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#$Date: 2025-08-23 02:36:08 +0300 (Sat, 23 Aug 2025) $
#$Revision: 301880 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/27/8102732.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_8102732
loop_
_publ_author_name
'Xue-Wen Zhu'
'Ying-Jun Zhang'
'Xu-Zhao Yang'
'Heng-Yu Qian'
'Chun-Xia Zhang'
_publ_section_title
;
 Crystal structure of 1-(1H-benzimidazole)methyl-1H-benztriazole
 dihydrate, C14H11N5 · 2H2O
;
_journal_issue                   2
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              405
_journal_volume                  225
_journal_year                    2010
_chemical_absolute_configuration unk
_chemical_formula_moiety         'C14 H11 N5, 2H2 O'
_chemical_formula_sum            'C14 H15 N5 O2'
_chemical_formula_weight         285.31
_chemical_name_common
'1-(1H-benzimidazole)methyl-1H-benztriazole dihydrate'
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      14
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_audit_update_record
;
2010-04-13 # Formatted by publCIF
;
_cell_angle_alpha                90.00
_cell_angle_beta                 97.03
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   12.437
_cell_length_b                   7.146
_cell_length_c                   15.922
_cell_measurement_reflns_used    500
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      26.4
_cell_measurement_theta_min      3.1
_cell_volume                     1404.426
_computing_cell_refinement       'CrysAlisPro, Oxford Diffraction Ltd.'
_computing_data_collection       'CrysAlisPro, Oxford Diffraction Ltd.'
_computing_data_reduction        'CrysAlisPro, Oxford Diffraction Ltd.'
_computing_molecular_graphics    'XP in SHELXTL (Sheldrick, 2008)'
_computing_publication_material  SHELXTL
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'φ and ω'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0299
_diffrn_reflns_av_sigmaI/netI    0.0438
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            6546
_diffrn_reflns_theta_full        26.37
_diffrn_reflns_theta_max         26.37
_diffrn_reflns_theta_min         3.13
_diffrn_source                   'fine-focus sealed tube'
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_number         6546
_exptl_absorpt_coefficient_mu    0.095
_exptl_absorpt_correction_T_max  0.9859
_exptl_absorpt_correction_T_min  0.9813
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            brown
_exptl_crystal_density_diffrn    1.349
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             600
_exptl_crystal_recrystallization_method ethanol/water
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.158
_refine_diff_density_min         -0.161
_refine_diff_density_rms         0.034
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.980
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     250
_refine_ls_number_reflns         2859
_refine_ls_number_restraints     6
_refine_ls_restrained_S_all      0.981
_refine_ls_R_factor_all          0.0741
_refine_ls_R_factor_gt           0.0409
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0427P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0863
_refine_ls_wR_factor_ref         0.0916
_reflns_number_gt                1670
_reflns_number_total             2859
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            1267-3018.cff
_cod_data_source_block           zxcv
_cod_original_cell_volume        1404.4
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               8102732
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'
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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.64651(11) -0.1998(2) 0.23105(9) 0.0685(4) Uani 1 1 d D . .
N5 N 0.59899(11) 0.2187(2) 0.44680(9) 0.0534(4) Uani 1 1 d . . .
C1 C 0.90307(12) -0.2423(2) 0.45565(9) 0.0396(4) Uani 1 1 d . . .
O2 O 0.67793(12) -0.52683(19) 0.32589(8) 0.0638(4) Uani 1 1 d D . .
N4 N 0.66264(9) -0.0626(2) 0.48980(7) 0.0422(3) Uani 1 1 d . . .
C13 C 0.64437(11) 0.0330(2) 0.56235(9) 0.0410(4) Uani 1 1 d . . .
N3 N 0.97117(12) -0.2753(2) 0.59189(8) 0.0557(4) Uani 1 1 d . . .
C3 C 1.09843(14) -0.2556(3) 0.48049(13) 0.0573(5) Uani 1 1 d . . .
C7 C 0.70648(14) -0.2478(3) 0.48533(12) 0.0479(4) Uani 1 1 d . . .
C2 C 0.99883(13) -0.2569(2) 0.51095(10) 0.0452(4) Uani 1 1 d . . .
C6 C 0.90341(14) -0.2238(3) 0.36840(10) 0.0498(5) Uani 1 1 d . . .
N2 N 0.86654(13) -0.2740(2) 0.58866(8) 0.0561(4) Uani 1 1 d . . .
C8 C 0.60466(12) 0.2067(3) 0.53487(10) 0.0452(4) Uani 1 1 d . . .
C14 C 0.63340(13) 0.0566(3) 0.42394(11) 0.0498(5) Uani 1 1 d . . .
C4 C 1.09945(15) -0.2397(3) 0.39527(14) 0.0623(5) Uani 1 1 d . . .
C12 C 0.65872(14) -0.0187(3) 0.64722(10) 0.0509(5) Uani 1 1 d . . .
C10 C 0.59265(16) 0.2878(3) 0.67785(14) 0.0638(6) Uani 1 1 d . . .
C9 C 0.57778(14) 0.3383(3) 0.59398(13) 0.0564(5) Uani 1 1 d . . .
C5 C 1.00202(15) -0.2238(3) 0.34034(13) 0.0606(5) Uani 1 1 d . . .
C11 C 0.63235(15) 0.1131(3) 0.70387(13) 0.0624(6) Uani 1 1 d . . .
N1 N 0.82330(10) -0.25418(19) 0.50677(8) 0.0434(3) Uani 1 1 d . . .
H7B H 0.6772(12) -0.327(2) 0.5248(10) 0.047(4) Uiso 1 1 d . . .
H14 H 0.6422(12) 0.014(2) 0.3684(11) 0.058(5) Uiso 1 1 d . . .
H4 H 1.1671(15) -0.240(2) 0.3702(10) 0.060(5) Uiso 1 1 d . . .
H12 H 0.6860(12) -0.141(3) 0.6650(10) 0.048(5) Uiso 1 1 d . . .
H6 H 0.8330(14) -0.215(2) 0.3308(10) 0.058(5) Uiso 1 1 d . . .
H7A H 0.6903(13) -0.301(2) 0.4287(11) 0.058(5) Uiso 1 1 d . . .
H2B H 0.7318(11) -0.585(3) 0.3107(11) 0.081(7) Uiso 1 1 d D . .
H10 H 0.5738(14) 0.372(3) 0.7205(11) 0.070(6) Uiso 1 1 d . . .
H9 H 0.5495(13) 0.458(3) 0.5738(10) 0.056(5) Uiso 1 1 d . . .
H5 H 1.0084(14) -0.207(2) 0.2830(12) 0.071(6) Uiso 1 1 d . . .
H2A H 0.6479(17) -0.591(3) 0.3606(12) 0.121(10) Uiso 1 1 d D . .
H1B H 0.6525(17) -0.3090(18) 0.2516(13) 0.091(8) Uiso 1 1 d D . .
H3 H 1.1627(16) -0.265(3) 0.5164(12) 0.075(6) Uiso 1 1 d . . .
H11 H 0.6413(14) 0.084(3) 0.7635(12) 0.077(6) Uiso 1 1 d . . .
H1A H 0.5931(16) -0.199(4) 0.1937(13) 0.149(12) Uiso 1 1 d 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'
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
H1B O1 H1A 107.9(19) . . ?
C14 N5 C8 104.37(15) . . ?
N1 C1 C2 104.27(13) . . ?
N1 C1 C6 133.82(15) . . ?
C2 C1 C6 121.90(15) . . ?
H2B O2 H2A 110.8(18) . . ?
C14 N4 C13 106.09(15) . . ?
C14 N4 C7 127.15(15) . . ?
C13 N4 C7 126.74(14) . . ?
N4 C13 C8 105.49(13) . . ?
N4 C13 C12 131.64(17) . . ?
C8 C13 C12 122.86(16) . . ?
N2 N3 C2 109.04(13) . . ?
C4 C3 C2 117.84(17) . . ?
C4 C3 H3 120.5(12) . . ?
C2 C3 H3 121.6(12) . . ?
N4 C7 N1 113.11(14) . . ?
N4 C7 H7B 109.9(9) . . ?
N1 C7 H7B 106.1(9) . . ?
N4 C7 H7A 111.5(10) . . ?
N1 C7 H7A 107.0(9) . . ?
H7B C7 H7A 109.0(14) . . ?
N3 C2 C3 131.58(16) . . ?
N3 C2 C1 107.76(14) . . ?
C3 C2 C1 120.63(16) . . ?
C5 C6 C1 116.17(17) . . ?
C5 C6 H6 124.3(9) . . ?
C1 C6 H6 119.5(9) . . ?
N3 N2 N1 108.48(13) . . ?
C13 C8 N5 110.09(14) . . ?
C13 C8 C9 119.64(16) . . ?
N5 C8 C9 130.27(18) . . ?
N5 C14 N4 113.96(16) . . ?
N5 C14 H14 128.3(10) . . ?
N4 C14 H14 117.7(10) . . ?
C3 C4 C5 120.81(18) . . ?
C3 C4 H4 121.4(9) . . ?
C5 C4 H4 117.7(10) . . ?
C11 C12 C13 116.3(2) . . ?
C11 C12 H12 122.1(9) . . ?
C13 C12 H12 121.6(9) . . ?
C9 C10 C11 121.8(2) . . ?
C9 C10 H10 120.5(11) . . ?
C11 C10 H10 117.7(11) . . ?
C10 C9 C8 117.5(2) . . ?
C10 C9 H9 123.8(9) . . ?
C8 C9 H9 118.7(9) . . ?
C6 C5 C4 122.64(19) . . ?
C6 C5 H5 120.7(11) . . ?
C4 C5 H5 116.6(11) . . ?
C12 C11 C10 121.79(19) . . ?
C12 C11 H11 119.2(12) . . ?
C10 C11 H11 119.0(12) . . ?
N2 N1 C1 110.45(13) . . ?
N2 N1 C7 119.81(14) . . ?
C1 N1 C7 129.74(13) . . ?
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 H1B 0.846(9) . ?
O1 H1A 0.836(10) . ?
N5 C14 1.302(2) . ?
N5 C8 1.398(2) . ?
C1 N1 1.3606(19) . ?
C1 C2 1.396(2) . ?
C1 C6 1.396(2) . ?
O2 H2B 0.848(9) . ?
O2 H2A 0.838(10) . ?
N4 C14 1.366(2) . ?
N4 C13 1.3848(19) . ?
N4 C7 1.436(2) . ?
C13 C8 1.387(2) . ?
C13 C12 1.391(2) . ?
N3 N2 1.296(2) . ?
N3 C2 1.380(2) . ?
C3 C4 1.363(3) . ?
C3 C2 1.384(3) . ?
C3 H3 0.93(2) . ?
C7 N1 1.452(2) . ?
C7 H7B 0.953(15) . ?
C7 H7A 0.976(17) . ?
C6 C5 1.356(2) . ?
C6 H6 1.000(17) . ?
N2 N1 1.3557(18) . ?
C8 C9 1.400(3) . ?
C14 H14 0.954(16) . ?
C4 C5 1.410(3) . ?
C4 H4 0.975(17) . ?
C12 C11 1.372(3) . ?
C12 H12 0.967(17) . ?
C10 C9 1.374(3) . ?
C10 C11 1.387(3) . ?
C10 H10 0.959(18) . ?
C9 H9 0.967(18) . ?
C5 H5 0.935(19) . ?
C11 H11 0.965(18) . ?
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
O2 H2B O1 0.848(9) 1.911(9) 2.7571(19) 175.1(19) 2_645
O2 H2A N5 0.838(10) 2.078(11) 2.905(2) 169(2) 1_545
O1 H1A N3 0.836(10) 2.088(11) 2.918(2) 172(3) 4
C11 H11 N2 0.956(19) 2.576(19) 3.399(2) 143.3(17) 2_656
C3 H3 Cg2 0.93(2) 2.89(2) 3.5677(19) 130.7(15) 3_756
C4 H4 Cg4 0.975(17) 2.714(19) 3.592(2) 150.2(12) 3_756
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
C14 N4 C13 C8 -0.02(15) . . . . ?
C7 N4 C13 C8 178.33(14) . . . . ?
C14 N4 C13 C12 179.58(15) . . . . ?
C7 N4 C13 C12 -2.1(3) . . . . ?
C14 N4 C7 N1 100.05(18) . . . . ?
C13 N4 C7 N1 -77.97(19) . . . . ?
N2 N3 C2 C3 -177.96(18) . . . . ?
N2 N3 C2 C1 0.43(19) . . . . ?
C4 C3 C2 N3 178.23(18) . . . . ?
C4 C3 C2 C1 0.0(3) . . . . ?
N1 C1 C2 N3 -0.42(17) . . . . ?
C6 C1 C2 N3 -179.38(15) . . . . ?
N1 C1 C2 C3 178.19(15) . . . . ?
C6 C1 C2 C3 -0.8(3) . . . . ?
N1 C1 C6 C5 -177.57(18) . . . . ?
C2 C1 C6 C5 1.0(3) . . . . ?
C2 N3 N2 N1 -0.26(19) . . . . ?
N4 C13 C8 N5 -0.31(16) . . . . ?
C12 C13 C8 N5 -179.95(14) . . . . ?
N4 C13 C8 C9 179.96(14) . . . . ?
C12 C13 C8 C9 0.3(2) . . . . ?
C14 N5 C8 C13 0.52(18) . . . . ?
C14 N5 C8 C9 -179.79(18) . . . . ?
C8 N5 C14 N4 -0.55(18) . . . . ?
C13 N4 C14 N5 0.37(18) . . . . ?
C7 N4 C14 N5 -177.97(14) . . . . ?
C2 C3 C4 C5 0.5(3) . . . . ?
N4 C13 C12 C11 179.80(16) . . . . ?
C8 C13 C12 C11 -0.7(2) . . . . ?
C11 C10 C9 C8 -0.2(3) . . . . ?
C13 C8 C9 C10 0.1(2) . . . . ?
N5 C8 C9 C10 -179.53(16) . . . . ?
C1 C6 C5 C4 -0.6(3) . . . . ?
C3 C4 C5 C6 -0.2(3) . . . . ?
C13 C12 C11 C10 0.6(3) . . . . ?
C9 C10 C11 C12 -0.1(3) . . . . ?
N3 N2 N1 C1 -0.01(19) . . . . ?
N3 N2 N1 C7 -179.77(14) . . . . ?
C2 C1 N1 N2 0.27(17) . . . . ?
C6 C1 N1 N2 179.05(18) . . . . ?
C2 C1 N1 C7 180.00(16) . . . . ?
C6 C1 N1 C7 -1.2(3) . . . . ?
N4 C7 N1 N2 87.25(18) . . . . ?
N4 C7 N1 C1 -92.5(2) . . . . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30653988
2 PubChem 139207286
