# Electronic Supplementary Material (ESI) for Dalton Transactions # This journal is © The Royal Society of Chemistry 2013 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # ####################################################################### data_lau1b_10a120 _database_code_depnum_ccdc_archive 'CCDC 912672' #TrackingRef 'CCDC912672.cif' _diffrn_measurement_method 'w scans' #Added by publCIF _audit_creation_date 2012-10-11T13:42:24-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' _audit_conform_dict_name cif_core.dic _audit_conform_dict_version 2.4 _audit_conform_dict_location ftp://ftp.iucr.org/pub/cif_core.dic #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ? _chemical_formula_sum 'C44 H42 Co N2 O9' _chemical_formula_weight 801.73 _chemical_formula_moiety 'C32 H18 Co N2 O6, 3(C4 H8 O)' #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_space_group_name_hall P22ab _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M 'P 21 21 2' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z' '-x+1/2, y+1/2, -z' 'x+1/2, -y+1/2, -z' _cell_length_a 9.1959(5) _cell_length_b 20.5009(13) _cell_length_c 9.7022(7) _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_volume 1829.1(2) _cell_formula_units_Z 2 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 2048 _cell_measurement_theta_min 2.9699 _cell_measurement_theta_max 29.4201 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description parallelepiped _exptl_crystal_colour 'dark red' _exptl_crystal_size_max 0.4121 _exptl_crystal_size_mid 0.0603 _exptl_crystal_size_min 0.0565 _exptl_crystal_density_diffrn 1.456 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 838 _exptl_special_details ? #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.536 _exptl_absorpt_correction_T_min 0.915 _exptl_absorpt_correction_T_max 0.972 _exptl_absorpt_correction_type analytical _exptl_absorpt_process_details ; CrysAlisPro, Agilent Technologies, Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET) (compiled Jan 23 2012,18:06:46) Analytical numeric absorption correction using a multifaceted crystal model based on expressions derived by R.C. Clark & J.S. Reid. (Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897) ; #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_ambient_temperature 119.95(10) _diffrn_radiation_wavelength 0.7107 _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_source 'Enhance (Mo) X-ray Source' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Xcalibur, Atlas, Gemini ultra' _diffrn_detector_area_resol_mean 10.4186 _diffrn_reflns_av_R_equivalents 0.0643 _diffrn_reflns_av_sigmaI/netI 0.0952 _diffrn_reflns_number 9171 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -25 _diffrn_reflns_limit_k_max 24 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 2.98 _diffrn_reflns_theta_max 26.35 _diffrn_reflns_theta_full 26.35 _diffrn_measured_fraction_theta_full 0.998 _diffrn_measured_fraction_theta_max 0.998 _reflns_number_total 3709 _reflns_number_gt 2583 _reflns_threshold_expression >2sigma(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_publication_material 'PublCIF (Westrip, 2010)' _computing_molecular_graphics 'ORTEP-3: Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_data_collection ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.49a (release 05-10-2009 CrysAlis171 .NET) (compiled Oct 5 2009,17:28:39) ; _computing_cell_refinement ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.49a (release 05-10-2009 CrysAlis171 .NET) (compiled Oct 5 2009,17:28:39) ; _computing_data_reduction ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.49a (release 05-10-2009 CrysAlis171 .NET) (compiled Oct 5 2009,17:28:39) ; #----------------------------------------------------------------------------# # STRUCTURE SOLUTION #----------------------------------------------------------------------------# _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _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. Twelve restrains were used in modeling of THF molecules and one more in 1,10-phenantroline. ; _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^)+(0.0957P)^2^+1.2656P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.09(5) _refine_ls_number_reflns 3709 _refine_ls_number_parameters 207 _refine_ls_number_restraints 13 _refine_ls_R_factor_all 0.1197 _refine_ls_R_factor_gt 0.0808 _refine_ls_wR_factor_ref 0.2144 _refine_ls_wR_factor_gt 0.1892 _refine_ls_goodness_of_fit_ref 1.018 _refine_ls_restrained_S_all 1.074 _refine_ls_shift/su_max 0.023 _refine_ls_shift/su_mean 0.002 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# 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 0 '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 0.006 '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' 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 0.0000 0.5000 0.07277(11) 0.0346(3) Uani 1 2 d S . . O2 O 0.0280(4) 0.4241(2) 0.2008(4) 0.0370(10) Uani 1 1 d . . . O1 O -0.2199(4) 0.4651(2) 0.1002(4) 0.0359(10) Uani 1 1 d . . . C1 C -0.2276(6) 0.4189(3) 0.1803(6) 0.0254(12) Uani 1 1 d . . . C9 C -0.6236(7) 0.3870(4) 0.2239(10) 0.047(2) Uani 1 1 d . . . H9 H -0.7135 0.4037 0.1912 0.056 Uiso 1 1 calc R . . O4 O -0.2220(5) 0.2640(3) 0.4449(6) 0.0617(16) Uani 1 1 d . . . C5 C -0.3638(7) 0.3387(3) 0.3160(7) 0.0306(16) Uani 1 1 d . . . C2 C -0.0873(6) 0.3941(3) 0.2401(6) 0.0288(13) Uani 1 1 d . . . N1 N -0.0626(7) 0.5561(3) -0.0968(6) 0.0524(17) Uani 1 1 d D . . C10 C -0.4937(8) 0.4128(3) 0.1748(7) 0.0401(14) Uani 1 1 d . . . H10 H -0.4949 0.4464 0.1075 0.048 Uiso 1 1 calc R . . C7 C -0.4930(9) 0.3123(3) 0.3639(6) 0.0403(14) Uani 1 1 d . . . H7 H -0.4921 0.2769 0.4272 0.048 Uiso 1 1 calc R . . C4 C -0.2226(7) 0.3118(3) 0.3700(7) 0.0350(14) Uani 1 1 d . . . C8 C -0.6229(7) 0.3381(4) 0.3181(9) 0.047(2) Uani 1 1 d . . . H8 H -0.7122 0.3216 0.3527 0.056 Uiso 1 1 calc R . . C6 C -0.3652(6) 0.3897(3) 0.2238(8) 0.0272(14) Uani 1 1 d . . . C3 C -0.0905(7) 0.3414(3) 0.3257(7) 0.0361(15) Uani 1 1 d . . . H3 H -0.0010 0.3237 0.3572 0.043 Uiso 1 1 calc R . . C15 C -0.1242(12) 0.6122(4) -0.0981(9) 0.094(3) Uani 1 1 d D . . H15 H -0.1435 0.6331 -0.0127 0.113 Uiso 1 1 calc RD . . C13 C -0.1652(16) 0.6447(6) -0.2228(11) 0.112(4) Uani 1 1 d . . . H13 H -0.2130 0.6856 -0.2164 0.134 Uiso 1 1 calc RD . . C12 C -0.0723(11) 0.5602(5) -0.3466(8) 0.071(3) Uani 1 1 d . . . C11 C -0.0360(10) 0.5309(4) -0.2216(8) 0.065(3) Uani 1 1 d . . . C16 C -0.0350(15) 0.5279(5) -0.4696(9) 0.101(6) Uani 1 1 d . . . H16 H -0.0614 0.5470 -0.5552 0.121 Uiso 1 1 calc R . . C17 C -0.1412(14) 0.6216(6) -0.3387(11) 0.094(3) Uani 1 1 d U . . H17 H -0.1683 0.6446 -0.4197 0.113 Uiso 1 1 calc R . . O23 O 0.0000 0.0000 0.219(3) 0.270(8) Uani 1 2 d SD . . C24 C -0.129(2) -0.009(2) 0.299(2) 0.270(8) Uani 1 1 d D . . H24A H -0.1846 -0.0471 0.2675 0.324 Uiso 1 1 calc R . . H24B H -0.1915 0.0304 0.2955 0.324 Uiso 1 1 calc R . . C25 C -0.0706(19) -0.0191(14) 0.439(2) 0.270(8) Uani 1 1 d D . . H25A H -0.0527 -0.0660 0.4569 0.324 Uiso 1 1 calc R . . H25B H -0.1385 -0.0021 0.5099 0.324 Uiso 1 1 calc R . . O18 O -0.2388(15) 0.8524(5) 0.1970(12) 0.250(8) Uiso 1 1 d G . . C22A C -0.3133(11) 0.8283(8) 0.0798(14) 0.26(3) Uiso 0.49(3) 1 d PG A 1 H22A H -0.3135 0.8613 0.0054 0.315 Uiso 0.49(3) 1 calc PR A 1 H22B H -0.4152 0.8176 0.1035 0.315 Uiso 0.49(3) 1 calc PR A 1 C19A C -0.234(2) 0.7685(5) 0.0345(11) 0.100(9) Uiso 0.49(3) 1 d PG A 1 H19A H -0.2347 0.7644 -0.0672 0.121 Uiso 0.49(3) 1 calc PRD A 1 H19B H -0.2775 0.7288 0.0754 0.121 Uiso 0.49(3) 1 calc PR A 1 C20A C -0.0804(16) 0.7797(6) 0.0884(16) 0.083(7) Uiso 0.49(3) 1 d PG A 1 H20A H -0.0294 0.7380 0.1055 0.099 Uiso 0.49(3) 1 calc PR A 1 H20B H -0.0223 0.8066 0.0239 0.099 Uiso 0.49(3) 1 calc PR A 1 C21A C -0.1098(13) 0.8146(7) 0.2171(13) 0.122(12) Uiso 0.49(3) 1 d PG A 1 H21A H -0.1238 0.7832 0.2935 0.146 Uiso 0.49(3) 1 calc PR A 1 H21B H -0.0270 0.8435 0.2404 0.146 Uiso 0.49(3) 1 calc PR A 1 C22B C -0.3008(11) 0.8032(7) 0.1064(13) 0.076(7) Uiso 0.51(3) 1 d PG A 2 H22C H -0.3480 0.8237 0.0256 0.091 Uiso 0.51(3) 1 calc PR A 2 H22D H -0.3736 0.7764 0.1560 0.091 Uiso 0.51(3) 1 calc PR A 2 C19B C -0.174(2) 0.7625(4) 0.0630(12) 0.058(5) Uiso 0.51(3) 1 d PG A 2 H19C H -0.1661 0.7608 -0.0386 0.070 Uiso 0.51(3) 1 calc PR A 2 H19D H -0.1825 0.7175 0.0993 0.070 Uiso 0.51(3) 1 calc PRD A 2 C20B C -0.0450(12) 0.7980(8) 0.1265(17) 0.153(13) Uiso 0.51(3) 1 d PG A 2 H20C H 0.0369 0.7679 0.1446 0.184 Uiso 0.51(3) 1 calc PR A 2 H20D H -0.0111 0.8341 0.0669 0.184 Uiso 0.51(3) 1 calc PR A 2 C21B C -0.1086(16) 0.8224(7) 0.2548(13) 0.155(16) Uiso 0.51(3) 1 d PG A 2 H21C H -0.1321 0.7867 0.3198 0.187 Uiso 0.51(3) 1 calc PR A 2 H21D H -0.0450 0.8548 0.3008 0.187 Uiso 0.51(3) 1 calc PR A 2 loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Co1 0.0341(6) 0.0417(6) 0.0281(6) 0.000 0.000 -0.0122(7) O2 0.024(2) 0.050(2) 0.037(2) 0.002(2) -0.0045(18) -0.008(2) O1 0.031(2) 0.037(2) 0.040(3) 0.011(2) -0.0098(18) -0.0103(19) C1 0.025(3) 0.026(3) 0.025(3) 0.002(2) -0.005(2) -0.002(2) C9 0.022(4) 0.039(4) 0.079(6) -0.001(5) 0.001(4) 0.005(3) O4 0.053(3) 0.063(3) 0.069(4) 0.046(3) -0.016(3) -0.011(3) C5 0.029(3) 0.038(4) 0.024(4) -0.006(3) 0.003(3) -0.004(3) C2 0.020(3) 0.039(3) 0.027(3) -0.004(3) -0.003(2) 0.002(3) N1 0.067(4) 0.059(4) 0.031(4) 0.019(3) 0.002(3) -0.015(3) C10 0.028(3) 0.031(3) 0.061(4) 0.006(3) -0.014(4) -0.005(4) C7 0.035(3) 0.045(3) 0.041(3) 0.003(3) 0.004(4) -0.005(4) C4 0.036(4) 0.032(3) 0.037(4) 0.005(3) -0.007(3) -0.009(3) C8 0.030(4) 0.040(5) 0.071(7) -0.004(4) 0.014(4) -0.016(3) C6 0.024(3) 0.026(3) 0.032(4) -0.006(3) -0.004(3) 0.000(2) C3 0.027(3) 0.038(4) 0.043(4) 0.008(3) -0.013(3) 0.000(3) C15 0.130(7) 0.112(6) 0.041(4) 0.046(4) -0.008(4) -0.024(5) C13 0.165(13) 0.110(9) 0.061(7) 0.054(7) -0.008(8) 0.000(8) C12 0.101(7) 0.089(7) 0.024(4) 0.015(4) -0.010(4) -0.050(5) C11 0.086(7) 0.081(5) 0.029(4) 0.012(3) -0.004(4) -0.055(5) C16 0.129(14) 0.134(10) 0.039(4) 0.024(5) -0.019(5) -0.083(11) C17 0.130(7) 0.112(6) 0.041(4) 0.046(4) -0.008(4) -0.024(5) O23 0.220(17) 0.398(18) 0.194(13) 0.000 0.000 0.05(2) C24 0.220(17) 0.398(18) 0.194(13) 0.000 0.000 0.05(2) C25 0.220(17) 0.398(18) 0.194(13) 0.000 0.000 0.05(2) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Co1 O2 2.007(4) . ? Co1 O2 2.008(4) 2_565 ? Co1 N1 2.088(6) . ? Co1 N1 2.088(6) 2_565 ? Co1 O1 2.162(4) 2_565 ? Co1 O1 2.162(4) . ? O2 C2 1.284(7) . ? O1 C1 1.227(7) . ? C1 C6 1.461(8) . ? C1 C2 1.504(8) . ? C9 C8 1.356(12) . ? C9 C10 1.390(10) . ? C9 H9 0.9500 . ? O4 C4 1.221(7) . ? C5 C6 1.377(10) . ? C5 C7 1.386(10) . ? C5 C4 1.504(9) . ? C2 C3 1.363(9) . ? N1 C15 1.283(8) . ? N1 C11 1.339(10) . ? C10 C6 1.359(9) . ? C10 H10 0.9500 . ? C7 C8 1.381(11) . ? C7 H7 0.9500 . ? C4 C3 1.424(9) . ? C8 H8 0.9500 . ? C3 H3 0.9500 . ? C15 C13 1.431(13) . ? C15 H15 0.9500 . ? C13 C17 1.240(15) . ? C13 H13 0.9500 . ? C12 C11 1.394(11) . ? C12 C16 1.407(13) . ? C12 C17 1.412(16) . ? C11 C11 1.430(19) 2_565 ? C16 C16 1.31(2) 2_565 ? C16 H16 0.9500 . ? C17 H17 0.9500 . ? O23 C24 1.425(7) 2 ? O23 C24 1.425(7) . ? C24 C25 1.473(18) . ? C24 H24A 0.9900 . ? C24 H24B 0.9900 . ? C25 C25 1.52(2) 2 ? C25 H25A 0.9900 . ? C25 H25B 0.9900 . ? O18 C22A 1.4162 . ? O18 C21A 1.4301 . ? O18 C22B 1.4544 . ? O18 C21B 1.4580 . ? C22A C19A 1.4918 . ? C22A H22A 0.9900 . ? C22A H22B 0.9900 . ? C19A C20A 1.5240 . ? C19A H19A 0.9900 . ? C19A H19B 0.9900 . ? C20A C21A 1.4640 . ? C20A H20A 0.9900 . ? C20A H20B 0.9900 . ? C21A H21A 0.9900 . ? C21A H21B 0.9900 . ? C22B C19B 1.4917 . ? C22B H22C 0.9900 . ? C22B H22D 0.9900 . ? C19B C20B 1.5239 . ? C19B H19C 0.9900 . ? C19B H19D 0.9900 . ? C20B C21B 1.4639 . ? C20B H20C 0.9900 . ? C20B H20D 0.9900 . ? C21B H21C 0.9900 . ? C21B H21D 0.9900 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O2 Co1 O2 103.5(3) . 2_565 ? O2 Co1 N1 161.8(2) . . ? O2 Co1 N1 91.5(2) 2_565 . ? O2 Co1 N1 91.5(2) . 2_565 ? O2 Co1 N1 161.8(2) 2_565 2_565 ? N1 Co1 N1 76.0(4) . 2_565 ? O2 Co1 O1 93.47(16) . 2_565 ? O2 Co1 O1 77.72(15) 2_565 2_565 ? N1 Co1 O1 99.9(2) . 2_565 ? N1 Co1 O1 91.23(19) 2_565 2_565 ? O2 Co1 O1 77.72(15) . . ? O2 Co1 O1 93.47(16) 2_565 . ? N1 Co1 O1 91.23(19) . . ? N1 Co1 O1 99.9(2) 2_565 . ? O1 Co1 O1 165.9(2) 2_565 . ? C2 O2 Co1 116.7(4) . . ? C1 O1 Co1 112.8(3) . . ? O1 C1 C6 123.3(5) . . ? O1 C1 C2 117.1(5) . . ? C6 C1 C2 119.5(5) . . ? C8 C9 C10 120.6(7) . . ? C8 C9 H9 119.7 . . ? C10 C9 H9 119.7 . . ? C6 C5 C7 120.4(6) . . ? C6 C5 C4 120.9(5) . . ? C7 C5 C4 118.7(6) . . ? O2 C2 C3 125.4(5) . . ? O2 C2 C1 115.6(5) . . ? C3 C2 C1 119.0(5) . . ? C15 N1 C11 114.7(7) . . ? C15 N1 Co1 128.6(6) . . ? C11 N1 Co1 116.7(5) . . ? C6 C10 C9 119.6(5) . . ? C6 C10 H10 120.2 . . ? C9 C10 H10 120.2 . . ? C8 C7 C5 119.0(5) . . ? C8 C7 H7 120.5 . . ? C5 C7 H7 120.5 . . ? O4 C4 C3 121.2(6) . . ? O4 C4 C5 120.4(6) . . ? C3 C4 C5 118.3(5) . . ? C9 C8 C7 120.3(6) . . ? C9 C8 H8 119.9 . . ? C7 C8 H8 119.9 . . ? C10 C6 C5 120.0(6) . . ? C10 C6 C1 120.6(6) . . ? C5 C6 C1 119.4(5) . . ? C2 C3 C4 122.7(6) . . ? C2 C3 H3 118.6 . . ? C4 C3 H3 118.6 . . ? N1 C15 C13 122.8(9) . . ? N1 C15 H15 118.6 . . ? C13 C15 H15 118.6 . . ? C17 C13 C15 122.9(12) . . ? C17 C13 H13 118.6 . . ? C15 C13 H13 118.6 . . ? C11 C12 C16 118.4(9) . . ? C11 C12 C17 116.4(8) . . ? C16 C12 C17 125.2(9) . . ? N1 C11 C12 125.2(9) . . ? N1 C11 C11 115.2(5) . 2_565 ? C12 C11 C11 119.5(6) . 2_565 ? O2 Co1 O2 103.5(3) . 2_565 ? O2 Co1 N1 161.8(2) . . ? O2 Co1 N1 91.5(2) 2_565 . ? O2 Co1 N1 91.5(2) . 2_565 ? O2 Co1 N1 161.8(2) 2_565 2_565 ? N1 Co1 N1 76.0(4) . 2_565 ? O2 Co1 O1 93.47(16) . 2_565 ? O2 Co1 O1 77.72(15) 2_565 2_565 ? N1 Co1 O1 99.9(2) . 2_565 ? N1 Co1 O1 91.23(19) 2_565 2_565 ? O2 Co1 O1 77.72(15) . . ? O2 Co1 O1 93.47(16) 2_565 . ? N1 Co1 O1 91.23(19) . . ? N1 Co1 O1 99.9(2) 2_565 . ? O1 Co1 O1 165.9(2) 2_565 . ? C2 O2 Co1 116.7(4) . . ? C1 O1 Co1 112.8(3) . . ? O1 C1 C6 123.3(5) . . ? O1 C1 C2 117.1(5) . . ? C6 C1 C2 119.5(5) . . ? C8 C9 C10 120.6(7) . . ? C8 C9 H9 119.7 . . ? C10 C9 H9 119.7 . . ? C6 C5 C7 120.4(6) . . ? C6 C5 C4 120.9(5) . . ? C7 C5 C4 118.7(6) . . ? O2 C2 C3 125.4(5) . . ? O2 C2 C1 115.6(5) . . ? C3 C2 C1 119.0(5) . . ? C15 N1 C11 114.7(7) . . ? C15 N1 Co1 128.6(6) . . ? C11 N1 Co1 116.7(5) . . ? C6 C10 C9 119.6(5) . . ? C6 C10 H10 120.2 . . ? C9 C10 H10 120.2 . . ? C16 C16 C12 122.0(6) 2_565 . ? C16 C16 H16 119.0 2_565 . ? C12 C16 H16 119.0 . . ? C13 C17 C12 118.0(9) . . ? C13 C17 H17 121.0 . . ? C12 C17 H17 121.0 . . ? C24 O23 C24 114(3) 2 . ? O23 C24 C25 103(2) . . ? O23 C24 H24A 111.2 . . ? C25 C24 H24A 111.2 . . ? O23 C24 H24B 111.2 . . ? C25 C24 H24B 111.2 . . ? H24A C24 H24B 109.1 . . ? C24 C25 C25 103.6(15) . 2 ? C24 C25 H25A 111.0 . . ? C25 C25 H25A 111.0 2 . ? C24 C25 H25B 111.0 . . ? C25 C25 H25B 111.0 2 . ? H25A C25 H25B 109.0 . . ? C22A O18 C21A 108.8 . . ? C22A O18 C22B 23.6 . . ? C21A O18 C22B 91.9 . . ? C22A O18 C21B 124.0 . . ? C21A O18 C21B 15.9 . . ? C22B O18 C21B 105.2 . . ? O18 C22A C19A 106.7 . . ? O18 C22A H22A 110.4 . . ? C19A C22A H22A 110.4 . . ? O18 C22A H22B 110.4 . . ? C19A C22A H22B 110.4 . . ? H22A C22A H22B 108.6 . . ? C22A C19A C20A 103.2 . . ? C22A C19A H19A 111.1 . . ? C20A C19A H19A 111.1 . . ? C22A C19A H19B 111.1 . . ? C20A C19A H19B 111.1 . . ? H19A C19A H19B 109.1 . . ? C21A C20A C19A 101.3 . . ? C21A C20A H20A 111.5 . . ? C19A C20A H20A 111.5 . . ? C21A C20A H20B 111.5 . . ? C19A C20A H20B 111.5 . . ? H20A C20A H20B 109.3 . . ? O18 C21A C20A 107.5 . . ? O18 C21A H21A 110.2 . . ? C20A C21A H21A 110.2 . . ? O18 C21A H21B 110.2 . . ? C20A C21A H21B 110.2 . . ? H21A C21A H21B 108.5 . . ? O18 C22B C19B 104.6 . . ? O18 C22B H22C 110.8 . . ? C19B C22B H22C 110.8 . . ? O18 C22B H22D 110.8 . . ? C19B C22B H22D 110.8 . . ? H22C C22B H22D 108.9 . . ? C22B C19B C20B 103.2 . . ? C22B C19B H19C 111.1 . . ? C20B C19B H19C 111.1 . . ? C22B C19B H19D 111.1 . . ? C20B C19B H19D 111.1 . . ? H19C C19B H19D 109.1 . . ? C21B C20B C19B 101.3 . . ? C21B C20B H20C 111.5 . . ? C19B C20B H20C 111.5 . . ? C21B C20B H20D 111.5 . . ? C19B C20B H20D 111.5 . . ? H20C C20B H20D 109.3 . . ? O18 C21B C20B 98.3 . . ? O18 C21B H21C 112.1 . . ? C20B C21B H21C 112.1 . . ? O18 C21B H21D 112.1 . . ? C20B C21B H21D 112.1 . . ? H21C C21B H21D 109.7 . . ? _refine_diff_density_max 0.749 _refine_diff_density_min -0.427 _refine_diff_density_rms 0.090 data_lau22_2 _database_code_depnum_ccdc_archive 'CCDC 912673' #TrackingRef 'CCDC912673.cif' _audit_creation_date 2013-01-10T17:38:57-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' _audit_conform_dict_name cif_core.dic _audit_conform_dict_version 2.4 _audit_conform_dict_location ftp://ftp.iucr.org/pub/cif_core.dic #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ? _chemical_formula_sum 'C59 H36 Co2 N8 O12' _chemical_formula_weight 1166.82 #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1' _symmetry_space_group_name_hall '-P 1' _cell_length_a 8.2264(4) _cell_length_b 11.0110(7) _cell_length_c 15.2164(8) _cell_angle_alpha 72.632(5) _cell_angle_beta 78.902(4) _cell_angle_gamma 82.156(5) _cell_volume 1286.27(12) _cell_formula_units_Z 1 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 8109 _cell_measurement_theta_min 2.9405 _cell_measurement_theta_max 29.5577 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description parallelepiped _exptl_crystal_colour 'dark red' _exptl_crystal_size_max 0.7507 _exptl_crystal_size_mid 0.2903 _exptl_crystal_size_min 0.0902 _exptl_crystal_density_diffrn 1.506 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 596 _exptl_special_details 'The big crystal was used because of reduced diffraction power of the samples besides we avoid damage samples by breaking them.' #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.724 _exptl_absorpt_correction_T_min 0.743 _exptl_absorpt_correction_T_max 0.943 _exptl_absorpt_correction_type analytical _exptl_absorpt_process_details ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.55 (release 05-01-2010 CrysAlis171 .NET) (compiled Jan 5 2010,16:28:46) Analytical numeric absorption correction using a multifaceted crystal model based on expressions derived by R.C. Clark & J.S. Reid. (Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897) ; #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 0.7107 _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_source 'Enhance (Mo) X-ray Source' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Xcalibur, Atlas, Gemini ultra' _diffrn_detector_area_resol_mean 10.4186 _diffrn_reflns_av_R_equivalents 0.0431 _diffrn_reflns_av_unetI/netI 0.0502 _diffrn_reflns_number 12960 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 2.95 _diffrn_reflns_theta_max 26.37 _diffrn_reflns_theta_full 26.37 _diffrn_measured_fraction_theta_full 0.998 _diffrn_measured_fraction_theta_max 0.998 _reflns_number_total 5244 _reflns_number_gt 4132 _reflns_threshold_expression >2sigma(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_publication_material 'PublCIF (Westrip, 2010)' _computing_molecular_graphics 'ORTEP-3: Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_data_collection ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.49a (release 05-10-2009 CrysAlis171 .NET) (compiled Oct 5 2009,17:28:39) ; _computing_cell_refinement ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.49a (release 05-10-2009 CrysAlis171 .NET) (compiled Oct 5 2009,17:28:39) ; _computing_data_reduction ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.49a (release 05-10-2009 CrysAlis171 .NET) (compiled Oct 5 2009,17:28:39) ; #----------------------------------------------------------------------------# # STRUCTURE SOLUTION #----------------------------------------------------------------------------# _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0640P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_number_reflns 5244 _refine_ls_number_parameters 379 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0517 _refine_ls_R_factor_gt 0.038 _refine_ls_wR_factor_ref 0.1018 _refine_ls_wR_factor_gt 0.0976 _refine_ls_goodness_of_fit_ref 0.986 _refine_ls_restrained_S_all 0.986 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0 _refine_diff_density_max 0.407 _refine_diff_density_min -0.459 _refine_diff_density_rms 0.069 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# 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' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.006 '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' H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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 0.20358(3) 0.69146(3) 0.777987(19) 0.01760(10) Uani 1 1 d . . . O1A O 0.13165(18) 0.87672(14) 0.80599(10) 0.0211(3) Uani 1 1 d . . . O2A O 0.29113(18) 0.66547(14) 0.90087(10) 0.0201(3) Uani 1 1 d . . . O1 O 0.15597(18) 0.77132(15) 0.63675(10) 0.0217(3) Uani 1 1 d . . . O2 O 0.42800(18) 0.76645(15) 0.70348(10) 0.0215(3) Uani 1 1 d . . . O4A O 0.3895(2) 0.89232(16) 1.09954(11) 0.0302(4) Uani 1 1 d . . . N3 N 0.2970(2) 0.51306(17) 0.76273(12) 0.0201(4) Uani 1 1 d . . . N1 N -0.0457(2) 0.65334(18) 0.81441(13) 0.0202(4) Uani 1 1 d . . . O4 O 0.7070(2) 0.90125(19) 0.39421(12) 0.0373(4) Uani 1 1 d . . . N2 N -0.3099(2) 0.67501(19) 0.80200(13) 0.0245(4) Uani 1 1 d . . . H2 H -0.4028 0.7032 0.7792 0.029 Uiso 1 1 calc R . . C1A C 0.1914(3) 0.8853(2) 0.87200(15) 0.0188(5) Uani 1 1 d . . . N4 N 0.4391(3) 0.3255(2) 0.78878(14) 0.0301(5) Uani 1 1 d . . . H4 H 0.5014 0.2582 0.8156 0.036 Uiso 1 1 calc R . . C1 C 0.2778(3) 0.8117(2) 0.57921(15) 0.0185(5) Uani 1 1 d . . . C6A C 0.1725(3) 1.0033(2) 0.90023(15) 0.0203(5) Uani 1 1 d . . . C2 C 0.4397(3) 0.8030(2) 0.61423(15) 0.0191(5) Uani 1 1 d . . . C5A C 0.2403(3) 1.0055(2) 0.97737(15) 0.0207(5) Uani 1 1 d . . . C4A C 0.3335(3) 0.8883(2) 1.03011(15) 0.0231(5) Uani 1 1 d . . . C7A C 0.2175(3) 1.1165(2) 1.00560(16) 0.0255(5) Uani 1 1 d . . . H7A H 0.2636 1.119 1.0576 0.031 Uiso 1 1 calc R . . C6 C 0.2693(3) 0.8663(2) 0.47961(15) 0.0199(5) Uani 1 1 d . . . C5 C 0.4154(3) 0.8965(2) 0.41688(15) 0.0233(5) Uani 1 1 d . . . C4 C 0.5789(3) 0.8772(2) 0.45147(16) 0.0263(5) Uani 1 1 d . . . C10 C 0.1165(3) 0.8881(2) 0.44817(15) 0.0241(5) Uani 1 1 d . . . H10 H 0.0176 0.8665 0.4912 0.029 Uiso 1 1 calc R . . C3A C 0.3526(3) 0.7760(2) 0.99970(16) 0.0257(5) Uani 1 1 d . . . H13 H 0.4162 0.7035 1.0319 0.031 Uiso 1 1 calc R . . C2A C 0.2851(3) 0.7663(2) 0.92691(15) 0.0204(5) Uani 1 1 d . . . C8A C 0.1273(3) 1.2237(2) 0.95783(17) 0.0270(5) Uani 1 1 d . . . H8A H 0.1108 1.2991 0.9777 0.032 Uiso 1 1 calc R . . C8 C 0.2552(3) 0.9680(2) 0.29149(16) 0.0303(6) Uani 1 1 d . . . H8 H 0.2507 1.0015 0.2267 0.036 Uiso 1 1 calc R . . C21 C -0.1603(3) 0.7131(2) 0.76296(16) 0.0243(5) Uani 1 1 d . . . H21 H -0.1381 0.776 0.7048 0.029 Uiso 1 1 calc R . . C23 C -0.1304(3) 0.5703(2) 0.89076(16) 0.0237(5) Uani 1 1 d . . . H23 H -0.0814 0.5122 0.9405 0.028 Uiso 1 1 calc R . . C25 C 0.3866(3) 0.4281(2) 0.81920(17) 0.0242(5) Uani 1 1 d . . . H25 H 0.4109 0.4386 0.8749 0.029 Uiso 1 1 calc R . . C22 C -0.2936(3) 0.5842(2) 0.88412(16) 0.0258(5) Uani 1 1 d . . . H22 H -0.3796 0.5396 0.9278 0.031 Uiso 1 1 calc R . . C10A C 0.0842(3) 1.1118(2) 0.85210(16) 0.0247(5) Uani 1 1 d . . . H10A H 0.0399 1.1107 0.7992 0.03 Uiso 1 1 calc R . . C9 C 0.1095(3) 0.9413(2) 0.35426(16) 0.0291(6) Uani 1 1 d . . . H9 H 0.0054 0.9595 0.3328 0.035 Uiso 1 1 calc R . . C7 C 0.4077(3) 0.9464(2) 0.32230(16) 0.0275(5) Uani 1 1 d . . . H7 H 0.5066 0.9656 0.2787 0.033 Uiso 1 1 calc R . . C9A C 0.0610(3) 1.2213(2) 0.88123(17) 0.0280(5) Uani 1 1 d . . . H9A H -0.0004 1.295 0.8487 0.034 Uiso 1 1 calc R . . C3 C 0.5792(3) 0.8331(2) 0.55040(16) 0.0241(5) Uani 1 1 d . . . H3 H 0.682 0.8244 0.5723 0.029 Uiso 1 1 calc R . . C24 C 0.2901(4) 0.4607(3) 0.69252(18) 0.0382(7) Uani 1 1 d . . . H24 H 0.2329 0.4994 0.6411 0.046 Uiso 1 1 calc R . . C26 C 0.3777(4) 0.3450(3) 0.70800(19) 0.0437(7) Uani 1 1 d . . . H26 H 0.3933 0.2884 0.6701 0.052 Uiso 1 1 calc R . . C1T C 0.8954(5) 0.5878(3) 0.4915(3) 0.0581(9) Uani 1 1 d . . -1 C2T C 1.1322(5) 0.5920(4) 0.3625(3) 0.0731(11) Uani 1 1 d . . -1 C3T C 0.9758(8) 0.6445(6) 0.4068(5) 0.0472(15) Uani 0.5 1 d P . . C5T C 1.1890(9) 0.4703(7) 0.4207(6) 0.064(2) Uani 0.5 1 d P . . C4T C 1.0506(9) 0.5331(7) 0.4500(5) 0.0574(18) Uani 0.5 1 d P . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Co1 0.01631(16) 0.01890(18) 0.01553(16) -0.00108(12) -0.00443(11) -0.00030(11) O1A 0.0215(8) 0.0205(8) 0.0200(8) -0.0027(7) -0.0067(6) 0.0010(6) O2A 0.0206(8) 0.0152(8) 0.0235(8) -0.0044(6) -0.0066(6) 0.0038(6) O1 0.0161(8) 0.0281(9) 0.0176(8) -0.0016(7) -0.0022(6) -0.0026(6) O2 0.0187(8) 0.0255(9) 0.0168(8) 0.0007(6) -0.0041(6) -0.0032(6) O4A 0.0380(10) 0.0312(10) 0.0236(9) -0.0096(8) -0.0130(8) 0.0052(8) N3 0.0218(9) 0.0173(10) 0.0208(9) -0.0045(8) -0.0040(8) -0.0007(8) N1 0.0191(9) 0.0203(10) 0.0200(9) -0.0024(8) -0.0060(8) -0.0012(7) O4 0.0249(9) 0.0477(12) 0.0299(10) -0.0030(9) 0.0048(8) -0.0027(8) N2 0.0164(10) 0.0272(11) 0.0274(10) -0.0028(9) -0.0065(8) -0.0001(8) C1A 0.0169(11) 0.0195(12) 0.0172(11) -0.0017(9) -0.0009(9) -0.0018(9) N4 0.0323(11) 0.0220(11) 0.0328(11) -0.0052(9) -0.0080(9) 0.0073(9) C1 0.0190(11) 0.0157(11) 0.0198(11) -0.0053(9) -0.0024(9) 0.0017(9) C6A 0.0192(11) 0.0199(12) 0.0189(11) -0.0028(9) 0.0003(9) -0.0027(9) C2 0.0207(11) 0.0150(11) 0.0209(11) -0.0036(9) -0.0049(9) 0.0003(9) C5A 0.0198(11) 0.0208(12) 0.0183(11) -0.0028(9) 0.0000(9) -0.0014(9) C4A 0.0220(12) 0.0274(13) 0.0181(11) -0.0057(10) -0.0019(9) 0.0006(10) C7A 0.0271(12) 0.0273(13) 0.0213(12) -0.0060(10) -0.0021(10) -0.0032(10) C6 0.0252(12) 0.0161(11) 0.0171(11) -0.0041(9) -0.0030(9) 0.0003(9) C5 0.0283(12) 0.0196(12) 0.0196(11) -0.0057(9) 0.0007(10) 0.0003(10) C4 0.0234(12) 0.0243(13) 0.0259(12) -0.0044(10) 0.0027(10) -0.0001(10) C10 0.0247(12) 0.0270(13) 0.0181(11) -0.0041(10) -0.0024(9) 0.0004(10) C3A 0.0278(12) 0.0239(13) 0.0245(12) -0.0057(10) -0.0107(10) 0.0073(10) C2A 0.0198(11) 0.0214(12) 0.0169(11) -0.0015(9) -0.0025(9) 0.0003(9) C8A 0.0298(13) 0.0208(13) 0.0285(13) -0.0076(10) 0.0008(10) -0.0025(10) C8 0.0449(15) 0.0267(14) 0.0170(11) -0.0041(10) -0.0066(11) 0.0030(11) C21 0.0207(12) 0.0240(13) 0.0232(12) 0.0014(10) -0.0056(10) -0.0002(9) C23 0.0268(12) 0.0227(13) 0.0199(11) -0.0015(9) -0.0064(10) -0.0028(10) C25 0.0256(12) 0.0224(13) 0.0261(12) -0.0080(10) -0.0070(10) -0.0009(10) C22 0.0251(12) 0.0292(14) 0.0207(12) -0.0027(10) -0.0016(10) -0.0068(10) C10A 0.0270(12) 0.0216(13) 0.0235(12) -0.0011(10) -0.0071(10) -0.0022(10) C9 0.0334(13) 0.0324(15) 0.0216(12) -0.0078(10) -0.0088(10) 0.0042(11) C7 0.0342(13) 0.0235(13) 0.0196(12) -0.0049(10) 0.0047(10) -0.0005(10) C9A 0.0299(13) 0.0185(13) 0.0309(13) 0.0003(10) -0.0062(10) -0.0001(10) C3 0.0192(11) 0.0241(13) 0.0264(12) -0.0043(10) -0.0033(9) -0.0002(9) C24 0.0594(18) 0.0303(15) 0.0281(14) -0.0087(12) -0.0204(13) 0.0056(13) C26 0.071(2) 0.0288(16) 0.0325(15) -0.0141(12) -0.0153(14) 0.0134(14) C1T 0.062(2) 0.041(2) 0.083(3) -0.027(2) -0.036(2) 0.0118(17) C2T 0.082(3) 0.061(3) 0.074(3) -0.014(2) -0.016(2) -0.004(2) C3T 0.049(4) 0.029(3) 0.066(4) -0.007(3) -0.022(3) -0.007(3) C5T 0.050(4) 0.054(5) 0.095(6) -0.037(5) -0.017(4) 0.010(3) C4T 0.072(5) 0.044(4) 0.066(4) -0.021(4) -0.033(4) 0.006(4) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _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 O2A 2.0590(15) . ? Co1 N3 2.0724(18) . ? Co1 N1 2.0849(18) . ? Co1 O2 2.1040(15) . ? Co1 O1 2.1557(15) . ? Co1 O1A 2.1875(15) . ? O1A C1A 1.232(3) . ? O2A C2A 1.277(3) . ? O1 C1 1.233(3) . ? O2 C2 1.284(3) . ? O4A C4A 1.246(3) . ? N3 C25 1.316(3) . ? N3 C24 1.370(3) . ? N1 C21 1.320(3) . ? N1 C23 1.378(3) . ? O4 C4 1.235(3) . ? N2 C21 1.324(3) . ? N2 C22 1.365(3) . ? N2 H2 0.88 . ? C1A C6A 1.466(3) . ? C1A C2A 1.526(3) . ? N4 C25 1.334(3) . ? N4 C26 1.365(3) . ? N4 H4 0.88 . ? C1 C6 1.466(3) . ? C1 C2 1.508(3) . ? C6A C10A 1.392(3) . ? C6A C5A 1.401(3) . ? C2 C3 1.361(3) . ? C5A C7A 1.390(3) . ? C5A C4A 1.499(3) . ? C4A C3A 1.424(3) . ? C7A C8A 1.389(3) . ? C7A H7A 0.95 . ? C6 C5 1.395(3) . ? C6 C10 1.395(3) . ? C5 C7 1.389(3) . ? C5 C4 1.503(3) . ? C4 C3 1.438(3) . ? C10 C9 1.382(3) . ? C10 H10 0.95 . ? C3A C2A 1.368(3) . ? C3A H13 0.95 . ? C8A C9A 1.387(3) . ? C8A H8A 0.95 . ? C8 C9 1.387(3) . ? C8 C7 1.388(4) . ? C8 H8 0.95 . ? C21 H21 0.95 . ? C23 C22 1.350(3) . ? C23 H23 0.95 . ? C25 H25 0.95 . ? C22 H22 0.95 . ? C10A C9A 1.382(3) . ? C10A H10A 0.95 . ? C9 H9 0.95 . ? C7 H7 0.95 . ? C9A H9A 0.95 . ? C3 H3 0.95 . ? C24 C26 1.354(4) . ? C24 H24 0.95 . ? C26 H26 0.95 . ? C1T C3T 1.339(8) . ? C1T C5T 1.389(9) 2_766 ? C1T C4T 1.430(8) 2_766 ? C1T C4T 1.449(8) . ? C2T C4T 1.379(8) . ? C2T C5T 1.441(9) . ? C2T C3T 1.462(8) . ? C3T C4T 1.336(9) . ? C5T C4T 1.322(10) . ? C5T C1T 1.389(9) 2_766 ? C4T C1T 1.430(8) 2_766 ? C4T C4T 1.598(16) 2_766 ? 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 O2A Co1 N3 95.02(6) . . ? O2A Co1 N1 106.57(7) . . ? N3 Co1 N1 96.60(7) . . ? O2A Co1 O2 89.37(6) . . ? N3 Co1 O2 89.88(7) . . ? N1 Co1 O2 162.10(7) . . ? O2A Co1 O1 161.73(6) . . ? N3 Co1 O1 95.57(7) . . ? N1 Co1 O1 86.93(6) . . ? O2 Co1 O1 75.82(6) . . ? O2A Co1 O1A 77.71(6) . . ? N3 Co1 O1A 172.06(6) . . ? N1 Co1 O1A 88.63(6) . . ? O2 Co1 O1A 86.87(6) . . ? O1 Co1 O1A 90.66(6) . . ? C1A O1A Co1 111.97(13) . . ? C2A O2A Co1 115.23(13) . . ? C1 O1 Co1 114.75(13) . . ? C2 O2 Co1 116.06(13) . . ? C25 N3 C24 105.5(2) . . ? C25 N3 Co1 124.99(15) . . ? C24 N3 Co1 129.41(16) . . ? C21 N1 C23 104.76(18) . . ? C21 N1 Co1 123.24(15) . . ? C23 N1 Co1 131.99(15) . . ? C21 N2 C22 107.47(19) . . ? C21 N2 H2 126.3 . . ? C22 N2 H2 126.3 . . ? O1A C1A C6A 122.7(2) . . ? O1A C1A C2A 117.74(19) . . ? C6A C1A C2A 119.59(19) . . ? C25 N4 C26 106.8(2) . . ? C25 N4 H4 126.6 . . ? C26 N4 H4 126.6 . . ? O1 C1 C6 122.19(19) . . ? O1 C1 C2 117.80(19) . . ? C6 C1 C2 120.00(19) . . ? C10A C6A C5A 120.0(2) . . ? C10A C6A C1A 120.3(2) . . ? C5A C6A C1A 119.7(2) . . ? O2 C2 C3 127.4(2) . . ? O2 C2 C1 114.33(19) . . ? C3 C2 C1 118.3(2) . . ? C7A C5A C6A 119.4(2) . . ? C7A C5A C4A 120.4(2) . . ? C6A C5A C4A 120.1(2) . . ? O4A C4A C3A 122.5(2) . . ? O4A C4A C5A 118.7(2) . . ? C3A C4A C5A 118.76(19) . . ? C8A C7A C5A 120.0(2) . . ? C8A C7A H7A 120 . . ? C5A C7A H7A 120 . . ? C5 C6 C10 120.5(2) . . ? C5 C6 C1 119.2(2) . . ? C10 C6 C1 120.3(2) . . ? C7 C5 C6 119.2(2) . . ? C7 C5 C4 120.5(2) . . ? C6 C5 C4 120.3(2) . . ? O4 C4 C3 122.6(2) . . ? O4 C4 C5 119.0(2) . . ? C3 C4 C5 118.4(2) . . ? C9 C10 C6 119.8(2) . . ? C9 C10 H10 120.1 . . ? C6 C10 H10 120.1 . . ? C2A C3A C4A 124.0(2) . . ? C2A C3A H13 118 . . ? C4A C3A H13 118 . . ? O2A C2A C3A 125.9(2) . . ? O2A C2A C1A 116.30(18) . . ? C3A C2A C1A 117.8(2) . . ? C9A C8A C7A 120.4(2) . . ? C9A C8A H8A 119.8 . . ? C7A C8A H8A 119.8 . . ? C9 C8 C7 120.7(2) . . ? C9 C8 H8 119.6 . . ? C7 C8 H8 119.6 . . ? N1 C21 N2 112.0(2) . . ? N1 C21 H21 124 . . ? N2 C21 H21 124 . . ? C22 C23 N1 109.6(2) . . ? C22 C23 H23 125.2 . . ? N1 C23 H23 125.2 . . ? N3 C25 N4 111.9(2) . . ? N3 C25 H25 124.1 . . ? N4 C25 H25 124.1 . . ? C23 C22 N2 106.1(2) . . ? C23 C22 H22 126.9 . . ? N2 C22 H22 126.9 . . ? C9A C10A C6A 120.1(2) . . ? C9A C10A H10A 120 . . ? C6A C10A H10A 120 . . ? C10 C9 C8 119.7(2) . . ? C10 C9 H9 120.1 . . ? C8 C9 H9 120.1 . . ? C8 C7 C5 120.0(2) . . ? C8 C7 H7 120 . . ? C5 C7 H7 120 . . ? C10A C9A C8A 120.1(2) . . ? C10A C9A H9A 120 . . ? C8A C9A H9A 120 . . ? C2 C3 C4 123.3(2) . . ? C2 C3 H3 118.4 . . ? C4 C3 H3 118.4 . . ? C26 C24 N3 109.2(2) . . ? C26 C24 H24 125.4 . . ? N3 C24 H24 125.4 . . ? C24 C26 N4 106.6(2) . . ? C24 C26 H26 126.7 . . ? N4 C26 H26 126.7 . . ? C3T C1T C5T 179.6(6) . 2_766 ? C3T C1T C4T 124.5(5) . 2_766 ? C5T C1T C4T 55.9(4) 2_766 2_766 ? C3T C1T C4T 57.1(4) . . ? C5T C1T C4T 123.3(5) 2_766 . ? C4T C1T C4T 67.4(5) 2_766 . ? C4T C2T C5T 55.8(4) . . ? C4T C2T C3T 56.0(4) . . ? C5T C2T C3T 111.8(5) . . ? C4T C3T C1T 65.6(5) . . ? C4T C3T C2T 58.9(4) . . ? C1T C3T C2T 124.5(5) . . ? C4T C5T C1T 63.6(5) . 2_766 ? C4T C5T C2T 59.7(5) . . ? C1T C5T C2T 123.3(5) 2_766 . ? C5T C4T C3T 129.6(8) . . ? C5T C4T C2T 64.5(6) . . ? C3T C4T C2T 65.1(5) . . ? C5T C4T C1T 60.5(5) . 2_766 ? C3T C4T C1T 169.8(7) . 2_766 ? C2T C4T C1T 124.9(6) . 2_766 ? C5T C4T C1T 172.9(8) . . ? C3T C4T C1T 57.3(4) . . ? C2T C4T C1T 122.5(6) . . ? C1T C4T C1T 112.6(5) 2_766 . ? C5T C4T C4T 117.3(8) . 2_766 ? C3T C4T C4T 113.0(8) . 2_766 ? C2T C4T C4T 177.7(8) . 2_766 ? C1T C4T C4T 56.9(4) 2_766 2_766 ? C1T C4T C4T 55.7(5) . 2_766 ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N2 H2 O2 0.88 1.9 2.768(2) 167 1_455 N4 H4 O4A 0.88 2 2.862(3) 168.1 2_667 data_lau25b _database_code_depnum_ccdc_archive 'CCDC 912674' #TrackingRef 'CCDC912674.cif' _audit_creation_date 2012-10-11T15:34:42-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' _audit_conform_dict_name cif_core.dic _audit_conform_dict_version 2.4 _audit_conform_dict_location ftp://ftp.iucr.org/pub/cif_core.dic #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ? _chemical_formula_sum 'C37 H26 Co N2 O6' _chemical_formula_weight 653.53 #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_space_group_name_hall '-P 1' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1' loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.5420(4) _cell_length_b 12.2546(8) _cell_length_c 15.9401(11) _cell_angle_alpha 96.822(5) _cell_angle_beta 90.829(5) _cell_angle_gamma 90.052(5) _cell_volume 1462.66(16) _cell_formula_units_Z 2 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 2451 _cell_measurement_theta_min 2.7899 _cell_measurement_theta_max 62.4358 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description needles _exptl_crystal_colour 'dark red' _exptl_crystal_size_max 0.1940 _exptl_crystal_size_mid 0.1655 _exptl_crystal_size_min 0.0230 _exptl_crystal_density_diffrn 1.484 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 674 _exptl_special_details 'This is the best measurement of all trials we have performed. It turned out that the symmetry was smaller than the one which we had measured and the data completeness is high than 0.9 only above 1A of resolution. However the Ratio reflections to parameters is 9.8, value quite close to 10 the required value of IUCr.' #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 5.051 _exptl_absorpt_correction_T_min 0.494 _exptl_absorpt_correction_T_max 0.892 _exptl_absorpt_correction_type analytical _exptl_absorpt_process_details ; CrysAlisPro, Agilent Technologies, Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET) (compiled Jan 23 2012,18:06:46) Analytical numeric absorption correction using a multifaceted crystal model based on expressions derived by R.C. Clark & J.S. Reid. (Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897) ; #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_ambient_temperature 150.00(10) _diffrn_radiation_wavelength 1.5418 _diffrn_radiation_type 'Cu K\a' _diffrn_radiation_source 'Enhance Ultra (Cu) X-ray Source' _diffrn_radiation_monochromator mirror _diffrn_measurement_device_type 'Xcalibur, Atlas, Gemini ultra' _diffrn_detector_area_resol_mean 10.4186 _diffrn_reflns_number 8301 _diffrn_reflns_av_R_equivalents 0.0359 _diffrn_reflns_av_sigmaI/netI 0.0643 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 2.79 _diffrn_reflns_theta_max 62.53 _reflns_number_total 4092 _reflns_number_gt 3060 _reflns_threshold_expression >2sigma(I) _diffrn_measurement_method '\w scans' _diffrn_measured_fraction_theta_max 0.873 _diffrn_reflns_theta_full 80 _diffrn_measured_fraction_theta_full 0.991 #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_publication_material 'PublCIF (Westrip, 2010)' _computing_molecular_graphics 'ORTEP-3: Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_data_collection ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.49a (release 05-10-2009 CrysAlis171 .NET) (compiled Oct 5 2009,17:28:39) ; _computing_cell_refinement ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.49a (release 05-10-2009 CrysAlis171 .NET) (compiled Oct 5 2009,17:28:39) ; _computing_data_reduction ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.49a (release 05-10-2009 CrysAlis171 .NET) (compiled Oct 5 2009,17:28:39) ; #----------------------------------------------------------------------------# # STRUCTURE SOLUTION #----------------------------------------------------------------------------# _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0657P)^2^+0.9772P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_number_reflns 4092 _refine_ls_number_parameters 416 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0868 _refine_ls_R_factor_gt 0.0601 _refine_ls_wR_factor_ref 0.1554 _refine_ls_wR_factor_gt 0.1374 _refine_ls_goodness_of_fit_ref 1.052 _refine_ls_restrained_S_all 1.052 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_diff_density_max 0.503 _refine_diff_density_min -0.296 _refine_diff_density_rms 0.066 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0311 0.018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Co Co -2.3653 3.6143 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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 Co Co 0.76958(10) 0.09124(6) 0.20590(5) 0.0383(3) Uani 1 1 d . . . O1A O 0.7466(4) 0.0028(3) 0.31312(19) 0.0408(8) Uani 1 1 d . . . O2 O 0.5103(4) 0.1319(3) 0.21249(19) 0.0392(8) Uani 1 1 d . . . O1 O 0.7761(4) 0.2438(3) 0.28823(19) 0.0407(8) Uani 1 1 d . . . O2A O 1.0228(4) 0.0400(3) 0.22117(19) 0.0406(8) Uani 1 1 d . . . N2 N 0.7070(5) -0.0313(3) 0.1071(2) 0.0389(10) Uani 1 1 d . . . N1 N 0.8432(5) 0.1656(3) 0.0988(2) 0.0365(9) Uani 1 1 d . . . C10 C 0.7420(7) 0.4527(4) 0.3874(3) 0.0448(13) Uani 1 1 d . . . H10 H 0.8574 0.4216 0.3853 0.054 Uiso 1 1 calc R . . C6A C 0.9072(6) -0.0925(4) 0.4110(3) 0.0356(11) Uani 1 1 d . . . C27 C 0.7028(6) -0.0806(4) -0.0426(3) 0.0468(13) Uani 1 1 d . . . H27 H 0.7289 -0.0628 -0.0975 0.056 Uiso 1 1 calc R . . C34 C 0.4151(16) 0.5220(9) 0.1226(6) 0.113(3) Uani 1 1 d . . . H34 H 0.3194 0.4872 0.0905 0.136 Uiso 1 1 calc R . . C1 C 0.6276(7) 0.2885(4) 0.2967(3) 0.0367(12) Uani 1 1 d . . . C6 C 0.6009(6) 0.3952(4) 0.3453(3) 0.0392(12) Uani 1 1 d . . . C30 C 0.6310(7) -0.1261(4) 0.1157(3) 0.0456(13) Uani 1 1 d . . . H30 H 0.6043 -0.1421 0.1710 0.055 Uiso 1 1 calc R . . C2 C 0.4736(6) 0.2251(4) 0.2537(3) 0.0359(12) Uani 1 1 d . . . C7A C 1.0884(7) -0.1907(4) 0.5023(3) 0.0448(13) Uani 1 1 d . . . H7A H 1.1992 -0.2215 0.5159 0.054 Uiso 1 1 calc R . . C2A C 1.0504(6) -0.0170(4) 0.2838(3) 0.0361(11) Uani 1 1 d . . . C5A C 1.0715(6) -0.1366(4) 0.4305(3) 0.0384(12) Uani 1 1 d . . . C21 C 0.9157(6) 0.2644(4) 0.0996(3) 0.0450(13) Uani 1 1 d . . . H21 H 0.9310 0.3084 0.1525 0.054 Uiso 1 1 calc R . . C4A C 1.2289(7) -0.1233(4) 0.3761(3) 0.0453(13) Uani 1 1 d . . . C25 C 0.8237(6) 0.1021(4) 0.0242(3) 0.0391(12) Uani 1 1 d . . . C29 C 0.5879(6) -0.2041(4) 0.0474(3) 0.0454(13) Uani 1 1 d . . . H29 H 0.5347 -0.2722 0.0558 0.054 Uiso 1 1 calc R . . C5 C 0.4311(7) 0.4415(4) 0.3477(3) 0.0428(13) Uani 1 1 d . . . C7 C 0.4059(7) 0.5440(4) 0.3923(3) 0.0506(14) Uani 1 1 d . . . H7 H 0.2911 0.5759 0.3941 0.061 Uiso 1 1 calc R . . C26 C 0.7429(6) -0.0072(4) 0.0279(3) 0.0387(12) Uani 1 1 d . . . C10A C 0.7618(6) -0.1025(4) 0.4625(3) 0.0397(12) Uani 1 1 d . . . H10A H 0.6503 -0.0727 0.4488 0.048 Uiso 1 1 calc R . . C3A C 1.2080(6) -0.0633(4) 0.3041(3) 0.0416(13) Uani 1 1 d . . . H3A H 1.3075 -0.0556 0.2694 0.050 Uiso 1 1 calc R . . C9 C 0.7147(8) 0.5541(4) 0.4317(3) 0.0511(14) Uani 1 1 d . . . H9 H 0.8110 0.5927 0.4607 0.061 Uiso 1 1 calc R . . C1A C 0.8895(6) -0.0336(4) 0.3359(3) 0.0371(12) Uani 1 1 d . . . C35 C 0.3871(13) 0.6131(11) 0.1868(8) 0.131(4) Uani 1 1 d . . . H35 H 0.2710 0.6401 0.1986 0.158 Uiso 1 1 calc R . . C24 C 0.8768(6) 0.1396(4) -0.0517(3) 0.0464(13) Uani 1 1 d . . . H24 H 0.8633 0.0942 -0.1040 0.056 Uiso 1 1 calc R . . C9A C 0.7810(7) -0.1561(4) 0.5340(3) 0.0436(13) Uani 1 1 d . . . H9A H 0.6825 -0.1631 0.5694 0.052 Uiso 1 1 calc R . . C8A C 0.9446(7) -0.1997(4) 0.5537(3) 0.0469(14) Uani 1 1 d . . . H8A H 0.9575 -0.2360 0.6029 0.056 Uiso 1 1 calc R . . C23 C 0.9484(7) 0.2430(5) -0.0486(4) 0.0551(15) Uani 1 1 d . . . H23 H 0.9829 0.2704 -0.0993 0.066 Uiso 1 1 calc R . . C3 C 0.3081(6) 0.2729(4) 0.2605(3) 0.0418(12) Uani 1 1 d . . . H3 H 0.2088 0.2320 0.2365 0.050 Uiso 1 1 calc R . . C4 C 0.2798(7) 0.3809(4) 0.3018(3) 0.0468(13) Uani 1 1 d . . . C28 C 0.6250(7) -0.1792(4) -0.0325(3) 0.0482(14) Uani 1 1 d . . . H28 H 0.5968 -0.2303 -0.0805 0.058 Uiso 1 1 calc R . . C22 C 0.9703(7) 0.3068(5) 0.0274(3) 0.0523(14) Uani 1 1 d . . . H22 H 1.0214 0.3781 0.0306 0.063 Uiso 1 1 calc R . . C8 C 0.5462(8) 0.6006(4) 0.4343(3) 0.0545(15) Uani 1 1 d . . . H8 H 0.5275 0.6710 0.4648 0.065 Uiso 1 1 calc R . . C36 C 0.5370(13) 0.6622(6) 0.2323(5) 0.089(3) Uani 1 1 d . . . H36 H 0.5220 0.7226 0.2747 0.107 Uiso 1 1 calc R . . C32 C 0.7262(13) 0.5343(6) 0.1527(5) 0.090(2) Uani 1 1 d . . . H32 H 0.8419 0.5070 0.1402 0.108 Uiso 1 1 calc R . . C31 C 0.7047(11) 0.6207(5) 0.2140(4) 0.076(2) Uani 1 1 d . . . C33 C 0.5872(15) 0.4879(7) 0.1102(6) 0.106(3) Uani 1 1 d . . . H33 H 0.6082 0.4273 0.0687 0.128 Uiso 1 1 calc R . . C37 C 0.8637(11) 0.6680(6) 0.2600(5) 0.107(3) Uani 1 1 d . . . H37A H 0.9605 0.6145 0.2540 0.160 Uiso 1 1 calc R . . H37B H 0.8364 0.6861 0.3199 0.160 Uiso 1 1 calc R . . H37C H 0.8996 0.7349 0.2365 0.160 Uiso 1 1 calc R . . O4A O 1.3719(5) -0.1656(3) 0.3938(2) 0.0567(10) Uani 1 1 d . . . O4 O 0.1316(5) 0.4258(3) 0.3008(3) 0.0626(11) 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 Co 0.0343(5) 0.0461(5) 0.0346(4) 0.0058(4) -0.0009(4) 0.0005(4) O1A 0.0306(19) 0.056(2) 0.0374(18) 0.0135(16) -0.0045(16) -0.0007(16) O2 0.0303(19) 0.049(2) 0.0372(18) 0.0025(16) -0.0034(15) 0.0012(16) O1 0.036(2) 0.047(2) 0.0392(19) 0.0020(16) -0.0014(16) 0.0029(16) O2A 0.0322(19) 0.052(2) 0.0387(18) 0.0116(17) -0.0004(15) 0.0018(16) N2 0.036(2) 0.045(2) 0.035(2) 0.0053(19) -0.0003(19) 0.003(2) N1 0.032(2) 0.043(2) 0.036(2) 0.0078(19) -0.0009(19) 0.0066(19) C10 0.044(3) 0.050(3) 0.041(3) 0.009(3) 0.000(3) 0.000(3) C6A 0.033(3) 0.038(3) 0.035(3) 0.005(2) 0.001(2) -0.004(2) C27 0.040(3) 0.064(4) 0.038(3) 0.014(3) -0.007(2) 0.000(3) C34 0.133(10) 0.126(9) 0.092(7) 0.060(6) -0.015(7) -0.021(7) C1 0.041(3) 0.045(3) 0.026(2) 0.011(2) 0.005(2) 0.004(2) C6 0.037(3) 0.046(3) 0.035(3) 0.009(2) 0.003(2) 0.000(2) C30 0.043(3) 0.056(3) 0.040(3) 0.012(3) 0.004(3) 0.004(3) C2 0.033(3) 0.048(3) 0.028(2) 0.011(2) 0.000(2) 0.000(2) C7A 0.047(3) 0.041(3) 0.047(3) 0.009(2) -0.015(3) 0.003(2) C2A 0.030(3) 0.042(3) 0.037(3) 0.004(2) -0.004(2) 0.000(2) C5A 0.039(3) 0.037(3) 0.039(3) 0.002(2) -0.005(2) 0.001(2) C21 0.039(3) 0.048(3) 0.049(3) 0.011(3) 0.001(3) -0.001(3) C4A 0.033(3) 0.050(3) 0.052(3) 0.001(3) -0.004(3) -0.002(3) C25 0.028(3) 0.050(3) 0.040(3) 0.008(2) 0.002(2) 0.006(2) C29 0.037(3) 0.042(3) 0.055(3) -0.002(3) 0.002(3) 0.004(2) C5 0.045(3) 0.045(3) 0.040(3) 0.011(2) 0.010(3) 0.003(3) C7 0.048(3) 0.049(3) 0.056(3) 0.010(3) 0.013(3) 0.005(3) C26 0.026(3) 0.056(3) 0.035(3) 0.007(2) -0.005(2) 0.006(2) C10A 0.036(3) 0.047(3) 0.036(3) 0.005(2) -0.007(2) -0.001(2) C3A 0.033(3) 0.055(3) 0.037(3) 0.007(2) 0.005(2) -0.001(2) C9 0.059(4) 0.045(3) 0.050(3) 0.006(3) -0.007(3) -0.005(3) C1A 0.034(3) 0.040(3) 0.036(3) 0.001(2) -0.008(2) -0.004(2) C35 0.076(6) 0.200(12) 0.145(9) 0.128(9) 0.024(7) 0.015(8) C24 0.038(3) 0.061(4) 0.041(3) 0.011(3) 0.006(3) 0.011(3) C9A 0.046(3) 0.045(3) 0.040(3) 0.005(2) 0.000(3) -0.007(3) C8A 0.057(4) 0.046(3) 0.038(3) 0.009(2) -0.010(3) -0.010(3) C23 0.046(4) 0.066(4) 0.059(4) 0.029(3) 0.010(3) 0.002(3) C3 0.034(3) 0.047(3) 0.044(3) 0.007(2) 0.003(2) -0.004(2) C4 0.035(3) 0.054(3) 0.054(3) 0.017(3) 0.005(3) 0.005(3) C28 0.045(3) 0.056(3) 0.042(3) 0.002(3) -0.005(3) 0.000(3) C22 0.047(4) 0.054(3) 0.059(4) 0.017(3) 0.003(3) 0.001(3) C8 0.072(4) 0.044(3) 0.048(3) 0.006(3) 0.004(3) 0.005(3) C36 0.113(7) 0.077(5) 0.087(5) 0.044(4) 0.056(5) 0.040(5) C32 0.144(8) 0.056(4) 0.073(5) 0.012(4) 0.025(5) 0.013(5) C31 0.114(7) 0.056(4) 0.060(4) 0.019(3) 0.011(4) 0.000(4) C33 0.127(8) 0.087(6) 0.107(7) 0.023(5) -0.025(7) -0.016(6) C37 0.124(7) 0.109(6) 0.091(6) 0.028(5) 0.002(5) -0.042(6) O4A 0.035(2) 0.069(3) 0.067(3) 0.017(2) -0.0051(19) 0.0070(19) O4 0.037(2) 0.062(3) 0.089(3) 0.008(2) 0.007(2) 0.0076(19) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _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 Co O2 2.019(3) . ? Co O2A 2.032(3) . ? Co N2 2.092(4) . ? Co N1 2.108(4) . ? Co O1A 2.139(3) . ? Co O1 2.153(3) . ? O1A C1A 1.234(5) . ? O2 C2 1.281(5) . ? O1 C1 1.249(5) . ? O2A C2A 1.299(5) . ? N2 C30 1.317(6) . ? N2 C26 1.361(6) . ? N1 C21 1.328(6) . ? N1 C25 1.348(6) . ? C10 C9 1.372(7) . ? C10 C6 1.394(6) . ? C10 H10 0.9500 . ? C6A C10A 1.393(6) . ? C6A C5A 1.397(6) . ? C6A C1A 1.475(6) . ? C27 C28 1.371(7) . ? C27 C26 1.383(7) . ? C27 H27 0.9500 . ? C34 C33 1.373(11) . ? C34 C35 1.440(13) . ? C34 H34 0.9500 . ? C1 C6 1.455(7) . ? C1 C2 1.506(6) . ? C6 C5 1.400(6) . ? C30 C29 1.395(7) . ? C30 H30 0.9500 . ? C2 C3 1.380(6) . ? C7A C8A 1.381(7) . ? C7A C5A 1.394(6) . ? C7A H7A 0.9500 . ? C2A C3A 1.369(6) . ? C2A C1A 1.507(6) . ? C5A C4A 1.500(7) . ? C21 C22 1.385(7) . ? C21 H21 0.9500 . ? C4A O4A 1.240(5) . ? C4A C3A 1.441(6) . ? C25 C24 1.407(6) . ? C25 C26 1.479(6) . ? C29 C28 1.378(7) . ? C29 H29 0.9500 . ? C5 C7 1.382(7) . ? C5 C4 1.495(7) . ? C7 C8 1.385(7) . ? C7 H7 0.9500 . ? C10A C9A 1.387(6) . ? C10A H10A 0.9500 . ? C3A H3A 0.9500 . ? C9 C8 1.392(7) . ? C9 H9 0.9500 . ? C35 C36 1.427(11) . ? C35 H35 0.9500 . ? C24 C23 1.372(7) . ? C24 H24 0.9500 . ? C9A C8A 1.392(7) . ? C9A H9A 0.9500 . ? C8A H8A 0.9500 . ? C23 C22 1.370(7) . ? C23 H23 0.9500 . ? C3 C4 1.425(7) . ? C3 H3 0.9500 . ? C4 O4 1.247(6) . ? C28 H28 0.9500 . ? C22 H22 0.9500 . ? C8 H8 0.9500 . ? C36 C31 1.386(10) . ? C36 H36 0.9500 . ? C32 C33 1.330(10) . ? C32 C31 1.364(9) . ? C32 H32 0.9500 . ? C31 C37 1.478(9) . ? C33 H33 0.9500 . ? C37 H37A 0.9800 . ? C37 H37B 0.9800 . ? C37 H37C 0.9800 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O2 Co O2A 168.99(12) . . ? O2 Co N2 88.99(14) . . ? O2A Co N2 94.97(14) . . ? O2 Co N1 100.40(13) . . ? O2A Co N1 90.48(13) . . ? N2 Co N1 77.89(15) . . ? O2 Co O1A 90.83(12) . . ? O2A Co O1A 78.33(12) . . ? N2 Co O1A 101.24(14) . . ? N1 Co O1A 168.70(14) . . ? O2 Co O1 77.88(13) . . ? O2A Co O1 99.96(13) . . ? N2 Co O1 162.88(13) . . ? N1 Co O1 93.57(14) . . ? O1A Co O1 90.01(12) . . ? C1A O1A Co 113.0(3) . . ? C2 O2 Co 116.3(3) . . ? C1 O1 Co 113.0(3) . . ? C2A O2A Co 115.7(3) . . ? C30 N2 C26 118.7(4) . . ? C30 N2 Co 125.3(3) . . ? C26 N2 Co 115.9(3) . . ? C21 N1 C25 118.5(4) . . ? C21 N1 Co 125.9(3) . . ? C25 N1 Co 115.4(3) . . ? C9 C10 C6 120.2(5) . . ? C9 C10 H10 119.9 . . ? C6 C10 H10 119.9 . . ? C10A C6A C5A 120.6(4) . . ? C10A C6A C1A 120.1(4) . . ? C5A C6A C1A 119.3(4) . . ? C28 C27 C26 119.4(5) . . ? C28 C27 H27 120.3 . . ? C26 C27 H27 120.3 . . ? C33 C34 C35 116.7(10) . . ? C33 C34 H34 121.7 . . ? C35 C34 H34 121.7 . . ? O1 C1 C6 123.0(4) . . ? O1 C1 C2 116.2(4) . . ? C6 C1 C2 120.8(5) . . ? C10 C6 C5 119.9(5) . . ? C10 C6 C1 121.1(5) . . ? C5 C6 C1 119.0(4) . . ? N2 C30 C29 123.1(5) . . ? N2 C30 H30 118.5 . . ? C29 C30 H30 118.5 . . ? O2 C2 C3 126.0(4) . . ? O2 C2 C1 116.2(4) . . ? C3 C2 C1 117.8(5) . . ? C8A C7A C5A 120.2(5) . . ? C8A C7A H7A 119.9 . . ? C5A C7A H7A 119.9 . . ? O2A C2A C3A 126.0(4) . . ? O2A C2A C1A 115.0(4) . . ? C3A C2A C1A 119.1(4) . . ? C7A C5A C6A 119.1(5) . . ? C7A C5A C4A 120.4(5) . . ? C6A C5A C4A 120.5(4) . . ? N1 C21 C22 123.4(5) . . ? N1 C21 H21 118.3 . . ? C22 C21 H21 118.3 . . ? O4A C4A C3A 122.2(5) . . ? O4A C4A C5A 119.0(5) . . ? C3A C4A C5A 118.8(4) . . ? N1 C25 C24 121.2(5) . . ? N1 C25 C26 115.7(4) . . ? C24 C25 C26 123.1(5) . . ? C28 C29 C30 117.9(5) . . ? C28 C29 H29 121.1 . . ? C30 C29 H29 121.1 . . ? C7 C5 C6 119.2(5) . . ? C7 C5 C4 120.6(5) . . ? C6 C5 C4 120.2(5) . . ? C5 C7 C8 120.7(5) . . ? C5 C7 H7 119.6 . . ? C8 C7 H7 119.6 . . ? N2 C26 C27 121.1(4) . . ? N2 C26 C25 115.0(4) . . ? C27 C26 C25 123.9(4) . . ? C9A C10A C6A 119.5(5) . . ? C9A C10A H10A 120.2 . . ? C6A C10A H10A 120.2 . . ? C2A C3A C4A 122.6(5) . . ? C2A C3A H3A 118.7 . . ? C4A C3A H3A 118.7 . . ? C10 C9 C8 120.2(5) . . ? C10 C9 H9 119.9 . . ? C8 C9 H9 119.9 . . ? O1A C1A C6A 122.5(4) . . ? O1A C1A C2A 117.9(4) . . ? C6A C1A C2A 119.6(4) . . ? C36 C35 C34 118.8(9) . . ? C36 C35 H35 120.6 . . ? C34 C35 H35 120.6 . . ? C23 C24 C25 118.7(5) . . ? C23 C24 H24 120.7 . . ? C25 C24 H24 120.7 . . ? C10A C9A C8A 120.0(5) . . ? C10A C9A H9A 120.0 . . ? C8A C9A H9A 120.0 . . ? C7A C8A C9A 120.5(5) . . ? C7A C8A H8A 119.8 . . ? C9A C8A H8A 119.8 . . ? C22 C23 C24 120.0(5) . . ? C22 C23 H23 120.0 . . ? C24 C23 H23 120.0 . . ? C2 C3 C4 122.8(5) . . ? C2 C3 H3 118.6 . . ? C4 C3 H3 118.6 . . ? O4 C4 C3 121.5(5) . . ? O4 C4 C5 119.4(5) . . ? C3 C4 C5 119.2(5) . . ? C27 C28 C29 119.7(5) . . ? C27 C28 H28 120.1 . . ? C29 C28 H28 120.1 . . ? C23 C22 C21 118.1(5) . . ? C23 C22 H22 120.9 . . ? C21 C22 H22 120.9 . . ? C7 C8 C9 119.8(5) . . ? C7 C8 H8 120.1 . . ? C9 C8 H8 120.1 . . ? C31 C36 C35 119.3(9) . . ? C31 C36 H36 120.3 . . ? C35 C36 H36 120.3 . . ? C33 C32 C31 120.8(9) . . ? C33 C32 H32 119.6 . . ? C31 C32 H32 119.6 . . ? C32 C31 C36 120.3(8) . . ? C32 C31 C37 118.5(9) . . ? C36 C31 C37 121.3(8) . . ? C32 C33 C34 124.2(10) . . ? C32 C33 H33 117.9 . . ? C34 C33 H33 117.9 . . ? C31 C37 H37A 109.5 . . ? C31 C37 H37B 109.5 . . ? H37A C37 H37B 109.5 . . ? C31 C37 H37C 109.5 . . ? H37A C37 H37C 109.5 . . ? H37B C37 H37C 109.5 . . ? data_lau_25_d-cu_def _database_code_depnum_ccdc_archive 'CCDC 912675' #TrackingRef 'CCDC912675.cif' _audit_creation_date 2012-10-11T16:20:01-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' _audit_conform_dict_name cif_core.dic _audit_conform_dict_version 2.4 _audit_conform_dict_location ftp://ftp.iucr.org/pub/cif_core.dic #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; ; _chemical_formula_sum 'C30 H18 Co N2 O6' _chemical_formula_weight 561.39 #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_space_group_name_hall 'A 2 -2ac' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M 'A b a 2' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z' '-x+1/2, y+1/2, z' 'x+1/2, -y+1/2, z' 'x, y+1/2, z+1/2' '-x, -y+1/2, z+1/2' '-x+1/2, y+1, z+1/2' 'x+1/2, -y+1, z+1/2' _cell_length_a 19.559(5) _cell_length_b 14.772(5) _cell_length_c 8.378(5) _cell_angle_alpha 90.000(5) _cell_angle_beta 90.000(5) _cell_angle_gamma 90.000(5) _cell_volume 2420.6(18) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 3138 _cell_measurement_theta_min 2.2578 _cell_measurement_theta_max 62.3720 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description needles _exptl_crystal_colour 'dark red' _exptl_crystal_size_max 0.2637 _exptl_crystal_size_mid 0.1369 _exptl_crystal_size_min 0.0771 _exptl_crystal_density_diffrn 1.54 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1148 _exptl_special_details ? #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 6.004 _exptl_absorpt_correction_T_min 0.317 _exptl_absorpt_correction_T_max 0.650 _exptl_absorpt_correction_type analytical _exptl_absorpt_process_details ; CrysAlisPro, Agilent Technologies, Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET) (compiled Jan 23 2012,18:06:46) Analytical numeric absorption correction using a multifaceted crystal model based on expressions derived by R.C. Clark & J.S. Reid. (Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897) ; #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_radiation_wavelength 1.5418 _diffrn_radiation_type 'Cu K\a' _diffrn_radiation_source 'Enhance Ultra (Cu) X-ray Source' _diffrn_radiation_monochromator mirror _diffrn_measurement_device_type 'Xcalibur, Atlas, Gemini ultra' _diffrn_detector_area_resol_mean 10.4186 _diffrn_ambient_temperature 293(2) _diffrn_reflns_number 7440 _diffrn_reflns_av_R_equivalents 0.0298 _diffrn_reflns_av_sigmaI/netI 0.0252 _diffrn_reflns_limit_h_min -22 _diffrn_reflns_limit_h_max 22 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -7 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_theta_min 4.52 _diffrn_reflns_theta_max 62.43 _reflns_number_total 1652 _reflns_threshold_expression >2sigma(I) _reflns_number_gt 1467 _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 62.43 _diffrn_measured_fraction_theta_full 0.996 _diffrn_measurement_method '\w scans' #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_publication_material 'PublCIF (Westrip, 2010)' _computing_molecular_graphics 'ORTEP-3: Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_data_collection ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.49a (release 05-10-2009 CrysAlis171 .NET) (compiled Oct 5 2009,17:28:39) ; _computing_cell_refinement ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.49a (release 05-10-2009 CrysAlis171 .NET) (compiled Oct 5 2009,17:28:39) ; _computing_data_reduction ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.49a (release 05-10-2009 CrysAlis171 .NET) (compiled Oct 5 2009,17:28:39) ; #----------------------------------------------------------------------------# # STRUCTURE SOLUTION #----------------------------------------------------------------------------# _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0349P)^2^+0.9294P] where P=(Fo^2^+2Fc^2^)/3' _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 -0.030(5) _refine_ls_number_reflns 1652 _refine_ls_number_parameters 177 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0373 _refine_ls_R_factor_gt 0.0296 _refine_ls_wR_factor_ref 0.0734 _refine_ls_wR_factor_gt 0.0685 _refine_ls_goodness_of_fit_ref 1.065 _refine_ls_restrained_S_all 1.064 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0311 0.018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Co Co -2.3653 3.6143 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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 Co Co 0.0000 0.0000 0.22927(12) 0.04264(18) Uani 1 2 d S . . O1 O 0.09025(10) 0.08387(13) 0.2168(3) 0.0493(5) Uani 1 1 d . . . O2 O 0.06141(11) -0.07323(16) 0.0844(3) 0.0582(6) Uani 1 1 d . . . C6 C 0.20731(15) 0.0836(2) 0.1458(4) 0.0468(8) Uani 1 1 d . . . N1 N -0.02821(13) 0.0799(2) 0.4284(4) 0.0530(8) Uani 1 1 d . . . O4 O 0.29137(14) -0.0916(2) -0.0804(4) 0.0891(10) Uani 1 1 d . . . C11 C -0.01409(16) 0.0462(3) 0.5741(5) 0.0616(10) Uani 1 1 d . . . C1 C 0.13834(15) 0.0445(2) 0.1502(4) 0.0443(7) Uani 1 1 d . . . C3 C 0.17635(18) -0.0869(2) -0.0060(5) 0.0609(10) Uani 1 1 d . . . H3 H 0.1671 -0.1409 -0.0588 0.073 Uiso 1 1 calc R . . C10 C 0.22123(15) 0.1664(2) 0.2183(6) 0.0552(9) Uani 1 1 d . . . H10 H 0.1860 0.1985 0.2669 0.066 Uiso 1 1 calc R . . C5 C 0.25975(16) 0.0356(2) 0.0737(5) 0.0538(8) Uani 1 1 d . . . C7 C 0.32534(16) 0.0707(3) 0.0753(5) 0.0664(11) Uani 1 1 d . . . H7 H 0.3609 0.0385 0.0282 0.080 Uiso 1 1 calc R . . C9 C 0.28700(16) 0.2014(2) 0.2188(7) 0.0687(10) Uani 1 1 d . . . H9 H 0.2963 0.2567 0.2673 0.082 Uiso 1 1 calc R . . C4 C 0.24473(19) -0.0519(2) -0.0105(6) 0.0590(8) Uani 1 1 d . . . C2 C 0.12415(15) -0.0444(2) 0.0725(4) 0.0491(8) Uani 1 1 d . . . C15 C -0.05338(19) 0.1634(3) 0.4149(6) 0.0772(13) Uani 1 1 d . . . H15 H -0.0635 0.1864 0.3143 0.093 Uiso 1 1 calc R . . C8 C 0.33825(18) 0.1526(3) 0.1458(5) 0.0735(12) Uani 1 1 d . . . H8 H 0.3825 0.1757 0.1444 0.088 Uiso 1 1 calc R . . C12 C -0.0256(2) 0.0978(4) 0.7100(6) 0.1005(19) Uani 1 1 d . . . H12 H -0.0161 0.0742 0.8105 0.121 Uiso 1 1 calc R . . C14 C -0.0647(2) 0.2162(4) 0.5477(10) 0.117(3) Uani 1 1 d . . . H14 H -0.0818 0.2745 0.5357 0.141 Uiso 1 1 calc R . . C13 C -0.0512(3) 0.1841(6) 0.6951(8) 0.133(3) Uani 1 1 d . . . H13 H -0.0590 0.2196 0.7849 0.159 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Co 0.0436(3) 0.0456(3) 0.0388(3) 0.000 0.000 -0.0017(3) O1 0.0449(10) 0.0447(11) 0.0581(16) -0.0069(13) 0.0082(13) 0.0025(9) O2 0.0591(14) 0.0581(15) 0.0573(16) -0.0151(13) 0.0075(13) -0.0089(12) C6 0.0414(16) 0.0491(19) 0.050(2) 0.0012(18) 0.0022(16) 0.0043(14) N1 0.0484(14) 0.0549(19) 0.056(2) -0.0096(16) 0.0114(15) -0.0064(14) O4 0.0695(16) 0.088(2) 0.109(3) -0.034(2) 0.0183(17) 0.0180(15) C11 0.0442(18) 0.095(3) 0.046(2) -0.017(2) 0.0083(17) -0.0239(18) C1 0.0501(17) 0.0423(18) 0.0404(18) 0.0060(16) 0.0014(15) 0.0042(15) C3 0.067(2) 0.056(2) 0.059(2) -0.014(2) 0.008(2) 0.0047(18) C10 0.0487(15) 0.0476(18) 0.069(3) 0.002(2) 0.007(2) 0.0022(13) C5 0.0495(17) 0.0570(19) 0.055(2) -0.0008(19) 0.0011(18) 0.0107(16) C7 0.0418(17) 0.082(3) 0.075(3) -0.004(2) 0.0090(19) 0.0096(18) C9 0.0592(19) 0.063(2) 0.084(3) -0.007(3) -0.002(3) -0.0080(16) C4 0.0546(18) 0.064(2) 0.059(2) -0.008(3) 0.0075(17) 0.016(2) C2 0.0575(18) 0.0456(18) 0.044(2) -0.0035(18) 0.0044(18) 0.0015(16) C15 0.069(2) 0.061(3) 0.102(4) -0.022(2) 0.022(2) -0.001(2) C8 0.0482(19) 0.083(3) 0.089(3) -0.005(3) 0.001(2) -0.008(2) C12 0.070(3) 0.177(5) 0.055(3) -0.044(4) 0.019(2) -0.043(3) C14 0.080(3) 0.098(4) 0.174(7) -0.083(5) 0.042(4) -0.012(3) C13 0.077(3) 0.196(7) 0.125(6) -0.116(6) 0.038(4) -0.039(4) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _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 Co O2 2.021(2) 2 ? Co O2 2.021(2) . ? Co N1 2.117(3) 2 ? Co N1 2.117(3) . ? Co O1 2.1592(19) . ? Co O1 2.1592(19) 2 ? O1 C1 1.238(4) . ? O2 C2 1.303(4) . ? C6 C5 1.385(4) . ? C6 C10 1.392(5) . ? C6 C1 1.468(4) . ? N1 C15 1.333(5) . ? N1 C11 1.347(5) . ? O4 C4 1.233(4) . ? C11 C12 1.389(6) . ? C11 C11 1.473(8) 2 ? C1 C2 1.493(5) . ? C3 C2 1.366(4) . ? C3 C4 1.434(5) . ? C3 H3 0.9300 . ? C10 C9 1.387(4) . ? C10 H10 0.9300 . ? C5 C7 1.384(5) . ? C5 C4 1.502(5) . ? C7 C8 1.370(5) . ? C7 H7 0.9300 . ? C9 C8 1.378(5) . ? C9 H9 0.9300 . ? C15 C14 1.376(7) . ? C15 H15 0.9300 . ? C8 H8 0.9300 . ? C12 C13 1.374(9) . ? C12 H12 0.9300 . ? C14 C13 1.349(10) . ? C14 H14 0.9300 . ? C13 H13 0.9300 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O2 Co O2 106.21(16) 2 . ? O2 Co N1 157.89(10) 2 2 ? O2 Co N1 91.13(12) . 2 ? O2 Co N1 91.13(12) 2 . ? O2 Co N1 157.89(10) . . ? N1 Co N1 75.99(18) 2 . ? O2 Co O1 98.61(9) 2 . ? O2 Co O1 78.01(9) . . ? N1 Co O1 98.34(10) 2 . ? N1 Co O1 86.06(10) . . ? O2 Co O1 78.01(9) 2 2 ? O2 Co O1 98.61(9) . 2 ? N1 Co O1 86.06(10) 2 2 ? N1 Co O1 98.34(10) . 2 ? O1 Co O1 174.45(16) . 2 ? C1 O1 Co 111.9(2) . . ? C2 O2 Co 115.5(2) . . ? C5 C6 C10 119.7(3) . . ? C5 C6 C1 119.4(3) . . ? C10 C6 C1 120.9(3) . . ? C15 N1 C11 119.6(3) . . ? C15 N1 Co 123.1(3) . . ? C11 N1 Co 117.1(3) . . ? N1 C11 C12 120.5(4) . . ? N1 C11 C11 114.8(2) . 2 ? C12 C11 C11 124.7(3) . 2 ? O1 C1 C6 121.7(3) . . ? O1 C1 C2 117.9(3) . . ? C6 C1 C2 120.4(3) . . ? C2 C3 C4 123.0(4) . . ? C2 C3 H3 118.5 . . ? C4 C3 H3 118.5 . . ? C9 C10 C6 120.7(3) . . ? C9 C10 H10 119.6 . . ? C6 C10 H10 119.6 . . ? C7 C5 C6 119.4(3) . . ? C7 C5 C4 120.6(3) . . ? C6 C5 C4 120.0(3) . . ? C8 C7 C5 120.4(3) . . ? C8 C7 H7 119.8 . . ? C5 C7 H7 119.8 . . ? C8 C9 C10 118.6(4) . . ? C8 C9 H9 120.7 . . ? C10 C9 H9 120.7 . . ? O4 C4 C3 122.1(4) . . ? O4 C4 C5 119.2(4) . . ? C3 C4 C5 118.7(3) . . ? O2 C2 C3 126.2(3) . . ? O2 C2 C1 115.4(3) . . ? C3 C2 C1 118.3(3) . . ? N1 C15 C14 121.0(6) . . ? N1 C15 H15 119.5 . . ? C14 C15 H15 119.5 . . ? C7 C8 C9 121.3(3) . . ? C7 C8 H8 119.4 . . ? C9 C8 H8 119.4 . . ? C13 C12 C11 119.5(6) . . ? C13 C12 H12 120.2 . . ? C11 C12 H12 120.2 . . ? C13 C14 C15 120.6(7) . . ? C13 C14 H14 119.7 . . ? C15 C14 H14 119.7 . . ? C14 C13 C12 118.8(6) . . ? C14 C13 H13 120.6 . . ? C12 C13 H13 120.6 . . ? data_colaupy _database_code_depnum_ccdc_archive 'CCDC 912676' #TrackingRef 'CCDC912676.cif' _audit_creation_date 2011-07-20T16:36:31-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ? _chemical_name_common 'Compound colaupy' _chemical_formula_moiety 'C30 H20 Co N2 O6, C H4 O' _chemical_formula_sum 'C31 H24 Co N2 O7' _chemical_formula_weight 595.45 _chemical_compound_source 'synthesis as described' #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'C 1 2/c 1' _symmetry_space_group_name_Hall '-C 2yc' _symmetry_Int_Tables_number 15 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 14.433(3) _cell_length_b 10.594(2) _cell_length_c 17.946(4) _cell_angle_alpha 90 _cell_angle_beta 101.47(3) _cell_angle_gamma 90 _cell_volume 2689.2(10) _cell_formula_units_Z 4 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 16061 _cell_measurement_theta_min 3.13 _cell_measurement_theta_max 25.02 _cell_measurement_wavelength 0.71073 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description prism _exptl_crystal_colour black _exptl_crystal_size_max 0.24 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.09 _exptl_crystal_density_diffrn 1.471 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1228 loop_ _exptl_crystal_face_index_h _exptl_crystal_face_index_k _exptl_crystal_face_index_l _exptl_crystal_face_perp_dist 0 -1 0 0.04 0 1 0 0.05 -1 0 1 0.02 1 0 -1 0.08 1 0 1 0.13 -1 0 -1 0.11 _exptl_special_details ? #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.691 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; 'SADABS (Sheldrick, 1996)' ; _exptl_absorpt_correction_T_min 0.92 _exptl_absorpt_correction_T_max 0.94 #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_ambient_temperature 298(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator 'horizonally mounted graphite crystal' _diffrn_radiation_probe x-ray _diffrn_source 'Enraf Nonius FR590' _diffrn_detector 'CCD plate' _diffrn_detector_area_resol_mean 9 _diffrn_measurement_device '95mm CCD camera on \k-goniostat' _diffrn_measurement_device_type KappaCCD _diffrn_measurement_method 'CCD rotation images, thick slices' _diffrn_reflns_number 8543 _diffrn_reflns_av_R_equivalents 0.0691 _diffrn_reflns_av_sigmaI/netI 0.0688 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 3.13 _diffrn_reflns_theta_max 25.02 _reflns_number_total 2380 _reflns_number_gt 1654 _reflns_threshold_expression >2sigma(I) _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 25.02 _diffrn_measured_fraction_theta_full 0.998 #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection 'Collect (Nonius, 1998)' _computing_cell_refinement 'Dirax/lsq (Duisenberg, 1992)' _computing_data_reduction 'EvalCCD (Duisenberg et al., 2003)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' #----------------------------------------------------------------------------# # STRUCTURE SOLUTION #----------------------------------------------------------------------------# _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0643P)^2^+0.4837P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2380 _refine_ls_number_parameters 187 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0781 _refine_ls_R_factor_gt 0.0447 _refine_ls_wR_factor_ref 0.1216 _refine_ls_wR_factor_gt 0.1089 _refine_ls_goodness_of_fit_ref 1.004 _refine_ls_restrained_S_all 1.007 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# 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 0 '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' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Co1 Co 0.5000 0.43768(6) 0.2500 0.0360(2) Uani 1 2 d S . . O1 O 0.39496(16) 0.3006(2) 0.19364(13) 0.0429(6) Uani 1 1 d . . . O2 O 0.54405(16) 0.3964(2) 0.15228(13) 0.0413(6) Uani 1 1 d . . . O4 O 0.4804(2) 0.1404(3) -0.06459(17) 0.0823(10) Uani 1 1 d . . . N1 N 0.39648(18) 0.5731(3) 0.20900(14) 0.0385(6) Uani 1 1 d . . . C2 C 0.4963(2) 0.3157(3) 0.10737(18) 0.0371(8) Uani 1 1 d . . . C1 C 0.4099(2) 0.2658(3) 0.13218(19) 0.0355(7) Uani 1 1 d . . . C6 C 0.3469(2) 0.1785(3) 0.08318(18) 0.0370(8) Uani 1 1 d . . . C10 C 0.2622(2) 0.1410(3) 0.1018(2) 0.0467(9) Uani 1 1 d . . . H10 H 0.2441 0.1733 0.1449 0.056 Uiso 1 1 calc R . . C9 C 0.2051(3) 0.0563(4) 0.0563(2) 0.0542(10) Uani 1 1 d . . . H9 H 0.1483 0.0309 0.0684 0.065 Uiso 1 1 calc R . . C8 C 0.2321(3) 0.0096(4) -0.0066(2) 0.0593(11) Uani 1 1 d . . . H8 H 0.1936 -0.0487 -0.0368 0.071 Uiso 1 1 calc R . . C7 C 0.3147(3) 0.0464(4) -0.0265(2) 0.0574(10) Uani 1 1 d . . . H7 H 0.3319 0.0133 -0.0699 0.069 Uiso 1 1 calc R . . C5 C 0.3725(3) 0.1326(3) 0.01780(19) 0.0434(8) Uani 1 1 d . . . C4 C 0.4604(3) 0.1797(4) -0.0055(2) 0.0530(10) Uani 1 1 d . . . C3 C 0.5162(2) 0.2712(3) 0.0416(2) 0.0478(9) Uani 1 1 d . . . H3 H 0.5697 0.3023 0.0262 0.057 Uiso 1 1 calc R . . C11 C 0.3092(2) 0.5637(4) 0.22262(19) 0.0487(9) Uani 1 1 d . . . H11 H 0.2948 0.4948 0.2503 0.058 Uiso 1 1 calc R . . C12 C 0.2395(3) 0.6508(4) 0.1977(2) 0.0571(11) Uani 1 1 d . . . H12 H 0.1794 0.6404 0.2083 0.069 Uiso 1 1 calc R . . C13 C 0.2596(3) 0.7531(4) 0.1573(2) 0.0596(11) Uani 1 1 d . . . H13 H 0.2138 0.8140 0.1405 0.071 Uiso 1 1 calc R . . C14 C 0.3490(3) 0.7641(4) 0.1417(2) 0.0585(11) Uani 1 1 d . . . H14 H 0.3643 0.8315 0.1133 0.070 Uiso 1 1 calc R . . C15 C 0.4147(2) 0.6737(3) 0.1690(2) 0.0460(9) Uani 1 1 d . . . H15 H 0.4753 0.6826 0.1594 0.055 Uiso 1 1 calc R . . C20 C 0.0219(11) 0.4870(10) 0.2524(9) 0.112(4) Uiso 0.50 1 d PD A -1 H20C H 0.0084 0.5437 0.2099 0.169 Uiso 0.50 1 calc PR A -1 H20A H 0.0035 0.4029 0.2358 0.169 Uiso 0.50 1 calc PR A -1 H20B H 0.0884 0.4886 0.2737 0.169 Uiso 0.50 1 calc PR A -1 O20 O -0.0299(8) 0.5256(10) 0.3092(6) 0.162(4) Uiso 0.50 1 d PD A -1 H20 H -0.0360 0.4653 0.3364 0.243 Uiso 0.50 1 calc PR A -1 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 0.0301(4) 0.0400(4) 0.0376(4) 0.000 0.0059(3) 0.000 O1 0.0441(13) 0.0483(14) 0.0390(14) -0.0050(11) 0.0144(11) -0.0092(11) O2 0.0333(12) 0.0482(13) 0.0426(13) -0.0043(11) 0.0082(10) -0.0089(10) O4 0.090(2) 0.106(3) 0.0606(19) -0.0346(18) 0.0388(17) -0.028(2) N1 0.0328(14) 0.0453(16) 0.0368(15) 0.0001(13) 0.0054(11) 0.0006(13) C2 0.0316(17) 0.0403(18) 0.0389(19) 0.0035(15) 0.0058(15) -0.0017(15) C1 0.0338(18) 0.0352(18) 0.0365(19) 0.0022(15) 0.0048(14) -0.0007(14) C6 0.0375(18) 0.0369(18) 0.0356(18) 0.0062(14) 0.0046(15) -0.0049(15) C10 0.044(2) 0.050(2) 0.044(2) 0.0037(17) 0.0043(16) -0.0085(17) C9 0.046(2) 0.053(2) 0.060(2) 0.004(2) 0.0010(18) -0.018(2) C8 0.060(3) 0.057(2) 0.055(2) -0.003(2) -0.005(2) -0.020(2) C7 0.070(3) 0.056(2) 0.044(2) -0.0101(19) 0.0059(19) -0.013(2) C5 0.047(2) 0.043(2) 0.0376(19) -0.0004(16) 0.0036(16) -0.0035(17) C4 0.053(2) 0.064(3) 0.044(2) -0.0041(18) 0.0148(18) -0.005(2) C3 0.040(2) 0.061(2) 0.047(2) -0.0078(18) 0.0175(17) -0.0107(17) C11 0.043(2) 0.060(2) 0.044(2) 0.0038(19) 0.0109(16) -0.001(2) C12 0.038(2) 0.078(3) 0.055(2) -0.004(2) 0.0095(18) 0.013(2) C13 0.056(3) 0.062(3) 0.057(3) -0.002(2) 0.001(2) 0.021(2) C14 0.061(3) 0.052(2) 0.057(3) 0.0075(19) 0.000(2) 0.001(2) C15 0.0378(19) 0.051(2) 0.048(2) 0.0013(18) 0.0045(16) -0.0004(17) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Co1 O2 2.028(2) 2_655 ? Co1 O2 2.028(2) . ? Co1 N1 2.096(3) . ? Co1 N1 2.096(3) 2_655 ? Co1 O1 2.196(2) . ? Co1 O1 2.196(2) 2_655 ? O1 C1 1.222(4) . ? O2 C2 1.278(4) . ? O4 C4 1.226(4) . ? N1 C11 1.334(4) . ? N1 C15 1.340(4) . ? C2 C3 1.353(5) . ? C2 C1 1.502(4) . ? C1 C6 1.462(4) . ? C6 C5 1.387(5) . ? C6 C10 1.388(5) . ? C10 C9 1.373(5) . ? C10 H10 0.9300 . ? C9 C8 1.359(5) . ? C9 H9 0.9300 . ? C8 C7 1.367(6) . ? C8 H8 0.9300 . ? C7 C5 1.378(5) . ? C7 H7 0.9300 . ? C5 C4 1.497(5) . ? C4 C3 1.427(5) . ? C3 H3 0.9300 . ? C11 C12 1.373(5) . ? C11 H11 0.9300 . ? C12 C13 1.367(6) . ? C12 H12 0.9300 . ? C13 C14 1.378(6) . ? C13 H13 0.9300 . ? C14 C15 1.367(5) . ? C14 H14 0.9300 . ? C15 H15 0.9300 . ? C20 O20 1.437(9) . ? C20 H20C 0.9600 . ? C20 H20A 0.9600 . ? C20 H20B 0.9600 . ? O20 H20 0.8200 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O2 Co1 O2 155.11(13) 2_655 . ? O2 Co1 N1 97.29(10) 2_655 . ? O2 Co1 N1 99.68(10) . . ? O2 Co1 N1 99.68(10) 2_655 2_655 ? O2 Co1 N1 97.29(10) . 2_655 ? N1 Co1 N1 93.64(15) . 2_655 ? O2 Co1 O1 87.09(9) 2_655 . ? O2 Co1 O1 76.44(9) . . ? N1 Co1 O1 84.97(10) . . ? N1 Co1 O1 173.21(9) 2_655 . ? O2 Co1 O1 76.44(9) 2_655 2_655 ? O2 Co1 O1 87.09(9) . 2_655 ? N1 Co1 O1 173.21(9) . 2_655 ? N1 Co1 O1 84.97(10) 2_655 2_655 ? O1 Co1 O1 97.17(13) . 2_655 ? C1 O1 Co1 112.7(2) . . ? C2 O2 Co1 117.8(2) . . ? C11 N1 C15 116.7(3) . . ? C11 N1 Co1 121.2(2) . . ? C15 N1 Co1 122.0(2) . . ? O2 C2 C3 127.0(3) . . ? O2 C2 C1 115.1(3) . . ? C3 C2 C1 117.9(3) . . ? O1 C1 C6 122.3(3) . . ? O1 C1 C2 117.8(3) . . ? C6 C1 C2 119.9(3) . . ? C5 C6 C10 119.9(3) . . ? C5 C6 C1 119.5(3) . . ? C10 C6 C1 120.6(3) . . ? C9 C10 C6 119.8(3) . . ? C9 C10 H10 120.1 . . ? C6 C10 H10 120.1 . . ? C8 C9 C10 119.7(4) . . ? C8 C9 H9 120.2 . . ? C10 C9 H9 120.2 . . ? C9 C8 C7 121.5(4) . . ? C9 C8 H8 119.3 . . ? C7 C8 H8 119.3 . . ? C8 C7 C5 119.8(4) . . ? C8 C7 H7 120.1 . . ? C5 C7 H7 120.1 . . ? C7 C5 C6 119.2(3) . . ? C7 C5 C4 120.5(3) . . ? C6 C5 C4 120.2(3) . . ? O4 C4 C3 122.7(4) . . ? O4 C4 C5 119.2(3) . . ? C3 C4 C5 118.1(3) . . ? C2 C3 C4 124.1(3) . . ? C2 C3 H3 117.9 . . ? C4 C3 H3 117.9 . . ? N1 C11 C12 123.2(4) . . ? N1 C11 H11 118.4 . . ? C12 C11 H11 118.4 . . ? C13 C12 C11 119.1(4) . . ? C13 C12 H12 120.5 . . ? C11 C12 H12 120.5 . . ? C12 C13 C14 118.7(4) . . ? C12 C13 H13 120.6 . . ? C14 C13 H13 120.6 . . ? C15 C14 C13 118.6(4) . . ? C15 C14 H14 120.7 . . ? C13 C14 H14 120.7 . . ? N1 C15 C14 123.6(3) . . ? N1 C15 H15 118.2 . . ? C14 C15 H15 118.2 . . ? C20 O20 H20 109.5 . . ? # END of CIF