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#$Date: 2025-08-18 17:20:24 +0300 (Mon, 18 Aug 2025) $
#$Revision: 301776 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/51/31/1513175.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_1513175
loop_
_publ_author_name
'Sema Caglar'
'Ekrem Adiguzel'
'Bulent Caglar'
'Tuba Saykal'
'Ertan Sahin'
'Orhan Buyukgungor'
_publ_section_title
;
 Synthesis, crystal structure, spectroscopic, thermal, catechol oxidase
 and catalase-like studies: New copper(II) complexes of 2-benzoylbenzoate
 and 2-pyridilpropanol ligands
;
_journal_name_full
;
Inorganica Chimica Acta
;
_journal_page_first              101
_journal_page_last               109
_journal_paper_doi               10.1016/j.ica.2012.11.028
_journal_volume                  397
_journal_year                    2013
_chemical_formula_moiety         'C44 H40 Cu N2 O8'
_chemical_formula_sum            'C44 H40 Cu N2 O8'
_chemical_formula_weight         788.32
_chemical_name_common
bis(2-benzoylbenzoato)bis(2-pyridilpropanol)copper(II)
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                89.973(3)
_cell_angle_beta                 90.088(4)
_cell_angle_gamma                111.135(3)
_cell_formula_units_Z            1
_cell_length_a                   8.4849(4)
_cell_length_b                   10.2733(4)
_cell_length_c                   11.8111(5)
_cell_measurement_reflns_used    14649
_cell_measurement_temperature    296
_cell_measurement_theta_max      28.04
_cell_measurement_theta_min      2.13
_cell_volume                     960.29(7)
_computing_cell_refinement       X-AREA
_computing_data_collection       'X-AREA (Stoe & Cie, 2002)'
_computing_data_reduction        'X-RED32 (Stoe & Cie, 2002)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296
_diffrn_detector_area_resol_mean 6.67
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'STOE IPDS 2'
_diffrn_measurement_method       'rotation method'
_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  0.0589
_diffrn_reflns_av_sigmaI/netI    0.0437
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            14649
_diffrn_reflns_theta_full        26.49
_diffrn_reflns_theta_max         26.49
_diffrn_reflns_theta_min         2.13
_diffrn_standards_decay_%        0
_exptl_absorpt_coefficient_mu    0.626
_exptl_absorpt_correction_T_max  0.8748
_exptl_absorpt_correction_T_min  0.7917
_exptl_absorpt_correction_type   integration
_exptl_absorpt_process_details   '(X-RED32, Stoe & Cie, 2002)'
_exptl_crystal_colour            blue
_exptl_crystal_density_diffrn    1.363
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             411
_exptl_crystal_size_max          0.340
_exptl_crystal_size_mid          0.307
_exptl_crystal_size_min          0.290
_refine_diff_density_max         0.568
_refine_diff_density_min         -0.399
_refine_diff_density_rms         0.148
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     253
_refine_ls_number_reflns         3978
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.045
_refine_ls_R_factor_all          0.0405
_refine_ls_R_factor_gt           0.0365
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0557P)²+0.1195P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0853
_refine_ls_wR_factor_ref         0.0871
_reflns_number_gt                3652
_reflns_number_total             3978
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            ICA-2013-397-101-109-1.cif
_cod_data_source_block           scaglar2
_cod_database_code               1513175
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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
C1 C 0.6664(2) 0.4003(2) 0.67176(15) 0.0519(4) Uani 1 1 d .
H1 H 0.5768 0.3198 0.6516 0.062 Uiso 1 1 calc R
C2 C 0.7699(3) 0.3924(3) 0.75868(17) 0.0683(6) Uani 1 1 d .
H2 H 0.7491 0.3095 0.7981 0.082 Uiso 1 1 calc R
C3 C 0.9054(3) 0.5105(3) 0.7859(2) 0.0791(7) Uani 1 1 d .
H3 H 0.9780 0.5091 0.8446 0.095 Uiso 1 1 calc R
C4 C 0.9318(3) 0.6299(3) 0.72570(19) 0.0705(6) Uani 1 1 d .
H4 H 1.0251 0.7094 0.7421 0.085 Uiso 1 1 calc R
C5 C 0.8211(2) 0.6342(2) 0.64008(15) 0.0520(4) Uani 1 1 d .
C6 C 0.8484(3) 0.7672(2) 0.57666(18) 0.0638(5) Uani 1 1 d .
H6A H 0.9030 0.8453 0.6268 0.077 Uiso 1 1 calc R
H6B H 0.7392 0.7704 0.5559 0.077 Uiso 1 1 calc R
C7 C 0.9547(3) 0.7851(3) 0.4701(2) 0.0735(6) Uani 1 1 d .
H7A H 0.9691 0.8747 0.4362 0.088 Uiso 1 1 calc R
H7B H 1.0658 0.7862 0.4910 0.088 Uiso 1 1 calc R
C8 C 0.8796(2) 0.6728(2) 0.38355(19) 0.0632(5) Uani 1 1 d .
H8A H 0.9454 0.6956 0.3144 0.076 Uiso 1 1 calc R
H8B H 0.8812 0.5846 0.4117 0.076 Uiso 1 1 calc R
C9 C 0.60614(18) 0.19530(15) 0.29984(13) 0.0388(3) Uani 1 1 d .
C10 C 0.6232(2) 0.10842(17) 0.38475(15) 0.0468(4) Uani 1 1 d .
H10 H 0.6133 0.1309 0.4600 0.056 Uiso 1 1 calc R
C11 C 0.6548(2) -0.01161(19) 0.35925(18) 0.0580(5) Uani 1 1 d .
H11 H 0.6656 -0.0693 0.4171 0.070 Uiso 1 1 calc R
C12 C 0.6700(3) -0.04509(19) 0.2481(2) 0.0629(5) Uani 1 1 d .
H12 H 0.6924 -0.1250 0.2307 0.075 Uiso 1 1 calc R
C13 C 0.6521(3) 0.03938(19) 0.16281(17) 0.0571(5) Uani 1 1 d .
H13 H 0.6618 0.0157 0.0879 0.068 Uiso 1 1 calc R
C14 C 0.6195(2) 0.16020(16) 0.18672(14) 0.0435(3) Uani 1 1 d .
C15 C 0.58493(19) 0.33078(15) 0.32872(13) 0.0396(3) Uani 1 1 d .
C16 C 0.5976(2) 0.24378(19) 0.08781(14) 0.0492(4) Uani 1 1 d .
C17 C 0.4241(2) 0.23851(18) 0.05964(14) 0.0484(4) Uani 1 1 d .
C18 C 0.2835(2) 0.1455(2) 0.11295(17) 0.0571(4) Uani 1 1 d .
H18 H 0.2963 0.0861 0.1687 0.069 Uiso 1 1 calc R
C19 C 0.1235(3) 0.1411(3) 0.0832(2) 0.0703(6) Uani 1 1 d .
H19 H 0.0287 0.0766 0.1174 0.084 Uiso 1 1 calc R
C20 C 0.1044(3) 0.2315(3) 0.0035(2) 0.0745(6) Uani 1 1 d .
H20 H -0.0029 0.2302 -0.0145 0.089 Uiso 1 1 calc R
C21 C 0.2440(3) 0.3244(3) -0.04997(19) 0.0706(6) Uani 1 1 d .
H21 H 0.2308 0.3854 -0.1041 0.085 Uiso 1 1 calc R
C22 C 0.4035(3) 0.3269(2) -0.02324(16) 0.0581(4) Uani 1 1 d .
H22 H 0.4974 0.3878 -0.0609 0.070 Uiso 1 1 calc R
N1 N 0.68761(17) 0.51800(14) 0.61423(11) 0.0444(3) Uani 1 1 d .
O1 O 0.71079(17) 0.66141(13) 0.36119(12) 0.0547(3) Uani 1 1 d .
H1A H 0.680(3) 0.603(3) 0.319(2) 0.082 Uiso 1 1 d .
O2 O 0.55239(15) 0.34548(11) 0.43221(9) 0.0450(3) Uani 1 1 d .
O3 O 0.60331(17) 0.41748(12) 0.25266(10) 0.0521(3) Uani 1 1 d .
O4 O 0.71753(18) 0.30348(18) 0.02706(12) 0.0720(4) Uani 1 1 d .
Cu1 Cu 0.5000 0.5000 0.5000 0.03789(10) Uani 1 2 d S
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_site_symmetry_1
_geom_angle_site_symmetry_3
N1 C1 C2 123.49(19) . .
N1 C1 H1 118.3 . .
C2 C1 H1 118.3 . .
C1 C2 C3 118.1(2) . .
C1 C2 H2 121.0 . .
C3 C2 H2 121.0 . .
C4 C3 C2 119.09(19) . .
C4 C3 H3 120.5 . .
C2 C3 H3 120.5 . .
C3 C4 C5 120.9(2) . .
C3 C4 H4 119.6 . .
C5 C4 H4 119.6 . .
N1 C5 C4 119.75(19) . .
N1 C5 C6 119.79(16) . .
C4 C5 C6 120.46(18) . .
C5 C6 C7 114.41(18) . .
C5 C6 H6A 108.7 . .
C7 C6 H6A 108.7 . .
C5 C6 H6B 108.7 . .
C7 C6 H6B 108.7 . .
H6A C6 H6B 107.6 . .
C8 C7 C6 113.71(18) . .
C8 C7 H7A 108.8 . .
C6 C7 H7A 108.8 . .
C8 C7 H7B 108.8 . .
C6 C7 H7B 108.8 . .
H7A C7 H7B 107.7 . .
O1 C8 C7 108.96(17) . .
O1 C8 H8A 109.9 . .
C7 C8 H8A 109.9 . .
O1 C8 H8B 109.9 . .
C7 C8 H8B 109.9 . .
H8A C8 H8B 108.3 . .
C10 C9 C14 119.23(14) . .
C10 C9 C15 120.45(14) . .
C14 C9 C15 120.19(14) . .
C9 C10 C11 120.97(16) . .
C9 C10 H10 119.5 . .
C11 C10 H10 119.5 . .
C12 C11 C10 119.74(18) . .
C12 C11 H11 120.1 . .
C10 C11 H11 120.1 . .
C13 C12 C11 120.03(16) . .
C13 C12 H12 120.0 . .
C11 C12 H12 120.0 . .
C12 C13 C14 121.08(17) . .
C12 C13 H13 119.5 . .
C14 C13 H13 119.5 . .
C13 C14 C9 118.94(16) . .
C13 C14 C16 117.16(15) . .
C9 C14 C16 123.89(14) . .
O3 C15 O2 126.08(14) . .
O3 C15 C9 118.39(13) . .
O2 C15 C9 115.51(14) . .
O4 C16 C17 121.55(17) . .
O4 C16 C14 119.68(16) . .
C17 C16 C14 118.44(15) . .
C18 C17 C22 119.52(17) . .
C18 C17 C16 121.24(17) . .
C22 C17 C16 119.22(17) . .
C17 C18 C19 119.9(2) . .
C17 C18 H18 120.1 . .
C19 C18 H18 120.1 . .
C20 C19 C18 120.2(2) . .
C20 C19 H19 119.9 . .
C18 C19 H19 119.9 . .
C19 C20 C21 120.1(2) . .
C19 C20 H20 119.9 . .
C21 C20 H20 119.9 . .
C20 C21 C22 120.0(2) . .
C20 C21 H21 120.0 . .
C22 C21 H21 120.0 . .
C21 C22 C17 120.1(2) . .
C21 C22 H22 119.9 . .
C17 C22 H22 119.9 . .
C1 N1 C5 118.65(15) . .
C1 N1 Cu1 113.94(12) . .
C5 N1 Cu1 127.34(12) . .
C8 O1 H1A 104(2) . .
C15 O2 Cu1 127.47(10) . .
O2 Cu1 O2 180.00(6) . 2_666
O2 Cu1 N1 86.93(5) . .
O2 Cu1 N1 93.07(5) 2_666 .
O2 Cu1 N1 93.07(5) . 2_666
O2 Cu1 N1 86.93(5) 2_666 2_666
N1 Cu1 N1 180.0 . 2_666
O1 Cu1 O1 180.00(6) . 2_666
O1 Cu1 O2 87.29(4) . .
O1 Cu1 O2 92.71(4) . 2_666
O1 Cu1 O2 92.71(4) 2_666 .
O1 Cu1 O2 87.29(4) 2_666 2_666
O1 Cu1 N1 91.41(5) . .
O1 Cu1 N1 88.59(5) . 2_666
O1 Cu1 N1 91.41(5) 2_666 2_666
O1 Cu1 N1 88.59(5) 2_666 .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 N1 1.341(2) .
C1 C2 1.371(3) .
C1 H1 0.9300 .
C2 C3 1.375(4) .
C2 H2 0.9300 .
C3 C4 1.364(4) .
C3 H3 0.9300 .
C4 C5 1.390(3) .
C4 H4 0.9300 .
C5 N1 1.351(2) .
C5 C6 1.501(3) .
C6 C7 1.521(3) .
C6 H6A 0.9700 .
C6 H6B 0.9700 .
C7 C8 1.501(3) .
C7 H7A 0.9700 .
C7 H7B 0.9700 .
C8 O1 1.419(2) .
C8 H8A 0.9700 .
C8 H8B 0.9700 .
C9 C10 1.384(2) .
C9 C14 1.399(2) .
C9 C15 1.5057(19) .
C10 C11 1.386(2) .
C10 H10 0.9300 .
C11 C12 1.376(3) .
C11 H11 0.9300 .
C12 C13 1.373(3) .
C12 H12 0.9300 .
C13 C14 1.395(2) .
C13 H13 0.9300 .
C14 C16 1.500(3) .
C15 O3 1.235(2) .
C15 O2 1.2745(19) .
C16 O4 1.216(2) .
C16 C17 1.490(2) .
C17 C18 1.383(3) .
C17 C22 1.388(3) .
C18 C19 1.387(3) .
C18 H18 0.9300 .
C19 C20 1.372(4) .
C19 H19 0.9300 .
C20 C21 1.378(4) .
C20 H20 0.9300 .
C21 C22 1.380(3) .
C21 H21 0.9300 .
C22 H22 0.9300 .
N1 Cu1 2.0420(13) .
O1 H1A 0.75(3) .
O2 Cu1 1.9672(10) .
Cu1 O2 1.9672(10) 2_666
Cu1 N1 2.0420(13) 2_666
Cu1 O1 2.5503(14) 2_666
O1 Cu1 2.5503(14) .
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
O1 H1A O3 0.75(3) 1.94(3) 2.6657(17) 162(3) .
C1 H1 O1 0.93 2.52 3.055(2) 116.8 2_666
C6 H6B O2 0.97 2.33 3.174(2) 144.9 2_666
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
_geom_torsion_site_symmetry_4
N1 C1 C2 C3 -2.0(3) .
C1 C2 C3 C4 -0.3(3) .
C2 C3 C4 C5 1.9(3) .
C3 C4 C5 N1 -1.5(3) .
C3 C4 C5 C6 178.2(2) .
N1 C5 C6 C7 -89.0(2) .
C4 C5 C6 C7 91.3(2) .
C5 C6 C7 C8 60.5(3) .
C6 C7 C8 O1 52.7(3) .
C14 C9 C10 C11 0.6(2) .
C15 C9 C10 C11 -175.38(16) .
C9 C10 C11 C12 0.2(3) .
C10 C11 C12 C13 -0.7(3) .
C11 C12 C13 C14 0.4(3) .
C12 C13 C14 C9 0.4(3) .
C12 C13 C14 C16 -178.49(17) .
C10 C9 C14 C13 -0.9(2) .
C15 C9 C14 C13 175.10(14) .
C10 C9 C14 C16 177.91(15) .
C15 C9 C14 C16 -6.1(2) .
C10 C9 C15 O3 165.99(15) .
C14 C9 C15 O3 -10.0(2) .
C10 C9 C15 O2 -12.6(2) .
C14 C9 C15 O2 171.40(14) .
C13 C14 C16 O4 -67.5(2) .
C9 C14 C16 O4 113.6(2) .
C13 C14 C16 C17 105.98(18) .
C9 C14 C16 C17 -72.9(2) .
O4 C16 C17 C18 164.94(18) .
C14 C16 C17 C18 -8.4(2) .
O4 C16 C17 C22 -13.8(2) .
C14 C16 C17 C22 172.83(15) .
C22 C17 C18 C19 0.1(3) .
C16 C17 C18 C19 -178.64(17) .
C17 C18 C19 C20 -2.0(3) .
C18 C19 C20 C21 2.0(3) .
C19 C20 C21 C22 -0.2(3) .
C20 C21 C22 C17 -1.7(3) .
C18 C17 C22 C21 1.7(3) .
C16 C17 C22 C21 -179.49(17) .
C2 C1 N1 C5 2.4(3) .
C2 C1 N1 Cu1 -174.57(15) .
C4 C5 N1 C1 -0.7(2) .
C6 C5 N1 C1 179.71(16) .
C4 C5 N1 Cu1 175.87(13) .
C6 C5 N1 Cu1 -3.8(2) .
O3 C15 O2 Cu1 6.4(2) .
C9 C15 O2 Cu1 -175.10(9) .
C15 O2 Cu1 N1 -127.37(14) .
C15 O2 Cu1 N1 52.63(14) 2_666
C1 N1 Cu1 O2 -56.53(12) .
C5 N1 Cu1 O2 126.80(14) .
C1 N1 Cu1 O2 123.47(12) 2_666
C5 N1 Cu1 O2 -53.20(14) 2_666
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139041704
