#------------------------------------------------------------------------------ #$Date: 2025-08-19 11:43:10 +0100 (Tue, 19 Aug 2025) $ #$Revision: 301803 $ #$URL: svn://www.crystallography.net/cod/cif/2/20/36/2203601.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_2203601 loop_ _publ_author_name 'Yang, Hui-Juan' 'Kou, Hui-Zhong' 'Gao, Fei' 'Cui, Ai-Li' 'Wang, Ru-Ji' _publ_section_title ; Bis(4,5-diazafluoren-9-one)dicyanamidocopper(II) ; _journal_issue 5 _journal_name_full 'Acta Crystallographica Section E' _journal_page_first m611 _journal_page_last m613 _journal_paper_doi 10.1107/S1600536804008876 _journal_volume 60 _journal_year 2004 _chemical_formula_iupac '[Cu (C2 N3)2 (C11 H6 N2 O)2]' _chemical_formula_moiety 'C26 H12 Cu N10 O2' _chemical_formula_sum 'C26 H12 Cu N10 O2' _chemical_formula_weight 560.00 _chemical_name_systematic ; Bis(4,5-diazafluorene-9-one)dicyanamidocopper(II) ; _space_group_IT_number 14 _symmetry_cell_setting monoclinic _symmetry_space_group_name_Hall '-P 2ybc' _symmetry_space_group_name_H-M 'P 1 21/c 1' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _audit_creation_method SHELXL97 _cell_angle_alpha 90.00 _cell_angle_beta 101.192(11) _cell_angle_gamma 90.00 _cell_formula_units_Z 2 _cell_length_a 8.2935(12) _cell_length_b 14.9729(10) _cell_length_c 9.7568(11) _cell_measurement_reflns_used 25 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 11.4 _cell_measurement_theta_min 5.9 _cell_volume 1188.5(2) _computing_cell_refinement XSCANS _computing_data_collection 'XSCANS (Bruker, 1997)' _computing_data_reduction XSCANS _computing_molecular_graphics SHELXTL _computing_publication_material SHELXTL _computing_structure_refinement SHELXTL _computing_structure_solution 'SHELXTL (Sheldrick, 1995)' _diffrn_ambient_temperature 293(2) _diffrn_measured_fraction_theta_full 0.997 _diffrn_measured_fraction_theta_max 0.997 _diffrn_measurement_device_type 'Bruker P4' _diffrn_measurement_method \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 0.0285 _diffrn_reflns_av_sigmaI/netI 0.0472 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_h_min -1 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_k_min -1 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_number 2758 _diffrn_reflns_theta_full 25.00 _diffrn_reflns_theta_max 25.00 _diffrn_reflns_theta_min 2.50 _diffrn_standards_decay_% 0 _diffrn_standards_interval_count 100 _diffrn_standards_number 3 _exptl_absorpt_coefficient_mu 0.967 _exptl_absorpt_correction_T_max 0.908 _exptl_absorpt_correction_T_min 0.855 _exptl_absorpt_correction_type '\y scan' _exptl_absorpt_process_details '(North et al., 1968)' _exptl_crystal_colour blue _exptl_crystal_density_diffrn 1.565 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_description platelet _exptl_crystal_F_000 566 _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.10 _refine_diff_density_max 0.483 _refine_diff_density_min -0.393 _refine_ls_extinction_coef 0 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.098 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 178 _refine_ls_number_reflns 2090 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.098 _refine_ls_R_factor_all 0.0604 _refine_ls_R_factor_gt 0.0434 _refine_ls_shift/su_max 0.006 _refine_ls_shift/su_mean 0.001 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w = 1/[\s^2^(Fo^2^)+(0.001P)^2^+1.2P] where P = (Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0925 _refine_ls_wR_factor_ref 0.1018 _reflns_number_gt 1524 _reflns_number_total 2090 _reflns_threshold_expression I>2\s(I) _cod_data_source_file hb6030.cif _cod_data_source_block I _cod_depositor_comments ; The following automatic conversions were performed: '_exptl_crystal_density_meas' value 'none' was changed to '?' - the value is perceived as not measured. Automatic conversion script Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas ; _cod_original_sg_symbol_H-M 'P 21/c' _cod_database_code 2203601 _cod_database_fobs_code 2203601 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' 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_type_symbol Cu1 1.0000 0.0000 0.0000 0.05003(19) Uani d S 1 Cu O1 0.7164(4) -0.0688(2) 0.5431(3) 0.0918(10) Uani d . 1 O N1 0.8154(3) 0.02041(19) 0.1013(3) 0.0516(7) Uani d . 1 N N2 1.0964(4) -0.0945(2) 0.2355(3) 0.0599(8) Uani d . 1 N N3 1.1946(5) 0.2309(3) 0.2451(4) 0.0965(13) Uani d . 1 N N4 1.1091(4) 0.1055(2) 0.0927(3) 0.0626(8) Uani d . 1 N N5 1.4638(6) 0.2838(3) 0.3530(5) 0.1172(16) Uani d . 1 N C1 0.6802(4) 0.0715(3) 0.0611(4) 0.0628(10) Uani d . 1 C H1A 0.6659 0.1000 -0.0251 0.075 Uiso calc R 1 H C2 0.5635(5) 0.0831(3) 0.1410(4) 0.0719(11) Uani d . 1 C H2A 0.4733 0.1195 0.1088 0.086 Uiso calc R 1 H C3 0.5786(5) 0.0412(3) 0.2695(4) 0.0697(11) Uani d . 1 C H3A 0.4994 0.0476 0.3245 0.084 Uiso calc R 1 H C4 0.7158(4) -0.0101(3) 0.3115(4) 0.0572(9) Uani d . 1 C C5 0.7804(5) -0.0625(3) 0.4420(4) 0.0660(10) Uani d . 1 C C6 0.9408(5) -0.1007(3) 0.4228(4) 0.0616(10) Uani d . 1 C C7 1.0551(6) -0.1542(3) 0.5031(4) 0.0739(12) Uani d . 1 C H7A 1.0420 -0.1742 0.5905 0.089 Uiso calc R 1 H C8 1.1909(6) -0.1773(3) 0.4484(4) 0.0773(12) Uani d . 1 C H8A 1.2716 -0.2137 0.4997 0.093 Uiso calc R 1 H C9 1.2084(5) -0.1469(3) 0.3176(4) 0.0722(11) Uani d . 1 C H9A 1.3021 -0.1634 0.2847 0.087 Uiso calc R 1 H C10 0.8296(4) -0.0185(2) 0.2249(4) 0.0513(9) Uani d . 1 C C11 0.9684(4) -0.0740(2) 0.2920(4) 0.0524(8) Uani d . 1 C C12 1.1588(5) 0.1622(3) 0.1629(4) 0.0634(10) Uani d . 1 C C13 1.3445(6) 0.2558(3) 0.2990(4) 0.0705(11) Uani d . 1 C 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 Cu1 0.0425(3) 0.0600(4) 0.0488(3) -0.0034(3) 0.0120(2) -0.0063(3) O1 0.107(2) 0.107(3) 0.0740(19) 0.009(2) 0.0494(18) 0.0108(18) N1 0.0435(15) 0.0612(19) 0.0502(16) -0.0002(13) 0.0092(12) -0.0038(14) N2 0.0575(19) 0.0617(19) 0.0609(18) 0.0052(15) 0.0124(15) -0.0033(15) N3 0.087(3) 0.071(2) 0.115(3) 0.010(2) -0.023(2) -0.029(2) N4 0.0501(18) 0.068(2) 0.069(2) -0.0039(16) 0.0100(15) -0.0160(18) N5 0.093(3) 0.101(3) 0.144(4) -0.022(3) -0.009(3) -0.035(3) C1 0.053(2) 0.077(3) 0.058(2) 0.005(2) 0.0102(18) -0.002(2) C2 0.052(2) 0.091(3) 0.074(3) 0.013(2) 0.015(2) -0.004(2) C3 0.055(2) 0.087(3) 0.072(3) 0.000(2) 0.025(2) -0.014(2) C4 0.055(2) 0.063(2) 0.058(2) -0.0050(19) 0.0210(17) -0.0074(18) C5 0.076(3) 0.068(3) 0.060(2) -0.005(2) 0.027(2) -0.008(2) C6 0.076(3) 0.056(2) 0.053(2) -0.004(2) 0.0128(19) -0.0040(18) C7 0.098(3) 0.067(3) 0.057(2) 0.000(2) 0.015(2) 0.000(2) C8 0.083(3) 0.072(3) 0.071(3) 0.014(2) 0.001(2) 0.002(2) C9 0.064(2) 0.075(3) 0.076(3) 0.014(2) 0.010(2) -0.007(2) C10 0.0479(19) 0.055(2) 0.053(2) -0.0078(16) 0.0154(15) -0.0098(16) C11 0.054(2) 0.053(2) 0.0510(19) -0.0032(17) 0.0124(16) -0.0063(16) C12 0.056(2) 0.064(3) 0.065(2) 0.009(2) 0.0016(19) 0.005(2) C13 0.074(3) 0.055(2) 0.078(3) -0.003(2) 0.001(2) -0.008(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_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle _geom_angle_publ_flag N2 Cu1 N1 . . 77.7(3) yes N4 Cu1 N2 . . 89.8(4) yes N4 Cu1 N4 3_755 . 180.0(2) yes N4 Cu1 N1 3_755 3_755 88.74(12) yes N4 Cu1 N1 . 3_755 91.26(12) yes N4 Cu1 N1 3_755 . 91.26(12) yes N4 Cu1 N1 . . 88.74(12) yes N1 Cu1 N1 3_755 . 180.0(2) no C10 N1 C1 . . 115.8(3) yes C10 N1 Cu1 . . 116.2(2) yes C1 N1 Cu1 . . 127.9(2) yes C11 N2 C9 . . 113.7(3) no C12 N3 C13 . . 124.0(4) yes C12 N4 Cu1 . . 168.6(3) yes N1 C1 C2 . . 123.1(4) no N1 C1 H1A . . 118.4 no C2 C1 H1A . . 118.4 no C1 C2 C3 . . 120.6(4) no C1 C2 H2A . . 119.7 no C3 C2 H2A . . 119.7 no C4 C3 C2 . . 116.7(4) no C4 C3 H3A . . 121.7 no C2 C3 H3A . . 121.7 no C3 C4 C10 . . 119.5(4) no C3 C4 C5 . . 133.3(3) no C10 C4 C5 . . 107.2(3) no O1 C5 C6 . . 127.9(4) no O1 C5 C4 . . 126.1(4) no C6 C5 C4 . . 105.9(3) no C7 C6 C11 . . 118.2(4) no C7 C6 C5 . . 133.6(4) no C11 C6 C5 . . 108.2(3) no C6 C7 C8 . . 116.9(4) no C6 C7 H7A . . 121.5 no C8 C7 H7A . . 121.5 no C7 C8 C9 . . 120.8(4) no C7 C8 H8A . . 119.6 no C9 C8 H8A . . 119.6 no N2 C9 C8 . . 123.5(4) no N2 C9 H9A . . 118.2 no C8 C9 H9A . . 118.2 no N1 C10 C4 . . 124.3(3) no N1 C10 C11 . . 125.4(3) no C4 C10 C11 . . 110.3(3) no N2 C11 C6 . . 126.9(4) no N2 C11 C10 . . 124.7(3) no C6 C11 C10 . . 108.4(3) no N4 C12 N3 . . 171.7(5) yes N5 C13 N3 . . 172.2(5) yes 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 Cu1 N4 3_755 1.954(3) yes Cu1 N4 . 1.954(3) yes Cu1 N1 3_755 2.001(3) yes Cu1 N1 . 2.001(3) yes Cu1 N2 . 2.684(3) yes O1 C5 . 1.211(4) no N1 C10 . 1.324(4) no N1 C1 . 1.350(4) no N2 C11 . 1.324(4) no N2 C9 . 1.354(5) no N3 C12 . 1.301(5) yes N3 C13 . 1.307(6) yes N4 C12 . 1.118(5) yes N5 C13 . 1.109(5) yes C1 C2 . 1.366(5) no C1 H1A . 0.9300 no C2 C3 . 1.386(6) no C2 H2A . 0.9300 no C3 C4 . 1.368(5) no C3 H3A . 0.9300 no C4 C10 . 1.390(5) no C4 C5 . 1.503(5) no C5 C6 . 1.493(6) no C6 C7 . 1.366(6) no C6 C11 . 1.398(5) no C7 C8 . 1.381(6) no C7 H7A . 0.9300 no C8 C9 . 1.388(6) no C8 H8A . 0.9300 no C9 H9A . 0.9300 no C10 C11 . 1.467(5) no 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 C1 H1A N5 4_465 0.93 2.54 3.260(3) 134 C9 H9A N5 2_845 0.93 2.69 3.605(3) 170 C3 H3A O1 3_656 0.93 2.42 3.352(3) 177 loop_ _cod_related_entry_id _cod_related_entry_database _cod_related_entry_code 1 PubChem 139066649