# Electronic Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2012 data_publication_text _journal_name_full Chem.Commun. #TrackingRef '- p21n.cif' _journal_coden_Cambridge 0182 _publ_contact_author_name 'Masaki Kawano' _publ_contact_author_address ;Division of Advanced Materials Science Pohang University of Science and Technology San 31, Hyoja-dong, Nam-gu, Pohang 790-784, Korea ; _publ_contact_author_email mkawano@postech.ac.kr _publ_contact_author_phone +82-54-279-8740 _publ_contact_author_fax +82-54-279-8739 loop_ _publ_author_name _publ_author_address 'Yumi Yakiyama' ;Division of Advanced Materials Science Pohang University of Science and Technology San 31, Hyoja-dong, Nam-gu, Pohang 790-784, Korea ; 'Akira Ueda' ;Department of Chemistry, Graduate School of Science Osaka University Machikaneyama 1-1, Toyonaka, Osaka 560-0043, Japan ; 'Yasushi Morita' ;Department of Chemistry, Graduate School of Science Osaka University Machikaneyama 1-1, Toyonaka, Osaka 560-0043, Japan ; 'Masaki Kawano' ;Division of Advanced Materials Science Pohang University of Science and Technology San 31, Hyoja-dong, Nam-gu, Pohang 790-784, Korea ; # Attachment '- p42n.cif' data_K-TPHAP_rt _database_code_depnum_ccdc_archive 'CCDC 885671' #TrackingRef '- p42n.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C23 H16 K N9 O' _chemical_formula_weight 473.55 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' K K 0.2009 0.2494 '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' _symmetry_cell_setting tetragonal _symmetry_space_group_name_H-M P4(2)/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y+1/2, z' '-y, x+1/2, z+1/2' 'y+1/2, -x, z+1/2' '-x, -y, -z' 'x-1/2, y-1/2, -z' 'y, -x-1/2, -z-1/2' '-y-1/2, x, -z-1/2' _cell_length_a 20.822(2) _cell_length_b 20.822 _cell_length_c 9.6348(11) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 4177.1(6) _cell_formula_units_Z 8 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min 5.040 _cell_measurement_theta_max 66.809 _exptl_crystal_description block _exptl_crystal_colour orange _exptl_crystal_size_max 0.16 _exptl_crystal_size_mid 0.16 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.506 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1952 _exptl_absorpt_coefficient_mu 0.294 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.9545 _exptl_absorpt_correction_T_max 0.9769 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'microfocus source 30W maximum continuous power' _diffrn_radiation_monochromator 'Wuazar(TM) Montel multilayer optic' _diffrn_measurement_device_type CCD _diffrn_measurement_method 'omega and phi scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 60741 _diffrn_reflns_av_R_equivalents 0.0392 _diffrn_reflns_av_sigmaI/netI 0.0272 _diffrn_reflns_limit_h_min -31 _diffrn_reflns_limit_h_max 32 _diffrn_reflns_limit_k_min -28 _diffrn_reflns_limit_k_max 30 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 1.38 _diffrn_reflns_theta_max 33.51 _reflns_number_total 8203 _reflns_number_gt 6324 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2 sofware Suite' _computing_cell_refinement 'Bruker APEX2 sofware Suite' _computing_data_reduction 'Bruker APEX2 sofware Suite' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Bruker APEX2 sofware Suite' _computing_publication_material 'Bruker APEX2 sofware Suite' _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. The bond distance between O1 and H1O is longer than normal value because of hydrogen bonding interaction between O1 and N1. ; _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^)+(0.0856P)^2^+2.5621P] 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 8203 _refine_ls_number_parameters 359 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0668 _refine_ls_R_factor_gt 0.0492 _refine_ls_wR_factor_ref 0.1570 _refine_ls_wR_factor_gt 0.1424 _refine_ls_goodness_of_fit_ref 1.049 _refine_ls_restrained_S_all 1.049 _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 K1 K 0.163369(14) -0.015634(15) -0.13870(3) 0.01757(8) Uani 1 1 d . . . H2C H -0.1299(11) -0.1757(11) 0.779(3) 0.030(6) Uiso 1 1 d . . . H3C H -0.0466(11) -0.1553(11) 0.620(2) 0.024(5) Uiso 1 1 d . . . H4C H -0.2399(12) -0.0445(11) 0.626(3) 0.032(6) Uiso 1 1 d . . . H5C H -0.1616(10) -0.0171(10) 0.462(2) 0.022(5) Uiso 1 1 d . . . H8C H 0.3667(11) -0.1089(12) 0.119(2) 0.032(6) Uiso 1 1 d . . . H9C H 0.2653(11) -0.0624(11) 0.097(2) 0.030(6) Uiso 1 1 d . . . H10C H 0.3129(11) -0.2145(12) 0.432(3) 0.032(6) Uiso 1 1 d . . . H11C H 0.2054(11) -0.1712(11) 0.428(3) 0.030(6) Uiso 1 1 d . . . H14C H -0.0898(11) 0.2345(12) -0.116(2) 0.031(6) Uiso 1 1 d . . . H15C H -0.0759(10) 0.1439(10) 0.032(2) 0.022(5) Uiso 1 1 d . . . H16C H 0.0812(13) 0.2126(13) -0.254(3) 0.044(7) Uiso 1 1 d . . . H17C H 0.1087(11) 0.1289(11) -0.104(2) 0.029(6) Uiso 1 1 d . . . C1 C -0.09561(6) -0.08343(7) 0.52149(15) 0.0156(2) Uani 1 1 d . . . C2 C -0.13321(8) -0.14604(8) 0.71318(19) 0.0243(3) Uani 1 1 d . . . C3 C -0.08561(7) -0.13269(7) 0.61683(16) 0.0200(3) Uani 1 1 d . . . C4 C -0.19863(7) -0.06791(8) 0.62696(17) 0.0226(3) Uani 1 1 d . . . C5 C -0.15410(7) -0.05096(7) 0.52622(16) 0.0188(3) Uani 1 1 d . . . C6 C -0.04444(6) -0.06389(6) 0.42189(14) 0.0150(2) Uani 1 1 d . . . C7 C 0.22441(6) -0.11305(7) 0.25843(15) 0.0164(2) Uani 1 1 d . . . C8 C 0.33366(7) -0.12232(8) 0.18074(17) 0.0223(3) Uani 1 1 d . . . C9 C 0.27312(7) -0.09463(8) 0.16752(16) 0.0207(3) Uani 1 1 d . . . C10 C 0.30116(8) -0.18342(8) 0.3636(2) 0.0272(3) Uani 1 1 d . . . C11 C 0.23932(7) -0.15859(7) 0.35858(18) 0.0230(3) Uani 1 1 d . . . C12 C 0.15903(6) -0.08332(6) 0.25286(14) 0.0151(2) Uani 1 1 d . . . C13 C 0.01472(7) 0.12431(6) -0.01765(15) 0.0167(2) Uani 1 1 d . . . C14 C -0.05098(8) 0.20711(7) -0.11541(17) 0.0228(3) Uani 1 1 d . . . C15 C -0.04372(8) 0.15630(7) -0.02344(16) 0.0203(3) Uani 1 1 d . . . C16 C 0.05173(9) 0.19681(8) -0.19252(19) 0.0261(3) Uani 1 1 d . . . C17 C 0.06380(8) 0.14572(7) -0.10442(17) 0.0216(3) Uani 1 1 d . . . C18 C 0.02477(7) 0.06884(6) 0.07736(14) 0.0159(2) Uani 1 1 d . . . C19 C -0.01365(6) 0.00430(6) 0.24897(14) 0.0147(2) Uani 1 1 d . . . C20 C 0.04650(6) -0.02592(6) 0.25210(14) 0.0146(2) Uani 1 1 d . . . C21 C 0.05845(6) -0.07599(6) 0.34559(14) 0.0147(2) Uani 1 1 d . . . C22 C 0.09396(7) -0.00743(6) 0.15745(14) 0.0151(2) Uani 1 1 d . . . C24 C 0.23521(15) 0.16932(13) -0.0464(3) 0.0557(6) Uani 1 1 d . . . H24A H 0.2541 0.1872 0.0383 0.084 Uiso 1 1 calc R . . H24B H 0.1965 0.1937 -0.0708 0.084 Uiso 1 1 calc R . . H24C H 0.2664 0.1721 -0.1224 0.084 Uiso 1 1 calc R . . N1 N -0.18898(7) -0.11399(7) 0.72137(16) 0.0252(3) Uani 1 1 d . . . N2 N -0.06089(6) -0.01615(6) 0.33413(13) 0.0156(2) Uani 1 1 d . . . N3 N 0.01157(6) -0.09501(6) 0.43412(13) 0.0162(2) Uani 1 1 d . . . N4 N 0.34837(6) -0.16645(6) 0.27670(16) 0.0232(3) Uani 1 1 d . . . N5 N 0.11697(6) -0.10445(6) 0.34813(13) 0.0163(2) Uani 1 1 d . . . N6 N 0.15119(6) -0.03822(6) 0.15475(13) 0.0166(2) Uani 1 1 d . . . N7 N -0.00449(7) 0.22786(6) -0.19936(15) 0.0240(3) Uani 1 1 d . . . N8 N 0.08284(6) 0.04095(6) 0.06786(13) 0.0169(2) Uani 1 1 d . . . N9 N -0.02463(6) 0.05345(6) 0.15990(12) 0.0159(2) Uani 1 1 d . . . O1 O 0.21836(7) 0.10275(8) -0.02318(15) 0.0368(3) Uani 1 1 d . . . H1O H 0.202(3) 0.090(3) 0.096(7) 0.15(2) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 K1 0.01490(13) 0.02179(15) 0.01601(14) 0.00246(10) 0.00309(9) 0.00073(10) C1 0.0143(5) 0.0160(5) 0.0164(6) 0.0001(4) 0.0007(4) -0.0014(4) C2 0.0237(7) 0.0201(6) 0.0291(8) 0.0080(6) 0.0069(6) 0.0015(5) C3 0.0188(6) 0.0170(6) 0.0242(7) 0.0034(5) 0.0044(5) 0.0018(5) C4 0.0155(6) 0.0251(7) 0.0271(7) 0.0028(6) 0.0033(5) 0.0002(5) C5 0.0140(5) 0.0222(6) 0.0201(6) 0.0034(5) 0.0002(5) 0.0007(5) C6 0.0150(5) 0.0157(5) 0.0143(5) 0.0002(4) 0.0000(4) 0.0000(4) C7 0.0142(5) 0.0158(5) 0.0191(6) -0.0012(5) -0.0001(4) 0.0011(4) C8 0.0172(6) 0.0289(7) 0.0208(7) -0.0030(6) 0.0024(5) 0.0018(5) C9 0.0180(6) 0.0262(7) 0.0177(6) 0.0017(5) 0.0017(5) 0.0025(5) C10 0.0173(6) 0.0208(7) 0.0434(10) 0.0102(7) -0.0005(6) 0.0012(5) C11 0.0165(6) 0.0192(6) 0.0332(8) 0.0085(6) 0.0014(5) 0.0017(5) C12 0.0150(5) 0.0149(5) 0.0153(5) 0.0001(4) 0.0005(4) 0.0012(4) C13 0.0206(6) 0.0136(5) 0.0159(6) 0.0009(4) -0.0003(5) 0.0010(4) C14 0.0269(7) 0.0178(6) 0.0237(7) 0.0037(5) -0.0013(6) 0.0040(5) C15 0.0219(6) 0.0174(6) 0.0214(7) 0.0044(5) 0.0004(5) 0.0021(5) C16 0.0298(8) 0.0203(7) 0.0282(8) 0.0090(6) 0.0076(6) 0.0021(6) C17 0.0247(7) 0.0168(6) 0.0234(7) 0.0056(5) 0.0035(5) 0.0029(5) C18 0.0184(6) 0.0135(5) 0.0159(6) 0.0012(4) -0.0004(4) 0.0015(4) C19 0.0155(5) 0.0141(5) 0.0144(5) 0.0003(4) -0.0004(4) 0.0005(4) C20 0.0142(5) 0.0155(5) 0.0140(5) 0.0009(4) 0.0003(4) 0.0012(4) C21 0.0149(5) 0.0155(5) 0.0138(5) 0.0011(4) -0.0004(4) 0.0014(4) C22 0.0160(5) 0.0151(5) 0.0141(5) 0.0010(4) 0.0011(4) 0.0013(4) C24 0.0640(17) 0.0441(13) 0.0589(16) -0.0016(12) 0.0009(13) -0.0031(12) N1 0.0210(6) 0.0249(6) 0.0297(7) 0.0066(5) 0.0068(5) -0.0005(5) N2 0.0155(5) 0.0158(5) 0.0155(5) 0.0017(4) 0.0004(4) 0.0006(4) N3 0.0144(5) 0.0182(5) 0.0161(5) 0.0024(4) 0.0007(4) 0.0008(4) N4 0.0166(5) 0.0196(6) 0.0333(7) -0.0023(5) 0.0004(5) 0.0019(4) N5 0.0142(5) 0.0177(5) 0.0170(5) 0.0022(4) 0.0007(4) 0.0020(4) N6 0.0162(5) 0.0170(5) 0.0165(5) 0.0021(4) 0.0019(4) 0.0024(4) N7 0.0315(7) 0.0171(6) 0.0233(6) 0.0053(5) 0.0008(5) 0.0030(5) N8 0.0187(5) 0.0162(5) 0.0156(5) 0.0027(4) 0.0018(4) 0.0022(4) N9 0.0171(5) 0.0144(5) 0.0162(5) 0.0022(4) -0.0005(4) 0.0017(4) O1 0.0328(7) 0.0463(8) 0.0312(7) -0.0026(6) 0.0072(5) -0.0063(6) _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 K1 N7 2.7599(13) 8_655 ? K1 N8 2.8567(13) . ? K1 N6 2.8774(13) . ? K1 N2 2.9216(12) 5 ? K1 O1 2.9370(16) . ? K1 N4 2.9473(14) 3_544 ? K1 N9 3.0012(13) 5 ? K1 C22 3.2031(14) . ? K1 C19 3.3019(14) 5 ? C1 C3 1.392(2) . ? C1 C5 1.3937(19) . ? C1 C6 1.4905(19) . ? C2 N1 1.342(2) . ? C2 C3 1.386(2) . ? C2 H2C 0.88(2) . ? C3 H3C 0.94(2) . ? C4 N1 1.337(2) . ? C4 C5 1.388(2) . ? C4 H4C 0.99(2) . ? C5 H5C 0.95(2) . ? C6 N3 1.3395(17) . ? C6 N2 1.3492(18) . ? C7 C11 1.388(2) . ? C7 C9 1.394(2) . ? C7 C12 1.4965(19) . ? C8 N4 1.339(2) . ? C8 C9 1.392(2) . ? C8 H8C 0.95(2) . ? C9 H9C 0.97(2) . ? C10 N4 1.339(2) . ? C10 C11 1.388(2) . ? C10 H10C 0.95(3) . ? C11 H11C 1.01(2) . ? C12 N6 1.3423(18) . ? C12 N5 1.3428(18) . ? C13 C15 1.388(2) . ? C13 C17 1.393(2) . ? C13 C18 1.4887(19) . ? C14 N7 1.333(2) . ? C14 C15 1.388(2) . ? C14 H14C 0.99(2) . ? C15 H15C 0.89(2) . ? C16 N7 1.339(2) . ? C16 C17 1.384(2) . ? C16 H16C 0.91(3) . ? C17 H17C 1.00(2) . ? C18 N9 1.3390(18) . ? C18 N8 1.3445(18) . ? C19 N2 1.3498(18) . ? C19 N9 1.3550(17) . ? C19 C20 1.4020(18) . ? C19 K1 3.3019(14) 5 ? C20 C22 1.3987(19) . ? C20 C21 1.4001(18) . ? C21 N3 1.3553(18) . ? C21 N5 1.3553(17) . ? C22 N8 1.3466(17) . ? C22 N6 1.3534(17) . ? C24 O1 1.447(3) . ? C24 H24A 0.9800 . ? C24 H24B 0.9800 . ? C24 H24C 0.9800 . ? N2 K1 2.9216(12) 5 ? N4 K1 2.9473(14) 4 ? N7 K1 2.7599(13) 7_565 ? N9 K1 3.0012(13) 5 ? O1 H1O 1.22(6) . ? 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 N7 K1 N8 147.23(4) 8_655 . ? N7 K1 N6 129.91(4) 8_655 . ? N8 K1 N6 48.02(3) . . ? N7 K1 N2 102.47(4) 8_655 5 ? N8 K1 N2 85.81(4) . 5 ? N6 K1 N2 127.30(4) . 5 ? N7 K1 O1 79.85(4) 8_655 . ? N8 K1 O1 67.59(4) . . ? N6 K1 O1 78.41(4) . . ? N2 K1 O1 109.81(4) 5 . ? N7 K1 N4 84.64(4) 8_655 3_544 ? N8 K1 N4 126.99(4) . 3_544 ? N6 K1 N4 96.70(4) . 3_544 ? N2 K1 N4 93.17(4) 5 3_544 ? O1 K1 N4 154.51(4) . 3_544 ? N7 K1 N9 140.66(4) 8_655 5 ? N8 K1 N9 65.83(4) . 5 ? N6 K1 N9 86.51(3) . 5 ? N2 K1 N9 46.57(3) 5 5 ? O1 K1 N9 128.41(4) . 5 ? N4 K1 N9 75.53(4) 3_544 5 ? N7 K1 C22 150.39(4) 8_655 . ? N8 K1 C22 24.84(3) . . ? N6 K1 C22 24.99(3) . . ? N2 K1 C22 103.44(4) 5 . ? O1 K1 C22 78.09(4) . . ? N4 K1 C22 107.90(4) 3_544 . ? N9 K1 C22 68.92(3) 5 . ? N7 K1 C19 125.93(4) 8_655 5 ? N8 K1 C19 68.93(4) . 5 ? N6 K1 C19 104.16(3) . 5 ? N2 K1 C19 24.07(3) 5 5 ? O1 K1 C19 115.47(4) . 5 ? N4 K1 C19 90.01(4) 3_544 5 ? N9 K1 C19 24.23(3) 5 5 ? C22 K1 C19 81.77(4) . 5 ? C3 C1 C5 117.80(13) . . ? C3 C1 C6 121.27(12) . . ? C5 C1 C6 120.87(12) . . ? N1 C2 C3 123.95(15) . . ? N1 C2 H2C 111.9(15) . . ? C3 C2 H2C 124.1(15) . . ? C2 C3 C1 118.87(14) . . ? C2 C3 H3C 119.7(14) . . ? C1 C3 H3C 121.4(14) . . ? N1 C4 C5 123.90(14) . . ? N1 C4 H4C 119.5(14) . . ? C5 C4 H4C 116.6(14) . . ? C4 C5 C1 118.90(14) . . ? C4 C5 H5C 122.1(13) . . ? C1 C5 H5C 119.0(13) . . ? N3 C6 N2 129.25(12) . . ? N3 C6 C1 115.70(12) . . ? N2 C6 C1 115.04(12) . . ? C11 C7 C9 117.52(13) . . ? C11 C7 C12 120.73(13) . . ? C9 C7 C12 121.70(13) . . ? N4 C8 C9 123.67(14) . . ? N4 C8 H8C 118.0(15) . . ? C9 C8 H8C 118.4(15) . . ? C8 C9 C7 119.18(14) . . ? C8 C9 H9C 120.1(14) . . ? C7 C9 H9C 120.7(14) . . ? N4 C10 C11 124.11(15) . . ? N4 C10 H10C 114.9(14) . . ? C11 C10 H10C 121.0(14) . . ? C7 C11 C10 119.09(14) . . ? C7 C11 H11C 118.8(14) . . ? C10 C11 H11C 122.0(14) . . ? N6 C12 N5 129.15(12) . . ? N6 C12 C7 115.17(12) . . ? N5 C12 C7 115.67(12) . . ? C15 C13 C17 117.73(13) . . ? C15 C13 C18 121.34(13) . . ? C17 C13 C18 120.93(13) . . ? N7 C14 C15 123.72(15) . . ? N7 C14 H14C 113.9(14) . . ? C15 C14 H14C 122.0(14) . . ? C13 C15 C14 119.12(14) . . ? C13 C15 H15C 119.6(14) . . ? C14 C15 H15C 121.2(14) . . ? N7 C16 C17 124.06(15) . . ? N7 C16 H16C 112.4(17) . . ? C17 C16 H16C 123.5(17) . . ? C16 C17 C13 118.73(14) . . ? C16 C17 H17C 116.2(14) . . ? C13 C17 H17C 125.0(14) . . ? N9 C18 N8 128.89(13) . . ? N9 C18 C13 116.30(12) . . ? N8 C18 C13 114.81(12) . . ? N2 C19 N9 120.02(12) . . ? N2 C19 C20 119.76(12) . . ? N9 C19 C20 120.22(12) . . ? N2 C19 K1 61.97(7) . 5 ? N9 C19 K1 65.35(7) . 5 ? C20 C19 K1 151.94(9) . 5 ? C22 C20 C21 119.93(12) . . ? C22 C20 C19 119.58(12) . . ? C21 C20 C19 120.45(12) . . ? N3 C21 N5 120.55(12) . . ? N3 C21 C20 119.64(12) . . ? N5 C21 C20 119.80(12) . . ? N8 C22 N6 119.56(12) . . ? N8 C22 C20 120.15(12) . . ? N6 C22 C20 120.28(12) . . ? N8 C22 K1 63.03(7) . . ? N6 C22 K1 63.92(7) . . ? C20 C22 K1 152.24(10) . . ? O1 C24 H24A 109.5 . . ? O1 C24 H24B 109.5 . . ? H24A C24 H24B 109.5 . . ? O1 C24 H24C 109.5 . . ? H24A C24 H24C 109.5 . . ? H24B C24 H24C 109.5 . . ? C4 N1 C2 116.54(14) . . ? C6 N2 C19 115.36(11) . . ? C6 N2 K1 139.13(9) . 5 ? C19 N2 K1 93.96(8) . 5 ? C6 N3 C21 115.48(12) . . ? C10 N4 C8 116.43(13) . . ? C10 N4 K1 122.56(11) . 4 ? C8 N4 K1 113.31(10) . 4 ? C12 N5 C21 115.52(12) . . ? C12 N6 C22 115.14(12) . . ? C12 N6 K1 142.71(9) . . ? C22 N6 K1 91.09(8) . . ? C14 N7 C16 116.64(13) . . ? C14 N7 K1 123.22(10) . 7_565 ? C16 N7 K1 119.84(10) . 7_565 ? C18 N8 C22 115.73(12) . . ? C18 N8 K1 138.89(9) . . ? C22 N8 K1 92.13(8) . . ? C18 N9 C19 115.30(12) . . ? C18 N9 K1 139.62(9) . 5 ? C19 N9 K1 90.42(8) . 5 ? C24 O1 K1 147.11(15) . . ? C24 O1 H1O 115(3) . . ? K1 O1 H1O 94(3) . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 33.51 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.769 _refine_diff_density_min -0.753 _refine_diff_density_rms 0.086 # Attachment '- pca21.cif' data_TPHAP-Cokin _database_code_depnum_ccdc_archive 'CCDC 885673' #TrackingRef '- pca21.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C57.28 H35 Co N19.31 O13.68' _chemical_formula_weight 1271.62 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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 Pca2(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z+1/2' 'x+1/2, -y, z' '-x+1/2, y, z+1/2' _cell_length_a 29.0224(5) _cell_length_b 8.4172(1) _cell_length_c 27.4938(4) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 6716.4(2) _cell_formula_units_Z 4 _cell_measurement_temperature 90(2) _cell_measurement_reflns_used 57846 _cell_measurement_theta_min 0.69 _cell_measurement_theta_max 50.00 _exptl_crystal_description block _exptl_crystal_colour 'pale red' _exptl_crystal_size_max 0.18 _exptl_crystal_size_mid 0.09 _exptl_crystal_size_min 0.03 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.258 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2601 _exptl_absorpt_coefficient_mu 0.328 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.9433 _exptl_absorpt_correction_T_max 0.9902 _exptl_absorpt_process_details HKL2000 _exptl_special_details ; ? ; _diffrn_ambient_temperature 90(2) _diffrn_radiation_wavelength 0.68890 _diffrn_radiation_type synchrotron _diffrn_radiation_source 'undulator KEK PF-NW2A' _diffrn_radiation_monochromator Si _diffrn_measurement_device_type CCD _diffrn_measurement_method omega_scan _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 111153 _diffrn_reflns_av_R_equivalents 0.1046 _diffrn_reflns_av_sigmaI/netI 0.0891 _diffrn_reflns_limit_h_min -41 _diffrn_reflns_limit_h_max 41 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -38 _diffrn_reflns_limit_l_max 39 _diffrn_reflns_theta_min 1.98 _diffrn_reflns_theta_max 29.90 _reflns_number_total 20585 _reflns_number_gt 13339 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Rigaku Crystal Clear' _computing_cell_refinement HKL2000 _computing_data_reduction HKL2000 _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Bruker XP' _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. Several restraints were applied to disordered methanol (O1A-C1A and O1F-C1F), nitrate ion (N1X to O3X), water (O1YW) on a basis of chemical symmetry of the molecules. The occupancy factors of the disordered molecules converged as follows: methanol A: 56%, F: 22%; nitrate ion: 32%; water O1YW: 19%. ; _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^)+(0.1075P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.261(13) _refine_ls_number_reflns 20585 _refine_ls_number_parameters 950 _refine_ls_number_restraints 201 _refine_ls_R_factor_all 0.0995 _refine_ls_R_factor_gt 0.0697 _refine_ls_wR_factor_ref 0.1905 _refine_ls_wR_factor_gt 0.1793 _refine_ls_goodness_of_fit_ref 0.998 _refine_ls_restrained_S_all 1.011 _refine_ls_shift/su_max 0.023 _refine_ls_shift/su_mean 0.002 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 0.883469(12) 1.44027(5) 0.872585(17) 0.02565(10) Uani 1 1 d . . . C1 C 0.84780(10) 1.2029(4) 0.71043(11) 0.0276(6) Uani 1 1 d . . . C2 C 0.87101(12) 1.1169(4) 0.74562(11) 0.0301(7) Uani 1 1 d . . . H2A H 0.8833 1.0152 0.7382 0.036 Uiso 1 1 calc R . . C3 C 0.87608(11) 1.1805(4) 0.79178(11) 0.0301(7) Uani 1 1 d . . . H3A H 0.8919 1.1192 0.8155 0.036 Uiso 1 1 calc R . . C4 C 0.82927(12) 1.3471(4) 0.72432(11) 0.0320(7) Uani 1 1 d . . . H4A H 0.8116 1.4073 0.7018 0.038 Uiso 1 1 calc R . . C5 C 0.83637(12) 1.4039(5) 0.77087(11) 0.0331(7) Uani 1 1 d . . . H5A H 0.8240 1.5047 0.7793 0.040 Uiso 1 1 calc R . . C6 C 0.84471(11) 1.1457(4) 0.65873(11) 0.0273(6) Uani 1 1 d . . . C7 C 0.94002(11) 0.7502(4) 0.51251(12) 0.0279(6) Uani 1 1 d . . . C8 C 0.93824(11) 0.7021(4) 0.46423(12) 0.0330(7) Uani 1 1 d . . . H8A H 0.9136 0.7357 0.4439 0.040 Uiso 1 1 calc R . . C9 C 0.97294(13) 0.6038(5) 0.44573(14) 0.0365(8) Uani 1 1 d . . . H9A H 0.9712 0.5713 0.4127 0.044 Uiso 1 1 calc R . . C10 C 0.97604(12) 0.6946(5) 0.54059(13) 0.0339(7) Uani 1 1 d . . . H10A H 0.9783 0.7231 0.5739 0.041 Uiso 1 1 calc R . . C11 C 1.00844(13) 0.5980(5) 0.51980(14) 0.0405(9) Uani 1 1 d . . . H11A H 1.0327 0.5593 0.5398 0.049 Uiso 1 1 calc R . . C12 C 0.90348(11) 0.8576(4) 0.53291(11) 0.0268(6) Uani 1 1 d . . . C13 C 0.74138(11) 1.2360(4) 0.47661(11) 0.0285(7) Uani 1 1 d . . . C14 C 0.71850(14) 1.3751(5) 0.48733(13) 0.0426(9) Uani 1 1 d . . . H14A H 0.7251 1.4308 0.5166 0.051 Uiso 1 1 calc R . . C15 C 0.68574(14) 1.4333(5) 0.45507(15) 0.0411(9) Uani 1 1 d . . . H15A H 0.6712 1.5314 0.4624 0.049 Uiso 1 1 calc R . . C16 C 0.72924(16) 1.1610(5) 0.43367(14) 0.0475(10) Uani 1 1 d . . . H16A H 0.7443 1.0656 0.4243 0.057 Uiso 1 1 calc R . . C17 C 0.69545(15) 1.2242(5) 0.40457(14) 0.0461(10) Uani 1 1 d . . . H17A H 0.6871 1.1689 0.3758 0.055 Uiso 1 1 calc R . . C18 C 0.77754(11) 1.1710(4) 0.50928(11) 0.0272(6) Uani 1 1 d . . . C19 C 0.80918(10) 1.1649(4) 0.58509(10) 0.0256(6) Uani 1 1 d . . . C20 C 0.87556(10) 0.9953(4) 0.59829(11) 0.0246(6) Uani 1 1 d . . . C21 C 0.84142(11) 1.0581(4) 0.56750(11) 0.0255(6) Uani 1 1 d . . . C22 C 0.84018(11) 1.0110(4) 0.51824(11) 0.0258(6) Uani 1 1 d . . . C35 C 1.17833(11) 0.5037(5) 0.91406(14) 0.0363(8) Uani 1 1 d . . . C38 C 1.19799(15) 0.3619(6) 0.92686(18) 0.0528(11) Uani 1 1 d . . . H38A H 1.1863 0.3022 0.9534 0.063 Uiso 1 1 calc R . . C39 C 1.23574(15) 0.3065(6) 0.9000(2) 0.0575(11) Uani 1 1 d . . . H39A H 1.2495 0.2089 0.9095 0.069 Uiso 1 1 calc R . . C36 C 1.19475(15) 0.5803(6) 0.8728(2) 0.0569(10) Uani 1 1 d . . . H36A H 1.1801 0.6736 0.8610 0.068 Uiso 1 1 calc R . . C37 C 1.23281(17) 0.5181(7) 0.84912(19) 0.0603(12) Uani 1 1 d . . . H37A H 1.2450 0.5748 0.8222 0.072 Uiso 1 1 calc R . . C40 C 1.14170(12) 0.5756(4) 0.94459(13) 0.0337(7) Uani 1 1 d . . . C29 C 1.06525(13) 0.5770(4) 1.14217(12) 0.0354(8) Uani 1 1 d . . . C32 C 1.04280(14) 0.6733(5) 1.17562(13) 0.0404(8) Uani 1 1 d . . . H32A H 1.0301 0.7724 1.1661 0.049 Uiso 1 1 calc R . . C33 C 1.03944(15) 0.6209(6) 1.22353(13) 0.0440(9) Uani 1 1 d . . . H33A H 1.0240 0.6863 1.2465 0.053 Uiso 1 1 calc R . . C30 C 1.08303(16) 0.4333(5) 1.15780(14) 0.0447(9) Uani 1 1 d . . . H30A H 1.0984 0.3645 1.1358 0.054 Uiso 1 1 calc R . . C31 C 1.07777(17) 0.3912(5) 1.20723(14) 0.0487(10) Uani 1 1 d . . . H31A H 1.0899 0.2925 1.2181 0.058 Uiso 1 1 calc R . . C34 C 1.07111(13) 0.6290(4) 1.09070(11) 0.0320(7) Uani 1 1 d . . . C23 C 0.98344(12) 1.0144(5) 0.93785(12) 0.0314(7) Uani 1 1 d . . . C26 C 0.98979(12) 1.0731(4) 0.89139(12) 0.0313(7) Uani 1 1 d . . . H26A H 1.0147 1.0366 0.8719 0.038 Uiso 1 1 calc R . . C27 C 0.95962(10) 1.1848(4) 0.87381(13) 0.0310(6) Uani 1 1 d . . . H27A H 0.9652 1.2261 0.8422 0.037 Uiso 1 1 calc R . . C24 C 0.94547(14) 1.0707(5) 0.96380(14) 0.0417(9) Uani 1 1 d . . . H24A H 0.9398 1.0332 0.9958 0.050 Uiso 1 1 calc R . . C25 C 0.91653(13) 1.1792(5) 0.94336(12) 0.0385(8) Uani 1 1 d . . . H25A H 0.8907 1.2142 0.9616 0.046 Uiso 1 1 calc R . . C28 C 1.01638(12) 0.8992(4) 0.95961(12) 0.0311(7) Uani 1 1 d . . . C41 C 1.07990(11) 0.7417(4) 0.94881(12) 0.0293(7) Uani 1 1 d . . . C44 C 1.10992(12) 0.6040(4) 1.01952(12) 0.0313(7) Uani 1 1 d . . . C43 C 1.07847(12) 0.7083(4) 0.99905(12) 0.0295(7) Uani 1 1 d . . . C42 C 1.04267(12) 0.7731(4) 1.02780(11) 0.0302(7) Uani 1 1 d . . . C45 C 0.85997(19) 1.7962(7) 0.8410(4) 0.114(3) Uani 1 1 d . . . H45A H 0.8335 1.8672 0.8370 0.170 Uiso 1 1 calc R . . H45B H 0.8760 1.7852 0.8098 0.170 Uiso 1 1 calc R . . H45C H 0.8811 1.8406 0.8652 0.170 Uiso 1 1 calc R . . C46 C 0.9109(3) 1.7180(9) 0.9420(3) 0.100(2) Uani 1 1 d . . . H46A H 0.9270 1.7423 0.9725 0.151 Uiso 1 1 calc R . . H46B H 0.8787 1.7519 0.9446 0.151 Uiso 1 1 calc R . . H46C H 0.9258 1.7746 0.9151 0.151 Uiso 1 1 calc R . . N1 N 0.86009(9) 1.3226(3) 0.80484(9) 0.0288(6) Uani 1 1 d . . . N2 N 1.00795(11) 0.5543(4) 0.47230(12) 0.0394(7) Uani 1 1 d . . . N3 N 0.67393(9) 1.3594(3) 0.41489(9) 0.0293(6) Uani 1 1 d . . . N4 N 0.81053(9) 1.2112(3) 0.63230(9) 0.0271(6) Uani 1 1 d . . . N5 N 0.87673(9) 1.0387(3) 0.64552(10) 0.0271(6) Uani 1 1 d . . . N6 N 0.90751(9) 0.8922(3) 0.58059(9) 0.0267(5) Uani 1 1 d . . . N7 N 0.87205(10) 0.9086(3) 0.50033(10) 0.0283(6) Uani 1 1 d . . . N8 N 0.80708(10) 1.0682(3) 0.48864(9) 0.0282(6) Uani 1 1 d . . . N9 N 0.77591(9) 1.2232(3) 0.55561(10) 0.0288(6) Uani 1 1 d . . . N10 N 0.92296(10) 1.2395(4) 0.89803(9) 0.0298(6) Uani 1 1 d . . . N11 N 1.05685(13) 0.4833(5) 1.23850(11) 0.0448(8) Uani 1 1 d . . . N12 N 1.25327(11) 0.3825(5) 0.86226(15) 0.0514(9) Uani 1 1 d . . . N13 N 1.04767(9) 0.8391(4) 0.92903(10) 0.0304(6) Uani 1 1 d . . . N14 N 1.01180(10) 0.8735(4) 1.00766(10) 0.0320(6) Uani 1 1 d . . . N15 N 1.03930(11) 0.7320(4) 1.07486(10) 0.0351(7) Uani 1 1 d . . . N16 N 1.10697(11) 0.5645(4) 1.06725(11) 0.0338(6) Uani 1 1 d . . . N17 N 1.14325(10) 0.5367(4) 0.99158(11) 0.0338(6) Uani 1 1 d . . . N18 N 1.11192(10) 0.6728(4) 0.92101(10) 0.0344(6) Uani 1 1 d . . . O1 O 0.93884(8) 1.5279(3) 0.83412(8) 0.0324(5) Uani 1 1 d . . . O2 O 0.84476(8) 1.6476(3) 0.85647(8) 0.0323(5) Uani 1 1 d . . . O3 O 0.91263(8) 1.5612(3) 0.93371(9) 0.0353(5) Uani 1 1 d . . . C1N C 1.2305(2) 2.1709(10) 0.5697(3) 0.088(2) Uani 1 1 d . . . C2N C 1.2268(3) 2.1062(9) 0.6117(3) 0.0840(19) Uani 1 1 d . . . H2NA H 1.2035 2.0291 0.6172 0.101 Uiso 1 1 calc R . . C3N C 1.2538(4) 2.1433(10) 0.6460(3) 0.107(3) Uani 1 1 d . . . H3NA H 1.2505 2.0935 0.6768 0.128 Uiso 1 1 calc R . . C4N C 1.2883(3) 2.2559(12) 0.6393(4) 0.121(4) Uani 1 1 d . . . H4NA H 1.3077 2.2819 0.6660 0.145 Uiso 1 1 calc R . . C5N C 1.2954(3) 2.3300(8) 0.5961(5) 0.111(3) Uani 1 1 d . . . H5NA H 1.3190 2.4066 0.5915 0.133 Uiso 1 1 calc R . . C6N C 1.2643(4) 2.2841(11) 0.5574(3) 0.117(4) Uani 1 1 d . . . H6NA H 1.2665 2.3278 0.5256 0.141 Uiso 1 1 calc R . . N1N N 1.2013(2) 2.1380(11) 0.5285(3) 0.112(2) Uani 1 1 d . . . O1N O 1.2056(2) 2.2031(10) 0.4898(2) 0.144(3) Uani 1 1 d . . . O2N O 1.1714(2) 2.0280(9) 0.5359(3) 0.124(2) Uani 1 1 d . . . C1B C 1.0512(3) 1.6386(15) 0.8128(3) 0.126(3) Uani 1 1 d D . . O1B O 1.01567(11) 1.7140(5) 0.83993(12) 0.0627(9) Uani 1 1 d D . . C1C C 0.9543(14) 0.830(3) 1.1104(16) 0.177(13) Uani 0.50 1 d PDU A 1 O1C O 0.9600(3) 0.9951(14) 1.0919(3) 0.088(3) Uani 0.50 1 d PDU A 1 O1GW O 1.0253(9) 1.060(4) 1.1689(12) 0.214(13) Uani 0.50 1 d PU B 1 C1G C 0.9825(9) 1.028(5) 1.1408(11) 0.239(13) Uani 0.50 1 d PDU C 2 O1G O 1.0206(7) 1.0759(12) 1.1727(6) 0.109(6) Uani 0.50 1 d PDU C 2 C1J C 0.9426(9) 0.739(4) 1.1078(9) 0.139(7) Uani 0.50 1 d PU D 2 O1J O 0.9310(6) 0.891(4) 1.1025(9) 0.202(10) Uani 0.50 1 d PU D 2 C1D C 1.1922(6) 0.7074(15) 0.6111(4) 0.091(4) Uani 0.50 1 d PDU E 1 O1D O 1.2169(7) 0.665(3) 0.6603(7) 0.206(9) Uani 0.50 1 d PDU E 1 C1I C 1.1737(9) 0.525(4) 0.6780(11) 0.188(12) Uani 0.50 1 d PU F 2 O1I O 1.1924(4) 0.6126(19) 0.6415(5) 0.115(4) Uani 0.50 1 d PU F 2 C1E C 1.0762(8) 0.495(4) 0.682(2) 0.43(3) Uani 0.50 1 d PDU G 1 O1E O 1.0545(7) 0.605(4) 0.648(2) 0.51(3) Uani 0.50 1 d PDU G 1 C1H C 1.1164(13) 0.695(3) 0.6251(11) 0.246(17) Uani 0.50 1 d PDU H 2 O1H O 1.1132(7) 0.757(3) 0.5774(12) 0.248(12) Uani 0.50 1 d PDU H 2 O1W O 0.9764(3) 1.9611(7) 0.7731(2) 0.132(2) Uani 1 1 d . I 2 O2W O 0.7185(15) 1.548(2) 0.7245(7) 0.293(17) Uani 0.50 1 d P J 1 N1X N 1.1627(5) 2.042(2) 0.8383(6) 0.073(4) Uani 0.321(7) 1 d PU K 1 O1X O 1.1882(5) 2.103(3) 0.8006(6) 0.110(6) Uani 0.321(7) 1 d PU K 1 O2X O 1.1167(5) 2.017(4) 0.8383(7) 0.131(8) Uani 0.321(7) 1 d PU K 1 O3X O 1.1818(2) 1.9879(9) 0.8837(2) 0.030(2) Uani 0.321(7) 1 d PU K 1 C1F C 1.2389(6) 2.066(3) 0.7964(6) 0.057(7) Uani 0.223(9) 1 d PDU L 2 O1F O 1.2610(4) 2.173(2) 0.7649(4) 0.061(5) Uani 0.223(9) 1 d PDU L 2 C1A C 1.2385(9) 1.883(4) 0.7824(10) 0.217(12) Uani 0.554(11) 1 d PDU M 1 O1A O 1.2558(2) 1.9773(11) 0.8215(3) 0.079(3) Uani 0.554(11) 1 d PDU M 1 O1YW O 1.1369(4) 2.0491(11) 0.8651(4) 0.079(5) Uani 0.427(18) 1 d PU N 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 Co1 0.02290(16) 0.0374(2) 0.01668(16) 0.0043(2) 0.00192(18) -0.00027(16) C1 0.0231(14) 0.0405(18) 0.0191(13) 0.0011(13) 0.0017(11) -0.0044(13) C2 0.0334(16) 0.0346(17) 0.0222(14) 0.0015(13) -0.0009(13) -0.0016(14) C3 0.0332(16) 0.0367(17) 0.0205(14) 0.0045(13) -0.0035(12) -0.0059(14) C4 0.0306(15) 0.049(2) 0.0165(13) 0.0049(14) -0.0020(12) 0.0025(15) C5 0.0348(17) 0.046(2) 0.0187(14) 0.0015(14) 0.0015(13) 0.0058(15) C6 0.0260(14) 0.0387(18) 0.0173(13) 0.0037(13) 0.0005(11) -0.0029(13) C7 0.0268(14) 0.0314(16) 0.0254(14) 0.0028(13) 0.0061(12) -0.0033(13) C8 0.0271(15) 0.0419(19) 0.0301(16) 0.0009(15) -0.0004(13) 0.0018(14) C9 0.0373(18) 0.0390(19) 0.0332(17) -0.0015(15) 0.0099(15) -0.0040(15) C10 0.0284(16) 0.0431(19) 0.0303(16) 0.0061(15) 0.0064(13) 0.0004(14) C11 0.0327(17) 0.052(2) 0.0371(19) 0.0105(17) 0.0080(15) 0.0070(16) C12 0.0254(14) 0.0314(16) 0.0236(14) 0.0040(13) -0.0004(12) -0.0036(13) C13 0.0278(15) 0.0370(17) 0.0208(14) 0.0016(13) -0.0042(12) 0.0003(13) C14 0.046(2) 0.052(2) 0.0299(17) -0.0131(17) -0.0154(16) 0.0140(18) C15 0.0407(19) 0.045(2) 0.0380(19) -0.0081(17) -0.0101(16) 0.0150(17) C16 0.063(3) 0.045(2) 0.0338(19) -0.0103(17) -0.0196(19) 0.020(2) C17 0.060(2) 0.049(2) 0.0297(17) -0.0151(17) -0.0262(17) 0.0216(19) C18 0.0247(14) 0.0360(17) 0.0209(14) 0.0009(13) -0.0031(11) 0.0002(13) C19 0.0238(13) 0.0336(16) 0.0194(13) 0.0035(12) -0.0024(11) -0.0034(12) C20 0.0222(14) 0.0306(15) 0.0211(14) 0.0032(12) 0.0005(11) -0.0054(12) C21 0.0244(14) 0.0318(16) 0.0202(13) 0.0030(12) -0.0018(11) -0.0014(12) C22 0.0261(15) 0.0299(15) 0.0215(14) 0.0026(12) -0.0016(12) -0.0039(12) C35 0.0240(15) 0.046(2) 0.0392(19) 0.0008(17) -0.0004(14) -0.0011(14) C38 0.042(2) 0.062(3) 0.055(3) 0.010(2) 0.0049(19) 0.004(2) C39 0.041(2) 0.059(3) 0.072(3) -0.003(3) 0.005(2) 0.012(2) C36 0.051(2) 0.065(3) 0.054(2) 0.014(3) 0.012(3) 0.010(2) C37 0.046(2) 0.079(3) 0.056(3) 0.011(3) 0.016(2) 0.005(2) C40 0.0276(15) 0.0401(19) 0.0335(17) 0.0026(15) -0.0025(13) -0.0048(14) C29 0.0434(19) 0.0410(19) 0.0218(15) 0.0007(14) -0.0139(14) -0.0095(16) C32 0.047(2) 0.049(2) 0.0256(16) 0.0037(16) -0.0051(15) -0.0038(17) C33 0.046(2) 0.060(2) 0.0256(17) 0.0037(17) -0.0064(16) -0.004(2) C30 0.067(3) 0.042(2) 0.0251(16) -0.0006(16) -0.0137(17) -0.0013(19) C31 0.072(3) 0.045(2) 0.0292(19) 0.0050(17) -0.0188(19) -0.012(2) C34 0.0418(19) 0.0354(17) 0.0187(14) 0.0006(13) -0.0070(13) -0.0069(15) C23 0.0330(17) 0.0385(19) 0.0229(15) 0.0018(13) -0.0050(13) 0.0002(14) C26 0.0296(15) 0.0392(18) 0.0250(14) -0.0025(14) 0.0006(12) -0.0007(14) C27 0.0350(14) 0.0407(16) 0.0173(12) 0.0026(15) 0.0000(15) -0.0034(13) C24 0.0420(19) 0.055(2) 0.0278(17) 0.0075(17) 0.0035(15) 0.0098(18) C25 0.0389(18) 0.051(2) 0.0255(16) 0.0072(15) 0.0109(15) 0.0087(17) C28 0.0341(16) 0.0349(17) 0.0244(15) 0.0030(13) -0.0065(13) -0.0031(14) C41 0.0255(14) 0.0361(17) 0.0264(15) -0.0017(13) -0.0058(12) -0.0067(13) C44 0.0297(16) 0.0369(17) 0.0272(15) -0.0005(14) -0.0048(13) -0.0085(13) C43 0.0331(16) 0.0310(17) 0.0244(15) -0.0005(13) -0.0062(13) -0.0081(13) C42 0.0348(16) 0.0323(17) 0.0237(15) -0.0008(13) -0.0109(13) -0.0033(14) C45 0.041(3) 0.059(3) 0.241(10) 0.066(5) 0.012(4) 0.004(2) C46 0.082(5) 0.092(5) 0.127(6) -0.014(5) -0.009(4) 0.001(4) N1 0.0258(12) 0.0400(16) 0.0204(12) 0.0045(11) 0.0025(10) -0.0037(12) N2 0.0326(15) 0.0410(17) 0.0446(18) 0.0008(14) 0.0128(14) 0.0024(13) N3 0.0300(13) 0.0356(15) 0.0223(12) 0.0005(11) -0.0067(11) 0.0029(11) N4 0.0273(13) 0.0383(15) 0.0155(11) 0.0015(11) -0.0011(10) -0.0010(11) N5 0.0254(12) 0.0369(15) 0.0191(12) 0.0034(10) -0.0034(10) -0.0011(11) N6 0.0243(12) 0.0364(14) 0.0194(12) 0.0035(11) 0.0014(10) 0.0000(11) N7 0.0300(13) 0.0333(14) 0.0217(12) 0.0010(11) -0.0024(10) 0.0002(11) N8 0.0298(13) 0.0359(15) 0.0190(12) -0.0004(11) -0.0048(10) 0.0043(11) N9 0.0280(13) 0.0373(15) 0.0212(12) 0.0010(11) -0.0036(10) 0.0017(11) N10 0.0314(13) 0.0387(15) 0.0195(12) 0.0026(11) -0.0005(11) -0.0005(12) N11 0.0511(19) 0.060(2) 0.0233(14) 0.0026(15) -0.0150(14) -0.0176(17) N12 0.0292(14) 0.063(2) 0.063(3) -0.0053(19) 0.0018(15) -0.0021(15) N13 0.0287(13) 0.0397(16) 0.0228(12) 0.0021(12) -0.0069(11) -0.0059(12) N14 0.0381(15) 0.0371(15) 0.0208(12) 0.0013(12) -0.0014(11) 0.0021(13) N15 0.0469(17) 0.0335(15) 0.0248(13) -0.0016(12) -0.0017(12) -0.0019(13) N16 0.0385(15) 0.0370(15) 0.0258(14) 0.0019(12) -0.0159(12) -0.0058(13) N17 0.0261(13) 0.0431(17) 0.0320(15) 0.0025(13) -0.0070(11) -0.0044(12) N18 0.0282(13) 0.0472(17) 0.0277(13) 0.0051(13) -0.0043(11) -0.0005(12) O1 0.0262(11) 0.0499(15) 0.0212(10) 0.0071(10) 0.0047(9) -0.0028(10) O2 0.0297(11) 0.0373(13) 0.0300(11) 0.0020(10) 0.0017(9) 0.0009(10) O3 0.0323(12) 0.0496(15) 0.0242(11) -0.0069(11) -0.0035(10) 0.0039(11) C1N 0.067(4) 0.106(5) 0.091(5) -0.004(4) 0.010(4) 0.037(4) C2N 0.083(5) 0.075(4) 0.094(5) -0.006(4) 0.029(4) 0.000(3) C3N 0.144(8) 0.088(5) 0.088(5) 0.016(5) 0.057(6) 0.024(6) C4N 0.111(7) 0.118(7) 0.133(7) -0.062(7) -0.036(6) 0.067(6) C5N 0.080(4) 0.054(3) 0.198(10) 0.034(5) 0.073(6) 0.018(3) C6N 0.153(8) 0.114(6) 0.084(5) 0.048(5) 0.044(5) 0.089(6) N1N 0.075(4) 0.159(7) 0.102(5) 0.051(5) 0.010(4) 0.037(4) O1N 0.129(5) 0.186(7) 0.118(5) 0.075(5) 0.026(4) 0.056(5) O2N 0.087(4) 0.149(5) 0.137(5) 0.006(4) 0.006(4) 0.018(4) C1B 0.092(5) 0.211(11) 0.076(5) -0.030(6) 0.009(4) -0.026(6) O1B 0.0497(18) 0.089(3) 0.0494(17) -0.0157(17) -0.0084(14) -0.0072(17) C1C 0.19(3) 0.18(2) 0.16(2) 0.05(2) 0.08(2) 0.01(2) O1C 0.072(5) 0.138(8) 0.054(4) 0.009(5) 0.015(4) 0.029(6) O1GW 0.127(15) 0.29(3) 0.23(2) -0.134(19) 0.100(15) -0.080(16) C1G 0.19(2) 0.29(3) 0.24(3) -0.12(2) 0.105(15) -0.12(2) O1G 0.156(12) 0.048(4) 0.123(9) -0.047(5) 0.124(9) -0.042(6) C1J 0.107(15) 0.22(2) 0.092(12) 0.028(17) 0.000(11) -0.060(14) O1J 0.110(11) 0.33(2) 0.169(15) 0.106(17) 0.048(11) 0.096(15) C1D 0.150(13) 0.064(7) 0.057(6) 0.009(6) 0.031(7) -0.026(8) O1D 0.157(15) 0.25(2) 0.211(18) 0.077(17) -0.068(14) -0.021(16) C1I 0.125(16) 0.23(3) 0.21(3) 0.11(2) 0.002(17) -0.057(18) O1I 0.070(6) 0.179(11) 0.095(7) 0.016(8) 0.004(6) -0.041(7) C1E 0.059(11) 0.14(2) 1.09(10) 0.16(4) 0.02(3) 0.008(13) O1E 0.104(14) 0.27(3) 1.15(10) 0.30(4) 0.02(3) -0.045(17) C1H 0.33(4) 0.15(2) 0.26(3) -0.091(18) -0.18(3) 0.09(2) O1H 0.132(14) 0.24(2) 0.37(3) 0.12(2) -0.023(17) -0.009(14) O1W 0.160(6) 0.121(5) 0.115(5) 0.001(3) -0.043(4) 0.058(4) O2W 0.62(5) 0.143(15) 0.114(13) 0.026(10) -0.06(2) 0.02(2) N1X 0.056(7) 0.105(12) 0.058(7) 0.025(7) -0.008(6) -0.004(7) O1X 0.078(8) 0.173(16) 0.080(9) 0.043(9) 0.016(7) 0.029(9) O2X 0.055(7) 0.28(2) 0.059(9) 0.009(12) -0.020(6) -0.036(11) O3X 0.030(4) 0.033(4) 0.026(4) 0.006(3) 0.013(3) 0.008(3) C1F 0.036(9) 0.111(17) 0.025(8) 0.014(9) -0.022(7) -0.042(10) O1F 0.032(6) 0.136(14) 0.016(5) 0.005(7) 0.001(5) 0.002(7) C1A 0.146(19) 0.33(3) 0.18(2) -0.031(19) -0.042(17) 0.00(2) O1A 0.047(3) 0.129(7) 0.060(4) 0.039(4) 0.003(3) 0.032(4) O1YW 0.095(8) 0.085(7) 0.057(7) -0.027(5) 0.028(6) -0.020(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 O1 2.060(2) . ? Co1 O2 2.122(2) . ? Co1 O3 2.139(2) . ? Co1 N3 2.143(3) 4_655 ? Co1 N10 2.158(3) . ? Co1 N1 2.216(3) . ? C1 C4 1.381(5) . ? C1 C2 1.384(5) . ? C1 C6 1.504(4) . ? C2 C3 1.385(5) . ? C2 H2A 0.9500 . ? C3 N1 1.332(5) . ? C3 H3A 0.9500 . ? C4 C5 1.382(4) . ? C4 H4A 0.9500 . ? C5 N1 1.347(4) . ? C5 H5A 0.9500 . ? C6 N5 1.344(4) . ? C6 N4 1.347(4) . ? C7 C10 1.381(5) . ? C7 C8 1.389(5) . ? C7 C12 1.502(5) . ? C8 C9 1.399(5) . ? C8 H8A 0.9500 . ? C9 N2 1.319(5) . ? C9 H9A 0.9500 . ? C10 C11 1.368(5) . ? C10 H10A 0.9500 . ? C11 N2 1.357(5) . ? C11 H11A 0.9500 . ? C12 N6 1.348(4) . ? C12 N7 1.349(4) . ? C13 C14 1.378(5) . ? C13 C16 1.384(5) . ? C13 C18 1.485(4) . ? C14 C15 1.390(5) . ? C14 H14A 0.9500 . ? C15 N3 1.313(5) . ? C15 H15A 0.9500 . ? C16 C17 1.373(5) . ? C16 H16A 0.9500 . ? C17 N3 1.328(5) . ? C17 H17A 0.9500 . ? C18 N8 1.344(4) . ? C18 N9 1.348(4) . ? C19 N9 1.353(4) . ? C19 N4 1.356(4) . ? C19 C21 1.385(5) . ? C20 N5 1.349(4) . ? C20 N6 1.360(4) . ? C20 C21 1.406(4) . ? C21 C22 1.411(4) . ? C22 N8 1.348(4) . ? C22 N7 1.357(4) . ? C35 C38 1.369(6) . ? C35 C36 1.389(6) . ? C35 C40 1.483(5) . ? C38 C39 1.401(6) . ? C38 H38A 0.9500 . ? C39 N12 1.321(7) . ? C39 H39A 0.9500 . ? C36 C37 1.385(7) . ? C36 H36A 0.9500 . ? C37 N12 1.337(6) . ? C37 H37A 0.9500 . ? C40 N17 1.333(5) . ? C40 N18 1.355(5) . ? C29 C30 1.383(6) . ? C29 C32 1.388(6) . ? C29 C34 1.491(5) . ? C32 C33 1.392(5) . ? C32 H32A 0.9500 . ? C33 N11 1.329(6) . ? C33 H33A 0.9500 . ? C30 C31 1.413(5) . ? C30 H30A 0.9500 . ? C31 N11 1.307(6) . ? C31 H31A 0.9500 . ? C34 N15 1.339(5) . ? C34 N16 1.339(5) . ? C23 C26 1.382(5) . ? C23 C24 1.396(5) . ? C23 C28 1.487(5) . ? C26 C27 1.373(5) . ? C26 H26A 0.9500 . ? C27 N10 1.337(4) . ? C27 H27A 0.9500 . ? C24 C25 1.362(5) . ? C24 H24A 0.9500 . ? C25 N10 1.358(4) . ? C25 H25A 0.9500 . ? C28 N13 1.337(5) . ? C28 N14 1.345(4) . ? C41 N18 1.336(5) . ? C41 N13 1.358(4) . ? C41 C43 1.410(4) . ? C44 N16 1.356(4) . ? C44 N17 1.359(5) . ? C44 C43 1.386(5) . ? C43 C42 1.415(5) . ? C42 N15 1.343(4) . ? C42 N14 1.350(4) . ? C45 O2 1.393(6) . ? C45 H45A 0.9800 . ? C45 H45B 0.9800 . ? C45 H45C 0.9800 . ? C46 O3 1.340(8) . ? C46 H46A 0.9800 . ? C46 H46B 0.9800 . ? C46 H46C 0.9800 . ? N3 Co1 2.143(3) 4_654 ? C1N C2N 1.281(11) . ? C1N C6N 1.407(13) . ? C1N N1N 1.440(11) . ? C2N C3N 1.265(13) . ? C2N H2NA 0.9500 . ? C3N C4N 1.391(14) . ? C3N H3NA 0.9500 . ? C4N C5N 1.358(14) . ? C4N H4NA 0.9500 . ? C5N C6N 1.446(14) . ? C5N H5NA 0.9500 . ? C6N H6NA 0.9500 . ? N1N O1N 1.204(8) . ? N1N O2N 1.285(10) . ? C1B O1B 1.424(9) . ? C1C O1C 1.486(16) . ? C1G O1G 1.469(17) . ? C1J O1J 1.33(4) . ? C1D O1D 1.571(15) . ? C1I O1I 1.36(2) . ? C1E O1E 1.447(18) . ? C1H O1H 1.412(17) . ? N1X O1X 1.37(2) . ? N1X O2X 1.35(2) . ? N1X O3X 1.438(16) . ? C1F O1F 1.404(15) . ? C1A O1A 1.428(16) . ? 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 O2 90.65(10) . . ? O1 Co1 O3 85.66(10) . . ? O2 Co1 O3 88.98(10) . . ? O1 Co1 N3 177.14(11) . 4_655 ? O2 Co1 N3 87.89(10) . 4_655 ? O3 Co1 N3 91.85(10) . 4_655 ? O1 Co1 N10 91.86(10) . . ? O2 Co1 N10 173.01(10) . . ? O3 Co1 N10 84.71(10) . . ? N3 Co1 N10 89.32(11) 4_655 . ? O1 Co1 N1 88.13(10) . . ? O2 Co1 N1 91.70(10) . . ? O3 Co1 N1 173.76(10) . . ? N3 Co1 N1 94.37(10) 4_655 . ? N10 Co1 N1 94.90(11) . . ? C4 C1 C2 117.1(3) . . ? C4 C1 C6 121.3(3) . . ? C2 C1 C6 121.5(3) . . ? C1 C2 C3 119.3(3) . . ? C1 C2 H2A 120.3 . . ? C3 C2 H2A 120.3 . . ? N1 C3 C2 123.8(3) . . ? N1 C3 H3A 118.1 . . ? C2 C3 H3A 118.1 . . ? C1 C4 C5 120.1(3) . . ? C1 C4 H4A 119.9 . . ? C5 C4 H4A 119.9 . . ? N1 C5 C4 122.9(3) . . ? N1 C5 H5A 118.6 . . ? C4 C5 H5A 118.6 . . ? N5 C6 N4 129.6(3) . . ? N5 C6 C1 115.4(3) . . ? N4 C6 C1 115.0(3) . . ? C10 C7 C8 117.6(3) . . ? C10 C7 C12 122.0(3) . . ? C8 C7 C12 120.4(3) . . ? C7 C8 C9 119.5(3) . . ? C7 C8 H8A 120.2 . . ? C9 C8 H8A 120.2 . . ? N2 C9 C8 122.7(3) . . ? N2 C9 H9A 118.7 . . ? C8 C9 H9A 118.7 . . ? C11 C10 C7 119.2(3) . . ? C11 C10 H10A 120.4 . . ? C7 C10 H10A 120.4 . . ? N2 C11 C10 123.8(4) . . ? N2 C11 H11A 118.1 . . ? C10 C11 H11A 118.1 . . ? N6 C12 N7 129.5(3) . . ? N6 C12 C7 115.6(3) . . ? N7 C12 C7 114.9(3) . . ? C14 C13 C16 116.5(3) . . ? C14 C13 C18 121.6(3) . . ? C16 C13 C18 121.9(3) . . ? C13 C14 C15 119.5(3) . . ? C13 C14 H14A 120.2 . . ? C15 C14 H14A 120.2 . . ? N3 C15 C14 123.3(4) . . ? N3 C15 H15A 118.4 . . ? C14 C15 H15A 118.4 . . ? C17 C16 C13 120.2(4) . . ? C17 C16 H16A 119.9 . . ? C13 C16 H16A 119.9 . . ? N3 C17 C16 122.9(3) . . ? N3 C17 H17A 118.5 . . ? C16 C17 H17A 118.5 . . ? N8 C18 N9 129.1(3) . . ? N8 C18 C13 115.6(3) . . ? N9 C18 C13 115.3(3) . . ? N9 C19 N4 119.3(3) . . ? N9 C19 C21 120.6(3) . . ? N4 C19 C21 120.1(3) . . ? N5 C20 N6 120.0(3) . . ? N5 C20 C21 119.7(3) . . ? N6 C20 C21 120.3(3) . . ? C19 C21 C20 120.6(3) . . ? C19 C21 C22 120.0(3) . . ? C20 C21 C22 119.4(3) . . ? N8 C22 N7 119.6(3) . . ? N8 C22 C21 119.8(3) . . ? N7 C22 C21 120.6(3) . . ? C38 C35 C36 118.1(4) . . ? C38 C35 C40 120.6(4) . . ? C36 C35 C40 121.3(4) . . ? C35 C38 C39 118.7(4) . . ? C35 C38 H38A 120.6 . . ? C39 C38 H38A 120.6 . . ? N12 C39 C38 123.7(4) . . ? N12 C39 H39A 118.2 . . ? C38 C39 H39A 118.2 . . ? C37 C36 C35 118.8(4) . . ? C37 C36 H36A 120.6 . . ? C35 C36 H36A 120.6 . . ? N12 C37 C36 123.4(4) . . ? N12 C37 H37A 118.3 . . ? C36 C37 H37A 118.3 . . ? N17 C40 N18 129.3(3) . . ? N17 C40 C35 115.1(3) . . ? N18 C40 C35 115.6(3) . . ? C30 C29 C32 118.7(3) . . ? C30 C29 C34 120.6(4) . . ? C32 C29 C34 120.7(3) . . ? C29 C32 C33 118.3(4) . . ? C29 C32 H32A 120.8 . . ? C33 C32 H32A 120.8 . . ? N11 C33 C32 122.8(4) . . ? N11 C33 H33A 118.6 . . ? C32 C33 H33A 118.6 . . ? C29 C30 C31 118.6(4) . . ? C29 C30 H30A 120.7 . . ? C31 C30 H30A 120.7 . . ? N11 C31 C30 122.3(4) . . ? N11 C31 H31A 118.9 . . ? C30 C31 H31A 118.9 . . ? N15 C34 N16 129.9(3) . . ? N15 C34 C29 114.8(3) . . ? N16 C34 C29 115.2(3) . . ? C26 C23 C24 117.2(3) . . ? C26 C23 C28 121.3(3) . . ? C24 C23 C28 121.6(3) . . ? C27 C26 C23 119.0(3) . . ? C27 C26 H26A 120.5 . . ? C23 C26 H26A 120.5 . . ? N10 C27 C26 124.6(3) . . ? N10 C27 H27A 117.7 . . ? C26 C27 H27A 117.7 . . ? C25 C24 C23 120.2(3) . . ? C25 C24 H24A 119.9 . . ? C23 C24 H24A 119.9 . . ? N10 C25 C24 123.0(3) . . ? N10 C25 H25A 118.5 . . ? C24 C25 H25A 118.5 . . ? N13 C28 N14 128.6(3) . . ? N13 C28 C23 115.5(3) . . ? N14 C28 C23 115.9(3) . . ? N18 C41 N13 120.8(3) . . ? N18 C41 C43 119.6(3) . . ? N13 C41 C43 119.5(3) . . ? N16 C44 N17 119.3(3) . . ? N16 C44 C43 120.4(3) . . ? N17 C44 C43 120.2(3) . . ? C44 C43 C41 120.3(3) . . ? C44 C43 C42 120.1(3) . . ? C41 C43 C42 119.5(3) . . ? N15 C42 N14 120.5(3) . . ? N15 C42 C43 119.5(3) . . ? N14 C42 C43 120.0(3) . . ? O2 C45 H45A 109.5 . . ? O2 C45 H45B 109.5 . . ? H45A C45 H45B 109.5 . . ? O2 C45 H45C 109.5 . . ? H45A C45 H45C 109.5 . . ? H45B C45 H45C 109.5 . . ? O3 C46 H46A 109.5 . . ? O3 C46 H46B 109.5 . . ? H46A C46 H46B 109.5 . . ? O3 C46 H46C 109.5 . . ? H46A C46 H46C 109.5 . . ? H46B C46 H46C 109.5 . . ? C3 N1 C5 116.6(3) . . ? C3 N1 Co1 121.4(2) . . ? C5 N1 Co1 120.8(2) . . ? C9 N2 C11 117.1(3) . . ? C15 N3 C17 117.6(3) . . ? C15 N3 Co1 120.6(2) . 4_654 ? C17 N3 Co1 121.5(2) . 4_654 ? C6 N4 C19 114.8(3) . . ? C6 N5 C20 115.1(3) . . ? C12 N6 C20 115.2(3) . . ? C12 N7 C22 115.0(3) . . ? C18 N8 C22 115.4(3) . . ? C18 N9 C19 115.0(3) . . ? C27 N10 C25 115.9(3) . . ? C27 N10 Co1 122.1(2) . . ? C25 N10 Co1 121.1(2) . . ? C31 N11 C33 119.3(3) . . ? C39 N12 C37 117.0(4) . . ? C28 N13 C41 116.4(3) . . ? C28 N14 C42 116.0(3) . . ? C34 N15 C42 115.5(3) . . ? C34 N16 C44 114.5(3) . . ? C40 N17 C44 114.9(3) . . ? C41 N18 C40 115.6(3) . . ? C45 O2 Co1 129.4(3) . . ? C46 O3 Co1 126.0(4) . . ? C2N C1N C6N 124.2(8) . . ? C2N C1N N1N 125.2(9) . . ? C6N C1N N1N 110.6(8) . . ? C3N C2N C1N 121.0(8) . . ? C3N C2N H2NA 119.5 . . ? C1N C2N H2NA 119.5 . . ? C2N C3N C4N 121.0(8) . . ? C2N C3N H3NA 119.5 . . ? C4N C3N H3NA 119.5 . . ? C5N C4N C3N 122.5(9) . . ? C5N C4N H4NA 118.8 . . ? C3N C4N H4NA 118.8 . . ? C4N C5N C6N 115.2(8) . . ? C4N C5N H5NA 122.4 . . ? C6N C5N H5NA 122.4 . . ? C1N C6N C5N 116.1(6) . . ? C1N C6N H6NA 122.0 . . ? C5N C6N H6NA 122.0 . . ? O1N N1N O2N 122.5(9) . . ? O1N N1N C1N 123.2(9) . . ? O2N N1N C1N 114.3(7) . . ? O1X N1X O2X 126.1(15) . . ? O1X N1X O3X 124.5(13) . . ? O2X N1X O3X 109.3(14) . . ? 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 C4 C1 C2 C3 -2.4(5) . . . . ? C6 C1 C2 C3 174.9(3) . . . . ? C1 C2 C3 N1 -0.5(5) . . . . ? C2 C1 C4 C5 3.5(5) . . . . ? C6 C1 C4 C5 -173.8(3) . . . . ? C1 C4 C5 N1 -1.7(5) . . . . ? C4 C1 C6 N5 156.9(3) . . . . ? C2 C1 C6 N5 -20.3(4) . . . . ? C4 C1 C6 N4 -22.3(4) . . . . ? C2 C1 C6 N4 160.6(3) . . . . ? C10 C7 C8 C9 -1.4(5) . . . . ? C12 C7 C8 C9 179.1(3) . . . . ? C7 C8 C9 N2 -0.3(6) . . . . ? C8 C7 C10 C11 1.1(5) . . . . ? C12 C7 C10 C11 -179.5(3) . . . . ? C7 C10 C11 N2 1.1(6) . . . . ? C10 C7 C12 N6 -1.8(5) . . . . ? C8 C7 C12 N6 177.6(3) . . . . ? C10 C7 C12 N7 176.5(3) . . . . ? C8 C7 C12 N7 -4.1(5) . . . . ? C16 C13 C14 C15 -1.0(6) . . . . ? C18 C13 C14 C15 178.4(4) . . . . ? C13 C14 C15 N3 2.4(7) . . . . ? C14 C13 C16 C17 -1.0(6) . . . . ? C18 C13 C16 C17 179.6(4) . . . . ? C13 C16 C17 N3 1.9(8) . . . . ? C14 C13 C18 N8 -159.3(4) . . . . ? C16 C13 C18 N8 20.1(5) . . . . ? C14 C13 C18 N9 21.0(5) . . . . ? C16 C13 C18 N9 -159.6(4) . . . . ? N9 C19 C21 C20 -178.9(3) . . . . ? N4 C19 C21 C20 0.6(5) . . . . ? N9 C19 C21 C22 1.0(5) . . . . ? N4 C19 C21 C22 -179.5(3) . . . . ? N5 C20 C21 C19 0.5(5) . . . . ? N6 C20 C21 C19 -179.1(3) . . . . ? N5 C20 C21 C22 -179.5(3) . . . . ? N6 C20 C21 C22 1.0(5) . . . . ? C19 C21 C22 N8 -1.2(5) . . . . ? C20 C21 C22 N8 178.8(3) . . . . ? C19 C21 C22 N7 178.8(3) . . . . ? C20 C21 C22 N7 -1.2(5) . . . . ? C36 C35 C38 C39 4.6(7) . . . . ? C40 C35 C38 C39 -173.3(4) . . . . ? C35 C38 C39 N12 -1.0(8) . . . . ? C38 C35 C36 C37 -5.9(7) . . . . ? C40 C35 C36 C37 171.9(4) . . . . ? C35 C36 C37 N12 3.9(8) . . . . ? C38 C35 C40 N17 27.3(5) . . . . ? C36 C35 C40 N17 -150.5(4) . . . . ? C38 C35 C40 N18 -153.6(4) . . . . ? C36 C35 C40 N18 28.6(5) . . . . ? C30 C29 C32 C33 0.3(6) . . . . ? C34 C29 C32 C33 -178.2(3) . . . . ? C29 C32 C33 N11 0.2(6) . . . . ? C32 C29 C30 C31 -0.3(6) . . . . ? C34 C29 C30 C31 178.2(4) . . . . ? C29 C30 C31 N11 -0.1(7) . . . . ? C30 C29 C34 N15 155.4(4) . . . . ? C32 C29 C34 N15 -26.1(5) . . . . ? C30 C29 C34 N16 -23.9(5) . . . . ? C32 C29 C34 N16 154.6(3) . . . . ? C24 C23 C26 C27 1.6(5) . . . . ? C28 C23 C26 C27 -176.9(3) . . . . ? C23 C26 C27 N10 -2.0(5) . . . . ? C26 C23 C24 C25 -0.2(6) . . . . ? C28 C23 C24 C25 178.3(4) . . . . ? C23 C24 C25 N10 -1.0(6) . . . . ? C26 C23 C28 N13 -9.9(5) . . . . ? C24 C23 C28 N13 171.6(3) . . . . ? C26 C23 C28 N14 167.9(3) . . . . ? C24 C23 C28 N14 -10.5(5) . . . . ? N16 C44 C43 C41 -176.1(3) . . . . ? N17 C44 C43 C41 2.0(5) . . . . ? N16 C44 C43 C42 -0.7(5) . . . . ? N17 C44 C43 C42 177.4(3) . . . . ? N18 C41 C43 C44 -0.3(5) . . . . ? N13 C41 C43 C44 177.3(3) . . . . ? N18 C41 C43 C42 -175.8(3) . . . . ? N13 C41 C43 C42 1.9(5) . . . . ? C44 C43 C42 N15 -0.4(5) . . . . ? C41 C43 C42 N15 175.1(3) . . . . ? C44 C43 C42 N14 -179.3(3) . . . . ? C41 C43 C42 N14 -3.8(5) . . . . ? C2 C3 N1 C5 2.4(5) . . . . ? C2 C3 N1 Co1 -165.1(3) . . . . ? C4 C5 N1 C3 -1.3(5) . . . . ? C4 C5 N1 Co1 166.3(3) . . . . ? O1 Co1 N1 C3 85.2(3) . . . . ? O2 Co1 N1 C3 175.8(2) . . . . ? O3 Co1 N1 C3 79.6(10) . . . . ? N3 Co1 N1 C3 -96.2(3) 4_655 . . . ? N10 Co1 N1 C3 -6.5(3) . . . . ? O1 Co1 N1 C5 -81.8(3) . . . . ? O2 Co1 N1 C5 8.8(3) . . . . ? O3 Co1 N1 C5 -87.4(10) . . . . ? N3 Co1 N1 C5 96.8(3) 4_655 . . . ? N10 Co1 N1 C5 -173.5(3) . . . . ? C8 C9 N2 C11 2.4(5) . . . . ? C10 C11 N2 C9 -2.8(6) . . . . ? C14 C15 N3 C17 -1.6(6) . . . . ? C14 C15 N3 Co1 171.2(3) . . . 4_654 ? C16 C17 N3 C15 -0.6(7) . . . . ? C16 C17 N3 Co1 -173.3(4) . . . 4_654 ? N5 C6 N4 C19 -1.9(5) . . . . ? C1 C6 N4 C19 177.1(3) . . . . ? N9 C19 N4 C6 179.5(3) . . . . ? C21 C19 N4 C6 0.0(4) . . . . ? N4 C6 N5 C20 3.0(5) . . . . ? C1 C6 N5 C20 -176.0(3) . . . . ? N6 C20 N5 C6 177.5(3) . . . . ? C21 C20 N5 C6 -2.0(4) . . . . ? N7 C12 N6 C20 -1.0(5) . . . . ? C7 C12 N6 C20 177.1(3) . . . . ? N5 C20 N6 C12 -179.5(3) . . . . ? C21 C20 N6 C12 0.0(4) . . . . ? N6 C12 N7 C22 0.8(5) . . . . ? C7 C12 N7 C22 -177.3(3) . . . . ? N8 C22 N7 C12 -179.6(3) . . . . ? C21 C22 N7 C12 0.4(4) . . . . ? N9 C18 N8 C22 -1.2(5) . . . . ? C13 C18 N8 C22 179.2(3) . . . . ? N7 C22 N8 C18 -178.8(3) . . . . ? C21 C22 N8 C18 1.2(4) . . . . ? N8 C18 N9 C19 1.0(5) . . . . ? C13 C18 N9 C19 -179.4(3) . . . . ? N4 C19 N9 C18 179.6(3) . . . . ? C21 C19 N9 C18 -0.9(4) . . . . ? C26 C27 N10 C25 0.9(5) . . . . ? C26 C27 N10 Co1 170.3(3) . . . . ? C24 C25 N10 C27 0.7(6) . . . . ? C24 C25 N10 Co1 -168.9(3) . . . . ? O1 Co1 N10 C27 -24.6(3) . . . . ? O2 Co1 N10 C27 -135.6(8) . . . . ? O3 Co1 N10 C27 -110.1(3) . . . . ? N3 Co1 N10 C27 158.0(3) 4_655 . . . ? N1 Co1 N10 C27 63.7(3) . . . . ? O1 Co1 N10 C25 144.4(3) . . . . ? O2 Co1 N10 C25 33.4(10) . . . . ? O3 Co1 N10 C25 58.9(3) . . . . ? N3 Co1 N10 C25 -33.0(3) 4_655 . . . ? N1 Co1 N10 C25 -127.4(3) . . . . ? C30 C31 N11 C33 0.6(6) . . . . ? C32 C33 N11 C31 -0.6(6) . . . . ? C38 C39 N12 C37 -1.2(7) . . . . ? C36 C37 N12 C39 -0.3(8) . . . . ? N14 C28 N13 C41 -1.6(5) . . . . ? C23 C28 N13 C41 175.9(3) . . . . ? N18 C41 N13 C28 178.4(3) . . . . ? C43 C41 N13 C28 0.7(4) . . . . ? N13 C28 N14 C42 -0.3(5) . . . . ? C23 C28 N14 C42 -177.8(3) . . . . ? N15 C42 N14 C28 -175.9(3) . . . . ? C43 C42 N14 C28 3.0(5) . . . . ? N16 C34 N15 C42 2.7(5) . . . . ? C29 C34 N15 C42 -176.5(3) . . . . ? N14 C42 N15 C34 178.5(3) . . . . ? C43 C42 N15 C34 -0.4(5) . . . . ? N15 C34 N16 C44 -3.7(5) . . . . ? C29 C34 N16 C44 175.5(3) . . . . ? N17 C44 N16 C34 -175.7(3) . . . . ? C43 C44 N16 C34 2.5(5) . . . . ? N18 C40 N17 C44 0.4(5) . . . . ? C35 C40 N17 C44 179.4(3) . . . . ? N16 C44 N17 C40 176.2(3) . . . . ? C43 C44 N17 C40 -1.9(5) . . . . ? N13 C41 N18 C40 -178.7(3) . . . . ? C43 C41 N18 C40 -1.1(5) . . . . ? N17 C40 N18 C41 1.1(5) . . . . ? C35 C40 N18 C41 -177.8(3) . . . . ? O1 Co1 O2 C45 -18.6(6) . . . . ? O3 Co1 O2 C45 67.1(6) . . . . ? N3 Co1 O2 C45 159.0(6) 4_655 . . . ? N10 Co1 O2 C45 92.5(10) . . . . ? N1 Co1 O2 C45 -106.7(6) . . . . ? O1 Co1 O3 C46 76.3(5) . . . . ? O2 Co1 O3 C46 -14.5(5) . . . . ? N3 Co1 O3 C46 -102.3(5) 4_655 . . . ? N10 Co1 O3 C46 168.5(5) . . . . ? N1 Co1 O3 C46 81.9(11) . . . . ? C6N C1N C2N C3N 1.1(12) . . . . ? N1N C1N C2N C3N -179.4(7) . . . . ? C1N C2N C3N C4N 0.2(12) . . . . ? C2N C3N C4N C5N -0.9(12) . . . . ? C3N C4N C5N C6N 0.3(10) . . . . ? C2N C1N C6N C5N -1.6(10) . . . . ? N1N C1N C6N C5N 178.8(6) . . . . ? C4N C5N C6N C1N 0.9(9) . . . . ? C2N C1N N1N O1N 179.0(8) . . . . ? C6N C1N N1N O1N -1.5(10) . . . . ? C2N C1N N1N O2N -3.8(11) . . . . ? C6N C1N N1N O2N 175.8(6) . . . . ? _diffrn_measured_fraction_theta_max 0.982 _diffrn_reflns_theta_full 29.90 _diffrn_measured_fraction_theta_full 0.982 _refine_diff_density_max 0.917 _refine_diff_density_min -0.587 _refine_diff_density_rms 0.098 # Attachment '- pnc2.cif' data_TPHAP-Co-Therm-1 _database_code_depnum_ccdc_archive 'CCDC 885674' #TrackingRef '- pnc2.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C54 H41 Co2 N21 O13' _chemical_formula_weight 1309.94 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Co Co 0.3494 0.9721 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M Pnc2 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z' 'x, -y+1/2, z+1/2' '-x, y+1/2, z+1/2' _cell_length_a 14.6913(3) _cell_length_b 27.1030(5) _cell_length_c 8.2799(1) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 3296.9(1) _cell_formula_units_Z 2 _cell_measurement_temperature 90(2) _cell_measurement_reflns_used 40031 _cell_measurement_theta_min 0.64 _cell_measurement_theta_max 50.00 _exptl_crystal_description platelet _exptl_crystal_colour red _exptl_crystal_size_max 0.17 _exptl_crystal_size_mid 0.08 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.320 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1340 _exptl_absorpt_coefficient_mu 0.576 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.9074 _exptl_absorpt_correction_T_max 0.9773 _exptl_absorpt_process_details HKL2000 _exptl_special_details ; ? ; _diffrn_ambient_temperature 90(2) _diffrn_radiation_wavelength 0.68890 _diffrn_radiation_type synchrotron _diffrn_radiation_source 'undulator KEK PF-NW2A' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type CCD _diffrn_measurement_method omega_scan _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 38936 _diffrn_reflns_av_R_equivalents 0.0887 _diffrn_reflns_av_sigmaI/netI 0.0878 _diffrn_reflns_limit_h_min -21 _diffrn_reflns_limit_h_max 22 _diffrn_reflns_limit_k_min -41 _diffrn_reflns_limit_k_max 41 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 1.98 _diffrn_reflns_theta_max 32.37 _reflns_number_total 12312 _reflns_number_gt 9066 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Rigaku CrystalClear' _computing_cell_refinement HKL2000 _computing_data_reduction HKL2000 _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Bruker XP' _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. Because C17A and C17B are closely located, a constraint was applied to the temperature factor to be equal. A nitrobeneze is disordered at two positions with occupancy of 0.5, respectively. A restraint was applied to disordered water (O1W) on a basis of chemical symmetry of the molecules. The occupancy of water molecule (O1W) is 0.5. ; _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^)+(0.1038P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.040(19) _refine_ls_number_reflns 12312 _refine_ls_number_parameters 481 _refine_ls_number_restraints 7 _refine_ls_R_factor_all 0.0902 _refine_ls_R_factor_gt 0.0722 _refine_ls_wR_factor_ref 0.2066 _refine_ls_wR_factor_gt 0.1940 _refine_ls_goodness_of_fit_ref 1.102 _refine_ls_restrained_S_all 1.102 _refine_ls_shift/su_max 0.002 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Co1 Co 1.20841(3) 0.631493(12) 0.03671(8) 0.01764(10) Uani 1 1 d . . . C1 C 0.6018(2) 0.72939(11) 0.8726(5) 0.0212(6) Uani 1 1 d . . . C1A C 0.8355(8) 0.9748(4) 0.0720(13) 0.052(3) Uani 0.50 1 d P A 1 C2A C 0.8229(10) 0.9255(6) 0.1122(19) 0.075(4) Uani 0.50 1 d P A 1 H2AA H 0.8680 0.9017 0.0861 0.089 Uiso 0.50 1 calc PR A 1 C3A C 0.7593(13) 0.9141(6) 0.175(3) 0.096(6) Uani 0.50 1 d P A 1 H3AA H 0.7472 0.8797 0.1810 0.115 Uiso 0.50 1 calc PR A 1 C4A C 0.6931(12) 0.9468(7) 0.250(2) 0.090(5) Uani 0.50 1 d P A 1 H4AA H 0.6481 0.9338 0.3208 0.108 Uiso 0.50 1 calc PR A 1 C5A C 0.6959(10) 0.9940(4) 0.2199(18) 0.062(3) Uani 0.50 1 d P A 1 H5AA H 0.6512 1.0158 0.2619 0.074 Uiso 0.50 1 calc PR A 1 C6A C 0.7638(12) 1.0103(4) 0.1277(19) 0.073(4) Uani 0.50 1 d P A 1 H6AA H 0.7668 1.0441 0.0976 0.088 Uiso 0.50 1 calc PR A 1 O1A O 0.9624(8) 0.9582(3) -0.0809(14) 0.085(3) Uani 0.50 1 d P . 1 O2A O 0.9171(9) 1.0354(3) -0.0628(13) 0.085(3) Uani 0.50 1 d P . 1 N1A N 0.9148(12) 0.9913(4) -0.0321(14) 0.084(4) Uani 0.50 1 d P A 1 O1W O 0.5471(9) 0.8984(8) 0.906(5) 0.28(2) Uani 0.50 1 d P B 1 C2 C 0.5973(4) 0.67838(15) 0.8726(8) 0.0523(15) Uani 1 1 d . . . H2A H 0.6423 0.6595 0.8180 0.063 Uiso 1 1 calc R . . C3 C 0.5271(4) 0.65513(15) 0.9523(8) 0.0585(17) Uani 1 1 d . . . H3 H 0.5248 0.6201 0.9509 0.070 Uiso 1 1 calc R . . C4 C 0.5363(2) 0.75476(12) 0.9605(5) 0.0252(7) Uani 1 1 d . . . H4A H 0.5389 0.7897 0.9688 0.030 Uiso 1 1 calc R . . C5 C 0.4676(2) 0.72883(11) 1.0358(6) 0.0261(6) Uani 1 1 d . . . H5A H 0.4222 0.7467 1.0930 0.031 Uiso 1 1 calc R . . C6 C 0.6770(2) 0.75568(12) 0.7857(5) 0.0196(6) Uani 1 1 d . . . C7 C 1.0040(2) 0.72098(11) 0.3936(4) 0.0185(6) Uani 1 1 d . . . C8 C 1.0803(3) 0.74243(12) 0.3235(5) 0.0284(8) Uani 1 1 d . . . H8 H 1.0913 0.7768 0.3361 0.034 Uiso 1 1 calc R . . C9 C 1.1400(2) 0.71391(11) 0.2358(5) 0.0252(7) Uani 1 1 d . . . H9 H 1.1921 0.7293 0.1901 0.030 Uiso 1 1 calc R . . C10 C 0.9930(2) 0.67000(11) 0.3714(4) 0.0214(6) Uani 1 1 d . . . H10A H 0.9425 0.6536 0.4186 0.026 Uiso 1 1 calc R . . C11 C 1.0544(2) 0.64405(11) 0.2825(5) 0.0226(7) Uani 1 1 d . . . H11A H 1.0456 0.6096 0.2692 0.027 Uiso 1 1 calc R . . C12 C 0.9348(2) 0.75050(11) 0.4824(4) 0.0166(5) Uani 1 1 d . . . N3 N 0.8079(2) 1.05627(10) 0.5869(4) 0.0225(6) Uani 1 1 d . . . C13 C 0.8109(2) 0.95343(11) 0.6105(5) 0.0231(7) Uani 1 1 d . . . C15A C 0.7333(14) 1.0304(7) 0.619(2) 0.052(5) Uani 0.50 1 d P C 1 H15A H 0.6780 1.0482 0.6313 0.063 Uiso 0.50 1 calc PR C 1 C14A C 0.7293(8) 0.9786(4) 0.636(2) 0.047(4) Uani 0.50 1 d P C 1 H14A H 0.6745 0.9620 0.6638 0.056 Uiso 0.50 1 calc PR C 1 C16A C 0.8848(7) 0.9781(4) 0.5745(16) 0.028(2) Uani 0.50 1 d P C 1 H16A H 0.9398 0.9608 0.5540 0.033 Uiso 0.50 1 calc PR C 1 C17A C 0.8834(6) 1.0292(3) 0.5661(12) 0.0272(16) Uani 0.50 1 d PU C 1 H17A H 0.9389 1.0460 0.5444 0.033 Uiso 0.50 1 calc PR C 1 C15B C 0.7514(15) 1.0317(6) 0.6849(18) 0.049(6) Uani 0.50 1 d P C 2 H15B H 0.7072 1.0498 0.7440 0.059 Uiso 0.50 1 calc PR C 2 C14B C 0.7542(8) 0.9827(4) 0.7032(16) 0.034(3) Uani 0.50 1 d P C 2 H14B H 0.7163 0.9676 0.7820 0.041 Uiso 0.50 1 calc PR C 2 C16B C 0.8709(9) 0.9789(5) 0.5053(12) 0.028(3) Uani 0.50 1 d P C 2 H16B H 0.9137 0.9609 0.4425 0.034 Uiso 0.50 1 calc PR C 2 C17B C 0.8676(7) 1.0292(4) 0.4939(13) 0.0272(16) Uani 0.50 1 d PU C 2 H17B H 0.9070 1.0457 0.4208 0.033 Uiso 0.50 1 calc PR C 2 C18 C 0.8101(2) 0.89855(10) 0.6202(5) 0.0199(6) Uani 1 1 d . C . C19 C 0.7385(2) 0.82871(11) 0.7074(4) 0.0187(6) Uani 1 1 d . C . C20 C 0.8052(2) 0.75000(10) 0.6352(4) 0.0156(5) Uani 1 1 d . . . C21 C 0.8066(2) 0.80147(10) 0.6289(4) 0.0159(5) Uani 1 1 d . . . C22 C 0.87697(19) 0.82614(9) 0.5469(5) 0.0178(5) Uani 1 1 d . C . C23 C 1.0771(5) 0.6281(3) -0.2775(7) 0.066(2) Uani 1 1 d . . . H23A H 1.0126 0.6310 -0.3067 0.099 Uiso 1 1 calc R . . H23B H 1.0999 0.5956 -0.3099 0.099 Uiso 1 1 calc R . . H23C H 1.1119 0.6539 -0.3330 0.099 Uiso 1 1 calc R . . C24 C 1.3302(3) 0.6479(2) 0.3413(6) 0.0441(11) Uani 1 1 d . . . H24A H 1.3943 0.6485 0.3734 0.066 Uiso 1 1 calc R . . H24B H 1.2982 0.6222 0.4023 0.066 Uiso 1 1 calc R . . H24C H 1.3024 0.6800 0.3639 0.066 Uiso 1 1 calc R . . N1 N 0.4620(2) 0.67961(10) 1.0316(5) 0.0303(6) Uani 1 1 d . . . N2 N 1.12788(19) 0.66554(9) 0.2121(4) 0.0202(5) Uani 1 1 d . . . N4 N 0.6718(2) 0.80517(9) 0.7873(4) 0.0213(6) Uani 1 1 d . . . N5 N 0.73881(19) 0.72627(9) 0.7164(4) 0.0187(5) Uani 1 1 d . . . N6 N 0.87095(18) 0.72368(8) 0.5573(4) 0.0184(5) Uani 1 1 d . . . N7 N 0.94389(19) 0.80008(9) 0.4733(4) 0.0179(5) Uani 1 1 d . . . N8 N 0.87896(17) 0.87583(8) 0.5429(5) 0.0212(5) Uani 1 1 d . . . N9 N 0.7399(2) 0.87854(10) 0.7017(4) 0.0228(6) Uani 1 1 d . . . N10 N 1.2943(3) 0.66847(16) -0.1996(5) 0.0396(9) Uani 1 1 d . . . O1 O 1.2547(2) 0.69526(9) -0.0968(4) 0.0316(6) Uani 1 1 d . . . O2 O 1.3358(3) 0.68559(16) -0.3136(4) 0.0677(13) Uani 1 1 d . . . O3 O 1.2893(2) 0.62196(12) -0.1746(4) 0.0376(7) Uani 1 1 d . . . O4 O 1.08719(19) 0.63394(8) -0.1034(4) 0.0257(5) Uani 1 1 d . . . O5 O 1.32368(17) 0.63767(9) 0.1742(3) 0.0230(5) 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 0.02031(17) 0.00886(14) 0.0238(2) -0.0006(2) 0.0048(2) -0.00052(12) C1 0.0213(14) 0.0150(12) 0.0273(17) -0.0011(12) 0.0107(13) -0.0038(10) C1A 0.055(6) 0.056(6) 0.044(7) -0.001(5) -0.013(5) -0.004(5) C2A 0.070(9) 0.079(9) 0.075(9) -0.034(7) -0.029(8) 0.038(8) C3A 0.088(12) 0.044(7) 0.155(19) -0.006(9) 0.013(13) -0.011(7) C4A 0.089(11) 0.086(12) 0.095(13) 0.019(10) -0.002(10) -0.045(9) C5A 0.080(9) 0.035(5) 0.070(8) -0.008(6) -0.008(7) 0.010(5) C6A 0.119(11) 0.017(4) 0.084(9) -0.013(5) -0.050(9) 0.000(5) O1A 0.116(9) 0.056(5) 0.082(7) -0.008(5) 0.008(6) 0.035(6) O2A 0.131(10) 0.049(5) 0.074(6) 0.006(5) 0.004(6) 0.009(5) N1A 0.154(13) 0.041(5) 0.058(6) -0.008(5) -0.024(8) 0.028(7) O1W 0.044(7) 0.23(2) 0.58(6) -0.14(3) 0.083(16) -0.019(10) C2 0.057(3) 0.0187(16) 0.082(4) -0.015(2) 0.048(3) -0.0113(17) C3 0.054(3) 0.0196(17) 0.102(4) -0.008(2) 0.049(3) -0.0123(17) C4 0.0225(15) 0.0163(13) 0.037(2) -0.0021(13) 0.0115(14) -0.0019(11) C5 0.0202(13) 0.0226(12) 0.0357(17) -0.0041(18) 0.0114(19) -0.0010(10) C6 0.0186(12) 0.0161(14) 0.0241(15) 0.0006(12) 0.0032(14) -0.0008(11) C7 0.0203(13) 0.0137(11) 0.0214(15) -0.0046(11) 0.0018(12) 0.0027(10) C8 0.0282(16) 0.0123(14) 0.045(2) -0.0095(13) 0.0138(16) -0.0035(11) C9 0.0264(16) 0.0135(12) 0.0356(19) -0.0058(13) 0.0127(15) -0.0041(11) C10 0.0229(14) 0.0148(12) 0.0264(16) 0.0011(12) 0.0081(13) 0.0002(10) C11 0.0238(15) 0.0117(11) 0.0322(19) -0.0010(12) 0.0092(14) 0.0012(10) C12 0.0178(12) 0.0131(11) 0.0191(13) -0.0019(10) 0.0029(11) -0.0012(9) N3 0.0246(13) 0.0100(10) 0.0328(16) -0.0001(9) 0.0019(11) 0.0000(8) C13 0.0261(15) 0.0088(11) 0.0344(19) 0.0009(12) 0.0046(14) 0.0016(10) C15A 0.035(5) 0.021(5) 0.101(15) 0.016(9) 0.037(10) 0.009(4) C14A 0.024(5) 0.007(3) 0.109(13) -0.001(6) 0.022(6) -0.006(3) C16A 0.013(3) 0.007(3) 0.062(7) 0.004(5) 0.002(4) 0.000(2) C17A 0.020(3) 0.0143(14) 0.047(5) 0.015(4) 0.002(3) 0.0004(18) C15B 0.080(14) 0.011(3) 0.057(9) 0.006(6) 0.057(10) 0.012(6) C14B 0.035(6) 0.013(3) 0.055(7) -0.001(4) 0.031(5) -0.005(4) C16B 0.037(6) 0.017(3) 0.032(5) 0.000(4) 0.008(4) 0.012(4) C17B 0.020(3) 0.0143(14) 0.047(5) 0.015(4) 0.002(3) 0.0004(18) C18 0.0220(14) 0.0087(11) 0.0291(18) 0.0008(11) 0.0033(13) 0.0004(9) C19 0.0187(13) 0.0143(12) 0.0230(16) -0.0007(11) 0.0029(12) 0.0007(10) C20 0.0182(12) 0.0097(10) 0.0191(15) -0.0004(10) 0.0014(11) 0.0007(9) C21 0.0166(12) 0.0102(11) 0.0210(15) -0.0005(10) 0.0028(11) 0.0013(8) C22 0.0170(11) 0.0130(10) 0.0233(15) -0.0004(13) 0.0024(14) 0.0000(8) C23 0.058(4) 0.098(5) 0.043(3) -0.032(3) -0.017(3) 0.031(3) C24 0.037(2) 0.064(3) 0.032(2) 0.000(2) 0.0039(19) -0.012(2) N1 0.0277(13) 0.0229(12) 0.0405(17) -0.0015(17) 0.0128(18) -0.0080(10) N2 0.0222(12) 0.0126(10) 0.0258(14) -0.0022(10) 0.0038(12) 0.0013(9) N4 0.0192(12) 0.0143(10) 0.0303(16) -0.0009(10) 0.0069(12) 0.0000(9) N5 0.0194(11) 0.0126(10) 0.0240(14) -0.0026(10) 0.0042(11) -0.0008(9) N6 0.0193(10) 0.0121(9) 0.0238(15) -0.0010(10) 0.0059(11) -0.0014(7) N7 0.0186(12) 0.0108(9) 0.0244(13) -0.0002(9) 0.0034(10) 0.0012(8) N8 0.0217(11) 0.0126(9) 0.0294(14) 0.0057(13) 0.0033(16) 0.0012(7) N9 0.0206(12) 0.0111(10) 0.0366(17) 0.0014(11) 0.0089(13) 0.0014(9) N10 0.047(2) 0.042(2) 0.0296(19) 0.0043(16) 0.0035(16) -0.0206(17) O1 0.0374(15) 0.0194(11) 0.0380(16) 0.0081(11) -0.0027(14) -0.0059(10) O2 0.093(3) 0.078(3) 0.0328(19) 0.0036(18) 0.020(2) -0.050(3) O3 0.0425(18) 0.0343(15) 0.0360(18) -0.0078(13) 0.0225(14) -0.0078(12) O4 0.0277(13) 0.0191(11) 0.0302(14) -0.0025(10) -0.0037(12) 0.0041(8) O5 0.0195(11) 0.0226(11) 0.0268(14) 0.0015(9) 0.0051(10) -0.0072(8) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Co1 O5 2.048(3) . ? Co1 N2 2.088(3) . ? Co1 N3 2.094(3) 4_744 ? Co1 O4 2.127(3) . ? Co1 O3 2.130(3) . ? Co1 O1 2.161(3) . ? C1 C2 1.384(5) . ? C1 C4 1.389(5) . ? C1 C6 1.498(5) . ? C1A C2A 1.39(2) . ? C1A C6A 1.50(2) . ? C1A N1A 1.517(19) . ? C2A C3A 1.11(2) . ? C2A H2AA 0.9500 . ? C3A C4A 1.45(3) . ? C3A H3AA 0.9500 . ? C4A C5A 1.30(2) . ? C4A H4AA 0.9500 . ? C5A C6A 1.33(2) . ? C5A H5AA 0.9500 . ? C6A H6AA 0.9500 . ? O1A N1A 1.205(14) . ? O1A O2A 1.786(18) 2_775 ? O2A N1A 1.222(13) . ? O2A O1A 1.786(18) 2_775 ? C2 C3 1.378(6) . ? C2 H2A 0.9500 . ? C3 N1 1.335(5) . ? C3 H3 0.9500 . ? C4 C5 1.380(4) . ? C4 H4A 0.9500 . ? C5 N1 1.337(4) . ? C5 H5A 0.9500 . ? C6 N5 1.338(4) . ? C6 N4 1.344(4) . ? C7 C8 1.390(5) . ? C7 C10 1.403(4) . ? C7 C12 1.488(4) . ? C8 C9 1.376(5) . ? C8 H8 0.9500 . ? C9 N2 1.338(4) . ? C9 H9 0.9500 . ? C10 C11 1.360(5) . ? C10 H10A 0.9500 . ? C11 N2 1.358(4) . ? C11 H11A 0.9500 . ? C12 N6 1.339(4) . ? C12 N7 1.352(4) . ? N3 C15A 1.33(2) . ? N3 C15B 1.339(18) . ? N3 C17A 1.340(10) . ? N3 C17B 1.379(11) . ? N3 Co1 2.094(3) 4_755 ? C13 C16A 1.309(10) . ? C13 C14B 1.382(12) . ? C13 C14A 1.396(13) . ? C13 C16B 1.419(13) . ? C13 C18 1.490(4) . ? C15A C14A 1.41(2) . ? C15A H15A 0.9500 . ? C14A H14A 0.9500 . ? C16A C17A 1.388(13) . ? C16A H16A 0.9500 . ? C17A H17A 0.9500 . ? C15B C14B 1.34(2) . ? C15B H15B 0.9500 . ? C14B H14B 0.9500 . ? C16B C17B 1.367(15) . ? C16B H16B 0.9500 . ? C17B H17B 0.9500 . ? C18 N8 1.346(4) . ? C18 N9 1.347(4) . ? C19 N4 1.343(4) . ? C19 N9 1.351(4) . ? C19 C21 1.403(4) . ? C20 N5 1.348(4) . ? C20 N6 1.363(4) . ? C20 C21 1.396(4) . ? C21 C22 1.406(4) . ? C22 N8 1.347(3) . ? C22 N7 1.355(4) . ? C23 O4 1.458(6) . ? C23 H23A 0.9800 . ? C23 H23B 0.9800 . ? C23 H23C 0.9800 . ? C24 O5 1.414(5) . ? C24 H24A 0.9800 . ? C24 H24B 0.9800 . ? C24 H24C 0.9800 . ? N10 O2 1.216(5) . ? N10 O1 1.261(5) . ? N10 O3 1.280(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 O5 Co1 N2 92.62(11) . . ? O5 Co1 N3 93.66(11) . 4_744 ? N2 Co1 N3 103.13(11) . 4_744 ? O5 Co1 O4 173.47(9) . . ? N2 Co1 O4 83.75(11) . . ? N3 Co1 O4 92.45(11) 4_744 . ? O5 Co1 O3 90.30(13) . . ? N2 Co1 O3 160.17(12) . . ? N3 Co1 O3 96.25(13) 4_744 . ? O4 Co1 O3 91.31(13) . . ? O5 Co1 O1 87.64(11) . . ? N2 Co1 O1 100.40(11) . . ? N3 Co1 O1 156.35(12) 4_744 . ? O4 Co1 O1 87.68(11) . . ? O3 Co1 O1 60.11(12) . . ? C2 C1 C4 117.5(3) . . ? C2 C1 C6 120.7(3) . . ? C4 C1 C6 121.8(3) . . ? C2A C1A C6A 116.7(12) . . ? C2A C1A N1A 121.5(11) . . ? C6A C1A N1A 121.6(11) . . ? C3A C2A C1A 119.4(14) . . ? C3A C2A H2AA 120.3 . . ? C1A C2A H2AA 120.3 . . ? C2A C3A C4A 126.3(15) . . ? C2A C3A H3AA 116.8 . . ? C4A C3A H3AA 116.8 . . ? C5A C4A C3A 119.6(15) . . ? C5A C4A H4AA 120.2 . . ? C3A C4A H4AA 120.2 . . ? C4A C5A C6A 117.4(14) . . ? C4A C5A H5AA 121.3 . . ? C6A C5A H5AA 121.3 . . ? C5A C6A C1A 119.2(10) . . ? C5A C6A H6AA 120.4 . . ? C1A C6A H6AA 120.4 . . ? N1A O1A O2A 118.3(12) . 2_775 ? N1A O2A O1A 98.0(11) . 2_775 ? O1A N1A O2A 129.9(16) . . ? O1A N1A C1A 114.6(12) . . ? O2A N1A C1A 115.3(12) . . ? C3 C2 C1 119.5(4) . . ? C3 C2 H2A 120.3 . . ? C1 C2 H2A 120.3 . . ? N1 C3 C2 123.0(4) . . ? N1 C3 H3 118.5 . . ? C2 C3 H3 118.5 . . ? C5 C4 C1 119.5(3) . . ? C5 C4 H4A 120.3 . . ? C1 C4 H4A 120.3 . . ? N1 C5 C4 122.8(3) . . ? N1 C5 H5A 118.6 . . ? C4 C5 H5A 118.6 . . ? N5 C6 N4 129.6(3) . . ? N5 C6 C1 115.0(3) . . ? N4 C6 C1 115.4(3) . . ? C8 C7 C10 116.7(3) . . ? C8 C7 C12 122.2(3) . . ? C10 C7 C12 121.0(3) . . ? C9 C8 C7 120.0(3) . . ? C9 C8 H8 120.0 . . ? C7 C8 H8 120.0 . . ? N2 C9 C8 122.9(3) . . ? N2 C9 H9 118.6 . . ? C8 C9 H9 118.6 . . ? C11 C10 C7 120.3(3) . . ? C11 C10 H10A 119.9 . . ? C7 C10 H10A 119.9 . . ? N2 C11 C10 122.5(3) . . ? N2 C11 H11A 118.7 . . ? C10 C11 H11A 118.7 . . ? N6 C12 N7 129.4(3) . . ? N6 C12 C7 114.5(3) . . ? N7 C12 C7 116.1(3) . . ? C15A N3 C15B 26.3(13) . . ? C15A N3 C17A 114.8(9) . . ? C15B N3 C17A 108.6(9) . . ? C15A N3 C17B 110.8(9) . . ? C15B N3 C17B 117.9(8) . . ? C17A N3 C17B 27.2(4) . . ? C15A N3 Co1 117.3(8) . 4_755 ? C15B N3 Co1 122.3(7) . 4_755 ? C17A N3 Co1 127.0(4) . 4_755 ? C17B N3 Co1 118.7(4) . 4_755 ? C16A C13 C14B 109.4(7) . . ? C16A C13 C14A 119.8(7) . . ? C14B C13 C14A 28.1(7) . . ? C16A C13 C16B 25.4(5) . . ? C14B C13 C16B 115.9(7) . . ? C14A C13 C16B 113.0(8) . . ? C16A C13 C18 121.9(5) . . ? C14B C13 C18 122.6(5) . . ? C14A C13 C18 118.3(5) . . ? C16B C13 C18 121.5(5) . . ? N3 C15A C14A 125.4(15) . . ? N3 C15A H15A 117.3 . . ? C14A C15A H15A 117.3 . . ? C13 C14A C15A 115.8(11) . . ? C13 C14A H14A 122.1 . . ? C15A C14A H14A 122.1 . . ? C13 C16A C17A 120.6(9) . . ? C13 C16A H16A 119.7 . . ? C17A C16A H16A 119.7 . . ? N3 C17A C16A 123.4(8) . . ? N3 C17A H17A 118.3 . . ? C16A C17A H17A 118.3 . . ? C14B C15B N3 123.0(13) . . ? C14B C15B H15B 118.5 . . ? N3 C15B H15B 118.5 . . ? C15B C14B C13 121.7(11) . . ? C15B C14B H14B 119.2 . . ? C13 C14B H14B 119.2 . . ? C17B C16B C13 120.3(9) . . ? C17B C16B H16B 119.8 . . ? C13 C16B H16B 119.8 . . ? C16B C17B N3 121.0(9) . . ? C16B C17B H17B 119.5 . . ? N3 C17B H17B 119.5 . . ? N8 C18 N9 129.0(3) . . ? N8 C18 C13 115.2(3) . . ? N9 C18 C13 115.8(3) . . ? N4 C19 N9 120.2(3) . . ? N4 C19 C21 119.9(3) . . ? N9 C19 C21 119.9(3) . . ? N5 C20 N6 119.9(3) . . ? N5 C20 C21 120.4(3) . . ? N6 C20 C21 119.6(3) . . ? C20 C21 C19 119.8(3) . . ? C20 C21 C22 120.3(3) . . ? C19 C21 C22 119.9(3) . . ? N8 C22 N7 119.6(3) . . ? N8 C22 C21 120.2(3) . . ? N7 C22 C21 120.2(2) . . ? O4 C23 H23A 109.5 . . ? O4 C23 H23B 109.5 . . ? H23A C23 H23B 109.5 . . ? O4 C23 H23C 109.5 . . ? H23A C23 H23C 109.5 . . ? H23B C23 H23C 109.5 . . ? O5 C24 H24A 109.5 . . ? O5 C24 H24B 109.5 . . ? H24A C24 H24B 109.5 . . ? O5 C24 H24C 109.5 . . ? H24A C24 H24C 109.5 . . ? H24B C24 H24C 109.5 . . ? C3 N1 C5 117.7(3) . . ? C9 N2 C11 117.6(3) . . ? C9 N2 Co1 117.4(2) . . ? C11 N2 Co1 124.0(2) . . ? C19 N4 C6 115.4(3) . . ? C6 N5 C20 114.9(3) . . ? C12 N6 C20 115.6(2) . . ? C12 N7 C22 114.9(3) . . ? C18 N8 C22 115.4(3) . . ? C18 N9 C19 115.5(3) . . ? O2 N10 O1 122.4(4) . . ? O2 N10 O3 122.0(5) . . ? O1 N10 O3 115.6(3) . . ? N10 O1 Co1 91.7(2) . . ? N10 O3 Co1 92.6(2) . . ? C23 O4 Co1 128.4(3) . . ? C24 O5 Co1 128.0(3) . . ? _diffrn_measured_fraction_theta_max 0.970 _diffrn_reflns_theta_full 32.37 _diffrn_measured_fraction_theta_full 0.970 _refine_diff_density_max 1.255 _refine_diff_density_min -1.075 _refine_diff_density_rms 0.167 data_TPHAP-Co-Therm-2 _database_code_depnum_ccdc_archive 'CCDC 885675' #TrackingRef '- p21n.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C35.25 H24 Co N11.75 O9.75' _chemical_formula_weight 827.09 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' Co Co 0.3494 0.9721 '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' _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 13.6756(3) _cell_length_b 21.2490(3) _cell_length_c 15.3455(3) _cell_angle_alpha 90.00 _cell_angle_beta 115.872(6) _cell_angle_gamma 90.00 _cell_volume 4012.3(1) _cell_formula_units_Z 4 _cell_measurement_temperature 90(2) _cell_measurement_reflns_used 61451 _cell_measurement_theta_min 0.66 _cell_measurement_theta_max 50.00 _exptl_crystal_description block _exptl_crystal_colour red _exptl_crystal_size_max 0.13 _exptl_crystal_size_mid 0.06 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.369 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1691 _exptl_absorpt_coefficient_mu 0.496 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.9383 _exptl_absorpt_correction_T_max 0.9756 _exptl_absorpt_process_details HKL2000 _exptl_special_details ; ? ; _diffrn_ambient_temperature 90(2) _diffrn_radiation_wavelength 0.68890 _diffrn_radiation_type synchrotron _diffrn_radiation_source 'undulator light in KEK PF-NW2A' _diffrn_radiation_monochromator Si _diffrn_measurement_device_type CCD _diffrn_measurement_method omega_scan _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 60523 _diffrn_reflns_av_R_equivalents 0.0978 _diffrn_reflns_av_sigmaI/netI 0.0897 _diffrn_reflns_limit_h_min -20 _diffrn_reflns_limit_h_max 20 _diffrn_reflns_limit_k_min -27 _diffrn_reflns_limit_k_max 31 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 2.45 _diffrn_reflns_theta_max 31.30 _reflns_number_total 13657 _reflns_number_gt 7919 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Rigaku CrystalClear' _computing_cell_refinement HKL2000 _computing_data_reduction HKL2000 _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker XP' _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. The occupancy factors of the disordered molecules converged as follows: nitrobenzene A, A*, B, C, D: 30%, 23%, 49%, 36%, 42%, respectively; methanol O1S-C1S and O2S-C2S: 47%, O3S-C3S and O4S-C4S: 19%; water O1W: 47%, O2W and O3W: 19%. The terminal pyridine ring of TPHAP is disordering in two positions (C8 to H11A and C8* to H11B). The ocupancy factor of each part is 74% (C8 to H11A) and 26% (C8* to H11B). Large residual electron density peaks sit around cobalt atoms. ; _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^)+(0.1434P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 13657 _refine_ls_number_parameters 891 _refine_ls_number_restraints 832 _refine_ls_R_factor_all 0.1198 _refine_ls_R_factor_gt 0.0777 _refine_ls_wR_factor_ref 0.2294 _refine_ls_wR_factor_gt 0.2127 _refine_ls_goodness_of_fit_ref 0.961 _refine_ls_restrained_S_all 0.976 _refine_ls_shift/su_max 0.076 _refine_ls_shift/su_mean 0.005 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 -0.10382(3) 0.165723(16) 0.85764(2) 0.03143(13) Uani 1 1 d . . . N1N N -0.2745(3) 0.23413(14) 0.7916(2) 0.0565(7) Uani 1 1 d . . . O1N O -0.3570(3) 0.26578(17) 0.7574(2) 0.0905(10) Uani 1 1 d . . . O2N O -0.2347(2) 0.21108(11) 0.87673(15) 0.0530(6) Uani 1 1 d . . . O3N O -0.22175(18) 0.22139(10) 0.74249(13) 0.0476(5) Uani 1 1 d . . . C1M C -0.3131(4) 0.0804(2) 0.7845(4) 0.0850(14) Uani 1 1 d . . . H1MA H -0.3380 0.0372 0.7643 0.127 Uiso 1 1 calc R . . H1MB H -0.3538 0.1094 0.7313 0.127 Uiso 1 1 calc R . . H1MC H -0.3252 0.0914 0.8410 0.127 Uiso 1 1 calc R . . O1M O -0.20312(16) 0.08477(10) 0.80827(13) 0.0412(4) Uani 1 1 d . . . N1 N -0.02367(18) 0.13262(10) 0.77608(14) 0.0329(5) Uani 1 1 d . . . N2 N -0.0336(2) 0.12455(10) -0.00409(14) 0.0379(5) Uani 1 1 d . . . N3 N 0.5047(2) -0.25228(10) 0.59718(14) 0.0356(5) Uani 1 1 d . . . N4 N 0.17041(19) 0.00975(10) 0.61961(14) 0.0336(5) Uani 1 1 d . . . N5 N 0.05624(19) 0.08259(10) 0.49531(14) 0.0330(5) Uani 1 1 d . . . N6 N 0.05104(19) 0.07915(10) 0.34048(14) 0.0338(5) Uani 1 1 d . . . N7 N 0.16226(19) 0.00343(10) 0.30592(14) 0.0327(5) Uani 1 1 d . . . N8 N 0.27066(19) -0.06842(10) 0.42546(14) 0.0324(5) Uani 1 1 d . . . N9 N 0.2731(2) -0.06614(10) 0.58439(15) 0.0364(5) Uani 1 1 d . . . C1 C 0.0588(2) 0.08455(12) 0.65194(17) 0.0321(5) Uani 1 1 d . . . C2 C -0.0196(2) 0.13079(13) 0.62129(17) 0.0353(6) Uani 1 1 d . . . H2A H -0.0461 0.1472 0.5575 0.042 Uiso 1 1 calc R . . C3 C -0.0597(2) 0.15321(13) 0.68407(17) 0.0348(6) Uani 1 1 d . . . H3A H -0.1149 0.1844 0.6614 0.042 Uiso 1 1 calc R . . C4 C 0.0970(3) 0.06282(15) 0.74710(19) 0.0422(7) Uani 1 1 d . . . H4A H 0.1519 0.0314 0.7711 0.051 Uiso 1 1 calc R . . C5 C 0.0536(3) 0.08771(15) 0.80560(18) 0.0432(7) Uani 1 1 d . . . H5A H 0.0796 0.0724 0.8700 0.052 Uiso 1 1 calc R . . C6 C 0.0993(2) 0.05715(12) 0.58387(16) 0.0323(5) Uani 1 1 d . . . C7 C 0.0474(2) 0.07569(11) 0.18385(17) 0.0344(6) Uani 1 1 d . . . C8 C 0.1200(3) 0.08455(18) 0.1401(2) 0.0363(9) Uani 0.737(6) 1 d P A 1 H8A H 0.1947 0.0736 0.1732 0.044 Uiso 0.737(6) 1 calc PR A 1 C9 C 0.0765(3) 0.10983(17) 0.0473(2) 0.0345(9) Uani 0.737(6) 1 d P A 1 H9A H 0.1235 0.1174 0.0176 0.041 Uiso 0.737(6) 1 calc PR A 1 C10 C -0.0548(4) 0.0932(3) 0.1349(3) 0.0498(12) Uani 0.737(6) 1 d P A 1 H10A H -0.1030 0.0904 0.1644 0.060 Uiso 0.737(6) 1 calc PR A 1 C11 C -0.0927(4) 0.1158(3) 0.0410(3) 0.0450(11) Uani 0.737(6) 1 d P A 1 H11A H -0.1679 0.1255 0.0075 0.054 Uiso 0.737(6) 1 calc PR A 1 C8* C 0.0517(10) 0.0445(5) 0.1075(7) 0.043(3) Uani 0.263(6) 1 d P A 2 H8*A H 0.0875 0.0049 0.1185 0.051 Uiso 0.263(6) 1 calc PR A 2 C9* C 0.0048(10) 0.0693(5) 0.0143(6) 0.040(3) Uani 0.263(6) 1 d P A 2 H9*A H 0.0014 0.0438 -0.0378 0.048 Uiso 0.263(6) 1 calc PR A 2 C10* C -0.0277(10) 0.1296(6) 0.1565(7) 0.037(3) Uani 0.263(6) 1 d P A 2 H10B H -0.0454 0.1493 0.2034 0.044 Uiso 0.263(6) 1 calc PR A 2 C11* C -0.0726(10) 0.1514(6) 0.0617(8) 0.035(3) Uani 0.263(6) 1 d P A 2 H11B H -0.1272 0.1830 0.0406 0.042 Uiso 0.263(6) 1 calc PR A 2 C12 C 0.0909(2) 0.05124(12) 0.28507(16) 0.0330(5) Uani 1 1 d . A . C13 C 0.3725(2) -0.14473(12) 0.54478(17) 0.0336(5) Uani 1 1 d . . . C14 C 0.4272(4) -0.16355(15) 0.6410(2) 0.0610(11) Uani 1 1 d . . . H14A H 0.4207 -0.1399 0.6908 0.073 Uiso 1 1 calc R . . C15 C 0.4905(4) -0.21671(16) 0.6631(2) 0.0657(11) Uani 1 1 d . . . H15A H 0.5265 -0.2291 0.7291 0.079 Uiso 1 1 calc R . . C16 C 0.3893(2) -0.17946(13) 0.47686(17) 0.0382(6) Uani 1 1 d . . . H16A H 0.3565 -0.1671 0.4107 0.046 Uiso 1 1 calc R . . C17 C 0.4542(2) -0.23245(13) 0.50579(16) 0.0361(6) Uani 1 1 d . . . H17A H 0.4635 -0.2562 0.4575 0.043 Uiso 1 1 calc R . . C18 C 0.3005(2) -0.08881(12) 0.51662(16) 0.0322(5) Uani 1 1 d . . . C19 C 0.2042(2) -0.01659(12) 0.55688(17) 0.0320(5) Uani 1 1 d . . . C20 C 0.0909(2) 0.05742(12) 0.43285(16) 0.0312(5) Uani 1 1 d . . . C21 C 0.1659(2) 0.00775(11) 0.46244(16) 0.0305(5) Uani 1 1 d . . . C22 C 0.2013(2) -0.01921(11) 0.39787(16) 0.0309(5) Uani 1 1 d . . . C1C C 0.2000(12) -0.2623(7) 0.6444(10) 0.095(4) Uani 0.363(6) 1 d PDU B 1 C2C C 0.2710(12) -0.2861(7) 0.7255(10) 0.094(5) Uani 0.363(6) 1 d PDU B 1 H2CA H 0.3260 -0.3125 0.7234 0.113 Uiso 0.363(6) 1 calc PR B 1 C3C C 0.2713(15) -0.2746(9) 0.8209(12) 0.115(6) Uani 0.363(6) 1 d PDU B 1 H3CA H 0.3241 -0.2914 0.8802 0.138 Uiso 0.363(6) 1 calc PR B 1 C4C C 0.1858(16) -0.2365(11) 0.8139(12) 0.134(6) Uani 0.363(6) 1 d PDU B 1 H4CA H 0.1800 -0.2264 0.8719 0.161 Uiso 0.363(6) 1 calc PR B 1 C5C C 0.1088(14) -0.2124(10) 0.7282(11) 0.132(7) Uani 0.363(6) 1 d PDU B 1 H5CA H 0.0453 -0.1941 0.7280 0.158 Uiso 0.363(6) 1 calc PR B 1 C6C C 0.1180(15) -0.2133(8) 0.6463(12) 0.106(5) Uani 0.363(6) 1 d PDU B 1 H6CA H 0.0779 -0.1862 0.5934 0.127 Uiso 0.363(6) 1 calc PR B 1 N1C N 0.2018(11) -0.2799(6) 0.5518(9) 0.098(4) Uani 0.363(6) 1 d PDU B 1 O1C O 0.2663(8) -0.3167(4) 0.5525(8) 0.087(3) Uani 0.363(6) 1 d PDU B 1 O2C O 0.1569(13) -0.2478(8) 0.4848(10) 0.135(5) Uani 0.363(6) 1 d PDU B 1 C1B C 0.0378(19) -0.4633(9) 0.9801(14) 0.168(11) Uani 0.487(6) 1 d PDU . 1 C2B C 0.0652(10) -0.4372(6) 0.9141(11) 0.110(5) Uani 0.487(6) 1 d PDU . 1 H2BA H 0.0330 -0.4554 0.8512 0.133 Uiso 0.487(6) 1 calc PR . 1 C3B C 0.1396(14) -0.3837(8) 0.9274(14) 0.160(8) Uani 0.487(6) 1 d PDU . 1 H3BA H 0.1588 -0.3677 0.8791 0.192 Uiso 0.487(6) 1 calc PR . 1 C4B C 0.1774(17) -0.3601(10) 1.0214(16) 0.166(10) Uani 0.487(6) 1 d PDU . 1 H4BA H 0.2210 -0.3233 1.0353 0.199 Uiso 0.487(6) 1 calc PR . 1 C5B C 0.1590(10) -0.3837(7) 1.0955(10) 0.106(5) Uani 0.487(6) 1 d PDU . 1 H5BA H 0.1909 -0.3639 1.1571 0.127 Uiso 0.487(6) 1 calc PR . 1 C6B C 0.0957(14) -0.4352(8) 1.0822(11) 0.165(11) Uani 0.487(6) 1 d PDU . 1 H6BA H 0.0874 -0.4536 1.1350 0.198 Uiso 0.487(6) 1 calc PR . 1 N1B N -0.0328(13) -0.5233(9) 0.9544(15) 0.212(10) Uani 0.487(6) 1 d PDU . 1 O1B O -0.0524(14) -0.5400(7) 1.0192(17) 0.233(11) Uani 0.487(6) 1 d PDU . 1 O2B O -0.0677(18) -0.5455(12) 0.8721(15) 0.310(17) Uani 0.487(6) 1 d PDU . 1 C1D C 0.2809(14) -0.2721(8) 0.8934(13) 0.139(6) Uani 0.418(8) 1 d PDU C 2 C2D C 0.2803(17) -0.2944(9) 0.9751(13) 0.166(8) Uani 0.418(8) 1 d PDU C 2 H2DA H 0.3404 -0.2828 1.0339 0.199 Uiso 0.418(8) 1 calc PR C 2 C3D C 0.196(2) -0.3351(12) 0.9845(19) 0.155(10) Uani 0.418(8) 1 d PDU C 2 H3DA H 0.1912 -0.3426 1.0434 0.187 Uiso 0.418(8) 1 calc PR C 2 C4D C 0.1275(19) -0.3604(14) 0.896(2) 0.226(13) Uani 0.418(8) 1 d PDU C 2 H4DA H 0.0908 -0.3992 0.8907 0.271 Uiso 0.418(8) 1 calc PR C 2 C5D C 0.1151(19) -0.3282(15) 0.8181(18) 0.240(14) Uani 0.418(8) 1 d PDU C 2 H5DA H 0.0432 -0.3273 0.7678 0.288 Uiso 0.418(8) 1 calc PR C 2 C6D C 0.1887(19) -0.2963(14) 0.7994(15) 0.213(11) Uani 0.418(8) 1 d PDU C 2 H6DA H 0.1842 -0.2897 0.7365 0.256 Uiso 0.418(8) 1 calc PR C 2 N1D N 0.3644(16) -0.2261(9) 0.8936(13) 0.166(6) Uani 0.418(8) 1 d PDU C 2 O1D O 0.424(2) -0.2090(16) 0.9745(18) 0.358(19) Uani 0.418(8) 1 d PDU C 2 O2D O 0.3807(16) -0.2239(9) 0.8228(12) 0.225(11) Uani 0.418(8) 1 d PDU C 2 C1A C 0.5927(12) 0.0131(8) 0.9333(17) 0.073(6) Uani 0.305(7) 1 d PDU D 1 C2A C 0.5673(13) 0.0717(9) 0.9457(14) 0.094(5) Uani 0.305(7) 1 d PDU D 1 H2AA H 0.6219 0.0974 0.9923 0.112 Uiso 0.305(7) 1 calc PR D 1 C3A C 0.4554(14) 0.0989(7) 0.8890(13) 0.115(7) Uani 0.305(7) 1 d PDU D 1 H3AA H 0.4325 0.1388 0.9014 0.139 Uiso 0.305(7) 1 calc PR D 1 C4A C 0.3913(10) 0.0586(7) 0.8172(8) 0.060(3) Uani 0.305(7) 1 d PDU D 1 H4AA H 0.3313 0.0762 0.7635 0.072 Uiso 0.305(7) 1 calc PR D 1 C5A C 0.4064(11) -0.0052(10) 0.8165(11) 0.102(6) Uani 0.305(7) 1 d PDU D 1 H5AA H 0.3465 -0.0311 0.7775 0.123 Uiso 0.305(7) 1 calc PR D 1 C6A C 0.5035(13) -0.0322(10) 0.8692(11) 0.111(5) Uani 0.305(7) 1 d PDU D 1 H6AA H 0.5157 -0.0761 0.8668 0.133 Uiso 0.305(7) 1 calc PR D 1 N1A N 0.6964(13) -0.0195(9) 1.0015(17) 0.126(8) Uani 0.305(7) 1 d PDU D 1 O1A O 0.7652(11) 0.0159(9) 1.0576(9) 0.118(7) Uani 0.305(7) 1 d PDU D 1 O2A O 0.7060(14) -0.0742(9) 0.9911(14) 0.171(9) Uani 0.305(7) 1 d PDU D 1 C1A* C 0.5750(14) 0.0087(10) 0.9384(18) 0.069(6) Uani 0.230(7) 1 d PDU E 3 C2A* C 0.4938(15) 0.0490(10) 0.8968(14) 0.089(5) Uani 0.230(7) 1 d PDU E 3 H2AB H 0.5061 0.0930 0.9058 0.107 Uiso 0.230(7) 1 calc PR E 3 C3A* C 0.3815(19) 0.0238(15) 0.835(3) 0.139(11) Uani 0.230(7) 1 d PDU E 3 H3AB H 0.3196 0.0503 0.8053 0.166 Uiso 0.230(7) 1 calc PR E 3 C4A* C 0.376(2) -0.0415(15) 0.825(2) 0.152(10) Uani 0.230(7) 1 d PDU E 3 H4AB H 0.3064 -0.0601 0.7916 0.183 Uiso 0.230(7) 1 calc PR E 3 C5A* C 0.463(2) -0.0800(13) 0.859(2) 0.147(11) Uani 0.230(7) 1 d PDU E 3 H5AB H 0.4523 -0.1227 0.8386 0.176 Uiso 0.230(7) 1 calc PR E 3 C6A* C 0.564(2) -0.0619(10) 0.9194(18) 0.113(7) Uani 0.230(7) 1 d PDU E 3 H6AB H 0.6234 -0.0903 0.9477 0.135 Uiso 0.230(7) 1 calc PR E 3 N1A* N 0.6909(14) 0.0229(11) 1.0110(13) 0.096(7) Uani 0.230(7) 1 d PDU E 3 O1A* O 0.6848(17) 0.0744(12) 1.0419(17) 0.173(12) Uani 0.230(7) 1 d PDU E 3 O2A* O 0.7491(15) -0.0202(12) 1.0090(19) 0.104(8) Uani 0.230(7) 1 d PDU E 3 O1W O 0.1650(6) -0.1415(4) 0.6908(6) 0.103(3) Uani 0.474(8) 1 d PU F 3 O2W O 0.2643(15) -0.0611(11) 0.8021(11) 0.112(8) Uani 0.193(6) 1 d PU G 2 C3S C 0.599(3) 0.0496(16) 0.992(3) 0.099(9) Uani 0.193(6) 1 d PDU G 2 O3S O 0.516(2) 0.0959(11) 0.9775(17) 0.135(9) Uani 0.193(6) 1 d PDU G 2 C4S C 0.627(2) -0.0640(11) 0.8390(15) 0.084(8) Uani 0.193(6) 1 d PDU G 2 O4S O 0.649(2) -0.0351(13) 0.9267(17) 0.134(9) Uani 0.193(6) 1 d PDU G 2 O3W O 0.461(2) 0.0048(15) 0.8190(15) 0.126(7) Uani 0.193(6) 1 d PU G 2 O1S O 0.5523(13) -0.2507(7) 1.0676(9) 0.177(6) Uani 0.474(8) 1 d PU F 3 C1S C 0.4617(19) -0.2481(9) 1.080(2) 0.179(9) Uani 0.474(8) 1 d PU F 3 O2S O 0.5826(15) -0.2041(7) 0.9169(12) 0.180(6) Uani 0.474(8) 1 d PU F 3 C2S C 0.6955(15) -0.1950(9) 0.9617(17) 0.156(8) Uani 0.474(8) 1 d PU F 3 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 0.0498(3) 0.0331(2) 0.02027(16) -0.00242(12) 0.02351(16) 0.00214(14) N1N 0.073(2) 0.0596(17) 0.0464(14) 0.0085(13) 0.0345(14) 0.0280(15) O1N 0.097(2) 0.107(2) 0.078(2) 0.0242(18) 0.0478(18) 0.056(2) O2N 0.0728(15) 0.0613(14) 0.0390(10) 0.0036(10) 0.0375(11) 0.0217(11) O3N 0.0619(13) 0.0567(13) 0.0279(9) -0.0004(8) 0.0231(9) 0.0107(10) C1M 0.095(3) 0.090(3) 0.104(4) -0.037(3) 0.076(3) -0.021(3) O1M 0.0478(12) 0.0510(11) 0.0352(9) -0.0119(8) 0.0277(9) -0.0086(9) N1 0.0506(13) 0.0345(11) 0.0244(9) -0.0032(8) 0.0264(9) -0.0041(9) N2 0.0666(16) 0.0309(11) 0.0241(9) -0.0010(8) 0.0272(10) -0.0010(10) N3 0.0591(14) 0.0320(11) 0.0232(9) 0.0006(8) 0.0251(10) -0.0002(10) N4 0.0523(13) 0.0342(11) 0.0268(9) -0.0016(8) 0.0287(10) 0.0004(9) N5 0.0512(13) 0.0340(11) 0.0247(9) -0.0033(8) 0.0268(9) -0.0009(9) N6 0.0539(14) 0.0333(11) 0.0247(9) -0.0008(8) 0.0267(9) 0.0012(9) N7 0.0513(13) 0.0337(11) 0.0235(9) -0.0016(8) 0.0259(9) 0.0015(9) N8 0.0497(13) 0.0330(11) 0.0258(9) -0.0002(8) 0.0271(9) -0.0002(9) N9 0.0579(14) 0.0364(11) 0.0279(9) 0.0025(9) 0.0307(10) 0.0032(10) C1 0.0464(15) 0.0354(13) 0.0259(10) -0.0048(9) 0.0263(11) -0.0051(10) C2 0.0545(16) 0.0372(13) 0.0240(10) -0.0009(10) 0.0263(11) 0.0013(11) C3 0.0500(16) 0.0384(13) 0.0250(10) -0.0052(9) 0.0248(11) -0.0006(11) C4 0.0607(18) 0.0500(16) 0.0303(11) 0.0038(11) 0.0333(13) 0.0121(13) C5 0.0597(18) 0.0566(17) 0.0263(11) 0.0031(11) 0.0308(12) 0.0106(14) C6 0.0497(15) 0.0343(12) 0.0240(10) -0.0056(9) 0.0262(11) -0.0059(11) C7 0.0606(18) 0.0288(12) 0.0235(10) -0.0022(9) 0.0275(12) -0.0010(11) C8 0.052(2) 0.040(2) 0.0267(15) 0.0045(14) 0.0256(16) 0.0057(17) C9 0.050(2) 0.040(2) 0.0250(14) 0.0019(13) 0.0268(16) 0.0037(16) C10 0.062(3) 0.069(3) 0.035(2) 0.018(2) 0.037(2) 0.012(3) C11 0.052(3) 0.062(3) 0.0307(18) 0.016(2) 0.0268(18) 0.011(2) C8* 0.068(8) 0.046(6) 0.031(5) 0.004(4) 0.037(5) 0.013(6) C9* 0.071(8) 0.037(5) 0.024(4) -0.006(4) 0.033(5) 0.006(5) C10* 0.063(7) 0.031(6) 0.033(5) -0.013(4) 0.035(5) -0.004(5) C11* 0.064(7) 0.023(5) 0.032(5) -0.006(4) 0.034(5) -0.005(5) C12 0.0522(16) 0.0339(13) 0.0214(9) -0.0018(9) 0.0241(10) -0.0018(11) C13 0.0543(16) 0.0310(12) 0.0258(10) 0.0007(9) 0.0271(11) -0.0014(11) C14 0.116(3) 0.0470(18) 0.0289(12) 0.0058(12) 0.0402(17) 0.0289(18) C15 0.126(3) 0.0519(19) 0.0262(12) 0.0087(12) 0.0392(17) 0.033(2) C16 0.0480(16) 0.0466(15) 0.0212(10) -0.0023(10) 0.0162(11) 0.0085(12) C17 0.0484(16) 0.0422(14) 0.0201(9) -0.0048(10) 0.0171(10) 0.0036(11) C18 0.0494(15) 0.0313(12) 0.0259(10) 0.0003(9) 0.0257(11) -0.0015(10) C19 0.0497(15) 0.0327(12) 0.0249(10) -0.0020(9) 0.0268(11) -0.0023(10) C20 0.0481(15) 0.0315(12) 0.0244(10) -0.0041(9) 0.0253(11) -0.0039(10) C21 0.0466(15) 0.0313(12) 0.0239(10) -0.0034(9) 0.0248(10) -0.0050(10) C22 0.0477(15) 0.0307(12) 0.0247(10) -0.0026(9) 0.0254(11) -0.0026(10) C1C 0.122(10) 0.094(9) 0.116(10) 0.023(8) 0.095(9) 0.014(8) C2C 0.104(10) 0.080(8) 0.095(9) -0.008(7) 0.040(8) 0.046(7) C3C 0.105(11) 0.112(11) 0.114(12) 0.014(10) 0.035(10) 0.046(9) C4C 0.157(13) 0.165(14) 0.093(10) 0.003(10) 0.066(10) 0.077(12) C5C 0.130(12) 0.165(15) 0.103(11) -0.012(11) 0.054(10) 0.090(11) C6C 0.143(13) 0.089(10) 0.103(11) 0.046(8) 0.070(10) 0.031(9) N1C 0.123(10) 0.092(8) 0.114(10) 0.051(7) 0.083(8) 0.040(7) O1C 0.084(6) 0.083(6) 0.108(8) 0.002(5) 0.054(6) 0.035(5) O2C 0.144(11) 0.179(14) 0.095(8) 0.036(9) 0.063(8) 0.055(11) C1B 0.103(13) 0.175(18) 0.208(18) -0.019(17) 0.052(13) 0.098(12) C2B 0.080(8) 0.104(9) 0.141(12) -0.036(9) 0.042(8) 0.030(7) C3B 0.123(11) 0.135(12) 0.161(15) -0.026(11) 0.005(11) 0.085(9) C4B 0.104(12) 0.131(17) 0.209(18) -0.081(14) 0.019(13) 0.069(11) C5B 0.089(8) 0.097(8) 0.106(9) -0.009(7) 0.018(7) 0.060(7) C6B 0.143(15) 0.168(15) 0.107(11) -0.063(11) -0.019(10) 0.122(12) N1B 0.121(15) 0.207(19) 0.37(3) 0.184(17) 0.162(17) 0.115(11) O1B 0.148(12) 0.159(12) 0.47(3) 0.209(16) 0.210(16) 0.106(9) O2B 0.30(2) 0.42(3) 0.24(2) 0.08(2) 0.15(2) 0.29(3) C1D 0.174(13) 0.129(12) 0.125(12) -0.010(11) 0.076(12) 0.046(10) C2D 0.202(17) 0.168(17) 0.155(15) -0.059(14) 0.102(14) 0.052(14) C3D 0.116(13) 0.117(16) 0.208(18) -0.067(13) 0.047(13) 0.048(11) C4D 0.110(14) 0.23(2) 0.23(2) 0.015(19) -0.033(16) 0.052(17) C5D 0.150(17) 0.27(2) 0.21(2) 0.051(19) -0.007(17) -0.105(17) C6D 0.137(15) 0.198(18) 0.197(17) -0.006(16) -0.027(15) -0.014(15) N1D 0.214(16) 0.186(15) 0.154(13) 0.008(12) 0.133(12) -0.017(12) O1D 0.43(4) 0.29(3) 0.25(3) -0.10(2) 0.05(3) -0.03(3) O2D 0.32(2) 0.259(19) 0.206(15) 0.157(14) 0.218(16) 0.192(17) C1A 0.039(7) 0.114(10) 0.081(10) 0.014(8) 0.041(7) -0.005(7) C2A 0.067(10) 0.130(13) 0.080(10) -0.020(10) 0.030(8) -0.001(10) C3A 0.131(14) 0.078(10) 0.077(10) 0.011(9) -0.011(10) 0.024(10) C4A 0.040(6) 0.104(10) 0.032(5) 0.008(6) 0.013(4) -0.016(6) C5A 0.027(7) 0.237(18) 0.044(6) 0.031(10) 0.018(6) -0.005(10) C6A 0.114(11) 0.182(15) 0.055(7) 0.020(10) 0.053(8) 0.041(11) N1A 0.069(11) 0.168(16) 0.091(11) 0.047(14) -0.013(11) -0.049(13) O1A 0.051(7) 0.202(17) 0.059(7) 0.060(9) -0.017(6) -0.021(9) O2A 0.080(11) 0.23(2) 0.147(15) 0.076(17) -0.002(10) 0.018(14) C1A* 0.034(9) 0.143(13) 0.039(7) 0.018(9) 0.024(7) 0.002(9) C2A* 0.071(10) 0.140(13) 0.061(9) 0.005(10) 0.032(8) -0.017(10) C3A* 0.096(16) 0.21(2) 0.081(14) 0.019(16) 0.012(13) 0.022(17) C4A* 0.140(16) 0.205(19) 0.074(13) 0.014(15) 0.012(14) -0.009(16) C5A* 0.20(2) 0.16(2) 0.065(13) -0.010(15) 0.041(15) -0.041(19) C6A* 0.114(15) 0.152(17) 0.075(12) 0.041(12) 0.044(11) 0.047(14) N1A* 0.085(13) 0.149(16) 0.058(9) 0.033(12) 0.035(9) -0.023(14) O1A* 0.073(13) 0.26(3) 0.125(18) 0.038(18) -0.015(12) -0.035(16) O2A* 0.040(12) 0.154(19) 0.102(16) 0.059(14) 0.016(12) 0.012(12) O1W 0.118(6) 0.120(6) 0.114(6) 0.072(5) 0.091(5) 0.050(5) O2W 0.107(12) 0.203(19) 0.058(8) 0.080(10) 0.064(9) 0.092(13) C3S 0.076(17) 0.12(2) 0.109(19) 0.070(16) 0.049(15) 0.026(15) O3S 0.21(2) 0.099(14) 0.092(14) -0.007(11) 0.063(16) 0.042(15) C4S 0.14(2) 0.064(13) 0.060(12) -0.004(10) 0.050(14) 0.013(13) O4S 0.104(16) 0.150(18) 0.117(16) -0.019(15) 0.018(14) 0.038(14) O3W 0.113(13) 0.216(16) 0.053(9) 0.034(10) 0.039(10) 0.029(13) O1S 0.218(14) 0.189(12) 0.103(9) -0.056(8) 0.051(9) 0.021(11) C1S 0.219(19) 0.141(14) 0.29(3) -0.003(15) 0.22(2) 0.020(14) O2S 0.258(17) 0.168(12) 0.194(14) -0.030(11) 0.173(14) -0.015(13) C2S 0.126(13) 0.133(13) 0.20(2) -0.062(13) 0.067(13) -0.083(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 N2 2.100(2) 1_556 ? Co1 N1 2.112(2) . ? Co1 O1M 2.116(2) . ? Co1 N3 2.129(2) 2_556 ? Co1 O3N 2.153(2) . ? Co1 O2N 2.162(2) . ? N1N O1N 1.218(4) . ? N1N O2N 1.274(3) . ? N1N O3N 1.278(3) . ? C1M O1M 1.387(5) . ? N1 C5 1.347(4) . ? N1 C3 1.349(3) . ? N2 C9* 1.267(11) . ? N2 C11 1.286(4) . ? N2 C9 1.396(4) . ? N2 C11* 1.448(10) . ? N2 Co1 2.100(2) 1_554 ? N3 C17 1.333(3) . ? N3 C15 1.343(3) . ? N3 Co1 2.129(2) 2_546 ? N4 C6 1.340(4) . ? N4 C19 1.357(3) . ? N5 C6 1.337(3) . ? N5 C20 1.351(3) . ? N6 C12 1.333(3) . ? N6 C20 1.358(3) . ? N7 C12 1.347(3) . ? N7 C22 1.360(3) . ? N8 C18 1.347(3) . ? N8 C22 1.350(3) . ? N9 C18 1.339(3) . ? N9 C19 1.352(4) . ? C1 C2 1.377(4) . ? C1 C4 1.397(3) . ? C1 C6 1.497(3) . ? C2 C3 1.384(3) . ? C4 C5 1.379(3) . ? C7 C10 1.319(5) . ? C7 C8* 1.370(9) . ? C7 C8 1.432(4) . ? C7 C10* 1.472(12) . ? C7 C12 1.493(3) . ? C8 C9 1.390(4) . ? C10 C11 1.387(5) . ? C8* C9* 1.391(13) . ? C10* C11* 1.390(14) . ? C13 C16 1.375(3) . ? C13 C14 1.391(4) . ? C13 C18 1.483(4) . ? C14 C15 1.373(4) . ? C16 C17 1.382(4) . ? C19 C21 1.407(3) . ? C20 C21 1.402(4) . ? C21 C22 1.400(3) . ? C1C C2C 1.301(15) . ? C1C N1C 1.480(14) . ? C1C C6C 1.540(15) . ? C2C C3C 1.483(17) . ? C3C C4C 1.388(16) . ? C4C C5C 1.375(18) . ? C5C C6C 1.316(16) . ? N1C O2C 1.160(13) . ? N1C O1C 1.176(12) . ? C1B O1B 0.21(3) 3_547 ? C1B C2B 1.344(17) . ? C1B C6B 1.535(17) . ? C1B N1B 1.542(16) . ? C2B C3B 1.480(18) . ? C3B C4B 1.395(15) . ? C4B C5B 1.36(2) . ? C5B C6B 1.353(18) . ? N1B O1B 1.192(16) . ? N1B O2B 1.232(16) . ? N1B O1B 1.71(2) 3_547 ? O1B C6B 1.50(3) 3_547 ? C1D C2D 1.343(17) . ? C1D N1D 1.502(16) . ? C1D C6D 1.533(17) . ? C2D C3D 1.49(2) . ? C3D C4D 1.386(17) . ? C4D C5D 1.32(2) . ? C5D C6D 1.344(19) . ? N1D O1D 1.207(16) . ? N1D O2D 1.201(14) . ? C1A C2A 1.327(17) . ? C1A N1A 1.514(16) . ? C1A C6A 1.529(17) . ? C2A C3A 1.507(18) . ? C3A C4A 1.369(15) . ? C4A C5A 1.37(2) . ? C5A C6A 1.345(18) . ? N1A O2A 1.188(17) . ? N1A O1A 1.218(16) . ? C1A* C2A* 1.324(17) . ? C1A* N1A* 1.517(16) . ? C1A* C6A* 1.523(18) . ? C2A* C3A* 1.51(2) . ? C3A* C4A* 1.395(19) . ? C4A* C5A* 1.35(2) . ? C5A* C6A* 1.34(2) . ? N1A* O1A* 1.209(17) . ? N1A* O2A* 1.223(17) . ? C3S O3S 1.448(19) . ? C4S O4S 1.388(18) . ? O1S C1S 1.33(2) . ? O2S C2S 1.40(2) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N2 Co1 N1 109.47(9) 1_556 . ? N2 Co1 O1M 87.83(9) 1_556 . ? N1 Co1 O1M 86.27(8) . . ? N2 Co1 N3 93.81(8) 1_556 2_556 ? N1 Co1 N3 92.53(8) . 2_556 ? O1M Co1 N3 178.22(7) . 2_556 ? N2 Co1 O3N 155.02(9) 1_556 . ? N1 Co1 O3N 95.35(8) . . ? O1M Co1 O3N 91.09(8) . . ? N3 Co1 O3N 87.72(9) 2_556 . ? N2 Co1 O2N 95.12(9) 1_556 . ? N1 Co1 O2N 154.57(8) . . ? O1M Co1 O2N 88.35(9) . . ? N3 Co1 O2N 92.18(9) 2_556 . ? O3N Co1 O2N 59.90(8) . . ? O1N N1N O2N 123.7(3) . . ? O1N N1N O3N 121.2(3) . . ? O2N N1N O3N 115.1(2) . . ? N1N O2N Co1 92.35(16) . . ? N1N O3N Co1 92.64(16) . . ? C1M O1M Co1 127.0(2) . . ? C5 N1 C3 117.1(2) . . ? C5 N1 Co1 124.80(15) . . ? C3 N1 Co1 117.71(18) . . ? C9* N2 C11 92.5(5) . . ? C9* N2 C9 55.0(6) . . ? C11 N2 C9 116.1(3) . . ? C9* N2 C11* 117.0(6) . . ? C11 N2 C11* 34.3(4) . . ? C9 N2 C11* 109.2(5) . . ? C9* N2 Co1 125.0(4) . 1_554 ? C11 N2 Co1 119.1(2) . 1_554 ? C9 N2 Co1 124.64(18) . 1_554 ? C11* N2 Co1 113.2(5) . 1_554 ? C17 N3 C15 115.9(2) . . ? C17 N3 Co1 124.41(17) . 2_546 ? C15 N3 Co1 119.72(18) . 2_546 ? C6 N4 C19 115.5(2) . . ? C6 N5 C20 115.2(2) . . ? C12 N6 C20 115.1(2) . . ? C12 N7 C22 115.38(19) . . ? C18 N8 C22 115.3(2) . . ? C18 N9 C19 115.5(2) . . ? C2 C1 C4 118.2(2) . . ? C2 C1 C6 120.6(2) . . ? C4 C1 C6 121.1(2) . . ? C1 C2 C3 119.6(2) . . ? N1 C3 C2 122.8(3) . . ? C5 C4 C1 118.9(3) . . ? N1 C5 C4 123.4(2) . . ? N5 C6 N4 129.7(2) . . ? N5 C6 C1 114.8(2) . . ? N4 C6 C1 115.5(2) . . ? C10 C7 C8* 94.6(6) . . ? C10 C7 C8 118.3(3) . . ? C8* C7 C8 50.7(5) . . ? C10 C7 C10* 35.3(4) . . ? C8* C7 C10* 114.7(6) . . ? C8 C7 C10* 107.7(5) . . ? C10 C7 C12 122.2(3) . . ? C8* C7 C12 125.1(5) . . ? C8 C7 C12 119.4(3) . . ? C10* C7 C12 118.6(4) . . ? C9 C8 C7 117.2(3) . . ? C8 C9 N2 122.6(3) . . ? C7 C10 C11 120.8(4) . . ? N2 C11 C10 124.8(4) . . ? C7 C8* C9* 121.5(9) . . ? N2 C9* C8* 122.7(8) . . ? C11* C10* C7 119.5(8) . . ? C10* C11* N2 118.0(9) . . ? N6 C12 N7 129.8(2) . . ? N6 C12 C7 114.9(2) . . ? N7 C12 C7 115.3(2) . . ? C16 C13 C14 117.4(3) . . ? C16 C13 C18 121.2(2) . . ? C14 C13 C18 121.4(2) . . ? C15 C14 C13 119.2(3) . . ? N3 C15 C14 124.0(3) . . ? C13 C16 C17 119.3(2) . . ? N3 C17 C16 124.1(2) . . ? N9 C18 N8 129.1(2) . . ? N9 C18 C13 115.9(2) . . ? N8 C18 C13 115.0(2) . . ? N9 C19 N4 120.4(2) . . ? N9 C19 C21 120.2(2) . . ? N4 C19 C21 119.4(2) . . ? N5 C20 N6 120.0(2) . . ? N5 C20 C21 120.1(2) . . ? N6 C20 C21 119.8(2) . . ? C22 C21 C20 120.6(2) . . ? C22 C21 C19 119.4(2) . . ? C20 C21 C19 120.1(2) . . ? N8 C22 N7 120.2(2) . . ? N8 C22 C21 120.5(2) . . ? N7 C22 C21 119.3(2) . . ? C2C C1C N1C 120.1(11) . . ? C2C C1C C6C 119.4(11) . . ? N1C C1C C6C 120.4(11) . . ? C1C C2C C3C 124.0(11) . . ? C4C C3C C2C 112.4(13) . . ? C5C C4C C3C 123.9(13) . . ? C6C C5C C4C 123.8(13) . . ? C5C C6C C1C 113.7(11) . . ? O2C N1C O1C 120.3(12) . . ? O2C N1C C1C 118.6(12) . . ? O1C N1C C1C 119.0(11) . . ? O1B C1B C2B 47(9) 3_547 . ? O1B C1B C6B 76(9) 3_547 . ? C2B C1B C6B 114.8(15) . . ? O1B C1B N1B 141(10) 3_547 . ? C2B C1B N1B 119.8(13) . . ? C6B C1B N1B 124.7(15) . . ? C1B C2B C3B 127.9(14) . . ? C4B C3B C2B 109.9(16) . . ? C5B C4B C3B 127.7(17) . . ? C6B C5B C4B 120.6(14) . . ? C5B C6B C1B 118.7(16) . . ? O1B N1B O2B 127.8(19) . . ? O1B N1B C1B 112.1(16) . . ? O2B N1B C1B 119.9(18) . . ? O1B N1B O1B 114.6(15) . 3_547 ? O2B N1B O1B 118(2) . 3_547 ? C1B N1B O1B 4.4(13) . 3_547 ? N1B O1B C6B 50.9(14) . 3_547 ? C2D C1D N1D 122.8(15) . . ? C2D C1D C6D 115.0(15) . . ? N1D C1D C6D 122.2(15) . . ? C1D C2D C3D 127.8(17) . . ? C4D C3D C2D 110.6(18) . . ? C5D C4D C3D 117(2) . . ? C4D C5D C6D 130(2) . . ? C5D C6D C1D 110.7(17) . . ? O1D N1D O2D 127(2) . . ? O1D N1D C1D 111.8(18) . . ? O2D N1D C1D 117.7(17) . . ? C2A C1A N1A 123.7(16) . . ? C2A C1A C6A 119.8(13) . . ? N1A C1A C6A 113.6(13) . . ? C1A C2A C3A 122.8(14) . . ? C4A C3A C2A 110.8(14) . . ? C3A C4A C5A 125.4(13) . . ? C6A C5A C4A 121.9(15) . . ? C5A C6A C1A 114.8(15) . . ? O2A N1A O1A 127.0(18) . . ? O2A N1A C1A 118.7(14) . . ? O1A N1A C1A 114.0(16) . . ? C2A* C1A* N1A* 127.8(16) . . ? C2A* C1A* C6A* 123.6(15) . . ? N1A* C1A* C6A* 108.6(14) . . ? C1A* C2A* C3A* 119.0(17) . . ? C4A* C3A* C2A* 114.3(19) . . ? C5A* C4A* C3A* 125(2) . . ? C6A* C5A* C4A* 124(2) . . ? C5A* C6A* C1A* 113.6(17) . . ? O1A* N1A* O2A* 148(2) . . ? O1A* N1A* C1A* 103.8(16) . . ? O2A* N1A* C1A* 108.4(16) . . ? _diffrn_measured_fraction_theta_max 0.947 _diffrn_reflns_theta_full 31.30 _diffrn_measured_fraction_theta_full 0.947 _refine_diff_density_max 1.704 _refine_diff_density_min -0.768 _refine_diff_density_rms 0.105