#------------------------------------------------------------------------------ #$Date: 2025-08-19 11:43:10 +0100 (Tue, 19 Aug 2025) $ #$Revision: 301803 $ #$URL: svn://www.crystallography.net/cod/cif/2/20/21/2202128.cif $ #------------------------------------------------------------------------------ # # This file is available in the Crystallography Open Database (COD), # http://www.crystallography.net/. The original data for this entry # were provided by IUCr Journals, http://journals.iucr.org/. # # The file may be used within the scientific community so long as # proper attribution is given to the journal article from which the # data were obtained. # data_2202128 loop_ _publ_author_name 'Li, Xing' 'Cao, Rong' 'Bi, Wenhua' 'Sun, Daofeng' 'Hong, Maochun' _publ_section_title ; Orotato(1,10-phenanthroline)copper(II) ; _journal_issue 5 _journal_name_full 'Acta Crystallographica Section E' _journal_page_first m228 _journal_page_last m229 _journal_paper_doi 10.1107/S1600536803007451 _journal_volume 59 _journal_year 2003 _chemical_formula_iupac '[Cu (C5 H2 N2 O4) (C12 H8 N2)]' _chemical_formula_moiety 'C17 H10 Cu N4 O4' _chemical_formula_sum 'C17 H10 Cu N4 O4' _chemical_formula_weight 397.83 _chemical_name_systematic ; Orotato(1,10-phenanthroline)copper(II) ; _space_group_IT_number 14 _symmetry_cell_setting monoclinic _symmetry_space_group_name_Hall '-P 2yn' _symmetry_space_group_name_H-M 'P 1 21/n 1' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _audit_creation_method SHELXL-97 _cell_angle_alpha 90.00 _cell_angle_beta 90.9160(10) _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 8.6703(2) _cell_length_b 7.8597(2) _cell_length_c 21.5279(2) _cell_measurement_reflns_used 80 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 25.00 _cell_measurement_theta_min 1.89 _cell_volume 1466.85(5) _computing_cell_refinement SMART _computing_data_collection 'SMART (Siemens, 1996)' _computing_data_reduction 'SAINT (Siemens, 1994)' _computing_molecular_graphics SHELXTL _computing_publication_material SHELXTL _computing_structure_refinement SHELXTL _computing_structure_solution 'SHELXTL (Siemens, 1994)' _diffrn_ambient_temperature 293(2) _diffrn_measured_fraction_theta_full 0.991 _diffrn_measured_fraction_theta_max 0.991 _diffrn_measurement_device_type 'Siemens SMART CCD area-detector' _diffrn_measurement_method '\f and \w' _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0240 _diffrn_reflns_av_sigmaI/netI 0.0318 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_l_max 25 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_number 5179 _diffrn_reflns_theta_full 25.00 _diffrn_reflns_theta_max 25.00 _diffrn_reflns_theta_min 1.89 _diffrn_standards_decay_% none _diffrn_standards_interval_count none _diffrn_standards_interval_time none _diffrn_standards_number none _exptl_absorpt_coefficient_mu 1.524 _exptl_absorpt_correction_T_max 0.913 _exptl_absorpt_correction_T_min 0.682 _exptl_absorpt_correction_type empirical _exptl_absorpt_process_details '(SADABS; Sheldrick, 1996)' _exptl_crystal_colour blue _exptl_crystal_density_diffrn 1.801 _exptl_crystal_density_method 'not measured' _exptl_crystal_description block _exptl_crystal_F_000 804 _exptl_crystal_size_max .58 _exptl_crystal_size_mid .26 _exptl_crystal_size_min .06 _refine_diff_density_max 0.427 _refine_diff_density_min -0.522 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.079 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 235 _refine_ls_number_reflns 2560 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.079 _refine_ls_R_factor_gt 0.0384 _refine_ls_shift/su_max <0.001 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w = 1/[\s^2^(Fo^2^)+(0.0483P)^2^+1.9946P] where P = (Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0961 _refine_ls_wR_factor_ref 0.1056 _reflns_number_gt 2127 _reflns_number_total 2560 _reflns_threshold_expression I>2\s(I) _cod_data_source_file ob6231.cif _cod_data_source_block I _cod_original_sg_symbol_H-M 'P 21/n' _cod_database_code 2202128 _cod_database_fobs_code 2202128 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' loop_ _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_calc_flag _atom_site_refinement_flags _atom_site_occupancy _atom_site_disorder_assembly _atom_site_disorder_group _atom_site_type_symbol Cu 0.22423(5) 0.43152(5) -0.034154(19) 0.03421(17) Uani d . 1 . . Cu O1 0.3815(3) 0.3674(3) 0.02713(11) 0.0408(6) Uani d . 1 . . O N2 0.1386(3) 0.9050(4) 0.05854(14) 0.0390(7) Uani d . 1 . . N H2A 0.0825 0.9941 0.0529 0.047 Uiso calc R 1 . . H N4 0.2592(3) 0.2062(4) -0.07521(14) 0.0370(7) Uani d . 1 . . N O2 0.5312(3) 0.4680(3) 0.10408(12) 0.0502(7) Uani d . 1 . . O N1 0.2074(3) 0.6347(4) 0.02113(13) 0.0326(6) Uani d . 1 . . N N3 0.0901(3) 0.4664(4) -0.11428(13) 0.0353(7) Uani d . 1 . . N O3 0.2549(4) 1.0384(4) 0.13973(13) 0.0559(8) Uani d . 1 . . O C7 0.3429(5) 0.0775(5) -0.0530(2) 0.0448(9) Uani d . 1 . . C H7A 0.3925 0.0898 -0.0147 0.054 Uiso calc R 1 . . H C6 0.1874(4) 0.1869(5) -0.13119(16) 0.0353(8) Uani d . 1 . . C O4 -0.0025(3) 0.7776(4) -0.01688(13) 0.0604(9) Uani d . 1 . . O C2 0.3174(4) 0.6363(5) 0.06778(15) 0.0324(7) Uani d . 1 . . C C3 0.3390(4) 0.7599(5) 0.10965(16) 0.0375(8) Uani d . 1 . . C H3A 0.4138 0.7476 0.1408 0.045 Uiso calc R 1 . . H C4 0.2468(4) 0.9118(5) 0.10664(15) 0.0374(8) Uani d . 1 . . C C17 0.0965(4) 0.3280(4) -0.15231(15) 0.0337(8) Uani d . 1 . . C C1 0.4198(4) 0.4781(5) 0.06788(16) 0.0364(8) Uani d . 1 . . C C5 0.1115(4) 0.7706(5) 0.01878(16) 0.0388(9) Uani d . 1 . . C C10 0.1974(5) 0.0377(5) -0.16661(18) 0.0432(9) Uani d . 1 . . C C16 0.0050(4) 0.5973(5) -0.13386(18) 0.0430(9) Uani d . 1 . . C H16A -0.0010 0.6933 -0.1088 0.052 Uiso calc R 1 . . H C15 -0.0762(5) 0.5964(5) -0.19078(18) 0.0496(10) Uani d . 1 . . C H15A -0.1340 0.6909 -0.2027 0.059 Uiso calc R 1 . . H C13 0.0165(4) 0.3164(5) -0.20972(16) 0.0392(8) Uani d . 1 . . C C11 0.1159(5) 0.0301(6) -0.22480(19) 0.0516(11) Uani d . 1 . . C H11A 0.1225 -0.0673 -0.2491 0.062 Uiso calc R 1 . . H C9 0.2867(5) -0.0958(5) -0.1410(2) 0.0509(10) Uani d . 1 . . C H9A 0.2961 -0.1980 -0.1624 0.061 Uiso calc R 1 . . H C14 -0.0708(5) 0.4584(5) -0.22854(18) 0.0490(10) Uani d . 1 . . C H14A -0.1242 0.4578 -0.2664 0.059 Uiso calc R 1 . . H C12 0.0295(5) 0.1624(6) -0.24490(18) 0.0503(10) Uani d . 1 . . C H12A -0.0232 0.1535 -0.2827 0.060 Uiso calc R 1 . . H C8 0.3591(5) -0.0748(5) -0.0851(2) 0.0539(11) Uani d . 1 . . C H8A 0.4191 -0.1619 -0.0683 0.065 Uiso calc R 1 . . H loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 Cu 0.0353(3) 0.0364(3) 0.0306(3) 0.00821(18) -0.00960(17) -0.00646(19) O1 0.0507(15) 0.0358(13) 0.0353(13) 0.0091(12) -0.0158(11) -0.0044(12) N2 0.0365(16) 0.0432(18) 0.0370(16) 0.0151(13) -0.0099(13) -0.0123(14) N4 0.0390(16) 0.0342(16) 0.0376(16) 0.0037(13) -0.0060(13) -0.0025(13) O2 0.0602(18) 0.0445(16) 0.0448(15) 0.0150(13) -0.0289(13) -0.0024(13) N1 0.0291(14) 0.0384(16) 0.0300(15) 0.0061(13) -0.0080(11) -0.0069(13) N3 0.0381(16) 0.0356(16) 0.0320(15) 0.0037(13) -0.0042(12) -0.0029(13) O3 0.070(2) 0.0505(17) 0.0462(16) 0.0142(14) -0.0250(14) -0.0216(14) C7 0.051(2) 0.0327(19) 0.050(2) 0.0062(17) -0.0097(18) 0.0006(18) C6 0.0330(18) 0.039(2) 0.0336(18) -0.0034(15) 0.0004(15) -0.0045(16) O4 0.0473(16) 0.072(2) 0.0613(18) 0.0302(15) -0.0312(14) -0.0330(16) C2 0.0347(18) 0.0346(18) 0.0279(17) 0.0017(15) -0.0028(14) 0.0001(15) C3 0.041(2) 0.042(2) 0.0289(18) 0.0067(16) -0.0143(15) -0.0004(16) C4 0.042(2) 0.045(2) 0.0249(17) 0.0051(17) -0.0077(14) -0.0036(16) C17 0.0328(18) 0.040(2) 0.0286(17) -0.0030(15) 0.0007(14) -0.0033(15) C1 0.042(2) 0.0357(19) 0.0311(18) 0.0049(16) -0.0069(15) 0.0025(16) C5 0.0342(19) 0.047(2) 0.0350(19) 0.0086(16) -0.0061(15) -0.0130(17) C10 0.046(2) 0.042(2) 0.041(2) -0.0050(17) 0.0068(17) -0.0108(18) C16 0.047(2) 0.043(2) 0.039(2) 0.0083(17) -0.0096(17) -0.0026(17) C15 0.059(3) 0.049(2) 0.040(2) 0.011(2) -0.0126(18) 0.0042(19) C13 0.040(2) 0.049(2) 0.0285(18) -0.0080(17) -0.0037(15) -0.0018(16) C11 0.060(3) 0.052(3) 0.043(2) -0.008(2) 0.0028(19) -0.018(2) C9 0.056(3) 0.034(2) 0.063(3) 0.0011(18) 0.006(2) -0.0127(19) C14 0.053(2) 0.063(3) 0.0310(19) -0.001(2) -0.0146(17) 0.0037(19) C12 0.057(2) 0.062(3) 0.032(2) -0.015(2) -0.0034(18) -0.0091(19) C8 0.057(3) 0.035(2) 0.069(3) 0.0102(19) -0.007(2) -0.002(2) 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' loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_publ_flag O1 Cu N1 81.97(10) yes O1 Cu N4 87.76(11) yes N1 Cu N4 168.99(12) yes O1 Cu N3 165.97(11) yes N1 Cu N3 110.06(11) yes N4 Cu N3 80.65(11) yes C1 O1 Cu 117.4(2) ? C5 N2 C4 126.9(3) ? C5 N2 H2A 116.6 ? C4 N2 H2A 116.6 ? C7 N4 C6 118.3(3) ? C7 N4 Cu 126.9(3) ? C6 N4 Cu 114.9(2) ? C5 N1 C2 116.0(3) ? C5 N1 Cu 131.2(2) ? C2 N1 Cu 112.7(2) ? C16 N3 C17 117.0(3) ? C16 N3 Cu 131.6(2) ? C17 N3 Cu 111.4(2) ? N4 C7 C8 122.4(4) ? N4 C7 H7A 118.8 ? C8 C7 H7A 118.8 ? N4 C6 C10 123.1(3) ? N4 C6 C17 116.0(3) ? C10 C6 C17 120.9(3) ? C3 C2 N1 126.1(3) ? C3 C2 C1 121.0(3) ? N1 C2 C1 113.0(3) ? C2 C3 C4 120.1(3) ? C2 C3 H3A 120.0 ? C4 C3 H3A 120.0 ? O3 C4 N2 119.8(3) ? O3 C4 C3 128.5(3) ? N2 C4 C3 111.7(3) ? N3 C17 C13 123.6(3) ? N3 C17 C6 117.1(3) ? C13 C17 C6 119.3(3) ? O2 C1 O1 125.6(3) ? O2 C1 C2 120.2(3) ? O1 C1 C2 114.1(3) ? O4 C5 N1 122.7(3) ? O4 C5 N2 118.4(3) ? N1 C5 N2 118.9(3) ? C6 C10 C9 116.6(4) ? C6 C10 C11 118.5(4) ? C9 C10 C11 124.8(4) ? N3 C16 C15 122.7(4) ? N3 C16 H16A 118.6 ? C15 C16 H16A 118.6 ? C14 C15 C16 120.4(4) ? C14 C15 H15A 119.8 ? C16 C15 H15A 119.8 ? C14 C13 C17 117.2(3) ? C14 C13 C12 124.4(3) ? C17 C13 C12 118.4(4) ? C12 C11 C10 120.9(4) ? C12 C11 H11A 119.6 ? C10 C11 H11A 119.6 ? C8 C9 C10 119.9(4) ? C8 C9 H9A 120.1 ? C10 C9 H9A 120.1 ? C15 C14 C13 119.1(3) ? C15 C14 H14A 120.5 ? C13 C14 H14A 120.5 ? C11 C12 C13 122.0(4) ? C11 C12 H12A 119.0 ? C13 C12 H12A 119.0 ? C9 C8 C7 119.7(4) ? C9 C8 H8A 120.1 ? C7 C8 H8A 120.1 ? loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag Cu O1 . 1.949(2) yes Cu N1 . 1.998(3) yes Cu N4 . 2.004(3) yes Cu N3 . 2.083(3) yes O1 C1 . 1.276(4) ? N2 C5 . 1.377(4) ? N2 C4 . 1.387(4) ? N2 H2A . 0.8600 ? N4 C7 . 1.329(5) ? N4 C6 . 1.356(4) ? O2 C1 . 1.234(4) ? N1 C5 . 1.354(4) ? N1 C2 . 1.374(4) ? N3 C16 . 1.331(5) ? N3 C17 . 1.363(4) ? O3 C4 . 1.225(4) ? C7 C8 . 1.389(5) ? C7 H7A . 0.9300 ? C6 C10 . 1.402(5) ? C6 C17 . 1.431(5) ? O4 C5 . 1.243(4) ? C2 C3 . 1.336(5) ? C2 C1 . 1.528(5) ? C3 C4 . 1.438(5) ? C3 H3A . 0.9300 ? C17 C13 . 1.410(5) ? C10 C9 . 1.411(6) ? C10 C11 . 1.430(6) ? C16 C15 . 1.403(5) ? C16 H16A . 0.9300 ? C15 C14 . 1.356(6) ? C15 H15A . 0.9300 ? C13 C14 . 1.405(6) ? C13 C12 . 1.433(6) ? C11 C12 . 1.349(6) ? C11 H11A . 0.9300 ? C9 C8 . 1.360(6) ? C9 H9A . 0.9300 ? C14 H14A . 0.9300 ? C12 H12A . 0.9300 ? C8 H8A . 0.9300 ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_site_symmetry_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_publ_flag N2 H2A O4 3_575 0.86 2.07 2.895(4) 161 yes loop_ _cod_related_entry_id _cod_related_entry_database _cod_related_entry_code 1 PubChem 139065855