# Supplementary Material (ESI) for Chemical Communications # This journal is (c) The Royal Society of Chemistry 2007 data_global _journal_name_full Chem.Commun. _journal_coden_Cambridge 0182 _publ_contact_letter ; These are the CIF format data (3 compounds) for the paper "Unusual Nickel-mediated C-S Activation of Alkyl and Aryl Sulfoxides " Thomas Schaub, Marc Backes, and Udo Radius ; _publ_section_title ; UnusualNickel-mediated C-S Activation of Alkyl and Aryl Sulfoxides ; _publ_contact_author_name 'Dr. Udo Radius' _publ_contact_author_address ;Institut fuer Anorganische Chemie University of Karlsruhe Engesserstr. 15 76131 Karlsruhe GERMANY ; _publ_contact_author_email radius@aoc1.uni-karlsruhe.de _publ_contact_author_phone 'Int + 721 608 8097' _publ_contact_author_fax 'Int + 721 608 8440' _audit_creation_method 'SHELXL-97 + manual editing' loop_ _publ_author_name 'Thomas Schaub' 'Marc Backes' 'Udo Radius' data_compound2 _database_code_depnum_ccdc_archive 'CCDC 626501' _audit_creation_method SHELXL-97 _chemical_name_systematic ; Bis-{1,3-di(isopropyl)imidazol-2-ylidene)(methylsulfoxyl)(methyl)nickel(II) ; _chemical_formula_sum 'C27 H46 N4 Ni O S' _chemical_formula_weight 533.45 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Ni Ni 0.3393 1.1124 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P2(1)/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 8.9991(6) _cell_length_b 12.2314(5) _cell_length_c 27.8178(18) _cell_angle_alpha 90.00 _cell_angle_beta 93.695(8) _cell_angle_gamma 90.00 _cell_volume 3055.6(3) _cell_formula_units_Z 4 _cell_measurement_temperature 203(2) _cell_measurement_reflns_used 8000 _cell_measurement_theta_min 1.85 _cell_measurement_theta_max 24.90 _exptl_crystal_description prism _exptl_crystal_colour yellow _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.15 _exptl_crystal_density_diffrn 1.160 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1152 _exptl_absorpt_coefficient_mu 0.727 _exptl_absorpt_correction_type numerical _exptl_absorpt_correction_T_min 0.712 _exptl_absorpt_correction_T_max 0.810 _diffrn_ambient_temperature 203(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'STOE IPDS 1' _diffrn_measurement_method rotation _diffrn_detector_area_resol_mean 6.67 _diffrn_reflns_number 11807 _diffrn_reflns_av_R_equivalents 0.0433 _diffrn_reflns_av_sigmaI/netI 0.0449 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -32 _diffrn_reflns_limit_l_max 25 _diffrn_reflns_theta_min 1.82 _diffrn_reflns_theta_max 24.95 _reflns_number_total 5239 _reflns_number_gt 3852 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'STOE X-AREA' _computing_cell_refinement 'STOE X-AREA' _computing_data_reduction 'STOE X-RED' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXL-97 (Sheldrick, 1997)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme 'calc w=1/[\s^2^(Fo^2^)+(0.0646P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_number_reflns 5239 _refine_ls_number_parameters 318 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0632 _refine_ls_R_factor_gt 0.0400 _refine_ls_wR_factor_ref 0.1047 _refine_ls_wR_factor_gt 0.0945 _refine_ls_goodness_of_fit_ref 0.989 _refine_ls_restrained_S_all 0.989 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O O 1.1552(2) 0.77168(19) 0.19460(9) 0.0557(6) Uani 1 d . . . S S 1.01497(7) 0.70878(6) 0.17634(3) 0.03883(18) Uani 1 d . . . Ni Ni 0.86308(3) 0.79338(3) 0.123449(11) 0.02729(12) Uani 1 d . . . C1 C 0.6954(3) 0.7131(2) 0.14099(9) 0.0292(5) Uani 1 d . . . C2 C 0.4704(3) 0.6704(2) 0.16798(11) 0.0403(7) Uani 1 d . . . H2 H 0.3798 0.6773 0.1827 0.048 Uiso 1 calc R . . C3 C 0.5190(3) 0.5826(2) 0.14537(11) 0.0387(7) Uani 1 d . . . H3 H 0.4692 0.5154 0.1413 0.046 Uiso 1 calc R . . C4 C 0.7451(3) 0.5368(2) 0.10000(12) 0.0455(7) Uani 1 d . . . H4 H 0.8411 0.5735 0.0951 0.055 Uiso 1 calc R . . C5 C 0.6643(6) 0.5187(4) 0.05089(15) 0.0830(13) Uani 1 d . . . H5A H 0.5739 0.4772 0.0547 0.125 Uiso 1 calc R . . H5B H 0.7283 0.4785 0.0304 0.125 Uiso 1 calc R . . H5C H 0.6390 0.5888 0.0363 0.125 Uiso 1 calc R . . C6 C 0.7774(4) 0.4296(3) 0.12584(15) 0.0574(9) Uani 1 d . . . H6A H 0.8276 0.4439 0.1571 0.086 Uiso 1 calc R . . H6B H 0.8407 0.3848 0.1069 0.086 Uiso 1 calc R . . H6C H 0.6846 0.3915 0.1300 0.086 Uiso 1 calc R . . C7 C 0.5719(3) 0.8602(2) 0.18615(11) 0.0393(6) Uani 1 d . . . H7 H 0.6693 0.8966 0.1836 0.047 Uiso 1 calc R . . C8 C 0.5399(5) 0.8540(3) 0.23845(13) 0.0690(10) Uani 1 d . . . H8A H 0.4431 0.8208 0.2414 0.104 Uiso 1 calc R . . H8B H 0.5403 0.9271 0.2520 0.104 Uiso 1 calc R . . H8C H 0.6158 0.8102 0.2557 0.104 Uiso 1 calc R . . C9 C 0.4539(4) 0.9263(3) 0.15780(15) 0.0620(10) Uani 1 d . . . H9A H 0.4754 0.9273 0.1241 0.093 Uiso 1 calc R . . H9B H 0.4538 1.0006 0.1701 0.093 Uiso 1 calc R . . H9C H 0.3570 0.8935 0.1611 0.093 Uiso 1 calc R . . C10 C 1.0137(2) 0.8894(2) 0.10537(9) 0.0291(5) Uani 1 d . . . C11 C 1.1849(3) 0.9800(3) 0.06508(11) 0.0436(7) Uani 1 d . . . H11 H 1.2537 0.9961 0.0421 0.052 Uiso 1 calc R . . C12 C 1.1481(3) 1.0439(2) 0.10125(11) 0.0414(7) Uani 1 d . . . H12 H 1.1862 1.1139 0.1086 0.050 Uiso 1 calc R . . C13 C 0.9748(3) 1.0270(2) 0.16880(12) 0.0463(7) Uani 1 d . . . H13 H 0.9136 0.9664 0.1804 0.056 Uiso 1 calc R . . C14 C 0.8719(5) 1.1211(4) 0.15672(17) 0.0904(15) Uani 1 d . . . H14A H 0.9291 1.1830 0.1463 0.136 Uiso 1 calc R . . H14B H 0.8205 1.1413 0.1850 0.136 Uiso 1 calc R . . H14C H 0.7996 1.0998 0.1311 0.136 Uiso 1 calc R . . C15 C 1.0919(4) 1.0539(3) 0.20883(14) 0.0685(10) Uani 1 d . . . H15A H 1.1585 0.9921 0.2141 0.103 Uiso 1 calc R . . H15B H 1.0436 1.0695 0.2382 0.103 Uiso 1 calc R . . H15C H 1.1484 1.1173 0.1998 0.103 Uiso 1 calc R . . C16 C 1.1163(3) 0.7870(3) 0.03785(11) 0.0479(7) Uani 1 d . . . H16 H 1.0294 0.7392 0.0422 0.057 Uiso 1 calc R . . C17 C 1.1159(6) 0.8164(4) -0.01462(14) 0.0878(14) Uani 1 d . . . H17A H 1.0305 0.8623 -0.0233 0.132 Uiso 1 calc R . . H17B H 1.1102 0.7502 -0.0339 0.132 Uiso 1 calc R . . H17C H 1.2066 0.8556 -0.0205 0.132 Uiso 1 calc R . . C18 C 1.2549(5) 0.7248(4) 0.05444(16) 0.0837(14) Uani 1 d . . . H18A H 1.3420 0.7683 0.0486 0.126 Uiso 1 calc R . . H18B H 1.2586 0.6566 0.0368 0.126 Uiso 1 calc R . . H18C H 1.2533 0.7094 0.0886 0.126 Uiso 1 calc R . . C19 C 0.7388(3) 0.8529(3) 0.06723(11) 0.0456(7) Uani 1 d . . . H19A H 0.7172 0.9294 0.0728 0.068 Uiso 1 calc R . . H19B H 0.6464 0.8122 0.0633 0.068 Uiso 1 calc R . . H19C H 0.7927 0.8461 0.0383 0.068 Uiso 1 calc R . . C20 C 0.9196(4) 0.6873(3) 0.23045(13) 0.0616(10) Uani 1 d . . . H20A H 0.9842 0.6480 0.2538 0.092 Uiso 1 calc R . . H20B H 0.8300 0.6449 0.2230 0.092 Uiso 1 calc R . . H20C H 0.8931 0.7574 0.2438 0.092 Uiso 1 calc R . . C21 C 0.3110(4) 0.3346(3) 0.17844(15) 0.0607(9) Uani 1 d . . . H21 H 0.3238 0.3260 0.2120 0.073 Uiso 1 calc R . . C22 C 0.1871(4) 0.4167(4) 0.1100(2) 0.0950(17) Uani 1 d . . . H22 H 0.1155 0.4658 0.0967 0.114 Uiso 1 calc R . . C23 C 0.2715(4) 0.3545(4) 0.08013(17) 0.0839(15) Uani 1 d . . . H23 H 0.2558 0.3619 0.0465 0.101 Uiso 1 calc R . . C24 C 0.4713(5) 0.2161(4) 0.06681(17) 0.0857(14) Uani 1 d . . . H24A H 0.4135 0.1988 0.0371 0.129 Uiso 1 calc R . . H24B H 0.5021 0.1489 0.0831 0.129 Uiso 1 calc R . . H24C H 0.5586 0.2579 0.0595 0.129 Uiso 1 calc R . . C25 C 0.2083(4) 0.4066(4) 0.15904(18) 0.0793(13) Uani 1 d . . . H25 H 0.1519 0.4493 0.1793 0.095 Uiso 1 calc R . . C26 C 0.3959(4) 0.2743(3) 0.14854(13) 0.0538(8) Uani 1 d . . . H26 H 0.4683 0.2265 0.1624 0.065 Uiso 1 calc R . . C27 C 0.3783(4) 0.2819(3) 0.09873(14) 0.0585(9) Uani 1 d . . . N1 N 0.5801(2) 0.74952(18) 0.16540(8) 0.0307(5) Uani 1 d . . . N2 N 0.6565(2) 0.60874(17) 0.12895(8) 0.0338(5) Uani 1 d . . . N3 N 1.1016(2) 0.88505(19) 0.06808(8) 0.0355(5) Uani 1 d . . . N4 N 1.0439(2) 0.98812(17) 0.12593(8) 0.0341(5) Uani 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O 0.0371(10) 0.0635(15) 0.0653(16) 0.0093(12) -0.0049(10) -0.0050(9) S 0.0411(4) 0.0338(4) 0.0416(4) 0.0019(3) 0.0023(3) 0.0018(3) Ni 0.02996(17) 0.02442(18) 0.02784(19) -0.00052(15) 0.00450(12) -0.00541(13) C1 0.0316(12) 0.0281(13) 0.0277(13) 0.0007(11) 0.0013(10) -0.0024(10) C2 0.0317(13) 0.0443(16) 0.0459(17) 0.0091(14) 0.0096(11) -0.0073(12) C3 0.0375(14) 0.0335(15) 0.0459(18) 0.0033(13) 0.0077(12) -0.0110(11) C4 0.0511(16) 0.0319(15) 0.055(2) -0.0128(14) 0.0167(14) -0.0099(12) C5 0.140(4) 0.066(3) 0.044(2) -0.011(2) 0.014(2) 0.006(3) C6 0.0545(18) 0.0411(18) 0.076(3) -0.0082(17) 0.0020(16) 0.0040(14) C7 0.0413(14) 0.0319(15) 0.0454(18) -0.0010(13) 0.0086(12) -0.0002(11) C8 0.108(3) 0.054(2) 0.047(2) -0.0086(17) 0.019(2) 0.011(2) C9 0.067(2) 0.0399(18) 0.079(3) 0.0046(18) 0.0037(18) 0.0097(15) C10 0.0308(12) 0.0294(13) 0.0272(14) -0.0020(11) 0.0036(10) -0.0014(10) C11 0.0391(14) 0.0498(18) 0.0428(18) 0.0137(15) 0.0099(12) -0.0115(13) C12 0.0436(15) 0.0319(15) 0.0490(19) 0.0065(14) 0.0058(13) -0.0126(12) C13 0.0558(17) 0.0346(16) 0.0504(19) -0.0137(14) 0.0173(14) -0.0086(13) C14 0.093(3) 0.095(3) 0.082(3) -0.030(3) 0.001(2) 0.048(3) C15 0.089(2) 0.070(2) 0.045(2) -0.0176(19) 0.0019(18) 0.002(2) C16 0.0550(17) 0.0512(18) 0.0384(17) -0.0145(15) 0.0107(13) -0.0024(14) C17 0.116(3) 0.109(4) 0.038(2) -0.016(2) -0.001(2) 0.041(3) C18 0.111(3) 0.074(3) 0.064(3) -0.018(2) -0.009(2) 0.044(2) C19 0.0331(14) 0.0594(19) 0.0438(18) 0.0096(15) -0.0015(12) -0.0066(13) C20 0.0555(18) 0.084(3) 0.045(2) 0.0183(19) -0.0017(15) -0.0164(17) C21 0.0585(19) 0.062(2) 0.063(2) 0.0083(19) 0.0119(17) -0.0191(17) C22 0.0391(19) 0.126(4) 0.121(4) 0.063(4) 0.008(2) -0.006(2) C23 0.057(2) 0.123(4) 0.070(3) 0.045(3) -0.009(2) -0.035(2) C24 0.106(3) 0.083(3) 0.069(3) -0.017(2) 0.018(2) -0.043(3) C25 0.051(2) 0.087(3) 0.103(4) 0.029(3) 0.027(2) -0.0065(19) C26 0.0602(19) 0.0466(19) 0.054(2) 0.0057(16) 0.0000(16) -0.0177(15) C27 0.0586(19) 0.060(2) 0.057(2) 0.0033(19) 0.0051(16) -0.0332(17) N1 0.0305(10) 0.0285(10) 0.0333(13) 0.0004(9) 0.0037(9) -0.0015(9) N2 0.0361(11) 0.0269(11) 0.0389(13) -0.0036(10) 0.0076(9) -0.0092(9) N3 0.0361(11) 0.0388(13) 0.0325(13) 0.0013(10) 0.0082(9) -0.0048(10) N4 0.0393(11) 0.0257(11) 0.0377(14) -0.0017(10) 0.0062(10) -0.0071(9) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O S 1.536(2) . ? S C20 1.800(4) . ? S Ni 2.2010(8) . ? Ni C10 1.886(2) . ? Ni C1 1.891(2) . ? Ni C19 2.000(3) . ? C1 N1 1.352(3) . ? C1 N2 1.359(3) . ? C2 C3 1.333(4) . ? C2 N1 1.388(3) . ? C3 N2 1.384(3) . ? C4 N2 1.463(4) . ? C4 C6 1.515(5) . ? C4 C5 1.522(5) . ? C7 N1 1.476(3) . ? C7 C8 1.503(5) . ? C7 C9 1.515(4) . ? C10 N3 1.346(3) . ? C10 N4 1.356(3) . ? C11 C12 1.332(4) . ? C11 N3 1.387(4) . ? C12 N4 1.379(3) . ? C13 N4 1.459(4) . ? C13 C14 1.502(5) . ? C13 C15 1.519(5) . ? C16 N3 1.476(4) . ? C16 C17 1.503(5) . ? C16 C18 1.508(5) . ? C21 C25 1.363(5) . ? C21 C26 1.379(5) . ? C22 C25 1.369(7) . ? C22 C23 1.389(7) . ? C23 C27 1.384(6) . ? C24 C27 1.494(6) . ? C26 C27 1.387(5) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O S C20 102.87(15) . . ? O S Ni 116.56(9) . . ? C20 S Ni 108.58(12) . . ? C10 Ni C1 172.54(10) . . ? C10 Ni C19 86.55(11) . . ? C1 Ni C19 88.62(11) . . ? C10 Ni S 92.58(8) . . ? C1 Ni S 93.14(8) . . ? C19 Ni S 170.26(10) . . ? N1 C1 N2 103.9(2) . . ? N1 C1 Ni 127.54(19) . . ? N2 C1 Ni 128.43(19) . . ? C3 C2 N1 106.3(2) . . ? C2 C3 N2 107.3(2) . . ? N2 C4 C6 110.7(3) . . ? N2 C4 C5 109.6(3) . . ? C6 C4 C5 111.4(3) . . ? N1 C7 C8 110.5(2) . . ? N1 C7 C9 109.7(2) . . ? C8 C7 C9 111.1(3) . . ? N3 C10 N4 104.4(2) . . ? N3 C10 Ni 130.47(19) . . ? N4 C10 Ni 124.74(19) . . ? C12 C11 N3 106.5(2) . . ? C11 C12 N4 107.2(2) . . ? N4 C13 C14 110.8(3) . . ? N4 C13 C15 111.0(3) . . ? C14 C13 C15 112.8(3) . . ? N3 C16 C17 111.4(3) . . ? N3 C16 C18 109.8(3) . . ? C17 C16 C18 111.6(3) . . ? C25 C21 C26 119.6(4) . . ? C25 C22 C23 120.0(4) . . ? C27 C23 C22 121.4(4) . . ? C21 C25 C22 120.0(4) . . ? C21 C26 C27 122.3(4) . . ? C23 C27 C26 116.6(4) . . ? C23 C27 C24 121.7(4) . . ? C26 C27 C24 121.7(4) . . ? C1 N1 C2 111.6(2) . . ? C1 N1 C7 123.9(2) . . ? C2 N1 C7 124.5(2) . . ? C1 N2 C3 110.9(2) . . ? C1 N2 C4 124.0(2) . . ? C3 N2 C4 125.0(2) . . ? C10 N3 C11 111.1(2) . . ? C10 N3 C16 123.4(2) . . ? C11 N3 C16 125.3(2) . . ? C10 N4 C12 110.8(2) . . ? C10 N4 C13 123.4(2) . . ? C12 N4 C13 125.8(2) . . ? _diffrn_measured_fraction_theta_max 0.981 _diffrn_reflns_theta_full 24.95 _diffrn_measured_fraction_theta_full 0.981 _refine_diff_density_max 0.542 _refine_diff_density_min -0.290 _refine_diff_density_rms 0.057 _chemical_name_common ;Bis-(1,3-di(isopropyl)imidazol-2- ylidene)(methylsulfoxyl)(methyl)nickel(ii) ; data_compound3 _database_code_depnum_ccdc_archive 'CCDC 626502' _audit_creation_method SHELXL-97 _chemical_name_systematic ; Bis-{1,3-di(isopropyl)imidazol-2-ylidene}(methylsulfoxyl)(phenyl)nickel(II) ; _chemical_formula_sum 'C30.50 H47.50 N4 Ni O1.50 S' _chemical_formula_weight 585.00 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Ni Ni 0.3393 1.1124 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M C2/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 39.4440(18) _cell_length_b 10.1660(14) _cell_length_c 17.216(3) _cell_angle_alpha 90.00 _cell_angle_beta 100.999(18) _cell_angle_gamma 90.00 _cell_volume 6776.5(14) _cell_formula_units_Z 8 _cell_measurement_temperature 203(2) _cell_measurement_reflns_used 8000 _cell_measurement_theta_min 2.2 _cell_measurement_theta_max 25.9 _exptl_crystal_description plate _exptl_crystal_colour yellow _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.50 _exptl_crystal_size_min 0.20 _exptl_crystal_density_diffrn 1.147 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2516 _exptl_absorpt_coefficient_mu 0.662 _exptl_absorpt_correction_type numerical _exptl_absorpt_correction_T_min 0.722 _exptl_absorpt_correction_T_max 0.837 _diffrn_ambient_temperature 203(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'STOE IPDS 1' _diffrn_measurement_method rotation _diffrn_detector_area_resol_mean 6.67 _diffrn_reflns_number 24628 _diffrn_reflns_av_R_equivalents 0.0541 _diffrn_reflns_av_sigmaI/netI 0.0362 _diffrn_reflns_limit_h_min -45 _diffrn_reflns_limit_h_max 48 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 2.07 _diffrn_reflns_theta_max 26.05 _reflns_number_total 6319 _reflns_number_gt 5261 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'STOE X-AREA' _computing_cell_refinement 'STOE X-AREA' _computing_data_reduction 'STOE X-RED' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXL-97 (Sheldrick, 1997)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme 'calc w=1/[\s^2^(Fo^2^)+(0.0947P)^2^+5.7097P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_number_reflns 6319 _refine_ls_number_parameters 358 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0587 _refine_ls_R_factor_gt 0.0486 _refine_ls_wR_factor_ref 0.1520 _refine_ls_wR_factor_gt 0.1420 _refine_ls_goodness_of_fit_ref 1.071 _refine_ls_restrained_S_all 1.072 _refine_ls_shift/su_max 0.003 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group S S 0.109683(17) 0.39912(7) 0.15362(4) 0.04016(18) Uani 1 d . . . Ni Ni 0.144174(8) 0.25743(3) 0.109337(18) 0.02943(13) Uani 1 d . . . O1 O 0.12344(6) 0.4631(2) 0.23392(13) 0.0547(6) Uani 1 d . . . N1 N 0.13110(6) 0.3415(2) -0.05593(13) 0.0354(5) Uani 1 d . . . N2 N 0.08815(6) 0.2308(3) -0.03124(15) 0.0424(6) Uani 1 d . . . N3 N 0.16637(6) 0.1736(2) 0.27369(13) 0.0360(5) Uani 1 d . . . N4 N 0.20273(5) 0.3046(2) 0.23614(13) 0.0339(5) Uani 1 d . . . C1 C 0.12000(6) 0.2751(2) 0.00301(16) 0.0328(5) Uani 1 d . . . C2 C 0.10656(7) 0.3396(3) -0.12464(17) 0.0446(6) Uani 1 d . . . H2 H 0.1082 0.3792 -0.1731 0.053 Uiso 1 calc R . . C3 C 0.08009(8) 0.2705(4) -0.10876(19) 0.0507(8) Uani 1 d . . . H3 H 0.0595 0.2521 -0.1444 0.061 Uiso 1 calc R . . C4 C 0.06567(8) 0.1512(4) 0.0095(2) 0.0562(8) Uani 1 d . . . H4 H 0.0776 0.1384 0.0650 0.067 Uiso 1 calc R . . C5 C 0.03158(10) 0.2221(6) 0.0099(3) 0.0848(14) Uani 1 d . . . H5A H 0.0362 0.3070 0.0354 0.127 Uiso 1 calc R . . H5B H 0.0175 0.1697 0.0386 0.127 Uiso 1 calc R . . H5C H 0.0194 0.2346 -0.0441 0.127 Uiso 1 calc R . . C6 C 0.05979(12) 0.0166(5) -0.0297(3) 0.0823(13) Uani 1 d . . . H6A H 0.0480 0.0272 -0.0842 0.123 Uiso 1 calc R . . H6B H 0.0458 -0.0368 -0.0014 0.123 Uiso 1 calc R . . H6C H 0.0819 -0.0262 -0.0285 0.123 Uiso 1 calc R . . C7 C 0.16523(8) 0.4046(3) -0.04778(18) 0.0464(7) Uani 1 d . . . H7 H 0.1775 0.3949 0.0077 0.056 Uiso 1 calc R . . C8 C 0.16087(14) 0.5501(4) -0.0665(3) 0.0886(15) Uani 1 d . . . H8A H 0.1555 0.5623 -0.1234 0.133 Uiso 1 calc R . . H8B H 0.1821 0.5960 -0.0449 0.133 Uiso 1 calc R . . H8C H 0.1422 0.5850 -0.0431 0.133 Uiso 1 calc R . . C9 C 0.18632(10) 0.3390(5) -0.1010(3) 0.0770(12) Uani 1 d . . . H9A H 0.1874 0.2452 -0.0906 0.115 Uiso 1 calc R . . H9B H 0.2095 0.3754 -0.0909 0.115 Uiso 1 calc R . . H9C H 0.1756 0.3543 -0.1558 0.115 Uiso 1 calc R . . C10 C 0.17200(7) 0.2441(2) 0.21116(17) 0.0318(5) Uani 1 d . . . C11 C 0.19315(7) 0.1905(3) 0.33702(17) 0.0430(6) Uani 1 d . . . H11 H 0.1951 0.1516 0.3872 0.052 Uiso 1 calc R . . C12 C 0.21590(7) 0.2725(3) 0.31391(17) 0.0409(6) Uani 1 d . . . H12 H 0.2368 0.3023 0.3447 0.049 Uiso 1 calc R . . C13 C 0.21793(7) 0.3990(3) 0.18874(17) 0.0404(6) Uani 1 d . . . H13 H 0.2076 0.3819 0.1326 0.049 Uiso 1 calc R . . C14 C 0.20812(10) 0.5374(3) 0.2071(3) 0.0704(11) Uani 1 d . . . H14A H 0.1833 0.5425 0.2037 0.106 Uiso 1 calc R . . H14B H 0.2150 0.5977 0.1692 0.106 Uiso 1 calc R . . H14C H 0.2198 0.5610 0.2601 0.106 Uiso 1 calc R . . C15 C 0.25670(9) 0.3814(4) 0.1975(3) 0.0698(11) Uani 1 d . . . H15A H 0.2680 0.4076 0.2503 0.105 Uiso 1 calc R . . H15B H 0.2651 0.4355 0.1587 0.105 Uiso 1 calc R . . H15C H 0.2618 0.2898 0.1890 0.105 Uiso 1 calc R . . C16 C 0.13493(8) 0.0959(3) 0.2750(2) 0.0491(7) Uani 1 d . . . H16 H 0.1211 0.0944 0.2206 0.059 Uiso 1 calc R . . C17 C 0.14463(12) -0.0444(4) 0.2988(3) 0.0856(14) Uani 1 d . . . H17A H 0.1592 -0.0797 0.2644 0.128 Uiso 1 calc R . . H17B H 0.1239 -0.0973 0.2939 0.128 Uiso 1 calc R . . H17C H 0.1570 -0.0463 0.3532 0.128 Uiso 1 calc R . . C18 C 0.11310(9) 0.1614(5) 0.3286(2) 0.0709(11) Uani 1 d . . . H18A H 0.1253 0.1575 0.3831 0.106 Uiso 1 calc R . . H18B H 0.0912 0.1157 0.3237 0.106 Uiso 1 calc R . . H18C H 0.1090 0.2526 0.3130 0.106 Uiso 1 calc R . . C19 C 0.16821(7) 0.1046(3) 0.08107(16) 0.0382(6) Uani 1 d . . . C20 C 0.15277(10) -0.0186(3) 0.0837(2) 0.0572(8) Uani 1 d . . . H20 H 0.1307 -0.0237 0.0965 0.069 Uiso 1 calc R . . C21 C 0.16912(11) -0.1335(3) 0.0681(2) 0.0662(10) Uani 1 d . . . H21 H 0.1581 -0.2147 0.0714 0.079 Uiso 1 calc R . . C22 C 0.20142(10) -0.1311(3) 0.0476(2) 0.0626(10) Uani 1 d . . . H22 H 0.2122 -0.2094 0.0363 0.075 Uiso 1 calc R . . C23 C 0.21724(9) -0.0125(4) 0.0444(2) 0.0620(9) Uani 1 d . . . H23 H 0.2392 -0.0087 0.0308 0.074 Uiso 1 calc R . . C24 C 0.20096(8) 0.1039(3) 0.0613(2) 0.0510(7) Uani 1 d . . . H24 H 0.2125 0.1843 0.0593 0.061 Uiso 1 calc R . . C25 C 0.10171(13) 0.5371(4) 0.0876(3) 0.0796(13) Uani 1 d . . . H25A H 0.0859 0.5974 0.1060 0.119 Uiso 1 calc R . . H25B H 0.0916 0.5066 0.0349 0.119 Uiso 1 calc R . . H25C H 0.1233 0.5819 0.0863 0.119 Uiso 1 calc R . . C26 C 0.01655(12) 0.4423(6) 0.1879(4) 0.1023(19) Uani 1 d D . . H26 H 0.0275 0.4444 0.1440 0.123 Uiso 1 calc R . . C27 C 0.03561(10) 0.4427(4) 0.2607(3) 0.0791(13) Uani 1 d D . . H27 H 0.0598 0.4456 0.2683 0.095 Uiso 1 calc R . . C28 C 0.01955(12) 0.4387(6) 0.3240(4) 0.0995(18) Uani 1 d D . . C29 C 0.0395(3) 0.3958(12) 0.3967(7) 0.098(3) Uani 0.50 d PD . . H29A H 0.0318 0.3091 0.4092 0.147 Uiso 0.50 calc PR . . H29B H 0.0367 0.4570 0.4382 0.147 Uiso 0.50 calc PR . . H29C H 0.0636 0.3919 0.3924 0.147 Uiso 0.50 calc PR . . O2 O 0.0000 0.8156(8) 0.2500 0.155(3) Uani 1 d S . . C30 C 0.0183(3) 1.0331(9) 0.2240(6) 0.314(13) Uani 1 d . . . H30A H 0.0120 1.0806 0.1738 0.376 Uiso 1 calc R . . H30B H 0.0381 1.0784 0.2563 0.376 Uiso 1 calc R . . C31 C 0.0294(3) 0.8790(10) 0.2067(5) 0.234(6) Uani 1 d . . . H31A H 0.0259 0.8578 0.1502 0.281 Uiso 1 calc R . . H31B H 0.0530 0.8567 0.2331 0.281 Uiso 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 S 0.0359(3) 0.0516(4) 0.0336(4) -0.0030(3) 0.0082(2) 0.0035(3) Ni 0.0303(2) 0.03300(19) 0.0242(2) -0.00017(11) 0.00310(13) -0.00427(11) O1 0.0572(13) 0.0685(14) 0.0386(13) -0.0150(10) 0.0096(9) 0.0087(10) N1 0.0424(12) 0.0382(11) 0.0247(12) 0.0010(8) 0.0042(8) 0.0009(9) N2 0.0315(11) 0.0636(15) 0.0310(14) -0.0081(10) 0.0034(9) -0.0068(10) N3 0.0382(11) 0.0392(11) 0.0295(12) 0.0057(9) 0.0033(8) -0.0012(9) N4 0.0319(10) 0.0379(11) 0.0310(12) -0.0040(9) 0.0042(8) -0.0033(8) C1 0.0310(12) 0.0375(12) 0.0298(15) -0.0031(10) 0.0058(10) -0.0016(9) C2 0.0469(15) 0.0592(17) 0.0257(15) 0.0011(11) 0.0021(11) 0.0080(13) C3 0.0372(15) 0.083(2) 0.0279(17) -0.0066(13) -0.0026(11) 0.0030(14) C4 0.0431(16) 0.085(2) 0.0421(19) -0.0124(16) 0.0121(13) -0.0248(15) C5 0.0433(19) 0.143(4) 0.073(3) -0.022(3) 0.0230(19) -0.017(2) C6 0.088(3) 0.092(3) 0.069(3) -0.023(2) 0.020(2) -0.046(2) C7 0.0588(18) 0.0497(16) 0.0303(16) 0.0029(11) 0.0074(12) -0.0183(13) C8 0.136(4) 0.047(2) 0.089(3) -0.0027(19) 0.037(3) -0.029(2) C9 0.057(2) 0.101(3) 0.080(3) -0.028(2) 0.0322(19) -0.030(2) C10 0.0316(12) 0.0321(12) 0.0313(15) -0.0013(9) 0.0053(10) -0.0011(9) C11 0.0490(15) 0.0488(15) 0.0286(15) 0.0023(11) 0.0011(11) 0.0070(12) C12 0.0378(14) 0.0510(15) 0.0298(16) -0.0063(11) -0.0040(11) 0.0022(11) C13 0.0427(14) 0.0429(14) 0.0359(16) -0.0039(11) 0.0081(11) -0.0091(11) C14 0.069(2) 0.0447(17) 0.106(3) -0.0003(18) 0.037(2) -0.0068(16) C15 0.0463(18) 0.072(2) 0.098(3) 0.012(2) 0.0303(19) -0.0006(16) C16 0.0499(16) 0.0521(17) 0.0441(19) 0.0138(13) 0.0061(13) -0.0140(13) C17 0.091(3) 0.054(2) 0.106(4) 0.030(2) 0.003(3) -0.015(2) C18 0.055(2) 0.102(3) 0.059(3) 0.010(2) 0.0202(17) -0.016(2) C19 0.0435(14) 0.0357(13) 0.0324(15) -0.0011(10) -0.0005(10) -0.0007(10) C20 0.069(2) 0.0404(15) 0.063(2) -0.0051(14) 0.0133(16) -0.0072(14) C21 0.093(3) 0.0377(16) 0.064(3) -0.0058(15) 0.007(2) -0.0039(16) C22 0.084(2) 0.0458(17) 0.047(2) -0.0143(13) -0.0155(17) 0.0213(16) C23 0.0528(18) 0.068(2) 0.060(2) -0.0206(17) -0.0032(15) 0.0156(16) C24 0.0482(16) 0.0460(16) 0.057(2) -0.0121(13) 0.0061(14) 0.0003(13) C25 0.122(4) 0.066(2) 0.054(3) 0.0091(17) 0.024(2) 0.041(2) C26 0.059(2) 0.130(4) 0.127(5) -0.063(4) 0.041(3) -0.009(3) C27 0.049(2) 0.068(2) 0.123(4) -0.008(2) 0.026(2) -0.0001(17) C28 0.064(2) 0.114(4) 0.120(5) 0.051(3) 0.017(3) 0.006(3) C29 0.074(6) 0.125(9) 0.094(8) 0.021(6) 0.011(5) -0.016(6) O2 0.161(6) 0.133(5) 0.126(6) 0.000 -0.090(5) 0.000 C30 0.390(19) 0.201(8) 0.225(13) 0.155(9) -0.257(14) -0.212(11) C31 0.245(10) 0.247(11) 0.135(7) 0.092(7) -0.155(7) -0.129(9) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag S O1 1.531(2) . ? S C25 1.795(4) . ? S Ni 2.2143(8) . ? Ni C10 1.887(3) . ? Ni C1 1.904(3) . ? Ni C19 1.930(3) . ? N1 C1 1.359(3) . ? N1 C2 1.378(3) . ? N1 C7 1.474(4) . ? N2 C1 1.359(3) . ? N2 C3 1.372(4) . ? N2 C4 1.473(4) . ? N3 C10 1.347(3) . ? N3 C11 1.377(4) . ? N3 C16 1.474(3) . ? N4 C10 1.354(3) . ? N4 C12 1.380(4) . ? N4 C13 1.461(3) . ? C2 C3 1.329(5) . ? C4 C6 1.523(5) . ? C4 C5 1.527(5) . ? C7 C9 1.506(5) . ? C7 C8 1.516(5) . ? C11 C12 1.340(4) . ? C13 C14 1.508(4) . ? C13 C15 1.519(4) . ? C16 C17 1.513(5) . ? C16 C18 1.529(5) . ? C19 C20 1.397(4) . ? C19 C24 1.397(4) . ? C20 C21 1.385(5) . ? C21 C22 1.385(6) . ? C22 C23 1.364(5) . ? C23 C24 1.403(4) . ? C26 C27 1.333(7) . ? C26 C28 1.400(6) 2 ? C27 C28 1.361(7) . ? C28 C26 1.400(6) 2 ? C28 C29 1.414(11) . ? O2 C31 1.627(11) 2 ? O2 C31 1.627(11) . ? C30 C31 1.669(16) . ? C30 C30 1.84(3) 2 ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 S C25 103.23(18) . . ? O1 S Ni 116.89(9) . . ? C25 S Ni 109.59(14) . . ? C10 Ni C1 174.53(10) . . ? C10 Ni C19 87.12(11) . . ? C1 Ni C19 90.78(11) . . ? C10 Ni S 90.78(8) . . ? C1 Ni S 92.39(8) . . ? C19 Ni S 166.93(9) . . ? C1 N1 C2 111.1(2) . . ? C1 N1 C7 124.3(2) . . ? C2 N1 C7 124.5(2) . . ? C1 N2 C3 110.4(3) . . ? C1 N2 C4 124.5(3) . . ? C3 N2 C4 125.1(3) . . ? C10 N3 C11 110.4(2) . . ? C10 N3 C16 124.4(2) . . ? C11 N3 C16 125.1(2) . . ? C10 N4 C12 110.4(2) . . ? C10 N4 C13 124.0(2) . . ? C12 N4 C13 125.4(2) . . ? N2 C1 N1 104.1(2) . . ? N2 C1 Ni 129.6(2) . . ? N1 C1 Ni 126.23(19) . . ? C3 C2 N1 106.3(3) . . ? C2 C3 N2 108.1(3) . . ? N2 C4 C6 109.7(3) . . ? N2 C4 C5 110.7(3) . . ? C6 C4 C5 111.5(3) . . ? N1 C7 C9 110.5(2) . . ? N1 C7 C8 109.9(3) . . ? C9 C7 C8 110.9(3) . . ? N3 C10 N4 105.2(2) . . ? N3 C10 Ni 128.70(19) . . ? N4 C10 Ni 126.1(2) . . ? C12 C11 N3 107.4(3) . . ? C11 C12 N4 106.6(2) . . ? N4 C13 C14 110.3(3) . . ? N4 C13 C15 112.3(3) . . ? C14 C13 C15 112.5(3) . . ? N3 C16 C17 109.8(3) . . ? N3 C16 C18 110.4(3) . . ? C17 C16 C18 113.0(3) . . ? C20 C19 C24 115.6(3) . . ? C20 C19 Ni 118.4(2) . . ? C24 C19 Ni 126.0(2) . . ? C21 C20 C19 121.9(3) . . ? C22 C21 C20 121.3(3) . . ? C23 C22 C21 118.4(3) . . ? C22 C23 C24 120.4(3) . . ? C19 C24 C23 122.4(3) . . ? C27 C26 C28 120.9(5) . 2 ? C26 C27 C28 119.1(4) . . ? C27 C28 C26 119.9(5) . 2 ? C27 C28 C29 116.9(6) . . ? C26 C28 C29 121.0(6) 2 . ? C31 O2 C31 133.3(10) 2 . ? C31 C30 C30 110.1(6) . 2 ? O2 C31 C30 93.2(9) . . ? _diffrn_measured_fraction_theta_max 0.942 _diffrn_reflns_theta_full 26.05 _diffrn_measured_fraction_theta_full 0.942 _refine_diff_density_max 0.820 _refine_diff_density_min -0.535 _refine_diff_density_rms 0.069 _chemical_name_common ;Bis-(1,3-di(isopropyl)imidazol-2- ylidene)(methylsulfoxyl)(phenyl)nickel(ii) ; data_compound4 _database_code_depnum_ccdc_archive 'CCDC 626503' _audit_creation_method SHELXL-97 _chemical_name_systematic ; Bis-{1,3-di(isopropyl)imidazol-2-ylidene-}(Phenylthiooxyl)(phenyl)nickel(II) ; _chemical_formula_sum 'C30 H42 N4 Ni O S' _chemical_formula_weight 565.45 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Ni Ni 0.3393 1.1124 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M Pbca loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' '-x, -y, -z' 'x-1/2, y, -z-1/2' 'x, -y-1/2, z-1/2' '-x-1/2, y-1/2, z' _cell_length_a 10.861(2) _cell_length_b 19.288(4) _cell_length_c 28.695(6) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 6011(2) _cell_formula_units_Z 8 _cell_measurement_temperature 203(2) _cell_measurement_reflns_used 6910 _cell_measurement_theta_min 2.3 _cell_measurement_theta_max 25.9 _exptl_crystal_description plate _exptl_crystal_colour yellow _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.15 _exptl_crystal_density_diffrn 1.250 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2416 _exptl_absorpt_coefficient_mu 0.743 _exptl_absorpt_correction_type numerical _exptl_absorpt_correction_T_min 0.6633 _exptl_absorpt_correction_T_max 0.8922 _diffrn_ambient_temperature 203(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'STOE STADI4-CCD' _diffrn_measurement_method rotation _diffrn_reflns_number 27925 _diffrn_reflns_av_R_equivalents 0.0718 _diffrn_reflns_av_sigmaI/netI 0.0411 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -21 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -31 _diffrn_reflns_limit_l_max 31 _diffrn_reflns_theta_min 3.90 _diffrn_reflns_theta_max 23.26 _reflns_number_total 4295 _reflns_number_gt 3813 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'STOE X-AREA' _computing_cell_refinement 'STOE X-AREA' _computing_data_reduction 'STOE X-RED' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXL-97 (Sheldrick, 1997)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme 'calc w=1/[\s^2^(Fo^2^)+(0.1166P)^2^+0.4949P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_number_reflns 4295 _refine_ls_number_parameters 342 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0816 _refine_ls_R_factor_gt 0.0645 _refine_ls_wR_factor_ref 0.2007 _refine_ls_wR_factor_gt 0.1696 _refine_ls_goodness_of_fit_ref 1.255 _refine_ls_restrained_S_all 1.255 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O O 1.0003(3) 0.4289(2) 0.13514(11) 0.0615(10) Uani 1 d . . . S S 1.12287(12) 0.41516(7) 0.10606(5) 0.0516(4) Uani 1 d . . . Ni Ni 0.86293(5) 0.36560(3) 0.128771(18) 0.0346(3) Uani 1 d . . . C1 C 0.8515(4) 0.3705(2) 0.19485(16) 0.0363(11) Uani 1 d . . . C2 C 0.8264(5) 0.4118(2) 0.26793(15) 0.0481(12) Uani 1 d . . . H2 H 0.8023 0.4407 0.2927 0.058 Uiso 1 calc R . . C3 C 0.8900(4) 0.3536(2) 0.27108(16) 0.0438(12) Uani 1 d . . . H3 H 0.9198 0.3332 0.2986 0.053 Uiso 1 calc R . . C4 C 0.9753(4) 0.2659(2) 0.21290(17) 0.0419(11) Uani 1 d . . . H4 H 0.9608 0.2571 0.1794 0.050 Uiso 1 calc R . . C5 C 1.1105(5) 0.2794(3) 0.2194(3) 0.0764(19) Uani 1 d . . . H5A H 1.1344 0.3195 0.2011 0.115 Uiso 1 calc R . . H5B H 1.1570 0.2393 0.2091 0.115 Uiso 1 calc R . . H5C H 1.1273 0.2881 0.2521 0.115 Uiso 1 calc R . . C6 C 0.9300(6) 0.2034(2) 0.23965(19) 0.0652(15) Uani 1 d . . . H6A H 0.9431 0.2107 0.2727 0.098 Uiso 1 calc R . . H6B H 0.9749 0.1626 0.2296 0.098 Uiso 1 calc R . . H6C H 0.8428 0.1968 0.2337 0.098 Uiso 1 calc R . . C7 C 0.7361(6) 0.4811(3) 0.20218(18) 0.0668(17) Uani 1 d . . . H7 H 0.7163 0.4709 0.1692 0.080 Uiso 1 calc R . . C8 C 0.8161(7) 0.5449(3) 0.2035(4) 0.168(6) Uani 1 d . . . H8A H 0.8244 0.5606 0.2354 0.253 Uiso 1 calc R . . H8B H 0.7786 0.5811 0.1849 0.253 Uiso 1 calc R . . H8C H 0.8967 0.5339 0.1910 0.253 Uiso 1 calc R . . C9 C 0.6186(5) 0.4942(3) 0.2274(3) 0.083(2) Uani 1 d . . . H9A H 0.5709 0.4517 0.2287 0.125 Uiso 1 calc R . . H9B H 0.5720 0.5296 0.2111 0.125 Uiso 1 calc R . . H9C H 0.6364 0.5098 0.2588 0.125 Uiso 1 calc R . . C10 C 0.8745(4) 0.36061(19) 0.06221(15) 0.0310(10) Uani 1 d . . . C11 C 0.9191(4) 0.3314(2) -0.01120(15) 0.0409(11) Uani 1 d . . . H11 H 0.9496 0.3065 -0.0369 0.049 Uiso 1 calc R . . C12 C 0.8589(4) 0.3910(2) -0.01291(15) 0.0398(11) Uani 1 d . . . H12 H 0.8391 0.4164 -0.0398 0.048 Uiso 1 calc R . . C13 C 0.7696(4) 0.47245(19) 0.04690(15) 0.0376(10) Uani 1 d . . . H13 H 0.7522 0.4687 0.0807 0.045 Uiso 1 calc R . . C14 C 0.6493(5) 0.4802(3) 0.02208(19) 0.0577(14) Uani 1 d . . . H14A H 0.6642 0.4894 -0.0107 0.087 Uiso 1 calc R . . H14B H 0.6036 0.5185 0.0356 0.087 Uiso 1 calc R . . H14C H 0.6020 0.4378 0.0252 0.087 Uiso 1 calc R . . C15 C 0.8536(5) 0.5334(2) 0.0398(2) 0.0589(15) Uani 1 d . . . H15A H 0.9301 0.5257 0.0564 0.088 Uiso 1 calc R . . H15B H 0.8143 0.5751 0.0515 0.088 Uiso 1 calc R . . H15C H 0.8707 0.5388 0.0068 0.088 Uiso 1 calc R . . C16 C 0.9893(5) 0.2495(2) 0.05192(18) 0.0514(13) Uani 1 d . . . H16 H 0.9874 0.2505 0.0864 0.062 Uiso 1 calc R . . C17 C 0.9161(7) 0.1861(3) 0.0354(2) 0.0762(18) Uani 1 d . . . H17A H 0.8307 0.1909 0.0448 0.114 Uiso 1 calc R . . H17B H 0.9505 0.1445 0.0493 0.114 Uiso 1 calc R . . H17C H 0.9207 0.1828 0.0017 0.114 Uiso 1 calc R . . C18 C 1.1260(6) 0.2485(4) 0.0361(3) 0.088(2) Uani 1 d . . . H18A H 1.1299 0.2424 0.0026 0.132 Uiso 1 calc R . . H18B H 1.1685 0.2105 0.0513 0.132 Uiso 1 calc R . . H18C H 1.1650 0.2920 0.0445 0.132 Uiso 1 calc R . . C19 C 0.7157(5) 0.3127(2) 0.12611(13) 0.0380(11) Uani 1 d . . . C20 C 0.6021(5) 0.3434(3) 0.11751(17) 0.0465(12) Uani 1 d . . . H20 H 0.5991 0.3916 0.1130 0.056 Uiso 1 calc R . . C21 C 0.4934(5) 0.3064(3) 0.11532(17) 0.0551(14) Uani 1 d . . . H21 H 0.4192 0.3298 0.1092 0.066 Uiso 1 calc R . . C22 C 0.4926(6) 0.2366(3) 0.12186(16) 0.0574(15) Uani 1 d . . . H22A H 0.4184 0.2115 0.1203 0.069 Uiso 1 calc R . . C23 C 0.6003(7) 0.2038(3) 0.13070(17) 0.0631(17) Uani 1 d . . . H23 H 0.6004 0.1555 0.1354 0.076 Uiso 1 calc R . . C24 C 0.7115(6) 0.2403(3) 0.13294(17) 0.0583(15) Uani 1 d . . . H24 H 0.7849 0.2161 0.1391 0.070 Uiso 1 calc R . . C25 C 1.2132(5) 0.4863(2) 0.11966(14) 0.0418(11) Uani 1 d . . . C26 C 1.3382(5) 0.4874(3) 0.10668(17) 0.0500(13) Uani 1 d . . . H26 H 1.3714 0.4496 0.0903 0.060 Uiso 1 calc R . . C27 C 1.4129(5) 0.5428(3) 0.11756(19) 0.0571(13) Uani 1 d . . . H27 H 1.4963 0.5422 0.1089 0.069 Uiso 1 calc R . . C28 C 1.3660(5) 0.5989(3) 0.1410(2) 0.0600(15) Uani 1 d . . . H28 H 1.4161 0.6373 0.1477 0.072 Uiso 1 calc R . . C29 C 1.2445(5) 0.5980(3) 0.15447(18) 0.0609(15) Uani 1 d . . . H29 H 1.2133 0.6361 0.1712 0.073 Uiso 1 calc R . . C30 C 1.1665(5) 0.5433(3) 0.14446(17) 0.0523(13) Uani 1 d . . . H30 H 1.0837 0.5443 0.1541 0.063 Uiso 1 calc R . . N1 N 0.8024(4) 0.42192(18) 0.22135(12) 0.0423(9) Uani 1 d . . . N2 N 0.9047(3) 0.32801(17) 0.22598(12) 0.0360(9) Uani 1 d . . . N3 N 0.9289(3) 0.31266(17) 0.03475(12) 0.0371(9) Uani 1 d . . . N4 N 0.8313(3) 0.40824(16) 0.03217(11) 0.0316(8) Uani 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O 0.048(2) 0.090(3) 0.046(2) -0.0209(18) 0.0124(16) -0.014(2) S 0.0525(8) 0.0588(8) 0.0434(8) -0.0020(6) 0.0084(6) 0.0004(6) Ni 0.0485(5) 0.0326(4) 0.0227(4) -0.0014(2) 0.0008(2) 0.0062(2) C1 0.044(3) 0.032(2) 0.033(3) -0.0052(19) 0.0004(19) 0.0004(19) C2 0.069(3) 0.051(3) 0.025(3) -0.010(2) 0.004(2) -0.009(3) C3 0.059(3) 0.048(3) 0.024(2) -0.001(2) -0.005(2) -0.007(2) C4 0.046(3) 0.038(2) 0.042(3) 0.002(2) -0.004(2) 0.002(2) C5 0.054(4) 0.075(4) 0.100(5) -0.025(4) -0.013(3) 0.003(3) C6 0.102(4) 0.038(3) 0.056(4) 0.005(2) 0.007(3) 0.002(3) C7 0.109(5) 0.059(3) 0.032(3) -0.010(2) 0.001(3) 0.041(3) C8 0.097(6) 0.069(4) 0.339(15) 0.108(7) 0.121(8) 0.040(4) C9 0.048(4) 0.056(4) 0.147(7) 0.014(4) -0.004(4) -0.002(3) C10 0.034(2) 0.031(2) 0.028(2) -0.0022(18) 0.0041(18) -0.0026(17) C11 0.052(3) 0.045(3) 0.025(2) -0.008(2) 0.008(2) -0.010(2) C12 0.052(3) 0.040(3) 0.027(3) 0.003(2) 0.004(2) -0.009(2) C13 0.046(3) 0.033(2) 0.034(2) 0.0030(19) 0.004(2) 0.007(2) C14 0.055(3) 0.065(3) 0.053(3) -0.001(3) -0.008(2) 0.015(3) C15 0.068(4) 0.036(3) 0.073(4) -0.003(2) 0.006(3) 0.000(2) C16 0.066(3) 0.044(3) 0.045(3) -0.008(2) -0.003(2) 0.021(2) C17 0.114(5) 0.038(3) 0.076(4) -0.005(3) -0.005(4) 0.012(3) C18 0.077(5) 0.097(5) 0.091(5) -0.023(4) 0.005(4) 0.040(4) C19 0.064(3) 0.032(2) 0.019(2) -0.0003(16) 0.0054(19) -0.002(2) C20 0.051(3) 0.045(3) 0.044(3) 0.003(2) 0.013(2) 0.000(2) C21 0.056(3) 0.066(4) 0.043(3) 0.002(3) 0.015(3) -0.007(3) C22 0.070(4) 0.070(4) 0.032(3) -0.004(2) 0.000(2) -0.019(3) C23 0.104(5) 0.038(3) 0.048(3) -0.001(2) -0.010(3) -0.020(3) C24 0.084(4) 0.040(3) 0.050(3) 0.000(2) -0.018(3) -0.003(3) C25 0.051(3) 0.050(3) 0.024(2) 0.010(2) -0.002(2) 0.005(2) C26 0.056(3) 0.053(3) 0.042(3) 0.004(2) 0.009(2) 0.006(3) C27 0.055(3) 0.064(3) 0.053(3) 0.005(3) 0.012(3) -0.003(3) C28 0.068(4) 0.059(4) 0.052(3) -0.002(3) -0.001(3) -0.011(3) C29 0.077(4) 0.057(3) 0.049(3) -0.010(3) -0.010(3) 0.010(3) C30 0.053(3) 0.069(4) 0.034(3) -0.002(3) -0.005(2) 0.015(3) N1 0.064(3) 0.038(2) 0.026(2) -0.0029(16) 0.0002(18) 0.0037(18) N2 0.048(2) 0.034(2) 0.0254(19) 0.0005(16) -0.0038(16) -0.0050(17) N3 0.045(2) 0.0329(19) 0.033(2) -0.0063(16) 0.0055(17) 0.0024(16) N4 0.0379(19) 0.0349(19) 0.0220(19) 0.0020(15) 0.0014(15) -0.0022(16) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O S 1.593(4) . ? O Ni 1.937(4) . ? S C25 1.731(5) . ? Ni C19 1.898(5) . ? Ni C1 1.903(5) . ? Ni C10 1.917(4) . ? C1 N2 1.343(5) . ? C1 N1 1.358(5) . ? C2 C3 1.322(7) . ? C2 N1 1.375(6) . ? C3 N2 1.394(5) . ? C4 N2 1.471(5) . ? C4 C5 1.503(7) . ? C4 C6 1.511(6) . ? C7 N1 1.458(6) . ? C7 C9 1.488(8) . ? C7 C8 1.506(9) . ? C10 N4 1.344(5) . ? C10 N3 1.351(5) . ? C11 C12 1.322(6) . ? C11 N3 1.371(5) . ? C12 N4 1.369(5) . ? C13 N4 1.471(5) . ? C13 C14 1.496(7) . ? C13 C15 1.502(6) . ? C16 N3 1.468(6) . ? C16 C17 1.534(7) . ? C16 C18 1.553(8) . ? C19 C20 1.391(7) . ? C19 C24 1.411(7) . ? C20 C21 1.380(7) . ? C21 C22 1.360(7) . ? C22 C23 1.354(8) . ? C23 C24 1.401(9) . ? C25 C30 1.405(7) . ? C25 C26 1.408(7) . ? C26 C27 1.377(7) . ? C27 C28 1.371(8) . ? C28 C29 1.375(7) . ? C29 C30 1.384(7) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag S O Ni 119.3(2) . . ? O S C25 102.9(2) . . ? C19 Ni C1 90.67(17) . . ? C19 Ni C10 89.31(16) . . ? C1 Ni C10 179.98(16) . . ? C19 Ni O 172.58(17) . . ? C1 Ni O 85.70(16) . . ? C10 Ni O 94.32(15) . . ? N2 C1 N1 104.0(4) . . ? N2 C1 Ni 127.2(3) . . ? N1 C1 Ni 128.3(3) . . ? C3 C2 N1 106.6(4) . . ? C2 C3 N2 107.3(4) . . ? N2 C4 C5 109.7(4) . . ? N2 C4 C6 110.5(4) . . ? C5 C4 C6 113.2(5) . . ? N1 C7 C9 111.9(5) . . ? N1 C7 C8 110.2(5) . . ? C9 C7 C8 110.1(5) . . ? N4 C10 N3 104.3(4) . . ? N4 C10 Ni 125.6(3) . . ? N3 C10 Ni 130.1(3) . . ? C12 C11 N3 107.7(4) . . ? C11 C12 N4 106.5(4) . . ? N4 C13 C14 110.2(4) . . ? N4 C13 C15 110.1(4) . . ? C14 C13 C15 112.8(4) . . ? N3 C16 C17 109.0(4) . . ? N3 C16 C18 109.9(5) . . ? C17 C16 C18 113.3(5) . . ? C20 C19 C24 114.7(5) . . ? C20 C19 Ni 121.7(3) . . ? C24 C19 Ni 123.6(4) . . ? C21 C20 C19 123.2(5) . . ? C22 C21 C20 120.8(5) . . ? C23 C22 C21 118.9(5) . . ? C22 C23 C24 121.2(5) . . ? C23 C24 C19 121.3(6) . . ? C30 C25 C26 118.0(5) . . ? C30 C25 S 122.0(4) . . ? C26 C25 S 120.0(4) . . ? C27 C26 C25 121.3(5) . . ? C28 C27 C26 120.3(5) . . ? C27 C28 C29 119.0(5) . . ? C28 C29 C30 122.6(5) . . ? C29 C30 C25 118.7(5) . . ? C1 N1 C2 111.5(4) . . ? C1 N1 C7 123.7(4) . . ? C2 N1 C7 124.8(4) . . ? C1 N2 C3 110.6(4) . . ? C1 N2 C4 123.5(4) . . ? C3 N2 C4 125.8(4) . . ? C10 N3 C11 110.2(4) . . ? C10 N3 C16 124.6(4) . . ? C11 N3 C16 125.2(4) . . ? C10 N4 C12 111.3(4) . . ? C10 N4 C13 123.4(3) . . ? C12 N4 C13 125.2(4) . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 23.26 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.814 _refine_diff_density_min -0.630 _refine_diff_density_rms 0.162 _chemical_name_common ;Bis-(1,3-di(isopropyl)imidazol-2-ylidene- )(Phenylthiooxyl)(phenyl)nickel(ii) ;