# Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2005 data_global _journal_name_full Chem.Commun. _journal_coden_cambridge 0182 _journal_year ? _journal_volume ? _journal_page_first ? _publ_contact_author_name 'M. Schroder' _publ_contact_author_email M.SCHRODER@NOTTINGHAM.AC.UK loop_ _publ_author_name M.Schroder A.J.Blake A.Marin-Becerra J.McMaster M.Schroder ; P.A.Stenson ; C.Wilson data_nfcoth _database_code_depnum_ccdc_archive 'CCDC 278856' _audit_creation_method SHELXL-97 _chemical_name_systematic ? _refine_special_details ; 2 toluene sites in asymmetric unit. One 1/2 occupied with Me group disordered over two sites. Second disordered over 2 orientations with occupancies of 0.75 and 0.25, modelled with restraints on toluene geometry and with isotropic displacement parameters. The half-occupied H atom on C101 is not included in the refinement model but is counted in the formula. C200 and C213 represent a common site. ; _chemical_name_common NiLFe(CO)3 _chemical_melting_point ? _chemical_formula_moiety 'C22 H20 Fe N2 Ni O3 S2, 1.5(C7 H8)' _chemical_formula_sum 'C32.50 H32 Fe N2 Ni O3 S2' _chemical_formula_weight 677.28 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' Fe Fe 0.3463 0.8444 '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 'P 21/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 12.245(2) _cell_length_b 15.779(2) _cell_length_c 16.870(2) _cell_angle_alpha 90.00 _cell_angle_beta 106.888(2) _cell_angle_gamma 90.00 _cell_volume 3118.9(7) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 3319 _cell_measurement_theta_min 2.15 _cell_measurement_theta_max 25.1 _exptl_crystal_description tablet _exptl_crystal_colour red _exptl_crystal_size_max 0.24 _exptl_crystal_size_mid 0.17 _exptl_crystal_size_min 0.075 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.442 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1404 _exptl_absorpt_coefficient_mu 1.238 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.771 _exptl_absorpt_correction_T_max 1.000 _exptl_absorpt_process_details 'Bruker SADABS v2.03' _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker SMART APEX CCD area detector' _diffrn_measurement_method omega _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count . _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 15495 _diffrn_reflns_av_R_equivalents 0.030 _diffrn_reflns_av_sigmaI/netI 0.044 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -20 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 2.16 _diffrn_reflns_theta_max 27.52 _reflns_number_total 6978 _reflns_number_gt 5624 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART version 5.625 (Bruker, 2001)' _computing_cell_refinement 'Bruker SAINT version 6.36a (Bruker, 2000)' _computing_data_reduction 'Bruker SAINT; Bruker SHELXTL (Bruker, 2001)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material 'enCIFer (Allen et al., 2004); PLATON (Spek, 2003)' _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^)+(0.0483P)^2^+3.3697P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens 'geometrically placed' _refine_ls_hydrogen_treatment 'riding model' _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 6978 _refine_ls_number_parameters 372 _refine_ls_number_restraints 75 _refine_ls_R_factor_all 0.0603 _refine_ls_R_factor_gt 0.0467 _refine_ls_wR_factor_ref 0.111 _refine_ls_wR_factor_gt 0.104 _refine_ls_goodness_of_fit_ref 1.02 _refine_ls_restrained_S_all 1.04 _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 0.67747(3) 0.97663(2) 0.16837(2) 0.02171(10) Uani 1 1 d . . . Fe1 Fe 0.84902(4) 0.93078(3) 0.32012(3) 0.02639(12) Uani 1 1 d . . . S1 S 0.67302(7) 1.00089(5) 0.29631(5) 0.02638(17) Uani 1 1 d . . . S2 S 0.63665(7) 1.10750(5) 0.13935(5) 0.02549(17) Uani 1 1 d . . . N1 N 0.7593(2) 0.87531(15) 0.21394(15) 0.0237(5) Uani 1 1 d . . . N2 N 0.6509(2) 0.93782(15) 0.05888(15) 0.0217(5) Uani 1 1 d . . . C1 C 0.7466(3) 0.82746(19) 0.28050(18) 0.0264(6) Uani 1 1 d . . . H1A H 0.7862 0.7713 0.2891 0.032 Uiso 1 1 calc R . . C2 C 0.6403(3) 0.83187(19) 0.30485(17) 0.0263(6) Uani 1 1 d . . . C3 C 0.5920(3) 0.91122(19) 0.30920(18) 0.0266(6) Uani 1 1 d . . . C4 C 0.4891(3) 0.9187(2) 0.3273(2) 0.0329(7) Uani 1 1 d . . . H4A H 0.4548 0.9727 0.3273 0.039 Uiso 1 1 calc R . . C5 C 0.4366(3) 0.8461(2) 0.3454(2) 0.0373(8) Uani 1 1 d . . . H5A H 0.3660 0.8506 0.3578 0.045 Uiso 1 1 calc R . . C6 C 0.4864(3) 0.7671(2) 0.3454(2) 0.0381(8) Uani 1 1 d . . . H6A H 0.4514 0.7181 0.3598 0.046 Uiso 1 1 calc R . . C7 C 0.5878(3) 0.7598(2) 0.32430(19) 0.0319(7) Uani 1 1 d . . . H7A H 0.6211 0.7056 0.3232 0.038 Uiso 1 1 calc R . . C8 C 0.8223(3) 0.8362(2) 0.16104(18) 0.0279(7) Uani 1 1 d . . . H8A H 0.8758 0.7933 0.1936 0.033 Uiso 1 1 calc R . . H8B H 0.8679 0.8802 0.1434 0.033 Uiso 1 1 calc R . . C9 C 0.7420(3) 0.79354(19) 0.08368(19) 0.0269(6) Uani 1 1 d . . . C10 C 0.7075(3) 0.7043(2) 0.1030(2) 0.0408(9) Uani 1 1 d . . . H10A H 0.6672 0.7076 0.1453 0.061 Uiso 1 1 calc R . . H10B H 0.7760 0.6692 0.1235 0.061 Uiso 1 1 calc R . . H10C H 0.6572 0.6789 0.0525 0.061 Uiso 1 1 calc R . . C11 C 0.8051(3) 0.7893(2) 0.0172(2) 0.0381(8) Uani 1 1 d . . . H11A H 0.7559 0.7624 -0.0329 0.057 Uiso 1 1 calc R . . H11B H 0.8751 0.7559 0.0381 0.057 Uiso 1 1 calc R . . H11C H 0.8246 0.8468 0.0040 0.057 Uiso 1 1 calc R . . C12 C 0.6318(2) 0.84501(18) 0.05226(18) 0.0248(6) Uani 1 1 d . . . H13A H 0.5945 0.8302 -0.0064 0.030 Uiso 1 1 calc R . . H13B H 0.5790 0.8290 0.0845 0.030 Uiso 1 1 calc R . . C1A C 0.6341(2) 0.97840(19) -0.00995(18) 0.0242(6) Uani 1 1 d . . . H1AA H 0.6150 0.9448 -0.0588 0.029 Uiso 1 1 calc R . . C2A C 0.6406(2) 1.06867(18) -0.02190(18) 0.0237(6) Uani 1 1 d . . . C3A C 0.6462(2) 1.12958(19) 0.04005(18) 0.0239(6) Uani 1 1 d . . . C4A C 0.6525(3) 1.2156(2) 0.01926(19) 0.0305(7) Uani 1 1 d . . . H4AA H 0.6581 1.2577 0.0605 0.037 Uiso 1 1 calc R . . C5A C 0.6508(3) 1.2400(2) -0.0594(2) 0.0362(8) Uani 1 1 d . . . H5AA H 0.6560 1.2984 -0.0716 0.043 Uiso 1 1 calc R . . C6A C 0.6414(3) 1.1796(2) -0.1214(2) 0.0380(8) Uani 1 1 d . . . H6AA H 0.6392 1.1965 -0.1759 0.046 Uiso 1 1 calc R . . C7A C 0.6355(3) 1.0954(2) -0.10227(19) 0.0322(7) Uani 1 1 d . . . H7AA H 0.6278 1.0542 -0.1446 0.039 Uiso 1 1 calc R . . C13 C 0.8713(3) 0.9422(2) 0.4293(2) 0.0363(8) Uani 1 1 d . . . C14 C 0.9181(3) 1.0260(2) 0.2969(2) 0.0309(7) Uani 1 1 d . . . C15 C 0.9764(3) 0.8705(2) 0.3401(2) 0.0368(8) Uani 1 1 d . . . O1 O 0.8878(3) 0.9497(2) 0.49907(16) 0.0577(8) Uani 1 1 d . . . O2 O 0.9664(2) 1.08458(16) 0.28639(17) 0.0439(6) Uani 1 1 d . . . O3 O 1.0596(2) 0.83339(19) 0.35703(18) 0.0598(8) Uani 1 1 d . . . C100 C 0.9818(4) 1.0260(3) 0.0717(3) 0.0590(12) Uani 1 1 d . . . H10D H 0.9684 1.0450 0.1215 0.071 Uiso 1 1 calc R . . C101 C 1.0488(4) 0.9543(3) 0.0747(3) 0.0570(12) Uani 1 1 d . . . C102 C 1.1051(7) 0.9022(6) 0.1574(6) 0.058(2) Uani 0.50 1 d P . . H10F H 1.0683 0.9178 0.1996 0.087 Uiso 0.50 1 calc PR . . H10G H 1.1868 0.9153 0.1775 0.087 Uiso 0.50 1 calc PR . . H10H H 1.0950 0.8414 0.1458 0.087 Uiso 0.50 1 calc PR . . C103 C 1.0658(3) 0.9292(3) 0.0000(3) 0.0556(11) Uani 1 1 d . . . H10E H 1.1109 0.8806 -0.0015 0.067 Uiso 1 1 calc R . . C200 C 0.6728(6) 0.8404(4) 0.7900(4) 0.106(2) Uiso 0.75 1 d PD A 1 H20F H 0.5969 0.8462 0.7978 0.159 Uiso 0.75 1 calc PR A 1 H20G H 0.7284 0.8721 0.8334 0.159 Uiso 0.75 1 calc PR A 1 H20H H 0.6944 0.7805 0.7932 0.159 Uiso 0.75 1 calc PR A 1 C201 C 0.6708(4) 0.8728(4) 0.7118(3) 0.0543(14) Uiso 0.75 1 d PD A 1 C202 C 0.5802(5) 0.8504(4) 0.6471(4) 0.0701(18) Uiso 0.75 1 d PD A 1 H20E H 0.5227 0.8137 0.6551 0.084 Uiso 0.75 1 calc PR A 1 C203 C 0.5731(7) 0.8821(5) 0.5691(5) 0.082(2) Uiso 0.75 1 d PD A 1 H20C H 0.5131 0.8629 0.5232 0.098 Uiso 0.75 1 calc PR A 1 C204 C 0.6500(5) 0.9406(4) 0.5555(4) 0.0600(15) Uiso 0.75 1 d PD A 1 H20B H 0.6419 0.9627 0.5017 0.072 Uiso 0.75 1 calc PR A 1 C205 C 0.7379(5) 0.9656(4) 0.6219(3) 0.0625(17) Uiso 0.75 1 d PD A 1 H20A H 0.7903 1.0076 0.6156 0.075 Uiso 0.75 1 calc PR A 1 C206 C 0.7495(6) 0.9285(4) 0.6991(5) 0.0633(16) Uiso 0.75 1 d PD A 1 H20D H 0.8141 0.9425 0.7442 0.076 Uiso 0.75 1 calc PR A 1 C210 C 0.602(2) 0.8714(19) 0.5431(10) 0.121(11) Uiso 0.25 1 d PD B 2 H21A H 0.6658 0.8747 0.5187 0.182 Uiso 0.25 1 calc PR B 2 H21B H 0.5494 0.9184 0.5224 0.182 Uiso 0.25 1 calc PR B 2 H21C H 0.5623 0.8174 0.5278 0.182 Uiso 0.25 1 calc PR B 2 C211 C 0.6451(9) 0.8767(7) 0.6299(7) 0.030(3) Uiso 0.25 1 d PD B 2 C212 C 0.633(2) 0.8416(18) 0.7031(6) 0.151(14) Uiso 0.25 1 d PD B 2 H21D H 0.5731 0.8014 0.6873 0.181 Uiso 0.25 1 calc PR B 2 C213 C 0.6728(6) 0.8404(4) 0.7900(4) 0.106(2) Uiso 0.25 1 d PD B 2 H21E H 0.6546 0.8042 0.8293 0.127 Uiso 0.25 1 calc PR B 2 C214 C 0.7459(13) 0.9083(9) 0.8001(11) 0.061(5) Uiso 0.25 1 d PD B 2 H21F H 0.7756 0.9299 0.8547 0.073 Uiso 0.25 1 calc PR B 2 C215 C 0.7801(19) 0.9476(14) 0.7390(11) 0.075(6) Uiso 0.25 1 d PD B 2 H21G H 0.8375 0.9898 0.7555 0.090 Uiso 0.25 1 calc PR B 2 C216 C 0.7378(15) 0.9308(13) 0.6550(14) 0.075(6) Uiso 0.25 1 d PD B 2 H21H H 0.7711 0.9555 0.6161 0.090 Uiso 0.25 1 calc PR B 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 0.02659(19) 0.01788(19) 0.01899(19) 0.00031(15) 0.00396(15) 0.00120(14) Fe1 0.0316(2) 0.0240(2) 0.0204(2) 0.00086(18) 0.00267(18) -0.00084(18) S1 0.0367(4) 0.0199(3) 0.0227(4) -0.0016(3) 0.0088(3) -0.0009(3) S2 0.0343(4) 0.0187(3) 0.0213(4) -0.0003(3) 0.0046(3) 0.0009(3) N1 0.0266(12) 0.0225(12) 0.0201(12) 0.0001(10) 0.0038(10) 0.0035(10) N2 0.0227(11) 0.0185(12) 0.0213(12) -0.0018(10) 0.0024(10) 0.0019(9) C1 0.0322(16) 0.0194(14) 0.0237(15) 0.0006(12) 0.0021(12) 0.0007(12) C2 0.0353(16) 0.0247(15) 0.0159(13) -0.0004(12) 0.0028(12) -0.0015(12) C3 0.0378(17) 0.0229(15) 0.0177(14) 0.0023(12) 0.0061(13) -0.0015(12) C4 0.0421(18) 0.0311(17) 0.0267(16) -0.0045(14) 0.0120(14) -0.0009(14) C5 0.0378(18) 0.044(2) 0.0334(18) -0.0022(16) 0.0150(15) -0.0069(15) C6 0.044(2) 0.0364(19) 0.0320(18) 0.0044(15) 0.0084(15) -0.0104(15) C7 0.0421(18) 0.0243(16) 0.0256(16) 0.0013(13) 0.0038(14) -0.0022(13) C8 0.0299(15) 0.0276(16) 0.0244(15) 0.0019(13) 0.0051(13) 0.0071(12) C9 0.0334(16) 0.0229(15) 0.0232(15) -0.0016(12) 0.0063(13) 0.0053(12) C10 0.054(2) 0.0238(17) 0.0376(19) 0.0019(15) 0.0028(17) 0.0072(15) C11 0.0425(19) 0.045(2) 0.0255(16) -0.0041(15) 0.0079(15) 0.0135(16) C12 0.0291(15) 0.0184(14) 0.0231(15) -0.0017(12) 0.0015(12) -0.0020(11) C1A 0.0224(14) 0.0256(15) 0.0214(14) -0.0034(12) 0.0013(11) 0.0022(12) C2A 0.0239(14) 0.0244(15) 0.0197(14) 0.0028(12) 0.0016(11) 0.0008(12) C3A 0.0225(14) 0.0242(15) 0.0209(14) 0.0025(12) -0.0005(11) -0.0001(11) C4A 0.0371(17) 0.0242(16) 0.0257(16) -0.0028(13) 0.0021(13) -0.0056(13) C5A 0.047(2) 0.0263(17) 0.0312(18) 0.0089(14) 0.0053(15) -0.0029(14) C6A 0.052(2) 0.0362(19) 0.0234(16) 0.0069(14) 0.0066(15) -0.0018(16) C7A 0.0415(18) 0.0311(17) 0.0207(15) 0.0002(13) 0.0042(14) 0.0019(14) C13 0.044(2) 0.0351(18) 0.0264(17) -0.0015(15) 0.0053(15) -0.0107(15) C14 0.0297(16) 0.0338(18) 0.0270(16) 0.0016(14) 0.0047(13) 0.0027(14) C15 0.0399(19) 0.0354(18) 0.0281(17) 0.0000(15) -0.0010(14) 0.0010(15) O1 0.072(2) 0.074(2) 0.0266(14) -0.0071(13) 0.0131(13) -0.0247(16) O2 0.0383(13) 0.0372(14) 0.0551(16) 0.0110(12) 0.0120(12) -0.0039(11) O3 0.0478(17) 0.0590(19) 0.0598(19) -0.0003(15) -0.0046(14) 0.0185(14) C100 0.050(2) 0.074(3) 0.061(3) -0.026(2) 0.029(2) -0.017(2) C101 0.046(2) 0.066(3) 0.066(3) -0.017(2) 0.027(2) -0.020(2) C102 0.047(5) 0.070(6) 0.063(6) -0.004(5) 0.028(4) -0.008(4) C103 0.041(2) 0.058(3) 0.071(3) -0.018(2) 0.022(2) -0.0130(19) _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 N1 1.925(2) . ? Ni1 N2 1.882(2) . ? Ni1 S1 2.2082(9) . ? Ni1 S2 2.1475(8) . ? Ni1 Fe1 2.8924(6) . ? Fe1 C15 1.774(4) . ? Fe1 C13 1.790(3) . ? Fe1 C14 1.822(3) . ? Fe1 N1 2.009(2) . ? Fe1 C1 2.047(3) . ? Fe1 S1 2.3510(9) . ? S1 C3 1.777(3) . ? S2 C3A 1.748(3) . ? N1 C1 1.399(4) . ? N1 C8 1.474(4) . ? N2 C1A 1.289(4) . ? N2 C12 1.482(3) . ? C1 C2 1.476(4) . ? C2 C7 1.392(4) . ? C2 C3 1.396(4) . ? C3 C4 1.384(5) . ? C4 C5 1.390(5) . ? C5 C6 1.388(5) . ? C6 C7 1.392(5) . ? C8 C9 1.542(4) . ? C9 C12 1.532(4) . ? C9 C10 1.533(4) . ? C9 C11 1.537(4) . ? C1A C2A 1.444(4) . ? C2A C7A 1.404(4) . ? C2A C3A 1.407(4) . ? C3A C4A 1.409(4) . ? C4A C5A 1.376(4) . ? C5A C6A 1.394(5) . ? C6A C7A 1.375(5) . ? C13 O1 1.142(4) . ? C14 O2 1.138(4) . ? C15 O3 1.137(4) . ? C100 C103 1.376(6) 3_775 ? C100 C101 1.390(6) . ? C101 C103 1.393(6) . ? C101 C102 1.593(10) . ? C103 C100 1.376(6) 3_775 ? C200 C201 1.407(8) . ? C201 C202 1.359(6) . ? C201 C206 1.366(6) . ? C202 C203 1.386(6) . ? C203 C204 1.384(6) . ? C204 C205 1.367(6) . ? C205 C206 1.397(6) . ? C210 C211 1.406(13) . ? C211 C216 1.385(8) . ? C211 C212 1.399(8) . ? C214 C215 1.369(8) . ? C215 C216 1.386(8) . ? 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 N2 Ni1 N1 92.47(10) . . ? N2 Ni1 S2 97.28(7) . . ? N1 Ni1 S2 161.73(8) . . ? N2 Ni1 S1 165.74(8) . . ? N1 Ni1 S1 84.92(7) . . ? S2 Ni1 S1 89.20(3) . . ? N2 Ni1 Fe1 131.38(7) . . ? N1 Ni1 Fe1 43.83(7) . . ? S2 Ni1 Fe1 120.23(3) . . ? S1 Ni1 Fe1 52.85(2) . . ? C15 Fe1 C13 89.75(16) . . ? C15 Fe1 C14 92.59(16) . . ? C13 Fe1 C14 101.33(15) . . ? C15 Fe1 N1 99.13(13) . . ? C13 Fe1 N1 147.27(13) . . ? C14 Fe1 N1 109.59(12) . . ? C15 Fe1 C1 93.27(14) . . ? C13 Fe1 C1 108.17(14) . . ? C14 Fe1 C1 149.92(13) . . ? N1 Fe1 C1 40.34(11) . . ? C15 Fe1 S1 175.41(12) . . ? C13 Fe1 S1 89.24(12) . . ? C14 Fe1 S1 92.00(10) . . ? N1 Fe1 S1 79.41(7) . . ? C1 Fe1 S1 82.79(9) . . ? C15 Fe1 Ni1 132.44(11) . . ? C13 Fe1 Ni1 137.71(12) . . ? C14 Fe1 Ni1 82.33(10) . . ? N1 Fe1 Ni1 41.55(7) . . ? C1 Fe1 Ni1 72.04(8) . . ? S1 Fe1 Ni1 48.47(2) . . ? C3 S1 Ni1 98.90(10) . . ? C3 S1 Fe1 96.96(11) . . ? Ni1 S1 Fe1 78.68(3) . . ? C3A S2 Ni1 109.52(10) . . ? C1 N1 C8 117.4(2) . . ? C1 N1 Ni1 127.0(2) . . ? C8 N1 Ni1 114.17(18) . . ? C1 N1 Fe1 71.29(16) . . ? C8 N1 Fe1 118.42(18) . . ? Ni1 N1 Fe1 94.62(10) . . ? C1A N2 C12 116.3(2) . . ? C1A N2 Ni1 131.2(2) . . ? C12 N2 Ni1 111.95(18) . . ? N1 C1 C2 120.7(3) . . ? N1 C1 Fe1 68.38(15) . . ? C2 C1 Fe1 112.2(2) . . ? C7 C2 C3 119.3(3) . . ? C7 C2 C1 122.1(3) . . ? C3 C2 C1 118.6(3) . . ? C4 C3 C2 121.0(3) . . ? C4 C3 S1 122.3(2) . . ? C2 C3 S1 116.6(2) . . ? C3 C4 C5 119.1(3) . . ? C6 C5 C4 120.6(3) . . ? C5 C6 C7 119.9(3) . . ? C2 C7 C6 120.0(3) . . ? N1 C8 C9 112.2(2) . . ? C12 C9 C10 106.9(3) . . ? C12 C9 C11 110.5(3) . . ? C10 C9 C11 110.1(3) . . ? C12 C9 C8 110.0(2) . . ? C10 C9 C8 111.6(3) . . ? C11 C9 C8 107.7(3) . . ? N2 C12 C9 113.2(2) . . ? N2 C1A C2A 127.9(3) . . ? C7A C2A C3A 119.4(3) . . ? C7A C2A C1A 116.3(3) . . ? C3A C2A C1A 124.3(3) . . ? C2A C3A C4A 117.9(3) . . ? C2A C3A S2 125.0(2) . . ? C4A C3A S2 117.0(2) . . ? C5A C4A C3A 121.5(3) . . ? C4A C5A C6A 120.4(3) . . ? C7A C6A C5A 118.9(3) . . ? C6A C7A C2A 121.7(3) . . ? O1 C13 Fe1 178.7(3) . . ? O2 C14 Fe1 176.0(3) . . ? O3 C15 Fe1 176.4(3) . . ? C103 C100 C101 123.0(4) 3_775 . ? C100 C101 C103 116.1(5) . . ? C100 C101 C102 123.6(5) . . ? C103 C101 C102 120.3(5) . . ? C100 C103 C101 120.9(4) 3_775 . ? C202 C201 C206 119.4(6) . . ? C202 C201 C200 116.5(6) . . ? C206 C201 C200 124.0(6) . . ? C201 C202 C203 118.7(7) . . ? C204 C203 C202 122.7(7) . . ? C205 C204 C203 117.9(6) . . ? C204 C205 C206 119.1(7) . . ? C201 C206 C205 122.0(7) . . ? C216 C211 C212 105.1(19) . . ? C216 C211 C210 112.3(19) . . ? C212 C211 C210 142.4(19) . . ? C214 C215 C216 125(2) . . ? C211 C216 C215 117(2) . . ? _diffrn_measured_fraction_theta_max 0.974 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.975 _refine_diff_density_max 0.64 _refine_diff_density_min -0.55 _refine_diff_density_rms 0.08 #===END of CIF data_compound2 #nfe2me _database_code_depnum_ccdc_archive 'CCDC 278857' # Chem Comm ref b509798c # revised CIF for compound 2 - model as before. _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common NiL'(C3)Fe2 _chemical_melting_point ? _chemical_formula_moiety 'C25 H20 Fe2 N2 Ni O6 S2' _chemical_formula_sum 'C25 H20 Fe2 N2 Ni O6 S2' _chemical_formula_weight 678.96 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' Fe Fe 0.3463 0.8444 '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 'C 2/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 18.1561(16) _cell_length_b 9.5235(9) _cell_length_c 15.6850(14) _cell_angle_alpha 90.00 _cell_angle_beta 91.571(2) _cell_angle_gamma 90.00 _cell_volume 2711.1(4) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 2139 _cell_measurement_theta_min 2.4 _cell_measurement_theta_max 27.25 _exptl_crystal_description block _exptl_crystal_colour red _exptl_crystal_size_max 0.17 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.663 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1376 _exptl_absorpt_coefficient_mu 1.940 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.901 _exptl_absorpt_correction_T_max 1.000 _exptl_absorpt_process_details 'Bruker SADABS v2.03' _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker SMART1000 CCD area detector' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count . _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 6675 _diffrn_reflns_av_R_equivalents 0.022 _diffrn_reflns_av_sigmaI/netI 0.0321 _diffrn_reflns_limit_h_min -23 _diffrn_reflns_limit_h_max 20 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 2.24 _diffrn_reflns_theta_max 27.51 _reflns_number_total 3196 _reflns_number_gt 2394 _reflns_threshold_expression >2\s(I) _computing_data_collection 'Bruker SMART version 5.624 (Bruker, 2001)' _computing_cell_refinement 'Bruker SAINT version 6.36a (Bruker, 2002)' _computing_data_reduction 'Bruker SAINT; Bruker SHELXTL (Bruker, 2001)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ' ?' _computing_publication_material 'enCIFer (CCDC, 2003); PLATON (Spek, 2003)' _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^)+(0.0356P)^2^+1.6966P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3020 _refine_ls_number_parameters 173 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0455 _refine_ls_R_factor_gt 0.0315 _refine_ls_wR_factor_ref 0.0745 _refine_ls_wR_factor_gt 0.0689 _refine_ls_goodness_of_fit_ref 1.033 _refine_ls_restrained_S_all 1.033 _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 0.0000 0.23528(4) 0.2500 0.02055(11) Uani 1 2 d S . . S1 S 0.08365(3) 0.38864(6) 0.21282(4) 0.02596(15) Uani 1 1 d . . . N1 N 0.06047(10) 0.09821(19) 0.19857(12) 0.0212(4) Uani 1 1 d . . . Fe1 Fe 0.093087(17) 0.22246(4) 0.10345(2) 0.02414(11) Uani 1 1 d . . . O1 O 0.21517(11) 0.3847(2) 0.03462(14) 0.0544(6) Uani 1 1 d . . . C12 C 0.10557(13) 0.0876(3) 0.02661(16) 0.0289(6) Uani 1 1 d . . . O2 O 0.11594(10) 0.0022(2) -0.02304(12) 0.0390(5) Uani 1 1 d . . . C13 C 0.01057(14) 0.2919(3) 0.04802(17) 0.0335(6) Uani 1 1 d . . . O3 O -0.03911(11) 0.3332(2) 0.01060(14) 0.0542(6) Uani 1 1 d . . . C1 C 0.13749(12) 0.1010(2) 0.19941(14) 0.0240(5) Uani 1 1 d . . . H1A H 0.1621 0.0124 0.1811 0.029 Uiso 1 1 calc R . . C2 C 0.17770(12) 0.1837(3) 0.26567(15) 0.0238(5) Uani 1 1 d . . . C3 C 0.15404(12) 0.3197(3) 0.28243(15) 0.0257(5) Uani 1 1 d . . . C4 C 0.18499(13) 0.3975(3) 0.34900(16) 0.0304(6) Uani 1 1 d . . . H4A H 0.1670 0.4886 0.3615 0.036 Uiso 1 1 calc R . . C5 C 0.24274(14) 0.3398(3) 0.39713(16) 0.0341(6) Uani 1 1 d . . . H5A H 0.2641 0.3918 0.4432 0.041 Uiso 1 1 calc R . . C6 C 0.26951(14) 0.2073(3) 0.37866(16) 0.0340(6) Uani 1 1 d . . . H6A H 0.3102 0.1702 0.4107 0.041 Uiso 1 1 calc R . . C7 C 0.23681(13) 0.1285(3) 0.31317(15) 0.0297(6) Uani 1 1 d . . . H7A H 0.2548 0.0372 0.3009 0.036 Uiso 1 1 calc R . . C8 C 0.02219(13) -0.0336(2) 0.17451(15) 0.0265(5) Uani 1 1 d . . . H8A H 0.0547 -0.0891 0.1377 0.032 Uiso 1 1 calc R . . H8B H -0.0227 -0.0098 0.1403 0.032 Uiso 1 1 calc R . . C9 C 0.0000 -0.1256(3) 0.2500 0.0285(8) Uani 1 2 d S . . C10 C -0.06467(16) -0.2172(3) 0.21860(19) 0.0427(7) Uani 1 1 d . . . H10A H -0.0806 -0.2776 0.2652 0.064 Uiso 1 1 calc R . . H10B H -0.0491 -0.2757 0.1710 0.064 Uiso 1 1 calc R . . H10C H -0.1057 -0.1570 0.1996 0.064 Uiso 1 1 calc R . . C11 C 0.16769(15) 0.3218(3) 0.06084(17) 0.0346(6) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Ni1 0.0194(2) 0.0164(2) 0.0260(2) 0.000 0.00207(16) 0.000 S1 0.0257(3) 0.0190(3) 0.0334(4) -0.0009(3) 0.0039(2) -0.0025(2) N1 0.0234(9) 0.0175(10) 0.0228(10) -0.0011(8) 0.0017(7) 0.0003(7) Fe1 0.02443(18) 0.02380(19) 0.0242(2) -0.00013(15) 0.00115(14) -0.00067(13) O1 0.0572(13) 0.0442(13) 0.0632(15) -0.0061(11) 0.0294(11) -0.0184(10) C12 0.0255(12) 0.0344(15) 0.0267(14) 0.0025(12) -0.0040(10) -0.0004(10) O2 0.0405(10) 0.0441(12) 0.0320(11) -0.0107(9) -0.0065(8) 0.0055(9) C13 0.0337(14) 0.0336(15) 0.0331(15) 0.0001(12) 0.0002(12) -0.0002(11) O3 0.0459(12) 0.0623(15) 0.0535(14) 0.0100(12) -0.0126(11) 0.0146(11) C1 0.0236(11) 0.0255(12) 0.0228(13) -0.0032(10) 0.0011(9) 0.0033(9) C2 0.0207(11) 0.0289(13) 0.0222(12) -0.0015(10) 0.0049(9) -0.0013(9) C3 0.0215(11) 0.0292(13) 0.0265(13) -0.0007(11) 0.0051(10) -0.0073(9) C4 0.0317(13) 0.0319(14) 0.0281(14) -0.0036(11) 0.0095(11) -0.0107(10) C5 0.0371(14) 0.0424(16) 0.0230(14) -0.0030(12) 0.0025(11) -0.0162(12) C6 0.0276(13) 0.0502(17) 0.0241(14) 0.0048(12) -0.0014(10) -0.0083(12) C7 0.0266(12) 0.0374(15) 0.0251(13) -0.0004(11) 0.0033(10) 0.0009(10) C8 0.0308(12) 0.0196(12) 0.0290(14) -0.0042(10) 0.0011(10) -0.0011(9) C9 0.0363(19) 0.0168(17) 0.032(2) 0.000 0.0011(15) 0.000 C10 0.0582(18) 0.0283(15) 0.0420(17) -0.0075(13) 0.0095(14) -0.0171(13) C11 0.0419(15) 0.0298(14) 0.0326(15) -0.0031(12) 0.0090(12) -0.0014(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 N1 1.8997(18) 2 ? Ni1 N1 1.8997(18) . ? Ni1 S1 2.1974(6) . ? Ni1 S1 2.1974(6) 2 ? Ni1 Fe1 2.8928(4) 2 ? Ni1 Fe1 2.8928(4) . ? S1 C3 1.783(2) . ? S1 Fe1 2.3438(7) . ? N1 C1 1.398(3) . ? N1 C8 1.479(3) . ? N1 Fe1 2.0063(19) . ? Fe1 C12 1.780(3) . ? Fe1 C11 1.796(3) . ? Fe1 C13 1.835(3) . ? Fe1 C1 2.046(2) . ? C11 O1 1.136(3) . ? C12 O2 1.145(3) . ? C13 O3 1.133(3) . ? C1 C2 1.481(3) . ? C2 C3 1.392(3) . ? C2 C7 1.393(3) . ? C3 C4 1.386(3) . ? C4 C5 1.388(4) . ? C5 C6 1.386(4) . ? C6 C7 1.392(3) . ? C8 C9 1.536(3) . ? C9 C10 1.533(3) . ? C9 C10 1.533(3) 2 ? C9 C8 1.536(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 N1 Ni1 N1 93.19(11) 2 . ? N1 Ni1 S1 168.86(6) 2 . ? N1 Ni1 S1 86.12(6) . . ? N1 Ni1 S1 86.12(6) 2 2 ? N1 Ni1 S1 168.86(6) . 2 ? S1 Ni1 S1 96.68(3) . 2 ? N1 Ni1 Fe1 43.66(6) 2 2 ? N1 Ni1 Fe1 131.72(6) . 2 ? S1 Ni1 Fe1 131.46(2) . 2 ? S1 Ni1 Fe1 52.704(18) 2 2 ? N1 Ni1 Fe1 131.72(6) 2 . ? N1 Ni1 Fe1 43.66(6) . . ? S1 Ni1 Fe1 52.704(18) . . ? S1 Ni1 Fe1 131.46(2) 2 . ? Fe1 Ni1 Fe1 175.16(2) 2 . ? C3 S1 Ni1 94.69(8) . . ? C3 S1 Fe1 97.71(8) . . ? Ni1 S1 Fe1 79.07(2) . . ? C1 N1 C8 118.77(18) . . ? C1 N1 Ni1 124.92(15) . . ? C8 N1 Ni1 114.74(14) . . ? C1 N1 Fe1 71.36(12) . . ? C8 N1 Fe1 117.20(15) . . ? Ni1 N1 Fe1 95.53(8) . . ? C12 Fe1 C11 90.97(11) . . ? C12 Fe1 C13 93.24(11) . . ? C11 Fe1 C13 104.38(12) . . ? C12 Fe1 N1 97.10(10) . . ? C11 Fe1 N1 145.93(10) . . ? C13 Fe1 N1 108.12(10) . . ? C12 Fe1 C1 92.02(10) . . ? C11 Fe1 C1 106.60(11) . . ? C13 Fe1 C1 148.47(10) . . ? N1 Fe1 C1 40.36(8) . . ? C12 Fe1 S1 174.90(8) . . ? C11 Fe1 S1 89.29(9) . . ? C13 Fe1 S1 91.63(9) . . ? N1 Fe1 S1 79.92(6) . . ? C1 Fe1 S1 83.03(7) . . ? C12 Fe1 Ni1 131.04(8) . . ? C11 Fe1 Ni1 137.42(9) . . ? C13 Fe1 Ni1 82.76(9) . . ? N1 Fe1 Ni1 40.82(5) . . ? C1 Fe1 Ni1 70.51(6) . . ? S1 Fe1 Ni1 48.229(17) . . ? O1 C11 Fe1 179.4(3) . . ? O2 C12 Fe1 177.8(2) . . ? O3 C13 Fe1 177.1(3) . . ? N1 C1 C2 119.37(19) . . ? N1 C1 Fe1 68.28(12) . . ? C2 C1 Fe1 113.10(16) . . ? C3 C2 C7 119.2(2) . . ? C3 C2 C1 118.6(2) . . ? C7 C2 C1 122.2(2) . . ? C4 C3 C2 121.2(2) . . ? C4 C3 S1 122.2(2) . . ? C2 C3 S1 116.52(17) . . ? C3 C4 C5 118.9(2) . . ? C6 C5 C4 120.7(2) . . ? C5 C6 C7 120.0(2) . . ? C6 C7 C2 119.9(2) . . ? N1 C8 C9 114.78(19) . . ? C10 C9 C10 110.6(3) . 2 ? C10 C9 C8 110.96(14) . 2 ? C10 C9 C8 106.97(14) 2 2 ? C10 C9 C8 106.97(14) . . ? C10 C9 C8 110.96(14) 2 . ? C8 C9 C8 110.4(3) 2 . ? _diffrn_measured_fraction_theta_max 0.970 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.970 _refine_diff_density_max 0.392 _refine_diff_density_min -0.276 _refine_diff_density_rms 0.076 #===END of CIF #===END data_NISNBU _database_code_depnum_ccdc_archive 'CCDC 278858' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common NiL _chemical_melting_point ? _chemical_formula_moiety 'C19 H20 N2 Ni S2' _chemical_formula_sum 'C19 H20 N2 Ni S2' _chemical_formula_weight 399.20 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' _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 8.570(2) _cell_length_b 9.057(2) _cell_length_c 11.767(3) _cell_angle_alpha 76.164(3) _cell_angle_beta 87.506(3) _cell_angle_gamma 89.673(3) _cell_volume 886.0(6) _cell_formula_units_Z 2 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 2192 _cell_measurement_theta_min 2.3 _cell_measurement_theta_max 28.4 _exptl_crystal_description plate _exptl_crystal_colour yellow _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.23 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas 0 _exptl_crystal_density_diffrn 1.496 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 416 _exptl_absorpt_coefficient_mu 1.333 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.890 _exptl_absorpt_correction_T_max 1.000 _exptl_absorpt_process_details 'SADABS (Bruker, 2000)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'normal-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker SMART1000 CCD area detector' _diffrn_measurement_method omega _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% none _diffrn_reflns_number 7692 _diffrn_reflns_av_R_equivalents 0.033 _diffrn_reflns_av_sigmaI/netI 0.057 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 1.78 _diffrn_reflns_theta_max 28.46 _reflns_number_total 3955 _reflns_number_gt 2958 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART version 5.624 (Bruker, 2001)' _computing_cell_refinement 'Bruker SAINT version 6.02a (Bruker, 2000)' _computing_data_reduction 'Bruker SAINT; Bruker SHELXTL (Bruker, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'SHELXL-97; PLATON (Spek, 2002)' _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^)+(0.0466P)^2^+0.0576P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary 'Direct Methods' _atom_sites_solution_secondary 'Difference Fourier map' _atom_sites_solution_hydrogens 'Geometrically placed' _refine_ls_hydrogen_treatment 'Riding Model' _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3955 _refine_ls_number_parameters 217 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0649 _refine_ls_R_factor_gt 0.0401 _refine_ls_wR_factor_ref 0.0958 _refine_ls_wR_factor_gt 0.0868 _refine_ls_goodness_of_fit_ref 1.036 _refine_ls_restrained_S_all 1.036 _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 0.45257(4) 0.78796(4) 0.00787(3) 0.01574(12) Uani 1 1 d . . . S1 S 0.41527(9) 0.90677(8) -0.17254(6) 0.02111(17) Uani 1 1 d . . . S2 S 0.20982(8) 0.84474(8) 0.03479(6) 0.02013(17) Uani 1 1 d . . . N1 N 0.6712(3) 0.7581(3) -0.01999(19) 0.0156(5) Uani 1 1 d . . . N2 N 0.4637(3) 0.6617(3) 0.1640(2) 0.0169(5) Uani 1 1 d . . . C1 C 0.5443(3) 0.8332(3) -0.2641(2) 0.0180(6) Uani 1 1 d . . . C2 C 0.6885(3) 0.7648(3) -0.2306(2) 0.0185(6) Uani 1 1 d . . . C3 C 0.7838(3) 0.7106(3) -0.3121(3) 0.0233(7) Uani 1 1 d . . . H3A H 0.8815 0.6660 -0.2888 0.028 Uiso 1 1 calc R . . C4 C 0.7389(4) 0.7207(3) -0.4246(3) 0.0246(7) Uani 1 1 d . . . H4A H 0.8030 0.6806 -0.4779 0.030 Uiso 1 1 calc R . . C5 C 0.5975(4) 0.7909(3) -0.4589(3) 0.0258(7) Uani 1 1 d . . . H5A H 0.5662 0.8010 -0.5368 0.031 Uiso 1 1 calc R . . C6 C 0.5022(4) 0.8460(3) -0.3806(2) 0.0232(7) Uani 1 1 d . . . H6A H 0.4065 0.8935 -0.4059 0.028 Uiso 1 1 calc R . . C7 C 0.7494(3) 0.7514(3) -0.1151(2) 0.0191(6) Uani 1 1 d . . . H7A H 0.8587 0.7359 -0.1089 0.023 Uiso 1 1 calc R . . C8 C 0.7638(3) 0.7470(3) 0.0850(2) 0.0172(6) Uani 1 1 d . . . H8A H 0.7285 0.8255 0.1261 0.021 Uiso 1 1 calc R . . H8B H 0.8753 0.7663 0.0607 0.021 Uiso 1 1 calc R . . C9 C 0.7459(3) 0.5887(3) 0.1691(2) 0.0171(6) Uani 1 1 d . . . C10 C 0.8518(4) 0.4721(3) 0.1284(3) 0.0256(7) Uani 1 1 d . . . H10A H 0.8233 0.4645 0.0502 0.038 Uiso 1 1 calc R . . H10B H 0.8387 0.3726 0.1835 0.038 Uiso 1 1 calc R . . H10C H 0.9610 0.5049 0.1255 0.038 Uiso 1 1 calc R . . C11 C 0.7903(4) 0.6018(4) 0.2915(2) 0.0255(7) Uani 1 1 d . . . H11A H 0.7221 0.6759 0.3172 0.038 Uiso 1 1 calc R . . H11B H 0.8992 0.6353 0.2884 0.038 Uiso 1 1 calc R . . H11C H 0.7778 0.5024 0.3469 0.038 Uiso 1 1 calc R . . C12 C 0.5756(3) 0.5346(3) 0.1717(2) 0.0183(6) Uani 1 1 d . . . H12A H 0.5618 0.4869 0.1053 0.022 Uiso 1 1 calc R . . H12B H 0.5528 0.4566 0.2452 0.022 Uiso 1 1 calc R . . C13 C 0.1761(3) 0.8526(3) 0.1805(2) 0.0176(6) Uani 1 1 d . . . C14 C 0.2625(3) 0.7699(3) 0.2744(2) 0.0209(6) Uani 1 1 d . . . C15 C 0.2186(3) 0.7772(4) 0.3901(3) 0.0263(7) Uani 1 1 d . . . H15A H 0.2757 0.7204 0.4533 0.032 Uiso 1 1 calc R . . C16 C 0.0949(4) 0.8649(4) 0.4132(3) 0.0283(7) Uani 1 1 d . . . H16A H 0.0686 0.8711 0.4912 0.034 Uiso 1 1 calc R . . C17 C 0.0089(3) 0.9443(3) 0.3207(3) 0.0263(7) Uani 1 1 d . . . H17A H -0.0776 1.0036 0.3361 0.032 Uiso 1 1 calc R . . C18 C 0.0475(3) 0.9381(3) 0.2071(3) 0.0212(6) Uani 1 1 d . . . H18A H -0.0137 0.9925 0.1455 0.025 Uiso 1 1 calc R . . C19 C 0.3866(3) 0.6671(3) 0.2591(3) 0.0212(6) Uani 1 1 d . . . H19A H 0.4149 0.5946 0.3277 0.025 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 0.01298(19) 0.0173(2) 0.0170(2) -0.00415(14) -0.00018(14) -0.00049(14) S1 0.0222(4) 0.0217(4) 0.0185(4) -0.0031(3) -0.0006(3) 0.0052(3) S2 0.0151(4) 0.0261(4) 0.0197(4) -0.0064(3) -0.0012(3) 0.0021(3) N1 0.0166(12) 0.0162(12) 0.0148(12) -0.0052(9) 0.0001(9) -0.0007(9) N2 0.0139(11) 0.0160(12) 0.0196(13) -0.0022(10) 0.0006(9) -0.0035(9) C1 0.0217(15) 0.0114(13) 0.0201(15) -0.0033(11) 0.0048(12) -0.0024(11) C2 0.0177(14) 0.0178(14) 0.0186(15) -0.0015(12) 0.0007(11) -0.0049(11) C3 0.0176(15) 0.0291(17) 0.0234(16) -0.0074(13) 0.0034(12) -0.0031(12) C4 0.0265(17) 0.0283(17) 0.0200(16) -0.0083(13) 0.0044(13) -0.0022(13) C5 0.0334(18) 0.0265(17) 0.0172(15) -0.0047(13) -0.0009(13) -0.0048(14) C6 0.0264(16) 0.0205(15) 0.0208(16) -0.0009(12) -0.0026(12) -0.0013(12) C7 0.0145(14) 0.0163(14) 0.0263(16) -0.0046(12) 0.0004(12) -0.0024(11) C8 0.0157(14) 0.0182(14) 0.0183(15) -0.0048(11) -0.0022(11) -0.0025(11) C9 0.0172(14) 0.0167(14) 0.0170(14) -0.0029(11) -0.0018(11) 0.0002(11) C10 0.0221(16) 0.0225(16) 0.0328(18) -0.0084(14) 0.0001(13) 0.0061(12) C11 0.0258(17) 0.0308(17) 0.0193(16) -0.0041(13) -0.0035(13) -0.0040(13) C12 0.0180(14) 0.0156(14) 0.0206(15) -0.0029(12) -0.0021(12) 0.0001(11) C13 0.0135(13) 0.0191(14) 0.0213(15) -0.0068(12) 0.0014(11) -0.0071(11) C14 0.0175(15) 0.0257(16) 0.0202(15) -0.0073(13) 0.0022(12) -0.0036(12) C15 0.0219(16) 0.0352(18) 0.0213(16) -0.0057(14) -0.0008(13) -0.0027(14) C16 0.0236(16) 0.0406(19) 0.0247(17) -0.0173(15) 0.0070(13) -0.0060(14) C17 0.0193(15) 0.0284(17) 0.0348(18) -0.0151(14) 0.0032(13) -0.0004(13) C18 0.0156(14) 0.0205(15) 0.0289(17) -0.0090(13) -0.0010(12) -0.0021(12) C19 0.0187(15) 0.0229(15) 0.0199(15) -0.0010(12) 0.0003(12) -0.0048(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 N1 1.917(2) . y Ni1 N2 1.924(2) . y Ni1 S1 2.1747(9) . y Ni1 S2 2.1681(9) . y S1 C1 1.748(3) . y S2 C13 1.744(3) . ? N1 C7 1.293(3) . y N1 C8 1.481(3) . ? N2 C19 1.286(4) . y N2 C12 1.483(3) . ? C1 C2 1.408(4) . ? C1 C6 1.411(4) . ? C2 C3 1.406(4) . ? C2 C7 1.455(4) . ? C3 C4 1.377(4) . ? C4 C5 1.396(4) . ? C5 C6 1.383(4) . ? C8 C9 1.539(4) . ? C9 C10 1.537(4) . ? C9 C11 1.537(4) . ? C9 C12 1.539(4) . ? C13 C18 1.410(4) . ? C13 C14 1.414(4) . ? C14 C15 1.413(4) . ? C14 C19 1.443(4) . ? C15 C16 1.378(4) . ? C16 C17 1.390(4) . ? C17 C18 1.377(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 N1 Ni1 N2 90.12(9) . . y N1 Ni1 S1 94.09(7) . . y N1 Ni1 S2 174.56(7) . . y N2 Ni1 S1 171.65(7) . . y N2 Ni1 S2 92.97(7) . . y S1 Ni1 S2 83.42(3) . . y Ni1 S1 C1 108.38(10) . . ? Ni1 S2 C13 109.08(9) . . ? C7 N1 C8 116.0(2) . . ? C7 N1 Ni1 130.6(2) . . ? C8 N1 Ni1 113.34(17) . . ? C19 N2 C12 116.4(2) . . ? C19 N2 Ni1 130.6(2) . . ? C12 N2 Ni1 112.99(18) . . ? C2 C1 C6 117.6(3) . . ? C2 C1 S1 124.8(2) . . ? C6 C1 S1 117.6(2) . . ? C3 C2 C1 119.9(3) . . ? C3 C2 C7 116.8(3) . . ? C1 C2 C7 123.2(3) . . ? C4 C3 C2 121.6(3) . . ? C3 C4 C5 118.7(3) . . ? C6 C5 C4 120.7(3) . . ? C5 C6 C1 121.4(3) . . ? N1 C7 C2 127.2(3) . . ? N1 C8 C9 111.0(2) . . ? C10 C9 C11 109.8(2) . . ? C10 C9 C8 111.1(2) . . ? C11 C9 C8 108.1(2) . . ? C10 C9 C12 108.1(2) . . ? C11 C9 C12 110.5(2) . . ? C8 C9 C12 109.2(2) . . ? N2 C12 C9 111.9(2) . . ? C18 C13 C14 118.0(3) . . ? C18 C13 S2 117.8(2) . . ? C14 C13 S2 124.1(2) . . ? C15 C14 C13 119.3(3) . . ? C15 C14 C19 117.6(3) . . ? C13 C14 C19 123.0(3) . . ? C16 C15 C14 121.4(3) . . ? C15 C16 C17 119.1(3) . . ? C18 C17 C16 120.9(3) . . ? C17 C18 C13 121.3(3) . . ? N2 C19 C14 127.9(3) . . ? _diffrn_measured_fraction_theta_max 0.883 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.954 _refine_diff_density_max 0.81 _refine_diff_density_min -0.35 _refine_diff_density_rms 0.09