# Electronic Supplementary Material (ESI) for CrystEngComm # 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_compound7 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C28 H20 N6 Ni ' _chemical_formula_sum 'C28 H20 N6 Ni' _chemical_formula_weight 499.21 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' 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 16.8518(3) _cell_length_b 9.3426(2) _cell_length_c 16.0838(3) _cell_angle_alpha 90.00 _cell_angle_beta 116.5070(10) _cell_angle_gamma 90.00 _cell_volume 2266.04(8) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 7233 _cell_measurement_theta_min 2.56 _cell_measurement_theta_max 29.96 _exptl_crystal_description plate _exptl_crystal_colour orange _exptl_crystal_size_max 0.18 _exptl_crystal_size_mid 0.11 _exptl_crystal_size_min 0.07 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.463 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1032 _exptl_absorpt_coefficient_mu 0.886 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8567 _exptl_absorpt_correction_T_max 0.9405 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(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_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 13713 _diffrn_reflns_av_R_equivalents 0.0196 _diffrn_reflns_av_sigmaI/netI 0.0165 _diffrn_reflns_limit_h_min -23 _diffrn_reflns_limit_h_max 21 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 2.56 _diffrn_reflns_theta_max 29.96 _reflns_number_total 3194 _reflns_number_gt 2909 _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^)+(0.0390P)^2^+2.3907P] 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 riding _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3194 _refine_ls_number_parameters 159 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0330 _refine_ls_R_factor_gt 0.0295 _refine_ls_wR_factor_ref 0.0804 _refine_ls_wR_factor_gt 0.0781 _refine_ls_goodness_of_fit_ref 1.057 _refine_ls_restrained_S_all 1.057 _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 C1 C 0.85027(10) 0.57608(15) 0.06202(10) 0.0257(3) Uani 1 1 d . . . H1 H 0.8881 0.6322 0.0477 0.031 Uiso 1 1 calc R . . C2 C 0.75835(10) 0.56237(16) 0.00389(10) 0.0278(3) Uani 1 1 d . . . H2 H 0.7259 0.6061 -0.0534 0.033 Uiso 1 1 calc R . . C3 C 0.72654(10) 0.47142(15) 0.04906(10) 0.0240(3) Uani 1 1 d . . . H3 H 0.6681 0.4413 0.0282 0.029 Uiso 1 1 calc R . . C4 C 0.80006(9) 0.43198(14) 0.13403(9) 0.0203(2) Uani 1 1 d . . . C5 C 0.79823(9) 0.34441(14) 0.20382(9) 0.0209(2) Uani 1 1 d . . . C6 C 0.87014(9) 0.30122(14) 0.28601(9) 0.0225(3) Uani 1 1 d . . . C7 C 0.86826(11) 0.20566(16) 0.35487(11) 0.0309(3) Uani 1 1 d . . . H7 H 0.8183 0.1638 0.3551 0.037 Uiso 1 1 calc R . . C8 C 0.95422(11) 0.18788(18) 0.42022(11) 0.0350(3) Uani 1 1 d . . . H8 H 0.9743 0.1316 0.4734 0.042 Uiso 1 1 calc R . . C9 C 1.00641(10) 0.27257(16) 0.39036(11) 0.0286(3) Uani 1 1 d . . . H9 H 1.0678 0.2794 0.4222 0.034 Uiso 1 1 calc R . . C10 C 0.71028(9) 0.28963(14) 0.19158(9) 0.0220(3) Uani 1 1 d . . . C11 C 0.67391(10) 0.34157(15) 0.24807(10) 0.0270(3) Uani 1 1 d . . . H11 H 0.6989 0.4203 0.2862 0.032 Uiso 1 1 calc R . . C12 C 0.60022(10) 0.27490(16) 0.24694(11) 0.0278(3) Uani 1 1 d . . . H12 H 0.5778 0.3095 0.2864 0.033 Uiso 1 1 calc R . . C13 C 0.59090(9) 0.12164(15) 0.13259(10) 0.0252(3) Uani 1 1 d . . . H13 H 0.5611 0.0493 0.0904 0.030 Uiso 1 1 calc R . . C14 C 0.66558(9) 0.18034(15) 0.13028(10) 0.0243(3) Uani 1 1 d . . . H14 H 0.6853 0.1468 0.0883 0.029 Uiso 1 1 calc R . . N1 N 0.87641(8) 0.49951(11) 0.13940(8) 0.0212(2) Uani 1 1 d . . . N2 N 0.95721(8) 0.34120(12) 0.31147(8) 0.0221(2) Uani 1 1 d . . . N3 N 0.55898(8) 0.16284(13) 0.19207(8) 0.0251(2) Uani 1 1 d . . . Ni1 Ni 1.0000 0.49324(2) 0.2500 0.01743(8) Uani 1 2 d S . . 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 C1 0.0250(7) 0.0288(6) 0.0261(7) 0.0042(5) 0.0137(6) -0.0001(5) C2 0.0273(8) 0.0321(7) 0.0218(6) 0.0038(5) 0.0090(6) 0.0029(6) C3 0.0183(7) 0.0295(6) 0.0221(6) -0.0016(5) 0.0072(6) 0.0004(5) C4 0.0161(6) 0.0239(6) 0.0214(6) -0.0007(4) 0.0088(5) -0.0003(4) C5 0.0172(6) 0.0240(6) 0.0240(6) -0.0020(5) 0.0114(5) -0.0028(4) C6 0.0197(7) 0.0252(6) 0.0239(6) 0.0020(5) 0.0110(5) -0.0026(5) C7 0.0297(8) 0.0333(7) 0.0311(7) 0.0077(6) 0.0148(7) -0.0053(6) C8 0.0334(9) 0.0354(8) 0.0321(8) 0.0136(6) 0.0110(7) -0.0010(6) C9 0.0220(7) 0.0309(7) 0.0289(7) 0.0072(5) 0.0077(6) 0.0017(5) C10 0.0175(6) 0.0265(6) 0.0234(6) 0.0006(5) 0.0102(5) -0.0028(5) C11 0.0250(7) 0.0291(6) 0.0312(7) -0.0070(5) 0.0164(6) -0.0067(5) C12 0.0237(7) 0.0316(7) 0.0334(7) -0.0045(6) 0.0175(6) -0.0034(5) C13 0.0213(7) 0.0302(6) 0.0234(6) -0.0023(5) 0.0094(6) -0.0070(5) C14 0.0214(7) 0.0296(6) 0.0237(6) -0.0018(5) 0.0117(6) -0.0035(5) N1 0.0167(6) 0.0245(5) 0.0235(5) 0.0017(4) 0.0100(5) -0.0002(4) N2 0.0171(5) 0.0245(5) 0.0243(5) 0.0029(4) 0.0089(5) 0.0001(4) N3 0.0207(6) 0.0291(6) 0.0265(6) -0.0020(5) 0.0115(5) -0.0051(4) Ni1 0.01212(13) 0.02116(12) 0.01988(12) 0.000 0.00792(10) 0.000 _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 C1 N1 1.3287(17) . ? C1 C2 1.413(2) . ? C1 H1 0.9300 . ? C2 C3 1.373(2) . ? C2 H2 0.9300 . ? C3 C4 1.424(2) . ? C3 H3 0.9300 . ? C4 C5 1.4003(18) . ? C4 N1 1.4006(16) . ? C5 C6 1.3961(19) . ? C5 C10 1.4956(18) . ? C6 N2 1.3871(17) . ? C6 C7 1.4338(18) . ? C7 C8 1.368(2) . ? C7 H7 0.9300 . ? C8 C9 1.417(2) . ? C8 H8 0.9300 . ? C9 N2 1.3302(18) . ? C9 H9 0.9300 . ? C10 C14 1.3854(19) . ? C10 C11 1.3907(18) . ? C11 C12 1.3819(19) . ? C11 H11 0.9300 . ? C12 N3 1.3456(18) . ? C12 H12 0.9300 . ? C13 N3 1.3462(18) . ? C13 C14 1.3884(18) . ? C13 H13 0.9300 . ? C14 H14 0.9300 . ? N1 Ni1 2.0490(12) . ? N2 Ni1 2.0374(11) . ? N3 Ni1 2.2789(12) 3_445 ? Ni1 N2 2.0374(11) 2_755 ? Ni1 N1 2.0490(12) 2_755 ? Ni1 N3 2.2789(12) 4_655 ? Ni1 N3 2.2789(12) 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 N1 C1 C2 112.21(12) . . ? N1 C1 H1 123.9 . . ? C2 C1 H1 123.9 . . ? C3 C2 C1 106.12(13) . . ? C3 C2 H2 126.9 . . ? C1 C2 H2 126.9 . . ? C2 C3 C4 106.86(13) . . ? C2 C3 H3 126.6 . . ? C4 C3 H3 126.6 . . ? C5 C4 N1 124.19(12) . . ? C5 C4 C3 126.84(12) . . ? N1 C4 C3 108.94(11) . . ? C6 C5 C4 127.41(12) . . ? C6 C5 C10 114.59(11) . . ? C4 C5 C10 118.00(12) . . ? N2 C6 C5 123.95(12) . . ? N2 C6 C7 108.95(12) . . ? C5 C6 C7 127.04(13) . . ? C8 C7 C6 106.75(13) . . ? C8 C7 H7 126.6 . . ? C6 C7 H7 126.6 . . ? C7 C8 C9 106.04(13) . . ? C7 C8 H8 127.0 . . ? C9 C8 H8 127.0 . . ? N2 C9 C8 112.06(14) . . ? N2 C9 H9 124.0 . . ? C8 C9 H9 124.0 . . ? C14 C10 C11 117.64(12) . . ? C14 C10 C5 122.55(12) . . ? C11 C10 C5 119.64(12) . . ? C12 C11 C10 119.31(13) . . ? C12 C11 H11 120.3 . . ? C10 C11 H11 120.3 . . ? N3 C12 C11 123.88(13) . . ? N3 C12 H12 118.1 . . ? C11 C12 H12 118.1 . . ? N3 C13 C14 124.09(13) . . ? N3 C13 H13 118.0 . . ? C14 C13 H13 118.0 . . ? C10 C14 C13 118.92(13) . . ? C10 C14 H14 120.5 . . ? C13 C14 H14 120.5 . . ? C1 N1 C4 105.87(12) . . ? C1 N1 Ni1 127.75(10) . . ? C4 N1 Ni1 126.19(9) . . ? C9 N2 C6 106.18(11) . . ? C9 N2 Ni1 126.44(10) . . ? C6 N2 Ni1 126.97(9) . . ? C12 N3 C13 115.81(12) . . ? C12 N3 Ni1 117.69(9) . 3_445 ? C13 N3 Ni1 118.51(9) . 3_445 ? N2 Ni1 N2 91.60(7) . 2_755 ? N2 Ni1 N1 89.91(5) . . ? N2 Ni1 N1 92.37(5) 2_755 . ? N2 Ni1 N1 92.37(5) . 2_755 ? N2 Ni1 N1 89.91(5) 2_755 2_755 ? N1 Ni1 N1 176.72(6) . 2_755 ? N2 Ni1 N3 88.45(5) . 4_655 ? N2 Ni1 N3 175.21(4) 2_755 4_655 ? N1 Ni1 N3 82.84(4) . 4_655 ? N1 Ni1 N3 94.87(4) 2_755 4_655 ? N2 Ni1 N3 175.21(4) . 3 ? N2 Ni1 N3 88.45(5) 2_755 3 ? N1 Ni1 N3 94.87(4) . 3 ? N1 Ni1 N3 82.84(4) 2_755 3 ? N3 Ni1 N3 91.90(6) 4_655 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 N1 C1 C2 C3 0.04(17) . . . . ? C1 C2 C3 C4 0.13(16) . . . . ? C2 C3 C4 C5 177.67(13) . . . . ? C2 C3 C4 N1 -0.25(15) . . . . ? N1 C4 C5 C6 -4.6(2) . . . . ? C3 C4 C5 C6 177.77(13) . . . . ? N1 C4 C5 C10 174.96(12) . . . . ? C3 C4 C5 C10 -2.7(2) . . . . ? C4 C5 C6 N2 0.3(2) . . . . ? C10 C5 C6 N2 -179.24(12) . . . . ? C4 C5 C6 C7 -176.56(14) . . . . ? C10 C5 C6 C7 3.9(2) . . . . ? N2 C6 C7 C8 -0.76(18) . . . . ? C5 C6 C7 C8 176.53(15) . . . . ? C6 C7 C8 C9 0.17(19) . . . . ? C7 C8 C9 N2 0.5(2) . . . . ? C6 C5 C10 C14 -105.39(15) . . . . ? C4 C5 C10 C14 74.98(18) . . . . ? C6 C5 C10 C11 69.70(17) . . . . ? C4 C5 C10 C11 -109.92(15) . . . . ? C14 C10 C11 C12 5.7(2) . . . . ? C5 C10 C11 C12 -169.68(14) . . . . ? C10 C11 C12 N3 -1.7(2) . . . . ? C11 C10 C14 C13 -4.4(2) . . . . ? C5 C10 C14 C13 170.78(13) . . . . ? N3 C13 C14 C10 -0.9(2) . . . . ? C2 C1 N1 C4 -0.19(16) . . . . ? C2 C1 N1 Ni1 -175.30(10) . . . . ? C5 C4 N1 C1 -177.72(13) . . . . ? C3 C4 N1 C1 0.27(15) . . . . ? C5 C4 N1 Ni1 -2.51(18) . . . . ? C3 C4 N1 Ni1 175.47(9) . . . . ? C8 C9 N2 C6 -0.96(18) . . . . ? C8 C9 N2 Ni1 172.04(11) . . . . ? C5 C6 N2 C9 -176.34(13) . . . . ? C7 C6 N2 C9 1.05(16) . . . . ? C5 C6 N2 Ni1 10.70(19) . . . . ? C7 C6 N2 Ni1 -171.91(10) . . . . ? C11 C12 N3 C13 -3.5(2) . . . . ? C11 C12 N3 Ni1 145.00(13) . . . 3_445 ? C14 C13 N3 C12 4.8(2) . . . . ? C14 C13 N3 Ni1 -143.37(12) . . . 3_445 ? C9 N2 Ni1 N2 83.24(12) . . . 2_755 ? C6 N2 Ni1 N2 -105.17(12) . . . 2_755 ? C9 N2 Ni1 N1 175.61(13) . . . . ? C6 N2 Ni1 N1 -12.81(11) . . . . ? C9 N2 Ni1 N1 -6.74(13) . . . 2_755 ? C6 N2 Ni1 N1 164.85(11) . . . 2_755 ? C9 N2 Ni1 N3 -101.55(13) . . . 4_655 ? C6 N2 Ni1 N3 70.03(11) . . . 4_655 ? C9 N2 Ni1 N3 -7.3(6) . . . 3 ? C6 N2 Ni1 N3 164.3(5) . . . 3 ? C1 N1 Ni1 N2 -177.00(12) . . . . ? C4 N1 Ni1 N2 8.83(11) . . . . ? C1 N1 Ni1 N2 -85.40(12) . . . 2_755 ? C4 N1 Ni1 N2 100.43(11) . . . 2_755 ? C1 N1 Ni1 N1 48.77(12) . . . 2_755 ? C4 N1 Ni1 N1 -125.40(10) . . . 2_755 ? C1 N1 Ni1 N3 94.55(12) . . . 4_655 ? C4 N1 Ni1 N3 -79.62(11) . . . 4_655 ? C1 N1 Ni1 N3 3.24(12) . . . 3 ? C4 N1 Ni1 N3 -170.92(10) . . . 3 ? _diffrn_measured_fraction_theta_max 0.965 _diffrn_reflns_theta_full 29.96 _diffrn_measured_fraction_theta_full 0.965 _refine_diff_density_max 0.389 _refine_diff_density_min -0.223 _refine_diff_density_rms 0.054 _database_code_depnum_ccdc_archive 'CCDC 927324' ####################################################################### # # 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_compound8 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C40 H28 N6 Ni, 2(C H Cl3), C4 H10 O' _chemical_formula_sum 'C46 H40 Cl6 N6 Ni O' _chemical_formula_weight 964.25 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' Ni Ni 0.3393 1.1124 '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' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Trigonal _symmetry_space_group_name_H-M 'P3(2)21 ' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-y, x-y, z+2/3' '-x+y, -x, z+1/3' 'x-y, -y, -z+1/3' '-x, -x+y, -z+2/3' 'y, x, -z' _cell_length_a 13.8377(3) _cell_length_b 13.8377(3) _cell_length_c 20.3849(4) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 120.00 _cell_volume 3380.39(12) _cell_formula_units_Z 3 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 9939 _cell_measurement_theta_min 2.62 _cell_measurement_theta_max 23.72 _exptl_crystal_description prism _exptl_crystal_colour orange _exptl_crystal_size_max 0.15 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.421 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1488 _exptl_absorpt_coefficient_mu 0.829 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8857 _exptl_absorpt_correction_T_max 0.9217 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(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_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 68908 _diffrn_reflns_av_R_equivalents 0.0595 _diffrn_reflns_av_sigmaI/netI 0.0387 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 19 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min -28 _diffrn_reflns_limit_l_max 28 _diffrn_reflns_theta_min 1.70 _diffrn_reflns_theta_max 30.23 _reflns_number_total 6705 _reflns_number_gt 5984 _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^)+(0.0634P)^2^+7.1358P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.04(2) _refine_ls_number_reflns 6705 _refine_ls_number_parameters 283 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0727 _refine_ls_R_factor_gt 0.0636 _refine_ls_wR_factor_ref 0.1748 _refine_ls_wR_factor_gt 0.1679 _refine_ls_goodness_of_fit_ref 1.160 _refine_ls_restrained_S_all 1.160 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.5945(3) 0.9072(3) 0.03049(19) 0.0249(8) Uani 1 1 d . . . H1 H 0.6639 0.9689 0.0215 0.030 Uiso 1 1 calc R . . C2 C 0.5382(4) 0.8160(4) -0.0123(2) 0.0328(9) Uani 1 1 d . . . H2 H 0.5629 0.8066 -0.0529 0.039 Uiso 1 1 calc R . . C3 C 0.4388(4) 0.7433(4) 0.0183(2) 0.0325(10) Uani 1 1 d . . . H3 H 0.3830 0.6752 0.0021 0.039 Uiso 1 1 calc R . . C4 C 0.4388(3) 0.7933(3) 0.07974(17) 0.0212(7) Uani 1 1 d . . . C5 C 0.3532(3) 0.7484(3) 0.12635(17) 0.0203(7) Uani 1 1 d . . . C6 C 0.3485(3) 0.7975(3) 0.18575(17) 0.0213(7) Uani 1 1 d . . . C7 C 0.2590(3) 0.7528(4) 0.2310(2) 0.0301(9) Uani 1 1 d . . . H7 H 0.1940 0.6837 0.2284 0.036 Uiso 1 1 calc R . . C8 C 0.2868(4) 0.8313(4) 0.2793(2) 0.0358(10) Uani 1 1 d . . . H8 H 0.2443 0.8262 0.3158 0.043 Uiso 1 1 calc R . . C9 C 0.3936(4) 0.9218(3) 0.2625(2) 0.0280(9) Uani 1 1 d . . . H9 H 0.4322 0.9869 0.2870 0.034 Uiso 1 1 calc R . . C10 C 0.2548(3) 0.6350(3) 0.1144(2) 0.0258(8) Uani 1 1 d . . . C11 C 0.2593(3) 0.5395(3) 0.1289(2) 0.0281(8) Uani 1 1 d . . . H11 H 0.3270 0.5453 0.1405 0.034 Uiso 1 1 calc R . . C12 C 0.1638(4) 0.4356(4) 0.1262(2) 0.0295(8) Uani 1 1 d . . . H12 H 0.1684 0.3723 0.1359 0.035 Uiso 1 1 calc R . . C13 C 0.0617(3) 0.4242(3) 0.10930(19) 0.0255(8) Uani 1 1 d . . . C14 C 0.0582(4) 0.5197(4) 0.09131(19) 0.0285(7) Uani 1 1 d . . . H14 H -0.0087 0.5134 0.0774 0.034 Uiso 1 1 calc R . . C15 C 0.1536(3) 0.6237(3) 0.0940(2) 0.0297(9) Uani 1 1 d . . . H15 H 0.1500 0.6868 0.0821 0.036 Uiso 1 1 calc R . . C16 C -0.0426(3) 0.3152(3) 0.11235(19) 0.0227(7) Uani 1 1 d . . . C17 C -0.0562(3) 0.2373(3) 0.1601(2) 0.0249(8) Uani 1 1 d . . . H17 H 0.0030 0.2505 0.1875 0.030 Uiso 1 1 calc R . . C18 C -0.1583(3) 0.1400(3) 0.16668(19) 0.0242(7) Uani 1 1 d . . . H18 H -0.1660 0.0896 0.1993 0.029 Uiso 1 1 calc R . . C19 C -0.2320(3) 0.1883(3) 0.08138(19) 0.0254(8) Uani 1 1 d . . . H19 H -0.2914 0.1717 0.0533 0.030 Uiso 1 1 calc R . . C20 C -0.1327(3) 0.2884(3) 0.07223(19) 0.0259(8) Uani 1 1 d . . . H20 H -0.1272 0.3372 0.0391 0.031 Uiso 1 1 calc R . . N1 N 0.5368(3) 0.8952(2) 0.08569(14) 0.0188(5) Uani 1 1 d . . . N2 N 0.4311(3) 0.9015(2) 0.20706(15) 0.0181(6) Uani 1 1 d . . . N3 N -0.2466(3) 0.1150(2) 0.12824(16) 0.0227(6) Uani 1 1 d . . . Ni1 Ni 0.58502(4) 1.0000 0.1667 0.01526(13) Uani 1 2 d S . . C21 C 0.4512(12) 0.5029(11) 0.0060(5) 0.052(3) Uani 0.50 1 d P A -1 H21 H 0.4103 0.5437 0.0068 0.063 Uiso 0.50 1 calc PR A -1 Cl1 Cl 0.5356(2) 0.5369(2) 0.07104(10) 0.0895(7) Uani 1 1 d . . . Cl2 Cl 0.3572(2) 0.3572(2) 0.0000 0.0867(10) Uani 1 2 d S . . C22 C 0.9918(16) 0.9781(18) 0.0194(7) 0.085(6) Uani 0.50 1 d P B -1 H22 H 1.0099 0.9627 0.0632 0.102 Uiso 0.50 1 calc PR B -1 Cl3 Cl 0.9769(4) 1.0872(4) 0.0293(2) 0.185(2) Uani 1 1 d . . . Cl4 Cl 0.8557(5) 0.8557(5) 0.0000 0.152(2) Uani 1 2 d S . . C23 C 0.2294(10) 0.0942(13) 0.1717(6) 0.129(5) Uani 1 1 d . . . H23A H 0.2760 0.0997 0.1347 0.155 Uiso 1 1 calc R . . H23B H 0.2668 0.0916 0.2113 0.155 Uiso 1 1 calc R . . C24 C 0.2176(11) 0.1928(13) 0.1734(10) 0.191(10) Uani 1 1 d . . . H24A H 0.2100 0.2132 0.1294 0.287 Uiso 1 1 calc R . . H24B H 0.2825 0.2533 0.1934 0.287 Uiso 1 1 calc R . . H24C H 0.1525 0.1772 0.1983 0.287 Uiso 1 1 calc R . . O1 O 0.1318(8) 0.0000 0.1667 0.206(10) Uani 1 2 d S . . 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 C1 0.0227(17) 0.0171(17) 0.0274(17) -0.0006(13) 0.0050(14) 0.0043(14) C2 0.041(2) 0.025(2) 0.0233(18) -0.0045(15) 0.0050(17) 0.0093(18) C3 0.033(2) 0.0230(19) 0.0264(18) -0.0057(15) 0.0014(16) 0.0023(17) C4 0.0198(16) 0.0123(16) 0.0232(16) -0.0014(12) -0.0003(13) 0.0018(14) C5 0.0152(15) 0.0159(16) 0.0232(15) -0.0015(12) -0.0043(12) 0.0028(13) C6 0.0177(16) 0.0193(17) 0.0211(15) 0.0007(13) -0.0013(13) 0.0050(14) C7 0.0192(18) 0.030(2) 0.0265(18) 0.0016(16) 0.0027(14) 0.0014(16) C8 0.032(2) 0.041(3) 0.0222(17) -0.0009(16) 0.0067(15) 0.0093(19) C9 0.030(2) 0.027(2) 0.0273(18) -0.0041(14) 0.0023(15) 0.0142(17) C10 0.0180(17) 0.0181(17) 0.0244(17) -0.0022(14) 0.0005(13) -0.0038(14) C11 0.0149(17) 0.0194(18) 0.037(2) -0.0031(15) -0.0011(14) -0.0007(14) C12 0.0197(18) 0.0203(19) 0.0360(19) 0.0007(16) 0.0011(16) 0.0007(14) C13 0.0204(18) 0.0163(17) 0.0256(17) 0.0000(13) 0.0011(14) -0.0014(14) C14 0.0204(19) 0.024(2) 0.0295(17) 0.0030(16) -0.0037(15) 0.0029(14) C15 0.025(2) 0.0216(18) 0.0301(19) 0.0047(14) -0.0052(15) 0.0025(16) C16 0.0168(16) 0.0177(17) 0.0242(17) 0.0015(13) 0.0006(13) 0.0015(14) C17 0.0165(17) 0.0196(17) 0.0303(18) 0.0009(14) -0.0015(14) 0.0029(14) C18 0.0206(16) 0.0159(17) 0.0309(17) 0.0034(14) 0.0016(13) 0.0052(14) C19 0.0209(17) 0.0221(18) 0.0245(17) -0.0003(14) -0.0006(13) 0.0042(14) C20 0.0191(18) 0.0257(18) 0.0245(16) 0.0043(13) 0.0007(13) 0.0048(15) N1 0.0178(14) 0.0114(12) 0.0231(13) -0.0013(10) -0.0002(11) 0.0042(12) N2 0.0182(14) 0.0123(13) 0.0216(13) -0.0006(10) 0.0014(11) 0.0061(11) N3 0.0182(15) 0.0132(12) 0.0292(14) 0.0000(10) -0.0017(12) 0.0021(12) Ni1 0.0148(2) 0.0083(3) 0.0205(2) -0.0004(2) -0.00021(11) 0.00417(13) C21 0.069(8) 0.064(7) 0.034(4) -0.011(4) -0.027(5) 0.040(7) Cl1 0.1196(19) 0.0952(16) 0.0704(12) -0.0156(11) -0.0383(12) 0.0662(15) Cl2 0.0719(13) 0.0719(13) 0.123(3) 0.0198(8) -0.0198(8) 0.0410(14) C22 0.110(14) 0.136(16) 0.052(8) -0.008(9) 0.012(7) 0.095(13) Cl3 0.218(5) 0.208(4) 0.202(4) -0.094(4) -0.010(4) 0.162(4) Cl4 0.173(4) 0.173(4) 0.111(3) -0.0064(17) 0.0064(17) 0.088(4) C23 0.087(8) 0.200(15) 0.106(8) 0.033(9) 0.018(6) 0.076(9) C24 0.096(9) 0.166(14) 0.34(2) 0.159(16) 0.069(12) 0.089(10) O1 0.079(4) 0.151(11) 0.41(3) 0.182(15) 0.091(8) 0.076(6) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 N1 1.341(5) . ? C1 C2 1.405(6) . ? C1 H1 0.9300 . ? C2 C3 1.381(6) . ? C2 H2 0.9300 . ? C3 C4 1.432(5) . ? C3 H3 0.9300 . ? C4 N1 1.389(4) . ? C4 C5 1.399(5) . ? C5 C6 1.406(5) . ? C5 C10 1.496(5) . ? C6 N2 1.386(5) . ? C6 C7 1.414(5) . ? C7 C8 1.371(6) . ? C7 H7 0.9300 . ? C8 C9 1.421(6) . ? C8 H8 0.9300 . ? C9 N2 1.331(5) . ? C9 H9 0.9300 . ? C10 C11 1.385(6) . ? C10 C15 1.393(6) . ? C11 C12 1.384(6) . ? C11 H11 0.9300 . ? C12 C13 1.385(6) . ? C12 H12 0.9300 . ? C13 C14 1.395(6) . ? C13 C16 1.478(5) . ? C14 C15 1.384(6) . ? C14 H14 0.9300 . ? C15 H15 0.9300 . ? C16 C20 1.378(5) . ? C16 C17 1.394(5) . ? C17 C18 1.387(5) . ? C17 H17 0.9300 . ? C18 N3 1.343(5) . ? C18 H18 0.9300 . ? C19 N3 1.333(5) . ? C19 C20 1.393(5) . ? C19 H19 0.9300 . ? C20 H20 0.9300 . ? N1 Ni1 2.075(3) . ? N2 Ni1 2.042(3) . ? N3 Ni1 2.206(3) 1_445 ? Ni1 N2 2.042(3) 4_675 ? Ni1 N1 2.075(3) 4_675 ? Ni1 N3 2.206(3) 4_665 ? Ni1 N3 2.206(3) 1_665 ? C21 Cl1 1.671(10) . ? C21 Cl2 1.775(13) . ? C21 Cl1 1.883(13) 6 ? C21 H21 0.9800 . ? Cl1 C21 1.883(13) 6 ? Cl2 C21 1.775(13) 6 ? C22 Cl3 1.64(2) . ? C22 Cl3 1.659(16) 6 ? C22 Cl4 1.84(2) . ? C22 H22 0.9800 . ? Cl3 C22 1.659(16) 6 ? Cl4 C22 1.84(2) 6 ? C23 O1 1.332(14) . ? C23 C24 1.454(18) . ? C23 H23A 0.9700 . ? C23 H23B 0.9700 . ? C24 H24A 0.9600 . ? C24 H24B 0.9600 . ? C24 H24C 0.9600 . ? O1 C23 1.332(14) 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 C1 C2 112.4(3) . . ? N1 C1 H1 123.8 . . ? C2 C1 H1 123.8 . . ? C3 C2 C1 106.1(4) . . ? C3 C2 H2 127.0 . . ? C1 C2 H2 127.0 . . ? C2 C3 C4 106.4(3) . . ? C2 C3 H3 126.8 . . ? C4 C3 H3 126.8 . . ? N1 C4 C5 124.9(3) . . ? N1 C4 C3 109.3(3) . . ? C5 C4 C3 125.8(3) . . ? C4 C5 C6 127.2(3) . . ? C4 C5 C10 118.6(3) . . ? C6 C5 C10 114.2(3) . . ? N2 C6 C5 123.9(3) . . ? N2 C6 C7 109.7(3) . . ? C5 C6 C7 126.3(3) . . ? C8 C7 C6 106.5(4) . . ? C8 C7 H7 126.8 . . ? C6 C7 H7 126.8 . . ? C7 C8 C9 106.4(4) . . ? C7 C8 H8 126.8 . . ? C9 C8 H8 126.8 . . ? N2 C9 C8 111.2(4) . . ? N2 C9 H9 124.4 . . ? C8 C9 H9 124.4 . . ? C11 C10 C15 118.6(4) . . ? C11 C10 C5 121.0(4) . . ? C15 C10 C5 120.1(4) . . ? C12 C11 C10 120.5(4) . . ? C12 C11 H11 119.7 . . ? C10 C11 H11 119.7 . . ? C11 C12 C13 121.2(4) . . ? C11 C12 H12 119.4 . . ? C13 C12 H12 119.4 . . ? C12 C13 C14 118.3(4) . . ? C12 C13 C16 121.7(4) . . ? C14 C13 C16 120.0(4) . . ? C15 C14 C13 120.5(4) . . ? C15 C14 H14 119.7 . . ? C13 C14 H14 119.7 . . ? C14 C15 C10 120.7(4) . . ? C14 C15 H15 119.7 . . ? C10 C15 H15 119.7 . . ? C20 C16 C17 116.9(3) . . ? C20 C16 C13 122.6(4) . . ? C17 C16 C13 120.3(4) . . ? C18 C17 C16 119.7(4) . . ? C18 C17 H17 120.1 . . ? C16 C17 H17 120.1 . . ? N3 C18 C17 123.2(4) . . ? N3 C18 H18 118.4 . . ? C17 C18 H18 118.4 . . ? N3 C19 C20 123.5(4) . . ? N3 C19 H19 118.3 . . ? C20 C19 H19 118.3 . . ? C16 C20 C19 119.9(4) . . ? C16 C20 H20 120.1 . . ? C19 C20 H20 120.1 . . ? C1 N1 C4 105.7(3) . . ? C1 N1 Ni1 128.1(2) . . ? C4 N1 Ni1 126.1(2) . . ? C9 N2 C6 106.2(3) . . ? C9 N2 Ni1 126.0(3) . . ? C6 N2 Ni1 127.6(2) . . ? C19 N3 C18 116.8(3) . . ? C19 N3 Ni1 120.4(3) . 1_445 ? C18 N3 Ni1 118.4(2) . 1_445 ? N2 Ni1 N2 89.64(16) . 4_675 ? N2 Ni1 N1 92.79(12) . 4_675 ? N2 Ni1 N1 89.46(12) 4_675 4_675 ? N2 Ni1 N1 89.46(12) . . ? N2 Ni1 N1 92.79(12) 4_675 . ? N1 Ni1 N1 176.82(19) 4_675 . ? N2 Ni1 N3 89.36(11) . 4_665 ? N2 Ni1 N3 176.07(12) 4_675 4_665 ? N1 Ni1 N3 94.38(12) 4_675 4_665 ? N1 Ni1 N3 83.40(12) . 4_665 ? N2 Ni1 N3 176.07(12) . 1_665 ? N2 Ni1 N3 89.36(12) 4_675 1_665 ? N1 Ni1 N3 83.40(12) 4_675 1_665 ? N1 Ni1 N3 94.38(12) . 1_665 ? N3 Ni1 N3 91.88(18) 4_665 1_665 ? Cl1 C21 Cl2 112.8(6) . . ? Cl1 C21 Cl1 109.1(8) . 6 ? Cl2 C21 Cl1 103.4(6) . 6 ? Cl1 C21 H21 110.5 . . ? Cl2 C21 H21 110.5 . . ? Cl1 C21 H21 110.5 6 . ? C21 Cl1 C21 41.1(8) . 6 ? C21 Cl2 C21 41.7(9) 6 . ? Cl3 C22 Cl3 123.5(13) . 6 ? Cl3 C22 Cl4 109.5(10) . . ? Cl3 C22 Cl4 108.4(9) 6 . ? Cl3 C22 H22 104.6 . . ? Cl3 C22 H22 104.6 6 . ? Cl4 C22 H22 104.6 . . ? C22 Cl3 C22 30.1(11) . 6 ? C22 Cl4 C22 26.9(10) . 6 ? O1 C23 C24 112.6(11) . . ? O1 C23 H23A 109.1 . . ? C24 C23 H23A 109.1 . . ? O1 C23 H23B 109.1 . . ? C24 C23 H23B 109.1 . . ? H23A C23 H23B 107.8 . . ? C23 C24 H24A 109.5 . . ? C23 C24 H24B 109.5 . . ? H24A C24 H24B 109.5 . . ? C23 C24 H24C 109.5 . . ? H24A C24 H24C 109.5 . . ? H24B C24 H24C 109.5 . . ? C23 O1 C23 116.6(15) . 4 ? 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 N1 C1 C2 C3 0.5(5) . . . . ? C1 C2 C3 C4 -0.5(5) . . . . ? C2 C3 C4 N1 0.4(5) . . . . ? C2 C3 C4 C5 179.3(4) . . . . ? N1 C4 C5 C6 1.7(6) . . . . ? C3 C4 C5 C6 -177.0(4) . . . . ? N1 C4 C5 C10 -177.2(4) . . . . ? C3 C4 C5 C10 4.1(6) . . . . ? C4 C5 C6 N2 0.3(6) . . . . ? C10 C5 C6 N2 179.2(4) . . . . ? C4 C5 C6 C7 177.2(4) . . . . ? C10 C5 C6 C7 -3.9(6) . . . . ? N2 C6 C7 C8 1.1(5) . . . . ? C5 C6 C7 C8 -176.1(4) . . . . ? C6 C7 C8 C9 -0.5(5) . . . . ? C7 C8 C9 N2 -0.3(5) . . . . ? C4 C5 C10 C11 81.6(5) . . . . ? C6 C5 C10 C11 -97.4(5) . . . . ? C4 C5 C10 C15 -104.3(5) . . . . ? C6 C5 C10 C15 76.6(5) . . . . ? C15 C10 C11 C12 -3.1(6) . . . . ? C5 C10 C11 C12 171.1(4) . . . . ? C10 C11 C12 C13 -0.2(6) . . . . ? C11 C12 C13 C14 3.6(6) . . . . ? C11 C12 C13 C16 -174.1(4) . . . . ? C12 C13 C14 C15 -3.7(6) . . . . ? C16 C13 C14 C15 174.1(4) . . . . ? C13 C14 C15 C10 0.4(6) . . . . ? C11 C10 C15 C14 3.0(6) . . . . ? C5 C10 C15 C14 -171.2(4) . . . . ? C12 C13 C16 C20 -151.5(4) . . . . ? C14 C13 C16 C20 30.9(6) . . . . ? C12 C13 C16 C17 33.2(6) . . . . ? C14 C13 C16 C17 -144.5(4) . . . . ? C20 C16 C17 C18 -1.9(6) . . . . ? C13 C16 C17 C18 173.6(4) . . . . ? C16 C17 C18 N3 0.9(6) . . . . ? C17 C16 C20 C19 1.1(6) . . . . ? C13 C16 C20 C19 -174.3(4) . . . . ? N3 C19 C20 C16 0.8(6) . . . . ? C2 C1 N1 C4 -0.3(5) . . . . ? C2 C1 N1 Ni1 176.3(3) . . . . ? C5 C4 N1 C1 -179.0(4) . . . . ? C3 C4 N1 C1 -0.1(5) . . . . ? C5 C4 N1 Ni1 4.4(6) . . . . ? C3 C4 N1 Ni1 -176.7(3) . . . . ? C8 C9 N2 C6 1.0(5) . . . . ? C8 C9 N2 Ni1 -174.7(3) . . . . ? C5 C6 N2 C9 176.0(4) . . . . ? C7 C6 N2 C9 -1.3(4) . . . . ? C5 C6 N2 Ni1 -8.4(5) . . . . ? C7 C6 N2 Ni1 174.3(3) . . . . ? C20 C19 N3 C18 -1.9(6) . . . . ? C20 C19 N3 Ni1 154.1(3) . . . 1_445 ? C17 C18 N3 C19 1.0(6) . . . . ? C17 C18 N3 Ni1 -155.5(3) . . . 1_445 ? C9 N2 Ni1 N2 -82.1(3) . . . 4_675 ? C6 N2 Ni1 N2 103.2(3) . . . 4_675 ? C9 N2 Ni1 N1 7.4(3) . . . 4_675 ? C6 N2 Ni1 N1 -167.4(3) . . . 4_675 ? C9 N2 Ni1 N1 -174.9(3) . . . . ? C6 N2 Ni1 N1 10.4(3) . . . . ? C9 N2 Ni1 N3 101.7(3) . . . 4_665 ? C6 N2 Ni1 N3 -73.0(3) . . . 4_665 ? C9 N2 Ni1 N3 -7(2) . . . 1_665 ? C6 N2 Ni1 N3 178(64) . . . 1_665 ? C1 N1 Ni1 N2 175.8(3) . . . . ? C4 N1 Ni1 N2 -8.4(3) . . . . ? C1 N1 Ni1 N2 86.2(3) . . . 4_675 ? C4 N1 Ni1 N2 -98.0(3) . . . 4_675 ? C1 N1 Ni1 N1 -49.0(3) . . . 4_675 ? C4 N1 Ni1 N1 126.9(3) . . . 4_675 ? C1 N1 Ni1 N3 -94.8(3) . . . 4_665 ? C4 N1 Ni1 N3 81.1(3) . . . 4_665 ? C1 N1 Ni1 N3 -3.4(4) . . . 1_665 ? C4 N1 Ni1 N3 172.5(3) . . . 1_665 ? Cl2 C21 Cl1 C21 61.4(7) . . . 6 ? Cl1 C21 Cl1 C21 -52.9(7) 6 . . 6 ? Cl1 C21 Cl2 C21 -67.0(8) . . . 6 ? Cl1 C21 Cl2 C21 50.7(8) 6 . . 6 ? Cl3 C22 Cl3 C22 59.3(14) 6 . . 6 ? Cl4 C22 Cl3 C22 -70.2(11) . . . 6 ? Cl3 C22 Cl4 C22 70(2) . . . 6 ? Cl3 C22 Cl4 C22 -67.1(18) 6 . . 6 ? C24 C23 O1 C23 176.9(14) . . . 4 ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 30.23 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.886 _refine_diff_density_min -0.807 _refine_diff_density_rms 0.104 _database_code_depnum_ccdc_archive 'CCDC 927325' ####################################################################### # # 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_compound9 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C40 H28 N6 Ni, C H Cl3 ' _chemical_formula_sum 'C41 H29 Cl3 N6 Ni' _chemical_formula_weight 770.76 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' Ni Ni 0.3393 1.1124 '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' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P2(1)/n ' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 9.1455(2) _cell_length_b 22.8915(4) _cell_length_c 17.1438(3) _cell_angle_alpha 90.00 _cell_angle_beta 103.4680(10) _cell_angle_gamma 90.00 _cell_volume 3490.43(12) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 9643 _cell_measurement_theta_min 2.33 _cell_measurement_theta_max 29.99 _exptl_crystal_description prism _exptl_crystal_colour orange _exptl_crystal_size_max 0.10 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.467 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1584 _exptl_absorpt_coefficient_mu 0.826 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9219 _exptl_absorpt_correction_T_max 0.9219 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(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_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 75580 _diffrn_reflns_av_R_equivalents 0.0398 _diffrn_reflns_av_sigmaI/netI 0.0345 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -30 _diffrn_reflns_limit_k_max 32 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_theta_min 1.51 _diffrn_reflns_theta_max 30.11 _reflns_number_total 10250 _reflns_number_gt 7731 _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^)+(0.0502P)^2^+3.4289P] 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 10250 _refine_ls_number_parameters 460 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0672 _refine_ls_R_factor_gt 0.0449 _refine_ls_wR_factor_ref 0.1209 _refine_ls_wR_factor_gt 0.1067 _refine_ls_goodness_of_fit_ref 1.048 _refine_ls_restrained_S_all 1.048 _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 C1 C 0.3400(3) 0.22672(11) 0.81230(17) 0.0396(6) Uani 1 1 d . . . H1 H 0.2788 0.1941 0.7985 0.048 Uiso 1 1 calc R . . C2 C 0.3193(4) 0.26930(11) 0.8682(2) 0.0502(8) Uani 1 1 d . . . H2 H 0.2453 0.2694 0.8974 0.060 Uiso 1 1 calc R . . C3 C 0.4290(3) 0.31025(10) 0.87124(16) 0.0350(5) Uani 1 1 d . . . H3 H 0.4428 0.3442 0.9019 0.042 Uiso 1 1 calc R . . C4 C 0.5185(2) 0.29080(9) 0.81820(12) 0.0229(4) Uani 1 1 d . . . C5 C 0.6463(2) 0.31728(8) 0.80278(12) 0.0205(4) Uani 1 1 d . . . C6 C 0.7340(2) 0.29493(9) 0.75230(12) 0.0216(4) Uani 1 1 d . . . C7 C 0.8808(3) 0.31460(11) 0.74934(15) 0.0321(5) Uani 1 1 d . . . H7 H 0.9324 0.3461 0.7772 0.039 Uiso 1 1 calc R . . C8 C 0.9313(3) 0.27819(11) 0.69759(16) 0.0354(5) Uani 1 1 d . . . H8 H 1.0238 0.2797 0.6839 0.042 Uiso 1 1 calc R . . C9 C 0.8145(2) 0.23811(10) 0.66958(14) 0.0274(4) Uani 1 1 d . . . H9 H 0.8188 0.2087 0.6328 0.033 Uiso 1 1 calc R . . C10 C 0.6933(2) 0.37492(9) 0.84149(12) 0.0223(4) Uani 1 1 d . . . C11 C 0.7227(3) 0.38362(9) 0.92410(12) 0.0256(4) Uani 1 1 d . . . H11 H 0.7125 0.3525 0.9572 0.031 Uiso 1 1 calc R . . C12 C 0.7667(3) 0.43758(9) 0.95798(12) 0.0250(4) Uani 1 1 d . . . H12 H 0.7870 0.4420 1.0134 0.030 Uiso 1 1 calc R . . C13 C 0.7808(2) 0.48534(9) 0.91009(12) 0.0231(4) Uani 1 1 d . . . C14 C 0.7466(3) 0.47719(10) 0.82737(13) 0.0326(5) Uani 1 1 d . . . H14 H 0.7517 0.5088 0.7941 0.039 Uiso 1 1 calc R . . C15 C 0.7051(3) 0.42297(10) 0.79368(13) 0.0311(5) Uani 1 1 d . . . H15 H 0.6848 0.4186 0.7383 0.037 Uiso 1 1 calc R . . C16 C 0.8263(2) 0.54395(9) 0.94425(12) 0.0234(4) Uani 1 1 d . . . C17 C 0.8025(3) 0.56251(10) 1.01718(13) 0.0292(5) Uani 1 1 d . . . H17 H 0.7628 0.5372 1.0494 0.035 Uiso 1 1 calc R . . C18 C 0.8392(3) 0.61945(11) 1.04124(16) 0.0363(5) Uani 1 1 d . . . H18 H 0.8277 0.6324 1.0909 0.044 Uiso 1 1 calc R . . C19 C 0.8925(3) 0.65661(11) 0.99158(16) 0.0357(5) Uani 1 1 d . . . H19 H 0.9096 0.6954 1.0072 0.043 Uiso 1 1 calc R . . C20 C 0.8919(2) 0.58398(9) 0.90138(13) 0.0255(4) Uani 1 1 d . . . H20 H 0.9173 0.5708 0.8550 0.031 Uiso 1 1 calc R . . C21 C 0.1795(2) 0.15780(10) 0.62124(14) 0.0275(4) Uani 1 1 d . . . H21 H 0.1595 0.1905 0.5884 0.033 Uiso 1 1 calc R . . C22 C 0.0701(3) 0.11633(10) 0.62892(16) 0.0336(5) Uani 1 1 d . . . H22 H -0.0309 0.1165 0.6024 0.040 Uiso 1 1 calc R . . C23 C 0.1417(3) 0.07597(10) 0.68286(15) 0.0312(5) Uani 1 1 d . . . H23 H 0.0985 0.0433 0.7007 0.037 Uiso 1 1 calc R . . C24 C 0.2961(2) 0.09338(9) 0.70693(12) 0.0224(4) Uani 1 1 d . . . C25 C 0.4080(2) 0.06598(8) 0.76447(12) 0.0216(4) Uani 1 1 d . . . C26 C 0.5581(2) 0.08273(8) 0.79069(12) 0.0214(4) Uani 1 1 d . . . C27 C 0.6744(3) 0.05054(9) 0.84247(12) 0.0258(4) Uani 1 1 d . . . H27 H 0.6631 0.0160 0.8690 0.031 Uiso 1 1 calc R . . C28 C 0.8059(3) 0.07991(10) 0.84595(14) 0.0305(5) Uani 1 1 d . . . H28 H 0.9013 0.0692 0.8748 0.037 Uiso 1 1 calc R . . C29 C 0.7673(2) 0.12979(10) 0.79686(13) 0.0266(4) Uani 1 1 d . . . H29 H 0.8364 0.1577 0.7889 0.032 Uiso 1 1 calc R . . C30 C 0.3626(2) 0.01179(9) 0.80206(12) 0.0233(4) Uani 1 1 d . . . C31 C 0.3393(3) -0.04068(9) 0.76021(13) 0.0286(5) Uani 1 1 d . . . H31 H 0.3505 -0.0422 0.7077 0.034 Uiso 1 1 calc R . . C32 C 0.2997(3) -0.09057(9) 0.79575(13) 0.0273(5) Uani 1 1 d . . . H32 H 0.2843 -0.1252 0.7667 0.033 Uiso 1 1 calc R . . C33 C 0.2824(2) -0.08987(9) 0.87450(12) 0.0224(4) Uani 1 1 d . . . C34 C 0.3047(3) -0.03701(9) 0.91610(13) 0.0268(4) Uani 1 1 d . . . H34 H 0.2926 -0.0353 0.9684 0.032 Uiso 1 1 calc R . . C35 C 0.3447(3) 0.01293(9) 0.88043(13) 0.0276(5) Uani 1 1 d . . . H35 H 0.3599 0.0477 0.9093 0.033 Uiso 1 1 calc R . . C36 C 0.2461(2) -0.14385(9) 0.91383(12) 0.0219(4) Uani 1 1 d . . . C37 C 0.3007(3) -0.15469(10) 0.99521(13) 0.0287(5) Uani 1 1 d . . . H37 H 0.3640 -0.1280 1.0275 0.034 Uiso 1 1 calc R . . C38 C 0.2595(3) -0.20578(10) 1.02736(14) 0.0345(5) Uani 1 1 d . . . H38 H 0.2936 -0.2138 1.0818 0.041 Uiso 1 1 calc R . . C39 C 0.1673(3) -0.24464(10) 0.97766(15) 0.0313(5) Uani 1 1 d . . . H39 H 0.1395 -0.2786 1.0003 0.038 Uiso 1 1 calc R . . C40 C 0.1546(2) -0.18609(9) 0.86875(13) 0.0244(4) Uani 1 1 d . . . H40 H 0.1180 -0.1791 0.8143 0.029 Uiso 1 1 calc R . . N1 N 0.4569(2) 0.23879(7) 0.78183(11) 0.0244(4) Uani 1 1 d . . . N2 N 0.69692(19) 0.24692(7) 0.70159(10) 0.0214(3) Uani 1 1 d . . . N3 N 0.9212(2) 0.63999(8) 0.92191(12) 0.0298(4) Uani 1 1 d . . . N4 N 0.31541(19) 0.14483(7) 0.66644(10) 0.0216(3) Uani 1 1 d . . . N5 N 0.62097(19) 0.13228(7) 0.76339(10) 0.0211(3) Uani 1 1 d . . . N6 N 0.1154(2) -0.23661(7) 0.89883(12) 0.0260(4) Uani 1 1 d . . . Ni1 Ni 0.50832(3) 0.195727(10) 0.686597(16) 0.01949(7) Uani 1 1 d . . . C41 C 0.1807(3) 0.12828(11) 0.05128(16) 0.0355(5) Uani 1 1 d . . . H41 H 0.1757 0.1556 0.0946 0.043 Uiso 1 1 calc R . . Cl1 Cl 0.36639(7) 0.10340(4) 0.06481(5) 0.04904(18) Uani 1 1 d . . . Cl2 Cl 0.06277(7) 0.06864(3) 0.05642(4) 0.04524(16) Uani 1 1 d . . . Cl3 Cl 0.12168(10) 0.16455(4) -0.04077(5) 0.0592(2) 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 C1 0.0467(15) 0.0223(11) 0.0604(16) -0.0119(11) 0.0342(13) -0.0118(11) C2 0.0629(18) 0.0286(13) 0.078(2) -0.0206(13) 0.0538(17) -0.0148(13) C3 0.0450(14) 0.0216(11) 0.0461(14) -0.0102(10) 0.0262(12) -0.0059(10) C4 0.0297(11) 0.0141(9) 0.0263(10) -0.0006(7) 0.0093(8) -0.0004(8) C5 0.0261(10) 0.0145(9) 0.0195(9) 0.0018(7) 0.0025(7) -0.0002(7) C6 0.0231(10) 0.0169(9) 0.0244(9) 0.0013(7) 0.0047(8) -0.0038(8) C7 0.0272(11) 0.0304(12) 0.0396(13) -0.0069(10) 0.0097(9) -0.0101(9) C8 0.0265(11) 0.0362(13) 0.0475(14) -0.0075(11) 0.0169(10) -0.0078(10) C9 0.0277(11) 0.0219(10) 0.0355(11) -0.0032(8) 0.0129(9) -0.0015(9) C10 0.0265(10) 0.0177(9) 0.0219(9) -0.0008(7) 0.0042(8) -0.0027(8) C11 0.0356(12) 0.0178(10) 0.0225(10) 0.0034(7) 0.0050(8) -0.0002(9) C12 0.0342(11) 0.0219(10) 0.0170(9) -0.0002(7) 0.0024(8) 0.0009(9) C13 0.0280(10) 0.0171(9) 0.0232(9) -0.0016(7) 0.0039(8) -0.0004(8) C14 0.0550(15) 0.0192(10) 0.0229(10) 0.0012(8) 0.0078(10) -0.0092(10) C15 0.0506(14) 0.0224(11) 0.0186(9) -0.0009(8) 0.0045(9) -0.0081(10) C16 0.0237(10) 0.0193(10) 0.0247(10) -0.0041(8) 0.0010(8) 0.0026(8) C17 0.0292(11) 0.0294(11) 0.0284(11) -0.0061(9) 0.0057(9) -0.0012(9) C18 0.0349(13) 0.0370(13) 0.0376(13) -0.0181(10) 0.0098(10) -0.0007(10) C19 0.0307(12) 0.0255(11) 0.0507(15) -0.0173(10) 0.0093(11) -0.0010(9) C20 0.0290(11) 0.0174(9) 0.0289(10) -0.0030(8) 0.0045(8) 0.0011(8) C21 0.0260(10) 0.0206(10) 0.0346(11) -0.0004(8) 0.0047(9) 0.0005(8) C22 0.0229(11) 0.0301(12) 0.0461(14) -0.0015(10) 0.0044(10) -0.0035(9) C23 0.0264(11) 0.0234(11) 0.0454(13) -0.0012(9) 0.0114(10) -0.0080(9) C24 0.0258(10) 0.0152(9) 0.0281(10) -0.0022(7) 0.0102(8) -0.0038(8) C25 0.0298(10) 0.0137(9) 0.0240(9) -0.0031(7) 0.0118(8) -0.0031(8) C26 0.0301(10) 0.0138(9) 0.0209(9) -0.0014(7) 0.0072(8) -0.0025(8) C27 0.0369(12) 0.0190(10) 0.0203(9) 0.0016(7) 0.0044(8) 0.0001(9) C28 0.0305(11) 0.0269(11) 0.0290(11) 0.0018(9) -0.0032(9) 0.0005(9) C29 0.0261(10) 0.0232(10) 0.0285(10) -0.0002(8) 0.0021(8) -0.0056(8) C30 0.0296(11) 0.0153(9) 0.0262(10) -0.0003(7) 0.0086(8) -0.0038(8) C31 0.0443(13) 0.0203(10) 0.0230(10) -0.0023(8) 0.0113(9) -0.0047(9) C32 0.0414(13) 0.0151(9) 0.0252(10) -0.0046(8) 0.0072(9) -0.0079(9) C33 0.0231(10) 0.0174(9) 0.0265(10) 0.0013(7) 0.0054(8) -0.0042(8) C34 0.0354(12) 0.0229(10) 0.0249(10) -0.0029(8) 0.0126(9) -0.0070(9) C35 0.0396(12) 0.0167(10) 0.0294(11) -0.0059(8) 0.0136(9) -0.0071(9) C36 0.0236(10) 0.0155(9) 0.0278(10) 0.0014(7) 0.0084(8) -0.0002(8) C37 0.0344(12) 0.0239(11) 0.0272(10) 0.0001(8) 0.0060(9) -0.0030(9) C38 0.0485(15) 0.0284(12) 0.0266(11) 0.0068(9) 0.0090(10) 0.0010(10) C39 0.0379(12) 0.0197(10) 0.0398(12) 0.0093(9) 0.0163(10) 0.0007(9) C40 0.0251(10) 0.0161(9) 0.0311(10) 0.0036(8) 0.0046(8) -0.0006(8) N1 0.0297(9) 0.0137(8) 0.0334(9) -0.0027(7) 0.0147(7) -0.0029(7) N2 0.0237(8) 0.0143(8) 0.0270(8) 0.0001(6) 0.0076(7) -0.0017(7) N3 0.0275(9) 0.0167(8) 0.0441(11) -0.0063(8) 0.0064(8) 0.0003(7) N4 0.0243(8) 0.0140(8) 0.0271(9) -0.0016(6) 0.0070(7) -0.0014(7) N5 0.0253(9) 0.0150(8) 0.0227(8) -0.0011(6) 0.0051(7) -0.0034(7) N6 0.0236(9) 0.0155(8) 0.0398(10) 0.0035(7) 0.0090(8) -0.0008(7) Ni1 0.02075(13) 0.01133(12) 0.02723(14) 0.00034(9) 0.00727(10) -0.00107(9) C41 0.0283(12) 0.0378(14) 0.0403(13) -0.0067(10) 0.0079(10) 0.0002(10) Cl1 0.0285(3) 0.0604(5) 0.0574(4) -0.0090(3) 0.0083(3) 0.0012(3) Cl2 0.0364(3) 0.0468(4) 0.0515(4) 0.0105(3) 0.0079(3) -0.0040(3) Cl3 0.0615(5) 0.0461(4) 0.0657(5) 0.0192(4) 0.0060(4) -0.0067(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 C1 N1 1.324(3) . ? C1 C2 1.411(3) . ? C1 H1 0.9300 . ? C2 C3 1.366(3) . ? C2 H2 0.9300 . ? C3 C4 1.429(3) . ? C3 H3 0.9300 . ? C4 C5 1.396(3) . ? C4 N1 1.400(3) . ? C5 C6 1.406(3) . ? C5 C10 1.494(3) . ? C6 N2 1.393(3) . ? C6 C7 1.428(3) . ? C7 C8 1.373(3) . ? C7 H7 0.9300 . ? C8 C9 1.406(3) . ? C8 H8 0.9300 . ? C9 N2 1.331(3) . ? C9 H9 0.9300 . ? C10 C15 1.391(3) . ? C10 C11 1.393(3) . ? C11 C12 1.384(3) . ? C11 H11 0.9300 . ? C12 C13 1.391(3) . ? C12 H12 0.9300 . ? C13 C14 1.392(3) . ? C13 C16 1.484(3) . ? C14 C15 1.384(3) . ? C14 H14 0.9300 . ? C15 H15 0.9300 . ? C16 C17 1.385(3) . ? C16 C20 1.395(3) . ? C17 C18 1.384(3) . ? C17 H17 0.9300 . ? C18 C19 1.371(4) . ? C18 H18 0.9300 . ? C19 N3 1.336(3) . ? C19 H19 0.9300 . ? C20 N3 1.340(3) . ? C20 H20 0.9300 . ? C21 N4 1.336(3) . ? C21 C22 1.407(3) . ? C21 H21 0.9300 . ? C22 C23 1.362(3) . ? C22 H22 0.9300 . ? C23 C24 1.432(3) . ? C23 H23 0.9300 . ? C24 C25 1.394(3) . ? C24 N4 1.399(3) . ? C25 C26 1.395(3) . ? C25 C30 1.500(3) . ? C26 N5 1.401(3) . ? C26 C27 1.422(3) . ? C27 C28 1.367(3) . ? C27 H27 0.9300 . ? C28 C29 1.413(3) . ? C28 H28 0.9300 . ? C29 N5 1.329(3) . ? C29 H29 0.9300 . ? C30 C31 1.390(3) . ? C30 C35 1.391(3) . ? C31 C32 1.382(3) . ? C31 H31 0.9300 . ? C32 C33 1.396(3) . ? C32 H32 0.9300 . ? C33 C34 1.395(3) . ? C33 C36 1.482(3) . ? C34 C35 1.386(3) . ? C34 H34 0.9300 . ? C35 H35 0.9300 . ? C36 C40 1.390(3) . ? C36 C37 1.390(3) . ? C37 C38 1.382(3) . ? C37 H37 0.9300 . ? C38 C39 1.376(4) . ? C38 H38 0.9300 . ? C39 N6 1.337(3) . ? C39 H39 0.9300 . ? C40 N6 1.348(3) . ? C40 H40 0.9300 . ? N1 Ni1 2.0533(17) . ? N2 Ni1 2.0514(17) . ? N4 Ni1 2.0749(17) . ? N5 Ni1 2.0669(17) . ? N6 Ni1 2.2477(19) 2_546 ? Ni1 N6 2.2477(19) 2_556 ? C41 Cl3 1.753(3) . ? C41 Cl2 1.755(3) . ? C41 Cl1 1.755(3) . ? C41 H41 0.9800 . ? 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 C1 C2 111.9(2) . . ? N1 C1 H1 124.1 . . ? C2 C1 H1 124.1 . . ? C3 C2 C1 106.6(2) . . ? C3 C2 H2 126.7 . . ? C1 C2 H2 126.7 . . ? C2 C3 C4 106.7(2) . . ? C2 C3 H3 126.7 . . ? C4 C3 H3 126.7 . . ? C5 C4 N1 123.56(18) . . ? C5 C4 C3 127.90(19) . . ? N1 C4 C3 108.54(18) . . ? C4 C5 C6 125.55(18) . . ? C4 C5 C10 117.78(18) . . ? C6 C5 C10 116.66(18) . . ? N2 C6 C5 125.46(18) . . ? N2 C6 C7 108.72(18) . . ? C5 C6 C7 125.65(19) . . ? C8 C7 C6 107.0(2) . . ? C8 C7 H7 126.5 . . ? C6 C7 H7 126.5 . . ? C7 C8 C9 105.9(2) . . ? C7 C8 H8 127.1 . . ? C9 C8 H8 127.1 . . ? N2 C9 C8 112.5(2) . . ? N2 C9 H9 123.7 . . ? C8 C9 H9 123.7 . . ? C15 C10 C11 117.58(19) . . ? C15 C10 C5 119.35(18) . . ? C11 C10 C5 123.05(18) . . ? C12 C11 C10 121.51(19) . . ? C12 C11 H11 119.2 . . ? C10 C11 H11 119.2 . . ? C11 C12 C13 120.76(19) . . ? C11 C12 H12 119.6 . . ? C13 C12 H12 119.6 . . ? C12 C13 C14 117.78(19) . . ? C12 C13 C16 122.25(18) . . ? C14 C13 C16 119.94(19) . . ? C15 C14 C13 121.3(2) . . ? C15 C14 H14 119.3 . . ? C13 C14 H14 119.3 . . ? C14 C15 C10 120.97(19) . . ? C14 C15 H15 119.5 . . ? C10 C15 H15 119.5 . . ? C17 C16 C20 116.8(2) . . ? C17 C16 C13 123.1(2) . . ? C20 C16 C13 120.08(19) . . ? C18 C17 C16 118.7(2) . . ? C18 C17 H17 120.7 . . ? C16 C17 H17 120.7 . . ? C19 C18 C17 119.7(2) . . ? C19 C18 H18 120.1 . . ? C17 C18 H18 120.1 . . ? N3 C19 C18 123.4(2) . . ? N3 C19 H19 118.3 . . ? C18 C19 H19 118.3 . . ? N3 C20 C16 125.1(2) . . ? N3 C20 H20 117.5 . . ? C16 C20 H20 117.5 . . ? N4 C21 C22 112.4(2) . . ? N4 C21 H21 123.8 . . ? C22 C21 H21 123.8 . . ? C23 C22 C21 106.3(2) . . ? C23 C22 H22 126.8 . . ? C21 C22 H22 126.8 . . ? C22 C23 C24 107.0(2) . . ? C22 C23 H23 126.5 . . ? C24 C23 H23 126.5 . . ? C25 C24 N4 124.94(18) . . ? C25 C24 C23 126.22(19) . . ? N4 C24 C23 108.75(19) . . ? C24 C25 C26 127.56(18) . . ? C24 C25 C30 116.40(18) . . ? C26 C25 C30 116.04(18) . . ? C25 C26 N5 124.39(18) . . ? C25 C26 C27 126.55(19) . . ? N5 C26 C27 108.82(18) . . ? C28 C27 C26 107.15(19) . . ? C28 C27 H27 126.4 . . ? C26 C27 H27 126.4 . . ? C27 C28 C29 106.0(2) . . ? C27 C28 H28 127.0 . . ? C29 C28 H28 127.0 . . ? N5 C29 C28 112.2(2) . . ? N5 C29 H29 123.9 . . ? C28 C29 H29 123.9 . . ? C31 C30 C35 118.47(19) . . ? C31 C30 C25 121.14(18) . . ? C35 C30 C25 120.38(18) . . ? C32 C31 C30 120.73(19) . . ? C32 C31 H31 119.6 . . ? C30 C31 H31 119.6 . . ? C31 C32 C33 121.17(19) . . ? C31 C32 H32 119.4 . . ? C33 C32 H32 119.4 . . ? C34 C33 C32 117.93(19) . . ? C34 C33 C36 120.81(18) . . ? C32 C33 C36 121.24(19) . . ? C35 C34 C33 120.81(19) . . ? C35 C34 H34 119.6 . . ? C33 C34 H34 119.6 . . ? C34 C35 C30 120.89(19) . . ? C34 C35 H35 119.6 . . ? C30 C35 H35 119.6 . . ? C40 C36 C37 117.58(19) . . ? C40 C36 C33 119.80(19) . . ? C37 C36 C33 122.62(19) . . ? C38 C37 C36 118.9(2) . . ? C38 C37 H37 120.5 . . ? C36 C37 H37 120.5 . . ? C39 C38 C37 119.0(2) . . ? C39 C38 H38 120.5 . . ? C37 C38 H38 120.5 . . ? N6 C39 C38 124.0(2) . . ? N6 C39 H39 118.0 . . ? C38 C39 H39 118.0 . . ? N6 C40 C36 124.3(2) . . ? N6 C40 H40 117.9 . . ? C36 C40 H40 117.9 . . ? C1 N1 C4 106.25(18) . . ? C1 N1 Ni1 124.69(16) . . ? C4 N1 Ni1 128.28(14) . . ? C9 N2 C6 105.91(17) . . ? C9 N2 Ni1 126.71(15) . . ? C6 N2 Ni1 127.18(14) . . ? C19 N3 C20 116.0(2) . . ? C21 N4 C24 105.47(17) . . ? C21 N4 Ni1 127.73(14) . . ? C24 N4 Ni1 126.23(14) . . ? C29 N5 C26 105.75(17) . . ? C29 N5 Ni1 127.43(14) . . ? C26 N5 Ni1 126.82(14) . . ? C39 N6 C40 116.17(19) . . ? C39 N6 Ni1 124.78(14) . 2_546 ? C40 N6 Ni1 118.70(15) . 2_546 ? N2 Ni1 N1 88.15(7) . . ? N2 Ni1 N5 92.40(7) . . ? N1 Ni1 N5 90.19(7) . . ? N2 Ni1 N4 177.64(7) . . ? N1 Ni1 N4 93.36(7) . . ? N5 Ni1 N4 89.42(7) . . ? N2 Ni1 N6 88.22(7) . 2_556 ? N1 Ni1 N6 90.78(7) . 2_556 ? N5 Ni1 N6 178.87(7) . 2_556 ? N4 Ni1 N6 89.94(7) . 2_556 ? Cl3 C41 Cl2 110.47(14) . . ? Cl3 C41 Cl1 110.97(14) . . ? Cl2 C41 Cl1 109.14(14) . . ? Cl3 C41 H41 108.7 . . ? Cl2 C41 H41 108.7 . . ? Cl1 C41 H41 108.7 . . ? 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 N1 C1 C2 C3 0.9(4) . . . . ? C1 C2 C3 C4 -1.7(4) . . . . ? C2 C3 C4 C5 -178.1(3) . . . . ? C2 C3 C4 N1 2.0(3) . . . . ? N1 C4 C5 C6 -2.9(3) . . . . ? C3 C4 C5 C6 177.2(2) . . . . ? N1 C4 C5 C10 175.76(19) . . . . ? C3 C4 C5 C10 -4.2(3) . . . . ? C4 C5 C6 N2 8.9(3) . . . . ? C10 C5 C6 N2 -169.75(18) . . . . ? C4 C5 C6 C7 -165.7(2) . . . . ? C10 C5 C6 C7 15.7(3) . . . . ? N2 C6 C7 C8 -0.5(3) . . . . ? C5 C6 C7 C8 174.9(2) . . . . ? C6 C7 C8 C9 0.8(3) . . . . ? C7 C8 C9 N2 -1.0(3) . . . . ? C4 C5 C10 C15 -122.1(2) . . . . ? C6 C5 C10 C15 56.6(3) . . . . ? C4 C5 C10 C11 56.2(3) . . . . ? C6 C5 C10 C11 -125.1(2) . . . . ? C15 C10 C11 C12 -2.0(3) . . . . ? C5 C10 C11 C12 179.7(2) . . . . ? C10 C11 C12 C13 1.0(3) . . . . ? C11 C12 C13 C14 1.2(3) . . . . ? C11 C12 C13 C16 179.4(2) . . . . ? C12 C13 C14 C15 -2.3(4) . . . . ? C16 C13 C14 C15 179.4(2) . . . . ? C13 C14 C15 C10 1.3(4) . . . . ? C11 C10 C15 C14 0.9(4) . . . . ? C5 C10 C15 C14 179.3(2) . . . . ? C12 C13 C16 C17 -25.7(3) . . . . ? C14 C13 C16 C17 152.4(2) . . . . ? C12 C13 C16 C20 156.3(2) . . . . ? C14 C13 C16 C20 -25.5(3) . . . . ? C20 C16 C17 C18 2.5(3) . . . . ? C13 C16 C17 C18 -175.4(2) . . . . ? C16 C17 C18 C19 2.4(4) . . . . ? C17 C18 C19 N3 -4.5(4) . . . . ? C17 C16 C20 N3 -6.1(3) . . . . ? C13 C16 C20 N3 171.9(2) . . . . ? N4 C21 C22 C23 1.0(3) . . . . ? C21 C22 C23 C24 -0.6(3) . . . . ? C22 C23 C24 C25 176.6(2) . . . . ? C22 C23 C24 N4 0.0(3) . . . . ? N4 C24 C25 C26 -2.1(3) . . . . ? C23 C24 C25 C26 -178.2(2) . . . . ? N4 C24 C25 C30 178.64(18) . . . . ? C23 C24 C25 C30 2.6(3) . . . . ? C24 C25 C26 N5 1.5(3) . . . . ? C30 C25 C26 N5 -179.23(18) . . . . ? C24 C25 C26 C27 -172.1(2) . . . . ? C30 C25 C26 C27 7.1(3) . . . . ? C25 C26 C27 C28 174.0(2) . . . . ? N5 C26 C27 C28 -0.5(2) . . . . ? C26 C27 C28 C29 0.6(2) . . . . ? C27 C28 C29 N5 -0.5(3) . . . . ? C24 C25 C30 C31 74.5(3) . . . . ? C26 C25 C30 C31 -104.9(2) . . . . ? C24 C25 C30 C35 -106.4(2) . . . . ? C26 C25 C30 C35 74.2(3) . . . . ? C35 C30 C31 C32 -0.1(4) . . . . ? C25 C30 C31 C32 179.0(2) . . . . ? C30 C31 C32 C33 -0.2(4) . . . . ? C31 C32 C33 C34 0.7(3) . . . . ? C31 C32 C33 C36 -177.5(2) . . . . ? C32 C33 C34 C35 -0.8(3) . . . . ? C36 C33 C34 C35 177.3(2) . . . . ? C33 C34 C35 C30 0.5(4) . . . . ? C31 C30 C35 C34 0.0(4) . . . . ? C25 C30 C35 C34 -179.2(2) . . . . ? C34 C33 C36 C40 147.8(2) . . . . ? C32 C33 C36 C40 -34.1(3) . . . . ? C34 C33 C36 C37 -32.5(3) . . . . ? C32 C33 C36 C37 145.6(2) . . . . ? C40 C36 C37 C38 -1.3(3) . . . . ? C33 C36 C37 C38 179.0(2) . . . . ? C36 C37 C38 C39 0.8(4) . . . . ? C37 C38 C39 N6 0.9(4) . . . . ? C37 C36 C40 N6 0.2(3) . . . . ? C33 C36 C40 N6 179.84(19) . . . . ? C2 C1 N1 C4 0.4(3) . . . . ? C2 C1 N1 Ni1 -170.2(2) . . . . ? C5 C4 N1 C1 178.6(2) . . . . ? C3 C4 N1 C1 -1.4(3) . . . . ? C5 C4 N1 Ni1 -11.2(3) . . . . ? C3 C4 N1 Ni1 168.74(16) . . . . ? C8 C9 N2 C6 0.7(3) . . . . ? C8 C9 N2 Ni1 -174.47(16) . . . . ? C5 C6 N2 C9 -175.5(2) . . . . ? C7 C6 N2 C9 -0.1(2) . . . . ? C5 C6 N2 Ni1 -0.4(3) . . . . ? C7 C6 N2 Ni1 174.99(15) . . . . ? C18 C19 N3 C20 1.3(4) . . . . ? C16 C20 N3 C19 4.2(3) . . . . ? C22 C21 N4 C24 -1.0(3) . . . . ? C22 C21 N4 Ni1 -172.65(16) . . . . ? C25 C24 N4 C21 -176.1(2) . . . . ? C23 C24 N4 C21 0.6(2) . . . . ? C25 C24 N4 Ni1 -4.3(3) . . . . ? C23 C24 N4 Ni1 172.41(14) . . . . ? C28 C29 N5 C26 0.2(2) . . . . ? C28 C29 N5 Ni1 -179.65(15) . . . . ? C25 C26 N5 C29 -174.40(19) . . . . ? C27 C26 N5 C29 0.2(2) . . . . ? C25 C26 N5 Ni1 5.4(3) . . . . ? C27 C26 N5 Ni1 -179.99(13) . . . . ? C38 C39 N6 C40 -2.0(3) . . . . ? C38 C39 N6 Ni1 171.12(19) . . . 2_546 ? C36 C40 N6 C39 1.4(3) . . . . ? C36 C40 N6 Ni1 -172.10(17) . . . 2_546 ? C9 N2 Ni1 N1 165.69(19) . . . . ? C6 N2 Ni1 N1 -8.46(17) . . . . ? C9 N2 Ni1 N5 75.58(19) . . . . ? C6 N2 Ni1 N5 -98.57(17) . . . . ? C9 N2 Ni1 N4 -64.6(17) . . . . ? C6 N2 Ni1 N4 121.3(16) . . . . ? C9 N2 Ni1 N6 -103.48(19) . . . 2_556 ? C6 N2 Ni1 N6 82.38(17) . . . 2_556 ? C1 N1 Ni1 N2 -177.4(2) . . . . ? C4 N1 Ni1 N2 14.09(19) . . . . ? C1 N1 Ni1 N5 -85.0(2) . . . . ? C4 N1 Ni1 N5 106.48(19) . . . . ? C1 N1 Ni1 N4 4.4(2) . . . . ? C4 N1 Ni1 N4 -164.09(18) . . . . ? C1 N1 Ni1 N6 94.4(2) . . . 2_556 ? C4 N1 Ni1 N6 -74.10(19) . . . 2_556 ? C29 N5 Ni1 N2 -6.86(18) . . . . ? C26 N5 Ni1 N2 173.37(16) . . . . ? C29 N5 Ni1 N1 -95.01(18) . . . . ? C26 N5 Ni1 N1 85.21(16) . . . . ? C29 N5 Ni1 N4 171.63(18) . . . . ? C26 N5 Ni1 N4 -8.15(16) . . . . ? C29 N5 Ni1 N6 116(3) . . . 2_556 ? C26 N5 Ni1 N6 -64(4) . . . 2_556 ? C21 N4 Ni1 N2 -42.2(17) . . . . ? C24 N4 Ni1 N2 147.8(16) . . . . ? C21 N4 Ni1 N1 87.41(19) . . . . ? C24 N4 Ni1 N1 -82.59(16) . . . . ? C21 N4 Ni1 N5 177.57(18) . . . . ? C24 N4 Ni1 N5 7.57(16) . . . . ? C21 N4 Ni1 N6 -3.36(18) . . . 2_556 ? C24 N4 Ni1 N6 -173.36(16) . . . 2_556 ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 30.11 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 1.210 _refine_diff_density_min -1.172 _refine_diff_density_rms 0.077 _database_code_depnum_ccdc_archive 'CCDC 927326' ####################################################################### # # 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_compound10 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C83 H81 N19 Ni2 O5' _chemical_formula_weight 1542.09 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' 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 'Cc ' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' 'x, -y, z+1/2' 'x+1/2, y+1/2, z' 'x+1/2, -y+1/2, z+1/2' _cell_length_a 23.9544(6) _cell_length_b 9.6535(2) _cell_length_c 17.2072(4) _cell_angle_alpha 90.00 _cell_angle_beta 107.043(2) _cell_angle_gamma 90.00 _cell_volume 3804.32(15) _cell_formula_units_Z 2 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 9926 _cell_measurement_theta_min 2.29 _cell_measurement_theta_max 30.00 _exptl_crystal_description prism _exptl_crystal_colour orange _exptl_crystal_size_max 0.10 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.346 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1616 _exptl_absorpt_coefficient_mu 0.561 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9460 _exptl_absorpt_correction_T_max 0.9460 _exptl_absorpt_process_details sadabs _exptl_special_details ; A DMF molecule and two MeOH molecules share the same site. ; _diffrn_ambient_temperature 173(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_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 70144 _diffrn_reflns_av_R_equivalents 0.0332 _diffrn_reflns_av_sigmaI/netI 0.0283 _diffrn_reflns_limit_h_min -33 _diffrn_reflns_limit_h_max 33 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_theta_min 1.78 _diffrn_reflns_theta_max 30.06 _reflns_number_total 10923 _reflns_number_gt 10180 _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^)+(0.0533P)^2^+0.6138P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.038(6) _refine_ls_number_reflns 10923 _refine_ls_number_parameters 534 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0348 _refine_ls_R_factor_gt 0.0311 _refine_ls_wR_factor_ref 0.0837 _refine_ls_wR_factor_gt 0.0815 _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 C1 C 1.03734(8) 0.19580(19) 0.28301(10) 0.0289(3) Uani 1 1 d . . . H1 H 1.0071 0.1732 0.2369 0.035 Uiso 1 1 calc R . . C2 C 1.08837(10) 0.2666(3) 0.28115(13) 0.0436(5) Uani 1 1 d . . . H2 H 1.0972 0.2999 0.2354 0.052 Uiso 1 1 calc R . . C3 C 1.12232(8) 0.2764(2) 0.36026(12) 0.0365(4) Uani 1 1 d . . . H3 H 1.1592 0.3163 0.3787 0.044 Uiso 1 1 calc R . . C4 C 1.09048(7) 0.21424(17) 0.40877(10) 0.0235(3) Uani 1 1 d . . . C5 C 1.10910(7) 0.19958(17) 0.49370(10) 0.0263(3) Uani 1 1 d . . . C6 C 1.07804(8) 0.1377(2) 0.54185(11) 0.0281(4) Uani 1 1 d . . . C7 C 1.09305(10) 0.1399(3) 0.62864(12) 0.0431(5) Uani 1 1 d . . . H7 H 1.1272 0.1758 0.6638 0.052 Uiso 1 1 calc R . . C8 C 1.04846(11) 0.0799(3) 0.65057(12) 0.0488(6) Uani 1 1 d . . . H8 H 1.0458 0.0676 0.7030 0.059 Uiso 1 1 calc R . . C9 C 1.00658(9) 0.0401(2) 0.57621(11) 0.0381(4) Uani 1 1 d . . . H9 H 0.9714 -0.0034 0.5735 0.046 Uiso 1 1 calc R . . C10 C 1.16803(7) 0.25741(18) 0.53801(10) 0.0281(3) Uani 1 1 d . . . C11 C 1.17738(8) 0.3999(2) 0.54463(12) 0.0351(4) Uani 1 1 d . . . H11 H 1.1468 0.4603 0.5213 0.042 Uiso 1 1 calc R . . C12 C 1.23193(9) 0.45230(19) 0.58576(13) 0.0355(4) Uani 1 1 d . . . H12 H 1.2376 0.5475 0.5914 0.043 Uiso 1 1 calc R . . C13 C 1.27785(7) 0.36317(18) 0.61837(10) 0.0277(3) Uani 1 1 d . . . C14 C 1.26973(8) 0.22049(19) 0.61129(12) 0.0327(4) Uani 1 1 d . . . H14 H 1.3009 0.1606 0.6327 0.039 Uiso 1 1 calc R . . C15 C 1.21477(8) 0.1685(2) 0.57193(12) 0.0347(4) Uani 1 1 d . . . H15 H 1.2090 0.0731 0.5681 0.042 Uiso 1 1 calc R . . C16 C 1.37107(8) 0.36941(19) 0.73034(11) 0.0258(3) Uani 1 1 d . . . H16 H 1.3656 0.2864 0.7545 0.031 Uiso 1 1 calc R . . C17 C 1.40765(9) 0.5601(2) 0.70530(13) 0.0418(5) Uani 1 1 d . . . H17 H 1.4330 0.6344 0.7092 0.050 Uiso 1 1 calc R . . C18 C 1.35693(11) 0.5425(2) 0.64444(14) 0.0491(6) Uani 1 1 d . . . H18 H 1.3411 0.6018 0.6009 0.059 Uiso 1 1 calc R . . C19 C 0.94187(8) 0.36063(18) 0.38520(12) 0.0329(4) Uani 1 1 d . . . H19 H 0.9791 0.3850 0.3836 0.039 Uiso 1 1 calc R . . C20 C 0.89500(11) 0.45487(19) 0.37323(17) 0.0464(6) Uani 1 1 d . . . H20 H 0.8959 0.5494 0.3633 0.056 Uiso 1 1 calc R . . C21 C 0.84807(9) 0.37953(19) 0.37909(14) 0.0384(4) Uani 1 1 d . . . H21 H 0.8107 0.4128 0.3736 0.046 Uiso 1 1 calc R . . C22 C 0.86768(7) 0.23977(17) 0.39520(11) 0.0255(3) Uani 1 1 d . . . C23 C 0.83352(7) 0.12471(16) 0.40215(10) 0.0234(3) Uani 1 1 d . . . C24 C 0.85258(6) -0.01252(16) 0.41650(10) 0.0222(3) Uani 1 1 d . . . C25 C 0.82066(7) -0.12372(17) 0.43890(11) 0.0273(3) Uani 1 1 d . . . H25 H 0.7820 -0.1215 0.4394 0.033 Uiso 1 1 calc R . . C26 C 0.85814(8) -0.23372(18) 0.45946(12) 0.0323(4) Uani 1 1 d . . . H26 H 0.8503 -0.3204 0.4774 0.039 Uiso 1 1 calc R . . C27 C 0.91151(7) -0.18797(17) 0.44774(10) 0.0272(3) Uani 1 1 d . . . H27 H 0.9447 -0.2431 0.4571 0.033 Uiso 1 1 calc R . . C28 C 0.77035(7) 0.15271(17) 0.39321(10) 0.0248(3) Uani 1 1 d . . . C29 C 0.75444(7) 0.23730(18) 0.44876(11) 0.0275(3) Uani 1 1 d . . . H29 H 0.7831 0.2761 0.4920 0.033 Uiso 1 1 calc R . . C30 C 0.69585(7) 0.26403(18) 0.43990(11) 0.0279(3) Uani 1 1 d . . . H30 H 0.6853 0.3185 0.4779 0.034 Uiso 1 1 calc R . . C31 C 0.65336(7) 0.20935(17) 0.37443(10) 0.0246(3) Uani 1 1 d . . . C32 C 0.66845(8) 0.12462(19) 0.31828(11) 0.0302(3) Uani 1 1 d . . . H32 H 0.6397 0.0879 0.2744 0.036 Uiso 1 1 calc R . . C33 C 0.72689(8) 0.09553(19) 0.32845(11) 0.0300(3) Uani 1 1 d . . . H33 H 0.7372 0.0374 0.2918 0.036 Uiso 1 1 calc R . . C34 C 0.57347(7) 0.36616(18) 0.38193(11) 0.0273(3) Uani 1 1 d . . . H34 H 0.5973 0.4422 0.4014 0.033 Uiso 1 1 calc R . . C35 C 0.49888(7) 0.23444(19) 0.33907(12) 0.0314(3) Uani 1 1 d . . . H35 H 0.4605 0.2033 0.3236 0.038 Uiso 1 1 calc R . . C36 C 0.54579(8) 0.15641(19) 0.33668(12) 0.0323(4) Uani 1 1 d . . . H36 H 0.5456 0.0649 0.3197 0.039 Uiso 1 1 calc R . . N1 N 1.03741(6) 0.16508(14) 0.35833(8) 0.0221(2) Uani 1 1 d . . . N2 N 1.02347(8) 0.07221(16) 0.51117(10) 0.0273(3) Uani 1 1 d . . . N3 N 1.33389(6) 0.41889(16) 0.66064(9) 0.0284(3) Uani 1 1 d . . . N4 N 1.41612(7) 0.45258(15) 0.76017(10) 0.0249(3) Uani 1 1 d . . . N5 N 0.92626(6) 0.23272(14) 0.39899(9) 0.0242(3) Uani 1 1 d . . . N6 N 0.90884(6) -0.05776(13) 0.42191(8) 0.0220(3) Uani 1 1 d . . . N7 N 0.59328(6) 0.24148(15) 0.36469(9) 0.0261(3) Uani 1 1 d . . . N8 N 0.51622(6) 0.36605(15) 0.36766(9) 0.0253(3) Uani 1 1 d . . . Ni1 Ni 0.972438(8) 0.055049(18) 0.389615(9) 0.01953(5) Uani 1 1 d . . . C37 C 0.40350(16) 0.8730(3) 0.58983(17) 0.0663(8) Uani 1 1 d . . . H37 H 0.4087 0.7954 0.5607 0.080 Uiso 1 1 calc R . . C38 C 0.44193(18) 1.0820(4) 0.6579(3) 0.0784(10) Uani 1 1 d . . . H38A H 0.4123 1.0669 0.6845 0.118 Uiso 1 1 calc R . . H38B H 0.4313 1.1598 0.6219 0.118 Uiso 1 1 calc R . . H38C H 0.4786 1.1002 0.6980 0.118 Uiso 1 1 calc R . . C39 C 0.5017(2) 0.9467(5) 0.5919(3) 0.0882(13) Uani 1 1 d . . . H39A H 0.5337 0.9404 0.6408 0.132 Uiso 1 1 calc R . . H39B H 0.5071 1.0256 0.5609 0.132 Uiso 1 1 calc R . . H39C H 0.5001 0.8641 0.5602 0.132 Uiso 1 1 calc R . . N9 N 0.44721(11) 0.9617(2) 0.61262(14) 0.0571(6) Uani 1 1 d . . . O1 O 0.35643(13) 0.8854(3) 0.60433(16) 0.0890(8) Uani 1 1 d . . . C41 C 0.1683(4) 0.1665(7) 0.1632(4) 0.0779(19) Uani 0.50 1 d P A 1 H41 H 0.1309 0.1376 0.1614 0.094 Uiso 0.50 1 calc PR A 1 C42 C 0.2715(5) 0.2114(12) 0.2339(8) 0.094(4) Uiso 0.50 1 d P A 1 H42A H 0.2809 0.2123 0.1834 0.141 Uiso 0.50 1 calc PR A 1 H42B H 0.3033 0.1713 0.2755 0.141 Uiso 0.50 1 calc PR A 1 H42C H 0.2649 0.3045 0.2488 0.141 Uiso 0.50 1 calc PR A 1 C43 C 0.2048(4) 0.0293(9) 0.2859(5) 0.090(2) Uani 0.50 1 d P A 1 H43A H 0.1639 0.0270 0.2816 0.135 Uiso 0.50 1 calc PR A 1 H43B H 0.2264 0.0621 0.3389 0.135 Uiso 0.50 1 calc PR A 1 H43C H 0.2178 -0.0622 0.2779 0.135 Uiso 0.50 1 calc PR A 1 N10 N 0.2145(3) 0.1225(6) 0.2240(4) 0.0782(16) Uani 0.50 1 d P A 1 O2 O 0.1751(4) 0.2439(7) 0.1107(4) 0.107(2) Uani 0.50 1 d P A 1 C44 C 0.2676(5) 0.1519(11) 0.2275(5) 0.084(2) Uani 0.50 1 d P B 2 H44A H 0.2957 0.2161 0.2592 0.126 Uiso 0.50 1 calc PR B 2 H44B H 0.2838 0.0602 0.2344 0.126 Uiso 0.50 1 calc PR B 2 H44C H 0.2332 0.1538 0.2453 0.126 Uiso 0.50 1 calc PR B 2 O3 O 0.25305(19) 0.1889(5) 0.1458(2) 0.0624(10) Uani 0.50 1 d P B 2 H3A H 0.2792 0.1647 0.1269 0.094 Uiso 0.50 1 calc PR B 2 C45 C 0.0911(5) 0.2448(11) 0.0702(5) 0.108(3) Uani 0.50 1 d P C 2 H45A H 0.0803 0.1794 0.1052 0.162 Uiso 0.50 1 calc PR C 2 H45B H 0.1023 0.1961 0.0285 0.162 Uiso 0.50 1 calc PR C 2 H45C H 0.0585 0.3040 0.0456 0.162 Uiso 0.50 1 calc PR C 2 O4 O 0.1383(3) 0.3256(6) 0.1159(4) 0.0962(16) Uani 0.50 1 d P C 2 H4 H 0.1600 0.2776 0.1516 0.144 Uiso 0.50 1 calc PR C 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 C1 0.0230(8) 0.0358(9) 0.0274(7) -0.0018(6) 0.0066(6) -0.0047(7) C2 0.0384(11) 0.0610(13) 0.0349(9) 0.0017(9) 0.0163(8) -0.0174(10) C3 0.0254(9) 0.0490(11) 0.0380(9) -0.0040(8) 0.0137(7) -0.0147(8) C4 0.0119(7) 0.0263(7) 0.0308(8) -0.0007(6) 0.0038(6) -0.0025(6) C5 0.0152(7) 0.0276(7) 0.0320(8) -0.0016(6) 0.0006(6) -0.0008(6) C6 0.0185(8) 0.0346(9) 0.0260(8) 0.0020(6) -0.0018(6) -0.0050(7) C7 0.0356(11) 0.0594(13) 0.0269(8) 0.0036(8) -0.0027(8) -0.0177(10) C8 0.0466(13) 0.0704(15) 0.0257(8) 0.0020(9) 0.0047(9) -0.0218(11) C9 0.0313(10) 0.0519(12) 0.0295(8) 0.0008(7) 0.0062(7) -0.0148(8) C10 0.0181(7) 0.0327(8) 0.0287(8) -0.0004(6) -0.0006(6) -0.0046(6) C11 0.0201(8) 0.0326(8) 0.0436(10) 0.0016(7) -0.0046(7) -0.0010(7) C12 0.0230(9) 0.0316(9) 0.0422(10) -0.0001(7) -0.0055(7) -0.0049(7) C13 0.0170(7) 0.0353(9) 0.0264(7) 0.0013(6) -0.0004(6) -0.0067(6) C14 0.0173(7) 0.0324(9) 0.0406(9) 0.0042(7) -0.0034(7) -0.0017(6) C15 0.0207(8) 0.0299(8) 0.0455(10) 0.0016(7) -0.0024(7) -0.0042(7) C16 0.0168(8) 0.0289(8) 0.0293(8) 0.0012(6) 0.0030(6) -0.0031(6) C17 0.0299(10) 0.0490(11) 0.0373(9) 0.0127(8) -0.0043(8) -0.0203(8) C18 0.0404(12) 0.0523(13) 0.0391(10) 0.0201(9) -0.0124(9) -0.0238(10) C19 0.0288(9) 0.0252(8) 0.0497(10) -0.0066(7) 0.0192(8) -0.0049(7) C20 0.0471(13) 0.0217(8) 0.0817(17) 0.0006(9) 0.0365(12) 0.0022(8) C21 0.0326(10) 0.0245(8) 0.0650(13) 0.0023(8) 0.0250(9) 0.0063(7) C22 0.0186(8) 0.0241(7) 0.0358(8) -0.0023(6) 0.0111(7) 0.0013(6) C23 0.0156(7) 0.0248(7) 0.0311(7) -0.0019(6) 0.0090(6) 0.0020(6) C24 0.0144(7) 0.0234(7) 0.0299(7) -0.0020(6) 0.0084(6) 0.0013(6) C25 0.0176(7) 0.0273(8) 0.0399(8) -0.0009(6) 0.0128(6) -0.0005(6) C26 0.0308(9) 0.0245(7) 0.0471(10) 0.0033(7) 0.0201(8) 0.0006(7) C27 0.0211(7) 0.0254(7) 0.0363(8) 0.0023(6) 0.0104(6) 0.0050(6) C28 0.0158(7) 0.0247(7) 0.0354(8) 0.0004(6) 0.0100(6) 0.0041(6) C29 0.0163(7) 0.0328(8) 0.0330(8) -0.0024(6) 0.0065(6) 0.0046(6) C30 0.0200(8) 0.0311(8) 0.0337(8) -0.0038(6) 0.0095(6) 0.0062(6) C31 0.0138(7) 0.0252(7) 0.0353(8) 0.0025(6) 0.0083(6) 0.0045(6) C32 0.0189(8) 0.0334(9) 0.0373(9) -0.0072(7) 0.0065(7) 0.0016(6) C33 0.0212(8) 0.0311(8) 0.0387(9) -0.0073(7) 0.0106(7) 0.0040(6) C34 0.0152(7) 0.0272(8) 0.0391(8) -0.0043(6) 0.0073(6) 0.0040(6) C35 0.0166(7) 0.0333(8) 0.0456(9) -0.0023(7) 0.0112(7) -0.0027(6) C36 0.0206(8) 0.0292(8) 0.0484(10) -0.0049(7) 0.0123(7) -0.0027(6) N1 0.0125(6) 0.0274(6) 0.0249(6) 0.0000(5) 0.0031(5) 0.0005(5) N2 0.0197(8) 0.0323(7) 0.0280(7) 0.0017(6) 0.0041(6) -0.0058(6) N3 0.0168(7) 0.0362(7) 0.0272(6) 0.0034(6) -0.0010(5) -0.0074(6) N4 0.0140(7) 0.0317(8) 0.0266(7) 0.0010(5) 0.0021(5) -0.0017(5) N5 0.0171(6) 0.0240(6) 0.0328(7) -0.0049(5) 0.0090(5) -0.0024(5) N6 0.0127(6) 0.0239(6) 0.0291(6) -0.0015(5) 0.0058(5) 0.0017(5) N7 0.0127(6) 0.0269(7) 0.0391(8) -0.0028(6) 0.0081(5) 0.0029(5) N8 0.0131(6) 0.0310(7) 0.0316(6) -0.0003(5) 0.0060(5) 0.0029(5) Ni1 0.00960(7) 0.02373(8) 0.02447(8) -0.00108(8) 0.00377(6) 0.00085(8) C37 0.084(2) 0.0510(15) 0.0511(14) -0.0080(11) 0.0009(14) -0.0122(14) C38 0.063(2) 0.0594(16) 0.096(3) -0.0332(17) -0.0011(18) 0.0034(15) C39 0.069(2) 0.117(4) 0.076(2) -0.0143(19) 0.018(2) 0.0058(19) N9 0.0536(13) 0.0515(11) 0.0561(12) -0.0143(9) 0.0006(10) 0.0059(10) O1 0.0776(17) 0.1061(19) 0.0740(14) -0.0009(14) 0.0077(13) -0.0367(15) C41 0.113(6) 0.059(3) 0.079(4) -0.003(3) 0.054(4) 0.005(4) C43 0.090(6) 0.093(5) 0.089(5) 0.024(4) 0.027(4) 0.018(4) N10 0.096(5) 0.074(4) 0.070(3) 0.001(3) 0.033(3) 0.007(3) O2 0.169(7) 0.091(4) 0.080(3) 0.020(3) 0.068(4) 0.002(4) C44 0.097(6) 0.085(6) 0.085(5) -0.015(5) 0.049(4) -0.017(5) O3 0.062(2) 0.061(2) 0.058(2) 0.0129(17) 0.0078(18) 0.0136(19) C45 0.144(8) 0.128(7) 0.066(4) -0.039(4) 0.055(5) -0.057(6) O4 0.099(4) 0.083(4) 0.111(4) 0.017(3) 0.038(3) -0.023(3) _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 C1 N1 1.329(2) . ? C1 C2 1.409(3) . ? C1 H1 0.9300 . ? C2 C3 1.369(3) . ? C2 H2 0.9300 . ? C3 C4 1.418(2) . ? C3 H3 0.9300 . ? C4 N1 1.396(2) . ? C4 C5 1.404(2) . ? C5 C6 1.399(3) . ? C5 C10 1.502(2) . ? C6 N2 1.408(2) . ? C6 C7 1.430(3) . ? C7 C8 1.362(3) . ? C7 H7 0.9300 . ? C8 C9 1.428(3) . ? C8 H8 0.9300 . ? C9 N2 1.333(3) . ? C9 H9 0.9300 . ? C10 C11 1.393(3) . ? C10 C15 1.396(3) . ? C11 C12 1.386(3) . ? C11 H11 0.9300 . ? C12 C13 1.380(3) . ? C12 H12 0.9300 . ? C13 C14 1.391(3) . ? C13 N3 1.431(2) . ? C14 C15 1.386(2) . ? C14 H14 0.9300 . ? C15 H15 0.9300 . ? C16 N4 1.322(2) . ? C16 N3 1.354(2) . ? C16 H16 0.9300 . ? C17 C18 1.362(3) . ? C17 N4 1.377(2) . ? C17 H17 0.9300 . ? C18 N3 1.377(2) . ? C18 H18 0.9300 . ? C19 N5 1.331(2) . ? C19 C20 1.413(3) . ? C19 H19 0.9300 . ? C20 C21 1.367(3) . ? C20 H20 0.9300 . ? C21 C22 1.429(2) . ? C21 H21 0.9300 . ? C22 N5 1.387(2) . ? C22 C23 1.405(2) . ? C23 C24 1.399(2) . ? C23 C28 1.500(2) . ? C24 N6 1.3935(19) . ? C24 C25 1.435(2) . ? C25 C26 1.368(2) . ? C25 H25 0.9300 . ? C26 C27 1.422(2) . ? C26 H26 0.9300 . ? C27 N6 1.329(2) . ? C27 H27 0.9300 . ? C28 C29 1.392(2) . ? C28 C33 1.396(2) . ? C29 C30 1.391(2) . ? C29 H29 0.9300 . ? C30 C31 1.383(2) . ? C30 H30 0.9300 . ? C31 C32 1.392(2) . ? C31 N7 1.4332(19) . ? C32 C33 1.388(2) . ? C32 H32 0.9300 . ? C33 H33 0.9300 . ? C34 N8 1.320(2) . ? C34 N7 1.358(2) . ? C34 H34 0.9300 . ? C35 C36 1.363(2) . ? C35 N8 1.382(2) . ? C35 H35 0.9300 . ? C36 N7 1.371(2) . ? C36 H36 0.9300 . ? N1 Ni1 2.0813(13) . ? N2 Ni1 2.0971(17) . ? N4 Ni1 2.2417(17) 4 ? N5 Ni1 2.0726(14) . ? N6 Ni1 2.0765(13) . ? N8 Ni1 2.1918(14) 3_455 ? Ni1 N8 2.1918(14) 3_545 ? Ni1 N4 2.2417(17) 4_454 ? C37 O1 1.230(4) . ? C37 N9 1.320(4) . ? C37 H37 0.9300 . ? C38 N9 1.424(4) . ? C38 H38A 0.9600 . ? C38 H38B 0.9600 . ? C38 H38C 0.9600 . ? C39 N9 1.457(5) . ? C39 H39A 0.9600 . ? C39 H39B 0.9600 . ? C39 H39C 0.9600 . ? C41 O2 1.219(8) . ? C41 N10 1.348(10) . ? C41 H41 0.9300 . ? C42 N10 1.579(13) . ? C42 H42A 0.9600 . ? C42 H42B 0.9600 . ? C42 H42C 0.9600 . ? C43 N10 1.464(10) . ? C43 H43A 0.9600 . ? C43 H43B 0.9600 . ? C43 H43C 0.9600 . ? C44 O3 1.392(10) . ? C44 H44A 0.9600 . ? C44 H44B 0.9600 . ? C44 H44C 0.9600 . ? O3 H3A 0.8200 . ? C45 O4 1.409(10) . ? C45 H45A 0.9600 . ? C45 H45B 0.9600 . ? C45 H45C 0.9600 . ? O4 H4 0.8200 . ? 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 C1 C2 112.16(16) . . ? N1 C1 H1 123.9 . . ? C2 C1 H1 123.9 . . ? C3 C2 C1 106.11(17) . . ? C3 C2 H2 126.9 . . ? C1 C2 H2 126.9 . . ? C2 C3 C4 106.90(16) . . ? C2 C3 H3 126.6 . . ? C4 C3 H3 126.6 . . ? N1 C4 C5 124.50(14) . . ? N1 C4 C3 109.08(15) . . ? C5 C4 C3 126.40(15) . . ? C6 C5 C4 126.68(15) . . ? C6 C5 C10 116.22(15) . . ? C4 C5 C10 117.10(15) . . ? C5 C6 N2 124.47(16) . . ? C5 C6 C7 126.70(17) . . ? N2 C6 C7 108.65(17) . . ? C8 C7 C6 107.79(18) . . ? C8 C7 H7 126.1 . . ? C6 C7 H7 126.1 . . ? C7 C8 C9 105.56(18) . . ? C7 C8 H8 127.2 . . ? C9 C8 H8 127.2 . . ? N2 C9 C8 112.53(18) . . ? N2 C9 H9 123.7 . . ? C8 C9 H9 123.7 . . ? C11 C10 C15 118.90(16) . . ? C11 C10 C5 120.88(16) . . ? C15 C10 C5 120.20(15) . . ? C12 C11 C10 120.44(17) . . ? C12 C11 H11 119.8 . . ? C10 C11 H11 119.8 . . ? C13 C12 C11 120.01(17) . . ? C13 C12 H12 120.0 . . ? C11 C12 H12 120.0 . . ? C12 C13 C14 120.49(15) . . ? C12 C13 N3 119.32(16) . . ? C14 C13 N3 120.19(16) . . ? C15 C14 C13 119.33(17) . . ? C15 C14 H14 120.3 . . ? C13 C14 H14 120.3 . . ? C14 C15 C10 120.79(17) . . ? C14 C15 H15 119.6 . . ? C10 C15 H15 119.6 . . ? N4 C16 N3 112.32(16) . . ? N4 C16 H16 123.8 . . ? N3 C16 H16 123.8 . . ? C18 C17 N4 110.62(17) . . ? C18 C17 H17 124.7 . . ? N4 C17 H17 124.7 . . ? C17 C18 N3 105.81(17) . . ? C17 C18 H18 127.1 . . ? N3 C18 H18 127.1 . . ? N5 C19 C20 111.75(16) . . ? N5 C19 H19 124.1 . . ? C20 C19 H19 124.1 . . ? C21 C20 C19 106.39(17) . . ? C21 C20 H20 126.8 . . ? C19 C20 H20 126.8 . . ? C20 C21 C22 106.62(17) . . ? C20 C21 H21 126.7 . . ? C22 C21 H21 126.7 . . ? N5 C22 C23 124.30(15) . . ? N5 C22 C21 109.02(15) . . ? C23 C22 C21 126.61(16) . . ? C24 C23 C22 126.52(14) . . ? C24 C23 C28 117.12(14) . . ? C22 C23 C28 116.35(14) . . ? N6 C24 C23 124.59(14) . . ? N6 C24 C25 109.19(14) . . ? C23 C24 C25 125.71(14) . . ? C26 C25 C24 106.81(14) . . ? C26 C25 H25 126.6 . . ? C24 C25 H25 126.6 . . ? C25 C26 C27 105.75(15) . . ? C25 C26 H26 127.1 . . ? C27 C26 H26 127.1 . . ? N6 C27 C26 112.59(15) . . ? N6 C27 H27 123.7 . . ? C26 C27 H27 123.7 . . ? C29 C28 C33 119.32(15) . . ? C29 C28 C23 120.40(15) . . ? C33 C28 C23 120.28(14) . . ? C30 C29 C28 120.26(16) . . ? C30 C29 H29 119.9 . . ? C28 C29 H29 119.9 . . ? C31 C30 C29 119.78(15) . . ? C31 C30 H30 120.1 . . ? C29 C30 H30 120.1 . . ? C30 C31 C32 120.73(15) . . ? C30 C31 N7 119.14(14) . . ? C32 C31 N7 120.13(15) . . ? C33 C32 C31 119.26(16) . . ? C33 C32 H32 120.4 . . ? C31 C32 H32 120.4 . . ? C32 C33 C28 120.61(15) . . ? C32 C33 H33 119.7 . . ? C28 C33 H33 119.7 . . ? N8 C34 N7 111.66(15) . . ? N8 C34 H34 124.2 . . ? N7 C34 H34 124.2 . . ? C36 C35 N8 110.76(15) . . ? C36 C35 H35 124.6 . . ? N8 C35 H35 124.6 . . ? C35 C36 N7 105.35(15) . . ? C35 C36 H36 127.3 . . ? N7 C36 H36 127.3 . . ? C1 N1 C4 105.73(13) . . ? C1 N1 Ni1 125.36(11) . . ? C4 N1 Ni1 128.80(11) . . ? C9 N2 C6 105.45(16) . . ? C9 N2 Ni1 125.96(14) . . ? C6 N2 Ni1 127.96(13) . . ? C16 N3 C18 106.63(15) . . ? C16 N3 C13 126.38(15) . . ? C18 N3 C13 126.50(16) . . ? C16 N4 C17 104.59(16) . . ? C16 N4 Ni1 123.43(13) . 4 ? C17 N4 Ni1 129.11(13) . 4 ? C19 N5 C22 106.21(14) . . ? C19 N5 Ni1 124.71(11) . . ? C22 N5 Ni1 126.33(11) . . ? C27 N6 C24 105.65(13) . . ? C27 N6 Ni1 128.21(11) . . ? C24 N6 Ni1 126.07(10) . . ? C34 N7 C36 107.49(14) . . ? C34 N7 C31 124.72(14) . . ? C36 N7 C31 127.80(14) . . ? C34 N8 C35 104.74(14) . . ? C34 N8 Ni1 119.38(12) . 3_455 ? C35 N8 Ni1 135.87(11) . 3_455 ? N5 Ni1 N6 87.88(5) . . ? N5 Ni1 N1 93.12(5) . . ? N6 Ni1 N1 178.85(6) . . ? N5 Ni1 N2 91.46(6) . . ? N6 Ni1 N2 91.92(6) . . ? N1 Ni1 N2 87.48(6) . . ? N5 Ni1 N8 174.58(6) . 3_545 ? N6 Ni1 N8 92.02(5) . 3_545 ? N1 Ni1 N8 87.04(5) . 3_545 ? N2 Ni1 N8 93.96(6) . 3_545 ? N5 Ni1 N4 85.70(5) . 4_454 ? N6 Ni1 N4 88.48(6) . 4_454 ? N1 Ni1 N4 92.16(6) . 4_454 ? N2 Ni1 N4 177.11(6) . 4_454 ? N8 Ni1 N4 88.88(5) 3_545 4_454 ? O1 C37 N9 124.8(3) . . ? O1 C37 H37 117.6 . . ? N9 C37 H37 117.6 . . ? N9 C38 H38A 109.5 . . ? N9 C38 H38B 109.5 . . ? H38A C38 H38B 109.5 . . ? N9 C38 H38C 109.5 . . ? H38A C38 H38C 109.5 . . ? H38B C38 H38C 109.5 . . ? N9 C39 H39A 109.5 . . ? N9 C39 H39B 109.5 . . ? H39A C39 H39B 109.5 . . ? N9 C39 H39C 109.5 . . ? H39A C39 H39C 109.5 . . ? H39B C39 H39C 109.5 . . ? C37 N9 C38 120.1(3) . . ? C37 N9 C39 123.5(3) . . ? C38 N9 C39 116.4(3) . . ? O2 C41 N10 120.7(9) . . ? O2 C41 H41 119.6 . . ? N10 C41 H41 119.6 . . ? C41 N10 C43 119.3(7) . . ? C41 N10 C42 113.5(7) . . ? C43 N10 C42 124.8(7) . . ? O3 C44 H44A 109.5 . . ? O3 C44 H44B 109.5 . . ? H44A C44 H44B 109.5 . . ? O3 C44 H44C 109.5 . . ? H44A C44 H44C 109.5 . . ? H44B C44 H44C 109.5 . . ? C44 O3 H3A 109.5 . . ? O4 C45 H45A 109.5 . . ? O4 C45 H45B 109.5 . . ? H45A C45 H45B 109.5 . . ? O4 C45 H45C 109.5 . . ? H45A C45 H45C 109.5 . . ? H45B C45 H45C 109.5 . . ? C45 O4 H4 109.5 . . ? 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 N1 C1 C2 C3 1.6(3) . . . . ? C1 C2 C3 C4 -1.4(2) . . . . ? C2 C3 C4 N1 0.8(2) . . . . ? C2 C3 C4 C5 179.08(19) . . . . ? N1 C4 C5 C6 -1.6(3) . . . . ? C3 C4 C5 C6 -179.66(19) . . . . ? N1 C4 C5 C10 179.17(15) . . . . ? C3 C4 C5 C10 1.2(3) . . . . ? C4 C5 C6 N2 3.9(3) . . . . ? C10 C5 C6 N2 -176.87(17) . . . . ? C4 C5 C6 C7 -170.5(2) . . . . ? C10 C5 C6 C7 8.7(3) . . . . ? C5 C6 C7 C8 173.9(2) . . . . ? N2 C6 C7 C8 -1.2(3) . . . . ? C6 C7 C8 C9 0.6(3) . . . . ? C7 C8 C9 N2 0.2(3) . . . . ? C6 C5 C10 C11 -108.7(2) . . . . ? C4 C5 C10 C11 70.6(2) . . . . ? C6 C5 C10 C15 72.6(2) . . . . ? C4 C5 C10 C15 -108.1(2) . . . . ? C15 C10 C11 C12 -1.4(3) . . . . ? C5 C10 C11 C12 179.92(19) . . . . ? C10 C11 C12 C13 1.9(3) . . . . ? C11 C12 C13 C14 -0.9(3) . . . . ? C11 C12 C13 N3 180.00(18) . . . . ? C12 C13 C14 C15 -0.8(3) . . . . ? N3 C13 C14 C15 178.36(18) . . . . ? C13 C14 C15 C10 1.4(3) . . . . ? C11 C10 C15 C14 -0.3(3) . . . . ? C5 C10 C15 C14 178.43(18) . . . . ? N4 C17 C18 N3 -1.6(3) . . . . ? N5 C19 C20 C21 -0.8(3) . . . . ? C19 C20 C21 C22 0.4(3) . . . . ? C20 C21 C22 N5 0.1(2) . . . . ? C20 C21 C22 C23 -176.8(2) . . . . ? N5 C22 C23 C24 2.3(3) . . . . ? C21 C22 C23 C24 178.77(19) . . . . ? N5 C22 C23 C28 -177.69(16) . . . . ? C21 C22 C23 C28 -1.2(3) . . . . ? C22 C23 C24 N6 -3.6(3) . . . . ? C28 C23 C24 N6 176.36(15) . . . . ? C22 C23 C24 C25 167.21(17) . . . . ? C28 C23 C24 C25 -12.8(2) . . . . ? N6 C24 C25 C26 1.4(2) . . . . ? C23 C24 C25 C26 -170.60(16) . . . . ? C24 C25 C26 C27 -1.0(2) . . . . ? C25 C26 C27 N6 0.3(2) . . . . ? C24 C23 C28 C29 116.63(18) . . . . ? C22 C23 C28 C29 -63.4(2) . . . . ? C24 C23 C28 C33 -64.2(2) . . . . ? C22 C23 C28 C33 115.83(18) . . . . ? C33 C28 C29 C30 0.2(3) . . . . ? C23 C28 C29 C30 179.44(16) . . . . ? C28 C29 C30 C31 -1.7(3) . . . . ? C29 C30 C31 C32 1.7(3) . . . . ? C29 C30 C31 N7 -178.00(15) . . . . ? C30 C31 C32 C33 -0.2(3) . . . . ? N7 C31 C32 C33 179.54(16) . . . . ? C31 C32 C33 C28 -1.4(3) . . . . ? C29 C28 C33 C32 1.3(3) . . . . ? C23 C28 C33 C32 -177.88(17) . . . . ? N8 C35 C36 N7 0.2(2) . . . . ? C2 C1 N1 C4 -1.1(2) . . . . ? C2 C1 N1 Ni1 -177.71(14) . . . . ? C5 C4 N1 C1 -178.14(16) . . . . ? C3 C4 N1 C1 0.2(2) . . . . ? C5 C4 N1 Ni1 -1.7(2) . . . . ? C3 C4 N1 Ni1 176.63(12) . . . . ? C8 C9 N2 C6 -0.9(3) . . . . ? C8 C9 N2 Ni1 -172.37(17) . . . . ? C5 C6 N2 C9 -173.99(19) . . . . ? C7 C6 N2 C9 1.3(2) . . . . ? C5 C6 N2 Ni1 -2.7(3) . . . . ? C7 C6 N2 Ni1 172.51(15) . . . . ? N4 C16 N3 C18 0.3(2) . . . . ? N4 C16 N3 C13 -172.03(17) . . . . ? C17 C18 N3 C16 0.8(3) . . . . ? C17 C18 N3 C13 173.1(2) . . . . ? C12 C13 N3 C16 138.9(2) . . . . ? C14 C13 N3 C16 -40.3(3) . . . . ? C12 C13 N3 C18 -31.9(3) . . . . ? C14 C13 N3 C18 148.9(2) . . . . ? N3 C16 N4 C17 -1.2(2) . . . . ? N3 C16 N4 Ni1 161.11(12) . . . 4 ? C18 C17 N4 C16 1.7(3) . . . . ? C18 C17 N4 Ni1 -159.22(18) . . . 4 ? C20 C19 N5 C22 0.8(2) . . . . ? C20 C19 N5 Ni1 163.00(16) . . . . ? C23 C22 N5 C19 176.43(17) . . . . ? C21 C22 N5 C19 -0.6(2) . . . . ? C23 C22 N5 Ni1 14.6(2) . . . . ? C21 C22 N5 Ni1 -162.36(13) . . . . ? C26 C27 N6 C24 0.6(2) . . . . ? C26 C27 N6 Ni1 -176.37(12) . . . . ? C23 C24 N6 C27 170.92(16) . . . . ? C25 C24 N6 C27 -1.22(18) . . . . ? C23 C24 N6 Ni1 -12.0(2) . . . . ? C25 C24 N6 Ni1 175.82(11) . . . . ? N8 C34 N7 C36 0.7(2) . . . . ? N8 C34 N7 C31 -179.60(15) . . . . ? C35 C36 N7 C34 -0.5(2) . . . . ? C35 C36 N7 C31 179.81(17) . . . . ? C30 C31 N7 C34 37.1(3) . . . . ? C32 C31 N7 C34 -142.62(18) . . . . ? C30 C31 N7 C36 -143.33(19) . . . . ? C32 C31 N7 C36 37.0(3) . . . . ? N7 C34 N8 C35 -0.6(2) . . . . ? N7 C34 N8 Ni1 -179.63(11) . . . 3_455 ? C36 C35 N8 C34 0.2(2) . . . . ? C36 C35 N8 Ni1 179.02(13) . . . 3_455 ? C19 N5 Ni1 N6 -179.66(15) . . . . ? C22 N5 Ni1 N6 -21.08(14) . . . . ? C19 N5 Ni1 N1 0.91(15) . . . . ? C22 N5 Ni1 N1 159.50(14) . . . . ? C19 N5 Ni1 N2 88.47(15) . . . . ? C22 N5 Ni1 N2 -112.94(15) . . . . ? C19 N5 Ni1 N8 -90.6(6) . . . 3_545 ? C22 N5 Ni1 N8 68.0(6) . . . 3_545 ? C19 N5 Ni1 N4 -91.03(15) . . . 4_454 ? C22 N5 Ni1 N4 67.56(14) . . . 4_454 ? C27 N6 Ni1 N5 -163.85(15) . . . . ? C24 N6 Ni1 N5 19.78(13) . . . . ? C27 N6 Ni1 N1 -14(3) . . . . ? C24 N6 Ni1 N1 170(13) . . . . ? C27 N6 Ni1 N2 -72.47(15) . . . . ? C24 N6 Ni1 N2 111.17(13) . . . . ? C27 N6 Ni1 N8 21.57(15) . . . 3_545 ? C24 N6 Ni1 N8 -154.80(13) . . . 3_545 ? C27 N6 Ni1 N4 110.39(15) . . . 4_454 ? C24 N6 Ni1 N4 -65.97(13) . . . 4_454 ? C1 N1 Ni1 N5 -90.82(14) . . . . ? C4 N1 Ni1 N5 93.37(14) . . . . ? C1 N1 Ni1 N6 119(3) . . . . ? C4 N1 Ni1 N6 -57(3) . . . . ? C1 N1 Ni1 N2 177.86(15) . . . . ? C4 N1 Ni1 N2 2.04(14) . . . . ? C1 N1 Ni1 N8 83.76(14) . . . 3_545 ? C4 N1 Ni1 N8 -92.06(14) . . . 3_545 ? C1 N1 Ni1 N4 -5.01(14) . . . 4_454 ? C4 N1 Ni1 N4 179.18(14) . . . 4_454 ? C9 N2 Ni1 N5 76.56(17) . . . . ? C6 N2 Ni1 N5 -93.00(17) . . . . ? C9 N2 Ni1 N6 -11.37(17) . . . . ? C6 N2 Ni1 N6 179.07(17) . . . . ? C9 N2 Ni1 N1 169.62(18) . . . . ? C6 N2 Ni1 N1 0.06(17) . . . . ? C9 N2 Ni1 N8 -103.53(17) . . . 3_545 ? C6 N2 Ni1 N8 86.91(17) . . . 3_545 ? C9 N2 Ni1 N4 86.6(15) . . . 4_454 ? C6 N2 Ni1 N4 -82.9(15) . . . 4_454 ? O1 C37 N9 C38 0.5(5) . . . . ? O1 C37 N9 C39 -177.6(4) . . . . ? O2 C41 N10 C43 -179.8(7) . . . . ? O2 C41 N10 C42 16.6(10) . . . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 30.06 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.380 _refine_diff_density_min -0.304 _refine_diff_density_rms 0.047 #===END _database_code_depnum_ccdc_archive 'CCDC 927327'