# Supplementary Material (ESI) for Dalton Transactions # This journal is (c) The Royal Society of Chemistry 2009 data_global _journal_name_full 'Dalton Trans.' _journal_coden_Cambridge 0222 _publ_contact_author_name 'Andy Hor' _publ_contact_author_email ANDYHOR@NUS.EDU.SG _publ_section_title ; Formation and Crystallographic Elucidation of Stable [4+2]-Coordinate Nickel(II) N,S-Heterocyclic Carbene (NSHC) Complexes ; loop_ _publ_author_name 'Andy Hor' 'Nini Ding.' 'Jun Zhang.' # Attachment 'NiNSPz.cif' data_Compound6 _database_code_depnum_ccdc_archive 'CCDC 699586' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C42 H38 Br2 N2 Ni S2' _chemical_formula_weight 853.39 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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' Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.3327(5) _cell_length_b 8.7543(5) _cell_length_c 14.4928(9) _cell_angle_alpha 98.2140(10) _cell_angle_beta 104.9500(10) _cell_angle_gamma 102.2930(10) _cell_volume 975.85(10) _cell_formula_units_Z 1 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 4425 _cell_measurement_theta_min 2.44 _cell_measurement_theta_max 26.90 _exptl_crystal_description Block _exptl_crystal_colour Red _exptl_crystal_size_max 0.60 _exptl_crystal_size_mid 0.40 _exptl_crystal_size_min 0.30 _exptl_crystal_density_meas 0 _exptl_crystal_density_diffrn 1.452 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 434 _exptl_absorpt_coefficient_mu 2.683 _exptl_absorpt_correction_type 'Sadabs, (Sheldrick 2001)' _exptl_absorpt_correction_T_min 0.2959 _exptl_absorpt_correction_T_max 0.5000 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 12903 _diffrn_reflns_av_R_equivalents 0.0262 _diffrn_reflns_av_sigmaI/netI 0.0302 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 1.49 _diffrn_reflns_theta_max 27.50 _reflns_number_total 4481 _reflns_number_gt 3640 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0590P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4481 _refine_ls_number_parameters 265 _refine_ls_number_restraints 86 _refine_ls_R_factor_all 0.0475 _refine_ls_R_factor_gt 0.0366 _refine_ls_wR_factor_ref 0.0956 _refine_ls_wR_factor_gt 0.0906 _refine_ls_goodness_of_fit_ref 1.043 _refine_ls_restrained_S_all 1.065 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Ni1 Ni 0.5000 0.0000 0.0000 0.03325(12) Uani 1 2 d S . . Br1 Br 0.61703(3) -0.08693(3) -0.119753(18) 0.04746(11) Uani 1 1 d . . . S1 S 0.59854(7) 0.35541(7) -0.02023(5) 0.04094(15) Uani 1 1 d . . . N1 N 0.8171(2) 0.2574(2) 0.09218(13) 0.0350(4) Uani 1 1 d . . . C1 C 0.6582(3) 0.2038(3) 0.03125(16) 0.0342(5) Uani 1 1 d . . . C2 C 0.8974(3) 0.4209(3) 0.10330(17) 0.0368(5) Uani 1 1 d . . . C3 C 1.0606(3) 0.5064(3) 0.16319(19) 0.0474(6) Uani 1 1 d . . . H3 H 1.1313 0.4579 0.2032 0.057 Uiso 1 1 calc R . . C4 C 1.1134(3) 0.6657(3) 0.1610(2) 0.0542(7) Uani 1 1 d . . . H4 H 1.2222 0.7253 0.2003 0.065 Uiso 1 1 calc R . . C5 C 1.0089(3) 0.7399(3) 0.1019(2) 0.0510(7) Uani 1 1 d . . . H5 H 1.0487 0.8476 0.1021 0.061 Uiso 1 1 calc R . . C6 C 0.8471(3) 0.6556(3) 0.0431(2) 0.0451(6) Uani 1 1 d . . . H6 H 0.7763 0.7046 0.0035 0.054 Uiso 1 1 calc R . . C7 C 0.7928(3) 0.4945(3) 0.04497(17) 0.0375(5) Uani 1 1 d . . . C8 C 0.9078(3) 0.1515(3) 0.14131(19) 0.0450(6) Uani 1 1 d . . . H8A H 1.0142 0.1580 0.1246 0.054 Uiso 1 1 calc R . . H8B H 0.8376 0.0422 0.1168 0.054 Uiso 1 1 calc R . . C9 C 0.9494(3) 0.1901(3) 0.2515(2) 0.0490(6) Uani 1 1 d . . . C10 C 1.0892(5) 0.1480(5) 0.3071(3) 0.0800(10) Uani 1 1 d . . . H10 H 1.1577 0.1008 0.2769 0.096 Uiso 1 1 calc R . . C11 C 1.1260(7) 0.1768(6) 0.4078(3) 0.1118(16) Uani 1 1 d . . . H11 H 1.2187 0.1473 0.4452 0.134 Uiso 1 1 calc R . . C12 C 1.0280(7) 0.2477(6) 0.4525(3) 0.1000(14) Uani 1 1 d . . . H12 H 1.0540 0.2666 0.5202 0.120 Uiso 1 1 calc R . . C13 C 0.8902(5) 0.2918(5) 0.3981(3) 0.0832(11) Uani 1 1 d . . . H13 H 0.8242 0.3420 0.4287 0.100 Uiso 1 1 calc R . . C14 C 0.8511(4) 0.2606(4) 0.2976(2) 0.0638(8) Uani 1 1 d . . . H14 H 0.7565 0.2879 0.2605 0.077 Uiso 1 1 calc R . . C1S C 0.5933(9) 0.6961(10) 0.3192(5) 0.131(7) Uani 0.482(8) 1 d PGU A 1 C2S C 0.5906(9) 0.8558(9) 0.3310(5) 0.077(3) Uani 0.482(8) 1 d PGU A 1 H2S H 0.6614 0.9265 0.3069 0.092 Uiso 0.482(8) 1 calc PR A 1 C3S C 0.4822(11) 0.9099(8) 0.3788(5) 0.111(4) Uani 0.482(8) 1 d PGU A 1 H3S H 0.4804 1.0168 0.3867 0.133 Uiso 0.482(8) 1 calc PR A 1 C4S C 0.3764(11) 0.8043(12) 0.4148(6) 0.105(4) Uani 0.482(8) 1 d PGU A 1 H4S H 0.3038 0.8405 0.4468 0.126 Uiso 0.482(8) 1 calc PR A 1 C5S C 0.3791(10) 0.6445(11) 0.4030(6) 0.107(4) Uani 0.482(8) 1 d PGU A 1 H5S H 0.3084 0.5739 0.4271 0.128 Uiso 0.482(8) 1 calc PR A 1 C6S C 0.4876(10) 0.5904(8) 0.3552(5) 0.084(3) Uani 0.482(8) 1 d PGU A 1 H6S H 0.4894 0.4836 0.3473 0.100 Uiso 0.482(8) 1 calc PR A 1 C7S C 0.6956(14) 0.6380(17) 0.2658(7) 0.112(4) Uani 0.482(8) 1 d PU A 1 H7S1 H 0.7540 0.7233 0.2418 0.169 Uiso 0.482(8) 1 calc PR A 1 H7S2 H 0.6235 0.5537 0.2117 0.169 Uiso 0.482(8) 1 calc PR A 1 H7S3 H 0.7788 0.5975 0.3075 0.169 Uiso 0.482(8) 1 calc PR A 1 C8S C 0.6037(9) 0.7251(8) 0.3120(5) 0.102(5) Uani 0.518(8) 1 d PGDU A 2 C9S C 0.5249(11) 0.8107(8) 0.3668(5) 0.087(3) Uani 0.518(8) 1 d PGU A 2 H9S H 0.5479 0.9212 0.3742 0.105 Uiso 0.518(8) 1 calc PR A 2 C10S C 0.4118(11) 0.7312(14) 0.4106(6) 0.147(7) Uani 0.518(8) 1 d PGU A 2 H10S H 0.3592 0.7885 0.4473 0.176 Uiso 0.518(8) 1 calc PR A 2 C11S C 0.3775(11) 0.5660(14) 0.3996(7) 0.166(7) Uani 0.518(8) 1 d PGU A 2 H11S H 0.3018 0.5128 0.4289 0.199 Uiso 0.518(8) 1 calc PR A 2 C12S C 0.4562(11) 0.4804(8) 0.3448(7) 0.153(6) Uani 0.518(8) 1 d PGU A 2 H12S H 0.4332 0.3699 0.3374 0.184 Uiso 0.518(8) 1 calc PR A 2 C13S C 0.5693(10) 0.5600(8) 0.3010(5) 0.087(3) Uani 0.518(8) 1 d PGU A 2 H13S H 0.6220 0.5027 0.2643 0.105 Uiso 0.518(8) 1 calc PR A 2 C14S C 0.7256(11) 0.8159(14) 0.2740(7) 0.116(4) Uani 0.518(8) 1 d PDU A 2 H14A H 0.6667 0.8369 0.2128 0.173 Uiso 0.518(8) 1 calc PR A 2 H14B H 0.8066 0.7567 0.2643 0.173 Uiso 0.518(8) 1 calc PR A 2 H14C H 0.7855 0.9154 0.3195 0.173 Uiso 0.518(8) 1 calc PR A 2 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 Ni1 0.0275(2) 0.0253(2) 0.0417(2) 0.00692(16) 0.00891(17) -0.00236(15) Br1 0.04500(17) 0.03958(15) 0.05395(18) 0.00468(11) 0.02191(12) -0.00237(11) S1 0.0302(3) 0.0302(3) 0.0553(4) 0.0121(2) 0.0066(3) -0.0017(2) N1 0.0301(9) 0.0304(9) 0.0388(10) 0.0049(8) 0.0080(8) 0.0006(7) C1 0.0308(11) 0.0301(11) 0.0394(12) 0.0064(9) 0.0122(9) 0.0014(9) C2 0.0307(11) 0.0318(11) 0.0419(12) 0.0007(9) 0.0131(10) -0.0028(9) C3 0.0357(13) 0.0461(14) 0.0481(14) -0.0008(11) 0.0073(11) -0.0017(11) C4 0.0378(13) 0.0462(15) 0.0615(17) -0.0105(13) 0.0185(13) -0.0147(11) C5 0.0496(15) 0.0299(12) 0.0685(18) -0.0006(12) 0.0292(14) -0.0075(11) C6 0.0424(13) 0.0337(12) 0.0596(16) 0.0103(11) 0.0237(12) -0.0002(10) C7 0.0299(11) 0.0321(11) 0.0453(13) 0.0045(10) 0.0135(10) -0.0030(9) C8 0.0387(13) 0.0398(13) 0.0507(14) 0.0074(11) 0.0056(11) 0.0090(10) C9 0.0472(15) 0.0436(14) 0.0477(15) 0.0100(11) 0.0059(12) 0.0041(11) C10 0.074(2) 0.094(3) 0.065(2) 0.0159(19) -0.0013(17) 0.033(2) C11 0.109(4) 0.149(4) 0.064(3) 0.030(3) -0.013(2) 0.046(3) C12 0.120(4) 0.119(4) 0.046(2) 0.015(2) 0.009(2) 0.019(3) C13 0.090(3) 0.099(3) 0.054(2) 0.0098(19) 0.0206(19) 0.016(2) C14 0.0628(19) 0.076(2) 0.0512(17) 0.0162(15) 0.0136(15) 0.0166(16) C1S 0.106(10) 0.264(18) 0.042(6) 0.002(8) 0.020(6) 0.109(11) C2S 0.090(6) 0.075(6) 0.056(5) 0.024(4) 0.003(4) 0.015(5) C3S 0.111(8) 0.108(8) 0.086(6) 0.004(6) 0.002(6) 0.018(6) C4S 0.126(9) 0.124(9) 0.067(5) 0.014(6) 0.028(6) 0.040(7) C5S 0.126(10) 0.118(11) 0.067(6) 0.027(6) 0.020(6) 0.015(7) C6S 0.090(6) 0.102(7) 0.054(4) 0.030(5) 0.014(4) 0.014(6) C7S 0.104(8) 0.172(12) 0.066(5) 0.007(6) 0.020(5) 0.066(8) C8S 0.090(9) 0.097(8) 0.082(9) 0.030(7) -0.025(6) -0.002(6) C9S 0.102(7) 0.084(6) 0.054(5) -0.008(4) -0.010(4) 0.034(6) C10S 0.122(10) 0.122(12) 0.135(11) 0.024(9) -0.038(8) -0.003(9) C11S 0.138(11) 0.158(14) 0.154(12) 0.046(10) -0.040(9) 0.033(10) C12S 0.098(8) 0.126(9) 0.186(12) 0.056(9) -0.031(8) 0.003(7) C13S 0.085(6) 0.070(5) 0.089(6) 0.005(4) -0.006(5) 0.027(4) C14S 0.093(6) 0.141(10) 0.085(6) 0.014(6) 0.011(5) 0.000(6) _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 Ni1 C1 1.893(2) 2_655 ? Ni1 C1 1.893(2) . ? Ni1 Br1 2.3138(3) 2_655 ? Ni1 Br1 2.3139(3) . ? S1 C1 1.714(2) . ? S1 C7 1.743(2) . ? N1 C1 1.329(3) . ? N1 C2 1.412(3) . ? N1 C8 1.465(3) . ? C2 C7 1.379(3) . ? C2 C3 1.391(3) . ? C3 C4 1.377(4) . ? C4 C5 1.389(4) . ? C5 C6 1.375(4) . ? C6 C7 1.393(3) . ? C8 C9 1.515(4) . ? C9 C14 1.370(4) . ? C9 C10 1.388(4) . ? C10 C11 1.386(6) . ? C11 C12 1.359(6) . ? C12 C13 1.378(6) . ? C13 C14 1.381(5) . ? C1S C2S 1.3900 . ? C1S C6S 1.3900 . ? C1S C7S 1.413(11) . ? C2S C3S 1.3900 . ? C3S C4S 1.3900 . ? C4S C5S 1.3900 . ? C5S C6S 1.3900 . ? C8S C9S 1.3900 . ? C8S C13S 1.3900 . ? C8S C14S 1.427(7) . ? C9S C10S 1.3900 . ? C10S C11S 1.3900 . ? C11S C12S 1.3900 . ? C12S C13S 1.3900 . ? 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 C1 Ni1 C1 180.0 2_655 . ? C1 Ni1 Br1 90.62(7) 2_655 2_655 ? C1 Ni1 Br1 89.38(7) . 2_655 ? C1 Ni1 Br1 89.38(7) 2_655 . ? C1 Ni1 Br1 90.62(7) . . ? Br1 Ni1 Br1 180.0 2_655 . ? C1 S1 C7 93.10(11) . . ? C1 N1 C2 116.25(19) . . ? C1 N1 C8 122.07(18) . . ? C2 N1 C8 121.60(19) . . ? N1 C1 S1 109.70(15) . . ? N1 C1 Ni1 130.58(17) . . ? S1 C1 Ni1 119.69(12) . . ? C7 C2 C3 120.8(2) . . ? C7 C2 N1 111.62(18) . . ? C3 C2 N1 127.6(2) . . ? C4 C3 C2 117.5(3) . . ? C3 C4 C5 121.9(2) . . ? C6 C5 C4 120.7(2) . . ? C5 C6 C7 117.8(2) . . ? C2 C7 C6 121.4(2) . . ? C2 C7 S1 109.30(16) . . ? C6 C7 S1 129.2(2) . . ? N1 C8 C9 114.0(2) . . ? C14 C9 C10 119.2(3) . . ? C14 C9 C8 122.3(3) . . ? C10 C9 C8 118.4(3) . . ? C11 C10 C9 119.5(4) . . ? C12 C11 C10 120.6(4) . . ? C11 C12 C13 120.3(4) . . ? C12 C13 C14 119.2(4) . . ? C9 C14 C13 121.1(3) . . ? C2S C1S C6S 120.0 . . ? C2S C1S C7S 120.4(8) . . ? C6S C1S C7S 119.5(8) . . ? C3S C2S C1S 120.0 . . ? C2S C3S C4S 120.0 . . ? C5S C4S C3S 120.0 . . ? C4S C5S C6S 120.0 . . ? C5S C6S C1S 120.0 . . ? C9S C8S C13S 120.0 . . ? C9S C8S C14S 116.7(8) . . ? C13S C8S C14S 123.2(8) . . ? C10S C9S C8S 120.0 . . ? C9S C10S C11S 120.0 . . ? C12S C11S C10S 120.0 . . ? C11S C12S C13S 120.0 . . ? C12S C13S C8S 120.0 . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.689 _refine_diff_density_min -0.264 _refine_diff_density_rms 0.083 # Attachment 'NiNSMe.cif' data_Compound7 _database_code_depnum_ccdc_archive 'CCDC 699587' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C16 H14 I2 N2 Ni S2' _chemical_formula_weight 610.92 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' 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' I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M Pna2(1) 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' _cell_length_a 15.503(2) _cell_length_b 10.9857(15) _cell_length_c 11.3689(16) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1936.2(5) _cell_formula_units_Z 4 _cell_measurement_temperature 223(2) _cell_measurement_reflns_used 2584 _cell_measurement_theta_min 2.27 _cell_measurement_theta_max 21.59 _exptl_crystal_description Block _exptl_crystal_colour Red _exptl_crystal_size_max 0.12 _exptl_crystal_size_mid 0.04 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas 'Not Measured' _exptl_crystal_density_diffrn 2.096 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1160 _exptl_absorpt_coefficient_mu 4.406 _exptl_absorpt_correction_type Empirical _exptl_absorpt_correction_T_min 0.6199 _exptl_absorpt_correction_T_max 0.8435 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 223(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 13192 _diffrn_reflns_av_R_equivalents 0.0453 _diffrn_reflns_av_sigmaI/netI 0.0482 _diffrn_reflns_limit_h_min -20 _diffrn_reflns_limit_h_max 20 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 2.27 _diffrn_reflns_theta_max 27.45 _reflns_number_total 4084 _reflns_number_gt 3547 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0545P)^2^+2.9481P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.50(4) _refine_ls_number_reflns 4084 _refine_ls_number_parameters 211 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0564 _refine_ls_R_factor_gt 0.0485 _refine_ls_wR_factor_ref 0.1128 _refine_ls_wR_factor_gt 0.1086 _refine_ls_goodness_of_fit_ref 1.025 _refine_ls_restrained_S_all 1.025 _refine_ls_shift/su_max 0.034 _refine_ls_shift/su_mean 0.003 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Ni1 Ni 0.11654(8) 0.48849(9) 0.88381(12) 0.0407(3) Uani 1 1 d . . . S1 S 0.24612(17) 0.7100(2) 0.8414(3) 0.0547(6) Uani 1 1 d . . . S2 S -0.01379(16) 0.2680(2) 0.9261(2) 0.0504(6) Uani 1 1 d . . . I1 I 0.21481(4) 0.41055(5) 1.03982(5) 0.04814(17) Uani 1 1 d . . . I2 I 0.01943(5) 0.56528(5) 0.72767(6) 0.0564(2) Uani 1 1 d . . . N1 N 0.1216(5) 0.7324(6) 0.9797(7) 0.0429(18) Uani 1 1 d . . . N2 N 0.1130(5) 0.2436(6) 0.7868(7) 0.0402(16) Uani 1 1 d . . . C1 C 0.1560(6) 0.6510(8) 0.9097(8) 0.046(2) Uani 1 1 d . . . C2 C 0.1638(6) 0.8451(7) 0.9867(8) 0.0384(19) Uani 1 1 d . . . C3 C 0.1403(6) 0.9478(8) 1.0532(9) 0.049(2) Uani 1 1 d . . . H3 H 0.0908 0.9482 1.1009 0.059 Uiso 1 1 calc R . . C4 C 0.1948(8) 1.0501(7) 1.0449(10) 0.056(3) Uani 1 1 d . . . H4 H 0.1815 1.1201 1.0888 0.067 Uiso 1 1 calc R . . C5 C 0.2627(6) 1.0503(8) 0.9784(11) 0.054(3) Uani 1 1 d . . . H5 H 0.2983 1.1196 0.9785 0.065 Uiso 1 1 calc R . . C6 C 0.2855(7) 0.9518(10) 0.9062(11) 0.058(3) Uani 1 1 d . . . H6 H 0.3324 0.9559 0.8540 0.070 Uiso 1 1 calc R . . C7 C 0.2357(6) 0.8495(8) 0.9159(8) 0.042(2) Uani 1 1 d . . . C8 C 0.0499(7) 0.7110(8) 1.0475(10) 0.061(3) Uani 1 1 d . . . H8A H 0.0230 0.6354 1.0231 0.092 Uiso 1 1 calc R . . H8B H 0.0093 0.7775 1.0379 0.092 Uiso 1 1 calc R . . H8C H 0.0667 0.7050 1.1295 0.092 Uiso 1 1 calc R . . C9 C 0.0777(5) 0.3277(7) 0.8560(8) 0.0377(19) Uani 1 1 d . . . C10 C 0.0709(5) 0.1301(7) 0.7829(8) 0.0360(18) Uani 1 1 d . . . C11 C 0.0958(6) 0.0262(7) 0.7198(9) 0.047(2) Uani 1 1 d . . . H11 H 0.1448 0.0270 0.6711 0.056 Uiso 1 1 calc R . . C12 C 0.0452(5) -0.0794(6) 0.7315(9) 0.0332(18) Uani 1 1 d . . . H12 H 0.0593 -0.1501 0.6891 0.040 Uiso 1 1 calc R . . C13 C -0.0245(7) -0.0787(8) 0.8045(9) 0.047(2) Uani 1 1 d . . . H13 H -0.0564 -0.1509 0.8138 0.056 Uiso 1 1 calc R . . C14 C -0.0500(6) 0.0235(10) 0.8652(9) 0.052(2) Uani 1 1 d . . . H14 H -0.1000 0.0226 0.9119 0.062 Uiso 1 1 calc R . . C15 C -0.0007(6) 0.1266(8) 0.8559(8) 0.041(2) Uani 1 1 d . . . C16 C 0.1847(7) 0.2650(7) 0.7202(9) 0.052(2) Uani 1 1 d . . . H16A H 0.1800 0.2214 0.6463 0.078 Uiso 1 1 calc R . . H16B H 0.2355 0.2371 0.7622 0.078 Uiso 1 1 calc R . . H16C H 0.1897 0.3515 0.7048 0.078 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Ni1 0.0497(6) 0.0269(5) 0.0456(6) -0.0053(5) -0.0079(5) -0.0012(4) S1 0.0536(14) 0.0480(13) 0.0626(17) -0.0059(12) 0.0149(13) -0.0020(11) S2 0.0534(14) 0.0449(13) 0.0531(15) -0.0088(11) 0.0104(12) -0.0019(11) I1 0.0533(3) 0.0417(3) 0.0494(4) 0.0028(3) -0.0132(3) -0.0067(3) I2 0.0747(4) 0.0370(3) 0.0574(4) 0.0000(3) -0.0248(4) -0.0019(3) N1 0.049(4) 0.037(4) 0.043(5) 0.002(3) -0.015(3) -0.005(3) N2 0.050(4) 0.033(3) 0.038(4) 0.003(3) -0.008(3) -0.006(3) C1 0.058(6) 0.036(4) 0.043(6) -0.007(4) -0.005(4) 0.003(4) C2 0.049(5) 0.029(4) 0.038(5) 0.008(3) -0.014(4) -0.006(3) C3 0.059(5) 0.045(5) 0.043(6) -0.008(4) 0.016(5) -0.004(4) C4 0.108(9) 0.028(4) 0.030(5) -0.009(5) 0.001(6) 0.001(4) C5 0.047(6) 0.036(5) 0.078(8) 0.003(5) -0.021(6) -0.013(4) C6 0.045(6) 0.063(6) 0.066(7) 0.021(6) -0.004(5) -0.001(5) C7 0.041(5) 0.041(5) 0.044(5) -0.003(4) -0.012(4) 0.009(4) C8 0.106(8) 0.035(4) 0.042(6) 0.002(5) 0.029(6) 0.011(5) C9 0.041(5) 0.033(4) 0.039(5) -0.004(4) -0.007(4) 0.001(3) C10 0.036(4) 0.033(4) 0.039(5) -0.004(3) -0.004(4) -0.001(3) C11 0.058(5) 0.045(4) 0.037(5) -0.002(4) -0.006(5) 0.005(4) C12 0.034(4) 0.028(3) 0.038(5) -0.016(4) -0.015(4) 0.010(3) C13 0.054(6) 0.033(4) 0.054(6) -0.001(4) -0.003(5) -0.008(4) C14 0.034(5) 0.072(7) 0.049(6) 0.011(5) -0.001(4) -0.014(5) C15 0.046(5) 0.040(4) 0.037(5) -0.004(4) -0.002(4) 0.008(4) C16 0.081(6) 0.037(4) 0.038(5) -0.003(4) 0.009(5) 0.009(4) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Ni1 C9 1.893(8) . ? Ni1 C1 1.910(9) . ? Ni1 I2 2.4757(14) . ? Ni1 I1 2.4900(14) . ? S1 C1 1.725(10) . ? S1 C7 1.758(9) . ? S2 C9 1.754(9) . ? S2 C15 1.758(9) . ? N1 C1 1.310(12) . ? N1 C8 1.373(12) . ? N1 C2 1.403(11) . ? N2 C9 1.331(11) . ? N2 C16 1.365(12) . ? N2 C10 1.409(10) . ? C2 C7 1.376(13) . ? C2 C3 1.406(12) . ? C3 C4 1.408(13) . ? C4 C5 1.296(15) . ? C5 C6 1.404(16) . ? C6 C7 1.368(14) . ? C10 C15 1.387(12) . ? C10 C11 1.403(12) . ? C11 C12 1.407(11) . ? C12 C13 1.362(14) . ? C13 C14 1.376(14) . ? C14 C15 1.370(13) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C9 Ni1 C1 179.3(4) . . ? C9 Ni1 I2 90.3(3) . . ? C1 Ni1 I2 89.3(3) . . ? C9 Ni1 I1 89.6(3) . . ? C1 Ni1 I1 90.9(3) . . ? I2 Ni1 I1 179.61(7) . . ? C1 S1 C7 92.1(4) . . ? C9 S2 C15 91.8(4) . . ? C1 N1 C8 123.7(8) . . ? C1 N1 C2 116.5(8) . . ? C8 N1 C2 119.8(8) . . ? C9 N2 C16 122.9(7) . . ? C9 N2 C10 116.2(8) . . ? C16 N2 C10 120.8(8) . . ? N1 C1 S1 110.3(7) . . ? N1 C1 Ni1 126.9(7) . . ? S1 C1 Ni1 122.8(5) . . ? C7 C2 N1 112.1(8) . . ? C7 C2 C3 119.7(8) . . ? N1 C2 C3 128.2(9) . . ? C2 C3 C4 116.7(9) . . ? C5 C4 C3 121.9(9) . . ? C4 C5 C6 122.9(9) . . ? C7 C6 C5 116.4(10) . . ? C6 C7 C2 122.2(9) . . ? C6 C7 S1 128.7(8) . . ? C2 C7 S1 109.0(7) . . ? N2 C9 S2 110.0(6) . . ? N2 C9 Ni1 128.0(7) . . ? S2 C9 Ni1 122.0(5) . . ? C15 C10 C11 120.3(8) . . ? C15 C10 N2 112.1(7) . . ? C11 C10 N2 127.5(8) . . ? C10 C11 C12 117.9(9) . . ? C13 C12 C11 119.7(8) . . ? C12 C13 C14 122.6(8) . . ? C15 C14 C13 118.4(9) . . ? C14 C15 C10 121.0(8) . . ? C14 C15 S2 129.1(8) . . ? C10 C15 S2 109.9(6) . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 27.45 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 1.015 _refine_diff_density_min -0.415 _refine_diff_density_rms 0.146 # Attachment 'NiNSEt.cif' data_Compound8 _database_code_depnum_ccdc_archive 'CCDC 699588' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C18 H18 I2 N2 Ni S2' _chemical_formula_weight 638.97 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' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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 9.0231(5) _cell_length_b 10.4549(5) _cell_length_c 11.1487(6) _cell_angle_alpha 90.00 _cell_angle_beta 93.8170(10) _cell_angle_gamma 90.00 _cell_volume 1049.39(10) _cell_formula_units_Z 2 _cell_measurement_temperature 223(2) _cell_measurement_reflns_used 5110 _cell_measurement_theta_min 2.67 _cell_measurement_theta_max 27.51 _exptl_crystal_description BLOCK _exptl_crystal_colour Red _exptl_crystal_size_max 0.56 _exptl_crystal_size_mid 0.40 _exptl_crystal_size_min 0.30 _exptl_crystal_density_meas 0 _exptl_crystal_density_diffrn 2.022 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 612 _exptl_absorpt_coefficient_mu 4.069 _exptl_absorpt_correction_type 'Sadabs, (Sheldrick 2001)' _exptl_absorpt_correction_T_min 0.2090 _exptl_absorpt_correction_T_max 0.3749 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 223(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 7234 _diffrn_reflns_av_R_equivalents 0.0208 _diffrn_reflns_av_sigmaI/netI 0.0212 _diffrn_reflns_limit_h_min -5 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 2.67 _diffrn_reflns_theta_max 27.49 _reflns_number_total 2404 _reflns_number_gt 2270 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0242P)^2^+0.9298P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2404 _refine_ls_number_parameters 116 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0232 _refine_ls_R_factor_gt 0.0218 _refine_ls_wR_factor_ref 0.0543 _refine_ls_wR_factor_gt 0.0536 _refine_ls_goodness_of_fit_ref 1.043 _refine_ls_restrained_S_all 1.043 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Ni1 Ni 0.5000 0.5000 0.0000 0.02656(10) Uani 1 2 d S . . I1 I 0.38607(2) 0.703697(16) 0.063573(15) 0.03825(7) Uani 1 1 d . . . S1 S 0.43030(7) 0.36395(6) 0.24182(5) 0.03144(13) Uani 1 1 d . . . N1 N 0.6649(2) 0.49221(18) 0.23496(17) 0.0275(4) Uani 1 1 d . . . C1 C 0.5475(3) 0.4585(2) 0.1635(2) 0.0275(4) Uani 1 1 d . . . C2 C 0.6701(3) 0.4448(2) 0.3535(2) 0.0267(4) Uani 1 1 d . . . C3 C 0.7805(3) 0.4656(2) 0.4449(2) 0.0327(5) Uani 1 1 d . . . H3 H 0.8647 0.5153 0.4318 0.039 Uiso 1 1 calc R . . C4 C 0.7615(3) 0.4104(3) 0.5550(2) 0.0393(6) Uani 1 1 d . . . H4 H 0.8346 0.4229 0.6180 0.047 Uiso 1 1 calc R . . C5 C 0.6379(3) 0.3371(3) 0.5756(2) 0.0392(6) Uani 1 1 d . . . H5 H 0.6288 0.3006 0.6517 0.047 Uiso 1 1 calc R . . C6 C 0.5276(3) 0.3172(2) 0.4852(2) 0.0339(5) Uani 1 1 d . . . H6 H 0.4428 0.2685 0.4990 0.041 Uiso 1 1 calc R . . C7 C 0.5462(3) 0.3713(2) 0.3736(2) 0.0272(4) Uani 1 1 d . . . C8 C 0.7843(3) 0.5730(2) 0.1941(2) 0.0351(5) Uani 1 1 d . . . H8A H 0.8131 0.6356 0.2568 0.042 Uiso 1 1 calc R . . H8B H 0.7475 0.6202 0.1222 0.042 Uiso 1 1 calc R . . C9 C 0.9198(3) 0.4958(3) 0.1651(3) 0.0461(7) Uani 1 1 d . . . H9A H 0.9519 0.4436 0.2339 0.069 Uiso 1 1 calc R . . H9B H 0.9993 0.5535 0.1464 0.069 Uiso 1 1 calc R . . H9C H 0.8948 0.4411 0.0965 0.069 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Ni1 0.0308(2) 0.0286(2) 0.01976(19) 0.00224(15) -0.00168(15) 0.00256(16) I1 0.04857(12) 0.03519(11) 0.03074(10) -0.00053(6) 0.00075(7) 0.01165(7) S1 0.0307(3) 0.0374(3) 0.0257(3) 0.0026(2) -0.0022(2) -0.0058(2) N1 0.0298(10) 0.0282(10) 0.0243(9) 0.0018(7) 0.0006(7) -0.0006(7) C1 0.0307(11) 0.0271(11) 0.0245(10) 0.0010(9) 0.0015(8) 0.0028(9) C2 0.0315(11) 0.0266(11) 0.0220(10) -0.0009(8) 0.0005(8) 0.0048(9) C3 0.0302(12) 0.0379(13) 0.0295(11) -0.0029(10) -0.0030(9) 0.0019(10) C4 0.0397(14) 0.0512(16) 0.0258(12) -0.0031(11) -0.0077(10) 0.0064(11) C5 0.0451(15) 0.0498(15) 0.0225(11) 0.0058(11) 0.0017(10) 0.0078(12) C6 0.0367(13) 0.0372(13) 0.0283(12) 0.0026(10) 0.0052(10) 0.0005(10) C7 0.0296(11) 0.0281(11) 0.0235(10) -0.0004(8) -0.0018(8) 0.0032(8) C8 0.0346(13) 0.0352(13) 0.0353(13) 0.0049(10) 0.0002(10) -0.0060(10) C9 0.0356(14) 0.0570(18) 0.0466(16) 0.0000(13) 0.0087(12) -0.0065(12) _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 Ni1 C1 1.895(2) 3_665 ? Ni1 C1 1.895(2) . ? Ni1 I1 2.48828(18) . ? Ni1 I1 2.48833(18) 3_665 ? S1 C1 1.726(2) . ? S1 C7 1.747(2) . ? N1 C1 1.330(3) . ? N1 C2 1.409(3) . ? N1 C8 1.466(3) . ? C2 C7 1.387(3) . ? C2 C3 1.394(3) . ? C3 C4 1.377(4) . ? C4 C5 1.385(4) . ? C5 C6 1.384(4) . ? C6 C7 1.387(3) . ? C8 C9 1.517(4) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 Ni1 C1 180.0 3_665 . ? C1 Ni1 I1 90.39(7) 3_665 . ? C1 Ni1 I1 89.61(7) . . ? C1 Ni1 I1 89.61(7) 3_665 3_665 ? C1 Ni1 I1 90.39(7) . 3_665 ? I1 Ni1 I1 180.0 . 3_665 ? C1 S1 C7 92.73(11) . . ? C1 N1 C2 116.34(19) . . ? C1 N1 C8 122.6(2) . . ? C2 N1 C8 121.02(19) . . ? N1 C1 S1 109.82(16) . . ? N1 C1 Ni1 129.47(17) . . ? S1 C1 Ni1 120.71(13) . . ? C7 C2 C3 120.8(2) . . ? C7 C2 N1 111.72(19) . . ? C3 C2 N1 127.4(2) . . ? C4 C3 C2 117.4(2) . . ? C3 C4 C5 121.9(2) . . ? C6 C5 C4 120.7(2) . . ? C5 C6 C7 117.8(2) . . ? C2 C7 C6 121.2(2) . . ? C2 C7 S1 109.39(17) . . ? C6 C7 S1 129.40(19) . . ? N1 C8 C9 112.3(2) . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 27.49 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.670 _refine_diff_density_min -0.884 _refine_diff_density_rms 0.080 # Attachment 'NiNSiPr.cif' data_Compound9 _database_code_depnum_ccdc_archive 'CCDC 699589' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C20 H22 I2 N2 Ni S2' _chemical_formula_weight 667.03 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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' I I -0.4742 1.8119 '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 8.4018(5) _cell_length_b 12.2872(7) _cell_length_c 11.0743(6) _cell_angle_alpha 90.00 _cell_angle_beta 90.5030(10) _cell_angle_gamma 90.00 _cell_volume 1143.21(11) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 7163 _cell_measurement_theta_min 2.48 _cell_measurement_theta_max 27.46 _exptl_crystal_description ROD _exptl_crystal_colour RED _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.08 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas 'Not Measured' _exptl_crystal_density_diffrn 1.938 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 644 _exptl_absorpt_coefficient_mu 3.740 _exptl_absorpt_correction_type 'Sadabs, (Sheldrick 2001)' _exptl_absorpt_correction_T_min 0.4000 _exptl_absorpt_correction_T_max 0.8067 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 14493 _diffrn_reflns_av_R_equivalents 0.0284 _diffrn_reflns_av_sigmaI/netI 0.0196 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 2.48 _diffrn_reflns_theta_max 27.49 _reflns_number_total 2612 _reflns_number_gt 2522 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0198P)^2^+1.4986P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2612 _refine_ls_number_parameters 126 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0277 _refine_ls_R_factor_gt 0.0263 _refine_ls_wR_factor_ref 0.0581 _refine_ls_wR_factor_gt 0.0573 _refine_ls_goodness_of_fit_ref 1.103 _refine_ls_restrained_S_all 1.103 _refine_ls_shift/su_max 0.002 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Ni1 Ni 1.0000 1.0000 0.0000 0.02549(11) Uani 1 2 d S . . I1 I 1.10036(3) 1.180491(16) 0.069361(17) 0.04241(8) Uani 1 1 d . . . S1 S 1.10548(8) 0.89701(6) 0.24894(6) 0.03156(15) Uani 1 1 d . . . N1 N 0.8287(2) 0.97131(17) 0.22573(18) 0.0247(4) Uani 1 1 d . . . C1 C 0.9616(3) 0.9592(2) 0.1622(2) 0.0253(5) Uani 1 1 d . . . C2 C 0.8334(3) 0.9320(2) 0.3452(2) 0.0251(5) Uani 1 1 d . . . C3 C 0.7130(3) 0.9315(2) 0.4313(2) 0.0344(6) Uani 1 1 d . . . H3 H 0.6131 0.9604 0.4137 0.041 Uiso 1 1 calc R . . C4 C 0.7462(4) 0.8870(3) 0.5432(3) 0.0414(7) Uani 1 1 d . . . H4 H 0.6670 0.8855 0.6013 0.050 Uiso 1 1 calc R . . C5 C 0.8945(4) 0.8446(3) 0.5710(3) 0.0404(7) Uani 1 1 d . . . H5 H 0.9134 0.8154 0.6473 0.048 Uiso 1 1 calc R . . C6 C 1.0142(4) 0.8450(2) 0.4873(3) 0.0354(6) Uani 1 1 d . . . H6 H 1.1141 0.8168 0.5062 0.042 Uiso 1 1 calc R . . C7 C 0.9826(3) 0.8883(2) 0.3739(2) 0.0256(5) Uani 1 1 d . . . C8 C 0.6870(3) 1.0250(2) 0.1697(2) 0.0331(6) Uani 1 1 d . . . H8 H 0.7168 1.0438 0.0870 0.040 Uiso 1 1 calc R . . C9 C 0.5469(4) 0.9467(3) 0.1597(3) 0.0475(8) Uani 1 1 d . . . H9A H 0.5768 0.8851 0.1117 0.071 Uiso 1 1 calc R . . H9B H 0.4583 0.9832 0.1221 0.071 Uiso 1 1 calc R . . H9C H 0.5174 0.9227 0.2389 0.071 Uiso 1 1 calc R . . C10 C 0.6503(4) 1.1315(3) 0.2331(3) 0.0498(8) Uani 1 1 d . . . H10A H 0.6284 1.1176 0.3166 0.075 Uiso 1 1 calc R . . H10B H 0.5591 1.1649 0.1957 0.075 Uiso 1 1 calc R . . H10C H 0.7401 1.1794 0.2271 0.075 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Ni1 0.0283(2) 0.0288(2) 0.0195(2) 0.00186(17) 0.00733(17) -0.00359(18) I1 0.06185(15) 0.03593(12) 0.02963(11) -0.00239(7) 0.01003(9) -0.01677(9) S1 0.0272(3) 0.0395(4) 0.0281(3) 0.0025(3) 0.0061(2) 0.0053(3) N1 0.0253(10) 0.0279(11) 0.0210(10) 0.0018(8) 0.0040(8) -0.0005(8) C1 0.0279(12) 0.0239(12) 0.0240(12) -0.0012(9) 0.0042(9) -0.0026(9) C2 0.0299(12) 0.0247(12) 0.0208(11) 0.0000(9) 0.0045(9) -0.0034(10) C3 0.0307(13) 0.0431(16) 0.0296(13) 0.0018(12) 0.0089(11) -0.0005(12) C4 0.0459(17) 0.0508(18) 0.0278(14) 0.0027(13) 0.0144(12) -0.0055(14) C5 0.0583(19) 0.0421(16) 0.0209(13) 0.0054(11) 0.0034(12) -0.0013(14) C6 0.0420(16) 0.0354(15) 0.0287(14) 0.0011(11) -0.0018(11) 0.0057(12) C7 0.0306(12) 0.0249(12) 0.0215(11) -0.0013(9) 0.0056(9) -0.0007(10) C8 0.0301(13) 0.0430(16) 0.0264(13) 0.0072(11) 0.0035(10) 0.0066(12) C9 0.0297(15) 0.072(2) 0.0411(17) 0.0045(16) -0.0030(12) -0.0030(15) C10 0.0494(19) 0.0418(18) 0.058(2) 0.0061(16) 0.0087(16) 0.0160(15) _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 Ni1 C1 1.896(2) 3_775 ? Ni1 C1 1.896(2) . ? Ni1 I1 2.4916(2) . ? Ni1 I1 2.4916(2) 3_775 ? S1 C1 1.717(3) . ? S1 C7 1.738(2) . ? N1 C1 1.333(3) . ? N1 C2 1.409(3) . ? N1 C8 1.492(3) . ? C2 C3 1.396(3) . ? C2 C7 1.398(4) . ? C3 C4 1.381(4) . ? C4 C5 1.382(5) . ? C5 C6 1.374(4) . ? C6 C7 1.388(4) . ? C8 C10 1.519(4) . ? C8 C9 1.523(4) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 Ni1 C1 180.00(14) 3_775 . ? C1 Ni1 I1 89.84(7) 3_775 . ? C1 Ni1 I1 90.17(7) . . ? C1 Ni1 I1 90.16(7) 3_775 3_775 ? C1 Ni1 I1 89.83(7) . 3_775 ? I1 Ni1 I1 179.999(10) . 3_775 ? C1 S1 C7 93.01(12) . . ? C1 N1 C2 116.2(2) . . ? C1 N1 C8 120.0(2) . . ? C2 N1 C8 123.9(2) . . ? N1 C1 S1 110.09(18) . . ? N1 C1 Ni1 128.38(19) . . ? S1 C1 Ni1 121.52(14) . . ? C3 C2 C7 119.8(2) . . ? C3 C2 N1 128.9(2) . . ? C7 C2 N1 111.3(2) . . ? C4 C3 C2 118.2(3) . . ? C3 C4 C5 121.6(3) . . ? C6 C5 C4 120.8(3) . . ? C5 C6 C7 118.5(3) . . ? C6 C7 C2 121.2(2) . . ? C6 C7 S1 129.4(2) . . ? C2 C7 S1 109.46(18) . . ? N1 C8 C10 110.7(2) . . ? N1 C8 C9 111.4(2) . . ? C10 C8 C9 114.7(3) . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 27.49 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.870 _refine_diff_density_min -0.428 _refine_diff_density_rms 0.081 # Attachment 'NiNSiBu.cif' data_Compound10 _database_code_depnum_ccdc_archive 'CCDC 699590' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C22 H26 I2 N2 Ni S2' _chemical_formula_weight 695.08 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' 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' I I -0.4742 1.8119 '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 17.3549(15) _cell_length_b 9.9210(9) _cell_length_c 14.9512(12) _cell_angle_alpha 90.00 _cell_angle_beta 93.931(2) _cell_angle_gamma 90.00 _cell_volume 2568.2(4) _cell_formula_units_Z 4 _cell_measurement_temperature 223(2) _cell_measurement_reflns_used 2814 _cell_measurement_theta_min 2.35 _cell_measurement_theta_max 27.54 _exptl_crystal_description BLOCK _exptl_crystal_colour RED _exptl_crystal_size_max 0.18 _exptl_crystal_size_mid 0.08 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas 'Not Measured' _exptl_crystal_density_diffrn 1.798 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1352 _exptl_absorpt_coefficient_mu 3.333 _exptl_absorpt_correction_type 'Sadabs, (Sheldrick 2001)' _exptl_absorpt_correction_T_min 0.5852 _exptl_absorpt_correction_T_max 0.7763 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 223(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 7236 _diffrn_reflns_av_R_equivalents 0.0318 _diffrn_reflns_av_sigmaI/netI 0.0411 _diffrn_reflns_limit_h_min -20 _diffrn_reflns_limit_h_max 20 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 2.35 _diffrn_reflns_theta_max 25.00 _reflns_number_total 2264 _reflns_number_gt 2126 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0698P)^2^+76.2837P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2264 _refine_ls_number_parameters 135 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0820 _refine_ls_R_factor_gt 0.0788 _refine_ls_wR_factor_ref 0.2055 _refine_ls_wR_factor_gt 0.2037 _refine_ls_goodness_of_fit_ref 1.264 _refine_ls_restrained_S_all 1.264 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Ni1 Ni 0.2500 0.7500 0.0000 0.0305(5) Uani 1 2 d S . . I1 I 0.12710(4) 0.72769(10) 0.07620(5) 0.0453(3) Uani 1 1 d . . . S1 S 0.3454(2) 0.5792(4) 0.1431(2) 0.0537(9) Uani 1 1 d . . . N1 N 0.3221(6) 0.8242(12) 0.1767(7) 0.050(3) Uani 1 1 d . . . C1 C 0.3064(6) 0.7355(12) 0.1123(8) 0.037(3) Uani 1 1 d . . . C2 C 0.3653(7) 0.7745(16) 0.2541(8) 0.047(3) Uani 1 1 d . . . C3 C 0.3885(8) 0.8506(18) 0.3314(8) 0.060(4) Uani 1 1 d . . . H3 H 0.3768 0.9426 0.3371 0.072 Uiso 1 1 calc R . . C4 C 0.4304(9) 0.777(2) 0.3989(9) 0.072(5) Uani 1 1 d . . . H4 H 0.4499 0.8236 0.4505 0.086 Uiso 1 1 calc R . . C5 C 0.4443(9) 0.642(2) 0.3931(10) 0.078(5) Uani 1 1 d . . . H5 H 0.4698 0.5974 0.4419 0.094 Uiso 1 1 calc R . . C6 C 0.4217(9) 0.571(2) 0.3172(10) 0.072(5) Uani 1 1 d . . . H6 H 0.4328 0.4792 0.3120 0.086 Uiso 1 1 calc R . . C7 C 0.3815(7) 0.6420(17) 0.2481(8) 0.056(4) Uani 1 1 d . . . C8 C 0.2924(7) 0.9619(13) 0.1700(8) 0.048(3) Uani 1 1 d . . . H8A H 0.2892 0.9980 0.2307 0.058 Uiso 1 1 calc R . . H8B H 0.2399 0.9596 0.1414 0.058 Uiso 1 1 calc R . . C9 C 0.3402(7) 1.0551(14) 0.1183(8) 0.048(3) Uani 1 1 d . . . H9 H 0.3395 1.0214 0.0559 0.057 Uiso 1 1 calc R . . C10 C 0.3027(10) 1.1988(19) 0.1159(12) 0.076(5) Uani 1 1 d . . . H10A H 0.2502 1.1931 0.0894 0.114 Uiso 1 1 calc R . . H10B H 0.3325 1.2586 0.0803 0.114 Uiso 1 1 calc R . . H10C H 0.3022 1.2337 0.1764 0.114 Uiso 1 1 calc R . . C11 C 0.4238(8) 1.0647(18) 0.1545(10) 0.069(4) Uani 1 1 d . . . H11A H 0.4263 1.1058 0.2135 0.103 Uiso 1 1 calc R . . H11B H 0.4524 1.1193 0.1144 0.103 Uiso 1 1 calc R . . H11C H 0.4461 0.9750 0.1586 0.103 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Ni1 0.0280(10) 0.0360(11) 0.0275(10) -0.0023(7) 0.0019(8) -0.0035(7) I1 0.0298(5) 0.0712(6) 0.0358(5) -0.0006(3) 0.0079(3) -0.0053(3) S1 0.053(2) 0.055(2) 0.0528(19) 0.0022(15) 0.0025(15) -0.0002(15) N1 0.042(6) 0.067(7) 0.039(5) -0.013(5) -0.010(4) 0.008(5) C1 0.026(5) 0.051(7) 0.034(6) 0.005(5) 0.001(4) 0.000(5) C2 0.028(6) 0.088(11) 0.025(6) 0.001(6) 0.001(4) -0.003(6) C3 0.060(8) 0.082(11) 0.039(7) -0.007(7) 0.003(6) -0.006(8) C4 0.047(8) 0.141(17) 0.027(6) 0.006(8) -0.004(6) -0.017(9) C5 0.062(10) 0.124(17) 0.047(9) 0.038(10) -0.005(7) -0.012(10) C6 0.062(9) 0.103(13) 0.051(8) 0.026(8) -0.001(7) -0.014(9) C7 0.044(7) 0.082(11) 0.040(7) 0.010(7) 0.005(5) -0.016(7) C8 0.045(7) 0.055(8) 0.045(7) 0.001(6) 0.002(5) 0.005(6) C9 0.045(7) 0.056(8) 0.043(7) -0.010(6) 0.011(5) -0.002(6) C10 0.069(11) 0.091(13) 0.070(10) -0.002(9) 0.012(8) 0.020(9) C11 0.045(8) 0.092(12) 0.071(10) 0.011(9) 0.009(7) -0.011(8) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Ni1 C1 1.890(11) . ? Ni1 C1 1.890(11) 7_565 ? Ni1 I1 2.4959(7) 7_565 ? Ni1 I1 2.4959(7) . ? S1 C1 1.742(12) . ? S1 C7 1.764(14) . ? N1 C1 1.319(16) . ? N1 C2 1.424(15) . ? N1 C8 1.461(17) . ? C2 C7 1.35(2) . ? C2 C3 1.415(18) . ? C3 C4 1.41(2) . ? C4 C5 1.36(3) . ? C5 C6 1.37(2) . ? C6 C7 1.40(2) . ? C8 C9 1.493(17) . ? C9 C11 1.516(18) . ? C9 C10 1.57(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 C1 Ni1 C1 180.000(1) . 7_565 ? C1 Ni1 I1 90.3(3) . 7_565 ? C1 Ni1 I1 89.7(3) 7_565 7_565 ? C1 Ni1 I1 89.7(3) . . ? C1 Ni1 I1 90.3(3) 7_565 . ? I1 Ni1 I1 180.0 7_565 . ? C1 S1 C7 91.6(7) . . ? C1 N1 C2 115.7(11) . . ? C1 N1 C8 121.3(10) . . ? C2 N1 C8 122.9(11) . . ? N1 C1 S1 110.1(9) . . ? N1 C1 Ni1 131.8(9) . . ? S1 C1 Ni1 118.1(7) . . ? C7 C2 C3 121.7(13) . . ? C7 C2 N1 112.6(11) . . ? C3 C2 N1 125.7(14) . . ? C4 C3 C2 114.5(16) . . ? C5 C4 C3 123.1(15) . . ? C4 C5 C6 121.0(15) . . ? C5 C6 C7 117.1(18) . . ? C2 C7 C6 122.4(14) . . ? C2 C7 S1 109.9(10) . . ? C6 C7 S1 127.7(14) . . ? N1 C8 C9 114.1(11) . . ? C8 C9 C11 114.0(12) . . ? C8 C9 C10 109.3(11) . . ? C11 C9 C10 109.7(13) . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 3.792 _refine_diff_density_min -0.904 _refine_diff_density_rms 0.217