#------------------------------------------------------------------------------
#$Date: 2024-04-05 02:03:31 +0300 (Fri, 05 Apr 2024) $
#$Revision: 290877 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/80/7248058.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_7248058
loop_
_publ_author_name
'Shishkina, Svitlana V.'
'Shaposhnyk, Anna M.'
'Dyakonenko, Viktoriya V.'
'Shyshkina, Mariia O.'
'Kovalenko, Sergiy M.'
_publ_section_title
;
 Use of quantum chemical methods to study concomitant polymorphs of a new
 benzimidazole-1,2,3-triazole hybrid compound
;
_journal_issue                   10
_journal_name_full               CrystEngComm
_journal_page_first              1481
_journal_page_last               1493
_journal_paper_doi               10.1039/D3CE01152F
_journal_volume                  26
_journal_year                    2024
_chemical_formula_moiety         'C16 H14 N6 O'
_chemical_formula_sum            'C16 H14 N6 O'
_chemical_formula_weight         306.33
_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   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2023-10-22
_audit_creation_method
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_audit_update_record
;
2023-11-10 deposited with the CCDC.	2024-01-30 downloaded from the CCDC.
;
_cell_angle_alpha                73.954(15)
_cell_angle_beta                 81.185(14)
_cell_angle_gamma                89.683(14)
_cell_formula_units_Z            2
_cell_length_a                   5.3231(9)
_cell_length_b                   11.4404(19)
_cell_length_c                   12.235(2)
_cell_measurement_reflns_used    1076
_cell_measurement_temperature    296.15
_cell_measurement_theta_max      25.5370
_cell_measurement_theta_min      3.6180
_cell_volume                     707.1(2)
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2016/6 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_diffrn_ambient_temperature      296.15
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.1827
_diffrn_detector_type            Sapphire3
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -57.00  -6.00   1.00   20.00    --  -20.51 -57.00 -60.00   51
  2  ω    -24.00  19.00   1.00   20.00    --  -20.51 -99.00 120.00   43
  3  ω    -92.00 -35.00   1.00   20.00    --  -20.51-178.00 -30.00   57
  4  ω    -23.00   4.00   1.00   20.00    --  -20.51 -99.00 -90.00   27
  5  ω      4.00  48.00   1.00   20.00    --   21.76 -37.00 -30.00   44
  6  ω      0.00  87.00   1.00   20.00    --   21.76  57.00 -90.00   87
  7  ω    -44.00  58.00   1.00   20.00    --   21.76 -19.00  90.00  102
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0500982000
_diffrn_orient_matrix_UB_12      -0.0457808000
_diffrn_orient_matrix_UB_13      0.0508524000
_diffrn_orient_matrix_UB_21      -0.0509489000
_diffrn_orient_matrix_UB_22      0.0454153000
_diffrn_orient_matrix_UB_23      0.0255138000
_diffrn_orient_matrix_UB_31      -0.1144739000
_diffrn_orient_matrix_UB_32      -0.0031279000
_diffrn_orient_matrix_UB_33      -0.0222425000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_unetI/netI     0.0979
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            2484
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        24.996
_diffrn_reflns_theta_max         24.996
_diffrn_reflns_theta_min         3.482
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.097
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.54633
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'light yellow'
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.439
_exptl_crystal_description       stick
_exptl_crystal_F_000             320
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.290
_refine_diff_density_min         -0.317
_refine_diff_density_rms         0.069
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     222
_refine_ls_number_reflns         2484
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.028
_refine_ls_R_factor_all          0.1126
_refine_ls_R_factor_gt           0.0819
_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)+(0.1147P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1984
_refine_ls_wR_factor_ref         0.2327
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1579
_reflns_number_total             2484
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d3ce01152f2.cif
_cod_data_source_block           1t
_cod_depositor_comments
'Adding full bibliography for 7248057--7248058.cif.'
_cod_database_code               7248058
_shelx_shelxl_version_number     2016/6
_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_max   0.995
_shelx_estimated_absorpt_t_min   0.983
_reflns_odcompleteness_completeness 99.82
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     27.50
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.786(5)
 0.214(5)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
3.a Aromatic/amide H refined with riding coordinates:
 C2(H2A), C3(H3), C4(H4), C5(H5), C11(H11), C12(H12), C13(H13), C14(H14)
3.b Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C)
;
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.731
_oxdiff_exptl_absorpt_empirical_full_min 0.657
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
O1 O -0.0445(5) 0.4379(2) 0.6687(2) 0.0499(8) Uani 1 1 d . . . . .
N1 N 0.6450(7) 0.2028(3) 0.3668(3) 0.0463(9) Uani 1 1 d . . . . .
N2 N 0.3221(6) 0.0778(3) 0.3676(3) 0.0379(8) Uani 1 1 d . . . . .
H2 H 0.192(11) 0.024(6) 0.395(5) 0.12(2) Uiso 1 1 d . . . . .
N3 N 0.0872(6) 0.1180(3) 0.5971(3) 0.0422(8) Uani 1 1 d . . . . .
N4 N 0.0425(6) 0.1594(3) 0.6876(3) 0.0444(9) Uani 1 1 d . . . . .
N5 N 0.2417(6) 0.2392(3) 0.6791(3) 0.0371(8) Uani 1 1 d . . . . .
N6 N 0.6203(7) 0.3217(3) 0.5472(4) 0.0482(10) Uani 1 1 d . . . . .
H6A H 0.731(13) 0.290(6) 0.482(6) 0.13(2) Uiso 1 1 d . . . . .
H6B H 0.688(9) 0.338(4) 0.603(4) 0.069(15) Uiso 1 1 d . . . . .
C1 C 0.6876(7) 0.1645(3) 0.2676(3) 0.0377(9) Uani 1 1 d . . . . .
C2 C 0.8903(8) 0.1905(4) 0.1769(4) 0.0474(11) Uani 1 1 d . . . . .
H2A H 1.025521 0.242165 0.175693 0.057 Uiso 1 1 calc R U . . .
C3 C 0.8846(8) 0.1375(4) 0.0896(4) 0.0473(10) Uani 1 1 d . . . . .
H3 H 1.018700 0.154010 0.028386 0.057 Uiso 1 1 calc R U . . .
C4 C 0.6844(8) 0.0599(4) 0.0896(3) 0.0481(11) Uani 1 1 d . . . . .
H4 H 0.687851 0.025224 0.029086 0.058 Uiso 1 1 calc R U . . .
C5 C 0.4808(8) 0.0336(4) 0.1782(3) 0.0424(10) Uani 1 1 d . . . . .
H5 H 0.345049 -0.017256 0.178296 0.051 Uiso 1 1 calc R U . . .
C6 C 0.4873(7) 0.0858(3) 0.2665(3) 0.0353(9) Uani 1 1 d . . . . .
C7 C 0.4237(7) 0.1483(3) 0.4235(3) 0.0384(9) Uani 1 1 d . . . . .
C8 C 0.3125(7) 0.1677(3) 0.5312(3) 0.0365(9) Uani 1 1 d . . . . .
C9 C 0.4115(7) 0.2454(3) 0.5835(3) 0.0361(9) Uani 1 1 d . . . . .
C10 C 0.2510(7) 0.3071(3) 0.7603(3) 0.0362(9) Uani 1 1 d . . . . .
C11 C 0.4123(8) 0.2764(4) 0.8402(3) 0.0458(11) Uani 1 1 d . . . . .
H11 H 0.514354 0.209874 0.842217 0.055 Uiso 1 1 calc R U . . .
C12 C 0.4253(8) 0.3428(4) 0.9176(4) 0.0480(11) Uani 1 1 d . . . . .
H12 H 0.533518 0.321127 0.972267 0.058 Uiso 1 1 calc R U . . .
C13 C 0.2765(8) 0.4409(4) 0.9127(4) 0.0500(11) Uani 1 1 d . . . . .
H13 H 0.283165 0.485886 0.964991 0.060 Uiso 1 1 calc R U . . .
C14 C 0.1163(8) 0.4749(4) 0.8318(4) 0.0499(11) Uani 1 1 d . . . . .
H14 H 0.017436 0.542490 0.829747 0.060 Uiso 1 1 calc R U . . .
C15 C 0.1021(7) 0.4092(3) 0.7540(3) 0.0378(9) Uani 1 1 d . . . . .
C16 C -0.1828(9) 0.5479(4) 0.6554(4) 0.0597(13) Uani 1 1 d . . . . .
H16A H -0.265066 0.561518 0.588698 0.089 Uiso 1 1 calc R U . . .
H16B H -0.067139 0.615244 0.646254 0.089 Uiso 1 1 calc R U . . .
H16C H -0.308445 0.540336 0.722499 0.089 Uiso 1 1 calc R U . . .
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'
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
C15 O1 C16 117.6(3) . . ?
C7 N1 C1 104.6(3) . . ?
C6 N2 H2 124(4) . . ?
C7 N2 H2 127(4) . . ?
C7 N2 C6 107.4(3) . . ?
N4 N3 C8 109.7(3) . . ?
N3 N4 N5 106.6(3) . . ?
N4 N5 C10 122.4(3) . . ?
C9 N5 N4 110.4(3) . . ?
C9 N5 C10 127.1(3) . . ?
H6A N6 H6B 122(5) . . ?
C9 N6 H6A 105(3) . . ?
C9 N6 H6B 115(3) . . ?
N1 C1 C2 130.5(4) . . ?
N1 C1 C6 110.2(3) . . ?
C2 C1 C6 119.3(4) . . ?
C1 C2 H2A 121.0 . . ?
C3 C2 C1 118.0(4) . . ?
C3 C2 H2A 121.0 . . ?
C2 C3 H3 119.0 . . ?
C2 C3 C4 122.0(4) . . ?
C4 C3 H3 119.0 . . ?
C3 C4 H4 119.5 . . ?
C5 C4 C3 121.0(4) . . ?
C5 C4 H4 119.5 . . ?
C4 C5 H5 121.4 . . ?
C6 C5 C4 117.1(4) . . ?
C6 C5 H5 121.4 . . ?
N2 C6 C1 104.9(3) . . ?
C5 C6 N2 132.5(3) . . ?
C5 C6 C1 122.6(4) . . ?
N1 C7 N2 112.9(3) . . ?
N1 C7 C8 121.2(3) . . ?
N2 C7 C8 126.0(3) . . ?
N3 C8 C7 126.7(3) . . ?
N3 C8 C9 108.1(3) . . ?
C9 C8 C7 125.1(3) . . ?
N5 C9 N6 124.6(3) . . ?
N5 C9 C8 105.1(3) . . ?
N6 C9 C8 130.1(3) . . ?
C11 C10 N5 120.7(4) . . ?
C11 C10 C15 120.2(3) . . ?
C15 C10 N5 119.1(3) . . ?
C10 C11 H11 119.5 . . ?
C10 C11 C12 120.9(4) . . ?
C12 C11 H11 119.5 . . ?
C11 C12 H12 120.6 . . ?
C13 C12 C11 118.7(4) . . ?
C13 C12 H12 120.6 . . ?
C12 C13 H13 119.3 . . ?
C12 C13 C14 121.4(4) . . ?
C14 C13 H13 119.3 . . ?
C13 C14 H14 119.8 . . ?
C15 C14 C13 120.3(4) . . ?
C15 C14 H14 119.8 . . ?
O1 C15 C10 117.1(3) . . ?
O1 C15 C14 124.5(4) . . ?
C14 C15 C10 118.4(4) . . ?
O1 C16 H16A 109.5 . . ?
O1 C16 H16B 109.5 . . ?
O1 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
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
O1 C15 1.365(4) . ?
O1 C16 1.437(5) . ?
N1 C1 1.387(5) . ?
N1 C7 1.333(5) . ?
N2 H2 0.89(6) . ?
N2 C6 1.384(5) . ?
N2 C7 1.354(5) . ?
N3 N4 1.310(4) . ?
N3 C8 1.367(5) . ?
N4 N5 1.376(4) . ?
N5 C9 1.350(5) . ?
N5 C10 1.427(4) . ?
N6 H6A 1.07(7) . ?
N6 H6B 0.88(5) . ?
N6 C9 1.357(5) . ?
C1 C2 1.392(5) . ?
C1 C6 1.404(5) . ?
C2 H2A 0.9300 . ?
C2 C3 1.371(6) . ?
C3 H3 0.9300 . ?
C3 C4 1.391(5) . ?
C4 H4 0.9300 . ?
C4 C5 1.380(5) . ?
C5 H5 0.9300 . ?
C5 C6 1.376(5) . ?
C7 C8 1.435(5) . ?
C8 C9 1.378(5) . ?
C10 C11 1.372(6) . ?
C10 C15 1.399(5) . ?
C11 H11 0.9300 . ?
C11 C12 1.377(5) . ?
C12 H12 0.9300 . ?
C12 C13 1.363(6) . ?
C13 H13 0.9300 . ?
C13 C14 1.378(6) . ?
C14 H14 0.9300 . ?
C14 C15 1.376(5) . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
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
N1 C1 C2 C3 178.8(4) . . . . ?
N1 C1 C6 N2 0.2(4) . . . . ?
N1 C1 C6 C5 -179.6(4) . . . . ?
N1 C7 C8 N3 179.6(4) . . . . ?
N1 C7 C8 C9 3.0(6) . . . . ?
N2 C7 C8 N3 0.7(6) . . . . ?
N2 C7 C8 C9 -176.0(4) . . . . ?
N3 N4 N5 C9 -0.9(4) . . . . ?
N3 N4 N5 C10 176.7(3) . . . . ?
N3 C8 C9 N5 0.1(4) . . . . ?
N3 C8 C9 N6 -174.7(4) . . . . ?
N4 N3 C8 C7 -177.8(4) . . . . ?
N4 N3 C8 C9 -0.7(4) . . . . ?
N4 N5 C9 N6 175.7(4) . . . . ?
N4 N5 C9 C8 0.4(4) . . . . ?
N4 N5 C10 C11 106.0(4) . . . . ?
N4 N5 C10 C15 -77.0(4) . . . . ?
N5 C10 C11 C12 178.9(3) . . . . ?
N5 C10 C15 O1 -0.2(5) . . . . ?
N5 C10 C15 C14 -179.0(3) . . . . ?
C1 N1 C7 N2 0.1(4) . . . . ?
C1 N1 C7 C8 -178.9(3) . . . . ?
C1 C2 C3 C4 0.0(6) . . . . ?
C2 C1 C6 N2 179.1(3) . . . . ?
C2 C1 C6 C5 -0.7(6) . . . . ?
C2 C3 C4 C5 0.5(6) . . . . ?
C3 C4 C5 C6 -1.0(6) . . . . ?
C4 C5 C6 N2 -178.6(4) . . . . ?
C4 C5 C6 C1 1.1(6) . . . . ?
C6 N2 C7 N1 0.0(4) . . . . ?
C6 N2 C7 C8 179.0(4) . . . . ?
C6 C1 C2 C3 0.1(6) . . . . ?
C7 N1 C1 C2 -178.9(4) . . . . ?
C7 N1 C1 C6 -0.2(4) . . . . ?
C7 N2 C6 C1 -0.1(4) . . . . ?
C7 N2 C6 C5 179.7(4) . . . . ?
C7 C8 C9 N5 177.3(3) . . . . ?
C7 C8 C9 N6 2.5(7) . . . . ?
C8 N3 N4 N5 1.0(4) . . . . ?
C9 N5 C10 C11 -76.9(5) . . . . ?
C9 N5 C10 C15 100.1(5) . . . . ?
C10 N5 C9 N6 -1.8(6) . . . . ?
C10 N5 C9 C8 -177.0(3) . . . . ?
C10 C11 C12 C13 -0.7(6) . . . . ?
C11 C10 C15 O1 176.8(3) . . . . ?
C11 C10 C15 C14 -2.0(6) . . . . ?
C11 C12 C13 C14 -0.5(6) . . . . ?
C12 C13 C14 C15 0.4(7) . . . . ?
C13 C14 C15 O1 -177.9(4) . . . . ?
C13 C14 C15 C10 0.8(6) . . . . ?
C15 C10 C11 C12 2.0(6) . . . . ?
C16 O1 C15 C10 -175.2(3) . . . . ?
C16 O1 C15 C14 3.5(6) . . . . ?
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.786(5)
2 0.214(5)
