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#$Date: 2023-06-07 10:49:56 +0300 (Wed, 07 Jun 2023) $
#$Revision: 284393 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/73/8107302.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_8107302
loop_
_publ_author_name
'Caracelli, Ignez'
'Teixeira, Wystan K. O.'
'de Albuquerque, Danilo Yano'
'Schwab, Ricardo S.'
'Tiekink, Edward R. T.'
_publ_section_title
;
 The crystal structure of 1-(2-iodophenyl)-4-phenyl-1H-1,2,3-triazole,
 C14H10IN3
;
_journal_issue                   6
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              1093
_journal_page_last               1096
_journal_paper_doi               10.1515/ncrs-2022-0408
_journal_volume                  237
_journal_year                    2022
_chemical_formula_moiety         'C14 H10 I N3'
_chemical_formula_sum            'C14 H10 I N3'
_chemical_formula_weight         347.15
_chemical_name_systematic
;
1-(2-iodophenyl)-4-phenyl-1H-1,2,3-triazole
;
_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
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.0778(6)
_cell_length_b                   11.1909(10)
_cell_length_c                   14.3114(12)
_cell_measurement_reflns_used    4599
_cell_measurement_temperature    290(2)
_cell_measurement_theta_max      26.32
_cell_measurement_theta_min      2.31
_cell_volume                     1293.72(19)
_computing_cell_refinement       'Bruker SAINT [2]'
_computing_data_collection       'Bruker APEX2 [2]'
_computing_data_reduction        'Bruker SAINT [2]'
_computing_molecular_graphics    'ORTEP-3 for Windows [5]'
_computing_publication_material  'SHELXL-2018/3 [4]'
_computing_structure_refinement  'SHELXL-2018/3 [4]'
_computing_structure_solution    'SIR2014      [3]'
_diffrn_ambient_temperature      290(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0563
_diffrn_reflns_av_unetI/netI     0.0504
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            9322
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.400
_diffrn_reflns_theta_min         2.310
_exptl_absorpt_coefficient_mu    2.460
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.4204
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS [1]
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.782
_exptl_crystal_description       irregular
_exptl_crystal_F_000             672
_exptl_crystal_size_max          0.364
_exptl_crystal_size_mid          0.222
_exptl_crystal_size_min          0.077
_refine_diff_density_max         0.708
_refine_diff_density_min         -0.546
_refine_diff_density_rms         0.070
_refine_ls_abs_structure_details
;
 Flack x determined using 917 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.01(2)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     163
_refine_ls_number_reflns         2639
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.041
_refine_ls_R_factor_all          0.0362
_refine_ls_R_factor_gt           0.0312
_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)+(0.0296P)²+0.1135P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0758
_refine_ls_wR_factor_ref         0.0790
_reflns_Friedel_coverage         0.717
_reflns_Friedel_fraction_full    0.995
_reflns_Friedel_fraction_max     0.993
_reflns_number_gt                2397
_reflns_number_total             2639
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            suppl_j_ncrs-2022-0408_suppl.cif
_cod_data_source_block           shelx
_cod_database_code               8107302
_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   0.468
_shelx_estimated_absorpt_t_max   0.833
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_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 0.4836(6) 0.6265(4) 0.5549(4) 0.0355(11) Uani 1 1 d . . . . .
H1 H 0.407661 0.683651 0.574636 0.043 Uiso 1 1 calc R U . . .
C2 C 0.5744(6) 0.6270(4) 0.4743(3) 0.0323(11) Uani 1 1 d . . . . .
C3 C 0.5759(6) 0.7139(5) 0.3971(3) 0.0339(11) Uani 1 1 d . . . . .
C4 C 0.6514(7) 0.6845(5) 0.3119(4) 0.0461(13) Uani 1 1 d . . . . .
H4 H 0.703740 0.610976 0.305167 0.055 Uiso 1 1 calc R U . . .
C5 C 0.6486(9) 0.7631(7) 0.2386(4) 0.0603(18) Uani 1 1 d . . . . .
H5 H 0.698820 0.742408 0.182370 0.072 Uiso 1 1 calc R U . . .
C6 C 0.5721(9) 0.8728(6) 0.2473(5) 0.0604(18) Uani 1 1 d . . . . .
H6 H 0.569121 0.925264 0.196884 0.072 Uiso 1 1 calc R U . . .
C7 C 0.5001(8) 0.9041(6) 0.3311(4) 0.0532(16) Uani 1 1 d . . . . .
H7 H 0.450221 0.978492 0.337640 0.064 Uiso 1 1 calc R U . . .
C8 C 0.5018(7) 0.8247(5) 0.4060(4) 0.0425(13) Uani 1 1 d . . . . .
H8 H 0.452923 0.846364 0.462359 0.051 Uiso 1 1 calc R U . . .
C9 C 0.4663(6) 0.4805(4) 0.6869(3) 0.0324(11) Uani 1 1 d . . . . .
C10 C 0.3563(7) 0.3857(5) 0.6890(3) 0.0365(11) Uani 1 1 d . . . . .
C11 C 0.2959(7) 0.3471(5) 0.7747(4) 0.0404(12) Uani 1 1 d . . . . .
H11 H 0.221803 0.283554 0.777409 0.049 Uiso 1 1 calc R U . . .
C12 C 0.3459(7) 0.4032(5) 0.8560(4) 0.0452(13) Uani 1 1 d . . . . .
H12 H 0.304888 0.376979 0.913166 0.054 Uiso 1 1 calc R U . . .
C13 C 0.4548(7) 0.4967(6) 0.8535(4) 0.0468(14) Uani 1 1 d . . . . .
H13 H 0.487990 0.533606 0.908679 0.056 Uiso 1 1 calc R U . . .
C14 C 0.5150(7) 0.5360(5) 0.7687(4) 0.0423(13) Uani 1 1 d . . . . .
H14 H 0.588430 0.599949 0.766623 0.051 Uiso 1 1 calc R U . . .
N1 N 0.5279(6) 0.5256(4) 0.5996(3) 0.0354(10) Uani 1 1 d . . . . .
N2 N 0.6421(6) 0.4650(4) 0.5499(3) 0.0512(13) Uani 1 1 d . . . . .
N3 N 0.6709(6) 0.5276(4) 0.4741(3) 0.0482(12) Uani 1 1 d . . . . .
I1 I 0.27255(6) 0.30037(4) 0.56765(3) 0.05942(17) 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'
I I -0.4742 1.8119 '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
N1 C1 C2 105.2(5) . .
N1 C1 H1 127.4 . .
C2 C1 H1 127.4 . .
N3 C2 C1 107.9(4) . .
N3 C2 C3 122.3(4) . .
C1 C2 C3 129.8(5) . .
C8 C3 C4 118.6(5) . .
C8 C3 C2 121.3(5) . .
C4 C3 C2 120.1(5) . .
C5 C4 C3 120.5(6) . .
C5 C4 H4 119.7 . .
C3 C4 H4 119.7 . .
C4 C5 C6 120.6(6) . .
C4 C5 H5 119.7 . .
C6 C5 H5 119.7 . .
C7 C6 C5 119.6(6) . .
C7 C6 H6 120.2 . .
C5 C6 H6 120.2 . .
C6 C7 C8 120.3(6) . .
C6 C7 H7 119.9 . .
C8 C7 H7 119.9 . .
C3 C8 C7 120.3(5) . .
C3 C8 H8 119.8 . .
C7 C8 H8 119.8 . .
C14 C9 C10 120.5(5) . .
C14 C9 N1 118.7(5) . .
C10 C9 N1 120.7(4) . .
C9 C10 C11 118.9(5) . .
C9 C10 I1 122.6(4) . .
C11 C10 I1 118.5(4) . .
C12 C11 C10 120.0(5) . .
C12 C11 H11 120.0 . .
C10 C11 H11 120.0 . .
C13 C12 C11 120.9(5) . .
C13 C12 H12 119.5 . .
C11 C12 H12 119.5 . .
C12 C13 C14 119.6(5) . .
C12 C13 H13 120.2 . .
C14 C13 H13 120.2 . .
C13 C14 C9 120.1(5) . .
C13 C14 H14 119.9 . .
C9 C14 H14 119.9 . .
C1 N1 N2 110.7(4) . .
C1 N1 C9 128.0(4) . .
N2 N1 C9 121.3(4) . .
N3 N2 N1 106.8(4) . .
N2 N3 C2 109.5(4) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 N1 1.347(7) .
C1 C2 1.367(7) .
C1 H1 0.9300 .
C2 N3 1.357(6) .
C2 C3 1.473(7) .
C3 C8 1.383(8) .
C3 C4 1.402(7) .
C4 C5 1.370(8) .
C4 H4 0.9300 .
C5 C6 1.380(10) .
C5 H5 0.9300 .
C6 C7 1.379(10) .
C6 H6 0.9300 .
C7 C8 1.392(8) .
C7 H7 0.9300 .
C8 H8 0.9300 .
C9 C14 1.383(7) .
C9 C10 1.385(7) .
C9 N1 1.435(6) .
C10 C11 1.389(7) .
C10 I1 2.094(5) .
C11 C12 1.382(7) .
C11 H11 0.9300 .
C12 C13 1.368(9) .
C12 H12 0.9300 .
C13 C14 1.379(8) .
C13 H13 0.9300 .
C14 H14 0.9300 .
N1 N2 1.348(6) .
N2 N3 1.313(6) .
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
N1 C1 C2 N3 -0.7(6) . . . .
N1 C1 C2 C3 178.7(5) . . . .
N3 C2 C3 C8 -167.6(5) . . . .
C1 C2 C3 C8 13.0(8) . . . .
N3 C2 C3 C4 13.3(7) . . . .
C1 C2 C3 C4 -166.1(6) . . . .
C8 C3 C4 C5 -1.3(8) . . . .
C2 C3 C4 C5 177.8(5) . . . .
C3 C4 C5 C6 0.2(10) . . . .
C4 C5 C6 C7 1.0(10) . . . .
C5 C6 C7 C8 -1.2(10) . . . .
C4 C3 C8 C7 1.2(8) . . . .
C2 C3 C8 C7 -178.0(5) . . . .
C6 C7 C8 C3 0.1(9) . . . .
C14 C9 C10 C11 -0.1(8) . . . .
N1 C9 C10 C11 -178.1(5) . . . .
C14 C9 C10 I1 178.4(4) . . . .
N1 C9 C10 I1 0.4(7) . . . .
C9 C10 C11 C12 -0.1(8) . . . .
I1 C10 C11 C12 -178.6(4) . . . .
C10 C11 C12 C13 0.0(9) . . . .
C11 C12 C13 C14 0.3(9) . . . .
C12 C13 C14 C9 -0.5(9) . . . .
C10 C9 C14 C13 0.3(8) . . . .
N1 C9 C14 C13 178.4(5) . . . .
C2 C1 N1 N2 0.3(6) . . . .
C2 C1 N1 C9 -178.5(5) . . . .
C14 C9 N1 C1 -73.6(7) . . . .
C10 C9 N1 C1 104.4(6) . . . .
C14 C9 N1 N2 107.7(6) . . . .
C10 C9 N1 N2 -74.2(7) . . . .
C1 N1 N2 N3 0.3(6) . . . .
C9 N1 N2 N3 179.1(4) . . . .
N1 N2 N3 C2 -0.7(6) . . . .
C1 C2 N3 N2 0.9(6) . . . .
C3 C2 N3 N2 -178.6(5) . . . .
