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#$Date: 2023-04-13 15:19:33 +0300 (Thu, 13 Apr 2023) $
#$Revision: 282621 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/71/25/7712589.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_7712589
loop_
_publ_author_name
'Ahumada, Guillermo'
'Hamon, Paul'
'Roisnel, Thierry'
'Dorcet, Vincent'
'Fuentealba, Mauricio'
'Hernández, Loreto A.'
'Carrillo, David'
'Hamon, Jean-René'
'Manzur, Carolina'
_publ_section_title
;
 Spectroscopy, molecular structure, and electropolymerization of Ni(ii)
 and Cu(ii) complexes containing a thiophene-appending fluorinated Schiff
 base ligand
;
_journal_issue                   13
_journal_name_full               'Dalton Transactions'
_journal_page_first              4224
_journal_page_last               4236
_journal_paper_doi               10.1039/D3DT00224A
_journal_volume                  52
_journal_year                    2023
_chemical_compound_source        'synthesis as described'
_chemical_formula_moiety         'C22 H14 Br2 Cu F6 N2 O2'
_chemical_formula_sum            'C22 H14 Br2 Cu F6 N2 O2'
_chemical_formula_weight         675.71
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_update_record
;
2022-06-20 deposited with the CCDC.	2023-03-10 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 100.103(5)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   19.941(3)
_cell_length_b                   9.7696(13)
_cell_length_c                   12.1230(16)
_cell_measurement_reflns_used    7416
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      27.46
_cell_measurement_theta_min      2.78
_cell_measurement_wavelength     0.71073
_cell_volume                     2325.1(6)
_computing_cell_refinement       'APEX3 (Bruker, 2015)'
_computing_data_collection       'Bruker APEX3 (Bruker, 2015)'
_computing_data_reduction        'SAINT (Bruker, 2014)'
_computing_molecular_graphics
;
   'SXGRAPH (L. Farrugia, 1999), Mercury (CSD, 2020)'
;
_computing_publication_material
'CRYSCALC (T. Roisnel, local program, ver. 2022)'
_computing_structure_refinement  'SHELXL-2018_3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT 2014_4 (Sheldrick, 2014)'
_diffrn_ambient_temperature      150(2)
_diffrn_detector                 '(CMOS) PHOTON 100'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'D8 VENTURE Bruker AXS'
_diffrn_measurement_method       'rotation images'
_diffrn_orient_matrix_UB_11      0.0257639
_diffrn_orient_matrix_UB_12      0.0576893
_diffrn_orient_matrix_UB_13      -0.0464391
_diffrn_orient_matrix_UB_21      -0.0434426
_diffrn_orient_matrix_UB_22      0.0217798
_diffrn_orient_matrix_UB_23      -0.0518691
_diffrn_orient_matrix_UB_31      -0.0066111
_diffrn_orient_matrix_UB_32      0.0817001
_diffrn_orient_matrix_UB_33      0.0466185
_diffrn_radiation_monochromator  'multilayer monochromator'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_source         'Incoatec microfocus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0474
_diffrn_reflns_av_unetI/netI     0.0408
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            11309
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.510
_diffrn_reflns_theta_min         2.329
_diffrn_source_current           1.0
_diffrn_source_power             50.0
_diffrn_source_voltage           50.0
_exptl_absorpt_coefficient_mu    4.448
_exptl_absorpt_correction_T_max  0.315
_exptl_absorpt_correction_T_min  0.111
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
  [Sheldrick, G.M. (2014). SADABS Bruker AXS Inc., Madison, Wisconsin, USA]
;
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.930
_exptl_crystal_description       block
_exptl_crystal_F_000             1316
_exptl_crystal_size_max          0.490
_exptl_crystal_size_mid          0.350
_exptl_crystal_size_min          0.260
_refine_diff_density_max         0.458
_refine_diff_density_min         -0.719
_refine_diff_density_rms         0.083
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     159
_refine_ls_number_reflns         2672
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.057
_refine_ls_R_factor_all          0.0462
_refine_ls_R_factor_gt           0.0331
_refine_ls_shift/su_max          0.005
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0372P)²+3.5266P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0817
_refine_ls_wR_factor_ref         0.0892
_reflns_number_gt                2139
_reflns_number_total             2672
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            d3dt00224a4.cif
_cod_data_source_block           G167_1
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               7712589
#BEGIN Tags that were not found in dictionaries:
#END Tags that were not found in dictionaries
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'
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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.45868(12) 0.3828(2) 0.65549(17) 0.0415(5) Uani 1 1 d . . . . .
C2 C 0.42348(15) 0.4044(3) 0.5579(2) 0.0322(6) Uani 1 1 d . . . . .
C3 C 0.39654(18) 0.2717(3) 0.5011(3) 0.0417(7) Uani 1 1 d . . . . .
F4 F 0.44509(13) 0.1794(2) 0.5002(2) 0.0716(7) Uani 1 1 d . . . . .
F5 F 0.34992(16) 0.2168(3) 0.5509(2) 0.0903(9) Uani 1 1 d . . . . .
F6 F 0.36838(14) 0.2878(2) 0.39378(17) 0.0737(7) Uani 1 1 d . . . . .
C7 C 0.40562(15) 0.5251(3) 0.5048(2) 0.0321(6) Uani 1 1 d . . . . .
H7 H 0.383419 0.521719 0.428861 0.039 Uiso 1 1 calc R U . . .
C8 C 0.41805(14) 0.6567(3) 0.5559(2) 0.0286(5) Uani 1 1 d . . . . .
N9 N 0.45610(12) 0.6721(2) 0.65487(18) 0.0306(5) Uani 1 1 d . . . . .
C10 C 0.46588(15) 0.8077(3) 0.7094(2) 0.0337(6) Uani 1 1 d . . . . .
H10A H 0.428255 0.826599 0.750769 0.040 Uiso 1 1 calc R U . . .
H10B H 0.465846 0.879955 0.652158 0.040 Uiso 1 1 calc R U . . .
C11 C 0.37965(14) 0.7719(3) 0.4920(2) 0.0289(6) Uani 1 1 d . . . . .
C12 C 0.38767(15) 0.8014(3) 0.3826(2) 0.0348(6) Uani 1 1 d . . . . .
H12 H 0.422374 0.756887 0.351412 0.042 Uiso 1 1 calc R U . . .
C13 C 0.34541(16) 0.8950(3) 0.3191(2) 0.0364(6) Uani 1 1 d . . . . .
H13 H 0.351325 0.916022 0.244865 0.044 Uiso 1 1 calc R U . . .
C14 C 0.29467(15) 0.9575(3) 0.3645(2) 0.0320(6) Uani 1 1 d . . . . .
C15 C 0.28635(15) 0.9319(3) 0.4734(2) 0.0352(6) Uani 1 1 d . . . . .
H15 H 0.251737 0.977206 0.504256 0.042 Uiso 1 1 calc R U . . .
C16 C 0.32939(15) 0.8390(3) 0.5368(2) 0.0340(6) Uani 1 1 d . . . . .
H16 H 0.324356 0.821016 0.611940 0.041 Uiso 1 1 calc R U . . .
Cu1 Cu 0.500000 0.52710(5) 0.750000 0.03021(14) Uani 1 2 d S T P . .
Br1 Br 0.23330(2) 1.07963(4) 0.27653(3) 0.05137(13) Uani 1 1 d . . . . .
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'
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 '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'
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'
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
_geom_angle_publ_flag
C2 O1 Cu1 122.71(18) . . ?
O1 C2 C7 129.4(3) . . ?
O1 C2 C3 111.7(2) . . ?
C7 C2 C3 118.8(3) . . ?
F5 C3 F4 107.7(3) . . ?
F5 C3 F6 106.6(3) . . ?
F4 C3 F6 104.8(3) . . ?
F5 C3 C2 111.4(3) . . ?
F4 C3 C2 112.5(3) . . ?
F6 C3 C2 113.3(3) . . ?
C2 C7 C8 124.3(3) . . ?
C2 C7 H7 117.8 . . ?
C8 C7 H7 117.8 . . ?
N9 C8 C7 121.9(3) . . ?
N9 C8 C11 123.2(2) . . ?
C7 C8 C11 114.7(2) . . ?
C8 N9 C10 121.5(2) . . ?
C8 N9 Cu1 126.14(19) . . ?
C10 N9 Cu1 112.26(16) . . ?
N9 C10 C10 108.65(17) . 2_656 ?
N9 C10 H10A 110.0 . . ?
C10 C10 H10A 110.0 2_656 . ?
N9 C10 H10B 110.0 . . ?
C10 C10 H10B 110.0 2_656 . ?
H10A C10 H10B 108.3 . . ?
C16 C11 C12 119.1(3) . . ?
C16 C11 C8 119.5(2) . . ?
C12 C11 C8 120.9(3) . . ?
C13 C12 C11 120.4(3) . . ?
C13 C12 H12 119.8 . . ?
C11 C12 H12 119.8 . . ?
C14 C13 C12 119.3(3) . . ?
C14 C13 H13 120.3 . . ?
C12 C13 H13 120.3 . . ?
C13 C14 C15 121.4(3) . . ?
C13 C14 Br1 120.0(2) . . ?
C15 C14 Br1 118.5(2) . . ?
C14 C15 C16 118.8(3) . . ?
C14 C15 H15 120.6 . . ?
C16 C15 H15 120.6 . . ?
C11 C16 C15 120.9(3) . . ?
C11 C16 H16 119.6 . . ?
C15 C16 H16 119.6 . . ?
O1 Cu1 O1 84.85(12) 2_656 . ?
O1 Cu1 N9 178.69(10) 2_656 . ?
O1 Cu1 N9 94.62(9) . . ?
O1 Cu1 N9 94.62(9) 2_656 2_656 ?
O1 Cu1 N9 178.69(10) . 2_656 ?
N9 Cu1 N9 85.95(13) . 2_656 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C2 1.283(3) . ?
O1 Cu1 1.910(2) . ?
C2 C7 1.360(4) . ?
C2 C3 1.521(4) . ?
C3 F5 1.308(4) . ?
C3 F4 1.324(4) . ?
C3 F6 1.333(4) . ?
C7 C8 1.430(4) . ?
C7 H7 0.9500 . ?
C8 N9 1.311(3) . ?
C8 C11 1.499(4) . ?
N9 C10 1.478(3) . ?
N9 Cu1 1.936(2) . ?
C10 C10 1.533(5) 2_656 ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 C16 1.385(4) . ?
C11 C12 1.395(4) . ?
C12 C13 1.383(4) . ?
C12 H12 0.9500 . ?
C13 C14 1.377(4) . ?
C13 H13 0.9500 . ?
C14 C15 1.382(4) . ?
C14 Br1 1.897(3) . ?
C15 C16 1.386(4) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?
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_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Cu1 O1 C2 C7 -3.5(5) . . . . ?
Cu1 O1 C2 C3 -179.9(2) . . . . ?
O1 C2 C3 F5 69.1(4) . . . . ?
C7 C2 C3 F5 -107.8(3) . . . . ?
O1 C2 C3 F4 -52.0(4) . . . . ?
C7 C2 C3 F4 131.1(3) . . . . ?
O1 C2 C3 F6 -170.7(3) . . . . ?
C7 C2 C3 F6 12.5(4) . . . . ?
O1 C2 C7 C8 -6.8(5) . . . . ?
C3 C2 C7 C8 169.4(3) . . . . ?
C2 C7 C8 N9 9.2(5) . . . . ?
C2 C7 C8 C11 -165.9(3) . . . . ?
C7 C8 N9 C10 -176.9(3) . . . . ?
C11 C8 N9 C10 -2.3(4) . . . . ?
C7 C8 N9 Cu1 -1.3(4) . . . . ?
C11 C8 N9 Cu1 173.34(19) . . . . ?
C8 N9 C10 C10 -154.0(3) . . . 2_656 ?
Cu1 N9 C10 C10 29.8(3) . . . 2_656 ?
N9 C8 C11 C16 -62.2(4) . . . . ?
C7 C8 C11 C16 112.8(3) . . . . ?
N9 C8 C11 C12 125.9(3) . . . . ?
C7 C8 C11 C12 -59.0(4) . . . . ?
C16 C11 C12 C13 -0.8(4) . . . . ?
C8 C11 C12 C13 171.1(3) . . . . ?
C11 C12 C13 C14 -0.9(5) . . . . ?
C12 C13 C14 C15 2.0(5) . . . . ?
C12 C13 C14 Br1 -177.0(2) . . . . ?
C13 C14 C15 C16 -1.4(5) . . . . ?
Br1 C14 C15 C16 177.6(2) . . . . ?
C12 C11 C16 C15 1.5(4) . . . . ?
C8 C11 C16 C15 -170.5(3) . . . . ?
C14 C15 C16 C11 -0.4(4) . . . . ?
