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#$Date: 2020-11-06 14:41:16 +0200 (Fri, 06 Nov 2020) $
#$Revision: 258890 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/05/99/7059941.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_7059941
loop_
_publ_author_name
'Espitia Cogollo, E.'
'Piro, O. E.'
'Echeverría, G. A.'
'Tuttolomondo, M. E.'
'Pérez, H.'
'Jios, J. L.'
'Ulic, S. E.'
_publ_section_title
;
 Hydrogen bonding interactions in fluorinated 1,2,3-triazole derivatives
;
_journal_issue                   37
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              16006
_journal_page_last               16019
_journal_paper_doi               10.1039/D0NJ02914A
_journal_volume                  44
_journal_year                    2020
_chemical_formula_sum            'C10 H5 Cl F3 N3 O2'
_chemical_formula_weight         291.62
_chemical_name_systematic
4-(2-hydroxy-5-chlorophenyl)carbonyl-5-trifluoromethyl-2H-1,2,3-triazol
_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   difmap
_atom_sites_solution_primary     dual
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2019-06-27 deposited with the CCDC.	2020-08-24 downloaded from the CCDC.
;
_cell_angle_alpha                106.450(9)
_cell_angle_beta                 101.623(11)
_cell_angle_gamma                93.168(9)
_cell_formula_units_Z            2
_cell_length_a                   6.6403(9)
_cell_length_b                   8.1037(7)
_cell_length_c                   11.1004(13)
_cell_measurement_reflns_used    1074
_cell_measurement_temperature    297(2)
_cell_measurement_theta_max      26.6750
_cell_measurement_theta_min      3.9250
_cell_volume                     557.10(12)
_computing_cell_refinement       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_molecular_graphics    'ORTEP-3 (Farrugia, 1997)'
_computing_publication_material  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      297(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0604
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.841
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0300
_diffrn_reflns_av_unetI/netI     0.0558
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.841
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            4085
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.841
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.502
_diffrn_reflns_theta_min         3.317
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.386
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.95290
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.738
_exptl_crystal_description       plate
_exptl_crystal_F_000             292
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: Ether:toluene (2:1)'
_exptl_crystal_size_max          0.337
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.027
_refine_diff_density_max         0.242
_refine_diff_density_min         -0.260
_refine_diff_density_rms         0.052
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     192
_refine_ls_number_reflns         2373
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.039
_refine_ls_R_factor_all          0.0808
_refine_ls_R_factor_gt           0.0482
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0511P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1044
_refine_ls_wR_factor_ref         0.1272
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1554
_reflns_number_total             2373
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d0nj02914a2.cif
_cod_data_source_block           shelx
_cod_depositor_comments
'Adding full bibliography for 7059939--7059942.cif.'
_cod_database_code               7059941
_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   0.881
_shelx_estimated_absorpt_t_max   0.990
_oxdiff_exptl_absorpt_empirical_full_min 0.904
_oxdiff_exptl_absorpt_empirical_full_max 1.149
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-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
C1 C 0.5822(4) 0.7811(3) 0.6307(2) 0.0353(6) Uani 1 1 d . . . . .
C2 C 0.7190(4) 0.8358(4) 0.5637(3) 0.0444(7) Uani 1 1 d . . . . .
C3 C 0.6500(5) 0.8190(4) 0.4328(3) 0.0548(8) Uani 1 1 d . . . . .
C4 C 0.4535(5) 0.7433(4) 0.3681(3) 0.0531(8) Uani 1 1 d . . . . .
C5 C 0.3222(4) 0.6816(3) 0.4321(3) 0.0448(7) Uani 1 1 d . . . . .
C6 C 0.3823(4) 0.7018(3) 0.5609(3) 0.0393(6) Uani 1 1 d . . . . .
C7 C 0.6505(4) 0.8065(3) 0.7682(2) 0.0341(6) Uani 1 1 d . . . . .
C8 C 0.5042(3) 0.7865(3) 0.8502(2) 0.0312(5) Uani 1 1 d . . . . .
C9 C 0.5487(3) 0.7535(3) 0.9691(2) 0.0316(5) Uani 1 1 d . . . . .
C10 C 0.7385(4) 0.7018(3) 1.0389(2) 0.0397(6) Uani 1 1 d . . . . .
N1 N 0.3803(3) 0.7652(3) 1.0182(2) 0.0404(5) Uani 1 1 d . . . . .
N2 N 0.2439(3) 0.8035(3) 0.9293(2) 0.0416(6) Uani 1 1 d . . . . .
N3 N 0.3067(3) 0.8173(3) 0.8261(2) 0.0392(5) Uani 1 1 d . . . . .
O1 O 0.9146(3) 0.9070(3) 0.6186(2) 0.0631(6) Uani 1 1 d . . . . .
O2 O 0.8343(2) 0.8516(2) 0.82585(17) 0.0446(5) Uani 1 1 d . . . . .
F1 F 0.8882(2) 0.8337(2) 1.09661(17) 0.0624(5) Uani 1 1 d . . . . .
F2 F 0.8200(2) 0.5840(2) 0.95894(16) 0.0556(5) Uani 1 1 d . . . . .
F3 F 0.6981(2) 0.6333(2) 1.12833(16) 0.0613(5) Uani 1 1 d . . . . .
Cl Cl 0.07778(12) 0.57812(12) 0.34712(8) 0.0697(3) Uani 1 1 d . . . . .
H1 H 0.936(5) 0.904(4) 0.693(3) 0.076(12) Uiso 1 1 d . . . . .
H2 H 0.106(4) 0.815(3) 0.937(3) 0.055(8) Uiso 1 1 d . . . . .
H3 H 0.740(5) 0.874(4) 0.395(3) 0.088(11) Uiso 1 1 d . . . . .
H4 H 0.417(5) 0.734(4) 0.281(3) 0.068(9) Uiso 1 1 d . . . . .
H6 H 0.292(4) 0.657(3) 0.606(3) 0.048(7) Uiso 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'
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
C2 C1 C6 118.4(2) . . ?
C2 C1 C7 119.6(2) . . ?
C6 C1 C7 122.0(2) . . ?
O1 C2 C3 116.6(3) . . ?
O1 C2 C1 123.8(3) . . ?
C3 C2 C1 119.6(3) . . ?
C4 C3 C2 120.4(3) . . ?
C3 C4 C5 120.1(3) . . ?
C6 C5 C4 120.8(3) . . ?
C6 C5 Cl 119.7(2) . . ?
C4 C5 Cl 119.5(2) . . ?
C5 C6 C1 120.5(2) . . ?
O2 C7 C1 122.0(2) . . ?
O2 C7 C8 115.5(2) . . ?
C1 C7 C8 122.5(2) . . ?
N3 C8 C9 108.1(2) . . ?
N3 C8 C7 123.6(2) . . ?
C9 C8 C7 127.9(2) . . ?
N1 C9 C8 109.3(2) . . ?
N1 C9 C10 119.5(2) . . ?
C8 C9 C10 131.1(2) . . ?
F1 C10 F3 107.7(2) . . ?
F1 C10 F2 105.8(2) . . ?
F3 C10 F2 107.2(2) . . ?
F1 C10 C9 113.0(2) . . ?
F3 C10 C9 111.51(19) . . ?
F2 C10 C9 111.3(2) . . ?
N2 N1 C9 102.6(2) . . ?
N1 N2 N3 117.0(2) . . ?
N2 N3 C8 103.1(2) . . ?
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
C1 C2 1.410(3) . ?
C1 C6 1.409(3) . ?
C1 C7 1.453(3) . ?
C2 O1 1.338(3) . ?
C2 C3 1.398(4) . ?
C3 C4 1.371(4) . ?
C4 C5 1.384(4) . ?
C5 C6 1.365(4) . ?
C5 Cl 1.735(3) . ?
C7 O2 1.239(3) . ?
C7 C8 1.491(3) . ?
C8 N3 1.337(3) . ?
C8 C9 1.396(3) . ?
C9 N1 1.336(3) . ?
C9 C10 1.488(3) . ?
C10 F1 1.334(3) . ?
C10 F3 1.330(3) . ?
C10 F2 1.328(3) . ?
N1 N2 1.317(3) . ?
N2 N3 1.325(3) . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O1 H1 O2 0.81(3) 1.89(3) 2.614(3) 149(3) .
N2 H2 O2 0.94(3) 2.06(3) 2.825(3) 137(2) 1_455
N2 H2 F1 0.94(3) 2.48(3) 3.265(3) 141(2) 1_455
C6 H6 N3 0.97(3) 2.40(3) 2.980(3) 117.9(19) .
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
C6 C1 C2 O1 -177.5(3) . . . . ?
C7 C1 C2 O1 2.0(4) . . . . ?
C6 C1 C2 C3 3.5(4) . . . . ?
C7 C1 C2 C3 -176.9(2) . . . . ?
O1 C2 C3 C4 178.3(3) . . . . ?
C1 C2 C3 C4 -2.7(4) . . . . ?
C2 C3 C4 C5 -0.5(5) . . . . ?
C3 C4 C5 C6 2.9(4) . . . . ?
C3 C4 C5 Cl -177.3(2) . . . . ?
C4 C5 C6 C1 -2.0(4) . . . . ?
Cl C5 C6 C1 178.22(19) . . . . ?
C2 C1 C6 C5 -1.2(4) . . . . ?
C7 C1 C6 C5 179.3(2) . . . . ?
C2 C1 C7 O2 -10.7(4) . . . . ?
C6 C1 C7 O2 168.8(2) . . . . ?
C2 C1 C7 C8 167.0(2) . . . . ?
C6 C1 C7 C8 -13.4(4) . . . . ?
O2 C7 C8 N3 148.2(2) . . . . ?
C1 C7 C8 N3 -29.7(3) . . . . ?
O2 C7 C8 C9 -23.9(3) . . . . ?
C1 C7 C8 C9 158.2(2) . . . . ?
N3 C8 C9 N1 -0.4(3) . . . . ?
C7 C8 C9 N1 172.7(2) . . . . ?
N3 C8 C9 C10 175.9(2) . . . . ?
C7 C8 C9 C10 -11.0(4) . . . . ?
N1 C9 C10 F1 -106.5(3) . . . . ?
C8 C9 C10 F1 77.5(3) . . . . ?
N1 C9 C10 F3 15.1(3) . . . . ?
C8 C9 C10 F3 -161.0(2) . . . . ?
N1 C9 C10 F2 134.7(2) . . . . ?
C8 C9 C10 F2 -41.3(3) . . . . ?
C8 C9 N1 N2 0.1(3) . . . . ?
C10 C9 N1 N2 -176.7(2) . . . . ?
C9 N1 N2 N3 0.3(3) . . . . ?
N1 N2 N3 C8 -0.5(3) . . . . ?
C9 C8 N3 N2 0.6(2) . . . . ?
C7 C8 N3 N2 -172.9(2) . . . . ?
