#------------------------------------------------------------------------------ #$Date: 2025-08-19 11:43:10 +0100 (Tue, 19 Aug 2025) $ #$Revision: 301803 $ #$URL: svn://www.crystallography.net/cod/cif/2/20/45/2204504.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_2204504 loop_ _publ_author_name 'Wu, Chuan-Bao' _publ_section_title ; {1,1'-[1,3-Propanediylbis(nitrilomethylidyne)]di-2-naphtholato}zinc(II), containing a square-planar ZnO~2~N~2~ group ; _journal_issue 11 _journal_name_full 'Acta Crystallographica Section E' _journal_page_first m1580 _journal_page_last m1581 _journal_paper_doi 10.1107/S1600536804023177 _journal_volume 60 _journal_year 2004 _chemical_formula_iupac '[Zn (C25 H20 N2 O2)]' _chemical_formula_moiety 'C25 H20 N2 O2 Zn' _chemical_formula_sum 'C25 H20 N2 O2 Zn' _chemical_formula_weight 445.80 _chemical_name_systematic ; {1,1'-[1,3-Propanediylbis(nitrilomethylidyne)]di-2-naphtholato}zinc(II) ; _space_group_IT_number 36 _symmetry_cell_setting orthorhombic _symmetry_space_group_name_Hall 'C 2c -2' _symmetry_space_group_name_H-M 'C m c 21' _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 90.00 _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 30.601(4) _cell_length_b 8.4526(11) _cell_length_c 7.7465(10) _cell_measurement_reflns_used 3565 _cell_measurement_temperature 273(2) _cell_measurement_theta_max 27.21 _cell_measurement_theta_min 2.50 _cell_volume 2003.7(5) _computing_cell_refinement 'SAINT (Bruker, 1998)' _computing_data_collection 'SMART (Bruker, 1998)' _computing_data_reduction SAINT _computing_molecular_graphics 'SHELXTL (Sheldrick, 1997b)' _computing_publication_material SHELXTL _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997a)' _computing_structure_solution 'SHELXS97 (Sheldrick, 1997a)' _diffrn_ambient_temperature 273(2) _diffrn_measured_fraction_theta_full 0.994 _diffrn_measured_fraction_theta_max 0.994 _diffrn_measurement_device_type 'Bruker SMART1000 CCD' _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 0.0248 _diffrn_reflns_av_sigmaI/netI 0.0343 _diffrn_reflns_limit_h_max 37 _diffrn_reflns_limit_h_min -37 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_number 5623 _diffrn_reflns_theta_full 26.48 _diffrn_reflns_theta_max 26.48 _diffrn_reflns_theta_min 1.33 _diffrn_standards_decay_% 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 1.251 _exptl_absorpt_correction_T_max 0.797 _exptl_absorpt_correction_T_min 0.729 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details '(SADABS; Sheldrick, 1996)' _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.478 _exptl_crystal_density_method 'not measured' _exptl_crystal_description block _exptl_crystal_F_000 920 _exptl_crystal_size_max 0.27 _exptl_crystal_size_mid 0.22 _exptl_crystal_size_min 0.19 _refine_diff_density_max 0.567 _refine_diff_density_min -0.350 _refine_ls_abs_structure_details 'Flack (1983), 844 Friedel pairs' _refine_ls_abs_structure_Flack 0.09(2) _refine_ls_extinction_coef 0.0049(10) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_extinction_method SHELXL97 _refine_ls_goodness_of_fit_ref 1.106 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 140 _refine_ls_number_reflns 1983 _refine_ls_number_restraints 1 _refine_ls_restrained_S_all 1.105 _refine_ls_R_factor_all 0.0425 _refine_ls_R_factor_gt 0.0412 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w = 1/[\s^2^(Fo^2^)+(0.0924P)^2^+0.1608P] where P = (Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1222 _refine_ls_wR_factor_ref 0.1240 _reflns_number_gt 1908 _reflns_number_total 1983 _reflns_threshold_expression I>2\s(I) _cod_data_source_file hb6099.cif _cod_data_source_block I _cod_depositor_comments ; The following automatic conversions were performed: '_symmetry_cell_setting' value 'Orthorhombic' changed to 'orthorhombic' according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic' dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29. Automatic conversion script Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius The following automatic conversions were performed: '_symmetry_cell_setting' value 'Orthorhombic' changed to 'orthorhombic' according to /home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29. Automatic conversion script Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana ; _cod_database_code 2204504 _cod_database_fobs_code 2204504 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z+1/2' 'x, -y, z+1/2' '-x, y, z' 'x+1/2, y+1/2, z' '-x+1/2, -y+1/2, z+1/2' 'x+1/2, -y+1/2, z+1/2' '-x+1/2, y+1/2, z' 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 Zn1 0.5000 0.07324(5) 0.38651(8) 0.0529(2) Uani d S 1 Zn O1 0.46015(8) 0.2317(3) 0.4355(3) 0.0556(6) Uani d . 1 O N1 0.45487(11) -0.0697(3) 0.3394(4) 0.0526(8) Uani d . 1 N C1 0.40010(10) 0.1321(4) 0.2722(4) 0.0512(7) Uani d . 1 C C2 0.42126(10) 0.2482(3) 0.3706(5) 0.0498(7) Uani d . 1 C C3 0.39833(12) 0.3918(4) 0.4094(6) 0.0580(8) Uani d . 1 C H3 0.4112 0.4667 0.4813 0.070 Uiso calc R 1 H C4 0.35824(15) 0.4195(4) 0.3423(6) 0.0671(13) Uani d . 1 C H4 0.3439 0.5131 0.3698 0.081 Uiso calc R 1 H C5 0.33754(11) 0.3091(5) 0.2309(5) 0.0604(8) Uani d . 1 C C6 0.29611(13) 0.3414(6) 0.1577(6) 0.0745(11) Uani d . 1 C H6 0.2820 0.4360 0.1831 0.089 Uiso calc R 1 H C7 0.27672(13) 0.2349(7) 0.0504(7) 0.0828(13) Uani d . 1 C H7 0.2496 0.2576 0.0021 0.099 Uiso calc R 1 H C8 0.29713(16) 0.0932(5) 0.0130(8) 0.0766(12) Uani d . 1 C H8 0.2837 0.0218 -0.0613 0.092 Uiso calc R 1 H C9 0.33675(14) 0.0567(5) 0.0835(6) 0.0666(10) Uani d . 1 C H9 0.3498 -0.0398 0.0575 0.080 Uiso calc R 1 H C10 0.35819(10) 0.1634(4) 0.1956(4) 0.0540(7) Uani d . 1 C C11 0.41737(11) -0.0268(5) 0.2789(5) 0.0564(8) Uani d . 1 C H11 0.3996 -0.1066 0.2350 0.068 Uiso calc R 1 H C12 0.45942(14) -0.2424(4) 0.3686(8) 0.0746(12) Uani d . 1 C H12A 0.4348 -0.2790 0.4364 0.090 Uiso calc R 1 H H12B 0.4584 -0.2961 0.2580 0.090 Uiso calc R 1 H C13 0.5000 -0.2867(7) 0.4575(10) 0.0813(19) Uani d S 1 C H13A 0.5000 -0.4004 0.4744 0.098 Uiso calc SR 1 H H13B 0.5000 -0.2378 0.5708 0.098 Uiso calc SR 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 Zn1 0.0610(3) 0.0465(3) 0.0513(3) 0.000 0.000 -0.0016(2) O1 0.0554(12) 0.0471(10) 0.0643(17) -0.0008(8) 0.0016(10) -0.0096(10) N1 0.0603(16) 0.0408(13) 0.057(2) -0.0040(9) 0.0071(12) -0.0018(10) C1 0.0497(16) 0.0564(18) 0.0475(16) -0.0020(14) 0.0136(13) -0.0023(13) C2 0.0540(14) 0.0485(13) 0.0469(16) -0.0025(10) 0.0139(16) 0.0018(15) C3 0.0615(17) 0.0494(14) 0.063(2) -0.0031(12) 0.0083(17) -0.0021(17) C4 0.065(2) 0.0573(19) 0.079(4) 0.0045(13) 0.0170(19) -0.0033(15) C5 0.0524(17) 0.071(2) 0.058(2) -0.0022(15) 0.0143(15) 0.0056(16) C6 0.0549(19) 0.089(3) 0.080(3) 0.008(2) 0.0125(19) 0.005(2) C7 0.053(2) 0.114(4) 0.082(3) -0.003(2) -0.001(2) 0.000(3) C8 0.056(2) 0.099(3) 0.075(3) -0.0074(19) -0.001(2) -0.010(2) C9 0.054(2) 0.082(3) 0.064(3) -0.0052(16) 0.0115(18) -0.0134(17) C10 0.0471(15) 0.0691(19) 0.0458(16) -0.0051(15) 0.0163(14) 0.0010(14) C11 0.0575(18) 0.0532(18) 0.058(2) -0.0069(15) 0.0087(16) -0.0082(15) C12 0.084(2) 0.0400(14) 0.100(3) -0.0043(13) -0.005(3) -0.001(2) C13 0.124(6) 0.049(3) 0.071(3) 0.000 0.000 0.006(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' Zn Zn 0.2839 1.4301 '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 O1 Zn1 O1 . 4_655 82.42(14) yes O1 Zn1 N1 . . 91.20(12) yes O1 Zn1 N1 4_655 . 173.59(11) yes O1 Zn1 N1 . 4_655 173.59(11) n O1 Zn1 N1 4_655 4_655 91.20(12) ? N1 Zn1 N1 . 4_655 95.17(18) yes C2 O1 Zn1 . . 127.0(2) ? C11 N1 C12 . . 114.5(3) ? C11 N1 Zn1 . . 123.1(2) ? C12 N1 Zn1 . . 122.4(3) ? C2 C1 C10 . . 120.5(3) ? C2 C1 C11 . . 117.6(3) ? C10 C1 C11 . . 120.8(3) ? O1 C2 C1 . . 124.0(3) ? O1 C2 C3 . . 117.3(3) ? C1 C2 C3 . . 118.7(3) ? C4 C3 C2 . . 120.6(4) ? C4 C3 H3 . . 119.7 ? C2 C3 H3 . . 119.7 ? C3 C4 C5 . . 121.6(3) ? C3 C4 H4 . . 119.2 ? C5 C4 H4 . . 119.2 ? C10 C5 C6 . . 119.5(4) ? C10 C5 C4 . . 119.4(3) ? C6 C5 C4 . . 121.1(4) ? C7 C6 C5 . . 120.5(4) ? C7 C6 H6 . . 119.8 ? C5 C6 H6 . . 119.8 ? C6 C7 C8 . . 120.3(4) ? C6 C7 H7 . . 119.9 ? C8 C7 H7 . . 119.9 ? C9 C8 C7 . . 120.9(4) ? C9 C8 H8 . . 119.5 ? C7 C8 H8 . . 119.5 ? C8 C9 C10 . . 120.9(4) ? C8 C9 H9 . . 119.5 ? C10 C9 H9 . . 119.5 ? C5 C10 C9 . . 117.9(3) ? C5 C10 C1 . . 118.7(3) ? C9 C10 C1 . . 123.4(4) ? N1 C11 C1 . . 126.8(3) ? N1 C11 H11 . . 116.6 ? C1 C11 H11 . . 116.6 ? C13 C12 N1 . . 113.7(4) ? C13 C12 H12A . . 108.8 ? N1 C12 H12A . . 108.8 ? C13 C12 H12B . . 108.8 ? N1 C12 H12B . . 108.8 ? H12A C12 H12B . . 107.7 ? C12 C13 C12 . 4_655 115.4(6) ? C12 C13 H13A . . 108.4 ? C12 C13 H13A 4_655 . 108.4 ? C12 C13 H13B . . 108.4 ? C12 C13 H13B 4_655 . 108.4 ? H13A C13 H13B . . 107.5 ? 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 Zn1 O1 . 1.851(2) yes Zn1 O1 4_655 1.851(2) ? Zn1 N1 . 1.871(3) yes Zn1 N1 4_655 1.871(3) ? O1 C2 . 1.299(4) ? N1 C11 . 1.291(5) ? N1 C12 . 1.484(4) ? C1 C2 . 1.401(5) ? C1 C10 . 1.438(5) ? C1 C11 . 1.444(5) ? C2 C3 . 1.434(4) ? C3 C4 . 1.352(6) ? C3 H3 . 0.9300 ? C4 C5 . 1.420(6) ? C4 H4 . 0.9300 ? C5 C10 . 1.411(5) ? C5 C6 . 1.415(6) ? C6 C7 . 1.361(7) ? C6 H6 . 0.9300 ? C7 C8 . 1.381(7) ? C7 H7 . 0.9300 ? C8 C9 . 1.365(7) ? C8 H8 . 0.9300 ? C9 C10 . 1.413(6) ? C9 H9 . 0.9300 ? C11 H11 . 0.9300 ? C12 C13 . 1.469(6) ? C12 H12A . 0.9700 ? C12 H12B . 0.9700 ? C13 C12 4_655 1.469(6) ? C13 H13A . 0.9700 ? C13 H13B . 0.9700 ? loop_ _cod_related_entry_id _cod_related_entry_database _cod_related_entry_code 1 PubChem 139067123