#------------------------------------------------------------------------------
#$Date: 2021-10-06 04:44:11 +0300 (Wed, 06 Oct 2021) $
#$Revision: 269597 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/02/24/2022482.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_2022482
loop_
_publ_author_name
'Pokhodylo, Nazariy T.'
'Slyvka, Yurii'
'Goreshnik, Evgeny'
'Lytvyn, Roman'
_publ_section_title
;
 Synthesis, crystal structure and Hirshfeld surface analysis of
 (4-methylphenyl)[1-(pentafluorophenyl)-5-(trifluoromethyl)-1H-1,2,3-triazol-4-yl]methanone
;
_journal_coeditor_code           HB7985
_journal_issue                   11
_journal_name_full
'Acta Crystallographica Section E Crystallographic Communications'
_journal_paper_doi               10.1107/S2056989021010070
_journal_volume                  77
_journal_year                    2021
_chemical_formula_iupac          'C17 H7 F8 N3 O'
_chemical_formula_moiety         'C17 H7 F8 N3 O'
_chemical_formula_sum            'C17 H7 F8 N3 O'
_chemical_formula_weight         421.26
_chemical_name_systematic
(4-Methylphenyl)[1-(pentafluorophenyl)-5-(trifluoromethyl)-1H-1,2,3-triazol-4-yl]methanone
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.7605(6)
_cell_length_b                   15.0650(10)
_cell_length_c                   16.0849(9)
_cell_measurement_reflns_used    2646
_cell_measurement_temperature    150.00(12)
_cell_measurement_theta_max      72.2010
_cell_measurement_theta_min      3.9490
_cell_volume                     1638.2(2)
_computing_cell_refinement
;
CrysAlisPro (Rigaku OD, 2021)
;
_computing_data_collection
;
CrysAlisPro (Rigaku OD, 2021)
;
_computing_data_reduction
;
CrysAlisPro (Rigaku OD, 2021)
;
_computing_molecular_graphics
;
OLEX2 (Dolomanov et al., 2009)
;
_computing_publication_material
;
OLEX2 (Dolomanov et al., 2009)
;
_computing_structure_refinement
;
SHELXL2018/3 (Sheldrick, 2015b)
;
_computing_structure_solution
;
SHELXT  (Sheldrick, 2015a)
;
_diffrn_ambient_temperature      150.15
_diffrn_detector_area_resol_mean 10.6426
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'New Gemini, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0876
_diffrn_reflns_av_unetI/netI     0.0646
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            15249
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.317
_diffrn_reflns_theta_min         4.020
_exptl_absorpt_coefficient_mu    1.548
_exptl_absorpt_correction_T_max  0.678
_exptl_absorpt_correction_T_min  0.320
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
(CrysalisPro; Rigaku OD, 2021)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.708
_exptl_crystal_description       irregular
_exptl_crystal_F_000             840
_exptl_crystal_size_max          0.432
_exptl_crystal_size_mid          0.124
_exptl_crystal_size_min          0.079
_refine_diff_density_max         0.179
_refine_diff_density_min         -0.178
_refine_ls_abs_structure_details
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.2(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     264
_refine_ls_number_reflns         3187
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.032
_refine_ls_R_factor_all          0.0778
_refine_ls_R_factor_gt           0.0469
_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)+(0.0310P)²+0.1487P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0920
_refine_ls_wR_factor_ref         0.1088
_reflns_number_gt                2311
_reflns_number_total             3187
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            hb7985sup1.cif
_cod_data_source_block           I
_cod_database_code               2022482
_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.
;
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -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
F F1 0.0932(5) 0.4231(2) 0.51007(19) 0.0563(9) Uani d 1 . .
F F2 0.2755(6) 0.52826(18) 0.4634(2) 0.0575(10) Uani d 1 . .
F F3 0.1757(5) 0.42585(19) 0.38129(17) 0.0456(8) Uani d 1 . .
F F4 0.5987(6) 0.50612(18) 0.33789(17) 0.0565(9) Uani d 1 . .
F F5 0.6160(6) 0.5157(2) 0.16979(18) 0.0609(10) Uani d 1 . .
F F6 0.5614(6) 0.3674(3) 0.07762(16) 0.0612(10) Uani d 1 . .
F F7 0.4985(6) 0.2089(2) 0.15264(18) 0.0566(9) Uani d 1 . .
F F8 0.4847(5) 0.19857(17) 0.32018(16) 0.0456(8) Uani d 1 . .
O O1 0.3633(7) 0.4664(2) 0.6435(2) 0.0496(10) Uani d 1 . .
N N1 0.5368(7) 0.3474(2) 0.4207(2) 0.0351(10) Uani d 1 . .
N N2 0.6809(7) 0.2985(3) 0.4582(2) 0.0418(11) Uani d 1 . .
N N3 0.6565(8) 0.3072(3) 0.5387(2) 0.0410(10) Uani d 1 . .
C C1 0.5367(8) 0.3525(3) 0.3316(3) 0.0339(11) Uani d 1 . .
C C2 0.5726(8) 0.4330(3) 0.2930(3) 0.0396(12) Uani d 1 . .
C C3 0.5793(9) 0.4382(4) 0.2066(3) 0.0451(13) Uani d 1 . .
C C4 0.5531(9) 0.3623(4) 0.1611(3) 0.0430(13) Uani d 1 . .
C C5 0.5215(9) 0.2822(3) 0.1983(3) 0.0405(12) Uani d 1 . .
C C6 0.5130(8) 0.2771(3) 0.2847(3) 0.0357(11) Uani d 1 . .
C C7 0.4210(8) 0.3878(3) 0.4781(3) 0.0319(11) Uani d 1 . .
C C8 0.4981(8) 0.3615(3) 0.5531(3) 0.0337(11) Uani d 1 . .
C C9 0.4375(9) 0.3934(3) 0.6379(3) 0.0385(13) Uani d 1 . .
C C10 0.4732(8) 0.3363(3) 0.7117(3) 0.0345(11) Uani d 1 . .
C C11 0.5049(8) 0.2451(3) 0.7063(3) 0.0340(10) Uani d 1 . .
H H11 0.509418 0.217046 0.653465 0.041 Uiso calc 1 . .
C C12 0.5297(8) 0.1955(3) 0.7776(3) 0.0360(11) Uani d 1 . .
H H12 0.549256 0.133197 0.773331 0.043 Uiso calc 1 . .
C C13 0.5267(8) 0.2352(3) 0.8560(3) 0.0374(12) Uani d 1 . .
C C14 0.4964(10) 0.3264(3) 0.8609(3) 0.0454(14) Uani d 1 . .
H H14 0.494442 0.354584 0.913774 0.054 Uiso calc 1 . .
C C15 0.4693(9) 0.3765(3) 0.7897(3) 0.0438(14) Uani d 1 . .
H H15 0.447771 0.438645 0.794080 0.053 Uiso calc 1 . .
C C16 0.5547(10) 0.1808(3) 0.9339(3) 0.0493(16) Uani d 1 . .
H H16A 0.562191 0.117776 0.919256 0.074 Uiso calc 1 . .
H H16B 0.442677 0.190607 0.971434 0.074 Uiso calc 1 . .
H H16C 0.677506 0.198827 0.961531 0.074 Uiso calc 1 . .
C C17 0.2417(9) 0.4415(3) 0.4588(3) 0.0405(12) Uani d 1 . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 -1 -10 0.0480
4 2 0 0.1999
-4 -2 -1 0.2089
0 10 -1 0.0324
0 -10 1 0.0646
0 5 9 0.0240
0 -5 -9 0.0459
0 -6 8 0.0535
-1 7 -8 0.0275
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
N2 N1 C1 . . 118.1(4) ?
C7 N1 N2 . . 110.8(4) ?
C7 N1 C1 . . 131.0(4) ?
N3 N2 N1 . . 107.1(4) ?
N2 N3 C8 . . 109.0(4) ?
C2 C1 N1 . . 119.6(4) ?
C6 C1 N1 . . 120.4(4) ?
C6 C1 C2 . . 119.9(4) ?
F4 C2 C1 . . 120.4(4) ?
F4 C2 C3 . . 119.4(5) ?
C1 C2 C3 . . 120.1(5) ?
F5 C3 C2 . . 119.9(5) ?
F5 C3 C4 . . 121.2(4) ?
C4 C3 C2 . . 118.9(5) ?
F6 C4 C3 . . 118.7(5) ?
F6 C4 C5 . . 119.7(5) ?
C5 C4 C3 . . 121.6(4) ?
F7 C5 C4 . . 120.6(4) ?
F7 C5 C6 . . 119.8(5) ?
C4 C5 C6 . . 119.6(5) ?
F8 C6 C1 . . 121.1(4) ?
F8 C6 C5 . . 119.0(4) ?
C1 C6 C5 . . 119.9(4) ?
N1 C7 C8 . . 104.5(4) ?
N1 C7 C17 . . 124.9(4) ?
C8 C7 C17 . . 130.4(4) ?
N3 C8 C7 . . 108.7(4) ?
N3 C8 C9 . . 123.9(4) ?
C7 C8 C9 . . 127.0(5) ?
O1 C9 C8 . . 118.0(4) ?
O1 C9 C10 . . 122.2(4) ?
C10 C9 C8 . . 119.7(4) ?
C11 C10 C9 . . 123.1(4) ?
C11 C10 C15 . . 119.1(4) ?
C15 C10 C9 . . 117.7(4) ?
C10 C11 H11 . . 119.9 ?
C12 C11 C10 . . 120.1(4) ?
C12 C11 H11 . . 119.9 ?
C11 C12 H12 . . 119.4 ?
C11 C12 C13 . . 121.1(4) ?
C13 C12 H12 . . 119.4 ?
C12 C13 C16 . . 121.0(4) ?
C14 C13 C12 . . 118.5(4) ?
C14 C13 C16 . . 120.5(4) ?
C13 C14 H14 . . 119.6 ?
C15 C14 C13 . . 120.7(4) ?
C15 C14 H14 . . 119.6 ?
C10 C15 H15 . . 119.8 ?
C14 C15 C10 . . 120.4(4) ?
C14 C15 H15 . . 119.8 ?
C13 C16 H16A . . 109.5 ?
C13 C16 H16B . . 109.5 ?
C13 C16 H16C . . 109.5 ?
H16A C16 H16B . . 109.5 ?
H16A C16 H16C . . 109.5 ?
H16B C16 H16C . . 109.5 ?
F1 C17 F2 . . 107.5(4) ?
F1 C17 F3 . . 106.8(5) ?
F1 C17 C7 . . 111.9(4) ?
F2 C17 F3 . . 106.3(4) ?
F2 C17 C7 . . 112.5(5) ?
F3 C17 C7 . . 111.6(4) ?
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
F1 C17 . 1.328(7) ?
F2 C17 . 1.329(6) ?
F3 C17 . 1.345(6) ?
F4 C2 . 1.328(6) ?
F5 C3 . 1.332(6) ?
F6 C4 . 1.346(5) ?
F7 C5 . 1.336(6) ?
F8 C6 . 1.328(5) ?
O1 C9 . 1.213(6) ?
N1 N2 . 1.362(6) ?
N1 C1 . 1.435(5) ?
N1 C7 . 1.355(6) ?
N2 N3 . 1.313(6) ?
N3 C8 . 1.368(7) ?
C1 C2 . 1.384(7) ?
C1 C6 . 1.373(7) ?
C2 C3 . 1.393(7) ?
C3 C4 . 1.369(8) ?
C4 C5 . 1.363(8) ?
C5 C6 . 1.393(6) ?
C7 C8 . 1.373(6) ?
C7 C17 . 1.490(8) ?
C8 C9 . 1.502(6) ?
C9 C10 . 1.485(6) ?
C10 C11 . 1.393(6) ?
C10 C15 . 1.394(6) ?
C11 H11 . 0.9500 ?
C11 C12 . 1.380(6) ?
C12 H12 . 0.9500 ?
C12 C13 . 1.395(6) ?
C13 C14 . 1.392(7) ?
C13 C16 . 1.508(6) ?
C14 H14 . 0.9500 ?
C14 C15 . 1.384(7) ?
C15 H15 . 0.9500 ?
C16 H16A . 0.9800 ?
C16 H16B . 0.9800 ?
C16 H16C . 0.9800 ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_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
C11 H11 F3 4_556 0.95 2.49 3.155(5) 127 yes
C15 H15 F3 2_565 0.95 2.61 3.463(6) 149 yes
C16 H16A F2 3_646 0.98 2.57 3.054(6) 111 yes
C16 H16A O1 3_646 0.98 2.54 3.505(6) 167 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
F4 C2 C3 F5 . . . . 1.5(9) ?
F4 C2 C3 C4 . . . . 179.7(5) ?
F5 C3 C4 F6 . . . . -1.2(9) ?
F5 C3 C4 C5 . . . . 178.0(6) ?
F6 C4 C5 F7 . . . . -0.1(9) ?
F6 C4 C5 C6 . . . . 180.0(5) ?
F7 C5 C6 F8 . . . . 0.9(9) ?
F7 C5 C6 C1 . . . . -180.0(5) ?
O1 C9 C10 C11 . . . . 161.5(6) ?
O1 C9 C10 C15 . . . . -16.8(9) ?
N1 N2 N3 C8 . . . . -0.2(6) ?
N1 C1 C2 F4 . . . . -2.9(9) ?
N1 C1 C2 C3 . . . . 177.9(5) ?
N1 C1 C6 F8 . . . . 1.8(9) ?
N1 C1 C6 C5 . . . . -177.3(5) ?
N1 C7 C8 N3 . . . . 0.3(5) ?
N1 C7 C8 C9 . . . . 174.0(5) ?
N1 C7 C17 F1 . . . . 136.6(5) ?
N1 C7 C17 F2 . . . . -102.3(5) ?
N1 C7 C17 F3 . . . . 17.1(7) ?
N2 N1 C1 C2 . . . . -114.2(6) ?
N2 N1 C1 C6 . . . . 61.9(7) ?
N2 N1 C7 C8 . . . . -0.4(5) ?
N2 N1 C7 C17 . . . . -175.8(4) ?
N2 N3 C8 C7 . . . . -0.1(6) ?
N2 N3 C8 C9 . . . . -174.1(5) ?
N3 C8 C9 O1 . . . . 147.4(5) ?
N3 C8 C9 C10 . . . . -31.3(8) ?
C1 N1 N2 N3 . . . . 177.1(4) ?
C1 N1 C7 C8 . . . . -176.5(5) ?
C1 N1 C7 C17 . . . . 8.1(8) ?
C1 C2 C3 F5 . . . . -179.3(5) ?
C1 C2 C3 C4 . . . . -1.1(10) ?
C2 C1 C6 F8 . . . . 177.8(5) ?
C2 C1 C6 C5 . . . . -1.2(9) ?
C2 C3 C4 F6 . . . . -179.4(5) ?
C2 C3 C4 C5 . . . . -0.3(10) ?
C3 C4 C5 F7 . . . . -179.3(6) ?
C3 C4 C5 C6 . . . . 0.9(10) ?
C4 C5 C6 F8 . . . . -179.2(5) ?
C4 C5 C6 C1 . . . . -0.1(9) ?
C6 C1 C2 F4 . . . . -179.0(5) ?
C6 C1 C2 C3 . . . . 1.8(9) ?
C7 N1 N2 N3 . . . . 0.4(6) ?
C7 N1 C1 C2 . . . . 61.7(8) ?
C7 N1 C1 C6 . . . . -122.2(6) ?
C7 C8 C9 O1 . . . . -25.4(9) ?
C7 C8 C9 C10 . . . . 155.8(5) ?
C8 C7 C17 F1 . . . . -37.5(7) ?
C8 C7 C17 F2 . . . . 83.6(7) ?
C8 C7 C17 F3 . . . . -157.0(5) ?
C8 C9 C10 C11 . . . . -19.9(9) ?
C8 C9 C10 C15 . . . . 161.9(5) ?
C9 C10 C11 C12 . . . . -177.5(5) ?
C9 C10 C15 C14 . . . . 178.3(6) ?
C10 C11 C12 C13 . . . . -0.9(9) ?
C11 C10 C15 C14 . . . . 0.0(9) ?
C11 C12 C13 C14 . . . . 0.5(9) ?
C11 C12 C13 C16 . . . . -179.7(6) ?
C12 C13 C14 C15 . . . . 0.2(10) ?
C13 C14 C15 C10 . . . . -0.5(10) ?
C15 C10 C11 C12 . . . . 0.7(9) ?
C16 C13 C14 C15 . . . . -179.5(6) ?
C17 C7 C8 N3 . . . . 175.3(5) ?
C17 C7 C8 C9 . . . . -11.0(9) ?
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.8(3)
2 0.2(3)

_cod_database_fobs_code 2022482
