# Electronic Supplementary Material (ESI) for Dalton Transactions # This journal is © The Royal Society of Chemistry 2013 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # ####################################################################### data_10019 _database_code_depnum_ccdc_archive 'CCDC 899079' #TrackingRef 'web_deposit_cif_file_0_ChangHoonLee_1355017869.NiCl structures.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C54 H72 Cl4 N4 Ni2' _chemical_formula_weight 1036.38 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' Cl Cl 0.1484 0.1585 '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 12.4363(8) _cell_length_b 13.7770(8) _cell_length_c 16.4633(10) _cell_angle_alpha 90.00 _cell_angle_beta 94.5330(10) _cell_angle_gamma 90.00 _cell_volume 2811.9(3) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 9612 _cell_measurement_theta_min 2.48 _cell_measurement_theta_max 29.58 _exptl_crystal_description block _exptl_crystal_colour purple _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.224 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1096 _exptl_absorpt_coefficient_mu 0.896 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8411 _exptl_absorpt_correction_T_max 0.9157 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(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 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 59460 _diffrn_reflns_av_R_equivalents 0.0260 _diffrn_reflns_av_sigmaI/netI 0.0155 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 1.93 _diffrn_reflns_theta_max 29.13 _reflns_number_total 7557 _reflns_number_gt 6775 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _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^)+(0.0265P)^2^+1.3500P] 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 7557 _refine_ls_number_parameters 297 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0284 _refine_ls_R_factor_gt 0.0242 _refine_ls_wR_factor_ref 0.0631 _refine_ls_wR_factor_gt 0.0605 _refine_ls_goodness_of_fit_ref 1.017 _refine_ls_restrained_S_all 1.017 _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 0.075067(11) 0.002164(9) 0.083004(8) 0.01625(4) Uani 1 1 d . . . Cl2 Cl 0.15901(3) 0.11791(2) 0.155013(18) 0.02731(7) Uani 1 1 d . . . Cl1 Cl -0.10603(2) 0.02888(2) 0.050253(16) 0.02196(6) Uani 1 1 d . . . C1 C 0.09554(8) -0.12066(7) 0.14467(6) 0.01474(19) Uani 1 1 d . . . N2 N 0.17998(7) -0.18322(6) 0.14504(5) 0.01549(17) Uani 1 1 d . . . N1 N 0.03869(7) -0.15225(6) 0.20651(5) 0.01656(17) Uani 1 1 d . . . C12 C -0.06265(9) -0.04714(8) 0.29221(7) 0.0203(2) Uani 1 1 d . . . C11 C -0.06342(9) -0.11342(8) 0.22797(7) 0.0178(2) Uani 1 1 d . . . C22 C 0.35032(9) -0.13157(8) 0.09360(7) 0.0193(2) Uani 1 1 d . . . C21 C 0.25641(9) -0.18736(8) 0.08343(6) 0.0172(2) Uani 1 1 d . . . C16 C -0.15803(9) -0.14634(8) 0.18446(7) 0.0215(2) Uani 1 1 d . . . C26 C 0.23213(10) -0.24968(9) 0.01720(7) 0.0229(2) Uani 1 1 d . . . C13 C -0.16293(11) -0.01596(9) 0.31519(8) 0.0271(3) Uani 1 1 d . . . H13 H -0.1660 0.0281 0.3594 0.032 Uiso 1 1 calc R . . C3 C 0.17653(9) -0.25162(8) 0.20656(7) 0.0205(2) Uani 1 1 d . . . H3 H 0.2269 -0.3024 0.2189 0.025 Uiso 1 1 calc R . . C221 C 0.37391(9) -0.06851(8) 0.16859(7) 0.0213(2) Uani 1 1 d . . . H221 H 0.3032 -0.0462 0.1868 0.026 Uiso 1 1 calc R . . C23 C 0.42246(11) -0.13953(9) 0.03330(8) 0.0283(3) Uani 1 1 d . . . H23 H 0.4873 -0.1027 0.0377 0.034 Uiso 1 1 calc R . . C121 C 0.04134(10) -0.01062(9) 0.33665(7) 0.0235(2) Uani 1 1 d . . . H121 H 0.1010 -0.0211 0.3003 0.028 Uiso 1 1 calc R . . C123 C 0.03616(12) 0.09813(9) 0.35545(8) 0.0308(3) Uani 1 1 d . . . H12A H 0.0152 0.1339 0.3052 0.046 Uiso 1 1 calc R . . H12B H 0.1071 0.1205 0.3780 0.046 Uiso 1 1 calc R . . H12C H -0.0171 0.1096 0.3952 0.046 Uiso 1 1 calc R . . C2 C 0.08797(10) -0.23186(8) 0.24523(7) 0.0213(2) Uani 1 1 d . . . H2 H 0.0637 -0.2659 0.2905 0.026 Uiso 1 1 calc R . . C15 C -0.25537(10) -0.11203(9) 0.20968(8) 0.0273(3) Uani 1 1 d . . . H15 H -0.3213 -0.1327 0.1820 0.033 Uiso 1 1 calc R . . C25 C 0.30747(12) -0.25512(10) -0.04107(8) 0.0307(3) Uani 1 1 d . . . H25 H 0.2944 -0.2968 -0.0868 0.037 Uiso 1 1 calc R . . C161 C -0.15584(10) -0.21621(9) 0.11298(8) 0.0273(3) Uani 1 1 d . . . H161 H -0.0902 -0.2010 0.0839 0.033 Uiso 1 1 calc R . . C24 C 0.40080(12) -0.20050(10) -0.03298(8) 0.0338(3) Uani 1 1 d . . . H24 H 0.4509 -0.2048 -0.0735 0.041 Uiso 1 1 calc R . . C14 C -0.25751(10) -0.04834(10) 0.27447(8) 0.0293(3) Uani 1 1 d . . . H14 H -0.3248 -0.0266 0.2912 0.035 Uiso 1 1 calc R . . C163 C -0.25406(12) -0.20685(12) 0.05123(9) 0.0368(3) Uani 1 1 d . . . H16A H -0.3181 -0.2319 0.0753 0.055 Uiso 1 1 calc R . . H16B H -0.2417 -0.2442 0.0022 0.055 Uiso 1 1 calc R . . H16C H -0.2652 -0.1384 0.0367 0.055 Uiso 1 1 calc R . . C261 C 0.12977(11) -0.31094(10) 0.00937(9) 0.0312(3) Uani 1 1 d . . . H261 H 0.0813 -0.2873 0.0508 0.037 Uiso 1 1 calc R . . C162 C -0.14563(14) -0.32129(10) 0.14319(11) 0.0430(4) Uani 1 1 d . . . H16D H -0.0778 -0.3290 0.1771 0.064 Uiso 1 1 calc R . . H16E H -0.1462 -0.3653 0.0964 0.064 Uiso 1 1 calc R . . H16F H -0.2063 -0.3367 0.1754 0.064 Uiso 1 1 calc R . . C262 C 0.15569(13) -0.41749(11) 0.02786(11) 0.0444(4) Uani 1 1 d . . . H26A H 0.2043 -0.4422 -0.0114 0.067 Uiso 1 1 calc R . . H26B H 0.0888 -0.4554 0.0237 0.067 Uiso 1 1 calc R . . H26C H 0.1906 -0.4232 0.0831 0.067 Uiso 1 1 calc R . . C223 C 0.43076(11) -0.12744(10) 0.23838(8) 0.0297(3) Uani 1 1 d . . . H22A H 0.3844 -0.1815 0.2524 0.045 Uiso 1 1 calc R . . H22B H 0.4452 -0.0855 0.2861 0.045 Uiso 1 1 calc R . . H22C H 0.4990 -0.1530 0.2213 0.045 Uiso 1 1 calc R . . C222 C 0.43998(11) 0.02198(9) 0.15161(9) 0.0318(3) Uani 1 1 d . . . H22D H 0.5119 0.0025 0.1374 0.048 Uiso 1 1 calc R . . H22E H 0.4467 0.0631 0.2003 0.048 Uiso 1 1 calc R . . H22F H 0.4036 0.0583 0.1062 0.048 Uiso 1 1 calc R . . C122 C 0.06748(12) -0.06968(10) 0.41487(8) 0.0344(3) Uani 1 1 d . . . H12D H 0.0060 -0.0672 0.4486 0.052 Uiso 1 1 calc R . . H12E H 0.1313 -0.0423 0.4453 0.052 Uiso 1 1 calc R . . H12F H 0.0818 -0.1373 0.4006 0.052 Uiso 1 1 calc R . . C263 C 0.06888(14) -0.30138(12) -0.07436(11) 0.0479(4) Uani 1 1 d . . . H26D H 0.0540 -0.2327 -0.0860 0.072 Uiso 1 1 calc R . . H26E H 0.0007 -0.3371 -0.0750 0.072 Uiso 1 1 calc R . . H26F H 0.1128 -0.3281 -0.1159 0.072 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 0.01843(8) 0.01432(7) 0.01526(7) 0.00154(5) -0.00335(5) 0.00040(5) Cl2 0.03183(16) 0.02167(13) 0.02669(14) -0.00558(10) -0.00859(11) -0.00208(11) Cl1 0.02033(13) 0.02713(13) 0.01833(12) 0.00339(10) 0.00088(9) 0.00608(10) C1 0.0135(5) 0.0147(4) 0.0156(4) -0.0010(3) -0.0014(4) 0.0000(4) N2 0.0142(4) 0.0149(4) 0.0171(4) 0.0008(3) -0.0010(3) 0.0012(3) N1 0.0160(4) 0.0152(4) 0.0185(4) 0.0022(3) 0.0012(3) 0.0004(3) C12 0.0218(6) 0.0199(5) 0.0196(5) 0.0027(4) 0.0040(4) -0.0004(4) C11 0.0157(5) 0.0174(5) 0.0208(5) 0.0036(4) 0.0049(4) 0.0004(4) C22 0.0170(5) 0.0172(5) 0.0236(5) 0.0023(4) 0.0010(4) 0.0027(4) C21 0.0152(5) 0.0182(5) 0.0181(5) 0.0004(4) 0.0006(4) 0.0043(4) C16 0.0182(5) 0.0214(5) 0.0253(5) 0.0025(4) 0.0036(4) -0.0027(4) C26 0.0212(6) 0.0229(5) 0.0238(5) -0.0040(4) -0.0028(4) 0.0052(4) C13 0.0279(6) 0.0272(6) 0.0273(6) -0.0003(5) 0.0096(5) 0.0030(5) C3 0.0206(5) 0.0169(5) 0.0235(5) 0.0052(4) -0.0021(4) 0.0021(4) C221 0.0167(5) 0.0200(5) 0.0267(5) -0.0011(4) -0.0010(4) -0.0016(4) C23 0.0240(6) 0.0259(6) 0.0363(7) 0.0007(5) 0.0110(5) 0.0005(5) C121 0.0251(6) 0.0247(6) 0.0208(5) -0.0022(4) 0.0022(4) -0.0019(4) C123 0.0385(8) 0.0261(6) 0.0281(6) -0.0043(5) 0.0050(5) -0.0049(5) C2 0.0233(6) 0.0173(5) 0.0232(5) 0.0070(4) 0.0014(4) 0.0010(4) C15 0.0168(6) 0.0304(6) 0.0349(6) 0.0037(5) 0.0042(5) -0.0018(5) C25 0.0374(7) 0.0307(6) 0.0242(6) -0.0064(5) 0.0041(5) 0.0081(5) C161 0.0208(6) 0.0278(6) 0.0331(6) -0.0063(5) 0.0007(5) -0.0060(5) C24 0.0380(8) 0.0340(7) 0.0319(7) -0.0008(5) 0.0182(6) 0.0069(6) C14 0.0206(6) 0.0326(6) 0.0360(7) 0.0041(5) 0.0113(5) 0.0038(5) C163 0.0280(7) 0.0455(8) 0.0360(7) -0.0054(6) -0.0032(6) -0.0104(6) C261 0.0233(6) 0.0323(6) 0.0368(7) -0.0153(5) -0.0050(5) 0.0015(5) C162 0.0427(9) 0.0258(7) 0.0588(10) -0.0087(6) -0.0065(7) -0.0052(6) C262 0.0350(8) 0.0328(7) 0.0635(10) -0.0038(7) -0.0082(7) -0.0077(6) C223 0.0253(6) 0.0313(6) 0.0309(6) 0.0030(5) -0.0075(5) -0.0034(5) C222 0.0279(7) 0.0234(6) 0.0435(8) 0.0003(5) -0.0012(6) -0.0064(5) C122 0.0414(8) 0.0341(7) 0.0262(6) 0.0018(5) -0.0059(5) -0.0038(6) C263 0.0430(9) 0.0431(8) 0.0531(9) -0.0195(7) -0.0242(7) 0.0088(7) _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 1.9794(10) . ? Ni1 Cl2 2.2006(3) . ? Ni1 Cl1 2.2974(3) 3 ? Ni1 Cl1 2.3036(3) . ? Cl1 Ni1 2.2974(3) 3 ? C1 N1 1.3562(13) . ? C1 N2 1.3581(13) . ? N2 C3 1.3864(13) . ? N2 C21 1.4450(14) . ? N1 C2 1.3867(13) . ? N1 C11 1.4472(14) . ? C12 C11 1.3968(15) . ? C12 C13 1.3991(17) . ? C12 C121 1.5203(17) . ? C11 C16 1.4036(16) . ? C22 C23 1.3941(16) . ? C22 C21 1.3971(15) . ? C22 C221 1.5190(16) . ? C21 C26 1.4019(15) . ? C16 C15 1.3931(17) . ? C16 C161 1.5224(17) . ? C26 C25 1.3949(18) . ? C26 C261 1.5243(18) . ? C13 C14 1.3811(19) . ? C3 C2 1.3429(17) . ? C221 C222 1.5310(17) . ? C221 C223 1.5333(17) . ? C23 C24 1.3865(19) . ? C121 C123 1.5323(17) . ? C121 C122 1.5362(17) . ? C15 C14 1.3830(19) . ? C25 C24 1.381(2) . ? C161 C163 1.5315(18) . ? C161 C162 1.533(2) . ? C261 C263 1.525(2) . ? C261 C262 1.528(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 Cl2 107.87(3) . . ? C1 Ni1 Cl1 107.83(3) . 3 ? Cl2 Ni1 Cl1 122.767(13) . 3 ? C1 Ni1 Cl1 109.90(3) . . ? Cl2 Ni1 Cl1 115.067(13) . . ? Cl1 Ni1 Cl1 92.336(11) 3 . ? Ni1 Cl1 Ni1 87.662(11) 3 . ? N1 C1 N2 103.99(9) . . ? N1 C1 Ni1 127.28(8) . . ? N2 C1 Ni1 127.80(8) . . ? C1 N2 C3 111.47(9) . . ? C1 N2 C21 124.97(9) . . ? C3 N2 C21 123.09(9) . . ? C1 N1 C2 111.17(9) . . ? C1 N1 C11 125.74(9) . . ? C2 N1 C11 122.99(9) . . ? C11 C12 C13 116.91(11) . . ? C11 C12 C121 122.37(10) . . ? C13 C12 C121 120.71(11) . . ? C12 C11 C16 123.57(10) . . ? C12 C11 N1 118.22(10) . . ? C16 C11 N1 118.19(10) . . ? C23 C22 C21 116.76(11) . . ? C23 C22 C221 122.00(11) . . ? C21 C22 C221 121.20(10) . . ? C22 C21 C26 123.84(10) . . ? C22 C21 N2 118.96(9) . . ? C26 C21 N2 117.19(10) . . ? C15 C16 C11 116.84(11) . . ? C15 C16 C161 120.93(11) . . ? C11 C16 C161 122.23(10) . . ? C25 C26 C21 116.92(11) . . ? C25 C26 C261 120.93(11) . . ? C21 C26 C261 122.14(11) . . ? C14 C13 C12 120.84(12) . . ? C2 C3 N2 106.40(9) . . ? C22 C221 C222 112.91(10) . . ? C22 C221 C223 110.74(10) . . ? C222 C221 C223 110.22(10) . . ? C24 C23 C22 120.81(12) . . ? C12 C121 C123 111.91(11) . . ? C12 C121 C122 110.10(10) . . ? C123 C121 C122 110.98(10) . . ? C3 C2 N1 106.95(10) . . ? C14 C15 C16 121.02(12) . . ? C24 C25 C26 120.64(12) . . ? C16 C161 C163 113.44(11) . . ? C16 C161 C162 110.64(11) . . ? C163 C161 C162 109.65(11) . . ? C25 C24 C23 121.04(12) . . ? C13 C14 C15 120.78(12) . . ? C26 C261 C263 112.35(13) . . ? C26 C261 C262 110.69(11) . . ? C263 C261 C262 110.18(12) . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 29.13 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.393 _refine_diff_density_min -0.234 _refine_diff_density_rms 0.045 data_10230 _database_code_depnum_ccdc_archive 'CCDC 899080' #TrackingRef 'web_deposit_cif_file_0_ChangHoonLee_1355017869.NiCl structures.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C34 H45 Cl2 N3 Ni' _chemical_formula_weight 625.34 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' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Ni Ni 0.3393 1.1124 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M C2/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 34.143(4) _cell_length_b 15.1633(19) _cell_length_c 12.8525(17) _cell_angle_alpha 90.00 _cell_angle_beta 106.720(2) _cell_angle_gamma 90.00 _cell_volume 6372.7(14) _cell_formula_units_Z 8 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 9415 _cell_measurement_theta_min 2.35 _cell_measurement_theta_max 30.48 _exptl_crystal_description needle _exptl_crystal_colour pink _exptl_crystal_size_max 0.45 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.304 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2656 _exptl_absorpt_coefficient_mu 0.804 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7137 _exptl_absorpt_correction_T_max 0.9239 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(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 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 52647 _diffrn_reflns_av_R_equivalents 0.0696 _diffrn_reflns_av_sigmaI/netI 0.0368 _diffrn_reflns_limit_h_min -41 _diffrn_reflns_limit_h_max 41 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 1.25 _diffrn_reflns_theta_max 25.35 _reflns_number_total 5835 _reflns_number_gt 4649 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _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^)+(0.0292P)^2^+8.8417P] 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 5835 _refine_ls_number_parameters 371 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0480 _refine_ls_R_factor_gt 0.0316 _refine_ls_wR_factor_ref 0.0766 _refine_ls_wR_factor_gt 0.0686 _refine_ls_goodness_of_fit_ref 1.032 _refine_ls_restrained_S_all 1.032 _refine_ls_shift/su_max 0.003 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Ni1 Ni 0.610642(8) 0.354143(18) 0.10578(2) 0.01383(8) Uani 1 1 d . . . Cl1 Cl 0.562369(15) 0.31500(4) 0.17692(4) 0.01928(13) Uani 1 1 d . . . N1 N 0.64715(5) 0.18387(11) 0.07724(14) 0.0139(4) Uani 1 1 d . . . C1 C 0.64098(6) 0.24904(14) 0.14388(16) 0.0135(4) Uani 1 1 d . . . C2 C 0.67627(6) 0.12415(14) 0.13479(17) 0.0160(5) Uani 1 1 d . . . H2 H 0.6858 0.0734 0.1062 0.019 Uiso 1 1 calc R . . C3 C 0.68841(6) 0.15170(14) 0.23852(17) 0.0172(5) Uani 1 1 d . . . H3 H 0.7082 0.1245 0.2971 0.021 Uiso 1 1 calc R . . C4 C 0.58522(6) 0.53161(15) 0.13173(18) 0.0181(5) Uani 1 1 d . . . C5 C 0.56353(7) 0.60959(15) 0.10097(19) 0.0224(5) Uani 1 1 d . . . H5 H 0.5668 0.6570 0.1511 0.027 Uiso 1 1 calc R . . C6 C 0.53714(7) 0.61788(16) -0.0028(2) 0.0249(5) Uani 1 1 d . . . H6 H 0.5223 0.6710 -0.0249 0.030 Uiso 1 1 calc R . . C7 C 0.53272(7) 0.54772(16) -0.07379(19) 0.0235(5) Uani 1 1 d . . . H7 H 0.5147 0.5522 -0.1454 0.028 Uiso 1 1 calc R . . C8 C 0.55464(6) 0.47063(15) -0.04011(17) 0.0179(5) Uani 1 1 d . . . C11 C 0.66661(6) 0.27356(14) 0.34338(16) 0.0153(5) Uani 1 1 d . . . C12 C 0.69309(6) 0.34517(14) 0.37693(17) 0.0162(5) Uani 1 1 d . . . C13 C 0.69046(7) 0.39041(15) 0.46971(17) 0.0201(5) Uani 1 1 d . . . H13 H 0.7076 0.4401 0.4947 0.024 Uiso 1 1 calc R . . C14 C 0.66342(7) 0.36405(15) 0.52548(18) 0.0221(5) Uani 1 1 d . . . H14 H 0.6616 0.3966 0.5871 0.027 Uiso 1 1 calc R . . C15 C 0.63884(7) 0.29028(15) 0.49239(17) 0.0203(5) Uani 1 1 d . . . H15 H 0.6212 0.2716 0.5334 0.024 Uiso 1 1 calc R . . C16 C 0.63966(6) 0.24322(14) 0.39977(17) 0.0169(5) Uani 1 1 d . . . C21 C 0.62573(6) 0.17513(14) -0.03755(16) 0.0151(5) Uani 1 1 d . . . C22 C 0.58431(6) 0.14904(14) -0.06679(18) 0.0172(5) Uani 1 1 d . . . C23 C 0.56476(7) 0.13945(15) -0.17796(18) 0.0213(5) Uani 1 1 d . . . H23 H 0.5367 0.1230 -0.2010 0.026 Uiso 1 1 calc R . . C24 C 0.58525(7) 0.15330(15) -0.25516(18) 0.0234(5) Uani 1 1 d . . . H24 H 0.5712 0.1465 -0.3301 0.028 Uiso 1 1 calc R . . C25 C 0.62593(7) 0.17688(15) -0.22342(17) 0.0204(5) Uani 1 1 d . . . H25 H 0.6397 0.1855 -0.2771 0.025 Uiso 1 1 calc R . . C26 C 0.64739(6) 0.18846(14) -0.11374(17) 0.0167(5) Uani 1 1 d . . . C41 C 0.61367(7) 0.51822(16) 0.24356(18) 0.0246(5) Uani 1 1 d . . . H41A H 0.6005 0.4805 0.2855 0.037 Uiso 1 1 calc R . . H41B H 0.6202 0.5754 0.2799 0.037 Uiso 1 1 calc R . . H41C H 0.6389 0.4900 0.2384 0.037 Uiso 1 1 calc R . . C81 C 0.54976(7) 0.39092(16) -0.11171(18) 0.0237(5) Uani 1 1 d . . . H81A H 0.5768 0.3675 -0.1090 0.036 Uiso 1 1 calc R . . H81B H 0.5352 0.4074 -0.1866 0.036 Uiso 1 1 calc R . . H81C H 0.5341 0.3458 -0.0864 0.036 Uiso 1 1 calc R . . C121 C 0.72558(6) 0.36919(15) 0.32241(18) 0.0191(5) Uani 1 1 d . . . H121 H 0.7176 0.3426 0.2481 0.023 Uiso 1 1 calc R . . C122 C 0.73109(7) 0.46840(16) 0.3107(2) 0.0290(6) Uani 1 1 d . . . H12A H 0.7052 0.4943 0.2676 0.044 Uiso 1 1 calc R . . H12B H 0.7522 0.4788 0.2741 0.044 Uiso 1 1 calc R . . H12C H 0.7394 0.4958 0.3828 0.044 Uiso 1 1 calc R . . C123 C 0.76618(7) 0.32751(19) 0.3874(2) 0.0329(6) Uani 1 1 d . . . H12D H 0.7738 0.3500 0.4620 0.049 Uiso 1 1 calc R . . H12E H 0.7876 0.3426 0.3533 0.049 Uiso 1 1 calc R . . H12F H 0.7631 0.2633 0.3883 0.049 Uiso 1 1 calc R . . C161 C 0.61359(6) 0.16102(15) 0.36515(18) 0.0202(5) Uani 1 1 d . . . H161 H 0.6084 0.1542 0.2849 0.024 Uiso 1 1 calc R . . C162 C 0.63655(7) 0.07824(16) 0.4197(2) 0.0268(6) Uani 1 1 d . . . H16A H 0.6628 0.0740 0.4033 0.040 Uiso 1 1 calc R . . H16B H 0.6201 0.0258 0.3921 0.040 Uiso 1 1 calc R . . H16C H 0.6414 0.0822 0.4985 0.040 Uiso 1 1 calc R . . C163 C 0.57189(7) 0.16656(16) 0.3876(2) 0.0254(5) Uani 1 1 d . . . H16D H 0.5759 0.1672 0.4662 0.038 Uiso 1 1 calc R . . H16E H 0.5553 0.1153 0.3555 0.038 Uiso 1 1 calc R . . H16F H 0.5579 0.2207 0.3553 0.038 Uiso 1 1 calc R . . C221 C 0.56236(7) 0.13063(15) 0.01830(18) 0.0213(5) Uani 1 1 d . . . H221 H 0.5714 0.1766 0.0761 0.026 Uiso 1 1 calc R . . C222 C 0.57390(7) 0.04085(16) 0.0728(2) 0.0260(5) Uani 1 1 d . . . H22A H 0.5647 -0.0060 0.0187 0.039 Uiso 1 1 calc R . . H22B H 0.5607 0.0336 0.1306 0.039 Uiso 1 1 calc R . . H22C H 0.6036 0.0375 0.1038 0.039 Uiso 1 1 calc R . . C223 C 0.51572(7) 0.13721(17) -0.0262(2) 0.0293(6) Uani 1 1 d . . . H22D H 0.5084 0.1929 -0.0656 0.044 Uiso 1 1 calc R . . H22E H 0.5036 0.1351 0.0342 0.044 Uiso 1 1 calc R . . H22F H 0.5054 0.0878 -0.0756 0.044 Uiso 1 1 calc R . . C261 C 0.69276(6) 0.21097(15) -0.08324(17) 0.0188(5) Uani 1 1 d . . . H261 H 0.7017 0.2283 -0.0049 0.023 Uiso 1 1 calc R . . C262 C 0.70190(7) 0.28792(16) -0.14958(19) 0.0240(5) Uani 1 1 d . . . H26A H 0.6930 0.2728 -0.2270 0.036 Uiso 1 1 calc R . . H26B H 0.7314 0.2997 -0.1273 0.036 Uiso 1 1 calc R . . H26C H 0.6872 0.3406 -0.1370 0.036 Uiso 1 1 calc R . . C263 C 0.71720(7) 0.12859(16) -0.09681(19) 0.0236(5) Uani 1 1 d . . . H26D H 0.7130 0.0818 -0.0486 0.035 Uiso 1 1 calc R . . H26E H 0.7463 0.1433 -0.0781 0.035 Uiso 1 1 calc R . . H26F H 0.7078 0.1083 -0.1723 0.035 Uiso 1 1 calc R . . Cl2 Cl 0.659460(15) 0.39967(4) 0.04042(4) 0.01865(13) Uani 1 1 d . . . N2 N 0.66637(5) 0.22768(12) 0.24343(13) 0.0139(4) Uani 1 1 d . . . N3 N 0.58073(5) 0.46355(12) 0.06104(14) 0.0154(4) 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 0.01248(14) 0.01325(15) 0.01584(15) 0.00112(11) 0.00420(11) 0.00209(11) Cl1 0.0169(3) 0.0192(3) 0.0238(3) 0.0031(2) 0.0092(2) 0.0026(2) N1 0.0115(8) 0.0141(9) 0.0170(9) 0.0003(7) 0.0054(7) 0.0000(7) C1 0.0105(10) 0.0144(11) 0.0164(11) -0.0006(9) 0.0052(8) -0.0033(8) C2 0.0141(10) 0.0136(11) 0.0212(11) 0.0006(9) 0.0068(9) 0.0028(8) C3 0.0150(11) 0.0176(12) 0.0192(11) 0.0042(9) 0.0053(9) 0.0046(9) C4 0.0151(11) 0.0191(12) 0.0228(12) 0.0012(10) 0.0097(9) -0.0014(9) C5 0.0210(12) 0.0160(12) 0.0338(13) -0.0009(10) 0.0137(10) 0.0014(10) C6 0.0226(12) 0.0194(13) 0.0369(14) 0.0110(11) 0.0152(11) 0.0071(10) C7 0.0184(12) 0.0297(14) 0.0228(12) 0.0101(11) 0.0064(9) 0.0058(10) C8 0.0125(10) 0.0228(13) 0.0194(11) 0.0025(10) 0.0062(9) -0.0002(9) C11 0.0145(10) 0.0165(12) 0.0139(10) -0.0004(9) 0.0024(8) 0.0053(9) C12 0.0145(10) 0.0154(11) 0.0158(11) 0.0021(9) -0.0005(9) 0.0037(9) C13 0.0208(12) 0.0178(12) 0.0197(11) -0.0021(9) 0.0026(9) 0.0015(9) C14 0.0265(12) 0.0223(13) 0.0179(11) -0.0028(10) 0.0069(10) 0.0065(10) C15 0.0192(11) 0.0249(13) 0.0182(11) 0.0038(10) 0.0078(9) 0.0036(10) C16 0.0157(11) 0.0178(12) 0.0159(11) 0.0028(9) 0.0026(9) 0.0054(9) C21 0.0153(10) 0.0130(11) 0.0155(11) -0.0025(9) 0.0021(9) 0.0019(9) C22 0.0166(11) 0.0113(11) 0.0232(12) -0.0015(9) 0.0049(9) 0.0021(9) C23 0.0154(11) 0.0196(13) 0.0250(12) -0.0044(10) -0.0003(9) -0.0022(9) C24 0.0243(12) 0.0257(13) 0.0165(11) -0.0038(10) 0.0000(10) 0.0001(10) C25 0.0229(12) 0.0231(13) 0.0161(11) 0.0006(9) 0.0069(9) 0.0014(10) C26 0.0177(11) 0.0137(11) 0.0180(11) -0.0005(9) 0.0040(9) 0.0018(9) C41 0.0240(12) 0.0227(13) 0.0262(13) -0.0045(10) 0.0055(10) 0.0012(10) C81 0.0221(12) 0.0280(14) 0.0196(12) 0.0002(10) 0.0036(10) 0.0020(10) C121 0.0166(11) 0.0215(13) 0.0187(11) -0.0018(9) 0.0041(9) 0.0002(9) C122 0.0254(13) 0.0221(14) 0.0439(15) -0.0044(12) 0.0169(12) -0.0043(11) C123 0.0219(13) 0.0473(18) 0.0309(14) 0.0096(12) 0.0102(11) 0.0088(12) C161 0.0189(11) 0.0212(13) 0.0216(11) 0.0024(10) 0.0077(9) -0.0006(10) C162 0.0261(13) 0.0218(13) 0.0344(14) 0.0028(11) 0.0119(11) -0.0006(10) C163 0.0205(12) 0.0266(14) 0.0308(13) 0.0040(11) 0.0104(10) -0.0010(10) C221 0.0177(11) 0.0223(13) 0.0250(12) -0.0054(10) 0.0076(10) -0.0038(9) C222 0.0241(13) 0.0254(14) 0.0310(13) 0.0002(11) 0.0120(11) -0.0040(10) C223 0.0191(12) 0.0312(15) 0.0394(15) -0.0036(12) 0.0113(11) -0.0027(10) C261 0.0161(11) 0.0248(13) 0.0164(11) -0.0003(10) 0.0065(9) -0.0006(9) C262 0.0200(12) 0.0282(14) 0.0251(12) -0.0013(11) 0.0090(10) -0.0029(10) C263 0.0206(12) 0.0281(14) 0.0231(12) 0.0015(10) 0.0081(10) 0.0036(10) Cl2 0.0173(3) 0.0172(3) 0.0233(3) 0.0026(2) 0.0088(2) 0.0008(2) N2 0.0131(9) 0.0138(9) 0.0150(9) 0.0000(7) 0.0042(7) 0.0005(7) N3 0.0135(9) 0.0172(10) 0.0168(9) 0.0016(8) 0.0066(7) 0.0013(7) _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 1.887(2) . ? Ni1 N3 1.9461(18) . ? Ni1 Cl2 2.1832(6) . ? Ni1 Cl1 2.1845(6) . ? N1 C1 1.363(3) . ? N1 C2 1.390(3) . ? N1 C21 1.452(3) . ? C1 N2 1.362(3) . ? C2 C3 1.344(3) . ? C3 N2 1.387(3) . ? C4 N3 1.354(3) . ? C4 C5 1.391(3) . ? C4 C41 1.499(3) . ? C5 C6 1.384(3) . ? C6 C7 1.381(3) . ? C7 C8 1.388(3) . ? C8 N3 1.352(3) . ? C8 C81 1.499(3) . ? C11 C12 1.399(3) . ? C11 C16 1.403(3) . ? C11 N2 1.459(3) . ? C12 C13 1.401(3) . ? C12 C121 1.517(3) . ? C13 C14 1.381(3) . ? C14 C15 1.390(3) . ? C15 C16 1.395(3) . ? C16 C161 1.522(3) . ? C21 C26 1.401(3) . ? C21 C22 1.411(3) . ? C22 C23 1.400(3) . ? C22 C221 1.519(3) . ? C23 C24 1.385(3) . ? C24 C25 1.378(3) . ? C25 C26 1.400(3) . ? C26 C261 1.523(3) . ? C121 C122 1.529(3) . ? C121 C123 1.534(3) . ? C161 C163 1.534(3) . ? C161 C162 1.538(3) . ? C221 C222 1.530(3) . ? C221 C223 1.533(3) . ? C261 C262 1.529(3) . ? C261 C263 1.540(3) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 Ni1 N3 177.17(8) . . ? C1 Ni1 Cl2 86.80(6) . . ? N3 Ni1 Cl2 90.60(5) . . ? C1 Ni1 Cl1 94.92(6) . . ? N3 Ni1 Cl1 87.73(5) . . ? Cl2 Ni1 Cl1 176.84(3) . . ? C1 N1 C2 110.74(17) . . ? C1 N1 C21 125.50(17) . . ? C2 N1 C21 123.73(17) . . ? N2 C1 N1 104.25(17) . . ? N2 C1 Ni1 126.73(15) . . ? N1 C1 Ni1 128.45(15) . . ? C3 C2 N1 107.13(19) . . ? C2 C3 N2 106.67(18) . . ? N3 C4 C5 120.6(2) . . ? N3 C4 C41 117.20(19) . . ? C5 C4 C41 122.2(2) . . ? C6 C5 C4 119.8(2) . . ? C7 C6 C5 118.9(2) . . ? C6 C7 C8 119.7(2) . . ? N3 C8 C7 120.9(2) . . ? N3 C8 C81 116.89(19) . . ? C7 C8 C81 122.2(2) . . ? C12 C11 C16 123.84(19) . . ? C12 C11 N2 118.75(18) . . ? C16 C11 N2 117.40(19) . . ? C11 C12 C13 116.6(2) . . ? C11 C12 C121 122.50(19) . . ? C13 C12 C121 120.68(19) . . ? C14 C13 C12 121.1(2) . . ? C13 C14 C15 120.6(2) . . ? C14 C15 C16 120.9(2) . . ? C15 C16 C11 116.8(2) . . ? C15 C16 C161 121.0(2) . . ? C11 C16 C161 122.21(19) . . ? C26 C21 C22 122.98(19) . . ? C26 C21 N1 118.94(18) . . ? C22 C21 N1 117.99(18) . . ? C23 C22 C21 116.6(2) . . ? C23 C22 C221 121.79(19) . . ? C21 C22 C221 121.60(19) . . ? C24 C23 C22 121.7(2) . . ? C25 C24 C23 120.1(2) . . ? C24 C25 C26 121.4(2) . . ? C25 C26 C21 117.19(19) . . ? C25 C26 C261 119.08(19) . . ? C21 C26 C261 123.69(18) . . ? C12 C121 C122 114.14(19) . . ? C12 C121 C123 108.43(18) . . ? C122 C121 C123 110.0(2) . . ? C16 C161 C163 113.37(19) . . ? C16 C161 C162 110.89(18) . . ? C163 C161 C162 109.76(19) . . ? C22 C221 C222 112.17(19) . . ? C22 C221 C223 113.22(19) . . ? C222 C221 C223 109.39(19) . . ? C26 C261 C262 112.53(18) . . ? C26 C261 C263 109.46(18) . . ? C262 C261 C263 110.58(18) . . ? C1 N2 C3 111.21(17) . . ? C1 N2 C11 123.69(17) . . ? C3 N2 C11 124.76(17) . . ? C8 N3 C4 120.03(18) . . ? C8 N3 Ni1 119.76(15) . . ? C4 N3 Ni1 120.19(14) . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 25.35 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.347 _refine_diff_density_min -0.279 _refine_diff_density_rms 0.059