Supplementary Material (ESI) for Dalton Transactions This journal is © The Royal Society of Chemistry 2003 data_global _journal_name_full 'Dalton Trans.' _journal_coden_Cambridge 0222 loop_ _publ_author_name 'W. David McFadyen' 'Alison M. Funston' 'Ken. Ghiggino' 'Martin J. Grannas' 'Peter A. Tregloan' _publ_contact_author_name 'Dr W. David McFadyen' _publ_contact_author_address ; School of Chemistry University of Melbourne Victoria 3010 AUSTRALIA ; _publ_contact_author_email WDMF@UNIMELB.EDU.AU _publ_section_title ; Sunthesis, Structural Studies and Photophysics of Cobalt(III) Complexes of Anthracenylcyclam Macrocycles ; data_8 _database_code_CSD 211119 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common bis(aminal) _chemical_melting_point 217-221 _chemical_formula_moiety C29H36N4 _chemical_formula_sum 'C29 H36 N4' _chemical_formula_weight 440.62 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 9.9553(6) _cell_length_b 11.6873(5) _cell_length_c 12.1534(5) _cell_angle_alpha 115.186(4) _cell_angle_beta 96.967(4) _cell_angle_gamma 107.303(5) _cell_volume 1170.35(10) _cell_formula_units_Z 2 _cell_measurement_temperature 291(2) _cell_measurement_reflns_used 25 _cell_measurement_theta_min 11.36 _cell_measurement_theta_max 26.60 _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.12 _exptl_crystal_size_mid 0.11 _exptl_crystal_size_min 0.07 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.250 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 476 _exptl_absorpt_coefficient_mu 0.568 _exptl_absorpt_correction_type Gaussian _exptl_absorpt_process_details 'Sheldrick, 1976' _exptl_absorpt_correction_T_min 0.8882 _exptl_absorpt_correction_T_max 0.9759 _exptl_special_details ; ? ; _diffrn_ambient_temperature 291(2) _diffrn_radiation_wavelength 1.54180 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Enraf Nonius CAD4-MachS Diffractometer' _diffrn_measurement_method \w:2\q _diffrn_detector_area_resol_mean ? _diffrn_standards_number 3 _diffrn_standards_interval_count ? _diffrn_standards_interval_time 120 _diffrn_standards_decay_% none _diffrn_reflns_number 5675 _diffrn_reflns_av_R_equivalents 0.0122 _diffrn_reflns_av_sigmaI/netI 0.0198 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 1 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 4.20 _diffrn_reflns_theta_max 74.96 _reflns_number_total 4812 _reflns_number_gt 3859 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CAD-4 Software (Enraf-Nonius, 1989)' _computing_cell_refinement 'CAD-4 Software' _computing_data_reduction 'PROCESS_DATA (Gable et al., 1993)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEPIII (Farrugia, 1997)' _computing_publication_material SHELXL _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^+0.1662P] 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 4812 _refine_ls_number_parameters 341 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0550 _refine_ls_R_factor_gt 0.0443 _refine_ls_wR_factor_ref 0.1263 _refine_ls_wR_factor_gt 0.1174 _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 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 N1 N 0.14868(11) 0.15543(10) 0.25218(8) 0.0358(2) Uani 1 1 d . . . N2 N 0.37463(12) 0.11152(11) 0.37719(10) 0.0430(2) Uani 1 1 d . . . N3 N 0.38123(11) 0.33730(10) 0.50823(9) 0.0412(2) Uani 1 1 d . . . N4 N 0.06868(11) 0.23396(11) 0.43917(9) 0.0418(2) Uani 1 1 d . . . C1 C -0.23242(15) 0.27008(14) 0.02905(12) 0.0465(3) Uani 1 1 d . . . C2 C -0.35643(18) 0.23591(19) 0.07334(16) 0.0628(4) Uani 1 1 d . . . H2 H -0.3422 0.2414 0.1528 0.081(6) Uiso 1 1 calc R . . C3 C -0.4950(2) 0.1955(2) 0.00277(19) 0.0767(5) Uani 1 1 d . . . H3 H -0.5737 0.1733 0.0344 0.102(7) Uiso 1 1 calc R . . C4 C -0.52149(19) 0.1868(2) -0.11777(19) 0.0729(5) Uani 1 1 d . . . H4 H -0.6169 0.1584 -0.1656 0.094(6) Uiso 1 1 calc R . . C5 C -0.40740(18) 0.21977(17) -0.16295(15) 0.0599(4) Uani 1 1 d . . . H5 H -0.4254 0.2146 -0.2422 0.072(5) Uiso 1 1 calc R . . C6 C -0.26017(15) 0.26235(14) -0.09305(13) 0.0468(3) Uani 1 1 d . . . C7 C -0.14377(16) 0.29686(14) -0.14005(13) 0.0491(3) Uani 1 1 d . . . H7 H -0.1623 0.2946 -0.2179 0.061(5) Uiso 1 1 calc R . . C8 C -0.00017(16) 0.33471(13) -0.07448(13) 0.0467(3) Uani 1 1 d . . . C9 C 0.11825(18) 0.36720(15) -0.12563(16) 0.0592(4) Uani 1 1 d . . . H9 H 0.0992 0.3658 -0.2031 0.079(6) Uiso 1 1 calc R . . C10 C 0.2576(2) 0.40000(18) -0.06357(18) 0.0696(5) Uani 1 1 d . . . H10 H 0.3337 0.4211 -0.0981 0.089(6) Uiso 1 1 calc R . . C11 C 0.28741(18) 0.40206(17) 0.05403(18) 0.0680(5) Uani 1 1 d . . . H11 H 0.3834 0.4235 0.0958 0.080(6) Uiso 1 1 calc R . . C12 C 0.17892(16) 0.37346(15) 0.10717(15) 0.0568(4) Uani 1 1 d . . . H12 H 0.2020 0.3760 0.1849 0.061(5) Uiso 1 1 calc R . . C13 C 0.02921(15) 0.33938(13) 0.04637(12) 0.0448(3) Uani 1 1 d . . . C14 C -0.08686(15) 0.30992(13) 0.09892(12) 0.0448(3) Uani 1 1 d . . . C15 C -0.05804(17) 0.32168(15) 0.22923(12) 0.0507(3) Uani 1 1 d . . . H151 H -0.1177 0.3658 0.2745 0.064(5) Uiso 1 1 calc R . . H152 H 0.0441 0.3809 0.2757 0.060(4) Uiso 1 1 calc R . . C16 C -0.09000(14) 0.18463(14) 0.22957(12) 0.0450(3) Uani 1 1 d . . . H16 H -0.1922 0.1258 0.1784 0.056(4) Uiso 1 1 calc R . . C17 C 0.00365(14) 0.10923(13) 0.16651(11) 0.0423(3) Uani 1 1 d . . . H171 H -0.0481 0.0118 0.1349 0.052(4) Uiso 1 1 calc R . . H172 H 0.0165 0.1224 0.0943 0.051(4) Uiso 1 1 calc R . . C18 C 0.22943(15) 0.07880(13) 0.18189(11) 0.0437(3) Uani 1 1 d . . . H181 H 0.2350 0.0903 0.1079 0.050(4) Uiso 1 1 calc R . . H182 H 0.1782 -0.0181 0.1530 0.050(4) Uiso 1 1 calc R . . C19 C 0.38130(15) 0.12866(15) 0.26459(13) 0.0472(3) Uani 1 1 d . . . H191 H 0.4343 0.0773 0.2170 0.062(5) Uiso 1 1 calc R . . H192 H 0.4337 0.2248 0.2909 0.052(4) Uiso 1 1 calc R . . C20 C 0.52318(16) 0.14881(16) 0.45290(15) 0.0548(4) Uani 1 1 d . . . H201 H 0.5725 0.0991 0.3981 0.072(5) Uiso 1 1 calc R . . H202 H 0.5154 0.1211 0.5174 0.068(5) Uiso 1 1 calc R . . C21 C 0.61506(16) 0.30168(17) 0.51660(16) 0.0601(4) Uani 1 1 d . . . H211 H 0.7047 0.3234 0.5764 0.079(5) Uiso 1 1 calc R . . H212 H 0.6419 0.3259 0.4530 0.064(5) Uiso 1 1 calc R . . C22 C 0.53186(15) 0.38536(15) 0.58586(14) 0.0537(4) Uani 1 1 d . . . H221 H 0.5285 0.3801 0.6631 0.067(5) Uiso 1 1 calc R . . H222 H 0.5842 0.4807 0.6097 0.059(4) Uiso 1 1 calc R . . C23 C 0.30501(16) 0.41780(14) 0.58000(12) 0.0494(3) Uani 1 1 d . . . H231 H 0.3635 0.5149 0.6156 0.053(4) Uiso 1 1 calc R . . H232 H 0.2896 0.3996 0.6492 0.060(4) Uiso 1 1 calc R . . C24 C 0.15988(15) 0.37964(13) 0.49275(12) 0.0476(3) Uani 1 1 d . . . H241 H 0.1090 0.4344 0.5393 0.054(4) Uiso 1 1 calc R . . H242 H 0.1762 0.3995 0.4245 0.055(4) Uiso 1 1 calc R . . C25 C -0.07895(14) 0.19682(15) 0.36236(12) 0.0483(3) Uani 1 1 d . . . H251 H -0.1162 0.2651 0.4095 0.060(4) Uiso 1 1 calc R . . H252 H -0.1429 0.1097 0.3517 0.055(4) Uiso 1 1 calc R . . C26 C 0.13884(13) 0.14321(12) 0.36817(10) 0.0366(3) Uani 1 1 d . . . C27 C 0.29681(13) 0.18806(12) 0.45502(11) 0.0383(3) Uani 1 1 d . . . C28 C 0.04825(15) -0.00526(14) 0.33574(13) 0.0480(3) Uani 1 1 d G . . H281 H 0.1040 -0.0608 0.3063 0.054(6) Uiso 0.88(3) 1 calc PR . . H282 H -0.0414 -0.0416 0.2705 0.050(6) Uiso 0.88(3) 1 calc PR . . H283 H 0.0258 -0.0058 0.4102 0.058(6) Uiso 0.88(3) 1 calc PR . . H284 H -0.0450 -0.0113 0.3517 0.08(5) Uiso 0.12(3) 1 calc PR . . H285 H 0.1003 -0.0305 0.3875 0.02(3) Uiso 0.12(3) 1 calc PR . . H286 H 0.0331 -0.0663 0.2478 0.04(4) Uiso 0.12(3) 1 calc PR . . C29 C 0.27815(16) 0.14965(15) 0.56094(13) 0.0504(3) Uani 1 1 d . . . H291 H 0.1964 0.1664 0.5889 0.064(5) Uiso 1 1 calc R . . H292 H 0.3659 0.2045 0.6311 0.066(5) Uiso 1 1 calc R . . H293 H 0.2607 0.0543 0.5286 0.066(5) 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 N1 0.0405(5) 0.0373(5) 0.0284(5) 0.0150(4) 0.0099(4) 0.0150(4) N2 0.0423(6) 0.0443(6) 0.0469(6) 0.0256(5) 0.0119(5) 0.0178(5) N3 0.0392(5) 0.0366(5) 0.0383(5) 0.0166(4) 0.0031(4) 0.0082(4) N4 0.0403(6) 0.0486(6) 0.0332(5) 0.0174(4) 0.0118(4) 0.0165(5) C1 0.0516(8) 0.0499(7) 0.0441(7) 0.0223(6) 0.0129(6) 0.0288(6) C2 0.0611(9) 0.0897(12) 0.0624(9) 0.0454(9) 0.0265(8) 0.0450(9) C3 0.0561(10) 0.1112(16) 0.0920(13) 0.0638(12) 0.0310(9) 0.0446(10) C4 0.0514(9) 0.0932(13) 0.0817(12) 0.0469(11) 0.0094(8) 0.0352(9) C5 0.0599(9) 0.0679(10) 0.0562(9) 0.0321(8) 0.0055(7) 0.0319(8) C6 0.0535(8) 0.0450(7) 0.0450(7) 0.0212(6) 0.0085(6) 0.0264(6) C7 0.0627(9) 0.0467(7) 0.0425(7) 0.0231(6) 0.0122(6) 0.0261(6) C8 0.0552(8) 0.0354(6) 0.0475(7) 0.0178(5) 0.0134(6) 0.0192(6) C9 0.0673(10) 0.0477(8) 0.0627(9) 0.0273(7) 0.0249(8) 0.0194(7) C10 0.0608(10) 0.0578(9) 0.0818(12) 0.0289(9) 0.0293(9) 0.0167(8) C11 0.0472(9) 0.0584(9) 0.0769(11) 0.0201(8) 0.0089(8) 0.0160(7) C12 0.0503(8) 0.0499(8) 0.0556(8) 0.0171(7) 0.0039(7) 0.0179(6) C13 0.0490(7) 0.0347(6) 0.0440(7) 0.0136(5) 0.0074(6) 0.0183(5) C14 0.0531(8) 0.0421(7) 0.0378(6) 0.0152(5) 0.0082(6) 0.0250(6) C15 0.0593(9) 0.0523(8) 0.0378(6) 0.0163(6) 0.0092(6) 0.0288(7) C16 0.0404(7) 0.0506(7) 0.0366(6) 0.0170(6) 0.0050(5) 0.0169(6) C17 0.0478(7) 0.0409(6) 0.0305(6) 0.0133(5) 0.0055(5) 0.0159(5) C18 0.0525(7) 0.0444(7) 0.0360(6) 0.0178(5) 0.0174(5) 0.0220(6) C19 0.0488(7) 0.0519(8) 0.0488(7) 0.0264(6) 0.0215(6) 0.0239(6) C20 0.0471(8) 0.0604(9) 0.0663(9) 0.0375(8) 0.0123(7) 0.0246(7) C21 0.0387(7) 0.0660(10) 0.0741(10) 0.0400(8) 0.0039(7) 0.0143(7) C22 0.0441(7) 0.0492(8) 0.0520(8) 0.0245(6) -0.0035(6) 0.0048(6) C23 0.0569(8) 0.0414(7) 0.0350(6) 0.0115(5) 0.0034(6) 0.0149(6) C24 0.0539(8) 0.0429(7) 0.0361(6) 0.0101(5) 0.0082(6) 0.0218(6) C25 0.0402(7) 0.0607(8) 0.0447(7) 0.0251(6) 0.0146(6) 0.0203(6) C26 0.0393(6) 0.0367(6) 0.0308(5) 0.0165(5) 0.0100(5) 0.0111(5) C27 0.0396(6) 0.0374(6) 0.0363(6) 0.0203(5) 0.0080(5) 0.0104(5) C28 0.0472(7) 0.0432(7) 0.0451(7) 0.0236(6) 0.0084(6) 0.0057(6) C29 0.0515(8) 0.0553(8) 0.0449(7) 0.0320(6) 0.0081(6) 0.0125(6) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag N1 C18 1.4566(15) . Y N1 C17 1.4674(15) . Y N1 C26 1.4879(14) . Y N2 C19 1.4712(16) . Y N2 C27 1.4713(16) . Y N2 C20 1.4727(16) . Y N3 C23 1.4521(17) . Y N3 C22 1.4694(16) . Y N3 C27 1.4843(15) . Y N4 C24 1.4632(17) . Y N4 C25 1.4705(16) . Y N4 C26 1.4715(16) . Y C1 C14 1.4148(18) . ? C1 C2 1.423(2) . ? C1 C6 1.4346(18) . ? C2 C3 1.358(2) . ? C2 H2 0.9300 . ? C3 C4 1.410(3) . ? C3 H3 0.9300 . ? C4 C5 1.346(2) . ? C4 H4 0.9300 . ? C5 C6 1.4220(19) . ? C5 H5 0.9300 . ? C6 C7 1.382(2) . ? C7 C8 1.3862(19) . ? C7 H7 0.9300 . ? C8 C9 1.426(2) . ? C8 C13 1.4366(19) . ? C9 C10 1.351(2) . ? C9 H9 0.9300 . ? C10 C11 1.412(3) . ? C10 H10 0.9300 . ? C11 C12 1.354(2) . ? C11 H11 0.9300 . ? C12 C13 1.4335(19) . ? C12 H12 0.9300 . ? C13 C14 1.411(2) . ? C14 C15 1.5134(18) . ? C15 C16 1.539(2) . ? C15 H151 0.9700 . ? C15 H152 0.9700 . ? C16 C17 1.5232(18) . ? C16 C25 1.5456(17) . ? C16 H16 0.9800 . ? C17 H171 0.9700 . ? C17 H172 0.9700 . ? C18 C19 1.4981(18) . ? C18 H181 0.9700 . ? C18 H182 0.9700 . ? C19 H191 0.9700 . ? C19 H192 0.9700 . ? C20 C21 1.519(2) . ? C20 H201 0.9700 . ? C20 H202 0.9700 . ? C21 C22 1.517(2) . ? C21 H211 0.9700 . ? C21 H212 0.9700 . ? C22 H221 0.9700 . ? C22 H222 0.9700 . ? C23 C24 1.5012(18) . ? C23 H231 0.9700 . ? C23 H232 0.9700 . ? C24 H241 0.9700 . ? C24 H242 0.9700 . ? C25 H251 0.9700 . ? C25 H252 0.9700 . ? C26 C28 1.5429(17) . ? C26 C27 1.5805(16) . ? C27 C29 1.5470(16) . ? C28 H281 0.9600 . ? C28 H282 0.9600 . ? C28 H283 0.9600 . ? C28 H284 0.9600 . ? C28 H285 0.9600 . ? C28 H286 0.9600 . ? C29 H291 0.9600 . ? C29 H292 0.9600 . ? C29 H293 0.9600 . ? 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 C18 N1 C17 108.67(9) . . Y C18 N1 C26 111.93(9) . . Y C17 N1 C26 112.37(9) . . Y C19 N2 C27 112.67(9) . . Y C19 N2 C20 110.45(11) . . Y C27 N2 C20 111.31(10) . . Y C23 N3 C22 110.22(10) . . Y C23 N3 C27 111.50(10) . . Y C22 N3 C27 113.31(10) . . Y C24 N4 C25 111.95(11) . . Y C24 N4 C26 113.01(10) . . Y C25 N4 C26 111.40(9) . . Y C14 C1 C2 123.28(13) . . ? C14 C1 C6 119.82(13) . . ? C2 C1 C6 116.90(13) . . ? C3 C2 C1 121.77(15) . . ? C3 C2 H2 119.1 . . ? C1 C2 H2 119.1 . . ? C2 C3 C4 120.97(17) . . ? C2 C3 H3 119.5 . . ? C4 C3 H3 119.5 . . ? C5 C4 C3 119.39(15) . . ? C5 C4 H4 120.3 . . ? C3 C4 H4 120.3 . . ? C4 C5 C6 121.90(15) . . ? C4 C5 H5 119.0 . . ? C6 C5 H5 119.0 . . ? C7 C6 C5 121.40(13) . . ? C7 C6 C1 119.54(12) . . ? C5 C6 C1 119.06(13) . . ? C6 C7 C8 121.94(13) . . ? C6 C7 H7 119.0 . . ? C8 C7 H7 119.0 . . ? C7 C8 C9 121.19(13) . . ? C7 C8 C13 119.25(13) . . ? C9 C8 C13 119.56(13) . . ? C10 C9 C8 121.20(16) . . ? C10 C9 H9 119.4 . . ? C8 C9 H9 119.4 . . ? C9 C10 C11 119.74(16) . . ? C9 C10 H10 120.1 . . ? C11 C10 H10 120.1 . . ? C12 C11 C10 121.26(16) . . ? C12 C11 H11 119.4 . . ? C10 C11 H11 119.4 . . ? C11 C12 C13 121.48(16) . . ? C11 C12 H12 119.3 . . ? C13 C12 H12 119.3 . . ? C14 C13 C12 123.27(13) . . ? C14 C13 C8 120.00(12) . . ? C12 C13 C8 116.73(13) . . ? C13 C14 C1 119.38(12) . . ? C13 C14 C15 121.12(12) . . ? C1 C14 C15 119.50(13) . . ? C14 C15 C16 115.01(11) . . ? C14 C15 H151 108.5 . . ? C16 C15 H151 108.5 . . ? C14 C15 H152 108.5 . . ? C16 C15 H152 108.5 . . ? H151 C15 H152 107.5 . . ? C17 C16 C15 113.14(11) . . ? C17 C16 C25 109.63(10) . . ? C15 C16 C25 114.09(11) . . ? C17 C16 H16 106.5 . . ? C15 C16 H16 106.5 . . ? C25 C16 H16 106.5 . . ? N1 C17 C16 113.30(9) . . ? N1 C17 H171 108.9 . . ? C16 C17 H171 108.9 . . ? N1 C17 H172 108.9 . . ? C16 C17 H172 108.9 . . ? H171 C17 H172 107.7 . . ? N1 C18 C19 110.15(10) . . ? N1 C18 H181 109.6 . . ? C19 C18 H181 109.6 . . ? N1 C18 H182 109.6 . . ? C19 C18 H182 109.6 . . ? H181 C18 H182 108.1 . . ? N2 C19 C18 110.27(10) . . ? N2 C19 H191 109.6 . . ? C18 C19 H191 109.6 . . ? N2 C19 H192 109.6 . . ? C18 C19 H192 109.6 . . ? H191 C19 H192 108.1 . . ? N2 C20 C21 112.48(11) . . ? N2 C20 H201 109.1 . . ? C21 C20 H201 109.1 . . ? N2 C20 H202 109.1 . . ? C21 C20 H202 109.1 . . ? H201 C20 H202 107.8 . . ? C22 C21 C20 111.32(12) . . ? C22 C21 H211 109.4 . . ? C20 C21 H211 109.4 . . ? C22 C21 H212 109.4 . . ? C20 C21 H212 109.4 . . ? H211 C21 H212 108.0 . . ? N3 C22 C21 112.37(12) . . ? N3 C22 H221 109.1 . . ? C21 C22 H221 109.1 . . ? N3 C22 H222 109.1 . . ? C21 C22 H222 109.1 . . ? H221 C22 H222 107.9 . . ? N3 C23 C24 108.75(10) . . ? N3 C23 H231 109.9 . . ? C24 C23 H231 109.9 . . ? N3 C23 H232 109.9 . . ? C24 C23 H232 109.9 . . ? H231 C23 H232 108.3 . . ? N4 C24 C23 110.99(11) . . ? N4 C24 H241 109.4 . . ? C23 C24 H241 109.4 . . ? N4 C24 H242 109.4 . . ? C23 C24 H242 109.4 . . ? H241 C24 H242 108.0 . . ? N4 C25 C16 116.07(10) . . ? N4 C25 H251 108.3 . . ? C16 C25 H251 108.3 . . ? N4 C25 H252 108.3 . . ? C16 C25 H252 108.3 . . ? H251 C25 H252 107.4 . . ? N4 C26 N1 108.11(9) . . ? N4 C26 C28 109.30(10) . . ? N1 C26 C28 111.95(9) . . ? N4 C26 C27 109.15(9) . . ? N1 C26 C27 110.78(9) . . ? C28 C26 C27 107.50(10) . . ? N2 C27 N3 109.11(10) . . ? N2 C27 C29 108.95(10) . . ? N3 C27 C29 111.64(10) . . ? N2 C27 C26 108.63(9) . . ? N3 C27 C26 110.27(9) . . ? C29 C27 C26 108.18(10) . . ? C26 C28 H281 109.5 . . ? C26 C28 H282 109.5 . . ? H281 C28 H282 109.5 . . ? C26 C28 H283 109.5 . . ? H281 C28 H283 109.5 . . ? H282 C28 H283 109.5 . . ? C26 C28 H284 109.5 . . ? H281 C28 H284 141.1 . . ? H282 C28 H284 56.3 . . ? H283 C28 H284 56.3 . . ? C26 C28 H285 109.5 . . ? H281 C28 H285 56.3 . . ? H282 C28 H285 141.1 . . ? H283 C28 H285 56.3 . . ? H284 C28 H285 109.5 . . ? C26 C28 H286 109.5 . . ? H281 C28 H286 56.3 . . ? H282 C28 H286 56.3 . . ? H283 C28 H286 141.1 . . ? H284 C28 H286 109.5 . . ? H285 C28 H286 109.5 . . ? C27 C29 H291 109.5 . . ? C27 C29 H292 109.5 . . ? H291 C29 H292 109.5 . . ? C27 C29 H293 109.5 . . ? H291 C29 H293 109.5 . . ? H292 C29 H293 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C14 C1 C2 C3 -178.72(16) . . . . ? C6 C1 C2 C3 1.1(2) . . . . ? C1 C2 C3 C4 -0.4(3) . . . . ? C2 C3 C4 C5 -0.4(3) . . . . ? C3 C4 C5 C6 0.6(3) . . . . ? C4 C5 C6 C7 -179.58(16) . . . . ? C4 C5 C6 C1 0.1(2) . . . . ? C14 C1 C6 C7 -1.40(19) . . . . ? C2 C1 C6 C7 178.77(13) . . . . ? C14 C1 C6 C5 178.89(12) . . . . ? C2 C1 C6 C5 -0.9(2) . . . . ? C5 C6 C7 C8 -178.11(13) . . . . ? C1 C6 C7 C8 2.2(2) . . . . ? C6 C7 C8 C9 178.66(13) . . . . ? C6 C7 C8 C13 -0.49(19) . . . . ? C7 C8 C9 C10 -177.95(14) . . . . ? C13 C8 C9 C10 1.2(2) . . . . ? C8 C9 C10 C11 0.1(2) . . . . ? C9 C10 C11 C12 -0.9(3) . . . . ? C10 C11 C12 C13 0.2(2) . . . . ? C11 C12 C13 C14 -179.53(14) . . . . ? C11 C12 C13 C8 1.1(2) . . . . ? C7 C8 C13 C14 -2.02(18) . . . . ? C9 C8 C13 C14 178.81(12) . . . . ? C7 C8 C13 C12 177.40(12) . . . . ? C9 C8 C13 C12 -1.77(18) . . . . ? C12 C13 C14 C1 -176.62(12) . . . . ? C8 C13 C14 C1 2.75(18) . . . . ? C12 C13 C14 C15 4.03(19) . . . . ? C8 C13 C14 C15 -176.59(11) . . . . ? C2 C1 C14 C13 178.76(14) . . . . ? C6 C1 C14 C13 -1.06(19) . . . . ? C2 C1 C14 C15 -1.9(2) . . . . ? C6 C1 C14 C15 178.29(11) . . . . ? C13 C14 C15 C16 -101.13(15) . . . . ? C1 C14 C15 C16 79.53(16) . . . . ? C14 C15 C16 C17 61.14(15) . . . . ? C14 C15 C16 C25 -172.60(11) . . . . ? C18 N1 C17 C16 -178.97(10) . . . . ? C26 N1 C17 C16 56.60(13) . . . . ? C15 C16 C17 N1 84.46(13) . . . . ? C25 C16 C17 N1 -44.14(14) . . . . ? C17 N1 C18 C19 176.96(10) . . . . ? C26 N1 C18 C19 -58.35(13) . . . . ? C27 N2 C19 C18 -59.88(14) . . . . ? C20 N2 C19 C18 174.95(10) . . . . ? N1 C18 C19 N2 59.42(14) . . . . ? C19 N2 C20 C21 69.18(16) . . . . ? C27 N2 C20 C21 -56.76(15) . . . . ? N2 C20 C21 C22 49.27(17) . . . . ? C23 N3 C22 C21 178.25(12) . . . . ? C27 N3 C22 C21 52.52(15) . . . . ? C20 C21 C22 N3 -46.77(17) . . . . ? C22 N3 C23 C24 172.13(11) . . . . ? C27 N3 C23 C24 -61.12(14) . . . . ? C25 N4 C24 C23 174.93(10) . . . . ? C26 N4 C24 C23 -58.31(14) . . . . ? N3 C23 C24 N4 60.43(14) . . . . ? C24 N4 C25 C16 75.63(14) . . . . ? C26 N4 C25 C16 -52.01(15) . . . . ? C17 C16 C25 N4 42.80(16) . . . . ? C15 C16 C25 N4 -85.27(15) . . . . ? C24 N4 C26 N1 -67.78(12) . . . . ? C25 N4 C26 N1 59.27(12) . . . . ? C24 N4 C26 C28 170.12(10) . . . . ? C25 N4 C26 C28 -62.82(12) . . . . ? C24 N4 C26 C27 52.80(12) . . . . ? C25 N4 C26 C27 179.86(9) . . . . ? C18 N1 C26 N4 174.58(9) . . . . ? C17 N1 C26 N4 -62.81(12) . . . . ? C18 N1 C26 C28 -64.97(13) . . . . ? C17 N1 C26 C28 57.64(13) . . . . ? C18 N1 C26 C27 55.02(12) . . . . ? C17 N1 C26 C27 177.63(9) . . . . ? C19 N2 C27 N3 -64.95(12) . . . . ? C20 N2 C27 N3 59.75(12) . . . . ? C19 N2 C27 C29 172.94(10) . . . . ? C20 N2 C27 C29 -62.36(13) . . . . ? C19 N2 C27 C26 55.30(13) . . . . ? C20 N2 C27 C26 180.00(10) . . . . ? C23 N3 C27 N2 176.63(9) . . . . ? C22 N3 C27 N2 -58.32(13) . . . . ? C23 N3 C27 C29 -62.89(13) . . . . ? C22 N3 C27 C29 62.15(14) . . . . ? C23 N3 C27 C26 57.40(12) . . . . ? C22 N3 C27 C26 -177.56(10) . . . . ? N4 C26 C27 N2 -171.18(9) . . . . ? N1 C26 C27 N2 -52.25(12) . . . . ? C28 C26 C27 N2 70.37(12) . . . . ? N4 C26 C27 N3 -51.65(12) . . . . ? N1 C26 C27 N3 67.28(12) . . . . ? C28 C26 C27 N3 -170.10(10) . . . . ? N4 C26 C27 C29 70.70(12) . . . . ? N1 C26 C27 C29 -170.37(10) . . . . ? C28 C26 C27 C29 -47.75(13) . . . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 74.96 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.120 _refine_diff_density_min -0.202 _refine_diff_density_rms 0.048 #===END data_coabs97 _database_code_CSD 211120 _audit_creation_method SHELXL-97 _chemical_name_systematic ; trans-[Co(6-(anthracen-9-ylmethyl)-1,4,8,11-tetraazacyclotetradecane)Cl2] Cl.4H2O ; _chemical_name_common ; trans-(Co(6-(anthracen-9-ylmethyl)-1,4,8,11- tetraazacyclotetradecane)Cl2) Cl.4H2O ; _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C25 H44 Cl3 Co N4 O5' _chemical_formula_weight 645.92 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Co Co 0.3494 0.9721 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P21 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 10.8717(15) _cell_length_b 6.3706(8) _cell_length_c 23.310(5) _cell_angle_alpha 90.00 _cell_angle_beta 91.034(12) _cell_angle_gamma 90.00 _cell_volume 1614.2(4) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 25 _cell_measurement_theta_min 7.83 _cell_measurement_theta_max 13.64 _exptl_crystal_description prismatic _exptl_crystal_colour green _exptl_crystal_size_max 0.37 _exptl_crystal_size_mid 0.09 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.329 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 680 _exptl_absorpt_coefficient_mu 0.818 _exptl_absorpt_correction_type Gaussian _exptl_absorpt_correction_T_min 0.8625 _exptl_absorpt_correction_T_max 0.9240 _exptl_absorpt_process_details '(Sheldrick, 1976)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Enraf-Nonius CAD-4 MachS Diffractometer' _diffrn_measurement_method \w:2\q _diffrn_detector_area_resol_mean ? _diffrn_standards_number 3 _diffrn_standards_interval_count ? _diffrn_standards_interval_time 120 _diffrn_standards_decay_% 0 _diffrn_reflns_number 3639 _diffrn_reflns_av_R_equivalents 0.0271 _diffrn_reflns_av_sigmaI/netI 0.0659 _diffrn_reflns_limit_h_min -1 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -27 _diffrn_reflns_limit_l_max 27 _diffrn_reflns_theta_min 2.05 _diffrn_reflns_theta_max 24.98 _reflns_number_total 3112 _reflns_number_gt 2066 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CAD-4 Software (Enraf-Nonius, 1989)' _computing_cell_refinement 'CAD-4 Software' _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEPIII (Farrugia, 1997)' _computing_publication_material 'WINGX v1.64.01 (Farrugia, 1999)' _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^)+(0.0994P)^2^+0.4060P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.03(6) _refine_ls_number_reflns 3112 _refine_ls_number_parameters 334 _refine_ls_number_restraints 4 _refine_ls_R_factor_all 0.1103 _refine_ls_R_factor_gt 0.0665 _refine_ls_wR_factor_ref 0.1843 _refine_ls_wR_factor_gt 0.1584 _refine_ls_goodness_of_fit_ref 1.087 _refine_ls_restrained_S_all 1.087 _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 0.10877(12) 0.9627(2) 0.83923(6) 0.0417(4) Uani 1 1 d . . . Cl1 Cl 0.1972(3) 0.6927(3) 0.79279(13) 0.0564(9) Uani 1 1 d . . . Cl2 Cl 0.0211(3) 1.2333(4) 0.88554(14) 0.0553(9) Uani 1 1 d . . . Cl3 Cl 0.4769(5) 0.6230(9) 0.9109(3) 0.152(2) Uani 1 1 d . . . N1 N -0.0285(7) 0.9639(17) 0.7837(3) 0.055(2) Uani 1 1 d . . . H1N H -0.0745 1.0787 0.7922 0.061(5) Uiso 1 1 calc R . . N2 N 0.0115(10) 0.7557(16) 0.8823(4) 0.048(3) Uani 1 1 d . . . H2N H 0.0421 0.6280 0.8724 0.061(5) Uiso 1 1 calc R . . N3 N 0.2485(7) 0.9537(17) 0.8943(3) 0.0460(19) Uani 1 1 d . . . H3N H 0.2942 0.8393 0.8851 0.061(5) Uiso 1 1 calc R . . N4 N 0.2035(8) 1.1677(15) 0.7959(4) 0.047(2) Uani 1 1 d . . . H4N H 0.1733 1.2954 0.8061 0.061(5) Uiso 1 1 calc R . . C1 C -0.0021(11) 0.981(2) 0.7215(4) 0.065(3) Uani 1 1 d . . . H11 H -0.0795 0.9846 0.7002 0.061(5) Uiso 1 1 calc R . . H12 H 0.0418 0.8559 0.7098 0.061(5) Uiso 1 1 calc R . . C2 C -0.1086(12) 0.778(2) 0.7956(6) 0.074(4) Uani 1 1 d . . . H21 H -0.0735 0.6516 0.7793 0.061(5) Uiso 1 1 calc R . . H22 H -0.1901 0.7984 0.7790 0.061(5) Uiso 1 1 calc R . . C3 C -0.1152(10) 0.759(2) 0.8596(5) 0.066(3) Uani 1 1 d . . . H31 H -0.1596 0.8771 0.8753 0.061(5) Uiso 1 1 calc R . . H32 H -0.1576 0.6308 0.8700 0.061(5) Uiso 1 1 calc R . . C4 C 0.0166(10) 0.7609(18) 0.9454(4) 0.056(3) Uani 1 1 d . . . H41 H -0.0308 0.6445 0.9602 0.061(5) Uiso 1 1 calc R . . H42 H -0.0209 0.8900 0.9586 0.061(5) Uiso 1 1 calc R . . C5 C 0.1445(11) 0.7480(19) 0.9687(5) 0.061(3) Uani 1 1 d . . . H51 H 0.1834 0.6236 0.9533 0.061(5) Uiso 1 1 calc R . . H52 H 0.1417 0.7320 1.0100 0.061(5) Uiso 1 1 calc R . . C6 C 0.2228(10) 0.937(2) 0.9549(4) 0.061(3) Uani 1 1 d . . . H61 H 0.1807 1.0634 0.9672 0.061(5) Uiso 1 1 calc R . . H62 H 0.2999 0.9281 0.9764 0.061(5) Uiso 1 1 calc R . . C7 C 0.3254(10) 1.1420(18) 0.8817(4) 0.054(3) Uani 1 1 d . . . H71 H 0.2889 1.2667 0.8982 0.061(5) Uiso 1 1 calc R . . H72 H 0.4075 1.1247 0.8980 0.061(5) Uiso 1 1 calc R . . C8 C 0.3309(10) 1.1627(18) 0.8185(4) 0.054(3) Uani 1 1 d . . . H81 H 0.3736 1.2908 0.8083 0.061(5) Uiso 1 1 calc R . . H82 H 0.3749 1.0447 0.8024 0.061(5) Uiso 1 1 calc R . . C9 C 0.2012(10) 1.1662(18) 0.7323(4) 0.054(3) Uani 1 1 d . . . H91 H 0.2427 1.0406 0.7192 0.061(5) Uiso 1 1 calc R . . H92 H 0.2473 1.2863 0.7188 0.061(5) Uiso 1 1 calc R . . C10 C 0.0731(11) 1.1725(18) 0.7056(4) 0.059(3) Uani 1 1 d . . . H10 H 0.0308 1.2988 0.7189 0.061(5) Uiso 1 1 calc R . . C11 C 0.0763(13) 1.176(2) 0.6406(5) 0.073(3) Uani 1 1 d . . . H111 H 0.0014 1.1107 0.6259 0.061(5) Uiso 1 1 calc R . . H112 H 0.1446 1.0893 0.6286 0.061(5) Uiso 1 1 calc R . . C12 C 0.0890(12) 1.3974(18) 0.6119(4) 0.061(3) Uani 1 1 d . . . C13 C -0.0153(13) 1.5135(18) 0.6039(5) 0.064(3) Uani 1 1 d . . . C14 C -0.1286(14) 1.466(3) 0.6274(6) 0.093(4) Uani 1 1 d . . . H14 H -0.1344 1.3490 0.6511 0.061(5) Uiso 1 1 calc R . . C15 C -0.2319(18) 1.584(4) 0.6173(9) 0.138(8) Uani 1 1 d . . . H15 H -0.3068 1.5440 0.6326 0.061(5) Uiso 1 1 calc R . . C16 C -0.223(3) 1.761(5) 0.5843(10) 0.153(10) Uani 1 1 d . . . H16 H -0.2928 1.8444 0.5788 0.061(5) Uiso 1 1 calc R . . C17 C -0.124(2) 1.815(3) 0.5613(8) 0.127(8) Uani 1 1 d . . . H17 H -0.1232 1.9325 0.5377 0.061(5) Uiso 1 1 calc R . . C18 C -0.0162(19) 1.699(2) 0.5705(5) 0.087(5) Uani 1 1 d . . . C19 C 0.094(2) 1.766(2) 0.5481(6) 0.098(6) Uani 1 1 d . . . H19 H 0.0948 1.8894 0.5267 0.061(5) Uiso 1 1 calc R . . C20 C 0.201(2) 1.656(3) 0.5563(6) 0.101(6) Uani 1 1 d D . . C21 C 0.319(2) 1.734(4) 0.5319(8) 0.151(10) Uani 1 1 d D . . H201 H 0.3229 1.8587 0.5111 0.061(5) Uiso 1 1 calc R . . C22 C 0.415(4) 1.620(4) 0.5414(9) 0.230(19) Uani 1 1 d D . . H202 H 0.4870 1.6695 0.5251 0.061(5) Uiso 1 1 calc R . . C23 C 0.4275(18) 1.423(6) 0.5742(10) 0.174(12) Uani 1 1 d D . . H23 H 0.5026 1.3563 0.5808 0.061(5) Uiso 1 1 calc R . . C24 C 0.3177(19) 1.345(3) 0.5944(6) 0.117(6) Uani 1 1 d D . . H24 H 0.3175 1.2137 0.6118 0.061(5) Uiso 1 1 calc R . . C25 C 0.2002(14) 1.463(2) 0.5894(5) 0.079(3) Uani 1 1 d D . . O1S O 0.7395(7) 1.2749(17) 0.7746(3) 0.078(3) Uani 1 1 d . . . O2S O 0.6269(10) 0.947(3) 0.9745(5) 0.142(4) Uani 1 1 d . . . O3S O 0.6692(10) 0.282(3) 0.8987(5) 0.137(5) Uani 1 1 d . . . O4SA O 0.566(2) 0.642(6) 0.7808(11) 0.298(12) Uiso 1 1 d . . . O5SA O 0.549(2) 1.028(7) 0.6993(12) 0.357(15) 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 0.0533(7) 0.0168(5) 0.0552(7) -0.0010(6) 0.0081(5) 0.0001(6) Cl1 0.079(2) 0.0216(13) 0.070(2) -0.0052(12) 0.0159(17) 0.0029(12) Cl2 0.071(2) 0.0226(13) 0.073(2) -0.0017(12) 0.0177(16) 0.0058(12) Cl3 0.156(5) 0.078(3) 0.220(6) -0.030(4) -0.004(4) 0.002(3) N1 0.069(5) 0.027(4) 0.070(5) 0.000(6) 0.002(4) -0.005(6) N2 0.068(7) 0.020(5) 0.055(6) -0.002(4) 0.010(5) 0.000(5) N3 0.058(4) 0.029(4) 0.052(4) 0.008(5) 0.006(4) 0.004(6) N4 0.058(6) 0.023(5) 0.060(6) -0.001(4) 0.017(5) -0.001(4) C1 0.087(7) 0.042(6) 0.065(7) -0.013(7) -0.008(6) -0.013(8) C2 0.070(8) 0.052(8) 0.098(10) 0.016(8) -0.020(7) -0.001(7) C3 0.066(8) 0.040(6) 0.093(9) 0.003(7) 0.016(7) -0.020(6) C4 0.073(8) 0.032(5) 0.063(7) 0.000(5) 0.019(6) 0.001(6) C5 0.085(9) 0.037(6) 0.062(7) 0.008(6) 0.015(6) 0.007(6) C6 0.077(7) 0.054(8) 0.053(6) 0.011(7) 0.003(5) 0.017(7) C7 0.054(6) 0.040(6) 0.067(7) -0.004(6) 0.000(5) -0.012(6) C8 0.060(7) 0.031(5) 0.072(7) 0.004(5) 0.014(6) 0.000(5) C9 0.081(8) 0.032(5) 0.050(6) 0.004(5) 0.019(6) -0.005(6) C10 0.095(9) 0.032(6) 0.049(6) 0.005(5) -0.009(6) 0.004(6) C11 0.106(10) 0.046(6) 0.066(7) 0.004(6) 0.003(7) -0.004(7) C12 0.096(9) 0.041(6) 0.045(6) 0.003(5) 0.000(6) -0.007(6) C13 0.096(9) 0.047(7) 0.050(6) -0.007(5) -0.021(6) -0.015(7) C14 0.123(11) 0.071(9) 0.084(9) 0.014(10) -0.020(8) 0.004(12) C15 0.089(12) 0.18(2) 0.140(16) 0.028(17) -0.047(11) -0.003(14) C16 0.16(2) 0.16(3) 0.14(2) 0.028(19) -0.046(17) 0.05(2) C17 0.22(3) 0.062(10) 0.094(14) 0.010(9) -0.062(16) 0.002(15) C18 0.164(16) 0.048(7) 0.047(7) -0.002(6) -0.019(9) 0.000(10) C19 0.200(19) 0.039(7) 0.055(8) 0.004(6) 0.007(11) 0.003(11) C20 0.189(18) 0.062(10) 0.052(8) -0.020(8) 0.033(10) -0.048(12) C21 0.22(3) 0.098(16) 0.135(17) 0.014(14) 0.044(18) -0.041(18) C22 0.28(5) 0.18(3) 0.23(3) 0.11(3) 0.02(3) -0.12(3) C23 0.099(13) 0.23(3) 0.20(2) 0.02(3) 0.055(14) 0.04(2) C24 0.175(17) 0.090(12) 0.088(11) -0.006(9) 0.059(12) -0.026(13) C25 0.131(11) 0.054(7) 0.052(6) -0.003(7) 0.015(7) 0.001(10) O1S 0.071(5) 0.087(7) 0.076(5) 0.006(5) 0.015(4) 0.025(5) O2S 0.144(9) 0.111(10) 0.170(10) -0.027(11) -0.015(8) -0.012(10) O3S 0.113(8) 0.153(13) 0.145(10) 0.010(10) 0.022(7) 0.021(9) _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 N4 1.955(9) . ? Co1 N1 1.959(8) . ? Co1 N3 1.972(8) . ? Co1 N2 1.976(10) . ? Co1 Cl2 2.254(3) . ? Co1 Cl1 2.257(3) . ? N1 C1 1.486(13) . ? N1 C2 1.499(16) . ? N2 C3 1.466(15) . ? N2 C4 1.471(13) . ? N3 C6 1.451(11) . ? N3 C7 1.494(14) . ? N4 C8 1.474(13) . ? N4 C9 1.483(12) . ? C1 C10 1.519(17) . ? C2 C3 1.501(16) . ? C4 C5 1.486(15) . ? C5 C6 1.514(17) . ? C7 C8 1.483(14) . ? C9 C10 1.517(14) . ? C10 C11 1.515(15) . ? C11 C12 1.571(16) . ? C12 C13 1.364(16) . ? C12 C25 1.390(17) . ? C13 C14 1.390(18) . ? C13 C18 1.417(17) . ? C14 C15 1.37(2) . ? C15 C16 1.37(3) . ? C16 C17 1.26(3) . ? C17 C18 1.40(2) . ? C18 C19 1.38(2) . ? C19 C20 1.37(2) . ? C20 C25 1.46(2) . ? C20 C21 1.50(3) . ? C21 C22 1.29(4) . ? C22 C23 1.48(4) . ? C23 C24 1.38(3) . ? C24 C25 1.48(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 N4 Co1 N1 93.3(4) . . ? N4 Co1 N3 87.1(4) . . ? N1 Co1 N3 178.4(5) . . ? N4 Co1 N2 179.3(5) . . ? N1 Co1 N2 86.0(4) . . ? N3 Co1 N2 93.6(4) . . ? N4 Co1 Cl2 88.1(3) . . ? N1 Co1 Cl2 89.4(3) . . ? N3 Co1 Cl2 92.2(3) . . ? N2 Co1 Cl2 91.8(3) . . ? N4 Co1 Cl1 91.6(3) . . ? N1 Co1 Cl1 90.7(3) . . ? N3 Co1 Cl1 87.7(3) . . ? N2 Co1 Cl1 88.4(3) . . ? Cl2 Co1 Cl1 179.75(15) . . ? C1 N1 C2 111.2(10) . . ? C1 N1 Co1 119.1(6) . . ? C2 N1 Co1 108.2(7) . . ? C3 N2 C4 112.3(9) . . ? C3 N2 Co1 108.3(7) . . ? C4 N2 Co1 118.8(8) . . ? C6 N3 C7 111.5(9) . . ? C6 N3 Co1 118.5(6) . . ? C7 N3 Co1 106.1(7) . . ? C8 N4 C9 110.8(8) . . ? C8 N4 Co1 107.6(7) . . ? C9 N4 Co1 120.9(7) . . ? N1 C1 C10 114.3(10) . . ? N1 C2 C3 106.6(11) . . ? N2 C3 C2 107.4(9) . . ? N2 C4 C5 112.4(9) . . ? C4 C5 C6 113.9(10) . . ? N3 C6 C5 112.5(11) . . ? C8 C7 N3 107.4(9) . . ? N4 C8 C7 107.6(8) . . ? N4 C9 C10 114.2(8) . . ? C11 C10 C9 111.9(10) . . ? C11 C10 C1 106.1(9) . . ? C9 C10 C1 111.9(9) . . ? C10 C11 C12 116.2(10) . . ? C13 C12 C25 120.9(12) . . ? C13 C12 C11 117.8(12) . . ? C25 C12 C11 120.9(13) . . ? C12 C13 C14 124.7(13) . . ? C12 C13 C18 121.6(14) . . ? C14 C13 C18 113.7(15) . . ? C15 C14 C13 122.9(18) . . ? C14 C15 C16 119(2) . . ? C17 C16 C15 122(3) . . ? C16 C17 C18 121(2) . . ? C19 C18 C17 120.7(16) . . ? C19 C18 C13 118.0(16) . . ? C17 C18 C13 121.3(17) . . ? C20 C19 C18 122.1(15) . . ? C19 C20 C25 119.4(16) . . ? C19 C20 C21 120.7(19) . . ? C25 C20 C21 120(2) . . ? C22 C21 C20 116(3) . . ? C21 C22 C23 129(3) . . ? C24 C23 C22 114(2) . . ? C23 C24 C25 123(2) . . ? C12 C25 C20 118.0(15) . . ? C12 C25 C24 125.0(13) . . ? C20 C25 C24 117.0(15) . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 24.98 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.541 _refine_diff_density_min -0.407 _refine_diff_density_rms 0.087 #===END data_[Co(12)Cl2] _database_code_CSD 211121 _audit_creation_method SHELXL-97 _chemical_name_systematic ; dichloro(5,7-hydroxy-6-oxo-1,4,8,11-tetraazacyclotetradecane-5,7- diene)cobalt( ; _chemical_name_common ;dichloro(5,7-hydroxy-6-oxo-1,4,8,11-tetraazacyclotetradecane- 5,7-diene)cobalt( ; _chemical_melting_point ? _chemical_formula_moiety C10H19N4O4Cl2Co _chemical_formula_sum 'C10 H17 Cl2 Co N4 O3.50' _chemical_formula_weight 379.11 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 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0311 0.0180 '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' Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M Pnnm loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z' '-x+1/2, y+1/2, z+1/2' 'x+1/2, -y+1/2, z+1/2' '-x, -y, -z' 'x, y, -z' 'x-1/2, -y-1/2, -z-1/2' '-x-1/2, y-1/2, -z-1/2' _cell_length_a 10.0111(11) _cell_length_b 14.891(3) _cell_length_c 9.692(2) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1444.8(4) _cell_formula_units_Z 4 _cell_measurement_temperature 150(1) _cell_measurement_reflns_used 25 _cell_measurement_theta_min 10.97 _cell_measurement_theta_max 27.91 _exptl_crystal_description cube _exptl_crystal_colour green _exptl_crystal_size_max 0.093 _exptl_crystal_size_mid 0.064 _exptl_crystal_size_min 0.057 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.743 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 776 _exptl_absorpt_coefficient_mu 12.887 _exptl_absorpt_correction_type Gaussian _exptl_absorpt_correction_T_min 0.1303 _exptl_absorpt_correction_T_max 0.3375 _exptl_absorpt_process_details 'Sheldrick, 1976' _exptl_special_details ; dichloro(5,7-hydroxy-6-oxo-1,4,8,11-tetraazacyclotetradecane-5,7- diene)cobalt( ; _diffrn_ambient_temperature 150(1) _diffrn_radiation_wavelength 1.54180 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator nickel _diffrn_measurement_device_type ? _diffrn_measurement_method \w:2\q _diffrn_detector_area_resol_mean ? _diffrn_standards_number 3 _diffrn_standards_interval_count ? _diffrn_standards_interval_time 120 _diffrn_standards_decay_% 4 _diffrn_reflns_number 1274 _diffrn_reflns_av_R_equivalents 0.0000 _diffrn_reflns_av_sigmaI/netI 0.0613 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 5.32 _diffrn_reflns_theta_max 69.95 _reflns_number_total 1274 _reflns_number_gt 848 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CAD-4 Software (Enraf-Nonius, 1989)' _computing_cell_refinement 'CAD-4 Software' _computing_data_reduction 'PROCESS_DATA (Gable et al., 1993)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEPIII for Windows (Farrugia, 1997)' _computing_publication_material SHELXL _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^)+(0.1680P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 1274 _refine_ls_number_parameters 113 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1199 _refine_ls_R_factor_gt 0.0854 _refine_ls_wR_factor_ref 0.2472 _refine_ls_wR_factor_gt 0.2246 _refine_ls_goodness_of_fit_ref 1.039 _refine_ls_restrained_S_all 1.039 _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 Co Co 0.18126(17) 0.28042(12) 0.0000 0.0295(6) Uani 1 2 d S . . N1 N 0.2349(7) 0.3623(4) 0.1497(8) 0.0339(17) Uani 1 1 d . . . H1 H 0.3248 0.3556 0.1593 0.07(4) Uiso 1 1 calc R . . C2 C 0.1758(9) 0.3297(6) 0.2780(11) 0.041(2) Uani 1 1 d . . . H2A H 0.0827 0.3472 0.2832 0.03(2) Uiso 1 1 calc R . . H2B H 0.2225 0.3550 0.3566 0.08(4) Uiso 1 1 calc R . . C3 C 0.1880(9) 0.2272(6) 0.2789(11) 0.039(2) Uani 1 1 d . . . H3A H 0.2803 0.2090 0.2905 0.07(4) Uiso 1 1 calc R . . H3B H 0.1353 0.2015 0.3531 0.018(19) Uiso 1 1 calc R . . N4 N 0.1366(7) 0.1983(5) 0.1437(9) 0.0365(17) Uani 1 1 d . . . C5 C 0.0600(8) 0.1294(6) 0.1374(10) 0.034(2) Uani 1 1 d . . . O5 O 0.0264(6) 0.0807(4) 0.2422(6) 0.0356(15) Uani 1 1 d . . . H5 H 0.00(2) 0.030(10) 0.221(16) 0.039 Uiso 0.50 1 d P . . C6 C -0.0036(11) 0.1056(8) 0.0000 0.034(3) Uani 1 2 d S . . O6 O -0.1061(8) 0.0654(5) 0.0000 0.038(2) Uani 1 2 d S . . C13 C 0.2755(11) 0.4929(8) 0.0000 0.036(3) Uani 1 2 d S . . H13A H 0.2734 0.5580 0.0000 0.07(5) Uiso 1 2 calc SR . . H13B H 0.3686 0.4747 0.0000 0.00(2) Uiso 1 2 calc SR . . C14 C 0.2114(9) 0.4597(6) 0.1323(11) 0.040(2) Uani 1 1 d . . . H14A H 0.2487 0.4919 0.2103 0.02(2) Uiso 1 1 calc R . . H14B H 0.1161 0.4714 0.1295 0.07(3) Uiso 1 1 calc R . . Cl2 Cl -0.0282(3) 0.33218(19) 0.0000 0.0342(8) Uani 1 2 d S . . Cl3 Cl 0.3936(3) 0.2285(2) 0.0000 0.0413(8) Uani 1 2 d S . . O1 O 0.5000 0.0000 0.0000 0.239(19) Uiso 1 4 d S . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Co 0.0250(9) 0.0206(11) 0.0430(12) 0.000 0.000 0.0001(7) N1 0.030(3) 0.026(4) 0.045(4) 0.000(4) 0.001(3) -0.005(3) C2 0.049(5) 0.023(4) 0.050(5) -0.013(5) -0.004(5) -0.007(4) C3 0.040(4) 0.032(5) 0.045(5) 0.011(5) -0.009(4) -0.005(4) N4 0.033(3) 0.031(4) 0.045(4) 0.001(4) -0.009(4) -0.003(3) C5 0.032(4) 0.022(4) 0.048(5) 0.001(5) 0.000(4) -0.001(3) O5 0.048(3) 0.023(3) 0.036(3) -0.001(3) 0.003(3) -0.008(3) C6 0.028(6) 0.021(6) 0.053(8) 0.000 0.000 0.004(4) O6 0.039(4) 0.027(5) 0.049(5) 0.000 0.000 0.001(3) C13 0.031(6) 0.020(6) 0.056(8) 0.000 0.000 -0.003(5) C14 0.041(4) 0.026(4) 0.054(6) -0.006(5) 0.010(5) -0.003(3) Cl2 0.0243(12) 0.0285(16) 0.0498(18) 0.000 0.000 0.0024(10) Cl3 0.0298(13) 0.0365(17) 0.058(2) 0.000 0.000 0.0070(12) _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 N4 1.907(8) 6 Y Co N4 1.907(8) . Y Co N1 1.970(7) 6 Y Co N1 1.970(7) . Y Co Cl2 2.234(3) . Y Co Cl3 2.262(3) . Y N1 C2 1.460(13) . Y N1 C14 1.479(11) . Y N1 H1 0.9100 . ? C2 C3 1.532(12) . Y C2 H2A 0.9700 . ? C2 H2B 0.9700 . ? C3 N4 1.472(12) . Y C3 H3A 0.9700 . ? C3 H3B 0.9700 . ? N4 C5 1.282(10) . Y C5 O5 1.292(10) . Y C5 C6 1.518(10) . Y O5 H5 0.84(17) . ? C6 O6 1.188(14) . Y C6 C5 1.518(10) 6 Y C13 C14 1.516(11) 6 Y C13 C14 1.516(11) . Y C13 H13A 0.9700 . ? C13 H13B 0.9700 . ? C14 H14A 0.9700 . ? C14 H14B 0.9700 . ? 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 N4 Co N4 93.8(4) 6 . Y N4 Co N1 85.6(3) 6 6 Y N4 Co N1 177.5(3) . 6 Y N4 Co N1 177.5(3) 6 . Y N4 Co N1 85.6(3) . . Y N1 Co N1 94.9(4) 6 . Y N4 Co Cl2 90.1(2) 6 . Y N4 Co Cl2 90.1(2) . . Y N1 Co Cl2 92.4(2) 6 . Y N1 Co Cl2 92.4(2) . . Y N4 Co Cl3 90.1(2) 6 . Y N4 Co Cl3 90.1(2) . . Y N1 Co Cl3 87.4(2) 6 . Y N1 Co Cl3 87.4(2) . . Y Cl2 Co Cl3 179.80(13) . . Y C2 N1 C14 111.1(7) . . ? C2 N1 Co 108.1(5) . . ? C14 N1 Co 118.7(6) . . ? C2 N1 H1 106.1 . . ? C14 N1 H1 106.1 . . ? Co N1 H1 106.1 . . ? N1 C2 C3 107.7(8) . . ? N1 C2 H2A 110.2 . . ? C3 C2 H2A 110.2 . . ? N1 C2 H2B 110.2 . . ? C3 C2 H2B 110.2 . . ? H2A C2 H2B 108.5 . . ? N4 C3 C2 105.0(7) . . ? N4 C3 H3A 110.8 . . ? C2 C3 H3A 110.8 . . ? N4 C3 H3B 110.8 . . ? C2 C3 H3B 110.8 . . ? H3A C3 H3B 108.8 . . ? C5 N4 C3 119.0(8) . . Y C5 N4 Co 128.2(7) . . Y C3 N4 Co 112.4(5) . . Y N4 C5 O5 124.6(8) . . Y N4 C5 C6 118.6(9) . . Y O5 C5 C6 116.7(7) . . Y C5 O5 H5 114(10) . . Y O6 C6 C5 118.7(5) . . Y O6 C6 C5 118.7(5) . 6 Y C5 C6 C5 122.6(10) . 6 Y C14 C13 C14 115.4(10) 6 . ? C14 C13 H13A 108.4 6 . ? C14 C13 H13A 108.4 . . ? C14 C13 H13B 108.4 6 . ? C14 C13 H13B 108.4 . . ? H13A C13 H13B 107.5 . . ? N1 C14 C13 110.4(8) . . ? N1 C14 H14A 109.6 . . ? C13 C14 H14A 109.6 . . ? N1 C14 H14B 109.6 . . ? C13 C14 H14B 109.6 . . ? H14A C14 H14B 108.1 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N4 Co N1 C2 -94(7) 6 . . . ? N4 Co N1 C2 -16.9(6) . . . . ? N1 Co N1 C2 165.6(4) 6 . . . ? Cl2 Co N1 C2 73.0(5) . . . . ? Cl3 Co N1 C2 -107.2(5) . . . . ? N4 Co N1 C14 138(7) 6 . . . ? N4 Co N1 C14 -144.5(6) . . . . ? N1 Co N1 C14 38.0(7) 6 . . . ? Cl2 Co N1 C14 -54.6(6) . . . . ? Cl3 Co N1 C14 125.3(6) . . . . ? C14 N1 C2 C3 172.6(7) . . . . ? Co N1 C2 C3 40.7(8) . . . . ? N1 C2 C3 N4 -49.5(9) . . . . ? C2 C3 N4 C5 -137.6(8) . . . . ? C2 C3 N4 Co 35.9(8) . . . . ? N4 Co N4 C5 -21.4(9) 6 . . . ? N1 Co N4 C5 -98(7) 6 . . . ? N1 Co N4 C5 161.1(8) . . . . ? Cl2 Co N4 C5 68.6(7) . . . . ? Cl3 Co N4 C5 -111.5(7) . . . . ? N4 Co N4 C3 165.7(4) 6 . . . ? N1 Co N4 C3 89(7) 6 . . . ? N1 Co N4 C3 -11.8(5) . . . . ? Cl2 Co N4 C3 -104.2(5) . . . . ? Cl3 Co N4 C3 75.7(5) . . . . ? C3 N4 C5 O5 -2.1(12) . . . . ? Co N4 C5 O5 -174.5(6) . . . . ? C3 N4 C5 C6 174.0(8) . . . . ? Co N4 C5 C6 1.6(12) . . . . ? N4 C5 C6 O6 -153.6(10) . . . . ? O5 C5 C6 O6 22.7(14) . . . . ? N4 C5 C6 C5 27.7(15) . . . 6 ? O5 C5 C6 C5 -156.0(7) . . . 6 ? C2 N1 C14 C13 178.9(7) . . . . ? Co N1 C14 C13 -54.9(9) . . . . ? C14 C13 C14 N1 68.9(12) 6 . . . ? 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 N1 H1 O5 0.91 2.43 3.215(9) 145.1 7_666 O5 H5 O5 0.84(17) 1.68(16) 2.460(12) 155(17) 2 O5 H5 O6 0.84(17) 2.79(16) 3.298(8) 121(16) 5 _diffrn_measured_fraction_theta_max 0.875 _diffrn_reflns_theta_full 69.95 _diffrn_measured_fraction_theta_full 0.875 _refine_diff_density_max 0.811 _refine_diff_density_min -1.627 _refine_diff_density_rms 0.155 #===END data_[Co(2)Cl2]Cl.0.5CH3OH _database_code_CSD 211122 _audit_creation_method SHELXL-97 _chemical_name_systematic ; [Co(6-(anthracen-9-ylmethyl)-1,4,8,11-tetraazacyclotetradecane-5,7-dione)Cl2]Cl ; _chemical_name_common ;(Co(6-(anthracen-9-ylmethyl)-1,4,8,11- tetraazacyclotetradecane-5,7-dione)Cl2)Cl ; _chemical_melting_point ? _chemical_formula_moiety C25H30N4Cl3O2Co _chemical_formula_sum 'C25.50 H32 Cl3 Co N4 O2.50' _chemical_formula_weight 599.84 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' Cl Cl 0.1484 0.1585 '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 10.408(4) _cell_length_b 10.8133(8) _cell_length_c 12.018(7) _cell_angle_alpha 93.22(3) _cell_angle_beta 107.21(5) _cell_angle_gamma 94.824(15) _cell_volume 1282.8(9) _cell_formula_units_Z 2 _cell_measurement_temperature 150(1) _cell_measurement_reflns_used 25 _cell_measurement_theta_min 9.49 _cell_measurement_theta_max 17.11 _exptl_crystal_description cube _exptl_crystal_colour green _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.13 _exptl_crystal_size_min 0.09 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.553 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 622 _exptl_absorpt_coefficient_mu 1.016 _exptl_absorpt_correction_type Gaussian _exptl_absorpt_process_details 'Sheldrick, 1976' _exptl_absorpt_correction_T_min 0.6032 _exptl_absorpt_correction_T_max 0.8040 _exptl_special_details ; [Co(6-(anthracen-9-ylmethyl)-1,4,8,11-tetraazacyclotetradecane-5,7-dione) Cl2]Cl ; _diffrn_ambient_temperature 150(1) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Enraf Nonius CAD4-MachS Diffractometer' _diffrn_measurement_method \w:2\q _diffrn_detector_area_resol_mean ? _diffrn_standards_number 3 _diffrn_standards_interval_count ? _diffrn_standards_interval_time 120 _diffrn_standards_decay_% none _diffrn_reflns_number 5212 _diffrn_reflns_av_R_equivalents 0.0592 _diffrn_reflns_av_sigmaI/netI 0.0423 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -1 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 2.06 _diffrn_reflns_theta_max 25.06 _reflns_number_total 4505 _reflns_number_gt 3621 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CAD-4 Software (Enraf-Nonius, 1989)' _computing_cell_refinement 'CAD-4 Software' _computing_data_reduction 'PROCESS_DATA (Gable et al., 1993)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEPIII (Farrugia, 1997)' _computing_publication_material SHELXL _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^)+(0.1001P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4505 _refine_ls_number_parameters 371 _refine_ls_number_restraints 12 _refine_ls_R_factor_all 0.0609 _refine_ls_R_factor_gt 0.0489 _refine_ls_wR_factor_ref 0.1390 _refine_ls_wR_factor_gt 0.1313 _refine_ls_goodness_of_fit_ref 1.023 _refine_ls_restrained_S_all 1.029 _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 Co Co 0.13235(4) 0.90067(4) 0.81183(4) 0.01330(17) Uani 1 1 d . . . Cl1 Cl 0.06229(9) 0.83929(8) 0.61986(7) 0.0212(2) Uani 1 1 d . . . Cl2 Cl 0.19969(8) 0.96189(8) 1.00536(7) 0.0182(2) Uani 1 1 d . . . N1 N -0.0537(3) 0.9209(3) 0.8093(3) 0.0166(6) Uani 1 1 d . . . H1 H -0.0482 0.9540 0.8821 0.030(12) Uiso 1 1 calc R . . C2 C -0.1260(4) 0.7946(3) 0.7965(3) 0.0213(8) Uani 1 1 d . . . H2A H -0.1528 0.7613 0.7154 0.025(11) Uiso 1 1 calc R . . H2B H -0.2068 0.7981 0.8206 0.030(11) Uiso 1 1 calc R . . C3 C -0.0327(4) 0.7123(3) 0.8719(3) 0.0208(8) Uani 1 1 d . . . H3A H -0.0229 0.7330 0.9537 0.013(9) Uiso 1 1 calc R . . H3B H -0.0686 0.6255 0.8518 0.031(11) Uiso 1 1 calc R . . N4 N 0.1000(3) 0.7346(3) 0.8495(3) 0.0183(6) Uani 1 1 d . . . C5 C 0.1792(3) 0.6484(3) 0.8658(3) 0.0160(7) Uani 1 1 d . . . O5 O 0.1359(3) 0.5410(3) 0.8961(3) 0.0269(6) Uani 1 1 d . . . H5 H 0.189(4) 0.493(4) 0.915(4) 0.019(11) Uiso 1 1 d . . . C6 C 0.3167(3) 0.6579(3) 0.8449(3) 0.0158(7) Uani 1 1 d . . . H6 H 0.3772 0.6146 0.9053 0.003(8) Uiso 1 1 calc R . . C7 C 0.3828(3) 0.7888(3) 0.8498(3) 0.0154(7) Uani 1 1 d . . . O7 O 0.5157(2) 0.8049(3) 0.8745(2) 0.0224(6) Uani 1 1 d . . . H7 H 0.550(5) 0.747(5) 0.909(4) 0.041(15) Uiso 1 1 d . . . N8 N 0.3181(3) 0.8836(3) 0.8241(2) 0.0136(6) Uani 1 1 d . . . C9 C 0.3942(4) 1.0037(3) 0.8227(3) 0.0210(8) Uani 1 1 d . . . H9A H 0.4693 0.9919 0.7924 0.001(7) Uiso 1 1 calc R . . H9B H 0.4294 1.0451 0.9010 0.029(11) Uiso 1 1 calc R . . C10 C 0.2953(4) 1.0804(3) 0.7440(3) 0.0210(8) Uani 1 1 d . . . H10A H 0.3346 1.1661 0.7507 0.022(10) Uiso 1 1 calc R . . H10B H 0.2734 1.0473 0.6631 0.023(10) Uiso 1 1 calc R . . N11 N 0.1720(3) 1.0743(3) 0.7814(3) 0.0185(6) Uani 1 1 d . . . H11 H 0.1953 1.1195 0.8519 0.020(10) Uiso 1 1 calc R . . C12 C 0.0648(4) 1.1376(3) 0.7017(3) 0.0221(8) Uani 1 1 d . . . H12A H 0.0430 1.0980 0.6230 0.029(11) Uiso 1 1 calc R . . H12B H 0.0981 1.2239 0.7007 0.013(9) Uiso 1 1 calc R . . C13 C -0.0607(4) 1.1324(3) 0.7391(3) 0.0238(8) Uani 1 1 d . . . H13A H -0.1220 1.1862 0.6929 0.022(10) Uiso 1 1 calc R . . H13B H -0.0365 1.1651 0.8202 0.027(11) Uiso 1 1 calc R . . C14 C -0.1344(4) 1.0028(3) 0.7264(3) 0.0226(8) Uani 1 1 d . . . H14A H -0.2206 1.0084 0.7410 0.033(12) Uiso 1 1 calc R . . H14B H -0.1522 0.9664 0.6470 0.025(11) Uiso 1 1 calc R . . C15 C 0.3002(3) 0.5866(3) 0.7245(3) 0.0187(7) Uani 1 1 d . . . H15A H 0.2631 0.5015 0.7259 0.021(10) Uiso 1 1 calc R . . H15B H 0.2346 0.6245 0.6647 0.034(12) Uiso 1 1 calc R . . C16 C 0.4281(3) 0.5832(3) 0.6893(3) 0.0177(7) Uani 1 1 d . . . C17 C 0.4565(3) 0.6663(3) 0.6120(3) 0.0181(7) Uani 1 1 d . . . C18 C 0.3735(4) 0.7625(3) 0.5679(3) 0.0223(8) Uani 1 1 d . . . H18 H 0.2966 0.7710 0.5909 0.021(10) Uiso 1 1 calc R . . C19 C 0.4040(4) 0.8413(4) 0.4939(3) 0.0263(8) Uani 1 1 d . . . H19 H 0.3494 0.9043 0.4685 0.028(11) Uiso 1 1 calc R . . C20 C 0.5183(4) 0.8290(4) 0.4545(4) 0.0287(9) Uani 1 1 d . . . H20 H 0.5364 0.8820 0.4015 0.033(12) Uiso 1 1 calc R . . C21 C 0.6009(4) 0.7406(3) 0.4938(3) 0.0239(8) Uani 1 1 d . . . H21 H 0.6761 0.7340 0.4680 0.041(13) Uiso 1 1 calc R . . C22 C 0.5745(4) 0.6569(3) 0.5744(3) 0.0194(7) Uani 1 1 d . . . C23 C 0.6615(4) 0.5682(3) 0.6169(3) 0.0213(8) Uani 1 1 d . . . H23 H 0.7370 0.5621 0.5913 0.024(10) Uiso 1 1 calc R . . C24 C 0.6382(4) 0.4888(3) 0.6965(3) 0.0201(8) Uani 1 1 d . . . C25 C 0.7311(4) 0.4006(4) 0.7441(3) 0.0249(8) Uani 1 1 d . . . H25 H 0.8101 0.3987 0.7232 0.043(13) Uiso 1 1 calc R . . C26 C 0.7054(4) 0.3204(4) 0.8189(4) 0.0277(9) Uani 1 1 d . . . H26 H 0.7664 0.2636 0.8488 0.067(18) Uiso 1 1 calc R . . C27 C 0.5864(4) 0.3224(3) 0.8519(3) 0.0220(8) Uani 1 1 d . . . H27 H 0.5687 0.2656 0.9022 0.007(8) Uiso 1 1 calc R . . C28 C 0.4970(4) 0.4064(3) 0.8111(3) 0.0202(8) Uani 1 1 d . . . H28 H 0.4197 0.4065 0.8349 0.036(12) Uiso 1 1 calc R . . C29 C 0.5192(3) 0.4945(3) 0.7328(3) 0.0175(7) Uani 1 1 d . . . Cl3 Cl 0.27898(9) 0.32599(8) 0.97062(8) 0.0223(2) Uani 1 1 d . . . O30 O 0.0231(12) 0.5264(14) 0.4440(12) 0.130(5) Uani 0.536(11) 1 d PU . . C30 C 0.0741(11) 0.4218(10) 0.5073(11) 0.060(3) Uani 0.536(11) 1 d PU . . 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 0.0143(3) 0.0122(3) 0.0138(3) -0.00189(18) 0.00527(19) 0.00167(18) Cl1 0.0237(4) 0.0242(5) 0.0153(4) -0.0034(3) 0.0057(4) 0.0051(4) Cl2 0.0193(4) 0.0205(4) 0.0147(4) -0.0017(3) 0.0054(3) 0.0023(3) N1 0.0184(14) 0.0158(15) 0.0175(15) -0.0008(12) 0.0076(12) 0.0054(12) C2 0.0169(17) 0.0200(18) 0.029(2) -0.0036(16) 0.0110(15) 0.0024(14) C3 0.0208(18) 0.0171(18) 0.028(2) 0.0005(15) 0.0134(16) 0.0001(14) N4 0.0179(15) 0.0195(15) 0.0198(16) -0.0005(12) 0.0106(12) -0.0011(12) C5 0.0204(17) 0.0136(17) 0.0152(17) 0.0009(13) 0.0071(14) 0.0022(14) O5 0.0274(14) 0.0177(14) 0.0436(18) 0.0109(12) 0.0201(13) 0.0075(12) C6 0.0173(17) 0.0165(17) 0.0150(17) -0.0001(14) 0.0069(14) 0.0034(13) C7 0.0131(16) 0.0204(18) 0.0121(17) -0.0024(14) 0.0044(13) -0.0012(13) O7 0.0132(12) 0.0234(14) 0.0292(15) 0.0026(12) 0.0045(11) 0.0014(11) N8 0.0130(13) 0.0137(14) 0.0153(14) -0.0007(11) 0.0059(11) 0.0023(11) C9 0.0189(17) 0.0192(18) 0.026(2) -0.0018(15) 0.0104(15) -0.0013(14) C10 0.0245(19) 0.0169(18) 0.024(2) 0.0025(15) 0.0112(16) -0.0019(14) N11 0.0218(15) 0.0166(15) 0.0185(16) -0.0031(12) 0.0091(13) 0.0020(12) C12 0.0259(19) 0.0178(18) 0.022(2) 0.0017(15) 0.0057(16) 0.0055(15) C13 0.0235(19) 0.023(2) 0.025(2) -0.0003(16) 0.0053(16) 0.0103(15) C14 0.0187(17) 0.025(2) 0.022(2) -0.0006(16) 0.0018(15) 0.0072(15) C15 0.0189(17) 0.0170(18) 0.0204(19) -0.0046(14) 0.0080(15) -0.0003(14) C16 0.0205(17) 0.0169(17) 0.0147(17) -0.0093(14) 0.0071(14) -0.0035(14) C17 0.0197(17) 0.0192(18) 0.0133(17) -0.0048(14) 0.0042(14) -0.0030(14) C18 0.0248(19) 0.0221(19) 0.0210(19) -0.0007(15) 0.0087(16) 0.0037(15) C19 0.029(2) 0.024(2) 0.024(2) 0.0015(16) 0.0050(17) 0.0078(16) C20 0.033(2) 0.028(2) 0.026(2) 0.0056(17) 0.0122(18) -0.0037(17) C21 0.0259(19) 0.025(2) 0.023(2) 0.0016(16) 0.0113(16) 0.0003(16) C22 0.0223(18) 0.0175(17) 0.0171(18) -0.0044(14) 0.0066(15) -0.0032(14) C23 0.0179(17) 0.0247(19) 0.0229(19) -0.0069(15) 0.0108(15) -0.0010(15) C24 0.0173(17) 0.0196(18) 0.0217(19) -0.0074(15) 0.0055(15) 0.0003(14) C25 0.0242(19) 0.025(2) 0.028(2) -0.0041(16) 0.0118(16) 0.0041(16) C26 0.029(2) 0.024(2) 0.029(2) -0.0024(17) 0.0075(17) 0.0064(17) C27 0.030(2) 0.0192(18) 0.0171(18) -0.0016(15) 0.0089(16) 0.0015(15) C28 0.0256(19) 0.0180(18) 0.0184(18) -0.0049(14) 0.0102(15) 0.0006(14) C29 0.0189(17) 0.0145(17) 0.0179(18) -0.0055(14) 0.0051(14) 0.0000(13) Cl3 0.0239(4) 0.0189(4) 0.0261(5) 0.0041(4) 0.0094(4) 0.0045(3) O30 0.092(7) 0.160(9) 0.129(8) -0.022(7) 0.033(6) -0.007(6) C30 0.054(5) 0.053(6) 0.081(7) -0.026(5) 0.042(5) -0.010(4) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Co N4 1.904(3) . y Co N8 1.920(3) . y Co N1 1.959(3) . y Co N11 1.966(3) . y Co Cl1 2.2463(17) . y Co Cl2 2.2635(17) . y N1 C2 1.480(5) . ? N1 C14 1.487(5) . ? N1 H1 0.9100 . ? C2 C3 1.507(5) . ? C2 H2A 0.9700 . ? C2 H2B 0.9700 . ? C3 N4 1.486(4) . ? C3 H3A 0.9700 . ? C3 H3B 0.9700 . ? N4 C5 1.280(4) . y C5 O5 1.319(4) . y C5 C6 1.521(5) . y O5 H5 0.78(4) . ? C6 C7 1.512(5) . y C6 C15 1.557(5) . y C6 H6 0.9800 . ? C7 N8 1.276(4) . y C7 O7 1.320(4) . y O7 H7 0.82(5) . ? N8 C9 1.468(4) . ? C9 C10 1.516(5) . ? C9 H9A 0.9700 . ? C9 H9B 0.9700 . ? C10 N11 1.478(4) . ? C10 H10A 0.9700 . ? C10 H10B 0.9700 . ? N11 C12 1.483(5) . ? N11 H11 0.9100 . ? C12 C13 1.499(5) . ? C12 H12A 0.9700 . ? C12 H12B 0.9700 . ? C13 C14 1.518(5) . ? C13 H13A 0.9700 . ? C13 H13B 0.9700 . ? C14 H14A 0.9700 . ? C14 H14B 0.9700 . ? C15 C16 1.514(5) . ? C15 H15A 0.9700 . ? C15 H15B 0.9700 . ? C16 C17 1.404(5) . ? C16 C29 1.416(5) . ? C17 C18 1.433(5) . ? C17 C22 1.437(5) . ? C18 C19 1.351(5) . ? C18 H18 0.9300 . ? C19 C20 1.417(5) . ? C19 H19 0.9300 . ? C20 C21 1.351(6) . ? C20 H20 0.9300 . ? C21 C22 1.430(5) . ? C21 H21 0.9300 . ? C22 C23 1.389(5) . ? C23 C24 1.381(5) . ? C23 H23 0.9300 . ? C24 C29 1.434(5) . ? C24 C25 1.435(5) . ? C25 C26 1.350(6) . ? C25 H25 0.9300 . ? C26 C27 1.409(5) . ? C26 H26 0.9300 . ? C27 C28 1.362(5) . ? C27 H27 0.9300 . ? C28 C29 1.428(5) . ? C28 H28 0.9300 . ? O30 C30 1.446(15) 2_566 ? O30 C30 1.449(18) . ? C30 O30 1.446(15) 2_566 ? 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 N4 Co N8 92.97(12) . . y N4 Co N1 86.83(12) . . y N8 Co N1 176.58(12) . . y N4 Co N11 176.97(13) . . y N8 Co N11 85.89(12) . . y N1 Co N11 94.14(12) . . y N4 Co Cl1 91.13(10) . . y N8 Co Cl1 92.63(10) . . y N1 Co Cl1 90.78(10) . . y N11 Co Cl1 91.72(10) . . y N4 Co Cl2 88.55(10) . . y N8 Co Cl2 88.19(10) . . y N1 Co Cl2 88.39(10) . . y N11 Co Cl2 88.61(10) . . y Cl1 Co Cl2 179.13(4) . . y C2 N1 C14 111.1(3) . . ? C2 N1 Co 107.2(2) . . ? C14 N1 Co 119.8(2) . . ? C2 N1 H1 105.9 . . ? C14 N1 H1 105.9 . . ? Co N1 H1 105.9 . . ? N1 C2 C3 108.5(3) . . ? N1 C2 H2A 110.0 . . ? C3 C2 H2A 110.0 . . ? N1 C2 H2B 110.0 . . ? C3 C2 H2B 110.0 . . ? H2A C2 H2B 108.4 . . ? N4 C3 C2 106.8(3) . . ? N4 C3 H3A 110.4 . . ? C2 C3 H3A 110.4 . . ? N4 C3 H3B 110.4 . . ? C2 C3 H3B 110.4 . . ? H3A C3 H3B 108.6 . . ? C5 N4 C3 119.0(3) . . y C5 N4 Co 129.0(2) . . y C3 N4 Co 111.7(2) . . y N4 C5 O5 118.1(3) . . y N4 C5 C6 124.5(3) . . y O5 C5 C6 117.2(3) . . y C5 O5 H5 117(3) . . ? C7 C6 C5 115.4(3) . . y C7 C6 C15 110.2(3) . . y C5 C6 C15 108.0(3) . . y C7 C6 H6 107.6 . . ? C5 C6 H6 107.6 . . ? C15 C6 H6 107.6 . . ? N8 C7 O7 117.8(3) . . y N8 C7 C6 124.2(3) . . y O7 C7 C6 117.9(3) . . y C7 O7 H7 110(3) . . ? C7 N8 C9 118.7(3) . . y C7 N8 Co 128.4(2) . . y C9 N8 Co 112.0(2) . . y N8 C9 C10 106.2(3) . . ? N8 C9 H9A 110.5 . . ? C10 C9 H9A 110.5 . . ? N8 C9 H9B 110.5 . . ? C10 C9 H9B 110.5 . . ? H9A C9 H9B 108.7 . . ? N11 C10 C9 107.6(3) . . ? N11 C10 H10A 110.2 . . ? C9 C10 H10A 110.2 . . ? N11 C10 H10B 110.2 . . ? C9 C10 H10B 110.2 . . ? H10A C10 H10B 108.5 . . ? C10 N11 C12 111.1(3) . . ? C10 N11 Co 107.2(2) . . ? C12 N11 Co 119.5(2) . . ? C10 N11 H11 106.1 . . ? C12 N11 H11 106.1 . . ? Co N11 H11 106.1 . . ? N11 C12 C13 111.6(3) . . ? N11 C12 H12A 109.3 . . ? C13 C12 H12A 109.3 . . ? N11 C12 H12B 109.3 . . ? C13 C12 H12B 109.3 . . ? H12A C12 H12B 108.0 . . ? C12 C13 C14 114.2(3) . . ? C12 C13 H13A 108.7 . . ? C14 C13 H13A 108.7 . . ? C12 C13 H13B 108.7 . . ? C14 C13 H13B 108.7 . . ? H13A C13 H13B 107.6 . . ? N1 C14 C13 111.4(3) . . ? N1 C14 H14A 109.4 . . ? C13 C14 H14A 109.4 . . ? N1 C14 H14B 109.4 . . ? C13 C14 H14B 109.4 . . ? H14A C14 H14B 108.0 . . ? C16 C15 C6 115.8(3) . . y C16 C15 H15A 108.3 . . ? C6 C15 H15A 108.3 . . ? C16 C15 H15B 108.3 . . ? C6 C15 H15B 108.3 . . ? H15A C15 H15B 107.4 . . ? C17 C16 C29 119.4(3) . . y C17 C16 C15 120.4(3) . . y C29 C16 C15 120.2(3) . . y C16 C17 C18 123.2(3) . . ? C16 C17 C22 119.6(3) . . ? C18 C17 C22 117.2(3) . . ? C19 C18 C17 121.7(3) . . ? C19 C18 H18 119.2 . . ? C17 C18 H18 119.2 . . ? C18 C19 C20 120.7(4) . . ? C18 C19 H19 119.7 . . ? C20 C19 H19 119.7 . . ? C21 C20 C19 120.3(4) . . ? C21 C20 H20 119.9 . . ? C19 C20 H20 119.9 . . ? C20 C21 C22 121.1(3) . . ? C20 C21 H21 119.5 . . ? C22 C21 H21 119.5 . . ? C23 C22 C21 120.9(3) . . ? C23 C22 C17 120.0(3) . . ? C21 C22 C17 119.0(3) . . ? C24 C23 C22 121.3(3) . . ? C24 C23 H23 119.4 . . ? C22 C23 H23 119.4 . . ? C23 C24 C29 119.5(3) . . ? C23 C24 C25 121.2(3) . . ? C29 C24 C25 119.3(3) . . ? C26 C25 C24 120.9(3) . . ? C26 C25 H25 119.5 . . ? C24 C25 H25 119.5 . . ? C25 C26 C27 120.2(4) . . ? C25 C26 H26 119.9 . . ? C27 C26 H26 119.9 . . ? C28 C27 C26 120.9(4) . . ? C28 C27 H27 119.6 . . ? C26 C27 H27 119.6 . . ? C27 C28 C29 121.6(3) . . ? C27 C28 H28 119.2 . . ? C29 C28 H28 119.2 . . ? C16 C29 C28 122.7(3) . . ? C16 C29 C24 120.1(3) . . ? C28 C29 C24 117.1(3) . . ? C30 O30 C30 109.5(11) 2_566 . ? O30 C30 O30 70.5(11) 2_566 . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N4 Co N1 C2 -18.9(2) . . . . ? N8 Co N1 C2 -105.6(19) . . . . ? N11 Co N1 C2 164.0(2) . . . . ? Cl1 Co N1 C2 72.2(2) . . . . ? Cl2 Co N1 C2 -107.5(2) . . . . ? N4 Co N1 C14 -146.6(3) . . . . ? N8 Co N1 C14 126.7(19) . . . . ? N11 Co N1 C14 36.3(3) . . . . ? Cl1 Co N1 C14 -55.5(2) . . . . ? Cl2 Co N1 C14 124.8(2) . . . . ? C14 N1 C2 C3 173.3(3) . . . . ? Co N1 C2 C3 40.7(3) . . . . ? N1 C2 C3 N4 -46.7(4) . . . . ? C2 C3 N4 C5 -154.1(3) . . . . ? C2 C3 N4 Co 31.0(3) . . . . ? N8 Co N4 C5 -4.8(3) . . . . ? N1 Co N4 C5 178.6(3) . . . . ? N11 Co N4 C5 -73(2) . . . . ? Cl1 Co N4 C5 87.9(3) . . . . ? Cl2 Co N4 C5 -92.9(3) . . . . ? N8 Co N4 C3 169.4(2) . . . . ? N1 Co N4 C3 -7.2(2) . . . . ? N11 Co N4 C3 101(2) . . . . ? Cl1 Co N4 C3 -97.9(2) . . . . ? Cl2 Co N4 C3 81.3(2) . . . . ? C3 N4 C5 O5 3.4(5) . . . . ? Co N4 C5 O5 177.2(2) . . . . ? C3 N4 C5 C6 179.1(3) . . . . ? Co N4 C5 C6 -7.0(5) . . . . ? N4 C5 C6 C7 23.5(5) . . . . ? O5 C5 C6 C7 -160.7(3) . . . . ? N4 C5 C6 C15 -100.3(4) . . . . ? O5 C5 C6 C15 75.4(4) . . . . ? C5 C6 C7 N8 -28.7(5) . . . . ? C15 C6 C7 N8 93.9(4) . . . . ? C5 C6 C7 O7 156.1(3) . . . . ? C15 C6 C7 O7 -81.3(4) . . . . ? O7 C7 N8 C9 0.4(5) . . . . ? C6 C7 N8 C9 -174.8(3) . . . . ? O7 C7 N8 Co -167.6(2) . . . . ? C6 C7 N8 Co 17.2(5) . . . . ? N4 Co N8 C7 -0.3(3) . . . . ? N1 Co N8 C7 86.3(19) . . . . ? N11 Co N8 C7 176.9(3) . . . . ? Cl1 Co N8 C7 -91.6(3) . . . . ? Cl2 Co N8 C7 88.2(3) . . . . ? N4 Co N8 C9 -169.0(2) . . . . ? N1 Co N8 C9 -82.5(19) . . . . ? N11 Co N8 C9 8.2(2) . . . . ? Cl1 Co N8 C9 99.7(2) . . . . ? Cl2 Co N8 C9 -80.6(2) . . . . ? C7 N8 C9 C10 156.9(3) . . . . ? Co N8 C9 C10 -33.2(3) . . . . ? N8 C9 C10 N11 49.3(4) . . . . ? C9 C10 N11 C12 -174.8(3) . . . . ? C9 C10 N11 Co -42.6(3) . . . . ? N4 Co N11 C10 88(2) . . . . ? N8 Co N11 C10 19.7(2) . . . . ? N1 Co N11 C10 -163.8(2) . . . . ? Cl1 Co N11 C10 -72.9(2) . . . . ? Cl2 Co N11 C10 107.9(2) . . . . ? N4 Co N11 C12 -145(2) . . . . ? N8 Co N11 C12 147.0(3) . . . . ? N1 Co N11 C12 -36.4(3) . . . . ? Cl1 Co N11 C12 54.5(2) . . . . ? Cl2 Co N11 C12 -124.7(2) . . . . ? C10 N11 C12 C13 -179.8(3) . . . . ? Co N11 C12 C13 54.7(4) . . . . ? N11 C12 C13 C14 -67.8(4) . . . . ? C2 N1 C14 C13 -179.9(3) . . . . ? Co N1 C14 C13 -54.0(4) . . . . ? C12 C13 C14 N1 67.4(4) . . . . ? C7 C6 C15 C16 54.4(4) . . . . ? C5 C6 C15 C16 -178.7(3) . . . . ? C6 C15 C16 C17 -98.9(4) . . . . ? C6 C15 C16 C29 82.1(4) . . . . ? C29 C16 C17 C18 -177.1(3) . . . . ? C15 C16 C17 C18 3.9(5) . . . . ? C29 C16 C17 C22 2.5(5) . . . . ? C15 C16 C17 C22 -176.4(3) . . . . ? C16 C17 C18 C19 179.8(4) . . . . ? C22 C17 C18 C19 0.1(5) . . . . ? C17 C18 C19 C20 1.7(6) . . . . ? C18 C19 C20 C21 -2.2(6) . . . . ? C19 C20 C21 C22 0.7(6) . . . . ? C20 C21 C22 C23 -178.3(4) . . . . ? C20 C21 C22 C17 1.2(5) . . . . ? C16 C17 C22 C23 -1.7(5) . . . . ? C18 C17 C22 C23 177.9(3) . . . . ? C16 C17 C22 C21 178.8(3) . . . . ? C18 C17 C22 C21 -1.6(5) . . . . ? C21 C22 C23 C24 178.7(3) . . . . ? C17 C22 C23 C24 -0.8(5) . . . . ? C22 C23 C24 C29 2.4(5) . . . . ? C22 C23 C24 C25 -177.4(3) . . . . ? C23 C24 C25 C26 -177.8(4) . . . . ? C29 C24 C25 C26 2.5(5) . . . . ? C24 C25 C26 C27 -0.3(6) . . . . ? C25 C26 C27 C28 -1.4(6) . . . . ? C26 C27 C28 C29 0.7(5) . . . . ? C17 C16 C29 C28 -179.6(3) . . . . ? C15 C16 C29 C28 -0.7(5) . . . . ? C17 C16 C29 C24 -0.9(5) . . . . ? C15 C16 C29 C24 178.0(3) . . . . ? C27 C28 C29 C16 -179.8(3) . . . . ? C27 C28 C29 C24 1.5(5) . . . . ? C23 C24 C29 C16 -1.5(5) . . . . ? C25 C24 C29 C16 178.3(3) . . . . ? C23 C24 C29 C28 177.2(3) . . . . ? C25 C24 C29 C28 -3.0(5) . . . . ? C30 O30 C30 O30 0.000(2) 2_566 . . 2_566 ? 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 N1 H1 Cl2 0.91 2.55 3.299(3) 139.8 2_577 O5 H5 Cl3 0.78(4) 2.16(4) 2.908(3) 162(4) . O7 H7 Cl3 0.82(5) 2.17(5) 2.913(3) 150(5) 2_667 N11 H11 Cl3 0.91 2.52 3.334(3) 148.8 1_565 _diffrn_measured_fraction_theta_max 0.989 _diffrn_reflns_theta_full 25.06 _diffrn_measured_fraction_theta_full 0.989 _refine_diff_density_max 0.770 _refine_diff_density_min -0.785 _refine_diff_density_rms 0.109