# Electronic Supplementary Material (ESI) for Dalton Transactions # This journal is © The Royal Society of Chemistry 2012 data_global _journal_name_full 'Dalton Trans.' _journal_coden_cambridge 0222 _journal_year ? _journal_volume ? _journal_page_first ? _publ_contact_author_name 'Liviu Mirica' _publ_contact_author_email mirica@wustl.edu loop_ _publ_author_name E.Evangelio N.Rath L.Mirica data_l11210 _database_code_depnum_ccdc_archive 'CCDC 864402' #TrackingRef '- Cif_Combined3New.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C34 H32 Cl4 Co2 N10 O4' _chemical_formula_weight 904.36 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' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 9.1697(7) _cell_length_b 14.4120(10) _cell_length_c 13.6075(11) _cell_angle_alpha 90.00 _cell_angle_beta 91.467(3) _cell_angle_gamma 90.00 _cell_volume 1797.7(2) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 9967 _cell_measurement_theta_min 2.63 _cell_measurement_theta_max 27.64 _exptl_crystal_description plate _exptl_crystal_colour purple _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.26 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas no _exptl_crystal_density_diffrn 1.671 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 920 _exptl_absorpt_coefficient_mu 1.276 _exptl_absorpt_correction_type numerical _exptl_absorpt_correction_T_min 0.7023 _exptl_absorpt_correction_T_max 0.9228 _exptl_absorpt_process_details 'sadabs v2008/1' _exptl_special_details ; All H atoms were added in their calculated positions and were treated using appropriate riding models. ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 40965 _diffrn_reflns_av_R_equivalents 0.0339 _diffrn_reflns_av_sigmaI/netI 0.0165 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 2.06 _diffrn_reflns_theta_max 27.70 _reflns_number_total 4196 _reflns_number_gt 3714 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. Shelx restraints used: sadi 0.002 c17 cl1 c17 cl2 ; _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^)+(0.0342P)^2^+1.3882P] 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 4196 _refine_ls_number_parameters 244 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0322 _refine_ls_R_factor_gt 0.0266 _refine_ls_wR_factor_ref 0.0702 _refine_ls_wR_factor_gt 0.0665 _refine_ls_goodness_of_fit_ref 1.075 _refine_ls_restrained_S_all 1.075 _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 0.86538(2) 0.029382(14) 0.551895(15) 0.01017(7) Uani 1 1 d . . . O1 O 0.96807(12) 0.12685(8) 0.61401(8) 0.0135(2) Uani 1 1 d . . . O2 O 0.96532(12) 0.05974(8) 0.43272(8) 0.0119(2) Uani 1 1 d . . . N1 N 0.77656(15) -0.01207(9) 0.66636(10) 0.0134(3) Uani 1 1 d . . . N2 N 0.75655(14) -0.06508(9) 0.48725(10) 0.0135(3) Uani 1 1 d . . . N3 N 0.70757(15) 0.11403(10) 0.52058(10) 0.0160(3) Uani 1 1 d . . . N4 N 0.65583(15) 0.15628(10) 0.58803(10) 0.0159(3) Uani 1 1 d . . . N5 N 0.59987(18) 0.19831(12) 0.64819(12) 0.0271(4) Uani 1 1 d . . . C1 C 0.97816(17) 0.14172(11) 0.70888(12) 0.0138(3) Uani 1 1 d . . . C2 C 1.06371(18) 0.21790(12) 0.74201(13) 0.0166(3) Uani 1 1 d . . . H2 H 1.1049 0.2586 0.6953 0.020 Uiso 1 1 calc R . . C3 C 1.08816(19) 0.23389(12) 0.84085(13) 0.0196(3) Uani 1 1 d . . . H3 H 1.1457 0.2856 0.8613 0.024 Uiso 1 1 calc R . . C4 C 1.02954(19) 0.17517(13) 0.91174(12) 0.0209(4) Uani 1 1 d . . . H4 H 1.0507 0.1851 0.9796 0.025 Uiso 1 1 calc R . . C5 C 0.94099(19) 0.10311(12) 0.88178(12) 0.0182(3) Uani 1 1 d . . . H5 H 0.8992 0.0640 0.9297 0.022 Uiso 1 1 calc R . . C6 C 0.91099(17) 0.08614(11) 0.78098(11) 0.0148(3) Uani 1 1 d . . . C7 C 0.80977(18) 0.01386(11) 0.75480(12) 0.0154(3) Uani 1 1 d . . . H7 H 0.7634 -0.0175 0.8069 0.019 Uiso 1 1 calc R . . C8 C 0.66059(19) -0.08131(12) 0.64743(12) 0.0192(3) Uani 1 1 d . . . H8A H 0.5653 -0.0502 0.6369 0.023 Uiso 1 1 calc R . . H8B H 0.6533 -0.1241 0.7040 0.023 Uiso 1 1 calc R . . C9 C 0.70219(19) -0.13422(12) 0.55585(12) 0.0188(3) Uani 1 1 d . . . H9A H 0.7787 -0.1806 0.5719 0.023 Uiso 1 1 calc R . . H9B H 0.6163 -0.1668 0.5269 0.023 Uiso 1 1 calc R . . C10 C 0.72175(17) -0.06728(12) 0.39579(12) 0.0157(3) Uani 1 1 d . . . H10 H 0.6591 -0.1156 0.3729 0.019 Uiso 1 1 calc R . . C11 C 0.77250(18) -0.00008(11) 0.32486(12) 0.0149(3) Uani 1 1 d . . . C12 C 0.70510(19) 0.00053(13) 0.23121(13) 0.0189(3) Uani 1 1 d . . . H12 H 0.6284 -0.0420 0.2166 0.023 Uiso 1 1 calc R . . C13 C 0.7487(2) 0.06223(13) 0.15957(12) 0.0212(4) Uani 1 1 d . . . H13 H 0.7029 0.0617 0.0961 0.025 Uiso 1 1 calc R . . C14 C 0.8601(2) 0.12483(12) 0.18166(12) 0.0196(3) Uani 1 1 d . . . H14 H 0.8893 0.1680 0.1333 0.024 Uiso 1 1 calc R . . C15 C 0.92938(19) 0.12493(11) 0.27411(12) 0.0162(3) Uani 1 1 d . . . H15 H 1.0049 0.1684 0.2883 0.019 Uiso 1 1 calc R . . C16 C 0.88872(17) 0.06168(11) 0.34592(11) 0.0132(3) Uani 1 1 d . . . C17 C 0.92856(17) 0.30254(13) 0.46422(12) 0.0225(4) Uani 1 1 d D . . H17A H 0.8494 0.2939 0.4142 0.027 Uiso 1 1 calc R . . H17B H 0.9524 0.2411 0.4929 0.027 Uiso 1 1 calc R . . Cl1 Cl 1.08389(5) 0.34782(3) 0.40744(3) 0.02556(11) Uani 1 1 d D . . Cl2 Cl 0.86786(6) 0.37687(5) 0.55721(4) 0.04113(14) Uani 1 1 d D . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Co1 0.01159(11) 0.00891(11) 0.00995(10) 0.00022(7) -0.00077(7) -0.00159(7) O1 0.0169(5) 0.0114(5) 0.0122(5) -0.0008(4) -0.0005(4) -0.0026(4) O2 0.0137(5) 0.0117(5) 0.0102(5) 0.0002(4) -0.0016(4) -0.0005(4) N1 0.0131(6) 0.0123(6) 0.0149(6) 0.0016(5) 0.0010(5) -0.0011(5) N2 0.0127(6) 0.0120(6) 0.0157(6) 0.0006(5) -0.0002(5) -0.0020(5) N3 0.0173(7) 0.0172(7) 0.0134(6) 0.0004(5) -0.0014(5) 0.0038(5) N4 0.0146(6) 0.0157(7) 0.0171(7) 0.0033(5) -0.0024(5) 0.0012(5) N5 0.0290(8) 0.0300(9) 0.0224(8) -0.0026(7) 0.0019(6) 0.0123(7) C1 0.0135(7) 0.0130(7) 0.0148(7) -0.0027(6) -0.0013(6) 0.0032(6) C2 0.0164(8) 0.0132(8) 0.0202(8) -0.0031(6) -0.0014(6) 0.0001(6) C3 0.0170(8) 0.0182(8) 0.0234(8) -0.0097(7) -0.0052(6) 0.0043(6) C4 0.0198(8) 0.0275(9) 0.0152(8) -0.0080(7) -0.0044(6) 0.0074(7) C5 0.0192(8) 0.0213(8) 0.0141(7) -0.0019(6) 0.0007(6) 0.0063(7) C6 0.0150(7) 0.0161(8) 0.0134(7) -0.0016(6) -0.0004(6) 0.0028(6) C7 0.0165(8) 0.0156(8) 0.0143(7) 0.0026(6) 0.0027(6) 0.0013(6) C8 0.0185(8) 0.0202(8) 0.0188(8) 0.0011(7) 0.0022(6) -0.0081(7) C9 0.0228(9) 0.0150(8) 0.0186(8) 0.0018(6) -0.0002(6) -0.0069(6) C10 0.0135(7) 0.0147(8) 0.0189(8) -0.0035(6) -0.0019(6) -0.0014(6) C11 0.0161(8) 0.0141(7) 0.0144(7) -0.0014(6) -0.0023(6) 0.0022(6) C12 0.0179(8) 0.0204(8) 0.0182(8) -0.0042(6) -0.0050(6) 0.0036(7) C13 0.0239(9) 0.0255(9) 0.0141(8) -0.0017(7) -0.0042(6) 0.0082(7) C14 0.0254(9) 0.0185(8) 0.0149(7) 0.0028(6) 0.0008(6) 0.0072(7) C15 0.0196(8) 0.0132(7) 0.0158(7) -0.0001(6) 0.0008(6) 0.0026(6) C16 0.0146(7) 0.0127(7) 0.0121(7) -0.0012(6) -0.0009(6) 0.0043(6) C17 0.0204(8) 0.0229(9) 0.0243(9) -0.0030(7) 0.0041(7) -0.0044(7) Cl1 0.0240(2) 0.0215(2) 0.0314(2) 0.00297(17) 0.00440(17) -0.00250(17) Cl2 0.0352(3) 0.0555(4) 0.0327(3) -0.0184(2) 0.0023(2) 0.0122(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 N1 1.8738(13) . ? Co1 O1 1.8798(11) . ? Co1 N2 1.8916(14) . ? Co1 N3 1.9319(14) . ? Co1 O2 1.9333(11) . ? Co1 O2 2.0217(11) 3_756 ? Co1 Co1 2.9976(4) 3_756 ? O1 C1 1.3096(19) . ? O2 C16 1.3589(18) . ? O2 Co1 2.0216(11) 3_756 ? N1 C7 1.289(2) . ? N1 C8 1.476(2) . ? N2 C10 1.277(2) . ? N2 C9 1.462(2) . ? N3 N4 1.209(2) . ? N4 N5 1.150(2) . ? C1 C2 1.416(2) . ? C1 C6 1.419(2) . ? C2 C3 1.377(2) . ? C2 H2 0.9500 . ? C3 C4 1.401(3) . ? C3 H3 0.9500 . ? C4 C5 1.374(3) . ? C4 H4 0.9500 . ? C5 C6 1.413(2) . ? C5 H5 0.9500 . ? C6 C7 1.434(2) . ? C7 H7 0.9500 . ? C8 C9 1.518(2) . ? C8 H8A 0.9900 . ? C8 H8B 0.9900 . ? C9 H9A 0.9900 . ? C9 H9B 0.9900 . ? C10 C11 1.452(2) . ? C10 H10 0.9500 . ? C11 C12 1.402(2) . ? C11 C16 1.412(2) . ? C12 C13 1.386(3) . ? C12 H12 0.9500 . ? C13 C14 1.390(3) . ? C13 H13 0.9500 . ? C14 C15 1.395(2) . ? C14 H14 0.9500 . ? C15 C16 1.394(2) . ? C15 H15 0.9500 . ? C17 Cl2 1.7591(14) . ? C17 Cl1 1.7630(14) . ? C17 H17A 0.9900 . ? C17 H17B 0.9900 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N1 Co1 O1 95.04(5) . . ? N1 Co1 N2 85.51(6) . . ? O1 Co1 N2 177.65(5) . . ? N1 Co1 N3 92.62(6) . . ? O1 Co1 N3 89.49(6) . . ? N2 Co1 N3 88.20(6) . . ? N1 Co1 O2 174.22(5) . . ? O1 Co1 O2 88.01(5) . . ? N2 Co1 O2 91.64(5) . . ? N3 Co1 O2 92.32(5) . . ? N1 Co1 O2 93.46(5) . 3_756 ? O1 Co1 O2 93.08(5) . 3_756 ? N2 Co1 O2 89.17(5) . 3_756 ? N3 Co1 O2 173.17(5) . 3_756 ? O2 Co1 O2 81.46(5) . 3_756 ? N1 Co1 Co1 133.02(4) . 3_756 ? O1 Co1 Co1 90.79(4) . 3_756 ? N2 Co1 Co1 90.50(4) . 3_756 ? N3 Co1 Co1 134.09(4) . 3_756 ? O2 Co1 Co1 41.83(3) . 3_756 ? O2 Co1 Co1 39.63(3) 3_756 3_756 ? C1 O1 Co1 125.98(10) . . ? C16 O2 Co1 119.22(10) . . ? C16 O2 Co1 118.79(9) . 3_756 ? Co1 O2 Co1 98.54(5) . 3_756 ? C7 N1 C8 120.72(14) . . ? C7 N1 Co1 125.89(12) . . ? C8 N1 Co1 113.39(10) . . ? C10 N2 C9 121.64(14) . . ? C10 N2 Co1 125.92(12) . . ? C9 N2 Co1 112.22(10) . . ? N4 N3 Co1 117.20(11) . . ? N5 N4 N3 175.73(17) . . ? O1 C1 C2 117.73(15) . . ? O1 C1 C6 124.62(14) . . ? C2 C1 C6 117.65(14) . . ? C3 C2 C1 121.04(16) . . ? C3 C2 H2 119.5 . . ? C1 C2 H2 119.5 . . ? C2 C3 C4 121.04(16) . . ? C2 C3 H3 119.5 . . ? C4 C3 H3 119.5 . . ? C5 C4 C3 119.13(15) . . ? C5 C4 H4 120.4 . . ? C3 C4 H4 120.4 . . ? C4 C5 C6 121.18(16) . . ? C4 C5 H5 119.4 . . ? C6 C5 H5 119.4 . . ? C5 C6 C1 119.74(15) . . ? C5 C6 C7 118.39(15) . . ? C1 C6 C7 121.85(14) . . ? N1 C7 C6 125.34(15) . . ? N1 C7 H7 117.3 . . ? C6 C7 H7 117.3 . . ? N1 C8 C9 106.72(13) . . ? N1 C8 H8A 110.4 . . ? C9 C8 H8A 110.4 . . ? N1 C8 H8B 110.4 . . ? C9 C8 H8B 110.4 . . ? H8A C8 H8B 108.6 . . ? N2 C9 C8 106.19(13) . . ? N2 C9 H9A 110.5 . . ? C8 C9 H9A 110.5 . . ? N2 C9 H9B 110.5 . . ? C8 C9 H9B 110.5 . . ? H9A C9 H9B 108.7 . . ? N2 C10 C11 123.69(15) . . ? N2 C10 H10 118.2 . . ? C11 C10 H10 118.2 . . ? C12 C11 C16 119.56(15) . . ? C12 C11 C10 117.84(15) . . ? C16 C11 C10 122.58(14) . . ? C13 C12 C11 121.01(17) . . ? C13 C12 H12 119.5 . . ? C11 C12 H12 119.5 . . ? C12 C13 C14 119.20(16) . . ? C12 C13 H13 120.4 . . ? C14 C13 H13 120.4 . . ? C13 C14 C15 120.73(16) . . ? C13 C14 H14 119.6 . . ? C15 C14 H14 119.6 . . ? C16 C15 C14 120.51(16) . . ? C16 C15 H15 119.7 . . ? C14 C15 H15 119.7 . . ? O2 C16 C15 118.76(14) . . ? O2 C16 C11 122.28(14) . . ? C15 C16 C11 118.94(15) . . ? Cl2 C17 Cl1 111.34(10) . . ? Cl2 C17 H17A 109.4 . . ? Cl1 C17 H17A 109.4 . . ? Cl2 C17 H17B 109.4 . . ? Cl1 C17 H17B 109.4 . . ? H17A C17 H17B 108.0 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N1 Co1 O1 C1 8.32(13) . . . . ? N3 Co1 O1 C1 100.90(13) . . . . ? O2 Co1 O1 C1 -166.76(13) . . . . ? O2 Co1 O1 C1 -85.43(12) 3_756 . . . ? Co1 Co1 O1 C1 -125.01(12) 3_756 . . . ? O1 Co1 O2 C16 -136.65(11) . . . . ? N2 Co1 O2 C16 41.03(11) . . . . ? N3 Co1 O2 C16 -47.24(11) . . . . ? O2 Co1 O2 C16 129.94(13) 3_756 . . . ? Co1 Co1 O2 C16 129.94(13) 3_756 . . . ? O1 Co1 O2 Co1 93.42(5) . . . 3_756 ? N2 Co1 O2 Co1 -88.91(6) . . . 3_756 ? N3 Co1 O2 Co1 -177.18(5) . . . 3_756 ? O2 Co1 O2 Co1 0.0 3_756 . . 3_756 ? O1 Co1 N1 C7 -11.24(15) . . . . ? N2 Co1 N1 C7 171.06(15) . . . . ? N3 Co1 N1 C7 -100.95(14) . . . . ? O2 Co1 N1 C7 82.17(14) 3_756 . . . ? Co1 Co1 N1 C7 84.58(15) 3_756 . . . ? O1 Co1 N1 C8 169.54(11) . . . . ? N2 Co1 N1 C8 -8.16(11) . . . . ? N3 Co1 N1 C8 79.83(12) . . . . ? O2 Co1 N1 C8 -97.05(11) 3_756 . . . ? Co1 Co1 N1 C8 -94.64(11) 3_756 . . . ? N1 Co1 N2 C10 157.31(14) . . . . ? N3 Co1 N2 C10 64.55(14) . . . . ? O2 Co1 N2 C10 -27.73(14) . . . . ? O2 Co1 N2 C10 -109.15(14) 3_756 . . . ? Co1 Co1 N2 C10 -69.55(14) 3_756 . . . ? N1 Co1 N2 C9 -17.30(11) . . . . ? N3 Co1 N2 C9 -110.07(11) . . . . ? O2 Co1 N2 C9 157.66(11) . . . . ? O2 Co1 N2 C9 76.23(11) 3_756 . . . ? Co1 Co1 N2 C9 115.84(11) 3_756 . . . ? N1 Co1 N3 N4 40.17(13) . . . . ? O1 Co1 N3 N4 -54.86(13) . . . . ? N2 Co1 N3 N4 125.59(13) . . . . ? O2 Co1 N3 N4 -142.84(13) . . . . ? Co1 Co1 N3 N4 -145.46(10) 3_756 . . . ? Co1 O1 C1 C2 178.53(11) . . . . ? Co1 O1 C1 C6 -0.6(2) . . . . ? O1 C1 C2 C3 -175.21(15) . . . . ? C6 C1 C2 C3 4.0(2) . . . . ? C1 C2 C3 C4 0.2(3) . . . . ? C2 C3 C4 C5 -3.0(3) . . . . ? C3 C4 C5 C6 1.4(2) . . . . ? C4 C5 C6 C1 2.8(2) . . . . ? C4 C5 C6 C7 -175.75(15) . . . . ? O1 C1 C6 C5 173.73(15) . . . . ? C2 C1 C6 C5 -5.4(2) . . . . ? O1 C1 C6 C7 -7.8(2) . . . . ? C2 C1 C6 C7 173.09(15) . . . . ? C8 N1 C7 C6 -174.22(15) . . . . ? Co1 N1 C7 C6 6.6(2) . . . . ? C5 C6 C7 N1 -176.87(16) . . . . ? C1 C6 C7 N1 4.6(3) . . . . ? C7 N1 C8 C9 -149.13(15) . . . . ? Co1 N1 C8 C9 30.14(16) . . . . ? C10 N2 C9 C8 -137.66(16) . . . . ? Co1 N2 C9 C8 37.22(15) . . . . ? N1 C8 C9 N2 -41.81(17) . . . . ? C9 N2 C10 C11 179.80(15) . . . . ? Co1 N2 C10 C11 5.7(2) . . . . ? N2 C10 C11 C12 -168.04(16) . . . . ? N2 C10 C11 C16 14.0(3) . . . . ? C16 C11 C12 C13 -1.4(3) . . . . ? C10 C11 C12 C13 -179.48(16) . . . . ? C11 C12 C13 C14 -0.6(3) . . . . ? C12 C13 C14 C15 1.1(3) . . . . ? C13 C14 C15 C16 0.4(3) . . . . ? Co1 O2 C16 C15 147.06(12) . . . . ? Co1 O2 C16 C15 -92.83(15) 3_756 . . . ? Co1 O2 C16 C11 -34.98(19) . . . . ? Co1 O2 C16 C11 85.12(16) 3_756 . . . ? C14 C15 C16 O2 175.60(14) . . . . ? C14 C15 C16 C11 -2.4(2) . . . . ? C12 C11 C16 O2 -175.06(15) . . . . ? C10 C11 C16 O2 2.9(2) . . . . ? C12 C11 C16 C15 2.9(2) . . . . ? C10 C11 C16 C15 -179.14(15) . . . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.698 _refine_diff_density_min -0.389 _refine_diff_density_rms 0.068 #===END data_l12110 _database_code_depnum_ccdc_archive 'CCDC 864403' #TrackingRef '- Cif_Combined3New.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C34 H32 Fe2 N10 O4' _chemical_formula_weight 756.40 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' Fe Fe 0.3463 0.8444 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 8.5467(9) _cell_length_b 13.5994(16) _cell_length_c 14.4097(18) _cell_angle_alpha 90.00 _cell_angle_beta 103.693(6) _cell_angle_gamma 90.00 _cell_volume 1627.2(3) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 3321 _cell_measurement_theta_min 2.91 _cell_measurement_theta_max 22.06 _exptl_crystal_description rectangular _exptl_crystal_colour purple _exptl_crystal_size_max 0.14 _exptl_crystal_size_mid 0.09 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas no _exptl_crystal_density_diffrn 1.544 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 780 _exptl_absorpt_coefficient_mu 0.948 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8802 _exptl_absorpt_correction_T_max 0.9550 _exptl_absorpt_process_details 'sadabs v2008/1' _exptl_special_details ; All H atoms were added in their calculated positions and were treated using appropriate riding models. ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 29917 _diffrn_reflns_av_R_equivalents 0.0985 _diffrn_reflns_av_sigmaI/netI 0.0586 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 2.09 _diffrn_reflns_theta_max 25.48 _reflns_number_total 3006 _reflns_number_gt 1934 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0598P)^2^+2.8838P] 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 3006 _refine_ls_number_parameters 227 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1011 _refine_ls_R_factor_gt 0.0553 _refine_ls_wR_factor_ref 0.1458 _refine_ls_wR_factor_gt 0.1238 _refine_ls_goodness_of_fit_ref 1.069 _refine_ls_restrained_S_all 1.069 _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 Fe1 Fe 0.14155(8) 0.49923(5) 0.09686(4) 0.0263(2) Uani 1 1 d . . . O1 O 0.3172(4) 0.4520(2) 0.0522(2) 0.0288(7) Uani 1 1 d . . . O2 O 0.0243(4) 0.5947(2) 0.0016(2) 0.0260(7) Uani 1 1 d . . . N1 N 0.1768(5) 0.3836(3) 0.1948(3) 0.0343(10) Uani 1 1 d . . . N2 N -0.0560(5) 0.5167(3) 0.1606(3) 0.0320(10) Uani 1 1 d . . . N3 N 0.2676(5) 0.6031(3) 0.1830(3) 0.0312(10) Uani 1 1 d . . . N4 N 0.4066(5) 0.5948(3) 0.2262(3) 0.0327(10) Uani 1 1 d . . . N5 N 0.5357(6) 0.5913(4) 0.2692(3) 0.0557(14) Uani 1 1 d . . . C1 C 0.4011(5) 0.3701(3) 0.0667(3) 0.0283(11) Uani 1 1 d . . . C2 C 0.5119(6) 0.3524(3) 0.0113(4) 0.0345(11) Uani 1 1 d . . . H2 H 0.5281 0.4006 -0.0332 0.041 Uiso 1 1 calc R . . C3 C 0.5977(6) 0.2663(4) 0.0204(4) 0.0414(14) Uani 1 1 d . . . H3 H 0.6712 0.2551 -0.0187 0.050 Uiso 1 1 calc R . . C4 C 0.5785(6) 0.1957(4) 0.0856(4) 0.0445(14) Uani 1 1 d . . . H4 H 0.6385 0.1363 0.0918 0.053 Uiso 1 1 calc R . . C5 C 0.4720(7) 0.2123(4) 0.1412(4) 0.0417(14) Uani 1 1 d . . . H5 H 0.4582 0.1633 0.1856 0.050 Uiso 1 1 calc R . . C6 C 0.3824(6) 0.2995(3) 0.1347(3) 0.0313(11) Uani 1 1 d . . . C7 C 0.2741(6) 0.3114(4) 0.1970(3) 0.0365(13) Uani 1 1 d . . . H7 H 0.2750 0.2617 0.2435 0.044 Uiso 1 1 calc R . . C8 C 0.0712(7) 0.3844(4) 0.2634(3) 0.0452(14) Uani 1 1 d . . . H8 H 0.0521 0.3150 0.2810 0.054 Uiso 1 1 calc R . . C9 C -0.0897(7) 0.4301(4) 0.2125(4) 0.0426(13) Uani 1 1 d . . . H9A H -0.1541 0.3821 0.1675 0.051 Uiso 1 1 calc R . . H9B H -0.1517 0.4490 0.2597 0.051 Uiso 1 1 calc R . . C10 C -0.1369(6) 0.5947(4) 0.1571(3) 0.0349(12) Uani 1 1 d . . . H10 H -0.2208 0.5960 0.1902 0.042 Uiso 1 1 calc R . . C11 C -0.1102(6) 0.6826(4) 0.1059(3) 0.0312(11) Uani 1 1 d . . . C12 C -0.1703(7) 0.7722(4) 0.1294(4) 0.0417(14) Uani 1 1 d . . . H12 H -0.2273 0.7743 0.1785 0.050 Uiso 1 1 calc R . . C13 C -0.1486(7) 0.8574(4) 0.0830(4) 0.0457(15) Uani 1 1 d . . . H13 H -0.1881 0.9180 0.1009 0.055 Uiso 1 1 calc R . . C14 C -0.0697(6) 0.8545(4) 0.0105(4) 0.0435(14) Uani 1 1 d . . . H14 H -0.0560 0.9135 -0.0219 0.052 Uiso 1 1 calc R . . C15 C -0.0094(6) 0.7669(3) -0.0163(3) 0.0331(12) Uani 1 1 d . . . H15 H 0.0443 0.7664 -0.0669 0.040 Uiso 1 1 calc R . . C16 C -0.0277(5) 0.6803(3) 0.0308(3) 0.0289(11) Uani 1 1 d . . . C17 C 0.1444(8) 0.4397(5) 0.3516(4) 0.0622(18) Uani 1 1 d . . . H17A H 0.2485 0.4104 0.3822 0.093 Uiso 1 1 calc R . . H17B H 0.0727 0.4370 0.3955 0.093 Uiso 1 1 calc R . . H17C H 0.1602 0.5084 0.3354 0.093 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 Fe1 0.0319(4) 0.0202(3) 0.0232(3) 0.0005(3) -0.0008(3) -0.0006(3) O1 0.0282(18) 0.0205(16) 0.0355(18) 0.0058(14) 0.0033(14) 0.0007(14) O2 0.0287(19) 0.0203(15) 0.0252(15) -0.0011(14) -0.0010(14) -0.0013(13) N1 0.043(3) 0.030(2) 0.025(2) 0.0023(18) -0.0016(19) -0.003(2) N2 0.040(2) 0.031(2) 0.0232(19) -0.0054(17) 0.0044(17) -0.0041(19) N3 0.030(2) 0.027(2) 0.032(2) -0.0046(17) -0.0020(19) -0.0001(18) N4 0.038(3) 0.030(2) 0.028(2) -0.0055(18) 0.006(2) -0.002(2) N5 0.030(3) 0.083(4) 0.047(3) -0.012(3) -0.005(2) -0.006(3) C1 0.024(3) 0.023(2) 0.032(3) -0.002(2) -0.007(2) -0.003(2) C2 0.031(3) 0.028(2) 0.041(3) 0.002(2) 0.002(2) -0.005(2) C3 0.031(3) 0.034(3) 0.053(3) -0.002(3) -0.001(3) 0.005(2) C4 0.031(3) 0.030(3) 0.062(4) 0.000(3) -0.011(3) 0.008(2) C5 0.041(3) 0.030(3) 0.043(3) 0.008(2) -0.011(3) 0.002(2) C6 0.026(3) 0.028(3) 0.031(3) 0.001(2) -0.012(2) -0.001(2) C7 0.049(3) 0.028(3) 0.023(2) 0.006(2) -0.010(2) -0.001(2) C8 0.068(4) 0.039(3) 0.029(3) 0.005(2) 0.012(3) 0.003(3) C9 0.056(4) 0.035(3) 0.039(3) 0.008(2) 0.017(3) 0.003(3) C10 0.038(3) 0.038(3) 0.027(3) -0.007(2) 0.003(2) 0.001(2) C11 0.027(3) 0.031(3) 0.030(3) -0.006(2) -0.005(2) -0.001(2) C12 0.044(3) 0.035(3) 0.037(3) -0.011(2) -0.008(3) 0.007(2) C13 0.043(3) 0.035(3) 0.047(3) -0.016(3) -0.013(3) 0.010(3) C14 0.035(3) 0.020(3) 0.061(4) 0.002(3) -0.018(3) -0.002(2) C15 0.029(3) 0.028(3) 0.035(3) 0.000(2) -0.007(2) -0.002(2) C16 0.024(3) 0.024(3) 0.031(3) -0.004(2) -0.008(2) -0.002(2) C17 0.063(4) 0.065(4) 0.054(4) 0.009(3) 0.004(3) -0.001(4) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Fe1 O1 1.881(3) . ? Fe1 O2 1.981(3) . ? Fe1 N3 2.015(4) . ? Fe1 N1 2.087(4) . ? Fe1 N2 2.118(4) . ? Fe1 O2 2.169(3) 3_565 ? O1 C1 1.315(5) . ? O2 C16 1.348(5) . ? O2 Fe1 2.169(3) 3_565 ? N1 C7 1.282(6) . ? N1 C8 1.488(7) . ? N2 C10 1.260(6) . ? N2 C9 1.461(6) . ? N3 N4 1.209(5) . ? N4 N5 1.132(6) . ? C1 C2 1.396(7) . ? C1 C6 1.408(7) . ? C2 C3 1.371(7) . ? C2 H2 0.9500 . ? C3 C4 1.380(8) . ? C3 H3 0.9500 . ? C4 C5 1.366(8) . ? C4 H4 0.9500 . ? C5 C6 1.403(7) . ? C5 H5 0.9500 . ? C6 C7 1.443(7) . ? C7 H7 0.9500 . ? C8 C17 1.482(8) . ? C8 C9 1.529(8) . ? C8 H8 1.0000 . ? C9 H9A 0.9900 . ? C9 H9B 0.9900 . ? C10 C11 1.451(7) . ? C10 H10 0.9500 . ? C11 C12 1.396(7) . ? C11 C16 1.424(7) . ? C12 C13 1.371(8) . ? C12 H12 0.9500 . ? C13 C14 1.371(8) . ? C13 H13 0.9500 . ? C14 C15 1.387(7) . ? C14 H14 0.9500 . ? C15 C16 1.386(7) . ? C15 H15 0.9500 . ? C17 H17A 0.9800 . ? C17 H17B 0.9800 . ? C17 H17C 0.9800 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 Fe1 O2 107.51(13) . . ? O1 Fe1 N3 95.53(15) . . ? O2 Fe1 N3 94.36(14) . . ? O1 Fe1 N1 88.56(15) . . ? O2 Fe1 N1 158.61(15) . . ? N3 Fe1 N1 98.12(15) . . ? O1 Fe1 N2 165.83(14) . . ? O2 Fe1 N2 84.40(14) . . ? N3 Fe1 N2 91.09(15) . . ? N1 Fe1 N2 78.08(16) . . ? O1 Fe1 O2 91.48(13) . 3_565 ? O2 Fe1 O2 77.75(12) . 3_565 ? N3 Fe1 O2 170.76(14) . 3_565 ? N1 Fe1 O2 88.05(13) . 3_565 ? N2 Fe1 O2 83.43(13) . 3_565 ? C1 O1 Fe1 133.2(3) . . ? C16 O2 Fe1 120.0(3) . . ? C16 O2 Fe1 120.0(3) . 3_565 ? Fe1 O2 Fe1 102.25(12) . 3_565 ? C7 N1 C8 118.7(4) . . ? C7 N1 Fe1 125.7(4) . . ? C8 N1 Fe1 115.5(3) . . ? C10 N2 C9 121.7(5) . . ? C10 N2 Fe1 124.3(4) . . ? C9 N2 Fe1 113.9(3) . . ? N4 N3 Fe1 124.6(3) . . ? N5 N4 N3 176.4(5) . . ? O1 C1 C2 118.3(4) . . ? O1 C1 C6 122.7(5) . . ? C2 C1 C6 119.0(4) . . ? C3 C2 C1 120.8(5) . . ? C3 C2 H2 119.6 . . ? C1 C2 H2 119.6 . . ? C2 C3 C4 120.8(5) . . ? C2 C3 H3 119.6 . . ? C4 C3 H3 119.6 . . ? C5 C4 C3 119.2(5) . . ? C5 C4 H4 120.4 . . ? C3 C4 H4 120.4 . . ? C4 C5 C6 122.0(5) . . ? C4 C5 H5 119.0 . . ? C6 C5 H5 119.0 . . ? C5 C6 C1 118.2(5) . . ? C5 C6 C7 118.3(5) . . ? C1 C6 C7 123.5(4) . . ? N1 C7 C6 125.3(5) . . ? N1 C7 H7 117.4 . . ? C6 C7 H7 117.4 . . ? C17 C8 N1 112.0(5) . . ? C17 C8 C9 110.7(5) . . ? N1 C8 C9 107.6(4) . . ? C17 C8 H8 108.8 . . ? N1 C8 H8 108.8 . . ? C9 C8 H8 108.8 . . ? N2 C9 C8 108.0(4) . . ? N2 C9 H9A 110.1 . . ? C8 C9 H9A 110.1 . . ? N2 C9 H9B 110.1 . . ? C8 C9 H9B 110.1 . . ? H9A C9 H9B 108.4 . . ? N2 C10 C11 124.2(5) . . ? N2 C10 H10 117.9 . . ? C11 C10 H10 117.9 . . ? C12 C11 C16 118.7(5) . . ? C12 C11 C10 119.0(5) . . ? C16 C11 C10 122.3(4) . . ? C13 C12 C11 121.3(6) . . ? C13 C12 H12 119.3 . . ? C11 C12 H12 119.3 . . ? C14 C13 C12 119.6(5) . . ? C14 C13 H13 120.2 . . ? C12 C13 H13 120.2 . . ? C13 C14 C15 121.3(5) . . ? C13 C14 H14 119.4 . . ? C15 C14 H14 119.4 . . ? C16 C15 C14 120.0(5) . . ? C16 C15 H15 120.0 . . ? C14 C15 H15 120.0 . . ? O2 C16 C15 119.8(5) . . ? O2 C16 C11 120.9(4) . . ? C15 C16 C11 119.1(5) . . ? C8 C17 H17A 109.5 . . ? C8 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? C8 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O2 Fe1 O1 C1 -154.5(4) . . . . ? N3 Fe1 O1 C1 109.2(4) . . . . ? N1 Fe1 O1 C1 11.2(4) . . . . ? N2 Fe1 O1 C1 -8.3(8) . . . . ? O2 Fe1 O1 C1 -76.8(4) 3_565 . . . ? O1 Fe1 O2 C16 -136.6(3) . . . . ? N3 Fe1 O2 C16 -39.4(3) . . . . ? N1 Fe1 O2 C16 86.3(5) . . . . ? N2 Fe1 O2 C16 51.3(3) . . . . ? O2 Fe1 O2 C16 135.8(4) 3_565 . . . ? O1 Fe1 O2 Fe1 87.67(15) . . . 3_565 ? N3 Fe1 O2 Fe1 -175.13(15) . . . 3_565 ? N1 Fe1 O2 Fe1 -49.5(4) . . . 3_565 ? N2 Fe1 O2 Fe1 -84.47(15) . . . 3_565 ? O2 Fe1 O2 Fe1 0.0 3_565 . . 3_565 ? O1 Fe1 N1 C7 -8.3(4) . . . . ? O2 Fe1 N1 C7 131.3(4) . . . . ? N3 Fe1 N1 C7 -103.7(4) . . . . ? N2 Fe1 N1 C7 166.9(4) . . . . ? O2 Fe1 N1 C7 83.2(4) 3_565 . . . ? O1 Fe1 N1 C8 175.4(3) . . . . ? O2 Fe1 N1 C8 -45.1(6) . . . . ? N3 Fe1 N1 C8 80.0(4) . . . . ? N2 Fe1 N1 C8 -9.4(3) . . . . ? O2 Fe1 N1 C8 -93.1(3) 3_565 . . . ? O1 Fe1 N2 C10 -178.5(5) . . . . ? O2 Fe1 N2 C10 -30.7(4) . . . . ? N3 Fe1 N2 C10 63.6(4) . . . . ? N1 Fe1 N2 C10 161.7(4) . . . . ? O2 Fe1 N2 C10 -108.9(4) 3_565 . . . ? O1 Fe1 N2 C9 3.1(7) . . . . ? O2 Fe1 N2 C9 150.9(3) . . . . ? N3 Fe1 N2 C9 -114.9(3) . . . . ? N1 Fe1 N2 C9 -16.8(3) . . . . ? O2 Fe1 N2 C9 72.6(3) 3_565 . . . ? O1 Fe1 N3 N4 -34.2(4) . . . . ? O2 Fe1 N3 N4 -142.3(4) . . . . ? N1 Fe1 N3 N4 55.1(4) . . . . ? N2 Fe1 N3 N4 133.2(4) . . . . ? O2 Fe1 N3 N4 -173.4(7) 3_565 . . . ? Fe1 N3 N4 N5 -169(8) . . . . ? Fe1 O1 C1 C2 171.2(3) . . . . ? Fe1 O1 C1 C6 -8.1(6) . . . . ? O1 C1 C2 C3 -177.1(4) . . . . ? C6 C1 C2 C3 2.2(7) . . . . ? C1 C2 C3 C4 -1.1(7) . . . . ? C2 C3 C4 C5 0.3(8) . . . . ? C3 C4 C5 C6 -0.6(8) . . . . ? C4 C5 C6 C1 1.7(7) . . . . ? C4 C5 C6 C7 -179.2(5) . . . . ? O1 C1 C6 C5 176.9(4) . . . . ? C2 C1 C6 C5 -2.4(6) . . . . ? O1 C1 C6 C7 -2.2(7) . . . . ? C2 C1 C6 C7 178.6(4) . . . . ? C8 N1 C7 C6 179.2(4) . . . . ? Fe1 N1 C7 C6 3.0(7) . . . . ? C5 C6 C7 N1 -175.0(5) . . . . ? C1 C6 C7 N1 4.0(8) . . . . ? C7 N1 C8 C17 93.4(6) . . . . ? Fe1 N1 C8 C17 -90.0(5) . . . . ? C7 N1 C8 C9 -144.7(4) . . . . ? Fe1 N1 C8 C9 31.9(5) . . . . ? C10 N2 C9 C8 -140.2(5) . . . . ? Fe1 N2 C9 C8 38.3(5) . . . . ? C17 C8 C9 N2 78.7(6) . . . . ? N1 C8 C9 N2 -44.0(5) . . . . ? C9 N2 C10 C11 -179.3(4) . . . . ? Fe1 N2 C10 C11 2.4(7) . . . . ? N2 C10 C11 C12 -160.7(5) . . . . ? N2 C10 C11 C16 20.7(7) . . . . ? C16 C11 C12 C13 -1.2(7) . . . . ? C10 C11 C12 C13 -179.8(5) . . . . ? C11 C12 C13 C14 1.5(8) . . . . ? C12 C13 C14 C15 -0.7(8) . . . . ? C13 C14 C15 C16 -0.4(7) . . . . ? Fe1 O2 C16 C15 137.1(3) . . . . ? Fe1 O2 C16 C15 -94.9(4) 3_565 . . . ? Fe1 O2 C16 C11 -46.7(5) . . . . ? Fe1 O2 C16 C11 81.3(4) 3_565 . . . ? C14 C15 C16 O2 176.9(4) . . . . ? C14 C15 C16 C11 0.6(6) . . . . ? C12 C11 C16 O2 -176.1(4) . . . . ? C10 C11 C16 O2 2.5(7) . . . . ? C12 C11 C16 C15 0.1(6) . . . . ? C10 C11 C16 C15 178.7(4) . . . . ? _diffrn_measured_fraction_theta_max 0.991 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.678 _refine_diff_density_min -0.451 _refine_diff_density_rms 0.086 #===END data_l17310 _database_code_depnum_ccdc_archive 'CCDC 864404' #TrackingRef '- Cif_Combined3New.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C14 H32 N7 Ni, F6 P' _chemical_formula_sum 'C14 H32 F6 N7 Ni P' _chemical_formula_weight 502.15 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' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' P P 0.1023 0.0942 '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 Orthorhombic _symmetry_space_group_name_H-M Pnma loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z' 'x+1/2, -y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, y, -z-1/2' 'x, -y-1/2, z' '-x-1/2, y-1/2, z-1/2' _cell_length_a 14.4194(15) _cell_length_b 9.7386(10) _cell_length_c 14.4293(15) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2026.2(4) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 9959 _cell_measurement_theta_min 2.52 _cell_measurement_theta_max 35.49 _exptl_crystal_description rod _exptl_crystal_colour green _exptl_crystal_size_max 0.28 _exptl_crystal_size_mid 0.16 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas no _exptl_crystal_density_diffrn 1.646 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1048 _exptl_absorpt_coefficient_mu 1.107 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7440 _exptl_absorpt_correction_T_max 0.8823 _exptl_absorpt_process_details 'sadabs v2008/1' _exptl_special_details ; All H atoms were added in their calculated positions and were treated using appropriate riding models. ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 84554 _diffrn_reflns_av_R_equivalents 0.0413 _diffrn_reflns_av_sigmaI/netI 0.0179 _diffrn_reflns_limit_h_min -23 _diffrn_reflns_limit_h_max 23 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 2.00 _diffrn_reflns_theta_max 35.88 _reflns_number_total 4952 _reflns_number_gt 4245 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0380P)^2^+0.8285P] 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 4952 _refine_ls_number_parameters 150 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0361 _refine_ls_R_factor_gt 0.0277 _refine_ls_wR_factor_ref 0.0740 _refine_ls_wR_factor_gt 0.0690 _refine_ls_goodness_of_fit_ref 1.013 _refine_ls_restrained_S_all 1.013 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Ni1 Ni 0.241056(11) 0.2500 0.113936(11) 0.01076(4) Uani 1 2 d S . . N1 N 0.14108(6) 0.08977(9) 0.12419(6) 0.01658(14) Uani 1 1 d . . . N2 N 0.33118(6) 0.09292(9) 0.06406(6) 0.01703(14) Uani 1 1 d . . . N3 N 0.29445(9) 0.2500 0.24102(8) 0.0198(2) Uani 1 2 d S . . N4 N 0.26117(11) 0.2500 0.31576(9) 0.0262(3) Uani 1 2 d S . . N5 N 0.23199(17) 0.2500 0.39015(11) 0.0463(5) Uani 1 2 d S . . C1 C 0.17774(8) -0.01874(10) 0.06152(7) 0.02066(17) Uani 1 1 d . . . H1A H 0.1663 0.0077 -0.0038 0.025 Uiso 1 1 calc R . . H1B H 0.1449 -0.1062 0.0735 0.025 Uiso 1 1 calc R . . C2 C 0.27980(8) -0.03825(10) 0.07670(8) 0.02200(18) Uani 1 1 d . . . H2A H 0.2905 -0.0733 0.1402 0.026 Uiso 1 1 calc R . . H2B H 0.3036 -0.1074 0.0324 0.026 Uiso 1 1 calc R . . C3 C 0.04500(7) 0.12060(12) 0.09325(7) 0.02098(18) Uani 1 1 d . . . H3A H 0.0046 0.0422 0.1101 0.025 Uiso 1 1 calc R . . H3B H 0.0447 0.1284 0.0248 0.025 Uiso 1 1 calc R . . C4 C 0.00392(10) 0.2500 0.13350(11) 0.0245(3) Uani 1 2 d S . . H4A H 0.0138 0.2500 0.2014 0.029 Uiso 1 2 calc SR . . H4B H -0.0638 0.2500 0.1222 0.029 Uiso 1 2 calc SR . . C5 C 0.34899(7) 0.11646(11) -0.03651(7) 0.02039(17) Uani 1 1 d . . . H5A H 0.2889 0.1155 -0.0696 0.024 Uiso 1 1 calc R . . H5B H 0.3864 0.0390 -0.0605 0.024 Uiso 1 1 calc R . . C6 C 0.39888(11) 0.2500 -0.05947(10) 0.0225(3) Uani 1 2 d S . . H6A H 0.4128 0.2500 -0.1267 0.027 Uiso 1 2 calc SR . . H6B H 0.4590 0.2500 -0.0263 0.027 Uiso 1 2 calc SR . . C7 C 0.13665(8) 0.03650(12) 0.22029(7) 0.0245(2) Uani 1 1 d . . . H7A H 0.0957 -0.0438 0.2223 0.037 Uiso 1 1 calc R . . H7B H 0.1123 0.1080 0.2614 0.037 Uiso 1 1 calc R . . H7C H 0.1990 0.0100 0.2407 0.037 Uiso 1 1 calc R . . C8 C 0.42020(8) 0.07320(13) 0.11359(8) 0.0250(2) Uani 1 1 d . . . H8A H 0.4090 0.0734 0.1806 0.037 Uiso 1 1 calc R . . H8B H 0.4628 0.1480 0.0976 0.037 Uiso 1 1 calc R . . H8C H 0.4476 -0.0148 0.0953 0.037 Uiso 1 1 calc R . . P1 P 0.38188(2) 0.7500 0.31467(2) 0.01486(6) Uani 1 2 d S . . F1 F 0.34570(6) 0.7500 0.42096(6) 0.01968(16) Uani 1 2 d S . . F2 F 0.27668(6) 0.7500 0.27931(6) 0.02112(17) Uani 1 2 d S . . F3 F 0.48631(6) 0.7500 0.35225(7) 0.02588(19) Uani 1 2 d S . . F4 F 0.38071(5) 0.91391(6) 0.31612(5) 0.02375(13) Uani 1 1 d . . . F5 F 0.41813(7) 0.7500 0.21061(7) 0.02567(19) Uani 1 2 d S . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Ni1 0.01031(7) 0.01131(7) 0.01064(7) 0.000 0.00075(5) 0.000 N1 0.0169(3) 0.0165(3) 0.0163(3) 0.0014(3) 0.0013(3) -0.0033(3) N2 0.0164(3) 0.0167(3) 0.0180(3) -0.0005(3) 0.0019(3) 0.0027(3) N3 0.0216(5) 0.0238(5) 0.0140(5) 0.000 -0.0038(4) 0.000 N4 0.0390(8) 0.0242(6) 0.0154(5) 0.000 -0.0036(5) 0.000 N5 0.0748(15) 0.0496(11) 0.0146(6) 0.000 0.0061(7) 0.000 C1 0.0254(5) 0.0149(4) 0.0216(4) -0.0017(3) -0.0007(3) -0.0037(3) C2 0.0275(5) 0.0146(4) 0.0239(4) -0.0003(3) -0.0003(4) 0.0029(3) C3 0.0142(4) 0.0265(5) 0.0222(4) 0.0010(4) 0.0004(3) -0.0069(3) C4 0.0123(5) 0.0356(8) 0.0256(7) 0.000 0.0051(5) 0.000 C5 0.0189(4) 0.0241(4) 0.0181(4) -0.0035(3) 0.0037(3) 0.0042(3) C6 0.0178(6) 0.0312(7) 0.0184(6) 0.000 0.0063(5) 0.000 C7 0.0291(5) 0.0256(5) 0.0189(4) 0.0072(4) 0.0009(4) -0.0076(4) C8 0.0202(4) 0.0281(5) 0.0267(5) 0.0017(4) -0.0026(4) 0.0083(4) P1 0.01484(14) 0.01376(13) 0.01597(14) 0.000 -0.00245(11) 0.000 F1 0.0201(4) 0.0229(4) 0.0161(4) 0.000 -0.0024(3) 0.000 F2 0.0171(4) 0.0240(4) 0.0224(4) 0.000 -0.0073(3) 0.000 F3 0.0142(4) 0.0328(5) 0.0306(5) 0.000 -0.0040(3) 0.000 F4 0.0312(3) 0.0137(2) 0.0264(3) 0.0005(2) -0.0043(3) -0.0024(2) F5 0.0306(5) 0.0282(5) 0.0182(4) 0.000 0.0043(3) 0.000 _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Ni1 N3 1.9887(12) . ? Ni1 N1 2.1295(8) 7_565 ? Ni1 N1 2.1296(8) . ? Ni1 N2 2.1323(8) 7_565 ? Ni1 N2 2.1323(8) . ? N1 C7 1.4818(13) . ? N1 C3 1.4863(13) . ? N1 C1 1.4879(13) . ? N2 C8 1.4818(14) . ? N2 C2 1.4879(14) . ? N2 C5 1.4914(13) . ? N3 N4 1.1805(18) . ? N4 N5 1.153(2) . ? C1 C2 1.5000(16) . ? C1 H1A 0.9900 . ? C1 H1B 0.9900 . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C3 C4 1.5087(14) . ? C3 H3A 0.9900 . ? C3 H3B 0.9900 . ? C4 C3 1.5087(14) 7_565 ? C4 H4A 0.9900 . ? C4 H4B 0.9900 . ? C5 C6 1.5227(13) . ? C5 H5A 0.9900 . ? C5 H5B 0.9900 . ? C6 C5 1.5227(13) 7_565 ? C6 H6A 0.9900 . ? C6 H6B 0.9900 . ? C7 H7A 0.9800 . ? C7 H7B 0.9800 . ? C7 H7C 0.9800 . ? C8 H8A 0.9800 . ? C8 H8B 0.9800 . ? C8 H8C 0.9800 . ? P1 F5 1.5899(10) . ? P1 F4 1.5965(7) . ? P1 F4 1.5965(6) 7_575 ? P1 F2 1.6005(9) . ? P1 F3 1.6005(10) . ? P1 F1 1.6200(10) . ? 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 Ni1 N1 101.42(3) . 7_565 ? N3 Ni1 N1 101.42(3) . . ? N1 Ni1 N1 94.24(5) 7_565 . ? N3 Ni1 N2 94.32(4) . 7_565 ? N1 Ni1 N2 84.85(3) 7_565 7_565 ? N1 Ni1 N2 164.09(3) . 7_565 ? N3 Ni1 N2 94.32(4) . . ? N1 Ni1 N2 164.09(3) 7_565 . ? N1 Ni1 N2 84.86(3) . . ? N2 Ni1 N2 91.68(5) 7_565 . ? C7 N1 C3 108.16(8) . . ? C7 N1 C1 109.60(8) . . ? C3 N1 C1 106.98(8) . . ? C7 N1 Ni1 110.53(6) . . ? C3 N1 Ni1 117.52(6) . . ? C1 N1 Ni1 103.75(6) . . ? C8 N2 C2 105.13(8) . . ? C8 N2 C5 109.88(8) . . ? C2 N2 C5 109.70(8) . . ? C8 N2 Ni1 117.26(7) . . ? C2 N2 Ni1 105.73(6) . . ? C5 N2 Ni1 108.85(6) . . ? N4 N3 Ni1 133.24(12) . . ? N5 N4 N3 177.4(2) . . ? N1 C1 C2 110.47(8) . . ? N1 C1 H1A 109.6 . . ? C2 C1 H1A 109.6 . . ? N1 C1 H1B 109.6 . . ? C2 C1 H1B 109.6 . . ? H1A C1 H1B 108.1 . . ? N2 C2 C1 111.22(8) . . ? N2 C2 H2A 109.4 . . ? C1 C2 H2A 109.4 . . ? N2 C2 H2B 109.4 . . ? C1 C2 H2B 109.4 . . ? H2A C2 H2B 108.0 . . ? N1 C3 C4 114.78(9) . . ? N1 C3 H3A 108.6 . . ? C4 C3 H3A 108.6 . . ? N1 C3 H3B 108.6 . . ? C4 C3 H3B 108.6 . . ? H3A C3 H3B 107.5 . . ? C3 C4 C3 113.29(12) . 7_565 ? C3 C4 H4A 108.9 . . ? C3 C4 H4A 108.9 7_565 . ? C3 C4 H4B 108.9 . . ? C3 C4 H4B 108.9 7_565 . ? H4A C4 H4B 107.7 . . ? N2 C5 C6 115.11(9) . . ? N2 C5 H5A 108.5 . . ? C6 C5 H5A 108.5 . . ? N2 C5 H5B 108.5 . . ? C6 C5 H5B 108.5 . . ? H5A C5 H5B 107.5 . . ? C5 C6 C5 117.31(12) . 7_565 ? C5 C6 H6A 108.0 . . ? C5 C6 H6A 108.0 7_565 . ? C5 C6 H6B 108.0 . . ? C5 C6 H6B 108.0 7_565 . ? H6A C6 H6B 107.2 . . ? N1 C7 H7A 109.5 . . ? N1 C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? N1 C7 H7C 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? N2 C8 H8A 109.5 . . ? N2 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? N2 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? F5 P1 F4 90.91(3) . . ? F5 P1 F4 90.91(3) . 7_575 ? F4 P1 F4 178.07(6) . 7_575 ? F5 P1 F2 90.60(5) . . ? F4 P1 F2 89.66(3) . . ? F4 P1 F2 89.66(3) 7_575 . ? F5 P1 F3 90.62(6) . . ? F4 P1 F3 90.32(3) . . ? F4 P1 F3 90.32(3) 7_575 . ? F2 P1 F3 178.78(6) . . ? F5 P1 F1 179.60(6) . . ? F4 P1 F1 89.09(3) . . ? F4 P1 F1 89.10(3) 7_575 . ? F2 P1 F1 89.80(5) . . ? F3 P1 F1 88.98(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 N3 Ni1 N1 C7 4.16(8) . . . . ? N1 Ni1 N1 C7 -98.40(7) 7_565 . . . ? N2 Ni1 N1 C7 175.52(11) 7_565 . . . ? N2 Ni1 N1 C7 97.54(7) . . . . ? N3 Ni1 N1 C3 128.94(7) . . . . ? N1 Ni1 N1 C3 26.38(8) 7_565 . . . ? N2 Ni1 N1 C3 -59.70(15) 7_565 . . . ? N2 Ni1 N1 C3 -137.68(7) . . . . ? N3 Ni1 N1 C1 -113.25(6) . . . . ? N1 Ni1 N1 C1 144.19(5) 7_565 . . . ? N2 Ni1 N1 C1 58.10(14) 7_565 . . . ? N2 Ni1 N1 C1 -19.87(6) . . . . ? N3 Ni1 N2 C8 -23.21(8) . . . . ? N1 Ni1 N2 C8 148.29(11) 7_565 . . . ? N1 Ni1 N2 C8 -124.31(8) . . . . ? N2 Ni1 N2 C8 71.25(8) 7_565 . . . ? N3 Ni1 N2 C2 93.54(7) . . . . ? N1 Ni1 N2 C2 -94.96(13) 7_565 . . . ? N1 Ni1 N2 C2 -7.56(6) . . . . ? N2 Ni1 N2 C2 -172.00(5) 7_565 . . . ? N3 Ni1 N2 C5 -148.68(7) . . . . ? N1 Ni1 N2 C5 22.82(16) 7_565 . . . ? N1 Ni1 N2 C5 110.22(7) . . . . ? N2 Ni1 N2 C5 -54.22(7) 7_565 . . . ? N1 Ni1 N3 N4 48.38(2) 7_565 . . . ? N1 Ni1 N3 N4 -48.38(2) . . . . ? N2 Ni1 N3 N4 133.99(2) 7_565 . . . ? N2 Ni1 N3 N4 -133.99(2) . . . . ? C7 N1 C1 C2 -73.14(10) . . . . ? C3 N1 C1 C2 169.82(8) . . . . ? Ni1 N1 C1 C2 44.92(9) . . . . ? C8 N2 C2 C1 159.40(9) . . . . ? C5 N2 C2 C1 -82.50(10) . . . . ? Ni1 N2 C2 C1 34.71(9) . . . . ? N1 C1 C2 N2 -56.28(11) . . . . ? C7 N1 C3 C4 75.55(11) . . . . ? C1 N1 C3 C4 -166.47(9) . . . . ? Ni1 N1 C3 C4 -50.41(11) . . . . ? N1 C3 C4 C3 72.75(15) . . . 7_565 ? C8 N2 C5 C6 -66.61(12) . . . . ? C2 N2 C5 C6 178.29(9) . . . . ? Ni1 N2 C5 C6 63.05(10) . . . . ? N2 C5 C6 C5 -63.70(16) . . . 7_565 ? _diffrn_measured_fraction_theta_max 0.992 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.743 _refine_diff_density_min -0.559 _refine_diff_density_rms 0.069 #===END data_l19210 _database_code_depnum_ccdc_archive 'CCDC 864405' #TrackingRef '- Cif_Combined3New.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C14 H32 Co N7, Cl O4' _chemical_formula_sum 'C14 H32 Cl Co N7 O4' _chemical_formula_weight 456.85 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' Cl Cl 0.1484 0.1585 '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 Orthorhombic _symmetry_space_group_name_H-M Pna2(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z+1/2' 'x+1/2, -y+1/2, z' '-x+1/2, y+1/2, z+1/2' _cell_length_a 13.9561(9) _cell_length_b 15.2417(10) _cell_length_c 9.2732(5) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1972.5(2) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 9963 _cell_measurement_theta_min 2.57 _cell_measurement_theta_max 27.12 _exptl_crystal_description rod _exptl_crystal_colour purple _exptl_crystal_size_max 0.45 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas no _exptl_crystal_density_diffrn 1.538 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 964 _exptl_absorpt_coefficient_mu 1.042 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6509 _exptl_absorpt_correction_T_max 0.9075 _exptl_absorpt_process_details 'sadabs v2008/1' _exptl_special_details ; All H atoms were added in their calculated positions and were treated using appropriate riding models. ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 23032 _diffrn_reflns_av_R_equivalents 0.0294 _diffrn_reflns_av_sigmaI/netI 0.0263 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 1.98 _diffrn_reflns_theta_max 27.23 _reflns_number_total 4337 _reflns_number_gt 4055 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0270P)^2^+0.1884P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.137(9) _refine_ls_number_reflns 4337 _refine_ls_number_parameters 249 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0244 _refine_ls_R_factor_gt 0.0214 _refine_ls_wR_factor_ref 0.0506 _refine_ls_wR_factor_gt 0.0495 _refine_ls_goodness_of_fit_ref 1.034 _refine_ls_restrained_S_all 1.033 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Co1 Co 0.764563(14) 0.877522(12) 0.00141(3) 0.01004(5) Uani 1 1 d . . . N1 N 0.85210(11) 0.87942(9) 0.18812(16) 0.0123(3) Uani 1 1 d . . . N2 N 0.88669(11) 0.84935(10) -0.14454(16) 0.0138(3) Uani 1 1 d . . . N3 N 0.71796(10) 0.95860(9) -0.16968(16) 0.0134(3) Uani 1 1 d . . . N4 N 0.65441(10) 0.93240(9) 0.15143(16) 0.0136(3) Uani 1 1 d . . . N5 N 0.70174(10) 0.76183(8) -0.0137(2) 0.0172(3) Uani 1 1 d . . . N6 N 0.72990(11) 0.68890(10) -0.02363(18) 0.0191(4) Uani 1 1 d . . . N7 N 0.75512(12) 0.61657(10) -0.0320(2) 0.0291(5) Uani 1 1 d . . . C1 C 0.95084(13) 0.91501(11) 0.1707(2) 0.0151(4) Uani 1 1 d . . . H1A H 0.9855 0.9074 0.2631 0.018 Uiso 1 1 calc R . . H1B H 0.9461 0.9788 0.1520 0.018 Uiso 1 1 calc R . . C2 C 1.00978(13) 0.87404(12) 0.0523(2) 0.0155(4) Uani 1 1 d . . . H2A H 1.0090 0.8096 0.0650 0.019 Uiso 1 1 calc R . . H2B H 1.0770 0.8939 0.0628 0.019 Uiso 1 1 calc R . . C3 C 0.97602(13) 0.89540(13) -0.0993(2) 0.0166(4) Uani 1 1 d . . . H3A H 0.9652 0.9595 -0.1062 0.020 Uiso 1 1 calc R . . H3B H 1.0278 0.8801 -0.1679 0.020 Uiso 1 1 calc R . . C4 C 0.85574(14) 0.88494(12) -0.2862(2) 0.0178(4) Uani 1 1 d . . . H4A H 0.8136 0.8419 -0.3349 0.021 Uiso 1 1 calc R . . H4B H 0.9125 0.8947 -0.3481 0.021 Uiso 1 1 calc R . . C5 C 0.80261(14) 0.97043(13) -0.2664(2) 0.0170(4) Uani 1 1 d . . . H5A H 0.8463 1.0147 -0.2243 0.020 Uiso 1 1 calc R . . H5B H 0.7809 0.9924 -0.3614 0.020 Uiso 1 1 calc R . . C6 C 0.68364(13) 1.04867(11) -0.1335(2) 0.0166(4) Uani 1 1 d . . . H6A H 0.6598 1.0767 -0.2228 0.020 Uiso 1 1 calc R . . H6B H 0.7390 1.0835 -0.0991 0.020 Uiso 1 1 calc R . . C7 C 0.60528(11) 1.05316(11) -0.0205(2) 0.0170(4) Uani 1 1 d . . . H7A H 0.5524 1.0137 -0.0499 0.020 Uiso 1 1 calc R . . H7B H 0.5796 1.1137 -0.0179 0.020 Uiso 1 1 calc R . . C8 C 0.63754(13) 1.02785(11) 0.1308(2) 0.0166(4) Uani 1 1 d . . . H8A H 0.6975 1.0598 0.1533 0.020 Uiso 1 1 calc R . . H8B H 0.5882 1.0474 0.2005 0.020 Uiso 1 1 calc R . . C9 C 0.69635(13) 0.91816(12) 0.29723(19) 0.0177(4) Uani 1 1 d . . . H9A H 0.6845 0.8569 0.3280 0.021 Uiso 1 1 calc R . . H9B H 0.6648 0.9577 0.3674 0.021 Uiso 1 1 calc R . . C10 C 0.80274(13) 0.93577(12) 0.2962(2) 0.0167(4) Uani 1 1 d . . . H10A H 0.8143 0.9983 0.2730 0.020 Uiso 1 1 calc R . . H10B H 0.8295 0.9240 0.3932 0.020 Uiso 1 1 calc R . . C11 C 0.85768(14) 0.78810(11) 0.2437(2) 0.0174(4) Uani 1 1 d . . . H11A H 0.8930 0.7876 0.3351 0.026 Uiso 1 1 calc R . . H11B H 0.8910 0.7511 0.1733 0.026 Uiso 1 1 calc R . . H11C H 0.7928 0.7654 0.2594 0.026 Uiso 1 1 calc R . . C12 C 0.90927(14) 0.75509(12) -0.1663(2) 0.0211(4) Uani 1 1 d . . . H12A H 0.9645 0.7496 -0.2310 0.032 Uiso 1 1 calc R . . H12B H 0.8538 0.7255 -0.2091 0.032 Uiso 1 1 calc R . . H12C H 0.9244 0.7280 -0.0732 0.032 Uiso 1 1 calc R . . C13 C 0.64203(14) 0.91123(13) -0.2489(2) 0.0191(4) Uani 1 1 d . . . H13A H 0.6234 0.9452 -0.3341 0.029 Uiso 1 1 calc R . . H13B H 0.5863 0.9034 -0.1861 0.029 Uiso 1 1 calc R . . H13C H 0.6661 0.8537 -0.2792 0.029 Uiso 1 1 calc R . . C14 C 0.56204(13) 0.88470(12) 0.1467(2) 0.0187(4) Uani 1 1 d . . . H14A H 0.5190 0.9082 0.2207 0.028 Uiso 1 1 calc R . . H14B H 0.5733 0.8222 0.1648 0.028 Uiso 1 1 calc R . . H14C H 0.5327 0.8921 0.0514 0.028 Uiso 1 1 calc R . . Cl1 Cl 0.88258(3) 1.19941(2) -0.01088(5) 0.01490(8) Uani 1 1 d . . . O1 O 0.91062(12) 1.11336(9) 0.03686(16) 0.0339(4) Uani 1 1 d . . . O2 O 0.79326(11) 1.22371(10) 0.05610(16) 0.0293(3) Uani 1 1 d . . . O3 O 0.86979(9) 1.19685(9) -0.16475(14) 0.0223(3) Uani 1 1 d . . . O4 O 0.95542(10) 1.26209(9) 0.02602(16) 0.0289(4) 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 Co1 0.01038(9) 0.00914(9) 0.01059(11) -0.00004(11) -0.00021(12) -0.00044(7) N1 0.0125(7) 0.0124(7) 0.0119(8) 0.0005(6) 0.0012(6) 0.0021(6) N2 0.0140(7) 0.0141(7) 0.0132(8) -0.0007(6) 0.0006(6) -0.0006(6) N3 0.0131(7) 0.0136(7) 0.0135(8) -0.0006(6) -0.0003(6) 0.0015(6) N4 0.0136(7) 0.0124(7) 0.0148(8) -0.0009(6) 0.0002(6) 0.0001(6) N5 0.0200(7) 0.0114(6) 0.0201(8) -0.0010(7) 0.0037(8) -0.0044(5) N6 0.0207(7) 0.0184(7) 0.0182(10) -0.0001(7) 0.0041(6) -0.0044(6) N7 0.0347(10) 0.0128(7) 0.0399(15) -0.0009(7) 0.0120(8) 0.0011(6) C1 0.0131(9) 0.0139(8) 0.0183(10) 0.0017(7) -0.0042(7) -0.0010(7) C2 0.0092(8) 0.0176(9) 0.0198(9) 0.0024(7) 0.0000(6) -0.0017(7) C3 0.0111(9) 0.0220(9) 0.0169(10) 0.0023(8) 0.0007(7) -0.0003(7) C4 0.0179(9) 0.0220(9) 0.0136(10) -0.0012(8) 0.0008(7) 0.0011(7) C5 0.0182(9) 0.0208(9) 0.0120(10) 0.0029(7) 0.0007(7) 0.0011(8) C6 0.0177(10) 0.0120(8) 0.0201(10) 0.0016(7) -0.0019(7) 0.0011(7) C7 0.0163(8) 0.0149(7) 0.0198(11) 0.0002(8) -0.0040(8) 0.0050(6) C8 0.0168(9) 0.0130(8) 0.0201(10) -0.0040(7) 0.0004(7) 0.0034(7) C9 0.0194(9) 0.0206(9) 0.0130(9) 0.0002(7) 0.0038(7) 0.0021(8) C10 0.0198(9) 0.0180(9) 0.0123(10) -0.0030(7) -0.0030(7) 0.0021(8) C11 0.0169(9) 0.0166(9) 0.0187(10) 0.0049(7) 0.0007(7) 0.0017(7) C12 0.0214(10) 0.0188(9) 0.0230(10) -0.0037(8) 0.0050(8) 0.0018(8) C13 0.0202(10) 0.0214(10) 0.0158(10) -0.0027(8) -0.0047(7) 0.0014(8) C14 0.0135(9) 0.0192(9) 0.0235(10) -0.0025(8) 0.0046(7) -0.0016(7) Cl1 0.01617(17) 0.01317(16) 0.0154(2) -0.00012(19) -0.0013(2) 0.00119(13) O1 0.0503(10) 0.0188(7) 0.0324(10) 0.0066(6) -0.0140(7) 0.0086(6) O2 0.0238(8) 0.0329(8) 0.0311(8) -0.0125(6) 0.0099(6) -0.0014(6) O3 0.0270(7) 0.0245(7) 0.0152(7) 0.0003(6) -0.0006(6) 0.0016(6) O4 0.0232(7) 0.0308(7) 0.0326(10) -0.0060(6) -0.0022(6) -0.0110(5) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Co1 N5 1.9742(13) . ? Co1 N3 2.1136(15) . ? Co1 N1 2.1192(15) . ? Co1 N2 2.2184(15) . ? Co1 N4 2.2357(15) . ? N1 C11 1.486(2) . ? N1 C10 1.489(2) . ? N1 C1 1.490(2) . ? N2 C12 1.485(2) . ? N2 C4 1.485(2) . ? N2 C3 1.491(2) . ? N3 C13 1.478(2) . ? N3 C6 1.492(2) . ? N3 C5 1.494(2) . ? N4 C14 1.481(2) . ? N4 C8 1.486(2) . ? N4 C9 1.489(2) . ? N5 N6 1.183(2) . ? N6 N7 1.160(2) . ? C1 C2 1.507(3) . ? C1 H1A 0.9900 . ? C1 H1B 0.9900 . ? C2 C3 1.518(3) . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C3 H3A 0.9900 . ? C3 H3B 0.9900 . ? C4 C5 1.510(3) . ? C4 H4A 0.9900 . ? C4 H4B 0.9900 . ? C5 H5A 0.9900 . ? C5 H5B 0.9900 . ? C6 C7 1.516(3) . ? C6 H6A 0.9900 . ? C6 H6B 0.9900 . ? C7 C8 1.523(3) . ? C7 H7A 0.9900 . ? C7 H7B 0.9900 . ? C8 H8A 0.9900 . ? C8 H8B 0.9900 . ? C9 C10 1.509(3) . ? C9 H9A 0.9900 . ? C9 H9B 0.9900 . ? C10 H10A 0.9900 . ? C10 H10B 0.9900 . ? C11 H11A 0.9800 . ? C11 H11B 0.9800 . ? C11 H11C 0.9800 . ? C12 H12A 0.9800 . ? C12 H12B 0.9800 . ? C12 H12C 0.9800 . ? C13 H13A 0.9800 . ? C13 H13B 0.9800 . ? C13 H13C 0.9800 . ? C14 H14A 0.9800 . ? C14 H14B 0.9800 . ? C14 H14C 0.9800 . ? Cl1 O4 1.4363(13) . ? Cl1 O3 1.4385(14) . ? Cl1 O1 1.4386(13) . ? Cl1 O2 1.4411(14) . ? 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 N5 Co1 N3 109.42(7) . . ? N5 Co1 N1 109.03(7) . . ? N3 Co1 N1 141.50(6) . . ? N5 Co1 N2 97.19(6) . . ? N3 Co1 N2 83.78(6) . . ? N1 Co1 N2 93.34(6) . . ? N5 Co1 N4 94.18(6) . . ? N3 Co1 N4 92.11(6) . . ? N1 Co1 N4 83.27(6) . . ? N2 Co1 N4 168.63(5) . . ? C11 N1 C10 109.33(15) . . ? C11 N1 C1 109.27(13) . . ? C10 N1 C1 106.90(14) . . ? C11 N1 Co1 107.50(11) . . ? C10 N1 Co1 106.93(11) . . ? C1 N1 Co1 116.73(11) . . ? C12 N2 C4 107.16(14) . . ? C12 N2 C3 108.44(15) . . ? C4 N2 C3 108.66(14) . . ? C12 N2 Co1 115.68(11) . . ? C4 N2 Co1 104.20(11) . . ? C3 N2 Co1 112.32(11) . . ? C13 N3 C6 109.34(14) . . ? C13 N3 C5 109.11(15) . . ? C6 N3 C5 106.14(14) . . ? C13 N3 Co1 107.95(11) . . ? C6 N3 Co1 117.88(11) . . ? C5 N3 Co1 106.13(11) . . ? C14 N4 C8 109.81(14) . . ? C14 N4 C9 107.32(14) . . ? C8 N4 C9 108.79(13) . . ? C14 N4 Co1 113.35(11) . . ? C8 N4 Co1 113.26(11) . . ? C9 N4 Co1 103.90(10) . . ? N6 N5 Co1 134.22(12) . . ? N7 N6 N5 178.13(19) . . ? N1 C1 C2 115.65(14) . . ? N1 C1 H1A 108.4 . . ? C2 C1 H1A 108.4 . . ? N1 C1 H1B 108.4 . . ? C2 C1 H1B 108.4 . . ? H1A C1 H1B 107.4 . . ? C1 C2 C3 114.62(15) . . ? C1 C2 H2A 108.6 . . ? C3 C2 H2A 108.6 . . ? C1 C2 H2B 108.6 . . ? C3 C2 H2B 108.6 . . ? H2A C2 H2B 107.6 . . ? N2 C3 C2 114.77(15) . . ? N2 C3 H3A 108.6 . . ? C2 C3 H3A 108.6 . . ? N2 C3 H3B 108.6 . . ? C2 C3 H3B 108.6 . . ? H3A C3 H3B 107.6 . . ? N2 C4 C5 110.51(15) . . ? N2 C4 H4A 109.5 . . ? C5 C4 H4A 109.5 . . ? N2 C4 H4B 109.5 . . ? C5 C4 H4B 109.5 . . ? H4A C4 H4B 108.1 . . ? N3 C5 C4 110.92(15) . . ? N3 C5 H5A 109.5 . . ? C4 C5 H5A 109.5 . . ? N3 C5 H5B 109.5 . . ? C4 C5 H5B 109.5 . . ? H5A C5 H5B 108.0 . . ? N3 C6 C7 115.38(15) . . ? N3 C6 H6A 108.4 . . ? C7 C6 H6A 108.4 . . ? N3 C6 H6B 108.4 . . ? C7 C6 H6B 108.4 . . ? H6A C6 H6B 107.5 . . ? C6 C7 C8 114.31(14) . . ? C6 C7 H7A 108.7 . . ? C8 C7 H7A 108.7 . . ? C6 C7 H7B 108.7 . . ? C8 C7 H7B 108.7 . . ? H7A C7 H7B 107.6 . . ? N4 C8 C7 114.43(14) . . ? N4 C8 H8A 108.7 . . ? C7 C8 H8A 108.7 . . ? N4 C8 H8B 108.7 . . ? C7 C8 H8B 108.7 . . ? H8A C8 H8B 107.6 . . ? N4 C9 C10 110.80(15) . . ? N4 C9 H9A 109.5 . . ? C10 C9 H9A 109.5 . . ? N4 C9 H9B 109.5 . . ? C10 C9 H9B 109.5 . . ? H9A C9 H9B 108.1 . . ? N1 C10 C9 110.91(15) . . ? N1 C10 H10A 109.5 . . ? C9 C10 H10A 109.5 . . ? N1 C10 H10B 109.5 . . ? C9 C10 H10B 109.5 . . ? H10A C10 H10B 108.0 . . ? N1 C11 H11A 109.5 . . ? N1 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? N1 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? N2 C12 H12A 109.5 . . ? N2 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? N2 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? N3 C13 H13A 109.5 . . ? N3 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? N3 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? N4 C14 H14A 109.5 . . ? N4 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? N4 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? O4 Cl1 O3 110.01(9) . . ? O4 Cl1 O1 109.91(9) . . ? O3 Cl1 O1 108.32(8) . . ? O4 Cl1 O2 109.79(9) . . ? O3 Cl1 O2 109.09(9) . . ? O1 Cl1 O2 109.69(10) . . ? 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 N5 Co1 N1 C11 10.44(13) . . . . ? N3 Co1 N1 C11 -172.54(10) . . . . ? N2 Co1 N1 C11 -88.34(11) . . . . ? N4 Co1 N1 C11 102.56(11) . . . . ? N5 Co1 N1 C10 -106.87(12) . . . . ? N3 Co1 N1 C10 70.15(15) . . . . ? N2 Co1 N1 C10 154.35(12) . . . . ? N4 Co1 N1 C10 -14.75(11) . . . . ? N5 Co1 N1 C1 133.55(11) . . . . ? N3 Co1 N1 C1 -49.43(16) . . . . ? N2 Co1 N1 C1 34.76(12) . . . . ? N4 Co1 N1 C1 -134.34(12) . . . . ? N5 Co1 N2 C12 -21.15(14) . . . . ? N3 Co1 N2 C12 -130.02(13) . . . . ? N1 Co1 N2 C12 88.51(13) . . . . ? N4 Co1 N2 C12 160.7(2) . . . . ? N5 Co1 N2 C4 96.19(11) . . . . ? N3 Co1 N2 C4 -12.67(11) . . . . ? N1 Co1 N2 C4 -154.14(11) . . . . ? N4 Co1 N2 C4 -81.9(3) . . . . ? N5 Co1 N2 C3 -146.38(12) . . . . ? N3 Co1 N2 C3 104.76(12) . . . . ? N1 Co1 N2 C3 -36.71(12) . . . . ? N4 Co1 N2 C3 35.5(3) . . . . ? N5 Co1 N3 C13 5.91(13) . . . . ? N1 Co1 N3 C13 -171.10(11) . . . . ? N2 Co1 N3 C13 101.36(12) . . . . ? N4 Co1 N3 C13 -89.27(11) . . . . ? N5 Co1 N3 C6 130.33(12) . . . . ? N1 Co1 N3 C6 -46.68(16) . . . . ? N2 Co1 N3 C6 -134.21(13) . . . . ? N4 Co1 N3 C6 35.16(13) . . . . ? N5 Co1 N3 C5 -110.96(12) . . . . ? N1 Co1 N3 C5 72.03(14) . . . . ? N2 Co1 N3 C5 -15.51(11) . . . . ? N4 Co1 N3 C5 153.86(11) . . . . ? N5 Co1 N4 C14 -20.75(13) . . . . ? N3 Co1 N4 C14 88.89(12) . . . . ? N1 Co1 N4 C14 -129.45(12) . . . . ? N2 Co1 N4 C14 157.4(3) . . . . ? N5 Co1 N4 C8 -146.73(12) . . . . ? N3 Co1 N4 C8 -37.08(12) . . . . ? N1 Co1 N4 C8 104.58(12) . . . . ? N2 Co1 N4 C8 31.4(3) . . . . ? N5 Co1 N4 C9 95.40(11) . . . . ? N3 Co1 N4 C9 -154.95(10) . . . . ? N1 Co1 N4 C9 -13.29(10) . . . . ? N2 Co1 N4 C9 -86.5(3) . . . . ? N3 Co1 N5 N6 122.3(2) . . . . ? N1 Co1 N5 N6 -59.7(2) . . . . ? N2 Co1 N5 N6 36.4(2) . . . . ? N4 Co1 N5 N6 -144.0(2) . . . . ? C11 N1 C1 C2 68.87(19) . . . . ? C10 N1 C1 C2 -172.92(15) . . . . ? Co1 N1 C1 C2 -53.32(17) . . . . ? N1 C1 C2 C3 69.3(2) . . . . ? C12 N2 C3 C2 -71.03(18) . . . . ? C4 N2 C3 C2 172.81(14) . . . . ? Co1 N2 C3 C2 58.06(17) . . . . ? C1 C2 C3 N2 -73.7(2) . . . . ? C12 N2 C4 C5 162.22(15) . . . . ? C3 N2 C4 C5 -80.80(18) . . . . ? Co1 N2 C4 C5 39.13(16) . . . . ? C13 N3 C5 C4 -73.76(18) . . . . ? C6 N3 C5 C4 168.52(15) . . . . ? Co1 N3 C5 C4 42.33(17) . . . . ? N2 C4 C5 N3 -57.5(2) . . . . ? C13 N3 C6 C7 69.85(19) . . . . ? C5 N3 C6 C7 -172.59(15) . . . . ? Co1 N3 C6 C7 -53.89(19) . . . . ? N3 C6 C7 C8 68.9(2) . . . . ? C14 N4 C8 C7 -69.45(19) . . . . ? C9 N4 C8 C7 173.37(15) . . . . ? Co1 N4 C8 C7 58.38(17) . . . . ? C6 C7 C8 N4 -73.2(2) . . . . ? C14 N4 C9 C10 159.91(14) . . . . ? C8 N4 C9 C10 -81.33(17) . . . . ? Co1 N4 C9 C10 39.59(15) . . . . ? C11 N1 C10 C9 -74.52(18) . . . . ? C1 N1 C10 C9 167.31(14) . . . . ? Co1 N1 C10 C9 41.58(17) . . . . ? N4 C9 C10 N1 -57.28(19) . . . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.303 _refine_diff_density_min -0.267 _refine_diff_density_rms 0.045 #===END data_l1611 _database_code_depnum_ccdc_archive 'CCDC 864406' #TrackingRef '- Cif_Combined3New.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C12 H25 Co N7 O2, Cl O4' _chemical_formula_sum 'C12 H25 Cl Co N7 O6' _chemical_formula_weight 457.77 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' 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' Cl Cl 0.1484 0.1585 '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 Orthorhombic _symmetry_space_group_name_H-M Pbca loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' '-x, -y, -z' 'x-1/2, y, -z-1/2' 'x, -y-1/2, z-1/2' '-x-1/2, y-1/2, z' _cell_length_a 13.4690(11) _cell_length_b 13.3584(12) _cell_length_c 20.0722(14) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 3611.5(5) _cell_formula_units_Z 8 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 5687 _cell_measurement_theta_min 2.38 _cell_measurement_theta_max 24.89 _exptl_crystal_description needle _exptl_crystal_colour purple _exptl_crystal_size_max 0.18 _exptl_crystal_size_mid 0.07 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas no _exptl_crystal_density_diffrn 1.684 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1904 _exptl_absorpt_coefficient_mu 1.146 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8185 _exptl_absorpt_correction_T_max 0.9439 _exptl_absorpt_process_details 'sadabs v2008/1' _exptl_special_details ; NH H atoms were located and refined with geometrical restraints. All other H atoms were added in their calculated positions and were treated using appropriate riding models. ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 80818 _diffrn_reflns_av_R_equivalents 0.1365 _diffrn_reflns_av_sigmaI/netI 0.0513 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -26 _diffrn_reflns_limit_l_max 26 _diffrn_reflns_theta_min 2.03 _diffrn_reflns_theta_max 27.71 _reflns_number_total 4182 _reflns_number_gt 2891 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0351P)^2^+1.6879P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4182 _refine_ls_number_parameters 256 _refine_ls_number_restraints 3 _refine_ls_R_factor_all 0.0734 _refine_ls_R_factor_gt 0.0374 _refine_ls_wR_factor_ref 0.0853 _refine_ls_wR_factor_gt 0.0725 _refine_ls_goodness_of_fit_ref 1.040 _refine_ls_restrained_S_all 1.040 _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 0.19714(2) 0.32614(3) 0.143599(16) 0.01083(9) Uani 1 1 d . . . Cl1 Cl 0.23524(5) 0.44038(5) 0.38824(3) 0.02224(17) Uani 1 1 d . . . O1 O 0.22815(13) 0.46326(13) 0.12964(8) 0.0136(4) Uani 1 1 d . . . O2 O 0.18349(15) 0.59426(14) 0.06974(10) 0.0226(5) Uani 1 1 d . . . O3 O 0.15816(17) 0.45009(17) 0.43701(10) 0.0343(6) Uani 1 1 d . . . O4 O 0.27023(19) 0.33958(17) 0.38635(11) 0.0399(6) Uani 1 1 d . . . O5 O 0.19809(17) 0.46716(17) 0.32366(10) 0.0342(5) Uani 1 1 d . . . O6 O 0.3160(2) 0.5053(2) 0.40478(12) 0.0513(8) Uani 1 1 d . . . N1 N 0.28035(16) 0.31847(18) 0.22368(10) 0.0140(5) Uani 1 1 d D . . N2 N 0.31212(17) 0.29907(18) 0.08363(11) 0.0150(5) Uani 1 1 d D . . N3 N 0.11430(15) 0.33374(16) 0.06214(10) 0.0125(4) Uani 1 1 d . . . N4 N 0.16279(16) 0.18549(17) 0.16251(10) 0.0121(5) Uani 1 1 d D . . N5 N 0.08550(16) 0.36266(17) 0.19927(11) 0.0147(5) Uani 1 1 d . . . N6 N 0.06479(16) 0.45009(19) 0.20575(10) 0.0161(5) Uani 1 1 d . . . N7 N 0.03889(19) 0.53133(19) 0.21351(12) 0.0244(6) Uani 1 1 d . . . C1 C 0.3786(2) 0.3680(2) 0.22268(13) 0.0164(6) Uani 1 1 d . . . H1A H 0.4115 0.3573 0.2662 0.020 Uiso 1 1 calc R . . H1B H 0.3689 0.4409 0.2169 0.020 Uiso 1 1 calc R . . C2 C 0.44618(19) 0.3298(2) 0.16777(13) 0.0195(6) Uani 1 1 d . . . H2A H 0.5123 0.3612 0.1727 0.023 Uiso 1 1 calc R . . H2B H 0.4546 0.2566 0.1729 0.023 Uiso 1 1 calc R . . C3 C 0.40671(19) 0.3517(2) 0.09874(13) 0.0175(6) Uani 1 1 d . . . H3A H 0.3961 0.4247 0.0943 0.021 Uiso 1 1 calc R . . H3B H 0.4572 0.3317 0.0655 0.021 Uiso 1 1 calc R . . C4 C 0.28015(18) 0.3241(2) 0.01483(12) 0.0161(6) Uani 1 1 d . . . H4A H 0.3229 0.2892 -0.0179 0.019 Uiso 1 1 calc R . . H4B H 0.2861 0.3971 0.0072 0.019 Uiso 1 1 calc R . . C5 C 0.17473(19) 0.2920(2) 0.00634(13) 0.0154(6) Uani 1 1 d . . . H5A H 0.1488 0.3167 -0.0368 0.018 Uiso 1 1 calc R . . H5B H 0.1706 0.2181 0.0065 0.018 Uiso 1 1 calc R . . C6 C 0.01629(19) 0.2816(2) 0.06403(14) 0.0164(6) Uani 1 1 d . . . H6A H -0.0159 0.2886 0.0199 0.020 Uiso 1 1 calc R . . H6B H -0.0266 0.3153 0.0972 0.020 Uiso 1 1 calc R . . C7 C 0.0225(2) 0.1715(2) 0.08127(13) 0.0174(6) Uani 1 1 d . . . H7A H -0.0440 0.1409 0.0759 0.021 Uiso 1 1 calc R . . H7B H 0.0681 0.1381 0.0496 0.021 Uiso 1 1 calc R . . C8 C 0.05866(19) 0.1533(2) 0.15145(13) 0.0166(6) Uani 1 1 d . . . H8A H 0.0150 0.1897 0.1829 0.020 Uiso 1 1 calc R . . H8B H 0.0531 0.0809 0.1615 0.020 Uiso 1 1 calc R . . C9 C 0.1892(2) 0.1652(2) 0.23352(12) 0.0168(6) Uani 1 1 d . . . H9A H 0.1384 0.1939 0.2636 0.020 Uiso 1 1 calc R . . H9B H 0.1931 0.0922 0.2416 0.020 Uiso 1 1 calc R . . C10 C 0.2875(2) 0.2129(2) 0.24595(13) 0.0178(6) Uani 1 1 d . . . H10A H 0.3040 0.2099 0.2940 0.021 Uiso 1 1 calc R . . H10B H 0.3401 0.1776 0.2208 0.021 Uiso 1 1 calc R . . C11 C 0.0964(2) 0.4427(2) 0.05219(13) 0.0149(6) Uani 1 1 d . . . H11A H 0.0308 0.4606 0.0709 0.018 Uiso 1 1 calc R . . H11B H 0.0950 0.4575 0.0039 0.018 Uiso 1 1 calc R . . C12 C 0.1751(2) 0.5059(2) 0.08478(13) 0.0152(6) Uani 1 1 d . . . H1 H 0.2446(19) 0.3506(18) 0.2509(12) 0.013(7) Uiso 1 1 d D . . H2 H 0.319(2) 0.2362(13) 0.0846(14) 0.020(8) Uiso 1 1 d D . . H4 H 0.198(2) 0.1473(19) 0.1389(13) 0.022(9) Uiso 1 1 d D . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Co1 0.00846(16) 0.01232(17) 0.01171(16) -0.00039(15) 0.00012(14) -0.00024(15) Cl1 0.0280(4) 0.0254(4) 0.0133(3) -0.0029(3) -0.0008(3) -0.0041(3) O1 0.0104(9) 0.0152(10) 0.0152(9) -0.0019(7) 0.0011(7) 0.0008(8) O2 0.0309(13) 0.0139(10) 0.0230(11) 0.0007(8) -0.0021(9) -0.0016(9) O3 0.0396(14) 0.0371(14) 0.0261(12) -0.0016(11) 0.0108(10) 0.0018(11) O4 0.0551(16) 0.0345(14) 0.0302(12) 0.0040(10) 0.0063(11) 0.0107(12) O5 0.0430(14) 0.0380(14) 0.0215(11) 0.0009(10) -0.0072(10) 0.0038(12) O6 0.0514(17) 0.0689(19) 0.0337(14) -0.0129(13) -0.0050(12) -0.0331(15) N1 0.0112(12) 0.0165(12) 0.0144(11) -0.0026(10) -0.0001(8) 0.0003(10) N2 0.0121(12) 0.0160(13) 0.0169(11) -0.0028(9) 0.0008(9) -0.0006(10) N3 0.0102(11) 0.0133(11) 0.0139(10) -0.0009(9) -0.0009(8) -0.0017(10) N4 0.0107(10) 0.0134(12) 0.0121(11) -0.0011(9) -0.0018(8) -0.0009(9) N5 0.0119(12) 0.0152(12) 0.0170(11) -0.0003(9) 0.0030(9) 0.0008(10) N6 0.0108(12) 0.0225(14) 0.0151(12) -0.0022(10) 0.0011(9) -0.0026(10) N7 0.0197(14) 0.0219(15) 0.0314(15) -0.0044(11) 0.0088(11) 0.0015(11) C1 0.0122(14) 0.0189(15) 0.0180(14) 0.0001(11) -0.0032(11) -0.0033(12) C2 0.0107(13) 0.0267(16) 0.0212(14) -0.0035(13) -0.0017(10) -0.0011(13) C3 0.0086(13) 0.0234(16) 0.0205(14) -0.0033(12) 0.0023(11) -0.0011(11) C4 0.0144(14) 0.0197(14) 0.0143(13) -0.0018(11) 0.0024(10) 0.0020(12) C5 0.0163(14) 0.0170(14) 0.0128(13) -0.0006(11) -0.0009(10) 0.0005(11) C6 0.0095(13) 0.0205(15) 0.0193(14) -0.0008(12) -0.0034(10) -0.0047(11) C7 0.0143(13) 0.0180(14) 0.0199(13) 0.0007(12) -0.0030(10) -0.0053(12) C8 0.0120(13) 0.0163(15) 0.0216(14) 0.0015(11) -0.0007(11) -0.0036(11) C9 0.0197(14) 0.0176(14) 0.0132(12) 0.0036(11) -0.0030(10) -0.0025(13) C10 0.0205(16) 0.0163(14) 0.0165(13) 0.0001(11) -0.0057(11) 0.0015(12) C11 0.0138(14) 0.0144(14) 0.0166(13) 0.0007(11) -0.0007(10) 0.0020(11) C12 0.0148(15) 0.0173(15) 0.0136(13) -0.0022(11) 0.0032(10) 0.0003(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 O1 1.8995(18) . ? Co1 N5 1.936(2) . ? Co1 N1 1.962(2) . ? Co1 N4 1.972(2) . ? Co1 N3 1.982(2) . ? Co1 N2 1.994(2) . ? Cl1 O4 1.427(2) . ? Cl1 O6 1.430(2) . ? Cl1 O3 1.433(2) . ? Cl1 O5 1.435(2) . ? O1 C12 1.283(3) . ? O2 C12 1.224(3) . ? N1 C1 1.479(3) . ? N1 C10 1.483(3) . ? N1 H1 0.845(17) . ? N2 C4 1.485(3) . ? N2 C3 1.486(3) . ? N2 H2 0.845(17) . ? N3 C11 1.489(3) . ? N3 C5 1.492(3) . ? N3 C6 1.493(3) . ? N4 C8 1.484(3) . ? N4 C9 1.494(3) . ? N4 H4 0.845(17) . ? N5 N6 1.208(3) . ? N6 N7 1.151(3) . ? C1 C2 1.518(4) . ? C1 H1A 0.9900 . ? C1 H1B 0.9900 . ? C2 C3 1.512(4) . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C3 H3A 0.9900 . ? C3 H3B 0.9900 . ? C4 C5 1.493(4) . ? C4 H4A 0.9900 . ? C4 H4B 0.9900 . ? C5 H5A 0.9900 . ? C5 H5B 0.9900 . ? C6 C7 1.513(4) . ? C6 H6A 0.9900 . ? C6 H6B 0.9900 . ? C7 C8 1.510(4) . ? C7 H7A 0.9900 . ? C7 H7B 0.9900 . ? C8 H8A 0.9900 . ? C8 H8B 0.9900 . ? C9 C10 1.490(4) . ? C9 H9A 0.9900 . ? C9 H9B 0.9900 . ? C10 H10A 0.9900 . ? C10 H10B 0.9900 . ? C11 C12 1.504(4) . ? C11 H11A 0.9900 . ? C11 H11B 0.9900 . ? 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 Co1 N5 90.74(9) . . ? O1 Co1 N1 92.61(9) . . ? N5 Co1 N1 89.08(9) . . ? O1 Co1 N4 177.21(8) . . ? N5 Co1 N4 86.95(9) . . ? N1 Co1 N4 85.79(9) . . ? O1 Co1 N3 87.29(8) . . ? N5 Co1 N3 91.49(9) . . ? N1 Co1 N3 179.42(9) . . ? N4 Co1 N3 94.33(9) . . ? O1 Co1 N2 85.13(9) . . ? N5 Co1 N2 175.68(10) . . ? N1 Co1 N2 92.37(9) . . ? N4 Co1 N2 97.22(10) . . ? N3 Co1 N2 87.05(9) . . ? O4 Cl1 O6 109.09(17) . . ? O4 Cl1 O3 110.05(14) . . ? O6 Cl1 O3 109.73(14) . . ? O4 Cl1 O5 109.05(13) . . ? O6 Cl1 O5 108.90(15) . . ? O3 Cl1 O5 109.99(14) . . ? C12 O1 Co1 114.13(17) . . ? C1 N1 C10 111.8(2) . . ? C1 N1 Co1 118.44(16) . . ? C10 N1 Co1 109.49(16) . . ? C1 N1 H1 106.9(19) . . ? C10 N1 H1 109.0(19) . . ? Co1 N1 H1 100.2(19) . . ? C4 N2 C3 109.4(2) . . ? C4 N2 Co1 107.17(16) . . ? C3 N2 Co1 117.17(16) . . ? C4 N2 H2 106(2) . . ? C3 N2 H2 112(2) . . ? Co1 N2 H2 105(2) . . ? C11 N3 C5 110.6(2) . . ? C11 N3 C6 108.5(2) . . ? C5 N3 C6 109.1(2) . . ? C11 N3 Co1 104.58(15) . . ? C5 N3 Co1 107.04(15) . . ? C6 N3 Co1 116.93(16) . . ? C8 N4 C9 108.4(2) . . ? C8 N4 Co1 118.00(17) . . ? C9 N4 Co1 107.50(16) . . ? C8 N4 H4 106(2) . . ? C9 N4 H4 107(2) . . ? Co1 N4 H4 110(2) . . ? N6 N5 Co1 119.03(18) . . ? N7 N6 N5 175.4(3) . . ? N1 C1 C2 113.3(2) . . ? N1 C1 H1A 108.9 . . ? C2 C1 H1A 108.9 . . ? N1 C1 H1B 108.9 . . ? C2 C1 H1B 108.9 . . ? H1A C1 H1B 107.7 . . ? C3 C2 C1 112.9(2) . . ? C3 C2 H2A 109.0 . . ? C1 C2 H2A 109.0 . . ? C3 C2 H2B 109.0 . . ? C1 C2 H2B 109.0 . . ? H2A C2 H2B 107.8 . . ? N2 C3 C2 113.4(2) . . ? N2 C3 H3A 108.9 . . ? C2 C3 H3A 108.9 . . ? N2 C3 H3B 108.9 . . ? C2 C3 H3B 108.9 . . ? H3A C3 H3B 107.7 . . ? N2 C4 C5 108.5(2) . . ? N2 C4 H4A 110.0 . . ? C5 C4 H4A 110.0 . . ? N2 C4 H4B 110.0 . . ? C5 C4 H4B 110.0 . . ? H4A C4 H4B 108.4 . . ? N3 C5 C4 109.0(2) . . ? N3 C5 H5A 109.9 . . ? C4 C5 H5A 109.9 . . ? N3 C5 H5B 109.9 . . ? C4 C5 H5B 109.9 . . ? H5A C5 H5B 108.3 . . ? N3 C6 C7 114.2(2) . . ? N3 C6 H6A 108.7 . . ? C7 C6 H6A 108.7 . . ? N3 C6 H6B 108.7 . . ? C7 C6 H6B 108.7 . . ? H6A C6 H6B 107.6 . . ? C8 C7 C6 112.8(2) . . ? C8 C7 H7A 109.0 . . ? C6 C7 H7A 109.0 . . ? C8 C7 H7B 109.0 . . ? C6 C7 H7B 109.0 . . ? H7A C7 H7B 107.8 . . ? N4 C8 C7 113.4(2) . . ? N4 C8 H8A 108.9 . . ? C7 C8 H8A 108.9 . . ? N4 C8 H8B 108.9 . . ? C7 C8 H8B 108.9 . . ? H8A C8 H8B 107.7 . . ? C10 C9 N4 107.1(2) . . ? C10 C9 H9A 110.3 . . ? N4 C9 H9A 110.3 . . ? C10 C9 H9B 110.3 . . ? N4 C9 H9B 110.3 . . ? H9A C9 H9B 108.6 . . ? N1 C10 C9 107.4(2) . . ? N1 C10 H10A 110.2 . . ? C9 C10 H10A 110.2 . . ? N1 C10 H10B 110.2 . . ? C9 C10 H10B 110.2 . . ? H10A C10 H10B 108.5 . . ? N3 C11 C12 112.1(2) . . ? N3 C11 H11A 109.2 . . ? C12 C11 H11A 109.2 . . ? N3 C11 H11B 109.2 . . ? C12 C11 H11B 109.2 . . ? H11A C11 H11B 107.9 . . ? O2 C12 O1 123.3(3) . . ? O2 C12 C11 119.9(2) . . ? O1 C12 C11 116.7(2) . . ? 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 N5 Co1 O1 C12 -80.87(18) . . . . ? N1 Co1 O1 C12 -169.98(18) . . . . ? N3 Co1 O1 C12 10.59(18) . . . . ? N2 Co1 O1 C12 97.86(18) . . . . ? O1 Co1 N1 C1 -42.1(2) . . . . ? N5 Co1 N1 C1 -132.8(2) . . . . ? N4 Co1 N1 C1 140.2(2) . . . . ? N2 Co1 N1 C1 43.1(2) . . . . ? O1 Co1 N1 C10 -171.91(17) . . . . ? N5 Co1 N1 C10 97.40(18) . . . . ? N4 Co1 N1 C10 10.39(17) . . . . ? N2 Co1 N1 C10 -86.68(18) . . . . ? O1 Co1 N2 C4 -73.79(17) . . . . ? N1 Co1 N2 C4 -166.21(17) . . . . ? N4 Co1 N2 C4 107.73(17) . . . . ? N3 Co1 N2 C4 13.74(17) . . . . ? O1 Co1 N2 C3 49.50(19) . . . . ? N1 Co1 N2 C3 -42.9(2) . . . . ? N4 Co1 N2 C3 -128.98(19) . . . . ? N3 Co1 N2 C3 137.03(19) . . . . ? O1 Co1 N3 C11 -18.81(15) . . . . ? N5 Co1 N3 C11 71.86(16) . . . . ? N4 Co1 N3 C11 158.91(15) . . . . ? N2 Co1 N3 C11 -104.06(16) . . . . ? O1 Co1 N3 C5 98.62(16) . . . . ? N5 Co1 N3 C5 -170.71(17) . . . . ? N4 Co1 N3 C5 -83.66(17) . . . . ? N2 Co1 N3 C5 13.36(17) . . . . ? O1 Co1 N3 C6 -138.74(19) . . . . ? N5 Co1 N3 C6 -48.07(19) . . . . ? N4 Co1 N3 C6 38.98(19) . . . . ? N2 Co1 N3 C6 136.00(19) . . . . ? N5 Co1 N4 C8 51.43(18) . . . . ? N1 Co1 N4 C8 140.73(19) . . . . ? N3 Co1 N4 C8 -39.84(19) . . . . ? N2 Co1 N4 C8 -127.41(18) . . . . ? N5 Co1 N4 C9 -71.39(17) . . . . ? N1 Co1 N4 C9 17.92(16) . . . . ? N3 Co1 N4 C9 -162.65(16) . . . . ? N2 Co1 N4 C9 109.78(17) . . . . ? O1 Co1 N5 N6 4.1(2) . . . . ? N1 Co1 N5 N6 96.7(2) . . . . ? N4 Co1 N5 N6 -177.5(2) . . . . ? N3 Co1 N5 N6 -83.2(2) . . . . ? C10 N1 C1 C2 70.3(3) . . . . ? Co1 N1 C1 C2 -58.4(3) . . . . ? N1 C1 C2 C3 64.1(3) . . . . ? C4 N2 C3 C2 -179.3(2) . . . . ? Co1 N2 C3 C2 58.6(3) . . . . ? C1 C2 C3 N2 -64.7(3) . . . . ? C3 N2 C4 C5 -166.3(2) . . . . ? Co1 N2 C4 C5 -38.3(2) . . . . ? C11 N3 C5 C4 75.2(3) . . . . ? C6 N3 C5 C4 -165.6(2) . . . . ? Co1 N3 C5 C4 -38.2(2) . . . . ? N2 C4 C5 N3 51.4(3) . . . . ? C11 N3 C6 C7 -173.8(2) . . . . ? C5 N3 C6 C7 65.6(3) . . . . ? Co1 N3 C6 C7 -55.9(3) . . . . ? N3 C6 C7 C8 65.8(3) . . . . ? C9 N4 C8 C7 179.1(2) . . . . ? Co1 N4 C8 C7 56.8(3) . . . . ? C6 C7 C8 N4 -65.6(3) . . . . ? C8 N4 C9 C10 -171.1(2) . . . . ? Co1 N4 C9 C10 -42.5(2) . . . . ? C1 N1 C10 C9 -169.9(2) . . . . ? Co1 N1 C10 C9 -36.6(2) . . . . ? N4 C9 C10 N1 51.9(3) . . . . ? C5 N3 C11 C12 -91.3(2) . . . . ? C6 N3 C11 C12 149.1(2) . . . . ? Co1 N3 C11 C12 23.7(2) . . . . ? Co1 O1 C12 O2 178.9(2) . . . . ? Co1 O1 C12 C11 1.5(3) . . . . ? N3 C11 C12 O2 164.4(2) . . . . ? N3 C11 C12 O1 -18.1(3) . . . . ? _diffrn_measured_fraction_theta_max 0.986 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.556 _refine_diff_density_min -0.461 _refine_diff_density_rms 0.092 #===END data_l2011 _database_code_depnum_ccdc_archive 'CCDC 864407' #TrackingRef '- Cif_Combined3New.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety '2(C20 H38 N7 Ni O4), Cl2 O8' _chemical_formula_sum 'C40 H76 Cl2 N14 Ni2 O16' _chemical_formula_weight 1197.47 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' Cl Cl 0.1484 0.1585 '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 12.2771(7) _cell_length_b 15.7842(9) _cell_length_c 14.1558(8) _cell_angle_alpha 90.00 _cell_angle_beta 104.624(3) _cell_angle_gamma 90.00 _cell_volume 2654.3(3) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 9894 _cell_measurement_theta_min 2.35 _cell_measurement_theta_max 32.40 _exptl_crystal_description plate _exptl_crystal_colour green _exptl_crystal_size_max 0.37 _exptl_crystal_size_mid 0.14 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas no _exptl_crystal_density_diffrn 1.498 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1264 _exptl_absorpt_coefficient_mu 0.889 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7339 _exptl_absorpt_correction_T_max 0.9469 _exptl_absorpt_process_details 'sadabs v2008/1' _exptl_special_details ; All H atoms were added in their calculated positions and were treated using appropriate riding models. ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 59394 _diffrn_reflns_av_R_equivalents 0.0427 _diffrn_reflns_av_sigmaI/netI 0.0238 _diffrn_reflns_limit_h_min -18 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_k_min -24 _diffrn_reflns_limit_k_max 24 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 2.15 _diffrn_reflns_theta_max 33.40 _reflns_number_total 5164 _reflns_number_gt 4381 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0475P)^2^+1.8543P] 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 5164 _refine_ls_number_parameters 242 _refine_ls_number_restraints 50 _refine_ls_R_factor_all 0.0439 _refine_ls_R_factor_gt 0.0331 _refine_ls_wR_factor_ref 0.0874 _refine_ls_wR_factor_gt 0.0815 _refine_ls_goodness_of_fit_ref 1.014 _refine_ls_restrained_S_all 1.031 _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 O1 O 1.12783(9) 0.47638(7) 0.95160(7) 0.0276(2) Uani 1 1 d . . . O2 O 1.00477(8) 0.55993(6) 0.85039(6) 0.02079(17) Uani 1 1 d . . . N4 N 1.03919(9) 0.34001(6) 0.82949(7) 0.01777(18) Uani 1 1 d . . . C8 C 1.02475(9) 0.42103(7) 0.80027(8) 0.01573(19) Uani 1 1 d . . . C9 C 1.05887(10) 0.48752(7) 0.87544(8) 0.01708(19) Uani 1 1 d . . . C10 C 1.03859(12) 0.62842(8) 0.91891(10) 0.0251(2) Uani 1 1 d . . . H10A H 1.0107 0.6178 0.9769 0.038 Uiso 1 1 calc R . . H10B H 1.0071 0.6818 0.8884 0.038 Uiso 1 1 calc R . . H10C H 1.1209 0.6322 0.9380 0.038 Uiso 1 1 calc R . . Ni1 Ni 1.0000 0.16735(3) 0.7500 0.01205(8) Uani 0.9180(18) 2 d SPD . 1 N1 N 0.85112(10) 0.12788(8) 0.64800(8) 0.0182(2) Uani 0.9180(18) 1 d PD . 1 N2 N 1.07662(10) 0.15744(8) 0.62964(8) 0.0180(2) Uani 0.9180(18) 1 d PD . 1 N3 N 1.0000 0.29413(10) 0.7500 0.0166(3) Uani 0.9180(18) 2 d SPD . 1 C1 C 0.88601(12) 0.10168(9) 0.55902(9) 0.0222(3) Uani 0.9180(18) 1 d PD . 1 H1A H 0.8206 0.1048 0.5015 0.027 Uiso 0.9180(18) 1 calc PR . 1 H1B H 0.9128 0.0423 0.5662 0.027 Uiso 0.9180(18) 1 calc PR . 1 C2 C 0.97847(12) 0.15833(9) 0.54333(9) 0.0214(3) Uani 0.9180(18) 1 d PD . 1 H2A H 1.0024 0.1390 0.4851 0.026 Uiso 0.9180(18) 1 calc PR . 1 H2B H 0.9497 0.2170 0.5311 0.026 Uiso 0.9180(18) 1 calc PR . 1 C3 C 0.79838(15) 0.05269(11) 0.68260(11) 0.0260(3) Uani 0.9180(18) 1 d PD . 1 H3A H 0.8522 0.0049 0.6915 0.031 Uiso 0.9180(18) 1 calc PR . 1 H3B H 0.7310 0.0363 0.6310 0.031 Uiso 0.9180(18) 1 calc PR . 1 C4 C 0.76351(18) 0.06548(13) 0.77730(12) 0.0277(4) Uani 0.9180(18) 1 d PD . 1 H4A H 0.7178 0.0163 0.7875 0.033 Uiso 0.9180(18) 1 calc PR . 1 H4B H 0.7152 0.1165 0.7708 0.033 Uiso 0.9180(18) 1 calc PR . 1 C5 C 0.86171(15) 0.07578(11) 0.86688(11) 0.0250(3) Uani 0.9180(18) 1 d PD . 1 H5A H 0.8330 0.0713 0.9261 0.030 Uiso 0.9180(18) 1 calc PR . 1 H5B H 0.9153 0.0286 0.8685 0.030 Uiso 0.9180(18) 1 calc PR . 1 C6 C 0.76653(11) 0.19630(10) 0.61992(10) 0.0233(3) Uani 0.9180(18) 1 d PD . 1 H6A H 0.7029 0.1759 0.5682 0.035 Uiso 0.9180(18) 1 calc PR . 1 H6B H 0.8009 0.2452 0.5961 0.035 Uiso 0.9180(18) 1 calc PR . 1 H6C H 0.7398 0.2130 0.6769 0.035 Uiso 0.9180(18) 1 calc PR . 1 C7 C 1.15232(12) 0.22677(10) 0.61534(11) 0.0241(3) Uani 0.9180(18) 1 d PD . 1 H7A H 1.1741 0.2177 0.5541 0.036 Uiso 0.9180(18) 1 calc PR . 1 H7B H 1.2198 0.2273 0.6699 0.036 Uiso 0.9180(18) 1 calc PR . 1 H7C H 1.1131 0.2811 0.6125 0.036 Uiso 0.9180(18) 1 calc PR . 1 Ni1' Ni 1.0000 0.1526(4) 0.7500 0.01205(8) Uani 0.0820(18) 2 d SPD . 2 N1' N 0.8349(10) 0.1541(8) 0.6486(9) 0.0182(2) Uani 0.0820(18) 1 d PD . 2 N2' N 1.0646(10) 0.1261(9) 0.6296(9) 0.0180(2) Uani 0.0820(18) 1 d PD . 2 N3' N 1.0000 0.2809(11) 0.7500 0.0166(3) Uani 0.0820(18) 2 d SPD . 2 C1' C 0.8616(11) 0.1545(9) 0.5525(9) 0.0222(3) Uani 0.0820(18) 1 d PD . 2 H1'1 H 0.8779 0.2132 0.5356 0.027 Uiso 0.0820(18) 1 calc PR . 2 H1'2 H 0.7956 0.1340 0.5020 0.027 Uiso 0.0820(18) 1 calc PR . 2 C2' C 0.9597(11) 0.1000(9) 0.5536(9) 0.0214(3) Uani 0.0820(18) 1 d PD . 2 H2'1 H 0.9755 0.1018 0.4884 0.026 Uiso 0.0820(18) 1 calc PR . 2 H2'2 H 0.9409 0.0408 0.5662 0.026 Uiso 0.0820(18) 1 calc PR . 2 C3' C 0.7854(19) 0.0711(12) 0.6644(13) 0.0260(3) Uani 0.0820(18) 1 d PD . 2 H3'1 H 0.7111 0.0668 0.6168 0.031 Uiso 0.0820(18) 1 calc PR . 2 H3'2 H 0.8337 0.0264 0.6472 0.031 Uiso 0.0820(18) 1 calc PR . 2 C4' C 0.769(2) 0.0501(19) 0.7612(14) 0.0277(4) Uani 0.0820(18) 1 d PD . 2 H4'1 H 0.7363 -0.0075 0.7566 0.033 Uiso 0.0820(18) 1 calc PR . 2 H4'2 H 0.7113 0.0894 0.7734 0.033 Uiso 0.0820(18) 1 calc PR . 2 C5' C 0.8658(18) 0.0517(14) 0.8503(13) 0.0250(3) Uani 0.0820(18) 1 d PD . 2 H5'1 H 0.8351 0.0414 0.9076 0.030 Uiso 0.0820(18) 1 calc PR . 2 H5'2 H 0.9153 0.0031 0.8459 0.030 Uiso 0.0820(18) 1 calc PR . 2 C6' C 0.7578(12) 0.2259(10) 0.6512(13) 0.0233(3) Uani 0.0820(18) 1 d PD . 2 H6'1 H 0.7966 0.2794 0.6465 0.035 Uiso 0.0820(18) 1 calc PR . 2 H6'2 H 0.7349 0.2245 0.7127 0.035 Uiso 0.0820(18) 1 calc PR . 2 H6'3 H 0.6911 0.2212 0.5962 0.035 Uiso 0.0820(18) 1 calc PR . 2 C7' C 1.1142(14) 0.1973(11) 0.5897(12) 0.0241(3) Uani 0.0820(18) 1 d PD . 2 H7'1 H 1.1857 0.2129 0.6351 0.036 Uiso 0.0820(18) 1 calc PR . 2 H7'2 H 1.0626 0.2457 0.5805 0.036 Uiso 0.0820(18) 1 calc PR . 2 H7'3 H 1.1276 0.1811 0.5268 0.036 Uiso 0.0820(18) 1 calc PR . 2 Cl1 Cl 0.5184(12) 0.3415(10) 0.7578(8) 0.0303(2) Uani 0.098(3) 1 d PD A -1 O3 O 0.6113(12) 0.3056(13) 0.8269(14) 0.0736(16) Uani 0.098(3) 1 d PD A -1 O4 O 0.5678(19) 0.3770(12) 0.6862(11) 0.0755(18) Uani 0.098(3) 1 d PD A -1 O3A O 0.4252(17) 0.2861(15) 0.7264(18) 0.0560(12) Uani 0.098(3) 1 d PD A -1 O4A O 0.488(4) 0.410(2) 0.811(3) 0.0523(9) Uani 0.098(3) 1 d PD A -1 Cl1' Cl 0.4780(3) 0.3420(2) 0.7379(2) 0.0303(2) Uani 0.402(3) 1 d PD A -2 O3' O 0.5855(3) 0.3176(4) 0.7263(5) 0.0736(16) Uani 0.402(3) 1 d PD A -2 O4' O 0.4150(5) 0.3739(3) 0.6466(2) 0.0755(18) Uani 0.402(3) 1 d PD A -2 O3'A O 0.4229(4) 0.2683(3) 0.7584(5) 0.0560(12) Uani 0.402(3) 1 d PD A -2 O4'A O 0.4869(10) 0.4040(6) 0.8125(7) 0.0523(9) Uani 0.402(3) 1 d PD A -2 loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0307(5) 0.0268(5) 0.0191(4) -0.0023(3) -0.0053(4) 0.0029(4) O2 0.0265(4) 0.0163(4) 0.0174(4) -0.0032(3) 0.0017(3) 0.0018(3) N4 0.0218(4) 0.0152(4) 0.0155(4) -0.0002(3) 0.0032(3) -0.0004(3) C8 0.0172(5) 0.0152(4) 0.0137(4) -0.0003(3) 0.0021(4) 0.0002(4) C9 0.0190(5) 0.0172(5) 0.0146(4) -0.0001(4) 0.0036(4) -0.0013(4) C10 0.0317(6) 0.0191(5) 0.0253(6) -0.0083(4) 0.0086(5) -0.0029(5) Ni1 0.01486(9) 0.01021(19) 0.00995(8) 0.000 0.00106(6) 0.000 N1 0.0181(5) 0.0206(6) 0.0141(4) 0.0012(4) 0.0006(4) -0.0029(4) N2 0.0192(5) 0.0209(6) 0.0134(4) -0.0002(4) 0.0029(3) 0.0033(4) N3 0.0224(6) 0.0123(7) 0.0148(5) 0.000 0.0042(5) 0.000 C1 0.0263(6) 0.0247(6) 0.0129(5) -0.0038(4) 0.0001(4) -0.0031(5) C2 0.0242(6) 0.0279(6) 0.0108(5) 0.0010(4) 0.0021(4) 0.0012(5) C3 0.0290(7) 0.0272(8) 0.0181(7) 0.0023(5) -0.0008(5) -0.0131(6) C4 0.0271(7) 0.0346(10) 0.0208(7) -0.0004(6) 0.0050(6) -0.0152(7) C5 0.0284(6) 0.0281(8) 0.0178(6) 0.0041(5) 0.0043(5) -0.0092(7) C6 0.0185(6) 0.0290(7) 0.0197(6) 0.0032(5) -0.0001(5) 0.0001(5) C7 0.0216(6) 0.0311(7) 0.0213(6) 0.0021(5) 0.0085(5) -0.0012(5) Ni1' 0.01486(9) 0.01021(19) 0.00995(8) 0.000 0.00106(6) 0.000 N1' 0.0181(5) 0.0206(6) 0.0141(4) 0.0012(4) 0.0006(4) -0.0029(4) N2' 0.0192(5) 0.0209(6) 0.0134(4) -0.0002(4) 0.0029(3) 0.0033(4) N3' 0.0224(6) 0.0123(7) 0.0148(5) 0.000 0.0042(5) 0.000 C1' 0.0263(6) 0.0247(6) 0.0129(5) -0.0038(4) 0.0001(4) -0.0031(5) C2' 0.0242(6) 0.0279(6) 0.0108(5) 0.0010(4) 0.0021(4) 0.0012(5) C3' 0.0290(7) 0.0272(8) 0.0181(7) 0.0023(5) -0.0008(5) -0.0131(6) C4' 0.0271(7) 0.0346(10) 0.0208(7) -0.0004(6) 0.0050(6) -0.0152(7) C5' 0.0284(6) 0.0281(8) 0.0178(6) 0.0041(5) 0.0043(5) -0.0092(7) C6' 0.0185(6) 0.0290(7) 0.0197(6) 0.0032(5) -0.0001(5) 0.0001(5) C7' 0.0216(6) 0.0311(7) 0.0213(6) 0.0021(5) 0.0085(5) -0.0012(5) Cl1 0.0407(8) 0.0185(2) 0.0346(7) -0.0008(5) 0.0149(5) 0.0003(4) O3 0.0355(19) 0.095(4) 0.095(4) -0.027(4) 0.024(2) -0.004(2) O4 0.138(5) 0.068(3) 0.0302(16) 0.0146(18) 0.038(2) 0.047(3) O3A 0.058(2) 0.033(2) 0.074(3) 0.0099(19) 0.011(2) -0.0228(18) O4A 0.089(2) 0.0320(19) 0.0416(15) -0.0151(14) 0.0265(17) -0.0038(17) Cl1' 0.0407(8) 0.0185(2) 0.0346(7) -0.0008(5) 0.0149(5) 0.0003(4) O3' 0.0355(19) 0.095(4) 0.095(4) -0.027(4) 0.024(2) -0.004(2) O4' 0.138(5) 0.068(3) 0.0302(16) 0.0146(18) 0.038(2) 0.047(3) O3'A 0.058(2) 0.033(2) 0.074(3) 0.0099(19) 0.011(2) -0.0228(18) O4'A 0.089(2) 0.0320(19) 0.0416(15) -0.0151(14) 0.0265(17) -0.0038(17) _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 O1 C9 1.2038(14) . ? O2 C9 1.3245(14) . ? O2 C10 1.4417(15) . ? N4 N3 1.3223(13) . ? N4 C8 1.3419(14) . ? N4 N3' 1.448(11) . ? C8 C8 1.399(2) 2_756 ? C8 C9 1.4779(16) . ? C10 H10A 0.9800 . ? C10 H10B 0.9800 . ? C10 H10C 0.9800 . ? Ni1 N3 2.0012(16) . ? Ni1 N1 2.1169(11) . ? Ni1 N1 2.1169(11) 2_756 ? Ni1 N2 2.1497(11) 2_756 ? Ni1 N2 2.1497(11) . ? N1 C6 1.4814(19) . ? N1 C1 1.4878(18) . ? N1 C3 1.4925(19) . ? N2 C7 1.482(2) . ? N2 C2 1.4838(17) . ? N2 C5 1.4893(19) 2_756 ? N3 N4 1.3223(13) 2_756 ? C1 C2 1.505(2) . ? C1 H1A 0.9900 . ? C1 H1B 0.9900 . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C3 C4 1.520(2) . ? C3 H3A 0.9900 . ? C3 H3B 0.9900 . ? C4 C5 1.522(2) . ? C4 H4A 0.9900 . ? C4 H4B 0.9900 . ? C5 N2 1.4894(19) 2_756 ? C5 H5A 0.9900 . ? C5 H5B 0.9900 . ? C6 H6A 0.9800 . ? C6 H6B 0.9800 . ? C6 H6C 0.9800 . ? C7 H7A 0.9800 . ? C7 H7B 0.9800 . ? C7 H7C 0.9800 . ? Ni1' N3' 2.024(17) . ? Ni1' N2' 2.096(11) . ? Ni1' N2' 2.096(11) 2_756 ? Ni1' N1' 2.168(12) 2_756 ? Ni1' N1' 2.168(12) . ? N1' C1' 1.477(14) . ? N1' C6' 1.482(15) . ? N1' C3' 1.485(15) . ? N2' C5' 1.44(2) 2_756 ? N2' C7' 1.458(15) . ? N2' C2' 1.512(14) . ? N3' N4 1.448(11) 2_756 ? C1' C2' 1.478(15) . ? C1' H1'1 0.9900 . ? C1' H1'2 0.9900 . ? C2' H2'1 0.9900 . ? C2' H2'2 0.9900 . ? C3' C4' 1.472(17) . ? C3' H3'1 0.9900 . ? C3' H3'2 0.9900 . ? C4' C5' 1.499(18) . ? C4' H4'1 0.9900 . ? C4' H4'2 0.9900 . ? C5' N2' 1.44(2) 2_756 ? C5' H5'1 0.9900 . ? C5' H5'2 0.9900 . ? C6' H6'1 0.9800 . ? C6' H6'2 0.9800 . ? C6' H6'3 0.9800 . ? C7' H7'1 0.9800 . ? C7' H7'2 0.9800 . ? C7' H7'3 0.9800 . ? Cl1 O3 1.419(7) . ? Cl1 O4 1.420(6) . ? Cl1 O3A 1.421(7) . ? Cl1 O4A 1.423(7) . ? Cl1' O3'A 1.412(3) . ? Cl1' O4' 1.420(3) . ? Cl1' O3' 1.423(3) . ? Cl1' O4'A 1.424(3) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C9 O2 C10 115.29(10) . . ? N3 N4 C8 105.56(10) . . ? C8 N4 N3' 112.5(5) . . ? N4 C8 C8 107.64(6) . 2_756 ? N4 C8 C9 117.61(9) . . ? C8 C8 C9 134.72(6) 2_756 . ? O1 C9 O2 123.89(11) . . ? O1 C9 C8 123.26(11) . . ? O2 C9 C8 112.84(9) . . ? O2 C10 H10A 109.5 . . ? O2 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? O2 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? N3 Ni1 N1 107.12(4) . . ? N3 Ni1 N1 107.12(4) . 2_756 ? N1 Ni1 N1 145.76(8) . 2_756 ? N3 Ni1 N2 94.17(3) . 2_756 ? N1 Ni1 N2 92.52(4) . 2_756 ? N1 Ni1 N2 85.02(5) 2_756 2_756 ? N3 Ni1 N2 94.17(3) . . ? N1 Ni1 N2 85.02(5) . . ? N1 Ni1 N2 92.52(4) 2_756 . ? N2 Ni1 N2 171.65(7) 2_756 . ? C6 N1 C1 107.92(11) . . ? C6 N1 C3 109.57(12) . . ? C1 N1 C3 107.36(12) . . ? C6 N1 Ni1 113.23(9) . . ? C1 N1 Ni1 106.00(8) . . ? C3 N1 Ni1 112.44(8) . . ? C7 N2 C2 106.70(11) . . ? C7 N2 C5 108.20(12) . 2_756 ? C2 N2 C5 109.62(12) . 2_756 ? C7 N2 Ni1 118.00(9) . . ? C2 N2 Ni1 103.01(8) . . ? C5 N2 Ni1 110.93(9) 2_756 . ? N4 N3 N4 113.59(14) 2_756 . ? N4 N3 Ni1 123.20(7) 2_756 . ? N4 N3 Ni1 123.20(7) . . ? N1 C1 C2 110.42(11) . . ? N1 C1 H1A 109.6 . . ? C2 C1 H1A 109.6 . . ? N1 C1 H1B 109.6 . . ? C2 C1 H1B 109.6 . . ? H1A C1 H1B 108.1 . . ? N2 C2 C1 111.03(11) . . ? N2 C2 H2A 109.4 . . ? C1 C2 H2A 109.4 . . ? N2 C2 H2B 109.4 . . ? C1 C2 H2B 109.4 . . ? H2A C2 H2B 108.0 . . ? N1 C3 C4 115.21(14) . . ? N1 C3 H3A 108.5 . . ? C4 C3 H3A 108.5 . . ? N1 C3 H3B 108.5 . . ? C4 C3 H3B 108.5 . . ? H3A C3 H3B 107.5 . . ? C3 C4 C5 114.13(15) . . ? C3 C4 H4A 108.7 . . ? C5 C4 H4A 108.7 . . ? C3 C4 H4B 108.7 . . ? C5 C4 H4B 108.7 . . ? H4A C4 H4B 107.6 . . ? N2 C5 C4 114.15(13) 2_756 . ? N2 C5 H5A 108.7 2_756 . ? C4 C5 H5A 108.7 . . ? N2 C5 H5B 108.7 2_756 . ? C4 C5 H5B 108.7 . . ? H5A C5 H5B 107.6 . . ? N3' Ni1' N2' 101.5(4) . . ? N3' Ni1' N2' 101.5(4) . 2_756 ? N2' Ni1' N2' 156.9(8) . 2_756 ? N3' Ni1' N1' 89.4(4) . 2_756 ? N2' Ni1' N1' 93.3(5) . 2_756 ? N2' Ni1' N1' 86.9(5) 2_756 2_756 ? N3' Ni1' N1' 89.4(4) . . ? N2' Ni1' N1' 86.9(5) . . ? N2' Ni1' N1' 93.3(5) 2_756 . ? N1' Ni1' N1' 178.8(8) 2_756 . ? C1' N1' C6' 108.1(11) . . ? C1' N1' C3' 109.6(12) . . ? C6' N1' C3' 112.5(14) . . ? C1' N1' Ni1' 102.8(8) . . ? C6' N1' Ni1' 119.2(10) . . ? C3' N1' Ni1' 103.9(10) . . ? C5' N2' C7' 114.9(14) 2_756 . ? C5' N2' C2' 106.0(13) 2_756 . ? C7' N2' C2' 107.3(12) . . ? C5' N2' Ni1' 109.3(10) 2_756 . ? C7' N2' Ni1' 116.2(10) . . ? C2' N2' Ni1' 101.8(8) . . ? N4 N3' N4 99.7(11) 2_756 . ? N4 N3' Ni1' 130.2(5) 2_756 . ? N4 N3' Ni1' 130.2(5) . . ? N1' C1' C2' 110.9(11) . . ? N1' C1' H1'1 109.5 . . ? C2' C1' H1'1 109.4 . . ? N1' C1' H1'2 109.5 . . ? C2' C1' H1'2 109.5 . . ? H1'1 C1' H1'2 108.0 . . ? C1' C2' N2' 113.3(11) . . ? C1' C2' H2'1 108.9 . . ? N2' C2' H2'1 108.9 . . ? C1' C2' H2'2 108.9 . . ? N2' C2' H2'2 108.9 . . ? H2'1 C2' H2'2 107.7 . . ? C4' C3' N1' 119.7(17) . . ? C4' C3' H3'1 107.4 . . ? N1' C3' H3'1 107.4 . . ? C4' C3' H3'2 107.4 . . ? N1' C3' H3'2 107.4 . . ? H3'1 C3' H3'2 106.9 . . ? C3' C4' C5' 121.1(19) . . ? C3' C4' H4'1 107.1 . . ? C5' C4' H4'1 107.1 . . ? C3' C4' H4'2 107.1 . . ? C5' C4' H4'2 107.1 . . ? H4'1 C4' H4'2 106.8 . . ? N2' C5' C4' 119.0(18) 2_756 . ? N2' C5' H5'1 107.6 2_756 . ? C4' C5' H5'1 107.6 . . ? N2' C5' H5'2 107.6 2_756 . ? C4' C5' H5'2 107.6 . . ? H5'1 C5' H5'2 107.0 . . ? N1' C6' H6'1 109.5 . . ? N1' C6' H6'2 109.5 . . ? H6'1 C6' H6'2 109.5 . . ? N1' C6' H6'3 109.5 . . ? H6'1 C6' H6'3 109.5 . . ? H6'2 C6' H6'3 109.5 . . ? N2' C7' H7'1 109.5 . . ? N2' C7' H7'2 109.5 . . ? H7'1 C7' H7'2 109.5 . . ? N2' C7' H7'3 109.5 . . ? H7'1 C7' H7'3 109.5 . . ? H7'2 C7' H7'3 109.5 . . ? O3 Cl1 O4 103.6(13) . . ? O3 Cl1 O3A 114.4(16) . . ? O4 Cl1 O3A 118.4(15) . . ? O3 Cl1 O4A 102(2) . . ? O4 Cl1 O4A 108(2) . . ? O3A Cl1 O4A 109(2) . . ? O3'A Cl1' O4' 107.5(4) . . ? O3'A Cl1' O3' 107.9(5) . . ? O4' Cl1' O3' 107.4(4) . . ? O3'A Cl1' O4'A 111.4(6) . . ? O4' Cl1' O4'A 110.7(5) . . ? O3' Cl1' O4'A 111.8(6) . . ? 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 N4 C8 C8 -0.05(15) . . . 2_756 ? N3' N4 C8 C8 -0.05(15) . . . 2_756 ? N3 N4 C8 C9 178.45(9) . . . . ? N3' N4 C8 C9 178.45(9) . . . . ? C10 O2 C9 O1 3.54(18) . . . . ? C10 O2 C9 C8 -177.11(10) . . . . ? N4 C8 C9 O1 23.83(18) . . . . ? C8 C8 C9 O1 -158.18(17) 2_756 . . . ? N4 C8 C9 O2 -155.52(11) . . . . ? C8 C8 C9 O2 22.5(2) 2_756 . . . ? N3 Ni1 N1 C6 -15.76(10) . . . . ? N1 Ni1 N1 C6 164.24(10) 2_756 . . . ? N2 Ni1 N1 C6 79.39(10) 2_756 . . . ? N2 Ni1 N1 C6 -108.60(10) . . . . ? N3 Ni1 N1 C1 102.37(8) . . . . ? N1 Ni1 N1 C1 -77.63(8) 2_756 . . . ? N2 Ni1 N1 C1 -162.48(9) 2_756 . . . ? N2 Ni1 N1 C1 9.52(9) . . . . ? N3 Ni1 N1 C3 -140.62(10) . . . . ? N1 Ni1 N1 C3 39.38(10) 2_756 . . . ? N2 Ni1 N1 C3 -45.47(11) 2_756 . . . ? N2 Ni1 N1 C3 126.54(11) . . . . ? N3 Ni1 N2 C7 28.70(9) . . . . ? N1 Ni1 N2 C7 135.56(10) . . . . ? N1 Ni1 N2 C7 -78.67(10) 2_756 . . . ? N3 Ni1 N2 C2 -88.48(8) . . . . ? N1 Ni1 N2 C2 18.38(9) . . . . ? N1 Ni1 N2 C2 164.15(10) 2_756 . . . ? N3 Ni1 N2 C5 154.31(9) . . . 2_756 ? N1 Ni1 N2 C5 -98.84(11) . . . 2_756 ? N1 Ni1 N2 C5 46.93(10) 2_756 . . 2_756 ? C8 N4 N3 N4 0.02(6) . . . 2_756 ? N3' N4 N3 N4 179.999(4) . . . 2_756 ? C8 N4 N3 Ni1 -179.98(6) . . . . ? N3' N4 N3 Ni1 0.000(3) . . . . ? N1 Ni1 N3 N4 -36.06(7) . . . 2_756 ? N1 Ni1 N3 N4 143.94(7) 2_756 . . 2_756 ? N2 Ni1 N3 N4 -129.99(6) 2_756 . . 2_756 ? N2 Ni1 N3 N4 50.01(6) . . . 2_756 ? N1 Ni1 N3 N4 143.94(7) . . . . ? N1 Ni1 N3 N4 -36.06(7) 2_756 . . . ? N2 Ni1 N3 N4 50.00(6) 2_756 . . . ? N2 Ni1 N3 N4 -129.99(6) . . . . ? C6 N1 C1 C2 85.09(13) . . . . ? C3 N1 C1 C2 -156.89(11) . . . . ? Ni1 N1 C1 C2 -36.51(13) . . . . ? C7 N2 C2 C1 -169.13(11) . . . . ? C5 N2 C2 C1 73.92(14) 2_756 . . . ? Ni1 N2 C2 C1 -44.22(12) . . . . ? N1 C1 C2 N2 57.33(15) . . . . ? C6 N1 C3 C4 -66.70(17) . . . . ? C1 N1 C3 C4 176.36(14) . . . . ? Ni1 N1 C3 C4 60.15(17) . . . . ? N1 C3 C4 C5 -68.4(2) . . . . ? N2' Ni1' N1' C1' -11.7(9) . . . . ? N2' Ni1' N1' C1' -168.6(9) 2_756 . . . ? N3' Ni1' N1' C6' -29.6(11) . . . . ? N2' Ni1' N1' C6' -131.2(11) . . . . ? N2' Ni1' N1' C6' 71.9(11) 2_756 . . . ? N3' Ni1' N1' C3' -155.8(11) . . . . ? N2' Ni1' N1' C3' 102.6(11) . . . . ? N2' Ni1' N1' C3' -54.3(11) 2_756 . . . ? N3' Ni1' N2' C5' 144.3(11) . . . 2_756 ? N2' Ni1' N2' C5' -35.7(11) 2_756 . . 2_756 ? N1' Ni1' N2' C5' 54.2(12) 2_756 . . 2_756 ? N1' Ni1' N2' C5' -127.0(12) . . . 2_756 ? N3' Ni1' N2' C7' 12.3(11) . . . . ? N2' Ni1' N2' C7' -167.7(11) 2_756 . . . ? N1' Ni1' N2' C7' -77.8(11) 2_756 . . . ? N1' Ni1' N2' C7' 101.0(11) . . . . ? N3' Ni1' N2' C2' -103.9(8) . . . . ? N2' Ni1' N2' C2' 76.1(8) 2_756 . . . ? N1' Ni1' N2' C2' 166.0(9) 2_756 . . . ? N1' Ni1' N2' C2' -15.2(9) . . . . ? N3 N4 N3' N4 -0.001(19) . . . 2_756 ? C8 N4 N3' N4 0.02(6) . . . 2_756 ? N3 N4 N3' Ni1' 180.00(2) . . . . ? C8 N4 N3' Ni1' -179.98(6) . . . . ? N2' Ni1' N3' N4 46.8(3) . . . 2_756 ? N2' Ni1' N3' N4 -133.2(3) 2_756 . . 2_756 ? N1' Ni1' N3' N4 140.1(3) 2_756 . . 2_756 ? N1' Ni1' N3' N4 -39.9(3) . . . 2_756 ? N2' Ni1' N3' N4 -133.2(3) . . . . ? N2' Ni1' N3' N4 46.8(3) 2_756 . . . ? N1' Ni1' N3' N4 -39.9(3) 2_756 . . . ? N1' Ni1' N3' N4 140.1(3) . . . . ? C6' N1' C1' C2' 165.1(12) . . . . ? C3' N1' C1' C2' -71.9(16) . . . . ? Ni1' N1' C1' C2' 38.1(13) . . . . ? N1' C1' C2' N2' -58.5(16) . . . . ? C5' N2' C2' C1' 156.7(14) 2_756 . . . ? C7' N2' C2' C1' -80.0(14) . . . . ? Ni1' N2' C2' C1' 42.4(13) . . . . ? C1' N1' C3' C4' 170.0(19) . . . . ? C6' N1' C3' C4' -70(2) . . . . ? Ni1' N1' C3' C4' 61(2) . . . . ? N1' C3' C4' C5' -57(3) . . . . ? C3' C4' C5' N2' 52(3) . . . 2_756 ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.811 _refine_diff_density_min -0.500 _refine_diff_density_rms 0.067 #===END data_l711rt _database_code_depnum_ccdc_archive 'CCDC 864408' #TrackingRef '- Cif_Combined3New.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C20 H38 Co N7 O4, Cl O4' _chemical_formula_sum 'C20 H38 Cl Co N7 O8' _chemical_formula_weight 598.95 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' Cl Cl 0.1484 0.1585 '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 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 12.4963(12) _cell_length_b 16.1164(15) _cell_length_c 14.2264(14) _cell_angle_alpha 90.00 _cell_angle_beta 105.206(5) _cell_angle_gamma 90.00 _cell_volume 2764.8(5) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 9845 _cell_measurement_theta_min 2.31 _cell_measurement_theta_max 27.16 _exptl_crystal_description rectangular _exptl_crystal_colour red _exptl_crystal_size_max 0.23 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.18 _exptl_crystal_density_meas no _exptl_crystal_density_diffrn 1.439 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1260 _exptl_absorpt_coefficient_mu 0.772 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8436 _exptl_absorpt_correction_T_max 0.8728 _exptl_absorpt_process_details 'sadabs v2008/1' _exptl_special_details ; All H atoms were added in their calculated positions and were treated using appropriate riding models. ; _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 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 56112 _diffrn_reflns_av_R_equivalents 0.0288 _diffrn_reflns_av_sigmaI/netI 0.0139 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -23 _diffrn_reflns_limit_k_max 23 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 2.11 _diffrn_reflns_theta_max 30.60 _reflns_number_total 4252 _reflns_number_gt 3596 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. Shelx restraints used: sadi 0.004 cl1 o3 cl1 o4 ; _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^)+(0.1025P)^2^+1.8868P] 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 4252 _refine_ls_number_parameters 172 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0591 _refine_ls_R_factor_gt 0.0495 _refine_ls_wR_factor_ref 0.1599 _refine_ls_wR_factor_gt 0.1487 _refine_ls_goodness_of_fit_ref 1.055 _refine_ls_restrained_S_all 1.056 _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 0.5000 0.32985(2) 0.2500 0.03292(13) Uani 1 2 d S . . O1 O 0.3698(2) 0.02344(14) 0.05203(15) 0.0748(6) Uani 1 1 d . . . O2 O 0.49591(15) -0.05573(11) 0.14957(12) 0.0534(4) Uani 1 1 d . . . N1 N 0.57542(18) 0.34452(14) 0.12763(14) 0.0495(4) Uani 1 1 d . . . N2 N 0.35428(16) 0.37402(13) 0.14831(13) 0.0477(4) Uani 1 1 d . . . N3 N 0.5000 0.20386(16) 0.2500 0.0481(6) Uani 1 2 d S . . N4 N 0.46112(18) 0.15851(11) 0.17058(14) 0.0463(4) Uani 1 1 d . . . C1 C 0.4778(2) 0.3457(2) 0.04278(17) 0.0608(7) Uani 1 1 d . . . H1A H 0.4488 0.2899 0.0296 0.073 Uiso 1 1 calc R . . H1B H 0.4997 0.3650 -0.0140 0.073 Uiso 1 1 calc R . . C2 C 0.3893(2) 0.4014(2) 0.06082(17) 0.0616(7) Uani 1 1 d . . . H2A H 0.4170 0.4578 0.0704 0.074 Uiso 1 1 calc R . . H2B H 0.3258 0.4008 0.0044 0.074 Uiso 1 1 calc R . . C3 C 0.3008(2) 0.44611(19) 0.1820(2) 0.0612(6) Uani 1 1 d . . . H3A H 0.2353 0.4610 0.1311 0.073 Uiso 1 1 calc R . . H3B H 0.3515 0.4928 0.1910 0.073 Uiso 1 1 calc R . . C4 C 0.2671(2) 0.4332(2) 0.2749(2) 0.0647(7) Uani 1 1 d . . . H4A H 0.2213 0.3838 0.2679 0.078 Uiso 1 1 calc R . . H4B H 0.2220 0.4799 0.2841 0.078 Uiso 1 1 calc R . . C5 C 0.6374(2) 0.42384(19) 0.1343(2) 0.0600(6) Uani 1 1 d . . . H5A H 0.5860 0.4693 0.1321 0.072 Uiso 1 1 calc R . . H5B H 0.6664 0.4287 0.0776 0.072 Uiso 1 1 calc R . . C6 C 0.6474(3) 0.2769(2) 0.1100(2) 0.0678(7) Uani 1 1 d . . . H6A H 0.6094 0.2248 0.1079 0.102 Uiso 1 1 calc R . . H6B H 0.7146 0.2758 0.1617 0.102 Uiso 1 1 calc R . . H6C H 0.6649 0.2860 0.0490 0.102 Uiso 1 1 calc R . . C7 C 0.2729(2) 0.3062(2) 0.1207(2) 0.0634(7) Uani 1 1 d . . . H7A H 0.2127 0.3239 0.0675 0.095 Uiso 1 1 calc R . . H7B H 0.2451 0.2919 0.1754 0.095 Uiso 1 1 calc R . . H7C H 0.3081 0.2586 0.1012 0.095 Uiso 1 1 calc R . . C8 C 0.47536(17) 0.07966(12) 0.19968(14) 0.0390(4) Uani 1 1 d . . . C9 C 0.44052(18) 0.01397(13) 0.12540(14) 0.0405(4) Uani 1 1 d . . . C10 C 0.4629(3) -0.12394(17) 0.0830(2) 0.0641(7) Uani 1 1 d . . . H10A H 0.3835 -0.1246 0.0589 0.096 Uiso 1 1 calc R . . H10B H 0.4874 -0.1751 0.1161 0.096 Uiso 1 1 calc R . . H10C H 0.4956 -0.1176 0.0294 0.096 Uiso 1 1 calc R . . Cl1 Cl 0.5000 -0.33905(7) 0.2500 0.1045(6) Uani 1 2 d SD . . O3 O 0.5809(6) -0.2874(5) 0.2505(10) 0.299(5) Uani 1 1 d D . . O4 O 0.4873(11) -0.3904(5) 0.1772(4) 0.330(6) Uani 1 1 d D . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Co1 0.0384(2) 0.03148(19) 0.02610(18) 0.000 0.00345(13) 0.000 O1 0.0856(14) 0.0624(11) 0.0539(11) -0.0057(9) -0.0216(10) 0.0078(10) O2 0.0625(10) 0.0433(8) 0.0483(9) -0.0089(6) 0.0037(7) 0.0066(7) N1 0.0506(10) 0.0642(11) 0.0338(8) 0.0003(8) 0.0114(7) -0.0052(9) N2 0.0454(9) 0.0589(11) 0.0348(8) 0.0025(7) 0.0032(7) 0.0096(8) N3 0.0644(16) 0.0347(11) 0.0454(13) 0.000 0.0148(12) 0.000 N4 0.0608(11) 0.0369(8) 0.0408(9) 0.0027(6) 0.0123(8) 0.0017(7) C1 0.0652(16) 0.0856(18) 0.0300(10) 0.0000(10) 0.0095(10) -0.0020(13) C2 0.0658(15) 0.0795(18) 0.0333(10) 0.0140(11) 0.0021(10) 0.0088(13) C3 0.0601(14) 0.0634(15) 0.0542(14) 0.0051(11) 0.0049(11) 0.0211(12) C4 0.0568(14) 0.0760(17) 0.0615(15) -0.0053(13) 0.0160(12) 0.0229(13) C5 0.0613(14) 0.0682(16) 0.0524(13) 0.0166(11) 0.0179(11) -0.0088(12) C6 0.0742(18) 0.0786(19) 0.0593(15) -0.0097(14) 0.0332(14) 0.0028(15) C7 0.0489(13) 0.0770(17) 0.0547(14) -0.0147(13) -0.0035(10) -0.0016(12) C8 0.0424(9) 0.0376(9) 0.0354(9) 0.0006(7) 0.0076(7) 0.0006(7) C9 0.0446(10) 0.0414(9) 0.0342(9) 0.0013(7) 0.0079(7) -0.0010(8) C10 0.0784(18) 0.0488(13) 0.0653(16) -0.0189(12) 0.0191(13) -0.0035(12) Cl1 0.1913(19) 0.0511(6) 0.0814(9) 0.000 0.0542(11) 0.000 O3 0.158(5) 0.223(8) 0.495(15) 0.039(9) 0.047(8) -0.079(6) O4 0.664(18) 0.229(8) 0.161(5) -0.115(5) 0.224(8) -0.185(10) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Co1 N3 2.030(3) . ? Co1 N2 2.1292(18) 2_655 ? Co1 N2 2.1293(18) . ? Co1 N1 2.1990(19) . ? Co1 N1 2.1991(19) 2_655 ? O1 C9 1.187(3) . ? O2 C9 1.317(3) . ? O2 C10 1.439(3) . ? N1 C1 1.474(3) . ? N1 C6 1.476(4) . ? N1 C5 1.485(3) . ? N2 C7 1.474(4) . ? N2 C3 1.482(3) . ? N2 C2 1.490(3) . ? N3 N4 1.326(2) 2_655 ? N3 N4 1.326(2) . ? N4 C8 1.334(3) . ? C1 C2 1.498(4) . ? C1 H1A 0.9700 . ? C1 H1B 0.9700 . ? C2 H2A 0.9700 . ? C2 H2B 0.9700 . ? C3 C4 1.503(4) . ? C3 H3A 0.9700 . ? C3 H3B 0.9700 . ? C4 C5 1.518(4) 2_655 ? C4 H4A 0.9700 . ? C4 H4B 0.9700 . ? C5 C4 1.518(4) 2_655 ? C5 H5A 0.9700 . ? C5 H5B 0.9700 . ? C6 H6A 0.9600 . ? C6 H6B 0.9600 . ? C6 H6C 0.9600 . ? C7 H7A 0.9600 . ? C7 H7B 0.9600 . ? C7 H7C 0.9600 . ? C8 C8 1.402(4) 2_655 ? C8 C9 1.478(3) . ? C10 H10A 0.9600 . ? C10 H10B 0.9600 . ? C10 H10C 0.9600 . ? Cl1 O4 1.302(4) . ? Cl1 O4 1.302(4) 2_655 ? Cl1 O3 1.309(5) 2_655 ? Cl1 O3 1.309(5) . ? 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 Co1 N2 109.53(6) . 2_655 ? N3 Co1 N2 109.53(6) . . ? N2 Co1 N2 140.94(12) 2_655 . ? N3 Co1 N1 96.17(6) . . ? N2 Co1 N1 91.96(8) 2_655 . ? N2 Co1 N1 83.91(8) . . ? N3 Co1 N1 96.17(6) . 2_655 ? N2 Co1 N1 83.91(8) 2_655 2_655 ? N2 Co1 N1 91.96(8) . 2_655 ? N1 Co1 N1 167.65(12) . 2_655 ? C9 O2 C10 116.0(2) . . ? C1 N1 C6 106.3(2) . . ? C1 N1 C5 110.3(2) . . ? C6 N1 C5 108.4(2) . . ? C1 N1 Co1 102.44(15) . . ? C6 N1 Co1 117.50(17) . . ? C5 N1 Co1 111.53(16) . . ? C7 N2 C3 109.2(2) . . ? C7 N2 C2 109.3(2) . . ? C3 N2 C2 107.1(2) . . ? C7 N2 Co1 109.91(17) . . ? C3 N2 Co1 114.86(15) . . ? C2 N2 Co1 106.27(14) . . ? N4 N3 N4 113.1(2) 2_655 . ? N4 N3 Co1 123.45(12) 2_655 . ? N4 N3 Co1 123.45(12) . . ? N3 N4 C8 105.75(18) . . ? N1 C1 C2 110.9(2) . . ? N1 C1 H1A 109.5 . . ? C2 C1 H1A 109.5 . . ? N1 C1 H1B 109.5 . . ? C2 C1 H1B 109.5 . . ? H1A C1 H1B 108.0 . . ? N2 C2 C1 111.0(2) . . ? N2 C2 H2A 109.4 . . ? C1 C2 H2A 109.4 . . ? N2 C2 H2B 109.4 . . ? C1 C2 H2B 109.4 . . ? H2A C2 H2B 108.0 . . ? N2 C3 C4 115.4(2) . . ? N2 C3 H3A 108.4 . . ? C4 C3 H3A 108.4 . . ? N2 C3 H3B 108.4 . . ? C4 C3 H3B 108.4 . . ? H3A C3 H3B 107.5 . . ? C3 C4 C5 115.1(2) . 2_655 ? C3 C4 H4A 108.5 . . ? C5 C4 H4A 108.5 2_655 . ? C3 C4 H4B 108.5 . . ? C5 C4 H4B 108.5 2_655 . ? H4A C4 H4B 107.5 . . ? N1 C5 C4 114.8(2) . 2_655 ? N1 C5 H5A 108.6 . . ? C4 C5 H5A 108.6 2_655 . ? N1 C5 H5B 108.6 . . ? C4 C5 H5B 108.6 2_655 . ? H5A C5 H5B 107.5 . . ? N1 C6 H6A 109.5 . . ? N1 C6 H6B 109.5 . . ? H6A C6 H6B 109.5 . . ? N1 C6 H6C 109.5 . . ? H6A C6 H6C 109.5 . . ? H6B C6 H6C 109.5 . . ? N2 C7 H7A 109.5 . . ? N2 C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? N2 C7 H7C 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? N4 C8 C8 107.70(12) . 2_655 ? N4 C8 C9 118.04(18) . . ? C8 C8 C9 134.26(11) 2_655 . ? O1 C9 O2 123.9(2) . . ? O1 C9 C8 123.2(2) . . ? O2 C9 C8 112.84(17) . . ? O2 C10 H10A 109.5 . . ? O2 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? O2 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? O4 Cl1 O4 101.1(7) . 2_655 ? O4 Cl1 O3 117.9(9) . 2_655 ? O4 Cl1 O3 110.0(8) 2_655 2_655 ? O4 Cl1 O3 110.0(8) . . ? O4 Cl1 O3 117.9(9) 2_655 . ? O3 Cl1 O3 100.9(9) 2_655 . ? 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 Co1 N1 C1 89.42(18) . . . . ? N2 Co1 N1 C1 -160.70(18) 2_655 . . . ? N2 Co1 N1 C1 -19.65(18) . . . . ? N1 Co1 N1 C1 -90.58(18) 2_655 . . . ? N3 Co1 N1 C6 -26.6(2) . . . . ? N2 Co1 N1 C6 83.3(2) 2_655 . . . ? N2 Co1 N1 C6 -135.7(2) . . . . ? N1 Co1 N1 C6 153.4(2) 2_655 . . . ? N3 Co1 N1 C5 -152.64(16) . . . . ? N2 Co1 N1 C5 -42.75(18) 2_655 . . . ? N2 Co1 N1 C5 98.29(18) . . . . ? N1 Co1 N1 C5 27.36(16) 2_655 . . . ? N3 Co1 N2 C7 15.19(18) . . . . ? N2 Co1 N2 C7 -164.81(18) 2_655 . . . ? N1 Co1 N2 C7 109.60(18) . . . . ? N1 Co1 N2 C7 -82.07(18) 2_655 . . . ? N3 Co1 N2 C3 138.83(17) . . . . ? N2 Co1 N2 C3 -41.17(17) 2_655 . . . ? N1 Co1 N2 C3 -126.76(19) . . . . ? N1 Co1 N2 C3 41.58(19) 2_655 . . . ? N3 Co1 N2 C2 -102.92(17) . . . . ? N2 Co1 N2 C2 77.08(17) 2_655 . . . ? N1 Co1 N2 C2 -8.51(18) . . . . ? N1 Co1 N2 C2 159.82(18) 2_655 . . . ? N2 Co1 N3 N4 36.05(13) 2_655 . . 2_655 ? N2 Co1 N3 N4 -143.95(13) . . . 2_655 ? N1 Co1 N3 N4 130.35(13) . . . 2_655 ? N1 Co1 N3 N4 -49.65(13) 2_655 . . 2_655 ? N2 Co1 N3 N4 -143.95(13) 2_655 . . . ? N2 Co1 N3 N4 36.06(13) . . . . ? N1 Co1 N3 N4 -49.65(13) . . . . ? N1 Co1 N3 N4 130.35(13) 2_655 . . . ? N4 N3 N4 C8 0.01(11) 2_655 . . . ? Co1 N3 N4 C8 180.00(11) . . . . ? C6 N1 C1 C2 169.5(2) . . . . ? C5 N1 C1 C2 -73.2(3) . . . . ? Co1 N1 C1 C2 45.7(3) . . . . ? C7 N2 C2 C1 -82.3(3) . . . . ? C3 N2 C2 C1 159.5(2) . . . . ? Co1 N2 C2 C1 36.3(3) . . . . ? N1 C1 C2 N2 -58.6(3) . . . . ? C7 N2 C3 C4 66.3(3) . . . . ? C2 N2 C3 C4 -175.4(2) . . . . ? Co1 N2 C3 C4 -57.7(3) . . . . ? N2 C3 C4 C5 68.1(4) . . . 2_655 ? C1 N1 C5 C4 173.8(2) . . . 2_655 ? C6 N1 C5 C4 -70.1(3) . . . 2_655 ? Co1 N1 C5 C4 60.7(3) . . . 2_655 ? N3 N4 C8 C8 0.0(3) . . . 2_655 ? N3 N4 C8 C9 -179.17(16) . . . . ? C10 O2 C9 O1 -2.7(4) . . . . ? C10 O2 C9 C8 177.1(2) . . . . ? N4 C8 C9 O1 -26.5(3) . . . . ? C8 C8 C9 O1 154.6(3) 2_655 . . . ? N4 C8 C9 O2 153.7(2) . . . . ? C8 C8 C9 O2 -25.2(4) 2_655 . . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.854 _refine_diff_density_min -0.635 _refine_diff_density_rms 0.075