Supplementary Material (ESI) for Dalton Transactions This journal is © The Royal Society of Chemistry 2003 data_global _journal_coden_Cambridge 186 _publ_requested_journal 'Dalton Transactions' _publ_contact_author_name ' Paul E. Kruger ' _publ_contact_author_address ; Department of Chemistry Trinity College Dublin Dublin 2 Ireland ; _publ_contact_author_phone ' 353 1 608 1422 ' _publ_contact_author_fax ' 353 1 671 2826 ' _publ_contact_author_email ' paul.kruger@tcd.ie ' loop_ _publ_author_name _publ_author_address ' Paul E. Kruger ' ; Department of Chemistry Trinity College Dublin Dublin 2 Ireland ; ' Eithne Tynan ' ; Department of Chemistry Trinity College Dublin Dublin 2 Ireland ; ' Anthea C. Lees ' ; Department of Chemistry Trinity College Dublin Dublin 2 Ireland ; ' Paul Jensen ' ; Department of Chemistry Trinity College Dublin Dublin 2 Ireland ; ' Mark Nieuwenhuyzen' ; Chemistry Department Queen's University Belfast, BT9 5AG UK ; _publ_section_title ; Coordination and Hydrogen-bonded Networks featuring 4,4' -dicarboxy-2,2'-bipyridine (H2dcbp): Structural characterisation of H2dcbp, [Co(dcbp)(H2O)4].4H2O, and {[Cu(dcbp)(H2O)2].2H2O}n. ; data_H2dcb _database_code_CSD 199918 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common "2,2'-bipyridine-4,4'-dicarboxylic acid" _chemical_melting_point ? _chemical_formula_moiety H2dcbp _chemical_formula_sum 'C12 H8 N2 O4' _chemical_formula_weight 244.20 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' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M Cc loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' 'x, -y, z+1/2' 'x+1/2, y+1/2, z' 'x+1/2, -y+1/2, z+1/2' _cell_length_a 3.6250(10) _cell_length_b 14.644(5) _cell_length_c 18.649(7) _cell_angle_alpha 90.00 _cell_angle_beta 91.199(5) _cell_angle_gamma 90.00 _cell_volume 989.8(6) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description Needle _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.4 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.1 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.639 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 504 _exptl_absorpt_coefficient_mu 0.126 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.833 _exptl_absorpt_correction_T_max 1.000 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(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 'Bruker SMART APEX CCD' _diffrn_measurement_method 'Omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 4020 _diffrn_reflns_av_R_equivalents 0.0380 _diffrn_reflns_av_sigmaI/netI 0.0432 _diffrn_reflns_limit_h_min -4 _diffrn_reflns_limit_h_max 4 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 2.18 _diffrn_reflns_theta_max 23.29 _reflns_number_total 1396 _reflns_number_gt 1300 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _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^)+(0.0367P)^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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.7(14) _refine_ls_number_reflns 1396 _refine_ls_number_parameters 169 _refine_ls_number_restraints 4 _refine_ls_R_factor_all 0.0370 _refine_ls_R_factor_gt 0.0329 _refine_ls_wR_factor_ref 0.0745 _refine_ls_wR_factor_gt 0.0718 _refine_ls_goodness_of_fit_ref 1.025 _refine_ls_restrained_S_all 1.025 _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 C1 C 0.0493(8) 0.37957(19) -0.22288(15) 0.0216(7) Uani 1 1 d . . . H1 H 0.0135 0.3380 -0.2615 0.026 Uiso 1 1 calc R . . C2 C 0.1500(8) 0.4682(2) -0.23845(15) 0.0230(7) Uani 1 1 d . . . H2 H 0.1850 0.4868 -0.2866 0.028 Uiso 1 1 calc R . . C3 C 0.1990(8) 0.52927(19) -0.18260(15) 0.0183(7) Uani 1 1 d . . . C4 C 0.1482(8) 0.49919(19) -0.11304(14) 0.0191(7) Uani 1 1 d . . . H4 H 0.1781 0.5400 -0.0738 0.023 Uiso 1 1 calc R . . C5 C 0.0534(7) 0.40882(18) -0.10152(14) 0.0176(7) Uani 1 1 d . . . C6 C 0.0118(7) 0.36958(18) -0.02786(14) 0.0181(7) Uani 1 1 d . . . C7 C 0.0985(7) 0.27882(19) -0.01459(14) 0.0183(7) Uani 1 1 d . . . H7 H 0.1955 0.2418 -0.0515 0.022 Uiso 1 1 calc R . . C8 C 0.0425(8) 0.24261(18) 0.05287(15) 0.0178(6) Uani 1 1 d . . . C9 C -0.0904(8) 0.29935(19) 0.10598(14) 0.0201(7) Uani 1 1 d . . . H9 H -0.1339 0.2764 0.1527 0.024 Uiso 1 1 calc R . . C10 C -0.1580(8) 0.38962(19) 0.08964(16) 0.0221(7) Uani 1 1 d . . . H10 H -0.2422 0.4288 0.1264 0.026 Uiso 1 1 calc R . . C11 C 0.1153(8) 0.14360(19) 0.06793(15) 0.0198(7) Uani 1 1 d . . . C12 C 0.3050(9) 0.62591(19) -0.19854(18) 0.0230(7) Uani 1 1 d . . . N1 N 0.0000(6) 0.34966(15) -0.15649(11) 0.0196(6) Uani 1 1 d . . . N2 N -0.1100(6) 0.42464(15) 0.02387(12) 0.0204(6) Uani 1 1 d . . . O1 O 0.0530(6) 0.10847(13) 0.12485(11) 0.0353(6) Uani 1 1 d . . . O2 O 0.2488(6) 0.10134(14) 0.01232(11) 0.0300(6) Uani 1 1 d D . . O3 O 0.4510(6) 0.64850(13) -0.25280(11) 0.0316(6) Uani 1 1 d . . . O4 O 0.2241(6) 0.68141(13) -0.14496(11) 0.0272(5) Uani 1 1 d D . . H2A H 0.280(9) 0.0436(14) 0.0231(16) 0.041 Uiso 1 1 d D . . H4A H 0.325(8) 0.7346(15) -0.1487(18) 0.041 Uiso 1 1 d 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 C1 0.0298(19) 0.0188(17) 0.0163(16) -0.0015(13) 0.0013(13) -0.0022(13) C2 0.0279(17) 0.0226(17) 0.0184(16) 0.0012(13) 0.0016(13) -0.0009(14) C3 0.0186(16) 0.0147(17) 0.0217(16) 0.0023(13) 0.0033(12) 0.0012(13) C4 0.0187(17) 0.0192(17) 0.0195(16) -0.0042(12) 0.0022(12) 0.0042(13) C5 0.0172(17) 0.0150(16) 0.0206(15) 0.0018(13) 0.0024(12) -0.0007(13) C6 0.0178(18) 0.0139(16) 0.0225(16) -0.0003(13) 0.0010(13) -0.0018(13) C7 0.0168(17) 0.0189(18) 0.0192(16) -0.0036(12) -0.0011(12) -0.0009(13) C8 0.0180(16) 0.0148(16) 0.0205(15) -0.0014(12) 0.0008(11) 0.0004(13) C9 0.0224(17) 0.0200(18) 0.0178(15) 0.0031(12) -0.0028(12) 0.0006(14) C10 0.0224(18) 0.0201(17) 0.0236(18) -0.0042(14) 0.0008(13) 0.0003(13) C11 0.0239(18) 0.0185(16) 0.0170(16) 0.0008(15) 0.0003(12) 0.0003(15) C12 0.0246(18) 0.0196(18) 0.0246(16) -0.0017(15) -0.0025(13) 0.0015(14) N1 0.0231(14) 0.0157(13) 0.0198(13) -0.0031(11) -0.0038(10) -0.0017(12) N2 0.0250(14) 0.0173(14) 0.0189(13) 0.0000(12) 0.0017(10) 0.0019(12) O1 0.0620(18) 0.0204(12) 0.0240(13) 0.0057(10) 0.0107(11) 0.0080(12) O2 0.0507(15) 0.0127(11) 0.0272(12) 0.0028(10) 0.0112(11) 0.0073(11) O3 0.0469(15) 0.0261(13) 0.0223(12) 0.0041(10) 0.0133(11) -0.0070(11) O4 0.0420(14) 0.0132(11) 0.0267(11) -0.0030(10) 0.0051(9) -0.0079(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 C1 N1 1.329(3) . ? C1 C2 1.380(4) . ? C2 C3 1.382(4) . ? C3 C4 1.386(4) . ? C3 C12 1.498(4) . ? C4 C5 1.385(4) . ? C5 N1 1.353(3) . ? C5 C6 1.500(3) . ? C6 N2 1.339(3) . ? C6 C7 1.387(4) . ? C7 C8 1.384(3) . ? C8 C9 1.387(4) . ? C8 C11 1.499(4) . ? C9 C10 1.377(4) . ? C10 N2 1.344(4) . ? C11 O1 1.205(3) . ? C11 O2 1.309(3) . ? C12 O3 1.198(3) . ? C12 O4 1.326(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 N1 C1 C2 123.2(3) . . ? C1 C2 C3 118.7(3) . . ? C2 C3 C4 118.8(3) . . ? C2 C3 C12 119.5(2) . . ? C4 C3 C12 121.7(3) . . ? C5 C4 C3 119.2(3) . . ? N1 C5 C4 121.8(2) . . ? N1 C5 C6 115.7(2) . . ? C4 C5 C6 122.6(2) . . ? N2 C6 C7 121.7(2) . . ? N2 C6 C5 118.0(2) . . ? C7 C6 C5 120.3(2) . . ? C8 C7 C6 119.5(2) . . ? C7 C8 C9 118.6(2) . . ? C7 C8 C11 120.8(2) . . ? C9 C8 C11 120.5(3) . . ? C10 C9 C8 118.7(3) . . ? N2 C10 C9 122.8(3) . . ? O1 C11 O2 125.1(3) . . ? O1 C11 C8 122.8(3) . . ? O2 C11 C8 112.1(2) . . ? O3 C12 O4 125.2(3) . . ? O3 C12 C3 123.2(3) . . ? O4 C12 C3 111.6(3) . . ? C1 N1 C5 118.4(2) . . ? C6 N2 C10 118.6(2) . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 23.29 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.167 _refine_diff_density_min -0.152 _refine_diff_density_rms 0.040 #---END data_etbip53f _database_code_CSD 199919 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety Co(dcbp)(H20)4.4H20 _chemical_formula_sum 'C12 H22 Co N2 O12' _chemical_formula_weight 445.25 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Co Co 0.3494 0.9721 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M Pccn loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y+1/2, z' '-x, y+1/2, -z+1/2' 'x+1/2, -y, -z+1/2' '-x, -y, -z' 'x-1/2, y-1/2, -z' 'x, -y-1/2, z-1/2' '-x-1/2, y, z-1/2' _cell_length_a 6.3780(10) _cell_length_b 12.938(2) _cell_length_c 21.558(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1778.9(5) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description Needle _exptl_crystal_colour Yellow _exptl_crystal_size_max 0.4 _exptl_crystal_size_mid 0.1 _exptl_crystal_size_min 0.1 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.662 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 924 _exptl_absorpt_coefficient_mu 1.032 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.842 _exptl_absorpt_correction_T_max 1.000 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(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 'Bruker SMART APEX CCD' _diffrn_measurement_method 'Omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 20361 _diffrn_reflns_av_R_equivalents 0.0655 _diffrn_reflns_av_sigmaI/netI 0.0436 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -28 _diffrn_reflns_limit_l_max 28 _diffrn_reflns_theta_min 1.89 _diffrn_reflns_theta_max 28.42 _reflns_number_total 2151 _reflns_number_gt 1661 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _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^)+(0.0535P)^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 2151 _refine_ls_number_parameters 147 _refine_ls_number_restraints 8 _refine_ls_R_factor_all 0.0572 _refine_ls_R_factor_gt 0.0413 _refine_ls_wR_factor_ref 0.1022 _refine_ls_wR_factor_gt 0.0973 _refine_ls_goodness_of_fit_ref 1.024 _refine_ls_restrained_S_all 1.024 _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 0.2500 0.2500 0.34466(2) 0.01704(15) Uani 1 2 d S . . N1 N 0.0793(3) 0.30893(15) 0.42123(9) 0.0171(4) Uani 1 1 d . . . C1 C 0.1534(3) 0.28157(17) 0.47723(11) 0.0150(5) Uani 1 1 d . . . C2 C 0.0522(3) 0.31148(17) 0.53148(11) 0.0178(5) Uani 1 1 d . . . H2C H 0.1062 0.2907 0.5706 0.021 Uiso 1 1 calc R . . C3 C -0.1269(3) 0.37142(17) 0.52856(11) 0.0175(5) Uani 1 1 d . . . C4 C -0.2036(4) 0.39888(18) 0.47083(11) 0.0198(5) Uani 1 1 d . . . H4 H -0.3271 0.4394 0.4670 0.024 Uiso 1 1 calc R . . C5 C -0.0960(4) 0.36596(19) 0.41880(11) 0.0212(5) Uani 1 1 d . . . H5C H -0.1492 0.3847 0.3792 0.025 Uiso 1 1 calc R . . C6 C -0.2311(4) 0.40765(19) 0.58741(11) 0.0197(5) Uani 1 1 d . . . O1 O 0.0757(3) 0.11762(14) 0.34164(9) 0.0300(5) Uani 1 1 d D . . H1A H 0.091(5) 0.0637(17) 0.3606(13) 0.045 Uiso 1 1 d D . . H1B H -0.003(4) 0.109(2) 0.3128(11) 0.045 Uiso 1 1 d D . . O2 O 0.4440(3) 0.20319(15) 0.27137(8) 0.0268(4) Uani 1 1 d D . . H2A H 0.380(4) 0.183(2) 0.2392(10) 0.040 Uiso 1 1 d D . . H2B H 0.551(3) 0.167(2) 0.2766(13) 0.040 Uiso 1 1 d D . . O3 O -0.1293(3) 0.39845(15) 0.63667(8) 0.0304(5) Uani 1 1 d . . . O4 O -0.4120(3) 0.44518(14) 0.58335(8) 0.0250(4) Uani 1 1 d . . . O5 O -0.2204(3) -0.10876(16) 0.32900(9) 0.0290(5) Uani 1 1 d D . . H5A H -0.335(3) -0.103(2) 0.3475(13) 0.044 Uiso 1 1 d D . . H5B H -0.140(4) -0.090(2) 0.3559(11) 0.044 Uiso 1 1 d D . . O6 O -0.2220(3) 0.07308(14) 0.25718(8) 0.0248(4) Uani 1 1 d D . . H6A H -0.188(4) 0.078(2) 0.2201(9) 0.037 Uiso 1 1 d D . . H6B H -0.235(4) 0.0117(15) 0.2685(13) 0.037 Uiso 1 1 d 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 0.0159(2) 0.0205(2) 0.0148(3) 0.000 0.000 0.00291(19) N1 0.0162(10) 0.0201(10) 0.0150(10) 0.0017(8) 0.0004(8) 0.0019(8) C1 0.0122(11) 0.0149(10) 0.0179(12) -0.0014(9) 0.0000(9) -0.0008(9) C2 0.0178(11) 0.0219(12) 0.0137(12) 0.0010(10) -0.0023(10) 0.0011(9) C3 0.0143(11) 0.0186(11) 0.0195(12) -0.0023(10) 0.0003(9) -0.0014(9) C4 0.0147(12) 0.0234(12) 0.0211(13) 0.0005(10) -0.0004(9) 0.0054(9) C5 0.0209(12) 0.0253(13) 0.0175(13) 0.0024(10) -0.0022(10) 0.0041(10) C6 0.0191(12) 0.0226(12) 0.0174(13) -0.0004(9) 0.0017(10) 0.0019(10) O1 0.0356(11) 0.0235(9) 0.0308(11) 0.0097(8) -0.0185(9) -0.0074(8) O2 0.0241(10) 0.0370(11) 0.0191(10) -0.0078(8) -0.0009(8) 0.0075(8) O3 0.0215(10) 0.0506(12) 0.0192(10) -0.0032(8) 0.0001(8) 0.0124(9) O4 0.0187(9) 0.0331(10) 0.0230(10) -0.0040(8) 0.0007(7) 0.0096(8) O5 0.0199(10) 0.0425(11) 0.0247(11) -0.0047(9) 0.0017(8) -0.0047(9) O6 0.0248(10) 0.0310(10) 0.0186(10) 0.0017(8) 0.0005(8) -0.0005(8) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Co1 O1 2.0430(18) 2 ? Co1 O1 2.0430(18) . ? Co1 O2 2.0962(18) . ? Co1 O2 2.0962(18) 2 ? Co1 N1 2.1193(19) 2 ? Co1 N1 2.1193(19) . ? N1 C5 1.341(3) . ? N1 C1 1.344(3) . ? C1 C2 1.391(3) . ? C1 C1 1.478(4) 2 ? C2 C3 1.382(3) . ? C3 C4 1.383(3) . ? C3 C6 1.507(3) . ? C4 C5 1.382(3) . ? C6 O3 1.251(3) . ? C6 O4 1.255(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 O1 Co1 O1 176.35(11) 2 . ? O1 Co1 O2 84.09(7) 2 . ? O1 Co1 O2 93.15(8) . . ? O1 Co1 O2 93.15(8) 2 2 ? O1 Co1 O2 84.09(7) . 2 ? O2 Co1 O2 82.17(10) . 2 ? O1 Co1 N1 92.69(8) 2 2 ? O1 Co1 N1 90.15(7) . 2 ? O2 Co1 N1 100.37(7) . 2 ? O2 Co1 N1 173.85(7) 2 2 ? O1 Co1 N1 90.15(7) 2 . ? O1 Co1 N1 92.69(8) . . ? O2 Co1 N1 173.85(7) . . ? O2 Co1 N1 100.37(7) 2 . ? N1 Co1 N1 77.68(10) 2 . ? C5 N1 C1 118.25(19) . . ? C5 N1 Co1 126.58(16) . . ? C1 N1 Co1 115.11(15) . . ? N1 C1 C2 121.26(19) . . ? N1 C1 C1 116.01(12) . 2 ? C2 C1 C1 122.73(13) . 2 ? C3 C2 C1 120.1(2) . . ? C2 C3 C4 118.5(2) . . ? C2 C3 C6 120.0(2) . . ? C4 C3 C6 121.5(2) . . ? C5 C4 C3 118.4(2) . . ? N1 C5 C4 123.5(2) . . ? O3 C6 O4 125.0(2) . . ? O3 C6 C3 117.2(2) . . ? O4 C6 C3 117.8(2) . . ? _diffrn_measured_fraction_theta_max 0.956 _diffrn_reflns_theta_full 28.42 _diffrn_measured_fraction_theta_full 0.956 _refine_diff_density_max 0.532 _refine_diff_density_min -0.228 _refine_diff_density_rms 0.077 #---END data_et24f _database_code_CSD 199920 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety Cu(dcbp)(H2O)2.2H2O _chemical_formula_sum 'C12 H14 Cu N2 O8' _chemical_formula_weight 377.79 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 Orthorhombic _symmetry_space_group_name_H-M Pnna loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z' '-x+1/2, y+1/2, -z+1/2' 'x, -y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, y, -z' 'x-1/2, -y-1/2, z-1/2' '-x, y-1/2, z-1/2' _cell_length_a 14.7685(9) _cell_length_b 10.8176(7) _cell_length_c 9.0272(5) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1442.18(15) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description Prism _exptl_crystal_colour Blue _exptl_crystal_size_max 0.2 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.1 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.740 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 772 _exptl_absorpt_coefficient_mu 1.560 _exptl_absorpt_correction_type Empirical _exptl_absorpt_correction_T_min 0.787 _exptl_absorpt_correction_T_max 1.000 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(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 'Bruker SMART APEX CCD' _diffrn_measurement_method 'Omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 10531 _diffrn_reflns_av_R_equivalents 0.0555 _diffrn_reflns_av_sigmaI/netI 0.0280 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 2.64 _diffrn_reflns_theta_max 25.00 _reflns_number_total 1276 _reflns_number_gt 1158 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _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^+8.7937P] 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 1276 _refine_ls_number_parameters 123 _refine_ls_number_restraints 6 _refine_ls_R_factor_all 0.0585 _refine_ls_R_factor_gt 0.0532 _refine_ls_wR_factor_ref 0.1076 _refine_ls_wR_factor_gt 0.1059 _refine_ls_goodness_of_fit_ref 1.274 _refine_ls_restrained_S_all 1.271 _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 Cu1 Cu 0.33224(5) 0.2500 0.7500 0.0152(2) Uani 1 2 d S . . N1 N 0.2290(2) 0.1987(4) 0.6200(4) 0.0156(9) Uani 1 1 d . . . C1 C 0.1457(3) 0.2243(4) 0.6730(5) 0.0124(10) Uani 1 1 d . . . C2 C 0.0687(3) 0.2048(4) 0.5908(5) 0.0135(10) Uani 1 1 d . . . H2 H 0.0107 0.2249 0.6294 0.016 Uiso 1 1 calc R . . C3 C 0.0780(3) 0.1544(4) 0.4485(5) 0.0134(10) Uani 1 1 d . . . C4 C 0.1632(3) 0.1291(4) 0.3946(5) 0.0174(10) Uani 1 1 d . . . H4 H 0.1710 0.0955 0.2982 0.021 Uiso 1 1 calc R . . C5 C 0.2376(3) 0.1539(4) 0.4844(5) 0.0176(11) Uani 1 1 d . . . H5 H 0.2966 0.1381 0.4470 0.021 Uiso 1 1 calc R . . C6 C -0.0063(3) 0.1281(4) 0.3551(5) 0.0147(10) Uani 1 1 d . . . O1 O 0.3341(3) 0.0591(4) 0.8946(4) 0.0269(9) Uani 1 1 d D . . H1A H 0.383(2) 0.038(6) 0.856(6) 0.040 Uiso 1 1 d D . . H1B H 0.283(4) 0.028(11) 0.876(12) 0.040 Uiso 0.50 1 d PD . . H1C H 0.343(9) 0.065(11) 0.986(3) 0.040 Uiso 0.50 1 d PD . . O2 O -0.0752(2) 0.1924(3) 0.3895(3) 0.0172(7) Uani 1 1 d . . . O3 O -0.0009(2) 0.0493(3) 0.2556(4) 0.0240(8) Uani 1 1 d . . . O4 O 0.1306(3) -0.1293(4) 0.1883(5) 0.0375(10) Uani 1 1 d D . . H4A H 0.092(3) -0.076(5) 0.210(8) 0.056 Uiso 1 1 d D . . H4B H 0.131(9) -0.196(7) 0.234(15) 0.056 Uiso 0.50 1 d PD . . H4C H 0.134(10) -0.120(13) 0.097(3) 0.056 Uiso 0.50 1 d PD . . 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 0.0083(4) 0.0242(5) 0.0130(4) -0.0001(4) 0.000 0.000 N1 0.0081(19) 0.023(2) 0.016(2) 0.0031(18) 0.0031(16) 0.0007(16) C1 0.009(2) 0.013(2) 0.015(2) 0.0027(19) 0.0000(18) -0.0013(18) C2 0.012(2) 0.016(2) 0.013(2) 0.0003(19) 0.0009(19) 0.0024(18) C3 0.014(2) 0.011(2) 0.015(2) 0.0035(19) -0.003(2) -0.0015(19) C4 0.016(2) 0.023(3) 0.014(2) -0.002(2) -0.001(2) 0.000(2) C5 0.013(2) 0.021(3) 0.019(3) 0.002(2) 0.003(2) 0.000(2) C6 0.013(2) 0.017(2) 0.014(2) 0.004(2) -0.0014(19) 0.000(2) O1 0.0165(18) 0.039(2) 0.025(2) 0.0057(19) 0.0026(17) -0.0021(18) O2 0.0123(16) 0.0268(19) 0.0126(16) -0.0015(15) -0.0029(14) 0.0031(15) O3 0.0207(17) 0.0285(19) 0.0229(18) -0.0089(17) -0.0060(16) 0.0053(16) O4 0.043(2) 0.043(3) 0.027(2) -0.009(2) -0.011(2) 0.022(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 Cu1 O2 1.960(3) 7_666 ? Cu1 O2 1.960(3) 6_656 ? Cu1 N1 2.002(4) . ? Cu1 N1 2.002(4) 4_556 ? N1 C5 1.323(6) . ? N1 C1 1.349(5) . ? C1 C2 1.374(6) . ? C1 C1 1.497(9) 4_556 ? C2 C3 1.402(6) . ? C3 C4 1.377(7) . ? C3 C6 1.530(6) . ? C4 C5 1.392(7) . ? C6 O3 1.241(6) . ? C6 O2 1.270(6) . ? O2 Cu1 1.960(3) 6_556 ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O2 Cu1 O2 91.55(19) 7_666 6_656 ? O2 Cu1 N1 174.60(15) 7_666 . ? O2 Cu1 N1 93.81(14) 6_656 . ? O2 Cu1 N1 93.81(14) 7_666 4_556 ? O2 Cu1 N1 174.60(15) 6_656 4_556 ? N1 Cu1 N1 80.8(2) . 4_556 ? C5 N1 C1 119.4(4) . . ? C5 N1 Cu1 124.8(3) . . ? C1 N1 Cu1 115.4(3) . . ? N1 C1 C2 122.1(4) . . ? N1 C1 C1 113.9(3) . 4_556 ? C2 C1 C1 124.0(3) . 4_556 ? C1 C2 C3 118.3(4) . . ? C4 C3 C2 119.4(4) . . ? C4 C3 C6 120.8(4) . . ? C2 C3 C6 119.9(4) . . ? C3 C4 C5 118.5(4) . . ? N1 C5 C4 122.3(4) . . ? O3 C6 O2 127.2(4) . . ? O3 C6 C3 118.3(4) . . ? O2 C6 C3 114.5(4) . . ? C6 O2 Cu1 125.1(3) . 6_556 ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.428 _refine_diff_density_min -0.538 _refine_diff_density_rms 0.093