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 _publ_contact_author_name 'M. Hardie' _publ_contact_author_address ; School of Chemistry University of Leeds Woodhouse Lane Leeds LS2 9JT UNITED KINGDOM ; _publ_contact_author_email M.J.HARDIE@LEEDS.AC.UK _publ_section_title ; Network structures with 2,2'-bipyridine-3,3'diol: a discrete Co(III) complex that forms a porous 3-D hydrogen bonded network, and Cu(II) coordination chains. ; loop_ _publ_author_name 'M. Hardie' 'Maria D. Stephenson' ####################################################################### #Complex 1 data_1 _database_code_depnum_ccdc_archive 'CCDC 629297' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common "tris(2,2'-bipyridine-3,3-diol-H)cobalt(iii) hydrate" _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C30 H23 Co N6 O7' _chemical_formula_weight 638.47 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Co Co 0.3494 0.9721 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Trigonal _symmetry_space_group_name_H-M P-31c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-y, x-y, z' '-x+y, -x, z' '-y, -x, -z+1/2' '-x+y, y, -z+1/2' 'x, x-y, -z+1/2' '-x, -y, -z' 'y, -x+y, -z' 'x-y, x, -z' 'y, x, z-1/2' 'x-y, -y, z-1/2' '-x, -x+y, z-1/2' _cell_length_a 14.2158(4) _cell_length_b 14.2158(4) _cell_length_c 9.4244(2) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 120.00 _cell_volume 1649.40(7) _cell_formula_units_Z 2 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description prism _exptl_crystal_colour 'dark red' _exptl_crystal_size_max 0.26 _exptl_crystal_size_mid 0.13 _exptl_crystal_size_min 0.09 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.286 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 656 _exptl_absorpt_coefficient_mu 0.572 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8656 _exptl_absorpt_correction_T_max 0.9503 _exptl_absorpt_process_details SORTAV _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(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 CCD _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 8029 _diffrn_reflns_av_R_equivalents 0.0406 _diffrn_reflns_av_sigmaI/netI 0.0278 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 3.95 _diffrn_reflns_theta_max 27.48 _reflns_number_total 1265 _reflns_number_gt 1188 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'COLLECT (Nonius)' _computing_cell_refinement 'DENZO (Nonius)' _computing_data_reduction 'DENZO (Nonius)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'X-Seed, (Barbour)' _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. The OH hydrogen of the bpydiol-H diol ligand was fully refined, while the H on the water was constrained to the position that it originally appeared in the difference map and given a Uiso of 1.5x that of the water O atom. ; _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^)+(0.1152P)^2^+2.7023P] 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 1265 _refine_ls_number_parameters 70 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0600 _refine_ls_R_factor_gt 0.0575 _refine_ls_wR_factor_ref 0.2173 _refine_ls_wR_factor_gt 0.2134 _refine_ls_goodness_of_fit_ref 1.257 _refine_ls_restrained_S_all 1.257 _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 0.3333 0.6667 0.2500 0.0181(4) Uani 1 6 d S . . O1 O 0.6053(2) 0.5266(2) 0.3295(3) 0.0330(6) Uani 1 1 d . . . N1 N 0.4474(2) 0.66315(19) 0.3571(3) 0.0205(6) Uani 1 1 d . . . H1 H 0.553(4) 0.447(4) 0.2500 0.08(3) Uiso 1 2 d S . . O2 O 0.8923(10) 0.785(2) 0.7500 0.097(7) Uiso 0.33 2 d SP . . H2 H 0.8432 0.8240 0.7512 0.145 Uiso 0.33 1 d P . . C2 C 0.4773(2) 0.5912(2) 0.3088(3) 0.0206(7) Uani 1 1 d . . . C3 C 0.5681(3) 0.5900(3) 0.3715(3) 0.0252(7) Uani 1 1 d . . . C4 C 0.6206(3) 0.6623(3) 0.4848(4) 0.0290(8) Uani 1 1 d . . . H4 H 0.6813 0.6636 0.5291 0.035 Uiso 1 1 calc R . . C5 C 0.5857(3) 0.7307(3) 0.5319(4) 0.0286(7) Uani 1 1 d . . . H5 H 0.6210 0.7780 0.6096 0.034 Uiso 1 1 calc R . . C6 C 0.4988(2) 0.7306(2) 0.4659(3) 0.0240(7) Uani 1 1 d . . . H6 H 0.4752 0.7788 0.4979 0.029 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 Co1 0.0180(4) 0.0180(4) 0.0184(6) 0.000 0.000 0.0090(2) O1 0.0364(13) 0.0444(15) 0.0316(13) -0.0081(11) -0.0072(10) 0.0304(12) N1 0.0208(12) 0.0194(12) 0.0205(12) -0.0010(8) -0.0005(9) 0.0095(10) C2 0.0209(14) 0.0222(14) 0.0191(14) 0.0002(11) -0.0002(11) 0.0111(12) C3 0.0259(15) 0.0293(15) 0.0238(14) 0.0004(12) -0.0006(11) 0.0163(13) C4 0.0283(16) 0.0337(18) 0.0286(16) -0.0029(13) -0.0082(13) 0.0182(14) C5 0.0300(16) 0.0287(16) 0.0261(15) -0.0050(12) -0.0081(12) 0.0140(13) C6 0.0248(15) 0.0237(15) 0.0232(14) -0.0032(11) -0.0031(11) 0.0118(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 Co1 N1 1.932(3) 2_665 ? Co1 N1 1.932(3) 5 ? Co1 N1 1.932(3) 6_565 ? Co1 N1 1.932(3) 3_565 ? Co1 N1 1.932(3) . ? Co1 N1 1.932(3) 4_665 ? O1 C3 1.313(4) . ? O1 H1 1.25(3) . ? N1 C6 1.343(4) . ? N1 C2 1.367(4) . ? O2 H2 1.092(11) . ? C2 C3 1.427(4) . ? C2 C2 1.475(6) 4_665 ? C3 C4 1.410(5) . ? C4 C5 1.368(5) . ? C4 H4 0.9500 . ? C5 C6 1.383(4) . ? C5 H5 0.9500 . ? C6 H6 0.9500 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N1 Co1 N1 86.73(15) 2_665 5 ? N1 Co1 N1 82.92(15) 2_665 6_565 ? N1 Co1 N1 95.20(10) 5 6_565 ? N1 Co1 N1 95.20(10) 2_665 3_565 ? N1 Co1 N1 82.92(15) 5 3_565 ? N1 Co1 N1 177.43(14) 6_565 3_565 ? N1 Co1 N1 95.20(10) 2_665 . ? N1 Co1 N1 177.43(14) 5 . ? N1 Co1 N1 86.73(15) 6_565 . ? N1 Co1 N1 95.20(10) 3_565 . ? N1 Co1 N1 177.43(14) 2_665 4_665 ? N1 Co1 N1 95.20(10) 5 4_665 ? N1 Co1 N1 95.20(10) 6_565 4_665 ? N1 Co1 N1 86.73(15) 3_565 4_665 ? N1 Co1 N1 82.92(15) . 4_665 ? C3 O1 H1 123(4) . . ? C6 N1 C2 121.8(3) . . ? C6 N1 Co1 123.0(2) . . ? C2 N1 Co1 115.11(19) . . ? N1 C2 C3 119.5(3) . . ? N1 C2 C2 113.23(16) . 4_665 ? C3 C2 C2 127.27(17) . 4_665 ? O1 C3 C4 118.7(3) . . ? O1 C3 C2 124.1(3) . . ? C4 C3 C2 117.2(3) . . ? C5 C4 C3 121.1(3) . . ? C5 C4 H4 119.5 . . ? C3 C4 H4 119.5 . . ? C4 C5 C6 119.7(3) . . ? C4 C5 H5 120.2 . . ? C6 C5 H5 120.2 . . ? N1 C6 C5 120.7(3) . . ? N1 C6 H6 119.7 . . ? C5 C6 H6 119.7 . . ? _diffrn_measured_fraction_theta_max 0.993 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.993 _refine_diff_density_max 0.913 _refine_diff_density_min -0.464 _refine_diff_density_rms 0.114 #===END #Compound 1a data_1a _database_code_depnum_ccdc_archive 'CCDC 629298' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ; _chemical_name_common tris(2,2'-bipyridine-3,3'-diol-H)cobalt(iii) _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C30 H21 Co N6 O6' _chemical_formula_weight 620.46 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 Trigonal _symmetry_space_group_name_H-M P-31c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-y, x-y, z' '-x+y, -x, z' '-y, -x, -z+1/2' '-x+y, y, -z+1/2' 'x, x-y, -z+1/2' '-x, -y, -z' 'y, -x+y, -z' 'x-y, x, -z' 'y, x, z-1/2' 'x-y, -y, z-1/2' '-x, -x+y, z-1/2' _cell_length_a 14.311(2) _cell_length_b 14.311(2) _cell_length_c 9.5165(19) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 120.00 _cell_volume 1687.8(5) _cell_formula_units_Z 2 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description prism _exptl_crystal_colour 'dark red' _exptl_crystal_size_max 0.17 _exptl_crystal_size_mid 0.17 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.221 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 636 _exptl_absorpt_coefficient_mu 0.555 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9116 _exptl_absorpt_correction_T_max 0.9364 _exptl_absorpt_process_details SORTAV _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(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 CCD _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 11083 _diffrn_reflns_av_R_equivalents 0.0948 _diffrn_reflns_av_sigmaI/netI 0.0371 _diffrn_reflns_limit_h_min -18 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 3.92 _diffrn_reflns_theta_max 27.45 _reflns_number_total 1291 _reflns_number_gt 1207 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'COLLECT (Nonius)' _computing_cell_refinement 'DENZO (Nonius)' _computing_data_reduction 'DENZO (Nonius)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'X-Seed (Barbour)' _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. The OH hydrogen of the ligand has been fully refined. There was diffuse residual electron density which could not be meaningfully modelled as solvent. ; _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^)+(0.2000P)^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 1291 _refine_ls_number_parameters 68 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1372 _refine_ls_R_factor_gt 0.1321 _refine_ls_wR_factor_ref 0.4634 _refine_ls_wR_factor_gt 0.4540 _refine_ls_goodness_of_fit_ref 2.358 _refine_ls_restrained_S_all 2.358 _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 0.6667 0.3333 0.2500 0.0260(9) Uani 1 6 d S . . N1 N 0.7834(4) 0.4463(3) 0.3555(5) 0.0288(12) Uani 1 1 d . . . C6 C 0.7671(4) 0.4963(4) 0.4648(6) 0.0344(13) Uani 1 1 d . . . H6 H 0.6956 0.4730 0.4953 0.041 Uiso 1 1 calc R . . C2 C 0.8844(4) 0.4757(4) 0.3074(5) 0.0298(13) Uani 1 1 d . . . C5 C 0.8536(5) 0.5816(5) 0.5339(6) 0.0413(15) Uani 1 1 d . . . H5 H 0.8417 0.6152 0.6126 0.050 Uiso 1 1 calc R . . O1 O 1.0759(3) 0.6043(3) 0.3277(5) 0.0438(13) Uani 1 1 d . . . C4 C 0.9565(5) 0.6162(5) 0.4858(7) 0.0383(15) Uani 1 1 d . . . H4 H 1.0157 0.6757 0.5304 0.046 Uiso 1 1 calc R . . C3 C 0.9761(4) 0.5652(4) 0.3714(6) 0.0349(13) Uani 1 1 d . . . H1 H 1.08(2) 0.540(12) 0.2500 0.14(7) Uiso 1 2 d S . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Co1 0.0220(10) 0.0220(10) 0.0340(12) 0.000 0.000 0.0110(5) N1 0.027(2) 0.023(2) 0.036(2) -0.0006(16) 0.0010(16) 0.0123(18) C6 0.033(3) 0.031(3) 0.042(3) -0.004(2) 0.002(2) 0.017(2) C2 0.025(2) 0.028(2) 0.034(2) 0.0001(18) 0.0008(17) 0.012(2) C5 0.040(3) 0.040(3) 0.045(3) -0.008(2) -0.002(2) 0.020(2) O1 0.027(2) 0.041(2) 0.050(2) -0.0083(18) 0.0013(16) 0.0065(16) C4 0.033(3) 0.035(3) 0.043(3) -0.010(2) -0.004(2) 0.014(2) C3 0.030(3) 0.033(3) 0.036(2) -0.006(2) -0.0022(19) 0.011(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Co1 N1 1.927(5) 6 ? Co1 N1 1.927(5) 3_665 ? Co1 N1 1.927(5) . ? Co1 N1 1.927(5) 4_665 ? Co1 N1 1.927(5) 5_655 ? Co1 N1 1.927(5) 2_655 ? N1 C6 1.346(7) . ? N1 C2 1.367(6) . ? C6 C5 1.394(8) . ? C2 C3 1.432(7) . ? C2 C2 1.453(9) 6 ? C5 C4 1.376(8) . ? O1 C3 1.314(7) . ? C4 C3 1.415(8) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N1 Co1 N1 86.8(2) 6 3_665 ? N1 Co1 N1 82.7(3) 6 . ? N1 Co1 N1 95.33(19) 3_665 . ? N1 Co1 N1 95.33(19) 6 4_665 ? N1 Co1 N1 82.7(3) 3_665 4_665 ? N1 Co1 N1 177.2(2) . 4_665 ? N1 Co1 N1 95.33(19) 6 5_655 ? N1 Co1 N1 177.2(2) 3_665 5_655 ? N1 Co1 N1 86.8(2) . 5_655 ? N1 Co1 N1 95.33(19) 4_665 5_655 ? N1 Co1 N1 177.2(2) 6 2_655 ? N1 Co1 N1 95.33(19) 3_665 2_655 ? N1 Co1 N1 95.33(19) . 2_655 ? N1 Co1 N1 86.8(3) 4_665 2_655 ? N1 Co1 N1 82.7(3) 5_655 2_655 ? C6 N1 C2 122.2(4) . . ? C6 N1 Co1 122.7(4) . . ? C2 N1 Co1 115.0(3) . . ? N1 C6 C5 121.0(5) . . ? N1 C2 C3 119.2(4) . . ? N1 C2 C2 113.4(3) . 6 ? C3 C2 C2 127.4(3) . 6 ? C4 C5 C6 118.7(5) . . ? C5 C4 C3 121.5(5) . . ? O1 C3 C4 118.5(5) . . ? O1 C3 C2 124.1(5) . . ? C4 C3 C2 117.4(5) . . ? _diffrn_measured_fraction_theta_max 0.993 _diffrn_reflns_theta_full 27.45 _diffrn_measured_fraction_theta_full 0.993 _refine_diff_density_max 1.953 _refine_diff_density_min -0.807 _refine_diff_density_rms 0.206 #===END #Compound 1b data_1b _database_code_depnum_ccdc_archive 'CCDC 629299' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common "tris(2,2'-bipyridine-3,3-diol-H)cobalt(iii) hydrate" _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C30 H23 Co N6 O7' _chemical_formula_weight 638.47 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Co Co 0.3494 0.9721 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Trigonal _symmetry_space_group_name_H-M P-31c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-y, x-y, z' '-x+y, -x, z' '-y, -x, -z+1/2' '-x+y, y, -z+1/2' 'x, x-y, -z+1/2' '-x, -y, -z' 'y, -x+y, -z' 'x-y, x, -z' 'y, x, z-1/2' 'x-y, -y, z-1/2' '-x, -x+y, z-1/2' _cell_length_a 14.1281(3) _cell_length_b 14.1281(3) _cell_length_c 9.4484(2) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 120.00 _cell_volume 1633.26(6) _cell_formula_units_Z 2 _cell_measurement_temperature 30(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description prism _exptl_crystal_colour 'dark red' _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.298 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 656 _exptl_absorpt_coefficient_mu 0.577 _exptl_absorpt_correction_type multiscan _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details SADABS _exptl_special_details ; Data collected to only 98% completion due to icing problems ; _diffrn_ambient_temperature 30(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'rotating anode' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type CCD _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 7876 _diffrn_reflns_av_R_equivalents 0.0418 _diffrn_reflns_av_sigmaI/netI 0.0496 _diffrn_reflns_limit_h_min -19 _diffrn_reflns_limit_h_max 19 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 2.72 _diffrn_reflns_theta_max 30.12 _reflns_number_total 1577 _reflns_number_gt 1201 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEX2 (Bruker-Nonius)' _computing_cell_refinement 'SAINT (Bruker)' _computing_data_reduction 'SAINT (Bruker)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'X-Seed (Barbour)' _computing_publication_material ? _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^)+(0.1375P)^2^+0.2202P] 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 noref _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 1577 _refine_ls_number_parameters 68 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0798 _refine_ls_R_factor_gt 0.0628 _refine_ls_wR_factor_ref 0.2086 _refine_ls_wR_factor_gt 0.1927 _refine_ls_goodness_of_fit_ref 1.102 _refine_ls_restrained_S_all 1.102 _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 0.6667 0.3333 0.2500 0.0139(3) Uani 1 6 d S . . O1 O 0.52650(18) 0.60992(18) 0.3270(2) 0.0231(5) Uani 1 1 d . . . H1 H 0.4588 0.5412 0.2500 0.035 Uiso 1 2 d S . . N1 N 0.66342(18) 0.44883(19) 0.3568(2) 0.0153(5) Uani 1 1 d . . . O2 O 0.7957(7) 0.8979(4) 0.7500 0.0243(18) Uiso 0.33 2 d SP . . H5 H 0.8279 0.9712 0.7182 0.036 Uiso 0.33 1 d P . . C2 C 0.7317(2) 0.5008(2) 0.4655(2) 0.0177(5) Uani 1 1 d . . . H2 H 0.7797 0.4764 0.4975 0.021 Uiso 1 1 calc R . . C3 C 0.7332(2) 0.5903(2) 0.5321(3) 0.0198(6) Uani 1 1 d . . . H3 H 0.7810 0.6257 0.6095 0.024 Uiso 1 1 calc R . . C4 C 0.6640(3) 0.6261(2) 0.4834(3) 0.0213(6) Uani 1 1 d . . . H4 H 0.6662 0.6880 0.5260 0.026 Uiso 1 1 calc R . . C5 C 0.5899(2) 0.5718(2) 0.3705(3) 0.0186(6) Uani 1 1 d . . . C6 C 0.5906(2) 0.4795(2) 0.3080(2) 0.0157(5) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Co1 0.0173(4) 0.0173(4) 0.0072(4) 0.000 0.000 0.00864(18) O1 0.0359(12) 0.0312(12) 0.0132(9) -0.0032(7) -0.0044(8) 0.0251(10) N1 0.0179(11) 0.0192(11) 0.0093(9) 0.0005(7) 0.0002(7) 0.0096(9) C2 0.0210(13) 0.0222(13) 0.0107(10) -0.0013(9) -0.0011(9) 0.0115(11) C3 0.0258(14) 0.0235(13) 0.0102(10) -0.0028(9) -0.0016(9) 0.0123(11) C4 0.0296(15) 0.0251(14) 0.0128(11) -0.0028(9) -0.0024(10) 0.0164(12) C5 0.0276(14) 0.0236(13) 0.0095(10) 0.0005(9) 0.0008(9) 0.0163(12) C6 0.0204(12) 0.0205(13) 0.0085(9) 0.0001(8) -0.0003(9) 0.0119(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 N1 1.938(2) 6 ? Co1 N1 1.938(2) 3_665 ? Co1 N1 1.938(2) 5_655 ? Co1 N1 1.938(2) 2_655 ? Co1 N1 1.938(2) 4_665 ? Co1 N1 1.938(2) . ? O1 C5 1.322(3) . ? N1 C2 1.348(3) . ? N1 C6 1.380(3) . ? C2 C3 1.403(4) . ? C3 C4 1.386(4) . ? C4 C5 1.421(4) . ? C5 C6 1.435(4) . ? C6 C6 1.477(5) 4_665 ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N1 Co1 N1 86.39(13) 6 3_665 ? N1 Co1 N1 95.37(9) 6 5_655 ? N1 Co1 N1 82.91(13) 3_665 5_655 ? N1 Co1 N1 82.91(13) 6 2_655 ? N1 Co1 N1 95.37(9) 3_665 2_655 ? N1 Co1 N1 177.65(13) 5_655 2_655 ? N1 Co1 N1 95.37(9) 6 4_665 ? N1 Co1 N1 177.65(13) 3_665 4_665 ? N1 Co1 N1 95.37(8) 5_655 4_665 ? N1 Co1 N1 86.39(13) 2_655 4_665 ? N1 Co1 N1 177.65(13) 6 . ? N1 Co1 N1 95.37(9) 3_665 . ? N1 Co1 N1 86.39(13) 5_655 . ? N1 Co1 N1 95.37(9) 2_655 . ? N1 Co1 N1 82.91(13) 4_665 . ? C2 N1 C6 121.8(2) . . ? C2 N1 Co1 122.89(18) . . ? C6 N1 Co1 115.18(16) . . ? N1 C2 C3 121.1(2) . . ? C4 C3 C2 119.0(2) . . ? C3 C4 C5 121.1(3) . . ? O1 C5 C4 118.7(2) . . ? O1 C5 C6 123.8(2) . . ? C4 C5 C6 117.5(2) . . ? N1 C6 C5 119.5(2) . . ? N1 C6 C6 113.12(14) . 4_665 ? C5 C6 C6 127.43(15) . 4_665 ? _diffrn_measured_fraction_theta_max 0.980 _diffrn_reflns_theta_full 30.12 _diffrn_measured_fraction_theta_full 0.980 _refine_diff_density_max 1.602 _refine_diff_density_min -0.419 _refine_diff_density_rms 0.127 #===END #Complex 2 data_2 _database_code_depnum_ccdc_archive 'CCDC 629300' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ;tris(2,2'-bipyridine-3,3-diol-H)cobalt(iii) 1,2- dibromobenzene clathrate ; _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C36 H25 Br2 Co N6 O6' _chemical_formula_weight 856.37 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' Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Trigonal _symmetry_space_group_name_H-M P-31c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-y, x-y, z' '-x+y, -x, z' '-y, -x, -z+1/2' '-x+y, y, -z+1/2' 'x, x-y, -z+1/2' '-x, -y, -z' 'y, -x+y, -z' 'x-y, x, -z' 'y, x, z-1/2' 'x-y, -y, z-1/2' '-x, -x+y, z-1/2' _cell_length_a 14.2706(5) _cell_length_b 14.2706(5) _cell_length_c 9.4516(4) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 120.00 _cell_volume 1666.94(11) _cell_formula_units_Z 2 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description prism _exptl_crystal_colour 'dark red' _exptl_crystal_size_max 0.26 _exptl_crystal_size_mid 0.13 _exptl_crystal_size_min 0.09 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.706 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 856 _exptl_absorpt_coefficient_mu 2.970 _exptl_absorpt_correction_type multiscan _exptl_absorpt_correction_T_min 0.5123 _exptl_absorpt_correction_T_max 0.7759 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'rotating anode' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type CCD _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 25702 _diffrn_reflns_av_R_equivalents 0.0673 _diffrn_reflns_av_sigmaI/netI 0.0310 _diffrn_reflns_limit_h_min -18 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 2.71 _diffrn_reflns_theta_max 27.20 _reflns_number_total 1245 _reflns_number_gt 977 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Apex2 (Bruker-Nonius)' _computing_cell_refinement 'SAINT (Bruker)' _computing_data_reduction 'SAINT (Bruker)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'X-Seed (Barbour)' _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. The three largest residual electron density peaks that occur after refinement of the [Co(bpydiol-H)3] moiety were assigned as partly occupied Br atoms. The Uiso values for these positions were initially set at 0.08 and their occupancies allowed to refine. This gave an overall Br occupancy of approximately two per [Co(bpydiol-H)3] molecule, as would be expected for the proposed formula. The Br occupancies were then set at levels to give exactly two Br per [Co(bpydiol-H)3], and their displacement parameters were refined anisotropically. Further residual electron density peaks were assigned as disordered carbon atoms and refined isotropically. Hydrogen atoms were not included for the 1,2-dibromobenzene due to its extreme disorder. ; _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^)+(0.0585P)^2^+3.9865P] 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 1245 _refine_ls_number_parameters 95 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0694 _refine_ls_R_factor_gt 0.0495 _refine_ls_wR_factor_ref 0.1378 _refine_ls_wR_factor_gt 0.1250 _refine_ls_goodness_of_fit_ref 1.054 _refine_ls_restrained_S_all 1.054 _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 0.3333 0.6667 0.2500 0.0152(3) Uani 1 6 d S . . N1 N 0.44762(19) 0.66337(19) 0.3572(2) 0.0164(5) Uani 1 1 d . . . O1 O 0.60634(19) 0.5273(2) 0.3286(2) 0.0305(6) Uani 1 1 d . . . C4 C 0.6218(3) 0.6628(3) 0.4840(3) 0.0260(7) Uani 1 1 d . . . H4 H 0.6825 0.6644 0.5277 0.031 Uiso 1 1 calc R . . C6 C 0.4992(2) 0.7309(2) 0.4655(3) 0.0211(6) Uani 1 1 d . . . H6 H 0.4758 0.7790 0.4972 0.025 Uiso 1 1 calc R . . C3 C 0.5691(2) 0.5905(2) 0.3710(3) 0.0211(6) Uani 1 1 d . . . C5 C 0.5864(3) 0.7311(3) 0.5317(3) 0.0254(7) Uani 1 1 d . . . H5 H 0.6214 0.7781 0.6093 0.030 Uiso 1 1 calc R . . C2 C 0.4779(2) 0.5916(2) 0.3088(3) 0.0176(6) Uani 1 1 d . . . Br2 Br 0.8362(3) 0.8237(4) 0.7691(6) 0.0863(13) Uani 0.18 1 d P . . Br3 Br 0.9032(5) 0.8063(9) 0.7500 0.103(6) Uani 0.14 2 d SP . . C7 C 0.9699(7) 0.9397(15) 0.7500 0.225(11) Uiso 1 2 d S . . Br1 Br 0.9226(18) 0.8207(8) 0.6690(14) 0.097(5) Uani 0.09 1 d P . . C8 C 0.844(3) 0.9222(13) 0.7500 0.305(15) Uiso 1 2 d S . . H(1) H 0.543(3) 0.457(3) 0.2500 0.08(2) Uiso 1 2 d S . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Co1 0.0139(3) 0.0139(3) 0.0177(5) 0.000 0.000 0.00696(16) N1 0.0153(11) 0.0147(11) 0.0188(11) -0.0001(10) 0.0011(9) 0.0072(10) O1 0.0314(13) 0.0424(14) 0.0312(13) -0.0101(11) -0.0092(10) 0.0287(12) C4 0.0236(16) 0.0320(17) 0.0266(16) -0.0021(14) -0.0075(13) 0.0172(14) C6 0.0200(14) 0.0187(14) 0.0243(16) -0.0022(12) -0.0027(12) 0.0095(12) C3 0.0191(14) 0.0248(15) 0.0223(14) 0.0000(12) -0.0001(12) 0.0130(13) C5 0.0242(16) 0.0240(16) 0.0247(16) -0.0058(13) -0.0069(13) 0.0096(13) C2 0.0169(14) 0.0160(13) 0.0197(14) 0.0009(12) 0.0008(11) 0.0081(11) Br2 0.0416(17) 0.078(2) 0.112(4) 0.014(2) -0.001(2) 0.0092(16) Br3 0.132(13) 0.030(4) 0.113(13) 0.000 -0.009(14) 0.0152(19) Br1 0.125(12) 0.031(4) 0.113(11) -0.038(6) -0.050(10) 0.023(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 Co1 N1 1.940(2) 5 ? Co1 N1 1.940(2) 2_665 ? Co1 N1 1.940(2) 6_565 ? Co1 N1 1.940(2) 3_565 ? Co1 N1 1.940(2) 4_665 ? Co1 N1 1.940(2) . ? N1 C6 1.345(4) . ? N1 C2 1.374(4) . ? O1 C3 1.317(4) . ? C4 C5 1.379(4) . ? C4 C3 1.413(4) . ? C6 C5 1.392(4) . ? C3 C2 1.435(4) . ? C2 C2 1.489(6) 4_665 ? Br2 Br1 1.08(2) 5_656 ? Br2 Br3 1.115(6) . ? Br2 C8 1.363(6) . ? Br2 Br1 1.57(2) . ? Br2 C7 1.804(15) . ? Br2 Br2 2.189(10) 5_656 ? Br2 Br2 2.719(10) 6_566 ? Br3 Br1 0.805(16) 5_656 ? Br3 Br1 0.805(16) . ? Br3 Br2 1.115(6) 5_656 ? Br3 C7 1.65(2) . ? Br3 C8 2.196(13) 2_765 ? Br3 C8 2.196(13) . ? C7 C7 1.29(3) 2_765 ? C7 C7 1.29(3) 3_675 ? C7 Br1 1.667(18) . ? C7 Br1 1.667(19) 5_656 ? C7 C8 1.68(3) 2_765 ? C7 C8 1.68(3) . ? C7 Br2 1.804(15) 5_656 ? Br1 Br2 1.08(2) 5_656 ? Br1 Br1 1.57(3) 5_656 ? Br1 C8 2.09(2) 2_765 ? Br1 C8 2.36(2) . ? C8 Br2 1.363(6) 6_566 ? C8 C7 1.68(3) 3_675 ? C8 Br1 2.09(2) 5_656 ? C8 Br1 2.09(2) 3_675 ? C8 Br3 2.196(13) 3_675 ? C8 Br1 2.36(2) 6_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 N1 Co1 N1 86.57(14) 5 2_665 ? N1 Co1 N1 95.23(9) 5 6_565 ? N1 Co1 N1 83.00(14) 2_665 6_565 ? N1 Co1 N1 83.00(14) 5 3_565 ? N1 Co1 N1 95.23(9) 2_665 3_565 ? N1 Co1 N1 177.59(14) 6_565 3_565 ? N1 Co1 N1 95.23(9) 5 4_665 ? N1 Co1 N1 177.59(14) 2_665 4_665 ? N1 Co1 N1 95.23(9) 6_565 4_665 ? N1 Co1 N1 86.57(14) 3_565 4_665 ? N1 Co1 N1 177.59(14) 5 . ? N1 Co1 N1 95.23(9) 2_665 . ? N1 Co1 N1 86.57(14) 6_565 . ? N1 Co1 N1 95.23(9) 3_565 . ? N1 Co1 N1 83.00(14) 4_665 . ? C6 N1 C2 121.6(2) . . ? C6 N1 Co1 123.1(2) . . ? C2 N1 Co1 115.18(19) . . ? C5 C4 C3 120.9(3) . . ? N1 C6 C5 120.9(3) . . ? O1 C3 C4 118.7(3) . . ? O1 C3 C2 124.1(3) . . ? C4 C3 C2 117.2(3) . . ? C4 C5 C6 119.6(3) . . ? N1 C2 C3 119.8(3) . . ? N1 C2 C2 113.09(16) . 4_665 ? C3 C2 C2 127.14(17) . 4_665 ? Br1 Br2 Br3 43.0(11) 5_656 . ? Br1 Br2 C8 117.6(14) 5_656 . ? Br3 Br2 C8 124.5(15) . . ? Br1 Br2 Br1 69.9(12) 5_656 . ? Br3 Br2 Br1 29.0(7) . . ? C8 Br2 Br1 106.5(11) . . ? Br1 Br2 C7 65.1(6) 5_656 . ? Br3 Br2 C7 63.7(7) . . ? C8 Br2 C7 62.2(15) . . ? Br1 Br2 C7 58.7(5) . . ? Br1 Br2 Br2 42.4(10) 5_656 5_656 ? Br3 Br2 Br2 11.1(6) . 5_656 ? C8 Br2 Br2 113.7(14) . 5_656 ? Br1 Br2 Br2 27.5(6) . 5_656 ? C7 Br2 Br2 52.6(4) . 5_656 ? Br1 Br2 Br2 121.2(8) 5_656 6_566 ? Br3 Br2 Br2 128.5(6) . 6_566 ? C8 Br2 Br2 4.3(14) . 6_566 ? Br1 Br2 Br2 109.6(5) . 6_566 ? C7 Br2 Br2 66.5(4) . 6_566 ? Br2 Br2 Br2 117.83(15) 5_656 6_566 ? Br1 Br3 Br1 155(3) 5_656 . ? Br1 Br3 Br2 108.8(17) 5_656 5_656 ? Br1 Br3 Br2 66.0(16) . 5_656 ? Br1 Br3 Br2 66.0(16) 5_656 . ? Br1 Br3 Br2 108.8(17) . . ? Br2 Br3 Br2 157.9(12) 5_656 . ? Br1 Br3 C7 77.3(13) 5_656 . ? Br1 Br3 C7 77.3(13) . . ? Br2 Br3 C7 78.9(6) 5_656 . ? Br2 Br3 C7 78.9(6) . . ? Br1 Br3 C8 91.3(16) 5_656 2_765 ? Br1 Br3 C8 72.0(15) . 2_765 ? Br2 Br3 C8 30.8(9) 5_656 2_765 ? Br2 Br3 C8 127.5(12) . 2_765 ? C7 Br3 C8 49.3(9) . 2_765 ? Br1 Br3 C8 72.0(15) 5_656 . ? Br1 Br3 C8 91.3(16) . . ? Br2 Br3 C8 127.5(12) 5_656 . ? Br2 Br3 C8 30.8(9) . . ? C7 Br3 C8 49.3(9) . . ? C8 Br3 C8 98.6(17) 2_765 . ? C7 C7 C7 60.000(5) 2_765 3_675 ? C7 C7 Br3 150.000(2) 2_765 . ? C7 C7 Br3 150.000(8) 3_675 . ? C7 C7 Br1 135.3(8) 2_765 . ? C7 C7 Br1 144.7(7) 3_675 . ? Br3 C7 Br1 28.1(6) . . ? C7 C7 Br1 144.7(7) 2_765 5_656 ? C7 C7 Br1 135.3(8) 3_675 5_656 ? Br3 C7 Br1 28.1(6) . 5_656 ? Br1 C7 Br1 56.2(12) . 5_656 ? C7 C7 C8 67.4(7) 2_765 2_765 ? C7 C7 C8 127.4(7) 3_675 2_765 ? Br3 C7 C8 82.6(7) . 2_765 ? Br1 C7 C8 77.4(10) . 2_765 ? Br1 C7 C8 89.5(11) 5_656 2_765 ? C7 C7 C8 127.4(7) 2_765 . ? C7 C7 C8 67.4(7) 3_675 . ? Br3 C7 C8 82.6(7) . . ? Br1 C7 C8 89.5(11) . . ? Br1 C7 C8 77.4(10) 5_656 . ? C8 C7 C8 165.2(15) 2_765 . ? C7 C7 Br2 112.9(4) 2_765 5_656 ? C7 C7 Br2 171.0(4) 3_675 5_656 ? Br3 C7 Br2 37.4(4) . 5_656 ? Br1 C7 Br2 35.9(8) . 5_656 ? Br1 C7 Br2 53.7(9) 5_656 5_656 ? C8 C7 Br2 45.9(5) 2_765 5_656 ? C8 C7 Br2 119.4(11) . 5_656 ? C7 C7 Br2 171.0(4) 2_765 . ? C7 C7 Br2 112.9(4) 3_675 . ? Br3 C7 Br2 37.4(4) . . ? Br1 C7 Br2 53.7(9) . . ? Br1 C7 Br2 35.9(8) 5_656 . ? C8 C7 Br2 119.4(11) 2_765 . ? C8 C7 Br2 45.9(5) . . ? Br2 C7 Br2 74.7(8) 5_656 . ? Br3 Br1 Br2 71.0(13) . 5_656 ? Br3 Br1 Br1 12.7(13) . 5_656 ? Br2 Br1 Br1 70.0(13) 5_656 5_656 ? Br3 Br1 Br2 42.2(12) . . ? Br2 Br1 Br2 110.0(11) 5_656 . ? Br1 Br1 Br2 40.1(12) 5_656 . ? Br3 Br1 C7 74.6(13) . . ? Br2 Br1 C7 79.0(6) 5_656 . ? Br1 Br1 C7 61.9(6) 5_656 . ? Br2 Br1 C7 67.6(6) . . ? Br3 Br1 C8 86.5(14) . 2_765 ? Br2 Br1 C8 35.3(9) 5_656 2_765 ? Br1 Br1 C8 78.6(12) 5_656 2_765 ? Br2 Br1 C8 109.5(8) . 2_765 ? C7 Br1 C8 51.6(10) . 2_765 ? Br3 Br1 C8 68.8(15) . . ? Br2 Br1 C8 117.5(9) 5_656 . ? Br1 Br1 C8 60.6(13) 5_656 . ? Br2 Br1 C8 33.7(6) . . ? C7 Br1 C8 45.5(9) . . ? C8 Br1 C8 96.8(16) 2_765 . ? Br2 C8 Br2 171(3) . 6_566 ? Br2 C8 C7 116.6(19) . 3_675 ? Br2 C8 C7 71.9(12) 6_566 3_675 ? Br2 C8 C7 71.9(12) . . ? Br2 C8 C7 116.6(19) 6_566 . ? C7 C8 C7 45.2(15) 3_675 . ? Br2 C8 Br1 27.1(6) . 5_656 ? Br2 C8 Br1 159.5(17) 6_566 5_656 ? C7 C8 Br1 92.5(14) 3_675 5_656 ? C7 C8 Br1 51.0(9) . 5_656 ? Br2 C8 Br1 159.5(17) . 3_675 ? Br2 C8 Br1 27.1(6) 6_566 3_675 ? C7 C8 Br1 51.0(9) 3_675 3_675 ? C7 C8 Br1 92.5(14) . 3_675 ? Br1 C8 Br1 143(2) 5_656 3_675 ? Br2 C8 Br3 163(2) . 3_675 ? Br2 C8 Br3 24.7(6) 6_566 3_675 ? C7 C8 Br3 48.1(8) 3_675 3_675 ? C7 C8 Br3 93.3(14) . 3_675 ? Br1 C8 Br3 136.1(15) 5_656 3_675 ? Br1 C8 Br3 21.5(5) 3_675 3_675 ? Br2 C8 Br3 24.7(6) . . ? Br2 C8 Br3 163(2) 6_566 . ? C7 C8 Br3 93.3(14) 3_675 . ? C7 C8 Br3 48.1(8) . . ? Br1 C8 Br3 21.5(5) 5_656 . ? Br1 C8 Br3 136.1(15) 3_675 . ? Br3 C8 Br3 141.4(17) 3_675 . ? Br2 C8 Br1 146.0(13) . 6_566 ? Br2 C8 Br1 39.8(6) 6_566 6_566 ? C7 C8 Br1 45.1(8) 3_675 6_566 ? C7 C8 Br1 87.0(13) . 6_566 ? Br1 C8 Br1 119.8(13) 5_656 6_566 ? Br1 C8 Br1 40.8(8) 3_675 6_566 ? Br3 C8 Br1 20.0(4) 3_675 6_566 ? Br3 C8 Br1 131.9(15) . 6_566 ? Br2 C8 Br1 39.8(6) . . ? Br2 C8 Br1 146.0(13) 6_566 . ? C7 C8 Br1 87.0(13) 3_675 . ? C7 C8 Br1 45.1(8) . . ? Br1 C8 Br1 40.8(8) 5_656 . ? Br1 C8 Br1 119.8(13) 3_675 . ? Br3 C8 Br1 131.9(15) 3_675 . ? Br3 C8 Br1 20.0(4) . . ? Br1 C8 Br1 131.5(17) 6_566 . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 27.20 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.802 _refine_diff_density_min -0.695 _refine_diff_density_rms 0.088 #===END #Complex 3 data_3 _database_code_depnum_ccdc_archive 'CCDC 629301' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common "(2,2'-bipyridine-3,3'-diol -H)chlorocopper(ii)" _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C10 H7 Cl Cu N2 O2' _chemical_formula_weight 286.17 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' Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Tetragonal _symmetry_space_group_name_H-M I4(1)/a loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-y+3/4, x+1/4, z+1/4' '-x, -y+1/2, z' 'y+1/4, -x+1/4, z+1/4' 'x+1/2, y+1/2, z+1/2' '-y+5/4, x+3/4, z+3/4' '-x+1/2, -y+1, z+1/2' 'y+3/4, -x+3/4, z+3/4' '-x, -y, -z' 'y-3/4, -x-1/4, -z-1/4' 'x, y-1/2, -z' '-y-1/4, x-1/4, -z-1/4' '-x+1/2, -y+1/2, -z+1/2' 'y-1/4, -x+1/4, -z+1/4' 'x+1/2, y, -z+1/2' '-y+1/4, x+1/4, -z+1/4' _cell_length_a 13.1259(3) _cell_length_b 13.1259(3) _cell_length_c 22.2808(6) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 3838.74(16) _cell_formula_units_Z 16 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour black _exptl_crystal_size_max 0.16 _exptl_crystal_size_mid 0.16 _exptl_crystal_size_min 0.09 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.981 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2288 _exptl_absorpt_coefficient_mu 2.535 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6872 _exptl_absorpt_correction_T_max 0.8040 _exptl_absorpt_process_details SORTAV _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(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 CCD _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 12365 _diffrn_reflns_av_R_equivalents 0.0652 _diffrn_reflns_av_sigmaI/netI 0.0410 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -28 _diffrn_reflns_limit_l_max 28 _diffrn_reflns_theta_min 3.59 _diffrn_reflns_theta_max 27.49 _reflns_number_total 2195 _reflns_number_gt 1855 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'COLLECT (Nonius)' _computing_cell_refinement 'DENZO (Nonius)' _computing_data_reduction 'DENZO (Nonius)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'X-Seed (Barbour)' _computing_publication_material ? _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^)+(0.0435P)^2^+8.2642P] 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 2195 _refine_ls_number_parameters 169 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0467 _refine_ls_R_factor_gt 0.0364 _refine_ls_wR_factor_ref 0.0949 _refine_ls_wR_factor_gt 0.0887 _refine_ls_goodness_of_fit_ref 1.074 _refine_ls_restrained_S_all 1.074 _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 Cu1 Cu 0.13268(3) 0.71075(3) 0.085357(15) 0.02404(14) Uani 1 1 d . . . Cl1 Cl 0.08542(6) 0.85263(6) 0.03803(3) 0.02987(19) Uani 1 1 d . . . O1 O 0.13156(18) 0.65190(18) 0.31945(9) 0.0335(5) Uani 1 1 d . . . H1 H 0.1300 0.5916 0.3068 0.040 Uiso 1 1 calc R . . N1 N 0.12057(18) 0.75965(18) 0.16917(11) 0.0237(5) Uani 1 1 d . . . O1A O 0.08790(17) 0.48363(16) 0.27701(9) 0.0298(5) Uani 1 1 d . . . N1A N 0.13256(18) 0.57888(18) 0.12680(10) 0.0223(5) Uani 1 1 d . . . C2 C 0.1205(2) 0.6856(2) 0.21230(13) 0.0224(6) Uani 1 1 d . . . C2A C 0.1194(2) 0.5804(2) 0.18741(12) 0.0211(5) Uani 1 1 d . . . C3 C 0.1251(2) 0.7160(2) 0.27324(13) 0.0249(6) Uani 1 1 d . . . C3A C 0.1059(2) 0.4868(2) 0.21855(13) 0.0240(6) Uani 1 1 d . . . C4 C 0.1267(2) 0.8192(2) 0.28677(14) 0.0283(6) Uani 1 1 d . . . H4 H 0.128(3) 0.835(3) 0.3218(16) 0.028(9) Uiso 1 1 d . . . C4A C 0.1121(2) 0.3964(2) 0.18526(14) 0.0267(6) Uani 1 1 d . . . H4A H 0.104(3) 0.343(3) 0.2045(16) 0.030(9) Uiso 1 1 d . . . C5 C 0.1271(2) 0.8910(2) 0.24209(14) 0.0286(6) Uani 1 1 d . . . H5 H 0.130(3) 0.959(3) 0.2503(16) 0.031(9) Uiso 1 1 d . . . C5A C 0.1258(2) 0.3986(2) 0.12424(14) 0.0284(6) Uani 1 1 d . . . H5A H 0.132(3) 0.340(3) 0.1038(18) 0.042(10) Uiso 1 1 d . . . C6 C 0.1244(2) 0.8584(2) 0.18302(14) 0.0262(6) Uani 1 1 d . . . H6 H 0.121(3) 0.906(3) 0.1499(17) 0.033(9) Uiso 1 1 d . . . C6A C 0.1347(2) 0.4914(2) 0.09593(14) 0.0280(6) Uani 1 1 d . . . H6A H 0.147(3) 0.497(3) 0.0544(17) 0.031(9) 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 Cu1 0.0313(2) 0.0239(2) 0.0169(2) 0.00173(13) 0.00449(13) 0.00195(13) Cl1 0.0363(4) 0.0278(4) 0.0256(4) 0.0053(3) -0.0018(3) 0.0004(3) O1 0.0475(14) 0.0355(12) 0.0176(10) 0.0005(9) -0.0008(9) -0.0043(10) N1 0.0253(12) 0.0246(12) 0.0212(12) 0.0014(9) 0.0023(9) 0.0001(9) O1A 0.0395(12) 0.0328(11) 0.0170(9) 0.0057(8) -0.0013(9) -0.0042(9) N1A 0.0254(12) 0.0253(12) 0.0163(11) 0.0007(9) 0.0021(9) 0.0009(9) C2 0.0208(13) 0.0272(14) 0.0190(13) -0.0007(11) 0.0018(10) 0.0005(10) C2A 0.0206(13) 0.0263(14) 0.0163(12) 0.0018(10) 0.0009(10) -0.0005(10) C3 0.0216(13) 0.0342(15) 0.0188(14) -0.0015(12) 0.0013(10) -0.0029(11) C3A 0.0231(13) 0.0278(14) 0.0211(13) 0.0038(11) -0.0031(11) 0.0008(10) C4 0.0246(14) 0.0390(17) 0.0213(15) -0.0086(13) 0.0026(12) -0.0021(12) C4A 0.0275(15) 0.0242(15) 0.0284(15) 0.0058(12) 0.0002(12) 0.0012(11) C5 0.0260(14) 0.0286(16) 0.0313(16) -0.0072(13) 0.0015(12) -0.0009(11) C5A 0.0325(16) 0.0232(14) 0.0295(15) -0.0025(12) 0.0018(12) 0.0012(12) C6 0.0251(14) 0.0269(15) 0.0267(15) -0.0001(12) 0.0019(12) -0.0006(11) C6A 0.0323(15) 0.0300(15) 0.0216(14) -0.0006(12) 0.0030(12) 0.0012(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 Cu1 N1A 1.962(2) . ? Cu1 O1A 1.963(2) 8_454 ? Cu1 N1 1.981(2) . ? Cu1 Cl1 2.2282(8) . ? O1 C3 1.332(4) . ? N1 C6 1.333(4) . ? N1 C2 1.366(4) . ? O1A C3A 1.324(3) . ? O1A Cu1 1.963(2) 2 ? N1A C6A 1.339(4) . ? N1A C2A 1.362(3) . ? C2 C3 1.416(4) . ? C2 C2A 1.488(4) . ? C2A C3A 1.422(4) . ? C3 C4 1.389(4) . ? C3A C4A 1.402(4) . ? C4 C5 1.370(5) . ? C4A C5A 1.372(4) . ? C5 C6 1.384(4) . ? C5A C6A 1.377(4) . ? 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 N1A Cu1 O1A 91.45(9) . 8_454 ? N1A Cu1 N1 80.91(10) . . ? O1A Cu1 N1 141.62(10) 8_454 . ? N1A Cu1 Cl1 163.73(7) . . ? O1A Cu1 Cl1 98.42(7) 8_454 . ? N1 Cu1 Cl1 98.80(7) . . ? C6 N1 C2 121.9(3) . . ? C6 N1 Cu1 122.0(2) . . ? C2 N1 Cu1 115.64(19) . . ? C3A O1A Cu1 136.96(19) . 2 ? C6A N1A C2A 121.7(2) . . ? C6A N1A Cu1 120.98(19) . . ? C2A N1A Cu1 116.97(18) . . ? N1 C2 C3 118.3(3) . . ? N1 C2 C2A 113.4(2) . . ? C3 C2 C2A 128.2(3) . . ? N1A C2A C3A 119.1(2) . . ? N1A C2A C2 112.5(2) . . ? C3A C2A C2 128.4(2) . . ? O1 C3 C4 116.6(3) . . ? O1 C3 C2 124.5(3) . . ? C4 C3 C2 118.9(3) . . ? O1A C3A C4A 120.2(3) . . ? O1A C3A C2A 122.0(3) . . ? C4A C3A C2A 117.8(3) . . ? C5 C4 C3 120.9(3) . . ? C5A C4A C3A 121.0(3) . . ? C4 C5 C6 118.6(3) . . ? C4A C5A C6A 118.9(3) . . ? N1 C6 C5 121.4(3) . . ? N1A C6A C5A 121.4(3) . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 27.49 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.424 _refine_diff_density_min -0.617 _refine_diff_density_rms 0.096 #===END #Complex 4 data_4 _database_code_depnum_ccdc_archive 'CCDC 629302' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common (2,2'-bipyridine-3,3'-diol-H)bromocopper(ii) _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C10 H7 Br Cu N2 O2' _chemical_formula_weight 330.63 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' Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Tetragonal _symmetry_space_group_name_H-M I4(1)/a loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-y+3/4, x+1/4, z+1/4' '-x, -y+1/2, z' 'y+1/4, -x+1/4, z+1/4' 'x+1/2, y+1/2, z+1/2' '-y+5/4, x+3/4, z+3/4' '-x+1/2, -y+1, z+1/2' 'y+3/4, -x+3/4, z+3/4' '-x, -y, -z' 'y-3/4, -x-1/4, -z-1/4' 'x, y-1/2, -z' '-y-1/4, x-1/4, -z-1/4' '-x+1/2, -y+1/2, -z+1/2' 'y-1/4, -x+1/4, -z+1/4' 'x+1/2, y, -z+1/2' '-y+1/4, x+1/4, -z+1/4' _cell_length_a 13.2775(1) _cell_length_b 13.2775(1) _cell_length_c 22.4184(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 3952.18(7) _cell_formula_units_Z 16 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour Black _exptl_crystal_size_max 0.13 _exptl_crystal_size_mid 0.13 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.223 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2576 _exptl_absorpt_coefficient_mu 6.236 _exptl_absorpt_correction_type multiscan _exptl_absorpt_correction_T_min 0.4978 _exptl_absorpt_correction_T_max 0.7060 _exptl_absorpt_process_details SORTAV _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(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 CCD _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 20539 _diffrn_reflns_av_R_equivalents 0.0618 _diffrn_reflns_av_sigmaI/netI 0.0240 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -29 _diffrn_reflns_limit_l_max 28 _diffrn_reflns_theta_min 1.78 _diffrn_reflns_theta_max 27.45 _reflns_number_total 2260 _reflns_number_gt 2150 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'COLLECT (Nonius)' _computing_cell_refinement 'DENZO (Nonius)' _computing_data_reduction 'DENZO (Nonius)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'X-Seed (Barbour)' _computing_publication_material ? _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^)+(0.0000P)^2^+142.6358P] 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 noref _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2260 _refine_ls_number_parameters 146 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0562 _refine_ls_R_factor_gt 0.0539 _refine_ls_wR_factor_ref 0.1413 _refine_ls_wR_factor_gt 0.1403 _refine_ls_goodness_of_fit_ref 1.287 _refine_ls_restrained_S_all 1.287 _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 Br1 Br 0.08623(6) 0.64135(6) 0.03853(3) 0.0207(2) Uani 1 1 d . . . Cu1 Cu 0.13671(7) 0.79076(7) 0.08857(4) 0.0164(2) Uani 1 1 d . . . O1 O 0.1344(5) 0.8507(5) 0.3209(2) 0.0276(13) Uani 1 1 d . . . H1 H 0.1198 0.9092 0.3094 0.041 Uiso 1 1 calc R . . N1 N 0.1212(4) 0.7430(4) 0.1720(3) 0.0154(12) Uani 1 1 d . . . O1A O 0.0885(4) 1.0145(4) 0.2790(2) 0.0219(11) Uani 1 1 d . . . N1A N 0.1371(4) 0.9221(4) 0.1296(2) 0.0145(11) Uani 1 1 d . . . C2 C 0.1220(5) 0.8166(5) 0.2146(3) 0.0141(13) Uani 1 1 d . . . C2A C 0.1212(5) 0.9200(5) 0.1903(3) 0.0136(13) Uani 1 1 d . . . C3 C 0.1274(5) 0.7872(6) 0.2751(3) 0.0191(14) Uani 1 1 d . . . C3A C 0.1064(5) 1.0121(5) 0.2210(3) 0.0145(13) Uani 1 1 d . . . C4 C 0.1267(6) 0.6849(6) 0.2896(3) 0.0233(16) Uani 1 1 d . . . H4 H 0.1263 0.6648 0.3302 0.028 Uiso 1 1 calc R . . C4A C 0.1114(5) 1.1026(5) 0.1877(3) 0.0182(14) Uani 1 1 d . . . H4A H 0.1036 1.1655 0.2074 0.022 Uiso 1 1 calc R . . C5 C 0.1267(5) 0.6135(6) 0.2455(4) 0.0209(15) Uani 1 1 d . . . H5 H 0.1280 0.5438 0.2551 0.025 Uiso 1 1 calc R . . C5A C 0.1276(6) 1.1000(6) 0.1270(4) 0.0216(15) Uani 1 1 d . . . H5A H 0.1308 1.1606 0.1046 0.026 Uiso 1 1 calc R . . C6 C 0.1247(5) 0.6453(5) 0.1860(3) 0.0176(14) Uani 1 1 d . . . H6 H 0.1259 0.5965 0.1550 0.021 Uiso 1 1 calc R . . C6A C 0.1392(6) 1.0073(5) 0.0990(3) 0.0194(15) Uani 1 1 d . . . H6A H 0.1487 1.0051 0.0570 0.023 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 Br1 0.0245(4) 0.0194(4) 0.0182(4) -0.0046(3) -0.0020(3) 0.0004(3) Cu1 0.0239(5) 0.0150(4) 0.0103(4) -0.0012(3) 0.0044(3) -0.0018(3) O1 0.042(4) 0.032(3) 0.009(2) 0.000(2) -0.001(2) 0.004(3) N1 0.018(3) 0.013(3) 0.015(3) 0.002(2) 0.001(2) 0.001(2) O1A 0.033(3) 0.024(3) 0.009(2) -0.007(2) -0.002(2) -0.003(2) N1A 0.018(3) 0.019(3) 0.007(3) 0.002(2) 0.002(2) -0.002(2) C2 0.015(3) 0.016(3) 0.011(3) 0.000(2) 0.004(2) 0.001(2) C2A 0.015(3) 0.019(3) 0.007(3) -0.002(2) 0.003(2) -0.001(2) C3 0.015(3) 0.029(4) 0.014(3) 0.003(3) 0.004(3) 0.004(3) C3A 0.012(3) 0.019(3) 0.012(3) -0.005(3) -0.001(2) -0.002(2) C4 0.021(4) 0.033(4) 0.017(4) 0.010(3) 0.000(3) 0.006(3) C4A 0.017(3) 0.015(3) 0.022(4) -0.003(3) -0.002(3) 0.002(3) C5 0.016(3) 0.018(3) 0.029(4) 0.009(3) 0.004(3) 0.003(3) C5A 0.023(4) 0.019(4) 0.022(4) 0.003(3) 0.003(3) 0.000(3) C6 0.017(3) 0.014(3) 0.022(4) -0.002(3) 0.001(3) -0.003(3) C6A 0.024(4) 0.018(3) 0.016(3) 0.005(3) 0.003(3) 0.001(3) _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 Br1 Cu1 2.3756(11) . ? Cu1 N1A 1.972(6) . ? Cu1 O1A 1.977(5) 6_554 ? Cu1 N1 1.985(6) . ? O1 C3 1.332(9) . ? N1 C6 1.336(9) . ? N1 C2 1.367(9) . ? O1A C3A 1.322(8) . ? O1A Cu1 1.977(5) 4_465 ? N1A C6A 1.323(9) . ? N1A C2A 1.378(8) . ? C2 C3 1.412(9) . ? C2 C2A 1.477(9) . ? C2A C3A 1.417(9) . ? C3 C4 1.396(11) . ? C3A C4A 1.415(10) . ? C4 C5 1.370(12) . ? C4A C5A 1.379(10) . ? C5 C6 1.400(10) . ? C5A C6A 1.390(11) . ? 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 N1A Cu1 O1A 91.7(2) . 6_554 ? N1A Cu1 N1 81.0(2) . . ? O1A Cu1 N1 143.9(2) 6_554 . ? N1A Cu1 Br1 163.69(18) . . ? O1A Cu1 Br1 97.80(16) 6_554 . ? N1 Cu1 Br1 98.55(17) . . ? C6 N1 C2 121.9(6) . . ? C6 N1 Cu1 121.9(5) . . ? C2 N1 Cu1 115.4(5) . . ? C3A O1A Cu1 137.6(5) . 4_465 ? C6A N1A C2A 122.2(6) . . ? C6A N1A Cu1 121.0(5) . . ? C2A N1A Cu1 116.2(5) . . ? N1 C2 C3 118.3(6) . . ? N1 C2 C2A 113.9(6) . . ? C3 C2 C2A 127.7(6) . . ? N1A C2A C3A 118.9(6) . . ? N1A C2A C2 112.5(6) . . ? C3A C2A C2 128.6(6) . . ? O1 C3 C4 115.9(7) . . ? O1 C3 C2 124.6(7) . . ? C4 C3 C2 119.5(7) . . ? O1A C3A C4A 120.4(6) . . ? O1A C3A C2A 121.5(6) . . ? C4A C3A C2A 118.1(6) . . ? C5 C4 C3 120.4(7) . . ? C5A C4A C3A 120.4(7) . . ? C4 C5 C6 118.6(7) . . ? C4A C5A C6A 119.1(7) . . ? N1 C6 C5 121.2(7) . . ? N1A C6A C5A 121.3(7) . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 27.45 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.864 _refine_diff_density_min -0.710 _refine_diff_density_rms 0.184 #===END #Complex 5 data_5 _database_code_depnum_ccdc_archive 'CCDC 629303' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common (2,2'-bipyridine-3,3'-diol-H)nitrocopper(ii) _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C10 H7 Cu N3 O5' _chemical_formula_weight 312.73 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' Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 9.1960(2) _cell_length_b 10.6603(3) _cell_length_c 11.4383(3) _cell_angle_alpha 90.00 _cell_angle_beta 103.196(1) _cell_angle_gamma 90.00 _cell_volume 1091.71(5) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description prism _exptl_crystal_colour brown _exptl_crystal_size_max 0.17 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.903 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 628 _exptl_absorpt_coefficient_mu 2.023 _exptl_absorpt_correction_type multiscan _exptl_absorpt_correction_T_min 0.7249 _exptl_absorpt_correction_T_max 0.9235 _exptl_absorpt_process_details SORTAV _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(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 CCD _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 10694 _diffrn_reflns_av_R_equivalents 0.0613 _diffrn_reflns_av_sigmaI/netI 0.0439 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 2.64 _diffrn_reflns_theta_max 27.48 _reflns_number_total 2489 _reflns_number_gt 2255 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'COLLECT (Nonius)' _computing_cell_refinement 'DENZO (Nonius)' _computing_data_reduction 'DENZO (Nonius)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'X-Seed (Barbour)' _computing_publication_material ? _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^)+(0.0558P)^2^+0.6961P] 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 noref _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2489 _refine_ls_number_parameters 172 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0376 _refine_ls_R_factor_gt 0.0342 _refine_ls_wR_factor_ref 0.0973 _refine_ls_wR_factor_gt 0.0944 _refine_ls_goodness_of_fit_ref 1.035 _refine_ls_restrained_S_all 1.035 _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 Cu1 Cu 0.12743(3) 0.82493(2) 0.72366(2) 0.01794(12) Uani 1 1 d . . . O1 O -0.25383(16) 0.98879(14) 0.34639(13) 0.0217(3) Uani 1 1 d . . . H1 H -0.1994 0.9401 0.3174 0.026 Uiso 1 1 calc R . . N1 N -0.0642(2) 0.90873(17) 0.65255(16) 0.0205(4) Uani 1 1 d . . . O2 O 0.15258(17) 0.90367(15) 0.88434(13) 0.0231(3) Uani 1 1 d . . . N2 N 0.0958(2) 0.82466(17) 0.94869(18) 0.0252(4) Uani 1 1 d . . . C2 C -0.1114(2) 0.8948(2) 0.53139(18) 0.0185(4) Uani 1 1 d . . . O3 O 0.0308(2) 0.73142(17) 0.89630(15) 0.0324(4) Uani 1 1 d . . . C3 C -0.2207(2) 0.9774(2) 0.46747(19) 0.0198(4) Uani 1 1 d . . . O4 O 0.1097(3) 0.8447(2) 1.05562(17) 0.0475(5) Uani 1 1 d . . . C4 C -0.2934(2) 1.0583(2) 0.5318(2) 0.0244(5) Uani 1 1 d . . . H4 H -0.3742 1.1087 0.4906 0.029 Uiso 1 1 calc R . . C5 C -0.2476(3) 1.0649(2) 0.6548(2) 0.0276(5) Uani 1 1 d . . . H5 H -0.2969 1.1190 0.6993 0.033 Uiso 1 1 calc R . . C6 C -0.1290(2) 0.9915(2) 0.71268(19) 0.0246(5) Uani 1 1 d . . . H6 H -0.0926 0.9999 0.7970 0.030 Uiso 1 1 calc R . . O1A O -0.19455(16) 0.77705(14) 0.28455(12) 0.0207(3) Uani 1 1 d . . . N1A N 0.08851(19) 0.74757(17) 0.56273(15) 0.0193(4) Uani 1 1 d . . . C2A C -0.0329(2) 0.7930(2) 0.48190(18) 0.0178(4) Uani 1 1 d . . . C3A C -0.0747(2) 0.7389(2) 0.36631(18) 0.0197(4) Uani 1 1 d . . . C4A C 0.0140(3) 0.6415(2) 0.33795(19) 0.0246(5) Uani 1 1 d . . . H4A H -0.0101 0.6052 0.2601 0.029 Uiso 1 1 calc R . . C5A C 0.1349(3) 0.5983(2) 0.4214(2) 0.0267(5) Uani 1 1 d . . . H5A H 0.1936 0.5312 0.4025 0.032 Uiso 1 1 calc R . . C6A C 0.1703(3) 0.6541(2) 0.5341(2) 0.0228(4) Uani 1 1 d . . . H6A H 0.2547 0.6250 0.5921 0.027 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 Cu1 0.01738(18) 0.02023(19) 0.01373(17) -0.00066(8) -0.00158(11) 0.00119(9) O1 0.0221(7) 0.0221(8) 0.0186(7) 0.0014(6) -0.0003(6) 0.0045(6) N1 0.0199(8) 0.0230(9) 0.0174(8) -0.0002(7) 0.0019(7) 0.0002(7) O2 0.0258(8) 0.0236(8) 0.0188(7) -0.0009(6) 0.0028(6) -0.0026(6) N2 0.0251(10) 0.0306(11) 0.0194(9) -0.0011(7) 0.0041(8) 0.0010(8) C2 0.0163(9) 0.0211(10) 0.0161(9) -0.0009(7) -0.0003(7) -0.0003(8) O3 0.0327(9) 0.0323(10) 0.0321(9) -0.0011(7) 0.0072(7) -0.0112(8) C3 0.0173(9) 0.0210(11) 0.0193(10) 0.0008(8) 0.0004(8) -0.0023(8) O4 0.0717(15) 0.0527(13) 0.0213(9) -0.0050(8) 0.0174(10) -0.0067(11) C4 0.0206(10) 0.0248(11) 0.0266(11) 0.0012(9) 0.0027(9) 0.0049(8) C5 0.0264(11) 0.0301(12) 0.0272(11) -0.0021(9) 0.0078(9) 0.0066(9) C6 0.0250(11) 0.0304(12) 0.0178(10) -0.0020(8) 0.0036(8) 0.0036(9) O1A 0.0191(7) 0.0227(8) 0.0160(7) -0.0001(6) -0.0047(5) -0.0009(6) N1A 0.0182(8) 0.0213(9) 0.0158(8) 0.0003(6) -0.0013(6) 0.0024(7) C2A 0.0161(9) 0.0190(10) 0.0166(9) 0.0001(8) 0.0001(7) -0.0008(8) C3A 0.0185(9) 0.0203(10) 0.0174(9) 0.0006(8) -0.0023(8) -0.0010(8) C4A 0.0259(11) 0.0266(11) 0.0189(10) -0.0052(9) 0.0001(9) 0.0026(9) C5A 0.0258(11) 0.0261(12) 0.0259(11) -0.0071(9) 0.0011(9) 0.0056(9) C6A 0.0213(10) 0.0244(11) 0.0195(10) -0.0007(8) -0.0021(8) 0.0059(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 Cu1 O1A 1.9561(15) 4_676 ? Cu1 N1A 1.9738(17) . ? Cu1 N1 1.9774(18) . ? Cu1 O2 1.9854(15) . ? O1 C3 1.354(2) . ? N1 C6 1.339(3) . ? N1 C2 1.363(3) . ? O2 N2 1.303(3) . ? N2 O4 1.219(3) . ? N2 O3 1.241(3) . ? C2 C3 1.410(3) . ? C2 C2A 1.485(3) . ? C3 C4 1.399(3) . ? C4 C5 1.374(3) . ? C5 C6 1.383(3) . ? O1A C3A 1.336(2) . ? O1A Cu1 1.9561(15) 4_575 ? N1A C6A 1.334(3) . ? N1A C2A 1.365(3) . ? C2A C3A 1.413(3) . ? C3A C4A 1.403(3) . ? C4A C5A 1.369(3) . ? C5A C6A 1.390(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 O1A Cu1 N1A 93.36(7) 4_676 . ? O1A Cu1 N1 172.88(7) 4_676 . ? N1A Cu1 N1 81.39(7) . . ? O1A Cu1 O2 89.67(6) 4_676 . ? N1A Cu1 O2 176.34(7) . . ? N1 Cu1 O2 95.41(7) . . ? C6 N1 C2 121.23(18) . . ? C6 N1 Cu1 123.06(14) . . ? C2 N1 Cu1 114.59(14) . . ? N2 O2 Cu1 105.81(12) . . ? O4 N2 O3 123.6(2) . . ? O4 N2 O2 119.3(2) . . ? O3 N2 O2 117.10(18) . . ? N1 C2 C3 118.89(19) . . ? N1 C2 C2A 113.44(17) . . ? C3 C2 C2A 127.63(18) . . ? O1 C3 C4 117.42(19) . . ? O1 C3 C2 123.61(19) . . ? C4 C3 C2 118.84(19) . . ? C5 C4 C3 119.9(2) . . ? C4 C5 C6 119.0(2) . . ? N1 C6 C5 121.4(2) . . ? C3A O1A Cu1 124.73(13) . 4_575 ? C6A N1A C2A 121.24(18) . . ? C6A N1A Cu1 123.27(14) . . ? C2A N1A Cu1 115.44(14) . . ? N1A C2A C3A 119.67(19) . . ? N1A C2A C2 113.22(17) . . ? C3A C2A C2 127.06(18) . . ? O1A C3A C4A 119.58(18) . . ? O1A C3A C2A 122.40(19) . . ? C4A C3A C2A 118.02(18) . . ? C5A C4A C3A 120.7(2) . . ? C4A C5A C6A 118.9(2) . . ? N1A C6A C5A 121.4(2) . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.565 _refine_diff_density_min -0.718 _refine_diff_density_rms 0.091