#------------------------------------------------------------------------------
#$Date: 2024-12-14 04:55:05 +0200 (Sat, 14 Dec 2024) $
#$Revision: 296872 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/02/33/2023333.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2023333
loop_
_publ_author_name
'Le Thi Hong, Hai'
'Nguyen Van, Hau'
'Hoang Tuan, Duong'
'Tran Quang, Hung'
'Dang Thanh, Tuan'
'Van Meervelt, Luc'
_publ_section_title
;
 Syntheses, structures and anticancer activities of CuII and ZnII
 complexes containing
 1,1′-[(3-fluorophenyl)methylene]bis[3-(3-fluorophenyl)imidazo[1,5-a]pyridine]
;
_journal_coeditor_code           WM5742
_journal_issue                   1
_journal_name_full
'Acta Crystallographica Section E Crystallographic Communications'
_journal_paper_doi               10.1107/S2056989024011617
_journal_volume                  81
_journal_year                    2025
_chemical_formula_iupac          '[Cu Cl2 (C33 H21 F3 N4)]'
_chemical_formula_moiety         'C33 H21 Cl2 Cu F3 N4'
_chemical_formula_sum            'C33 H21 Cl2 Cu F3 N4'
_chemical_formula_weight         664.98
_chemical_name_systematic
Dichlorido{1,1'-[(3-fluorophenyl)methylene]bis[3-(3-fluorophenyl)imidazo[1,5-a]pyridine]-κ²N,N'}copper(II)
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_cell_angle_alpha                104.272(2)
_cell_angle_beta                 99.186(2)
_cell_angle_gamma                101.529(2)
_cell_formula_units_Z            2
_cell_length_a                   9.3994(2)
_cell_length_b                   10.8016(3)
_cell_length_c                   15.2355(4)
_cell_measurement_reflns_used    12271
_cell_measurement_temperature    294(2)
_cell_measurement_theta_max      26.4330
_cell_measurement_theta_min      2.6180
_cell_volume                     1432.86(7)
_computing_cell_refinement
;
CrysAlisPro (Rigaku OD, 2023)
;
_computing_data_collection
;
CrysAlisPro (Rigaku OD, 2023)
;
_computing_data_reduction
;
CrysAlisPro (Rigaku OD, 2023)
;
_computing_molecular_graphics
;
Olex2 (Dolomanov et al.,  2009)
;
_computing_publication_material
;
Olex2 (Dolomanov et al.,  2009)
;
_computing_structure_refinement
;
SHELXL (Sheldrick, 2015b)
;
_computing_structure_solution
;
SHELXT (Sheldrick, 2015a)
;
_diffrn_ambient_temperature      294(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 15.9631
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Single source at offset/far, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0326
_diffrn_reflns_av_unetI/netI     0.0273
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            29600
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.370
_diffrn_reflns_theta_min         2.393
_diffrn_source                   'micro-focus sealed X-ray tube'
_exptl_absorpt_coefficient_mu    1.000
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.74149
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(CrysAlisPro; Rigaku OD, 2023)
;
_exptl_crystal_colour            green
_exptl_crystal_density_diffrn    1.541
_exptl_crystal_description       plate
_exptl_crystal_F_000             674
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.726
_refine_diff_density_min         -0.420
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.070
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     388
_refine_ls_number_reflns         5864
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.070
_refine_ls_R_factor_all          0.0451
_refine_ls_R_factor_gt           0.0352
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0333P)²+0.9126P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0827
_refine_ls_wR_factor_ref         0.0889
_reflns_number_gt                4963
_reflns_number_total             5864
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            wm5742.cif
_cod_data_source_block           I
_cod_original_cell_volume        1432.87(7)
_cod_database_code               2023333
_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   0.754
_shelx_estimated_absorpt_t_max   0.907
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu Cu1 0.35886(3) 0.61095(3) 0.72622(2) 0.03217(9) Uani d 1 . .
Cl Cl1 0.47558(8) 0.45051(7) 0.70330(6) 0.05887(19) Uani d 1 . .
F F1 0.2895(2) 0.16205(17) 0.34675(15) 0.0867(6) Uani d 1 . .
N N1 0.3092(2) 0.67074(18) 0.60887(12) 0.0326(4) Uani d 1 . .
C C1 0.2618(2) 0.5909(2) 0.52193(15) 0.0321(5) Uani d 1 . .
Cl Cl2 0.15785(7) 0.57489(7) 0.78641(5) 0.05071(17) Uani d 1 . .
F F2 -0.0417(2) 0.9011(2) 0.82735(14) 0.0835(6) Uani d 1 . .
N N2 0.26041(19) 0.66471(17) 0.46111(12) 0.0309(4) Uani d 1 . .
C C2 0.2068(3) 0.6273(2) 0.36579(15) 0.0363(5) Uani d 1 . .
H H2 0.170531 0.538609 0.332765 0.044 Uiso calc 1 . .
F F3 0.9069(3) 0.5333(2) 0.9251(2) 0.1161(9) Uani d 1 . .
N N3 0.4955(2) 0.79439(18) 0.79499(13) 0.0349(4) Uani d 1 . .
C C3 0.2079(3) 0.7207(2) 0.32181(16) 0.0406(5) Uani d 1 . .
H H3 0.170817 0.696206 0.257997 0.049 Uiso calc 1 . .
N N4 0.6629(2) 0.95568(19) 0.90043(13) 0.0369(4) Uani d 1 . .
C C4 0.2652(3) 0.8570(2) 0.37145(16) 0.0400(5) Uani d 1 . .
H H4 0.268768 0.920211 0.339433 0.048 Uiso calc 1 . .
C C5 0.3143(2) 0.8951(2) 0.46476(16) 0.0351(5) Uani d 1 . .
H H5 0.350175 0.984130 0.497013 0.042 Uiso calc 1 . .
C C6 0.3107(2) 0.7979(2) 0.51320(15) 0.0304(5) Uani d 1 . .
C C7 0.3401(2) 0.7989(2) 0.60494(15) 0.0310(5) Uani d 1 . .
C C8 0.3920(2) 0.9203(2) 0.68733(15) 0.0331(5) Uani d 1 . .
H H8 0.451210 0.987882 0.665955 0.040 Uiso calc 1 . .
C C9 0.4942(2) 0.9085(2) 0.77024(15) 0.0321(5) Uani d 1 . .
C C10 0.5982(2) 1.0114(2) 0.83562(15) 0.0345(5) Uani d 1 . .
C C11 0.6495(3) 1.1494(2) 0.85004(17) 0.0422(6) Uani d 1 . .
H H11 0.608484 1.189958 0.808583 0.051 Uiso calc 1 . .
C C12 0.7586(3) 1.2208(3) 0.92489(19) 0.0545(7) Uani d 1 . .
H H12 0.793561 1.310941 0.934285 0.065 Uiso calc 1 . .
C C13 0.8212(3) 1.1605(3) 0.9897(2) 0.0597(8) Uani d 1 . .
H H13 0.895268 1.212013 1.041211 0.072 Uiso calc 1 . .
C C14 0.7747(3) 1.0308(3) 0.97746(18) 0.0511(7) Uani d 1 . .
H H14 0.816306 0.991523 1.019597 0.061 Uiso calc 1 . .
C C15 0.5985(2) 0.8244(2) 0.87332(16) 0.0366(5) Uani d 1 . .
C C16 0.2168(2) 0.4460(2) 0.49540(15) 0.0337(5) Uani d 1 . .
C C17 0.2754(3) 0.3710(2) 0.42919(17) 0.0433(6) Uani d 1 . .
H H17 0.342033 0.410741 0.399214 0.052 Uiso calc 1 . .
C C18 0.2314(3) 0.2358(3) 0.40951(19) 0.0506(7) Uani d 1 . .
C C19 0.1331(3) 0.1725(3) 0.4508(2) 0.0499(6) Uani d 1 . .
H H19 0.104923 0.080823 0.434727 0.060 Uiso calc 1 . .
C C20 0.0768(3) 0.2477(2) 0.51667(18) 0.0455(6) Uani d 1 . .
H H20 0.010776 0.206716 0.546413 0.055 Uiso calc 1 . .
C C21 0.1176(3) 0.3841(2) 0.53914(16) 0.0384(5) Uani d 1 . .
H H21 0.078456 0.434347 0.583540 0.046 Uiso calc 1 . .
C C22 0.2634(3) 0.9763(2) 0.71679(15) 0.0353(5) Uani d 1 . .
C C23 0.1630(3) 0.9087(3) 0.75644(17) 0.0440(6) Uani d 1 . .
H H23 0.167992 0.825824 0.762208 0.053 Uiso calc 1 . .
C C24 0.0557(3) 0.9667(3) 0.78711(19) 0.0535(7) Uani d 1 . .
C C25 0.0420(3) 1.0879(3) 0.7803(2) 0.0594(8) Uani d 1 . .
H H25 -0.031877 1.124201 0.802104 0.071 Uiso calc 1 . .
C C26 0.1412(4) 1.1541(3) 0.7400(2) 0.0599(8) Uani d 1 . .
H H26 0.134416 1.236611 0.734309 0.072 Uiso calc 1 . .
C C27 0.2515(3) 1.0991(2) 0.70780(18) 0.0470(6) Uani d 1 . .
H H27 0.317434 1.144510 0.680199 0.056 Uiso calc 1 . .
C C28 0.6448(3) 0.7346(2) 0.92467(16) 0.0390(5) Uani d 1 . .
C C29 0.7529(3) 0.6719(3) 0.8994(2) 0.0534(7) Uani d 1 . .
H H29 0.791538 0.681133 0.848171 0.064 Uiso calc 1 . .
C C30 0.8018(3) 0.5958(3) 0.9516(2) 0.0614(8) Uani d 1 . .
C C31 0.7501(4) 0.5788(3) 1.0267(2) 0.0659(9) Uani d 1 . .
H H31 0.786550 0.526765 1.060648 0.079 Uiso calc 1 . .
C C32 0.6423(5) 0.6407(4) 1.0515(2) 0.0765(10) Uani d 1 . .
H H32 0.604302 0.630202 1.102705 0.092 Uiso calc 1 . .
C C33 0.5898(4) 0.7190(3) 1.0003(2) 0.0651(8) Uani d 1 . .
H H33 0.516962 0.760891 1.017591 0.078 Uiso calc 1 . .
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'
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'
N N 0.0061 0.0033 '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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
Cl1 Cu1 Cl2 . . 116.29(3) ?
N1 Cu1 Cl1 . . 112.26(6) ?
N1 Cu1 Cl2 . . 110.16(6) ?
N3 Cu1 Cl1 . . 114.35(6) ?
N3 Cu1 N1 . . 90.32(7) ?
N3 Cu1 Cl2 . . 110.56(6) ?
C1 N1 Cu1 . . 125.46(15) ?
C1 N1 C7 . . 108.16(18) ?
C7 N1 Cu1 . . 125.71(14) ?
N1 C1 N2 . . 109.51(19) ?
N1 C1 C16 . . 125.6(2) ?
N2 C1 C16 . . 124.88(19) ?
C1 N2 C2 . . 130.42(19) ?
C1 N2 C6 . . 107.59(17) ?
C2 N2 C6 . . 121.66(19) ?
N2 C2 H2 . . 120.4 ?
C3 C2 N2 . . 119.2(2) ?
C3 C2 H2 . . 120.4 ?
C9 N3 Cu1 . . 126.13(15) ?
C15 N3 Cu1 . . 125.70(16) ?
C15 N3 C9 . . 108.14(19) ?
C2 C3 H3 . . 119.5 ?
C2 C3 C4 . . 121.0(2) ?
C4 C3 H3 . . 119.5 ?
C14 N4 C10 . . 122.1(2) ?
C15 N4 C10 . . 108.36(18) ?
C15 N4 C14 . . 129.5(2) ?
C3 C4 H4 . . 119.8 ?
C5 C4 C3 . . 120.5(2) ?
C5 C4 H4 . . 119.8 ?
C4 C5 H5 . . 120.2 ?
C4 C5 C6 . . 119.5(2) ?
C6 C5 H5 . . 120.2 ?
N2 C6 C5 . . 118.08(19) ?
C7 C6 N2 . . 106.10(18) ?
C7 C6 C5 . . 135.8(2) ?
N1 C7 C6 . . 108.62(18) ?
N1 C7 C8 . . 125.69(19) ?
C6 C7 C8 . . 125.6(2) ?
C7 C8 H8 . . 105.6 ?
C7 C8 C9 . . 115.73(18) ?
C7 C8 C22 . . 112.84(18) ?
C9 C8 H8 . . 105.6 ?
C9 C8 C22 . . 110.64(18) ?
C22 C8 H8 . . 105.6 ?
N3 C9 C8 . . 125.95(19) ?
C10 C9 N3 . . 108.66(19) ?
C10 C9 C8 . . 125.3(2) ?
N4 C10 C11 . . 118.2(2) ?
C9 C10 N4 . . 105.58(19) ?
C9 C10 C11 . . 136.2(2) ?
C10 C11 H11 . . 120.5 ?
C12 C11 C10 . . 119.0(3) ?
C12 C11 H11 . . 120.5 ?
C11 C12 H12 . . 119.4 ?
C11 C12 C13 . . 121.2(3) ?
C13 C12 H12 . . 119.4 ?
C12 C13 H13 . . 119.6 ?
C14 C13 C12 . . 120.8(3) ?
C14 C13 H13 . . 119.6 ?
N4 C14 H14 . . 120.7 ?
C13 C14 N4 . . 118.7(3) ?
C13 C14 H14 . . 120.7 ?
N3 C15 N4 . . 109.3(2) ?
N3 C15 C28 . . 128.2(2) ?
N4 C15 C28 . . 122.5(2) ?
C17 C16 C1 . . 120.7(2) ?
C21 C16 C1 . . 119.2(2) ?
C21 C16 C17 . . 120.0(2) ?
C16 C17 H17 . . 121.2 ?
C18 C17 C16 . . 117.6(2) ?
C18 C17 H17 . . 121.2 ?
F1 C18 C17 . . 118.3(2) ?
F1 C18 C19 . . 118.2(2) ?
C19 C18 C17 . . 123.6(2) ?
C18 C19 H19 . . 120.9 ?
C18 C19 C20 . . 118.2(2) ?
C20 C19 H19 . . 120.9 ?
C19 C20 H20 . . 119.7 ?
C19 C20 C21 . . 120.5(2) ?
C21 C20 H20 . . 119.7 ?
C16 C21 H21 . . 120.0 ?
C20 C21 C16 . . 120.0(2) ?
C20 C21 H21 . . 120.0 ?
C23 C22 C8 . . 120.7(2) ?
C23 C22 C27 . . 119.4(2) ?
C27 C22 C8 . . 119.9(2) ?
C22 C23 H23 . . 120.8 ?
C24 C23 C22 . . 118.5(2) ?
C24 C23 H23 . . 120.8 ?
F2 C24 C23 . . 118.5(3) ?
F2 C24 C25 . . 117.9(3) ?
C25 C24 C23 . . 123.6(3) ?
C24 C25 H25 . . 121.1 ?
C24 C25 C26 . . 117.7(3) ?
C26 C25 H25 . . 121.1 ?
C25 C26 H26 . . 119.6 ?
C25 C26 C27 . . 120.7(3) ?
C27 C26 H26 . . 119.6 ?
C22 C27 H27 . . 119.9 ?
C26 C27 C22 . . 120.1(3) ?
C26 C27 H27 . . 119.9 ?
C29 C28 C15 . . 119.1(2) ?
C33 C28 C15 . . 121.2(2) ?
C33 C28 C29 . . 119.5(3) ?
C28 C29 H29 . . 120.8 ?
C30 C29 C28 . . 118.4(3) ?
C30 C29 H29 . . 120.8 ?
F3 C30 C29 . . 117.6(3) ?
C31 C30 F3 . . 118.8(3) ?
C31 C30 C29 . . 123.5(3) ?
C30 C31 H31 . . 120.9 ?
C30 C31 C32 . . 118.1(3) ?
C32 C31 H31 . . 120.9 ?
C31 C32 H32 . . 119.9 ?
C31 C32 C33 . . 120.2(3) ?
C33 C32 H32 . . 119.9 ?
C28 C33 C32 . . 120.3(3) ?
C28 C33 H33 . . 119.9 ?
C32 C33 H33 . . 119.9 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
Cu1 Cl1 . 2.2164(7) ?
Cu1 N1 . 2.0626(18) ?
Cu1 Cl2 . 2.2356(7) ?
Cu1 N3 . 2.0503(19) ?
F1 C18 . 1.346(3) ?
N1 C1 . 1.338(3) ?
N1 C7 . 1.375(3) ?
C1 N2 . 1.363(3) ?
C1 C16 . 1.470(3) ?
F2 C24 . 1.360(3) ?
N2 C2 . 1.386(3) ?
N2 C6 . 1.403(3) ?
C2 H2 . 0.9300 ?
C2 C3 . 1.341(3) ?
F3 C30 . 1.362(4) ?
N3 C9 . 1.376(3) ?
N3 C15 . 1.334(3) ?
C3 H3 . 0.9300 ?
C3 C4 . 1.426(3) ?
N4 C10 . 1.398(3) ?
N4 C14 . 1.391(3) ?
N4 C15 . 1.355(3) ?
C4 H4 . 0.9300 ?
C4 C5 . 1.353(3) ?
C5 H5 . 0.9300 ?
C5 C6 . 1.422(3) ?
C6 C7 . 1.378(3) ?
C7 C8 . 1.507(3) ?
C8 H8 . 0.9800 ?
C8 C9 . 1.508(3) ?
C8 C22 . 1.536(3) ?
C9 C10 . 1.376(3) ?
C10 C11 . 1.421(3) ?
C11 H11 . 0.9300 ?
C11 C12 . 1.351(4) ?
C12 H12 . 0.9300 ?
C12 C13 . 1.425(4) ?
C13 H13 . 0.9300 ?
C13 C14 . 1.338(4) ?
C14 H14 . 0.9300 ?
C15 C28 . 1.476(3) ?
C16 C17 . 1.389(3) ?
C16 C21 . 1.389(3) ?
C17 H17 . 0.9300 ?
C17 C18 . 1.378(3) ?
C18 C19 . 1.365(4) ?
C19 H19 . 0.9300 ?
C19 C20 . 1.374(4) ?
C20 H20 . 0.9300 ?
C20 C21 . 1.386(3) ?
C21 H21 . 0.9300 ?
C22 C23 . 1.383(3) ?
C22 C27 . 1.391(3) ?
C23 H23 . 0.9300 ?
C23 C24 . 1.374(4) ?
C24 C25 . 1.368(4) ?
C25 H25 . 0.9300 ?
C25 C26 . 1.374(4) ?
C26 H26 . 0.9300 ?
C26 C27 . 1.391(4) ?
C27 H27 . 0.9300 ?
C28 C29 . 1.382(4) ?
C28 C33 . 1.370(4) ?
C29 H29 . 0.9300 ?
C29 C30 . 1.370(4) ?
C30 C31 . 1.350(5) ?
C31 H31 . 0.9300 ?
C31 C32 . 1.372(5) ?
C32 H32 . 0.9300 ?
C32 C33 . 1.392(4) ?
C33 H33 . 0.9300 ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_D
_geom_hbond_site_symmetry_H
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
C12 H12 F3 1_555 1_555 1_565 0.93 2.47 3.384(4) 166 yes
C23 H23 Cl2 1_555 1_555 1_555 0.93 2.81 3.736(3) 174 yes
C20 H20 Cg1 1_555 1_555 2_566 0.93 2.77 3.477(3) 133 yes
C18 F1 Cg2 1_555 1_555 2_666 1.346(4) 3.234(2) 4.484(3) 154.19(18) yes
C24 F2 Cg3 1_555 1_555 1_455 1.360(4) 3.569(2) 4.284(3) 112.78(17) yes
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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
Cu1 N1 C1 N2 . . . . -171.40(14) ?
Cu1 N1 C1 C16 . . . . 9.1(3) ?
Cu1 N1 C7 C6 . . . . 171.14(14) ?
Cu1 N1 C7 C8 . . . . -10.9(3) ?
Cu1 N3 C9 C8 . . . . -0.3(3) ?
Cu1 N3 C9 C10 . . . . 177.62(15) ?
Cu1 N3 C15 N4 . . . . -177.56(14) ?
Cu1 N3 C15 C28 . . . . 4.4(4) ?
F1 C18 C19 C20 . . . . 178.3(3) ?
N1 C1 N2 C2 . . . . -172.9(2) ?
N1 C1 N2 C6 . . . . 0.4(2) ?
N1 C1 C16 C17 . . . . -129.4(3) ?
N1 C1 C16 C21 . . . . 48.9(3) ?
N1 C7 C8 C9 . . . . 35.2(3) ?
N1 C7 C8 C22 . . . . -93.7(3) ?
C1 N1 C7 C6 . . . . 0.1(2) ?
C1 N1 C7 C8 . . . . 178.1(2) ?
C1 N2 C2 C3 . . . . 174.9(2) ?
C1 N2 C6 C5 . . . . -177.90(19) ?
C1 N2 C6 C7 . . . . -0.4(2) ?
C1 C16 C17 C18 . . . . 178.3(2) ?
C1 C16 C21 C20 . . . . -178.4(2) ?
F2 C24 C25 C26 . . . . 179.6(3) ?
N2 C1 C16 C17 . . . . 51.1(3) ?
N2 C1 C16 C21 . . . . -130.6(2) ?
N2 C2 C3 C4 . . . . 0.9(4) ?
N2 C6 C7 N1 . . . . 0.1(2) ?
N2 C6 C7 C8 . . . . -177.80(19) ?
C2 N2 C6 C5 . . . . -3.9(3) ?
C2 N2 C6 C7 . . . . 173.66(19) ?
C2 C3 C4 C5 . . . . -2.6(4) ?
F3 C30 C31 C32 . . . . -178.9(3) ?
N3 C9 C10 N4 . . . . 0.3(2) ?
N3 C9 C10 C11 . . . . -179.9(3) ?
N3 C15 C28 C29 . . . . 85.9(3) ?
N3 C15 C28 C33 . . . . -98.4(3) ?
C3 C4 C5 C6 . . . . 1.0(3) ?
N4 C10 C11 C12 . . . . 0.4(3) ?
N4 C15 C28 C29 . . . . -91.9(3) ?
N4 C15 C28 C33 . . . . 83.8(3) ?
C4 C5 C6 N2 . . . . 2.1(3) ?
C4 C5 C6 C7 . . . . -174.5(2) ?
C5 C6 C7 N1 . . . . 177.0(2) ?
C5 C6 C7 C8 . . . . -0.9(4) ?
C6 N2 C2 C3 . . . . 2.4(3) ?
C6 C7 C8 C9 . . . . -147.2(2) ?
C6 C7 C8 C22 . . . . 83.9(3) ?
C7 N1 C1 N2 . . . . -0.3(2) ?
C7 N1 C1 C16 . . . . -179.9(2) ?
C7 C8 C9 N3 . . . . -29.1(3) ?
C7 C8 C9 C10 . . . . 153.3(2) ?
C7 C8 C22 C23 . . . . 69.4(3) ?
C7 C8 C22 C27 . . . . -113.8(2) ?
C8 C9 C10 N4 . . . . 178.2(2) ?
C8 C9 C10 C11 . . . . -1.9(4) ?
C8 C22 C23 C24 . . . . 175.8(2) ?
C8 C22 C27 C26 . . . . -175.7(2) ?
C9 N3 C15 N4 . . . . 0.6(3) ?
C9 N3 C15 C28 . . . . -177.5(2) ?
C9 C8 C22 C23 . . . . -62.1(3) ?
C9 C8 C22 C27 . . . . 114.8(2) ?
C9 C10 C11 C12 . . . . -179.4(3) ?
C10 N4 C14 C13 . . . . 0.2(4) ?
C10 N4 C15 N3 . . . . -0.4(3) ?
C10 N4 C15 C28 . . . . 177.7(2) ?
C10 C11 C12 C13 . . . . -0.8(4) ?
C11 C12 C13 C14 . . . . 0.9(5) ?
C12 C13 C14 N4 . . . . -0.5(4) ?
C14 N4 C10 C9 . . . . 179.8(2) ?
C14 N4 C10 C11 . . . . -0.1(3) ?
C14 N4 C15 N3 . . . . 179.9(2) ?
C14 N4 C15 C28 . . . . -1.9(4) ?
C15 N3 C9 C8 . . . . -178.4(2) ?
C15 N3 C9 C10 . . . . -0.5(3) ?
C15 N4 C10 C9 . . . . 0.1(2) ?
C15 N4 C10 C11 . . . . -179.8(2) ?
C15 N4 C14 C13 . . . . 179.8(3) ?
C15 C28 C29 C30 . . . . 175.7(2) ?
C15 C28 C33 C32 . . . . -175.7(3) ?
C16 C1 N2 C2 . . . . 6.7(4) ?
C16 C1 N2 C6 . . . . 180.0(2) ?
C16 C17 C18 F1 . . . . -178.8(2) ?
C16 C17 C18 C19 . . . . 0.6(4) ?
C17 C16 C21 C20 . . . . -0.1(4) ?
C17 C18 C19 C20 . . . . -1.1(4) ?
C18 C19 C20 C21 . . . . 1.0(4) ?
C19 C20 C21 C16 . . . . -0.4(4) ?
C21 C16 C17 C18 . . . . 0.0(4) ?
C22 C8 C9 N3 . . . . 100.8(2) ?
C22 C8 C9 C10 . . . . -76.8(3) ?
C22 C23 C24 F2 . . . . -179.0(2) ?
C22 C23 C24 C25 . . . . 0.3(4) ?
C23 C22 C27 C26 . . . . 1.2(4) ?
C23 C24 C25 C26 . . . . 0.3(4) ?
C24 C25 C26 C27 . . . . -0.2(4) ?
C25 C26 C27 C22 . . . . -0.6(4) ?
C27 C22 C23 C24 . . . . -1.0(4) ?
C28 C29 C30 F3 . . . . 179.2(3) ?
C28 C29 C30 C31 . . . . -0.1(5) ?
C29 C28 C33 C32 . . . . 0.1(5) ?
C29 C30 C31 C32 . . . . 0.4(5) ?
C30 C31 C32 C33 . . . . -0.4(5) ?
C31 C32 C33 C28 . . . . 0.2(5) ?
C33 C28 C29 C30 . . . . -0.1(4) ?
