#------------------------------------------------------------------------------
#$Date: 2022-08-18 03:13:29 +0200 (Thu 18 de Aug de 2022) $
#$Revision: 277301 $
#$URL: svn://www.crystallography.net/cod/cif/7/24/53/7245351.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_7245351
loop_
_publ_author_name
'Omoregie, Helen Oluwatola'
'Oloba-Whenu, Oluwakemi A.'
'Olowu, Olawale J.'
'Fasina, Tolulope M.'
'Friedrich, Alexandra'
'Haehnel, Martin'
'Marder, Todd B.'
_publ_section_title
;
 Mixed-ligand complexes of copper(ii) with thienoyltrifluoroacetonate and
 nitrogen containing ligands: synthesis, structures, antimicrobial
 activity, cytotoxicity, Hirshfeld surface analysis and DFT studies
;
_journal_issue                   36
_journal_name_full               'RSC Advances'
_journal_page_first              23513
_journal_page_last               23526
_journal_paper_doi               10.1039/D2RA02428D
_journal_volume                  12
_journal_year                    2022
_chemical_formula_moiety         'C20 H12 Cu F3 N3 O5 S'
_chemical_formula_sum            'C20 H12 Cu F3 N3 O5 S'
_chemical_formula_weight         526.93
_space_group_crystal_system      triclinic
_space_group_IT_number           1
_space_group_name_Hall           'P 1'
_space_group_name_H-M_alt        'P 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_secondary   iterative
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2021-01-15 deposited with the CCDC.	2022-08-02 downloaded from the CCDC.
;
_cell_angle_alpha                95.380(2)
_cell_angle_beta                 108.445(2)
_cell_angle_gamma                110.266(2)
_cell_formula_units_Z            1
_cell_length_a                   7.6341(4)
_cell_length_b                   7.7048(4)
_cell_length_c                   9.5687(4)
_cell_measurement_reflns_used    7182
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      28.75
_cell_measurement_theta_min      2.30
_cell_volume                     487.61(4)
_computing_cell_refinement       'Saint+ ver. V8.34A (Bruker AXS)'
_computing_data_collection       'APEX2 ver. 2014.9 (Bruker AXS)'
_computing_data_reduction        'Saint+ ver. V8.34A (Bruker AXS)'
_computing_molecular_graphics    'ShelXLe (Huebschle et all, 2011)'
_computing_publication_material  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXT (Sheldrick, 2012)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'CCD area detector (Apex2)'
_diffrn_detector_area_resol_mean 8.333
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker X8-APEX II'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0219
_diffrn_reflns_av_unetI/netI     0.0252
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            10769
_diffrn_reflns_point_group_measured_fraction_full 0.831
_diffrn_reflns_point_group_measured_fraction_max 0.805
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.992
_diffrn_reflns_theta_min         2.305
_diffrn_source                   'rotating anode (Nonius FR-591)'
_exptl_absorpt_coefficient_mu    1.297
_exptl_absorpt_correction_T_max  0.7458
_exptl_absorpt_correction_T_min  0.6801
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SadAbs 2014/5 (Bruker AXS)'
_exptl_crystal_colour            green
_exptl_crystal_density_diffrn    1.794
_exptl_crystal_description       block
_exptl_crystal_F_000             265
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: Methanol/diethylether'
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.200
_refine_diff_density_max         0.251
_refine_diff_density_min         -0.241
_refine_diff_density_rms         0.051
_refine_ls_abs_structure_details
;
 Flack x determined using 1229 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.011(5)
_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     298
_refine_ls_number_reflns         3411
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.056
_refine_ls_R_factor_all          0.0220
_refine_ls_R_factor_gt           0.0211
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0269P)²+0.1082P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0494
_refine_ls_wR_factor_ref         0.0498
_reflns_Friedel_coverage         0.611
_reflns_Friedel_fraction_full    0.662
_reflns_Friedel_fraction_max     0.611
_reflns_number_gt                3339
_reflns_number_total             3411
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d2ra02428d2.cif
_cod_data_source_block           cmpd1_CuTTAphenNO3
_cod_database_code               7245351
_shelx_shelxl_version_number     2014/7
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_min   0.781
_shelx_estimated_absorpt_t_max   0.781
loop_
_space_group_symop_operation_xyz
'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_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
Cu1 Cu 0.21808(3) 0.22447(3) 0.32236(3) 0.01204(10) Uani 1 1 d . . . . .
S1 S 0.76371(12) 0.75790(12) 0.68051(9) 0.01783(19) Uani 1 1 d . . . . .
F1 F 0.1310(3) 0.7102(3) -0.0071(2) 0.0231(4) Uani 1 1 d . . . . .
F2 F 0.2036(3) 0.4906(3) -0.0993(2) 0.0235(4) Uani 1 1 d . . . . .
F3 F -0.0854(3) 0.4200(3) -0.0821(2) 0.0218(4) Uani 1 1 d . . . . .
O1 O 0.4157(4) 0.4701(3) 0.4442(3) 0.0149(5) Uani 1 1 d . . . . .
O2 O 0.1033(3) 0.3272(3) 0.1576(3) 0.0137(5) Uani 1 1 d . . . . .
O3 O 0.4434(3) 0.1419(4) 0.2619(2) 0.0207(5) Uani 1 1 d . . . . .
O4 O 0.5617(4) 0.0481(4) 0.1071(3) 0.0306(6) Uani 1 1 d . . . . .
O5 O 0.3363(4) 0.1638(4) 0.0280(3) 0.0231(5) Uani 1 1 d . . . . .
N1 N -0.0016(4) -0.0340(4) 0.2280(3) 0.0127(7) Uani 1 1 d . . . . .
N2 N 0.2858(4) 0.1059(4) 0.5004(3) 0.0134(6) Uani 1 1 d . . . . .
N3 N 0.4459(4) 0.1160(4) 0.1300(3) 0.0141(6) Uani 1 1 d . . . . .
C1 C 0.0136(5) -0.1592(5) 0.3174(4) 0.0115(6) Uani 1 1 d . . . . .
C2 C -0.1153(5) -0.3509(5) 0.2733(4) 0.0161(7) Uani 1 1 d . . . . .
C3 C -0.2687(5) -0.4136(5) 0.1287(4) 0.0176(7) Uani 1 1 d . . . . .
H3 H -0.3604 -0.5431 0.0929 0.021 Uiso 1 1 calc R U . . .
C4 C -0.2843(5) -0.2855(5) 0.0398(4) 0.0180(7) Uani 1 1 d . . . . .
H4 H -0.3885 -0.3258 -0.0575 0.022 Uiso 1 1 calc R U . . .
C5 C -0.1470(5) -0.0963(5) 0.0924(4) 0.0156(7) Uani 1 1 d . . . . .
H5 H -0.1583 -0.0098 0.0290 0.019 Uiso 1 1 calc R U . . .
C6 C 0.1701(5) -0.0821(5) 0.4651(4) 0.0125(7) Uani 1 1 d . . . . .
C7 C 0.1948(5) -0.2007(5) 0.5658(4) 0.0156(6) Uani 1 1 d . . . . .
C8 C 0.3458(5) -0.1139(5) 0.7103(4) 0.0187(7) Uani 1 1 d . . . . .
H8 H 0.3665 -0.1874 0.7835 0.022 Uiso 1 1 calc R U . . .
C9 C 0.4633(5) 0.0764(5) 0.7458(4) 0.0195(7) Uani 1 1 d . . . . .
H9 H 0.5660 0.1357 0.8433 0.023 Uiso 1 1 calc R U . . .
C10 C 0.4303(5) 0.1828(5) 0.6365(4) 0.0162(7) Uani 1 1 d . . . . .
H10 H 0.5142 0.3143 0.6608 0.019 Uiso 1 1 calc R U . . .
C11 C -0.0847(5) -0.4711(5) 0.3765(4) 0.0200(7) Uani 1 1 d . . . . .
H11 H -0.1689 -0.6029 0.3468 0.024 Uiso 1 1 calc R U . . .
C12 C 0.0641(5) -0.3980(5) 0.5167(4) 0.0207(7) Uani 1 1 d . . . . .
H12 H 0.0814 -0.4800 0.5833 0.025 Uiso 1 1 calc R U . . .
C13 C 0.9254(5) 0.9906(5) 0.7363(4) 0.0196(7) Uani 1 1 d . . . . .
H13 H 1.0315 1.0466 0.8326 0.024 Uiso 1 1 calc R U . . .
C14 C 0.8847(5) 1.0874(5) 0.6263(4) 0.0200(7) Uani 1 1 d . . . . .
H14 H 0.9598 1.2185 0.6372 0.024 Uiso 1 1 calc R U . . .
C15 C 0.7177(5) 0.9703(5) 0.4942(4) 0.0171(7) Uani 1 1 d . . . . .
H15 H 0.6683 1.0148 0.4068 0.021 Uiso 1 1 calc R U . . .
C16 C 0.6352(5) 0.7862(5) 0.5057(4) 0.0131(7) Uani 1 1 d . . . . .
C17 C 0.4642(5) 0.6228(5) 0.3985(4) 0.0125(7) Uani 1 1 d . . . . .
C18 C 0.3636(5) 0.6408(5) 0.2513(3) 0.0132(6) Uani 1 1 d . . . . .
H18 H 0.4139 0.7585 0.2242 0.016 Uiso 1 1 calc R U . . .
C19 C 0.1970(5) 0.4949(5) 0.1473(4) 0.0121(7) Uani 1 1 d . . . . .
C20 C 0.1101(5) 0.5302(5) -0.0108(4) 0.0149(7) 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'
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'
F F 0.0171 0.0103 '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'
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
_geom_angle_publ_flag
O1 Cu1 O2 93.59(10) . . ?
O1 Cu1 N1 169.70(11) . . ?
O2 Cu1 N1 92.12(11) . . ?
O1 Cu1 N2 90.44(11) . . ?
O2 Cu1 N2 168.58(10) . . ?
N1 Cu1 N2 82.40(12) . . ?
O1 Cu1 O3 93.52(10) . . ?
O2 Cu1 O3 104.97(9) . . ?
N1 Cu1 O3 93.27(11) . . ?
N2 Cu1 O3 85.41(10) . . ?
C13 S1 C16 92.09(17) . . ?
C17 O1 Cu1 126.0(2) . . ?
C19 O2 Cu1 121.3(2) . . ?
N3 O3 Cu1 124.75(18) . . ?
C5 N1 C1 118.5(3) . . ?
C5 N1 Cu1 128.8(2) . . ?
C1 N1 Cu1 112.5(2) . . ?
C10 N2 C6 118.7(3) . . ?
C10 N2 Cu1 129.5(2) . . ?
C6 N2 Cu1 111.6(2) . . ?
O4 N3 O5 121.7(3) . . ?
O4 N3 O3 118.7(2) . . ?
O5 N3 O3 119.6(3) . . ?
N1 C1 C2 123.4(3) . . ?
N1 C1 C6 116.0(3) . . ?
C2 C1 C6 120.6(3) . . ?
C1 C2 C3 117.0(3) . . ?
C1 C2 C11 118.8(3) . . ?
C3 C2 C11 124.2(3) . . ?
C4 C3 C2 119.2(3) . . ?
C4 C3 H3 120.4 . . ?
C2 C3 H3 120.4 . . ?
C3 C4 C5 120.0(3) . . ?
C3 C4 H4 120.0 . . ?
C5 C4 H4 120.0 . . ?
N1 C5 C4 121.8(3) . . ?
N1 C5 H5 119.1 . . ?
C4 C5 H5 119.1 . . ?
N2 C6 C7 123.2(3) . . ?
N2 C6 C1 116.9(3) . . ?
C7 C6 C1 119.8(3) . . ?
C6 C7 C8 116.6(3) . . ?
C6 C7 C12 118.6(3) . . ?
C8 C7 C12 124.7(3) . . ?
C9 C8 C7 120.1(3) . . ?
C9 C8 H8 119.9 . . ?
C7 C8 H8 119.9 . . ?
C8 C9 C10 119.2(3) . . ?
C8 C9 H9 120.4 . . ?
C10 C9 H9 120.4 . . ?
N2 C10 C9 122.1(3) . . ?
N2 C10 H10 118.9 . . ?
C9 C10 H10 118.9 . . ?
C12 C11 C2 120.6(3) . . ?
C12 C11 H11 119.7 . . ?
C2 C11 H11 119.7 . . ?
C11 C12 C7 121.5(3) . . ?
C11 C12 H12 119.3 . . ?
C7 C12 H12 119.3 . . ?
C14 C13 S1 112.0(3) . . ?
C14 C13 H13 124.0 . . ?
S1 C13 H13 124.0 . . ?
C13 C14 C15 112.4(3) . . ?
C13 C14 H14 123.8 . . ?
C15 C14 H14 123.8 . . ?
C16 C15 C14 112.8(3) . . ?
C16 C15 H15 123.6 . . ?
C14 C15 H15 123.6 . . ?
C15 C16 C17 130.6(3) . . ?
C15 C16 S1 110.7(3) . . ?
C17 C16 S1 118.7(2) . . ?
O1 C17 C18 124.1(3) . . ?
O1 C17 C16 116.4(3) . . ?
C18 C17 C16 119.5(3) . . ?
C19 C18 C17 122.4(3) . . ?
C19 C18 H18 118.8 . . ?
C17 C18 H18 118.8 . . ?
O2 C19 C18 130.1(3) . . ?
O2 C19 C20 112.9(3) . . ?
C18 C19 C20 116.9(3) . . ?
F3 C20 F1 107.4(3) . . ?
F3 C20 F2 106.5(3) . . ?
F1 C20 F2 106.8(3) . . ?
F3 C20 C19 112.2(3) . . ?
F1 C20 C19 112.9(3) . . ?
F2 C20 C19 110.7(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
Cu1 O1 1.927(2) . ?
Cu1 O2 1.929(2) . ?
Cu1 N1 1.996(3) . ?
Cu1 N2 2.017(3) . ?
Cu1 O3 2.241(2) . ?
S1 C13 1.701(4) . ?
S1 C16 1.728(3) . ?
F1 C20 1.336(4) . ?
F2 C20 1.343(4) . ?
F3 C20 1.336(4) . ?
O1 C17 1.269(4) . ?
O2 C19 1.272(4) . ?
O3 N3 1.266(3) . ?
O4 N3 1.234(3) . ?
O5 N3 1.246(3) . ?
N1 C5 1.323(5) . ?
N1 C1 1.358(4) . ?
N2 C10 1.325(4) . ?
N2 C6 1.351(5) . ?
C1 C2 1.393(5) . ?
C1 C6 1.435(5) . ?
C2 C3 1.406(5) . ?
C2 C11 1.436(4) . ?
C3 C4 1.373(5) . ?
C3 H3 0.9500 . ?
C4 C5 1.396(5) . ?
C4 H4 0.9500 . ?
C5 H5 0.9500 . ?
C6 C7 1.403(4) . ?
C7 C8 1.404(5) . ?
C7 C12 1.430(5) . ?
C8 C9 1.368(5) . ?
C8 H8 0.9500 . ?
C9 C10 1.403(4) . ?
C9 H9 0.9500 . ?
C10 H10 0.9500 . ?
C11 C12 1.363(5) . ?
C11 H11 0.9500 . ?
C12 H12 0.9500 . ?
C13 C14 1.364(5) . ?
C13 H13 0.9500 . ?
C14 C15 1.417(5) . ?
C14 H14 0.9500 . ?
C15 C16 1.369(5) . ?
C15 H15 0.9500 . ?
C16 C17 1.454(5) . ?
C17 C18 1.421(4) . ?
C18 C19 1.368(5) . ?
C18 H18 0.9500 . ?
C19 C20 1.539(4) . ?
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 O3 N3 O4 -171.1(2) . . . . ?
Cu1 O3 N3 O5 10.7(4) . . . . ?
C5 N1 C1 C2 0.6(5) . . . . ?
Cu1 N1 C1 C2 -176.4(2) . . . . ?
C5 N1 C1 C6 -178.0(3) . . . . ?
Cu1 N1 C1 C6 5.0(3) . . . . ?
N1 C1 C2 C3 -0.6(5) . . . . ?
C6 C1 C2 C3 178.0(3) . . . . ?
N1 C1 C2 C11 179.5(3) . . . . ?
C6 C1 C2 C11 -1.9(4) . . . . ?
C1 C2 C3 C4 -0.2(5) . . . . ?
C11 C2 C3 C4 179.7(3) . . . . ?
C2 C3 C4 C5 1.0(5) . . . . ?
C1 N1 C5 C4 0.2(5) . . . . ?
Cu1 N1 C5 C4 176.6(2) . . . . ?
C3 C4 C5 N1 -1.0(5) . . . . ?
C10 N2 C6 C7 0.2(5) . . . . ?
Cu1 N2 C6 C7 176.0(2) . . . . ?
C10 N2 C6 C1 179.2(3) . . . . ?
Cu1 N2 C6 C1 -5.1(3) . . . . ?
N1 C1 C6 N2 0.1(4) . . . . ?
C2 C1 C6 N2 -178.6(3) . . . . ?
N1 C1 C6 C7 179.1(3) . . . . ?
C2 C1 C6 C7 0.4(4) . . . . ?
N2 C6 C7 C8 1.4(5) . . . . ?
C1 C6 C7 C8 -177.6(3) . . . . ?
N2 C6 C7 C12 -179.9(3) . . . . ?
C1 C6 C7 C12 1.1(4) . . . . ?
C6 C7 C8 C9 -1.5(5) . . . . ?
C12 C7 C8 C9 179.8(3) . . . . ?
C7 C8 C9 C10 0.2(5) . . . . ?
C6 N2 C10 C9 -1.6(5) . . . . ?
Cu1 N2 C10 C9 -176.6(2) . . . . ?
C8 C9 C10 N2 1.4(5) . . . . ?
C1 C2 C11 C12 1.8(5) . . . . ?
C3 C2 C11 C12 -178.0(3) . . . . ?
C2 C11 C12 C7 -0.2(5) . . . . ?
C6 C7 C12 C11 -1.3(5) . . . . ?
C8 C7 C12 C11 177.3(3) . . . . ?
C16 S1 C13 C14 -0.2(3) . . . . ?
S1 C13 C14 C15 0.4(4) . . . . ?
C13 C14 C15 C16 -0.3(4) . . . . ?
C14 C15 C16 C17 179.5(3) . . . . ?
C14 C15 C16 S1 0.2(4) . . . . ?
C13 S1 C16 C15 0.0(3) . . . . ?
C13 S1 C16 C17 -179.4(3) . . . . ?
Cu1 O1 C17 C18 7.0(4) . . . . ?
Cu1 O1 C17 C16 -172.4(2) . . . . ?
C15 C16 C17 O1 -176.5(3) . . . . ?
S1 C16 C17 O1 2.8(4) . . . . ?
C15 C16 C17 C18 4.1(5) . . . . ?
S1 C16 C17 C18 -176.5(2) . . . . ?
O1 C17 C18 C19 3.3(5) . . . . ?
C16 C17 C18 C19 -177.3(3) . . . . ?
Cu1 O2 C19 C18 -12.9(5) . . . . ?
Cu1 O2 C19 C20 164.12(19) . . . . ?
C17 C18 C19 O2 0.3(5) . . . . ?
C17 C18 C19 C20 -176.7(3) . . . . ?
O2 C19 C20 F3 27.4(4) . . . . ?
C18 C19 C20 F3 -155.1(3) . . . . ?
O2 C19 C20 F1 148.9(3) . . . . ?
C18 C19 C20 F1 -33.6(4) . . . . ?
O2 C19 C20 F2 -91.4(3) . . . . ?
C18 C19 C20 F2 86.1(4) . . . . ?
