Electronic Supplementary Material for CrystEngComm This Journal is © The Royal Society of Chemistry 2003 data_global _publ_contact_author_email KATHARINA.FROMM@UNIBAS.CH _publ_contact_author_name 'ProfD Katharina M. Fromm' _journal_name_full CrystEngComm _journal_coden_Cambridge 1350 _journal_volume ? _journal_year ? _journal_page_first ? _publ_contact_author_address ; ProfD Katharina M. Fromm Department of Chemistry University of Basel Basel 4056 SWITZERLAN ; _publ_section_title ; Structural relationship of two coordination polymers of Cu(I) with the ligand ethanediyl bis(isonicotinate) ; loop_ _publ_author_name 'Katharina M. Fromm' 'Gerald Bernardinelli' 'H. Goesmann' 'Adeline Y. Robin' data_Compound2 _database_code_depnum_ccdc_archive 'CCDC 206524' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety [CuCl(C14H12N2O4)] _chemical_formula_sum 'C14 H12 Cl Cu N2 O4' _chemical_formula_weight 371.26 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' O O 0.0106 0.0060 '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' Cu Cu 0.3201 1.2651 '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' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'C 2/c' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 11.4740(11) _cell_length_b 11.5821(14) _cell_length_c 10.9650(14) _cell_angle_alpha 90.00 _cell_angle_beta 106.670(18) _cell_angle_gamma 90.00 _cell_volume 1395.9(3) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour orange _exptl_crystal_size_max 0.2 _exptl_crystal_size_mid 0.2 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.766 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 752 _exptl_absorpt_coefficient_mu 1.775 _exptl_absorpt_correction_type numerical _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Stoe IPDS' _diffrn_measurement_method 'Omega scan' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 5896 _diffrn_reflns_av_R_equivalents 0.0596 _diffrn_reflns_av_sigmaI/netI 0.0442 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 2.55 _diffrn_reflns_theta_max 28.26 _reflns_number_total 1655 _reflns_number_gt 1324 _reflns_threshold_expression >2sigma(I) _computing_data_collection Stoe _computing_cell_refinement Xred _computing_data_reduction Xred _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics Schakal _computing_publication_material Word _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^)+(0.0825P)^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 SHELXL _refine_ls_extinction_coef 0.0063(11) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 1655 _refine_ls_number_parameters 126 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0617 _refine_ls_R_factor_gt 0.0467 _refine_ls_wR_factor_ref 0.1221 _refine_ls_wR_factor_gt 0.1147 _refine_ls_goodness_of_fit_ref 0.990 _refine_ls_restrained_S_all 0.990 _refine_ls_shift/su_max 0.003 _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 0.0000 0.05969(5) 0.2500 0.0319(2) Uani 1 2 d S . . Cl2 Cl 0.0000 0.25909(10) 0.2500 0.0351(3) Uani 1 2 d S . . N1 N -0.1001(2) 0.0042(2) 0.0847(3) 0.0308(6) Uani 1 1 d . . . C1 C -0.1079(3) -0.1080(3) 0.0501(3) 0.0320(7) Uani 1 1 d . . . C2 C -0.1802(3) -0.1473(3) -0.0660(3) 0.0320(7) Uani 1 1 d . . . C3 C -0.2486(3) -0.0679(3) -0.1525(3) 0.0310(6) Uani 1 1 d . . . C4 C -0.2395(3) 0.0488(3) -0.1203(4) 0.0328(7) Uani 1 1 d . . . C5 C -0.1648(3) 0.0805(3) -0.0018(3) 0.0324(7) Uani 1 1 d . . . C6 C -0.3350(3) -0.1102(3) -0.2737(3) 0.0325(7) Uani 1 1 d . . . C7 C -0.4775(3) -0.0562(3) -0.4670(3) 0.0340(7) Uani 1 1 d . . . O1 O -0.3619(2) -0.2111(2) -0.2956(3) 0.0414(6) Uani 1 1 d . . . O2 O -0.3823(2) -0.0244(2) -0.3539(2) 0.0345(5) Uani 1 1 d . . . H1 H -0.059(4) -0.161(4) 0.112(5) 0.048(13) Uiso 1 1 d . . . H2 H -0.181(3) -0.232(3) -0.090(4) 0.027(9) Uiso 1 1 d . . . H3 H -0.281(5) 0.105(5) -0.176(5) 0.056(13) Uiso 1 1 d . . . H4 H -0.150(4) 0.163(3) 0.026(4) 0.034(10) Uiso 1 1 d . . . H5 H -0.441(4) -0.113(4) -0.522(4) 0.042(11) Uiso 1 1 d . . . H6 H -0.454(3) 0.096(3) -0.557(4) 0.022(8) 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 0.0308(3) 0.0355(3) 0.0260(3) 0.000 0.0028(2) 0.000 Cl2 0.0378(6) 0.0334(5) 0.0315(6) 0.000 0.0059(5) 0.000 N1 0.0299(13) 0.0344(15) 0.0268(15) -0.0008(10) 0.0059(11) 0.0001(10) C1 0.0311(15) 0.0345(16) 0.0275(18) 0.0021(13) 0.0036(13) 0.0003(12) C2 0.0309(15) 0.0335(16) 0.0293(18) -0.0014(12) 0.0048(13) -0.0006(12) C3 0.0290(14) 0.0370(17) 0.0254(17) 0.0004(12) 0.0051(13) -0.0001(12) C4 0.0314(15) 0.0355(17) 0.0300(19) 0.0033(12) 0.0063(14) 0.0020(12) C5 0.0306(14) 0.0324(16) 0.0316(19) 0.0002(12) 0.0048(14) 0.0000(12) C6 0.0270(14) 0.0407(17) 0.0285(18) 0.0000(13) 0.0060(13) 0.0011(12) C7 0.0300(15) 0.0421(18) 0.0246(17) -0.0015(14) -0.0007(13) -0.0018(14) O1 0.0453(13) 0.0339(13) 0.0374(15) -0.0005(10) -0.0003(11) -0.0051(11) O2 0.0350(11) 0.0369(11) 0.0251(13) -0.0027(9) -0.0018(10) -0.0007(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 N1 1.955(3) . ? Cu1 N1 1.955(3) 2 ? Cu1 Cl2 2.3094(13) . ? N1 C1 1.350(4) . ? N1 C5 1.352(4) . ? C1 C2 1.382(5) . ? C2 C3 1.390(5) . ? C3 C4 1.394(5) . ? C3 C6 1.495(5) . ? C4 C5 1.385(5) . ? C6 O1 1.215(5) . ? C6 O2 1.335(4) . ? C7 O2 1.446(4) . ? C7 C7 1.507(7) 5_454 ? 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 Cu1 N1 141.63(17) . 2 ? N1 Cu1 Cl2 109.19(8) . . ? N1 Cu1 Cl2 109.19(8) 2 . ? C1 N1 C5 116.9(3) . . ? C1 N1 Cu1 123.5(2) . . ? C5 N1 Cu1 119.6(2) . . ? N1 C1 C2 123.4(3) . . ? C1 C2 C3 118.9(3) . . ? C2 C3 C4 118.8(3) . . ? C2 C3 C6 119.4(3) . . ? C4 C3 C6 121.7(3) . . ? C5 C4 C3 118.4(3) . . ? N1 C5 C4 123.6(3) . . ? O1 C6 O2 123.6(3) . . ? O1 C6 C3 123.8(3) . . ? O2 C6 C3 112.5(3) . . ? O2 C7 C7 105.2(3) . 5_454 ? C6 O2 C7 116.1(3) . . ? _diffrn_measured_fraction_theta_max 0.956 _diffrn_reflns_theta_full 28.26 _diffrn_measured_fraction_theta_full 0.956 _refine_diff_density_max 0.642 _refine_diff_density_min -0.808 _refine_diff_density_rms 0.125 data_Compound3 _database_code_depnum_ccdc_archive 'CCDC 206525' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety [Cu2Cl2(C14H12N2O4)2].C4H8O _chemical_formula_sum 'C32 H32 Cl2 Cu2 N4 O9' _chemical_formula_weight 814.60 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' O O 0.0106 0.0060 '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' Cu Cu 0.3201 1.2651 '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' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 6.9874(10) _cell_length_b 11.7096(19) _cell_length_c 11.8247(17) _cell_angle_alpha 112.339(17) _cell_angle_beta 96.728(17) _cell_angle_gamma 102.930(18) _cell_volume 850.0(2) _cell_formula_units_Z 1 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour Red _exptl_crystal_size_max 0.32 _exptl_crystal_size_mid 0.08 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.591 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 416 _exptl_absorpt_coefficient_mu 1.468 _exptl_absorpt_correction_type numerical _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Stoe IPDS' _diffrn_measurement_method 'Omega scan' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 7365 _diffrn_reflns_av_R_equivalents 0.0387 _diffrn_reflns_av_sigmaI/netI 0.0519 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 3.07 _diffrn_reflns_theta_max 26.07 _reflns_number_total 3106 _reflns_number_gt 2161 _reflns_threshold_expression >2sigma(I) _computing_data_collection Stoe _computing_cell_refinement Xred _computing_data_reduction Xred _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics Schakal _computing_publication_material Word _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^)+(0.0647P)^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 3106 _refine_ls_number_parameters 226 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0525 _refine_ls_R_factor_gt 0.0328 _refine_ls_wR_factor_ref 0.0879 _refine_ls_wR_factor_gt 0.0800 _refine_ls_goodness_of_fit_ref 0.785 _refine_ls_restrained_S_all 0.785 _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 0.46837(5) 0.46261(4) 0.86988(4) 0.04203(14) Uani 1 1 d . . . Cl2 Cl 0.31858(9) 0.61274(6) 1.02872(7) 0.03585(18) Uani 1 1 d . . . N1 N 0.2223(3) 0.3366(2) 0.7413(2) 0.0349(6) Uani 1 1 d . . . C1 C 0.0367(4) 0.3408(3) 0.7597(3) 0.0370(7) Uani 1 1 d . . . H1 H 0.0247 0.3972 0.8372 0.044 Uiso 1 1 calc R . . C2 C -0.1358(4) 0.2647(3) 0.6681(3) 0.0396(7) Uani 1 1 d . . . H2 H -0.2613 0.2705 0.6843 0.047 Uiso 1 1 calc R . . C3 C 0.2334(4) 0.2516(3) 0.6295(3) 0.0388(7) Uani 1 1 d . . . H3 H 0.3601 0.2461 0.6160 0.047 Uiso 1 1 calc R . . C4 C 0.0677(4) 0.1720(3) 0.5338(3) 0.0361(7) Uani 1 1 d . . . H4 H 0.0826 0.1140 0.4581 0.043 Uiso 1 1 calc R . . C5 C -0.1223(4) 0.1802(3) 0.5528(3) 0.0328(6) Uani 1 1 d . . . C6 C -0.3090(4) 0.1055(3) 0.4498(3) 0.0386(7) Uani 1 1 d . . . O1 O -0.4722(3) 0.1196(3) 0.4592(2) 0.0742(9) Uani 1 1 d . . . O2 O -0.2703(3) 0.02413(19) 0.34799(19) 0.0411(5) Uani 1 1 d . . . C7 C -0.4318(4) -0.0455(3) 0.2363(3) 0.0424(8) Uani 1 1 d . . . H7A H -0.5087 0.0109 0.2263 0.051 Uiso 1 1 calc R . . H7B H -0.5221 -0.1180 0.2423 0.051 Uiso 1 1 calc R . . C8 C -0.3367(4) -0.0918(3) 0.1277(3) 0.0417(7) Uani 1 1 d . . . H8A H -0.2583 -0.1469 0.1391 0.050 Uiso 1 1 calc R . . H8B H -0.4402 -0.1419 0.0511 0.050 Uiso 1 1 calc R . . O3 O -0.2062(3) 0.01898(19) 0.1183(2) 0.0421(5) Uani 1 1 d . . . C9 C -0.0085(4) 0.0482(3) 0.1655(3) 0.0381(7) Uani 1 1 d . . . O4 O 0.0695(3) -0.0133(2) 0.2067(2) 0.0493(6) Uani 1 1 d . . . C10 C 0.8931(4) 0.8304(3) 0.8398(3) 0.0350(7) Uani 1 1 d . . . C11 C 0.9732(4) 0.7690(3) 0.9048(3) 0.0367(7) Uani 1 1 d . . . H11 H 1.1072 0.8021 0.9483 0.044 Uiso 1 1 calc R . . C12 C 0.8514(4) 0.6578(3) 0.9040(3) 0.0347(6) Uani 1 1 d . . . H12 H 0.9070 0.6175 0.9480 0.042 Uiso 1 1 calc R . . C13 C 0.6924(4) 0.7743(3) 0.7738(3) 0.0440(8) Uani 1 1 d . . . H13 H 0.6341 0.8113 0.7272 0.053 Uiso 1 1 calc R . . C14 C 0.5826(4) 0.6645(3) 0.7784(3) 0.0471(8) Uani 1 1 d . . . H14 H 0.4488 0.6289 0.7345 0.057 Uiso 1 1 calc R . . N2 N 0.6570(3) 0.6049(2) 0.8429(2) 0.0369(6) Uani 1 1 d . . . O5 O 0.2143(9) 0.6223(7) 0.5590(6) 0.0767(17) Uani 0.50 1 d P . . C15 C 0.0362(8) 0.5834(6) 0.6024(5) 0.0942(16) Uani 1 1 d . . . H15A H 0.0144 0.6627 0.6581 0.113 Uiso 1 1 calc R . . H15B H 0.0732 0.5414 0.6547 0.113 Uiso 1 1 calc R . . C16 C 0.1609(11) 0.4986(6) 0.4777(7) 0.135(3) Uani 1 1 d . . . H16A H 0.1991 0.4534 0.5263 0.162 Uiso 1 1 calc R . . H16B H 0.2514 0.4944 0.4210 0.162 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 0.02724(19) 0.0436(2) 0.0434(3) 0.01289(17) 0.00336(15) 0.00006(14) Cl2 0.0267(3) 0.0319(3) 0.0410(4) 0.0090(3) 0.0057(3) 0.0059(3) N1 0.0291(11) 0.0362(13) 0.0365(15) 0.0143(11) 0.0069(10) 0.0060(10) C1 0.0285(13) 0.0437(16) 0.0292(16) 0.0075(13) 0.0068(11) 0.0059(11) C2 0.0263(13) 0.0453(17) 0.0384(18) 0.0107(14) 0.0078(12) 0.0062(12) C3 0.0284(13) 0.0438(17) 0.0392(18) 0.0116(14) 0.0085(12) 0.0111(12) C4 0.0294(13) 0.0362(15) 0.0354(17) 0.0072(12) 0.0066(12) 0.0103(11) C5 0.0276(13) 0.0355(15) 0.0299(16) 0.0093(12) 0.0067(11) 0.0071(11) C6 0.0281(14) 0.0386(16) 0.0373(18) 0.0074(13) 0.0044(12) 0.0045(12) O1 0.0294(12) 0.104(2) 0.0477(16) -0.0110(14) 0.0011(10) 0.0215(12) O2 0.0303(10) 0.0405(11) 0.0349(12) 0.0011(9) 0.0027(8) 0.0064(8) C7 0.0331(14) 0.0379(16) 0.0367(18) 0.0038(13) -0.0006(13) -0.0009(12) C8 0.0422(16) 0.0306(15) 0.0397(18) 0.0087(13) 0.0082(13) -0.0019(12) O3 0.0356(10) 0.0381(11) 0.0431(13) 0.0154(9) 0.0025(9) -0.0009(8) C9 0.0398(15) 0.0344(15) 0.0334(17) 0.0091(13) 0.0076(12) 0.0078(13) O4 0.0495(12) 0.0418(12) 0.0589(15) 0.0238(11) 0.0099(11) 0.0142(10) C10 0.0316(14) 0.0345(15) 0.0334(17) 0.0107(12) 0.0074(12) 0.0058(11) C11 0.0273(13) 0.0407(16) 0.0337(17) 0.0124(13) 0.0030(11) 0.0019(11) C12 0.0292(13) 0.0370(15) 0.0353(17) 0.0140(13) 0.0072(12) 0.0070(11) C13 0.0346(15) 0.0463(18) 0.050(2) 0.0214(15) 0.0016(13) 0.0104(13) C14 0.0319(15) 0.0514(19) 0.051(2) 0.0206(16) 0.0008(14) 0.0061(13) N2 0.0262(11) 0.0419(13) 0.0364(14) 0.0130(11) 0.0047(10) 0.0058(10) O5 0.075(4) 0.098(5) 0.062(4) 0.035(3) 0.008(3) 0.036(3) C15 0.103(4) 0.132(5) 0.065(3) 0.041(3) 0.030(3) 0.062(3) C16 0.139(6) 0.109(5) 0.136(6) 0.034(4) -0.028(5) 0.060(4) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cu1 N1 1.998(2) . ? Cu1 N2 2.033(3) . ? Cu1 Cl2 2.3251(9) 2_667 ? Cu1 Cl2 2.5472(10) . ? Cu1 Cu1 2.8092(10) 2_667 ? Cl2 Cu1 2.3251(9) 2_667 ? N1 C3 1.342(4) . ? N1 C1 1.348(4) . ? C1 C2 1.379(4) . ? C2 C5 1.376(4) . ? C3 C4 1.378(4) . ? C4 C5 1.390(4) . ? C5 C6 1.503(4) . ? C6 O1 1.200(4) . ? C6 O2 1.323(4) . ? O2 C7 1.450(3) . ? C7 C8 1.489(5) . ? C8 O3 1.460(3) . ? O3 C9 1.341(3) . ? C9 O4 1.198(4) . ? C9 C10 1.497(4) 2_666 ? C10 C11 1.385(4) . ? C10 C13 1.396(4) . ? C10 C9 1.497(4) 2_666 ? C11 C12 1.383(4) . ? C12 N2 1.343(3) . ? C13 C14 1.366(5) . ? C14 N2 1.347(4) . ? O5 C16 1.332(8) . ? O5 C15 1.447(8) . ? C15 C16 1.458(8) 2_566 ? C15 C16 1.869(10) . ? C16 C15 1.458(8) 2_566 ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N1 Cu1 N2 122.93(10) . . ? N1 Cu1 Cl2 119.12(7) . 2_667 ? N2 Cu1 Cl2 104.46(7) . 2_667 ? N1 Cu1 Cl2 101.99(7) . . ? N2 Cu1 Cl2 95.36(8) . . ? Cl2 Cu1 Cl2 109.75(3) 2_667 . ? N1 Cu1 Cu1 126.24(8) . 2_667 ? N2 Cu1 Cu1 106.94(8) . 2_667 ? Cl2 Cu1 Cu1 58.58(3) 2_667 2_667 ? Cl2 Cu1 Cu1 51.17(2) . 2_667 ? Cu1 Cl2 Cu1 70.25(3) 2_667 . ? C3 N1 C1 117.0(2) . . ? C3 N1 Cu1 121.93(18) . . ? C1 N1 Cu1 120.8(2) . . ? N1 C1 C2 122.5(3) . . ? C5 C2 C1 119.9(3) . . ? N1 C3 C4 123.7(3) . . ? C3 C4 C5 118.5(3) . . ? C2 C5 C4 118.2(2) . . ? C2 C5 C6 119.8(3) . . ? C4 C5 C6 122.0(3) . . ? O1 C6 O2 124.6(3) . . ? O1 C6 C5 123.7(3) . . ? O2 C6 C5 111.7(2) . . ? C6 O2 C7 118.0(2) . . ? O2 C7 C8 107.1(2) . . ? O3 C8 C7 109.3(2) . . ? C9 O3 C8 116.3(2) . . ? O4 C9 O3 125.6(3) . . ? O4 C9 C10 123.2(3) . 2_666 ? O3 C9 C10 111.3(3) . 2_666 ? C11 C10 C13 117.7(3) . . ? C11 C10 C9 124.3(2) . 2_666 ? C13 C10 C9 118.0(3) . 2_666 ? C12 C11 C10 119.2(3) . . ? N2 C12 C11 123.4(3) . . ? C14 C13 C10 119.3(3) . . ? N2 C14 C13 123.8(3) . . ? C12 N2 C14 116.6(3) . . ? C12 N2 Cu1 122.3(2) . . ? C14 N2 Cu1 120.14(19) . . ? C16 O5 C15 84.4(6) . . ? O5 C15 C16 125.5(6) . 2_566 ? O5 C15 C16 45.2(4) . . ? C16 C15 C16 90.1(5) 2_566 . ? O5 C16 C15 128.9(6) . 2_566 ? O5 C16 C15 50.4(4) . . ? C15 C16 C15 89.9(5) 2_566 . ? _diffrn_measured_fraction_theta_max 0.923 _diffrn_reflns_theta_full 26.07 _diffrn_measured_fraction_theta_full 0.923 _refine_diff_density_max 0.339 _refine_diff_density_min -0.388 _refine_diff_density_rms 0.062 data_LigandL,1 _database_code_depnum_ccdc_archive 'CCDC 206593' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety C14H12N2O4 _chemical_formula_sum 'C14 H12 N2 O4' _chemical_formula_weight 272.26 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' O O 0.0106 0.0060 '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' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 6.9688(11) _cell_length_b 10.6469(14) _cell_length_c 8.8115(14) _cell_angle_alpha 90.00 _cell_angle_beta 109.047(18) _cell_angle_gamma 90.00 _cell_volume 617.99(16) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.4 _exptl_crystal_size_mid 0.4 _exptl_crystal_size_min 0.25 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.463 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 284 _exptl_absorpt_coefficient_mu 0.109 _exptl_absorpt_correction_type numerical _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Stoe IPDS' _diffrn_measurement_method 'Omega scan' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 6383 _diffrn_reflns_av_R_equivalents 0.0425 _diffrn_reflns_av_sigmaI/netI 0.0362 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 3.09 _diffrn_reflns_theta_max 28.08 _reflns_number_total 1393 _reflns_number_gt 919 _reflns_threshold_expression >2sigma(I) _computing_data_collection Stoe _computing_cell_refinement Xred _computing_data_reduction Xred _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics Schakal _computing_publication_material Word _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^)+(0.0655P)^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 1393 _refine_ls_number_parameters 91 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0589 _refine_ls_R_factor_gt 0.0371 _refine_ls_wR_factor_ref 0.0983 _refine_ls_wR_factor_gt 0.0926 _refine_ls_goodness_of_fit_ref 0.884 _refine_ls_restrained_S_all 0.884 _refine_ls_shift/su_max 0.008 _refine_ls_shift/su_mean 0.003 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 O2 O 0.11568(15) 1.00125(8) -0.28568(10) 0.0306(3) Uani 1 1 d . . . O1 O 0.16346(18) 0.80731(9) -0.17920(11) 0.0406(3) Uani 1 1 d . . . C2 C 0.2435(2) 1.11468(12) 0.01087(14) 0.0285(3) Uani 1 1 d . . . H2 H 0.1950 1.1656 -0.0794 0.034 Uiso 1 1 calc R . . C1 C 0.3133(2) 1.16672(13) 0.16408(15) 0.0340(4) Uani 1 1 d . . . H1 H 0.3105 1.2536 0.1735 0.041 Uiso 1 1 calc R . . C3 C 0.3863(2) 0.97415(13) 0.28164(16) 0.0337(4) Uani 1 1 d . . . H3 H 0.4347 0.9253 0.3738 0.040 Uiso 1 1 calc R . . C4 C 0.3204(2) 0.91312(12) 0.13441(15) 0.0295(3) Uani 1 1 d . . . H4 H 0.3247 0.8260 0.1285 0.035 Uiso 1 1 calc R . . C5 C 0.24789(19) 0.98547(11) -0.00398(13) 0.0233(3) Uani 1 1 d . . . C6 C 0.1732(2) 0.91942(12) -0.16279(15) 0.0257(3) Uani 1 1 d . . . C7 C 0.0337(2) 0.94536(12) -0.44370(14) 0.0327(4) Uani 1 1 d . . . H7A H -0.0801 0.8909 -0.4494 0.039 Uiso 1 1 calc R . . H7B H 0.1366 0.8967 -0.4695 0.039 Uiso 1 1 calc R . . N1 N 0.38438(19) 1.09837(11) 0.29907(13) 0.0352(3) 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 O2 0.0450(6) 0.0272(5) 0.0147(4) -0.0008(3) 0.0031(4) -0.0005(4) O1 0.0660(8) 0.0259(5) 0.0255(5) -0.0020(4) 0.0090(5) 0.0028(5) C2 0.0345(8) 0.0296(7) 0.0192(6) 0.0018(5) 0.0061(6) 0.0001(6) C1 0.0436(9) 0.0287(7) 0.0265(7) -0.0023(5) 0.0069(6) -0.0019(6) C3 0.0389(9) 0.0386(8) 0.0197(7) 0.0036(5) 0.0046(6) 0.0013(6) C4 0.0344(8) 0.0281(7) 0.0239(6) 0.0022(5) 0.0069(6) -0.0001(6) C5 0.0217(7) 0.0296(6) 0.0189(6) -0.0006(4) 0.0070(6) -0.0012(5) C6 0.0286(7) 0.0284(7) 0.0201(6) 0.0008(5) 0.0078(5) 0.0017(5) C7 0.0488(10) 0.0287(7) 0.0162(6) -0.0032(5) 0.0045(6) -0.0009(6) N1 0.0413(8) 0.0385(7) 0.0218(6) -0.0033(4) 0.0049(5) -0.0012(5) _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 O2 C6 1.3450(16) . ? O2 C7 1.4492(15) . ? O1 C6 1.2015(16) . ? C2 C5 1.3832(17) . ? C2 C1 1.3919(17) . ? C1 N1 1.3435(18) . ? C3 N1 1.3320(18) . ? C3 C4 1.3883(18) . ? C4 C5 1.3904(17) . ? C5 C6 1.4995(16) . ? C7 C7 1.501(3) 3_574 ? 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 C6 O2 C7 115.35(10) . . ? C5 C2 C1 118.43(11) . . ? N1 C1 C2 123.66(13) . . ? N1 C3 C4 124.04(12) . . ? C3 C4 C5 118.36(12) . . ? C2 C5 C4 118.75(11) . . ? C2 C5 C6 122.89(10) . . ? C4 C5 C6 118.34(11) . . ? O1 C6 O2 123.80(12) . . ? O1 C6 C5 124.54(12) . . ? O2 C6 C5 111.66(11) . . ? O2 C7 C7 104.89(13) . 3_574 ? C3 N1 C1 116.77(12) . . ? _diffrn_measured_fraction_theta_max 0.926 _diffrn_reflns_theta_full 28.08 _diffrn_measured_fraction_theta_full 0.926 _refine_diff_density_max 0.180 _refine_diff_density_min -0.277 _refine_diff_density_rms 0.073