Supplementary Material (ESI) for Dalton Transactions This journal is © The Royal Society of Chemistry 2004 data_global _publ_contact_author_email powell@chemie.uni-karlsruhe.de _publ_contact_author_name 'Prof Annie Powell' _journal_name_full 'Dalton Trans.' _journal_coden_Cambridge 0222 _publ_contact_author_address ; Institute for Inorganic Chemistry University of Karlsruhe Engesserstrasse Geb. 30.45 Karlsruhe D 76128 GERMANY ; _publ_contact_author_phone '+44 721 608 2135' _publ_section_title ; The Building-Block Approach to Extended Solids: 3,5-dicarboxylate Coordination Comounds of Increasing Dimensionality ; loop_ _publ_author_name _publ_author_address 'Philippa King' ; Institut fur Anorganische Chemie Universitat Karlsruhe Engesserstr. Geb. 30.45 D-76128 Karlsruhe Germany ; 'Rodolphe Clerac' ; Centre de Recherche Paul Pascal CNRS UPR 8641 Avenur Dr. A. Schweitzer 33600 Pessac France ; 'Christopher E. Anson' ; Institut fur Anorganische Chemie Universitat Karlsruhe Engesserstr. Geb. 30.45 D-76128 Karlsruhe Germany ; 'Annie K. Powell' ; Institut fur Anorganische Chemie Universitat Karlsruhe Engesserstr. Geb. 30.45 D-76128 Karlsruhe Germany ; data_p116 _database_code_depnum_ccdc_archive 'CCDC 224515' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C10 H20 N4 Ni2 O16' _chemical_formula_weight 569.72 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' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 6.1094(6) _cell_length_b 7.6907(7) _cell_length_c 10.7409(10) _cell_angle_alpha 87.090(2) _cell_angle_beta 80.617(2) _cell_angle_gamma 78.216(2) _cell_volume 487.34(8) _cell_formula_units_Z 1 _cell_measurement_temperature 200(2) _cell_measurement_reflns_used 2673 _cell_measurement_theta_min 2.76 _cell_measurement_theta_max 27.96 _exptl_crystal_description plate _exptl_crystal_colour green _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.941 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 292 _exptl_absorpt_coefficient_mu 2.024 _exptl_absorpt_correction_type multiscan _exptl_absorpt_correction_T_min 0.670 _exptl_absorpt_correction_T_max 0.928 _exptl_absorpt_process_details 'SADABS (Bruker AXS Inc., 2000)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 200(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'rotating anode' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker SMART Apex' _diffrn_measurement_method 'CCD area detector' _diffrn_detector_area_resol_mean 8.333 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 2455 _diffrn_reflns_av_R_equivalents 0.0223 _diffrn_reflns_av_sigmaI/netI 0.0149 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 2.71 _diffrn_reflns_theta_max 27.96 _reflns_number_total 2075 _reflns_number_gt 2002 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART-NT 5.6 (Bruker AXS Inc., 2000)' _computing_cell_refinement 'SMART-NT 5.6 (Bruker AXS Inc., 2000)' _computing_data_reduction 'SAINT+ 6.0 (Bruker AXS Inc., 2000)' _computing_structure_solution 'XS: SHELXTL 5.1 (Bruker AXS Inc., 1997)' _computing_structure_refinement 'XL: SHELXTL 5.1 (Bruker AXS Inc., 1997)' _computing_molecular_graphics 'XP: SHELXTL 5.1 (Bruker AXS Inc., 1997)' _computing_publication_material 'XCIF: SHELXTL 5.1 (Bruker AXS Inc., 1997)' _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^)+(0.0901P)^2^+0.1128P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_ls_hydrogen_treatment refall _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2075 _refine_ls_number_parameters 185 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0445 _refine_ls_R_factor_gt 0.0437 _refine_ls_wR_factor_ref 0.1140 _refine_ls_wR_factor_gt 0.1126 _refine_ls_goodness_of_fit_ref 1.143 _refine_ls_restrained_S_all 1.143 _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 Ni1 Ni 0.27892(4) 0.23940(3) 0.35901(2) 0.01231(16) Uani 1 1 d . . . N1 N 0.3590(3) 0.2758(3) 0.16532(18) 0.0159(4) Uani 1 1 d . . . N2 N 0.2598(3) 0.3371(3) 0.06604(17) 0.0157(4) Uani 1 1 d . . . H2 H 0.112(6) 0.403(4) 0.079(3) 0.024(7) Uiso 1 1 d . . . C1 C 0.5678(3) 0.1919(3) 0.1181(2) 0.0145(4) Uani 1 1 d . . . C2 C 0.6029(4) 0.1999(3) -0.0135(2) 0.0158(4) Uani 1 1 d . . . H2A H 0.747(6) 0.143(5) -0.065(3) 0.033(9) Uiso 1 1 d . . . C3 C 0.4011(4) 0.2950(3) -0.0440(2) 0.0144(4) Uani 1 1 d . . . C4 C 0.7179(4) 0.1130(3) 0.2107(2) 0.0156(4) Uani 1 1 d . . . O1 O 0.6276(3) 0.1384(2) 0.32800(15) 0.0154(3) Uani 1 1 d . . . O2 O 0.9117(3) 0.0356(3) 0.17493(17) 0.0259(4) Uani 1 1 d . . . C5 C 0.3264(4) 0.3540(3) -0.1670(2) 0.0146(4) Uani 1 1 d . . . O3 O 0.1470(3) 0.4648(3) -0.16556(16) 0.0250(4) Uani 1 1 d . . . O4 O 0.4535(3) 0.2894(2) -0.26521(14) 0.0158(3) Uani 1 1 d . . . O5 O -0.0697(3) 0.3453(2) 0.37786(16) 0.0155(3) Uani 1 1 d . . . H51 H -0.095(6) 0.413(5) 0.316(4) 0.032(9) Uiso 1 1 d . . . H52 H -0.153(6) 0.272(5) 0.374(3) 0.027(8) Uiso 1 1 d . . . O6 O 0.2428(3) 0.1864(2) 0.54738(16) 0.0195(4) Uani 1 1 d . . . H61 H 0.260(5) 0.078(5) 0.576(3) 0.025(8) Uiso 1 1 d . . . H62 H 0.324(7) 0.232(5) 0.588(4) 0.043(10) Uiso 1 1 d . . . O7 O 0.2096(3) -0.0057(2) 0.33726(16) 0.0169(3) Uani 1 1 d . . . H71 H 0.105(6) 0.003(4) 0.285(3) 0.023(7) Uiso 1 1 d . . . H72 H 0.314(8) -0.083(6) 0.307(4) 0.053(12) Uiso 1 1 d . . . O8 O 0.3119(4) 0.4842(3) 0.4025(2) 0.0285(5) Uani 1 1 d . . . H81 H 0.393(7) 0.535(5) 0.362(4) 0.039(11) Uiso 1 1 d . . . H82 H 0.237(7) 0.536(5) 0.461(4) 0.035(10) 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 Ni1 0.0120(2) 0.0143(2) 0.0098(2) -0.00158(13) -0.00206(13) -0.00004(13) N1 0.0130(9) 0.0204(10) 0.0125(9) -0.0007(7) -0.0033(7) 0.0022(7) N2 0.0129(9) 0.0206(9) 0.0098(9) 0.0004(7) -0.0015(7) 0.0049(7) C1 0.0104(9) 0.0187(10) 0.0134(10) -0.0018(8) -0.0033(7) 0.0006(8) C2 0.0110(9) 0.0209(10) 0.0140(10) -0.0017(8) -0.0013(8) -0.0001(8) C3 0.0148(10) 0.0170(10) 0.0097(9) -0.0014(7) -0.0014(8) 0.0009(8) C4 0.0139(10) 0.0187(10) 0.0144(10) -0.0015(8) -0.0050(8) -0.0009(8) O1 0.0128(7) 0.0212(8) 0.0111(8) -0.0003(6) -0.0034(6) 0.0000(6) O2 0.0130(8) 0.0417(11) 0.0183(8) -0.0068(7) -0.0040(6) 0.0080(7) C5 0.0124(9) 0.0170(10) 0.0131(10) 0.0000(8) -0.0020(7) -0.0001(8) O3 0.0202(8) 0.0326(10) 0.0149(8) 0.0000(7) -0.0024(6) 0.0116(7) O4 0.0154(7) 0.0177(7) 0.0114(7) -0.0016(6) -0.0011(6) 0.0027(6) O5 0.0133(8) 0.0179(8) 0.0147(8) -0.0008(6) -0.0035(6) -0.0006(6) O6 0.0263(9) 0.0201(9) 0.0134(8) 0.0008(6) -0.0059(7) -0.0060(7) O7 0.0152(8) 0.0155(8) 0.0194(8) -0.0039(6) -0.0050(7) 0.0007(6) O8 0.0386(11) 0.0221(9) 0.0232(10) -0.0111(8) 0.0137(9) -0.0143(9) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Ni1 N1 2.0762(19) . yes Ni1 O1 2.0906(16) . yes Ni1 O5 2.0995(17) . yes Ni1 O6 2.0288(18) . yes Ni1 O7 2.0466(17) . yes Ni1 O8 2.0194(19) . yes N1 N2 1.331(3) . ? N1 C1 1.337(3) . ? N2 C3 1.356(3) . ? N2 H2 0.93(3) . ? C1 C2 1.395(3) . ? C1 C4 1.486(3) . ? C2 C3 1.379(3) . ? C2 H2A 0.99(4) . ? C3 C5 1.487(3) . ? C4 O2 1.221(3) . ? C4 O1 1.298(3) . ? C5 O3 1.242(3) . ? C5 O4 1.261(3) . ? O5 H51 0.84(4) . ? O5 H52 0.84(4) . ? O6 H61 0.87(3) . ? O6 H62 0.84(4) . ? O7 H71 0.91(3) . ? O7 H72 0.82(5) . ? O8 H81 0.76(4) . ? O8 H82 0.78(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 O8 Ni1 O6 86.29(8) . . yes O8 Ni1 O7 171.71(8) . . yes O6 Ni1 O7 87.38(7) . . yes O8 Ni1 N1 95.07(8) . . yes O6 Ni1 N1 172.54(7) . . yes O7 Ni1 N1 91.89(7) . . yes O8 Ni1 O1 94.07(8) . . yes O6 Ni1 O1 94.44(7) . . yes O7 Ni1 O1 91.75(7) . . yes N1 Ni1 O1 78.16(7) . . yes O8 Ni1 O5 85.99(8) . . yes O6 Ni1 O5 89.22(7) . . yes O7 Ni1 O5 88.58(7) . . yes N1 Ni1 O5 98.18(7) . . yes O1 Ni1 O5 176.34(6) . . yes N2 N1 C1 105.76(18) . . ? N2 N1 Ni1 140.18(15) . . ? C1 N1 Ni1 113.25(14) . . ? N1 N2 C3 111.53(18) . . ? N1 N2 H2 119(2) . . ? C3 N2 H2 129(2) . . ? N1 C1 C2 111.12(19) . . ? N1 C1 C4 116.69(19) . . ? C2 C1 C4 132.18(19) . . ? C3 C2 C1 104.41(18) . . ? C3 C2 H2A 133(2) . . ? C1 C2 H2A 123(2) . . ? N2 C3 C2 107.17(19) . . ? N2 C3 C5 120.59(19) . . ? C2 C3 C5 132.2(2) . . ? O2 C4 O1 124.8(2) . . ? O2 C4 C1 120.6(2) . . ? O1 C4 C1 114.61(19) . . ? C4 O1 Ni1 115.31(13) . . ? O3 C5 O4 125.1(2) . . ? O3 C5 C3 117.89(19) . . ? O4 C5 C3 117.02(19) . . ? Ni1 O5 H51 109(2) . . ? Ni1 O5 H52 116(2) . . ? H51 O5 H52 102(3) . . ? Ni1 O6 H61 121(2) . . ? Ni1 O6 H62 116(3) . . ? H61 O6 H62 103(3) . . ? Ni1 O7 H71 110(2) . . ? Ni1 O7 H72 118(3) . . ? H71 O7 H72 104(4) . . ? Ni1 O8 H81 123(3) . . ? Ni1 O8 H82 122(3) . . ? H81 O8 H82 115(4) . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N2 H2 O3 0.93(3) 1.83(3) 2.719(3) 158(3) 2_565 O5 H51 O3 0.84(4) 1.87(4) 2.700(2) 172(4) 2_565 O5 H52 O1 0.84(4) 1.98(4) 2.802(3) 165(3) 1_455 O6 H61 O1 0.87(3) 1.97(3) 2.803(2) 160(3) 2_656 O6 H62 O4 0.84(4) 1.99(4) 2.786(2) 158(4) 1_556 O7 H71 O2 0.91(3) 1.78(3) 2.683(2) 175(3) 1_455 O7 H72 O4 0.82(5) 1.92(5) 2.723(2) 169(4) 2_655 O8 H81 O4 0.76(4) 1.96(4) 2.707(3) 168(4) 2_665 O8 H82 O5 0.78(4) 2.02(4) 2.803(3) 174(4) 2_566 _diffrn_measured_fraction_theta_max 0.888 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.982 _refine_diff_density_max 0.685 _refine_diff_density_min -1.287 _refine_diff_density_rms 0.229 data_p34fa _database_code_depnum_ccdc_archive 'CCDC 224516' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C10 H14 Co N4 O12' _chemical_formula_weight 441.18 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' Co Co 0.3494 0.9721 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 1 21/c 1' 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 9.9994(7) _cell_length_b 12.4504(10) _cell_length_c 6.8223(9) _cell_angle_alpha 90.00 _cell_angle_beta 108.486(4) _cell_angle_gamma 90.00 _cell_volume 805.53(14) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 26 _cell_measurement_theta_min 12.303 _cell_measurement_theta_max 12.489 _exptl_crystal_description block _exptl_crystal_colour orange _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.819 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 450 _exptl_absorpt_coefficient_mu 1.143 _exptl_absorpt_correction_type psi-scans _exptl_absorpt_correction_T_min 0.661 _exptl_absorpt_correction_T_max 0.764 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_measurement_device 'Siemens P4' _diffrn_measurement_method \w-scans _diffrn_detector_area_resol_mean ? _diffrn_standards_number 3 _diffrn_standards_interval_count 100 _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0.0 _diffrn_reflns_number 1950 _diffrn_reflns_av_R_equivalents 0.0289 _diffrn_reflns_av_sigmaI/netI 0.0369 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -1 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -1 _diffrn_reflns_limit_l_max 8 _diffrn_reflns_theta_min 2.70 _diffrn_reflns_theta_max 25.01 _reflns_number_total 1405 _reflns_number_gt 1240 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'XSCANS 2.2 (Siemens, 1996)' _computing_cell_refinement 'XSCANS 2.2 (Siemens, 1996)' _computing_data_reduction 'XSCANS 2.2 (Siemens, 1996)' _computing_structure_solution 'XS: SHELXTL/PC 5.03 (Siemens, 1995)' _computing_structure_refinement 'XL: SHELXTL/PC 5.03 (Siemens, 1995)' _computing_molecular_graphics 'XP: SHELXTL/PC 5.03 (Siemens, 1995)' _computing_publication_material 'XCIF: SHELXTL/PC 5.03 (Siemens, 1995)' _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^)+(0.0404P)^2^+0.4913P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0095(16) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 1405 _refine_ls_number_parameters 151 _refine_ls_number_restraints 3 _refine_ls_R_factor_all 0.0360 _refine_ls_R_factor_gt 0.0302 _refine_ls_wR_factor_ref 0.0825 _refine_ls_wR_factor_gt 0.0789 _refine_ls_goodness_of_fit_ref 1.050 _refine_ls_restrained_S_all 1.055 _refine_ls_shift/su_max 0.003 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Co1 Co 0.5000 0.5000 0.5000 0.01992(19) Uani 1 2 d S . . N1 N 0.71926(19) 0.52720(15) 0.6145(3) 0.0207(4) Uani 1 1 d . . . C1 C 0.7583(2) 0.62748(18) 0.5848(4) 0.0198(5) Uani 1 1 d . . . C2 C 0.9048(2) 0.63515(19) 0.6451(4) 0.0221(5) Uani 1 1 d . . . H21 H 0.954(3) 0.694(2) 0.640(4) 0.030(7) Uiso 1 1 d . . . C3 C 0.9523(2) 0.53333(19) 0.7142(4) 0.0205(5) Uani 1 1 d . . . N2 N 0.8375(2) 0.47163(16) 0.6927(3) 0.0207(4) Uani 1 1 d . . . H22 H 0.829(3) 0.406(2) 0.722(4) 0.026(7) Uiso 1 1 d . . . C4 C 0.6398(2) 0.70409(18) 0.4944(4) 0.0212(5) Uani 1 1 d . . . O1 O 0.51882(16) 0.66451(13) 0.4333(3) 0.0276(4) Uani 1 1 d . . . O2 O 0.66590(17) 0.80262(13) 0.4853(3) 0.0298(4) Uani 1 1 d . . . C5 C 1.0963(3) 0.48964(18) 0.7982(4) 0.0218(5) Uani 1 1 d . . . O3 O 1.09560(18) 0.38938(14) 0.8538(3) 0.0308(4) Uani 1 1 d . . . H3 H 1.180(4) 0.359(3) 0.905(5) 0.049(9) Uiso 1 1 d . . . O4 O 1.20014(17) 0.54330(15) 0.8126(3) 0.0345(5) Uani 1 1 d . . . O5 O 0.4786(2) 0.54404(17) 0.7797(3) 0.0347(5) Uani 1 1 d . . . H51 H 0.537(4) 0.594(3) 0.853(5) 0.054(10) Uiso 1 1 d . . . H52 H 0.410(5) 0.534(4) 0.793(7) 0.069(14) Uiso 1 1 d . . . O6 O 0.7623(2) 0.26972(18) 0.7731(5) 0.0595(7) Uani 1 1 d D . . H61 H 0.774(5) 0.250(4) 0.652(6) 0.089 Uiso 1 1 d D . . H62 H 0.664(3) 0.281(4) 0.728(7) 0.089 Uiso 1 1 d 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 Co1 0.0133(3) 0.0150(3) 0.0294(3) -0.00016(17) 0.00390(19) -0.00235(15) N1 0.0133(9) 0.0154(9) 0.0312(11) -0.0001(8) 0.0039(8) -0.0002(8) C1 0.0172(11) 0.0155(11) 0.0255(12) -0.0001(9) 0.0049(9) -0.0018(9) C2 0.0168(11) 0.0153(12) 0.0327(14) 0.0005(10) 0.0057(10) -0.0019(9) C3 0.0147(11) 0.0193(11) 0.0260(12) -0.0006(9) 0.0044(9) -0.0006(9) N2 0.0160(10) 0.0133(10) 0.0304(11) 0.0027(8) 0.0037(8) 0.0001(8) C4 0.0179(11) 0.0166(11) 0.0271(12) 0.0015(9) 0.0042(9) 0.0004(9) O1 0.0138(8) 0.0177(9) 0.0460(11) 0.0038(8) 0.0022(7) -0.0012(6) O2 0.0199(8) 0.0152(9) 0.0476(11) 0.0062(8) 0.0011(8) -0.0019(7) C5 0.0183(12) 0.0193(12) 0.0263(12) -0.0038(9) 0.0050(10) 0.0014(9) O3 0.0189(9) 0.0217(9) 0.0477(12) 0.0074(8) 0.0046(8) 0.0053(7) O4 0.0171(9) 0.0281(10) 0.0564(13) 0.0028(9) 0.0089(8) -0.0008(8) O5 0.0260(10) 0.0422(12) 0.0374(11) -0.0115(9) 0.0122(9) -0.0139(9) O6 0.0393(12) 0.0283(11) 0.105(2) 0.0045(12) 0.0142(13) -0.0005(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 Co1 O5 2.061(2) 3_666 ? Co1 O5 2.061(2) . ? Co1 N1 2.1085(18) . ? Co1 N1 2.1085(18) 3_666 ? Co1 O1 2.1194(16) . ? Co1 O1 2.1194(16) 3_666 ? N1 N2 1.327(3) . ? N1 C1 1.342(3) . ? C1 C2 1.394(3) . ? C1 C4 1.493(3) . ? C2 C3 1.383(3) . ? C2 H21 0.89(3) . ? C3 N2 1.349(3) . ? C3 C5 1.475(3) . ? N2 H22 0.85(3) . ? C4 O1 1.249(3) . ? C4 O2 1.260(3) . ? C5 O4 1.212(3) . ? C5 O3 1.305(3) . ? O3 H3 0.88(4) . ? O5 H51 0.89(4) . ? O5 H52 0.74(4) . ? O6 H61 0.91(3) . ? O6 H62 0.94(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 O5 Co1 O5 180.00(3) 3_666 . ? O5 Co1 N1 89.13(8) 3_666 . ? O5 Co1 N1 90.87(8) . . ? O5 Co1 N1 90.87(8) 3_666 3_666 ? O5 Co1 N1 89.13(8) . 3_666 ? N1 Co1 N1 180.0 . 3_666 ? O5 Co1 O1 90.91(8) 3_666 . ? O5 Co1 O1 89.09(8) . . ? N1 Co1 O1 76.80(7) . . ? N1 Co1 O1 103.20(7) 3_666 . ? O5 Co1 O1 89.09(8) 3_666 3_666 ? O5 Co1 O1 90.91(8) . 3_666 ? N1 Co1 O1 103.20(7) . 3_666 ? N1 Co1 O1 76.80(7) 3_666 3_666 ? O1 Co1 O1 180.0 . 3_666 ? N2 N1 C1 106.33(19) . . ? N2 N1 Co1 138.98(16) . . ? C1 N1 Co1 114.27(15) . . ? N1 C1 C2 110.3(2) . . ? N1 C1 C4 115.22(19) . . ? C2 C1 C4 134.4(2) . . ? C3 C2 C1 104.6(2) . . ? C3 C2 H21 129.3(18) . . ? C1 C2 H21 126.0(18) . . ? N2 C3 C2 107.3(2) . . ? N2 C3 C5 121.6(2) . . ? C2 C3 C5 131.1(2) . . ? N1 N2 C3 111.4(2) . . ? N1 N2 H22 116.9(19) . . ? C3 N2 H22 131.6(19) . . ? O1 C4 O2 124.2(2) . . ? O1 C4 C1 116.3(2) . . ? O2 C4 C1 119.5(2) . . ? C4 O1 Co1 116.88(14) . . ? O4 C5 O3 126.0(2) . . ? O4 C5 C3 122.3(2) . . ? O3 C5 C3 111.8(2) . . ? C5 O3 H3 115(2) . . ? Co1 O5 H51 118(2) . . ? Co1 O5 H52 117(4) . . ? H51 O5 H52 122(4) . . ? H61 O6 H62 99(3) . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N2 H22 O6 0.85(3) 1.90(3) 2.729(3) 166(3) . O3 H3 O2 0.88(4) 1.65(4) 2.530(2) 176(3) 2_746 O5 H51 O2 0.89(4) 1.85(4) 2.730(3) 174(3) 4_576 O5 H52 O4 0.74(4) 2.14(4) 2.864(3) 166(5) 1_455 O6 H61 O4 0.91(3) 2.59(5) 2.927(3) 103(3) 2_746 O6 H62 O1 0.94(3) 1.93(3) 2.837(3) 160(4) 3_666 _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.423 _refine_diff_density_min -0.258 _refine_diff_density_rms 0.063 data_p120c _database_code_depnum_ccdc_archive 'CCDC 224517' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C10 H28 N4 Na2 Ni O20' _chemical_formula_weight 629.05 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' Na Na 0.0362 0.0249 '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 1 21/c 1' 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 13.0446(14) _cell_length_b 12.8483(12) _cell_length_c 7.3416(8) _cell_angle_alpha 90.00 _cell_angle_beta 94.951(13) _cell_angle_gamma 90.00 _cell_volume 1225.9(2) _cell_formula_units_Z 2 _cell_measurement_temperature 200(2) _cell_measurement_reflns_used 8000 _cell_measurement_theta_min 2.23 _cell_measurement_theta_max 24.76 _exptl_crystal_description plate _exptl_crystal_colour 'pale blue' _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.704 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 652 _exptl_absorpt_coefficient_mu 0.924 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 200(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 'Stoe IPDS' _diffrn_measurement_method 'area detector' _diffrn_detector_area_resol_mean 6.667 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 7253 _diffrn_reflns_av_R_equivalents 0.0473 _diffrn_reflns_av_sigmaI/netI 0.0332 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_theta_min 2.23 _diffrn_reflns_theta_max 26.11 _reflns_number_total 2392 _reflns_number_gt 2060 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'IPDS 2.92 (Stoe & Cie GmbH, 1999)' _computing_cell_refinement 'IPDS 2.92 (Stoe & Cie GmbH, 1999)' _computing_data_reduction 'IPDS 2.92 (Stoe & Cie GmbH, 1999)' _computing_structure_solution 'SHELXTL 5.1 (Bruker AXS Inc., 1997)' _computing_structure_refinement 'SHELXTL 5.1 (Bruker AXS Inc., 1997)' _computing_molecular_graphics 'SHELXTL 5.1 (Bruker AXS Inc., 1997)' _computing_publication_material 'SHELXTL 5.1 (Bruker AXS Inc., 1997)' _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^)+(0.1030P)^2^+0.4022P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_ls_hydrogen_treatment refxyz _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2392 _refine_ls_number_parameters 214 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0535 _refine_ls_R_factor_gt 0.0478 _refine_ls_wR_factor_ref 0.1383 _refine_ls_wR_factor_gt 0.1331 _refine_ls_goodness_of_fit_ref 1.042 _refine_ls_restrained_S_all 1.042 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Ni1 Ni 0.5000 0.5000 0.5000 0.0233(2) Uani 1 2 d S . . N1 N 0.41888(16) 0.63562(16) 0.5169(3) 0.0243(4) Uani 1 1 d . . . N2 N 0.33083(16) 0.67064(17) 0.5746(3) 0.0245(4) Uani 1 1 d . . . H2 H 0.290(3) 0.629(3) 0.624(4) 0.029 Uiso 1 1 d . . . C1 C 0.47021(19) 0.71938(19) 0.4678(3) 0.0247(5) Uani 1 1 d . . . C2 C 0.41544(19) 0.8095(2) 0.4967(3) 0.0256(5) Uani 1 1 d . . . H2A H 0.433(3) 0.878(3) 0.475(4) 0.031 Uiso 1 1 d . . . C3 C 0.32600(19) 0.77556(19) 0.5661(3) 0.0251(5) Uani 1 1 d . . . C4 C 0.57282(19) 0.7001(2) 0.3988(3) 0.0264(5) Uani 1 1 d . . . O1 O 0.60049(14) 0.60483(14) 0.3978(3) 0.0290(4) Uani 1 1 d . . . O2 O 0.62495(15) 0.77394(15) 0.3493(3) 0.0346(5) Uani 1 1 d . . . C5 C 0.23726(19) 0.8342(2) 0.6284(3) 0.0282(5) Uani 1 1 d . . . O3 O 0.16208(16) 0.78429(16) 0.6762(3) 0.0394(5) Uani 1 1 d . . . O4 O 0.24587(15) 0.93241(15) 0.6293(3) 0.0343(4) Uani 1 1 d . . . O5 O 0.56836(15) 0.52802(17) 0.7630(2) 0.0296(4) Uani 1 1 d . . . H51 H 0.628(4) 0.489(3) 0.785(6) 0.044 Uiso 1 1 d . . . H52 H 0.580(3) 0.591(3) 0.786(5) 0.044 Uiso 1 1 d . . . Na1 Na 0.09343(11) 0.06953(12) 0.1299(2) 0.0547(4) Uani 1 1 d . . . O6 O 0.24908(18) -0.00183(16) 0.2624(4) 0.0371(5) Uani 1 1 d . . . H61 H 0.257(4) -0.015(3) 0.367(7) 0.056 Uiso 1 1 d . . . H62 H 0.294(4) 0.034(4) 0.245(6) 0.056 Uiso 1 1 d . . . O7 O 0.1611(3) 0.2471(3) 0.1445(7) 0.0886(11) Uani 1 1 d . . . O8A O -0.0740(3) 0.1149(3) 0.0183(6) 0.0498(9) Uani 0.60 1 d P . . O9A O 0.0281(6) 0.1144(6) 0.4280(12) 0.0631(17) Uani 0.60 1 d P . . O10A O 0.1967(4) 0.0828(4) -0.1246(7) 0.0674(13) Uani 0.60 1 d P . . O8B O -0.0365(5) 0.1027(5) -0.1396(10) 0.0540(16) Uani 0.40 1 d P . . O9B O 0.0071(13) 0.0672(15) 0.384(3) 0.135(8) Uani 0.40 1 d P . . O10B O 0.1073(10) 0.0497(13) -0.1768(18) 0.136(6) Uani 0.40 1 d P . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Ni1 0.0253(3) 0.0164(3) 0.0287(3) -0.00019(15) 0.00566(19) 0.00106(14) N1 0.0245(10) 0.0212(10) 0.0277(10) -0.0014(8) 0.0041(7) 0.0013(8) N2 0.0232(10) 0.0221(11) 0.0288(10) -0.0010(8) 0.0062(8) 0.0007(8) C1 0.0266(12) 0.0216(12) 0.0259(11) 0.0018(9) 0.0019(9) 0.0006(9) C2 0.0275(12) 0.0205(12) 0.0288(12) 0.0004(9) 0.0031(9) 0.0018(9) C3 0.0297(12) 0.0207(12) 0.0251(11) -0.0019(9) 0.0022(9) 0.0017(9) C4 0.0287(12) 0.0222(12) 0.0288(12) 0.0017(9) 0.0048(9) 0.0025(10) O1 0.0287(9) 0.0199(9) 0.0397(9) 0.0017(7) 0.0111(7) 0.0008(7) O2 0.0323(10) 0.0229(10) 0.0501(11) 0.0076(8) 0.0115(8) -0.0009(7) C5 0.0283(12) 0.0284(13) 0.0281(11) -0.0037(10) 0.0031(9) 0.0026(10) O3 0.0323(10) 0.0344(11) 0.0536(12) 0.0008(9) 0.0153(9) 0.0009(8) O4 0.0349(10) 0.0242(10) 0.0446(10) -0.0040(8) 0.0070(8) 0.0048(8) O5 0.0354(10) 0.0213(9) 0.0318(9) -0.0016(7) 0.0011(7) 0.0005(8) Na1 0.0476(8) 0.0470(8) 0.0698(9) 0.0038(7) 0.0068(6) 0.0127(6) O6 0.0350(12) 0.0337(13) 0.0441(12) 0.0034(8) 0.0121(10) -0.0002(8) O7 0.0538(17) 0.074(2) 0.139(3) 0.001(2) 0.0156(19) -0.0119(16) O8A 0.0393(19) 0.049(2) 0.061(2) -0.0019(18) 0.0006(17) 0.0102(16) O9A 0.050(3) 0.068(4) 0.072(3) -0.001(3) 0.005(2) 0.015(3) O10A 0.058(3) 0.068(3) 0.079(3) -0.020(2) 0.022(2) -0.001(2) O8B 0.044(3) 0.033(3) 0.084(5) 0.007(3) 0.001(3) 0.008(2) O9B 0.086(11) 0.146(17) 0.185(18) 0.055(13) 0.083(11) 0.061(10) O10B 0.093(8) 0.194(13) 0.119(9) -0.081(10) -0.007(6) 0.067(9) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Ni1 N1 2.048(2) 3_666 ? Ni1 N1 2.048(2) . yes Ni1 O1 2.0652(18) . yes Ni1 O1 2.0652(18) 3_666 ? Ni1 O5 2.0872(18) 3_666 ? Ni1 O5 2.0872(18) . yes N1 C1 1.334(3) . ? N1 N2 1.336(3) . ? N2 C3 1.351(3) . ? N2 H2 0.85(4) . ? C1 C2 1.387(4) . ? C1 C4 1.492(4) . ? C2 C3 1.383(4) . ? C2 H2A 0.93(3) . ? C3 C5 1.486(3) . ? C4 O2 1.240(3) . ? C4 O1 1.276(3) . ? C5 O3 1.247(3) . ? C5 O4 1.267(3) . ? O5 H51 0.93(4) . ? O5 H52 0.84(4) . ? Na1 O9B 2.265(18) . ? Na1 O10B 2.288(12) . ? Na1 O8B 2.337(6) 3 ? Na1 O8A 2.340(4) . ? Na1 O6 2.360(3) . ? Na1 O10A 2.402(5) . ? Na1 O7 2.445(4) . ? Na1 O9A 2.484(9) . ? Na1 O8B 2.528(7) . ? Na1 O8A 2.610(4) 3 ? Na1 Na1 3.459(3) 3 ? O6 H61 0.78(5) . ? O6 H62 0.76(5) . ? O8A O8B 1.306(8) . ? O8A Na1 2.610(4) 3 ? O9A O9B 0.73(2) . ? O10A O10B 1.269(14) . ? O8B Na1 2.337(6) 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 Ni1 N1 180.0 3_666 . yes N1 Ni1 O1 100.68(7) 3_666 . ? N1 Ni1 O1 79.32(7) . . yes N1 Ni1 O1 79.32(7) 3_666 3_666 ? N1 Ni1 O1 100.68(7) . 3_666 yes O1 Ni1 O1 180.0 . 3_666 yes N1 Ni1 O5 88.79(8) 3_666 3_666 ? N1 Ni1 O5 91.21(8) . 3_666 yes O1 Ni1 O5 90.59(8) . 3_666 yes O1 Ni1 O5 89.41(8) 3_666 3_666 ? N1 Ni1 O5 91.21(8) 3_666 . ? N1 Ni1 O5 88.79(8) . . yes O1 Ni1 O5 89.41(8) . . yes O1 Ni1 O5 90.59(8) 3_666 . ? O5 Ni1 O5 180.0 3_666 . yes C1 N1 N2 106.2(2) . . ? C1 N1 Ni1 113.33(16) . . ? N2 N1 Ni1 140.23(17) . . ? N1 N2 C3 111.1(2) . . ? N1 N2 H2 120(2) . . ? C3 N2 H2 128(2) . . ? N1 C1 C2 110.8(2) . . ? N1 C1 C4 116.4(2) . . ? C2 C1 C4 132.8(2) . . ? C3 C2 C1 104.8(2) . . ? C3 C2 H2A 127(2) . . ? C1 C2 H2A 129(2) . . ? N2 C3 C2 107.1(2) . . ? N2 C3 C5 121.8(2) . . ? C2 C3 C5 131.1(2) . . ? O2 C4 O1 124.7(2) . . ? O2 C4 C1 120.2(2) . . ? O1 C4 C1 115.1(2) . . ? C4 O1 Ni1 115.77(16) . . ? O3 C5 O4 125.6(2) . . ? O3 C5 C3 118.6(2) . . ? O4 C5 C3 115.8(2) . . ? Ni1 O5 H51 111(3) . . ? Ni1 O5 H52 114(3) . . ? H51 O5 H52 111(4) . . ? O9B Na1 O10B 153.9(7) . . ? O9B Na1 O8B 77.3(6) . 3 ? O10B Na1 O8B 88.7(5) . 3 ? O9B Na1 O8A 77.1(5) . . ? O10B Na1 O8A 80.4(3) . . ? O8B Na1 O8A 87.53(18) 3 . ? O9B Na1 O6 97.2(5) . . ? O10B Na1 O6 103.0(3) . . ? O8B Na1 O6 83.34(17) 3 . ? O8A Na1 O6 170.15(15) . . ? O9B Na1 O10A 174.5(6) . . ? O10B Na1 O10A 31.3(4) . . ? O8B Na1 O10A 107.0(2) 3 . ? O8A Na1 O10A 106.22(18) . . ? O6 Na1 O10A 80.10(16) . . ? O9B Na1 O7 100.4(5) . . ? O10B Na1 O7 95.1(5) . . ? O8B Na1 O7 175.2(2) 3 . ? O8A Na1 O7 96.07(15) . . ? O6 Na1 O7 92.85(12) . . ? O10A Na1 O7 75.13(16) . . ? O9B Na1 O9A 16.8(6) . . ? O10B Na1 O9A 162.7(3) . . ? O8B Na1 O9A 93.4(3) 3 . ? O8A Na1 O9A 82.5(2) . . ? O6 Na1 O9A 94.3(2) . . ? O10A Na1 O9A 158.0(2) . . ? O7 Na1 O9A 84.0(2) . . ? O9B Na1 O8B 107.5(5) . . ? O10B Na1 O8B 49.7(3) . . ? O8B Na1 O8B 89.4(2) 3 . ? O8A Na1 O8B 30.82(19) . . ? O6 Na1 O8B 152.02(18) . . ? O10A Na1 O8B 76.3(2) . . ? O7 Na1 O8B 95.30(18) . . ? O9A Na1 O8B 113.1(2) . . ? O9B Na1 O8A 107.1(5) . 3 ? O10B Na1 O8A 60.1(5) . 3 ? O8B Na1 O8A 30.0(2) 3 3 ? O8A Na1 O8A 91.50(14) . 3 ? O6 Na1 O8A 82.42(11) . 3 ? O10A Na1 O8A 77.36(16) . 3 ? O7 Na1 O8A 152.49(16) . 3 ? O9A Na1 O8A 123.3(2) . 3 ? O8B Na1 O8A 78.03(17) . 3 ? O9B Na1 Na1 94.1(6) . 3 ? O10B Na1 Na1 60.8(4) . 3 ? O8B Na1 Na1 46.94(16) 3 3 ? O8A Na1 Na1 48.96(11) . 3 ? O6 Na1 Na1 124.53(9) . 3 ? O10A Na1 Na1 91.36(14) . 3 ? O7 Na1 Na1 137.79(13) . 3 ? O9A Na1 Na1 109.05(19) . 3 ? O8B Na1 Na1 42.50(14) . 3 ? O8A Na1 Na1 42.54(9) 3 3 ? Na1 O6 H61 121(4) . . ? Na1 O6 H62 110(3) . . ? H61 O6 H62 105(5) . . ? O8B O8A Na1 82.6(3) . . ? O8B O8A Na1 63.4(3) . 3 ? Na1 O8A Na1 88.50(14) . 3 ? O9B O9A Na1 64.3(18) . . ? O10B O10A Na1 69.4(6) . . ? O8A O8B Na1 86.7(4) . 3 ? O8A O8B Na1 66.6(3) . . ? Na1 O8B Na1 90.6(2) 3 . ? O9A O9B Na1 99(2) . . ? O10A O10B Na1 79.3(6) . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N2 H2 O6 0.85(4) 2.02(4) 2.828(3) 157(3) 4_566 O5 H51 O4 0.93(4) 1.86(5) 2.771(3) 167(4) 2_646 O5 H52 O2 0.84(4) 1.87(4) 2.709(3) 171(4) 4_576 O6 H61 O4 0.78(5) 2.06(5) 2.826(3) 167(5) 1_545 O6 H62 O1 0.76(5) 2.02(5) 2.741(3) 158(5) 2_645 _diffrn_measured_fraction_theta_max 0.983 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.992 _refine_diff_density_max 0.852 _refine_diff_density_min -0.507 _refine_diff_density_rms 0.096 data_p34 _database_code_depnum_ccdc_archive 'CCDC 224518' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C10 H14 Cu N4 O12' _chemical_formula_weight 445.79 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' Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 5.023(2) _cell_length_b 6.476(3) _cell_length_c 13.392(2) _cell_angle_alpha 99.74(2) _cell_angle_beta 96.17(2) _cell_angle_gamma 108.99(5) _cell_volume 399.8(3) _cell_formula_units_Z 1 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description chunk _exptl_crystal_colour 'pale blue' _exptl_crystal_size_max 0.19 _exptl_crystal_size_mid 0.07 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.852 _exptl_crystal_density_method ? _exptl_crystal_F_000 227 _exptl_absorpt_coefficient_mu 1.444 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'rotating anode' _diffrn_radiation_monochromator graphite _diffrn_measurement_device 'Rigaku R-Axis IIc' _diffrn_measurement_method 'area detector' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 2380 _diffrn_reflns_av_R_equivalents 0.1141 _diffrn_reflns_av_sigmaI/netI 0.1158 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 3.13 _diffrn_reflns_theta_max 28.48 _reflns_number_total 1307 _reflns_number_gt 1053 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'RAXIS software (Rikagu Corp., 1994)' _computing_cell_refinement ; HKL suite of programs: DENZO, XDISPLAYF (Otwinowski and Minor, 1997) ; _computing_data_reduction ; HKL suite of programs: SCALEPACK (Otwinowski and Minor, 1997) ; _computing_structure_solution 'XS: SHELXTL/PC 5.03 (Siemens, 1995)' _computing_structure_refinement 'XL: SHELXTL/PC 5.03 (Siemens, 1995)' _computing_molecular_graphics 'XP: SHELXTL/PC 5.03 (Siemens, 1995)' _computing_publication_material 'XCIF: SHELXTL/PC 5.03 (Siemens, 1995)' _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^)+(0.1119P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_ls_hydrogen_treatment refall _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.04(3) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 1307 _refine_ls_number_parameters 153 _refine_ls_number_restraints 4 _refine_ls_R_factor_all 0.0748 _refine_ls_R_factor_gt 0.0585 _refine_ls_wR_factor_ref 0.1598 _refine_ls_wR_factor_gt 0.1494 _refine_ls_goodness_of_fit_ref 1.018 _refine_ls_restrained_S_all 1.017 _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 Cu1 Cu 0.5000 0.5000 0.5000 0.0497(4) Uani 1 2 d S . . N1 N 0.2549(10) 0.4864(7) 0.3615(3) 0.0490(10) Uani 1 1 d . . . C1 C 0.4296(12) 0.6075(8) 0.3089(3) 0.0498(12) Uani 1 1 d . . . C2 C 0.2424(12) 0.5597(9) 0.2069(4) 0.0543(13) Uani 1 1 d . . . H21 H 0.312(14) 0.635(11) 0.157(5) 0.066(17) Uiso 1 1 d . . . C3 C -0.0489(12) 0.4084(9) 0.2020(4) 0.0513(12) Uani 1 1 d . . . N2 N -0.0324(10) 0.3681(7) 0.2964(3) 0.0491(10) Uani 1 1 d D . . H22 H -0.165(10) 0.285(8) 0.311(4) 0.056(17) Uiso 1 1 d D . . C4 C 0.7660(12) 0.7423(8) 0.3689(4) 0.0502(12) Uani 1 1 d . . . O1 O 0.8438(8) 0.7188(6) 0.4607(2) 0.0509(9) Uani 1 1 d . . . O2 O 0.9479(9) 0.8616(6) 0.3287(3) 0.0573(9) Uani 1 1 d . . . C5 C -0.3503(13) 0.2869(9) 0.1173(4) 0.0567(13) Uani 1 1 d . . . O3 O -0.5826(10) 0.1602(9) 0.1322(3) 0.0780(13) Uani 1 1 d . . . O4 O -0.3342(11) 0.3301(9) 0.0290(3) 0.0805(13) Uani 1 1 d . . . H4 H -0.522(17) 0.244(12) -0.027(5) 0.073(18) Uiso 1 1 d . . . O5 O 0.5732(10) 0.1866(7) 0.4107(3) 0.0543(9) Uani 1 1 d . . . H51 H 0.415(14) 0.080(9) 0.396(4) 0.043(15) Uiso 1 1 d . . . H52 H 0.742(15) 0.192(10) 0.458(5) 0.060(16) Uiso 1 1 d . . . O6 O 0.8315(11) 0.8832(9) 0.1222(3) 0.0824(14) Uani 1 1 d D . . H61 H 1.002(7) 0.948(10) 0.124(4) 0.066(19) Uiso 1 1 d D . . H62 H 0.857(13) 0.861(12) 0.178(3) 0.08(2) Uiso 1 1 d 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 Cu1 0.0547(7) 0.0609(6) 0.0409(6) 0.0187(4) 0.0199(4) 0.0225(4) N1 0.057(3) 0.054(2) 0.043(2) 0.0145(17) 0.0250(19) 0.022(2) C1 0.060(4) 0.056(3) 0.043(2) 0.017(2) 0.023(2) 0.025(2) C2 0.062(4) 0.066(3) 0.042(2) 0.019(2) 0.022(2) 0.025(3) C3 0.054(3) 0.065(3) 0.042(2) 0.014(2) 0.021(2) 0.026(3) N2 0.053(3) 0.054(2) 0.046(2) 0.0150(17) 0.023(2) 0.020(2) C4 0.058(3) 0.054(3) 0.046(2) 0.013(2) 0.025(2) 0.024(2) O1 0.058(2) 0.0616(19) 0.0424(17) 0.0186(14) 0.0204(15) 0.0255(17) O2 0.064(3) 0.068(2) 0.0465(18) 0.0207(15) 0.0263(17) 0.0233(19) C5 0.058(4) 0.065(3) 0.049(3) 0.012(2) 0.021(2) 0.020(3) O3 0.063(3) 0.109(3) 0.062(2) 0.023(2) 0.025(2) 0.023(3) O4 0.075(3) 0.112(4) 0.046(2) 0.025(2) 0.016(2) 0.016(3) O5 0.056(3) 0.062(2) 0.055(2) 0.0213(17) 0.0242(19) 0.026(2) O6 0.067(3) 0.120(4) 0.052(2) 0.028(2) 0.020(2) 0.015(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 Cu1 O1 2.030(4) . ? Cu1 O1 2.030(4) 2_666 ? Cu1 N1 2.085(4) 2_666 ? Cu1 N1 2.085(4) . ? Cu1 O5 2.333(4) 2_666 ? Cu1 O5 2.333(4) . ? N1 C1 1.324(6) . ? N1 N2 1.488(7) . ? C1 C2 1.496(8) . ? C1 C4 1.666(8) . ? C2 C3 1.460(8) . ? C2 H21 0.92(6) . ? C3 N2 1.333(6) . ? C3 C5 1.659(8) . ? N2 H22 0.77(3) . ? C4 O2 1.228(6) . ? C4 O1 1.299(6) . ? C5 O3 1.248(8) . ? C5 O4 1.265(6) . ? O4 H4 1.07(8) . ? O5 H51 0.84(6) . ? O5 H52 0.99(7) . ? O6 H61 0.82(3) . ? O6 H62 0.79(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 O1 Cu1 O1 180.0 . 2_666 ? O1 Cu1 N1 90.72(15) . 2_666 ? O1 Cu1 N1 89.28(15) 2_666 2_666 ? O1 Cu1 N1 89.28(15) . . ? O1 Cu1 N1 90.72(15) 2_666 . ? N1 Cu1 N1 180.000(1) 2_666 . ? O1 Cu1 O5 86.45(14) . 2_666 ? O1 Cu1 O5 93.55(14) 2_666 2_666 ? N1 Cu1 O5 85.27(15) 2_666 2_666 ? N1 Cu1 O5 94.73(15) . 2_666 ? O1 Cu1 O5 93.55(14) . . ? O1 Cu1 O5 86.45(14) 2_666 . ? N1 Cu1 O5 94.73(15) 2_666 . ? N1 Cu1 O5 85.27(15) . . ? O5 Cu1 O5 180.000(1) 2_666 . ? C1 N1 N2 109.8(4) . . ? C1 N1 Cu1 107.2(4) . . ? N2 N1 Cu1 142.4(3) . . ? N1 C1 C2 102.4(5) . . ? N1 C1 C4 116.1(4) . . ? C2 C1 C4 141.4(4) . . ? C3 C2 C1 113.5(4) . . ? C3 C2 H21 127(4) . . ? C1 C2 H21 119(4) . . ? N2 C3 C2 100.7(5) . . ? N2 C3 C5 120.7(4) . . ? C2 C3 C5 138.6(4) . . ? C3 N2 N1 113.6(4) . . ? C3 N2 H22 119(5) . . ? N1 N2 H22 127(5) . . ? O2 C4 O1 118.0(5) . . ? O2 C4 C1 122.3(4) . . ? O1 C4 C1 119.7(4) . . ? C4 O1 Cu1 107.6(3) . . ? O3 C5 O4 118.6(6) . . ? O3 C5 C3 126.8(4) . . ? O4 C5 C3 114.5(5) . . ? C5 O4 H4 115(4) . . ? Cu1 O5 H51 108(3) . . ? Cu1 O5 H52 99(3) . . ? H51 O5 H52 125(5) . . ? H61 O6 H62 93(4) . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N2 H22 O5 0.77(3) 2.02(4) 2.720(6) 152(6) 1_455 O4 H4 O6 1.07(8) 1.76(8) 2.823(7) 177(6) 2_565 O5 H51 O2 0.84(6) 2.30(7) 3.111(7) 163(5) 1_445 O5 H51 O1 0.84(6) 2.81(5) 2.996(5) 95(4) 2_666 O6 H61 O3 0.82(3) 2.07(3) 2.880(7) 170(6) 1_765 O6 H62 O2 0.79(3) 2.02(3) 2.801(5) 170(7) . _diffrn_measured_fraction_theta_max 0.646 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.849 _refine_diff_density_max 0.332 _refine_diff_density_min -0.809 _refine_diff_density_rms 0.089 data_p211a _database_code_depnum_ccdc_archive 'CCDC 224519' _chemical_name_common ;trans-diaquo-bis(pyrazole-3-carboxylic acid-5- carboxylate)zinc(ii) dihydrate ; _audit_creation_method SHELXL-97 _chemical_name_systematic ; trans-diaquo-bis(pyrazole-3-carboxylic acid-5-carboxylate)zinc(II) dihydrate ; _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C10 H14 N4 O12 Zn' _chemical_formula_weight 447.62 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' Zn Zn 0.2839 1.4301 '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 1 21/c 1' 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 10.021(2) _cell_length_b 12.456(5) _cell_length_c 6.871(3) _cell_angle_alpha 90.00 _cell_angle_beta 108.23(3) _cell_angle_gamma 90.00 _cell_volume 814.6(5) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description chunk _exptl_crystal_colour colourless _exptl_crystal_size_max 0.10 _exptl_crystal_size_mid 0.04 _exptl_crystal_size_min 0.03 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.825 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 456 _exptl_absorpt_coefficient_mu 1.584 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'rotating anode' _diffrn_radiation_monochromator graphite _diffrn_measurement_device 'Rigaku R-AXIS IIC' _diffrn_measurement_method 'area detector' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 2886 _diffrn_reflns_av_R_equivalents 0.0323 _diffrn_reflns_av_sigmaI/netI 0.0508 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -8 _diffrn_reflns_limit_l_max 8 _diffrn_reflns_theta_min 2.14 _diffrn_reflns_theta_max 25.43 _reflns_number_total 1498 _reflns_number_gt 1103 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'RAXIS software (Rikagu Corp., 1994)' _computing_cell_refinement ; HKL suite of programs: DENZO, XDISPLAYF (Otwinowski and Minor, 1997) ; _computing_data_reduction ; HKL suite of programs: SCALEPACK (Otwinowski and Minor, 1997) ; _computing_structure_solution 'XS: SHELXTL/PC 5.03 (Siemens, 1995)' _computing_structure_refinement 'XL: SHELXTL/PC 5.03 (Siemens, 1995)' _computing_molecular_graphics 'XP: SHELXTL/PC 5.03 (Siemens, 1995)' _computing_publication_material 'XCIF: SHELXTL/PC 5.03 (Siemens, 1995)' _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^)+(0.0384P)^2^+0.0112P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.007(2) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 1498 _refine_ls_number_parameters 140 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0523 _refine_ls_R_factor_gt 0.0318 _refine_ls_wR_factor_ref 0.0802 _refine_ls_wR_factor_gt 0.0736 _refine_ls_goodness_of_fit_ref 1.008 _refine_ls_restrained_S_all 1.008 _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 Zn1 Zn 0.5000 0.5000 0.5000 0.03480(19) Uani 1 2 d S . . N1 N 0.7183(3) 0.52528(18) 0.6130(4) 0.0301(5) Uani 1 1 d . . . C1 C 0.7580(3) 0.6251(2) 0.5841(4) 0.0299(6) Uani 1 1 d . . . C2 C 0.9033(3) 0.6328(2) 0.6453(5) 0.0320(7) Uani 1 1 d . . . H21 H 0.953(3) 0.687(3) 0.637(4) 0.038 Uiso 1 1 d . . . C3 C 0.9507(3) 0.5317(2) 0.7131(4) 0.0315(7) Uani 1 1 d . . . H3 H 1.171(4) 0.363(3) 0.903(5) 0.038 Uiso 1 1 d . . . N2 N 0.8359(3) 0.4693(2) 0.6906(4) 0.0318(6) Uani 1 1 d . . . H22 H 0.830(3) 0.400(3) 0.715(4) 0.038 Uiso 1 1 d . . . C4 C 0.6407(3) 0.7034(2) 0.4935(4) 0.0324(7) Uani 1 1 d . . . O1 O 0.5192(2) 0.66430(16) 0.4317(3) 0.0400(5) Uani 1 1 d . . . O2 O 0.6688(2) 0.80085(16) 0.4841(3) 0.0421(5) Uani 1 1 d . . . C5 C 1.0944(3) 0.4879(2) 0.7986(4) 0.0320(6) Uani 1 1 d . . . O3 O 1.0930(2) 0.38785(17) 0.8519(4) 0.0421(6) Uani 1 1 d . . . O4 O 1.1977(2) 0.54142(19) 0.8142(4) 0.0471(6) Uani 1 1 d . . . O5 O 0.4788(3) 0.5462(2) 0.7837(4) 0.0532(7) Uani 1 1 d . . . H51 H 0.535(5) 0.592(4) 0.859(6) 0.080 Uiso 1 1 d . . . H52 H 0.421(5) 0.532(4) 0.823(7) 0.080 Uiso 1 1 d . . . O6 O 0.7608(3) 0.2681(2) 0.7664(5) 0.0827(10) Uani 1 1 d . . . H61 H 0.7682 0.1815 0.7844 0.124 Uiso 1 1 d . . . H62 H 0.6769 0.2795 0.6940 0.124 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 Zn1 0.0211(3) 0.0292(3) 0.0510(3) -0.0005(2) 0.0069(2) -0.0045(2) N1 0.0197(13) 0.0267(13) 0.0407(13) 0.0014(9) 0.0047(10) -0.0001(9) C1 0.0227(16) 0.0261(15) 0.0390(15) 0.0007(12) 0.0068(12) -0.0007(12) C2 0.0228(17) 0.0272(16) 0.0445(17) 0.0025(13) 0.0083(13) -0.0007(12) C3 0.0217(16) 0.0336(16) 0.0369(15) -0.0006(12) 0.0061(12) 0.0004(12) N2 0.0218(15) 0.0243(13) 0.0469(14) 0.0015(10) 0.0070(11) 0.0008(10) C4 0.0244(16) 0.0284(16) 0.0422(16) 0.0037(12) 0.0072(13) 0.0019(12) O1 0.0192(12) 0.0274(11) 0.0663(14) 0.0046(9) 0.0031(10) -0.0007(8) O2 0.0277(12) 0.0254(11) 0.0649(14) 0.0069(9) 0.0025(10) -0.0028(9) C5 0.0254(16) 0.0311(16) 0.0377(15) 0.0007(12) 0.0074(12) 0.0031(13) O3 0.0240(13) 0.0318(12) 0.0652(15) 0.0096(10) 0.0065(11) 0.0057(9) O4 0.0238(13) 0.0378(12) 0.0768(16) 0.0056(11) 0.0116(12) -0.0012(10) O5 0.0368(16) 0.0667(17) 0.0591(15) -0.0206(12) 0.0197(12) -0.0201(12) O6 0.0488(19) 0.0375(15) 0.151(3) 0.0130(16) 0.0164(18) 0.0001(13) _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 Zn1 N1 2.104(2) . ? Zn1 N1 2.104(2) 3_666 ? Zn1 O5 2.106(3) 3_666 ? Zn1 O5 2.106(3) . ? Zn1 O1 2.122(2) 3_666 ? Zn1 O1 2.122(2) . ? N1 N2 1.328(3) . ? N1 C1 1.339(4) . ? C1 C2 1.387(4) . ? C1 C4 1.504(4) . ? C2 C3 1.374(4) . ? C2 H21 0.85(3) . ? C3 N2 1.357(4) . ? C3 C5 1.479(4) . ? N2 H22 0.88(3) . ? C4 O2 1.252(4) . ? C4 O1 1.256(3) . ? C5 O4 1.207(4) . ? C5 O3 1.301(4) . ? O3 H3 0.81(3) . ? O5 H51 0.85(4) . ? O5 H52 0.73(5) . ? O6 H61 1.085(3) . ? O6 H62 0.845(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 Zn1 N1 180.00(5) . 3_666 ? N1 Zn1 O5 89.33(10) . 3_666 ? N1 Zn1 O5 90.67(10) 3_666 3_666 ? N1 Zn1 O5 90.67(10) . . ? N1 Zn1 O5 89.33(10) 3_666 . ? O5 Zn1 O5 180.00(4) 3_666 . ? N1 Zn1 O1 102.62(8) . 3_666 ? N1 Zn1 O1 77.38(8) 3_666 3_666 ? O5 Zn1 O1 89.06(10) 3_666 3_666 ? O5 Zn1 O1 90.94(10) . 3_666 ? N1 Zn1 O1 77.38(8) . . ? N1 Zn1 O1 102.62(8) 3_666 . ? O5 Zn1 O1 90.94(10) 3_666 . ? O5 Zn1 O1 89.06(10) . . ? O1 Zn1 O1 180.0 3_666 . ? N2 N1 C1 106.2(2) . . ? N2 N1 Zn1 139.35(19) . . ? C1 N1 Zn1 114.01(19) . . ? N1 C1 C2 110.6(3) . . ? N1 C1 C4 115.7(3) . . ? C2 C1 C4 133.7(3) . . ? C3 C2 C1 105.0(3) . . ? C3 C2 H21 127(2) . . ? C1 C2 H21 128(2) . . ? N2 C3 C2 107.2(3) . . ? N2 C3 C5 121.3(3) . . ? C2 C3 C5 131.5(3) . . ? N1 N2 C3 111.0(2) . . ? N1 N2 H22 119(2) . . ? C3 N2 H22 130(2) . . ? O2 C4 O1 124.6(3) . . ? O2 C4 C1 119.4(3) . . ? O1 C4 C1 116.0(2) . . ? C4 O1 Zn1 116.42(18) . . ? O4 C5 O3 126.0(3) . . ? O4 C5 C3 122.2(3) . . ? O3 C5 C3 111.8(3) . . ? C5 O3 H3 113(2) . . ? Zn1 O5 H51 120(3) . . ? Zn1 O5 H52 127(4) . . ? H51 O5 H52 113(5) . . ? H61 O6 H62 104.7(3) . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N2 H22 O6 0.88(3) 1.86(3) 2.714(4) 161(3) . O3 H3 O2 0.81(3) 1.73(3) 2.541(3) 175(3) 2_746 O5 H51 O2 0.85(4) 1.90(5) 2.740(3) 170(4) 4_576 O5 H52 O4 0.73(5) 2.22(5) 2.890(4) 152(5) 1_455 O6 H61 O4 1.085(3) 1.940(2) 2.931(4) 150.1(2) 2_746 O6 H62 O1 0.845(3) 2.009(2) 2.837(4) 166.4(2) 3_666 _diffrn_measured_fraction_theta_max 0.993 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.380 _refine_diff_density_min -0.319 _refine_diff_density_rms 0.060 data_p35s _database_code_depnum_ccdc_archive 'CCDC 224520' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C10 H12 Mn2 N4 O12' _chemical_formula_weight 490.12 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' Mn Mn 0.3368 0.7283 '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 1 21/c 1' 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 6.4681(6) _cell_length_b 6.1154(6) _cell_length_c 19.932(2) _cell_angle_alpha 90.00 _cell_angle_beta 91.956(8) _cell_angle_gamma 90.00 _cell_volume 787.95(13) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 42 _cell_measurement_theta_min 9.643 _cell_measurement_theta_max 13.256 _exptl_crystal_description needle _exptl_crystal_colour colourless _exptl_crystal_size_max 0.33 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 2.066 _exptl_crystal_density_method ? _exptl_crystal_F_000 492 _exptl_absorpt_coefficient_mu 1.683 _exptl_absorpt_correction_type psi-scans _exptl_absorpt_correction_T_min 0.664 _exptl_absorpt_correction_T_max 0.828 _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device 'Siemens P4' _diffrn_measurement_method \w-scans _diffrn_detector_area_resol_mean ? _diffrn_standards_number 3 _diffrn_standards_interval_count 100 _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0.0 _diffrn_reflns_number 2146 _diffrn_reflns_av_R_equivalents 0.0239 _diffrn_reflns_av_sigmaI/netI 0.0312 _diffrn_reflns_limit_h_min -1 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -1 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 3.15 _diffrn_reflns_theta_max 25.00 _reflns_number_total 1391 _reflns_number_gt 1251 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'XSCANS 2.2 (Siemens, 1996)' _computing_cell_refinement 'XSCANS 2.2 (Siemens, 1996)' _computing_data_reduction 'XSCANS 2.2 (Siemens, 1996)' _computing_structure_solution 'XS: SHELXTL/PC 5.03 (Siemens, 1995)' _computing_structure_refinement 'XL: SHELXTL/PC 5.03 (Siemens, 1995)' _computing_molecular_graphics 'XP: SHELXTL/PC 5.03 (Siemens, 1995)' _computing_publication_material 'XCIF: SHELXTL/PC 5.03 (Siemens, 1995)' _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^)+(0.0338P)^2^+0.3866P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0019(7) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 1391 _refine_ls_number_parameters 152 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0291 _refine_ls_R_factor_gt 0.0249 _refine_ls_wR_factor_ref 0.0679 _refine_ls_wR_factor_gt 0.0648 _refine_ls_goodness_of_fit_ref 1.046 _refine_ls_restrained_S_all 1.046 _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 Mn1 Mn 0.07632(5) 0.65458(4) 0.299570(14) 0.01532(14) Uani 1 1 d . . . N1 N 0.2204(3) 0.7983(3) 0.39114(8) 0.0176(4) Uani 1 1 d . . . C1 C 0.1793(3) 1.0094(3) 0.40382(9) 0.0133(4) Uani 1 1 d . . . C2 C 0.2183(3) 1.0569(3) 0.47152(10) 0.0149(4) Uani 1 1 d . . . H21 H 0.204(3) 1.195(4) 0.4953(11) 0.014(5) Uiso 1 1 d . . . C3 C 0.2845(3) 0.8621(3) 0.49959(10) 0.0152(4) Uani 1 1 d . . . N2 N 0.2836(3) 0.7132(3) 0.44979(8) 0.0185(4) Uani 1 1 d . . . H22 H 0.343(4) 0.584(5) 0.4507(12) 0.030(7) Uiso 1 1 d . . . C4 C 0.1053(3) 1.1418(3) 0.34517(10) 0.0147(4) Uani 1 1 d . . . O1 O 0.0544(2) 1.0316(2) 0.29289(6) 0.0181(3) Uani 1 1 d . . . O2 O 0.1001(3) 1.3434(2) 0.35057(8) 0.0244(4) Uani 1 1 d . . . C5 C 0.3443(3) 0.7903(3) 0.56953(10) 0.0155(4) Uani 1 1 d . . . O3 O 0.4023(3) 0.5953(3) 0.57539(7) 0.0244(4) Uani 1 1 d . . . O4 O 0.3308(2) 0.9259(3) 0.61583(6) 0.0218(4) Uani 1 1 d . . . O5 O 0.3669(3) 0.6554(3) 0.24969(10) 0.0342(5) Uani 1 1 d . . . H51 H 0.375(5) 0.645(5) 0.2091(16) 0.046(9) Uiso 1 1 d . . . H52 H 0.464(5) 0.662(4) 0.2663(15) 0.029(9) Uiso 1 1 d . . . O6 O -0.2441(3) 0.6781(3) 0.33436(9) 0.0235(4) Uani 1 1 d . . . H61 H -0.282(4) 0.587(5) 0.3614(14) 0.033(8) Uiso 1 1 d . . . H62 H -0.273(5) 0.777(6) 0.3537(15) 0.046(10) 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 Mn1 0.0235(2) 0.0096(2) 0.0126(2) -0.00122(11) -0.00363(13) -0.00017(12) N1 0.0274(9) 0.0104(8) 0.0146(8) 0.0009(7) -0.0048(7) 0.0027(7) C1 0.0155(9) 0.0086(9) 0.0157(9) 0.0003(8) -0.0012(7) -0.0001(8) C2 0.0190(10) 0.0108(9) 0.0147(9) -0.0009(8) -0.0006(7) -0.0005(8) C3 0.0182(10) 0.0141(10) 0.0132(9) 0.0005(7) -0.0008(8) 0.0004(8) N2 0.0307(10) 0.0099(8) 0.0143(9) 0.0012(7) -0.0055(7) 0.0043(8) C4 0.0160(9) 0.0120(10) 0.0162(10) 0.0019(7) 0.0005(7) 0.0005(8) O1 0.0259(8) 0.0155(7) 0.0126(7) 0.0009(6) -0.0042(6) 0.0006(6) O2 0.0392(9) 0.0088(8) 0.0249(8) 0.0037(5) -0.0053(7) 0.0018(6) C5 0.0169(10) 0.0154(10) 0.0143(10) 0.0026(8) 0.0003(7) 0.0005(8) O3 0.0378(9) 0.0159(7) 0.0198(7) 0.0061(6) 0.0025(6) 0.0086(7) O4 0.0337(9) 0.0190(8) 0.0127(7) -0.0029(6) -0.0007(6) 0.0031(7) O5 0.0243(10) 0.0581(14) 0.0200(9) -0.0109(8) -0.0007(8) -0.0024(9) O6 0.0297(9) 0.0134(8) 0.0280(9) 0.0007(7) 0.0077(7) 0.0009(7) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Mn1 O1 2.1378(13) 2_545 ? Mn1 O5 2.1560(19) . ? Mn1 O2 2.1607(14) 1_545 ? Mn1 N1 2.2036(17) . ? Mn1 O6 2.2127(17) . ? Mn1 O1 2.3138(16) . ? N1 N2 1.331(2) . ? N1 C1 1.344(3) . ? C1 C2 1.395(3) . ? C1 C4 1.488(3) . ? C2 C3 1.378(3) . ? C2 H21 0.97(2) . ? C3 N2 1.347(3) . ? C3 C5 1.500(3) . ? N2 H22 0.88(3) . ? C4 O2 1.238(2) . ? C4 O1 1.275(2) . ? O1 Mn1 2.1378(13) 2 ? O2 Mn1 2.1607(14) 1_565 ? C5 O4 1.246(3) . ? C5 O3 1.254(3) . ? O5 H51 0.82(3) . ? O5 H52 0.70(3) . ? O6 H61 0.82(3) . ? O6 H62 0.74(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 O1 Mn1 O5 85.90(7) 2_545 . ? O1 Mn1 O2 96.63(6) 2_545 1_545 ? O5 Mn1 O2 99.78(7) . 1_545 ? O1 Mn1 N1 176.30(6) 2_545 . ? O5 Mn1 N1 91.74(7) . . ? O2 Mn1 N1 86.58(6) 1_545 . ? O1 Mn1 O6 86.90(6) 2_545 . ? O5 Mn1 O6 170.07(7) . . ? O2 Mn1 O6 87.83(7) 1_545 . ? N1 Mn1 O6 95.09(7) . . ? O1 Mn1 O1 106.22(4) 2_545 . ? O5 Mn1 O1 91.37(6) . . ? O2 Mn1 O1 155.25(5) 1_545 . ? N1 Mn1 O1 70.95(5) . . ? O6 Mn1 O1 84.08(6) . . ? N2 N1 C1 105.49(16) . . ? N2 N1 Mn1 132.85(14) . . ? C1 N1 Mn1 117.27(13) . . ? N1 C1 C2 110.61(16) . . ? N1 C1 C4 115.83(17) . . ? C2 C1 C4 133.56(18) . . ? C3 C2 C1 104.82(17) . . ? C3 C2 H21 125.8(13) . . ? C1 C2 H21 129.4(13) . . ? N2 C3 C2 106.96(16) . . ? N2 C3 C5 118.79(17) . . ? C2 C3 C5 134.21(18) . . ? N1 N2 C3 112.12(17) . . ? N1 N2 H22 119.4(15) . . ? C3 N2 H22 127.0(16) . . ? O2 C4 O1 126.18(19) . . ? O2 C4 C1 118.87(18) . . ? O1 C4 C1 114.95(17) . . ? C4 O1 Mn1 127.04(13) . 2 ? C4 O1 Mn1 117.78(12) . . ? Mn1 O1 Mn1 114.94(6) 2 . ? C4 O2 Mn1 146.92(15) . 1_565 ? O4 C5 O3 126.30(18) . . ? O4 C5 C3 118.11(18) . . ? O3 C5 C3 115.59(17) . . ? Mn1 O5 H51 123(2) . . ? Mn1 O5 H52 124(2) . . ? H51 O5 H52 112(3) . . ? Mn1 O6 H61 118(2) . . ? Mn1 O6 H62 118(3) . . ? H61 O6 H62 97(3) . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O5 H51 O4 0.82(3) 1.92(3) 2.716(2) 165(3) 4_575 O5 H52 O6 0.70(3) 2.29(3) 2.985(3) 172(3) 1_655 O6 H61 O3 0.82(3) 1.87(3) 2.684(2) 172(3) 3_566 O6 H62 O4 0.74(3) 1.96(4) 2.684(2) 166(3) 3_576 N2 H22 O3 0.88(3) 2.06(3) 2.830(2) 146(2) 3_666 _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.345 _refine_diff_density_min -0.451 _refine_diff_density_rms 0.062 data_pk1 _database_code_depnum_ccdc_archive 'CCDC 224521' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C10 H24 Mn2 N4 O18' _chemical_formula_weight 598.21 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' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Mn Mn 0.3368 0.7283 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.2808(7) _cell_length_b 7.3579(10) _cell_length_c 12.0107(11) _cell_angle_alpha 103.890(8) _cell_angle_beta 92.257(7) _cell_angle_gamma 112.480(7) _cell_volume 570.95(11) _cell_formula_units_Z 1 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 46 _cell_measurement_theta_min 5.18 _cell_measurement_theta_max 19.73 _exptl_crystal_description 'multi-faceted block' _exptl_crystal_colour colourless _exptl_crystal_size_max 0.45 _exptl_crystal_size_mid 0.40 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.740 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 306 _exptl_absorpt_coefficient_mu 1.197 _exptl_absorpt_correction_type psi-scans _exptl_absorpt_correction_T_min 0.469 _exptl_absorpt_correction_T_max 0.618 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device 'Siemens P4' _diffrn_measurement_method \w-scans _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 2513 _diffrn_reflns_av_R_equivalents 0.0163 _diffrn_reflns_av_sigmaI/netI 0.0285 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 1 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 3.06 _diffrn_reflns_theta_max 25.00 _reflns_number_total 1998 _reflns_number_gt 1853 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'XSCANS 2.2 (Siemens, 1996)' _computing_cell_refinement 'XSCANS 2.2 (Siemens, 1996)' _computing_data_reduction 'XSCANS 2.2 (Siemens, 1996)' _computing_structure_solution 'XS: SHELXTL/PC 5.03 (Siemens, 1995)' _computing_structure_refinement 'XL: SHELXTL/PC 5.03 (Siemens, 1995)' _computing_molecular_graphics 'XP: SHELXTL/PC 5.03 (Siemens, 1995)' _computing_publication_material 'XCIF: SHELXTL/PC 5.03 (Siemens, 1995)' _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^)+(0.0374P)^2^+0.2177P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.067(4) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 1998 _refine_ls_number_parameters 206 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0283 _refine_ls_R_factor_gt 0.0263 _refine_ls_wR_factor_ref 0.0719 _refine_ls_wR_factor_gt 0.0706 _refine_ls_goodness_of_fit_ref 1.042 _refine_ls_restrained_S_all 1.042 _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 Mn1 Mn 0.5000 0.5000 0.5000 0.02409(15) Uani 1 2 d S . . N1 N 0.7596(2) 0.6803(2) 0.42645(12) 0.0230(3) Uani 1 1 d . . . C1 C 0.9371(3) 0.7264(2) 0.48719(14) 0.0202(4) Uani 1 1 d . . . C2 C 1.0931(3) 0.8081(3) 0.42610(14) 0.0213(4) Uani 1 1 d . . . H21 H 1.226(4) 0.851(3) 0.4502(19) 0.031(5) Uiso 1 1 d . . . C3 C 0.9991(3) 0.8080(3) 0.32409(15) 0.0213(4) Uani 1 1 d . . . N2 N 0.8003(2) 0.7307(2) 0.32811(13) 0.0238(3) Uani 1 1 d . . . H22 H 0.703(4) 0.720(3) 0.279(2) 0.039(6) Uiso 1 1 d . . . C4 C 0.9342(3) 0.6831(3) 0.60314(14) 0.0206(4) Uani 1 1 d . . . O1 O 0.76239(19) 0.5964(2) 0.62984(11) 0.0279(3) Uani 1 1 d . . . O2 O 1.09683(18) 0.7344(2) 0.66502(10) 0.0291(3) Uani 1 1 d . . . C5 C 1.0809(3) 0.8756(3) 0.22266(15) 0.0215(4) Uani 1 1 d . . . O3 O 0.95493(18) 0.8538(2) 0.14003(10) 0.0275(3) Uani 1 1 d . . . O4 O 1.26767(19) 0.9482(2) 0.22662(11) 0.0307(3) Uani 1 1 d . . . O5 O 0.5467(2) 0.2263(2) 0.41222(14) 0.0336(3) Uani 1 1 d . . . H51 H 0.649(4) 0.235(4) 0.386(2) 0.040(7) Uiso 1 1 d . . . H52 H 0.464(4) 0.153(4) 0.364(2) 0.039(7) Uiso 1 1 d . . . Mn2 Mn 1.0000 1.0000 0.0000 0.02597(15) Uani 1 2 d S . . O6 O 0.6803(3) 0.8347(3) -0.06903(19) 0.0581(6) Uani 1 1 d . . . H61 H 0.591(5) 0.760(5) -0.058(3) 0.054(9) Uiso 1 1 d . . . H62 H 0.660(5) 0.878(5) -0.120(3) 0.079(11) Uiso 1 1 d . . . O7 O 0.9452(3) 1.2549(3) 0.10585(15) 0.0476(4) Uani 1 1 d . . . H71 H 0.871(5) 1.291(5) 0.079(3) 0.056(9) Uiso 1 1 d . . . H72 H 0.925(5) 1.258(5) 0.174(3) 0.075(10) Uiso 1 1 d . . . O8 O 0.5822(2) 0.3561(3) 0.78374(14) 0.0368(4) Uani 1 1 d . . . H81 H 0.612(5) 0.260(5) 0.762(3) 0.070(10) Uiso 1 1 d . . . H82 H 0.656(4) 0.440(4) 0.753(3) 0.052(8) Uiso 1 1 d . . . O9 O 0.6924(2) 0.4249(3) 0.02464(15) 0.0399(4) Uani 1 1 d . . . H91 H 0.754(6) 0.558(6) 0.058(3) 0.097(12) Uiso 1 1 d . . . H92 H 0.673(5) 0.413(5) -0.044(3) 0.060(9) 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 Mn1 0.0175(2) 0.0338(2) 0.0228(2) 0.01264(16) 0.00644(15) 0.00901(17) N1 0.0212(7) 0.0310(8) 0.0193(7) 0.0123(6) 0.0046(6) 0.0100(6) C1 0.0214(8) 0.0230(8) 0.0172(8) 0.0068(6) 0.0020(6) 0.0093(7) C2 0.0187(9) 0.0268(9) 0.0194(8) 0.0088(7) 0.0038(7) 0.0089(7) C3 0.0207(8) 0.0250(8) 0.0200(8) 0.0098(7) 0.0034(7) 0.0090(7) N2 0.0215(7) 0.0346(8) 0.0182(7) 0.0139(6) 0.0037(6) 0.0105(6) C4 0.0219(9) 0.0260(8) 0.0163(8) 0.0069(6) 0.0046(7) 0.0115(7) O1 0.0225(7) 0.0438(8) 0.0218(6) 0.0165(6) 0.0070(5) 0.0133(6) O2 0.0229(7) 0.0462(8) 0.0192(6) 0.0118(5) 0.0022(5) 0.0134(6) C5 0.0233(9) 0.0227(8) 0.0191(8) 0.0083(6) 0.0046(7) 0.0084(7) O3 0.0251(6) 0.0366(7) 0.0209(6) 0.0157(5) 0.0015(5) 0.0080(5) O4 0.0229(7) 0.0420(8) 0.0275(7) 0.0180(6) 0.0056(5) 0.0084(6) O5 0.0210(7) 0.0387(8) 0.0355(8) 0.0033(7) 0.0020(7) 0.0105(6) Mn2 0.0271(2) 0.0339(2) 0.0212(2) 0.01577(16) 0.00561(16) 0.01168(18) O6 0.0292(9) 0.0783(13) 0.0675(13) 0.0549(11) -0.0001(8) 0.0024(9) O7 0.0722(12) 0.0676(11) 0.0263(8) 0.0191(8) 0.0133(8) 0.0488(10) O8 0.0318(8) 0.0434(9) 0.0394(8) 0.0189(7) 0.0047(6) 0.0155(7) O9 0.0430(9) 0.0397(9) 0.0346(9) 0.0151(7) 0.0021(7) 0.0115(7) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Mn1 O1 2.1870(13) 2_666 ? Mn1 O1 2.1870(13) . ? Mn1 O5 2.1944(15) 2_666 ? Mn1 O5 2.1944(15) . ? Mn1 N1 2.2114(14) . ? Mn1 N1 2.2114(14) 2_666 ? N1 N2 1.332(2) . ? N1 C1 1.338(2) . ? C1 C2 1.395(2) . ? C1 C4 1.501(2) . ? C2 C3 1.379(2) . ? C2 H21 0.91(2) . ? C3 N2 1.345(2) . ? C3 C5 1.486(2) . ? N2 H22 0.87(2) . ? C4 O2 1.246(2) . ? C4 O1 1.263(2) . ? C5 O4 1.251(2) . ? C5 O3 1.261(2) . ? O3 Mn2 2.1761(12) . ? O5 H51 0.80(3) . ? O5 H52 0.75(3) . ? Mn2 O3 2.1761(12) 2_775 ? Mn2 O7 2.1819(17) . ? Mn2 O7 2.1819(17) 2_775 ? Mn2 O6 2.1872(18) 2_775 ? Mn2 O6 2.1872(18) . ? O6 H61 0.71(3) . ? O6 H62 0.79(4) . ? O7 H71 0.77(3) . ? O7 H72 0.83(4) . ? O8 H81 0.81(3) . ? O8 H82 0.83(3) . ? O9 H91 0.88(4) . ? O9 H92 0.81(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 O1 Mn1 O1 180.0 2_666 . ? O1 Mn1 O5 90.63(6) 2_666 2_666 ? O1 Mn1 O5 89.37(6) . 2_666 ? O1 Mn1 O5 89.37(6) 2_666 . ? O1 Mn1 O5 90.63(6) . . ? O5 Mn1 O5 180.0 2_666 . ? O1 Mn1 N1 105.55(5) 2_666 . ? O1 Mn1 N1 74.45(5) . . ? O5 Mn1 N1 92.17(6) 2_666 . ? O5 Mn1 N1 87.83(6) . . ? O1 Mn1 N1 74.45(5) 2_666 2_666 ? O1 Mn1 N1 105.55(5) . 2_666 ? O5 Mn1 N1 87.83(6) 2_666 2_666 ? O5 Mn1 N1 92.17(6) . 2_666 ? N1 Mn1 N1 180.0 . 2_666 ? N2 N1 C1 106.03(14) . . ? N2 N1 Mn1 139.21(11) . . ? C1 N1 Mn1 113.47(11) . . ? N1 C1 C2 110.44(15) . . ? N1 C1 C4 117.04(15) . . ? C2 C1 C4 132.52(16) . . ? C3 C2 C1 104.75(15) . . ? C3 C2 H21 129.1(14) . . ? C1 C2 H21 126.2(14) . . ? N2 C3 C2 107.16(15) . . ? N2 C3 C5 121.41(15) . . ? C2 C3 C5 131.43(16) . . ? N1 N2 C3 111.62(14) . . ? N1 N2 H22 119.6(17) . . ? C3 N2 H22 128.6(17) . . ? O2 C4 O1 125.25(16) . . ? O2 C4 C1 118.90(15) . . ? O1 C4 C1 115.85(15) . . ? C4 O1 Mn1 118.08(11) . . ? O4 C5 O3 125.90(16) . . ? O4 C5 C3 117.30(15) . . ? O3 C5 C3 116.80(15) . . ? C5 O3 Mn2 129.26(11) . . ? Mn1 O5 H51 121.2(18) . . ? Mn1 O5 H52 114(2) . . ? H51 O5 H52 105(3) . . ? O3 Mn2 O3 180.00(6) . 2_775 ? O3 Mn2 O7 90.77(6) . . ? O3 Mn2 O7 89.23(6) 2_775 . ? O3 Mn2 O7 89.23(6) . 2_775 ? O3 Mn2 O7 90.77(6) 2_775 2_775 ? O7 Mn2 O7 180.00(9) . 2_775 ? O3 Mn2 O6 89.86(6) . 2_775 ? O3 Mn2 O6 90.14(6) 2_775 2_775 ? O7 Mn2 O6 89.10(8) . 2_775 ? O7 Mn2 O6 90.90(9) 2_775 2_775 ? O3 Mn2 O6 90.14(6) . . ? O3 Mn2 O6 89.86(6) 2_775 . ? O7 Mn2 O6 90.90(8) . . ? O7 Mn2 O6 89.10(8) 2_775 . ? O6 Mn2 O6 180.0 2_775 . ? Mn2 O6 H61 140(2) . . ? Mn2 O6 H62 107(3) . . ? H61 O6 H62 113(3) . . ? Mn2 O7 H71 119(2) . . ? Mn2 O7 H72 120(2) . . ? H71 O7 H72 107(3) . . ? H81 O8 H82 103(3) . . ? H91 O9 H92 106(3) . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N2 H22 O8 0.87(2) 2.00(2) 2.811(2) 156(2) 2_666 O5 H51 O2 0.80(3) 1.92(3) 2.725(2) 176(3) 2_766 O5 H52 O4 0.75(3) 2.01(3) 2.749(2) 173(3) 1_445 O6 H61 O9 0.71(3) 2.11(3) 2.817(2) 171(3) 2_665 O6 H62 O4 0.79(4) 1.97(4) 2.706(2) 155(3) 2_775 O7 H71 O9 0.77(3) 2.08(3) 2.847(2) 172(3) 1_565 O7 H72 O2 0.83(4) 1.94(4) 2.767(2) 174(3) 2_776 O8 H81 O4 0.81(3) 2.06(4) 2.824(2) 158(3) 2_766 O8 H82 O1 0.83(3) 2.08(3) 2.872(2) 161(3) . O9 H91 O3 0.88(4) 2.07(4) 2.935(2) 167(4) . O9 H92 O8 0.81(3) 2.04(3) 2.842(2) 172(3) 1_554 _diffrn_measured_fraction_theta_max 0.992 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.992 _refine_diff_density_max 0.346 _refine_diff_density_min -0.322 _refine_diff_density_rms 0.058 data_p12121 _database_code_depnum_ccdc_archive 'CCDC 224522' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C10 H12 N4 Ni2 O12' _chemical_formula_weight 497.66 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' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 6.8212(7) _cell_length_b 7.3875(8) _cell_length_c 8.5066(9) _cell_angle_alpha 105.248(2) _cell_angle_beta 90.594(2) _cell_angle_gamma 111.650(2) _cell_volume 381.63(7) _cell_formula_units_Z 1 _cell_measurement_temperature 200(2) _cell_measurement_reflns_used 2034 _cell_measurement_theta_min 2.50 _cell_measurement_theta_max 27.84 _exptl_crystal_description plate _exptl_crystal_colour green _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.165 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 252 _exptl_absorpt_coefficient_mu 2.550 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.606 _exptl_absorpt_correction_T_max 0.928 _exptl_absorpt_process_details 'SADABS (Bruker AXS Inc., 2000)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 200(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'rotating anode' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker SMART Apex' _diffrn_measurement_method 'CCD area detector' _diffrn_detector_area_resol_mean 8.333 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 1849 _diffrn_reflns_av_R_equivalents 0.0222 _diffrn_reflns_av_sigmaI/netI 0.0128 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -8 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 3.24 _diffrn_reflns_theta_max 27.84 _reflns_number_total 1602 _reflns_number_gt 1584 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART-NT 5.6 (Bruker AXS Inc., 2000)' _computing_cell_refinement 'SMART-NT 5.6 (Bruker AXS Inc., 2000)' _computing_data_reduction 'SAINT+ 6.0 (Bruker AXS Inc., 2000)' _computing_structure_solution 'XS: SHELXTL 5.1 (Bruker AXS Inc., 1997)' _computing_structure_refinement 'XL: SHELXTL 5.1 (Bruker AXS Inc., 1997)' _computing_molecular_graphics 'XP: SHELXTL 5.1 (Bruker AXS Inc., 1997)' _computing_publication_material 'XCIF: SHELXTL 5.1 (Bruker AXS Inc., 1997)' _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^)+(0.0928P)^2^+0.3829P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_extinction_expression ? _refine_ls_number_reflns 1602 _refine_ls_number_parameters 143 _refine_ls_number_restraints 5 _refine_ls_R_factor_all 0.0509 _refine_ls_R_factor_gt 0.0501 _refine_ls_wR_factor_ref 0.1244 _refine_ls_wR_factor_gt 0.1240 _refine_ls_goodness_of_fit_ref 1.151 _refine_ls_restrained_S_all 1.153 _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 Ni1 Ni 0.20400(5) 0.21545(5) 0.05605(4) 0.0109(3) Uani 1 1 d . . . C1 C 0.4124(4) 0.2454(4) 0.3574(3) 0.0117(6) Uani 1 1 d . . . C2 C 0.4147(5) 0.2382(4) 0.5194(3) 0.0138(6) Uani 1 1 d . . . H2A H 0.5237 0.2358 0.5844 0.017 Uiso 1 1 calc R . . C3 C 0.2194(4) 0.2353(4) 0.5617(3) 0.0129(6) Uani 1 1 d . . . N1 N 0.2264(4) 0.2434(4) 0.3029(3) 0.0121(5) Uani 1 1 d . . . N2 N 0.1103(4) 0.2373(4) 0.4286(3) 0.0124(5) Uani 1 1 d D . . H2 H -0.014(5) 0.234(6) 0.415(5) 0.015 Uiso 1 1 d D . . C4 C 0.5738(4) 0.2588(4) 0.2395(3) 0.0123(6) Uani 1 1 d . . . O1 O 0.5172(3) 0.2693(3) 0.1001(3) 0.0142(5) Uani 1 1 d . . . O2 O 0.7497(3) 0.2578(4) 0.2786(3) 0.0186(5) Uani 1 1 d . . . C5 C 0.1265(5) 0.2234(4) 0.7182(3) 0.0125(6) Uani 1 1 d . . . O3 O -0.0519(3) 0.2348(3) 0.7334(3) 0.0160(5) Uani 1 1 d . . . O4 O 0.2402(4) 0.1983(3) 0.8214(3) 0.0153(5) Uani 1 1 d . . . O5 O 0.1234(3) -0.1060(3) -0.0011(3) 0.0116(5) Uani 1 1 d D . . H51 H 0.153(6) -0.170(6) -0.081(4) 0.014 Uiso 1 1 d D . . H52 H 0.136(6) -0.139(6) 0.093(4) 0.014 Uiso 1 1 d D . . O6 O 0.2438(4) 0.5118(4) 0.1002(3) 0.0206(5) Uani 1 1 d D . . H61 H 0.303(7) 0.578(7) 0.039(5) 0.031 Uiso 1 1 d D . . H62 H 0.170(7) 0.563(7) 0.145(6) 0.031 Uiso 1 1 d D . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Ni1 0.0105(3) 0.0158(3) 0.0080(3) 0.00536(19) 0.00288(17) 0.0054(2) C1 0.0107(13) 0.0139(13) 0.0108(13) 0.0045(10) 0.0029(10) 0.0045(10) C2 0.0144(13) 0.0189(13) 0.0088(12) 0.0048(10) 0.0007(10) 0.0066(11) C3 0.0151(15) 0.0138(13) 0.0106(15) 0.0056(10) 0.0027(11) 0.0050(11) N1 0.0131(12) 0.0153(11) 0.0092(11) 0.0046(9) 0.0047(9) 0.0061(9) N2 0.0112(11) 0.0175(12) 0.0107(12) 0.0062(9) 0.0046(9) 0.0066(9) C4 0.0133(13) 0.0128(12) 0.0109(13) 0.0035(9) 0.0046(10) 0.0050(10) O1 0.0110(10) 0.0222(11) 0.0108(10) 0.0068(8) 0.0039(8) 0.0065(8) O2 0.0142(10) 0.0321(12) 0.0136(10) 0.0073(9) 0.0027(8) 0.0130(9) C5 0.0138(13) 0.0129(12) 0.0095(12) 0.0028(10) 0.0035(10) 0.0039(10) O3 0.0162(11) 0.0215(11) 0.0142(10) 0.0083(8) 0.0058(8) 0.0093(9) O4 0.0163(10) 0.0237(11) 0.0096(10) 0.0079(8) 0.0043(8) 0.0097(9) O5 0.0120(10) 0.0164(10) 0.0093(10) 0.0059(8) 0.0053(7) 0.0069(8) O6 0.0259(12) 0.0190(11) 0.0233(12) 0.0120(9) 0.0153(9) 0.0114(9) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Ni1 N1 2.053(2) . yes Ni1 O1 2.035(2) . yes Ni1 O4 1.990(2) 1_554 yes Ni1 O5 2.075(2) 2 yes Ni1 O5 2.145(2) . yes Ni1 O6 2.034(2) . yes C1 N1 1.340(4) . ? C1 C2 1.393(4) . ? C1 C4 1.491(4) . ? C2 C3 1.378(4) . ? C2 H2A 0.9300 . ? C3 N2 1.355(4) . ? C3 C5 1.490(4) . ? N1 N2 1.338(3) . ? N2 H2 0.84(3) . ? C4 O2 1.245(4) . ? C4 O1 1.274(4) . ? C5 O3 1.256(4) . ? C5 O4 1.259(4) . ? O4 Ni1 1.990(2) 1_556 ? O5 Ni1 2.075(2) 2 ? O5 H51 0.80(3) . ? O5 H52 0.91(3) . ? O6 H61 0.82(3) . ? O6 H62 0.78(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 O4 Ni1 O6 89.73(10) 1_554 . yes O4 Ni1 O1 89.20(9) 1_554 . yes O6 Ni1 O1 96.08(10) . . yes O4 Ni1 N1 169.22(10) 1_554 . yes O6 Ni1 N1 91.34(10) . . yes O1 Ni1 N1 80.02(9) . . yes O4 Ni1 O5 90.45(9) 1_554 2 yes O6 Ni1 O5 94.18(10) . 2 yes O1 Ni1 O5 169.73(9) . 2 yes N1 Ni1 O5 100.17(9) . 2 yes O4 Ni1 O5 89.27(9) 1_554 . yes O6 Ni1 O5 173.16(9) . . yes O1 Ni1 O5 90.67(9) . . yes N1 Ni1 O5 90.90(9) . . yes O5 Ni1 O5 79.06(9) 2 . yes N1 C1 C2 110.9(2) . . ? N1 C1 C4 116.1(2) . . ? C2 C1 C4 132.9(3) . . ? C3 C2 C1 104.5(2) . . ? C3 C2 H2A 127.7 . . ? C1 C2 H2A 127.7 . . ? N2 C3 C2 107.6(2) . . ? N2 C3 C5 122.6(2) . . ? C2 C3 C5 129.8(3) . . ? N2 N1 C1 105.9(2) . . ? N2 N1 Ni1 141.8(2) . . ? C1 N1 Ni1 111.60(18) . . ? N1 N2 C3 111.0(2) . . ? N1 N2 H2 119(3) . . ? C3 N2 H2 131(3) . . ? O2 C4 O1 124.0(3) . . ? O2 C4 C1 120.6(3) . . ? O1 C4 C1 115.4(2) . . ? C4 O1 Ni1 115.11(18) . . ? O3 C5 O4 127.2(3) . . ? O3 C5 C3 119.0(3) . . ? O4 C5 C3 113.8(2) . . ? C5 O4 Ni1 127.87(19) . 1_556 ? Ni1 O5 Ni1 100.94(9) . 2 yes Ni1 O5 H51 101(3) 2 . ? Ni1 O5 H51 123(3) . . ? Ni1 O5 H52 102(3) 2 . ? Ni1 O5 H52 109(2) . . ? H51 O5 H52 117(4) . . ? Ni1 O6 H61 121(3) . . ? Ni1 O6 H62 127(4) . . ? H61 O6 H62 107(5) . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N2 H2 O2 0.84(3) 2.06(3) 2.830(3) 151(4) 1_455 O5 H51 O2 0.80(3) 1.86(3) 2.635(3) 166(4) 2_655 O5 H52 O3 0.91(3) 1.81(3) 2.674(3) 158(4) 2_556 O6 H61 O1 0.82(3) 1.97(3) 2.782(3) 172(5) 2_665 O6 H62 O3 0.78(3) 2.01(3) 2.770(3) 164(5) 2_566 _diffrn_measured_fraction_theta_max 0.884 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.982 _refine_diff_density_max 0.719 _refine_diff_density_min -1.562 _refine_diff_density_rms 0.226 data_p45et _database_code_depnum_ccdc_archive 'CCDC 224523' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C22 H38 Cu2 N6 O10' _chemical_formula_weight 673.66 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' Cu Cu 0.3201 1.2651 '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 1 21/c 1' 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 12.1421(7) _cell_length_b 17.6251(14) _cell_length_c 13.6226(8) _cell_angle_alpha 90.00 _cell_angle_beta 101.174(7) _cell_angle_gamma 90.00 _cell_volume 2860.0(3) _cell_formula_units_Z 4 _cell_measurement_temperature 200(2) _cell_measurement_reflns_used 8000 _cell_measurement_theta_min 2.06 _cell_measurement_theta_max 23.87 _exptl_crystal_description block _exptl_crystal_colour blue _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.565 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1400 _exptl_absorpt_coefficient_mu 1.550 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 200(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 'Stoe IPDS' _diffrn_measurement_method 'area detector' _diffrn_detector_area_resol_mean 6.667 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 16853 _diffrn_reflns_av_R_equivalents 0.0635 _diffrn_reflns_av_sigmaI/netI 0.0916 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -21 _diffrn_reflns_limit_k_max 21 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 2.06 _diffrn_reflns_theta_max 26.00 _reflns_number_total 5502 _reflns_number_gt 3394 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'IPDS 2.92 (Stoe & Cie GmbH, 1999)' _computing_cell_refinement 'IPDS 2.92 (Stoe & Cie GmbH, 1999)' _computing_data_reduction 'IPDS 2.92 (Stoe & Cie GmbH, 1999)' _computing_structure_solution 'SHELXTL 5.1 (Bruker AXS Inc., 1997)' _computing_structure_refinement 'SHELXTL 5.1 (Bruker AXS Inc., 1997)' _computing_molecular_graphics 'SHELXTL 5.1 (Bruker AXS Inc., 1997)' _computing_publication_material 'SHELXTL 5.1 (Bruker AXS Inc., 1997)' _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^)+(0.0968P)^2^+0.7868P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 5502 _refine_ls_number_parameters 379 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0947 _refine_ls_R_factor_gt 0.0634 _refine_ls_wR_factor_ref 0.1849 _refine_ls_wR_factor_gt 0.1781 _refine_ls_goodness_of_fit_ref 1.064 _refine_ls_restrained_S_all 1.064 _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 Cu1 Cu 0.29196(7) 0.52904(4) 0.69553(6) 0.0230(2) Uani 1 1 d . . . Cu2 Cu 0.23512(7) 0.40167(5) 0.45123(6) 0.0239(2) Uani 1 1 d . . . N1 N 0.1586(5) 0.4807(3) 0.6208(4) 0.0223(12) Uani 1 1 d . . . N2 N 0.1421(5) 0.4365(3) 0.5411(4) 0.0220(12) Uani 1 1 d . . . C1 C 0.0667(5) 0.4785(3) 0.6622(5) 0.0204(13) Uani 1 1 d . . . C2 C -0.0122(6) 0.4317(4) 0.6057(5) 0.0243(14) Uani 1 1 d . . . H2 H -0.0839 0.4204 0.6160 0.029 Uiso 1 1 calc R . . C3 C 0.0395(5) 0.4053(4) 0.5299(5) 0.0217(13) Uani 1 1 d . . . C4 C 0.0809(6) 0.5227(4) 0.7578(5) 0.0231(14) Uani 1 1 d . . . O1 O 0.1816(4) 0.5462(3) 0.7889(3) 0.0262(10) Uani 1 1 d . . . O2 O 0.0015(4) 0.5340(3) 0.7993(3) 0.0314(11) Uani 1 1 d . . . C5 C 0.0162(6) 0.3492(4) 0.4434(5) 0.0234(14) Uani 1 1 d . . . O3 O 0.0986(4) 0.3414(3) 0.3992(3) 0.0311(11) Uani 1 1 d . . . O4 O -0.0713(4) 0.3145(3) 0.4264(4) 0.0307(11) Uani 1 1 d . . . N3 N 0.3903(5) 0.4809(3) 0.6175(4) 0.0231(12) Uani 1 1 d . . . N4 N 0.3705(5) 0.4370(3) 0.5363(4) 0.0237(12) Uani 1 1 d . . . C6 C 0.4977(5) 0.4772(3) 0.6599(5) 0.0200(13) Uani 1 1 d . . . C7 C 0.5525(6) 0.4291(4) 0.6038(5) 0.0238(14) Uani 1 1 d . . . H7 H 0.6284 0.4169 0.6148 0.029 Uiso 1 1 calc R . . C8 C 0.4668(5) 0.4035(3) 0.5270(5) 0.0209(13) Uani 1 1 d . . . C9 C 0.5268(6) 0.5217(4) 0.7546(5) 0.0236(14) Uani 1 1 d . . . O5 O 0.4412(4) 0.5461(3) 0.7869(3) 0.0277(11) Uani 1 1 d . . . O6 O 0.6257(4) 0.5309(3) 0.7954(3) 0.0284(11) Uani 1 1 d . . . C10 C 0.4540(6) 0.3465(4) 0.4435(5) 0.0221(14) Uani 1 1 d . . . O7 O 0.3508(4) 0.3361(3) 0.4023(3) 0.0293(11) Uani 1 1 d . . . O8 O 0.5331(4) 0.3117(3) 0.4251(4) 0.0301(11) Uani 1 1 d . . . O9 O 0.2845(5) 0.6475(3) 0.6543(5) 0.0386(14) Uani 1 1 d . . . H91 H 0.329(10) 0.654(6) 0.628(8) 0.058 Uiso 1 1 d . . . H92 H 0.227(9) 0.666(6) 0.626(7) 0.058 Uiso 1 1 d . . . O10 O 0.2118(6) 0.4783(3) 0.3213(4) 0.0325(12) Uani 1 1 d . . . H101 H 0.142(9) 0.473(5) 0.295(7) 0.049 Uiso 1 1 d . . . H102 H 0.264(9) 0.470(5) 0.297(7) 0.049 Uiso 1 1 d . . . N21 N 0.2542(6) 0.6317(3) 0.9565(5) 0.0304(14) Uani 1 1 d . . . H21 H 0.222(7) 0.603(5) 0.913(6) 0.037 Uiso 1 1 d . . . C21 C 0.3537(7) 0.5813(5) 0.9961(6) 0.0406(19) Uani 1 1 d . . . H21A H 0.3270 0.5354 1.0231 0.049 Uiso 1 1 calc R . . H21B H 0.3892 0.5668 0.9410 0.049 Uiso 1 1 calc R . . C22 C 0.4399(8) 0.6179(5) 1.0759(7) 0.055(2) Uani 1 1 d . . . H22A H 0.5002 0.5830 1.0980 0.082 Uiso 1 1 calc R . . H22B H 0.4059 0.6317 1.1314 0.082 Uiso 1 1 calc R . . H22C H 0.4687 0.6626 1.0493 0.082 Uiso 1 1 calc R . . C23 C 0.2867(7) 0.6996(5) 0.9027(6) 0.041(2) Uani 1 1 d . . . H23A H 0.3299 0.7339 0.9512 0.049 Uiso 1 1 calc R . . H23B H 0.3347 0.6834 0.8574 0.049 Uiso 1 1 calc R . . C24 C 0.1890(9) 0.7416(5) 0.8445(7) 0.057(2) Uani 1 1 d . . . H24A H 0.2152 0.7845 0.8122 0.085 Uiso 1 1 calc R . . H24B H 0.1417 0.7588 0.8890 0.085 Uiso 1 1 calc R . . H24C H 0.1469 0.7086 0.7950 0.085 Uiso 1 1 calc R . . C25 C 0.1882(8) 0.6519(5) 1.0323(6) 0.048(2) Uani 1 1 d . . . H25A H 0.1282 0.6861 1.0030 0.057 Uiso 1 1 calc R . . H25B H 0.2360 0.6783 1.0871 0.057 Uiso 1 1 calc R . . C26 C 0.1387(9) 0.5825(7) 1.0722(9) 0.077(4) Uani 1 1 d . . . H26A H 0.0967 0.5976 1.1219 0.115 Uiso 1 1 calc R . . H26B H 0.1981 0.5488 1.1017 0.115 Uiso 1 1 calc R . . H26C H 0.0899 0.5571 1.0184 0.115 Uiso 1 1 calc R . . N31 N 0.2597(6) 0.2562(4) 0.2371(5) 0.0371(16) Uani 1 1 d . . . H31 H 0.299(7) 0.276(5) 0.301(7) 0.045 Uiso 1 1 d . . . C31 C 0.3430(8) 0.2198(5) 0.1822(8) 0.054(2) Uani 1 1 d . . . H31A H 0.3784 0.1772 0.2213 0.064 Uiso 1 1 calc R . . H31B H 0.3029 0.2000 0.1189 0.064 Uiso 1 1 calc R . . C32 C 0.4312(9) 0.2724(6) 0.1630(8) 0.068(3) Uani 1 1 d . . . H32A H 0.4812 0.2461 0.1281 0.102 Uiso 1 1 calc R . . H32B H 0.4726 0.2913 0.2255 0.102 Uiso 1 1 calc R . . H32C H 0.3970 0.3141 0.1229 0.102 Uiso 1 1 calc R . . C33 C 0.1832(8) 0.2002(5) 0.2701(7) 0.048(2) Uani 1 1 d . . . H33A H 0.1470 0.1709 0.2126 0.057 Uiso 1 1 calc R . . H33B H 0.1251 0.2273 0.2956 0.057 Uiso 1 1 calc R . . C34 C 0.2403(10) 0.1469(6) 0.3490(8) 0.065(3) Uani 1 1 d . . . H34A H 0.1862 0.1123 0.3665 0.098 Uiso 1 1 calc R . . H34B H 0.2746 0.1752 0.4072 0.098 Uiso 1 1 calc R . . H34C H 0.2970 0.1189 0.3241 0.098 Uiso 1 1 calc R . . C35 C 0.1965(8) 0.3220(5) 0.1809(6) 0.045(2) Uani 1 1 d . . . H35A H 0.1495 0.3450 0.2228 0.054 Uiso 1 1 calc R . . H35B H 0.2503 0.3599 0.1689 0.054 Uiso 1 1 calc R . . C36 C 0.1243(10) 0.3002(6) 0.0827(7) 0.065(3) Uani 1 1 d . . . H36A H 0.0866 0.3444 0.0516 0.097 Uiso 1 1 calc R . . H36B H 0.0697 0.2634 0.0940 0.097 Uiso 1 1 calc R . . H36C H 0.1704 0.2788 0.0399 0.097 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cu1 0.0176(5) 0.0264(4) 0.0248(4) -0.0038(3) 0.0036(3) -0.0013(3) Cu2 0.0194(5) 0.0285(4) 0.0231(4) -0.0042(3) 0.0028(3) -0.0022(3) N1 0.014(3) 0.027(3) 0.026(3) -0.006(2) 0.006(2) 0.004(2) N2 0.016(3) 0.028(3) 0.020(3) -0.003(2) -0.003(2) -0.002(2) C1 0.015(4) 0.019(3) 0.026(3) 0.001(3) 0.000(3) 0.002(3) C2 0.017(4) 0.026(3) 0.031(4) 0.000(3) 0.008(3) 0.003(3) C3 0.017(4) 0.023(3) 0.024(3) 0.005(3) 0.002(3) -0.002(3) C4 0.017(4) 0.022(3) 0.030(4) 0.002(3) 0.005(3) -0.001(3) O1 0.024(3) 0.029(2) 0.024(2) -0.0068(19) 0.0022(19) -0.004(2) O2 0.027(3) 0.037(3) 0.031(3) -0.007(2) 0.010(2) 0.000(2) C5 0.019(4) 0.023(3) 0.028(3) 0.002(3) 0.003(3) 0.000(3) O3 0.025(3) 0.037(3) 0.029(3) -0.009(2) -0.001(2) -0.005(2) O4 0.023(3) 0.033(3) 0.035(3) -0.004(2) 0.002(2) -0.007(2) N3 0.017(3) 0.029(3) 0.024(3) -0.004(2) 0.006(2) -0.005(2) N4 0.020(3) 0.029(3) 0.023(3) -0.005(2) 0.007(2) 0.000(2) C6 0.015(4) 0.019(3) 0.025(3) 0.002(3) 0.000(2) -0.003(3) C7 0.014(4) 0.026(3) 0.032(4) 0.001(3) 0.004(3) 0.001(3) C8 0.021(4) 0.019(3) 0.023(3) 0.003(3) 0.005(3) -0.001(3) C9 0.017(4) 0.024(3) 0.030(3) 0.002(3) 0.004(3) 0.001(3) O5 0.023(3) 0.033(3) 0.027(2) -0.008(2) 0.004(2) -0.002(2) O6 0.022(3) 0.033(3) 0.027(2) -0.005(2) -0.002(2) -0.008(2) C10 0.023(4) 0.019(3) 0.024(3) -0.001(3) 0.005(3) -0.004(3) O7 0.025(3) 0.030(3) 0.033(3) -0.009(2) 0.006(2) 0.001(2) O8 0.027(3) 0.032(3) 0.033(3) -0.004(2) 0.010(2) 0.004(2) O9 0.028(4) 0.035(3) 0.053(4) 0.007(3) 0.009(3) 0.007(3) O10 0.044(4) 0.028(3) 0.023(3) 0.001(2) 0.001(2) 0.001(3) N21 0.036(4) 0.027(3) 0.028(3) -0.007(3) 0.006(3) -0.002(3) C21 0.038(5) 0.046(5) 0.038(4) -0.003(4) 0.006(4) 0.000(4) C22 0.041(6) 0.057(5) 0.061(6) 0.019(5) -0.007(4) -0.008(4) C23 0.047(6) 0.042(4) 0.035(4) -0.002(3) 0.006(4) -0.009(4) C24 0.064(7) 0.050(5) 0.054(6) 0.007(4) 0.007(5) 0.009(5) C25 0.050(6) 0.059(5) 0.036(4) 0.003(4) 0.016(4) 0.013(4) C26 0.053(7) 0.103(9) 0.083(8) 0.049(7) 0.035(6) 0.020(6) N31 0.036(4) 0.037(3) 0.038(4) -0.018(3) 0.006(3) -0.008(3) C31 0.040(6) 0.056(5) 0.067(6) -0.033(5) 0.016(4) -0.003(4) C32 0.071(8) 0.071(7) 0.071(7) -0.039(6) 0.038(6) -0.024(6) C33 0.045(6) 0.039(5) 0.058(5) -0.013(4) 0.008(4) -0.014(4) C34 0.088(9) 0.049(5) 0.055(6) -0.007(5) 0.006(5) -0.014(5) C35 0.046(6) 0.043(5) 0.045(5) -0.012(4) 0.005(4) -0.007(4) C36 0.066(8) 0.069(7) 0.054(6) -0.006(5) -0.004(5) -0.012(5) _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 Cu1 N1 1.935(5) . yes Cu1 N3 1.941(5) . yes Cu1 O1 2.042(5) . yes Cu1 O5 2.012(5) . yes Cu1 O9 2.159(6) . yes Cu2 N2 1.920(6) . yes Cu2 N4 1.922(6) . yes Cu2 O3 1.981(5) . yes Cu2 O7 2.029(5) . yes Cu2 O10 2.201(5) . yes N1 N2 1.321(7) . ? N1 C1 1.344(8) . ? N2 C3 1.342(8) . ? C1 C2 1.381(9) . ? C1 C4 1.498(9) . ? C2 C3 1.389(9) . ? C2 H2 0.9300 . ? C3 C5 1.522(9) . ? C4 O2 1.225(8) . ? C4 O1 1.282(8) . ? C5 O4 1.209(8) . ? C5 O3 1.271(8) . ? N3 C6 1.322(8) . ? N3 N4 1.333(7) . ? N4 C8 1.337(8) . ? C6 C7 1.393(9) . ? C6 C9 1.493(9) . ? C7 C8 1.400(9) . ? C7 H7 0.9300 . ? C8 C10 1.504(9) . ? C9 O6 1.231(8) . ? C9 O5 1.280(8) . ? C10 O8 1.205(8) . ? C10 O7 1.283(8) . ? O9 H91 0.71(11) . ? O9 H92 0.81(11) . ? O10 H101 0.86(10) . ? O10 H102 0.79(10) . ? N21 C25 1.468(10) . ? N21 C23 1.497(10) . ? N21 C21 1.512(10) . ? N21 H21 0.81(9) . ? C21 C22 1.500(12) . ? C21 H21A 0.9700 . ? C21 H21B 0.9700 . ? C22 H22A 0.9600 . ? C22 H22B 0.9600 . ? C22 H22C 0.9600 . ? C23 C24 1.490(12) . ? C23 H23A 0.9700 . ? C23 H23B 0.9700 . ? C24 H24A 0.9600 . ? C24 H24B 0.9600 . ? C24 H24C 0.9600 . ? C25 C26 1.509(13) . ? C25 H25A 0.9700 . ? C25 H25B 0.9700 . ? C26 H26A 0.9600 . ? C26 H26B 0.9600 . ? C26 H26C 0.9600 . ? N31 C33 1.484(10) . ? N31 C35 1.513(11) . ? N31 C31 1.512(10) . ? N31 H31 0.97(9) . ? C31 C32 1.478(13) . ? C31 H31A 0.9700 . ? C31 H31B 0.9700 . ? C32 H32A 0.9600 . ? C32 H32B 0.9600 . ? C32 H32C 0.9600 . ? C33 C34 1.493(14) . ? C33 H33A 0.9700 . ? C33 H33B 0.9700 . ? C34 H34A 0.9600 . ? C34 H34B 0.9600 . ? C34 H34C 0.9600 . ? C35 C36 1.500(12) . ? C35 H35A 0.9700 . ? C35 H35B 0.9700 . ? C36 H36A 0.9600 . ? C36 H36B 0.9600 . ? C36 H36C 0.9600 . ? 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 Cu1 N3 93.4(2) . . yes N1 Cu1 O5 162.3(2) . . yes N3 Cu1 O5 80.1(2) . . yes N1 Cu1 O1 79.0(2) . . yes N3 Cu1 O1 162.5(2) . . yes O5 Cu1 O1 102.33(18) . . yes N1 Cu1 O9 107.5(2) . . yes N3 Cu1 O9 106.3(2) . . yes O5 Cu1 O9 90.2(2) . . yes O1 Cu1 O9 91.1(2) . . yes N2 Cu2 N4 93.0(2) . . yes N2 Cu2 O3 81.0(2) . . yes N4 Cu2 O3 161.5(2) . . yes N2 Cu2 O7 157.2(2) . . yes N4 Cu2 O7 79.4(2) . . yes O3 Cu2 O7 99.3(2) . . yes N2 Cu2 O10 108.5(2) . . yes N4 Cu2 O10 104.3(2) . . yes O3 Cu2 O10 94.2(2) . . yes O7 Cu2 O10 94.3(2) . . yes N2 N1 C1 108.8(5) . . ? N2 N1 Cu1 132.1(4) . . yes C1 N1 Cu1 118.0(4) . . ? N1 N2 C3 109.0(5) . . ? N1 N2 Cu2 134.3(4) . . yes C3 N2 Cu2 116.4(4) . . ? N1 C1 C2 109.0(6) . . ? N1 C1 C4 112.6(5) . . ? C2 C1 C4 138.2(6) . . ? C1 C2 C3 104.4(6) . . ? C1 C2 H2 127.8 . . ? C3 C2 H2 127.8 . . ? N2 C3 C2 108.8(6) . . ? N2 C3 C5 112.5(5) . . ? C2 C3 C5 138.6(6) . . ? O2 C4 O1 125.4(6) . . ? O2 C4 C1 121.2(6) . . ? O1 C4 C1 113.4(5) . . ? C4 O1 Cu1 116.4(4) . . ? O4 C5 O3 126.7(6) . . ? O4 C5 C3 120.1(6) . . ? O3 C5 C3 113.0(6) . . ? C5 O3 Cu2 117.0(4) . . ? C6 N3 N4 109.7(5) . . ? C6 N3 Cu1 116.2(4) . . ? N4 N3 Cu1 132.6(4) . . yes N3 N4 C8 108.3(5) . . ? N3 N4 Cu2 133.1(4) . . yes C8 N4 Cu2 117.5(4) . . ? N3 C6 C7 109.1(6) . . ? N3 C6 C9 113.6(6) . . ? C7 C6 C9 137.3(6) . . ? C6 C7 C8 103.9(6) . . ? C6 C7 H7 128.0 . . ? C8 C7 H7 128.0 . . ? N4 C8 C7 108.9(6) . . ? N4 C8 C10 113.7(6) . . ? C7 C8 C10 137.2(6) . . ? O6 C9 O5 125.9(6) . . ? O6 C9 C6 120.4(6) . . ? O5 C9 C6 113.7(6) . . ? C9 O5 Cu1 115.6(4) . . ? O8 C10 O7 125.9(6) . . ? O8 C10 C8 121.8(6) . . ? O7 C10 C8 112.0(6) . . ? C10 O7 Cu2 117.1(4) . . ? Cu1 O9 H91 107(9) . . ? Cu1 O9 H92 121(7) . . ? H91 O9 H92 112(10) . . ? Cu2 O10 H101 104(6) . . ? Cu2 O10 H102 104(7) . . ? H101 O10 H102 128(10) . . ? C25 N21 C23 112.4(6) . . ? C25 N21 C21 113.5(6) . . ? C23 N21 C21 112.1(6) . . ? C25 N21 H21 114(6) . . ? C23 N21 H21 106(6) . . ? C21 N21 H21 98(6) . . ? C22 C21 N21 113.8(7) . . ? C22 C21 H21A 108.8 . . ? N21 C21 H21A 108.8 . . ? C22 C21 H21B 108.8 . . ? N21 C21 H21B 108.8 . . ? H21A C21 H21B 107.7 . . ? C21 C22 H22A 109.5 . . ? C21 C22 H22B 109.5 . . ? H22A C22 H22B 109.5 . . ? C21 C22 H22C 109.5 . . ? H22A C22 H22C 109.5 . . ? H22B C22 H22C 109.5 . . ? C24 C23 N21 113.5(7) . . ? C24 C23 H23A 108.9 . . ? N21 C23 H23A 108.9 . . ? C24 C23 H23B 108.9 . . ? N21 C23 H23B 108.9 . . ? H23A C23 H23B 107.7 . . ? 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 . . ? N21 C25 C26 111.5(8) . . ? N21 C25 H25A 109.3 . . ? C26 C25 H25A 109.3 . . ? N21 C25 H25B 109.3 . . ? C26 C25 H25B 109.3 . . ? H25A C25 H25B 108.0 . . ? C25 C26 H26A 109.5 . . ? C25 C26 H26B 109.5 . . ? H26A C26 H26B 109.5 . . ? C25 C26 H26C 109.5 . . ? H26A C26 H26C 109.5 . . ? H26B C26 H26C 109.5 . . ? C33 N31 C35 112.1(7) . . ? C33 N31 C31 112.6(6) . . ? C35 N31 C31 113.4(7) . . ? C33 N31 H31 101(5) . . ? C35 N31 H31 107(5) . . ? C31 N31 H31 109(5) . . ? C32 C31 N31 113.4(7) . . ? C32 C31 H31A 108.9 . . ? N31 C31 H31A 108.9 . . ? C32 C31 H31B 108.9 . . ? N31 C31 H31B 108.9 . . ? H31A C31 H31B 107.7 . . ? C31 C32 H32A 109.5 . . ? C31 C32 H32B 109.5 . . ? H32A C32 H32B 109.5 . . ? C31 C32 H32C 109.5 . . ? H32A C32 H32C 109.5 . . ? H32B C32 H32C 109.5 . . ? N31 C33 C34 113.9(8) . . ? N31 C33 H33A 108.8 . . ? C34 C33 H33A 108.8 . . ? N31 C33 H33B 108.8 . . ? C34 C33 H33B 108.8 . . ? H33A C33 H33B 107.7 . . ? C33 C34 H34A 109.5 . . ? C33 C34 H34B 109.5 . . ? H34A C34 H34B 109.5 . . ? C33 C34 H34C 109.5 . . ? H34A C34 H34C 109.5 . . ? H34B C34 H34C 109.5 . . ? C36 C35 N31 114.0(7) . . ? C36 C35 H35A 108.8 . . ? N31 C35 H35A 108.8 . . ? C36 C35 H35B 108.8 . . ? N31 C35 H35B 108.8 . . ? H35A C35 H35B 107.7 . . ? C35 C36 H36A 109.5 . . ? C35 C36 H36B 109.5 . . ? H36A C36 H36B 109.5 . . ? C35 C36 H36C 109.5 . . ? H36A C36 H36C 109.5 . . ? H36B C36 H36C 109.5 . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O9 H91 O8 0.71(11) 2.04(11) 2.743(8) 169(12) 3_666 O9 H92 O4 0.81(11) 1.91(11) 2.694(8) 163(10) 3_566 O10 H101 O2 0.86(10) 1.96(10) 2.794(8) 164(9) 3_566 O10 H102 O6 0.79(10) 2.00(10) 2.769(8) 164(10) 3_666 N21 H21 O1 0.81(9) 1.95(9) 2.735(8) 163(8) . N31 H31 O7 0.97(9) 1.76(9) 2.702(8) 163(7) . _diffrn_measured_fraction_theta_max 0.979 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.987 _refine_diff_density_max 1.218 _refine_diff_density_min -0.550 _refine_diff_density_rms 0.157 data_p8119 _database_code_depnum_ccdc_archive 'CCDC 224524' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C10 H6 Cu2 N4 Na2 O10' _chemical_formula_weight 515.25 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' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Na Na 0.0362 0.0249 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 3.5938(14) _cell_length_b 9.659(4) _cell_length_c 10.934(4) _cell_angle_alpha 111.01(3) _cell_angle_beta 93.30(3) _cell_angle_gamma 95.59(3) _cell_volume 350.9(2) _cell_formula_units_Z 1 _cell_measurement_temperature 200(2) _cell_measurement_reflns_used 2263 _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description needle _exptl_crystal_colour purple _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.07 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.438 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 254 _exptl_absorpt_coefficient_mu 3.167 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 200(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'rotating anode' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Stoe IPDS II' _diffrn_measurement_method 'area detector' _diffrn_detector_area_resol_mean 6.667 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 2386 _diffrn_reflns_av_R_equivalents 0.0451 _diffrn_reflns_av_sigmaI/netI 0.0385 _diffrn_reflns_limit_h_min -4 _diffrn_reflns_limit_h_max 4 _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 3.54 _diffrn_reflns_theta_max 27.24 _reflns_number_total 1437 _reflns_number_gt 1283 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'WinXpose 1.05 (Stoe & Cie GmbH, 2000)' _computing_cell_refinement 'X-Area 1.09 (Stoe & Cie GmbH, 2000)' _computing_data_reduction 'X-Area 1.09 (Stoe & Cie GmbH, 2000)' _computing_structure_solution 'XS: SHELXTL 5.1 (Bruker AXS Inc., 1997)' _computing_structure_refinement 'XL: SHELXTL 5.1 (Bruker AXS Inc., 1997)' _computing_molecular_graphics 'XP: SHELXTL 5.1 (Bruker AXS Inc., 1997)' _computing_publication_material 'XCIF: SHELXTL 5.1 (Bruker AXS Inc., 1997)' _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^)+(0.0703P)^2^+0.3446P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_ls_hydrogen_treatment refall _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.095(13) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 1437 _refine_ls_number_parameters 140 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0457 _refine_ls_R_factor_gt 0.0404 _refine_ls_wR_factor_ref 0.1105 _refine_ls_wR_factor_gt 0.1063 _refine_ls_goodness_of_fit_ref 1.126 _refine_ls_restrained_S_all 1.126 _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 Cu1 Cu 0.27889(11) 0.43725(4) 0.31624(4) 0.0140(2) Uani 1 1 d . . . O1 O 0.2509(7) 0.2383(3) 0.1757(3) 0.0177(6) Uani 1 1 d . . . O2 O 0.3793(7) 0.0063(3) 0.1371(3) 0.0178(6) Uani 1 1 d . . . C1 C 0.3941(9) 0.1376(4) 0.2100(4) 0.0143(7) Uani 1 1 d . . . C2 C 0.5713(9) 0.1945(4) 0.3482(4) 0.0131(7) Uani 1 1 d . . . N1 N 0.5547(8) 0.3401(3) 0.4095(3) 0.0146(6) Uani 1 1 d . . . N2 N 0.6969(8) 0.3815(4) 0.5346(3) 0.0152(6) Uani 1 1 d . . . C3 C 0.7377(9) 0.1373(4) 0.4361(4) 0.0132(7) Uani 1 1 d . . . H3 H 0.781(13) 0.030(6) 0.420(5) 0.020(12) Uiso 1 1 d . . . C4 C 0.8125(9) 0.2625(4) 0.5535(4) 0.0140(7) Uani 1 1 d . . . C5 C 0.9788(9) 0.2997(4) 0.6919(4) 0.0149(7) Uani 1 1 d . . . O3 O 0.9726(7) 0.4412(3) 0.7676(3) 0.0191(6) Uani 1 1 d . . . O4 O 1.1101(8) 0.2092(3) 0.7291(3) 0.0210(6) Uani 1 1 d . . . Na1 Na 0.1740(4) 0.16807(17) -0.06276(16) 0.0184(4) Uani 1 1 d . . . O5 O 0.7071(8) 0.3475(4) -0.0142(4) 0.0218(7) Uani 1 1 d . . . H51 H 0.765(15) 0.401(7) 0.046(7) 0.022(15) Uiso 1 1 d . . . H52 H 0.724(17) 0.363(7) -0.066(7) 0.03(2) 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 Cu1 0.0174(3) 0.0120(3) 0.0112(3) 0.0028(2) -0.00262(16) 0.00345(17) O1 0.0199(11) 0.0155(13) 0.0154(15) 0.0037(11) -0.0035(9) 0.0028(10) O2 0.0189(12) 0.0139(13) 0.0163(16) 0.0006(11) -0.0005(10) 0.0027(9) C1 0.0099(13) 0.0166(17) 0.016(2) 0.0060(14) 0.0001(11) 0.0011(12) C2 0.0133(13) 0.0132(16) 0.0109(19) 0.0022(13) 0.0014(11) 0.0021(12) N1 0.0180(13) 0.0109(14) 0.0126(17) 0.0021(12) -0.0017(11) 0.0011(11) N2 0.0163(12) 0.0138(15) 0.0157(18) 0.0061(13) -0.0037(11) 0.0026(11) C3 0.0153(14) 0.0145(17) 0.009(2) 0.0037(14) 0.0003(11) 0.0019(12) C4 0.0127(13) 0.0158(17) 0.014(2) 0.0067(14) 0.0006(12) 0.0021(12) C5 0.0153(14) 0.0165(17) 0.012(2) 0.0041(14) -0.0010(12) 0.0029(12) O3 0.0255(13) 0.0148(13) 0.0137(15) 0.0012(11) -0.0044(10) 0.0064(10) O4 0.0277(13) 0.0195(14) 0.0159(16) 0.0063(11) -0.0027(10) 0.0077(11) Na1 0.0162(6) 0.0192(8) 0.0168(9) 0.0039(6) -0.0013(5) 0.0014(5) O5 0.0255(14) 0.0215(17) 0.0152(19) 0.0047(15) -0.0012(12) -0.0018(11) _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 Cu1 N1 1.911(3) . yes Cu1 N2 1.908(3) 2_666 yes Cu1 O1 1.973(3) . yes Cu1 O3 1.979(3) 2_666 yes Cu1 N1 3.034(3) 1_455 yes Cu1 O3 3.145(3) 2_766 yes O1 C1 1.299(4) . ? O1 Na1 2.439(4) . yes O2 C1 1.226(5) . ? O2 Na1 2.373(3) 2 ? O2 Na1 2.402(3) 2_655 ? C1 C2 1.489(5) . ? C2 N1 1.333(5) . ? C2 C3 1.402(5) . ? N1 N2 1.334(4) . ? N2 C4 1.338(5) . ? N2 Cu1 1.908(3) 2_666 ? C3 C4 1.403(5) . ? C3 H3 1.01(5) . ? C4 C5 1.497(5) . ? C5 O4 1.211(5) . ? C5 O3 1.324(5) . ? O3 Cu1 1.979(3) 2_666 ? O4 Na1 2.448(3) 1_656 ? Na1 O2 2.373(3) 2 yes Na1 O2 2.402(3) 2_655 yes Na1 O4 2.448(3) 1_454 yes Na1 O5 2.352(3) . yes Na1 O5 2.472(4) 1_455 yes Na1 Na1 3.5938(14) 1_655 ? Na1 Na1 3.5938(14) 1_455 ? Na1 Na1 4.073(3) 2 ? O5 Na1 2.472(4) 1_655 ? O5 H51 0.68(7) . ? O5 H52 0.64(7) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N2 Cu1 N1 93.82(14) 2_666 . yes N2 Cu1 O1 173.68(12) 2_666 . yes N1 Cu1 O1 80.95(13) . . yes N2 Cu1 O3 80.81(12) 2_666 2_666 yes N1 Cu1 O3 173.64(12) . 2_666 yes O1 Cu1 O3 104.61(12) . 2_666 yes N2 Cu1 N1 86.10(12) 2_666 1_455 yes N1 Cu1 N1 90.27(12) . 1_455 yes O1 Cu1 N1 90.35(11) . 1_455 yes O3 Cu1 N1 92.76(10) 2_666 1_455 yes N2 Cu1 O3 90.33(11) 2_666 2_766 yes N1 Cu1 O3 90.76(11) . 2_766 yes O1 Cu1 O3 93.28(10) . 2_766 yes O3 Cu1 O3 85.88(10) 2_666 2_766 yes N1 Cu1 O3 176.34(7) 1_455 2_766 yes C1 O1 Cu1 115.4(2) . . ? C1 O1 Na1 112.0(2) . . ? Cu1 O1 Na1 129.63(14) . . yes C1 O2 Na1 125.5(2) . 2 ? C1 O2 Na1 135.7(2) . 2_655 ? Na1 O2 Na1 97.62(11) 2 2_655 yes O2 C1 O1 123.6(4) . . ? O2 C1 C2 122.3(3) . . ? O1 C1 C2 114.0(3) . . ? N1 C2 C3 109.6(3) . . ? N1 C2 C1 112.2(3) . . ? C3 C2 C1 138.1(3) . . ? C2 N1 N2 109.0(3) . . ? C2 N1 Cu1 117.1(3) . . ? N2 N1 Cu1 133.0(2) . . yes N1 N2 C4 108.7(3) . . ? N1 N2 Cu1 133.1(2) . 2_666 yes C4 N2 Cu1 117.9(3) . 2_666 ? C2 C3 C4 103.2(3) . . ? C2 C3 H3 129(3) . . ? C4 C3 H3 128(3) . . ? N2 C4 C3 109.5(3) . . ? N2 C4 C5 112.2(3) . . ? C3 C4 C5 138.3(3) . . ? O4 C5 O3 124.0(4) . . ? O4 C5 C4 122.9(3) . . ? O3 C5 C4 113.1(3) . . ? C5 O3 Cu1 115.6(2) . 2_666 ? C5 O4 Na1 135.7(3) . 1_656 ? O5 Na1 O2 172.55(15) . 2 ? O5 Na1 O2 83.56(11) . 2_655 ? O2 Na1 O2 97.62(11) 2 2_655 ? O5 Na1 O1 81.26(13) . . ? O2 Na1 O1 105.53(12) 2 . ? O2 Na1 O1 103.15(11) 2_655 . ? O5 Na1 O4 84.01(13) . 1_454 ? O2 Na1 O4 88.57(11) 2 1_454 ? O2 Na1 O4 93.39(11) 2_655 1_454 ? O1 Na1 O4 156.38(12) . 1_454 ? O5 Na1 O5 96.28(13) . 1_455 ? O2 Na1 O5 81.64(11) 2 1_455 ? O2 Na1 O5 172.95(14) 2_655 1_455 ? O1 Na1 O5 83.77(13) . 1_455 ? O4 Na1 O5 79.59(13) 1_454 1_455 ? O5 Na1 Na1 43.13(9) . 1_655 ? O2 Na1 Na1 138.50(7) 2 1_655 ? O2 Na1 Na1 40.88(7) 2_655 1_655 ? O1 Na1 Na1 88.58(8) . 1_655 ? O4 Na1 Na1 93.21(8) 1_454 1_655 ? O5 Na1 Na1 139.42(8) 1_455 1_655 ? O5 Na1 Na1 136.87(9) . 1_455 ? O2 Na1 Na1 41.50(7) 2 1_455 ? O2 Na1 Na1 139.12(7) 2_655 1_455 ? O1 Na1 Na1 91.42(8) . 1_455 ? O4 Na1 Na1 86.79(8) 1_454 1_455 ? O5 Na1 Na1 40.58(8) 1_455 1_455 ? Na1 Na1 Na1 180.00(11) 1_655 1_455 ? O5 Na1 Na1 135.42(12) . 2 ? O2 Na1 Na1 51.72(8) 2 2 ? O2 Na1 Na1 76.12(9) 2_655 2 ? O1 Na1 Na1 65.82(8) . 2 ? O4 Na1 Na1 135.73(10) 1_454 2 ? O5 Na1 Na1 108.43(11) 1_455 2 ? Na1 Na1 Na1 104.40(5) 1_655 2 ? Na1 Na1 Na1 75.60(5) 1_455 2 ? Na1 O5 Na1 96.28(13) . 1_655 yes Na1 O5 H51 125(5) . . ? Na1 O5 H51 107(5) 1_655 . ? Na1 O5 H52 106(6) . . ? Na1 O5 H52 95(6) 1_655 . ? H51 O5 H52 119(8) . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O5 H51 O3 0.68(7) 2.15(7) 2.828(5) 172(6) 2_766 O5 H52 O3 0.64(7) 2.39(7) 3.011(5) 163(7) 1_554 _diffrn_measured_fraction_theta_max 0.908 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.930 _refine_diff_density_max 0.664 _refine_diff_density_min -1.218 _refine_diff_density_rms 0.159 data_82c _database_code_depnum_ccdc_archive 'CCDC 224525' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C10 H18 N4 Ni3 O16' _chemical_formula_weight 626.41 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 'C 1 2/c 1' 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 7.0477(9) _cell_length_b 12.5228(14) _cell_length_c 21.422(3) _cell_angle_alpha 90.00 _cell_angle_beta 94.699(14) _cell_angle_gamma 90.00 _cell_volume 1884.3(4) _cell_formula_units_Z 4 _cell_measurement_temperature 200(2) _cell_measurement_reflns_used 3309 _cell_measurement_theta_min 3.51 _cell_measurement_theta_max 23.91 _exptl_crystal_description plate _exptl_crystal_colour 'pale blue' _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.208 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1272 _exptl_absorpt_coefficient_mu 3.064 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 200(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 'Stoe IPDS' _diffrn_measurement_method 'area detector' _diffrn_detector_area_resol_mean 6.667 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 5202 _diffrn_reflns_av_R_equivalents 0.1275 _diffrn_reflns_av_sigmaI/netI 0.1234 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -26 _diffrn_reflns_limit_l_max 26 _diffrn_reflns_theta_min 3.33 _diffrn_reflns_theta_max 26.14 _reflns_number_total 1836 _reflns_number_gt 1054 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'IPDS 2.92 (Stoe & Cie GmbH, 1999)' _computing_cell_refinement 'IPDS 2.92 (Stoe & Cie GmbH, 1999)' _computing_data_reduction 'IPDS 2.92 (Stoe & Cie GmbH, 1999)' _computing_structure_solution 'SHELXTL 5.1 (Bruker AXS Inc., 1997)' _computing_structure_refinement 'SHELXTL 5.1 (Bruker AXS Inc., 1997)' _computing_molecular_graphics 'SHELXTL 5.1 (Bruker AXS Inc., 1997)' _computing_publication_material 'SHELXTL 5.1 (Bruker AXS Inc., 1997)' _refine_special_details ; Crystals are twinned; the structure may be primitive triclinic, although refinement in P-1 with apprpriate TWIN command did not lead to an improvement in the refinement. 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^)+(0.1517P)^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 mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 1836 _refine_ls_number_parameters 180 _refine_ls_number_restraints 4 _refine_ls_R_factor_all 0.1350 _refine_ls_R_factor_gt 0.0892 _refine_ls_wR_factor_ref 0.2482 _refine_ls_wR_factor_gt 0.2204 _refine_ls_goodness_of_fit_ref 0.947 _refine_ls_restrained_S_all 0.946 _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 Ni1 Ni 0.23660(19) 0.25860(12) 0.40778(7) 0.0351(5) Uani 1 1 d . . . N1 N 0.0624(13) 0.3109(7) 0.4683(4) 0.034(2) Uani 1 1 d . . . N2 N 0.0721(13) 0.3064(8) 0.5294(5) 0.036(2) Uani 1 1 d . . . C1 C -0.1007(14) 0.3652(9) 0.4478(6) 0.033(2) Uani 1 1 d . . . C2 C -0.1941(13) 0.3957(10) 0.5004(5) 0.032(2) Uani 1 1 d . . . H2 H -0.3072 0.4337 0.5013 0.039 Uiso 1 1 calc R . . C3 C -0.0775(15) 0.3557(9) 0.5513(5) 0.035(2) Uani 1 1 d . . . C4 C -0.1322(14) 0.3753(9) 0.3800(6) 0.034(2) Uani 1 1 d . . . O1 O -0.0039(10) 0.3364(7) 0.3477(3) 0.0365(18) Uani 1 1 d . . . O2 O -0.2780(10) 0.4237(7) 0.3564(4) 0.0391(19) Uani 1 1 d . . . C5 C -0.0830(15) 0.3563(9) 0.6185(6) 0.037(3) Uani 1 1 d . . . O3 O 0.0509(11) 0.3059(7) 0.6503(4) 0.0392(19) Uani 1 1 d . . . O4 O -0.2120(11) 0.4017(7) 0.6459(4) 0.042(2) Uani 1 1 d . . . O5 O 0.0937(13) 0.1193(7) 0.3921(8) 0.079(4) Uani 1 1 d D . . H51 H 0.11(4) 0.056(8) 0.407(11) 0.118 Uiso 1 1 d D . . H52 H -0.026(9) 0.119(19) 0.381(11) 0.118 Uiso 1 1 d D . . O6 O 0.3740(12) 0.4011(7) 0.4063(4) 0.0398(19) Uani 1 1 d D . . H61 H 0.279(15) 0.443(11) 0.401(7) 0.060 Uiso 1 1 d D . . H62 H 0.41(2) 0.420(13) 0.371(4) 0.060 Uiso 1 1 d D . . Ni2 Ni 0.0000 0.33825(19) 0.2500 0.0405(6) Uani 1 2 d S . . O11 O 0.045(3) 0.1755(18) 0.2440(11) 0.016(5) Uiso 0.25 1 d P . 1 O12 O 0.292(3) 0.3443(16) 0.2616(10) 0.058(5) Uani 0.50 1 d P . 1 O13 O 0.0000 0.5005(19) 0.2500 0.042(5) Uani 0.50 2 d SP . 1 O14 O 0.198(4) 0.217(2) 0.2514(11) 0.083(8) Uani 0.50 1 d P . 2 O15 O 0.216(3) 0.4459(19) 0.2610(9) 0.063(6) Uani 0.50 1 d P . 2 loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Ni1 0.0217(7) 0.0350(8) 0.0484(9) 0.0008(7) 0.0016(5) 0.0022(6) N1 0.024(4) 0.032(5) 0.045(5) 0.002(4) 0.005(4) 0.001(4) N2 0.027(5) 0.035(5) 0.044(5) 0.000(4) 0.003(4) -0.005(4) C1 0.016(4) 0.030(5) 0.053(7) -0.003(5) -0.004(4) -0.004(4) C2 0.005(4) 0.050(7) 0.043(6) 0.003(5) 0.007(4) 0.000(4) C3 0.023(5) 0.035(6) 0.048(6) -0.007(5) 0.006(4) -0.001(5) C4 0.015(5) 0.027(5) 0.060(7) 0.000(5) 0.003(5) -0.002(4) O1 0.028(4) 0.045(5) 0.037(4) -0.002(3) 0.000(3) 0.009(3) O2 0.020(4) 0.045(5) 0.052(5) -0.003(4) -0.002(3) 0.003(3) C5 0.022(5) 0.028(5) 0.062(7) 0.002(5) 0.003(5) 0.001(4) O3 0.026(4) 0.047(5) 0.044(4) -0.002(4) 0.002(3) 0.005(4) O4 0.026(4) 0.048(5) 0.051(5) -0.011(4) 0.004(3) 0.002(4) O5 0.019(4) 0.021(4) 0.193(14) -0.012(6) -0.013(6) -0.009(4) O6 0.032(4) 0.034(4) 0.054(5) 0.001(4) 0.004(4) 0.000(3) Ni2 0.0344(11) 0.0394(13) 0.0474(13) 0.000 0.0011(9) 0.000 O12 0.051(11) 0.052(12) 0.069(12) -0.013(10) 0.000(9) 0.022(10) O13 0.032(12) 0.036(12) 0.058(15) 0.000 0.012(10) 0.000 O14 0.10(2) 0.074(16) 0.071(15) -0.008(12) -0.010(13) 0.045(15) O15 0.063(14) 0.077(15) 0.051(11) -0.013(10) 0.020(10) -0.027(12) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Ni1 N1 1.969(9) . yes Ni1 N2 1.998(10) 7_556 yes Ni1 O1 2.263(7) . yes? Ni1 O3 2.179(8) 7_556 yes Ni1 O5 2.028(8) . yes Ni1 O6 2.031(9) . yes N1 N2 1.307(14) . ? N1 C1 1.376(14) . ? N2 C3 1.339(15) . ? N2 Ni1 1.998(10) 7_556 ? C1 C2 1.404(16) . ? C1 C4 1.458(17) . ? C2 C3 1.403(16) . ? C2 H2 0.9300 . ? C3 C5 1.444(17) . ? C4 O2 1.262(13) . ? C4 O1 1.278(13) . ? O1 Ni2 2.096(7) . ? C5 O4 1.257(14) . ? C5 O3 1.282(14) . ? O3 Ni1 2.179(8) 7_556 ? O5 H51 0.85(4) . ? O5 H52 0.86(4) . ? O6 H61 0.85(4) . ? O6 H62 0.84(4) . ? Ni2 O1 2.096(7) 2 yes Ni2 O11 2.07(2) 2 ? Ni2 O11 2.07(2) . yes Ni2 O12 2.06(2) . yes Ni2 O12 2.06(2) 2 ? Ni2 O13 2.03(2) . yes Ni2 O14 2.06(2) 2 ? Ni2 O14 2.06(2) . yes Ni2 O15 2.03(2) . yes Ni2 O15 2.03(2) 2 ? O11 O11 0.70(4) 2 ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N1 Ni1 N2 96.6(4) . 7_556 yes N1 Ni1 O5 93.8(5) . . yes N2 Ni1 O5 93.4(4) 7_556 . yes N1 Ni1 O6 92.4(4) . . yes N2 Ni1 O6 94.1(4) 7_556 . yes O5 Ni1 O6 169.6(6) . . yes N1 Ni1 O3 173.6(4) . 7_556 yes N2 Ni1 O3 77.0(3) 7_556 7_556 yes O5 Ni1 O3 86.7(4) . 7_556 yes O6 Ni1 O3 88.0(3) . 7_556 yes N1 Ni1 O1 75.7(3) . . yes N2 Ni1 O1 172.2(3) 7_556 . yes O5 Ni1 O1 86.4(4) . . yes O6 Ni1 O1 87.1(3) . . yes O3 Ni1 O1 110.7(3) 7_556 . yes N2 N1 C1 108.3(9) . . ? N2 N1 Ni1 131.4(8) . . yes C1 N1 Ni1 120.3(8) . . ? N1 N2 C3 110.7(10) . . ? N1 N2 Ni1 132.0(8) . 7_556 yes C3 N2 Ni1 117.3(8) . 7_556 ? N1 C1 C2 108.2(10) . . ? N1 C1 C4 114.6(10) . . ? C2 C1 C4 137.2(10) . . ? C3 C2 C1 104.1(9) . . ? C3 C2 H2 128.0 . . ? C1 C2 H2 128.0 . . ? N2 C3 C2 108.7(10) . . ? N2 C3 C5 116.0(10) . . ? C2 C3 C5 135.4(10) . . ? O2 C4 O1 123.7(11) . . ? O2 C4 C1 119.6(10) . . ? O1 C4 C1 116.7(9) . . ? C4 O1 Ni2 127.1(7) . . ? C4 O1 Ni1 112.8(7) . . ? Ni2 O1 Ni1 120.1(3) . . yes O4 C5 O3 120.3(11) . . ? O4 C5 C3 123.1(11) . . ? O3 C5 C3 116.6(10) . . ? C5 O3 Ni1 113.0(7) . 7_556 ? Ni1 O5 H51 134(10) . . ? Ni1 O5 H52 121(10) . . ? H51 O5 H52 100(10) . . ? Ni1 O6 H61 100(10) . . ? Ni1 O6 H62 115(10) . . ? H61 O6 H62 89(10) . . ? O15 Ni2 O15 96.8(15) . 2 ? O15 Ni2 O13 48.4(7) . . yes O15 Ni2 O13 48.4(7) 2 . ? O15 Ni2 O12 39.5(9) . . yes O15 Ni2 O12 136.2(10) 2 . ? O13 Ni2 O12 87.9(6) . . yes O15 Ni2 O12 136.2(10) . 2 ? O15 Ni2 O12 39.5(9) 2 2 ? O13 Ni2 O12 87.9(6) . 2 ? O12 Ni2 O12 175.8(12) . 2 ? O15 Ni2 O14 172.0(10) . 2 ? O15 Ni2 O14 89.3(11) 2 2 ? O13 Ni2 O14 137.4(9) . 2 ? O12 Ni2 O14 134.4(11) . 2 ? O12 Ni2 O14 49.8(10) 2 2 ? O15 Ni2 O14 89.3(11) . . yes O15 Ni2 O14 172.0(10) 2 . ? O13 Ni2 O14 137.4(9) . . yes O12 Ni2 O14 49.8(10) . . yes O12 Ni2 O14 134.4(11) 2 . ? O14 Ni2 O14 85.2(18) 2 . ? O15 Ni2 O11 139.9(10) . 2 ? O15 Ni2 O11 123.0(9) 2 2 ? O13 Ni2 O11 170.2(6) . 2 ? O12 Ni2 O11 100.7(8) . 2 ? O12 Ni2 O11 83.5(8) 2 2 ? O14 Ni2 O11 33.7(10) 2 2 ? O14 Ni2 O11 51.8(11) . 2 ? O15 Ni2 O11 123.0(9) . . yes O15 Ni2 O11 139.9(10) 2 . ? O13 Ni2 O11 170.2(6) . . yes O12 Ni2 O11 83.5(8) . . yes O12 Ni2 O11 100.7(8) 2 . ? O14 Ni2 O11 51.8(11) 2 . ? O14 Ni2 O11 33.7(10) . . yes O11 Ni2 O11 19.6(11) 2 . ? O15 Ni2 O1 93.0(6) . 2 ? O15 Ni2 O1 87.9(6) 2 2 ? O13 Ni2 O1 90.6(2) . 2 ? O12 Ni2 O1 91.5(6) . 2 ? O12 Ni2 O1 88.6(6) 2 2 ? O14 Ni2 O1 92.4(7) 2 2 ? O14 Ni2 O1 86.7(7) . 2 ? O11 Ni2 O1 93.8(7) 2 2 ? O11 Ni2 O1 85.0(7) . 2 ? O15 Ni2 O1 87.9(6) . . yes O15 Ni2 O1 93.0(6) 2 . ? O13 Ni2 O1 90.6(2) . . yes O12 Ni2 O1 88.6(6) . . yes O12 Ni2 O1 91.5(6) 2 . ? O14 Ni2 O1 86.7(7) 2 . ? O14 Ni2 O1 92.4(7) . . yes O11 Ni2 O1 85.0(7) 2 . ? O11 Ni2 O1 93.8(7) . . yes O1 Ni2 O1 178.7(5) 2 . ? O11 O11 Ni2 80.2(5) 2 . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O5 H51 O2 0.85(4) 2.2(2) 2.742(13) 123(21) 3_545 O5 H52 O4 0.86(4) 1.91(6) 2.758(12) 172(23) 7_456 O6 H61 O4 0.85(4) 2.22(12) 2.906(12) 137(14) 5_566 O6 H62 O2 0.84(4) 2.27(15) 2.770(12) 119(14) 1_655 _diffrn_measured_fraction_theta_max 0.971 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.984 _refine_diff_density_max 2.733 _refine_diff_density_min -0.995 _refine_diff_density_rms 0.215