# Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2002 data_global _journal_coden_Cambridge 182 _publ_requested_journal 'Chemical Communications' loop_ _publ_author_name 'Sun, Wen-Hua' 'Chen, Yong' 'Shao, Chang-Xing' 'Wang, Ruji' 'Xi, Chanjuan' _publ_contact_author_name 'Prof Wen-Hua Sun' _publ_contact_author_address ; Institute of Chemistry Chinese Academy of Sciences Beiyijie No.2, Zhongguancun Haidian Sub. Beijing 100080 CHINA ; _publ_contact_author_email 'WHSUN@INFOC3.ICAS.AC.CN' _publ_section_title ; Self-assembly of Dinuclear M2Cl4(C13H9N3)2: Stepwise Supramolecular Array by p-p Stacking ; data_1 _database_code_CSD 175420 _audit_creation_method SHELXL-97 _chemical_name_common ; Dinuclear 2-(2'-pyridyl)quinoxaline cobalt(II) dichloride ; _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C13 H9 Cl2 Co N3' _chemical_formula_weight 337.07 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' 'Co' 'Co' 0.3494 0.9721 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P21/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 7.861(3) _cell_length_b 15.196(5) _cell_length_c 10.740(4) _cell_angle_alpha 90.00 _cell_angle_beta 91.534(6) _cell_angle_gamma 90.00 _cell_volume 1282.5(7) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.25 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.751 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 680 _exptl_absorpt_coefficient_mu 1.740 _exptl_absorpt_correction_type MULTI-SCAN _exptl_absorpt_correction_T_min 0.6233 _exptl_absorpt_correction_T_max 0.6701 _exptl_absorpt_process_details SADABS _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 5191 _diffrn_reflns_av_R_equivalents 0.0256 _diffrn_reflns_av_sigmaI/netI 0.0348 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 2.32 _diffrn_reflns_theta_max 25.03 _reflns_number_total 2261 _reflns_number_gt 1737 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SHELXTL' _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^)+(0.0300P)^2^+0.8986P] 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 2261 _refine_ls_number_parameters 172 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0443 _refine_ls_R_factor_gt 0.0275 _refine_ls_wR_factor_ref 0.0669 _refine_ls_wR_factor_gt 0.0604 _refine_ls_goodness_of_fit_ref 0.924 _refine_ls_restrained_S_all 0.924 _refine_ls_shift/su_max 0.005 _refine_ls_shift/su_mean 0.001 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 Co1 Co 1.06055(5) 0.01363(2) 0.15992(3) 0.02990(13) Uani 1 1 d . . . Cl1 Cl 1.32560(9) 0.05333(5) 0.23195(7) 0.0395(2) Uani 1 1 d . . . Cl2 Cl 1.14265(11) -0.07492(5) -0.01859(7) 0.0462(2) Uani 1 1 d . . . N1 N 0.9357(3) 0.08679(14) 0.30477(19) 0.0259(5) Uani 1 1 d . . . N2 N 0.7301(3) 0.15958(16) 0.4889(2) 0.0400(6) Uani 1 1 d . . . N3 N 0.9604(3) -0.08450(14) 0.2674(2) 0.0314(5) Uani 1 1 d . . . C1 C 0.9332(3) 0.17591(16) 0.3244(2) 0.0257(6) Uani 1 1 d . . . C2 C 1.0358(4) 0.23269(18) 0.2550(3) 0.0330(7) Uani 1 1 d . . . H2A H 1.1028 0.2102 0.1924 0.040 Uiso 1 1 calc R . . C3 C 1.0366(4) 0.32076(18) 0.2797(3) 0.0358(7) Uani 1 1 d . . . H3A H 1.1055 0.3578 0.2341 0.043 Uiso 1 1 calc R . . C4 C 0.9352(4) 0.35655(19) 0.3729(3) 0.0391(7) Uani 1 1 d . . . H4A H 0.9384 0.4167 0.3889 0.047 Uiso 1 1 calc R . . C5 C 0.8327(4) 0.30351(18) 0.4397(3) 0.0355(7) Uani 1 1 d . . . H5A H 0.7640 0.3278 0.5000 0.043 Uiso 1 1 calc R . . C6 C 0.8297(3) 0.21194(18) 0.4184(2) 0.0301(6) Uani 1 1 d . . . C7 C 0.7392(4) 0.0749(2) 0.4690(3) 0.0402(7) Uani 1 1 d . . . H7A H 0.6741 0.0378 0.5174 0.048 Uiso 1 1 calc R . . C8 C 0.8428(3) 0.03672(17) 0.3779(2) 0.0285(6) Uani 1 1 d . . . C9 C 0.8588(4) -0.05935(17) 0.3610(2) 0.0309(6) Uani 1 1 d . . . C10 C 0.7827(4) -0.12034(19) 0.4373(3) 0.0413(8) Uani 1 1 d . . . H10A H 0.7134 -0.1019 0.5012 0.050 Uiso 1 1 calc R . . C11 C 0.8109(4) -0.2089(2) 0.4176(3) 0.0462(8) Uani 1 1 d . . . H11A H 0.7595 -0.2507 0.4674 0.055 Uiso 1 1 calc R . . C12 C 0.9155(4) -0.2348(2) 0.3237(3) 0.0443(8) Uani 1 1 d . . . H12A H 0.9377 -0.2941 0.3100 0.053 Uiso 1 1 calc R . . C13 C 0.9868(4) -0.17075(18) 0.2503(3) 0.0383(7) Uani 1 1 d . . . H13A H 1.0563 -0.1883 0.1861 0.046 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 Co1 0.0423(2) 0.0274(2) 0.0200(2) -0.00156(15) 0.00143(16) 0.00212(17) Cl1 0.0418(4) 0.0375(4) 0.0394(4) -0.0015(3) 0.0032(3) -0.0013(3) Cl2 0.0654(5) 0.0473(5) 0.0256(4) -0.0098(3) -0.0048(4) 0.0259(4) N1 0.0322(13) 0.0273(12) 0.0182(11) -0.0019(9) 0.0005(10) -0.0014(10) N2 0.0481(16) 0.0425(15) 0.0300(14) -0.0033(11) 0.0125(12) -0.0005(12) N3 0.0408(14) 0.0260(12) 0.0272(13) -0.0035(10) -0.0045(11) -0.0016(10) C1 0.0306(14) 0.0266(14) 0.0197(14) -0.0014(11) -0.0041(11) 0.0016(12) C2 0.0400(17) 0.0321(16) 0.0273(15) -0.0011(12) 0.0083(13) 0.0010(13) C3 0.0424(17) 0.0307(16) 0.0344(17) 0.0030(12) 0.0023(14) -0.0044(13) C4 0.0476(19) 0.0266(16) 0.0427(18) -0.0076(13) -0.0063(16) 0.0024(14) C5 0.0432(18) 0.0364(16) 0.0270(16) -0.0076(13) 0.0008(13) 0.0078(14) C6 0.0333(16) 0.0354(16) 0.0214(14) -0.0030(12) -0.0001(13) 0.0034(12) C7 0.0495(19) 0.0406(18) 0.0311(16) 0.0028(13) 0.0135(15) -0.0049(15) C8 0.0312(15) 0.0331(16) 0.0211(14) 0.0002(11) -0.0034(12) -0.0034(12) C9 0.0395(17) 0.0299(16) 0.0229(14) 0.0015(12) -0.0078(13) -0.0061(13) C10 0.054(2) 0.0418(19) 0.0280(16) 0.0052(13) -0.0007(15) -0.0111(15) C11 0.062(2) 0.0353(18) 0.0400(19) 0.0109(14) -0.0141(17) -0.0154(15) C12 0.058(2) 0.0263(16) 0.047(2) 0.0041(14) -0.0242(17) -0.0052(14) C13 0.0475(18) 0.0302(16) 0.0365(17) -0.0040(13) -0.0102(14) 0.0018(14) _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 Co1 N3 2.055(2) . ? Co1 N1 2.168(2) . ? Co1 Cl1 2.2842(10) . ? Co1 Cl2 2.3651(10) 3_755 ? Co1 Cl2 2.4432(9) . ? Cl2 Co1 2.3651(10) 3_755 ? N1 C8 1.326(3) . ? N1 C1 1.371(3) . ? N2 C7 1.306(4) . ? N2 C6 1.360(3) . ? N3 C13 1.340(3) . ? N3 C9 1.356(3) . ? C1 C2 1.408(4) . ? C1 C6 1.424(3) . ? C2 C3 1.364(4) . ? C3 C4 1.405(4) . ? C4 C5 1.358(4) . ? C5 C6 1.410(4) . ? C7 C8 1.415(4) . ? C8 C9 1.477(4) . ? C9 C10 1.384(4) . ? C10 C11 1.380(4) . ? C11 C12 1.376(4) . ? C12 C13 1.381(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 N3 Co1 N1 77.39(9) . . ? N3 Co1 Cl1 111.17(7) . . ? N1 Co1 Cl1 92.74(6) . . ? N3 Co1 Cl2 112.57(7) . 3_755 ? N1 Co1 Cl2 87.00(6) . 3_755 ? Cl1 Co1 Cl2 135.05(4) . 3_755 ? N3 Co1 Cl2 98.87(7) . . ? N1 Co1 Cl2 168.41(6) . . ? Cl1 Co1 Cl2 98.83(3) . . ? Cl2 Co1 Cl2 84.34(3) 3_755 . ? Co1 Cl2 Co1 95.66(3) 3_755 . ? C8 N1 C1 117.7(2) . . ? C8 N1 Co1 113.42(17) . . ? C1 N1 Co1 128.72(17) . . ? C7 N2 C6 116.8(2) . . ? C13 N3 C9 118.2(2) . . ? C13 N3 Co1 124.8(2) . . ? C9 N3 Co1 117.00(17) . . ? N1 C1 C2 120.9(2) . . ? N1 C1 C6 120.0(2) . . ? C2 C1 C6 119.1(2) . . ? C3 C2 C1 119.8(3) . . ? C2 C3 C4 121.2(3) . . ? C5 C4 C3 120.1(3) . . ? C4 C5 C6 120.5(3) . . ? N2 C6 C5 119.6(2) . . ? N2 C6 C1 121.2(2) . . ? C5 C6 C1 119.1(2) . . ? N2 C7 C8 123.5(3) . . ? N1 C8 C7 120.7(2) . . ? N1 C8 C9 116.4(2) . . ? C7 C8 C9 122.9(2) . . ? N3 C9 C10 121.5(3) . . ? N3 C9 C8 115.1(2) . . ? C10 C9 C8 123.3(3) . . ? C11 C10 C9 119.2(3) . . ? C12 C11 C10 119.6(3) . . ? C11 C12 C13 118.4(3) . . ? N3 C13 C12 123.0(3) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N3 Co1 Cl2 Co1 112.02(7) . . . 3_755 ? N1 Co1 Cl2 Co1 41.8(3) . . . 3_755 ? Cl1 Co1 Cl2 Co1 -134.77(4) . . . 3_755 ? Cl2 Co1 Cl2 Co1 0.0 3_755 . . 3_755 ? N3 Co1 N1 C8 -7.87(17) . . . . ? Cl1 Co1 N1 C8 -118.95(17) . . . . ? Cl2 Co1 N1 C8 106.06(17) 3_755 . . . ? Cl2 Co1 N1 C8 64.4(4) . . . . ? N3 Co1 N1 C1 176.4(2) . . . . ? Cl1 Co1 N1 C1 65.3(2) . . . . ? Cl2 Co1 N1 C1 -69.7(2) 3_755 . . . ? Cl2 Co1 N1 C1 -111.4(3) . . . . ? N1 Co1 N3 C13 -174.7(2) . . . . ? Cl1 Co1 N3 C13 -86.7(2) . . . . ? Cl2 Co1 N3 C13 104.0(2) 3_755 . . . ? Cl2 Co1 N3 C13 16.4(2) . . . . ? N1 Co1 N3 C9 6.13(18) . . . . ? Cl1 Co1 N3 C9 94.18(19) . . . . ? Cl2 Co1 N3 C9 -75.18(19) 3_755 . . . ? Cl2 Co1 N3 C9 -162.70(18) . . . . ? C8 N1 C1 C2 176.5(2) . . . . ? Co1 N1 C1 C2 -7.9(4) . . . . ? C8 N1 C1 C6 -1.6(3) . . . . ? Co1 N1 C1 C6 173.97(18) . . . . ? N1 C1 C2 C3 -177.2(3) . . . . ? C6 C1 C2 C3 0.9(4) . . . . ? C1 C2 C3 C4 -0.6(4) . . . . ? C2 C3 C4 C5 -0.6(4) . . . . ? C3 C4 C5 C6 1.5(4) . . . . ? C7 N2 C6 C5 -176.6(3) . . . . ? C7 N2 C6 C1 2.5(4) . . . . ? C4 C5 C6 N2 178.0(3) . . . . ? C4 C5 C6 C1 -1.1(4) . . . . ? N1 C1 C6 N2 -1.0(4) . . . . ? C2 C1 C6 N2 -179.2(2) . . . . ? N1 C1 C6 C5 178.1(2) . . . . ? C2 C1 C6 C5 -0.1(4) . . . . ? C6 N2 C7 C8 -1.4(4) . . . . ? C1 N1 C8 C7 2.8(4) . . . . ? Co1 N1 C8 C7 -173.5(2) . . . . ? C1 N1 C8 C9 -175.3(2) . . . . ? Co1 N1 C8 C9 8.4(3) . . . . ? N2 C7 C8 N1 -1.3(4) . . . . ? N2 C7 C8 C9 176.7(3) . . . . ? C13 N3 C9 C10 -0.3(4) . . . . ? Co1 N3 C9 C10 178.9(2) . . . . ? C13 N3 C9 C8 177.1(2) . . . . ? Co1 N3 C9 C8 -3.7(3) . . . . ? N1 C8 C9 N3 -3.5(4) . . . . ? C7 C8 C9 N3 178.5(3) . . . . ? N1 C8 C9 C10 173.9(3) . . . . ? C7 C8 C9 C10 -4.1(4) . . . . ? N3 C9 C10 C11 0.0(4) . . . . ? C8 C9 C10 C11 -177.2(3) . . . . ? C9 C10 C11 C12 0.8(5) . . . . ? C10 C11 C12 C13 -1.2(4) . . . . ? C9 N3 C13 C12 -0.1(4) . . . . ? Co1 N3 C13 C12 -179.2(2) . . . . ? C11 C12 C13 N3 0.9(4) . . . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.03 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.487 _refine_diff_density_min -0.299 _refine_diff_density_rms 0.059 data_compound_2 _database_code_CSD 175421 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ; Dinuclear 2-(2'-pyridyl)quinoxaline nickel(II) dichloride ; _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C26 H18 Cl4 N6 Ni2' _chemical_formula_weight 673.68 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 ? _symmetry_space_group_name_H-M ? 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 8.1937(19) _cell_length_b 14.854(4) _cell_length_c 10.577(3) _cell_angle_alpha 90.00 _cell_angle_beta 92.29(2) _cell_angle_gamma 90.00 _cell_volume 1286.4(6) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max ? _exptl_crystal_size_mid ? _exptl_crystal_size_min ? _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.739 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 680 _exptl_absorpt_coefficient_mu 1.909 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _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 ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 2860 _diffrn_reflns_av_R_equivalents 0.0568 _diffrn_reflns_av_sigmaI/netI 0.0705 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 1 _diffrn_reflns_limit_k_min -1 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 2.37 _diffrn_reflns_theta_max 25.02 _reflns_number_total 2216 _reflns_number_gt 1365 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _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^)+(0.0010P)^2^+7.0000P] 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 SHELXL _refine_ls_extinction_coef 0.0004(2) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_number_reflns 2216 _refine_ls_number_parameters 173 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0994 _refine_ls_R_factor_gt 0.0482 _refine_ls_wR_factor_ref 0.1486 _refine_ls_wR_factor_gt 0.1004 _refine_ls_goodness_of_fit_ref 1.059 _refine_ls_restrained_S_all 1.059 _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 1.06125(12) 0.02111(6) 0.15941(9) 0.0484(3) Uani 1 1 d . . . Cl1 Cl 1.3138(2) 0.05542(13) 0.24591(19) 0.0557(5) Uani 1 1 d . . . Cl2 Cl 1.1614(3) -0.05804(14) -0.01791(17) 0.0582(6) Uani 1 1 d . . . N1 N 0.9428(7) 0.0907(4) 0.2963(5) 0.0445(14) Uani 1 1 d . . . N2 N 0.9741(8) -0.0828(4) 0.2588(5) 0.0482(15) Uani 1 1 d . . . N3 N 0.7471(8) 0.1644(5) 0.4832(6) 0.0581(18) Uani 1 1 d . . . C1 C 0.8556(9) 0.0383(5) 0.3694(6) 0.0455(17) Uani 1 1 d . . . C2 C 0.7570(10) 0.0769(5) 0.4636(7) 0.056(2) Uani 1 1 d . . . H2A H 0.6970 0.0386 0.5134 0.067 Uiso 1 1 calc R . . C3 C 0.8420(10) 0.2178(5) 0.4119(7) 0.0502(19) Uani 1 1 d . . . C4 C 0.8441(10) 0.3122(5) 0.4321(7) 0.058(2) Uani 1 1 d . . . H4A H 0.7783 0.3372 0.4925 0.069 Uiso 1 1 calc R . . C5 C 0.9398(10) 0.3659(5) 0.3650(7) 0.058(2) Uani 1 1 d . . . H5A H 0.9418 0.4274 0.3811 0.069 Uiso 1 1 calc R . . C6 C 1.0368(10) 0.3303(5) 0.2709(8) 0.059(2) Uani 1 1 d . . . H6A H 1.1014 0.3687 0.2248 0.071 Uiso 1 1 calc R . . C7 C 1.0381(10) 0.2391(5) 0.2455(7) 0.0520(19) Uani 1 1 d . . . H7A H 1.1022 0.2159 0.1826 0.062 Uiso 1 1 calc R . . C8 C 0.9398(9) 0.1819(5) 0.3171(6) 0.0452(17) Uani 1 1 d . . . C9 C 0.8725(9) -0.0584(5) 0.3511(6) 0.0481(18) Uani 1 1 d . . . C10 C 0.8010(10) -0.1233(5) 0.4266(7) 0.058(2) Uani 1 1 d . . . H10A H 0.7337 -0.1062 0.4912 0.070 Uiso 1 1 calc R . . C11 C 0.8315(11) -0.2132(5) 0.4042(8) 0.063(2) Uani 1 1 d . . . H11A H 0.7834 -0.2575 0.4525 0.075 Uiso 1 1 calc R . . C12 C 0.9336(10) -0.2363(5) 0.3098(8) 0.060(2) Uani 1 1 d . . . H12A H 0.9564 -0.2965 0.2945 0.071 Uiso 1 1 calc R . . C13 C 1.0023(10) -0.1704(5) 0.2379(7) 0.054(2) Uani 1 1 d . . . H13A H 1.0698 -0.1870 0.1732 0.065 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 0.0633(7) 0.0398(5) 0.0430(5) -0.0026(4) 0.0141(4) 0.0014(5) Cl1 0.0606(12) 0.0483(11) 0.0589(11) -0.0011(9) 0.0102(9) -0.0010(9) Cl2 0.0709(13) 0.0576(12) 0.0468(10) -0.0073(9) 0.0109(9) 0.0144(10) N1 0.049(4) 0.043(3) 0.041(3) 0.002(3) 0.007(3) -0.002(3) N2 0.056(4) 0.044(4) 0.044(3) -0.001(3) 0.002(3) 0.004(3) N3 0.070(5) 0.058(4) 0.048(4) -0.003(3) 0.022(3) -0.001(4) C1 0.049(4) 0.046(4) 0.042(4) -0.005(3) 0.007(3) -0.002(3) C2 0.067(5) 0.051(5) 0.051(4) 0.000(4) 0.020(4) -0.006(4) C3 0.064(5) 0.046(4) 0.041(4) -0.004(3) 0.004(4) 0.000(4) C4 0.071(6) 0.049(5) 0.054(5) -0.015(4) 0.012(4) 0.013(4) C5 0.071(6) 0.040(4) 0.063(5) -0.005(4) 0.005(4) 0.006(4) C6 0.065(5) 0.050(5) 0.063(5) -0.001(4) 0.010(4) 0.003(4) C7 0.061(5) 0.051(4) 0.046(4) 0.000(3) 0.017(4) 0.002(4) C8 0.054(5) 0.037(4) 0.044(4) -0.006(3) 0.002(3) 0.004(4) C9 0.062(5) 0.044(4) 0.038(4) -0.001(3) -0.002(3) -0.006(4) C10 0.069(6) 0.053(5) 0.055(5) 0.003(4) 0.010(4) -0.014(4) C11 0.081(6) 0.047(5) 0.059(5) 0.011(4) 0.009(5) -0.006(4) C12 0.069(6) 0.040(4) 0.069(5) -0.003(4) -0.009(5) -0.005(4) C13 0.066(5) 0.046(4) 0.051(4) 0.001(4) 0.009(4) 0.006(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 N2 2.015(6) . ? Ni1 N1 2.054(6) . ? Ni1 Cl1 2.286(2) . ? Ni1 Cl2 2.377(2) 3_755 ? Ni1 Cl2 2.387(2) . ? Cl2 Ni1 2.377(2) 3_755 ? N1 C1 1.326(8) . ? N1 C8 1.373(9) . ? N2 C13 1.342(9) . ? N2 C9 1.356(9) . ? N3 C2 1.319(9) . ? N3 C3 1.360(9) . ? C1 C2 1.427(10) . ? C1 C9 1.458(10) . ? C3 C8 1.413(9) . ? C3 C4 1.419(10) . ? C4 C5 1.341(10) . ? C5 C6 1.402(10) . ? C6 C7 1.381(11) . ? C7 C8 1.411(10) . ? C9 C10 1.396(10) . ? C10 C11 1.381(11) . ? C11 C12 1.372(11) . ? C12 C13 1.373(10) . ? 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 80.2(2) . . ? N2 Ni1 Cl1 107.22(18) . . ? N1 Ni1 Cl1 92.94(18) . . ? N2 Ni1 Cl2 103.08(19) . 3_755 ? N1 Ni1 Cl2 87.44(17) . 3_755 ? Cl1 Ni1 Cl2 149.32(8) . 3_755 ? N2 Ni1 Cl2 99.95(18) . . ? N1 Ni1 Cl2 171.42(18) . . ? Cl1 Ni1 Cl2 95.18(8) . . ? Cl2 Ni1 Cl2 84.16(8) 3_755 . ? Ni1 Cl2 Ni1 95.84(8) 3_755 . ? C1 N1 C8 118.2(6) . . ? C1 N1 Ni1 113.4(5) . . ? C8 N1 Ni1 128.4(5) . . ? C13 N2 C9 119.5(6) . . ? C13 N2 Ni1 126.2(5) . . ? C9 N2 Ni1 114.3(5) . . ? C2 N3 C3 116.5(6) . . ? N1 C1 C2 120.3(7) . . ? N1 C1 C9 116.4(6) . . ? C2 C1 C9 123.3(7) . . ? N3 C2 C1 123.1(7) . . ? N3 C3 C8 121.8(7) . . ? N3 C3 C4 119.8(7) . . ? C8 C3 C4 118.4(7) . . ? C5 C4 C3 120.8(7) . . ? C4 C5 C6 120.7(7) . . ? C7 C6 C5 121.1(8) . . ? C6 C7 C8 118.5(7) . . ? N1 C8 C7 119.6(6) . . ? N1 C8 C3 120.0(7) . . ? C7 C8 C3 120.4(7) . . ? N2 C9 C10 120.8(7) . . ? N2 C9 C1 115.1(6) . . ? C10 C9 C1 124.0(7) . . ? C11 C10 C9 119.1(8) . . ? C12 C11 C10 119.1(7) . . ? C11 C12 C13 120.1(8) . . ? N2 C13 C12 121.5(7) . . ? _diffrn_measured_fraction_theta_max 0.974 _diffrn_reflns_theta_full 25.02 _diffrn_measured_fraction_theta_full 0.974 _refine_diff_density_max 0.791 _refine_diff_density_min -0.699 _refine_diff_density_rms 0.129