# Electronic Supplementary Material (ESI) for Dalton Transactions # This journal is © The Royal Society of Chemistry 2011 data_global _journal_name_full 'Dalton Trans.' _journal_coden_cambridge 0222 _journal_year ? _journal_volume ? _journal_page_first ? _publ_contact_author_name 'M. Fatima C. Guedes da Silva' _publ_contact_author_email fatima.guedes@ist.utl.pt loop_ _publ_author_name 'Maximilian N. Kopylovich' 'Kamran T. Mahmudov' 'M. Fatima C. Guedes da Silva' 'Alexander M. Kirillov' 'Armando J. L. Pombeiro' data_compound3 _database_code_depnum_ccdc_archive 'CCDC 831174' #TrackingRef '- CIFS.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C11 H9 K N4 O7' _chemical_formula_sum 'C11 H9 K N4 O7' _chemical_formula_weight 348.32 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' K K 0.2009 0.2494 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting MONOCLINIC _symmetry_space_group_name_H-M 'P 21/c' _symmetry_space_group_name_Hall '-P 2ybc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 5.6530(16) _cell_length_b 13.404(4) _cell_length_c 19.2441(18) _cell_angle_alpha 90.00 _cell_angle_beta 102.459(5) _cell_angle_gamma 90.00 _cell_volume 1423.8(6) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 902 _cell_measurement_theta_min 2.65 _cell_measurement_theta_max 23.05 _exptl_crystal_description rod _exptl_crystal_colour red _exptl_crystal_size_max 0.26 _exptl_crystal_size_mid 0.21 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.625 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 712 _exptl_absorpt_coefficient_mu 0.418 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8991 _exptl_absorpt_correction_T_max 0.9673 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(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 8721 _diffrn_reflns_av_R_equivalents 0.1620 _diffrn_reflns_av_sigmaI/netI 0.2032 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 3.04 _diffrn_reflns_theta_max 25.35 _reflns_number_total 2598 _reflns_number_gt 1143 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SIR97 (Giacovazzo et al, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' _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^)+(0.1377P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2598 _refine_ls_number_parameters 210 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.2059 _refine_ls_R_factor_gt 0.0889 _refine_ls_wR_factor_ref 0.2713 _refine_ls_wR_factor_gt 0.2053 _refine_ls_goodness_of_fit_ref 0.963 _refine_ls_restrained_S_all 0.963 _refine_ls_shift/su_max 0.007 _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 0.0457(16) 0.1401(6) 0.6242(4) 0.024(2) Uani 1 1 d . . . C2 C -0.1414(14) 0.1072(6) 0.6580(4) 0.0214(18) Uani 1 1 d . . . C3 C -0.1958(16) 0.1548(6) 0.7162(4) 0.025(2) Uani 1 1 d . . . H3 H -0.3186 0.1297 0.7383 0.030 Uiso 1 1 calc R . . C4 C -0.0693(16) 0.2389(6) 0.7414(4) 0.024(2) Uani 1 1 d . . . C5 C 0.1141(16) 0.2783(6) 0.7113(4) 0.028(2) Uani 1 1 d . . . H5 H 0.1987 0.3371 0.7297 0.034 Uiso 1 1 calc R . . C6 C 0.1675(15) 0.2289(6) 0.6539(4) 0.0225(19) Uani 1 1 d . . . C11 C 0.832(2) 0.3790(7) 0.4936(5) 0.055(3) Uani 1 1 d . . . H11A H 0.8339 0.3389 0.4511 0.083 Uiso 1 1 calc R . . H11B H 0.9961 0.3833 0.5230 0.083 Uiso 1 1 calc R . . H11C H 0.7725 0.4462 0.4792 0.083 Uiso 1 1 calc R . . C12 C 0.6684(17) 0.3312(7) 0.5354(4) 0.028(2) Uani 1 1 d . . . C13 C 0.6056(16) 0.3836(6) 0.5961(4) 0.028(2) Uani 1 1 d . . . C14 C 0.709(2) 0.4798(8) 0.6225(6) 0.056(3) Uani 1 1 d . . . C15 C 0.612(2) 0.5304(8) 0.6797(5) 0.055(3) Uani 1 1 d . . . H15A H 0.6853 0.5008 0.7258 0.083 Uiso 1 1 calc R . . H15B H 0.4357 0.5220 0.6704 0.083 Uiso 1 1 calc R . . H15C H 0.6512 0.6017 0.6803 0.083 Uiso 1 1 calc R . . N1 N 0.3400(12) 0.2627(5) 0.6168(3) 0.0230(17) Uani 1 1 d . . . H1 H 0.3757 0.2260 0.5826 0.028 Uiso 1 1 calc R . . N2 N 0.4478(13) 0.3482(5) 0.6329(3) 0.0295(18) Uani 1 1 d . . . N3 N -0.2958(13) 0.0254(5) 0.6312(3) 0.0271(17) Uani 1 1 d . . . N4 N -0.1365(15) 0.2920(6) 0.8006(4) 0.037(2) Uani 1 1 d . . . O1 O 0.1099(10) 0.0995(4) 0.5713(3) 0.0274(14) Uani 1 1 d . . . O2 O 0.5873(11) 0.2469(4) 0.5193(3) 0.0315(15) Uani 1 1 d . . . O3 O 0.876(2) 0.5152(7) 0.6020(6) 0.131(5) Uani 1 1 d . . . O31 O -0.2969(11) -0.0078(4) 0.5703(3) 0.0333(16) Uani 1 1 d . . . O32 O -0.4281(12) -0.0116(4) 0.6674(3) 0.0358(16) Uani 1 1 d . . . O41 O -0.0368(16) 0.3704(6) 0.8194(4) 0.073(3) Uani 1 1 d . . . O42 O -0.2939(13) 0.2559(5) 0.8282(3) 0.0465(19) Uani 1 1 d . . . K1 K -0.2193(4) 0.09590(14) 0.44540(8) 0.0288(6) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.038(6) 0.024(5) 0.014(4) -0.001(3) 0.013(4) 0.003(4) C2 0.026(5) 0.030(5) 0.008(4) 0.004(3) 0.003(3) -0.003(4) C3 0.034(5) 0.030(5) 0.012(4) 0.003(3) 0.010(4) -0.001(4) C4 0.037(6) 0.023(5) 0.017(4) -0.005(3) 0.016(4) 0.000(4) C5 0.038(6) 0.032(5) 0.017(4) -0.005(4) 0.011(4) -0.005(4) C6 0.028(5) 0.030(5) 0.010(4) 0.001(3) 0.005(4) -0.004(4) C11 0.086(9) 0.055(7) 0.038(6) -0.021(5) 0.040(6) -0.026(6) C12 0.039(6) 0.027(5) 0.021(5) 0.005(4) 0.013(4) 0.004(4) C13 0.037(6) 0.028(5) 0.021(4) 0.000(3) 0.011(4) -0.003(4) C14 0.086(10) 0.046(7) 0.047(7) -0.012(5) 0.037(7) -0.032(6) C15 0.088(9) 0.054(7) 0.036(6) -0.024(5) 0.041(6) -0.024(6) N1 0.032(4) 0.029(4) 0.012(3) -0.005(3) 0.015(3) -0.004(3) N2 0.035(5) 0.041(5) 0.015(4) 0.001(3) 0.010(3) 0.000(4) N3 0.036(5) 0.030(4) 0.016(4) 0.002(3) 0.006(3) -0.008(3) N4 0.053(6) 0.039(5) 0.026(4) -0.023(3) 0.025(4) -0.011(4) O1 0.038(4) 0.033(3) 0.015(3) -0.005(3) 0.014(3) -0.003(3) O2 0.048(4) 0.034(4) 0.017(3) -0.004(3) 0.018(3) -0.005(3) O3 0.188(12) 0.110(8) 0.142(9) -0.087(7) 0.143(10) -0.109(8) O31 0.047(4) 0.043(4) 0.011(3) -0.006(2) 0.009(3) -0.010(3) O32 0.048(4) 0.045(4) 0.020(3) -0.004(3) 0.021(3) -0.010(3) O41 0.103(7) 0.068(6) 0.069(5) -0.050(4) 0.065(5) -0.044(5) O42 0.064(5) 0.054(4) 0.033(4) -0.014(3) 0.037(4) -0.019(4) K1 0.0425(12) 0.0362(11) 0.0095(8) -0.0036(8) 0.0099(7) -0.0028(10) _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 O1 1.275(8) . ? C1 C2 1.425(10) . ? C1 C6 1.432(11) . ? C1 K1 3.495(8) . ? C2 C3 1.380(10) . ? C2 N3 1.427(10) . ? C3 C4 1.366(11) . ? C3 H3 0.9500 . ? C4 C5 1.396(11) . ? C4 N4 1.462(9) . ? C5 C6 1.376(10) . ? C5 H5 0.9500 . ? C6 N1 1.401(9) . ? C11 C12 1.494(11) . ? C11 H11A 0.9800 . ? C11 H11B 0.9800 . ? C11 H11C 0.9800 . ? C12 O2 1.233(10) . ? C12 C13 1.472(11) . ? C13 N2 1.340(10) . ? C13 C14 1.461(12) . ? C14 O3 1.195(11) . ? C14 C15 1.494(13) . ? C15 H15A 0.9800 . ? C15 H15B 0.9800 . ? C15 H15C 0.9800 . ? N1 N2 1.303(9) . ? N1 H1 0.8800 . ? N3 O32 1.232(8) . ? N3 O31 1.251(8) . ? N3 K1 3.254(7) 3_456 ? N4 O41 1.211(9) . ? N4 O42 1.229(9) . ? N4 K1 3.287(6) 4_566 ? O1 K1 2.718(6) . ? O1 K1 2.726(6) 3_556 ? O2 K1 2.825(6) 1_655 ? O31 K1 2.890(5) . ? O31 K1 2.934(6) 3_456 ? O31 K1 3.222(6) 3_556 ? O32 K1 2.845(6) 3_456 ? O41 K1 2.868(6) 4_566 ? O42 K1 2.966(6) 4_566 ? K1 O1 2.726(6) 3_556 ? K1 O2 2.825(6) 1_455 ? K1 O32 2.845(6) 3_456 ? K1 O41 2.868(6) 4_565 ? K1 O31 2.934(6) 3_456 ? K1 O42 2.966(6) 4_565 ? K1 O31 3.223(6) 3_556 ? K1 N3 3.254(7) 3_456 ? K1 N4 3.287(6) 4_565 ? 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 O1 C1 C2 126.9(8) . . ? O1 C1 C6 118.5(7) . . ? C2 C1 C6 114.6(6) . . ? O1 C1 K1 43.6(4) . . ? C2 C1 K1 101.2(5) . . ? C6 C1 K1 126.9(5) . . ? C3 C2 C1 123.0(8) . . ? C3 C2 N3 115.0(7) . . ? C1 C2 N3 121.9(6) . . ? C4 C3 C2 118.5(7) . . ? C4 C3 H3 120.7 . . ? C2 C3 H3 120.7 . . ? C3 C4 C5 123.0(7) . . ? C3 C4 N4 118.3(7) . . ? C5 C4 N4 118.7(7) . . ? C6 C5 C4 117.5(8) . . ? C6 C5 H5 121.2 . . ? C4 C5 H5 121.2 . . ? C5 C6 N1 123.4(7) . . ? C5 C6 C1 123.4(7) . . ? N1 C6 C1 113.2(6) . . ? C12 C11 H11A 109.5 . . ? C12 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? C12 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? O2 C12 C13 119.8(7) . . ? O2 C12 C11 119.8(7) . . ? C13 C12 C11 120.4(8) . . ? N2 C13 C14 113.0(7) . . ? N2 C13 C12 123.6(8) . . ? C14 C13 C12 123.4(7) . . ? O3 C14 C13 121.4(9) . . ? O3 C14 C15 120.2(9) . . ? C13 C14 C15 118.3(8) . . ? C14 C15 H15A 109.5 . . ? C14 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? C14 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? N2 N1 C6 120.3(6) . . ? N2 N1 H1 119.9 . . ? C6 N1 H1 119.9 . . ? N1 N2 C13 121.1(7) . . ? O32 N3 O31 120.4(7) . . ? O32 N3 C2 120.2(6) . . ? O31 N3 C2 119.4(6) . . ? O32 N3 K1 60.0(4) . 3_456 ? O31 N3 K1 64.2(4) . 3_456 ? C2 N3 K1 159.6(5) . 3_456 ? O41 N4 O42 123.1(7) . . ? O41 N4 C4 118.3(7) . . ? O42 N4 C4 118.7(7) . . ? O41 N4 K1 59.5(4) . 4_566 ? O42 N4 K1 64.2(4) . 4_566 ? C4 N4 K1 172.8(6) . 4_566 ? C1 O1 K1 117.5(5) . . ? C1 O1 K1 127.9(5) . 3_556 ? K1 O1 K1 90.40(17) . 3_556 ? C12 O2 K1 128.3(5) . 1_655 ? N3 O31 K1 129.6(5) . . ? N3 O31 K1 93.2(4) . 3_456 ? K1 O31 K1 114.4(2) . 3_456 ? N3 O31 K1 113.3(5) . 3_556 ? K1 O31 K1 78.18(14) . 3_556 ? K1 O31 K1 133.3(2) 3_456 3_556 ? N3 O32 K1 98.0(4) . 3_456 ? N4 O41 K1 99.2(5) . 4_566 ? N4 O42 K1 93.9(5) . 4_566 ? O1 K1 O1 89.60(16) . 3_556 ? O1 K1 O2 78.68(17) . 1_455 ? O1 K1 O2 150.42(16) 3_556 1_455 ? O1 K1 O32 156.83(18) . 3_456 ? O1 K1 O32 70.61(18) 3_556 3_456 ? O2 K1 O32 112.64(19) 1_455 3_456 ? O1 K1 O41 116.7(2) . 4_565 ? O1 K1 O41 85.38(18) 3_556 4_565 ? O2 K1 O41 124.16(19) 1_455 4_565 ? O32 K1 O41 74.8(2) 3_456 4_565 ? O1 K1 O31 57.66(17) . . ? O1 K1 O31 73.45(15) 3_556 . ? O2 K1 O31 77.36(16) 1_455 . ? O32 K1 O31 103.69(17) 3_456 . ? O41 K1 O31 157.7(2) 4_565 . ? O1 K1 O31 122.87(16) . 3_456 ? O1 K1 O31 80.27(17) 3_556 3_456 ? O2 K1 O31 83.52(17) 1_455 3_456 ? O32 K1 O31 43.75(15) 3_456 3_456 ? O41 K1 O31 118.3(2) 4_565 3_456 ? O31 K1 O31 65.6(2) . 3_456 ? O1 K1 O42 128.6(2) . 4_565 ? O1 K1 O42 123.53(16) 3_556 4_565 ? O2 K1 O42 84.03(16) 1_455 4_565 ? O32 K1 O42 74.00(19) 3_456 4_565 ? O41 K1 O42 43.11(18) 4_565 4_565 ? O31 K1 O42 158.73(18) . 4_565 ? O31 K1 O42 102.41(19) 3_456 4_565 ? O1 K1 O31 68.30(15) . 3_556 ? O1 K1 O31 53.39(16) 3_556 3_556 ? O2 K1 O31 140.03(18) 1_455 3_556 ? O32 K1 O31 106.40(16) 3_456 3_556 ? O41 K1 O31 58.69(18) 4_565 3_556 ? O31 K1 O31 101.82(14) . 3_556 ? O31 K1 O31 133.3(2) 3_456 3_556 ? O42 K1 O31 99.05(16) 4_565 3_556 ? O1 K1 N3 139.51(17) . 3_456 ? O1 K1 N3 69.94(17) 3_556 3_456 ? O2 K1 N3 101.89(19) 1_455 3_456 ? O41 K1 N3 96.7(2) 4_565 3_456 ? O31 K1 N3 82.66(17) . 3_456 ? O42 K1 N3 91.29(19) 4_565 3_456 ? O31 K1 N3 117.77(17) 3_556 3_456 ? O1 K1 N4 123.5(2) . 4_565 ? O1 K1 N4 105.19(17) 3_556 4_565 ? O2 K1 N4 103.91(18) 1_455 4_565 ? O32 K1 N4 74.88(19) 3_456 4_565 ? O31 K1 N4 178.35(19) . 4_565 ? O31 K1 N4 113.38(19) 3_456 4_565 ? O31 K1 N4 77.92(17) 3_556 4_565 ? N3 K1 N4 96.01(19) 3_456 4_565 ? O1 K1 C1 18.89(17) . . ? O1 K1 C1 102.65(18) 3_556 . ? O2 K1 C1 60.87(18) 1_455 . ? O32 K1 C1 154.10(18) 3_456 . ? O41 K1 C1 130.5(2) 4_565 . ? O31 K1 C1 51.12(17) . . ? O31 K1 C1 111.20(17) 3_456 . ? O42 K1 C1 126.6(2) 4_565 . ? O31 K1 C1 87.14(17) 3_556 . ? N3 K1 C1 132.14(18) 3_456 . ? N4 K1 C1 130.4(2) 4_565 . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 25.35 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 1.288 _refine_diff_density_min -0.724 _refine_diff_density_rms 0.126 #===END============================================================== data_compound4 _database_code_depnum_ccdc_archive 'CCDC 831175' #TrackingRef '- CIFS.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C11 H14 N4 Ni O10, H2 O' _chemical_formula_sum 'C11 H16 N4 Ni O11' _chemical_formula_weight 438.99 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 triclinic _symmetry_space_group_name_H-M P-1 _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.2053(2) _cell_length_b 10.2393(3) _cell_length_c 10.9106(2) _cell_angle_alpha 67.0990(10) _cell_angle_beta 73.6950(10) _cell_angle_gamma 85.8660(10) _cell_volume 809.74(4) _cell_formula_units_Z 2 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 4970 _cell_measurement_theta_min 2.16 _cell_measurement_theta_max 28.52 _exptl_crystal_description block _exptl_crystal_colour red _exptl_crystal_size_max 0.39 _exptl_crystal_size_mid 0.28 _exptl_crystal_size_min 0.17 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.800 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 452 _exptl_absorpt_coefficient_mu 1.270 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.636 _exptl_absorpt_correction_T_max 0.799 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71069 _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 9045 _diffrn_reflns_av_R_equivalents 0.0181 _diffrn_reflns_av_sigmaI/netI 0.0195 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 2.59 _diffrn_reflns_theta_max 25.35 _reflns_number_total 2777 _reflns_number_gt 2487 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SIR97 (Giacovazzo et al, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' _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^)+(0.0652P)^2^+2.9167P] 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 2777 _refine_ls_number_parameters 265 _refine_ls_number_restraints 25 _refine_ls_R_factor_all 0.0561 _refine_ls_R_factor_gt 0.0495 _refine_ls_wR_factor_ref 0.1338 _refine_ls_wR_factor_gt 0.1283 _refine_ls_goodness_of_fit_ref 1.073 _refine_ls_restrained_S_all 1.082 _refine_ls_shift/su_max 0.006 _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 0.6189(5) 0.3290(4) 0.2897(4) 0.0218(8) Uani 1 1 d . . . C2 C 0.7483(5) 0.3391(4) 0.1635(4) 0.0204(8) Uani 1 1 d . . . C3 C 0.7632(5) 0.4536(4) 0.0417(4) 0.0223(8) Uani 1 1 d . . . H3 H 0.8471 0.4581 -0.0377 0.027 Uiso 1 1 calc R . . C4 C 0.6514(5) 0.5631(4) 0.0380(4) 0.0239(9) Uani 1 1 d . . . C5 C 0.5272(5) 0.5621(4) 0.1525(4) 0.0247(9) Uani 1 1 d . . . H5 H 0.4543 0.6368 0.1476 0.030 Uiso 1 1 calc R . . C6 C 0.5133(6) 0.4460(5) 0.2765(4) 0.0264(9) Uani 1 1 d . A . C7 C 1.0707(5) 0.1178(4) 0.0712(4) 0.0217(8) Uani 1 1 d . . . C8 C 1.1747(6) 0.1408(5) -0.0702(4) 0.0268(10) Uani 1 1 d . . . C9 C 1.1426(7) 0.2681(5) -0.1876(5) 0.0378(12) Uani 1 1 d . . . H9A H 1.2312 0.2801 -0.2707 0.057 Uiso 1 1 calc R . . H9B H 1.1409 0.3510 -0.1666 0.057 Uiso 1 1 calc R . . H9C H 1.0350 0.2547 -0.2007 0.057 Uiso 1 1 calc R . . C10 C 1.0936(5) 0.0005(5) 0.1913(4) 0.0226(9) Uani 1 1 d . . . C11 C 1.2412(6) -0.0938(5) 0.1812(5) 0.0319(10) Uani 1 1 d . . . H11A H 1.2349 -0.1659 0.2710 0.048 Uiso 1 1 calc R . . H11B H 1.3454 -0.0383 0.1477 0.048 Uiso 1 1 calc R . . H11C H 1.2376 -0.1375 0.1185 0.048 Uiso 1 1 calc R . . N1 N 0.8491(4) 0.2200(4) 0.1812(3) 0.0202(7) Uani 1 1 d . . . N2 N 0.9579(4) 0.2217(4) 0.0711(3) 0.0211(7) Uani 1 1 d . . . N4 N 0.6608(5) 0.6807(4) -0.0927(4) 0.0279(8) Uani 1 1 d . . . N6 N 0.3783(6) 0.4479(4) 0.3917(4) 0.0478(13) Uani 1 1 d . . . O1 O 0.6078(4) 0.2186(3) 0.4007(3) 0.0244(6) Uani 1 1 d . . . O2 O 0.9925(4) -0.0282(3) 0.3102(3) 0.0238(6) Uani 1 1 d . . . O3 O 0.7165(4) -0.0571(3) 0.5755(3) 0.0303(7) Uani 1 1 d . . . O4 O 0.9519(4) 0.1758(3) 0.4346(3) 0.0307(7) Uani 1 1 d D . . O5 O 0.6119(4) -0.0358(3) 0.3421(3) 0.0231(6) Uani 1 1 d . . . O6 O 1.2833(4) 0.0582(4) -0.0956(3) 0.0349(8) Uani 1 1 d . . . O10 O 0.9453(9) 0.4361(8) 0.3810(8) 0.122(3) Uani 1 1 d . . . O41 O 0.5595(4) 0.7752(3) -0.0961(3) 0.0360(8) Uani 1 1 d . . . O42 O 0.7711(4) 0.6797(4) -0.1960(3) 0.0363(8) Uani 1 1 d . . . Ni1 Ni 0.79040(6) 0.07911(5) 0.37372(5) 0.01955(19) Uani 1 1 d . . . O62B O 0.3896(14) 0.3761(11) 0.5102(10) 0.065(3) Uani 0.493(12) 1 d PU A 2 O61A O 0.3231(16) 0.5565(12) 0.3997(12) 0.069(3) Uani 0.507(12) 1 d PU A 1 O61B O 0.2668(9) 0.5398(7) 0.3696(7) 0.0282(19) Uani 0.493(12) 1 d PU A 2 O62A O 0.3133(9) 0.3341(7) 0.4837(7) 0.035(2) Uani 0.507(12) 1 d PU A 1 H3B H 0.7524 -0.0986 0.6475 0.052 Uiso 1 1 d . . . H3A H 0.6276 -0.0165 0.6267 0.052 Uiso 1 1 d . . . H4B H 0.9460 0.1219 0.5305 0.052 Uiso 1 1 d . . . H4C H 0.9162 0.2704 0.4236 0.052 Uiso 1 1 d D . . H5B H 0.5881 -0.1278 0.4163 0.052 Uiso 1 1 d . . . H5C H 0.6587 -0.0471 0.2558 0.052 Uiso 1 1 d . . . H10A H 1.0133 0.5106 0.3555 0.052 Uiso 1 1 d . . . H10B H 0.8459 0.4640 0.4129 0.052 Uiso 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 0.021(2) 0.024(2) 0.0134(19) -0.0025(16) -0.0005(16) -0.0028(17) C2 0.0185(19) 0.026(2) 0.0128(18) -0.0035(16) -0.0025(15) -0.0034(16) C3 0.022(2) 0.026(2) 0.0145(18) -0.0033(16) -0.0038(16) -0.0041(17) C4 0.029(2) 0.021(2) 0.0165(19) 0.0019(16) -0.0084(17) -0.0076(17) C5 0.024(2) 0.019(2) 0.026(2) -0.0031(17) -0.0066(17) 0.0007(17) C6 0.026(2) 0.025(2) 0.021(2) -0.0048(17) -0.0001(17) 0.0008(17) C7 0.0193(19) 0.026(2) 0.0165(19) -0.0085(16) 0.0011(16) -0.0046(16) C8 0.025(2) 0.036(2) 0.020(2) -0.0133(19) -0.0007(17) -0.0100(19) C9 0.050(3) 0.040(3) 0.016(2) -0.008(2) 0.002(2) -0.007(2) C10 0.019(2) 0.028(2) 0.020(2) -0.0110(17) -0.0010(16) -0.0034(17) C11 0.029(2) 0.034(2) 0.025(2) -0.0080(19) -0.0024(19) 0.008(2) N1 0.0193(17) 0.0227(17) 0.0135(16) -0.0036(13) -0.0012(13) -0.0018(14) N2 0.0207(17) 0.0260(18) 0.0122(15) -0.0041(13) -0.0007(13) -0.0062(14) N4 0.029(2) 0.0257(19) 0.0244(19) -0.0011(15) -0.0111(16) -0.0045(17) N6 0.059(3) 0.025(2) 0.027(2) 0.0035(17) 0.015(2) 0.016(2) O1 0.0236(15) 0.0245(15) 0.0149(14) -0.0010(12) 0.0002(11) 0.0034(12) O2 0.0207(14) 0.0293(15) 0.0152(14) -0.0041(12) -0.0023(11) 0.0021(12) O3 0.0233(15) 0.0403(18) 0.0124(13) 0.0027(12) -0.0018(12) 0.0056(14) O4 0.0290(16) 0.0391(18) 0.0178(14) -0.0044(13) -0.0054(12) -0.0021(14) O5 0.0220(14) 0.0273(15) 0.0139(13) -0.0054(11) 0.0010(11) -0.0002(12) O6 0.0274(17) 0.053(2) 0.0228(15) -0.0195(15) 0.0008(13) 0.0043(15) O10 0.106(5) 0.114(5) 0.120(6) -0.041(5) -0.002(5) 0.027(4) O41 0.0406(19) 0.0261(16) 0.0325(18) 0.0002(14) -0.0136(15) 0.0028(15) O42 0.0393(19) 0.0364(18) 0.0173(15) 0.0030(13) -0.0021(14) -0.0017(15) Ni1 0.0170(3) 0.0239(3) 0.0099(3) -0.0010(2) -0.00008(19) 0.0018(2) O62B 0.065(3) 0.064(3) 0.064(3) -0.0242(16) -0.0154(13) 0.0057(11) O61A 0.070(3) 0.068(3) 0.068(3) -0.0271(15) -0.0172(13) 0.0044(10) O61B 0.027(2) 0.027(2) 0.029(2) -0.0108(12) -0.0059(11) 0.0036(10) O62A 0.034(2) 0.033(2) 0.033(2) -0.0115(13) -0.0059(11) 0.0048(10) _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 O1 1.281(5) . ? C1 C6 1.412(6) . ? C1 C2 1.456(5) . ? C2 C3 1.368(6) . ? C2 N1 1.404(6) . ? C3 C4 1.393(6) . ? C3 H3 0.9300 . ? C4 C5 1.370(6) . ? C4 N4 1.450(5) . ? C5 C6 1.392(6) . ? C5 H5 0.9300 . ? C6 N6 1.429(6) . ? C7 N2 1.358(6) . ? C7 C10 1.441(6) . ? C7 C8 1.474(5) . ? C8 O6 1.233(6) . ? C8 C9 1.500(7) . ? C9 H9A 0.9600 . ? C9 H9B 0.9600 . ? C9 H9C 0.9600 . ? C10 O2 1.261(5) . ? C10 C11 1.500(6) . ? C11 H11A 0.9600 . ? C11 H11B 0.9600 . ? C11 H11C 0.9600 . ? N1 N2 1.275(5) . ? N1 Ni1 1.974(3) . ? N4 O41 1.226(5) . ? N4 O42 1.235(5) . ? N6 O61A 1.196(11) . ? N6 O62A 1.237(8) . ? N6 O62B 1.240(11) . ? N6 O61B 1.267(8) . ? O1 Ni1 2.035(3) . ? O2 Ni1 2.031(3) . ? O3 Ni1 2.035(3) . ? O3 H3B 0.858 . ? O3 H3A 0.962 . ? O4 Ni1 2.091(3) . ? O4 H4B 0.963 . ? O4 H4C 0.963 . ? O5 Ni1 2.121(3) . ? O5 H5B 0.961 . ? O5 H5C 0.961 . ? O10 H10A 0.883 . ? O10 H10B 0.868 . ? 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 O1 C1 C6 125.5(4) . . ? O1 C1 C2 119.5(4) . . ? C6 C1 C2 115.0(4) . . ? C3 C2 N1 125.3(4) . . ? C3 C2 C1 121.7(4) . . ? N1 C2 C1 113.0(3) . . ? C2 C3 C4 119.3(4) . . ? C2 C3 H3 120.4 . . ? C4 C3 H3 120.4 . . ? C5 C4 C3 122.6(4) . . ? C5 C4 N4 118.1(4) . . ? C3 C4 N4 119.3(4) . . ? C4 C5 C6 118.0(4) . . ? C4 C5 H5 121.0 . . ? C6 C5 H5 121.0 . . ? C5 C6 C1 123.4(4) . . ? C5 C6 N6 115.8(4) . . ? C1 C6 N6 120.7(4) . . ? N2 C7 C10 126.2(3) . . ? N2 C7 C8 111.3(4) . . ? C10 C7 C8 122.5(4) . . ? O6 C8 C7 122.7(4) . . ? O6 C8 C9 119.2(4) . . ? C7 C8 C9 118.1(4) . . ? C8 C9 H9A 109.5 . . ? C8 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? C8 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? O2 C10 C7 122.3(4) . . ? O2 C10 C11 116.4(4) . . ? C7 C10 C11 121.3(4) . . ? C10 C11 H11A 109.5 . . ? C10 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? C10 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? N2 N1 C2 114.7(3) . . ? N2 N1 Ni1 132.3(3) . . ? C2 N1 Ni1 112.9(2) . . ? N1 N2 C7 122.2(3) . . ? O41 N4 O42 123.1(4) . . ? O41 N4 C4 119.1(4) . . ? O42 N4 C4 117.8(4) . . ? O61A N6 O62A 119.0(7) . . ? O61A N6 O62B 103.3(8) . . ? O62A N6 O62B 45.0(5) . . ? O62A N6 O61B 110.7(6) . . ? O62B N6 O61B 121.9(6) . . ? O61A N6 C6 121.9(6) . . ? O62A N6 C6 119.1(5) . . ? O62B N6 C6 118.6(6) . . ? O61B N6 C6 118.5(5) . . ? C1 O1 Ni1 112.1(2) . . ? C10 O2 Ni1 129.6(3) . . ? Ni1 O3 H3B 142.8 . . ? Ni1 O3 H3A 109.5 . . ? H3B O3 H3A 90.1 . . ? Ni1 O4 H4B 109.4 . . ? Ni1 O4 H4C 109.4 . . ? H4B O4 H4C 109.0 . . ? Ni1 O5 H5B 109.3 . . ? Ni1 O5 H5C 109.3 . . ? H5B O5 H5C 109.3 . . ? H10A O10 H10B 103.3 . . ? N1 Ni1 O2 86.55(13) . . ? N1 Ni1 O3 175.94(13) . . ? O2 Ni1 O3 97.51(12) . . ? N1 Ni1 O1 82.35(13) . . ? O2 Ni1 O1 168.61(11) . . ? O3 Ni1 O1 93.59(12) . . ? N1 Ni1 O4 93.94(13) . . ? O2 Ni1 O4 87.80(12) . . ? O3 Ni1 O4 86.03(12) . . ? O1 Ni1 O4 90.44(13) . . ? N1 Ni1 O5 93.93(12) . . ? O2 Ni1 O5 94.43(11) . . ? O3 Ni1 O5 85.98(12) . . ? O1 Ni1 O5 88.87(12) . . ? O4 Ni1 O5 171.93(11) . . ? _diffrn_measured_fraction_theta_max 0.938 _diffrn_reflns_theta_full 25.35 _diffrn_measured_fraction_theta_full 0.938 _refine_diff_density_max 1.261 _refine_diff_density_min -0.964 _refine_diff_density_rms 0.105