# Electronic Supplementary Material (ESI) for CrystEngComm # This journal is © The Royal Society of Chemistry 2011 data_global _journal_name_full CrystEngComm _journal_coden_Cambridge 1350 _publ_contact_author_name 'Liya Wang' _publ_contact_author_address ; ; _publ_contact_author_email wlya@lynu.edu.cn loop_ _publ_author_name 'Lufang Ma' 'Xiuqin Li' 'Liya Wang' 'Hongwei Hou' # Attachment '- 1.cif' data_c _database_code_depnum_ccdc_archive 'CCDC 800355' #TrackingRef '- 1.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C42 H36 Co2 N4 O8' _chemical_formula_weight 842.61 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 Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 9.808(3) _cell_length_b 10.109(3) _cell_length_c 10.965(3) _cell_angle_alpha 77.197(4) _cell_angle_beta 81.634(4) _cell_angle_gamma 68.888(4) _cell_volume 986.5(5) _cell_formula_units_Z 1 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 1468 _cell_measurement_theta_min 2.63 _cell_measurement_theta_max 22.81 _exptl_crystal_description block _exptl_crystal_colour purple _exptl_crystal_size_max 0.17 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.03 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.418 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 434 _exptl_absorpt_coefficient_mu 0.899 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8622 _exptl_absorpt_correction_T_max 0.9735 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 7520 _diffrn_reflns_av_R_equivalents 0.0518 _diffrn_reflns_av_sigmaI/netI 0.0893 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 2.54 _diffrn_reflns_theta_max 25.50 _reflns_number_total 3633 _reflns_number_gt 2368 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0379P)^2^+0.7572P] 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 3633 _refine_ls_number_parameters 254 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0970 _refine_ls_R_factor_gt 0.0498 _refine_ls_wR_factor_ref 0.1190 _refine_ls_wR_factor_gt 0.0986 _refine_ls_goodness_of_fit_ref 1.035 _refine_ls_restrained_S_all 1.035 _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 Co1 Co 0.04168(7) 0.63678(6) 0.61788(5) 0.02701(19) Uani 1 1 d . . . O1 O 0.1202(3) 0.4190(3) 0.6741(2) 0.0324(7) Uani 1 1 d . . . O2 O 0.0950(3) 0.3272(3) 0.5149(2) 0.0352(7) Uani 1 1 d . . . O3 O 0.0020(3) -0.1460(3) 0.6305(3) 0.0347(7) Uani 1 1 d . . . O4 O 0.1550(3) -0.3132(3) 0.7585(3) 0.0402(8) Uani 1 1 d . . . N1 N 0.2224(4) 0.6436(4) 0.4786(3) 0.0344(9) Uani 1 1 d . . . N2 N 0.8610(4) 0.6378(4) -0.2397(3) 0.0324(9) Uani 1 1 d . . . C1 C 0.1294(4) 0.1760(4) 0.7161(4) 0.0271(9) Uani 1 1 d . . . C2 C 0.1072(4) 0.0638(4) 0.6764(4) 0.0293(10) Uani 1 1 d . . . H2 H 0.0818 0.0765 0.5950 0.035 Uiso 1 1 calc R . . C3 C 0.1227(5) -0.0661(4) 0.7573(4) 0.0304(10) Uani 1 1 d . . . C4 C 0.1622(5) -0.0848(5) 0.8787(4) 0.0368(11) Uani 1 1 d . . . H4 H 0.1757 -0.1734 0.9318 0.044 Uiso 1 1 calc R . . C5 C 0.1818(5) 0.0248(5) 0.9220(4) 0.0339(10) Uani 1 1 d . . . C6 C 0.1643(5) 0.1550(4) 0.8391(4) 0.0323(10) Uani 1 1 d . . . H6 H 0.1763 0.2303 0.8669 0.039 Uiso 1 1 calc R . . C7 C 0.1128(4) 0.3175(4) 0.6282(4) 0.0261(9) Uani 1 1 d . . . C8 C 0.0907(5) -0.1822(5) 0.7133(4) 0.0321(11) Uani 1 1 d . . . C9 C 0.2201(6) 0.0076(5) 1.0542(4) 0.0501(13) Uani 1 1 d . . . H9A H 0.1954 -0.0715 1.1062 0.075 Uiso 1 1 calc R . . H9B H 0.1662 0.0946 1.0860 0.075 Uiso 1 1 calc R . . H9C H 0.3233 -0.0112 1.0545 0.075 Uiso 1 1 calc R . . C10 C 0.2497(5) 0.7655(5) 0.4309(4) 0.0473(13) Uani 1 1 d . . . H10 H 0.1919 0.8486 0.4614 0.057 Uiso 1 1 calc R . . C11 C 0.3597(5) 0.7748(5) 0.3381(4) 0.0482(13) Uani 1 1 d . . . H11 H 0.3752 0.8624 0.3093 0.058 Uiso 1 1 calc R . . C12 C 0.4459(5) 0.6560(5) 0.2884(4) 0.0406(12) Uani 1 1 d . . . C13 C 0.4198(6) 0.5294(6) 0.3395(5) 0.0587(16) Uani 1 1 d . . . H13 H 0.4776 0.4447 0.3115 0.070 Uiso 1 1 calc R . . C14 C 0.3085(6) 0.5273(5) 0.4319(5) 0.0560(15) Uani 1 1 d . . . H14 H 0.2926 0.4403 0.4634 0.067 Uiso 1 1 calc R . . C15 C 0.5622(5) 0.6637(6) 0.1838(4) 0.0482(13) Uani 1 1 d . . . H15A H 0.6549 0.5913 0.2084 0.058 Uiso 1 1 calc R . . H15B H 0.5733 0.7576 0.1698 0.058 Uiso 1 1 calc R . . C16 C 0.5253(5) 0.6399(6) 0.0635(4) 0.0596(16) Uani 1 1 d . . . H16A H 0.4343 0.7148 0.0378 0.072 Uiso 1 1 calc R . . H16B H 0.5093 0.5481 0.0792 0.072 Uiso 1 1 calc R . . C17 C 0.7283(5) 0.7353(5) -0.2469(4) 0.0437(12) Uani 1 1 d . . . H17 H 0.7086 0.8048 -0.3195 0.052 Uiso 1 1 calc R . . C18 C 0.6167(5) 0.7407(6) -0.1531(4) 0.0485(13) Uani 1 1 d . . . H18 H 0.5250 0.8113 -0.1640 0.058 Uiso 1 1 calc R . . C19 C 0.6423(5) 0.6403(5) -0.0431(4) 0.0398(12) Uani 1 1 d . . . C20 C 0.7816(6) 0.5395(5) -0.0341(4) 0.0491(14) Uani 1 1 d . . . H20 H 0.8050 0.4701 0.0382 0.059 Uiso 1 1 calc R . . C21 C 0.8858(5) 0.5418(5) -0.1326(4) 0.0450(13) Uani 1 1 d . . . H21 H 0.9787 0.4727 -0.1242 0.054 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Co1 0.0409(4) 0.0254(3) 0.0205(3) -0.0088(2) 0.0096(2) -0.0198(3) O1 0.0478(19) 0.0278(16) 0.0288(17) -0.0109(13) 0.0060(14) -0.0215(14) O2 0.055(2) 0.0344(18) 0.0235(17) -0.0072(13) 0.0042(14) -0.0254(15) O3 0.050(2) 0.0366(18) 0.0268(17) -0.0103(14) 0.0026(15) -0.0257(15) O4 0.063(2) 0.0243(18) 0.0375(19) -0.0069(14) 0.0017(16) -0.0210(16) N1 0.042(2) 0.036(2) 0.028(2) -0.0113(17) 0.0119(17) -0.0186(18) N2 0.041(2) 0.036(2) 0.022(2) -0.0078(17) 0.0084(17) -0.0174(18) C1 0.037(2) 0.025(2) 0.024(2) -0.0084(18) 0.0036(19) -0.0157(19) C2 0.043(3) 0.027(2) 0.023(2) -0.0076(18) 0.0048(19) -0.019(2) C3 0.044(3) 0.029(2) 0.023(2) -0.0054(19) 0.0020(19) -0.020(2) C4 0.056(3) 0.027(2) 0.028(3) -0.001(2) 0.000(2) -0.019(2) C5 0.049(3) 0.032(3) 0.024(2) -0.002(2) -0.007(2) -0.017(2) C6 0.047(3) 0.032(3) 0.026(2) -0.011(2) 0.005(2) -0.021(2) C7 0.032(2) 0.023(2) 0.026(2) -0.0050(18) 0.0068(18) -0.0146(18) C8 0.048(3) 0.029(3) 0.025(2) -0.010(2) 0.015(2) -0.024(2) C9 0.076(4) 0.048(3) 0.032(3) -0.007(2) -0.012(3) -0.024(3) C10 0.061(3) 0.036(3) 0.044(3) -0.012(2) 0.022(3) -0.024(3) C11 0.059(3) 0.051(3) 0.040(3) -0.009(2) 0.016(3) -0.033(3) C12 0.044(3) 0.057(3) 0.026(3) -0.008(2) 0.007(2) -0.028(3) C13 0.069(4) 0.055(3) 0.054(3) -0.031(3) 0.034(3) -0.026(3) C14 0.076(4) 0.044(3) 0.055(3) -0.021(3) 0.035(3) -0.036(3) C15 0.046(3) 0.079(4) 0.030(3) -0.018(3) 0.016(2) -0.036(3) C16 0.049(3) 0.104(5) 0.039(3) -0.026(3) 0.020(3) -0.043(3) C17 0.050(3) 0.051(3) 0.027(3) -0.007(2) 0.009(2) -0.018(3) C18 0.037(3) 0.064(4) 0.040(3) -0.018(3) 0.007(2) -0.010(3) C19 0.039(3) 0.058(3) 0.029(3) -0.017(2) 0.010(2) -0.025(3) C20 0.063(4) 0.047(3) 0.030(3) -0.002(2) 0.014(2) -0.019(3) C21 0.047(3) 0.048(3) 0.030(3) -0.008(2) 0.017(2) -0.012(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 Co1 O2 2.007(3) 2_566 ? Co1 O1 2.033(3) . ? Co1 O3 2.120(3) 1_565 ? Co1 N1 2.176(3) . ? Co1 N2 2.184(3) 1_456 ? Co1 O4 2.262(3) 1_565 ? Co1 C8 2.511(4) 1_565 ? O1 C7 1.267(4) . ? O2 C7 1.258(4) . ? O2 Co1 2.007(3) 2_566 ? O3 C8 1.252(5) . ? O3 Co1 2.120(3) 1_545 ? O4 C8 1.263(5) . ? O4 Co1 2.262(3) 1_545 ? N1 C10 1.332(5) . ? N1 C14 1.335(5) . ? N2 C17 1.321(5) . ? N2 C21 1.337(5) . ? N2 Co1 2.184(3) 1_654 ? C1 C6 1.391(5) . ? C1 C2 1.396(5) . ? C1 C7 1.506(5) . ? C2 C3 1.383(5) . ? C2 H2 0.9300 . ? C3 C4 1.394(6) . ? C3 C8 1.506(6) . ? C4 C5 1.379(6) . ? C4 H4 0.9300 . ? C5 C6 1.393(6) . ? C5 C9 1.508(6) . ? C6 H6 0.9300 . ? C8 Co1 2.511(4) 1_545 ? C9 H9A 0.9600 . ? C9 H9B 0.9600 . ? C9 H9C 0.9600 . ? C10 C11 1.386(6) . ? C10 H10 0.9300 . ? C11 C12 1.371(6) . ? C11 H11 0.9300 . ? C12 C13 1.376(6) . ? C12 C15 1.505(6) . ? C13 C14 1.380(6) . ? C13 H13 0.9300 . ? C14 H14 0.9300 . ? C15 C16 1.508(6) . ? C15 H15A 0.9700 . ? C15 H15B 0.9700 . ? C16 C19 1.514(6) . ? C16 H16A 0.9700 . ? C16 H16B 0.9700 . ? C17 C18 1.383(6) . ? C17 H17 0.9300 . ? C18 C19 1.382(6) . ? C18 H18 0.9300 . ? C19 C20 1.381(6) . ? C20 C21 1.377(6) . ? C20 H20 0.9300 . ? C21 H21 0.9300 . ? 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 Co1 O1 105.50(11) 2_566 . ? O2 Co1 O3 98.56(12) 2_566 1_565 ? O1 Co1 O3 155.32(11) . 1_565 ? O2 Co1 N1 91.99(13) 2_566 . ? O1 Co1 N1 94.81(12) . . ? O3 Co1 N1 89.72(12) 1_565 . ? O2 Co1 N2 89.19(13) 2_566 1_456 ? O1 Co1 N2 86.91(12) . 1_456 ? O3 Co1 N2 88.01(12) 1_565 1_456 ? N1 Co1 N2 177.57(14) . 1_456 ? O2 Co1 O4 158.43(11) 2_566 1_565 ? O1 Co1 O4 95.73(11) . 1_565 ? O3 Co1 O4 59.96(11) 1_565 1_565 ? N1 Co1 O4 89.98(12) . 1_565 ? N2 Co1 O4 88.15(12) 1_456 1_565 ? O2 Co1 C8 128.44(14) 2_566 1_565 ? O1 Co1 C8 125.81(14) . 1_565 ? O3 Co1 C8 29.88(12) 1_565 1_565 ? N1 Co1 C8 88.75(13) . 1_565 ? N2 Co1 C8 88.86(13) 1_456 1_565 ? O4 Co1 C8 30.11(12) 1_565 1_565 ? C7 O1 Co1 131.6(3) . . ? C7 O2 Co1 148.7(3) . 2_566 ? C8 O3 Co1 92.6(2) . 1_545 ? C8 O4 Co1 85.9(3) . 1_545 ? C10 N1 C14 116.1(4) . . ? C10 N1 Co1 121.9(3) . . ? C14 N1 Co1 122.0(3) . . ? C17 N2 C21 116.1(4) . . ? C17 N2 Co1 124.3(3) . 1_654 ? C21 N2 Co1 119.4(3) . 1_654 ? C6 C1 C2 118.5(4) . . ? C6 C1 C7 121.0(4) . . ? C2 C1 C7 120.5(4) . . ? C3 C2 C1 120.4(4) . . ? C3 C2 H2 119.8 . . ? C1 C2 H2 119.8 . . ? C2 C3 C4 119.5(4) . . ? C2 C3 C8 118.9(4) . . ? C4 C3 C8 121.5(4) . . ? C5 C4 C3 121.7(4) . . ? C5 C4 H4 119.2 . . ? C3 C4 H4 119.2 . . ? C4 C5 C6 117.7(4) . . ? C4 C5 C9 122.3(4) . . ? C6 C5 C9 120.0(4) . . ? C1 C6 C5 122.2(4) . . ? C1 C6 H6 118.9 . . ? C5 C6 H6 118.9 . . ? O2 C7 O1 124.2(4) . . ? O2 C7 C1 118.7(4) . . ? O1 C7 C1 117.0(4) . . ? O3 C8 O4 121.4(4) . . ? O3 C8 C3 118.8(4) . . ? O4 C8 C3 119.9(4) . . ? O3 C8 Co1 57.5(2) . 1_545 ? O4 C8 Co1 64.0(2) . 1_545 ? C3 C8 Co1 174.2(3) . 1_545 ? C5 C9 H9A 109.5 . . ? C5 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? C5 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? N1 C10 C11 123.3(4) . . ? N1 C10 H10 118.3 . . ? C11 C10 H10 118.3 . . ? C12 C11 C10 120.5(4) . . ? C12 C11 H11 119.8 . . ? C10 C11 H11 119.8 . . ? C11 C12 C13 116.1(4) . . ? C11 C12 C15 121.9(4) . . ? C13 C12 C15 122.0(4) . . ? C12 C13 C14 120.5(5) . . ? C12 C13 H13 119.8 . . ? C14 C13 H13 119.8 . . ? N1 C14 C13 123.4(5) . . ? N1 C14 H14 118.3 . . ? C13 C14 H14 118.3 . . ? C12 C15 C16 112.1(4) . . ? C12 C15 H15A 109.2 . . ? C16 C15 H15A 109.2 . . ? C12 C15 H15B 109.2 . . ? C16 C15 H15B 109.2 . . ? H15A C15 H15B 107.9 . . ? C15 C16 C19 114.0(4) . . ? C15 C16 H16A 108.8 . . ? C19 C16 H16A 108.8 . . ? C15 C16 H16B 108.8 . . ? C19 C16 H16B 108.8 . . ? H16A C16 H16B 107.7 . . ? N2 C17 C18 124.1(5) . . ? N2 C17 H17 117.9 . . ? C18 C17 H17 117.9 . . ? C19 C18 C17 119.6(5) . . ? C19 C18 H18 120.2 . . ? C17 C18 H18 120.2 . . ? C20 C19 C18 116.5(4) . . ? C20 C19 C16 121.1(5) . . ? C18 C19 C16 122.4(5) . . ? C21 C20 C19 119.9(5) . . ? C21 C20 H20 120.1 . . ? C19 C20 H20 120.1 . . ? N2 C21 C20 123.8(4) . . ? N2 C21 H21 118.1 . . ? C20 C21 H21 118.1 . . ? 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 Co1 O1 C7 11.6(4) 2_566 . . . ? O3 Co1 O1 C7 178.3(3) 1_565 . . . ? N1 Co1 O1 C7 -81.8(3) . . . . ? N2 Co1 O1 C7 99.9(3) 1_456 . . . ? O4 Co1 O1 C7 -172.3(3) 1_565 . . . ? C8 Co1 O1 C7 -173.8(3) 1_565 . . . ? O2 Co1 N1 C10 91.3(4) 2_566 . . . ? O1 Co1 N1 C10 -162.9(4) . . . . ? O3 Co1 N1 C10 -7.2(4) 1_565 . . . ? N2 Co1 N1 C10 -28(4) 1_456 . . . ? O4 Co1 N1 C10 -67.2(4) 1_565 . . . ? C8 Co1 N1 C10 -37.1(4) 1_565 . . . ? O2 Co1 N1 C14 -85.7(4) 2_566 . . . ? O1 Co1 N1 C14 20.1(4) . . . . ? O3 Co1 N1 C14 175.8(4) 1_565 . . . ? N2 Co1 N1 C14 155(3) 1_456 . . . ? O4 Co1 N1 C14 115.8(4) 1_565 . . . ? C8 Co1 N1 C14 145.9(4) 1_565 . . . ? C6 C1 C2 C3 -1.3(6) . . . . ? C7 C1 C2 C3 179.9(4) . . . . ? C1 C2 C3 C4 -0.6(6) . . . . ? C1 C2 C3 C8 177.0(4) . . . . ? C2 C3 C4 C5 2.1(7) . . . . ? C8 C3 C4 C5 -175.5(4) . . . . ? C3 C4 C5 C6 -1.6(7) . . . . ? C3 C4 C5 C9 178.2(4) . . . . ? C2 C1 C6 C5 1.9(6) . . . . ? C7 C1 C6 C5 -179.3(4) . . . . ? C4 C5 C6 C1 -0.5(7) . . . . ? C9 C5 C6 C1 179.8(4) . . . . ? Co1 O2 C7 O1 -96.4(6) 2_566 . . . ? Co1 O2 C7 C1 84.7(6) 2_566 . . . ? Co1 O1 C7 O2 24.3(6) . . . . ? Co1 O1 C7 C1 -156.8(3) . . . . ? C6 C1 C7 O2 173.3(4) . . . . ? C2 C1 C7 O2 -7.9(6) . . . . ? C6 C1 C7 O1 -5.6(6) . . . . ? C2 C1 C7 O1 173.2(4) . . . . ? Co1 O3 C8 O4 -3.9(4) 1_545 . . . ? Co1 O3 C8 C3 174.9(3) 1_545 . . . ? Co1 O4 C8 O3 3.7(4) 1_545 . . . ? Co1 O4 C8 C3 -175.1(3) 1_545 . . . ? C2 C3 C8 O3 -26.8(6) . . . . ? C4 C3 C8 O3 150.8(4) . . . . ? C2 C3 C8 O4 152.0(4) . . . . ? C4 C3 C8 O4 -30.4(6) . . . . ? C2 C3 C8 Co1 22(3) . . . 1_545 ? C4 C3 C8 Co1 -161(3) . . . 1_545 ? C14 N1 C10 C11 0.2(7) . . . . ? Co1 N1 C10 C11 -177.0(4) . . . . ? N1 C10 C11 C12 1.3(8) . . . . ? C10 C11 C12 C13 -2.5(8) . . . . ? C10 C11 C12 C15 177.4(4) . . . . ? C11 C12 C13 C14 2.5(8) . . . . ? C15 C12 C13 C14 -177.4(5) . . . . ? C10 N1 C14 C13 -0.2(8) . . . . ? Co1 N1 C14 C13 177.0(4) . . . . ? C12 C13 C14 N1 -1.2(9) . . . . ? C11 C12 C15 C16 -112.5(6) . . . . ? C13 C12 C15 C16 67.4(7) . . . . ? C12 C15 C16 C19 -177.5(5) . . . . ? C21 N2 C17 C18 -1.5(7) . . . . ? Co1 N2 C17 C18 -175.9(4) 1_654 . . . ? N2 C17 C18 C19 0.8(8) . . . . ? C17 C18 C19 C20 0.3(7) . . . . ? C17 C18 C19 C16 179.9(4) . . . . ? C15 C16 C19 C20 61.6(7) . . . . ? C15 C16 C19 C18 -118.0(5) . . . . ? C18 C19 C20 C21 -0.7(7) . . . . ? C16 C19 C20 C21 179.7(4) . . . . ? C17 N2 C21 C20 1.0(7) . . . . ? Co1 N2 C21 C20 175.8(4) 1_654 . . . ? C19 C20 C21 N2 0.0(8) . . . . ? _diffrn_measured_fraction_theta_max 0.988 _diffrn_reflns_theta_full 25.50 _diffrn_measured_fraction_theta_full 0.988 _refine_diff_density_max 0.362 _refine_diff_density_min -0.558 _refine_diff_density_rms 0.083 # Attachment '- 2.cif' data_a _database_code_depnum_ccdc_archive 'CCDC 800356' #TrackingRef '- 2.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C44 H40 Co2 N4 O8' _chemical_formula_weight 870.66 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Co Co 0.3494 0.9721 '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 8.9767(9) _cell_length_b 10.1680(11) _cell_length_c 11.8647(12) _cell_angle_alpha 68.4050(10) _cell_angle_beta 84.3380(10) _cell_angle_gamma 78.1870(10) _cell_volume 985.29(18) _cell_formula_units_Z 1 _cell_measurement_temperature 294(2) _cell_measurement_reflns_used 5086 _cell_measurement_theta_min 2.32 _cell_measurement_theta_max 28.16 _exptl_crystal_description block _exptl_crystal_colour purple _exptl_crystal_size_max 0.41 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.27 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.467 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 450 _exptl_absorpt_coefficient_mu 0.902 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7075 _exptl_absorpt_correction_T_max 0.7953 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 294(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 7031 _diffrn_reflns_av_R_equivalents 0.0127 _diffrn_reflns_av_sigmaI/netI 0.0179 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 2.32 _diffrn_reflns_theta_max 25.50 _reflns_number_total 3553 _reflns_number_gt 3312 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0585P)^2^+0.5359P] 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 3553 _refine_ls_number_parameters 263 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0339 _refine_ls_R_factor_gt 0.0318 _refine_ls_wR_factor_ref 0.0946 _refine_ls_wR_factor_gt 0.0924 _refine_ls_goodness_of_fit_ref 1.048 _refine_ls_restrained_S_all 1.048 _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 Co1 Co 0.35524(3) 0.84583(3) 1.05583(2) 0.02552(12) Uani 1 1 d . . . O1 O 0.16079(17) 0.72915(16) 1.11845(15) 0.0370(4) Uani 1 1 d . . . O2 O 0.36937(18) 0.64099(16) 1.03982(16) 0.0396(4) Uani 1 1 d . . . O3 O 0.42329(17) 0.15491(17) 1.00284(16) 0.0399(4) Uani 1 1 d . . . O4 O 0.25043(17) 0.02107(15) 1.09653(14) 0.0346(4) Uani 1 1 d . . . N1 N 0.2776(2) 0.95466(19) 0.87250(17) 0.0320(4) Uani 1 1 d . . . N2 N 0.5607(2) 1.2461(2) 0.76045(17) 0.0366(4) Uani 1 1 d . . . C1 C 0.1769(2) 0.49577(19) 1.10636(17) 0.0231(4) Uani 1 1 d . . . C2 C 0.2660(2) 0.3845(2) 1.07389(17) 0.0229(4) Uani 1 1 d . . . H2 H 0.3623 0.3939 1.0384 0.028 Uiso 1 1 calc R . . C3 C 0.2090(2) 0.25902(19) 1.09526(16) 0.0223(4) Uani 1 1 d . . . C4 C 0.0642(2) 0.2464(2) 1.14908(18) 0.0263(4) Uani 1 1 d . . . H4 H 0.0272 0.1624 1.1638 0.032 Uiso 1 1 calc R . . C5 C -0.0258(2) 0.3568(2) 1.18103(19) 0.0280(4) Uani 1 1 d . . . C6 C 0.0325(2) 0.4820(2) 1.15850(18) 0.0265(4) Uani 1 1 d . . . H6 H -0.0263 0.5572 1.1787 0.032 Uiso 1 1 calc R . . C7 C 0.2385(2) 0.6303(2) 1.08684(18) 0.0255(4) Uani 1 1 d . . . C8 C 0.3024(2) 0.1363(2) 1.06235(17) 0.0230(4) Uani 1 1 d . . . C9 C -0.1822(3) 0.3404(3) 1.2381(3) 0.0443(6) Uani 1 1 d . . . H9A H -0.2570 0.3820 1.1762 0.066 Uiso 1 1 calc R . . H9B H -0.2033 0.3886 1.2955 0.066 Uiso 1 1 calc R . . H9C H -0.1858 0.2401 1.2788 0.066 Uiso 1 1 calc R . . C10 C 0.3626(3) 0.9313(2) 0.7798(2) 0.0375(5) Uani 1 1 d . . . H10 H 0.4507 0.8617 0.7974 0.045 Uiso 1 1 calc R . . C11 C 0.3261(3) 1.0051(3) 0.6600(2) 0.0419(5) Uani 1 1 d . . . H11 H 0.3892 0.9846 0.5992 0.050 Uiso 1 1 calc R . . C12 C 0.1951(3) 1.1103(3) 0.6293(2) 0.0424(5) Uani 1 1 d . . . C13 C 0.1052(3) 1.1317(3) 0.7254(2) 0.0443(6) Uani 1 1 d . . . H13 H 0.0151 1.1989 0.7102 0.053 Uiso 1 1 calc R . . C14 C 0.1487(3) 1.0539(3) 0.8434(2) 0.0381(5) Uani 1 1 d . . . H14 H 0.0862 1.0706 0.9059 0.046 Uiso 1 1 calc R . . C15 C 0.1518(3) 1.1966(4) 0.4985(3) 0.0605(8) Uani 1 1 d . . . H15A H 0.0797 1.2827 0.4964 0.073 Uiso 1 1 calc R . . H15B H 0.1001 1.1401 0.4702 0.073 Uiso 1 1 calc R . . C16 C 0.2840(4) 1.2420(4) 0.4092(3) 0.0691(9) Uani 1 1 d . . . H16A H 0.3662 1.1597 0.4236 0.083 Uiso 1 1 calc R . . H16B H 0.2498 1.2683 0.3274 0.083 Uiso 1 1 calc R . . C17 C 0.3467(5) 1.3676(4) 0.4167(3) 0.0686(9) Uani 1 1 d . . . H17A H 0.4184 1.3972 0.3495 0.082 Uiso 1 1 calc R . . H17B H 0.2635 1.4481 0.4074 0.082 Uiso 1 1 calc R . . C18 C 0.4224(3) 1.3287(3) 0.7375(2) 0.0468(6) Uani 1 1 d . . . H18 H 0.3703 1.3572 0.7988 0.056 Uiso 1 1 calc R . . C19 C 0.3531(3) 1.3736(3) 0.6275(3) 0.0539(7) Uani 1 1 d . . . H19 H 0.2569 1.4313 0.6164 0.065 Uiso 1 1 calc R . . C20 C 0.4256(3) 1.3335(3) 0.5340(2) 0.0508(7) Uani 1 1 d . . . C21 C 0.5726(3) 1.2528(3) 0.5558(2) 0.0528(7) Uani 1 1 d . . . H21 H 0.6285 1.2268 0.4946 0.063 Uiso 1 1 calc R . . C22 C 0.6351(3) 1.2114(3) 0.6680(2) 0.0455(6) Uani 1 1 d . . . H22 H 0.7329 1.1571 0.6805 0.055 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Co1 0.02825(17) 0.01671(16) 0.03596(18) -0.01436(12) 0.00703(11) -0.00792(11) O1 0.0374(8) 0.0226(7) 0.0586(10) -0.0241(7) 0.0110(7) -0.0096(6) O2 0.0359(8) 0.0276(8) 0.0649(11) -0.0271(8) 0.0186(7) -0.0160(6) O3 0.0313(8) 0.0318(9) 0.0644(11) -0.0280(8) 0.0161(7) -0.0106(6) O4 0.0416(8) 0.0190(7) 0.0482(9) -0.0188(6) 0.0136(7) -0.0110(6) N1 0.0362(10) 0.0250(9) 0.0377(10) -0.0133(8) 0.0049(7) -0.0107(7) N2 0.0425(10) 0.0309(10) 0.0403(10) -0.0152(8) 0.0000(8) -0.0107(8) C1 0.0282(10) 0.0166(9) 0.0261(9) -0.0084(7) -0.0008(7) -0.0060(7) C2 0.0241(9) 0.0195(9) 0.0269(9) -0.0097(7) 0.0029(7) -0.0067(7) C3 0.0270(9) 0.0165(9) 0.0251(9) -0.0092(7) -0.0007(7) -0.0042(7) C4 0.0298(10) 0.0198(9) 0.0332(10) -0.0120(8) 0.0021(8) -0.0101(8) C5 0.0275(10) 0.0250(10) 0.0342(11) -0.0135(9) 0.0042(8) -0.0078(8) C6 0.0284(10) 0.0206(9) 0.0333(10) -0.0145(8) 0.0037(8) -0.0038(8) C7 0.0292(10) 0.0188(9) 0.0309(10) -0.0110(8) 0.0021(8) -0.0071(8) C8 0.0260(9) 0.0189(9) 0.0263(9) -0.0108(7) -0.0005(7) -0.0043(7) C9 0.0369(12) 0.0379(13) 0.0666(16) -0.0287(12) 0.0191(11) -0.0159(10) C10 0.0409(12) 0.0308(12) 0.0429(13) -0.0170(10) 0.0028(10) -0.0056(9) C11 0.0485(14) 0.0423(13) 0.0384(12) -0.0189(11) 0.0065(10) -0.0110(11) C12 0.0453(13) 0.0411(13) 0.0422(13) -0.0121(11) -0.0025(10) -0.0157(10) C13 0.0354(12) 0.0441(14) 0.0509(14) -0.0147(11) -0.0016(10) -0.0056(10) C14 0.0338(11) 0.0385(13) 0.0435(13) -0.0161(10) 0.0068(9) -0.0105(9) C15 0.0586(17) 0.074(2) 0.0457(15) -0.0147(14) -0.0105(13) -0.0138(15) C16 0.083(2) 0.075(2) 0.0455(16) -0.0145(15) -0.0122(15) -0.0135(18) C17 0.101(3) 0.0548(18) 0.0455(16) -0.0005(13) -0.0220(16) -0.0265(17) C18 0.0558(15) 0.0339(13) 0.0514(15) -0.0201(11) -0.0049(12) 0.0014(11) C19 0.0598(17) 0.0378(14) 0.0614(17) -0.0163(13) -0.0164(13) 0.0014(12) C20 0.0699(18) 0.0396(14) 0.0437(14) -0.0073(11) -0.0071(12) -0.0234(13) C21 0.0630(17) 0.0615(17) 0.0394(13) -0.0199(12) 0.0096(12) -0.0252(14) C22 0.0419(13) 0.0499(15) 0.0465(14) -0.0177(12) 0.0066(11) -0.0149(11) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Co1 O4 2.0373(14) 1_565 ? Co1 O3 2.0400(15) 2_667 ? Co1 O2 2.1374(15) . ? Co1 N1 2.1571(19) . ? Co1 N2 2.175(2) 2_677 ? Co1 O1 2.2247(15) . ? Co1 C7 2.5116(19) . ? O1 C7 1.256(2) . ? O2 C7 1.257(3) . ? O3 C8 1.244(2) . ? O3 Co1 2.0400(15) 2_667 ? O4 C8 1.261(2) . ? O4 Co1 2.0374(14) 1_545 ? N1 C10 1.341(3) . ? N1 C14 1.349(3) . ? N2 C18 1.339(3) . ? N2 C22 1.348(3) . ? N2 Co1 2.175(2) 2_677 ? C1 C6 1.391(3) . ? C1 C2 1.399(3) . ? C1 C7 1.510(3) . ? C2 C3 1.400(3) . ? C2 H2 0.9300 . ? C3 C4 1.399(3) . ? C3 C8 1.509(3) . ? C4 C5 1.392(3) . ? C4 H4 0.9300 . ? C5 C6 1.401(3) . ? C5 C9 1.511(3) . ? C6 H6 0.9300 . ? C9 H9A 0.9600 . ? C9 H9B 0.9600 . ? C9 H9C 0.9600 . ? C10 C11 1.378(3) . ? C10 H10 0.9300 . ? C11 C12 1.394(4) . ? C11 H11 0.9300 . ? C12 C13 1.388(4) . ? C12 C15 1.519(4) . ? C13 C14 1.380(4) . ? C13 H13 0.9300 . ? C14 H14 0.9300 . ? C15 C16 1.536(5) . ? C15 H15A 0.9700 . ? C15 H15B 0.9700 . ? C16 C17 1.531(5) . ? C16 H16A 0.9700 . ? C16 H16B 0.9700 . ? C17 C20 1.516(4) . ? C17 H17A 0.9700 . ? C17 H17B 0.9700 . ? C18 C19 1.379(4) . ? C18 H18 0.9300 . ? C19 C20 1.379(4) . ? C19 H19 0.9300 . ? C20 C21 1.396(4) . ? C21 C22 1.379(4) . ? C21 H21 0.9300 . ? C22 H22 0.9300 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O4 Co1 O3 115.54(6) 1_565 2_667 ? O4 Co1 O2 154.98(6) 1_565 . ? O3 Co1 O2 89.47(6) 2_667 . ? O4 Co1 N1 89.37(7) 1_565 . ? O3 Co1 N1 91.10(7) 2_667 . ? O2 Co1 N1 90.97(7) . . ? O4 Co1 N2 87.04(7) 1_565 2_677 ? O3 Co1 N2 87.19(7) 2_667 2_677 ? O2 Co1 N2 93.82(7) . 2_677 ? N1 Co1 N2 174.89(6) . 2_677 ? O4 Co1 O1 95.02(6) 1_565 . ? O3 Co1 O1 149.02(6) 2_667 . ? O2 Co1 O1 60.00(6) . . ? N1 Co1 O1 94.34(7) . . ? N2 Co1 O1 89.59(7) 2_677 . ? O4 Co1 C7 125.00(6) 1_565 . ? O3 Co1 C7 119.31(6) 2_667 . ? O2 Co1 C7 30.03(6) . . ? N1 Co1 C7 93.35(7) . . ? N2 Co1 C7 91.68(7) 2_677 . ? O1 Co1 C7 29.98(6) . . ? C7 O1 Co1 87.76(12) . . ? C7 O2 Co1 91.69(12) . . ? C8 O3 Co1 166.17(16) . 2_667 ? C8 O4 Co1 123.01(13) . 1_545 ? C10 N1 C14 116.51(19) . . ? C10 N1 Co1 120.25(15) . . ? C14 N1 Co1 123.13(15) . . ? C18 N2 C22 116.6(2) . . ? C18 N2 Co1 120.29(17) . 2_677 ? C22 N2 Co1 122.68(17) . 2_677 ? C6 C1 C2 120.24(17) . . ? C6 C1 C7 119.79(17) . . ? C2 C1 C7 119.97(17) . . ? C3 C2 C1 119.35(17) . . ? C3 C2 H2 120.3 . . ? C1 C2 H2 120.3 . . ? C2 C3 C4 119.63(17) . . ? C2 C3 C8 120.85(17) . . ? C4 C3 C8 119.52(16) . . ? C5 C4 C3 121.47(18) . . ? C5 C4 H4 119.3 . . ? C3 C4 H4 119.3 . . ? C4 C5 C6 118.25(18) . . ? C4 C5 C9 120.22(18) . . ? C6 C5 C9 121.53(19) . . ? C1 C6 C5 121.06(18) . . ? C1 C6 H6 119.5 . . ? C5 C6 H6 119.5 . . ? O1 C7 O2 120.53(18) . . ? O1 C7 C1 120.41(18) . . ? O2 C7 C1 119.05(17) . . ? O1 C7 Co1 62.26(10) . . ? O2 C7 Co1 58.28(10) . . ? C1 C7 Co1 176.90(14) . . ? O3 C8 O4 124.28(18) . . ? O3 C8 C3 118.71(17) . . ? O4 C8 C3 117.00(17) . . ? C5 C9 H9A 109.5 . . ? C5 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? C5 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? N1 C10 C11 123.4(2) . . ? N1 C10 H10 118.3 . . ? C11 C10 H10 118.3 . . ? C10 C11 C12 120.3(2) . . ? C10 C11 H11 119.9 . . ? C12 C11 H11 119.9 . . ? C13 C12 C11 116.2(2) . . ? C13 C12 C15 121.6(2) . . ? C11 C12 C15 122.2(2) . . ? C14 C13 C12 120.4(2) . . ? C14 C13 H13 119.8 . . ? C12 C13 H13 119.8 . . ? N1 C14 C13 123.2(2) . . ? N1 C14 H14 118.4 . . ? C13 C14 H14 118.4 . . ? C12 C15 C16 115.9(2) . . ? C12 C15 H15A 108.3 . . ? C16 C15 H15A 108.3 . . ? C12 C15 H15B 108.3 . . ? C16 C15 H15B 108.3 . . ? H15A C15 H15B 107.4 . . ? C17 C16 C15 115.0(3) . . ? C17 C16 H16A 108.5 . . ? C15 C16 H16A 108.5 . . ? C17 C16 H16B 108.5 . . ? C15 C16 H16B 108.5 . . ? H16A C16 H16B 107.5 . . ? C20 C17 C16 114.2(2) . . ? C20 C17 H17A 108.7 . . ? C16 C17 H17A 108.7 . . ? C20 C17 H17B 108.7 . . ? C16 C17 H17B 108.7 . . ? H17A C17 H17B 107.6 . . ? N2 C18 C19 123.4(2) . . ? N2 C18 H18 118.3 . . ? C19 C18 H18 118.3 . . ? C18 C19 C20 120.4(3) . . ? C18 C19 H19 119.8 . . ? C20 C19 H19 119.8 . . ? C19 C20 C21 116.4(2) . . ? C19 C20 C17 121.9(3) . . ? C21 C20 C17 121.7(3) . . ? C22 C21 C20 120.2(3) . . ? C22 C21 H21 119.9 . . ? C20 C21 H21 119.9 . . ? N2 C22 C21 123.0(2) . . ? N2 C22 H22 118.5 . . ? C21 C22 H22 118.5 . . ? 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 O4 Co1 O1 C7 178.92(13) 1_565 . . . ? O3 Co1 O1 C7 -10.2(2) 2_667 . . . ? O2 Co1 O1 C7 0.56(12) . . . . ? N1 Co1 O1 C7 89.18(13) . . . . ? N2 Co1 O1 C7 -94.09(13) 2_677 . . . ? O4 Co1 O2 C7 -4.4(2) 1_565 . . . ? O3 Co1 O2 C7 173.90(14) 2_667 . . . ? N1 Co1 O2 C7 -95.01(13) . . . . ? N2 Co1 O2 C7 86.76(14) 2_677 . . . ? O1 Co1 O2 C7 -0.56(12) . . . . ? O4 Co1 N1 C10 147.35(17) 1_565 . . . ? O3 Co1 N1 C10 31.82(17) 2_667 . . . ? O2 Co1 N1 C10 -57.67(17) . . . . ? N2 Co1 N1 C10 102.1(7) 2_677 . . . ? O1 Co1 N1 C10 -117.66(16) . . . . ? C7 Co1 N1 C10 -87.63(17) . . . . ? O4 Co1 N1 C14 -28.82(17) 1_565 . . . ? O3 Co1 N1 C14 -144.36(17) 2_667 . . . ? O2 Co1 N1 C14 126.16(17) . . . . ? N2 Co1 N1 C14 -74.1(8) 2_677 . . . ? O1 Co1 N1 C14 66.17(17) . . . . ? C7 Co1 N1 C14 96.20(17) . . . . ? C6 C1 C2 C3 -0.5(3) . . . . ? C7 C1 C2 C3 178.42(17) . . . . ? C1 C2 C3 C4 -0.2(3) . . . . ? C1 C2 C3 C8 -179.51(16) . . . . ? C2 C3 C4 C5 0.7(3) . . . . ? C8 C3 C4 C5 179.93(18) . . . . ? C3 C4 C5 C6 -0.3(3) . . . . ? C3 C4 C5 C9 179.5(2) . . . . ? C2 C1 C6 C5 0.8(3) . . . . ? C7 C1 C6 C5 -178.07(18) . . . . ? C4 C5 C6 C1 -0.4(3) . . . . ? C9 C5 C6 C1 179.8(2) . . . . ? Co1 O1 C7 O2 -1.0(2) . . . . ? Co1 O1 C7 C1 178.21(17) . . . . ? Co1 O2 C7 O1 1.0(2) . . . . ? Co1 O2 C7 C1 -178.18(16) . . . . ? C6 C1 C7 O1 0.7(3) . . . . ? C2 C1 C7 O1 -178.24(18) . . . . ? C6 C1 C7 O2 179.86(19) . . . . ? C2 C1 C7 O2 0.9(3) . . . . ? C6 C1 C7 Co1 150(3) . . . . ? C2 C1 C7 Co1 -29(3) . . . . ? O4 Co1 C7 O1 -1.31(15) 1_565 . . . ? O3 Co1 C7 O1 173.97(12) 2_667 . . . ? O2 Co1 C7 O1 -179.0(2) . . . . ? N1 Co1 C7 O1 -92.88(13) . . . . ? N2 Co1 C7 O1 86.25(13) 2_677 . . . ? O4 Co1 C7 O2 177.72(12) 1_565 . . . ? O3 Co1 C7 O2 -7.00(16) 2_667 . . . ? N1 Co1 C7 O2 86.15(14) . . . . ? N2 Co1 C7 O2 -94.71(14) 2_677 . . . ? O1 Co1 C7 O2 179.0(2) . . . . ? O4 Co1 C7 C1 -151(3) 1_565 . . . ? O3 Co1 C7 C1 24(3) 2_667 . . . ? O2 Co1 C7 C1 31(3) . . . . ? N1 Co1 C7 C1 117(3) . . . . ? N2 Co1 C7 C1 -64(3) 2_677 . . . ? O1 Co1 C7 C1 -150(3) . . . . ? Co1 O3 C8 O4 -73.8(6) 2_667 . . . ? Co1 O3 C8 C3 107.1(6) 2_667 . . . ? Co1 O4 C8 O3 -1.5(3) 1_545 . . . ? Co1 O4 C8 C3 177.65(12) 1_545 . . . ? C2 C3 C8 O3 -8.5(3) . . . . ? C4 C3 C8 O3 172.27(18) . . . . ? C2 C3 C8 O4 172.33(18) . . . . ? C4 C3 C8 O4 -6.9(3) . . . . ? C14 N1 C10 C11 1.6(3) . . . . ? Co1 N1 C10 C11 -174.81(18) . . . . ? N1 C10 C11 C12 0.0(4) . . . . ? C10 C11 C12 C13 -1.6(4) . . . . ? C10 C11 C12 C15 178.7(2) . . . . ? C11 C12 C13 C14 1.6(4) . . . . ? C15 C12 C13 C14 -178.7(2) . . . . ? C10 N1 C14 C13 -1.6(3) . . . . ? Co1 N1 C14 C13 174.71(18) . . . . ? C12 C13 C14 N1 0.0(4) . . . . ? C13 C12 C15 C16 141.2(3) . . . . ? C11 C12 C15 C16 -39.1(4) . . . . ? C12 C15 C16 C17 -76.0(4) . . . . ? C15 C16 C17 C20 66.8(4) . . . . ? C22 N2 C18 C19 2.4(4) . . . . ? Co1 N2 C18 C19 -170.5(2) 2_677 . . . ? N2 C18 C19 C20 0.3(4) . . . . ? C18 C19 C20 C21 -3.0(4) . . . . ? C18 C19 C20 C17 173.5(3) . . . . ? C16 C17 C20 C19 -99.3(4) . . . . ? C16 C17 C20 C21 77.1(4) . . . . ? C19 C20 C21 C22 3.1(4) . . . . ? C17 C20 C21 C22 -173.4(3) . . . . ? C18 N2 C22 C21 -2.3(4) . . . . ? Co1 N2 C22 C21 170.4(2) 2_677 . . . ? C20 C21 C22 N2 -0.4(4) . . . . ? _diffrn_measured_fraction_theta_max 0.970 _diffrn_reflns_theta_full 25.50 _diffrn_measured_fraction_theta_full 0.970 _refine_diff_density_max 1.025 _refine_diff_density_min -0.470 _refine_diff_density_rms 0.071 # Attachment '- 3.cif' data_b _database_code_depnum_ccdc_archive 'CCDC 800357' #TrackingRef '- 3.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C21 H18 N2 Ni O4' _chemical_formula_weight 421.08 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 Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 9.7609(10) _cell_length_b 10.1202(11) _cell_length_c 10.9656(12) _cell_angle_alpha 76.4430(10) _cell_angle_beta 81.0920(10) _cell_angle_gamma 68.7420(10) _cell_volume 978.45(18) _cell_formula_units_Z 2 _cell_measurement_temperature 291(2) _cell_measurement_reflns_used 4807 _cell_measurement_theta_min 2.62 _cell_measurement_theta_max 28.22 _exptl_crystal_description block _exptl_crystal_colour green _exptl_crystal_size_max 0.41 _exptl_crystal_size_mid 0.33 _exptl_crystal_size_min 0.23 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.429 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 436 _exptl_absorpt_coefficient_mu 1.020 _exptl_absorpt_correction_type MULTI-SCAN _exptl_absorpt_correction_T_min 0.6774 _exptl_absorpt_correction_T_max 0.7955 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 291(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 7316 _diffrn_reflns_av_R_equivalents 0.0141 _diffrn_reflns_av_sigmaI/netI 0.0209 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 2.56 _diffrn_reflns_theta_max 25.50 _reflns_number_total 3616 _reflns_number_gt 3318 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0368P)^2^+0.5229P] 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 3616 _refine_ls_number_parameters 254 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0305 _refine_ls_R_factor_gt 0.0270 _refine_ls_wR_factor_ref 0.0718 _refine_ls_wR_factor_gt 0.0695 _refine_ls_goodness_of_fit_ref 1.025 _refine_ls_restrained_S_all 1.025 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Ni1 Ni 0.54524(2) 0.63951(2) 0.62026(2) 0.02253(9) Uani 1 1 d . . . O1 O 0.65441(15) 0.68740(13) 0.75577(12) 0.0319(3) Uani 1 1 d . . . O2 O 0.49915(15) 0.85775(13) 0.62816(12) 0.0280(3) Uani 1 1 d . . . O3 O 0.59395(15) 1.33245(14) 0.51201(12) 0.0304(3) Uani 1 1 d . . . O4 O 0.62117(14) 1.42073(13) 0.67166(12) 0.0278(3) Uani 1 1 d . . . N1 N 0.72023(18) 0.64776(17) 0.48159(14) 0.0304(4) Uani 1 1 d . . . N2 N 1.36855(17) 0.63866(16) -0.24058(14) 0.0277(3) Uani 1 1 d . . . C1 C 0.5897(2) 0.81983(19) 0.71154(16) 0.0253(4) Uani 1 1 d . . . C2 C 0.6204(2) 0.93554(19) 0.75569(17) 0.0265(4) Uani 1 1 d . . . C3 C 0.6610(2) 0.9141(2) 0.87649(18) 0.0307(4) Uani 1 1 d . . . H3 H 0.6749 0.8246 0.9296 0.037 Uiso 1 1 calc R . . C4 C 0.6813(2) 1.0245(2) 0.91987(17) 0.0302(4) Uani 1 1 d . . . C5 C 0.6624(2) 1.15639(19) 0.83701(17) 0.0279(4) Uani 1 1 d . . . H5 H 0.6740 1.2315 0.8647 0.033 Uiso 1 1 calc R . . C6 C 0.6266(2) 1.17880(18) 0.71374(17) 0.0250(4) Uani 1 1 d . . . C7 C 0.6040(2) 1.06759(19) 0.67317(17) 0.0260(4) Uani 1 1 d . . . H7 H 0.5783 1.0815 0.5918 0.031 Uiso 1 1 calc R . . C8 C 0.7219(3) 1.0045(2) 1.0524(2) 0.0448(5) Uani 1 1 d . . . H8A H 0.8261 0.9837 1.0516 0.067 Uiso 1 1 calc R . . H8B H 0.6958 0.9257 1.1052 0.067 Uiso 1 1 calc R . . H8C H 0.6696 1.0913 1.0845 0.067 Uiso 1 1 calc R . . C9 C 0.61060(19) 1.32177(18) 0.62483(16) 0.0233(4) Uani 1 1 d . . . C10 C 0.8023(3) 0.5327(3) 0.4323(2) 0.0558(7) Uani 1 1 d . . . H10 H 0.7832 0.4468 0.4629 0.067 Uiso 1 1 calc R . . C11 C 0.9142(3) 0.5338(3) 0.3382(3) 0.0622(8) Uani 1 1 d . . . H11 H 0.9687 0.4496 0.3083 0.075 Uiso 1 1 calc R . . C12 C 0.9455(2) 0.6591(2) 0.28853(18) 0.0343(4) Uani 1 1 d . . . C13 C 0.8618(3) 0.7774(2) 0.3400(2) 0.0437(5) Uani 1 1 d . . . H13 H 0.8794 0.8642 0.3113 0.052 Uiso 1 1 calc R . . C14 C 0.7515(3) 0.7690(2) 0.4340(2) 0.0424(5) Uani 1 1 d . . . H14 H 0.6963 0.8517 0.4659 0.051 Uiso 1 1 calc R . . C15 C 1.0624(2) 0.6666(3) 0.18178(19) 0.0413(5) Uani 1 1 d . . . H15A H 1.1567 0.5972 0.2077 0.050 Uiso 1 1 calc R . . H15B H 1.0704 0.7622 0.1637 0.050 Uiso 1 1 calc R . . C16 C 1.0284(3) 0.6356(3) 0.0632(2) 0.0491(6) Uani 1 1 d . . . H16A H 1.0178 0.5411 0.0823 0.059 Uiso 1 1 calc R . . H16B H 0.9349 0.7064 0.0367 0.059 Uiso 1 1 calc R . . C17 C 1.1454(2) 0.6392(2) -0.04422(19) 0.0367(5) Uani 1 1 d . . . C18 C 1.1201(2) 0.7415(3) -0.1552(2) 0.0427(5) Uani 1 1 d . . . H18 H 1.0279 0.8126 -0.1660 0.051 Uiso 1 1 calc R . . C19 C 1.2334(2) 0.7371(2) -0.24984(19) 0.0375(5) Uani 1 1 d . . . H19 H 1.2141 0.8063 -0.3235 0.045 Uiso 1 1 calc R . . C20 C 1.3922(2) 0.5403(2) -0.13351(19) 0.0384(5) Uani 1 1 d . . . H20 H 1.4854 0.4706 -0.1249 0.046 Uiso 1 1 calc R . . C21 C 1.2855(3) 0.5367(2) -0.0350(2) 0.0432(5) Uani 1 1 d . . . H21 H 1.3076 0.4656 0.0372 0.052 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Ni1 0.03333(15) 0.01799(13) 0.01978(13) -0.00576(9) 0.00414(9) -0.01400(10) O1 0.0481(8) 0.0179(7) 0.0321(7) -0.0033(5) -0.0040(6) -0.0146(6) O2 0.0419(8) 0.0218(6) 0.0249(7) -0.0048(5) -0.0014(6) -0.0165(6) O3 0.0457(8) 0.0278(7) 0.0228(7) -0.0037(5) -0.0028(6) -0.0191(6) O4 0.0419(8) 0.0187(6) 0.0269(7) -0.0064(5) 0.0005(5) -0.0153(6) N1 0.0377(9) 0.0305(9) 0.0259(8) -0.0081(7) 0.0069(7) -0.0173(7) N2 0.0371(9) 0.0260(8) 0.0226(8) -0.0061(6) 0.0043(6) -0.0154(7) C1 0.0375(10) 0.0209(9) 0.0210(9) -0.0049(7) 0.0038(7) -0.0158(8) C2 0.0356(10) 0.0201(9) 0.0276(9) -0.0063(7) -0.0010(8) -0.0134(8) C3 0.0444(11) 0.0207(9) 0.0282(10) -0.0004(7) -0.0048(8) -0.0143(8) C4 0.0401(11) 0.0280(10) 0.0257(10) -0.0042(8) -0.0055(8) -0.0147(8) C5 0.0372(10) 0.0228(9) 0.0296(10) -0.0085(7) -0.0026(8) -0.0149(8) C6 0.0322(10) 0.0197(9) 0.0260(9) -0.0050(7) -0.0005(7) -0.0127(7) C7 0.0380(10) 0.0216(9) 0.0218(9) -0.0054(7) -0.0015(7) -0.0138(8) C8 0.0676(16) 0.0412(12) 0.0323(11) -0.0018(9) -0.0159(11) -0.0247(11) C9 0.0274(9) 0.0194(8) 0.0254(9) -0.0059(7) 0.0021(7) -0.0114(7) C10 0.0779(18) 0.0419(13) 0.0560(15) -0.0249(11) 0.0376(13) -0.0379(13) C11 0.0808(19) 0.0471(15) 0.0621(17) -0.0308(13) 0.0404(14) -0.0319(14) C12 0.0338(11) 0.0476(12) 0.0263(10) -0.0095(9) 0.0041(8) -0.0205(9) C13 0.0565(14) 0.0405(12) 0.0399(12) -0.0085(10) 0.0138(10) -0.0299(11) C14 0.0541(14) 0.0320(11) 0.0411(12) -0.0124(9) 0.0177(10) -0.0197(10) C15 0.0379(12) 0.0600(15) 0.0336(11) -0.0152(10) 0.0094(9) -0.0266(11) C16 0.0436(13) 0.0800(18) 0.0360(12) -0.0226(12) 0.0139(10) -0.0351(13) C17 0.0392(11) 0.0521(13) 0.0274(10) -0.0150(9) 0.0073(8) -0.0251(10) C18 0.0348(11) 0.0525(14) 0.0368(12) -0.0130(10) 0.0025(9) -0.0097(10) C19 0.0411(12) 0.0385(12) 0.0281(10) -0.0036(9) 0.0017(9) -0.0113(9) C20 0.0406(12) 0.0344(11) 0.0300(11) -0.0023(8) 0.0061(9) -0.0067(9) C21 0.0542(14) 0.0413(12) 0.0272(11) -0.0006(9) 0.0101(9) -0.0172(11) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Ni1 O4 2.0307(12) 1_545 ? Ni1 O3 2.0414(13) 2_676 ? Ni1 O2 2.1083(12) . ? Ni1 N1 2.1157(15) . ? Ni1 N2 2.1197(15) 1_456 ? Ni1 O1 2.1865(13) . ? Ni1 C1 2.4670(17) . ? O1 C1 1.267(2) . ? O2 C1 1.267(2) . ? O3 C9 1.247(2) . ? O3 Ni1 2.0415(13) 2_676 ? O4 C9 1.269(2) . ? O4 Ni1 2.0307(12) 1_565 ? N1 C10 1.332(3) . ? N1 C14 1.339(3) . ? N2 C19 1.336(3) . ? N2 C20 1.339(3) . ? N2 Ni1 2.1196(15) 1_654 ? C1 C2 1.503(2) . ? C2 C3 1.387(3) . ? C2 C7 1.398(2) . ? C3 C4 1.398(3) . ? C3 H3 0.9300 . ? C4 C5 1.395(3) . ? C4 C8 1.514(3) . ? C5 C6 1.395(3) . ? C5 H5 0.9300 . ? C6 C7 1.399(2) . ? C6 C9 1.513(2) . ? C7 H7 0.9300 . ? C8 H8A 0.9600 . ? C8 H8B 0.9600 . ? C8 H8C 0.9600 . ? C10 C11 1.383(3) . ? C10 H10 0.9300 . ? C11 C12 1.379(3) . ? C11 H11 0.9300 . ? C12 C13 1.373(3) . ? C12 C15 1.512(3) . ? C13 C14 1.382(3) . ? C13 H13 0.9300 . ? C14 H14 0.9300 . ? C15 C16 1.516(3) . ? C15 H15A 0.9700 . ? C15 H15B 0.9700 . ? C16 C17 1.512(3) . ? C16 H16A 0.9700 . ? C16 H16B 0.9700 . ? C17 C21 1.386(3) . ? C17 C18 1.390(3) . ? C18 C19 1.390(3) . ? C18 H18 0.9300 . ? C19 H19 0.9300 . ? C20 C21 1.383(3) . ? C20 H20 0.9300 . ? C21 H21 0.9300 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O4 Ni1 O3 100.86(5) 1_545 2_676 ? O4 Ni1 O2 159.21(5) 1_545 . ? O3 Ni1 O2 99.15(5) 2_676 . ? O4 Ni1 N1 94.67(6) 1_545 . ? O3 Ni1 N1 91.99(6) 2_676 . ? O2 Ni1 N1 90.24(6) . . ? O4 Ni1 N2 87.14(6) 1_545 1_456 ? O3 Ni1 N2 88.35(6) 2_676 1_456 ? O2 Ni1 N2 87.82(5) . 1_456 ? N1 Ni1 N2 178.06(6) . 1_456 ? O4 Ni1 O1 97.96(5) 1_545 . ? O3 Ni1 O1 160.68(5) 2_676 . ? O2 Ni1 O1 61.72(5) . . ? N1 Ni1 O1 90.84(6) . . ? N2 Ni1 O1 88.21(6) 1_456 . ? O4 Ni1 C1 128.79(6) 1_545 . ? O3 Ni1 C1 130.04(6) 2_676 . ? O2 Ni1 C1 30.89(6) . . ? N1 Ni1 C1 89.49(6) . . ? N2 Ni1 C1 88.83(6) 1_456 . ? O1 Ni1 C1 30.87(5) . . ? C1 O1 Ni1 86.88(11) . . ? C1 O2 Ni1 90.39(10) . . ? C9 O3 Ni1 147.76(13) . 2_676 ? C9 O4 Ni1 132.22(12) . 1_565 ? C10 N1 C14 115.85(18) . . ? C10 N1 Ni1 121.42(13) . . ? C14 N1 Ni1 122.66(13) . . ? C19 N2 C20 116.62(17) . . ? C19 N2 Ni1 123.55(13) . 1_654 ? C20 N2 Ni1 119.73(13) . 1_654 ? O2 C1 O1 120.86(16) . . ? O2 C1 C2 118.47(16) . . ? O1 C1 C2 120.67(17) . . ? O2 C1 Ni1 58.72(9) . . ? O1 C1 Ni1 62.25(9) . . ? C2 C1 Ni1 175.00(13) . . ? C3 C2 C7 120.18(16) . . ? C3 C2 C1 121.21(16) . . ? C7 C2 C1 118.59(16) . . ? C2 C3 C4 121.18(17) . . ? C2 C3 H3 119.4 . . ? C4 C3 H3 119.4 . . ? C5 C4 C3 117.93(17) . . ? C5 C4 C8 120.08(17) . . ? C3 C4 C8 122.00(17) . . ? C4 C5 C6 121.88(16) . . ? C4 C5 H5 119.1 . . ? C6 C5 H5 119.1 . . ? C5 C6 C7 119.15(16) . . ? C5 C6 C9 120.74(15) . . ? C7 C6 C9 120.10(16) . . ? C2 C7 C6 119.62(17) . . ? C2 C7 H7 120.2 . . ? C6 C7 H7 120.2 . . ? C4 C8 H8A 109.5 . . ? C4 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? C4 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? O3 C9 O4 125.06(16) . . ? O3 C9 C6 118.70(15) . . ? O4 C9 C6 116.18(15) . . ? N1 C10 C11 123.7(2) . . ? N1 C10 H10 118.1 . . ? C11 C10 H10 118.1 . . ? C12 C11 C10 120.4(2) . . ? C12 C11 H11 119.8 . . ? C10 C11 H11 119.8 . . ? C13 C12 C11 115.92(19) . . ? C13 C12 C15 122.00(19) . . ? C11 C12 C15 122.1(2) . . ? C12 C13 C14 120.8(2) . . ? C12 C13 H13 119.6 . . ? C14 C13 H13 119.6 . . ? N1 C14 C13 123.3(2) . . ? N1 C14 H14 118.4 . . ? C13 C14 H14 118.4 . . ? C12 C15 C16 112.42(18) . . ? C12 C15 H15A 109.1 . . ? C16 C15 H15A 109.1 . . ? C12 C15 H15B 109.1 . . ? C16 C15 H15B 109.1 . . ? H15A C15 H15B 107.9 . . ? C17 C16 C15 113.50(18) . . ? C17 C16 H16A 108.9 . . ? C15 C16 H16A 108.9 . . ? C17 C16 H16B 108.9 . . ? C15 C16 H16B 108.9 . . ? H16A C16 H16B 107.7 . . ? C21 C17 C18 116.88(18) . . ? C21 C17 C16 120.0(2) . . ? C18 C17 C16 123.1(2) . . ? C17 C18 C19 119.6(2) . . ? C17 C18 H18 120.2 . . ? C19 C18 H18 120.2 . . ? N2 C19 C18 123.47(19) . . ? N2 C19 H19 118.3 . . ? C18 C19 H19 118.3 . . ? N2 C20 C21 123.6(2) . . ? N2 C20 H20 118.2 . . ? C21 C20 H20 118.2 . . ? C20 C21 C17 119.8(2) . . ? C20 C21 H21 120.1 . . ? C17 C21 H21 120.1 . . ? 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 O4 Ni1 O1 C1 -177.57(10) 1_545 . . . ? O3 Ni1 O1 C1 -10.9(2) 2_676 . . . ? O2 Ni1 O1 C1 -2.23(10) . . . . ? N1 Ni1 O1 C1 87.59(11) . . . . ? N2 Ni1 O1 C1 -90.71(11) 1_456 . . . ? O4 Ni1 O2 C1 15.31(19) 1_545 . . . ? O3 Ni1 O2 C1 179.34(10) 2_676 . . . ? N1 Ni1 O2 C1 -88.61(11) . . . . ? N2 Ni1 O2 C1 91.37(11) 1_456 . . . ? O1 Ni1 O2 C1 2.22(10) . . . . ? O4 Ni1 N1 C10 20.1(2) 1_545 . . . ? O3 Ni1 N1 C10 -81.0(2) 2_676 . . . ? O2 Ni1 N1 C10 179.88(19) . . . . ? N2 Ni1 N1 C10 179(100) 1_456 . . . ? O1 Ni1 N1 C10 118.16(19) . . . . ? C1 Ni1 N1 C10 149.0(2) . . . . ? O4 Ni1 N1 C14 -162.87(17) 1_545 . . . ? O3 Ni1 N1 C14 96.07(17) 2_676 . . . ? O2 Ni1 N1 C14 -3.09(17) . . . . ? N2 Ni1 N1 C14 -3.9(19) 1_456 . . . ? O1 Ni1 N1 C14 -64.82(17) . . . . ? C1 Ni1 N1 C14 -33.98(18) . . . . ? Ni1 O2 C1 O1 -3.94(17) . . . . ? Ni1 O2 C1 C2 175.24(14) . . . . ? Ni1 O1 C1 O2 3.80(17) . . . . ? Ni1 O1 C1 C2 -175.36(15) . . . . ? O4 Ni1 C1 O2 -173.10(9) 1_545 . . . ? O3 Ni1 C1 O2 -0.85(13) 2_676 . . . ? N1 Ni1 C1 O2 91.32(11) . . . . ? N2 Ni1 C1 O2 -87.71(10) 1_456 . . . ? O1 Ni1 C1 O2 -176.18(17) . . . . ? O4 Ni1 C1 O1 3.08(13) 1_545 . . . ? O3 Ni1 C1 O1 175.33(9) 2_676 . . . ? O2 Ni1 C1 O1 176.18(17) . . . . ? N1 Ni1 C1 O1 -92.50(11) . . . . ? N2 Ni1 C1 O1 88.47(11) 1_456 . . . ? O4 Ni1 C1 C2 130.0(16) 1_545 . . . ? O3 Ni1 C1 C2 -57.7(16) 2_676 . . . ? O2 Ni1 C1 C2 -56.9(16) . . . . ? N1 Ni1 C1 C2 34.4(16) . . . . ? N2 Ni1 C1 C2 -144.6(16) 1_456 . . . ? O1 Ni1 C1 C2 126.9(16) . . . . ? O2 C1 C2 C3 151.21(18) . . . . ? O1 C1 C2 C3 -29.6(3) . . . . ? Ni1 C1 C2 C3 -154.3(15) . . . . ? O2 C1 C2 C7 -27.4(3) . . . . ? O1 C1 C2 C7 151.80(18) . . . . ? Ni1 C1 C2 C7 27.1(17) . . . . ? C7 C2 C3 C4 2.2(3) . . . . ? C1 C2 C3 C4 -176.31(18) . . . . ? C2 C3 C4 C5 -1.3(3) . . . . ? C2 C3 C4 C8 178.5(2) . . . . ? C3 C4 C5 C6 -1.0(3) . . . . ? C8 C4 C5 C6 179.30(19) . . . . ? C4 C5 C6 C7 2.2(3) . . . . ? C4 C5 C6 C9 -178.39(17) . . . . ? C3 C2 C7 C6 -1.0(3) . . . . ? C1 C2 C7 C6 177.61(17) . . . . ? C5 C6 C7 C2 -1.2(3) . . . . ? C9 C6 C7 C2 179.40(16) . . . . ? Ni1 O3 C9 O4 -103.4(2) 2_676 . . . ? Ni1 O3 C9 C6 79.5(3) 2_676 . . . ? Ni1 O4 C9 O3 26.4(3) 1_565 . . . ? Ni1 O4 C9 C6 -156.41(12) 1_565 . . . ? C5 C6 C9 O3 172.51(17) . . . . ? C7 C6 C9 O3 -8.1(3) . . . . ? C5 C6 C9 O4 -4.8(3) . . . . ? C7 C6 C9 O4 174.55(17) . . . . ? C14 N1 C10 C11 0.3(4) . . . . ? Ni1 N1 C10 C11 177.5(2) . . . . ? N1 C10 C11 C12 -0.9(5) . . . . ? C10 C11 C12 C13 1.3(4) . . . . ? C10 C11 C12 C15 -177.3(2) . . . . ? C11 C12 C13 C14 -1.3(4) . . . . ? C15 C12 C13 C14 177.3(2) . . . . ? C10 N1 C14 C13 -0.2(4) . . . . ? Ni1 N1 C14 C13 -177.41(18) . . . . ? C12 C13 C14 N1 0.8(4) . . . . ? C13 C12 C15 C16 -117.0(3) . . . . ? C11 C12 C15 C16 61.6(3) . . . . ? C12 C15 C16 C17 -178.69(19) . . . . ? C15 C16 C17 C21 65.9(3) . . . . ? C15 C16 C17 C18 -114.5(3) . . . . ? C21 C17 C18 C19 -0.1(3) . . . . ? C16 C17 C18 C19 -179.7(2) . . . . ? C20 N2 C19 C18 0.3(3) . . . . ? Ni1 N2 C19 C18 -175.96(16) 1_654 . . . ? C17 C18 C19 N2 -0.3(3) . . . . ? C19 N2 C20 C21 -0.1(3) . . . . ? Ni1 N2 C20 C21 176.39(17) 1_654 . . . ? N2 C20 C21 C17 -0.3(4) . . . . ? C18 C17 C21 C20 0.4(3) . . . . ? C16 C17 C21 C20 180.0(2) . . . . ? _diffrn_measured_fraction_theta_max 0.992 _diffrn_reflns_theta_full 25.50 _diffrn_measured_fraction_theta_full 0.992 _refine_diff_density_max 0.291 _refine_diff_density_min -0.231 _refine_diff_density_rms 0.048 # Attachment '- 4.cif' data_b4 _database_code_depnum_ccdc_archive 'CCDC 800358' #TrackingRef '- 4.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C22 H22 N2 Ni O5' _chemical_formula_weight 453.13 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 10.1421(11) _cell_length_b 10.3265(11) _cell_length_c 11.6938(12) _cell_angle_alpha 70.9700(10) _cell_angle_beta 77.5240(10) _cell_angle_gamma 65.5670(10) _cell_volume 1049.40(19) _cell_formula_units_Z 2 _cell_measurement_temperature 291(2) _cell_measurement_reflns_used 5499 _cell_measurement_theta_min 2.50 _cell_measurement_theta_max 28.21 _exptl_crystal_description block _exptl_crystal_colour green _exptl_crystal_size_max 0.44 _exptl_crystal_size_mid 0.37 _exptl_crystal_size_min 0.28 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.434 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 472 _exptl_absorpt_coefficient_mu 0.960 _exptl_absorpt_correction_type MULTI-SCAN _exptl_absorpt_correction_T_min 0.6751 _exptl_absorpt_correction_T_max 0.7715 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 291(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 7832 _diffrn_reflns_av_R_equivalents 0.0118 _diffrn_reflns_av_sigmaI/netI 0.0175 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 2.50 _diffrn_reflns_theta_max 25.50 _reflns_number_total 3881 _reflns_number_gt 3607 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0294P)^2^+0.4421P] 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 3881 _refine_ls_number_parameters 272 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0271 _refine_ls_R_factor_gt 0.0249 _refine_ls_wR_factor_ref 0.0641 _refine_ls_wR_factor_gt 0.0628 _refine_ls_goodness_of_fit_ref 1.053 _refine_ls_restrained_S_all 1.053 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Ni1 Ni 0.12861(2) 0.64103(2) 1.256436(18) 0.02625(8) Uani 1 1 d . . . O1 O 0.17364(12) 0.84184(12) 1.22053(11) 0.0336(3) Uani 1 1 d . . . O2 O 0.34066(12) 0.61712(12) 1.26279(11) 0.0334(3) Uani 1 1 d . . . O3 O 0.82431(15) 0.56091(16) 1.36140(13) 0.0554(4) Uani 1 1 d . . . O4 O 0.91305(13) 0.73078(15) 1.24333(13) 0.0451(3) Uani 1 1 d . . . O5 O 0.07550(16) 0.64999(15) 1.43941(11) 0.0498(3) Uani 1 1 d . . . H1W H 0.0139 0.6620 1.4463 0.075 Uiso 1 1 d R . . H2W H 0.1058 0.5838 1.5028 0.075 Uiso 1 1 d R . . N1 N 0.16333(15) 0.66848(15) 1.06860(13) 0.0313(3) Uani 1 1 d . . . N2 N 0.18079(15) 1.41396(15) 0.30656(13) 0.0312(3) Uani 1 1 d . . . C1 C 0.30364(17) 0.75662(17) 1.23607(14) 0.0276(3) Uani 1 1 d . . . C2 C 0.41939(16) 0.81778(17) 1.22060(14) 0.0256(3) Uani 1 1 d . . . C3 C 0.55517(17) 0.72559(17) 1.26256(14) 0.0262(3) Uani 1 1 d . . . H3 H 0.5730 0.6270 1.3033 0.031 Uiso 1 1 calc R . . C4 C 0.66397(17) 0.78178(18) 1.24323(14) 0.0266(3) Uani 1 1 d . . . C5 C 0.63489(18) 0.93063(18) 1.18336(15) 0.0302(4) Uani 1 1 d . . . H5A H 0.7083 0.9674 1.1691 0.036 Uiso 1 1 calc R . . C6 C 0.49840(18) 1.02503(17) 1.14462(15) 0.0297(3) Uani 1 1 d . . . C7 C 0.39178(17) 0.96637(17) 1.16282(15) 0.0286(3) Uani 1 1 d . . . H7 H 0.3006 1.0274 1.1359 0.034 Uiso 1 1 calc R . . C8 C 0.81209(17) 0.68159(19) 1.28704(15) 0.0311(4) Uani 1 1 d . . . C9 C 0.4657(2) 1.18740(19) 1.08637(18) 0.0430(4) Uani 1 1 d . . . H9A H 0.4307 1.2395 1.1482 0.065 Uiso 1 1 calc R . . H9B H 0.3929 1.2248 1.0310 0.065 Uiso 1 1 calc R . . H9C H 0.5527 1.2013 1.0429 0.065 Uiso 1 1 calc R . . C10 C 0.07661(19) 0.79094(19) 0.99475(16) 0.0373(4) Uani 1 1 d . . . H10 H -0.0044 0.8553 1.0298 0.045 Uiso 1 1 calc R . . C11 C 0.1020(2) 0.8256(2) 0.86964(16) 0.0390(4) Uani 1 1 d . . . H11 H 0.0402 0.9129 0.8227 0.047 Uiso 1 1 calc R . . C12 C 0.22016(19) 0.73003(18) 0.81349(16) 0.0332(4) Uani 1 1 d . . . C13 C 0.3096(2) 0.60297(19) 0.89021(17) 0.0390(4) Uani 1 1 d . . . H13 H 0.3900 0.5354 0.8577 0.047 Uiso 1 1 calc R . . C14 C 0.2783(2) 0.57799(19) 1.01460(17) 0.0375(4) Uani 1 1 d . . . H14 H 0.3406 0.4935 1.0638 0.045 Uiso 1 1 calc R . . C15 C 0.2531(2) 0.7614(2) 0.67704(16) 0.0399(4) Uani 1 1 d . . . H15A H 0.1965 0.7266 0.6457 0.048 Uiso 1 1 calc R . . H15B H 0.3551 0.7055 0.6585 0.048 Uiso 1 1 calc R . . C16 C 0.2212(3) 0.9235(2) 0.61122(17) 0.0475(5) Uani 1 1 d . . . H16A H 0.2732 0.9604 0.6455 0.057 Uiso 1 1 calc R . . H16B H 0.1180 0.9790 0.6249 0.057 Uiso 1 1 calc R . . C17 C 0.2645(2) 0.95008(19) 0.47477(16) 0.0403(4) Uani 1 1 d . . . H17A H 0.3666 0.8911 0.4608 0.048 Uiso 1 1 calc R . . H17B H 0.2088 0.9182 0.4395 0.048 Uiso 1 1 calc R . . C18 C 0.2387(2) 1.11085(19) 0.41223(15) 0.0335(4) Uani 1 1 d . . . C19 C 0.3103(2) 1.1834(2) 0.44187(17) 0.0390(4) Uani 1 1 d . . . H19 H 0.3789 1.1316 0.4982 0.047 Uiso 1 1 calc R . . C20 C 0.27973(19) 1.33199(19) 0.38787(17) 0.0359(4) Uani 1 1 d . . . H20 H 0.3299 1.3775 0.4087 0.043 Uiso 1 1 calc R . . C21 C 0.11391(19) 1.34377(19) 0.27571(16) 0.0345(4) Uani 1 1 d . . . H21 H 0.0468 1.3976 0.2182 0.041 Uiso 1 1 calc R . . C22 C 0.1400(2) 1.1951(2) 0.32538(16) 0.0359(4) Uani 1 1 d . . . H22 H 0.0913 1.1513 0.3006 0.043 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Ni1 0.02063(11) 0.02677(12) 0.03052(12) -0.00320(8) -0.00425(8) -0.01048(8) O1 0.0199(6) 0.0306(6) 0.0484(7) -0.0079(5) -0.0067(5) -0.0078(5) O2 0.0249(6) 0.0266(6) 0.0488(7) -0.0043(5) -0.0085(5) -0.0117(5) O3 0.0322(7) 0.0569(9) 0.0555(9) 0.0171(7) -0.0136(6) -0.0155(6) O4 0.0218(6) 0.0485(8) 0.0601(9) -0.0022(6) -0.0072(6) -0.0160(6) O5 0.0519(8) 0.0485(8) 0.0321(7) -0.0047(6) -0.0017(6) -0.0081(7) N1 0.0322(8) 0.0278(7) 0.0318(7) -0.0038(6) -0.0058(6) -0.0107(6) N2 0.0285(7) 0.0301(7) 0.0334(7) -0.0051(6) -0.0014(6) -0.0127(6) C1 0.0240(8) 0.0298(8) 0.0296(8) -0.0066(7) -0.0044(6) -0.0107(7) C2 0.0216(8) 0.0276(8) 0.0287(8) -0.0093(7) -0.0016(6) -0.0093(6) C3 0.0238(8) 0.0247(8) 0.0288(8) -0.0056(6) -0.0026(6) -0.0089(6) C4 0.0219(8) 0.0328(8) 0.0256(8) -0.0076(7) -0.0024(6) -0.0107(7) C5 0.0288(8) 0.0351(9) 0.0324(9) -0.0094(7) -0.0003(7) -0.0184(7) C6 0.0326(9) 0.0266(8) 0.0301(8) -0.0082(7) -0.0006(7) -0.0119(7) C7 0.0245(8) 0.0264(8) 0.0313(9) -0.0071(7) -0.0046(7) -0.0054(6) C8 0.0240(8) 0.0400(10) 0.0289(9) -0.0079(7) -0.0041(7) -0.0117(7) C9 0.0489(11) 0.0290(9) 0.0483(11) -0.0056(8) -0.0017(9) -0.0165(8) C10 0.0328(9) 0.0328(9) 0.0364(10) -0.0079(8) -0.0058(7) -0.0025(7) C11 0.0398(10) 0.0331(9) 0.0342(10) -0.0025(8) -0.0114(8) -0.0052(8) C12 0.0394(10) 0.0276(8) 0.0329(9) -0.0049(7) -0.0045(7) -0.0147(7) C13 0.0419(10) 0.0265(9) 0.0403(10) -0.0077(7) -0.0014(8) -0.0069(8) C14 0.0405(10) 0.0242(8) 0.0386(10) -0.0017(7) -0.0080(8) -0.0059(7) C15 0.0506(11) 0.0319(9) 0.0349(10) -0.0082(8) -0.0023(8) -0.0145(8) C16 0.0757(15) 0.0342(10) 0.0326(10) -0.0077(8) 0.0024(9) -0.0252(10) C17 0.0574(12) 0.0311(9) 0.0336(10) -0.0087(8) -0.0013(8) -0.0189(9) C18 0.0399(10) 0.0309(9) 0.0283(8) -0.0086(7) 0.0037(7) -0.0146(7) C19 0.0414(10) 0.0337(9) 0.0394(10) -0.0028(8) -0.0122(8) -0.0126(8) C20 0.0347(9) 0.0328(9) 0.0425(10) -0.0063(8) -0.0083(8) -0.0154(8) C21 0.0336(9) 0.0373(9) 0.0328(9) -0.0073(7) -0.0046(7) -0.0143(8) C22 0.0405(10) 0.0392(10) 0.0350(9) -0.0124(8) -0.0007(8) -0.0211(8) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Ni1 O4 2.0095(12) 1_455 ? Ni1 O2 2.0760(11) . ? Ni1 N2 2.0817(14) 1_546 ? Ni1 N1 2.0908(14) . ? Ni1 O5 2.1134(13) . ? Ni1 O1 2.1949(12) . ? Ni1 C1 2.4531(16) . ? O1 C1 1.2591(19) . ? O2 C1 1.2742(19) . ? O3 C8 1.240(2) . ? O4 C8 1.266(2) . ? O4 Ni1 2.0095(12) 1_655 ? O5 H1W 0.5765 . ? O5 H2W 0.8399 . ? N1 C14 1.341(2) . ? N1 C10 1.347(2) . ? N2 C21 1.341(2) . ? N2 C20 1.346(2) . ? N2 Ni1 2.0816(14) 1_564 ? C1 C2 1.502(2) . ? C2 C7 1.393(2) . ? C2 C3 1.395(2) . ? C3 C4 1.393(2) . ? C3 H3 0.9300 . ? C4 C5 1.397(2) . ? C4 C8 1.514(2) . ? C5 C6 1.392(2) . ? C5 H5A 0.9300 . ? C6 C7 1.393(2) . ? C6 C9 1.509(2) . ? C7 H7 0.9300 . ? C9 H9A 0.9600 . ? C9 H9B 0.9600 . ? C9 H9C 0.9600 . ? C10 C11 1.381(3) . ? C10 H10 0.9300 . ? C11 C12 1.395(3) . ? C11 H11 0.9300 . ? C12 C13 1.396(2) . ? C12 C15 1.512(2) . ? C13 C14 1.381(3) . ? C13 H13 0.9300 . ? C14 H14 0.9300 . ? C15 C16 1.522(2) . ? C15 H15A 0.9700 . ? C15 H15B 0.9700 . ? C16 C17 1.525(2) . ? C16 H16A 0.9700 . ? C16 H16B 0.9700 . ? C17 C18 1.514(2) . ? C17 H17A 0.9700 . ? C17 H17B 0.9700 . ? C18 C22 1.390(3) . ? C18 C19 1.391(3) . ? C19 C20 1.382(2) . ? C19 H19 0.9300 . ? C20 H20 0.9300 . ? C21 C22 1.384(2) . ? C21 H21 0.9300 . ? C22 H22 0.9300 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O4 Ni1 O2 161.93(5) 1_455 . ? O4 Ni1 N2 105.20(5) 1_455 1_546 ? O2 Ni1 N2 92.69(5) . 1_546 ? O4 Ni1 N1 89.24(6) 1_455 . ? O2 Ni1 N1 91.20(5) . . ? N2 Ni1 N1 96.84(5) 1_546 . ? O4 Ni1 O5 86.03(6) 1_455 . ? O2 Ni1 O5 90.91(5) . . ? N2 Ni1 O5 91.91(5) 1_546 . ? N1 Ni1 O5 170.89(5) . . ? O4 Ni1 O1 99.92(5) 1_455 . ? O2 Ni1 O1 62.08(4) . . ? N2 Ni1 O1 154.64(5) 1_546 . ? N1 Ni1 O1 86.83(5) . . ? O5 Ni1 O1 86.33(5) . . ? O4 Ni1 C1 130.71(5) 1_455 . ? O2 Ni1 C1 31.29(5) . . ? N2 Ni1 C1 123.95(5) 1_546 . ? N1 Ni1 C1 88.54(5) . . ? O5 Ni1 C1 88.67(6) . . ? O1 Ni1 C1 30.80(5) . . ? C1 O1 Ni1 86.00(9) . . ? C1 O2 Ni1 90.92(9) . . ? C8 O4 Ni1 132.81(12) . 1_655 ? Ni1 O5 H1W 102.3 . . ? Ni1 O5 H2W 129.2 . . ? H1W O5 H2W 102.8 . . ? C14 N1 C10 116.54(15) . . ? C14 N1 Ni1 123.40(11) . . ? C10 N1 Ni1 119.64(12) . . ? C21 N2 C20 116.88(15) . . ? C21 N2 Ni1 125.94(12) . 1_564 ? C20 N2 Ni1 116.76(11) . 1_564 ? O1 C1 O2 120.99(14) . . ? O1 C1 C2 120.51(14) . . ? O2 C1 C2 118.49(14) . . ? O1 C1 Ni1 63.20(8) . . ? O2 C1 Ni1 57.80(8) . . ? C2 C1 Ni1 175.74(12) . . ? C7 C2 C3 119.92(14) . . ? C7 C2 C1 119.95(14) . . ? C3 C2 C1 120.13(14) . . ? C4 C3 C2 119.76(14) . . ? C4 C3 H3 120.1 . . ? C2 C3 H3 120.1 . . ? C3 C4 C5 119.45(14) . . ? C3 C4 C8 119.92(14) . . ? C5 C4 C8 120.63(14) . . ? C6 C5 C4 121.40(15) . . ? C6 C5 H5A 119.3 . . ? C4 C5 H5A 119.3 . . ? C5 C6 C7 118.32(15) . . ? C5 C6 C9 120.94(15) . . ? C7 C6 C9 120.73(15) . . ? C2 C7 C6 121.09(15) . . ? C2 C7 H7 119.5 . . ? C6 C7 H7 119.5 . . ? O3 C8 O4 125.99(16) . . ? O3 C8 C4 118.24(15) . . ? O4 C8 C4 115.77(15) . . ? C6 C9 H9A 109.5 . . ? C6 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? C6 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? N1 C10 C11 123.25(16) . . ? N1 C10 H10 118.4 . . ? C11 C10 H10 118.4 . . ? C10 C11 C12 120.14(16) . . ? C10 C11 H11 119.9 . . ? C12 C11 H11 119.9 . . ? C11 C12 C13 116.48(16) . . ? C11 C12 C15 122.60(16) . . ? C13 C12 C15 120.91(16) . . ? C14 C13 C12 119.75(17) . . ? C14 C13 H13 120.1 . . ? C12 C13 H13 120.1 . . ? N1 C14 C13 123.81(16) . . ? N1 C14 H14 118.1 . . ? C13 C14 H14 118.1 . . ? C12 C15 C16 114.51(15) . . ? C12 C15 H15A 108.6 . . ? C16 C15 H15A 108.6 . . ? C12 C15 H15B 108.6 . . ? C16 C15 H15B 108.6 . . ? H15A C15 H15B 107.6 . . ? C15 C16 C17 113.10(15) . . ? C15 C16 H16A 109.0 . . ? C17 C16 H16A 109.0 . . ? C15 C16 H16B 109.0 . . ? C17 C16 H16B 109.0 . . ? H16A C16 H16B 107.8 . . ? C18 C17 C16 112.16(15) . . ? C18 C17 H17A 109.2 . . ? C16 C17 H17A 109.2 . . ? C18 C17 H17B 109.2 . . ? C16 C17 H17B 109.2 . . ? H17A C17 H17B 107.9 . . ? C22 C18 C19 116.40(16) . . ? C22 C18 C17 122.33(16) . . ? C19 C18 C17 121.24(16) . . ? C20 C19 C18 120.22(17) . . ? C20 C19 H19 119.9 . . ? C18 C19 H19 119.9 . . ? N2 C20 C19 123.07(16) . . ? N2 C20 H20 118.5 . . ? C19 C20 H20 118.5 . . ? N2 C21 C22 123.09(16) . . ? N2 C21 H21 118.5 . . ? C22 C21 H21 118.5 . . ? C21 C22 C18 120.28(16) . . ? C21 C22 H22 119.9 . . ? C18 C22 H22 119.9 . . ? 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 O4 Ni1 O1 C1 178.87(10) 1_455 . . . ? O2 Ni1 O1 C1 0.58(9) . . . . ? N2 Ni1 O1 C1 6.84(17) 1_546 . . . ? N1 Ni1 O1 C1 -92.46(10) . . . . ? O5 Ni1 O1 C1 93.56(10) . . . . ? O4 Ni1 O2 C1 -6.0(2) 1_455 . . . ? N2 Ni1 O2 C1 -177.90(10) 1_546 . . . ? N1 Ni1 O2 C1 85.20(10) . . . . ? O5 Ni1 O2 C1 -85.94(10) . . . . ? O1 Ni1 O2 C1 -0.58(9) . . . . ? O4 Ni1 N1 C14 -149.17(14) 1_455 . . . ? O2 Ni1 N1 C14 48.90(14) . . . . ? N2 Ni1 N1 C14 -43.95(15) 1_546 . . . ? O5 Ni1 N1 C14 152.2(3) . . . . ? O1 Ni1 N1 C14 110.85(14) . . . . ? C1 Ni1 N1 C14 80.08(14) . . . . ? O4 Ni1 N1 C10 38.48(14) 1_455 . . . ? O2 Ni1 N1 C10 -123.45(13) . . . . ? N2 Ni1 N1 C10 143.70(13) 1_546 . . . ? O5 Ni1 N1 C10 -20.1(4) . . . . ? O1 Ni1 N1 C10 -61.50(13) . . . . ? C1 Ni1 N1 C10 -92.27(13) . . . . ? Ni1 O1 C1 O2 -0.98(15) . . . . ? Ni1 O1 C1 C2 177.60(14) . . . . ? Ni1 O2 C1 O1 1.03(16) . . . . ? Ni1 O2 C1 C2 -177.58(13) . . . . ? O4 Ni1 C1 O1 -1.47(13) 1_455 . . . ? O2 Ni1 C1 O1 -179.01(15) . . . . ? N2 Ni1 C1 O1 -176.47(9) 1_546 . . . ? N1 Ni1 C1 O1 86.26(10) . . . . ? O5 Ni1 C1 O1 -85.07(10) . . . . ? O4 Ni1 C1 O2 177.54(9) 1_455 . . . ? N2 Ni1 C1 O2 2.53(12) 1_546 . . . ? N1 Ni1 C1 O2 -94.73(10) . . . . ? O5 Ni1 C1 O2 93.94(10) . . . . ? O1 Ni1 C1 O2 179.01(15) . . . . ? O4 Ni1 C1 C2 -152.5(15) 1_455 . . . ? O2 Ni1 C1 C2 30.0(15) . . . . ? N2 Ni1 C1 C2 32.5(16) 1_546 . . . ? N1 Ni1 C1 C2 -64.7(16) . . . . ? O5 Ni1 C1 C2 123.9(16) . . . . ? O1 Ni1 C1 C2 -151.0(16) . . . . ? O1 C1 C2 C7 -14.6(2) . . . . ? O2 C1 C2 C7 163.99(15) . . . . ? Ni1 C1 C2 C7 135.2(15) . . . . ? O1 C1 C2 C3 166.22(15) . . . . ? O2 C1 C2 C3 -15.2(2) . . . . ? Ni1 C1 C2 C3 -43.9(16) . . . . ? C7 C2 C3 C4 -1.9(2) . . . . ? C1 C2 C3 C4 177.26(14) . . . . ? C2 C3 C4 C5 0.9(2) . . . . ? C2 C3 C4 C8 -179.13(14) . . . . ? C3 C4 C5 C6 1.3(2) . . . . ? C8 C4 C5 C6 -178.69(15) . . . . ? C4 C5 C6 C7 -2.4(2) . . . . ? C4 C5 C6 C9 176.53(16) . . . . ? C3 C2 C7 C6 0.8(2) . . . . ? C1 C2 C7 C6 -178.39(15) . . . . ? C5 C6 C7 C2 1.4(2) . . . . ? C9 C6 C7 C2 -177.56(16) . . . . ? Ni1 O4 C8 O3 6.6(3) 1_655 . . . ? Ni1 O4 C8 C4 -173.60(11) 1_655 . . . ? C3 C4 C8 O3 -15.3(2) . . . . ? C5 C4 C8 O3 164.69(17) . . . . ? C3 C4 C8 O4 164.88(16) . . . . ? C5 C4 C8 O4 -15.1(2) . . . . ? C14 N1 C10 C11 -0.5(3) . . . . ? Ni1 N1 C10 C11 172.40(14) . . . . ? N1 C10 C11 C12 1.7(3) . . . . ? C10 C11 C12 C13 -1.4(3) . . . . ? C10 C11 C12 C15 179.66(17) . . . . ? C11 C12 C13 C14 0.0(3) . . . . ? C15 C12 C13 C14 179.04(17) . . . . ? C10 N1 C14 C13 -1.0(3) . . . . ? Ni1 N1 C14 C13 -173.53(14) . . . . ? C12 C13 C14 N1 1.2(3) . . . . ? C11 C12 C15 C16 36.3(3) . . . . ? C13 C12 C15 C16 -142.61(19) . . . . ? C12 C15 C16 C17 176.41(17) . . . . ? C15 C16 C17 C18 -177.15(17) . . . . ? C16 C17 C18 C22 -116.6(2) . . . . ? C16 C17 C18 C19 61.5(2) . . . . ? C22 C18 C19 C20 1.3(3) . . . . ? C17 C18 C19 C20 -176.83(17) . . . . ? C21 N2 C20 C19 -2.1(3) . . . . ? Ni1 N2 C20 C19 170.88(14) 1_564 . . . ? C18 C19 C20 N2 0.7(3) . . . . ? C20 N2 C21 C22 1.5(3) . . . . ? Ni1 N2 C21 C22 -170.72(13) 1_564 . . . ? N2 C21 C22 C18 0.5(3) . . . . ? C19 C18 C22 C21 -1.9(3) . . . . ? C17 C18 C22 C21 176.28(16) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O5 H2W O3 0.84 1.82 2.6618(18) 178.7 2_668 O5 H1W O4 0.58 2.56 2.8135(19) 110.9 1_455 _diffrn_measured_fraction_theta_max 0.991 _diffrn_reflns_theta_full 25.50 _diffrn_measured_fraction_theta_full 0.991 _refine_diff_density_max 0.306 _refine_diff_density_min -0.245 _refine_diff_density_rms 0.044