#------------------------------------------------------------------------------
#$Date: 2022-08-18 03:13:29 +0200 (Thu 18 de Aug de 2022) $
#$Revision: 277301 $
#$URL: svn://www.crystallography.net/cod/cif/7/24/53/7245356.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_7245356
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         'C18 H12 Cl Cu F3 N2 O2 S'
_chemical_formula_sum            'C18 H12 Cl Cu F3 N2 O2 S'
_chemical_formula_weight         476.35
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   iterative
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2021-01-15 deposited with the CCDC.	2022-08-02 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 106.899(13)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.023(6)
_cell_length_b                   8.377(4)
_cell_length_c                   17.040(7)
_cell_measurement_reflns_used    9982
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      26.91
_cell_measurement_theta_min      2.50
_cell_volume                     1778.7(14)
_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 1.000
_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  0.0254
_diffrn_reflns_av_unetI/netI     0.0086
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            64883
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.000
_diffrn_reflns_theta_min         1.634
_diffrn_source                   'rotating anode (Nonius FR-591)'
_exptl_absorpt_coefficient_mu    1.543
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.6300
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SadAbs 2014/5 (Bruker AXS)'
_exptl_crystal_colour            green
_exptl_crystal_density_diffrn    1.779
_exptl_crystal_description       block
_exptl_crystal_F_000             956
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: Methanol/diethylether'
_exptl_crystal_size_max          0.500
_exptl_crystal_size_mid          0.450
_exptl_crystal_size_min          0.400
_refine_diff_density_max         0.710
_refine_diff_density_min         -0.626
_refine_diff_density_rms         0.064
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     283
_refine_ls_number_reflns         3500
_refine_ls_number_restraints     58
_refine_ls_restrained_S_all      1.182
_refine_ls_R_factor_all          0.0261
_refine_ls_R_factor_gt           0.0249
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0275P)²+2.7644P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0618
_refine_ls_wR_factor_ref         0.0629
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3350
_reflns_number_total             3500
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d2ra02428d2.cif
_cod_data_source_block           cmpd4_CuTTAbipyCl
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7245356
_shelx_shelxl_version_number     2018/3
_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   0.512
_shelx_estimated_absorpt_t_max   0.577
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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
Cu1 Cu 0.24073(2) 0.53148(3) 0.43355(2) 0.01129(8) Uani 1 1 d . . . . .
Cl1 Cl 0.13392(3) 0.76737(5) 0.37132(3) 0.01487(10) Uani 1 1 d . . . . .
F1A F 0.3476(4) 0.2813(4) 0.2317(2) 0.0243(7) Uani 0.772(11) 1 d . U P A 3
F2A F 0.3059(4) 0.5139(5) 0.17732(19) 0.0315(8) Uani 0.772(11) 1 d . U P A 3
F3A F 0.4718(3) 0.4490(6) 0.2304(2) 0.0317(8) Uani 0.772(11) 1 d . U P A 3
F2B F 0.2794(9) 0.4688(15) 0.1807(7) 0.0273(15) Uani 0.228(11) 1 d . U P A 4
F3B F 0.4474(10) 0.5053(16) 0.2161(6) 0.0314(14) Uani 0.228(11) 1 d . U P A 4
F1B F 0.3820(10) 0.2893(19) 0.2401(9) 0.0266(15) Uani 0.228(11) 1 d . U P A 4
O1 O 0.27917(10) 0.46242(16) 0.33661(8) 0.0155(3) Uani 1 1 d . . . . .
O2 O 0.37753(10) 0.63932(16) 0.47883(8) 0.0150(3) Uani 1 1 d . . . . .
N1 N 0.12423(12) 0.36781(18) 0.41355(9) 0.0118(3) Uani 1 1 d . . . . .
N2 N 0.21794(13) 0.52988(18) 0.54524(9) 0.0127(3) Uani 1 1 d . . . . .
C1 C 0.37295(16) 0.4377(2) 0.24026(12) 0.0161(4) Uani 1 1 d . . . . .
C2 C 0.36549(15) 0.5037(2) 0.32198(11) 0.0135(4) Uani 1 1 d . . . . .
C3 C 0.44830(15) 0.5974(2) 0.36702(11) 0.0151(4) Uani 1 1 d . . . . .
H3 H 0.506186 0.620245 0.345381 0.018 Uiso 1 1 calc R U . . .
C4 C 0.45064(14) 0.6613(2) 0.44473(11) 0.0129(4) Uani 1 1 d . . . . .
C5 C 0.54000(14) 0.7600(2) 0.49030(10) 0.0146(4) Uani 1 1 d D . . . .
C7 C 0.69816(16) 0.9175(2) 0.52801(14) 0.0275(5) Uani 1 1 d D . . . .
H7A H 0.763078 0.965465 0.525160 0.033 Uiso 0.7855(16) 1 calc R U P B 1
H7B H 0.764102 0.967216 0.529049 0.033 Uiso 0.2145(16) 1 calc R U P B 2
C8 C 0.65037(17) 0.9431(2) 0.58767(14) 0.0271(5) Uani 1 1 d D . . . .
H8A H 0.680481 1.011906 0.632812 0.033 Uiso 0.7855(16) 1 calc R U P B 1
H8B H 0.674524 1.010635 0.634186 0.033 Uiso 0.2145(16) 1 calc R U P B 2
C9 C 0.08215(15) 0.2894(2) 0.34312(11) 0.0145(4) Uani 1 1 d . . . . .
H9 H 0.107231 0.313377 0.297378 0.017 Uiso 1 1 calc R U . . .
C10 C 0.00323(15) 0.1745(2) 0.33468(12) 0.0168(4) Uani 1 1 d . . . . .
H10 H -0.025187 0.119756 0.284168 0.020 Uiso 1 1 calc R U . . .
C11 C -0.03326(15) 0.1411(2) 0.40141(12) 0.0169(4) Uani 1 1 d . . . . .
H11 H -0.086984 0.062209 0.397250 0.020 Uiso 1 1 calc R U . . .
C12 C 0.00874(15) 0.2231(2) 0.47448(11) 0.0145(4) Uani 1 1 d . . . . .
H12 H -0.016321 0.202560 0.520592 0.017 Uiso 1 1 calc R U . . .
C13 C 0.08824(14) 0.3359(2) 0.47860(11) 0.0115(3) Uani 1 1 d . . . . .
C14 C 0.14078(14) 0.4293(2) 0.55326(11) 0.0117(3) Uani 1 1 d . . . . .
C15 C 0.11383(15) 0.4171(2) 0.62618(11) 0.0142(4) Uani 1 1 d . . . . .
H15 H 0.058885 0.346160 0.630660 0.017 Uiso 1 1 calc R U . . .
C16 C 0.16884(16) 0.5105(2) 0.69236(12) 0.0168(4) Uani 1 1 d . . . . .
H16 H 0.151778 0.504590 0.742827 0.020 Uiso 1 1 calc R U . . .
C17 C 0.24876(16) 0.6125(2) 0.68412(11) 0.0176(4) Uani 1 1 d . . . . .
H17 H 0.287730 0.676533 0.728888 0.021 Uiso 1 1 calc R U . . .
C18 C 0.27090(15) 0.6193(2) 0.60942(11) 0.0166(4) Uani 1 1 d . . . . .
H18 H 0.325375 0.689717 0.603528 0.020 Uiso 1 1 calc R U . . .
S1A S 0.53814(5) 0.84836(10) 0.57705(4) 0.01225(15) Uani 0.7855(16) 1 d D U P B
1
C6A C 0.6367(3) 0.8094(5) 0.4715(2) 0.01225(15) Uani 0.7855(16) 1 d D . P B 1
H6A H 0.656235 0.771881 0.425222 0.015 Uiso 0.7855(16) 1 calc R U P B 1
S1B S 0.6404(3) 0.8044(4) 0.45893(17) 0.01225(15) Uani 0.2145(16) 1 d D U P B 2
C6B C 0.5575(8) 0.8483(16) 0.5660(6) 0.01225(15) Uani 0.2145(16) 1 d D U P B 2
H6B H 0.509639 0.842572 0.598656 0.015 Uiso 0.2145(16) 1 calc R U P B 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'
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'
S S 0.1246 0.1234 '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'
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
O2 Cu1 O1 92.45(6) . . ?
O2 Cu1 N1 161.43(6) . . ?
O1 Cu1 N1 91.21(6) . . ?
O2 Cu1 N2 89.87(6) . . ?
O1 Cu1 N2 161.11(6) . . ?
N1 Cu1 N2 80.98(6) . . ?
O2 Cu1 Cl1 97.77(5) . . ?
O1 Cu1 Cl1 97.18(5) . . ?
N1 Cu1 Cl1 99.83(6) . . ?
N2 Cu1 Cl1 101.08(5) . . ?
C2 O1 Cu1 123.14(12) . . ?
C4 O2 Cu1 127.60(12) . . ?
C9 N1 C13 119.34(16) . . ?
C9 N1 Cu1 125.61(13) . . ?
C13 N1 Cu1 115.04(12) . . ?
C18 N2 C14 119.26(16) . . ?
C18 N2 Cu1 125.92(13) . . ?
C14 N2 Cu1 114.82(12) . . ?
F1B C1 F3B 110.9(7) . . ?
F2A C1 F1A 107.2(2) . . ?
F2A C1 F3A 106.9(2) . . ?
F1A C1 F3A 105.5(2) . . ?
F1B C1 F2B 104.7(7) . . ?
F3B C1 F2B 105.7(6) . . ?
F1B C1 C2 113.1(7) . . ?
F3B C1 C2 112.7(5) . . ?
F2A C1 C2 111.1(2) . . ?
F1A C1 C2 111.8(2) . . ?
F3A C1 C2 113.83(19) . . ?
F2B C1 C2 109.2(5) . . ?
O1 C2 C3 130.01(18) . . ?
O1 C2 C1 112.04(16) . . ?
C3 C2 C1 117.94(17) . . ?
C2 C3 C4 122.47(17) . . ?
C2 C3 H3 118.8 . . ?
C4 C3 H3 118.8 . . ?
O2 C4 C3 123.94(17) . . ?
O2 C4 C5 115.46(16) . . ?
C3 C4 C5 120.60(16) . . ?
C6B C5 C4 131.4(3) . . ?
C6A C5 C4 131.08(19) . . ?
C6B C5 S1B 104.3(3) . . ?
C4 C5 S1B 124.10(17) . . ?
C6A C5 S1A 107.97(17) . . ?
C4 C5 S1A 120.83(13) . . ?
C8 C7 C6A 108.9(2) . . ?
C8 C7 S1B 116.45(19) . . ?
C8 C7 H7A 125.5 . . ?
C6A C7 H7A 125.5 . . ?
C8 C7 H7B 121.8 . . ?
S1B C7 H7B 121.8 . . ?
C7 C8 C6B 105.2(3) . . ?
C7 C8 S1A 115.68(16) . . ?
C7 C8 H8A 122.2 . . ?
S1A C8 H8A 122.2 . . ?
C7 C8 H8B 127.4 . . ?
C6B C8 H8B 127.4 . . ?
N1 C9 C10 122.18(17) . . ?
N1 C9 H9 118.9 . . ?
C10 C9 H9 118.9 . . ?
C11 C10 C9 118.50(17) . . ?
C11 C10 H10 120.7 . . ?
C9 C10 H10 120.7 . . ?
C10 C11 C12 119.87(18) . . ?
C10 C11 H11 120.1 . . ?
C12 C11 H11 120.1 . . ?
C11 C12 C13 118.42(18) . . ?
C11 C12 H12 120.8 . . ?
C13 C12 H12 120.8 . . ?
N1 C13 C12 121.68(17) . . ?
N1 C13 C14 114.63(16) . . ?
C12 C13 C14 123.69(17) . . ?
N2 C14 C15 121.74(17) . . ?
N2 C14 C13 114.52(16) . . ?
C15 C14 C13 123.74(17) . . ?
C16 C15 C14 118.67(18) . . ?
C16 C15 H15 120.7 . . ?
C14 C15 H15 120.7 . . ?
C17 C16 C15 119.40(18) . . ?
C17 C16 H16 120.3 . . ?
C15 C16 H16 120.3 . . ?
C16 C17 C18 118.81(18) . . ?
C16 C17 H17 120.6 . . ?
C18 C17 H17 120.6 . . ?
N2 C18 C17 122.11(18) . . ?
N2 C18 H18 118.9 . . ?
C17 C18 H18 118.9 . . ?
C8 S1A C5 94.09(11) . . ?
C7 C6A C5 113.3(3) . . ?
C7 C6A H6A 123.4 . . ?
C5 C6A H6A 123.4 . . ?
C7 S1B C5 98.90(16) . . ?
C8 C6B C5 115.1(5) . . ?
C8 C6B H6B 122.4 . . ?
C5 C6B H6B 122.4 . . ?
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 O2 1.9458(15) . ?
Cu1 O1 1.9480(15) . ?
Cu1 N1 1.9993(17) . ?
Cu1 N2 2.0096(17) . ?
Cu1 Cl1 2.4712(10) . ?
F1A C1 1.348(4) . ?
F2A C1 1.332(4) . ?
F3A C1 1.349(3) . ?
F2B C1 1.365(11) . ?
F3B C1 1.289(10) . ?
F1B C1 1.249(16) . ?
O1 C2 1.268(2) . ?
O2 C4 1.265(2) . ?
N1 C9 1.338(2) . ?
N1 C13 1.350(2) . ?
N2 C18 1.340(2) . ?
N2 C14 1.348(2) . ?
C1 C2 1.527(3) . ?
C2 C3 1.373(3) . ?
C3 C4 1.421(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.454(3) . ?
C5 C6B 1.446(6) . ?
C5 C6A 1.447(4) . ?
C5 S1B 1.593(3) . ?
C5 S1A 1.6599(19) . ?
C7 C8 1.355(4) . ?
C7 C6A 1.393(4) . ?
C7 S1B 1.528(3) . ?
C7 H7A 0.9500 . ?
C7 H7B 0.9500 . ?
C8 C6B 1.403(5) . ?
C8 S1A 1.626(2) . ?
C8 H8A 0.9500 . ?
C8 H8B 0.9500 . ?
C9 C10 1.385(3) . ?
C9 H9 0.9500 . ?
C10 C11 1.382(3) . ?
C10 H10 0.9500 . ?
C11 C12 1.388(3) . ?
C11 H11 0.9500 . ?
C12 C13 1.388(3) . ?
C12 H12 0.9500 . ?
C13 C14 1.481(3) . ?
C14 C15 1.390(3) . ?
C15 C16 1.389(3) . ?
C15 H15 0.9500 . ?
C16 C17 1.385(3) . ?
C16 H16 0.9500 . ?
C17 C18 1.386(3) . ?
C17 H17 0.9500 . ?
C18 H18 0.9500 . ?
C6A H6A 0.9500 . ?
C6B H6B 0.9500 . ?
