#------------------------------------------------------------------------------ #$Date: 2010-01-30 13:59:17 +0000 (Sat, 30 Jan 2010) $ #$Revision: 966 $ #$URL: svn://www.crystallography.net/cod/cif/1/1100146.cif $ #------------------------------------------------------------------------------ # # This file is available in the Crystallography Open Database (COD), # http://www.crystallography.net/ # # All data on this site have been placed in the public domain by the # contributors. # data_1100146 _space_group_IT_number 14 _symmetry_space_group_name_Hall '-P 2yn' _symmetry_space_group_name_H-M 'P 1 21/n 1' _[local]_cod_cif_authors_sg_H-M 'P 2(1)/n' loop_ _publ_author_name 'Esther R. Acuna-Cueva' 'Rene Faure' 'Nuria A. Illan-Cabeza' 'Sonia B. Jimenez-Pulido' 'Miguel N. Moreno-Carretero' 'Miguel Quiros' _journal_name_full 'Inorganica Chimica Acta' _journal_volume 351 _journal_page_first 356 _journal_page_last 362 _journal_year 2003 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C9 H12 Cl2 Cu N4 O3' _chemical_formula_weight 358.67 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 monoclinic 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 8.8152(10) _cell_length_b 10.0526(12) _cell_length_c 15.344(2) _cell_angle_alpha 90.00 _cell_angle_beta 91.521(9) _cell_angle_gamma 90.00 _cell_volume 1359.3(3) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 39 _cell_measurement_theta_min 5.05 _cell_measurement_theta_max 12.50 _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.4 _exptl_crystal_size_mid 0.4 _exptl_crystal_size_min 0.1 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.753 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 724 _exptl_absorpt_coefficient_mu 2.008 _exptl_absorpt_correction_type 'integration' _exptl_absorpt_correction_T_min 0.4755 _exptl_absorpt_correction_T_max 0.8319 loop_ _exptl_crystal_face_index_h _exptl_crystal_face_index_k _exptl_crystal_face_index_l _exptl_crystal_face_perp_dist -1.00 0.00 1.00 0.0500 1.00 0.00 -1.00 0.0500 1.00 0.00 2.00 0.2000 0.00 -1.00 -1.00 0.2000 0.00 -1.00 1.00 0.2000 -1.00 0.00 0.00 0.1500 -1.00 1.00 0.00 0.2000 1.00 1.00 0.00 0.2000 _exptl_absorpt_process_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 'Siemens P4' _diffrn_measurement_method '2\q/\w scans' _diffrn_standards_number 3 _diffrn_standards_interval_count 97 _diffrn_standards_decay_% 21.64 _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 5152 _diffrn_reflns_av_R_equivalents 0.0665 _diffrn_reflns_av_sigmaI/netI 0.0489 _diffrn_reflns_limit_h_min -1 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -1 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 2.42 _diffrn_reflns_theta_max 30.00 _reflns_number_total 3958 _reflns_number_gt 3330 _reflns_threshold_expression >2sigma(I) _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^)+(0.0600P)^2^+0.6500P] 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 3958 _refine_ls_number_parameters 181 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0504 _refine_ls_R_factor_gt 0.0411 _refine_ls_wR_factor_ref 0.1178 _refine_ls_wR_factor_gt 0.1111 _refine_ls_goodness_of_fit_ref 1.072 _refine_ls_restrained_S_all 1.072 _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 Cu Cu 0.35109(3) 0.21134(3) 0.402136(17) 0.03049(10) Uani 1 1 d . . . Cl1 Cl 0.16476(7) 0.36401(7) 0.42076(4) 0.03879(15) Uani 1 1 d . . . Cl2 Cl 0.47076(9) 0.02221(7) 0.36180(5) 0.04615(17) Uani 1 1 d . . . N1 N 0.6450(2) 0.59668(19) 0.25277(12) 0.0289(4) Uani 1 1 d . . . C1 C 0.6703(3) 0.6950(3) 0.18370(17) 0.0404(6) Uani 1 1 d . . . H11 H 0.6891 0.7808 0.2093 0.049 Uiso 1 1 d R . . H12 H 0.5822 0.6996 0.1457 0.049 Uiso 1 1 d R . . H13 H 0.7565 0.6684 0.1509 0.049 Uiso 1 1 d R . . C1A C 0.5517(2) 0.4879(2) 0.23703(13) 0.0238(4) Uani 1 1 d . . . C2 C 0.7088(3) 0.6200(2) 0.33401(15) 0.0301(4) Uani 1 1 d . . . O2 O 0.7908(2) 0.71622(19) 0.34879(13) 0.0406(4) Uani 1 1 d . . . N3 N 0.6753(2) 0.5302(2) 0.39899(12) 0.0321(4) Uani 1 1 d . . . H3 H 0.7211 0.5416 0.4486 0.039 Uiso 1 1 d R . . C4 C 0.5772(2) 0.4254(2) 0.39270(14) 0.0264(4) Uani 1 1 d . . . O4 O 0.5479(2) 0.35334(18) 0.45487(11) 0.0348(4) Uani 1 1 d . . . C4A C 0.5118(2) 0.4063(2) 0.30543(13) 0.0239(4) Uani 1 1 d . . . N5 N 0.4108(2) 0.30680(18) 0.29203(12) 0.0262(3) Uani 1 1 d . . . C6 C 0.3547(3) 0.2858(2) 0.21218(14) 0.0281(4) Uani 1 1 d . . . C61 C 0.2373(3) 0.1799(3) 0.19899(19) 0.0430(6) Uani 1 1 d . . . H61 H 0.2837 0.1007 0.1771 0.052 Uiso 1 1 d R . . H62 H 0.1610 0.2105 0.1579 0.052 Uiso 1 1 d R . . H63 H 0.1912 0.1608 0.2536 0.052 Uiso 1 1 d R . . C7 C 0.4076(2) 0.3646(2) 0.14184(13) 0.0264(4) Uani 1 1 d . . . C71 C 0.3623(3) 0.3331(3) 0.04978(15) 0.0375(5) Uani 1 1 d . . . H71 H 0.4065 0.3972 0.0117 0.045 Uiso 1 1 d R . . H72 H 0.2537 0.3364 0.0432 0.045 Uiso 1 1 d R . . H73 H 0.3973 0.2457 0.0352 0.045 Uiso 1 1 d R . . N8 N 0.5008(2) 0.46672(18) 0.15516(11) 0.0268(3) Uani 1 1 d . . . O1W O 0.2999(3) 0.1289(2) 0.51296(13) 0.0446(5) Uani 1 1 d D . . H11W H 0.259(4) 0.176(3) 0.551(2) 0.054 Uiso 1 1 d D . . H12W H 0.366(3) 0.079(3) 0.536(2) 0.054 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 Cu 0.04165(18) 0.02633(15) 0.02366(15) 0.00389(10) 0.00383(10) -0.00530(11) Cl1 0.0413(3) 0.0432(3) 0.0318(3) 0.0004(2) 0.0004(2) 0.0012(2) Cl2 0.0666(4) 0.0334(3) 0.0388(3) 0.0035(2) 0.0071(3) 0.0058(3) N1 0.0340(9) 0.0285(9) 0.0243(8) 0.0023(7) 0.0040(7) -0.0076(7) C1 0.0481(14) 0.0403(13) 0.0330(12) 0.0116(10) 0.0008(10) -0.0155(11) C1A 0.0250(9) 0.0232(8) 0.0235(9) 0.0001(7) 0.0033(7) -0.0008(7) C2 0.0338(10) 0.0303(10) 0.0264(10) -0.0021(8) 0.0051(8) -0.0053(8) O2 0.0489(10) 0.0399(10) 0.0331(9) -0.0031(7) 0.0041(7) -0.0202(8) N3 0.0401(10) 0.0339(10) 0.0223(8) -0.0003(7) -0.0013(7) -0.0099(8) C4 0.0306(10) 0.0256(9) 0.0231(9) 0.0009(7) 0.0014(7) -0.0008(8) O4 0.0473(10) 0.0337(8) 0.0233(7) 0.0053(6) -0.0009(6) -0.0071(7) C4A 0.0285(9) 0.0226(8) 0.0208(8) -0.0001(7) 0.0020(7) -0.0006(7) N5 0.0320(9) 0.0227(8) 0.0238(8) 0.0006(6) 0.0012(6) -0.0029(6) C6 0.0347(10) 0.0245(9) 0.0250(9) -0.0032(8) 0.0012(8) -0.0025(8) C61 0.0523(15) 0.0410(13) 0.0356(12) -0.0019(10) -0.0033(11) -0.0194(11) C7 0.0295(9) 0.0288(10) 0.0209(9) -0.0011(7) 0.0015(7) 0.0019(8) C71 0.0483(14) 0.0425(13) 0.0216(10) -0.0039(9) -0.0006(9) -0.0047(11) N8 0.0311(9) 0.0277(8) 0.0217(8) 0.0018(7) 0.0031(6) -0.0007(7) O1W 0.0677(13) 0.0369(10) 0.0298(9) 0.0073(8) 0.0127(8) 0.0012(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 Cu O1W 1.9552(19) . ? Cu N5 2.0248(19) . ? Cu Cl2 2.2684(8) . ? Cu Cl1 2.2715(7) . ? Cu O4 2.3725(18) . ? N1 C2 1.374(3) . ? N1 C1A 1.386(3) . ? N1 C1 1.470(3) . ? C1A N8 1.340(3) . ? C1A C4A 1.385(3) . ? C2 O2 1.225(3) . ? C2 N3 1.383(3) . ? N3 C4 1.365(3) . ? C4 O4 1.231(3) . ? C4 C4A 1.456(3) . ? C4A N5 1.351(3) . ? N5 C6 1.326(3) . ? C6 C7 1.427(3) . ? C6 C61 1.494(3) . ? C7 N8 1.328(3) . ? C7 C71 1.492(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 O1W Cu N5 176.14(8) . . ? O1W Cu Cl2 90.09(7) . . ? N5 Cu Cl2 92.09(6) . . ? O1W Cu Cl1 89.59(7) . . ? N5 Cu Cl1 89.41(6) . . ? Cl2 Cu Cl1 160.68(3) . . ? O1W Cu O4 98.16(8) . . ? N5 Cu O4 78.20(7) . . ? Cl2 Cu O4 104.84(5) . . ? Cl1 Cu O4 94.32(5) . . ? C2 N1 C1A 121.30(18) . . ? C2 N1 C1 118.24(19) . . ? C1A N1 C1 120.35(19) . . ? N8 C1A C4A 122.08(18) . . ? N8 C1A N1 118.11(18) . . ? C4A C1A N1 119.80(18) . . ? O2 C2 N1 121.9(2) . . ? O2 C2 N3 121.2(2) . . ? N1 C2 N3 116.90(19) . . ? C4 N3 C2 126.87(19) . . ? O4 C4 N3 123.0(2) . . ? O4 C4 C4A 123.3(2) . . ? N3 C4 C4A 113.68(18) . . ? C4 O4 Cu 104.84(14) . . ? N5 C4A C1A 120.19(18) . . ? N5 C4A C4 118.74(18) . . ? C1A C4A C4 121.07(18) . . ? C6 N5 C4A 119.13(19) . . ? C6 N5 Cu 126.63(15) . . ? C4A N5 Cu 114.12(14) . . ? N5 C6 C7 119.28(19) . . ? N5 C6 C61 118.6(2) . . ? C7 C6 C61 122.1(2) . . ? N8 C7 C6 121.75(19) . . ? N8 C7 C71 117.3(2) . . ? C6 C7 C71 120.9(2) . . ? C7 N8 C1A 117.24(18) . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O1W H11W O2 0.839(18) 1.94(2) 2.767(3) 167(4) 3_666 O1W H12W Cl2 0.836(18) 2.34(2) 3.143(2) 162(4) 3_656 N3 H3 Cl1 0.86 2.41 3.250(2) 164.4 3_666 _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 30.00 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.904 _refine_diff_density_min -0.757 _refine_diff_density_rms 0.089 _cod_database_code 1100146