#------------------------------------------------------------------------------
#$Date: 2023-04-13 15:19:33 +0300 (Thu, 13 Apr 2023) $
#$Revision: 282621 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/71/25/7712588.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_7712588
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         'C30 H20 F6 N2 Ni O2 S2, C H2 Cl2'
_chemical_formula_sum            'C31 H22 Cl2 F6 N2 Ni O2 S2'
_chemical_formula_weight         762.23
_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                 105.310(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   18.4962(6)
_cell_length_b                   12.7149(6)
_cell_length_c                   14.2500(6)
_cell_measurement_reflns_used    9842
_cell_measurement_temperature    170(2)
_cell_measurement_theta_max      26.48
_cell_measurement_theta_min      2.27
_cell_measurement_wavelength     0.71073
_cell_volume                     3232.3(2)
_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, 2021)'
_computing_structure_refinement  'SHELXL-2018_3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      170(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker D8 QUEST CMOS'
_diffrn_measurement_method       'rotation images'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0406
_diffrn_reflns_av_unetI/netI     0.0084
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            142587
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         26.473
_diffrn_reflns_theta_min         2.274
_exptl_absorpt_coefficient_mu    0.962
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.6192
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS 2014/5'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.566
_exptl_crystal_description       block
_exptl_crystal_F_000             1544
_exptl_crystal_size_max          0.380
_exptl_crystal_size_mid          0.340
_exptl_crystal_size_min          0.230
_refine_diff_density_max         0.896
_refine_diff_density_min         -0.770
_refine_diff_density_rms         0.104
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     213
_refine_ls_number_reflns         3310
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.058
_refine_ls_R_factor_all          0.0952
_refine_ls_R_factor_gt           0.0731
_refine_ls_shift/su_max          0.039
_refine_ls_shift/su_mean         0.003
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.1012P)²+21.3528P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1845
_refine_ls_wR_factor_ref         0.2159
_reflns_number_gt                2715
_reflns_number_total             3310
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            d3dt00224a4.cif
_cod_data_source_block           dv_ga_174
_cod_original_cell_volume        3232.4(2)
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               7712588
#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
Ni1 Ni 0.500000 0.62774(6) 0.250000 0.0377(3) Uani 1 2 d S T P . .
S1 S 0.19963(9) 0.16480(14) -0.23175(11) 0.0708(5) Uani 1 1 d . . . . .
F1 F 0.4210(3) 0.8878(3) 0.0311(5) 0.1185(18) Uani 1 1 d . . . . .
F2 F 0.3155(3) 0.8188(3) -0.0334(3) 0.1047(16) Uani 1 1 d . . . . .
F3 F 0.3383(4) 0.8810(4) 0.1066(4) 0.127(2) Uani 1 1 d . . . . .
O1 O 0.45258(17) 0.7360(2) 0.1716(2) 0.0450(7) Uani 1 1 d . . . . .
N1 N 0.45661(17) 0.5221(2) 0.1638(2) 0.0336(7) Uani 1 1 d . . . . .
C15 C 0.2090(4) 0.0373(6) -0.2564(4) 0.0735(17) Uani 1 1 d . . . . .
H15 H 0.170634 -0.003047 -0.298465 0.088 Uiso 1 1 calc R U . . .
C14 C 0.2765(4) -0.0016(5) -0.2104(5) 0.0761(17) Uani 1 1 d . . . . .
H14 H 0.289400 -0.073145 -0.216366 0.091 Uiso 1 1 calc R U . . .
C13 C 0.3290(3) 0.0734(3) -0.1503(3) 0.0488(11) Uani 1 1 d . . . . .
H13 H 0.378892 0.059863 -0.113431 0.059 Uiso 1 1 calc R U . . .
C12 C 0.2885(3) 0.1739(4) -0.1587(3) 0.0458(10) Uani 1 1 d . . . . .
C9 C 0.3170(2) 0.2695(3) -0.1043(3) 0.0397(9) Uani 1 1 d . . . . .
C8 C 0.3942(3) 0.2906(4) -0.0785(3) 0.0459(10) Uani 1 1 d . . . . .
H8 H 0.427012 0.246299 -0.101819 0.055 Uiso 1 1 calc R U . . .
C7 C 0.4232(2) 0.3752(3) -0.0194(3) 0.0433(10) Uani 1 1 d . . . . .
H7 H 0.475581 0.388515 -0.002807 0.052 Uiso 1 1 calc R U . . .
C10 C 0.2705(2) 0.3380(4) -0.0721(3) 0.0412(9) Uani 1 1 d . . . . .
H10 H 0.217908 0.326280 -0.090305 0.049 Uiso 1 1 calc R U . . .
C11 C 0.2995(2) 0.4237(3) -0.0137(3) 0.0372(8) Uani 1 1 d . . . . .
H11 H 0.266533 0.470767 0.006235 0.045 Uiso 1 1 calc R U . . .
C6 C 0.3765(2) 0.4409(3) 0.0159(3) 0.0362(8) Uani 1 1 d . . . . .
C4 C 0.4053(2) 0.5322(3) 0.0806(3) 0.0341(8) Uani 1 1 d . . . . .
C3 C 0.3753(2) 0.6321(3) 0.0464(3) 0.0417(9) Uani 1 1 d . . . . .
H3 H 0.335241 0.634926 -0.011163 0.050 Uiso 1 1 calc R U . . .
C2 C 0.4010(2) 0.7234(3) 0.0917(3) 0.0411(9) Uani 1 1 d . . . . .
C1 C 0.3685(3) 0.8275(4) 0.0482(4) 0.0630(14) Uani 1 1 d . . . . .
C5 C 0.4896(2) 0.4181(3) 0.1956(3) 0.0445(10) Uani 1 1 d . . . . .
H5A H 0.534527 0.406139 0.171630 0.053 Uiso 1 1 calc R U . . .
H5B H 0.452812 0.361646 0.169841 0.053 Uiso 1 1 calc R U . . .
C16 C 0.500000 0.0478(12) 0.250000 0.144(6) Uani 1 2 d DS T P . .
H16A H 0.539333 0.001968 0.236492 0.173 Uiso 0.247(6) 1 calc R U P A 1
H16B H 0.460665 0.001972 0.263509 0.173 Uiso 0.247(6) 1 calc R U P A 1
H16D H 0.544360 0.001684 0.272144 0.173 Uiso 0.253(6) 1 calc R U P A 2
H16C H 0.455639 0.001686 0.227856 0.173 Uiso 0.253(6) 1 calc R U P A 2
Cl2 Cl 0.4598(9) 0.1264(9) 0.1444(8) 0.166(3) Uani 0.494(11) 1 d D . P A 1
Cl1 Cl 0.5101(9) 0.1185(8) 0.1523(9) 0.166(3) Uani 0.506(11) 1 d D . P A 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'
Cl Cl 0.1484 0.1585 '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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Ni Ni 0.3393 1.1124 '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'
S S 0.1246 0.1234 '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
O1 Ni1 O1 83.33(19) 2_655 . ?
O1 Ni1 N1 94.93(14) 2_655 2_655 ?
O1 Ni1 N1 175.25(14) . 2_655 ?
O1 Ni1 N1 175.25(14) 2_655 . ?
O1 Ni1 N1 94.93(14) . . ?
N1 Ni1 N1 87.15(19) 2_655 . ?
C15 S1 C12 93.3(3) . . ?
C2 O1 Ni1 124.5(3) . . ?
C4 N1 C5 120.4(3) . . ?
C4 N1 Ni1 127.6(3) . . ?
C5 N1 Ni1 112.0(2) . . ?
C14 C15 S1 112.9(5) . . ?
C14 C15 H15 123.6 . . ?
S1 C15 H15 123.6 . . ?
C15 C14 C13 115.6(6) . . ?
C15 C14 H14 122.2 . . ?
C13 C14 H14 122.2 . . ?
C14 C13 C12 105.9(5) . . ?
C14 C13 H13 127.0 . . ?
C12 C13 H13 127.0 . . ?
C9 C12 C13 125.1(4) . . ?
C9 C12 S1 122.3(4) . . ?
C13 C12 S1 112.3(3) . . ?
C10 C9 C8 118.1(4) . . ?
C10 C9 C12 122.0(4) . . ?
C8 C9 C12 119.8(4) . . ?
C7 C8 C9 120.8(4) . . ?
C7 C8 H8 119.6 . . ?
C9 C8 H8 119.6 . . ?
C8 C7 C6 120.7(4) . . ?
C8 C7 H7 119.7 . . ?
C6 C7 H7 119.7 . . ?
C9 C10 C11 121.1(4) . . ?
C9 C10 H10 119.5 . . ?
C11 C10 H10 119.5 . . ?
C10 C11 C6 120.5(4) . . ?
C10 C11 H11 119.8 . . ?
C6 C11 H11 119.8 . . ?
C7 C6 C11 118.8(4) . . ?
C7 C6 C4 122.5(4) . . ?
C11 C6 C4 118.7(4) . . ?
N1 C4 C3 121.4(4) . . ?
N1 C4 C6 122.4(3) . . ?
C3 C4 C6 116.1(3) . . ?
C2 C3 C4 123.2(4) . . ?
C2 C3 H3 118.4 . . ?
C4 C3 H3 118.4 . . ?
O1 C2 C3 127.8(4) . . ?
O1 C2 C1 112.0(4) . . ?
C3 C2 C1 120.2(4) . . ?
F3 C1 F1 106.0(6) . . ?
F3 C1 F2 105.2(5) . . ?
F1 C1 F2 107.6(5) . . ?
F3 C1 C2 112.6(5) . . ?
F1 C1 C2 110.8(5) . . ?
F2 C1 C2 114.2(5) . . ?
N1 C5 C5 106.9(3) . 2_655 ?
N1 C5 H5A 110.3 . . ?
C5 C5 H5A 110.3 2_655 . ?
N1 C5 H5B 110.3 . . ?
C5 C5 H5B 110.3 2_655 . ?
H5A C5 H5B 108.6 . . ?
Cl1 C16 Cl1 116.5(12) . 2_655 ?
Cl2 C16 Cl2 112.4(12) . 2_655 ?
Cl2 C16 H16A 109.1 . . ?
Cl2 C16 H16A 109.1 2_655 . ?
Cl2 C16 H16B 109.1 . . ?
Cl2 C16 H16B 109.1 2_655 . ?
H16A C16 H16B 107.9 . . ?
Cl1 C16 H16D 108.2 . . ?
Cl1 C16 H16D 108.2 2_655 . ?
Cl1 C16 H16C 108.2 . . ?
Cl1 C16 H16C 108.2 2_655 . ?
H16D C16 H16C 107.3 . . ?
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
Ni1 O1 1.842(3) 2_655 ?
Ni1 O1 1.842(3) . ?
Ni1 N1 1.854(3) 2_655 ?
Ni1 N1 1.854(3) . ?
S1 C15 1.677(7) . ?
S1 C12 1.702(5) . ?
F1 C1 1.309(8) . ?
F2 C1 1.314(7) . ?
F3 C1 1.309(8) . ?
O1 C2 1.288(5) . ?
N1 C4 1.314(5) . ?
N1 C5 1.477(5) . ?
C15 C14 1.342(9) . ?
C15 H15 0.9500 . ?
C14 C13 1.465(7) . ?
C14 H14 0.9500 . ?
C13 C12 1.469(7) . ?
C13 H13 0.9500 . ?
C12 C9 1.463(6) . ?
C9 C10 1.385(6) . ?
C9 C8 1.403(6) . ?
C8 C7 1.384(6) . ?
C8 H8 0.9500 . ?
C7 C6 1.387(6) . ?
C7 H7 0.9500 . ?
C10 C11 1.390(6) . ?
C10 H10 0.9500 . ?
C11 C6 1.392(5) . ?
C11 H11 0.9500 . ?
C6 C4 1.492(5) . ?
C4 C3 1.420(5) . ?
C3 C2 1.352(6) . ?
C3 H3 0.9500 . ?
C2 C1 1.516(6) . ?
C5 C5 1.496(9) 2_655 ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C16 Cl1 1.708(12) . ?
C16 Cl1 1.708(12) 2_655 ?
C16 Cl2 1.795(13) . ?
C16 Cl2 1.795(13) 2_655 ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C16 H16D 0.9900 . ?
C16 H16C 0.9900 . ?
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
O1 Ni1 O1 C2 -177.1(4) 2_655 . . . ?
N1 Ni1 O1 C2 7.3(4) . . . . ?
O1 Ni1 N1 C4 -4.6(4) . . . . ?
N1 Ni1 N1 C4 171.1(4) 2_655 . . . ?
O1 Ni1 N1 C5 172.0(3) . . . . ?
N1 Ni1 N1 C5 -12.3(2) 2_655 . . . ?
C12 S1 C15 C14 1.3(5) . . . . ?
S1 C15 C14 C13 -1.4(8) . . . . ?
C15 C14 C13 C12 0.7(7) . . . . ?
C14 C13 C12 C9 174.7(4) . . . . ?
C14 C13 C12 S1 0.2(5) . . . . ?
C15 S1 C12 C9 -175.5(4) . . . . ?
C15 S1 C12 C13 -0.8(4) . . . . ?
C13 C12 C9 C10 -144.2(5) . . . . ?
S1 C12 C9 C10 29.7(6) . . . . ?
C13 C12 C9 C8 32.0(6) . . . . ?
S1 C12 C9 C8 -154.1(4) . . . . ?
C10 C9 C8 C7 2.4(6) . . . . ?
C12 C9 C8 C7 -173.9(4) . . . . ?
C9 C8 C7 C6 0.2(7) . . . . ?
C8 C9 C10 C11 -1.7(6) . . . . ?
C12 C9 C10 C11 174.5(4) . . . . ?
C9 C10 C11 C6 -1.6(6) . . . . ?
C8 C7 C6 C11 -3.6(6) . . . . ?
C8 C7 C6 C4 179.3(4) . . . . ?
C10 C11 C6 C7 4.3(6) . . . . ?
C10 C11 C6 C4 -178.5(3) . . . . ?
C5 N1 C4 C3 -177.1(4) . . . . ?
Ni1 N1 C4 C3 -0.7(6) . . . . ?
C5 N1 C4 C6 1.6(6) . . . . ?
Ni1 N1 C4 C6 178.0(3) . . . . ?
C7 C6 C4 N1 -56.7(6) . . . . ?
C11 C6 C4 N1 126.2(4) . . . . ?
C7 C6 C4 C3 122.0(4) . . . . ?
C11 C6 C4 C3 -55.1(5) . . . . ?
N1 C4 C3 C2 5.5(7) . . . . ?
C6 C4 C3 C2 -173.2(4) . . . . ?
Ni1 O1 C2 C3 -5.0(7) . . . . ?
Ni1 O1 C2 C1 175.3(3) . . . . ?
C4 C3 C2 O1 -2.6(8) . . . . ?
C4 C3 C2 C1 177.1(5) . . . . ?
O1 C2 C1 F3 -60.0(7) . . . . ?
C3 C2 C1 F3 120.2(6) . . . . ?
O1 C2 C1 F1 58.5(7) . . . . ?
C3 C2 C1 F1 -121.2(6) . . . . ?
O1 C2 C1 F2 -179.9(5) . . . . ?
C3 C2 C1 F2 0.4(8) . . . . ?
C4 N1 C5 C5 -150.0(4) . . . 2_655 ?
Ni1 N1 C5 C5 33.1(5) . . . 2_655 ?
