Electronic Supplementary Material for CrystEngComm This Journal is (c) The Royal Society of Chemistry 2007 data_global _journal_name_full CrystEngComm _journal_coden_cambridge 1350 _journal_year ? _journal_volume ? _journal_page_first ? _publ_contact_author_address ; Laboratorio de Rayos X y Materiales Moleculares Dpto. F\'isica Fundamental II. Facultad de F\'isica Universidad de La Laguna E-38204. La Laguna. Tenerife Spain ; _publ_contact_author_email caruiz@ull.es _publ_contact_author_name 'Professor Catalina Ruiz-Perez' _publ_section_title ;Structural versatility in cobalt (II) complexes with 1,2,3,4-benzenetetracarboxylic acid (H4bta) and 4,4'-bipyridine-N,N'-dioxide (dpo) ; _publ_contact_author_fax +34922318320 _publ_contact_author_phone '+34 922318236' loop_ _publ_author_name C.Ruiz-Perez O.Fabelo M.Julve F.Lloret J.Pasan # Attachment 'compound-1-revised.cif' data_compound1 _database_code_depnum_ccdc_archive 'CCDC 633306' _ccdc_journal_manuscript_code B700877E _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C20 H32 Co N2 O20' _chemical_formula_weight 679.41 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Co Co 0.3494 0.9721 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1' _symmetry_space_group_name_Hall '-P 1' _symmetry_Int_Tables_number 2 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.4425(11) _cell_length_b 14.654(2) _cell_length_c 14.796(3) _cell_angle_alpha 114.311(10) _cell_angle_beta 102.450(11) _cell_angle_gamma 95.860(14) _cell_volume 1402.6(4) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description needle _exptl_crystal_colour colourless _exptl_crystal_size_max 0.6 _exptl_crystal_size_mid 0.02 _exptl_crystal_size_min 0.02 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.609 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 706 _exptl_absorpt_coefficient_mu 0.706 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator '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_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 16419 _diffrn_reflns_av_R_equivalents 0.0000 _diffrn_reflns_av_sigmaI/netI 0.0451 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 4.52 _diffrn_reflns_theta_max 27.88 _reflns_number_total 16419 _reflns_number_gt 12532 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius BV, 1997-2000)' _computing_cell_refinement 'Dirax/lsq (Duisenberg & Schreurs, 1989-2000)' _computing_data_reduction 'EvalCCD (Duisenberg & Schreurs 1990-2000)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics CRYSTALMAKER _computing_publication_material 'PARST97 (Nardelli, 1997)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. Based on theta max, the number of symmetry unique reflections should be 6703, however this structure was solved as a twin and the data were read into SHELXL with HKLF5. As a result, more reflections were used. ; _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^)+(0.0315P)^2^+3.2072P] 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 16419 _refine_ls_number_parameters 508 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0923 _refine_ls_R_factor_gt 0.0615 _refine_ls_wR_factor_ref 0.1532 _refine_ls_wR_factor_gt 0.1331 _refine_ls_goodness_of_fit_ref 1.217 _refine_ls_restrained_S_all 1.217 _refine_ls_shift/su_max 0.008 _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 1.0000 0.0000 0.5000 0.02973(18) Uani 1 2 d S . . Co2 Co 0.5000 1.0000 0.0000 0.02908(18) Uani 1 2 d S . . C1 C 0.7033(6) 0.3303(3) -0.1560(4) 0.0473(11) Uani 1 1 d . . . C2 C 0.6978(5) 0.3298(3) -0.0004(4) 0.0452(10) Uani 1 1 d . . . C3 C 0.7322(5) 0.4351(3) -0.1113(3) 0.0400(10) Uani 1 1 d . . . C4 C 0.7280(5) 0.4347(3) 0.0464(3) 0.0416(10) Uani 1 1 d . . . C5 C 0.7470(4) 0.4907(2) -0.0075(3) 0.0284(7) Uani 1 1 d . . . C6 C 0.7843(4) 0.6040(2) 0.0417(3) 0.0273(8) Uani 1 1 d . . . C7 C 0.8194(5) 0.6599(3) -0.0101(3) 0.0402(10) Uani 1 1 d . . . C8 C 0.7871(5) 0.6595(3) 0.1444(3) 0.0397(9) Uani 1 1 d . . . C9 C 0.8567(5) 0.7654(3) 0.0379(3) 0.0408(9) Uani 1 1 d . . . C10 C 0.8241(5) 0.7646(3) 0.1904(3) 0.0405(9) Uani 1 1 d . . . C11 C 0.4528(4) 0.3975(2) 0.4491(3) 0.0255(8) Uani 1 1 d . . . C12 C 0.5010(4) 0.4499(2) 0.3953(3) 0.0220(7) Uani 1 1 d . . . C13 C 0.4488(4) 0.4420(2) 0.5510(3) 0.0231(7) Uani 1 1 d . . . C14 C 0.4957(4) 0.3796(3) 0.2839(3) 0.0334(8) Uani 1 1 d . . . C15 C 0.3933(4) 0.3664(3) 0.5917(3) 0.0333(8) Uani 1 1 d . . . C16 C 0.0210(4) 0.5878(2) 0.5848(3) 0.0260(8) Uani 1 1 d . . . C17 C 0.0310(4) 0.5035(2) 0.4096(3) 0.0220(7) Uani 1 1 d . . . C18 C 0.0531(4) 0.5950(2) 0.4996(3) 0.0222(7) Uani 1 1 d . . . C19 C 0.0587(4) 0.4896(3) 0.3065(3) 0.0317(8) Uani 1 1 d . . . C20 C 0.1090(4) 0.7048(3) 0.5158(3) 0.0352(9) Uani 1 1 d . . . N1 N 0.8583(3) 0.8154(2) 0.1366(2) 0.0342(7) Uani 1 1 d . . . N2 N 0.6896(4) 0.2788(2) -0.1002(3) 0.0394(8) Uani 1 1 d . . . O1 O 0.8941(3) 0.91799(16) 0.1823(2) 0.0389(6) Uani 1 1 d . . . O2 O 0.6700(4) 0.17823(18) -0.1433(2) 0.0588(8) Uani 1 1 d . . . O3 O 0.5532(4) 0.4182(2) 0.2290(2) 0.0544(8) Uani 1 1 d . . . O4 O 0.4402(3) 0.28763(18) 0.2499(2) 0.0532(7) Uani 1 1 d . . . O5 O 0.3691(4) 0.27383(18) 0.5344(2) 0.0592(8) Uani 1 1 d . . . O6 O 0.3679(4) 0.3990(2) 0.6801(2) 0.0557(7) Uani 1 1 d . . . O7 O 0.1149(4) 0.7209(2) 0.4396(3) 0.0632(9) Uani 1 1 d . . . O8 O 0.1501(4) 0.77436(18) 0.6041(2) 0.0546(7) Uani 1 1 d . . . O9 O 0.0776(4) 0.5672(2) 0.2873(2) 0.0625(9) Uani 1 1 d . . . O10 O 0.0609(3) 0.40617(19) 0.2419(2) 0.0504(7) Uani 1 1 d . . . O1W O 0.9436(4) 0.0436(2) 0.3830(3) 0.0555(9) Uani 1 1 d . . . O2W O 0.7582(4) -0.1183(2) 0.4214(2) 0.0426(7) Uani 1 1 d . . . O3W O 1.1429(4) -0.1041(2) 0.4206(2) 0.0470(8) Uani 1 1 d . . . O4W O 0.5908(4) 1.15679(16) 0.1073(2) 0.0494(7) Uani 1 1 d . . . O5W O 0.2231(3) 0.99981(18) 0.0099(2) 0.0417(6) Uani 1 1 d . . . O6W O 0.5601(4) 0.9616(2) 0.1199(2) 0.0491(8) Uani 1 1 d . . . O10W O 0.4767(5) 0.1294(2) 0.3754(3) 0.0508(8) Uani 1 1 d . . . O11W O 0.5646(4) 0.0661(3) 0.6481(3) 0.0433(7) Uani 1 1 d . . . O12W O 0.9805(4) 0.1946(3) 0.1534(3) 0.0562(9) Uani 1 1 d . . . O13W O 0.1802(5) 0.0625(2) 0.1980(3) 0.0497(8) Uani 1 1 d . . . H1 H 0.701(5) 0.294(3) -0.220(3) 0.060(13) Uiso 1 1 d . . . H1A H 0.415(4) 0.325(2) 0.412(3) 0.043(9) Uiso 1 1 d . . . H1B H 0.033(4) 0.640(2) 0.638(3) 0.027(9) Uiso 1 1 d . . . H2 H 0.687(4) 0.287(2) 0.034(3) 0.049(10) Uiso 1 1 d . . . H2A H 0.583(5) 0.488(3) 0.259(4) 0.080(15) Uiso 1 1 d . . . H2B H 0.096(7) 0.646(5) 0.357(5) 0.15(2) Uiso 1 1 d . . . H3 H 0.745(4) 0.463(2) -0.151(3) 0.055(11) Uiso 1 1 d . . . H4 H 0.733(5) 0.464(3) 0.115(3) 0.075(14) Uiso 1 1 d . . . H7 H 0.829(4) 0.631(2) -0.071(3) 0.041(11) Uiso 1 1 d . . . H8 H 0.758(4) 0.627(2) 0.181(3) 0.041(9) Uiso 1 1 d . . . H9 H 0.891(4) 0.811(2) 0.009(3) 0.062(11) Uiso 1 1 d . . . H10 H 0.827(4) 0.804(2) 0.262(3) 0.043(10) Uiso 1 1 d . . . H11 H 0.918(4) 0.091(3) 0.384(3) 0.046(13) Uiso 1 1 d . . . H12 H 0.917(7) 0.000(4) 0.315(5) 0.12(2) Uiso 1 1 d . . . H21 H 0.654(5) -0.098(3) 0.404(3) 0.069(15) Uiso 1 1 d . . . H22 H 0.738(5) -0.158(3) 0.438(3) 0.068(15) Uiso 1 1 d . . . H31 H 1.153(5) -0.151(3) 0.432(3) 0.070(15) Uiso 1 1 d . . . H32 H 1.245(4) -0.085(2) 0.406(3) 0.037(10) Uiso 1 1 d . . . H41 H 0.6991 1.1649 0.1247 0.11(2) Uiso 1 1 d . . . H42 H 0.4982 1.1914 0.1378 0.128(19) Uiso 1 1 d . . . H51 H 0.1766 1.0549 0.0788 0.24(3) Uiso 1 1 d . . . H52 H 0.1515 0.9350 -0.0361 0.079(14) Uiso 1 1 d . . . H61 H 0.502(5) 0.914(3) 0.116(3) 0.063(15) Uiso 1 1 d . . . H62 H 0.692(7) 0.952(3) 0.141(4) 0.121(19) Uiso 1 1 d . . . H101 H 0.566(5) 0.152(3) 0.369(4) 0.072(17) Uiso 1 1 d . . . H102 H 0.441(5) 0.163(3) 0.416(3) 0.045(15) Uiso 1 1 d . . . H111 H 0.598(6) 0.094(4) 0.708(4) 0.08(2) Uiso 1 1 d . . . H112 H 0.540(6) 0.005(4) 0.633(4) 0.094(19) Uiso 1 1 d . . . H121 H 1.045(6) 0.167(3) 0.181(4) 0.08(2) Uiso 1 1 d . . . H122 H 1.009(6) 0.250(4) 0.177(4) 0.10(2) Uiso 1 1 d . . . H131 H 0.272(6) 0.080(3) 0.251(4) 0.081(19) Uiso 1 1 d . . . H132 H 0.116(6) 0.016(4) 0.198(4) 0.11(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 Co1 0.0416(4) 0.0206(4) 0.0329(5) 0.0149(3) 0.0157(3) 0.0071(3) Co2 0.0319(3) 0.0264(4) 0.0298(5) 0.0113(3) 0.0122(3) 0.0080(3) C1 0.072(3) 0.036(3) 0.029(3) 0.010(2) 0.021(2) 0.001(2) C2 0.066(3) 0.038(3) 0.040(3) 0.024(2) 0.021(2) 0.0074(19) C3 0.064(3) 0.032(2) 0.027(3) 0.014(2) 0.019(2) 0.0048(17) C4 0.062(3) 0.039(2) 0.028(3) 0.017(2) 0.018(2) 0.0081(18) C5 0.0272(16) 0.035(2) 0.024(2) 0.0146(18) 0.0091(14) 0.0047(13) C6 0.0293(17) 0.0296(19) 0.024(2) 0.0120(17) 0.0108(15) 0.0045(13) C7 0.061(3) 0.034(2) 0.024(3) 0.010(2) 0.018(2) 0.0039(18) C8 0.059(2) 0.038(2) 0.031(3) 0.021(2) 0.019(2) 0.0097(18) C9 0.063(2) 0.033(2) 0.028(3) 0.016(2) 0.015(2) 0.0032(18) C10 0.058(2) 0.038(2) 0.030(3) 0.017(2) 0.018(2) 0.0106(18) C11 0.0291(18) 0.0176(18) 0.031(2) 0.0102(17) 0.0128(16) 0.0053(13) C12 0.0214(16) 0.0243(18) 0.023(2) 0.0109(17) 0.0092(14) 0.0077(12) C13 0.0238(16) 0.0267(18) 0.025(2) 0.0142(17) 0.0122(14) 0.0076(13) C14 0.0349(18) 0.040(2) 0.025(2) 0.012(2) 0.0124(17) 0.0084(16) C15 0.0376(19) 0.037(2) 0.036(3) 0.024(2) 0.0139(18) 0.0084(16) C16 0.0329(18) 0.0154(18) 0.027(2) 0.0058(17) 0.0108(16) 0.0070(14) C17 0.0240(16) 0.0218(18) 0.026(2) 0.0135(17) 0.0103(14) 0.0082(12) C18 0.0269(16) 0.0204(17) 0.024(2) 0.0141(16) 0.0084(15) 0.0056(13) C19 0.037(2) 0.036(2) 0.029(2) 0.019(2) 0.0122(17) 0.0108(15) C20 0.046(2) 0.023(2) 0.041(3) 0.017(2) 0.0160(19) 0.0037(15) N1 0.0387(16) 0.0329(18) 0.031(2) 0.0147(17) 0.0097(14) 0.0062(13) N2 0.0491(18) 0.0286(18) 0.041(2) 0.0160(17) 0.0158(16) 0.0023(13) O1 0.0508(14) 0.0253(14) 0.0329(17) 0.0084(13) 0.0080(12) 0.0046(10) O2 0.0914(19) 0.0286(15) 0.053(2) 0.0138(16) 0.0273(16) 0.0030(13) O3 0.089(2) 0.0434(18) 0.0315(19) 0.0126(16) 0.0329(16) 0.0016(15) O4 0.0860(18) 0.0266(15) 0.0390(19) 0.0015(14) 0.0316(15) 0.0062(13) O5 0.103(2) 0.0284(15) 0.063(2) 0.0258(16) 0.0472(18) 0.0117(14) O6 0.092(2) 0.0459(18) 0.037(2) 0.0240(16) 0.0307(16) 0.0006(14) O7 0.124(2) 0.0269(16) 0.051(2) 0.0232(17) 0.0402(19) 0.0078(15) O8 0.0938(19) 0.0200(14) 0.044(2) 0.0110(14) 0.0192(16) 0.0018(13) O9 0.125(2) 0.0381(17) 0.046(2) 0.0272(17) 0.0481(19) 0.0189(16) O10 0.0856(18) 0.0399(16) 0.0350(19) 0.0171(15) 0.0303(15) 0.0219(14) O1W 0.112(2) 0.0267(17) 0.035(2) 0.0185(16) 0.0208(18) 0.0256(16) O2W 0.0437(17) 0.0306(16) 0.059(2) 0.0271(16) 0.0138(14) 0.0022(12) O3W 0.0597(18) 0.0316(16) 0.074(2) 0.0320(16) 0.0437(16) 0.0191(13) O4W 0.0486(17) 0.0309(15) 0.053(2) 0.0020(14) 0.0177(14) 0.0089(11) O5W 0.0341(12) 0.0407(15) 0.0439(18) 0.0110(14) 0.0149(13) 0.0084(12) O6W 0.0496(18) 0.0528(19) 0.056(2) 0.0360(18) 0.0146(15) 0.0080(14) O10W 0.058(2) 0.0333(18) 0.056(3) 0.0143(18) 0.0213(19) 0.0046(15) O11W 0.0517(17) 0.0346(18) 0.047(2) 0.0197(17) 0.0184(16) 0.0067(13) O12W 0.0565(19) 0.035(2) 0.052(2) 0.0050(19) 0.0018(16) 0.0033(16) O13W 0.0535(18) 0.0496(19) 0.045(2) 0.0219(18) 0.0149(17) 0.0024(15) _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 O3W 2.057(2) 2_756 ? Co1 O3W 2.057(2) . ? Co1 O1W 2.057(3) . ? Co1 O1W 2.057(3) 2_756 ? Co1 O2W 2.097(2) . ? Co1 O2W 2.097(2) 2_756 ? Co2 O6W 2.048(3) . ? Co2 O6W 2.048(3) 2_675 ? Co2 O5W 2.0972(19) . ? Co2 O5W 2.0972(19) 2_675 ? Co2 O4W 2.115(2) . ? Co2 O4W 2.115(2) 2_675 ? C1 N2 1.340(4) . ? C1 C3 1.370(5) . ? C2 N2 1.336(5) . ? C2 C4 1.371(5) . ? C3 C5 1.383(5) . ? C4 C5 1.377(5) . ? C5 C6 1.478(4) . ? C6 C7 1.374(4) . ? C6 C8 1.391(5) . ? C7 C9 1.377(5) . ? C8 C10 1.371(5) . ? C9 N1 1.334(4) . ? C10 N1 1.338(4) . ? C11 C13 1.383(4) . ? C11 C12 1.387(4) . ? C12 C13 1.412(4) 2_666 ? C12 C14 1.530(4) . ? C13 C12 1.412(4) 2_666 ? C13 C15 1.523(4) . ? C14 O4 1.216(4) . ? C14 O3 1.282(4) . ? C15 O5 1.237(4) . ? C15 O6 1.259(4) . ? C16 C18 1.375(4) . ? C16 C17 1.394(4) 2_566 ? C17 C16 1.394(4) 2_566 ? C17 C18 1.410(4) . ? C17 C19 1.518(4) . ? C18 C20 1.524(4) . ? C19 O10 1.207(4) . ? C19 O9 1.282(4) . ? C20 O8 1.228(4) . ? C20 O7 1.253(4) . ? N1 O1 1.338(3) . ? N2 O2 1.320(3) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O3W Co1 O3W 180.00(18) 2_756 . ? O3W Co1 O1W 89.90(12) 2_756 . ? O3W Co1 O1W 90.10(12) . . ? O3W Co1 O1W 90.10(12) 2_756 2_756 ? O3W Co1 O1W 89.90(12) . 2_756 ? O1W Co1 O1W 180.000(1) . 2_756 ? O3W Co1 O2W 93.27(11) 2_756 . ? O3W Co1 O2W 86.73(11) . . ? O1W Co1 O2W 90.01(13) . . ? O1W Co1 O2W 89.99(13) 2_756 . ? O3W Co1 O2W 86.73(11) 2_756 2_756 ? O3W Co1 O2W 93.27(11) . 2_756 ? O1W Co1 O2W 89.99(13) . 2_756 ? O1W Co1 O2W 90.01(13) 2_756 2_756 ? O2W Co1 O2W 180.0 . 2_756 ? O6W Co2 O6W 180.00(14) . 2_675 ? O6W Co2 O5W 89.57(11) . . ? O6W Co2 O5W 90.43(11) 2_675 . ? O6W Co2 O5W 90.43(11) . 2_675 ? O6W Co2 O5W 89.57(11) 2_675 2_675 ? O5W Co2 O5W 180.00(16) . 2_675 ? O6W Co2 O4W 89.51(11) . . ? O6W Co2 O4W 90.49(11) 2_675 . ? O5W Co2 O4W 91.74(10) . . ? O5W Co2 O4W 88.26(10) 2_675 . ? O6W Co2 O4W 90.49(11) . 2_675 ? O6W Co2 O4W 89.51(11) 2_675 2_675 ? O5W Co2 O4W 88.26(10) . 2_675 ? O5W Co2 O4W 91.74(10) 2_675 2_675 ? O4W Co2 O4W 180.00(8) . 2_675 ? N2 C1 C3 120.8(4) . . ? N2 C2 C4 120.5(4) . . ? C1 C3 C5 121.1(4) . . ? C2 C4 C5 121.6(4) . . ? C4 C5 C3 116.1(3) . . ? C4 C5 C6 122.6(3) . . ? C3 C5 C6 121.2(3) . . ? C7 C6 C8 116.5(3) . . ? C7 C6 C5 122.4(3) . . ? C8 C6 C5 121.1(3) . . ? C6 C7 C9 121.3(4) . . ? C10 C8 C6 121.0(3) . . ? N1 C9 C7 120.0(4) . . ? N1 C10 C8 120.1(4) . . ? C13 C11 C12 125.7(3) . . ? C11 C12 C13 117.4(3) . 2_666 ? C11 C12 C14 113.6(3) . . ? C13 C12 C14 129.0(3) 2_666 . ? C11 C13 C12 117.0(3) . 2_666 ? C11 C13 C15 114.9(3) . . ? C12 C13 C15 128.1(3) 2_666 . ? O4 C14 O3 121.2(3) . . ? O4 C14 C12 119.2(3) . . ? O3 C14 C12 119.7(3) . . ? O5 C15 O6 122.0(3) . . ? O5 C15 C13 118.1(3) . . ? O6 C15 C13 119.9(3) . . ? C18 C16 C17 125.3(3) . 2_566 ? C16 C17 C18 116.5(3) 2_566 . ? C16 C17 C19 114.5(3) 2_566 . ? C18 C17 C19 129.0(3) . . ? C16 C18 C17 118.2(3) . . ? C16 C18 C20 113.9(3) . . ? C17 C18 C20 127.9(3) . . ? O10 C19 O9 119.7(3) . . ? O10 C19 C17 120.7(3) . . ? O9 C19 C17 119.6(3) . . ? O8 C20 O7 122.4(3) . . ? O8 C20 C18 118.3(3) . . ? O7 C20 C18 119.3(3) . . ? C9 N1 C10 121.0(3) . . ? C9 N1 O1 119.4(3) . . ? C10 N1 O1 119.6(3) . . ? O2 N2 C2 120.1(3) . . ? O2 N2 C1 120.1(3) . . ? C2 N2 C1 119.8(3) . . ? _diffrn_measured_fraction_theta_max 0.934 _diffrn_reflns_theta_full 27.88 _diffrn_measured_fraction_theta_full 0.834 _refine_diff_density_max 0.592 _refine_diff_density_min -0.628 _refine_diff_density_rms 0.110 data_Compound-2 _database_code_depnum_ccdc_archive 'CCDC 633307' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C15 H21 Co N2 O12' _chemical_formula_weight 480.27 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Co Co 0.3494 0.9721 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.4119(14) _cell_length_b 8.5298(9) _cell_length_c 13.321(3) _cell_angle_alpha 85.328(11) _cell_angle_beta 76.027(14) _cell_angle_gamma 80.489(13) _cell_volume 913.9(3) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description prism _exptl_crystal_colour red _exptl_crystal_size_max 0.8 _exptl_crystal_size_mid 0.8 _exptl_crystal_size_min 0.4 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.745 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 496 _exptl_absorpt_coefficient_mu 1.012 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.463 _exptl_absorpt_correction_T_max 0.667 _exptl_absorpt_process_details sadbas _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator '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_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 9838 _diffrn_reflns_av_R_equivalents 0.0297 _diffrn_reflns_av_sigmaI/netI 0.0569 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 5.04 _diffrn_reflns_theta_max 27.50 _reflns_number_total 4084 _reflns_number_gt 2950 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius BV, 1997-2000)' _computing_cell_refinement 'Dirax/lsq (Duisenberg & Schreurs, 1989-2000)' _computing_data_reduction 'EvalCCD (Duisenberg & Schreurs 1990-2000)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics CRYSTALMAKER _computing_publication_material 'PARST97 (Nardelli, 1997)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0293P)^2^+0.3610P] 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 4084 _refine_ls_number_parameters 355 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0692 _refine_ls_R_factor_gt 0.0368 _refine_ls_wR_factor_ref 0.0738 _refine_ls_wR_factor_gt 0.0665 _refine_ls_goodness_of_fit_ref 1.007 _refine_ls_restrained_S_all 1.007 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Co1 Co 0.79955(4) 0.13831(4) 0.37846(2) 0.02078(10) Uani 1 1 d . . . C1 C 0.9889(2) 0.3771(2) 0.07645(15) 0.0155(4) Uani 1 1 d . . . C2 C 0.9892(2) 0.3499(3) -0.02508(16) 0.0175(5) Uani 1 1 d . . . C3 C 0.9998(2) 0.4704(2) -0.10225(15) 0.0153(4) Uani 1 1 d . . . C4 C 0.9657(3) 0.2432(2) 0.15710(15) 0.0177(5) Uani 1 1 d . . . C5 C 0.9946(3) 0.4328(3) -0.21065(16) 0.0199(5) Uani 1 1 d . . . C10 C 0.6912(3) 0.0013(3) 0.16764(17) 0.0250(5) Uani 1 1 d . . . C11 C 0.4635(3) 0.1853(3) 0.24159(19) 0.0279(6) Uani 1 1 d . . . C12 C 0.6745(3) 0.0550(3) 0.07084(18) 0.0239(5) Uani 1 1 d . . . C13 C 0.4414(3) 0.2397(3) 0.14583(18) 0.0260(5) Uani 1 1 d . . . C14 C 0.5502(2) 0.1784(3) 0.05659(16) 0.0204(5) Uani 1 1 d . . . C15 C 0.5359(2) 0.2403(3) -0.04831(16) 0.0197(5) Uani 1 1 d . . . C16 C 0.6384(3) 0.1700(3) -0.13623(18) 0.0277(6) Uani 1 1 d . . . C17 C 0.4199(3) 0.3691(3) -0.06588(18) 0.0244(5) Uani 1 1 d . . . C18 C 0.6249(3) 0.2247(3) -0.23309(19) 0.0301(6) Uani 1 1 d . . . C19 C 0.4096(3) 0.4236(3) -0.16372(18) 0.0252(5) Uani 1 1 d . . . N1 N 0.5893(2) 0.0700(2) 0.25140(14) 0.0240(4) Uani 1 1 d . . . N2 N 0.5112(2) 0.3512(2) -0.24623(14) 0.0244(4) Uani 1 1 d . . . O1 O 0.84712(17) 0.26927(17) 0.23476(10) 0.0197(3) Uani 1 1 d . . . O2 O 1.0621(2) 0.11543(19) 0.14008(12) 0.0342(4) Uani 1 1 d . . . O3 O 0.89972(18) 0.52856(19) -0.25489(11) 0.0269(4) Uani 1 1 d . . . O4 O 1.0821(2) 0.3089(2) -0.24687(12) 0.0370(4) Uani 1 1 d . . . O5 O 0.6159(2) 0.0249(2) 0.34539(11) 0.0306(4) Uani 1 1 d . . . O6 O 0.5023(2) 0.4026(2) -0.34068(12) 0.0378(5) Uani 1 1 d . . . O1W O 0.6251(2) 0.3273(2) 0.43210(14) 0.0317(4) Uani 1 1 d . . . O2W O 0.9864(2) 0.2457(2) 0.41374(17) 0.0310(4) Uani 1 1 d . . . O3W O 0.7508(4) 0.0215(3) 0.52715(15) 0.0430(5) Uani 1 1 d . . . O4W O 0.9885(2) -0.0458(2) 0.32132(15) 0.0307(4) Uani 1 1 d . . . O5W O 0.8326(3) 0.4359(2) 0.56915(14) 0.0345(4) Uani 1 1 d . . . O6W O 0.7013(3) -0.2795(3) 0.47301(19) 0.0450(5) Uani 1 1 d . . . H2 H 0.983(2) 0.248(3) -0.0407(15) 0.009(5) Uiso 1 1 d . . . H19 H 0.327(3) 0.513(3) -0.1810(17) 0.029(6) Uiso 1 1 d . . . H10 H 0.773(3) -0.085(3) 0.1801(18) 0.033(7) Uiso 1 1 d . . . H18 H 0.688(3) 0.180(3) -0.294(2) 0.036(7) Uiso 1 1 d . . . H16 H 0.714(3) 0.086(3) -0.1307(17) 0.030(7) Uiso 1 1 d . . . H12 H 0.750(3) 0.005(3) 0.0142(18) 0.026(6) Uiso 1 1 d . . . H13 H 0.348(3) 0.316(3) 0.1441(17) 0.029(6) Uiso 1 1 d . . . H11 H 0.398(3) 0.222(3) 0.2999(19) 0.027(6) Uiso 1 1 d . . . H17 H 0.348(3) 0.420(3) -0.0147(19) 0.034(7) Uiso 1 1 d . . . H5W2 H 0.860(3) 0.447(3) 0.623(2) 0.042(9) Uiso 1 1 d . . . H1W1 H 0.600(3) 0.400(4) 0.395(2) 0.041(9) Uiso 1 1 d . . . H5W1 H 0.737(4) 0.416(4) 0.584(2) 0.063(11) Uiso 1 1 d . . . H1W2 H 0.532(4) 0.308(4) 0.461(3) 0.076(13) Uiso 1 1 d . . . H4W2 H 1.022(4) -0.012(4) 0.263(3) 0.073(12) Uiso 1 1 d . . . H4W1 H 0.961(4) -0.132(4) 0.316(2) 0.063(12) Uiso 1 1 d . . . H6W2 H 0.760(5) -0.357(5) 0.493(3) 0.083(14) Uiso 1 1 d . . . H6W1 H 0.708(6) -0.287(6) 0.419(4) 0.12(2) Uiso 1 1 d . . . H2W1 H 1.016(4) 0.296(4) 0.368(2) 0.047(10) Uiso 1 1 d . . . H2W2 H 0.946(4) 0.299(4) 0.469(3) 0.054(10) Uiso 1 1 d . . . H3W1 H 0.708(6) -0.040(6) 0.523(4) 0.12(2) Uiso 1 1 d . . . H3W2 H 0.818(9) -0.029(8) 0.549(5) 0.20(3) 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 Co1 0.03136(18) 0.01658(18) 0.01417(16) 0.00075(12) -0.00612(12) -0.00233(12) C1 0.0149(10) 0.0152(11) 0.0137(10) -0.0007(8) 0.0005(8) -0.0004(8) C2 0.0224(11) 0.0104(12) 0.0194(11) -0.0029(9) -0.0030(9) -0.0032(9) C3 0.0159(10) 0.0148(12) 0.0141(10) -0.0017(8) -0.0018(8) -0.0009(8) C4 0.0221(11) 0.0145(12) 0.0178(11) -0.0014(9) -0.0070(9) -0.0024(9) C5 0.0263(12) 0.0175(13) 0.0163(11) -0.0013(9) -0.0025(9) -0.0078(10) C10 0.0288(13) 0.0206(14) 0.0257(13) -0.0010(10) -0.0074(10) -0.0026(10) C11 0.0292(13) 0.0305(15) 0.0203(13) -0.0051(11) 0.0017(10) -0.0033(11) C12 0.0239(12) 0.0244(14) 0.0225(12) -0.0033(10) -0.0055(10) -0.0002(10) C13 0.0226(12) 0.0252(14) 0.0286(13) -0.0014(10) -0.0042(10) -0.0012(11) C14 0.0187(11) 0.0201(13) 0.0232(11) -0.0023(9) -0.0044(9) -0.0054(9) C15 0.0178(11) 0.0185(12) 0.0231(11) -0.0009(9) -0.0046(9) -0.0037(9) C16 0.0258(13) 0.0241(14) 0.0272(13) 0.0018(10) -0.0041(10) 0.0087(11) C17 0.0193(12) 0.0260(14) 0.0249(13) -0.0043(10) -0.0026(10) 0.0027(10) C18 0.0308(13) 0.0296(15) 0.0215(13) 0.0007(11) 0.0017(10) 0.0073(11) C19 0.0196(12) 0.0249(14) 0.0286(13) 0.0011(10) -0.0055(10) 0.0022(10) N1 0.0299(11) 0.0238(11) 0.0202(10) 0.0007(8) -0.0062(8) -0.0098(9) N2 0.0217(10) 0.0274(12) 0.0216(10) 0.0059(8) -0.0045(8) -0.0006(8) O1 0.0238(8) 0.0181(8) 0.0144(7) 0.0009(6) -0.0009(6) -0.0009(6) O2 0.0396(10) 0.0198(10) 0.0295(9) 0.0043(7) 0.0062(7) 0.0109(8) O3 0.0328(9) 0.0271(10) 0.0232(8) -0.0026(7) -0.0145(7) 0.0011(7) O4 0.0614(12) 0.0242(10) 0.0229(9) -0.0105(7) -0.0135(8) 0.0104(9) O5 0.0458(10) 0.0330(11) 0.0166(8) 0.0064(7) -0.0111(7) -0.0143(8) O6 0.0390(10) 0.0457(12) 0.0217(9) 0.0105(8) -0.0070(7) 0.0078(8) O1W 0.0366(11) 0.0251(11) 0.0268(10) 0.0041(8) -0.0005(8) 0.0014(8) O2W 0.0404(11) 0.0302(11) 0.0238(10) -0.0014(10) -0.0094(9) -0.0066(9) O3W 0.0707(15) 0.0340(13) 0.0253(10) 0.0098(9) -0.0132(10) -0.0133(12) O4W 0.0402(11) 0.0176(11) 0.0315(11) 0.0000(8) -0.0071(8) 0.0010(8) O5W 0.0385(12) 0.0466(13) 0.0235(10) -0.0058(8) -0.0101(9) -0.0147(9) O6W 0.0569(14) 0.0480(15) 0.0355(13) 0.0080(11) -0.0167(11) -0.0192(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 O1W 2.0401(18) . ? Co1 O4W 2.0871(18) . ? Co1 O5 2.0997(16) . ? Co1 O2W 2.1051(19) . ? Co1 O1 2.1218(14) . ? Co1 O3W 2.1227(19) . ? C1 C2 1.390(3) . ? C1 C3 1.396(3) 2_765 ? C1 C4 1.506(3) . ? C2 C3 1.391(3) . ? C3 C1 1.396(3) 2_765 ? C3 C5 1.517(3) . ? C4 O2 1.248(3) . ? C4 O1 1.257(2) . ? C5 O4 1.243(3) . ? C5 O3 1.259(2) . ? C10 N1 1.342(3) . ? C10 C12 1.365(3) . ? C11 N1 1.344(3) . ? C11 C13 1.366(3) . ? C12 C14 1.392(3) . ? C13 C14 1.393(3) . ? C14 C15 1.479(3) . ? C15 C17 1.388(3) . ? C15 C16 1.390(3) . ? C16 C18 1.360(3) . ? C17 C19 1.366(3) . ? C18 N2 1.349(3) . ? C19 N2 1.342(3) . ? N1 O5 1.340(2) . ? N2 O6 1.314(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 O1W Co1 O4W 176.58(9) . . ? O1W Co1 O5 90.12(8) . . ? O4W Co1 O5 92.91(8) . . ? O1W Co1 O2W 91.04(8) . . ? O4W Co1 O2W 85.97(8) . . ? O5 Co1 O2W 178.30(7) . . ? O1W Co1 O1 86.79(7) . . ? O4W Co1 O1 91.34(7) . . ? O5 Co1 O1 95.44(6) . . ? O2W Co1 O1 85.87(7) . . ? O1W Co1 O3W 90.37(9) . . ? O4W Co1 O3W 91.37(9) . . ? O5 Co1 O3W 87.05(9) . . ? O2W Co1 O3W 91.70(10) . . ? O1 Co1 O3W 176.22(8) . . ? C2 C1 C3 119.33(18) . 2_765 ? C2 C1 C4 118.88(19) . . ? C3 C1 C4 121.68(18) 2_765 . ? C1 C2 C3 122.0(2) . . ? C2 C3 C1 118.67(19) . 2_765 ? C2 C3 C5 119.03(19) . . ? C1 C3 C5 122.28(17) 2_765 . ? O2 C4 O1 125.68(19) . . ? O2 C4 C1 117.64(18) . . ? O1 C4 C1 116.65(18) . . ? O4 C5 O3 126.0(2) . . ? O4 C5 C3 117.05(18) . . ? O3 C5 C3 116.90(19) . . ? N1 C10 C12 120.1(2) . . ? N1 C11 C13 120.5(2) . . ? C10 C12 C14 121.2(2) . . ? C11 C13 C14 120.7(2) . . ? C12 C14 C13 116.6(2) . . ? C12 C14 C15 121.2(2) . . ? C13 C14 C15 122.3(2) . . ? C17 C15 C16 115.8(2) . . ? C17 C15 C14 123.0(2) . . ? C16 C15 C14 121.18(19) . . ? C18 C16 C15 121.7(2) . . ? C19 C17 C15 121.7(2) . . ? N2 C18 C16 120.3(2) . . ? N2 C19 C17 120.2(2) . . ? O5 N1 C10 119.35(19) . . ? O5 N1 C11 119.93(19) . . ? C10 N1 C11 120.7(2) . . ? O6 N2 C19 120.77(18) . . ? O6 N2 C18 119.00(19) . . ? C19 N2 C18 120.23(19) . . ? C4 O1 Co1 129.05(13) . . ? N1 O5 Co1 111.67(12) . . ? _diffrn_measured_fraction_theta_max 0.976 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.976 _refine_diff_density_max 0.363 _refine_diff_density_min -0.350 _refine_diff_density_rms 0.066 # Attachment 'compound-3-revised.cif' data_COMPOUND3 _database_code_depnum_ccdc_archive 'CCDC 633308' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C30 H24 Co N4 O14' _chemical_formula_weight 723.46 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Co Co 0.3494 0.9721 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.6523(8) _cell_length_b 9.5220(10) _cell_length_c 10.7629(8) _cell_angle_alpha 112.019(6) _cell_angle_beta 92.828(7) _cell_angle_gamma 100.950(9) _cell_volume 707.51(12) _cell_formula_units_Z 1 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description prism _exptl_crystal_colour red _exptl_crystal_size_max 0.6 _exptl_crystal_size_mid 0.6 _exptl_crystal_size_min 0.4 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.698 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 371 _exptl_absorpt_coefficient_mu 0.693 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.666 _exptl_absorpt_correction_T_max 0.758 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator '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_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 3874 _diffrn_reflns_av_R_equivalents 0.0175 _diffrn_reflns_av_sigmaI/netI 0.0253 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 5.06 _diffrn_reflns_theta_max 27.50 _reflns_number_total 2970 _reflns_number_gt 1775 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius BV, 1997-2000)' _computing_cell_refinement 'Dirax/lsq (Duisenberg & Schreurs, 1989-2000)' _computing_data_reduction 'EvalCCD (Duisenberg & Schreurs 1990-2000)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics CRYSTALMAKER _computing_publication_material 'PARST97 (Nardelli, 1997)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0245P)^2^+0.4407P] 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 2970 _refine_ls_number_parameters 271 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0319 _refine_ls_R_factor_gt 0.0257 _refine_ls_wR_factor_ref 0.0635 _refine_ls_wR_factor_gt 0.0607 _refine_ls_goodness_of_fit_ref 1.133 _refine_ls_restrained_S_all 1.133 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Co1 Co 0.0000 0.5000 0.5000 0.01508(15) Uani 1 2 d S . . C1 C -0.0760(3) 0.9789(2) 0.87213(19) 0.0152(5) Uani 1 1 d . . . C2 C -0.0430(3) 0.8513(2) 0.89554(19) 0.0149(5) Uani 1 1 d . . . C3 C 0.0315(3) 0.8743(3) 1.0240(2) 0.0167(5) Uani 1 1 d . . . C4 C -0.1691(3) 0.9575(3) 0.7385(2) 0.0193(5) Uani 1 1 d . . . C5 C -0.0729(3) 0.6917(2) 0.78263(19) 0.0155(5) Uani 1 1 d . . . C10 C 0.3733(3) 0.5956(3) 0.7336(2) 0.0237(5) Uani 1 1 d . . . C11 C 0.1786(3) 0.4491(3) 0.8232(2) 0.0223(5) Uani 1 1 d . . . C12 C 0.4610(3) 0.6879(3) 0.8602(2) 0.0222(5) Uani 1 1 d . . . C13 C 0.2647(3) 0.5389(3) 0.9511(2) 0.0216(5) Uani 1 1 d . . . C14 C 0.4077(3) 0.6641(2) 0.9741(2) 0.0180(5) Uani 1 1 d . . . C15 C 0.4985(3) 0.7693(2) 1.1112(2) 0.0175(5) Uani 1 1 d . . . C16 C 0.6017(3) 0.9160(3) 1.1357(2) 0.0248(5) Uani 1 1 d . . . C17 C 0.4869(3) 0.7284(3) 1.2220(2) 0.0218(5) Uani 1 1 d . . . C18 C 0.6836(3) 1.0146(3) 1.2623(2) 0.0238(5) Uani 1 1 d . . . C19 C 0.5713(3) 0.8284(3) 1.3479(2) 0.0235(5) Uani 1 1 d . . . N1 N 0.2306(2) 0.4796(2) 0.71676(17) 0.0200(4) Uani 1 1 d . . . N2 N 0.6661(2) 0.9705(2) 1.36657(17) 0.0200(4) Uani 1 1 d . . . O1 O -0.0894(3) 1.0596(2) 0.69271(18) 0.0376(5) Uani 1 1 d . . . O2 O -0.3042(2) 0.8596(2) 0.68352(16) 0.0329(4) Uani 1 1 d . . . O3 O 0.00634(19) 0.68811(16) 0.68194(13) 0.0198(4) Uani 1 1 d . . . O4 O -0.1658(2) 0.57941(17) 0.79856(14) 0.0271(4) Uani 1 1 d . . . O5 O 0.1428(2) 0.39271(17) 0.59438(14) 0.0276(4) Uani 1 1 d . . . O6 O 0.7409(2) 1.07183(18) 1.48892(15) 0.0326(4) Uani 1 1 d . . . O1W O -0.2368(2) 0.3751(2) 0.53651(17) 0.0228(4) Uani 1 1 d . . . H3 H 0.055(3) 0.787(3) 1.041(2) 0.013(5) Uiso 1 1 d . . . H17 H 0.427(3) 0.633(3) 1.213(2) 0.020(6) Uiso 1 1 d . . . H16 H 0.618(3) 0.954(3) 1.069(2) 0.026(6) Uiso 1 1 d . . . H10 H 0.403(3) 0.611(3) 0.654(3) 0.030(6) Uiso 1 1 d . . . H12 H 0.558(3) 0.765(3) 0.866(2) 0.024(6) Uiso 1 1 d . . . H19 H 0.569(3) 0.805(3) 1.423(2) 0.026(6) Uiso 1 1 d . . . H18 H 0.757(3) 1.109(3) 1.282(2) 0.021(6) Uiso 1 1 d . . . H13 H 0.225(3) 0.515(3) 1.021(2) 0.027(6) Uiso 1 1 d . . . H11 H 0.077(3) 0.367(3) 0.802(2) 0.031(7) Uiso 1 1 d . . . H2W1 H -0.232(4) 0.280(4) 0.521(3) 0.046(9) Uiso 1 1 d . . . H1W1 H -0.229(4) 0.423(4) 0.617(3) 0.047(9) Uiso 1 1 d . . . H1 H -0.149(5) 1.047(4) 0.622(4) 0.068(11) 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 Co1 0.0204(3) 0.0117(2) 0.0079(2) -0.00001(17) 0.00070(17) -0.00014(17) C1 0.0180(11) 0.0156(12) 0.0101(10) 0.0031(9) 0.0028(9) 0.0035(9) C2 0.0173(11) 0.0142(12) 0.0110(11) 0.0025(9) 0.0042(9) 0.0027(9) C3 0.0231(12) 0.0132(12) 0.0144(11) 0.0051(10) 0.0034(9) 0.0062(10) C4 0.0262(13) 0.0164(12) 0.0134(11) 0.0028(10) 0.0012(10) 0.0075(11) C5 0.0193(12) 0.0142(12) 0.0105(11) 0.0023(9) -0.0011(9) 0.0042(10) C10 0.0279(14) 0.0259(14) 0.0165(12) 0.0091(11) 0.0004(10) 0.0033(11) C11 0.0232(13) 0.0179(13) 0.0222(13) 0.0069(10) -0.0012(10) -0.0009(11) C12 0.0192(13) 0.0230(13) 0.0216(12) 0.0085(11) -0.0005(10) -0.0007(11) C13 0.0244(13) 0.0206(13) 0.0193(12) 0.0087(10) 0.0030(10) 0.0022(10) C14 0.0178(12) 0.0180(12) 0.0170(11) 0.0053(9) -0.0001(9) 0.0051(10) C15 0.0153(11) 0.0182(12) 0.0178(11) 0.0058(10) 0.0014(9) 0.0039(9) C16 0.0297(14) 0.0255(14) 0.0181(12) 0.0113(11) 0.0008(10) -0.0012(11) C17 0.0267(13) 0.0160(13) 0.0200(12) 0.0064(10) 0.0027(10) 0.0003(11) C18 0.0280(14) 0.0199(14) 0.0200(13) 0.0083(11) -0.0007(10) -0.0025(11) C19 0.0335(14) 0.0201(13) 0.0169(12) 0.0082(10) 0.0030(10) 0.0044(11) N1 0.0248(11) 0.0164(10) 0.0145(10) 0.0025(8) -0.0055(8) 0.0039(8) N2 0.0245(10) 0.0164(10) 0.0141(10) 0.0023(8) -0.0033(8) 0.0023(8) O1 0.0496(12) 0.0353(11) 0.0225(10) 0.0188(9) -0.0168(9) -0.0128(9) O2 0.0315(10) 0.0349(10) 0.0246(9) 0.0116(8) -0.0095(8) -0.0072(9) O3 0.0266(9) 0.0149(8) 0.0107(7) -0.0007(6) 0.0044(7) -0.0005(7) O4 0.0415(10) 0.0141(8) 0.0186(8) 0.0021(7) 0.0093(7) -0.0026(7) O5 0.0395(10) 0.0187(9) 0.0156(8) -0.0001(7) -0.0109(7) 0.0039(7) O6 0.0538(12) 0.0193(9) 0.0151(8) 0.0019(7) -0.0127(8) 0.0002(8) O1W 0.0313(10) 0.0154(9) 0.0159(9) 0.0024(7) 0.0031(7) -0.0005(7) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Co1 O5 2.0886(15) . ? Co1 O5 2.0886(15) 2_566 ? Co1 O3 2.0912(13) . ? Co1 O3 2.0912(13) 2_566 ? Co1 O1W 2.1108(16) . ? Co1 O1W 2.1108(16) 2_566 ? C1 C3 1.389(3) 2_577 ? C1 C2 1.394(3) . ? C1 C4 1.497(3) . ? C2 C3 1.390(3) . ? C2 C5 1.515(3) . ? C3 C1 1.389(3) 2_577 ? C3 H3 0.96(2) . ? C4 O2 1.203(3) . ? C4 O1 1.313(3) . ? C5 O4 1.241(3) . ? C5 O3 1.260(2) . ? C10 N1 1.348(3) . ? C10 C12 1.367(3) . ? C10 H10 0.95(2) . ? C11 N1 1.344(3) . ? C11 C13 1.369(3) . ? C11 H11 0.94(3) . ? C12 C14 1.393(3) . ? C12 H12 0.92(2) . ? C13 C14 1.391(3) . ? C13 H13 0.92(2) . ? C14 C15 1.480(3) . ? C15 C16 1.388(3) . ? C15 C17 1.389(3) . ? C16 C18 1.365(3) . ? C16 H16 0.92(2) . ? C17 C19 1.368(3) . ? C17 H17 0.90(2) . ? C18 N2 1.342(3) . ? C18 H18 0.91(2) . ? C19 N2 1.345(3) . ? C19 H19 0.92(2) . ? N1 O5 1.325(2) . ? N2 O6 1.325(2) . ? O1 H1 0.82(4) . ? O1W H2W1 0.87(3) . ? O1W H1W1 0.80(3) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O5 Co1 O5 180.0 . 2_566 ? O5 Co1 O3 92.50(6) . . ? O5 Co1 O3 87.50(6) 2_566 . ? O5 Co1 O3 87.50(6) . 2_566 ? O5 Co1 O3 92.50(6) 2_566 2_566 ? O3 Co1 O3 180.0 . 2_566 ? O5 Co1 O1W 87.36(7) . . ? O5 Co1 O1W 92.64(7) 2_566 . ? O3 Co1 O1W 90.50(7) . . ? O3 Co1 O1W 89.50(7) 2_566 . ? O5 Co1 O1W 92.64(7) . 2_566 ? O5 Co1 O1W 87.36(7) 2_566 2_566 ? O3 Co1 O1W 89.50(7) . 2_566 ? O3 Co1 O1W 90.50(7) 2_566 2_566 ? O1W Co1 O1W 180.0 . 2_566 ? C3 C1 C2 119.71(19) 2_577 . ? C3 C1 C4 119.72(19) 2_577 . ? C2 C1 C4 120.47(18) . . ? C3 C2 C1 118.77(19) . . ? C3 C2 C5 119.34(18) . . ? C1 C2 C5 121.73(17) . . ? C1 C3 C2 121.5(2) 2_577 . ? C1 C3 H3 119.0(12) 2_577 . ? C2 C3 H3 119.5(13) . . ? O2 C4 O1 125.2(2) . . ? O2 C4 C1 122.5(2) . . ? O1 C4 C1 112.2(2) . . ? O4 C5 O3 126.81(19) . . ? O4 C5 C2 118.53(17) . . ? O3 C5 C2 114.62(18) . . ? N1 C10 C12 120.1(2) . . ? N1 C10 H10 116.2(15) . . ? C12 C10 H10 123.6(15) . . ? N1 C11 C13 120.7(2) . . ? N1 C11 H11 114.6(15) . . ? C13 C11 H11 124.6(15) . . ? C10 C12 C14 121.4(2) . . ? C10 C12 H12 116.3(14) . . ? C14 C12 H12 122.3(14) . . ? C11 C13 C14 120.9(2) . . ? C11 C13 H13 118.0(15) . . ? C14 C13 H13 121.2(15) . . ? C13 C14 C12 116.4(2) . . ? C13 C14 C15 122.71(19) . . ? C12 C14 C15 120.9(2) . . ? C16 C15 C17 116.1(2) . . ? C16 C15 C14 121.17(19) . . ? C17 C15 C14 122.7(2) . . ? C18 C16 C15 121.5(2) . . ? C18 C16 H16 115.8(15) . . ? C15 C16 H16 122.7(15) . . ? C19 C17 C15 121.4(2) . . ? C19 C17 H17 117.5(14) . . ? C15 C17 H17 121.0(14) . . ? N2 C18 C16 120.1(2) . . ? N2 C18 H18 115.2(14) . . ? C16 C18 H18 124.6(14) . . ? N2 C19 C17 119.9(2) . . ? N2 C19 H19 115.8(15) . . ? C17 C19 H19 124.2(15) . . ? O5 N1 C11 119.53(18) . . ? O5 N1 C10 120.07(18) . . ? C11 N1 C10 120.39(19) . . ? O6 N2 C18 118.40(18) . . ? O6 N2 C19 120.77(18) . . ? C18 N2 C19 120.81(19) . . ? C4 O1 H1 109(2) . . ? C5 O3 Co1 129.14(13) . . ? N1 O5 Co1 117.33(12) . . ? Co1 O1W H2W1 112.3(18) . . ? Co1 O1W H1W1 98(2) . . ? H2W1 O1W H1W1 109(3) . . ? _diffrn_measured_fraction_theta_max 0.969 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.969 _refine_diff_density_max 0.263 _refine_diff_density_min -0.253 _refine_diff_density_rms 0.049 # Attachment 'compound-4-revised.cif' data_compound-4 _database_code_depnum_ccdc_archive 'CCDC 633309' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C15 H15 Co N2 O9' _chemical_formula_weight 426.22 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Co Co 0.3494 0.9721 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/c' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 10.9277(9) _cell_length_b 11.1926(6) _cell_length_c 12.7187(9) _cell_angle_alpha 90.00 _cell_angle_beta 97.006(6) _cell_angle_gamma 90.00 _cell_volume 1544.00(19) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description cube _exptl_crystal_colour red _exptl_crystal_size_max 0.12 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.834 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 872 _exptl_absorpt_coefficient_mu 1.172 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.869 _exptl_absorpt_correction_T_max 0.889 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator '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_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 12144 _diffrn_reflns_av_R_equivalents 0.0717 _diffrn_reflns_av_sigmaI/netI 0.1037 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 4.18 _diffrn_reflns_theta_max 27.50 _reflns_number_total 3518 _reflns_number_gt 2147 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius BV, 1997-2000)' _computing_cell_refinement 'Dirax/lsq (Duisenberg & Schreurs, 1989-2000)' _computing_data_reduction 'EvalCCD (Duisenberg & Schreurs 1990-2000)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics CRYSTALMAKER _computing_publication_material 'PARST97 (Nardelli, 1997)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0267P)^2^+0.6279P] 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 3518 _refine_ls_number_parameters 304 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1257 _refine_ls_R_factor_gt 0.0594 _refine_ls_wR_factor_ref 0.0923 _refine_ls_wR_factor_gt 0.0785 _refine_ls_goodness_of_fit_ref 1.104 _refine_ls_restrained_S_all 1.104 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Co1 Co 0.04717(4) 0.23112(4) 0.34445(4) 0.01741(15) Uani 1 1 d . . . C1 C 0.3748(3) 0.0141(3) 0.4642(3) 0.0135(8) Uani 1 1 d . . . C2 C 0.4640(3) 0.0765(3) 0.4178(3) 0.0151(8) Uani 1 1 d . . . C3 C 0.5893(3) 0.0634(3) 0.4519(3) 0.0123(8) Uani 1 1 d . . . C4 C 0.2411(3) 0.0310(3) 0.4181(3) 0.0154(8) Uani 1 1 d . . . C5 C 0.6818(3) 0.1203(3) 0.3887(3) 0.0169(9) Uani 1 1 d . . . C10 C 0.3188(3) 0.3770(4) 0.3808(4) 0.0269(10) Uani 1 1 d . . . C11 C 0.2304(3) 0.5633(4) 0.4027(3) 0.0276(10) Uani 1 1 d . . . C12 C 0.4293(4) 0.4288(4) 0.3705(3) 0.0262(10) Uani 1 1 d . . . C13 C 0.3406(3) 0.6173(4) 0.3940(3) 0.0272(10) Uani 1 1 d . . . C14 C 0.4446(3) 0.5513(3) 0.3761(3) 0.0197(9) Uani 1 1 d . . . C15 C 0.5655(3) 0.6070(3) 0.3646(3) 0.0194(9) Uani 1 1 d . . . C16 C 0.6690(3) 0.5373(4) 0.3533(3) 0.0242(10) Uani 1 1 d . . . C17 C 0.5824(3) 0.7297(4) 0.3644(3) 0.0253(9) Uani 1 1 d . . . C18 C 0.7802(3) 0.5884(4) 0.3376(3) 0.0244(10) Uani 1 1 d . . . C19 C 0.6929(3) 0.7797(4) 0.3488(3) 0.0227(9) Uani 1 1 d . . . N1 N 0.2198(3) 0.4430(3) 0.3954(2) 0.0230(8) Uani 1 1 d . . . N2 N 0.7883(2) 0.7085(3) 0.3320(2) 0.0218(8) Uani 1 1 d . . . O1 O 0.20932(19) 0.1374(2) 0.3996(2) 0.0245(7) Uani 1 1 d . . . O2 O 0.1752(2) -0.0590(2) 0.3989(2) 0.0235(6) Uani 1 1 d . . . O3 O 0.6694(2) 0.2278(2) 0.3640(2) 0.0324(7) Uani 1 1 d . . . O4 O 0.7630(2) 0.0511(2) 0.3645(2) 0.0301(7) Uani 1 1 d . . . O5 O 0.1137(2) 0.3910(2) 0.4076(2) 0.0285(7) Uani 1 1 d . . . O6 O 0.89312(19) 0.7591(2) 0.3090(2) 0.0251(6) Uani 1 1 d . . . O1W O -0.0283(3) 0.2142(3) 0.4909(2) 0.0330(8) Uani 1 1 d . . . O2W O -0.0251(3) 0.0670(3) 0.2960(2) 0.0237(7) Uani 1 1 d . . . O3W O -0.1222(3) 0.3084(3) 0.2882(3) 0.0286(8) Uani 1 1 d . . . H2 H 0.442(3) 0.128(3) 0.359(3) 0.014(9) Uiso 1 1 d . . . H10 H 0.307(3) 0.297(4) 0.385(3) 0.025(11) Uiso 1 1 d . . . H11 H 0.148(3) 0.610(4) 0.419(3) 0.045(12) Uiso 1 1 d . . . H1W2 H 0.020(4) 0.217(4) 0.552(4) 0.062(16) Uiso 1 1 d . . . H12 H 0.495(3) 0.375(4) 0.358(3) 0.042(12) Uiso 1 1 d . . . H1W1 H -0.072(4) 0.166(4) 0.506(4) 0.041(16) Uiso 1 1 d . . . H13 H 0.346(3) 0.703(3) 0.399(3) 0.009(9) Uiso 1 1 d . . . H16 H 0.657(3) 0.451(3) 0.348(3) 0.014(9) Uiso 1 1 d . . . H17 H 0.517(3) 0.779(3) 0.373(3) 0.019(10) Uiso 1 1 d . . . H18 H 0.866(3) 0.543(3) 0.346(3) 0.040(12) Uiso 1 1 d . . . H19 H 0.706(3) 0.857(3) 0.347(3) 0.019(10) Uiso 1 1 d . . . H2W2 H 0.017(3) 0.019(4) 0.327(3) 0.030(14) Uiso 1 1 d . . . H2W1 H -0.097(4) 0.060(4) 0.305(3) 0.040(14) Uiso 1 1 d . . . H3W1 H -0.175(4) 0.282(4) 0.306(4) 0.033(15) Uiso 1 1 d . . . H3W2 H -0.140(4) 0.343(5) 0.224(5) 0.074(19) 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 Co1 0.0115(2) 0.0188(3) 0.0217(3) 0.0041(3) 0.00106(18) -0.0006(2) C1 0.0123(16) 0.013(2) 0.016(2) -0.0022(16) 0.0032(15) -0.0013(14) C2 0.0188(18) 0.013(2) 0.013(2) 0.0055(17) 0.0008(16) 0.0040(15) C3 0.0107(16) 0.013(2) 0.014(2) -0.0012(16) 0.0030(14) -0.0006(14) C4 0.0116(17) 0.020(2) 0.015(2) 0.0004(18) 0.0029(15) -0.0003(16) C5 0.0124(17) 0.022(2) 0.015(2) 0.0047(18) -0.0021(15) -0.0055(16) C10 0.025(2) 0.019(3) 0.037(3) -0.002(2) 0.0072(18) -0.0035(19) C11 0.025(2) 0.021(2) 0.037(3) 0.000(2) 0.0056(19) -0.0015(18) C12 0.027(2) 0.021(2) 0.032(3) -0.004(2) 0.0082(19) -0.0031(19) C13 0.025(2) 0.021(3) 0.036(3) 0.001(2) 0.0032(18) -0.0053(18) C14 0.0218(19) 0.022(2) 0.015(2) -0.0014(18) 0.0034(16) -0.0046(17) C15 0.0219(19) 0.019(2) 0.017(2) -0.0009(17) 0.0007(16) -0.0019(16) C16 0.030(2) 0.017(2) 0.025(3) -0.001(2) 0.0036(18) -0.0034(18) C17 0.0229(19) 0.022(2) 0.032(2) -0.008(2) 0.0090(17) 0.0000(19) C18 0.026(2) 0.021(2) 0.026(3) 0.0048(19) 0.0017(18) -0.0054(18) C19 0.025(2) 0.016(2) 0.027(2) -0.005(2) 0.0084(16) -0.0028(19) N1 0.0215(17) 0.025(2) 0.023(2) -0.0002(16) 0.0036(14) -0.0054(15) N2 0.0189(16) 0.025(2) 0.0217(19) -0.0046(16) 0.0042(13) -0.0068(14) O1 0.0128(12) 0.0179(15) 0.0414(19) 0.0097(14) -0.0028(12) -0.0021(11) O2 0.0180(12) 0.0205(15) 0.0306(17) 0.0032(13) -0.0028(12) -0.0059(11) O3 0.0293(14) 0.0204(16) 0.051(2) 0.0147(16) 0.0192(13) 0.0002(13) O4 0.0215(13) 0.0254(16) 0.048(2) 0.0029(15) 0.0216(13) 0.0045(12) O5 0.0193(13) 0.0266(16) 0.0413(19) -0.0023(14) 0.0104(12) -0.0137(12) O6 0.0192(12) 0.0299(17) 0.0276(16) -0.0051(13) 0.0088(11) -0.0113(12) O1W 0.0277(16) 0.044(2) 0.0263(18) 0.0070(17) 0.0012(14) -0.0174(16) O2W 0.0119(15) 0.0252(18) 0.0338(19) 0.0006(14) 0.0015(13) -0.0003(13) O3W 0.0150(15) 0.034(2) 0.037(2) 0.0160(16) 0.0055(14) 0.0021(13) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Co1 O5 2.058(3) . ? Co1 O2W 2.064(3) . ? Co1 O3W 2.088(3) . ? Co1 O1 2.104(2) . ? Co1 O1W 2.135(3) . ? Co1 O6 2.155(3) 2_645 ? C1 C2 1.387(5) . ? C1 C3 1.394(5) 3_656 ? C1 C4 1.518(4) . ? C2 C3 1.392(4) . ? C3 C1 1.394(5) 3_656 ? C3 C5 1.508(5) . ? C4 O2 1.245(4) . ? C4 O1 1.255(4) . ? C5 O4 1.244(4) . ? C5 O3 1.247(4) . ? C10 N1 1.342(5) . ? C10 C12 1.360(5) . ? C11 N1 1.353(5) . ? C11 C13 1.365(5) . ? C12 C14 1.381(5) . ? C13 C14 1.397(5) . ? C14 C15 1.485(5) . ? C15 C17 1.386(5) . ? C15 C16 1.396(5) . ? C16 C18 1.380(5) . ? C17 C19 1.367(5) . ? C18 N2 1.349(5) . ? C19 N2 1.350(5) . ? N1 O5 1.323(3) . ? N2 O6 1.342(3) . ? O6 Co1 2.155(3) 2_655 ? 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 O2W 174.15(12) . . ? O5 Co1 O3W 91.72(11) . . ? O2W Co1 O3W 88.59(12) . . ? O5 Co1 O1 93.45(10) . . ? O2W Co1 O1 86.09(11) . . ? O3W Co1 O1 174.54(11) . . ? O5 Co1 O1W 83.81(12) . . ? O2W Co1 O1W 90.39(13) . . ? O3W Co1 O1W 85.15(14) . . ? O1 Co1 O1W 93.68(11) . . ? O5 Co1 O6 95.48(10) . 2_645 ? O2W Co1 O6 90.37(11) . 2_645 ? O3W Co1 O6 89.03(12) . 2_645 ? O1 Co1 O6 92.20(10) . 2_645 ? O1W Co1 O6 174.11(10) . 2_645 ? C2 C1 C3 119.5(3) . 3_656 ? C2 C1 C4 117.8(3) . . ? C3 C1 C4 122.7(3) 3_656 . ? C1 C2 C3 122.0(3) . . ? C2 C3 C1 118.6(3) . 3_656 ? C2 C3 C5 119.2(3) . . ? C1 C3 C5 121.8(3) 3_656 . ? O2 C4 O1 126.2(3) . . ? O2 C4 C1 118.8(3) . . ? O1 C4 C1 114.9(3) . . ? O4 C5 O3 126.7(3) . . ? O4 C5 C3 114.4(3) . . ? O3 C5 C3 118.9(3) . . ? N1 C10 C12 121.3(4) . . ? N1 C11 C13 120.3(4) . . ? C10 C12 C14 121.4(4) . . ? C11 C13 C14 121.5(4) . . ? C12 C14 C13 116.0(3) . . ? C12 C14 C15 121.0(3) . . ? C13 C14 C15 123.0(3) . . ? C17 C15 C16 116.4(3) . . ? C17 C15 C14 122.5(3) . . ? C16 C15 C14 121.2(3) . . ? C18 C16 C15 121.5(4) . . ? C19 C17 C15 121.7(4) . . ? N2 C18 C16 119.0(4) . . ? N2 C19 C17 119.6(4) . . ? O5 N1 C10 120.4(3) . . ? O5 N1 C11 119.9(3) . . ? C10 N1 C11 119.6(3) . . ? O6 N2 C18 119.7(3) . . ? O6 N2 C19 118.8(3) . . ? C18 N2 C19 121.6(3) . . ? C4 O1 Co1 137.6(2) . . ? N1 O5 Co1 127.6(2) . . ? N2 O6 Co1 119.80(19) . 2_655 ? _diffrn_measured_fraction_theta_max 0.990 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.990 _refine_diff_density_max 0.421 _refine_diff_density_min -0.524 _refine_diff_density_rms 0.107