0.026(4) 0.027(4) -0.007(4) C6 0.069(4) 0.081(5) 0.067(4) 0.024(4) 0.017(4) -0.001(4) C7 0.064(4) 0.061(4) 0.063(4) 0.016(3) 0.023(3) 0.003(3) C8 0.041(3) 0.046(3) 0.046(3) 0.006(2) 0.013(2) -0.006(3) C9 0.053(3) 0.056(4) 0.046(3) 0.001(3) 0.018(3) -0.001(3) C10 0.045(3) 0.047(3) 0.046(3) -0.001(2) 0.019(2) 0.009(3) C11 0.049(3) 0.064(4) 0.046(3) 0.000(3) 0.013(3) 0.010(3) C12 0.076(5) 0.081(6) 0.056(4) 0.008(4) 0.007(3) 0.025(4) C13 0.112(6) 0.054(5) 0.076(5) 0.018(4) 0.034(5) 0.018(4) C14 0.079(4) 0.045(4) 0.079(4) 0.001(3) 0.027(4) -0.002(3) C15 0.059(3) 0.043(4) 0.058(3) -0.004(3) 0.016(3) 0.004(3) C17 0.037(3) 0.049(3) 0.037(2) -0.006(2) 0.012(2) -0.001(2) C19 0.075(4) 0.060(4) 0.040(3) 0.006(3) 0.010(3) 0.001(3) C20 0.082(4) 0.049(4) 0.055(3) 0.011(3) 0.022(3) -0.004(3) C21 0.066(4) 0.057(4) 0.050(3) -0.003(3) 0.021(3) -0.016(3) C22 0.055(3) 0.054(4) 0.036(3) -0.001(2) 0.011(2) -0.009(3) C23 0.039(3) 0.042(3) 0.032(2) 0.001(2) 0.010(2) 0.001(2) C24 0.045(3) 0.051(4) 0.040(3) -0.004(2) 0.010(2) -0.003(3) C25 0.050(3) 0.050(4) 0.037(3) -0.010(2) 0.011(2) -0.012(3) C26 0.047(3) 0.071(4) 0.041(3) -0.012(3) 0.011(3) -0.015(3) C27 0.060(4) 0.085(6) 0.075(4) -0.012(4) 0.018(4) -0.032(4) C28 0.102(6) 0.074(6) 0.078(5) -0.009(4) 0.024(5) -0.034(5) C29 0.077(5) 0.054(4) 0.076(4) -0.007(3) 0.010(4) -0.009(4) C30 0.059(4) 0.047(4) 0.057(3) -0.007(3) 0.007(3) -0.006(3) C36 0.080(4) 0.112(6) 0.123(5) 0.000(5) 0.046(5) 0.009(4) C37 0.085(6) 0.121(7) 0.123(6) -0.009(6) 0.050(5) 0.009(6) C38 0.076(3) 0.101(6) 0.123(5) 0.001(5) 0.038(5) 0.009(5) C39 0.074(5) 0.099(6) 0.120(7) 0.003(6) 0.042(6) 0.005(6) C41 0.237(9) 0.173(7) 0.172(7) -0.053(5) 0.008(7) 0.072(7) C42 0.234(9) 0.176(8) 0.175(7) -0.054(6) 0.006(8) 0.071(8) N1 0.043(2) 0.046(3) 0.043(2) 0.005(2) 0.0120(19) -0.002(2) N3 0.052(3) 0.060(3) 0.054(3) 0.000(2) 0.024(2) 0.005(2) N16 0.037(2) 0.046(3) 0.036(2) -0.0028(19) 0.0068(18) -0.007(2) N18 0.042(2) 0.065(3) 0.037(2) -0.002(2) -0.0021(19) -0.005(2) O35 0.075(3) 0.101(4) 0.116(4) -0.002(3) 0.042(3) 0.014(3) O40 0.246(8) 0.166(7) 0.177(7) -0.061(5) -0.009(6) 0.084(7) S31 0.0504(9) 0.0991(14) 0.0600(9) -0.0144(9) 0.0224(7) -0.0099(9) S32 0.0428(8) 0.0989(14) 0.0503(8) -0.0159(8) 0.0069(7) -0.0048(8) Cd1 0.0395(2) 0.0473(2) 0.03764(19) 0.00296(17) 0.00897(15) -0.00247(18) Br33 0.0520(3) 0.0475(3) 0.0408(3) 0.0030(2) 0.0008(2) -0.0056(3) Br34 0.0593(4) 0.0592(4) 0.0731(4) 0.0017(3) 0.0097(3) 0.0145(3) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 _geom_bond_publ_flag C2 C10 1.490(8) . . yes C2 N1 1.325(7) . . yes C2 N3 1.345(7) . . yes C4 C5 1.371(10) . . yes C4 C9 1.402(8) . . yes C4 H4 0.949 . . no C5 C6 1.388(9) . . yes C5 H5 0.949 . . no C6 C7 1.385(8) . . yes C6 H6 0.97 . . no C7 C8 1.375(8) . . yes C7 H7 0.976 . . no C8 C9 1.376(8) . . yes C8 N1 1.408(6) . . yes C9 N3 1.384(7) . . yes C10 C11 1.392(7) . . yes C10 C15 1.379(8) . . yes C11 C12 1.386(9) . . yes C11 S31 1.782(6) . . yes C12 C13 1.365(10) . . yes C12 H12 0.94 . . no C13 C14 1.379(9) . . yes C13 H13 0.941 . . no C14 C15 1.378(8) . . yes C14 H14 0.97 . . no C15 H15 0.951 . . no C17 C25 1.462(8) . . yes C17 N16 1.331(6) . . yes C17 N18 1.353(6) . . yes C19 C20 1.358(9) . . yes C19 C24 1.398(8) . . yes C19 H19 0.952 . . no C20 C21 1.400(8) . . yes C20 H20 0.96 . . no C21 C22 1.373(8) . . yes C21 H21 0.971 . . no C22 C23 1.392(7) . . yes C22 H22 0.948 . . no C23 C24 1.388(7) . . yes C23 N16 1.383(7) . . yes C24 N18 1.381(7) . . yes C25 C26 1.412(7) . . yes C25 C30 1.386(8) . . yes C26 C27 1.391(9) . . yes C26 S32 1.783(7) . . yes C27 C28 1.367(11) . . yes C27 H27 0.955 . . no C28 C29 1.381(10) . . yes C28 H28 0.948 . . no C29 C30 1.373(9) . . yes C29 H29 0.967 . . no C30 H30 0.965 . . no C36 C37 1.541(5) . . yes C36 H361 0.99 . . no C36 H362 0.99 . . no C36 O35 1.413(5) . . yes C37 H371 0.98 . . no C37 H372 0.98 . . no C37 H373 0.98 . . no C38 C39 1.539(5) . . yes C38 H381 1.007 . . no C38 H382 0.981 . . no C38 O35 1.411(5) . . yes C39 H391 0.98 . . no C39 H392 0.98 . . no C39 H393 0.98 . . no C41 C42 1.52(2) . . yes C41 H411 0.998 . . no C41 H412 1.016 . . no C41 O40 1.545(16) . . yes C42 H421 1 . . no C42 H422 1 . . no C42 H423 1 . . no H3 N3 0.887 . . no H18 N18 0.869 . . no H35 O35 0.868 . . no H40 O40 0.82 . . no N1 Cd1 2.234(4) . . yes N16 Cd1 2.244(4) . . yes S31 S32 2.056(2) . . yes Cd1 Br33 2.5882(7) . . yes Cd1 Br34 2.5585(8) . . yes 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_2 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C10 C2 N1 123.9(5) . . . yes C10 C2 N3 123.7(5) . . . yes N1 C2 N3 112.3(5) . . . yes C5 C4 C9 115.1(6) . . . yes C5 C4 H4 123 . . . no C9 C4 H4 122 . . . no C4 C5 C6 123.0(6) . . . yes C4 C5 H5 118.5 . . . no C6 C5 H5 118.6 . . . no C5 C6 C7 120.9(7) . . . yes C5 C6 H6 120.9 . . . no C7 C6 H6 118.2 . . . no C6 C7 C8 117.1(6) . . . yes C6 C7 H7 121.5 . . . no C8 C7 H7 121.4 . . . no C7 C8 C9 121.3(5) . . . yes C7 C8 N1 129.9(5) . . . yes C9 C8 N1 108.8(5) . . . yes C4 C9 C8 122.6(6) . . . yes C4 C9 N3 131.1(6) . . . yes C8 C9 N3 106.3(5) . . . yes C2 C10 C11 121.1(5) . . . yes C2 C10 C15 119.2(5) . . . yes C11 C10 C15 119.7(5) . . . yes C10 C11 C12 118.2(6) . . . yes C10 C11 S31 121.2(5) . . . yes C12 C11 S31 120.6(5) . . . yes C11 C12 C13 121.3(6) . . . yes C11 C12 H12 119.5 . . . no C13 C12 H12 119.2 . . . no C12 C13 C14 121.0(6) . . . yes C12 C13 H13 119.2 . . . no C14 C13 H13 119.9 . . . no C13 C14 C15 118.0(6) . . . yes C13 C14 H14 121.4 . . . no C15 C14 H14 120.6 . . . no C10 C15 C14 121.8(6) . . . yes C10 C15 H15 118.9 . . . no C14 C15 H15 119.3 . . . no C25 C17 N16 124.4(5) . . . yes C25 C17 N18 125.6(4) . . . yes N16 C17 N18 109.9(5) . . . yes C20 C19 C24 116.5(5) . . . yes C20 C19 H19 122.4 . . . no C24 C19 H19 121.1 . . . no C19 C20 C21 121.7(6) . . . yes C19 C20 H20 119.4 . . . no C21 C20 H20 118.9 . . . no C20 C21 C22 121.7(6) . . . yes C20 C21 H21 118.9 . . . no C22 C21 H21 119.4 . . . no C21 C22 C23 117.6(5) . . . yes C21 C22 H22 121.9 . . . no C23 C22 H22 120.5 . . . no C22 C23 C24 119.8(5) . . . yes C22 C23 N16 130.5(4) . . . yes C24 C23 N16 109.7(4) . . . yes C19 C24 C23 122.7(5) . . . yes C19 C24 N18 132.8(5) . . . yes C23 C24 N18 104.4(5) . . . yes C17 C25 C26 124.1(5) . . . yes C17 C25 C30 117.2(5) . . . yes C26 C25 C30 118.7(6) . . . yes C25 C26 C27 118.6(6) . . . yes C25 C26 S32 123.0(5) . . . yes C27 C26 S32 118.4(5) . . . yes C26 C27 C28 121.3(6) . . . yes C26 C27 H27 119 . . . no C28 C27 H27 119.7 . . . no C27 C28 C29 120.4(7) . . . yes C27 C28 H28 120.4 . . . no C29 C28 H28 119.2 . . . no C28 C29 C30 119.2(7) . . . yes C28 C29 H29 120.6 . . . no C30 C29 H29 120.2 . . . no C25 C30 C29 121.8(6) . . . yes C25 C30 H30 119 . . . no C29 C30 H30 119.2 . . . no C37 C36 H361 111.5 . . . no C37 C36 H362 108.8 . . . no H361 C36 H362 109.5 . . . no C37 C36 O35 105.4(11) . . . yes H361 C36 O35 113 . . . no H362 C36 O35 108.6 . . . no C36 C37 H371 109.4 . . . no C36 C37 H372 108.2 . . . no H371 C37 H372 109.5 . . . no C36 C37 H373 110.8 . . . no H371 C37 H373 109.5 . . . no H372 C37 H373 109.5 . . . no C39 C38 H381 114.6 . . . no C39 C38 H382 108.6 . . . no H381 C38 H382 108.9 . . . no C39 C38 O35 102.0(10) . . . yes H381 C38 O35 112.3 . . . no H382 C38 O35 110.3 . . . no C38 C39 H391 108.7 . . . no C38 C39 H392 107.3 . . . no H391 C39 H392 109.5 . . . no C38 C39 H393 112.4 . . . no H391 C39 H393 109.5 . . . no H392 C39 H393 109.5 . . . no C42 C41 H411 108.4 . . . no C42 C41 H412 108.1 . . . no H411 C41 H412 107.9 . . . no C42 C41 O40 91.9(11) . . . yes H411 C41 O40 119.1 . . . no H412 C41 O40 119.2 . . . no C41 C42 H421 108.1 . . . no C41 C42 H422 110.6 . . . no H421 C42 H422 109.5 . . . no C41 C42 H423 109.7 . . . no H421 C42 H423 109.5 . . . no H422 C42 H423 109.5 . . . no C8 N1 C2 105.2(4) . . . yes C8 N1 Cd1 126.3(3) . . . yes C2 N1 Cd1 127.9(4) . . . yes C9 N3 C2 107.3(5) . . . yes C9 N3 H3 126.1 . . . no C2 N3 H3 126.5 . . . no C23 N16 C17 106.6(4) . . . yes C23 N16 Cd1 125.9(3) . . . yes C17 N16 Cd1 126.6(4) . . . yes C24 N18 C17 109.3(4) . . . yes C24 N18 H18 125.7 . . . no C17 N18 H18 124.9 . . . no C36 O35 H35 110.5 . . . no C41 O40 H40 109 . . . no C11 S31 S32 102.8(2) . . . yes C26 S32 S31 102.56(19) . . . yes N16 Cd1 N1 104.13(15) . . . yes N16 Cd1 Br33 113.71(11) . . . yes N1 Cd1 Br33 103.26(11) . . . yes N16 Cd1 Br34 112.89(11) . . . yes N1 Cd1 Br34 116.70(12) . . . yes Br33 Cd1 Br34 106.00(2) . . . yes # Attachment '- CCDC 758102.cif' #\#CIF_1.1 # CIF produced by WinGX routine CIF_UPDATE # Created on 2009-12-07 at 18:06:24 # Using CIFtbx version 2.6.2 16 Jun 1998 # Dictionary name : cif_core.dic # Dictionary vers : 2.3 # Request file : c:\wingx\files\archive.dat # CIF files read : publish rosalinda722 dreduc struct data_6 _database_code_depnum_ccdc_archive 'CCDC 758102' #TrackingRef '- CCDC 758102.cif' _audit_creation_date 2009-12-07T18:06:24-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' _audit_conform_dict_name cif_core.dic _audit_conform_dict_version 2.3 _audit_conform_dict_location ftp://ftp.iucr.org/pub/cif_core.dic _publ_section_abstract ; Herein we report the synthesis, structural and spectroscopic characterization of coordination compounds with bis[2-(1H-benzimidazol-2-yl)phenyl]disulfide [bis-(2phSbz)] (1) and cobalt(II), zinc(II) and cadmium halides (2-7). Their X-ray diffraction analyses showed that the metal ions present similar distorted tetrahedral structure, with the disulfide ligand coordinated through the imidazolic nitrogen atoms, forming a twisted eleven membered chelate. Structures of nickel(II) compounds 8 and 9, showed that the disulfide bond in the ligand was broken and the two halves were coordinated to the nickel(II) through the sulfur and one imidazole nitrogen atom forming six membered rings. In 8, the two ligands were sulfides, however in 9 one of them was oxidized to a sulfone. In both compounds the nickel(II) has a distorted square planar geometry and the sulfur atoms are in cis positions. The oxidation reaction of bis-(2phSbz) was performed in KMnO4/NaOH, giving the 2-(1H,3H-benzimidazolium-2-yl)-benzene sulfonate (10). The solid state structure of compounds 2-5 and 7-10 was determined by X-ray diffraction analyses. ; #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C26 H18 N4 Ni O2 S2, 2(C2 H6 O)' _chemical_formula_sum 'C30 H30 N4 Ni1 O4 S2' _chemical_formula_weight 633.43 _chemical_compound_source 'synthesis as described' _chemical_absolute_configuration ad #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M 'P 21 21 21' _symmetry_space_group_name_Hall 'P 2ac 2ab' _symmetry_Int_Tables_number 19 loop_ _symmetry_equiv_pos_as_xyz x,y,z x+1/2,-y+1/2,-z -x,y+1/2,-z+1/2 -x+1/2,-y,z+1/2 _cell_length_a 10.1005(4) _cell_length_b 13.0781(5) _cell_length_c 21.7855(10) _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_volume 2877.8(2) _cell_formula_units_Z 4 _cell_measurement_temperature 173 _cell_measurement_reflns_used 33980 _cell_measurement_theta_min 1 _cell_measurement_theta_max 27 _cell_measurement_wavelength 0.71073 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description needle _exptl_crystal_colour green _exptl_crystal_size_max 0.4 _exptl_crystal_size_mid 0.13 _exptl_crystal_size_min 0.05 _exptl_crystal_density_diffrn 1.462 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1320 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.863 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SADABS (Siemens, 1996)' _exptl_absorpt_correction_T_min 0.61 _exptl_absorpt_correction_T_max 0.96 #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_source 'Enraf Nonius FR590' _diffrn_ambient_temperature 173 _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_detector 'CCD plate' _diffrn_detector_area_resol_mean 9 _diffrn_orient_matrix_type 'by Bruker AXS Collect from scalepack cell' _diffrn_orient_matrix_ub_11 0.538462E-1 _diffrn_orient_matrix_ub_12 -0.409047E-1 _diffrn_orient_matrix_ub_13 -0.296779E-1 _diffrn_orient_matrix_ub_21 0.719088E-1 _diffrn_orient_matrix_ub_22 -0.65623E-2 _diffrn_orient_matrix_ub_23 0.313045E-1 _diffrn_orient_matrix_ub_31 -0.416137E-1 _diffrn_orient_matrix_ub_32 -0.642685E-1 _diffrn_orient_matrix_ub_33 0.156925E-1 _diffrn_measurement_device '95mm CCD camera on \k-goniostat' _diffrn_measurement_device_type 'Nonius KappaCCD' _diffrn_measurement_method '\f & \w scans' _diffrn_standards_number 0 _diffrn_reflns_av_R_equivalents 0.078 _diffrn_reflns_av_unetI/netI 0.1075 _diffrn_reflns_number 14452 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 28 _diffrn_reflns_theta_min 1.816 _diffrn_reflns_theta_max 27.398 _diffrn_reflns_theta_full 25.206 _diffrn_measured_fraction_theta_full 0.971 _diffrn_measured_fraction_theta_max 0.956 _reflns_number_total 5987 _reflns_number_gt 3272 _reflns_threshold_expression I>3.0\s(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection 'COLLECT (Nonius, 1997-2001).' _computing_cell_refinement 'DENZO/SCALEPACK (Otwinowski & Minor, 1997)' _computing_data_reduction 'DENZO/SCALEPACK (Otwinowski & Minor, 1997)' _computing_structure_solution 'SHELXS 97 (Sheldrick, 1997)' _computing_structure_refinement 'CRYSTALS (Betteridge et al., 2003)' _computing_molecular_graphics 'CAMERON (Watkin et al., 1996)' _computing_publication_material 'CRYSTALS (Betteridge et al., 2003)' #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _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^ > 2\s(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 F _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details ; Method= Modified Sheldrick w=1/[\s^2^(F^2^) + ( 0.01P)^2^ + 0.00P] ,where P=(max(Fo^2^,0) + 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_number_reflns 3272 _refine_ls_number_parameters 389 _refine_ls_number_restraints 48 _refine_ls_R_factor_all 0.0958 _refine_ls_R_factor_gt 0.0446 _refine_ls_wR_factor_ref 0.0512 _refine_ls_wR_factor_gt 0.0512 _refine_ls_wR_factor_all 0.1873 _refine_ls_goodness_of_fit_ref 1.0044 _refine_ls_restrained_S_all 1.058 _refine_ls_shift/su_max 0.00024 _refine_ls_shift/su_mean 0 _refine_ls_abs_structure_details 'Flack (1983), 2478 Friedel-pairs' _refine_ls_abs_structure_Flack -0.05(2) _refine_diff_density_max 0.6 _refine_diff_density_min -0.37 _refine_diff_density_rms 0.177 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# loop_ _atom_type_symbol _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C 0.0033 0.0016 'International Tables Vol C 4.2.6.8 and 6.1.1.4' H 0 0 'International Tables Vol C 4.2.6.8 and 6.1.1.4' N 0.0061 0.0033 'International Tables Vol C 4.2.6.8 and 6.1.1.4' Ni 0.3393 1.1124 'International Tables Vol C 4.2.6.8 and 6.1.1.4' O 0.0106 0.006 'International Tables Vol C 4.2.6.8 and 6.1.1.4' S 0.1246 0.1234 'International Tables Vol C 4.2.6.8 and 6.1.1.4' 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_disorder_assembly _atom_site_disorder_group C2 C 0.6374(7) 0.9666(4) 0.0888(3) 0.0278 Uani 1 . . C4 C 0.8649(8) 1.1127(5) 0.1793(3) 0.0368 Uani 1 . . C5 C 0.8383(8) 1.1493(5) 0.2368(3) 0.0318 Uani 1 . . C6 C 0.7202(9) 1.1290(5) 0.2663(3) 0.0345 Uani 1 . . C7 C 0.6176(7) 1.0736(4) 0.2382(2) 0.0276 Uani 1 . . C8 C 0.6438(7) 1.0378(4) 0.1788(3) 0.0262 Uani 1 . . C9 C 0.7656(7) 1.0562(4) 0.1504(3) 0.0275 Uani 1 . . C10 C 0.5933(7) 0.9097(4) 0.0342(3) 0.026 Uani 1 . . C11 C 0.4600(7) 0.9044(4) 0.0188(3) 0.0246 Uani 1 . . C12 C 0.4159(8) 0.8463(5) -0.0304(3) 0.0337 Uani 1 . . C13 C 0.5104(9) 0.7926(5) -0.0645(3) 0.0384 Uani 1 . . C14 C 0.6409(7) 0.7980(5) -0.0513(3) 0.034 Uani 1 . . C15 C 0.6855(8) 0.8550(4) -0.0007(3) 0.0327 Uani 1 . . C17 C 0.3835(8) 0.8581(4) 0.2816(3) 0.0281 Uani 1 . . C19 C 0.6720(8) 0.7049(5) 0.3120(3) 0.0302 Uani 1 . . C20 C 0.7633(8) 0.6765(5) 0.2697(3) 0.0398 Uani 1 . . C21 C 0.7548(8) 0.7084(5) 0.2086(3) 0.0407 Uani 1 . . C22 C 0.6542(8) 0.7718(5) 0.1892(3) 0.0348 Uani 1 . . C23 C 0.5598(7) 0.8043(4) 0.2318(3) 0.027 Uani 1 . . C24 C 0.5691(7) 0.7691(4) 0.2931(3) 0.0263 Uani 1 . . C25 C 0.2516(7) 0.8948(4) 0.2969(3) 0.0266 Uani 1 . . C26 C 0.1561(8) 0.9096(4) 0.2514(3) 0.0328 Uani 1 . . C27 C 0.0248(8) 0.9287(6) 0.2693(3) 0.0385 Uani 1 . . C28 C -0.0085(9) 0.9371(6) 0.3310(3) 0.0499 Uani 1 . . C29 C 0.0886(8) 0.9256(5) 0.3759(3) 0.0425 Uani 1 . . C30 C 0.2159(8) 0.9045(5) 0.3590(3) 0.0385 Uani 1 . . C36 C 0.364(2) 0.7560(12) 0.4948(5) 0.0629 Uani 0.5 . 1 C37 C 0.318(2) 0.6736(13) 0.5398(8) 0.0647 Uani 0.5 . 1 C38 C 0.4148(17) 0.7501(14) 0.5038(3) 0.0556 Uani 0.5 . 2 C39 C 0.2901(18) 0.6886(13) 0.5193(8) 0.0558 Uani 0.5 . 2 C41 C 0.4545(8) 0.5029(6) 0.0547(2) 0.0568 Uani 1 . . C42 C 0.5117(9) 0.5967(6) 0.0867(3) 0.0622 Uani 1 . . H3 H 0.8197 1.0101 0.0665 0.0319 Uiso 1 . . H4 H 0.9459 1.1252 0.1604 0.0441 Uiso 1 . . H5 H 0.9012 1.1877 0.2569 0.0387 Uiso 1 . . H6 H 0.7062 1.1549 0.3067 0.0427 Uiso 1 . . H7 H 0.5369 1.0594 0.2572 0.0335 Uiso 1 . . H12 H 0.3258 0.8429 -0.0404 0.04 Uiso 1 . . H13 H 0.4818 0.7525 -0.0978 0.0458 Uiso 1 . . H14 H 0.7025 0.7641 -0.0769 0.0417 Uiso 1 . . H15 H 0.7745 0.8563 0.0099 0.0396 Uiso 1 . . H18 H 0.4428 0.7988 0.3611 0.035 Uiso 1 . . H19 H 0.679 0.6822 0.3518 0.0373 Uiso 1 . . H20 H 0.8326 0.6348 0.2812 0.0495 Uiso 1 . . H21 H 0.8178 0.6874 0.1804 0.0491 Uiso 1 . . H22 H 0.649 0.7913 0.1479 0.0407 Uiso 1 . . H27 H -0.0412 0.9376 0.2403 0.0457 Uiso 1 . . H28 H -0.0939 0.9543 0.3418 0.0612 Uiso 1 . . H29 H 0.0662 0.9326 0.4181 0.052 Uiso 1 . . H30 H 0.2809 0.8972 0.3898 0.0457 Uiso 1 . . H35 H 0.4962 0.6952 0.4486 0.0643 Uiso 1 . . H40 H 0.5352 0.5176 -0.0214 0.0615 Uiso 1 . . H361 H 0.4265 0.7979 0.5185 0.0731 Uiso 0.5 . 1 H362 H 0.2885 0.7979 0.4825 0.0731 Uiso 0.5 . 1 H371 H 0.2742 0.708 0.5755 0.0752 Uiso 0.5 . 1 H372 H 0.3922 0.63 0.5547 0.0752 Uiso 0.5 . 1 H373 H 0.2513 0.6299 0.518 0.0752 Uiso 0.5 . 1 H381 H 0.397 0.8231 0.5096 0.0653 Uiso 0.5 . 2 H382 H 0.4921 0.7303 0.5283 0.0653 Uiso 0.5 . 2 H391 H 0.2667 0.6989 0.5635 0.0656 Uiso 0.5 . 2 H392 H 0.2137 0.7096 0.493 0.0656 Uiso 0.5 . 2 H393 H 0.3108 0.6149 0.512 0.0656 Uiso 0.5 . 2 H411 H 0.506 0.4429 0.0676 0.0672 Uiso 1 . . H412 H 0.3644 0.4954 0.069 0.0671 Uiso 1 . . H421 H 0.5096 0.5847 0.1306 0.0921 Uiso 1 . . H422 H 0.601 0.6047 0.073 0.0922 Uiso 1 . . H423 H 0.4617 0.6571 0.0764 0.0918 Uiso 1 . . N1 N 0.5654(6) 0.9812(4) 0.1381(2) 0.025 Uani 1 . . N3 N 0.7593(6) 1.0084(4) 0.0947(2) 0.0261 Uani 1 . . N16 N 0.4434(6) 0.8616(4) 0.2264(2) 0.0242 Uani 1 . . N18 N 0.4601(6) 0.8053(4) 0.3227(2) 0.0277 Uani 1 . . O33 O 0.2121(5) 0.9445(3) 0.0359(2) 0.0418 Uani 1 . . O34 O 0.3718(5) 1.0858(3) 0.04728(18) 0.0379 Uani 1 . . O35 O 0.4303(6) 0.7291(4) 0.4401(2) 0.0556 Uani 1 . . O40 O 0.4580(6) 0.5114(4) -0.0104(2) 0.0531 Uani 1 . . S31 S 0.34009(17) 0.97810(11) 0.06186(7) 0.025 Uani 1 . . S32 S 0.18089(17) 0.90356(12) 0.17069(7) 0.0284 Uani 1 . . Ni1 Ni 0.38792(9) 0.93107(5) 0.15369(3) 0.0234 Uani 1 . . 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 C2 0.031(5) 0.024(3) 0.028(4) 0.006(3) 0.003(3) 0.007(3) C4 0.032(4) 0.035(3) 0.043(4) 0.003(3) -0.006(4) 0.004(3) C5 0.034(4) 0.027(3) 0.034(4) -0.006(3) -0.012(4) -0.005(3) C6 0.047(5) 0.029(4) 0.027(4) -0.005(3) -0.011(4) 0.005(3) C7 0.029(3) 0.027(3) 0.026(3) 0.002(3) -0.004(3) -0.006(3) C8 0.041(5) 0.015(3) 0.023(3) 0.001(2) -0.005(3) 0.002(2) C9 0.035(4) 0.024(3) 0.023(3) 0.005(3) -0.009(3) 0.001(3) C10 0.033(4) 0.020(3) 0.025(4) 0.002(2) 0.008(3) -0.001(3) C11 0.038(4) 0.019(3) 0.017(3) 0.007(2) 0.000(3) 0.003(3) C12 0.041(5) 0.035(3) 0.025(4) 0.006(3) 0.000(4) -0.002(3) C13 0.056(5) 0.030(4) 0.029(4) -0.003(3) -0.002(4) 0.009(3) C14 0.040(5) 0.036(4) 0.026(4) -0.006(3) -0.003(3) 0.006(3) C15 0.034(5) 0.026(3) 0.039(4) 0.002(3) 0.004(4) 0.009(3) C17 0.043(4) 0.020(3) 0.021(4) -0.004(2) -0.004(4) -0.009(3) C19 0.028(4) 0.035(3) 0.028(4) 0.002(3) -0.010(4) -0.003(3) C20 0.040(5) 0.037(4) 0.042(5) 0.007(3) -0.009(4) 0.005(3) C21 0.034(5) 0.051(4) 0.037(5) 0.008(4) 0.010(4) 0.010(3) C22 0.043(5) 0.031(3) 0.030(4) 0.005(3) 0.002(4) 0.005(3) C23 0.028(4) 0.022(3) 0.031(4) 0.002(3) -0.003(3) -0.005(3) C24 0.034(4) 0.022(3) 0.023(4) 0.002(3) 0.002(3) -0.006(3) C25 0.028(4) 0.030(3) 0.022(4) 0.001(3) 0.007(3) -0.002(3) C26 0.046(5) 0.023(3) 0.030(4) 0.006(3) 0.010(4) -0.004(3) C27 0.031(4) 0.049(4) 0.036(4) 0.005(4) 0.002(3) 0.013(4) C28 0.052(5) 0.050(4) 0.048(5) 0.003(4) 0.019(4) 0.015(4) C29 0.045(5) 0.047(4) 0.035(4) -0.005(3) 0.014(4) 0.003(4) C30 0.047(5) 0.040(4) 0.029(4) -0.006(3) 0.005(4) -0.004(3) C36 0.064(6) 0.073(5) 0.052(4) 0.016(4) 0.023(4) 0.033(5) C37 0.065(7) 0.077(6) 0.053(6) 0.020(5) 0.020(6) 0.033(6) C38 0.065(6) 0.061(5) 0.041(3) 0.019(4) 0.014(5) 0.025(5) C39 0.065(7) 0.059(6) 0.043(6) 0.018(5) 0.014(6) 0.025(5) C41 0.040(4) 0.081(4) 0.049(3) 0.001(3) -0.007(3) 0.008(3) C42 0.047(4) 0.091(4) 0.049(4) -0.008(3) -0.002(4) 0.004(4) N1 0.033(3) 0.025(2) 0.017(3) 0.002(2) -0.006(2) 0.002(2) N3 0.034(4) 0.023(3) 0.021(3) -0.002(2) 0.001(3) -0.006(2) N16 0.029(3) 0.028(3) 0.016(3) 0.001(2) -0.001(3) -0.001(2) N18 0.035(4) 0.032(3) 0.016(3) 0.000(2) -0.001(3) -0.006(2) O33 0.038(3) 0.045(3) 0.042(3) 0.002(2) -0.006(3) 0.002(2) O34 0.044(3) 0.036(3) 0.033(2) 0.0015(19) 0.003(2) 0.004(2) O35 0.066(4) 0.063(3) 0.038(2) 0.019(2) 0.017(3) 0.023(3) O40 0.033(3) 0.079(3) 0.047(3) -0.003(3) -0.011(3) 0.004(3) S31 0.0278(9) 0.0261(7) 0.0210(8) 0.0015(6) -0.0041(8) 0.0027(6) S32 0.0257(9) 0.0351(9) 0.0243(9) -0.0001(6) 0.0008(8) -0.0014(7) Ni1 0.0257(4) 0.0249(3) 0.0197(4) 0.0020(3) 0.0004(4) -0.0001(3) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 _geom_bond_publ_flag C2 C10 1.472(8) . . yes C2 N1 1.311(8) . . yes C2 N3 1.354(9) . . yes C4 C5 1.368(9) . . yes C4 C9 1.395(9) . . yes C4 H4 0.93 . . no C5 C6 1.380(10) . . yes C5 H5 0.921 . . no C6 C7 1.405(9) . . yes C6 H6 0.953 . . no C7 C8 1.402(7) . . yes C7 H7 0.932 . . no C8 C9 1.398(9) . . yes C8 N1 1.400(8) . . yes C9 N3 1.368(7) . . yes C10 C11 1.389(9) . . yes C10 C15 1.400(9) . . yes C11 C12 1.386(8) . . yes C11 S31 1.811(7) . . yes C12 C13 1.399(10) . . yes C12 H12 0.937 . . no C13 C14 1.351(11) . . yes C13 H13 0.94 . . no C14 C15 1.406(9) . . yes C14 H14 0.946 . . no C15 H15 0.928 . . no C17 C25 1.455(10) . . yes C17 N16 1.346(8) . . yes C17 N18 1.370(8) . . yes C19 C20 1.356(10) . . yes C19 C24 1.397(9) . . yes C19 H19 0.919 . . no C20 C21 1.396(9) . . yes C20 H20 0.922 . . no C21 C22 1.377(10) . . yes C21 H21 0.928 . . no C22 C23 1.397(9) . . yes C22 H22 0.936 . . no C23 C24 1.417(8) . . yes C23 N16 1.398(9) . . yes C24 N18 1.361(9) . . yes C25 C26 1.398(10) . . yes C25 C30 1.405(9) . . yes C26 C27 1.405(10) . . yes C26 S32 1.777(6) . . yes C27 C28 1.390(9) . . yes C27 H27 0.926 . . no C28 C29 1.393(10) . . yes C28 H28 0.922 . . no C29 C30 1.366(10) . . yes C29 H29 0.95 . . no C30 H30 0.943 . . no C36 C37 1.531(5) . . yes C36 H361 0.98 . . no C36 H362 0.98 . . no C36 O35 1.409(5) . . yes C37 H371 1 . . no C37 H372 1 . . no C37 H373 1 . . no C38 C39 1.533(5) . . yes C38 H381 0.98 . . no C38 H382 0.98 . . no C38 O35 1.422(5) . . yes C39 H391 1 . . no C39 H392 1 . . no C39 H393 1 . . no C41 C42 1.525(10) . . yes C41 H411 0.982 . . no C41 H412 0.967 . . no C41 O40 1.423(4) . . yes C42 H421 0.97 . . no C42 H422 0.957 . . no C42 H423 0.963 . . no H3 N3 0.865 . . no H18 N18 0.858 . . no H35 O35 0.82 . . no H40 O40 0.82 . . no N1 Ni1 1.939(6) . . yes N16 Ni1 1.911(5) . . yes O33 S31 1.478(5) . . yes O34 S31 1.479(4) . . yes S31 Ni1 2.1480(16) . . yes S32 Ni1 2.1539(19) . . yes 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_2 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C10 C2 N1 124.6(6) . . . yes C10 C2 N3 123.8(6) . . . yes N1 C2 N3 111.6(6) . . . yes C5 C4 C9 117.2(7) . . . yes C5 C4 H4 121.1 . . . no C9 C4 H4 121.7 . . . no C4 C5 C6 121.9(6) . . . yes C4 C5 H5 119.4 . . . no C6 C5 H5 118.7 . . . no C5 C6 C7 122.3(6) . . . yes C5 C6 H6 119.3 . . . no C7 C6 H6 118.4 . . . no C6 C7 C8 115.8(7) . . . yes C6 C7 H7 123.7 . . . no C8 C7 H7 120.5 . . . no C7 C8 C9 121.2(6) . . . yes C7 C8 N1 130.9(6) . . . yes C9 C8 N1 108.0(5) . . . yes C8 C9 C4 121.6(6) . . . yes C8 C9 N3 105.9(6) . . . yes C4 C9 N3 132.6(7) . . . yes C2 C10 C11 121.0(6) . . . yes C2 C10 C15 119.7(6) . . . yes C11 C10 C15 119.2(6) . . . yes C10 C11 C12 121.7(6) . . . yes C10 C11 S31 119.7(5) . . . yes C12 C11 S31 118.5(6) . . . yes C11 C12 C13 117.8(7) . . . yes C11 C12 H12 121.2 . . . no C13 C12 H12 121 . . . no C12 C13 C14 121.7(7) . . . yes C12 C13 H13 118.8 . . . no C14 C13 H13 119.5 . . . no C13 C14 C15 120.5(7) . . . yes C13 C14 H14 119.5 . . . no C15 C14 H14 120 . . . no C14 C15 C10 119.0(7) . . . yes C14 C15 H15 121.1 . . . no C10 C15 H15 120 . . . no C25 C17 N16 127.3(6) . . . yes C25 C17 N18 122.2(6) . . . yes N16 C17 N18 110.3(7) . . . yes C20 C19 C24 118.1(6) . . . yes C20 C19 H19 120.1 . . . no C24 C19 H19 121.9 . . . no C19 C20 C21 121.5(7) . . . yes C19 C20 H20 119.6 . . . no C21 C20 H20 118.9 . . . no C20 C21 C22 121.2(7) . . . yes C20 C21 H21 120.1 . . . no C22 C21 H21 118.7 . . . no C21 C22 C23 118.9(6) . . . yes C21 C22 H22 120.1 . . . no C23 C22 H22 121.1 . . . no C22 C23 C24 118.8(6) . . . yes C22 C23 N16 133.0(6) . . . yes C24 C23 N16 108.0(6) . . . yes C23 C24 C19 121.5(6) . . . yes C23 C24 N18 106.2(6) . . . yes C19 C24 N18 132.2(6) . . . yes C17 C25 C26 121.0(6) . . . yes C17 C25 C30 119.1(6) . . . yes C26 C25 C30 119.6(7) . . . yes C25 C26 C27 118.6(6) . . . yes C25 C26 S32 126.8(6) . . . yes C27 C26 S32 114.6(6) . . . yes C26 C27 C28 120.7(7) . . . yes C26 C27 H27 120.8 . . . no C28 C27 H27 118.5 . . . no C27 C28 C29 120.0(7) . . . yes C27 C28 H28 119.5 . . . no C29 C28 H28 120.4 . . . no C28 C29 C30 119.7(6) . . . yes C28 C29 H29 120 . . . no C30 C29 H29 120.3 . . . no C25 C30 C29 121.3(7) . . . yes C25 C30 H30 119.8 . . . no C29 C30 H30 118.9 . . . no C37 C36 H361 104.7 . . . no C37 C36 H362 109.1 . . . no H361 C36 H362 109.5 . . . no C37 C36 O35 120.7(13) . . . yes H361 C36 O35 106.4 . . . no H362 C36 O35 106.1 . . . no C36 C37 H371 108.5 . . . no C36 C37 H372 112.2 . . . no H371 C37 H372 109.5 . . . no C36 C37 H373 107.7 . . . no H371 C37 H373 109.5 . . . no H372 C37 H373 109.5 . . . no C39 C38 H381 109.3 . . . no C39 C38 H382 113.3 . . . no H381 C38 H382 109.5 . . . no C39 C38 O35 101.8(11) . . . yes H381 C38 O35 109.6 . . . no H382 C38 O35 113.1 . . . no C38 C39 H391 109.7 . . . no C38 C39 H392 111.3 . . . no H391 C39 H392 109.5 . . . no C38 C39 H393 107.4 . . . no H391 C39 H393 109.5 . . . no H392 C39 H393 109.5 . . . no C42 C41 H411 108.2 . . . no C42 C41 H412 106.9 . . . no H411 C41 H412 109.1 . . . no C42 C41 O40 112.5(6) . . . yes H411 C41 O40 109.5 . . . no H412 C41 O40 110.6 . . . no C41 C42 H421 108.2 . . . no C41 C42 H422 107.7 . . . no H421 C42 H422 110.2 . . . no C41 C42 H423 110.8 . . . no H421 C42 H423 110.5 . . . no H422 C42 H423 109.3 . . . no C8 N1 C2 106.4(6) . . . yes C8 N1 Ni1 126.2(4) . . . yes C2 N1 Ni1 127.4(4) . . . yes C9 N3 C2 108.1(6) . . . yes C9 N3 H3 125.8 . . . no C2 N3 H3 125.8 . . . no C23 N16 C17 106.6(5) . . . yes C23 N16 Ni1 124.8(4) . . . yes C17 N16 Ni1 128.6(5) . . . yes C17 N18 C24 108.8(5) . . . yes C17 N18 H18 124.9 . . . no C24 N18 H18 126.2 . . . no C36 O35 H35 109.2 . . . no C41 O40 H40 108.8 . . . no C11 S31 O34 104.5(3) . . . yes C11 S31 O33 103.2(3) . . . yes O34 S31 O33 113.0(3) . . . yes C11 S31 Ni1 100.4(2) . . . yes O34 S31 Ni1 115.08(19) . . . yes O33 S31 Ni1 117.9(2) . . . yes C26 S32 Ni1 107.4(3) . . . yes N1 Ni1 N16 92.0(2) . . . yes N1 Ni1 S32 169.81(15) . . . yes N16 Ni1 S32 93.60(18) . . . yes N1 Ni1 S31 87.02(15) . . . yes N16 Ni1 S31 167.03(15) . . . yes S32 Ni1 S31 89.41(7) . . . yes 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_D _geom_hbond_site_symmetry_H _geom_hbond_site_symmetry_A _geom_hbond_publ_flag N3 H3 O40 0.86 1.88 2.733(8) 169 . . 2_565 yes N18 H18 O35 0.86 1.95 2.762(6) 157 . . . yes O35 H35 O34 0.82 1.96 2.754(7) 163 . . 3_645 yes O40 H40 O33 0.82 1.88 2.689(8) 168 . . 2_565 yes # Attachment '- CCDC 758103.cif' #\#CIF_1.1 # CIF produced by WinGX routine CIF_UPDATE # Created on 2006-07-24 at 15:22:03 # Using CIFtbx version 2.6.2 16 Jun 1998 # Dictionary name : cif_core.dic # Dictionary vers : 2.3 # Request file : e:\wingx\files\archive.dat # CIF files read : publish ldsal dreduc struct data_7 _database_code_depnum_ccdc_archive 'CCDC 758103' #TrackingRef '- CCDC 758103.cif' _audit_creation_date 2006-07-24T15:22:03-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' _audit_conform_dict_name cif_core.dic _audit_conform_dict_version 2.3 _audit_conform_dict_location ftp://ftp.iucr.org/pub/cif_core.dic _publ_section_abstract ; Herein we report the synthesis, structural and spectroscopic characterization of coordination compounds with bis[2-(1H-benzimidazol-2-yl)phenyl]disulfide [bis-(2phSbz)] (1) and cobalt(II), zinc(II) and cadmium halides (2-7). Their X-ray diffraction analyses showed that the metal ions present similar distorted tetrahedral structure, with the disulfide ligand coordinated through the imidazolic nitrogen atoms, forming a twisted eleven membered chelate. Structures of nickel(II) compounds 8 and 9, showed that the disulfide bond in the ligand was broken and the two halves were coordinated to the nickel(II) through the sulfur and one imidazole nitrogen atom forming six membered rings. In 8, the two ligands were sulfides, however in 9 one of them was oxidized to a sulfone. In both compounds the nickel(II) has a distorted square planar geometry and the sulfur atoms are in cis positions. The oxidation reaction of bis-(2phSbz) was performed in KMnO4/NaOH, giving the 2-(1H,3H-benzimidazolium-2-yl)-benzene sulfonate (10). The solid state structure of compounds 2-5 and 7-10 was determined by X-ray diffraction analyses. ; #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C13 H10 N2 O3 S, C2 H6 O S' _chemical_formula_sum 'C15 H16 N2 O4 S2' _chemical_formula_weight 352.44 _chemical_compound_source 'synthesis as described' _chemical_absolute_configuration . #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M 'P -1' _symmetry_space_group_name_Hall '-P 1' _symmetry_Int_Tables_number 2 loop_ _symmetry_equiv_pos_as_xyz x,y,z -x,-y,-z _cell_length_a 8.2067(4) _cell_length_b 10.0694(6) _cell_length_c 10.4613(6) _cell_angle_alpha 92.409(2) _cell_angle_beta 109.175(2) _cell_angle_gamma 98.036(3) _cell_volume 804.92(8) _cell_formula_units_Z 2 _cell_measurement_temperature 293 _cell_measurement_reflns_used 3086 _cell_measurement_theta_min 2 _cell_measurement_theta_max 27 _cell_measurement_wavelength 0.71073 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.6 _exptl_crystal_size_mid 0.55 _exptl_crystal_size_min 0.1 _exptl_crystal_density_diffrn 1.454 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 368 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.352 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min 0.8241 _exptl_absorpt_correction_T_max 0.9654 #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_source 'Enraf Nonius FR590' _diffrn_ambient_temperature 293 _diffrn_radiation_wavelength 0.7107 _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_detector 'CCD plate' _diffrn_detector_area_resol_mean 9 _diffrn_orient_matrix_type 'by Nonius Collect from scalepack cell' _diffrn_orient_matrix_ub_11 0.631304E-1 _diffrn_orient_matrix_ub_12 -0.584814E-1 _diffrn_orient_matrix_ub_13 0.680303E-1 _diffrn_orient_matrix_ub_21 -0.354094E-1 _diffrn_orient_matrix_ub_22 -0.768849E-1 _diffrn_orient_matrix_ub_23 -0.723481E-1 _diffrn_orient_matrix_ub_31 0.10889 _diffrn_orient_matrix_ub_32 0.285942E-1 _diffrn_orient_matrix_ub_33 -0.217156E-1 _diffrn_measurement_device '95mm CCD camera on \k-goniostat' _diffrn_measurement_device_type 'Nonius KappaCCD' _diffrn_measurement_method '\f & \w scans' _diffrn_standards_number 0 _diffrn_reflns_av_R_equivalents 0.05 _diffrn_reflns_av_unetI/netI 0.0675 _diffrn_reflns_number 5818 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 3.888 _diffrn_reflns_theta_max 27.555 _diffrn_reflns_theta_full 25.075 _diffrn_measured_fraction_theta_full 0.97 _diffrn_measured_fraction_theta_max 0.938 _reflns_number_total 3491 _reflns_number_gt 2143 _reflns_threshold_expression I>3.0\s(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection 'COLLECT (Nonius, 1997-2001).' _computing_cell_refinement 'DENZO/SCALEPACK (Otwinowski & Minor, 1997)' _computing_data_reduction 'DENZO/SCALEPACK (Otwinowski & Minor, 1997)' _computing_structure_solution 'SHELXS 97 (Sheldrick, 1997)' _computing_structure_refinement 'CRYSTALS (Betteridge et al., 2003)' _computing_molecular_graphics 'CAMERON (Watkin et al., 1996)' _computing_publication_material 'CRYSTALS (Betteridge et al., 2003)' #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _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 F _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details ; Method= Quasi-Unit weights W = 1.0 or 1./2F ; _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_ls_hydrogen_treatment refxyz _refine_ls_extinction_method None _refine_ls_number_reflns 2143 _refine_ls_number_parameters 256 _refine_ls_number_restraints 9 _refine_ls_R_factor_all 0.0819 _refine_ls_R_factor_gt 0.0426 _refine_ls_wR_factor_ref 0.0467 _refine_ls_wR_factor_gt 0.0467 _refine_ls_wR_factor_all 0.1014 _refine_ls_goodness_of_fit_ref 1.0915 _refine_ls_restrained_S_all 1.041 _refine_ls_shift/su_max 0.000382 _refine_ls_shift/su_mean 0 _refine_diff_density_max 0.23 _refine_diff_density_min -0.26 _refine_diff_density_rms 0.045 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# loop_ _atom_type_symbol _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C 0.0033 0.0016 'International Tables Vol C 4.2.6.8 and 6.1.1.4' H 0 0 'International Tables Vol C 4.2.6.8 and 6.1.1.4' N 0.0061 0.0033 'International Tables Vol C 4.2.6.8 and 6.1.1.4' S 0.1246 0.1234 'International Tables Vol C 4.2.6.8 and 6.1.1.4' O 0.0106 0.006 'International Tables Vol C 4.2.6.8 and 6.1.1.4' 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_disorder_assembly _atom_site_disorder_group H1 H -0.088(4) 0.587(4) 0.374(3) 0.0494 Uiso 1 . . H3 H 0.123(5) 0.907(4) 0.607(4) 0.0506 Uiso 1 . . H4 H 0.338(5) 1.038(4) 0.480(4) 0.0599 Uiso 1 . . H5 H 0.403(5) 0.999(4) 0.283(4) 0.0721 Uiso 1 . . H6 H 0.270(5) 0.801(4) 0.126(4) 0.0693 Uiso 1 . . H7 H 0.067(5) 0.634(4) 0.168(4) 0.0591 Uiso 1 . . H12 H -0.124(5) 0.598(4) 0.904(4) 0.0661 Uiso 1 . . H13 H -0.425(6) 0.597(4) 0.800(4) 0.0799 Uiso 1 . . H14 H -0.538(5) 0.654(4) 0.571(4) 0.0744 Uiso 1 . . H15 H -0.352(5) 0.708(4) 0.451(4) 0.0634 Uiso 1 . . H221 H 0.297(3) 0.108(4) 1.051(2) 0.1498 Uiso 1 . . H222 H 0.178(5) -0.016(2) 0.950(4) 0.1498 Uiso 1 . . H223 H 0.125(4) 0.128(4) 0.933(3) 0.1499 Uiso 1 . . H231 H 0.449(6) 0.317(5) 0.820(5) 0.094 Uiso 1 . . H232 H 0.455(7) 0.308(5) 0.962(5) 0.0941 Uiso 1 . . H233 H 0.279(7) 0.320(5) 0.867(5) 0.0939 Uiso 1 . . N1 N -0.0274(3) 0.6669(3) 0.4075(2) 0.0414 Uani 1 . . C2 C -0.0181(4) 0.7347(3) 0.5224(3) 0.0397 Uani 1 . . N3 N 0.0965(3) 0.8476(3) 0.5451(3) 0.0426 Uani 1 . . C4 C 0.2828(4) 0.9529(4) 0.4150(4) 0.0516 Uani 1 . . C5 C 0.3196(5) 0.9297(4) 0.2976(4) 0.0593 Uani 1 . . C6 C 0.2421(5) 0.8128(4) 0.2091(4) 0.0553 Uani 1 . . C7 C 0.1244(5) 0.7145(4) 0.2340(3) 0.0489 Uani 1 . . C8 C 0.0877(4) 0.7384(3) 0.3529(3) 0.0414 Uani 1 . . C9 C 0.1648(4) 0.8544(3) 0.4406(3) 0.0412 Uani 1 . . C10 C -0.1304(4) 0.6929(3) 0.6036(3) 0.0409 Uani 1 . . C11 C -0.0610(4) 0.6593(3) 0.7376(3) 0.0413 Uani 1 . . C12 C -0.1744(5) 0.6246(4) 0.8094(4) 0.0522 Uani 1 . . C13 C -0.3519(5) 0.6234(4) 0.7484(4) 0.062 Uani 1 . . C14 C -0.4196(5) 0.6543(4) 0.6171(4) 0.0607 Uani 1 . . C15 C -0.3090(5) 0.6888(4) 0.5443(4) 0.0533 Uani 1 . . S16 S 0.16567(11) 0.65023(8) 0.81309(8) 0.0435 Uani 1 . . O17 O 0.2568(3) 0.7864(2) 0.8483(2) 0.0589 Uani 1 . . O18 O 0.1780(3) 0.5724(3) 0.9282(2) 0.0633 Uani 1 . . O19 O 0.2086(3) 0.5807(2) 0.7054(2) 0.0493 Uani 1 . . S20 S 0.34456(12) 0.10879(9) 0.85259(8) 0.053 Uani 1 . . O21 O 0.2187(3) 0.0788(2) 0.7098(2) 0.0584 Uani 1 . . C22 C 0.2201(7) 0.0789(5) 0.9607(5) 0.0882 Uani 1 . . C23 C 0.3885(6) 0.2873(4) 0.8802(5) 0.0683 Uani 1 . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 N1 0.0458(15) 0.0392(14) 0.0353(13) -0.0004(11) 0.0116(11) 0.0005(12) C2 0.0447(17) 0.0406(16) 0.0305(14) 0.0029(12) 0.0083(13) 0.0067(14) N3 0.0487(16) 0.0428(15) 0.0322(13) -0.0024(11) 0.0115(12) 0.0007(12) C4 0.0471(19) 0.054(2) 0.0484(19) -0.0009(16) 0.0132(16) -0.0012(16) C5 0.054(2) 0.066(2) 0.058(2) 0.0084(18) 0.0221(18) 0.0006(18) C6 0.057(2) 0.070(2) 0.0435(18) 0.0087(17) 0.0218(17) 0.0107(18) C7 0.054(2) 0.053(2) 0.0383(17) -0.0004(15) 0.0149(15) 0.0086(16) C8 0.0415(17) 0.0451(17) 0.0358(15) 0.0063(13) 0.0095(13) 0.0091(14) C9 0.0399(17) 0.0461(17) 0.0363(15) 0.0033(13) 0.0116(13) 0.0060(14) C10 0.0430(17) 0.0410(16) 0.0383(15) 0.0008(13) 0.0144(13) 0.0050(13) C11 0.0457(18) 0.0418(16) 0.0365(15) 0.0018(13) 0.0141(13) 0.0072(13) C12 0.066(2) 0.052(2) 0.0451(18) 0.0019(15) 0.0285(17) 0.0095(17) C13 0.059(2) 0.066(2) 0.074(3) 0.004(2) 0.040(2) 0.0102(19) C14 0.043(2) 0.069(2) 0.071(2) 0.004(2) 0.0205(19) 0.0066(18) C15 0.046(2) 0.059(2) 0.0490(19) 0.0023(17) 0.0096(16) 0.0072(16) S16 0.0467(5) 0.0415(4) 0.0376(4) 0.0014(3) 0.0088(3) 0.0056(3) O17 0.0637(16) 0.0420(12) 0.0561(14) -0.0054(11) 0.0055(12) -0.0008(11) O18 0.0674(16) 0.0693(16) 0.0492(14) 0.0238(12) 0.0120(12) 0.0117(13) O19 0.0438(12) 0.0501(13) 0.0517(13) -0.0057(10) 0.0152(10) 0.0052(10) S20 0.0574(5) 0.0552(5) 0.0415(5) -0.0014(4) 0.0075(4) 0.0174(4) O21 0.0733(17) 0.0525(14) 0.0369(12) -0.0037(10) 0.0047(11) 0.0055(12) C22 0.147(5) 0.076(3) 0.073(3) 0.023(2) 0.068(3) 0.043(3) C23 0.063(3) 0.062(2) 0.059(2) -0.008(2) -0.004(2) 0.005(2) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _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_1 _geom_bond_site_symmetry_2 _geom_bond_publ_flag H1 N1 0.87(3) . . no H3 N3 0.82(3) . . no H4 C4 1.02(4) . . no H5 C5 0.96(4) . . no H6 C6 0.98(4) . . no H7 C7 0.99(4) . . no H12 C12 1.00(4) . . no H13 C13 0.95(4) . . no H14 C14 0.93(4) . . no H15 C15 0.96(4) . . no H221 C22 0.953(19) . . no H222 C22 0.958(19) . . no H223 C22 0.955(29) . . no H231 C23 0.95(5) . . no H232 C23 0.85(5) . . no H233 C23 0.97(5) . . no N1 C2 1.331(4) . . yes N1 C8 1.392(4) . . yes C2 N3 1.328(4) . . yes C2 C10 1.478(4) . . yes N3 C9 1.383(4) . . yes C4 C5 1.377(5) . . yes C4 C9 1.385(4) . . yes C5 C6 1.400(5) . . yes C6 C7 1.379(5) . . yes C7 C8 1.392(4) . . yes C8 C9 1.389(4) . . yes C10 C11 1.405(4) . . yes C10 C15 1.385(4) . . yes C11 C12 1.393(4) . . yes C11 S16 1.784(3) . . yes C12 C13 1.384(5) . . yes C13 C14 1.370(6) . . yes C14 C15 1.383(5) . . yes S16 O17 1.437(2) . . yes S16 O18 1.448(2) . . yes S16 O19 1.465(2) . . yes S20 O21 1.501(2) . . yes S20 C22 1.765(4) . . yes S20 C23 1.775(4) . . yes 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_2 _geom_angle_site_symmetry_3 _geom_angle_publ_flag H1 N1 C2 127(2) . . . no H1 N1 C8 124(2) . . . no C2 N1 C8 108.8(3) . . . yes N1 C2 N3 109.5(3) . . . yes N1 C2 C10 123.8(3) . . . yes N3 C2 C10 126.5(3) . . . yes C2 N3 H3 128(2) . . . no C2 N3 C9 108.8(2) . . . yes H3 N3 C9 123(2) . . . no H4 C4 C5 123(2) . . . no H4 C4 C9 121(2) . . . no C5 C4 C9 116.3(3) . . . yes H5 C5 C4 115(2) . . . no H5 C5 C6 124(2) . . . no C4 C5 C6 121.7(3) . . . yes H6 C6 C5 119(2) . . . no H6 C6 C7 119(2) . . . no C5 C6 C7 122.2(3) . . . yes H7 C7 C6 121(2) . . . no H7 C7 C8 123(2) . . . no C6 C7 C8 115.9(3) . . . yes N1 C8 C7 132.1(3) . . . yes N1 C8 C9 105.9(3) . . . yes C7 C8 C9 121.9(3) . . . yes C8 C9 C4 122.0(3) . . . yes C8 C9 N3 106.9(3) . . . yes C4 C9 N3 131.2(3) . . . yes C2 C10 C11 122.0(3) . . . yes C2 C10 C15 118.0(3) . . . yes C11 C10 C15 120.0(3) . . . yes C10 C11 C12 118.8(3) . . . yes C10 C11 S16 121.4(2) . . . yes C12 C11 S16 119.6(2) . . . yes H12 C12 C11 118(2) . . . no H12 C12 C13 122(2) . . . no C11 C12 C13 120.0(3) . . . yes H13 C13 C12 117(3) . . . no H13 C13 C14 122(3) . . . no C12 C13 C14 121.1(4) . . . yes H14 C14 C13 125(2) . . . no H14 C14 C15 116(3) . . . no C13 C14 C15 119.7(4) . . . yes H15 C15 C10 117(2) . . . no H15 C15 C14 122(2) . . . no C10 C15 C14 120.4(3) . . . yes C11 S16 O17 106.93(14) . . . yes C11 S16 O18 105.37(15) . . . yes O17 S16 O18 114.39(15) . . . yes C11 S16 O19 103.98(13) . . . yes O17 S16 O19 112.19(14) . . . yes O18 S16 O19 112.97(15) . . . yes O21 S20 C22 106.5(2) . . . yes O21 S20 C23 104.80(18) . . . yes C22 S20 C23 97.9(2) . . . yes S20 C22 H222 107.1(16) . . . no S20 C22 H223 108.0(16) . . . no H222 C22 H223 110.5(17) . . . no S20 C22 H221 106.7(17) . . . no H222 C22 H221 112.0(17) . . . no H223 C22 H221 112.3(17) . . . no S20 C23 H233 108(3) . . . no S20 C23 H231 106(3) . . . no H233 C23 H231 116(4) . . . no S20 C23 H232 107(3) . . . no H233 C23 H232 109(4) . . . no H231 C23 H232 110(4) . . . no # Attachment '- CCDC 766376.cif' #\#CIF_1.1 # CIF produced by WinGX routine CIF_UPDATE # Created on 2010-01-28 at 15:57:56 # Using CIFtbx version 2.6.2 16 Jun 1998 # Dictionary name : cif_core.dic # Dictionary vers : 2.4 # Request file : c:\wingx\files\archive.reqdat # CIF files read : publish 1 dreduc struct data_8 _database_code_depnum_ccdc_archive 'CCDC 766376' #TrackingRef '- CCDC 766376.cif' _audit_creation_date 2010-01-28T15:57:56-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' _audit_conform_dict_name cif_core.dic _audit_conform_dict_version 2.4 _audit_conform_dict_location ftp://ftp.iucr.org/pub/cif_core.dic _publ_section_abstract ; Herein we report the synthesis, structural and spectroscopic characterization of coordination compounds with bis[2-(1H-benzimidazol-2-yl)phenyl]disulfide [bis-(2phSbz)] (1) and cobalt(II), zinc(II) and cadmium halides (2-7). Their X-ray diffraction analyses showed that the metal ions present similar distorted tetrahedral structure, with the disulfide ligand coordinated through the imidazolic nitrogen atoms, forming a twisted eleven membered chelate. Structures of nickel(II) compounds 8 and 9, showed that the disulfide bond in the ligand was broken and the two halves were coordinated to the nickel(II) through the sulfur and one imidazole nitrogen atom forming six membered rings. In 8, the two ligands were sulfides, however in 9 one of them was oxidized to a sulfone. In both compounds the nickel(II) has a distorted square planar geometry and the sulfur atoms are in cis positions. The oxidation reaction of bis-(2phSbz) was performed in KMnO4/NaOH, giving the 2-(1H,3H-benzimidazolium-2-yl)-benzene sulfonate (10). The solid state structure of compounds 2-5 and 7-10 was determined by X-ray diffraction analyses. ; #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_formula_moiety '2(C26 H18 N4 Ni S2), 3(C2 H6 O), 2(H2 O)' _chemical_formula_sum 'C58 H58 N8 Ni2 O5 S4' _chemical_formula_weight 1192.83 _chemical_compound_source 'synthesis as described' _chemical_absolute_configuration . #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1' _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz x,y,z -x,-y,-z _cell_length_a 10.0074(2) _cell_length_b 13.0002(3) _cell_length_c 22.6833(4) _cell_angle_alpha 99.475(1) _cell_angle_beta 100.966(1) _cell_angle_gamma 102.611(1) _cell_volume 2761.05(10) _cell_formula_units_Z 2 _cell_measurement_temperature 173 _cell_measurement_reflns_used 57740 _cell_measurement_theta_min 1 _cell_measurement_theta_max 27 _cell_measurement_wavelength 0.71073 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description fragment _exptl_crystal_colour green _exptl_crystal_size_max 0.2 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.05 _exptl_crystal_density_diffrn 1.435 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1244 _exptl_special_details ; The crystal was placed in the cold stream of an Oxford Cryosystems open-flow nitrogen cryostat (Cosier & Glazer, 1986) with a nominal stability of 0.1K. Cosier, J. & Glazer, A.M., 1986. J. Appl. Cryst. 105 107. ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.89 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SADABS (Siemens, 1996)' _exptl_absorpt_correction_T_min 0.76 _exptl_absorpt_correction_T_max 0.96 #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_source 'Enraf Nonius FR590' _diffrn_ambient_temperature 173 _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_detector 'CCD plate' _diffrn_detector_area_resol_mean 9 _diffrn_orient_matrix_type 'by Bruker AXS Collect from scalepack cell' _diffrn_orient_matrix_ub_11 -0.657467E-1 _diffrn_orient_matrix_ub_12 -0.73875E-1 _diffrn_orient_matrix_ub_13 -0.111662E-1 _diffrn_orient_matrix_ub_21 -0.235682E-1 _diffrn_orient_matrix_ub_22 0.121362E-1 _diffrn_orient_matrix_ub_23 0.410733E-1 _diffrn_orient_matrix_ub_31 -0.788643E-1 _diffrn_orient_matrix_ub_32 0.301654E-1 _diffrn_orient_matrix_ub_33 -0.173974E-1 _diffrn_measurement_device Area _diffrn_measurement_device_type 'Nonius KappaCCD' _diffrn_measurement_method '\f & \w scans' _diffrn_standards_number 0 _diffrn_reflns_av_R_equivalents 0.082 _diffrn_reflns_number 40504 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -29 _diffrn_reflns_limit_l_max 29 _diffrn_reflns_theta_min 1.644 _diffrn_reflns_theta_max 27.467 _diffrn_reflns_theta_full 25.269 _diffrn_measured_fraction_theta_full 0.963 _diffrn_measured_fraction_theta_max 0.954 _reflns_number_total 12043 _reflns_number_gt 8180 _reflns_threshold_expression I>2.0\s(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection 'COLLECT (Nonius, 2001).' _computing_cell_refinement 'DENZO/SCALEPACK (Otwinowski & Minor, 1997)' _computing_data_reduction 'DENZO/SCALEPACK (Otwinowski & Minor, 1997)' _computing_structure_solution 'SHELXS 97 (Sheldrick, 1997)' _computing_structure_refinement 'CRYSTALS (Betteridge et al., 2003)' _computing_molecular_graphics 'CAMERON (Watkin et al., 1996)' _computing_publication_material 'CRYSTALS (Betteridge et al., 2003)' #----------------------------------------------------------------------------# # STRUCTURE SOLUTION #----------------------------------------------------------------------------# _atom_sites_solution_primary direct _atom_sites_solution_hydrogens difmap #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _refine_special_details ; ? ; _refine_ls_structure_factor_coef F _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details ; Method= Modified Sheldrick w=1/[\s^2^(F) + ( 0.00P)^2^ + 0.09P] ,where P=(max(Fo,0) + 2Fc)/3 ; _refine_ls_hydrogen_treatment . _refine_ls_extinction_method None _refine_ls_number_reflns 7203 _refine_ls_number_parameters 712 _refine_ls_number_restraints 60 _refine_ls_R_factor_all 0.1356 _refine_ls_R_factor_gt 0.0491 _refine_ls_wR_factor_ref 0.0639 _refine_ls_wR_factor_gt 0.0809 _refine_ls_wR_factor_all 0.1277 _refine_ls_goodness_of_fit_ref 1.0159 _refine_ls_shift/su_max 0.0005854 _refine_ls_shift/su_mean 0.1514644 _refine_diff_density_max 0.5 _refine_diff_density_min -0.51 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# loop_ _atom_type_symbol _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C 0.0033 0.0016 'International Tables Vol C 4.2.6.8 and 6.1.1.4' H 0 0 'International Tables Vol C 4.2.6.8 and 6.1.1.4' N 0.0061 0.0033 'International Tables Vol C 4.2.6.8 and 6.1.1.4' O 0.0106 0.006 'International Tables Vol C 4.2.6.8 and 6.1.1.4' S 0.1246 0.1234 'International Tables Vol C 4.2.6.8 and 6.1.1.4' Ni 0.3393 1.1124 'International Tables Vol C 4.2.6.8 and 6.1.1.4' 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_disorder_assembly _atom_site_disorder_group C2 C 0.6155(4) 0.6560(3) 0.0435(2) 0.0254 Uani 1 . . C4 C 0.4487(5) 0.5179(3) 0.1458(2) 0.031 Uani 1 . . C5 C 0.5180(5) 0.5048(4) 0.2010(2) 0.0343 Uani 1 . . C6 C 0.6645(5) 0.5447(3) 0.2221(2) 0.0349 Uani 1 . . C7 C 0.7463(5) 0.5979(3) 0.1879(2) 0.0308 Uani 1 . . C8 C 0.6766(4) 0.6127(3) 0.1319(2) 0.0256 Uani 1 . . C9 C 0.5305(4) 0.5738(3) 0.1118(2) 0.0251 Uani 1 . . C10 C 0.6161(4) 0.6998(3) -0.0113(2) 0.0279 Uani 1 . . C11 C 0.7361(4) 0.7140(3) -0.0372(2) 0.0295 Uani 1 . . C12 C 0.7282(5) 0.7543(4) -0.0905(2) 0.0352 Uani 1 . . C13 C 0.6074(5) 0.7789(4) -0.1188(2) 0.0409 Uani 1 . . C14 C 0.4906(5) 0.7651(4) -0.0935(3) 0.042 Uani 1 . . C15 C 0.4957(5) 0.7263(4) -0.0409(2) 0.0362 Uani 1 . . C17 C 1.0359(4) 0.8188(3) 0.2248(2) 0.0261 Uani 1 . . C19 C 0.8082(5) 0.9671(4) 0.2848(3) 0.0388 Uani 1 . . C20 C 0.6969(5) 0.9907(4) 0.2488(3) 0.0423 Uani 1 . . C21 C 0.6596(5) 0.9554(4) 0.1853(3) 0.041 Uani 1 . . C22 C 0.7326(5) 0.8933(3) 0.1550(2) 0.033 Uani 1 . . C23 C 0.8455(4) 0.8681(3) 0.1907(2) 0.0273 Uani 1 . . C24 C 0.8827(4) 0.9054(3) 0.2541(2) 0.0301 Uani 1 . . C25 C 1.1645(5) 0.7834(3) 0.2279(2) 0.0311 Uani 1 . . C26 C 1.2228(4) 0.7689(3) 0.1758(2) 0.03 Uani 1 . . C27 C 1.3581(5) 0.7526(3) 0.1842(3) 0.0367 Uani 1 . . C28 C 1.4321(5) 0.7462(4) 0.2412(3) 0.0432 Uani 1 . . C29 C 1.3736(5) 0.7554(3) 0.2914(3) 0.0425 Uani 1 . . C30 C 1.2414(5) 0.7740(3) 0.2846(2) 0.0378 Uani 1 . . C34 C -0.0011(4) 0.2077(3) 0.2957(2) 0.0211 Uani 1 . . C36 C 0.1888(4) 0.0746(3) 0.2029(2) 0.028 Uani 1 . . C37 C 0.3029(4) 0.0369(3) 0.2264(2) 0.0304 Uani 1 . . C38 C 0.3556(4) 0.0509(3) 0.2892(2) 0.0293 Uani 1 . . C39 C 0.2998(4) 0.1047(3) 0.3324(2) 0.0253 Uani 1 . . C40 C 0.1849(4) 0.1443(3) 0.3093(2) 0.0219 Uani 1 . . C41 C 0.1321(4) 0.1288(3) 0.2465(2) 0.0233 Uani 1 . . C42 C -0.1243(4) 0.2459(3) 0.3049(2) 0.0239 Uani 1 . . C43 C -0.1754(4) 0.2379(3) 0.3583(2) 0.0237 Uani 1 . . C44 C -0.3051(4) 0.2607(3) 0.3604(2) 0.0291 Uani 1 . . C45 C -0.3810(5) 0.2917(3) 0.3112(2) 0.0335 Uani 1 . . C46 C -0.3285(4) 0.3020(3) 0.2598(2) 0.0327 Uani 1 . . C47 C -0.2010(4) 0.2797(3) 0.2568(2) 0.028 Uani 1 . . C49 C 0.4340(4) 0.2862(3) 0.48167(19) 0.0204 Uani 1 . . C51 C 0.6086(4) 0.5065(3) 0.4241(2) 0.0265 Uani 1 . . C52 C 0.5438(5) 0.5524(3) 0.3796(2) 0.0326 Uani 1 . . C53 C 0.3972(5) 0.5143(3) 0.3533(2) 0.0315 Uani 1 . . C54 C 0.3134(4) 0.4299(3) 0.3707(2) 0.0262 Uani 1 . . C55 C 0.3791(4) 0.3830(3) 0.4146(2) 0.0216 Uani 1 . . C56 C 0.5240(4) 0.4211(3) 0.4406(2) 0.0222 Uani 1 . . C57 C 0.4277(4) 0.2037(3) 0.5180(2) 0.0251 Uani 1 . . C58 C 0.3032(4) 0.1621(3) 0.5362(2) 0.0264 Uani 1 . . C59 C 0.3009(5) 0.0782(4) 0.5678(2) 0.0348 Uani 1 . . C60 C 0.4176(5) 0.0390(4) 0.5825(3) 0.0414 Uani 1 . . C61 C 0.5412(5) 0.0830(4) 0.5673(2) 0.0383 Uani 1 . . C62 C 0.5470(5) 0.1638(3) 0.5347(2) 0.0303 Uani 1 . . C66 C 0.0201(5) 0.4738(4) 0.1402(3) 0.0444 Uani 1 . . C67 C 0.0888(7) 0.4672(5) 0.2030(3) 0.0593 Uani 1 . . C69 C 0.0409(6) 0.5459(5) 0.4327(3) 0.0596 Uani 1 . . C70 C -0.0023(7) 0.5717(6) 0.3721(3) 0.0733 Uani 1 . . C72 C 0.8166(14) 0.1100(11) 0.0616(4) 0.076 Uani 0.5 . 1 C73 C 0.8955(16) 0.0319(12) 0.0346(8) 0.0873 Uani 0.5 . 1 C74 C 0.8816(11) 0.0894(8) 0.0685(4) 0.0516 Uani 0.5 . 2 C75 C 0.7354(11) 0.0529(9) 0.0236(5) 0.0575 Uani 0.5 . 2 H31 H 0.412 0.5893 0.0329 0.0338 Uiso 1 . . H41 H 0.3518 0.4922 0.1316 0.0367 Uiso 1 . . H51 H 0.4678 0.4694 0.2253 0.0411 Uiso 1 . . H61 H 0.7108 0.5349 0.2602 0.0419 Uiso 1 . . H71 H 0.8447 0.623 0.2016 0.0371 Uiso 1 . . H121 H 0.8065 0.7655 -0.1074 0.0419 Uiso 1 . . H131 H 0.6058 0.8044 -0.1546 0.0492 Uiso 1 . . H141 H 0.4091 0.7819 -0.1118 0.05 Uiso 1 . . H151 H 0.4173 0.7188 -0.0241 0.0441 Uiso 1 . . H181 H 1.0452 0.8803 0.3127 0.0374 Uiso 1 . . H191 H 0.8332 0.9913 0.327 0.0456 Uiso 1 . . H201 H 0.6437 1.0319 0.2677 0.051 Uiso 1 . . H211 H 0.5845 0.9741 0.1624 0.0488 Uiso 1 . . H221 H 0.7075 0.8711 0.1128 0.0396 Uiso 1 . . H271 H 1.3998 0.746 0.1503 0.0443 Uiso 1 . . H281 H 1.5227 0.7357 0.2459 0.0524 Uiso 1 . . H291 H 1.4219 0.7504 0.3302 0.0506 Uiso 1 . . H301 H 1.202 0.7813 0.3186 0.0451 Uiso 1 . . H351 H -0.0376 0.1706 0.2049 0.0282 Uiso 1 . . H361 H 0.151 0.0638 0.162 0.0337 Uiso 1 . . H371 H 0.3452 0.002 0.1993 0.0359 Uiso 1 . . H381 H 0.4291 0.021 0.3022 0.0349 Uiso 1 . . H391 H 0.3363 0.114 0.3746 0.0295 Uiso 1 . . H441 H -0.3422 0.2533 0.3951 0.0349 Uiso 1 . . H451 H -0.467 0.3051 0.3134 0.0403 Uiso 1 . . H461 H -0.3798 0.3233 0.2276 0.0388 Uiso 1 . . H471 H -0.1644 0.2881 0.2221 0.0337 Uiso 1 . . H501 H 0.6372 0.3639 0.505 0.0256 Uiso 1 . . H511 H 0.7031 0.5315 0.4427 0.0317 Uiso 1 . . H521 H 0.5963 0.6097 0.3661 0.0389 Uiso 1 . . H531 H 0.3544 0.5466 0.3236 0.038 Uiso 1 . . H541 H 0.2166 0.4056 0.3536 0.0313 Uiso 1 . . H591 H 0.2198 0.0483 0.5792 0.042 Uiso 1 . . H601 H 0.4128 -0.0183 0.6027 0.0499 Uiso 1 . . H611 H 0.62 0.0576 0.5786 0.046 Uiso 1 . . H621 H 0.629 0.1927 0.5238 0.0362 Uiso 1 . . H651 H -0.1526 0.3949 0.0838 0.0672 Uiso 1 . . H661 H -0.0054 0.5426 0.141 0.0533 Uiso 1 . . H662 H 0.0857 0.469 0.1138 0.0532 Uiso 1 . . H672 H 0.1102 0.3977 0.2018 0.0889 Uiso 1 . . H671 H 0.1755 0.5245 0.2182 0.089 Uiso 1 . . H673 H 0.0252 0.4755 0.2299 0.089 Uiso 1 . . H681 H 0.1368 0.6784 0.4885 0.0791 Uiso 1 . . H692 H -0.0398 0.5403 0.4518 0.0721 Uiso 1 . . H691 H 0.0661 0.4764 0.427 0.0723 Uiso 1 . . H701 H 0.0799 0.5843 0.3549 0.1098 Uiso 1 . . H703 H -0.0765 0.5113 0.3461 0.11 Uiso 1 . . H702 H -0.0342 0.6362 0.3778 0.1103 Uiso 1 . . H711 H 0.8935 0.2363 0.1169 0.0849 Uiso 1 . . H721 H 0.7965 0.1562 0.0327 0.0913 Uiso 0.5 . 1 H722 H 0.7264 0.0673 0.066 0.0911 Uiso 0.5 . 1 H732 H 0.8389 -0.0069 -0.0058 0.131 Uiso 0.5 . 1 H731 H 0.9085 -0.0179 0.0612 0.131 Uiso 0.5 . 1 H733 H 0.9853 0.0728 0.031 0.131 Uiso 0.5 . 1 H741 H 0.9011 0.0278 0.0845 0.0618 Uiso 0.5 . 2 H742 H 0.9505 0.1137 0.0449 0.062 Uiso 0.5 . 2 H752 H 0.7213 0.1074 0.0008 0.0858 Uiso 0.5 . 2 H751 H 0.7295 -0.0121 -0.005 0.0859 Uiso 0.5 . 2 H753 H 0.663 0.039 0.0455 0.0859 Uiso 0.5 . 2 H761 H 0.0979 -0.004 0.4269 0.071 Uiso 1 . . H762 H 0.0594 -0.115 0.4255 0.071 Uiso 1 . . H771 H 0.8188 0.4855 -0.011 0.0572 Uiso 1 . . H772 H 0.8245 0.3806 -0.0254 0.0573 Uiso 1 . . N1 N 0.7274(3) 0.6648(3) 0.08787(17) 0.0245 Uani 1 . . N3 N 0.4954(4) 0.6026(3) 0.05620(17) 0.0271 Uani 1 . . N16 N 0.9407(3) 0.8119(3) 0.17393(17) 0.0255 Uani 1 . . N18 N 1.0031(4) 0.8731(3) 0.27498(18) 0.031 Uani 1 . . N33 N 0.1012(3) 0.1965(2) 0.34010(16) 0.0201 Uani 1 . . N35 N 0.0160(3) 0.1707(3) 0.23944(16) 0.0238 Uani 1 . . N48 N 0.3255(3) 0.2972(3) 0.44147(16) 0.0216 Uani 1 . . N50 N 0.5560(3) 0.3583(2) 0.48217(16) 0.021 Uani 1 . . O65 O -0.1030(4) 0.3871(3) 0.11604(18) 0.045 Uani 1 . . O68 O 0.1591(3) 0.6256(3) 0.47298(19) 0.0529 Uani 1 . . O71 O 0.8956(4) 0.1742(3) 0.11914(18) 0.057 Uani 1 . . O76 O 0.0845(4) -0.0660(3) 0.40900(17) 0.0477 Uani 1 . . O77 O 0.7949(3) 0.4240(3) -0.00440(16) 0.0379 Uani 1 . . S31 S 0.89437(11) 0.68239(9) -0.00559(5) 0.0308 Uani 1 . . S32 S 1.14412(11) 0.77742(9) 0.10088(6) 0.0306 Uani 1 . . S63 S -0.09495(10) 0.19319(8) 0.42229(5) 0.0245 Uani 1 . . S64 S 0.15139(11) 0.21087(9) 0.52233(5) 0.0302 Uani 1 . . Ni1 Ni 0.91955(5) 0.73400(4) 0.09298(3) 0.0241 Uani 1 . . Ni2 Ni 0.12859(5) 0.22828(4) 0.42738(2) 0.0205 Uani 1 . . 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 C2 0.024(2) 0.025(2) 0.025(3) 0.0018(17) 0.0056(17) 0.0053(16) C4 0.028(2) 0.033(2) 0.033(3) 0.007(2) 0.0104(19) 0.0086(18) C5 0.035(2) 0.033(2) 0.037(3) 0.011(2) 0.013(2) 0.0064(19) C6 0.045(3) 0.034(2) 0.028(3) 0.012(2) 0.006(2) 0.012(2) C7 0.029(2) 0.034(2) 0.027(3) 0.0088(19) -0.0003(18) 0.0076(18) C8 0.028(2) 0.025(2) 0.026(3) 0.0035(17) 0.0088(18) 0.0109(16) C9 0.029(2) 0.0236(19) 0.021(3) 0.0012(17) 0.0050(17) 0.0067(16) C10 0.028(2) 0.031(2) 0.018(3) -0.0005(17) 0.0014(17) 0.0024(17) C11 0.028(2) 0.031(2) 0.023(3) -0.0015(18) 0.0030(18) 0.0004(17) C12 0.031(2) 0.043(3) 0.025(3) 0.006(2) 0.0052(19) -0.001(2) C13 0.039(3) 0.055(3) 0.025(3) 0.018(2) 0.003(2) 0.001(2) C14 0.036(3) 0.054(3) 0.034(3) 0.015(2) 0.002(2) 0.009(2) C15 0.029(2) 0.044(3) 0.036(3) 0.014(2) 0.007(2) 0.006(2) C17 0.031(2) 0.0226(19) 0.021(3) 0.0024(17) 0.0067(18) 0.0006(16) C19 0.048(3) 0.032(2) 0.031(3) -0.006(2) 0.023(2) -0.004(2) C20 0.035(3) 0.036(2) 0.054(4) -0.005(2) 0.023(2) 0.003(2) C21 0.033(3) 0.037(2) 0.050(4) 0.000(2) 0.012(2) 0.008(2) C22 0.033(2) 0.034(2) 0.029(3) -0.0011(19) 0.008(2) 0.0073(19) C23 0.026(2) 0.024(2) 0.031(3) 0.0021(18) 0.0127(18) 0.0020(16) C24 0.030(2) 0.027(2) 0.029(3) 0.0004(18) 0.0107(19) -0.0019(17) C25 0.031(2) 0.0196(19) 0.035(3) 0.0016(18) 0.0022(19) -0.0011(16) C26 0.027(2) 0.025(2) 0.034(3) 0.0048(19) 0.0022(19) 0.0041(17) C27 0.031(2) 0.031(2) 0.045(3) 0.002(2) 0.008(2) 0.0085(19) C28 0.035(3) 0.031(2) 0.054(4) -0.002(2) -0.008(2) 0.012(2) C29 0.051(3) 0.029(2) 0.037(3) 0.002(2) -0.011(2) 0.011(2) C30 0.043(3) 0.025(2) 0.035(3) 0.003(2) -0.005(2) 0.0029(19) C34 0.0223(19) 0.0193(18) 0.022(3) 0.0054(16) 0.0053(16) 0.0038(15) C36 0.033(2) 0.030(2) 0.023(3) 0.0058(18) 0.0124(18) 0.0070(18) C37 0.032(2) 0.025(2) 0.036(3) 0.0032(19) 0.016(2) 0.0073(17) C38 0.027(2) 0.028(2) 0.034(3) 0.0058(19) 0.0090(19) 0.0094(17) C39 0.021(2) 0.027(2) 0.026(3) 0.0070(17) 0.0043(17) 0.0045(16) C40 0.0202(19) 0.0216(18) 0.025(3) 0.0072(16) 0.0078(16) 0.0043(15) C41 0.025(2) 0.0228(19) 0.022(3) 0.0084(17) 0.0060(17) 0.0045(16) C42 0.0220(19) 0.0228(19) 0.026(3) 0.0028(17) 0.0056(16) 0.0053(15) C43 0.022(2) 0.0229(19) 0.023(3) 0.0015(17) 0.0015(16) 0.0050(16) C44 0.025(2) 0.035(2) 0.025(3) -0.0015(19) 0.0074(18) 0.0099(18) C45 0.027(2) 0.036(2) 0.035(3) -0.003(2) 0.0011(19) 0.0157(19) C46 0.029(2) 0.031(2) 0.035(3) 0.0045(19) -0.0027(19) 0.0134(18) C47 0.027(2) 0.030(2) 0.027(3) 0.0065(18) 0.0031(18) 0.0098(17) C49 0.0212(19) 0.0249(19) 0.014(2) 0.0007(16) 0.0033(15) 0.0061(15) C51 0.024(2) 0.028(2) 0.026(3) 0.0010(18) 0.0119(17) 0.0029(16) C52 0.038(2) 0.026(2) 0.033(3) 0.0076(19) 0.015(2) 0.0004(18) C53 0.036(2) 0.030(2) 0.030(3) 0.0113(19) 0.008(2) 0.0069(18) C54 0.023(2) 0.029(2) 0.024(3) 0.0047(18) 0.0044(17) 0.0035(16) C55 0.025(2) 0.0242(19) 0.016(2) 0.0021(16) 0.0098(16) 0.0061(16) C56 0.024(2) 0.0246(19) 0.017(2) -0.0006(16) 0.0047(16) 0.0063(16) C57 0.030(2) 0.0238(19) 0.017(3) 0.0008(16) -0.0009(17) 0.0058(16) C58 0.027(2) 0.029(2) 0.018(3) 0.0050(17) 0.0007(17) 0.0023(17) C59 0.039(3) 0.037(2) 0.021(3) 0.012(2) -0.0017(19) -0.001(2) C60 0.051(3) 0.032(2) 0.037(3) 0.014(2) 0.000(2) 0.006(2) C61 0.045(3) 0.035(2) 0.030(3) 0.008(2) -0.007(2) 0.014(2) C62 0.031(2) 0.032(2) 0.023(3) 0.0020(18) -0.0019(18) 0.0094(18) C66 0.045(2) 0.046(2) 0.040(3) 0.006(2) 0.0100(19) 0.0091(16) C67 0.063(3) 0.056(3) 0.045(3) 0.010(2) -0.001(2) -0.001(2) C69 0.039(2) 0.079(3) 0.050(3) -0.006(2) 0.004(2) 0.011(2) C70 0.065(3) 0.089(4) 0.056(3) -0.001(3) -0.003(3) 0.025(3) C72 0.098(5) 0.069(4) 0.043(4) 0.002(3) -0.004(4) 0.007(4) C73 0.103(6) 0.079(6) 0.057(6) -0.008(5) 0.000(5) 0.009(5) C74 0.068(4) 0.051(4) 0.031(4) 0.009(2) 0.002(3) 0.014(3) C75 0.071(5) 0.054(5) 0.037(5) 0.007(4) -0.003(4) 0.010(4) N1 0.0224(17) 0.0296(17) 0.020(2) 0.0022(15) 0.0071(14) 0.0049(14) N3 0.0223(17) 0.0342(19) 0.023(2) 0.0050(16) 0.0034(14) 0.0052(14) N16 0.0236(17) 0.0296(18) 0.021(2) 0.0018(15) 0.0055(14) 0.0038(14) N18 0.037(2) 0.0308(19) 0.020(2) 0.0012(15) 0.0054(16) 0.0026(16) N33 0.0204(16) 0.0227(16) 0.017(2) 0.0038(13) 0.0039(13) 0.0050(13) N35 0.0250(17) 0.0325(18) 0.014(2) 0.0079(14) 0.0048(14) 0.0063(14) N48 0.0214(16) 0.0250(16) 0.017(2) 0.0063(14) 0.0026(13) 0.0040(13) N50 0.0173(16) 0.0256(16) 0.018(2) 0.0025(14) 0.0004(13) 0.0050(13) O65 0.0439(18) 0.0480(18) 0.039(2) 0.0106(15) 0.0023(15) 0.0086(14) O68 0.0298(16) 0.074(2) 0.047(2) -0.0128(18) 0.0038(15) 0.0194(15) O71 0.083(3) 0.051(2) 0.031(2) 0.0092(15) 0.0001(18) 0.0170(19) O76 0.054(2) 0.047(2) 0.036(2) 0.0054(17) 0.0147(17) -0.0003(17) O77 0.0287(16) 0.0446(18) 0.039(2) 0.0087(15) 0.0053(14) 0.0082(14) S31 0.0284(5) 0.0406(6) 0.0223(7) 0.0020(5) 0.0078(4) 0.0083(5) S32 0.0243(5) 0.0383(6) 0.0272(7) 0.0038(5) 0.0068(4) 0.0059(4) S63 0.0219(5) 0.0295(5) 0.0219(6) 0.0056(4) 0.0061(4) 0.0050(4) S64 0.0267(5) 0.0422(6) 0.0223(7) 0.0126(5) 0.0063(4) 0.0056(4) Ni1 0.0217(3) 0.0289(3) 0.0196(3) 0.0013(2) 0.0049(2) 0.0053(2) Ni2 0.0186(3) 0.0242(3) 0.0173(3) 0.0048(2) 0.0033(2) 0.00337(19) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 _geom_bond_publ_flag C2 C10 1.452(6) . . yes C2 N1 1.326(6) . . yes C2 N3 1.357(5) . . yes C4 C5 1.367(7) . . yes C4 C9 1.400(6) . . yes C4 H41 0.928 . . no C5 C6 1.403(6) . . yes C5 H51 0.925 . . no C6 C7 1.385(6) . . yes C6 H61 0.942 . . no C7 C8 1.393(6) . . yes C7 H71 0.939 . . no C8 C9 1.397(6) . . yes C8 N1 1.407(6) . . yes C9 N3 1.377(6) . . yes C10 C11 1.423(6) . . yes C10 C15 1.403(6) . . yes C11 C12 1.391(7) . . yes C11 S31 1.772(5) . . yes C12 C13 1.384(7) . . yes C12 H121 0.929 . . no C13 C14 1.387(7) . . yes C13 H131 0.927 . . no C14 C15 1.367(7) . . yes C14 H141 0.929 . . no C15 H151 0.929 . . no C17 C25 1.451(6) . . yes C17 N16 1.326(6) . . yes C17 N18 1.371(6) . . yes C19 C20 1.374(8) . . yes C19 C24 1.400(6) . . yes C19 H191 0.922 . . no C20 C21 1.388(8) . . yes C20 H201 0.943 . . no C21 C22 1.388(6) . . yes C21 H211 0.931 . . no C22 C23 1.393(7) . . yes C22 H221 0.922 . . no C23 C24 1.389(7) . . yes C23 N16 1.392(5) . . yes C24 N18 1.386(6) . . yes C25 C26 1.419(7) . . yes C25 C30 1.405(7) . . yes C26 C27 1.398(6) . . yes C26 S32 1.763(5) . . yes C27 C28 1.388(8) . . yes C27 H271 0.942 . . no C28 C29 1.375(8) . . yes C28 H281 0.935 . . no C29 C30 1.381(7) . . yes C29 H291 0.94 . . no C30 H301 0.931 . . no C34 C42 1.463(5) . . yes C34 N33 1.344(5) . . yes C34 N35 1.344(5) . . yes C36 C37 1.389(6) . . yes C36 C41 1.396(6) . . yes C36 H361 0.909 . . no C37 C38 1.387(7) . . yes C37 H371 0.924 . . no C38 C39 1.383(6) . . yes C38 H381 0.927 . . no C39 C40 1.407(6) . . yes C39 H391 0.935 . . no C40 C41 1.386(6) . . yes C40 N33 1.402(5) . . yes C41 N35 1.381(5) . . yes C42 C43 1.412(6) . . yes C42 C47 1.399(6) . . yes C43 C44 1.400(6) . . yes C43 S63 1.770(4) . . yes C44 C45 1.394(7) . . yes C44 H441 0.942 . . no C45 C46 1.381(7) . . yes C45 H451 0.923 . . no C46 C47 1.381(6) . . yes C46 H461 0.927 . . no C47 H471 0.941 . . no C49 C57 1.453(6) . . yes C49 N48 1.329(5) . . yes C49 N50 1.365(5) . . yes C51 C52 1.383(7) . . yes C51 C56 1.392(6) . . yes C51 H511 0.92 . . no C52 C53 1.416(6) . . yes C52 H521 0.944 . . no C53 C54 1.389(6) . . yes C53 H531 0.935 . . no C54 C55 1.386(6) . . yes C54 H541 0.934 . . no C55 C56 1.400(6) . . yes C55 N48 1.411(5) . . yes C56 N50 1.383(5) . . yes C57 C58 1.411(6) . . yes C57 C62 1.415(6) . . yes C58 C59 1.400(6) . . yes C58 S64 1.764(4) . . yes C59 C60 1.379(7) . . yes C59 H591 0.923 . . no C60 C61 1.376(7) . . yes C60 H601 0.934 . . no C61 C62 1.378(6) . . yes C61 H611 0.928 . . no C62 H621 0.921 . . no C66 C67 1.484(8) . . yes C66 H661 0.981 . . no C66 H662 0.974 . . no C66 O65 1.422(6) . . yes C67 H672 0.971 . . no C67 H671 0.973 . . no C67 H673 0.971 . . no C69 C70 1.475(10) . . yes C69 H692 0.982 . . no C69 H691 0.984 . . no C69 O68 1.431(6) . . yes C70 H701 0.97 . . no C70 H703 0.971 . . no C70 H702 0.959 . . no C72 C73 1.535(5) . . yes C72 H721 0.982 . . no C72 H722 0.983 . . no C72 O71 1.410(5) . . yes C73 H732 0.969 . . no C73 H731 0.967 . . no C73 H733 0.965 . . no C74 C75 1.541(5) . . yes C74 H741 0.973 . . no C74 H742 0.98 . . no C74 O71 1.418(5) . . yes C75 H752 0.961 . . no C75 H751 0.959 . . no C75 H753 0.957 . . no H31 N3 0.863 . . no H181 N18 0.86 . . no H351 N35 0.86 . . no H501 N50 0.857 . . no H651 O65 0.837 . . no H681 O68 0.814 . . no H711 O71 0.822 . . no H761 O76 0.811 . . no H762 O76 0.807 . . no H771 O77 0.83 . . no H772 O77 0.819 . . no N1 Ni1 1.909(3) . . yes N16 Ni1 1.894(4) . . yes N33 Ni2 1.908(3) . . yes N48 Ni2 1.919(3) . . yes S31 Ni1 2.1752(13) . . yes S32 Ni1 2.1589(11) . . yes S63 Ni2 2.1598(11) . . yes S64 Ni2 2.1767(13) . . yes 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_2 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C10 C2 N1 125.8(4) . . . yes C10 C2 N3 122.7(4) . . . yes N1 C2 N3 111.5(4) . . . yes C5 C4 C9 116.9(4) . . . yes C5 C4 H41 122 . . . no C9 C4 H41 121.1 . . . no C4 C5 C6 121.4(4) . . . yes C4 C5 H51 119.8 . . . no C6 C5 H51 118.8 . . . no C5 C6 C7 121.9(5) . . . yes C5 C6 H61 120.3 . . . no C7 C6 H61 117.7 . . . no C6 C7 C8 117.2(4) . . . yes C6 C7 H71 122 . . . no C8 C7 H71 120.8 . . . no C7 C8 C9 120.3(4) . . . yes C7 C8 N1 131.2(4) . . . yes C9 C8 N1 108.5(4) . . . yes C4 C9 C8 122.2(4) . . . yes C4 C9 N3 132.0(4) . . . yes C8 C9 N3 105.8(4) . . . yes C2 C10 C11 121.2(4) . . . yes C2 C10 C15 120.1(4) . . . yes C11 C10 C15 118.7(4) . . . yes C10 C11 C12 118.1(4) . . . yes C10 C11 S31 123.8(4) . . . yes C12 C11 S31 118.1(3) . . . yes C11 C12 C13 121.7(4) . . . yes C11 C12 H121 119 . . . no C13 C12 H121 119.2 . . . no C12 C13 C14 120.1(5) . . . yes C12 C13 H131 119.1 . . . no C14 C13 H131 120.8 . . . no C13 C14 C15 119.4(5) . . . yes C13 C14 H141 121.1 . . . no C15 C14 H141 119.6 . . . no C10 C15 C14 122.0(4) . . . yes C10 C15 H151 119.6 . . . no C14 C15 H151 118.4 . . . no C25 C17 N16 125.9(4) . . . yes C25 C17 N18 123.4(4) . . . yes N16 C17 N18 110.5(4) . . . yes C20 C19 C24 116.5(5) . . . yes C20 C19 H191 121.8 . . . no C24 C19 H191 121.7 . . . no C19 C20 C21 122.1(4) . . . yes C19 C20 H201 119.2 . . . no C21 C20 H201 118.7 . . . no C20 C21 C22 121.4(5) . . . yes C20 C21 H211 119.6 . . . no C22 C21 H211 119 . . . no C21 C22 C23 117.4(5) . . . yes C21 C22 H221 120.6 . . . no C23 C22 H221 122 . . . no C22 C23 C24 120.5(4) . . . yes C22 C23 N16 130.8(4) . . . yes C24 C23 N16 108.7(4) . . . yes C19 C24 C23 122.2(5) . . . yes C19 C24 N18 131.7(5) . . . yes C23 C24 N18 106.0(4) . . . yes C17 C25 C26 121.0(4) . . . yes C17 C25 C30 120.1(5) . . . yes C26 C25 C30 118.6(4) . . . yes C25 C26 C27 118.1(4) . . . yes C25 C26 S32 125.8(3) . . . yes C27 C26 S32 116.0(4) . . . yes C26 C27 C28 121.5(5) . . . yes C26 C27 H271 119 . . . no C28 C27 H271 119.4 . . . no C27 C28 C29 120.6(5) . . . yes C27 C28 H281 120.2 . . . no C29 C28 H281 119.2 . . . no C28 C29 C30 119.0(5) . . . yes C28 C29 H291 121.7 . . . no C30 C29 H291 119.3 . . . no C25 C30 C29 122.1(5) . . . yes C25 C30 H301 118.7 . . . no C29 C30 H301 119.2 . . . no C42 C34 N33 126.1(4) . . . yes C42 C34 N35 122.2(4) . . . yes N33 C34 N35 111.5(3) . . . yes C37 C36 C41 115.7(4) . . . yes C37 C36 H361 122.9 . . . no C41 C36 H361 121.4 . . . no C36 C37 C38 121.9(4) . . . yes C36 C37 H371 118.8 . . . no C38 C37 H371 119.3 . . . no C37 C38 C39 122.4(4) . . . yes C37 C38 H381 118.1 . . . no C39 C38 H381 119.4 . . . no C38 C39 C40 116.3(4) . . . yes C38 C39 H391 121.8 . . . no C40 C39 H391 121.9 . . . no C39 C40 C41 120.8(4) . . . yes C39 C40 N33 130.4(4) . . . yes C41 C40 N33 108.7(3) . . . yes C36 C41 C40 122.9(4) . . . yes C36 C41 N35 130.9(4) . . . yes C40 C41 N35 106.2(3) . . . yes C34 C42 C43 121.1(4) . . . yes C34 C42 C47 118.8(4) . . . yes C43 C42 C47 119.7(4) . . . yes C42 C43 C44 118.4(4) . . . yes C42 C43 S63 125.7(3) . . . yes C44 C43 S63 115.8(3) . . . yes C43 C44 C45 120.7(4) . . . yes C43 C44 H441 119.5 . . . no C45 C44 H441 119.8 . . . no C44 C45 C46 120.5(4) . . . yes C44 C45 H451 119.1 . . . no C46 C45 H451 120.4 . . . no C45 C46 C47 119.7(4) . . . yes C45 C46 H461 119.5 . . . no C47 C46 H461 120.8 . . . no C42 C47 C46 120.9(5) . . . yes C42 C47 H471 119.4 . . . no C46 C47 H471 119.7 . . . no C57 C49 N48 125.1(3) . . . yes C57 C49 N50 123.3(3) . . . yes N48 C49 N50 111.5(3) . . . yes C52 C51 C56 117.0(4) . . . yes C52 C51 H511 122.1 . . . no C56 C51 H511 120.8 . . . no C51 C52 C53 120.7(4) . . . yes C51 C52 H521 120.7 . . . no C53 C52 H521 118.6 . . . no C52 C53 C54 121.8(4) . . . yes C52 C53 H531 119.9 . . . no C54 C53 H531 118.3 . . . no C53 C54 C55 117.4(4) . . . yes C53 C54 H541 121.5 . . . no C55 C54 H541 121.1 . . . no C54 C55 C56 120.7(4) . . . yes C54 C55 N48 131.4(4) . . . yes C56 C55 N48 107.9(4) . . . yes C55 C56 C51 122.4(4) . . . yes C55 C56 N50 106.4(3) . . . yes C51 C56 N50 131.1(4) . . . yes C49 C57 C58 120.7(4) . . . yes C49 C57 C62 119.8(4) . . . yes C58 C57 C62 119.5(4) . . . yes C57 C58 C59 118.0(4) . . . yes C57 C58 S64 123.8(3) . . . yes C59 C58 S64 118.2(3) . . . yes C58 C59 C60 121.4(4) . . . yes C58 C59 H591 119.5 . . . no C60 C59 H591 119.1 . . . no C59 C60 C61 120.6(4) . . . yes C59 C60 H601 119.8 . . . no C61 C60 H601 119.5 . . . no C60 C61 C62 119.8(4) . . . yes C60 C61 H611 119.9 . . . no C62 C61 H611 120.2 . . . no C57 C62 C61 120.5(4) . . . yes C57 C62 H621 119.3 . . . no C61 C62 H621 120.2 . . . no C67 C66 H661 110.5 . . . no C67 C66 H662 108.9 . . . no H661 C66 H662 108.7 . . . no C67 C66 O65 110.1(4) . . . yes H661 C66 O65 109.4 . . . no H662 C66 O65 109.1 . . . no C66 C67 H672 109.5 . . . no C66 C67 H671 109.3 . . . no H672 C67 H671 109.5 . . . no C66 C67 H673 109 . . . no H672 C67 H673 109.8 . . . no H671 C67 H673 109.7 . . . no C70 C69 H692 107.4 . . . no C70 C69 H691 109.3 . . . no H692 C69 H691 109.7 . . . no C70 C69 O68 113.4(6) . . . yes H692 C69 O68 108.8 . . . no H691 C69 O68 108.1 . . . no C69 C70 H701 107.6 . . . no C69 C70 H703 108.7 . . . no H701 C70 H703 111.1 . . . no C69 C70 H702 108.8 . . . no H701 C70 H702 109.3 . . . no H703 C70 H702 111.1 . . . no C73 C72 H721 109 . . . no C73 C72 H722 108.3 . . . no H721 C72 H722 108.2 . . . no C73 C72 O71 111.5(10) . . . yes H721 C72 O71 109.9 . . . no H722 C72 O71 109.8 . . . no C72 C73 H732 107.8 . . . no C72 C73 H731 109.3 . . . no H732 C73 H731 110.4 . . . no C72 C73 H733 109 . . . no H732 C73 H733 109.8 . . . no H731 C73 H733 110.5 . . . no C75 C74 H741 108.6 . . . no C75 C74 H742 107.1 . . . no H741 C74 H742 109.9 . . . no C75 C74 O71 114.6(8) . . . yes H741 C74 O71 108 . . . no H742 C74 O71 108.6 . . . no C74 C75 H752 110.4 . . . no C74 C75 H751 109.2 . . . no H752 C75 H751 108.5 . . . no C74 C75 H753 110.4 . . . no H752 C75 H753 109.4 . . . no H751 C75 H753 108.8 . . . no C8 N1 C2 106.0(3) . . . yes C8 N1 Ni1 125.9(3) . . . yes C2 N1 Ni1 128.1(3) . . . yes C9 N3 C2 108.3(4) . . . yes C9 N3 H31 126.7 . . . no C2 N3 H31 125 . . . no C23 N16 C17 107.0(4) . . . yes C23 N16 Ni1 123.3(3) . . . yes C17 N16 Ni1 129.5(3) . . . yes C24 N18 C17 107.7(4) . . . yes C24 N18 H181 126.3 . . . no C17 N18 H181 125.7 . . . no C40 N33 C34 105.5(3) . . . yes C40 N33 Ni2 123.6(3) . . . yes C34 N33 Ni2 130.7(3) . . . yes C41 N35 C34 108.1(3) . . . yes C41 N35 H351 125.6 . . . no C34 N35 H351 126.3 . . . no C55 N48 C49 106.4(3) . . . yes C55 N48 Ni2 123.7(3) . . . yes C49 N48 Ni2 129.4(3) . . . yes C56 N50 C49 107.7(3) . . . yes C56 N50 H501 126.8 . . . no C49 N50 H501 125.5 . . . no C66 O65 H651 112.4 . . . no C69 O68 H681 112.2 . . . no C72 O71 H711 105 . . . no H761 O76 H762 120.2 . . . no H771 O77 H772 111.8 . . . no C11 S31 Ni1 103.18(16) . . . yes C26 S32 Ni1 106.18(15) . . . yes C43 S63 Ni2 107.88(14) . . . yes C58 S64 Ni2 103.15(16) . . . yes N1 Ni1 N16 91.55(15) . . . yes N1 Ni1 S31 92.08(11) . . . yes N16 Ni1 S31 166.00(11) . . . yes N1 Ni1 S32 167.15(11) . . . yes N16 Ni1 S32 91.94(10) . . . yes S31 Ni1 S32 87.48(5) . . . yes N48 Ni2 N33 93.74(14) . . . yes N48 Ni2 S64 91.91(11) . . . yes N33 Ni2 S64 162.22(10) . . . yes N48 Ni2 S63 164.78(10) . . . yes N33 Ni2 S63 92.85(10) . . . yes S64 Ni2 S63 85.91(4) . . . yes # END of CIF