# Supplementary Material (ESI) for CrystEngComm # This journal is (c) The Royal Society of Chemistry 2010 data_global _journal_coden_Cambridge 1350 loop_ _publ_author_name 'Jimin Zheng' 'Yun-Xia Che' 'Yan Qi' 'Li-Xin Sun' 'You-Ming Wang' _publ_contact_author_name 'Jimin Zheng' _publ_contact_author_email JMZHENG@NANKAI.EDU.CN _publ_section_title ; A Variety of Novel Complexes Constructed from Biphenyl-3,3',4,4'-tetracarboxylate and Flexible Bis(imidazole) Ligands ; # Attachment '1.cif' data_shelxl _database_code_depnum_ccdc_archive 'CCDC 731980' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C22 H17 Co N4 O4' _chemical_formula_weight 460.33 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 P2(1)/c 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 9.3106(19) _cell_length_b 11.023(2) _cell_length_c 20.395(6) _cell_angle_alpha 90.00 _cell_angle_beta 107.92(3) _cell_angle_gamma 90.00 _cell_volume 1991.6(8) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 8673 _cell_measurement_theta_min 3.18 _cell_measurement_theta_max 27 _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.535 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 944 _exptl_absorpt_coefficient_mu 0.900 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8405 _exptl_absorpt_correction_T_max 0.8405 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(2) _diffrn_radiation_probe x-ray _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_source 'rotating anode' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'rigaku r-axis rapid IP area detector' _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 18692 _diffrn_reflns_av_R_equivalents 0.2189 _diffrn_reflns_av_sigmaI/netI 0.1949 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -25 _diffrn_reflns_limit_l_max 26 _diffrn_reflns_theta_min 3.18 _diffrn_reflns_theta_max 27.48 _reflns_number_total 4550 _reflns_number_gt 1944 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'RAXIS-RAPID Auto(Rigaku, 2004)' _computing_cell_refinement 'RAXIS-RAPID Auto(Rigaku, 2004)' _computing_data_reduction 'CrystalStructure(Rigaku/MSC, 2004)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXL-97 (Sheldrick, 2001)' _computing_publication_material 'SHELXL-97 (Sheldrick, 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^)+(0.0479P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4550 _refine_ls_number_parameters 280 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1924 _refine_ls_R_factor_gt 0.0672 _refine_ls_wR_factor_ref 0.1404 _refine_ls_wR_factor_gt 0.1081 _refine_ls_goodness_of_fit_ref 0.909 _refine_ls_restrained_S_all 0.909 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.7278(6) 0.1910(5) 0.2220(3) 0.0432(15) Uani 1 1 d . . . H1 H 0.6770 0.1518 0.2487 0.052 Uiso 1 1 calc R . . C2 C 0.7868(6) 0.3167(5) 0.1535(3) 0.0450(15) Uani 1 1 d . . . H2 H 0.7834 0.3818 0.1241 0.054 Uiso 1 1 calc R . . C3 C 0.8982(7) 0.2336(6) 0.1722(3) 0.0579(18) Uani 1 1 d . . . H3 H 0.9840 0.2306 0.1580 0.070 Uiso 1 1 calc R . . C4 C 0.9515(7) 0.0492(6) 0.2507(3) 0.072(2) Uani 1 1 d . . . H4A H 0.9030 0.0124 0.2816 0.086 Uiso 1 1 calc R . . H4B H 1.0508 0.0766 0.2781 0.086 Uiso 1 1 calc R . . C5 C 0.9680(6) -0.0440(6) 0.1999(3) 0.0468(16) Uani 1 1 d . . . C6 C 1.0901(6) -0.0465(5) 0.1769(3) 0.0482(15) Uani 1 1 d . . . H6 H 1.1681 0.0085 0.1946 0.058 Uiso 1 1 calc R . . C7 C 1.1006(6) -0.1288(6) 0.1278(3) 0.0513(16) Uani 1 1 d . . . H7 H 1.1850 -0.1273 0.1126 0.062 Uiso 1 1 calc R . . C8 C 0.9891(7) -0.2132(6) 0.1009(3) 0.0527(17) Uani 1 1 d . . . C9 C 0.8691(7) -0.2138(7) 0.1268(4) 0.075(2) Uani 1 1 d . . . H9 H 0.7935 -0.2715 0.1110 0.090 Uiso 1 1 calc R . . C10 C 0.8585(7) -0.1307(8) 0.1756(4) 0.081(3) Uani 1 1 d . . . H10 H 0.7761 -0.1334 0.1923 0.097 Uiso 1 1 calc R . . C11 C 1.0008(7) -0.3016(6) 0.0462(3) 0.077(2) Uani 1 1 d . . . H11A H 1.0981 -0.2924 0.0387 0.092 Uiso 1 1 calc R . . H11B H 0.9939 -0.3838 0.0619 0.092 Uiso 1 1 calc R . . C12 C 0.7793(6) -0.3620(5) -0.0541(3) 0.0547(17) Uani 1 1 d . . . H12 H 0.7739 -0.4418 -0.0402 0.066 Uiso 1 1 calc R . . C13 C 0.8549(7) -0.1760(6) -0.0564(3) 0.0576(18) Uani 1 1 d . . . H13 H 0.9088 -0.1039 -0.0455 0.069 Uiso 1 1 calc R . . C14 C 0.7350(6) -0.1986(5) -0.1127(3) 0.0471(15) Uani 1 1 d . . . H14 H 0.6914 -0.1427 -0.1472 0.057 Uiso 1 1 calc R . . C15 C 0.4997(5) 0.3510(5) 0.3025(3) 0.0328(13) Uani 1 1 d . . . C16 C 0.5150(5) 0.3391(5) 0.3765(2) 0.0275(12) Uani 1 1 d . . . C17 C 0.5055(5) 0.4438(5) 0.4130(2) 0.0308(12) Uani 1 1 d . . . H17 H 0.4971 0.5179 0.3903 0.037 Uiso 1 1 calc R . . C18 C 0.5079(6) 0.4441(4) 0.4817(3) 0.0303(12) Uani 1 1 d . . . C19 C 0.5247(6) 0.3304(5) 0.5135(3) 0.0394(14) Uani 1 1 d . . . H19 H 0.5281 0.3253 0.5595 0.047 Uiso 1 1 calc R . . C20 C 0.5364(6) 0.2253(5) 0.4784(3) 0.0422(14) Uani 1 1 d . . . H20 H 0.5477 0.1512 0.5013 0.051 Uiso 1 1 calc R . . C21 C 0.5317(5) 0.2283(5) 0.4100(3) 0.0309(12) Uani 1 1 d . . . C22 C 0.5494(6) 0.1112(5) 0.3759(2) 0.0373(13) Uani 1 1 d . . . Co1 Co 0.49436(8) 0.39433(7) 0.18036(4) 0.0315(2) Uani 1 1 d . . . N1 N 0.6880(5) -0.3147(4) -0.1113(2) 0.0402(12) Uani 1 1 d . . . N2 N 0.8804(5) -0.2810(5) -0.0187(3) 0.0548(15) Uani 1 1 d . . . N3 N 0.8611(5) 0.1550(5) 0.2159(2) 0.0501(13) Uani 1 1 d . . . N4 N 0.6785(5) 0.2904(4) 0.1848(2) 0.0367(11) Uani 1 1 d . . . O1 O 0.5275(4) 0.4508(3) 0.27907(17) 0.0400(9) Uani 1 1 d . . . O2 O 0.4529(4) 0.2623(3) 0.26303(17) 0.0397(9) Uani 1 1 d . . . O3 O 0.6636(4) 0.0901(3) 0.35914(19) 0.0455(10) Uani 1 1 d . . . O4 O 0.4445(4) 0.0316(3) 0.37014(18) 0.0455(10) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.057(4) 0.042(4) 0.036(4) -0.006(3) 0.023(3) 0.007(3) C2 0.057(4) 0.050(4) 0.034(3) 0.001(3) 0.023(3) -0.003(3) C3 0.047(4) 0.074(5) 0.060(5) -0.005(4) 0.027(3) 0.016(4) C4 0.086(5) 0.078(5) 0.044(4) 0.008(4) 0.011(3) 0.047(4) C5 0.048(4) 0.058(4) 0.031(3) 0.000(3) 0.008(3) 0.019(3) C6 0.050(4) 0.041(4) 0.054(4) -0.003(3) 0.016(3) -0.002(3) C7 0.048(3) 0.059(5) 0.049(4) -0.009(3) 0.017(3) 0.008(3) C8 0.049(4) 0.044(4) 0.052(4) -0.011(3) -0.004(3) 0.009(3) C9 0.048(4) 0.096(7) 0.066(5) -0.013(5) -0.002(4) -0.016(4) C10 0.041(4) 0.138(8) 0.065(5) -0.016(5) 0.015(3) 0.001(5) C11 0.070(5) 0.071(5) 0.058(5) -0.030(4) -0.026(4) 0.034(4) C12 0.070(4) 0.036(4) 0.046(4) -0.006(3) 0.000(3) 0.008(3) C13 0.066(4) 0.043(4) 0.060(5) -0.013(4) 0.014(4) -0.007(3) C14 0.060(4) 0.035(4) 0.046(4) -0.004(3) 0.016(3) -0.003(3) C15 0.037(3) 0.038(4) 0.028(3) 0.002(3) 0.017(3) 0.009(3) C16 0.035(3) 0.026(3) 0.024(3) -0.008(2) 0.014(2) -0.001(2) C17 0.042(3) 0.030(3) 0.023(3) 0.006(2) 0.014(2) 0.001(2) C18 0.047(3) 0.024(3) 0.022(3) -0.002(2) 0.013(2) -0.003(3) C19 0.071(4) 0.032(3) 0.019(3) 0.002(3) 0.019(3) 0.000(3) C20 0.075(4) 0.022(3) 0.034(4) -0.002(3) 0.024(3) -0.005(3) C21 0.043(3) 0.027(3) 0.026(3) -0.002(2) 0.016(2) -0.003(2) C22 0.066(4) 0.024(3) 0.023(3) 0.003(3) 0.015(3) 0.001(3) Co1 0.0447(4) 0.0284(4) 0.0241(4) 0.0004(4) 0.0147(3) 0.0028(4) N1 0.046(3) 0.032(3) 0.038(3) 0.001(2) 0.008(2) 0.005(2) N2 0.057(3) 0.047(3) 0.045(3) -0.014(3) -0.008(2) 0.007(3) N3 0.061(3) 0.058(4) 0.032(3) 0.002(3) 0.015(2) 0.022(3) N4 0.049(3) 0.038(3) 0.025(3) 0.003(2) 0.014(2) 0.004(2) O1 0.067(2) 0.029(2) 0.028(2) 0.0024(18) 0.0191(18) 0.008(2) O2 0.057(2) 0.040(3) 0.023(2) -0.0087(18) 0.0141(17) -0.0032(19) O3 0.059(2) 0.039(3) 0.048(2) 0.003(2) 0.030(2) 0.011(2) O4 0.067(2) 0.031(2) 0.045(3) -0.012(2) 0.027(2) -0.010(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 N4 1.331(6) . ? C1 N3 1.345(6) . ? C1 H1 0.9300 . ? C2 C3 1.348(7) . ? C2 N4 1.379(6) . ? C2 H2 0.9300 . ? C3 N3 1.362(7) . ? C3 H3 0.9300 . ? C4 N3 1.485(7) . ? C4 C5 1.499(8) . ? C4 H4A 0.9700 . ? C4 H4B 0.9700 . ? C5 C6 1.357(7) . ? C5 C10 1.375(9) . ? C6 C7 1.376(7) . ? C6 H6 0.9300 . ? C7 C8 1.376(7) . ? C7 H7 0.9300 . ? C8 C9 1.375(9) . ? C8 C11 1.509(8) . ? C9 C10 1.379(9) . ? C9 H9 0.9300 . ? C10 H10 0.9300 . ? C11 N2 1.466(7) . ? C11 H11A 0.9700 . ? C11 H11B 0.9700 . ? C12 N1 1.321(6) . ? C12 N2 1.337(6) . ? C12 H12 0.9300 . ? C13 C14 1.356(7) . ? C13 N2 1.369(7) . ? C13 H13 0.9300 . ? C14 N1 1.356(7) . ? C14 H14 0.9300 . ? C15 O2 1.257(6) . ? C15 O1 1.258(6) . ? C15 C16 1.477(7) . ? C16 C21 1.386(7) . ? C16 C17 1.391(6) . ? C17 C18 1.395(6) . ? C17 H17 0.9300 . ? C18 C19 1.397(6) . ? C18 C18 1.471(9) 3_666 ? C19 C20 1.384(7) . ? C19 H19 0.9300 . ? C20 C21 1.382(6) . ? C20 H20 0.9300 . ? C21 C22 1.499(7) . ? C22 O3 1.236(6) . ? C22 O4 1.290(6) . ? Co1 O4 2.009(4) 2_655 ? Co1 O1 2.038(3) . ? Co1 N1 2.041(4) 3_655 ? Co1 N4 2.041(4) . ? Co1 O2 2.348(4) . ? N1 Co1 2.041(4) 3_655 ? O4 Co1 2.009(4) 2_645 ? 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 N4 C1 N3 110.9(5) . . ? N4 C1 H1 124.6 . . ? N3 C1 H1 124.6 . . ? C3 C2 N4 109.6(5) . . ? C3 C2 H2 125.2 . . ? N4 C2 H2 125.2 . . ? C2 C3 N3 106.8(5) . . ? C2 C3 H3 126.6 . . ? N3 C3 H3 126.6 . . ? N3 C4 C5 111.8(5) . . ? N3 C4 H4A 109.3 . . ? C5 C4 H4A 109.3 . . ? N3 C4 H4B 109.3 . . ? C5 C4 H4B 109.3 . . ? H4A C4 H4B 107.9 . . ? C6 C5 C10 117.9(6) . . ? C6 C5 C4 121.9(6) . . ? C10 C5 C4 120.2(6) . . ? C5 C6 C7 121.4(6) . . ? C5 C6 H6 119.3 . . ? C7 C6 H6 119.3 . . ? C6 C7 C8 121.5(6) . . ? C6 C7 H7 119.3 . . ? C8 C7 H7 119.3 . . ? C9 C8 C7 116.9(6) . . ? C9 C8 C11 122.1(6) . . ? C7 C8 C11 121.0(6) . . ? C8 C9 C10 121.5(7) . . ? C8 C9 H9 119.3 . . ? C10 C9 H9 119.3 . . ? C5 C10 C9 120.8(6) . . ? C5 C10 H10 119.6 . . ? C9 C10 H10 119.6 . . ? N2 C11 C8 111.0(5) . . ? N2 C11 H11A 109.4 . . ? C8 C11 H11A 109.4 . . ? N2 C11 H11B 109.4 . . ? C8 C11 H11B 109.4 . . ? H11A C11 H11B 108.0 . . ? N1 C12 N2 111.6(5) . . ? N1 C12 H12 124.2 . . ? N2 C12 H12 124.2 . . ? C14 C13 N2 106.0(5) . . ? C14 C13 H13 127.0 . . ? N2 C13 H13 127.0 . . ? N1 C14 C13 110.0(5) . . ? N1 C14 H14 125.0 . . ? C13 C14 H14 125.0 . . ? O2 C15 O1 120.5(5) . . ? O2 C15 C16 119.4(5) . . ? O1 C15 C16 120.0(5) . . ? C21 C16 C17 118.9(5) . . ? C21 C16 C15 122.9(5) . . ? C17 C16 C15 118.1(5) . . ? C16 C17 C18 123.7(5) . . ? C16 C17 H17 118.1 . . ? C18 C17 H17 118.1 . . ? C17 C18 C19 115.4(4) . . ? C17 C18 C18 122.5(6) . 3_666 ? C19 C18 C18 122.1(6) . 3_666 ? C20 C19 C18 121.8(5) . . ? C20 C19 H19 119.1 . . ? C18 C19 H19 119.1 . . ? C19 C20 C21 121.2(5) . . ? C19 C20 H20 119.4 . . ? C21 C20 H20 119.4 . . ? C20 C21 C16 118.9(5) . . ? C20 C21 C22 118.3(5) . . ? C16 C21 C22 122.8(5) . . ? O3 C22 O4 122.6(5) . . ? O3 C22 C21 121.2(5) . . ? O4 C22 C21 116.1(5) . . ? O4 Co1 O1 107.19(15) 2_655 . ? O4 Co1 N1 106.06(17) 2_655 3_655 ? O1 Co1 N1 130.87(17) . 3_655 ? O4 Co1 N4 94.54(16) 2_655 . ? O1 Co1 N4 104.93(15) . . ? N1 Co1 N4 107.36(17) 3_655 . ? O4 Co1 O2 166.03(14) 2_655 . ? O1 Co1 O2 59.22(13) . . ? N1 Co1 O2 86.77(16) 3_655 . ? N4 Co1 O2 86.64(15) . . ? C12 N1 C14 105.5(5) . . ? C12 N1 Co1 127.8(4) . 3_655 ? C14 N1 Co1 126.6(4) . 3_655 ? C12 N2 C13 106.8(5) . . ? C12 N2 C11 126.9(6) . . ? C13 N2 C11 126.2(6) . . ? C1 N3 C3 107.5(5) . . ? C1 N3 C4 126.3(5) . . ? C3 N3 C4 126.3(5) . . ? C1 N4 C2 105.3(5) . . ? C1 N4 Co1 128.7(4) . . ? C2 N4 Co1 125.8(4) . . ? C15 O1 Co1 97.0(3) . . ? C15 O2 Co1 82.9(3) . . ? C22 O4 Co1 103.5(3) . 2_645 ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N4 C2 C3 N3 -0.5(7) . . . . ? N3 C4 C5 C6 94.8(7) . . . . ? N3 C4 C5 C10 -85.6(8) . . . . ? C10 C5 C6 C7 3.5(9) . . . . ? C4 C5 C6 C7 -176.9(6) . . . . ? C5 C6 C7 C8 -1.0(10) . . . . ? C6 C7 C8 C9 -1.9(9) . . . . ? C6 C7 C8 C11 179.0(6) . . . . ? C7 C8 C9 C10 2.3(11) . . . . ? C11 C8 C9 C10 -178.6(6) . . . . ? C6 C5 C10 C9 -3.1(10) . . . . ? C4 C5 C10 C9 177.3(6) . . . . ? C8 C9 C10 C5 0.2(12) . . . . ? C9 C8 C11 N2 65.4(9) . . . . ? C7 C8 C11 N2 -115.5(6) . . . . ? N2 C13 C14 N1 -1.0(7) . . . . ? O2 C15 C16 C21 23.0(7) . . . . ? O1 C15 C16 C21 -159.8(5) . . . . ? O2 C15 C16 C17 -154.1(5) . . . . ? O1 C15 C16 C17 23.1(7) . . . . ? C21 C16 C17 C18 -1.7(7) . . . . ? C15 C16 C17 C18 175.5(4) . . . . ? C16 C17 C18 C19 1.6(7) . . . . ? C16 C17 C18 C18 -177.7(6) . . . 3_666 ? C17 C18 C19 C20 -0.7(8) . . . . ? C18 C18 C19 C20 178.7(6) 3_666 . . . ? C18 C19 C20 C21 -0.1(8) . . . . ? C19 C20 C21 C16 0.1(8) . . . . ? C19 C20 C21 C22 178.3(5) . . . . ? C17 C16 C21 C20 0.8(7) . . . . ? C15 C16 C21 C20 -176.3(4) . . . . ? C17 C16 C21 C22 -177.4(5) . . . . ? C15 C16 C21 C22 5.6(8) . . . . ? C20 C21 C22 O3 -110.7(6) . . . . ? C16 C21 C22 O3 67.5(7) . . . . ? C20 C21 C22 O4 64.2(6) . . . . ? C16 C21 C22 O4 -117.6(5) . . . . ? N2 C12 N1 C14 0.9(7) . . . . ? N2 C12 N1 Co1 -175.4(4) . . . 3_655 ? C13 C14 N1 C12 0.1(7) . . . . ? C13 C14 N1 Co1 176.5(4) . . . 3_655 ? N1 C12 N2 C13 -1.6(7) . . . . ? N1 C12 N2 C11 -178.8(6) . . . . ? C14 C13 N2 C12 1.6(7) . . . . ? C14 C13 N2 C11 178.8(6) . . . . ? C8 C11 N2 C12 -123.9(7) . . . . ? C8 C11 N2 C13 59.5(9) . . . . ? N4 C1 N3 C3 -0.8(7) . . . . ? N4 C1 N3 C4 179.0(5) . . . . ? C2 C3 N3 C1 0.7(7) . . . . ? C2 C3 N3 C4 -179.0(5) . . . . ? C5 C4 N3 C1 117.0(6) . . . . ? C5 C4 N3 C3 -63.3(8) . . . . ? N3 C1 N4 C2 0.4(6) . . . . ? N3 C1 N4 Co1 -174.1(3) . . . . ? C3 C2 N4 C1 0.0(6) . . . . ? C3 C2 N4 Co1 174.8(4) . . . . ? O4 Co1 N4 C1 167.7(5) 2_655 . . . ? O1 Co1 N4 C1 58.5(5) . . . . ? N1 Co1 N4 C1 -83.9(5) 3_655 . . . ? O2 Co1 N4 C1 1.6(5) . . . . ? O4 Co1 N4 C2 -5.9(4) 2_655 . . . ? O1 Co1 N4 C2 -115.0(4) . . . . ? N1 Co1 N4 C2 102.5(4) 3_655 . . . ? O2 Co1 N4 C2 -171.9(4) . . . . ? O2 C15 O1 Co1 -5.8(5) . . . . ? C16 C15 O1 Co1 177.0(4) . . . . ? O4 Co1 O1 C15 -173.3(3) 2_655 . . . ? N1 Co1 O1 C15 56.1(4) 3_655 . . . ? N4 Co1 O1 C15 -73.6(3) . . . . ? O2 Co1 O1 C15 3.1(3) . . . . ? O1 C15 O2 Co1 5.0(5) . . . . ? C16 C15 O2 Co1 -177.8(4) . . . . ? O4 Co1 O2 C15 11.2(7) 2_655 . . . ? O1 Co1 O2 C15 -3.1(3) . . . . ? N1 Co1 O2 C15 -145.9(3) 3_655 . . . ? N4 Co1 O2 C15 106.5(3) . . . . ? O3 C22 O4 Co1 -7.2(6) . . . 2_645 ? C21 C22 O4 Co1 177.9(3) . . . 2_645 ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.392 _refine_diff_density_min -0.609 _refine_diff_density_rms 0.087 # Attachment '2.cif' data_shelxl2 _database_code_depnum_ccdc_archive 'CCDC 731981' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C18 H19 N4 Ni O5' _chemical_formula_weight 430.08 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 C2/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 23.795(5) _cell_length_b 10.089(2) _cell_length_c 17.189(3) _cell_angle_alpha 90.00 _cell_angle_beta 111.31(3) _cell_angle_gamma 90.00 _cell_volume 3844.4(13) _cell_formula_units_Z 8 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 12005 _cell_measurement_theta_min 3.11 _cell_measurement_theta_max 27.50 _exptl_crystal_description block _exptl_crystal_colour green _exptl_crystal_size_max 0.21 _exptl_crystal_size_mid 0.19 _exptl_crystal_size_min 0.17 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.486 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1784 _exptl_absorpt_coefficient_mu 1.047 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8101 _exptl_absorpt_correction_T_max 0.8421 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(2) _diffrn_radiation_probe x-ray _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_source 'rotating anode' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'rigaku r-axis rapid IP area detector' _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 18137 _diffrn_reflns_av_R_equivalents 0.0717 _diffrn_reflns_av_sigmaI/netI 0.0598 _diffrn_reflns_limit_h_min -30 _diffrn_reflns_limit_h_max 30 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 3.11 _diffrn_reflns_theta_max 27.48 _reflns_number_total 4391 _reflns_number_gt 3219 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'RAXIS-RAPID Auto(Rigaku, 2004)' _computing_cell_refinement 'RAXIS-RAPID Auto(Rigaku, 2004)' _computing_data_reduction 'CrystalStructure(Rigaku/MSC, 2004)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXL-97 (Sheldrick, 2001)' _computing_publication_material 'SHELXL-97 (Sheldrick, 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^)+(0.0677P)^2^+4.7290P] 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 refu _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4391 _refine_ls_number_parameters 262 _refine_ls_number_restraints 6 _refine_ls_R_factor_all 0.0749 _refine_ls_R_factor_gt 0.0492 _refine_ls_wR_factor_ref 0.1348 _refine_ls_wR_factor_gt 0.1214 _refine_ls_goodness_of_fit_ref 1.039 _refine_ls_restrained_S_all 1.039 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.34920(14) 0.5895(3) 0.7364(2) 0.0246(6) Uani 1 1 d . . . C2 C 0.37874(14) 0.7228(3) 0.74375(19) 0.0232(6) Uani 1 1 d . . . C3 C 0.43548(14) 0.7276(3) 0.7382(2) 0.0270(7) Uani 1 1 d . . . H3 H 0.4516 0.6503 0.7255 0.032 Uiso 1 1 calc R . . C4 C 0.46889(14) 0.8436(3) 0.7509(2) 0.0256(6) Uani 1 1 d . . . C5 C 0.44241(16) 0.9591(3) 0.7664(2) 0.0323(7) Uani 1 1 d . . . H5 H 0.4629 1.0393 0.7727 0.039 Uiso 1 1 calc R . . C6 C 0.38596(15) 0.9555(3) 0.7724(2) 0.0305(7) Uani 1 1 d . . . H6 H 0.3693 1.0336 0.7831 0.037 Uiso 1 1 calc R . . C7 C 0.35375(14) 0.8382(3) 0.76297(19) 0.0239(6) Uani 1 1 d . . . C8 C 0.29267(14) 0.8441(3) 0.7704(2) 0.0254(7) Uani 1 1 d . . . C9 C 0.26870(15) 0.1136(3) 0.6280(2) 0.0296(7) Uani 1 1 d . . . H9 H 0.2454 0.0899 0.6590 0.036 Uiso 1 1 calc R . . C10 C 0.3294(2) 0.2178(4) 0.5842(3) 0.0501(11) Uani 1 1 d . . . H10 H 0.3568 0.2801 0.5795 0.060 Uiso 1 1 calc R . . C11 C 0.3085(2) 0.1107(4) 0.5329(3) 0.0540(12) Uani 1 1 d . . . H11 H 0.3183 0.0876 0.4870 0.065 Uiso 1 1 calc R . . C12 C 0.23367(18) -0.0725(3) 0.5262(2) 0.0409(9) Uani 1 1 d . . . H12A H 0.2045 -0.0494 0.4717 0.049 Uiso 1 1 calc R . . H12B H 0.2114 -0.0975 0.5613 0.049 Uiso 1 1 calc R . . C13 C 0.26986(19) -0.1899(3) 0.5170(3) 0.0430(9) Uani 1 1 d . . . H13A H 0.3001 -0.2115 0.5709 0.052 Uiso 1 1 calc R . . H13B H 0.2906 -0.1671 0.4795 0.052 Uiso 1 1 calc R . . C14 C 0.3892(2) 0.2415(4) 0.8869(3) 0.0508(11) Uani 1 1 d . . . H14 H 0.3556 0.2078 0.8956 0.061 Uiso 1 1 calc R . . C15 C 0.4449(2) 0.3352(5) 0.8304(4) 0.0801(18) Uani 1 1 d . . . H15 H 0.4575 0.3793 0.7920 0.096 Uiso 1 1 calc R . . C16 C 0.4818(3) 0.2919(6) 0.9072(4) 0.104(3) Uani 1 1 d . . . H16 H 0.5235 0.3011 0.9309 0.125 Uiso 1 1 calc R . . C17 C 0.4643(4) 0.1627(6) 1.0219(3) 0.110(3) Uani 1 1 d . . . H17A H 0.4339 0.1749 1.0466 0.132 Uiso 1 1 calc R . . H17B H 0.5018 0.2005 1.0597 0.132 Uiso 1 1 calc R . . C18 C 0.4731(3) 0.0149(6) 1.0119(4) 0.094(2) Uani 1 1 d . . . H18A H 0.4782 -0.0297 1.0640 0.113 Uiso 1 1 calc R . . H18B H 0.4372 -0.0205 0.9693 0.113 Uiso 1 1 calc R . . N1 N 0.30381(13) 0.2187(3) 0.64342(17) 0.0311(6) Uani 1 1 d . . . N2 N 0.27046(14) 0.0449(3) 0.56237(17) 0.0337(7) Uani 1 1 d . . . N3 N 0.38739(14) 0.3039(3) 0.81889(19) 0.0373(7) Uani 1 1 d . . . N4 N 0.4457(2) 0.2331(4) 0.9419(3) 0.0746(14) Uani 1 1 d . . . Ni1 Ni 0.309681(18) 0.36249(4) 0.72803(2) 0.02329(14) Uani 1 1 d . . . O1 O 0.32649(11) 0.5551(2) 0.78883(14) 0.0303(5) Uani 1 1 d . . . O2 O 0.35035(11) 0.5104(2) 0.68010(14) 0.0311(5) Uani 1 1 d . . . O3 O 0.24818(10) 0.7867(2) 0.71670(14) 0.0304(5) Uani 1 1 d . . . O4 O 0.28645(10) 0.9100(2) 0.82820(14) 0.0345(5) Uani 1 1 d . . . O5 O 0.3851(3) 0.3415(8) 0.4492(3) 0.075(2) Uani 0.50 1 d PD . . H5A H 0.3479 0.3560 0.4313 0.090 Uiso 0.50 1 d PRD . . H5B H 0.4082 0.4083 0.4500 0.090 Uiso 0.50 1 d PRD . . O6 O 0.4273(4) 0.4669(10) 0.0851(6) 0.123(4) Uani 0.50 1 d PD . . H6A H 0.4223 0.5170 0.0432 0.147 Uiso 0.50 1 d PRD . . H6B H 0.4053 0.4829 0.1134 0.147 Uiso 0.50 1 d PRD . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0201(15) 0.0189(13) 0.0358(16) 0.0008(13) 0.0115(13) 0.0019(12) C2 0.0226(16) 0.0187(13) 0.0294(15) -0.0010(12) 0.0106(13) -0.0002(12) C3 0.0245(17) 0.0181(13) 0.0407(18) -0.0033(13) 0.0146(14) 0.0020(12) C4 0.0201(16) 0.0220(14) 0.0349(16) 0.0024(13) 0.0103(13) 0.0017(12) C5 0.0283(18) 0.0186(14) 0.051(2) -0.0007(14) 0.0158(16) -0.0008(13) C6 0.0267(17) 0.0188(14) 0.0471(19) -0.0027(14) 0.0147(15) 0.0031(12) C7 0.0201(15) 0.0217(14) 0.0288(15) -0.0007(12) 0.0077(12) 0.0029(12) C8 0.0217(16) 0.0205(14) 0.0349(16) 0.0036(13) 0.0111(13) 0.0044(12) C9 0.0320(18) 0.0262(15) 0.0332(17) -0.0043(14) 0.0149(14) -0.0033(13) C10 0.064(3) 0.040(2) 0.065(3) -0.015(2) 0.046(2) -0.016(2) C11 0.079(3) 0.044(2) 0.059(3) -0.014(2) 0.049(3) -0.012(2) C12 0.046(2) 0.0287(17) 0.045(2) -0.0120(16) 0.0122(17) -0.0045(16) C13 0.051(2) 0.0322(18) 0.045(2) -0.0116(17) 0.0172(19) -0.0031(18) C14 0.060(3) 0.043(2) 0.044(2) -0.0017(19) 0.012(2) 0.016(2) C15 0.034(3) 0.068(3) 0.121(5) 0.036(3) 0.007(3) -0.003(2) C16 0.044(3) 0.075(4) 0.135(6) 0.030(4) -0.036(3) -0.008(3) C17 0.140(7) 0.105(5) 0.050(3) 0.014(3) -0.008(4) 0.054(5) C18 0.119(6) 0.083(4) 0.058(3) 0.031(3) 0.004(3) 0.039(4) N1 0.0346(16) 0.0257(13) 0.0382(15) -0.0046(12) 0.0193(13) -0.0040(12) N2 0.0425(18) 0.0250(13) 0.0353(15) -0.0069(12) 0.0161(13) -0.0032(12) N3 0.0324(17) 0.0272(14) 0.0443(17) 0.0011(13) 0.0042(14) 0.0033(12) N4 0.073(3) 0.058(2) 0.058(2) 0.004(2) -0.018(2) 0.019(2) Ni1 0.0214(2) 0.0194(2) 0.0304(2) -0.00303(16) 0.01100(16) -0.00291(16) O1 0.0351(13) 0.0225(10) 0.0402(12) -0.0024(10) 0.0219(11) -0.0035(9) O2 0.0359(13) 0.0250(11) 0.0368(12) -0.0072(10) 0.0185(11) -0.0072(10) O3 0.0232(12) 0.0296(12) 0.0397(13) -0.0029(10) 0.0129(10) 0.0023(10) O4 0.0303(13) 0.0399(13) 0.0375(12) -0.0080(11) 0.0173(11) 0.0000(11) O5 0.053(4) 0.144(7) 0.020(2) 0.023(3) 0.003(2) 0.045(4) O6 0.099(7) 0.168(10) 0.121(7) 0.073(7) 0.065(6) 0.047(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 C1 O1 1.257(4) . ? C1 O2 1.262(4) . ? C1 C2 1.501(4) . ? C1 Ni1 2.460(3) . ? C2 C3 1.389(4) . ? C2 C7 1.400(4) . ? C3 C4 1.387(4) . ? C3 H3 0.9300 . ? C4 C5 1.396(4) . ? C4 C4 1.492(6) 2_656 ? C5 C6 1.385(5) . ? C5 H5 0.9300 . ? C6 C7 1.387(4) . ? C6 H6 0.9300 . ? C7 C8 1.505(4) . ? C8 O4 1.249(4) . ? C8 O3 1.264(4) . ? C8 Ni1 2.453(3) 4_556 ? C9 N1 1.316(4) . ? C9 N2 1.337(4) . ? C9 H9 0.9300 . ? C10 N1 1.362(4) . ? C10 C11 1.369(5) . ? C10 H10 0.9300 . ? C11 N2 1.361(5) . ? C11 H11 0.9300 . ? C12 N2 1.470(4) . ? C12 C13 1.507(5) . ? C12 H12A 0.9700 . ? C12 H12B 0.9700 . ? C13 C13 1.517(7) 7_546 ? C13 H13A 0.9700 . ? C13 H13B 0.9700 . ? C14 N3 1.314(5) . ? C14 N4 1.335(6) . ? C14 H14 0.9300 . ? C15 N3 1.348(6) . ? C15 C16 1.365(8) . ? C15 H15 0.9300 . ? C16 N4 1.350(8) . ? C16 H16 0.9300 . ? C17 N4 1.466(7) . ? C17 C18 1.524(8) . ? C17 H17A 0.9700 . ? C17 H17B 0.9700 . ? C18 C18 1.507(13) 5_657 ? C18 H18A 0.9700 . ? C18 H18B 0.9700 . ? N1 Ni1 2.023(3) . ? N3 Ni1 2.027(3) . ? Ni1 O3 2.082(2) 4_546 ? Ni1 O2 2.103(2) . ? Ni1 O1 2.174(2) . ? Ni1 O4 2.189(2) 4_546 ? Ni1 C8 2.453(3) 4_546 ? O3 Ni1 2.082(2) 4_556 ? O4 Ni1 2.189(2) 4_556 ? O5 H5A 0.8381 . ? O5 H5B 0.8664 . ? O6 H6A 0.8524 . ? O6 H6B 0.8511 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 C1 O2 120.7(3) . . ? O1 C1 C2 119.8(3) . . ? O2 C1 C2 119.4(3) . . ? O1 C1 Ni1 61.96(15) . . ? O2 C1 Ni1 58.71(15) . . ? C2 C1 Ni1 175.0(2) . . ? C3 C2 C7 119.6(3) . . ? C3 C2 C1 117.5(3) . . ? C7 C2 C1 122.6(3) . . ? C4 C3 C2 122.3(3) . . ? C4 C3 H3 118.9 . . ? C2 C3 H3 118.9 . . ? C3 C4 C5 117.5(3) . . ? C3 C4 C4 120.87(19) . 2_656 ? C5 C4 C4 121.6(2) . 2_656 ? C6 C5 C4 120.7(3) . . ? C6 C5 H5 119.7 . . ? C4 C5 H5 119.7 . . ? C5 C6 C7 121.6(3) . . ? C5 C6 H6 119.2 . . ? C7 C6 H6 119.2 . . ? C6 C7 C2 118.2(3) . . ? C6 C7 C8 117.8(3) . . ? C2 C7 C8 123.9(3) . . ? O4 C8 O3 121.0(3) . . ? O4 C8 C7 119.0(3) . . ? O3 C8 C7 119.9(3) . . ? O4 C8 Ni1 62.95(17) . 4_556 ? O3 C8 Ni1 58.06(16) . 4_556 ? C7 C8 Ni1 175.6(2) . 4_556 ? N1 C9 N2 112.1(3) . . ? N1 C9 H9 124.0 . . ? N2 C9 H9 124.0 . . ? N1 C10 C11 109.3(3) . . ? N1 C10 H10 125.3 . . ? C11 C10 H10 125.3 . . ? N2 C11 C10 106.2(3) . . ? N2 C11 H11 126.9 . . ? C10 C11 H11 126.9 . . ? N2 C12 C13 113.8(3) . . ? N2 C12 H12A 108.8 . . ? C13 C12 H12A 108.8 . . ? N2 C12 H12B 108.8 . . ? C13 C12 H12B 108.8 . . ? H12A C12 H12B 107.7 . . ? C12 C13 C13 111.6(4) . 7_546 ? C12 C13 H13A 109.3 . . ? C13 C13 H13A 109.3 7_546 . ? C12 C13 H13B 109.3 . . ? C13 C13 H13B 109.3 7_546 . ? H13A C13 H13B 108.0 . . ? N3 C14 N4 111.1(5) . . ? N3 C14 H14 124.4 . . ? N4 C14 H14 124.4 . . ? N3 C15 C16 109.2(5) . . ? N3 C15 H15 125.4 . . ? C16 C15 H15 125.4 . . ? N4 C16 C15 106.2(5) . . ? N4 C16 H16 126.9 . . ? C15 C16 H16 126.9 . . ? N4 C17 C18 112.0(5) . . ? N4 C17 H17A 109.2 . . ? C18 C17 H17A 109.2 . . ? N4 C17 H17B 109.2 . . ? C18 C17 H17B 109.2 . . ? H17A C17 H17B 107.9 . . ? C18 C18 C17 113.0(8) 5_657 . ? C18 C18 H18A 109.0 5_657 . ? C17 C18 H18A 109.0 . . ? C18 C18 H18B 109.0 5_657 . ? C17 C18 H18B 109.0 . . ? H18A C18 H18B 107.8 . . ? C9 N1 C10 105.5(3) . . ? C9 N1 Ni1 126.6(2) . . ? C10 N1 Ni1 127.5(2) . . ? C9 N2 C11 106.9(3) . . ? C9 N2 C12 125.3(3) . . ? C11 N2 C12 127.6(3) . . ? C14 N3 C15 106.2(4) . . ? C14 N3 Ni1 123.4(3) . . ? C15 N3 Ni1 129.6(3) . . ? C14 N4 C16 107.3(4) . . ? C14 N4 C17 125.4(6) . . ? C16 N4 C17 127.2(5) . . ? N1 Ni1 N3 98.63(12) . . ? N1 Ni1 O3 100.39(10) . 4_546 ? N3 Ni1 O3 96.35(11) . 4_546 ? N1 Ni1 O2 98.55(10) . . ? N3 Ni1 O2 95.05(11) . . ? O3 Ni1 O2 156.12(9) 4_546 . ? N1 Ni1 O1 159.96(10) . . ? N3 Ni1 O1 86.18(11) . . ? O3 Ni1 O1 98.37(9) 4_546 . ? O2 Ni1 O1 61.54(8) . . ? N1 Ni1 O4 92.96(11) . 4_546 ? N3 Ni1 O4 156.71(11) . 4_546 ? O3 Ni1 O4 61.54(9) 4_546 4_546 ? O2 Ni1 O4 103.16(9) . 4_546 ? O1 Ni1 O4 89.81(9) . 4_546 ? N1 Ni1 C8 98.30(11) . 4_546 ? N3 Ni1 C8 126.92(12) . 4_546 ? O3 Ni1 C8 31.01(9) 4_546 4_546 ? O2 Ni1 C8 131.18(10) . 4_546 ? O1 Ni1 C8 94.14(9) . 4_546 ? O4 Ni1 C8 30.54(9) 4_546 4_546 ? N1 Ni1 C1 129.40(11) . . ? N3 Ni1 C1 90.25(11) . . ? O3 Ni1 C1 128.13(10) 4_546 . ? O2 Ni1 C1 30.87(9) . . ? O1 Ni1 C1 30.68(9) . . ? O4 Ni1 C1 97.92(10) 4_546 . ? C8 Ni1 C1 115.46(10) 4_546 . ? C1 O1 Ni1 87.36(18) . . ? C1 O2 Ni1 90.42(18) . . ? C8 O3 Ni1 90.93(18) . 4_556 ? C8 O4 Ni1 86.51(19) . 4_556 ? H5A O5 H5B 116.6 . . ? H6A O6 H6B 116.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O1 C1 C2 C3 131.7(3) . . . . ? O2 C1 C2 C3 -44.5(4) . . . . ? Ni1 C1 C2 C3 22(3) . . . . ? O1 C1 C2 C7 -42.7(5) . . . . ? O2 C1 C2 C7 141.1(3) . . . . ? Ni1 C1 C2 C7 -152(2) . . . . ? C7 C2 C3 C4 -0.1(5) . . . . ? C1 C2 C3 C4 -174.6(3) . . . . ? C2 C3 C4 C5 -2.6(5) . . . . ? C2 C3 C4 C4 176.5(4) . . . 2_656 ? C3 C4 C5 C6 2.8(5) . . . . ? C4 C4 C5 C6 -176.3(4) 2_656 . . . ? C4 C5 C6 C7 -0.4(5) . . . . ? C5 C6 C7 C2 -2.4(5) . . . . ? C5 C6 C7 C8 -179.8(3) . . . . ? C3 C2 C7 C6 2.6(5) . . . . ? C1 C2 C7 C6 176.9(3) . . . . ? C3 C2 C7 C8 179.9(3) . . . . ? C1 C2 C7 C8 -5.9(5) . . . . ? C6 C7 C8 O4 -44.3(4) . . . . ? C2 C7 C8 O4 138.5(3) . . . . ? C6 C7 C8 O3 133.2(3) . . . . ? C2 C7 C8 O3 -44.1(4) . . . . ? C6 C7 C8 Ni1 71(3) . . . 4_556 ? C2 C7 C8 Ni1 -106(3) . . . 4_556 ? N1 C10 C11 N2 -1.0(5) . . . . ? N2 C12 C13 C13 177.5(4) . . . 7_546 ? N3 C15 C16 N4 0.4(7) . . . . ? N4 C17 C18 C18 68.9(9) . . . 5_657 ? N2 C9 N1 C10 0.2(4) . . . . ? N2 C9 N1 Ni1 173.2(2) . . . . ? C11 C10 N1 C9 0.5(5) . . . . ? C11 C10 N1 Ni1 -172.4(3) . . . . ? N1 C9 N2 C11 -0.8(4) . . . . ? N1 C9 N2 C12 -176.1(3) . . . . ? C10 C11 N2 C9 1.1(5) . . . . ? C10 C11 N2 C12 176.1(4) . . . . ? C13 C12 N2 C9 -127.8(4) . . . . ? C13 C12 N2 C11 58.0(5) . . . . ? N4 C14 N3 C15 0.7(5) . . . . ? N4 C14 N3 Ni1 -170.2(3) . . . . ? C16 C15 N3 C14 -0.7(6) . . . . ? C16 C15 N3 Ni1 169.5(4) . . . . ? N3 C14 N4 C16 -0.5(6) . . . . ? N3 C14 N4 C17 -176.0(5) . . . . ? C15 C16 N4 C14 0.1(7) . . . . ? C15 C16 N4 C17 175.4(5) . . . . ? C18 C17 N4 C14 83.2(8) . . . . ? C18 C17 N4 C16 -91.4(8) . . . . ? C9 N1 Ni1 N3 102.0(3) . . . . ? C10 N1 Ni1 N3 -86.5(4) . . . . ? C9 N1 Ni1 O3 3.9(3) . . . 4_546 ? C10 N1 Ni1 O3 175.4(3) . . . 4_546 ? C9 N1 Ni1 O2 -161.5(3) . . . . ? C10 N1 Ni1 O2 10.0(4) . . . . ? C9 N1 Ni1 O1 -155.3(3) . . . . ? C10 N1 Ni1 O1 16.2(6) . . . . ? C9 N1 Ni1 O4 -57.7(3) . . . 4_546 ? C10 N1 Ni1 O4 113.8(3) . . . 4_546 ? C9 N1 Ni1 C8 -27.5(3) . . . 4_546 ? C10 N1 Ni1 C8 144.0(3) . . . 4_546 ? C9 N1 Ni1 C1 -160.5(3) . . . . ? C10 N1 Ni1 C1 11.0(4) . . . . ? C14 N3 Ni1 N1 -103.0(3) . . . . ? C15 N3 Ni1 N1 88.4(4) . . . . ? C14 N3 Ni1 O3 -1.4(3) . . . 4_546 ? C15 N3 Ni1 O3 -170.0(4) . . . 4_546 ? C14 N3 Ni1 O2 157.6(3) . . . . ? C15 N3 Ni1 O2 -11.1(5) . . . . ? C14 N3 Ni1 O1 96.6(3) . . . . ? C15 N3 Ni1 O1 -72.0(4) . . . . ? C14 N3 Ni1 O4 16.0(5) . . . 4_546 ? C15 N3 Ni1 O4 -152.6(4) . . . 4_546 ? C14 N3 Ni1 C8 4.3(3) . . . 4_546 ? C15 N3 Ni1 C8 -164.3(4) . . . 4_546 ? C14 N3 Ni1 C1 127.1(3) . . . . ? C15 N3 Ni1 C1 -41.6(4) . . . . ? O1 C1 Ni1 N1 176.51(18) . . . . ? O2 C1 Ni1 N1 -1.9(2) . . . . ? C2 C1 Ni1 N1 -72(3) . . . . ? O1 C1 Ni1 N3 -82.1(2) . . . . ? O2 C1 Ni1 N3 99.5(2) . . . . ? C2 C1 Ni1 N3 30(3) . . . . ? O1 C1 Ni1 O3 16.2(2) . . . 4_546 ? O2 C1 Ni1 O3 -162.26(17) . . . 4_546 ? C2 C1 Ni1 O3 128(3) . . . 4_546 ? O1 C1 Ni1 O2 178.5(3) . . . . ? C2 C1 Ni1 O2 -70(3) . . . . ? O2 C1 Ni1 O1 -178.5(3) . . . . ? C2 C1 Ni1 O1 112(3) . . . . ? O1 C1 Ni1 O4 76.04(19) . . . 4_546 ? O2 C1 Ni1 O4 -102.42(18) . . . 4_546 ? C2 C1 Ni1 O4 -172(3) . . . 4_546 ? O1 C1 Ni1 C8 49.8(2) . . . 4_546 ? O2 C1 Ni1 C8 -128.68(18) . . . 4_546 ? C2 C1 Ni1 C8 162(3) . . . 4_546 ? O2 C1 O1 Ni1 1.5(3) . . . . ? C2 C1 O1 Ni1 -174.6(3) . . . . ? N1 Ni1 O1 C1 -7.9(4) . . . . ? N3 Ni1 O1 C1 96.9(2) . . . . ? O3 Ni1 O1 C1 -167.19(18) 4_546 . . . ? O2 Ni1 O1 C1 -0.90(17) . . . . ? O4 Ni1 O1 C1 -106.01(19) 4_546 . . . ? C8 Ni1 O1 C1 -136.27(19) 4_546 . . . ? O1 C1 O2 Ni1 -1.6(3) . . . . ? C2 C1 O2 Ni1 174.6(3) . . . . ? N1 Ni1 O2 C1 178.48(19) . . . . ? N3 Ni1 O2 C1 -82.0(2) . . . . ? O3 Ni1 O2 C1 36.3(3) 4_546 . . . ? O1 Ni1 O2 C1 0.89(17) . . . . ? O4 Ni1 O2 C1 83.39(19) 4_546 . . . ? C8 Ni1 O2 C1 69.5(2) 4_546 . . . ? O4 C8 O3 Ni1 2.0(3) . . . 4_556 ? C7 C8 O3 Ni1 -175.4(2) . . . 4_556 ? O3 C8 O4 Ni1 -1.9(3) . . . 4_556 ? C7 C8 O4 Ni1 175.5(2) . . . 4_556 ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 1.039 _refine_diff_density_min -0.435 _refine_diff_density_rms 0.086 # Attachment '3.cif' data_shelxl3 _database_code_depnum_ccdc_archive 'CCDC 731982' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C20 H21 N4 Ni O4' _chemical_formula_weight 440.12 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' Ni Ni 0.3393 1.1124 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M C2/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 23.288(5) _cell_length_b 10.373(2) _cell_length_c 17.348(4) _cell_angle_alpha 90.00 _cell_angle_beta 108.92(3) _cell_angle_gamma 90.00 _cell_volume 3964.1(14) _cell_formula_units_Z 8 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 11507 _cell_measurement_theta_min 3.06 _cell_measurement_theta_max 27.51 _exptl_crystal_description block _exptl_crystal_colour green _exptl_crystal_size_max 0.10 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.475 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1832 _exptl_absorpt_coefficient_mu 1.013 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9054 _exptl_absorpt_correction_T_max 0.9054 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(2) _diffrn_radiation_probe x-ray _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_source 'rotating anode' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'rigaku r-axis rapid IP area detector' _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 18917 _diffrn_reflns_av_R_equivalents 0.0791 _diffrn_reflns_av_sigmaI/netI 0.0657 _diffrn_reflns_limit_h_min -30 _diffrn_reflns_limit_h_max 30 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 3.06 _diffrn_reflns_theta_max 27.48 _reflns_number_total 4535 _reflns_number_gt 3019 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'RAXIS-RAPID Auto(Rigaku, 2004)' _computing_cell_refinement 'RAXIS-RAPID Auto(Rigaku, 2004)' _computing_data_reduction 'CrystalStructure(Rigaku/MSC, 2004)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXL-97 (Sheldrick, 2001)' _computing_publication_material 'SHELXL-97 (Sheldrick, 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^)+(0.0660P)^2^+6.5068P] 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 conf _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0008(2) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 4535 _refine_ls_number_parameters 263 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0949 _refine_ls_R_factor_gt 0.0559 _refine_ls_wR_factor_ref 0.1472 _refine_ls_wR_factor_gt 0.1305 _refine_ls_goodness_of_fit_ref 1.034 _refine_ls_restrained_S_all 1.034 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.7154(2) 0.7796(4) 0.8675(3) 0.0446(10) Uani 1 1 d . . . H1 H 0.7495 0.7931 0.8519 0.054 Uiso 1 1 calc R . . C2 C 0.6488(3) 0.8032(5) 0.9275(3) 0.0709(16) Uani 1 1 d . . . H2 H 0.6275 0.8337 0.9607 0.085 Uiso 1 1 calc R . . C3 C 0.6330(2) 0.7026(5) 0.8750(3) 0.0578(13) Uani 1 1 d . . . H3 H 0.5986 0.6516 0.8661 0.069 Uiso 1 1 calc R . . C4 C 0.70983(17) 0.0706(3) 0.7224(2) 0.0332(8) Uani 1 1 d . . . C5 C 0.55652(17) -0.0439(4) 0.7242(2) 0.0364(8) Uani 1 1 d . . . H5 H 0.5355 -0.1217 0.7163 0.044 Uiso 1 1 calc R . . C6 C 0.61354(17) -0.0381(4) 0.7150(2) 0.0367(8) Uani 1 1 d . . . H6 H 0.6302 -0.1124 0.7009 0.044 Uiso 1 1 calc R . . C7 C 0.53095(16) 0.0647(3) 0.7450(2) 0.0300(8) Uani 1 1 d . . . C8 C 0.62071(16) 0.1873(3) 0.7470(2) 0.0300(8) Uani 1 1 d . . . C9 C 0.56428(16) 0.1793(3) 0.7569(2) 0.0317(8) Uani 1 1 d . . . H9 H 0.5478 0.2530 0.7720 0.038 Uiso 1 1 calc R . . C10 C 0.64824(16) 0.3189(3) 0.7543(2) 0.0330(8) Uani 1 1 d . . . C11 C 0.64624(17) 0.0761(3) 0.7263(2) 0.0305(8) Uani 1 1 d . . . C12 C 0.6161(2) 0.6497(4) 0.6016(3) 0.0485(10) Uani 1 1 d . . . H12 H 0.6531 0.6750 0.5967 0.058 Uiso 1 1 calc R . . C13 C 0.4991(2) 0.9270(4) 0.4946(3) 0.0564(12) Uani 1 1 d . . . H13A H 0.4974 0.8867 0.5443 0.068 Uiso 1 1 calc R . . H13B H 0.4624 0.9036 0.4511 0.068 Uiso 1 1 calc R . . C14 C 0.5490(2) 0.5741(5) 0.6489(3) 0.0540(12) Uani 1 1 d . . . H14 H 0.5307 0.5349 0.6832 0.065 Uiso 1 1 calc R . . C15 C 0.5538(3) 0.8754(5) 0.4748(3) 0.0641(14) Uani 1 1 d . . . H15A H 0.5551 0.9155 0.4249 0.077 Uiso 1 1 calc R . . H15B H 0.5904 0.9000 0.5181 0.077 Uiso 1 1 calc R . . C16 C 0.5197(2) 0.6191(5) 0.5739(3) 0.0626(13) Uani 1 1 d . . . H16 H 0.4779 0.6190 0.5479 0.075 Uiso 1 1 calc R . . C17 C 0.5534(3) 0.7311(5) 0.4646(3) 0.0680(15) Uani 1 1 d . . . H17A H 0.5149 0.7046 0.4258 0.082 Uiso 1 1 calc R . . H17B H 0.5854 0.7063 0.4431 0.082 Uiso 1 1 calc R . . C18 C 0.7386(3) 0.9527(5) 0.9742(4) 0.089(2) Uani 1 1 d . . . H18A H 0.7419 0.9349 1.0303 0.107 Uiso 1 1 calc R . . H18B H 0.7792 0.9482 0.9703 0.107 Uiso 1 1 calc R . . C19 C 0.7160(2) 1.0840(4) 0.9546(3) 0.0513(11) Uani 1 1 d . . . H19A H 0.6756 1.0902 0.9593 0.062 Uiso 1 1 calc R . . H19B H 0.7128 1.1033 0.8987 0.062 Uiso 1 1 calc R . . C20 C 0.7571(3) 1.1823(5) 1.0106(3) 0.0680(14) Uani 1 1 d . . . H20A H 0.7558 1.1683 1.0653 0.082 Uiso 1 1 calc R . . H20B H 0.7984 1.1661 1.0117 0.082 Uiso 1 1 calc R . . N1 N 0.61030(16) 0.5947(3) 0.6672(2) 0.0432(8) Uani 1 1 d . . . N2 N 0.56252(18) 0.6651(4) 0.5430(2) 0.0548(10) Uani 1 1 d . . . N3 N 0.67565(15) 0.6885(3) 0.8377(2) 0.0397(8) Uani 1 1 d . . . N4 N 0.7015(2) 0.8508(3) 0.9224(2) 0.0568(10) Uani 1 1 d . . . Ni1 Ni 0.68299(2) 0.54226(4) 0.76382(3) 0.03265(17) Uani 1 1 d . . . O1 O 0.63693(12) 0.3989(2) 0.80295(17) 0.0390(6) Uani 1 1 d . . . O2 O 0.67905(12) 0.3520(2) 0.70997(18) 0.0406(7) Uani 1 1 d . . . O3 O 0.75227(11) 0.1201(3) 0.77948(16) 0.0369(6) Uani 1 1 d . . . O4 O 0.72011(13) 0.0100(3) 0.66589(18) 0.0453(7) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.044(3) 0.035(2) 0.056(3) -0.0013(18) 0.017(2) -0.0035(19) C2 0.082(4) 0.056(3) 0.090(4) -0.019(3) 0.049(3) 0.004(3) C3 0.050(3) 0.046(3) 0.090(4) -0.008(2) 0.041(3) -0.005(2) C4 0.029(2) 0.0245(19) 0.048(2) 0.0035(15) 0.0158(17) 0.0054(15) C5 0.028(2) 0.0223(17) 0.059(2) -0.0025(17) 0.0139(17) -0.0014(15) C6 0.030(2) 0.0233(18) 0.059(2) -0.0023(16) 0.0165(17) 0.0060(16) C7 0.0232(19) 0.0236(18) 0.044(2) -0.0007(14) 0.0115(15) -0.0013(14) C8 0.0254(19) 0.0250(18) 0.040(2) 0.0015(14) 0.0118(15) -0.0001(14) C9 0.026(2) 0.0251(18) 0.045(2) -0.0023(15) 0.0132(16) 0.0010(14) C10 0.0212(19) 0.0267(19) 0.052(2) 0.0017(16) 0.0129(16) 0.0025(15) C11 0.0267(19) 0.0248(18) 0.042(2) 0.0015(14) 0.0141(15) 0.0038(14) C12 0.039(3) 0.042(2) 0.062(3) 0.001(2) 0.013(2) 0.0043(19) C13 0.054(3) 0.053(3) 0.060(3) 0.010(2) 0.015(2) 0.006(2) C14 0.037(3) 0.051(3) 0.071(3) 0.007(2) 0.012(2) 0.001(2) C15 0.069(4) 0.065(3) 0.060(3) 0.012(2) 0.023(3) 0.016(3) C16 0.035(3) 0.062(3) 0.081(4) 0.001(3) 0.005(2) 0.002(2) C17 0.073(4) 0.074(4) 0.048(3) 0.007(2) 0.008(3) 0.024(3) C18 0.104(5) 0.046(3) 0.084(4) -0.022(3) -0.017(4) 0.011(3) C19 0.054(3) 0.038(2) 0.062(3) -0.006(2) 0.021(2) -0.006(2) C20 0.076(4) 0.044(3) 0.075(3) -0.005(2) 0.012(3) -0.007(3) N1 0.038(2) 0.0318(18) 0.059(2) -0.0009(16) 0.0153(17) 0.0021(15) N2 0.046(2) 0.047(2) 0.063(2) 0.0028(18) 0.0068(19) 0.0115(19) N3 0.039(2) 0.0280(17) 0.057(2) -0.0013(14) 0.0219(16) -0.0029(14) N4 0.063(3) 0.031(2) 0.071(3) -0.0105(18) 0.015(2) 0.0022(18) Ni1 0.0250(3) 0.0244(3) 0.0506(3) -0.0004(2) 0.0151(2) -0.0019(2) O1 0.0384(16) 0.0272(14) 0.0575(17) -0.0089(12) 0.0239(13) -0.0078(12) O2 0.0372(16) 0.0270(14) 0.0654(18) 0.0023(12) 0.0274(14) -0.0006(12) O3 0.0244(14) 0.0365(15) 0.0500(16) -0.0023(12) 0.0123(12) 0.0042(11) O4 0.0350(16) 0.0464(17) 0.0605(18) -0.0118(13) 0.0238(14) -0.0010(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 C1 N3 1.305(5) . ? C1 N4 1.325(5) . ? C2 N4 1.351(6) . ? C2 C3 1.354(7) . ? C3 N3 1.357(5) . ? C4 O4 1.252(4) . ? C4 O3 1.259(5) . ? C4 C11 1.505(5) . ? C4 Ni1 2.447(4) 4_646 ? C5 C7 1.376(5) . ? C5 C6 1.389(5) . ? C6 C11 1.387(5) . ? C7 C9 1.398(5) . ? C7 C7 1.506(7) 2_656 ? C8 C9 1.382(5) . ? C8 C11 1.397(5) . ? C8 C10 1.495(5) . ? C10 O2 1.258(4) . ? C10 O1 1.270(4) . ? C10 Ni1 2.442(4) . ? C12 N1 1.319(5) . ? C12 N2 1.339(6) . ? C13 C15 1.521(7) . ? C13 C13 1.525(9) 5_676 ? C14 C16 1.343(7) . ? C14 N1 1.374(5) . ? C15 C17 1.506(7) . ? C16 N2 1.362(6) . ? C17 N2 1.475(6) . ? C18 C19 1.461(7) . ? C18 N4 1.472(6) . ? C19 C20 1.515(7) . ? C20 C20 1.462(10) 7_677 ? N1 Ni1 2.032(4) . ? N3 Ni1 2.029(3) . ? Ni1 O3 2.055(2) 4_656 ? Ni1 O1 2.073(3) . ? Ni1 O2 2.173(3) . ? Ni1 O4 2.215(3) 4_656 ? Ni1 C4 2.447(4) 4_656 ? O3 Ni1 2.055(2) 4_646 ? O4 Ni1 2.215(3) 4_646 ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N3 C1 N4 112.4(4) . . ? N4 C2 C3 107.0(4) . . ? C2 C3 N3 108.8(4) . . ? O4 C4 O3 121.3(3) . . ? O4 C4 C11 119.7(3) . . ? O3 C4 C11 118.8(3) . . ? O4 C4 Ni1 64.4(2) . 4_646 ? O3 C4 Ni1 57.08(18) . 4_646 ? C11 C4 Ni1 170.9(3) . 4_646 ? C7 C5 C6 120.4(3) . . ? C11 C6 C5 121.5(3) . . ? C5 C7 C9 117.9(3) . . ? C5 C7 C7 122.8(2) . 2_656 ? C9 C7 C7 119.3(2) . 2_656 ? C9 C8 C11 118.9(3) . . ? C9 C8 C10 116.3(3) . . ? C11 C8 C10 124.7(3) . . ? C8 C9 C7 122.6(3) . . ? O2 C10 O1 120.7(3) . . ? O2 C10 C8 120.7(3) . . ? O1 C10 C8 118.5(3) . . ? O2 C10 Ni1 62.63(19) . . ? O1 C10 Ni1 58.07(18) . . ? C8 C10 Ni1 174.3(3) . . ? C6 C11 C8 118.8(3) . . ? C6 C11 C4 117.7(3) . . ? C8 C11 C4 123.3(3) . . ? N1 C12 N2 112.1(4) . . ? C15 C13 C13 112.6(5) . 5_676 ? C16 C14 N1 109.5(4) . . ? C17 C15 C13 113.7(5) . . ? C14 C16 N2 107.2(4) . . ? N2 C17 C15 111.1(4) . . ? C19 C18 N4 115.6(5) . . ? C18 C19 C20 111.9(5) . . ? C20 C20 C19 116.2(6) 7_677 . ? C12 N1 C14 104.9(4) . . ? C12 N1 Ni1 122.4(3) . . ? C14 N1 Ni1 132.4(3) . . ? C12 N2 C16 106.3(4) . . ? C12 N2 C17 125.1(4) . . ? C16 N2 C17 128.3(4) . . ? C1 N3 C3 105.5(4) . . ? C1 N3 Ni1 126.7(3) . . ? C3 N3 Ni1 127.3(3) . . ? C1 N4 C2 106.4(4) . . ? C1 N4 C18 127.3(5) . . ? C2 N4 C18 126.0(5) . . ? N3 Ni1 N1 95.89(14) . . ? N3 Ni1 O3 99.16(12) . 4_656 ? N1 Ni1 O3 96.16(12) . 4_656 ? N3 Ni1 O1 99.84(11) . . ? N1 Ni1 O1 94.64(13) . . ? O3 Ni1 O1 157.01(11) 4_656 . ? N3 Ni1 O2 161.88(11) . . ? N1 Ni1 O2 88.90(12) . . ? O3 Ni1 O2 97.68(10) 4_656 . ? O1 Ni1 O2 62.27(10) . . ? N3 Ni1 O4 92.55(13) . 4_656 ? N1 Ni1 O4 157.21(12) . 4_656 ? O3 Ni1 O4 61.54(10) 4_656 4_656 ? O1 Ni1 O4 104.73(11) . 4_656 ? O2 Ni1 O4 89.60(11) . 4_656 ? N3 Ni1 C10 131.15(12) . . ? N1 Ni1 C10 91.66(13) . . ? O3 Ni1 C10 127.91(11) 4_656 . ? O1 Ni1 C10 31.34(10) . . ? O2 Ni1 C10 30.93(10) . . ? O4 Ni1 C10 98.62(11) 4_656 . ? N3 Ni1 C4 98.09(13) . 4_656 ? N1 Ni1 C4 126.79(13) . 4_656 ? O3 Ni1 C4 30.95(11) 4_656 4_656 ? O1 Ni1 C4 132.39(12) . 4_656 ? O2 Ni1 C4 92.91(11) . 4_656 ? O4 Ni1 C4 30.64(11) 4_656 4_656 ? C10 Ni1 C4 115.21(12) . 4_656 ? C10 O1 Ni1 90.6(2) . . ? C10 O2 Ni1 86.4(2) . . ? C4 O3 Ni1 92.0(2) . 4_646 ? C4 O4 Ni1 85.0(2) . 4_646 ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N4 C2 C3 N3 -0.1(6) . . . . ? C7 C5 C6 C11 0.0(6) . . . . ? C6 C5 C7 C9 -0.4(6) . . . . ? C6 C5 C7 C7 179.3(4) . . . 2_656 ? C11 C8 C9 C7 -1.6(6) . . . . ? C10 C8 C9 C7 174.6(3) . . . . ? C5 C7 C9 C8 1.3(6) . . . . ? C7 C7 C9 C8 -178.5(4) 2_656 . . . ? C9 C8 C10 O2 -143.5(4) . . . . ? C11 C8 C10 O2 32.4(6) . . . . ? C9 C8 C10 O1 32.5(5) . . . . ? C11 C8 C10 O1 -151.6(4) . . . . ? C9 C8 C10 Ni1 -19(3) . . . . ? C11 C8 C10 Ni1 157(3) . . . . ? C5 C6 C11 C8 -0.4(6) . . . . ? C5 C6 C11 C4 174.6(4) . . . . ? C9 C8 C11 C6 1.2(5) . . . . ? C10 C8 C11 C6 -174.7(4) . . . . ? C9 C8 C11 C4 -173.6(3) . . . . ? C10 C8 C11 C4 10.6(6) . . . . ? O4 C4 C11 C6 46.0(5) . . . . ? O3 C4 C11 C6 -129.2(4) . . . . ? Ni1 C4 C11 C6 -68.3(18) 4_646 . . . ? O4 C4 C11 C8 -139.2(4) . . . . ? O3 C4 C11 C8 45.6(5) . . . . ? Ni1 C4 C11 C8 106.4(16) 4_646 . . . ? C13 C13 C15 C17 179.5(5) 5_676 . . . ? N1 C14 C16 N2 1.9(6) . . . . ? C13 C15 C17 N2 -68.8(6) . . . . ? N4 C18 C19 C20 -179.7(5) . . . . ? C18 C19 C20 C20 172.2(7) . . . 7_677 ? N2 C12 N1 C14 -0.1(5) . . . . ? N2 C12 N1 Ni1 174.3(3) . . . . ? C16 C14 N1 C12 -1.1(5) . . . . ? C16 C14 N1 Ni1 -174.8(3) . . . . ? N1 C12 N2 C16 1.2(5) . . . . ? N1 C12 N2 C17 175.8(4) . . . . ? C14 C16 N2 C12 -1.9(6) . . . . ? C14 C16 N2 C17 -176.2(5) . . . . ? C15 C17 N2 C12 -78.9(6) . . . . ? C15 C17 N2 C16 94.4(6) . . . . ? N4 C1 N3 C3 0.8(5) . . . . ? N4 C1 N3 Ni1 -171.4(3) . . . . ? C2 C3 N3 C1 -0.4(6) . . . . ? C2 C3 N3 Ni1 171.7(4) . . . . ? N3 C1 N4 C2 -0.9(6) . . . . ? N3 C1 N4 C18 173.4(4) . . . . ? C3 C2 N4 C1 0.6(6) . . . . ? C3 C2 N4 C18 -173.8(5) . . . . ? C19 C18 N4 C1 109.9(6) . . . . ? C19 C18 N4 C2 -76.9(8) . . . . ? C1 N3 Ni1 N1 -117.2(4) . . . . ? C3 N3 Ni1 N1 72.3(4) . . . . ? C1 N3 Ni1 O3 -20.0(4) . . . 4_656 ? C3 N3 Ni1 O3 169.5(4) . . . 4_656 ? C1 N3 Ni1 O1 147.0(4) . . . . ? C3 N3 Ni1 O1 -23.4(4) . . . . ? C1 N3 Ni1 O2 138.1(4) . . . . ? C3 N3 Ni1 O2 -32.4(7) . . . . ? C1 N3 Ni1 O4 41.6(4) . . . 4_656 ? C3 N3 Ni1 O4 -128.9(4) . . . 4_656 ? C1 N3 Ni1 C10 145.4(3) . . . . ? C3 N3 Ni1 C10 -25.1(5) . . . . ? C1 N3 Ni1 C4 11.3(4) . . . 4_656 ? C3 N3 Ni1 C4 -159.2(4) . . . 4_656 ? C12 N1 Ni1 N3 105.1(3) . . . . ? C14 N1 Ni1 N3 -82.1(4) . . . . ? C12 N1 Ni1 O3 5.2(3) . . . 4_656 ? C14 N1 Ni1 O3 178.0(4) . . . 4_656 ? C12 N1 Ni1 O1 -154.4(3) . . . . ? C14 N1 Ni1 O1 18.3(4) . . . . ? C12 N1 Ni1 O2 -92.4(3) . . . . ? C14 N1 Ni1 O2 80.4(4) . . . . ? C12 N1 Ni1 O4 -6.0(6) . . . 4_656 ? C14 N1 Ni1 O4 166.7(3) . . . 4_656 ? C12 N1 Ni1 C10 -123.2(3) . . . . ? C14 N1 Ni1 C10 49.5(4) . . . . ? C12 N1 Ni1 C4 0.4(4) . . . 4_656 ? C14 N1 Ni1 C4 173.2(4) . . . 4_656 ? O2 C10 Ni1 N3 -175.6(2) . . . . ? O1 C10 Ni1 N3 3.1(3) . . . . ? C8 C10 Ni1 N3 57(3) . . . . ? O2 C10 Ni1 N1 85.1(2) . . . . ? O1 C10 Ni1 N1 -96.2(2) . . . . ? C8 C10 Ni1 N1 -42(3) . . . . ? O2 C10 Ni1 O3 -14.0(3) . . . 4_656 ? O1 C10 Ni1 O3 164.7(2) . . . 4_656 ? C8 C10 Ni1 O3 -141(3) . . . 4_656 ? O2 C10 Ni1 O1 -178.7(4) . . . . ? C8 C10 Ni1 O1 54(3) . . . . ? O1 C10 Ni1 O2 178.7(4) . . . . ? C8 C10 Ni1 O2 -127(3) . . . . ? O2 C10 Ni1 O4 -74.5(2) . . . 4_656 ? O1 C10 Ni1 O4 104.2(2) . . . 4_656 ? C8 C10 Ni1 O4 159(3) . . . 4_656 ? O2 C10 Ni1 C4 -47.4(3) . . . 4_656 ? O1 C10 Ni1 C4 131.3(2) . . . 4_656 ? C8 C10 Ni1 C4 -174(3) . . . 4_656 ? O2 C10 O1 Ni1 1.3(4) . . . . ? C8 C10 O1 Ni1 -174.7(3) . . . . ? N3 Ni1 O1 C10 -177.6(2) . . . . ? N1 Ni1 O1 C10 85.6(2) . . . . ? O3 Ni1 O1 C10 -32.3(4) 4_656 . . . ? O2 Ni1 O1 C10 -0.7(2) . . . . ? O4 Ni1 O1 C10 -82.3(2) 4_656 . . . ? C4 Ni1 O1 C10 -67.0(3) 4_656 . . . ? O1 C10 O2 Ni1 -1.3(4) . . . . ? C8 C10 O2 Ni1 174.7(3) . . . . ? N3 Ni1 O2 C10 10.7(5) . . . . ? N1 Ni1 O2 C10 -95.1(2) . . . . ? O3 Ni1 O2 C10 168.9(2) 4_656 . . . ? O1 Ni1 O2 C10 0.7(2) . . . . ? O4 Ni1 O2 C10 107.7(2) 4_656 . . . ? C4 Ni1 O2 C10 138.1(2) 4_656 . . . ? O4 C4 O3 Ni1 -4.6(4) . . . 4_646 ? C11 C4 O3 Ni1 170.5(3) . . . 4_646 ? O3 C4 O4 Ni1 4.3(3) . . . 4_646 ? C11 C4 O4 Ni1 -170.8(3) . . . 4_646 ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 1.193 _refine_diff_density_min -0.433 _refine_diff_density_rms 0.083 # Attachment '4.cif' data_shelxl4 _database_code_depnum_ccdc_archive 'CCDC 731983' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C18 H25 N4 Ni O9' _chemical_formula_weight 500.11 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 7.2130(14) _cell_length_b 12.080(2) _cell_length_c 12.795(3) _cell_angle_alpha 73.96(3) _cell_angle_beta 84.82(3) _cell_angle_gamma 88.36(3) _cell_volume 1067.1(4) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 7435 _cell_measurement_theta_min 3.15 _cell_measurement_theta_max 27.49 _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.556 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 520 _exptl_absorpt_coefficient_mu 0.968 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8300 _exptl_absorpt_correction_T_max 0.8300 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(2) _diffrn_radiation_probe x-ray _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_source 'rotating anode' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'rigaku r-axis rapid IP area detector' _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 10670 _diffrn_reflns_av_R_equivalents 0.0528 _diffrn_reflns_av_sigmaI/netI 0.0722 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 3.16 _diffrn_reflns_theta_max 27.48 _reflns_number_total 4863 _reflns_number_gt 3648 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'RAXIS-RAPID Auto(Rigaku, 2004)' _computing_cell_refinement 'RAXIS-RAPID Auto(Rigaku, 2004)' _computing_data_reduction 'CrystalStructure(Rigaku/MSC, 2004)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXL-97 (Sheldrick, 2001)' _computing_publication_material 'SHELXL-97 (Sheldrick, 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^)+(0.0244P)^2^+1.9145P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4863 _refine_ls_number_parameters 286 _refine_ls_number_restraints 12 _refine_ls_R_factor_all 0.0770 _refine_ls_R_factor_gt 0.0504 _refine_ls_wR_factor_ref 0.1164 _refine_ls_wR_factor_gt 0.1006 _refine_ls_goodness_of_fit_ref 1.042 _refine_ls_restrained_S_all 1.041 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.9110(5) 0.8083(3) 0.9756(3) 0.0321(8) Uani 1 1 d . . . H1 H 1.0095 0.7755 0.9424 0.039 Uiso 1 1 calc R . . C2 C 0.6399(5) 0.8711(3) 1.0137(3) 0.0345(9) Uani 1 1 d . . . H2 H 0.5142 0.8899 1.0112 0.041 Uiso 1 1 calc R . . C3 C 0.7486(5) 0.8923(4) 1.0858(3) 0.0379(9) Uani 1 1 d . . . H3 H 0.7139 0.9270 1.1410 0.046 Uiso 1 1 calc R . . C4 C 1.0943(5) 0.8512(4) 1.1150(3) 0.0365(9) Uani 1 1 d . . . H4A H 1.1413 0.9292 1.0968 0.044 Uiso 1 1 calc R . . H4B H 1.1882 0.8045 1.0879 0.044 Uiso 1 1 calc R . . C5 C 1.0640(6) 0.8057(3) 1.2366(3) 0.0365(9) Uani 1 1 d . . . H5A H 0.9862 0.7376 1.2560 0.044 Uiso 1 1 calc R . . H5B H 1.1823 0.7848 1.2675 0.044 Uiso 1 1 calc R . . C6 C 0.9220(6) 0.8543(4) 1.3913(3) 0.0388(9) Uani 1 1 d . . . C7 C 0.8308(5) 0.9564(3) 1.4232(3) 0.0361(9) Uani 1 1 d . . . H7B H 0.7958 0.9344 1.5012 0.043 Uiso 1 1 calc R . . H7A H 0.9200 1.0187 1.4076 0.043 Uiso 1 1 calc R . . C8 C 0.5039(5) 0.9380(3) 1.3735(3) 0.0366(9) Uani 1 1 d . . . H8 H 0.4757 0.8644 1.4180 0.044 Uiso 1 1 calc R . . C9 C 0.3930(5) 1.0084(3) 1.3036(3) 0.0343(8) Uani 1 1 d . . . H9 H 0.2737 0.9905 1.2915 0.041 Uiso 1 1 calc R . . C10 C 0.6474(5) 1.1001(3) 1.2923(3) 0.0301(8) Uani 1 1 d . . . H10 H 0.7386 1.1567 1.2720 0.036 Uiso 1 1 calc R . . C11 C 0.5276(4) 0.6605(3) 0.6509(2) 0.0225(7) Uani 1 1 d . . . C12 C 0.3713(4) 0.6106(3) 0.6085(2) 0.0212(6) Uani 1 1 d . . . C13 C 0.3775(5) 0.6163(3) 0.4976(3) 0.0253(7) Uani 1 1 d . . . H13 H 0.4791 0.6502 0.4509 0.030 Uiso 1 1 calc R . . C14 C 0.2343(5) 0.5722(3) 0.4565(3) 0.0262(7) Uani 1 1 d . . . H14 H 0.2434 0.5754 0.3827 0.031 Uiso 1 1 calc R . . C15 C 0.0777(4) 0.5231(3) 0.5220(2) 0.0209(6) Uani 1 1 d . . . C16 C 0.0737(4) 0.5170(3) 0.6328(3) 0.0244(7) Uani 1 1 d . . . H16 H -0.0292 0.4843 0.6791 0.029 Uiso 1 1 calc R . . C17 C 0.2177(4) 0.5581(3) 0.6761(2) 0.0209(6) Uani 1 1 d . . . C18 C 0.1971(4) 0.5414(3) 0.7982(3) 0.0242(7) Uani 1 1 d . . . N1 N 0.4832(4) 1.1101(2) 1.2532(2) 0.0277(6) Uani 1 1 d . . . N2 N 0.6661(4) 0.9973(3) 1.3654(2) 0.0297(6) Uani 1 1 d . . . N3 N 0.7383(4) 0.8185(2) 0.9450(2) 0.0279(6) Uani 1 1 d . . . N4 N 0.9245(4) 0.8513(3) 1.0602(2) 0.0295(7) Uani 1 1 d . . . Ni1 Ni 0.63326(6) 0.74070(4) 0.83922(3) 0.02162(12) Uani 1 1 d . . . O1 O 0.9758(3) 0.8935(2) 1.27766(19) 0.0312(6) Uani 1 1 d . . . O2 O 0.5158(3) 0.6453(2) 0.75324(17) 0.0253(5) Uani 1 1 d . . . O3 O 0.6535(4) 0.7140(2) 0.58571(19) 0.0397(7) Uani 1 1 d . . . O4 O 0.2498(4) 0.4471(2) 0.85734(19) 0.0363(6) Uani 1 1 d . . . O5 O 0.1181(3) 0.6206(2) 0.83312(19) 0.0305(6) Uani 1 1 d . . . O6 O 0.3836(3) 0.7062(2) 0.93938(19) 0.0303(5) Uani 1 1 d D . . H6C H 0.3314 0.6655 0.9066 0.036 Uiso 1 1 d RD . . H6D H 0.3663 0.6663 1.0050 0.036 Uiso 1 1 d RD . . O7 O 0.7581(3) 0.58362(19) 0.92506(18) 0.0262(5) Uani 1 1 d D . . H7C H 0.7290 0.5696 0.9932 0.031 Uiso 1 1 d RD . . H7D H 0.8714 0.5910 0.9003 0.031 Uiso 1 1 d RD . . O8 O 0.8687(3) 0.77291(15) 0.72372(14) 0.0285(5) Uani 1 1 d D . . H8A H 0.9602 0.7294 0.7455 0.034 Uiso 1 1 d RD . . H8B H 0.8285 0.7463 0.6752 0.034 Uiso 1 1 d RD . . O9 O 0.6314(3) 0.39639(15) 0.83972(14) 0.0490(7) Uani 1 1 d RD . . H9A H 0.5153 0.3967 0.8309 0.059 Uiso 1 1 d RD . . H9B H 0.6779 0.4559 0.8503 0.059 Uiso 1 1 d RD . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0277(18) 0.042(2) 0.0331(19) -0.0208(18) -0.0047(15) 0.0032(16) C2 0.0207(17) 0.046(2) 0.044(2) -0.0232(19) -0.0098(15) 0.0075(16) C3 0.033(2) 0.050(2) 0.040(2) -0.028(2) -0.0036(16) 0.0080(17) C4 0.0287(19) 0.052(2) 0.035(2) -0.0210(19) -0.0083(16) 0.0051(17) C5 0.043(2) 0.033(2) 0.037(2) -0.0125(17) -0.0140(17) 0.0103(17) C6 0.042(2) 0.046(2) 0.0246(18) -0.0046(17) -0.0047(16) 0.0159(18) C7 0.033(2) 0.050(2) 0.0254(18) -0.0080(17) -0.0129(15) 0.0131(17) C8 0.032(2) 0.0287(19) 0.043(2) 0.0004(17) -0.0033(17) -0.0002(15) C9 0.0287(19) 0.0327(19) 0.040(2) -0.0079(17) -0.0041(16) -0.0035(15) C10 0.0293(19) 0.0289(18) 0.0303(18) -0.0043(16) -0.0064(15) 0.0006(15) C11 0.0221(16) 0.0279(17) 0.0180(15) -0.0064(14) -0.0035(12) -0.0015(13) C12 0.0233(16) 0.0233(16) 0.0184(15) -0.0065(13) -0.0069(12) 0.0001(13) C13 0.0260(17) 0.0321(18) 0.0175(15) -0.0065(14) 0.0001(13) -0.0038(14) C14 0.0295(18) 0.0348(19) 0.0163(15) -0.0094(14) -0.0046(13) -0.0031(14) C15 0.0254(17) 0.0210(15) 0.0180(15) -0.0065(13) -0.0069(12) -0.0007(13) C16 0.0218(16) 0.0332(18) 0.0193(15) -0.0078(14) -0.0039(13) -0.0041(14) C17 0.0230(16) 0.0253(16) 0.0159(15) -0.0067(13) -0.0060(12) 0.0013(13) C18 0.0186(16) 0.0362(19) 0.0182(15) -0.0073(15) -0.0041(12) -0.0020(14) N1 0.0238(15) 0.0308(16) 0.0279(15) -0.0059(13) -0.0072(12) 0.0012(12) N2 0.0301(16) 0.0318(16) 0.0253(15) -0.0037(13) -0.0068(12) 0.0056(13) N3 0.0261(15) 0.0331(16) 0.0284(15) -0.0129(13) -0.0102(12) 0.0050(12) N4 0.0242(15) 0.0405(17) 0.0287(15) -0.0168(14) -0.0075(12) 0.0046(13) Ni1 0.0205(2) 0.0265(2) 0.0186(2) -0.00629(17) -0.00570(15) 0.00065(16) O1 0.0352(14) 0.0329(13) 0.0247(12) -0.0068(11) -0.0044(10) 0.0064(11) O2 0.0249(12) 0.0341(13) 0.0171(11) -0.0054(10) -0.0060(9) -0.0065(10) O3 0.0343(15) 0.0628(18) 0.0210(12) -0.0087(13) 0.0015(11) -0.0234(13) O4 0.0512(17) 0.0352(14) 0.0183(12) 0.0002(11) -0.0054(11) 0.0018(12) O5 0.0202(12) 0.0496(16) 0.0258(12) -0.0167(12) -0.0049(10) 0.0059(11) O6 0.0269(13) 0.0425(15) 0.0227(12) -0.0110(11) -0.0010(10) -0.0043(11) O7 0.0259(12) 0.0317(13) 0.0196(11) -0.0040(10) -0.0042(9) 0.0018(10) O8 0.0247(12) 0.0343(13) 0.0267(12) -0.0077(11) -0.0053(10) -0.0004(10) O9 0.0583(19) 0.0400(16) 0.0466(17) -0.0093(14) -0.0036(15) 0.0076(14) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 N3 1.332(4) . ? C1 N4 1.336(4) . ? C1 H1 0.9300 . ? C2 C3 1.342(5) . ? C2 N3 1.361(4) . ? C2 H2 0.9300 . ? C3 N4 1.393(4) . ? C3 H3 0.9300 . ? C4 N4 1.465(4) . ? C4 C5 1.498(5) . ? C4 H4A 0.9700 . ? C4 H4B 0.9700 . ? C5 O1 1.420(4) . ? C5 H5A 0.9700 . ? C5 H5B 0.9700 . ? C6 O1 1.420(4) . ? C6 C7 1.518(5) . ? C7 N2 1.458(4) . ? C7 H7B 0.9700 . ? C7 H7A 0.9700 . ? C8 C9 1.354(5) . ? C8 N2 1.371(5) . ? C8 H8 0.9300 . ? C9 N1 1.371(5) . ? C9 H9 0.9300 . ? C10 N1 1.317(4) . ? C10 N2 1.343(4) . ? C10 H10 0.9300 . ? C11 O3 1.240(4) . ? C11 O2 1.266(4) . ? C11 C12 1.503(4) . ? C12 C17 1.393(5) . ? C12 C13 1.399(4) . ? C13 C14 1.383(4) . ? C13 H13 0.9300 . ? C14 C15 1.387(5) . ? C14 H14 0.9300 . ? C15 C16 1.397(4) . ? C15 C15 1.487(6) 2_566 ? C16 C17 1.385(4) . ? C16 H16 0.9300 . ? C17 C18 1.513(4) . ? C18 O4 1.251(4) . ? C18 O5 1.264(4) . ? N1 Ni1 2.065(3) 2_677 ? N3 Ni1 2.053(3) . ? Ni1 O2 2.045(2) . ? Ni1 N1 2.065(3) 2_677 ? Ni1 O6 2.095(2) . ? Ni1 O8 2.118(2) . ? Ni1 O7 2.132(2) . ? O6 H6C 0.8429 . ? O6 H6D 0.8452 . ? O7 H7C 0.8490 . ? O7 H7D 0.8472 . ? O8 H8A 0.8501 . ? O8 H8B 0.8492 . ? O9 H9A 0.8549 . ? O9 H9B 0.8504 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N3 C1 N4 111.2(3) . . ? N3 C1 H1 124.4 . . ? N4 C1 H1 124.4 . . ? C3 C2 N3 111.0(3) . . ? C3 C2 H2 124.5 . . ? N3 C2 H2 124.5 . . ? C2 C3 N4 105.5(3) . . ? C2 C3 H3 127.3 . . ? N4 C3 H3 127.3 . . ? N4 C4 C5 112.9(3) . . ? N4 C4 H4A 109.0 . . ? C5 C4 H4A 109.0 . . ? N4 C4 H4B 109.0 . . ? C5 C4 H4B 109.0 . . ? H4A C4 H4B 107.8 . . ? O1 C5 C4 107.9(3) . . ? O1 C5 H5A 110.1 . . ? C4 C5 H5A 110.1 . . ? O1 C5 H5B 110.1 . . ? C4 C5 H5B 110.1 . . ? H5A C5 H5B 108.4 . . ? O1 C6 C7 106.3(3) . . ? N2 C7 C6 112.3(3) . . ? N2 C7 H7B 109.1 . . ? C6 C7 H7B 109.1 . . ? N2 C7 H7A 109.1 . . ? C6 C7 H7A 109.1 . . ? H7B C7 H7A 107.9 . . ? C9 C8 N2 105.9(3) . . ? C9 C8 H8 127.0 . . ? N2 C8 H8 127.0 . . ? C8 C9 N1 109.8(3) . . ? C8 C9 H9 125.1 . . ? N1 C9 H9 125.1 . . ? N1 C10 N2 111.2(3) . . ? N1 C10 H10 124.4 . . ? N2 C10 H10 124.4 . . ? O3 C11 O2 125.2(3) . . ? O3 C11 C12 119.4(3) . . ? O2 C11 C12 115.3(3) . . ? C17 C12 C13 118.0(3) . . ? C17 C12 C11 122.3(3) . . ? C13 C12 C11 119.7(3) . . ? C14 C13 C12 120.8(3) . . ? C14 C13 H13 119.6 . . ? C12 C13 H13 119.6 . . ? C13 C14 C15 121.9(3) . . ? C13 C14 H14 119.0 . . ? C15 C14 H14 119.0 . . ? C14 C15 C16 116.8(3) . . ? C14 C15 C15 122.1(3) . 2_566 ? C16 C15 C15 121.1(4) . 2_566 ? C17 C16 C15 122.2(3) . . ? C17 C16 H16 118.9 . . ? C15 C16 H16 118.9 . . ? C16 C17 C12 120.3(3) . . ? C16 C17 C18 116.2(3) . . ? C12 C17 C18 123.5(3) . . ? O4 C18 O5 124.8(3) . . ? O4 C18 C17 117.3(3) . . ? O5 C18 C17 117.7(3) . . ? C10 N1 C9 105.7(3) . . ? C10 N1 Ni1 126.5(2) . 2_677 ? C9 N1 Ni1 126.7(2) . 2_677 ? C10 N2 C8 107.4(3) . . ? C10 N2 C7 125.9(3) . . ? C8 N2 C7 126.7(3) . . ? C1 N3 C2 105.3(3) . . ? C1 N3 Ni1 126.4(2) . . ? C2 N3 Ni1 127.1(2) . . ? C1 N4 C3 107.0(3) . . ? C1 N4 C4 125.0(3) . . ? C3 N4 C4 128.0(3) . . ? O2 Ni1 N3 171.86(11) . . ? O2 Ni1 N1 91.07(10) . 2_677 ? N3 Ni1 N1 94.62(11) . 2_677 ? O2 Ni1 O6 83.76(9) . . ? N3 Ni1 O6 90.47(11) . . ? N1 Ni1 O6 89.57(11) 2_677 . ? O2 Ni1 O8 90.40(8) . . ? N3 Ni1 O8 95.61(10) . . ? N1 Ni1 O8 87.80(10) 2_677 . ? O6 Ni1 O8 173.55(8) . . ? O2 Ni1 O7 86.23(9) . . ? N3 Ni1 O7 88.32(10) . . ? N1 Ni1 O7 176.29(10) 2_677 . ? O6 Ni1 O7 92.67(10) . . ? O8 Ni1 O7 89.66(9) . . ? C5 O1 C6 112.2(3) . . ? C11 O2 Ni1 128.2(2) . . ? Ni1 O6 H6C 98.9 . . ? Ni1 O6 H6D 128.8 . . ? H6C O6 H6D 101.6 . . ? Ni1 O7 H7C 110.6 . . ? Ni1 O7 H7D 103.6 . . ? H7C O7 H7D 120.1 . . ? Ni1 O8 H8A 112.4 . . ? Ni1 O8 H8B 99.2 . . ? H8A O8 H8B 104.2 . . ? H9A O9 H9B 118.4 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N3 C2 C3 N4 0.3(5) . . . . ? N4 C4 C5 O1 -77.3(4) . . . . ? O1 C6 C7 N2 60.9(4) . . . . ? N2 C8 C9 N1 -0.4(4) . . . . ? O3 C11 C12 C17 -174.4(3) . . . . ? O2 C11 C12 C17 4.2(5) . . . . ? O3 C11 C12 C13 5.5(5) . . . . ? O2 C11 C12 C13 -175.9(3) . . . . ? C17 C12 C13 C14 0.6(5) . . . . ? C11 C12 C13 C14 -179.3(3) . . . . ? C12 C13 C14 C15 1.5(5) . . . . ? C13 C14 C15 C16 -1.9(5) . . . . ? C13 C14 C15 C15 179.2(4) . . . 2_566 ? C14 C15 C16 C17 0.3(5) . . . . ? C15 C15 C16 C17 179.2(3) 2_566 . . . ? C15 C16 C17 C12 1.8(5) . . . . ? C15 C16 C17 C18 -177.7(3) . . . . ? C13 C12 C17 C16 -2.2(5) . . . . ? C11 C12 C17 C16 177.7(3) . . . . ? C13 C12 C17 C18 177.2(3) . . . . ? C11 C12 C17 C18 -2.9(5) . . . . ? C16 C17 C18 O4 85.4(4) . . . . ? C12 C17 C18 O4 -94.1(4) . . . . ? C16 C17 C18 O5 -90.5(4) . . . . ? C12 C17 C18 O5 90.0(4) . . . . ? N2 C10 N1 C9 -0.3(4) . . . . ? N2 C10 N1 Ni1 168.3(2) . . . 2_677 ? C8 C9 N1 C10 0.4(4) . . . . ? C8 C9 N1 Ni1 -168.0(3) . . . 2_677 ? N1 C10 N2 C8 0.0(4) . . . . ? N1 C10 N2 C7 178.8(3) . . . . ? C9 C8 N2 C10 0.3(4) . . . . ? C9 C8 N2 C7 -178.6(3) . . . . ? C6 C7 N2 C10 -114.2(4) . . . . ? C6 C7 N2 C8 64.4(5) . . . . ? N4 C1 N3 C2 0.4(4) . . . . ? N4 C1 N3 Ni1 -168.0(2) . . . . ? C3 C2 N3 C1 -0.4(5) . . . . ? C3 C2 N3 Ni1 167.8(3) . . . . ? N3 C1 N4 C3 -0.2(4) . . . . ? N3 C1 N4 C4 178.6(3) . . . . ? C2 C3 N4 C1 -0.1(5) . . . . ? C2 C3 N4 C4 -178.8(4) . . . . ? C5 C4 N4 C1 -130.3(4) . . . . ? C5 C4 N4 C3 48.2(5) . . . . ? C1 N3 Ni1 O2 94.2(8) . . . . ? C2 N3 Ni1 O2 -71.6(8) . . . . ? C1 N3 Ni1 N1 -131.5(3) . . . 2_677 ? C2 N3 Ni1 N1 62.7(3) . . . 2_677 ? C1 N3 Ni1 O6 138.9(3) . . . . ? C2 N3 Ni1 O6 -26.9(3) . . . . ? C1 N3 Ni1 O8 -43.2(3) . . . . ? C2 N3 Ni1 O8 150.9(3) . . . . ? C1 N3 Ni1 O7 46.3(3) . . . . ? C2 N3 Ni1 O7 -119.6(3) . . . . ? C4 C5 O1 C6 173.4(3) . . . . ? C7 C6 O1 C5 180.0(3) . . . . ? O3 C11 O2 Ni1 22.5(5) . . . . ? C12 C11 O2 Ni1 -156.0(2) . . . . ? N3 Ni1 O2 C11 -171.8(6) . . . . ? N1 Ni1 O2 C11 53.7(3) 2_677 . . . ? O6 Ni1 O2 C11 143.2(3) . . . . ? O8 Ni1 O2 C11 -34.1(3) . . . . ? O7 Ni1 O2 C11 -123.7(3) . . . . ? _diffrn_measured_fraction_theta_max 0.993 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.993 _refine_diff_density_max 0.804 _refine_diff_density_min -0.713 _refine_diff_density_rms 0.089 # Attachment '5.cif' data_shelxl5 _database_code_depnum_ccdc_archive 'CCDC 731984' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C18 H17 N4 O5 Zn' _chemical_formula_weight 434.73 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 Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 9.6580(19) _cell_length_b 10.131(2) _cell_length_c 10.721(2) _cell_angle_alpha 84.56(3) _cell_angle_beta 64.35(3) _cell_angle_gamma 71.02(3) _cell_volume 892.9(3) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 6157 _cell_measurement_theta_min 3.08 _cell_measurement_theta_max 27.52 _exptl_crystal_description block _exptl_crystal_colour ? _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.617 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 446 _exptl_absorpt_coefficient_mu 1.415 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7650 _exptl_absorpt_correction_T_max 0.7650 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(2) _diffrn_radiation_probe x-ray _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_source 'rotating anode' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'rigaku r-axis rapid IP area detector' _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 8890 _diffrn_reflns_av_R_equivalents 0.0657 _diffrn_reflns_av_sigmaI/netI 0.0897 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 3.08 _diffrn_reflns_theta_max 27.48 _reflns_number_total 4053 _reflns_number_gt 2873 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'RAXIS-RAPID Auto(Rigaku, 2004)' _computing_cell_refinement 'RAXIS-RAPID Auto(Rigaku, 2004)' _computing_data_reduction 'CrystalStructure(Rigaku/MSC, 2004)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXL-97 (Sheldrick, 2001)' _computing_publication_material 'SHELXL-97 (Sheldrick, 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^)+(0.0619P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4053 _refine_ls_number_parameters 253 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0846 _refine_ls_R_factor_gt 0.0521 _refine_ls_wR_factor_ref 0.1353 _refine_ls_wR_factor_gt 0.1225 _refine_ls_goodness_of_fit_ref 1.066 _refine_ls_restrained_S_all 1.066 _refine_ls_shift/su_max 0.002 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.8559(5) 0.2869(4) 0.5973(4) 0.0280(8) Uani 1 1 d . . . C2 C 0.7819(4) 0.3010(4) 0.7542(4) 0.0230(8) Uani 1 1 d . . . C3 C 0.6489(5) 0.4166(4) 0.8211(4) 0.0272(8) Uani 1 1 d . . . H3 H 0.6102 0.4831 0.7680 0.033 Uiso 1 1 calc R . . C4 C 0.5711(4) 0.4371(4) 0.9648(4) 0.0257(8) Uani 1 1 d . . . C5 C 0.6307(5) 0.3342(5) 1.0415(4) 0.0342(9) Uani 1 1 d . . . H5 H 0.5803 0.3438 1.1378 0.041 Uiso 1 1 calc R . . C6 C 0.7639(5) 0.2180(4) 0.9761(4) 0.0336(9) Uani 1 1 d . . . H6 H 0.8011 0.1505 1.0293 0.040 Uiso 1 1 calc R . . C7 C 0.8429(5) 0.2007(4) 0.8321(4) 0.0271(8) Uani 1 1 d . . . C8 C 0.9857(5) 0.0713(4) 0.7697(4) 0.0289(9) Uani 1 1 d . . . C9 C 0.5777(5) 0.1070(5) 0.3396(4) 0.0364(10) Uani 1 1 d . . . H9 H 0.6507 0.0244 0.2888 0.044 Uiso 1 1 calc R . . C10 C 0.4752(5) 0.3049(5) 0.4550(5) 0.0453(11) Uani 1 1 d . . . H10 H 0.4653 0.3848 0.4986 0.054 Uiso 1 1 calc R . . C11 C 0.3505(5) 0.2743(5) 0.4480(5) 0.0472(12) Uani 1 1 d . . . H11 H 0.2417 0.3278 0.4858 0.057 Uiso 1 1 calc R . . C12 C 0.3322(5) 0.0725(6) 0.3388(5) 0.0464(12) Uani 1 1 d . . . H12A H 0.2208 0.1307 0.3651 0.056 Uiso 1 1 calc R . . H12B H 0.3312 -0.0112 0.3909 0.056 Uiso 1 1 calc R . . C13 C 0.4113(6) 0.0325(6) 0.1870(5) 0.0477(12) Uani 1 1 d . . . H13A H 0.3443 -0.0073 0.1664 0.057 Uiso 1 1 calc R . . H13B H 0.4163 0.1164 0.1357 0.057 Uiso 1 1 calc R . . C14 C 0.5741(6) -0.2049(6) 0.1706(5) 0.0518(13) Uani 1 1 d . . . H14A H 0.5374 -0.2403 0.1135 0.062 Uiso 1 1 calc R . . H14B H 0.5021 -0.2088 0.2670 0.062 Uiso 1 1 calc R . . C15 C 0.7432(6) -0.2929(6) 0.1430(4) 0.0515(13) Uani 1 1 d . . . H15A H 0.7840 -0.2486 0.1901 0.062 Uiso 1 1 calc R . . H15B H 0.7416 -0.3832 0.1816 0.062 Uiso 1 1 calc R . . C16 C 0.9438(5) -0.2333(4) -0.0781(4) 0.0342(9) Uani 1 1 d . . . H16 H 0.9487 -0.1569 -0.0404 0.041 Uiso 1 1 calc R . . C17 C 0.8769(6) -0.4134(5) -0.0964(5) 0.0474(12) Uani 1 1 d . . . H17 H 0.8289 -0.4836 -0.0752 0.057 Uiso 1 1 calc R . . C18 C 0.9813(6) -0.3905(5) -0.2221(5) 0.0430(11) Uani 1 1 d . . . H18 H 1.0184 -0.4431 -0.3034 0.052 Uiso 1 1 calc R . . N1 N 0.6178(4) 0.1985(4) 0.3872(3) 0.0326(8) Uani 1 1 d . . . N2 N 0.4186(4) 0.1495(4) 0.3743(4) 0.0350(8) Uani 1 1 d . . . N3 N 0.8544(4) -0.3142(4) -0.0053(3) 0.0372(8) Uani 1 1 d . . . N4 N 1.0247(4) -0.2758(4) -0.2112(3) 0.0347(8) Uani 1 1 d . . . O1 O 0.7665(3) 0.2623(3) 0.5497(3) 0.0380(7) Uani 1 1 d . . . O2 O 0.9870(4) 0.3052(4) 0.5296(3) 0.0470(8) Uani 1 1 d . . . O3 O 1.0032(4) 0.0131(3) 0.6615(3) 0.0396(7) Uani 1 1 d . . . O4 O 1.0730(4) 0.0247(3) 0.8308(3) 0.0419(8) Uani 1 1 d . . . O5 O 0.5705(4) -0.0650(3) 0.1400(3) 0.0413(8) Uani 1 1 d . . . Zn1 Zn 0.84280(5) 0.17846(5) 0.36571(4) 0.02588(15) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.025(2) 0.026(2) 0.0241(18) -0.0052(16) -0.0063(16) -0.0021(17) C2 0.0196(17) 0.024(2) 0.0233(17) -0.0041(15) -0.0087(15) -0.0037(16) C3 0.027(2) 0.027(2) 0.0264(19) 0.0003(16) -0.0114(16) -0.0058(17) C4 0.0210(18) 0.030(2) 0.0231(17) -0.0038(15) -0.0070(15) -0.0066(17) C5 0.035(2) 0.036(2) 0.0223(18) -0.0020(17) -0.0084(17) -0.003(2) C6 0.032(2) 0.034(2) 0.028(2) -0.0004(17) -0.0121(17) -0.002(2) C7 0.0222(18) 0.027(2) 0.0293(19) -0.0073(16) -0.0107(16) -0.0027(17) C8 0.0229(19) 0.028(2) 0.0286(19) 0.0029(17) -0.0072(16) -0.0043(17) C9 0.024(2) 0.044(3) 0.038(2) -0.0113(19) -0.0110(18) -0.005(2) C10 0.032(2) 0.044(3) 0.054(3) -0.015(2) -0.017(2) -0.003(2) C11 0.024(2) 0.050(3) 0.058(3) -0.022(2) -0.013(2) 0.001(2) C12 0.028(2) 0.063(3) 0.050(3) -0.018(2) -0.013(2) -0.016(2) C13 0.037(3) 0.062(3) 0.050(3) -0.004(2) -0.024(2) -0.014(3) C14 0.042(3) 0.057(3) 0.044(3) -0.002(2) -0.001(2) -0.023(3) C15 0.053(3) 0.058(3) 0.032(2) 0.009(2) -0.004(2) -0.025(3) C16 0.036(2) 0.031(2) 0.033(2) -0.0043(17) -0.0104(19) -0.012(2) C17 0.055(3) 0.047(3) 0.046(3) 0.003(2) -0.017(2) -0.030(3) C18 0.049(3) 0.039(3) 0.038(2) -0.008(2) -0.012(2) -0.016(2) N1 0.0261(17) 0.039(2) 0.0331(17) -0.0052(15) -0.0139(15) -0.0068(16) N2 0.0226(17) 0.043(2) 0.0389(18) -0.0062(16) -0.0140(15) -0.0064(17) N3 0.0304(19) 0.043(2) 0.0327(18) 0.0026(16) -0.0071(16) -0.0144(18) N4 0.0291(18) 0.041(2) 0.0295(17) -0.0064(15) -0.0075(15) -0.0097(17) O1 0.0298(15) 0.052(2) 0.0287(14) -0.0136(13) -0.0127(12) -0.0039(15) O2 0.0314(17) 0.073(3) 0.0309(15) -0.0021(15) -0.0043(13) -0.0204(18) O3 0.0429(18) 0.0294(16) 0.0362(15) -0.0122(13) -0.0169(14) 0.0052(14) O4 0.0297(16) 0.047(2) 0.0399(16) -0.0028(14) -0.0155(14) 0.0018(15) O5 0.0342(17) 0.053(2) 0.0371(16) -0.0049(15) -0.0089(14) -0.0206(17) Zn1 0.0218(2) 0.0288(3) 0.0238(2) -0.00435(17) -0.00875(18) -0.00369(19) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 O2 1.223(5) . ? C1 O1 1.271(5) . ? C1 C2 1.516(5) . ? C2 C3 1.385(5) . ? C2 C7 1.398(5) . ? C3 C4 1.393(5) . ? C3 H3 0.9300 . ? C4 C5 1.397(6) . ? C4 C4 1.492(8) 2_667 ? C5 C6 1.387(6) . ? C5 H5 0.9300 . ? C6 C7 1.393(5) . ? C6 H6 0.9300 . ? C7 C8 1.503(6) . ? C8 O4 1.235(5) . ? C8 O3 1.272(5) . ? C9 N1 1.328(5) . ? C9 N2 1.338(5) . ? C9 H9 0.9300 . ? C10 C11 1.370(6) . ? C10 N1 1.379(6) . ? C10 H10 0.9300 . ? C11 N2 1.362(6) . ? C11 H11 0.9300 . ? C12 N2 1.486(5) . ? C12 C13 1.498(6) . ? C12 H12A 0.9700 . ? C12 H12B 0.9700 . ? C13 O5 1.425(6) . ? C13 H13A 0.9700 . ? C13 H13B 0.9700 . ? C14 O5 1.417(6) . ? C14 C15 1.495(7) . ? C14 H14A 0.9700 . ? C14 H14B 0.9700 . ? C15 N3 1.471(5) . ? C15 H15A 0.9700 . ? C15 H15B 0.9700 . ? C16 N4 1.329(5) . ? C16 N3 1.335(5) . ? C16 H16 0.9300 . ? C17 C18 1.343(6) . ? C17 N3 1.368(6) . ? C17 H17 0.9300 . ? C18 N4 1.388(5) . ? C18 H18 0.9300 . ? N1 Zn1 2.026(3) . ? N4 Zn1 2.008(3) 2_755 ? O1 Zn1 1.951(3) . ? O3 Zn1 1.979(3) 2_756 ? Zn1 O3 1.979(3) 2_756 ? Zn1 N4 2.008(3) 2_755 ? 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 O2 C1 O1 126.5(4) . . ? O2 C1 C2 119.7(4) . . ? O1 C1 C2 113.8(3) . . ? C3 C2 C7 119.6(3) . . ? C3 C2 C1 118.4(3) . . ? C7 C2 C1 122.0(3) . . ? C2 C3 C4 122.5(4) . . ? C2 C3 H3 118.8 . . ? C4 C3 H3 118.8 . . ? C3 C4 C5 117.3(4) . . ? C3 C4 C4 121.8(4) . 2_667 ? C5 C4 C4 120.9(4) . 2_667 ? C6 C5 C4 120.9(4) . . ? C6 C5 H5 119.5 . . ? C4 C5 H5 119.5 . . ? C5 C6 C7 121.1(4) . . ? C5 C6 H6 119.5 . . ? C7 C6 H6 119.5 . . ? C6 C7 C2 118.6(4) . . ? C6 C7 C8 117.7(4) . . ? C2 C7 C8 123.8(3) . . ? O4 C8 O3 124.4(4) . . ? O4 C8 C7 117.9(4) . . ? O3 C8 C7 117.6(4) . . ? N1 C9 N2 111.1(4) . . ? N1 C9 H9 124.5 . . ? N2 C9 H9 124.5 . . ? C11 C10 N1 109.2(4) . . ? C11 C10 H10 125.4 . . ? N1 C10 H10 125.4 . . ? N2 C11 C10 105.9(4) . . ? N2 C11 H11 127.1 . . ? C10 C11 H11 127.1 . . ? N2 C12 C13 111.4(4) . . ? N2 C12 H12A 109.4 . . ? C13 C12 H12A 109.4 . . ? N2 C12 H12B 109.4 . . ? C13 C12 H12B 109.4 . . ? H12A C12 H12B 108.0 . . ? O5 C13 C12 114.0(4) . . ? O5 C13 H13A 108.8 . . ? C12 C13 H13A 108.8 . . ? O5 C13 H13B 108.8 . . ? C12 C13 H13B 108.8 . . ? H13A C13 H13B 107.6 . . ? O5 C14 C15 109.3(4) . . ? O5 C14 H14A 109.8 . . ? C15 C14 H14A 109.8 . . ? O5 C14 H14B 109.8 . . ? C15 C14 H14B 109.8 . . ? H14A C14 H14B 108.3 . . ? N3 C15 C14 113.3(4) . . ? N3 C15 H15A 108.9 . . ? C14 C15 H15A 108.9 . . ? N3 C15 H15B 108.9 . . ? C14 C15 H15B 108.9 . . ? H15A C15 H15B 107.7 . . ? N4 C16 N3 111.4(4) . . ? N4 C16 H16 124.3 . . ? N3 C16 H16 124.3 . . ? C18 C17 N3 107.2(4) . . ? C18 C17 H17 126.4 . . ? N3 C17 H17 126.4 . . ? C17 C18 N4 109.0(4) . . ? C17 C18 H18 125.5 . . ? N4 C18 H18 125.5 . . ? C9 N1 C10 105.6(4) . . ? C9 N1 Zn1 125.8(3) . . ? C10 N1 Zn1 128.6(3) . . ? C9 N2 C11 108.2(4) . . ? C9 N2 C12 125.5(4) . . ? C11 N2 C12 126.2(4) . . ? C16 N3 C17 107.1(3) . . ? C16 N3 C15 125.9(4) . . ? C17 N3 C15 126.8(4) . . ? C16 N4 C18 105.3(3) . . ? C16 N4 Zn1 126.7(3) . 2_755 ? C18 N4 Zn1 127.6(3) . 2_755 ? C1 O1 Zn1 125.0(3) . . ? C8 O3 Zn1 108.6(3) . 2_756 ? C14 O5 C13 113.9(4) . . ? O1 Zn1 O3 112.35(13) . 2_756 ? O1 Zn1 N4 113.84(14) . 2_755 ? O3 Zn1 N4 101.71(14) 2_756 2_755 ? O1 Zn1 N1 94.24(13) . . ? O3 Zn1 N1 117.48(14) 2_756 . ? N4 Zn1 N1 117.84(14) 2_755 . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O2 C1 C2 C3 107.9(5) . . . . ? O1 C1 C2 C3 -69.1(5) . . . . ? O2 C1 C2 C7 -72.7(5) . . . . ? O1 C1 C2 C7 110.3(4) . . . . ? C7 C2 C3 C4 -0.7(6) . . . . ? C1 C2 C3 C4 178.8(3) . . . . ? C2 C3 C4 C5 -1.0(6) . . . . ? C2 C3 C4 C4 179.4(4) . . . 2_667 ? C3 C4 C5 C6 1.1(6) . . . . ? C4 C4 C5 C6 -179.3(4) 2_667 . . . ? C4 C5 C6 C7 0.4(7) . . . . ? C5 C6 C7 C2 -2.0(6) . . . . ? C5 C6 C7 C8 -179.7(4) . . . . ? C3 C2 C7 C6 2.1(6) . . . . ? C1 C2 C7 C6 -177.2(3) . . . . ? C3 C2 C7 C8 179.6(3) . . . . ? C1 C2 C7 C8 0.3(6) . . . . ? C6 C7 C8 O4 -34.3(5) . . . . ? C2 C7 C8 O4 148.2(4) . . . . ? C6 C7 C8 O3 142.0(4) . . . . ? C2 C7 C8 O3 -35.5(5) . . . . ? N1 C10 C11 N2 -0.6(6) . . . . ? N2 C12 C13 O5 65.2(6) . . . . ? O5 C14 C15 N3 -70.2(5) . . . . ? N3 C17 C18 N4 -0.3(6) . . . . ? N2 C9 N1 C10 -0.4(5) . . . . ? N2 C9 N1 Zn1 178.3(3) . . . . ? C11 C10 N1 C9 0.6(5) . . . . ? C11 C10 N1 Zn1 -178.0(3) . . . . ? N1 C9 N2 C11 0.0(5) . . . . ? N1 C9 N2 C12 -179.7(4) . . . . ? C10 C11 N2 C9 0.4(5) . . . . ? C10 C11 N2 C12 -180.0(4) . . . . ? C13 C12 N2 C9 -51.6(6) . . . . ? C13 C12 N2 C11 128.8(5) . . . . ? N4 C16 N3 C17 -0.8(5) . . . . ? N4 C16 N3 C15 -176.4(4) . . . . ? C18 C17 N3 C16 0.7(6) . . . . ? C18 C17 N3 C15 176.3(5) . . . . ? C14 C15 N3 C16 90.5(6) . . . . ? C14 C15 N3 C17 -84.3(6) . . . . ? N3 C16 N4 C18 0.6(5) . . . . ? N3 C16 N4 Zn1 173.4(3) . . . 2_755 ? C17 C18 N4 C16 -0.2(5) . . . . ? C17 C18 N4 Zn1 -172.8(3) . . . 2_755 ? O2 C1 O1 Zn1 24.6(6) . . . . ? C2 C1 O1 Zn1 -158.6(3) . . . . ? O4 C8 O3 Zn1 12.1(5) . . . 2_756 ? C7 C8 O3 Zn1 -163.9(3) . . . 2_756 ? C15 C14 O5 C13 -168.8(4) . . . . ? C12 C13 O5 C14 78.6(5) . . . . ? C1 O1 Zn1 O3 62.0(4) . . . 2_756 ? C1 O1 Zn1 N4 -53.0(4) . . . 2_755 ? C1 O1 Zn1 N1 -176.0(3) . . . . ? C9 N1 Zn1 O1 -142.6(3) . . . . ? C10 N1 Zn1 O1 35.8(4) . . . . ? C9 N1 Zn1 O3 -24.6(4) . . . 2_756 ? C10 N1 Zn1 O3 153.7(4) . . . 2_756 ? C9 N1 Zn1 N4 97.6(4) . . . 2_755 ? C10 N1 Zn1 N4 -84.1(4) . . . 2_755 ? _diffrn_measured_fraction_theta_max 0.993 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.993 _refine_diff_density_max 0.519 _refine_diff_density_min -0.582 _refine_diff_density_rms 0.117 # Attachment '6.cif' data_shelxl6 _database_code_depnum_ccdc_archive 'CCDC 731985' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C18 H19 Cd N4 O6' _chemical_formula_weight 499.77 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' O O 0.0106 0.0060 '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' Cd Cd -0.8075 1.2024 '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 8.6752(17) _cell_length_b 11.569(2) _cell_length_c 11.626(2) _cell_angle_alpha 65.46(3) _cell_angle_beta 68.83(3) _cell_angle_gamma 79.80(3) _cell_volume 989.3(3) _cell_formula_units_Z 2 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 8469 _cell_measurement_theta_min 3.13 _cell_measurement_theta_max 27.53 _exptl_crystal_description block _exptl_crystal_colour ? _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.678 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 502 _exptl_absorpt_coefficient_mu 1.147 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8031 _exptl_absorpt_correction_T_max 0.8031 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(2) _diffrn_radiation_probe x-ray _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_source 'rotating anode' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'rigaku r-axis rapid IP area detector' _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 9832 _diffrn_reflns_av_R_equivalents 0.0356 _diffrn_reflns_av_sigmaI/netI 0.0461 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 3.13 _diffrn_reflns_theta_max 27.48 _reflns_number_total 4499 _reflns_number_gt 3979 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'RAXIS-RAPID Auto(Rigaku, 2004)' _computing_cell_refinement 'RAXIS-RAPID Auto(Rigaku, 2004)' _computing_data_reduction 'CrystalStructure(Rigaku/MSC, 2004)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXL-97 (Sheldrick, 2001)' _computing_publication_material 'SHELXL-97 (Sheldrick, 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^)+(0.0522P)^2^+0.3309P] 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 refu _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4499 _refine_ls_number_parameters 270 _refine_ls_number_restraints 3 _refine_ls_R_factor_all 0.0414 _refine_ls_R_factor_gt 0.0340 _refine_ls_wR_factor_ref 0.1027 _refine_ls_wR_factor_gt 0.0893 _refine_ls_goodness_of_fit_ref 1.125 _refine_ls_restrained_S_all 1.125 _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 C2 C 0.8181(3) 0.6586(3) 0.6965(3) 0.0308(6) Uani 1 1 d . . . C5 C 0.5658(3) 0.5336(3) 0.9359(3) 0.0303(6) Uani 1 1 d . . . C1 C 0.9627(4) 0.7222(3) 0.5737(3) 0.0355(7) Uani 1 1 d . . . C8 C 0.7143(4) 0.8693(3) 0.7258(4) 0.0417(8) Uani 1 1 d . . . C4 C 0.5846(4) 0.6635(3) 0.8867(3) 0.0363(7) Uani 1 1 d . . . H4 H 0.5126 0.7099 0.9345 0.044 Uiso 1 1 calc R . . C3 C 0.7072(3) 0.7276(3) 0.7686(3) 0.0309(6) Uani 1 1 d . . . C7 C 0.7985(4) 0.5299(3) 0.7429(3) 0.0390(7) Uani 1 1 d . . . H7 H 0.8692 0.4841 0.6939 0.047 Uiso 1 1 calc R . . O5 O 0.8857(4) 0.6375(3) 0.1428(3) 0.0706(9) Uani 1 1 d . . . C6 C 0.6760(4) 0.4658(3) 0.8612(3) 0.0381(7) Uani 1 1 d . . . H6 H 0.6672 0.3785 0.8906 0.046 Uiso 1 1 calc R . . C9 C 1.0672(5) 0.8315(3) 0.1482(3) 0.0464(8) Uani 1 1 d . . . H9 H 0.9683 0.8035 0.2166 0.056 Uiso 1 1 calc R . . C16 C 0.6624(5) 0.6861(5) 0.4102(4) 0.0612(11) Uani 1 1 d . . . H16 H 0.7550 0.6731 0.4371 0.073 Uiso 1 1 calc R . . C18 C 0.4759(4) 0.6658(4) 0.3355(4) 0.0479(9) Uani 1 1 d . . . H18 H 0.4178 0.6347 0.3016 0.058 Uiso 1 1 calc R . . C12 C 0.9781(7) 0.8299(5) -0.0338(5) 0.0714(13) Uani 1 1 d . . . H12A H 1.0166 0.8722 -0.1303 0.086 Uiso 1 1 calc R . . H12B H 0.8710 0.8676 -0.0004 0.086 Uiso 1 1 calc R . . C14 C 0.7905(6) 0.5340(4) 0.1908(5) 0.0685(13) Uani 1 1 d . . . H14A H 0.8598 0.4628 0.1754 0.082 Uiso 1 1 calc R . . H14B H 0.7095 0.5541 0.1450 0.082 Uiso 1 1 calc R . . C10 C 1.3135(5) 0.8943(4) 0.0397(4) 0.0577(11) Uani 1 1 d . . . H10 H 1.4197 0.9186 0.0200 0.069 Uiso 1 1 calc R . . C17 C 0.5505(5) 0.7811(4) 0.4084(4) 0.0575(10) Uani 1 1 d . . . H17 H 0.5516 0.8462 0.4353 0.069 Uiso 1 1 calc R . . C11 C 1.2522(6) 0.8913(4) -0.0489(4) 0.0605(12) Uani 1 1 d . . . H11 H 1.3066 0.9122 -0.1397 0.073 Uiso 1 1 calc R . . C13 C 0.9592(6) 0.6952(5) 0.0018(4) 0.0652(12) Uani 1 1 d . . . H13A H 0.8895 0.6855 -0.0426 0.078 Uiso 1 1 calc R . . H13B H 1.0662 0.6549 -0.0262 0.078 Uiso 1 1 calc R . . C15 C 0.7047(6) 0.4999(4) 0.3377(5) 0.0653(12) Uani 1 1 d . . . H15A H 0.6286 0.4324 0.3713 0.078 Uiso 1 1 calc R . . H15B H 0.7858 0.4689 0.3843 0.078 Uiso 1 1 calc R . . Cd1 Cd 1.19400(3) 0.882933(19) 0.34873(2) 0.03578(10) Uani 1 1 d . . . N1 N 0.4332(4) 0.7688(3) 0.3609(3) 0.0460(7) Uani 1 1 d . . . N2 N 0.6136(4) 0.6104(3) 0.3642(3) 0.0494(8) Uani 1 1 d . . . N3 N 1.1964(4) 0.8561(3) 0.1649(3) 0.0452(7) Uani 1 1 d . . . N4 N 1.0937(5) 0.8514(3) 0.0199(3) 0.0536(8) Uani 1 1 d . . . O1 O 0.9927(3) 0.6985(3) 0.4736(3) 0.0573(7) Uani 1 1 d . . . O2 O 1.0506(3) 0.7921(2) 0.5824(2) 0.0453(6) Uani 1 1 d . . . O3 O 0.7264(4) 0.9391(2) 0.6090(3) 0.0617(8) Uani 1 1 d . . . O4 O 0.7085(4) 0.9103(3) 0.8108(3) 0.0650(8) Uani 1 1 d . . . O6 O 0.9381(3) 1.0037(3) 0.3558(3) 0.0484(6) Uani 1 1 d D . . H6A H 0.882(10) 0.947(6) 0.428(5) 0.20(4) Uiso 1 1 d D . . H6B H 0.918(13) 1.067(6) 0.380(10) 0.22(5) 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 C2 0.0280(13) 0.0264(14) 0.0275(14) -0.0029(11) -0.0025(12) -0.0087(11) C5 0.0301(13) 0.0241(14) 0.0269(14) -0.0012(11) -0.0042(12) -0.0096(11) C1 0.0298(14) 0.0251(15) 0.0339(16) -0.0018(11) -0.0005(13) -0.0035(11) C8 0.0315(14) 0.0272(16) 0.0436(18) -0.0068(13) 0.0093(14) -0.0095(12) C4 0.0332(14) 0.0276(15) 0.0348(16) -0.0081(12) 0.0021(13) -0.0065(12) C3 0.0291(13) 0.0192(13) 0.0331(15) -0.0029(11) -0.0022(12) -0.0084(10) C7 0.0384(16) 0.0311(16) 0.0343(16) -0.0093(12) 0.0023(14) -0.0075(12) O5 0.075(2) 0.082(2) 0.0477(17) -0.0144(15) -0.0151(15) -0.0216(17) C6 0.0434(16) 0.0196(14) 0.0369(17) -0.0058(12) 0.0008(14) -0.0087(12) C9 0.055(2) 0.0403(19) 0.0313(17) -0.0102(13) -0.0023(16) -0.0055(15) C16 0.043(2) 0.079(3) 0.060(3) -0.022(2) -0.0171(19) -0.0088(19) C18 0.0403(17) 0.048(2) 0.053(2) -0.0193(17) -0.0128(16) 0.0005(15) C12 0.097(4) 0.064(3) 0.054(3) -0.015(2) -0.038(3) 0.006(3) C14 0.067(3) 0.050(3) 0.081(3) -0.031(2) -0.009(2) 0.004(2) C10 0.062(2) 0.035(2) 0.056(2) -0.0188(17) 0.010(2) -0.0135(17) C17 0.055(2) 0.054(2) 0.066(3) -0.029(2) -0.009(2) -0.0115(18) C11 0.086(3) 0.034(2) 0.0362(19) -0.0101(15) 0.007(2) -0.0084(19) C13 0.075(3) 0.077(3) 0.048(2) -0.029(2) -0.019(2) -0.003(2) C15 0.057(2) 0.053(3) 0.067(3) -0.020(2) -0.007(2) 0.0131(19) Cd1 0.03542(14) 0.02260(14) 0.03460(15) -0.00609(9) 0.00188(10) -0.00632(8) N1 0.0426(15) 0.0335(15) 0.0557(19) -0.0166(13) -0.0111(14) 0.0022(12) N2 0.0422(15) 0.0401(17) 0.0515(18) -0.0103(13) -0.0109(14) 0.0055(12) N3 0.0548(17) 0.0336(15) 0.0377(15) -0.0138(12) 0.0002(14) -0.0108(13) N4 0.075(2) 0.0395(17) 0.0365(16) -0.0093(12) -0.0147(16) 0.0024(15) O1 0.0562(16) 0.0713(19) 0.0330(13) -0.0180(12) 0.0072(12) -0.0262(14) O2 0.0369(11) 0.0347(13) 0.0492(14) -0.0105(10) 0.0020(11) -0.0134(9) O3 0.0679(17) 0.0265(13) 0.0480(15) 0.0049(11) 0.0036(14) 0.0042(11) O4 0.081(2) 0.0325(14) 0.0716(19) -0.0187(13) -0.0086(16) -0.0160(14) O6 0.0523(15) 0.0459(15) 0.0372(13) -0.0128(11) -0.0061(12) -0.0046(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 C2 C7 1.376(4) . ? C2 C3 1.403(4) . ? C2 C1 1.521(4) . ? C5 C4 1.385(4) . ? C5 C6 1.409(4) . ? C5 C5 1.501(5) 2_667 ? C1 O1 1.233(4) . ? C1 O2 1.261(4) . ? C8 O3 1.234(4) . ? C8 O4 1.244(5) . ? C8 C3 1.508(4) . ? C4 C3 1.395(4) . ? C7 C6 1.394(4) . ? O5 C14 1.375(6) . ? O5 C13 1.424(5) . ? C9 N3 1.300(5) . ? C9 N4 1.348(5) . ? C16 C17 1.330(6) . ? C16 N2 1.385(6) . ? C18 N1 1.304(5) . ? C18 N2 1.337(5) . ? C12 N4 1.458(6) . ? C12 C13 1.460(7) . ? C14 C15 1.501(6) . ? C10 C11 1.333(7) . ? C10 N3 1.379(5) . ? C17 N1 1.372(6) . ? C11 N4 1.366(6) . ? C15 N2 1.465(5) . ? Cd1 N1 2.271(3) 1_655 ? Cd1 N3 2.276(3) . ? Cd1 O2 2.384(3) . ? Cd1 O6 2.398(3) . ? Cd1 O4 2.404(3) 2_776 ? Cd1 O3 2.558(3) 2_776 ? Cd1 O1 2.574(3) . ? N1 Cd1 2.270(3) 1_455 ? O3 Cd1 2.558(3) 2_776 ? O4 Cd1 2.403(3) 2_776 ? 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 C7 C2 C3 118.5(3) . . ? C7 C2 C1 120.2(3) . . ? C3 C2 C1 121.2(3) . . ? C4 C5 C6 117.4(2) . . ? C4 C5 C5 121.8(3) . 2_667 ? C6 C5 C5 120.8(3) . 2_667 ? O1 C1 O2 123.4(3) . . ? O1 C1 C2 118.8(3) . . ? O2 C1 C2 117.7(3) . . ? O3 C8 O4 123.0(3) . . ? O3 C8 C3 119.1(3) . . ? O4 C8 C3 117.9(3) . . ? C5 C4 C3 122.7(3) . . ? C4 C3 C2 119.3(3) . . ? C4 C3 C8 117.5(3) . . ? C2 C3 C8 123.2(2) . . ? C2 C7 C6 122.1(3) . . ? C14 O5 C13 116.9(4) . . ? C7 C6 C5 119.9(3) . . ? N3 C9 N4 111.9(3) . . ? C17 C16 N2 106.4(4) . . ? N1 C18 N2 111.8(4) . . ? N4 C12 C13 112.9(4) . . ? O5 C14 C15 108.5(4) . . ? C11 C10 N3 110.0(4) . . ? C16 C17 N1 109.9(4) . . ? C10 C11 N4 106.6(3) . . ? O5 C13 C12 108.2(4) . . ? N2 C15 C14 110.8(4) . . ? N1 Cd1 N3 94.59(12) 1_655 . ? N1 Cd1 O2 95.13(11) 1_655 . ? N3 Cd1 O2 135.63(10) . . ? N1 Cd1 O6 174.64(10) 1_655 . ? N3 Cd1 O6 90.70(11) . . ? O2 Cd1 O6 80.46(9) . . ? N1 Cd1 O4 102.42(12) 1_655 2_776 ? N3 Cd1 O4 83.20(11) . 2_776 ? O2 Cd1 O4 135.92(10) . 2_776 ? O6 Cd1 O4 79.01(11) . 2_776 ? N1 Cd1 O3 93.62(11) 1_655 2_776 ? N3 Cd1 O3 135.10(9) . 2_776 ? O2 Cd1 O3 87.22(9) . 2_776 ? O6 Cd1 O3 83.18(10) . 2_776 ? O4 Cd1 O3 51.94(10) 2_776 2_776 ? N1 Cd1 O1 98.84(11) 1_655 . ? N3 Cd1 O1 83.36(10) . . ? O2 Cd1 O1 52.38(9) . . ? O6 Cd1 O1 80.92(11) . . ? O4 Cd1 O1 155.63(12) 2_776 . ? O3 Cd1 O1 138.42(8) 2_776 . ? C18 N1 C17 105.7(3) . . ? C18 N1 Cd1 124.3(3) . 1_455 ? C17 N1 Cd1 129.6(3) . 1_455 ? C18 N2 C16 106.3(3) . . ? C18 N2 C15 126.6(4) . . ? C16 N2 C15 126.7(4) . . ? C9 N3 C10 105.1(3) . . ? C9 N3 Cd1 124.6(2) . . ? C10 N3 Cd1 128.2(3) . . ? C9 N4 C11 106.4(4) . . ? C9 N4 C12 126.7(4) . . ? C11 N4 C12 126.9(4) . . ? C1 O1 Cd1 87.0(2) . . ? C1 O2 Cd1 95.2(2) . . ? C8 O3 Cd1 88.0(2) . 2_776 ? C8 O4 Cd1 95.0(2) . 2_776 ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C7 C2 C1 O1 47.5(5) . . . . ? C3 C2 C1 O1 -135.8(3) . . . . ? C7 C2 C1 O2 -129.2(3) . . . . ? C3 C2 C1 O2 47.5(4) . . . . ? C6 C5 C4 C3 -0.3(5) . . . . ? C5 C5 C4 C3 179.2(4) 2_667 . . . ? C5 C4 C3 C2 -0.8(5) . . . . ? C5 C4 C3 C8 179.8(3) . . . . ? C7 C2 C3 C4 2.0(5) . . . . ? C1 C2 C3 C4 -174.7(3) . . . . ? C7 C2 C3 C8 -178.6(3) . . . . ? C1 C2 C3 C8 4.6(5) . . . . ? O3 C8 C3 C4 -132.5(4) . . . . ? O4 C8 C3 C4 47.8(5) . . . . ? O3 C8 C3 C2 48.1(5) . . . . ? O4 C8 C3 C2 -131.5(4) . . . . ? C3 C2 C7 C6 -2.2(5) . . . . ? C1 C2 C7 C6 174.6(3) . . . . ? C2 C7 C6 C5 1.1(6) . . . . ? C4 C5 C6 C7 0.2(5) . . . . ? C5 C5 C6 C7 -179.3(4) 2_667 . . . ? C13 O5 C14 C15 -171.6(4) . . . . ? N2 C16 C17 N1 -0.8(5) . . . . ? N3 C10 C11 N4 0.3(5) . . . . ? C14 O5 C13 C12 151.0(4) . . . . ? N4 C12 C13 O5 65.0(5) . . . . ? O5 C14 C15 N2 53.5(5) . . . . ? N2 C18 N1 C17 0.2(4) . . . . ? N2 C18 N1 Cd1 -173.3(2) . . . 1_455 ? C16 C17 N1 C18 0.4(5) . . . . ? C16 C17 N1 Cd1 173.4(3) . . . 1_455 ? N1 C18 N2 C16 -0.7(4) . . . . ? N1 C18 N2 C15 -174.4(4) . . . . ? C17 C16 N2 C18 0.9(4) . . . . ? C17 C16 N2 C15 174.6(4) . . . . ? C14 C15 N2 C18 70.7(5) . . . . ? C14 C15 N2 C16 -101.8(5) . . . . ? N4 C9 N3 C10 0.0(4) . . . . ? N4 C9 N3 Cd1 164.6(2) . . . . ? C11 C10 N3 C9 -0.2(4) . . . . ? C11 C10 N3 Cd1 -164.0(3) . . . . ? N1 Cd1 N3 C9 138.0(3) 1_655 . . . ? O2 Cd1 N3 C9 35.8(4) . . . . ? O6 Cd1 N3 C9 -41.2(3) . . . . ? O4 Cd1 N3 C9 -120.0(3) 2_776 . . . ? O3 Cd1 N3 C9 -122.2(3) 2_776 . . . ? O1 Cd1 N3 C9 39.6(3) . . . . ? N1 Cd1 N3 C10 -61.2(3) 1_655 . . . ? O2 Cd1 N3 C10 -163.3(3) . . . . ? O6 Cd1 N3 C10 119.7(3) . . . . ? O4 Cd1 N3 C10 40.8(3) 2_776 . . . ? O3 Cd1 N3 C10 38.6(4) 2_776 . . . ? O1 Cd1 N3 C10 -159.6(3) . . . . ? N3 C9 N4 C11 0.2(4) . . . . ? N3 C9 N4 C12 178.0(4) . . . . ? C10 C11 N4 C9 -0.3(4) . . . . ? C10 C11 N4 C12 -178.1(4) . . . . ? C13 C12 N4 C9 -73.5(6) . . . . ? C13 C12 N4 C11 103.9(5) . . . . ? O2 C1 O1 Cd1 -14.2(3) . . . . ? C2 C1 O1 Cd1 169.3(3) . . . . ? N1 Cd1 O1 C1 97.5(2) 1_655 . . . ? N3 Cd1 O1 C1 -168.8(2) . . . . ? O2 Cd1 O1 C1 7.86(19) . . . . ? O6 Cd1 O1 C1 -77.0(2) . . . . ? O4 Cd1 O1 C1 -111.9(3) 2_776 . . . ? O3 Cd1 O1 C1 -8.2(3) 2_776 . . . ? O1 C1 O2 Cd1 15.4(4) . . . . ? C2 C1 O2 Cd1 -168.1(2) . . . . ? N1 Cd1 O2 C1 -104.9(2) 1_655 . . . ? N3 Cd1 O2 C1 -3.0(3) . . . . ? O6 Cd1 O2 C1 78.1(2) . . . . ? O4 Cd1 O2 C1 141.3(2) 2_776 . . . ? O3 Cd1 O2 C1 161.69(19) 2_776 . . . ? O1 Cd1 O2 C1 -7.71(18) . . . . ? O4 C8 O3 Cd1 14.5(4) . . . 2_776 ? C3 C8 O3 Cd1 -165.2(3) . . . 2_776 ? O3 C8 O4 Cd1 -15.5(4) . . . 2_776 ? C3 C8 O4 Cd1 164.2(2) . . . 2_776 ? _diffrn_measured_fraction_theta_max 0.992 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.992 _refine_diff_density_max 1.174 _refine_diff_density_min -0.862 _refine_diff_density_rms 0.154