#------------------------------------------------------------------------------ #$Date: 2025-08-19 11:43:10 +0100 (Tue, 19 Aug 2025) $ #$Revision: 301803 $ #$URL: svn://www.crystallography.net/cod/cif/2/20/51/2205158.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_2205158 loop_ _publ_author_name 'Sun, Yu-Xi' _publ_section_title ; [4-Bromo-2-(pyridin-2-ylmethyliminomethyl)phenolato](methanol)copper(II) perchlorate ; _journal_issue 2 _journal_name_full 'Acta Crystallographica Section E' _journal_page_first m338 _journal_page_last m340 _journal_paper_doi 10.1107/S1600536805001194 _journal_volume 61 _journal_year 2005 _chemical_formula_iupac '[Cu (C13 H10 Br N2 O) (C H4 O)] Cl O4' _chemical_formula_moiety 'C14 H14 Br Cu N2 O2 +, Cl O4 -' _chemical_formula_sum 'C14 H14 Br Cl Cu N2 O6' _chemical_formula_weight 485.17 _chemical_name_systematic ; [4-Bromo-2-(pyridin-2-ylmethylaminomethyl)phenolato](methanol)copper(II) perchlorate ; _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 95.93(2) _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 7.204(2) _cell_length_b 19.175(2) _cell_length_c 12.716(2) _cell_measurement_reflns_used 3964 _cell_measurement_temperature 295(2) _cell_measurement_theta_max 23.303 _cell_measurement_theta_min 2.666 _cell_volume 1747.1(6) _computing_cell_refinement SMART _computing_data_collection 'SMART (Bruker, 2002)' _computing_data_reduction 'SAINT (Bruker, 2002)' _computing_molecular_graphics 'SHELXTL (Bruker, 2002)' _computing_publication_material SHELXTL _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_structure_solution 'SHELXS97 (Sheldrick, 1997)' _diffrn_ambient_temperature 295(2) _diffrn_measured_fraction_theta_full 0.995 _diffrn_measured_fraction_theta_max 0.995 _diffrn_measurement_device_type 'Bruker SMART APEX area-detector' _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 0.0416 _diffrn_reflns_av_sigmaI/netI 0.0405 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_k_max 24 _diffrn_reflns_limit_k_min -24 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_number 19666 _diffrn_reflns_theta_full 27.50 _diffrn_reflns_theta_max 27.50 _diffrn_reflns_theta_min 1.93 _diffrn_standards_decay_% 0 _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 3.723 _exptl_absorpt_correction_T_max 0.6237 _exptl_absorpt_correction_T_min 0.4947 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details '(SADABS; Sheldrick, 1996)' _exptl_crystal_colour blue _exptl_crystal_density_diffrn 1.844 _exptl_crystal_density_method 'not measured' _exptl_crystal_description block _exptl_crystal_F_000 964 _exptl_crystal_size_max 0.22 _exptl_crystal_size_mid 0.21 _exptl_crystal_size_min 0.14 _refine_diff_density_max 0.894 _refine_diff_density_min -0.644 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.028 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 268 _refine_ls_number_reflns 3994 _refine_ls_number_restraints 76 _refine_ls_restrained_S_all 1.044 _refine_ls_R_factor_all 0.0652 _refine_ls_R_factor_gt 0.0410 _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^)+(0.0404P)^2^+1.3881P] where P = (Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0919 _refine_ls_wR_factor_ref 0.1034 _reflns_number_gt 2920 _reflns_number_total 3994 _reflns_threshold_expression I>2\s(I) _cod_data_source_file su6157.cif _cod_data_source_block I _cod_depositor_comments ; The following automatic conversions were performed: '_exptl_absorpt_correction_type' value 'Multi-scan' changed to 'multi-scan' 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: '_exptl_absorpt_correction_type' value 'Multi-scan' changed to 'multi-scan' 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_original_cell_volume 1747.2(6) _cod_original_sg_symbol_H-M 'P 21/n' _cod_database_code 2205158 _cod_database_fobs_code 2205158 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 Cu1 0.36089(6) 0.12246(2) 0.50968(3) 0.03977(13) Uani d . 1 . . Cu Br1 0.20435(8) 0.06398(3) 1.06586(3) 0.0872(2) Uani d . 1 . . Br Cl1 0.84688(13) 0.15856(5) 0.45612(7) 0.0536(2) Uani d D 1 . . Cl O1 0.3857(3) 0.05105(11) 0.61400(18) 0.0471(6) Uani d . 1 . . O O2 0.3592(4) 0.05019(13) 0.39674(19) 0.0475(6) Uani d D 1 . . O O3 0.7047(9) 0.1411(7) 0.5222(7) 0.064(3) Uani d PD 0.476(18) A 1 O O4 0.9173(14) 0.2274(3) 0.4870(7) 0.066(2) Uani d PD 0.476(18) A 1 O O5 0.7856(19) 0.1558(8) 0.3484(5) 0.082(4) Uani d PD 0.476(18) A 1 O O6 1.0004(13) 0.1119(6) 0.4835(10) 0.066(3) Uani d PD 0.476(18) A 1 O O3' 0.6921(8) 0.1121(5) 0.4705(12) 0.078(3) Uani d PD 0.524(18) A 2 O O4' 0.792(3) 0.2274(3) 0.4820(7) 0.100(5) Uani d PD 0.524(18) A 2 O O5' 0.8727(19) 0.1574(6) 0.3451(5) 0.077(3) Uani d PD 0.524(18) A 2 O O6' 1.0062(13) 0.1328(7) 0.5170(10) 0.081(4) Uani d PD 0.524(18) A 2 O N1 0.3436(4) 0.19637(14) 0.6123(2) 0.0447(7) Uani d . 1 . . N N2 0.3401(4) 0.20136(14) 0.4081(2) 0.0437(7) Uani d . 1 . . N C1 0.3151(5) 0.12148(18) 0.7624(3) 0.0440(8) Uani d . 1 . . C C2 0.3435(5) 0.05696(17) 0.7126(3) 0.0416(8) Uani d . 1 . . C C3 0.3287(6) -0.0040(2) 0.7720(3) 0.0590(10) Uani d . 1 . . C H3 0.3457 -0.0471 0.7407 0.071 Uiso calc R 1 . . H C4 0.2896(6) -0.0015(2) 0.8756(3) 0.0626(11) Uani d . 1 . . C H4 0.2811 -0.0426 0.9137 0.075 Uiso calc R 1 . . H C5 0.2632(6) 0.0617(2) 0.9228(3) 0.0578(10) Uani d . 1 . . C C6 0.2755(5) 0.1221(2) 0.8685(3) 0.0544(9) Uani d . 1 . . C H6 0.2575 0.1644 0.9018 0.065 Uiso calc R 1 . . H C7 0.3197(5) 0.18780(18) 0.7098(3) 0.0491(9) Uani d . 1 . . C H7 0.3039 0.2276 0.7497 0.059 Uiso calc R 1 . . H C8 0.3382(6) 0.26706(19) 0.5687(3) 0.0625(11) Uani d . 1 . . C H8A 0.4495 0.2922 0.5962 0.075 Uiso calc R 1 . . H H8B 0.2307 0.2917 0.5901 0.075 Uiso calc R 1 . . H C9 0.3269(5) 0.26451(19) 0.4506(3) 0.0487(9) Uani d . 1 . . C C11 0.3085(6) 0.3241(2) 0.3893(4) 0.0681(12) Uani d . 1 . . C H11 0.2979 0.3676 0.4205 0.082 Uiso calc R 1 . . H C12 0.3060(7) 0.3180(2) 0.2820(4) 0.0786(14) Uani d . 1 . . C H12 0.2938 0.3575 0.2394 0.094 Uiso calc R 1 . . H C13 0.3215(6) 0.2535(2) 0.2376(4) 0.0710(12) Uani d . 1 . . C H13 0.3204 0.2485 0.1648 0.085 Uiso calc R 1 . . H C14 0.3387(5) 0.1962(2) 0.3030(3) 0.0568(10) Uani d . 1 . . C H14 0.3498 0.1523 0.2731 0.068 Uiso calc R 1 . . H C15 0.1877(7) 0.0141(2) 0.3553(4) 0.0795(14) Uani d . 1 . . C H15A 0.1368 -0.0102 0.4117 0.119 Uiso calc R 1 . . H H15B 0.2155 -0.0186 0.3019 0.119 Uiso calc R 1 . . H H15C 0.0985 0.0476 0.3250 0.119 Uiso calc R 1 . . H H2 0.453(4) 0.0243(18) 0.397(3) 0.064(13) Uiso d D 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 Cu1 0.0481(2) 0.0337(2) 0.0385(2) 0.00449(18) 0.00920(17) 0.00136(17) Br1 0.1068(4) 0.1173(5) 0.0410(2) 0.0131(3) 0.0238(2) -0.0002(2) Cl1 0.0524(5) 0.0511(5) 0.0583(6) -0.0006(4) 0.0111(4) 0.0032(4) O1 0.0673(16) 0.0381(13) 0.0378(13) 0.0117(11) 0.0152(11) 0.0016(10) O2 0.0577(16) 0.0429(14) 0.0428(14) 0.0097(12) 0.0100(12) -0.0029(11) O3 0.038(3) 0.094(7) 0.063(5) -0.001(4) 0.013(3) 0.000(4) O4 0.057(5) 0.051(4) 0.090(5) 0.007(3) 0.013(4) -0.007(3) O5 0.087(8) 0.108(7) 0.051(4) -0.019(7) 0.000(4) -0.012(4) O6 0.040(4) 0.061(5) 0.097(9) 0.005(4) 0.009(4) -0.003(5) O3' 0.044(3) 0.068(5) 0.122(9) -0.006(3) 0.010(4) 0.010(5) O4' 0.170(14) 0.048(4) 0.084(5) 0.014(5) 0.017(6) -0.009(3) O5' 0.089(8) 0.083(5) 0.057(4) 0.004(6) 0.000(4) 0.007(4) O6' 0.055(5) 0.122(9) 0.062(6) -0.025(5) -0.015(4) 0.010(6) N1 0.0503(17) 0.0353(15) 0.0483(17) -0.0019(13) 0.0049(14) -0.0021(12) N2 0.0391(15) 0.0419(16) 0.0503(17) 0.0026(12) 0.0066(13) 0.0068(13) C1 0.0444(18) 0.0454(19) 0.0427(19) 0.0009(16) 0.0070(15) -0.0080(15) C2 0.0410(18) 0.0461(19) 0.0385(18) 0.0031(15) 0.0083(14) 0.0002(15) C3 0.083(3) 0.047(2) 0.050(2) 0.011(2) 0.020(2) 0.0009(17) C4 0.083(3) 0.060(3) 0.048(2) 0.008(2) 0.024(2) 0.0109(19) C5 0.061(2) 0.077(3) 0.0365(19) 0.006(2) 0.0113(17) -0.0031(19) C6 0.059(2) 0.057(2) 0.048(2) 0.0010(19) 0.0115(18) -0.0115(18) C7 0.055(2) 0.0403(19) 0.052(2) 0.0009(16) 0.0068(17) -0.0134(16) C8 0.083(3) 0.035(2) 0.070(3) -0.0022(19) 0.007(2) -0.0002(18) C9 0.0392(19) 0.042(2) 0.064(2) -0.0033(15) 0.0042(17) 0.0088(17) C11 0.079(3) 0.044(2) 0.081(3) 0.001(2) 0.004(2) 0.010(2) C12 0.088(3) 0.059(3) 0.087(4) -0.004(2) -0.002(3) 0.035(3) C13 0.080(3) 0.075(3) 0.058(3) -0.002(2) 0.004(2) 0.023(2) C14 0.063(2) 0.055(2) 0.052(2) 0.0024(19) 0.0068(19) 0.0137(18) C15 0.101(4) 0.067(3) 0.070(3) 0.015(3) 0.007(3) -0.003(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' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Br Br -0.2901 2.4595 '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 Cu1 N1 93.71(11) y O1 Cu1 N2 176.32(11) y N1 Cu1 N2 82.83(12) y O1 Cu1 O2 89.72(10) y N1 Cu1 O2 174.94(11) y N2 Cu1 O2 93.82(11) y O5 Cl1 O6' 133.2(7) ? O5 Cl1 O4' 101.2(7) ? O6' Cl1 O4' 115.4(5) ? O5 Cl1 O3 113.2(5) ? O6' Cl1 O3 100.8(7) ? O4' Cl1 O3 81.2(5) ? O5 Cl1 O6 111.9(6) ? O4' Cl1 O6 138.2(6) ? O3 Cl1 O6 107.0(6) ? O6' Cl1 O5' 110.7(6) ? O4' Cl1 O5' 107.9(5) ? O3 Cl1 O5' 138.1(5) ? O6 Cl1 O5' 93.1(7) ? O5 Cl1 O4 111.4(6) ? O6' Cl1 O4 85.8(5) ? O3 Cl1 O4 107.7(5) ? O6 Cl1 O4 105.1(5) ? O5' Cl1 O4 101.6(6) ? O5 Cl1 O3' 86.1(6) ? O6' Cl1 O3' 107.9(6) ? O4' Cl1 O3' 107.7(5) ? O6 Cl1 O3' 99.7(6) ? O5' Cl1 O3' 107.0(5) ? O4 Cl1 O3' 140.7(5) ? C2 O1 Cu1 125.7(2) ? C15 O2 Cu1 122.0(2) ? C15 O2 H2 112(3) ? Cu1 O2 H2 117(3) ? C7 N1 C8 119.0(3) ? C7 N1 Cu1 125.6(2) ? C8 N1 Cu1 115.0(2) ? C9 N2 C14 118.6(3) ? C9 N2 Cu1 115.6(2) ? C14 N2 Cu1 125.8(3) ? C6 C1 C2 119.3(3) ? C6 C1 C7 117.1(3) ? C2 C1 C7 123.6(3) ? O1 C2 C3 118.4(3) ? O1 C2 C1 123.8(3) ? C3 C2 C1 117.8(3) ? C4 C3 C2 121.4(4) ? C4 C3 H3 119.3 ? C2 C3 H3 119.3 ? C5 C4 C3 120.1(4) ? C5 C4 H4 120.0 ? C3 C4 H4 120.0 ? C6 C5 C4 120.7(3) ? C6 C5 Br1 119.9(3) ? C4 C5 Br1 119.4(3) ? C5 C6 C1 120.8(3) ? C5 C6 H6 119.6 ? C1 C6 H6 119.6 ? N1 C7 C1 125.2(3) ? N1 C7 H7 117.4 ? C1 C7 H7 117.4 ? N1 C8 C9 110.3(3) ? N1 C8 H8A 109.6 ? C9 C8 H8A 109.6 ? N1 C8 H8B 109.6 ? C9 C8 H8B 109.6 ? H8A C8 H8B 108.1 ? N2 C9 C11 121.9(4) ? N2 C9 C8 116.0(3) ? C11 C9 C8 122.1(4) ? C12 C11 C9 118.9(4) ? C12 C11 H11 120.6 ? C9 C11 H11 120.6 ? C11 C12 C13 119.7(4) ? C11 C12 H12 120.1 ? C13 C12 H12 120.1 ? C12 C13 C14 118.6(4) ? C12 C13 H13 120.7 ? C14 C13 H13 120.7 ? N2 C14 C13 122.3(4) ? N2 C14 H14 118.8 ? C13 C14 H14 118.8 ? O2 C15 H15A 109.5 ? O2 C15 H15B 109.5 ? H15A C15 H15B 109.5 ? O2 C15 H15C 109.5 ? H15A C15 H15C 109.5 ? H15B C15 H15C 109.5 ? loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_publ_flag Cu1 O1 1.902(2) y Cu1 O3 2.491(7) yes Cu1 N1 1.939(3) y Cu1 N2 1.985(3) y Cu1 O2 1.995(2) y Br1 C5 1.910(4) ? Cl1 O5 1.396(6) ? Cl1 O6' 1.406(6) ? Cl1 O4' 1.427(6) ? Cl1 O3 1.430(5) ? Cl1 O6 1.437(6) ? Cl1 O5' 1.443(6) ? Cl1 O4 1.453(5) ? Cl1 O3' 1.453(5) ? O1 C2 1.325(4) ? O2 C15 1.465(5) ? O2 H2 0.84(3) ? N1 C7 1.279(4) ? N1 C8 1.464(4) ? N2 C9 1.333(5) ? N2 C14 1.340(5) ? C1 C6 1.408(5) ? C1 C2 1.414(5) ? C1 C7 1.439(5) ? C2 C3 1.402(5) ? C3 C4 1.377(5) ? C3 H3 0.9300 ? C4 C5 1.374(6) ? C4 H4 0.9300 ? C5 C6 1.355(5) ? C6 H6 0.9300 ? C7 H7 0.9300 ? C8 C9 1.495(6) ? C8 H8A 0.9700 ? C8 H8B 0.9700 ? C9 C11 1.382(5) ? C11 C12 1.368(7) ? C11 H11 0.9300 ? C12 C13 1.369(6) ? C12 H12 0.9300 ? C13 C14 1.376(5) ? C13 H13 0.9300 ? C14 H14 0.9300 ? C15 H15A 0.9600 ? C15 H15B 0.9600 ? C15 H15C 0.9600 ? 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 O2 H2 O1 3_656 0.84(3) 1.87(3) 2.686(4) 165(3) yes C6 H6 O4' 4_566 0.93 2.31 3.223(8) 166 yes C7 H7 O5' 4_566 0.93 2.54 3.432(11) 161 yes C13 H13 O4' 4_565 0.93 2.36 3.256(10) 162 yes C14 H14 O2 . 0.93 2.51 3.041(5) 117 ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion N1 Cu1 O1 C2 17.1(3) O2 Cu1 O1 C2 -159.2(3) O1 Cu1 O2 C15 85.2(3) N2 Cu1 O2 C15 -95.8(3) O1 Cu1 N1 C7 -12.0(3) N2 Cu1 N1 C7 169.3(3) O1 Cu1 N1 C8 174.8(3) N2 Cu1 N1 C8 -3.9(3) N1 Cu1 N2 C9 0.7(2) N1 Cu1 N2 C14 -179.4(3) O2 Cu1 N2 C14 -3.2(3) Cu1 O1 C2 C3 165.5(3) Cu1 O1 C2 C1 -15.4(5) C6 C1 C2 O1 -178.4(3) C7 C1 C2 O1 3.2(5) C6 C1 C2 C3 0.6(5) C7 C1 C2 C3 -177.8(4) O1 C2 C3 C4 178.5(4) C1 C2 C3 C4 -0.6(6) C2 C3 C4 C5 0.4(7) C3 C4 C5 C6 -0.1(7) C3 C4 C5 Br1 178.8(3) C4 C5 C6 C1 0.2(6) Br1 C5 C6 C1 -178.8(3) C2 C1 C6 C5 -0.4(6) C7 C1 C6 C5 178.1(4) C8 N1 C7 C1 177.8(3) Cu1 N1 C7 C1 4.9(5) C6 C1 C7 N1 -176.1(4) C2 C1 C7 N1 2.3(6) C7 N1 C8 C9 -167.6(3) Cu1 N1 C8 C9 6.1(4) C14 N2 C9 C11 1.2(5) Cu1 N2 C9 C11 -178.9(3) C14 N2 C9 C8 -177.2(3) Cu1 N2 C9 C8 2.6(4) N1 C8 C9 N2 -5.6(5) N1 C8 C9 C11 176.0(4) N2 C9 C11 C12 -0.8(6) C8 C9 C11 C12 177.6(4) C9 C11 C12 C13 0.1(7) C11 C12 C13 C14 0.2(7) C9 N2 C14 C13 -1.0(6) Cu1 N2 C14 C13 179.2(3) C12 C13 C14 N2 0.3(7) loop_ _cod_related_entry_id _cod_related_entry_database _cod_related_entry_code 1 PubChem 139067454