#------------------------------------------------------------------------------
#$Date: 2025-08-18 18:33:07 +0300 (Mon, 18 Aug 2025) $
#$Revision: 301779 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/54/66/1546647.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_1546647
loop_
_publ_author_name
'Sahbi, Azzeddine'
'Fichtali, Ismail'
'Mague, Joel T.'
'Ben-Tama, Abdeslem'
'El Hadrami, El Mestafa'
'Kandri Rodi, Youssef'
_publ_section_title
;
 1-[(1-Benzyl-1H-1,2,3-triazol-4-yl)methyl]-1H-1,3-benzodiazole
;
_journal_coeditor_code           VM4024
_journal_issue                   6
_journal_name_full               IUCrData
_journal_page_first              x170944
_journal_paper_doi               10.1107/S2414314617009440
_journal_volume                  2
_journal_year                    2017
_chemical_formula_iupac          'C17 H15 N5'
_chemical_formula_moiety         'C17 H15 N5'
_chemical_formula_sum            'C17 H15 N5'
_chemical_formula_weight         289.34
_chemical_name_systematic
;
1-[(1-Benzyl-1H-1,2,3-triazol-4-yl)methyl]-1H-1,3-benzodiazole
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 97.4510(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   5.34830(10)
_cell_length_b                   14.1861(4)
_cell_length_c                   19.1408(5)
_cell_measurement_reflns_used    8031
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      72.3826
_cell_measurement_theta_min      3.8903
_cell_volume                     1439.98(6)
_computing_cell_refinement
;
SAINT (Bruker, 2016)
;
_computing_data_collection
;
APEX3 (Bruker, 2016)
;
_computing_data_reduction
;
SAINT  (Bruker, 2016)
;
_computing_molecular_graphics
;
DIAMOND (Brandenburg & Putz, 2012)
;
_computing_publication_material
;
SHELXTL (Sheldrick, 2008)
;
_computing_structure_refinement
;
SHELXL2014 (Sheldrick, 2015b)
;
_computing_structure_solution
;
SHELXT (Sheldrick, 2015a)
;
_diffrn_ambient_temperature      150(2)
_diffrn_detector_area_resol_mean 10.4167
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measurement_device_type  'Bruker D8 VENTURE PHOTON 100 CMOS'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0368
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            10936
_diffrn_reflns_theta_full        70.000
_diffrn_reflns_theta_max         72.375
_diffrn_reflns_theta_min         3.890
_exptl_absorpt_coefficient_mu    0.668
_exptl_absorpt_correction_T_max  0.99
_exptl_absorpt_correction_T_min  0.88
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Bruker, 2016)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.335
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       column
_exptl_crystal_F_000             608
_exptl_crystal_size_max          0.126
_exptl_crystal_size_mid          0.027
_exptl_crystal_size_min          0.018
_refine_diff_density_max         0.222
_refine_diff_density_min         -0.191
_refine_ls_extinction_coef       0.0040(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method
;
SHELXL2014 (Sheldrick, 2015b)
;
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     260
_refine_ls_number_reflns         2817
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.044
_refine_ls_R_factor_all          0.0477
_refine_ls_R_factor_gt           0.0398
_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)+(0.0421P)²+0.4698P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0919
_refine_ls_wR_factor_ref         0.0974
_reflns_number_gt                2427
_reflns_number_total             2817
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            vm4024sup1.cif
_cod_data_source_block           I
_cod_database_code               1546647
_cod_database_fobs_code          1546647
_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   0.921
_shelx_estimated_absorpt_t_max   0.988
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
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
N N1 0.7517(2) 0.58381(8) 0.31394(6) 0.0260(3) Uani d 1
N N2 0.5371(2) 0.57393(8) 0.34255(7) 0.0304(3) Uani d 1
N N3 0.5770(2) 0.50948(8) 0.39222(6) 0.0311(3) Uani d 1
N N4 0.8363(2) 0.30988(8) 0.42456(6) 0.0294(3) Uani d 1
N N5 0.8012(2) 0.17383(9) 0.36442(7) 0.0333(3) Uani d 1
C C1 0.8262(3) 0.75148(10) 0.28669(7) 0.0288(3) Uani d 1
C C2 0.6539(3) 0.82402(11) 0.26945(8) 0.0361(4) Uani d 1
H H2 0.501(3) 0.8069(11) 0.2382(9) 0.032(4) Uiso d 1
C C3 0.7079(3) 0.91481(11) 0.29475(9) 0.0400(4) Uani d 1
H H3 0.583(4) 0.9651(14) 0.2822(11) 0.054(6) Uiso d 1
C C4 0.9291(3) 0.93358(11) 0.33753(9) 0.0374(4) Uani d 1
H H4 0.968(4) 0.9963(14) 0.3562(10) 0.049(5) Uiso d 1
C C5 1.1014(3) 0.86152(11) 0.35485(9) 0.0369(4) Uani d 1
H H5 1.261(4) 0.8760(14) 0.3857(11) 0.057(6) Uiso d 1
C C6 1.0509(3) 0.77114(10) 0.32907(8) 0.0325(3) Uani d 1
H H6 1.180(4) 0.7212(14) 0.3406(10) 0.048(5) Uiso d 1
C C7 0.7674(3) 0.65365(11) 0.25806(8) 0.0345(3) Uani d 1
H H7A 0.597(4) 0.6530(13) 0.2267(10) 0.046(5) Uiso d 1
H H7B 0.906(4) 0.6283(13) 0.2324(10) 0.047(5) Uiso d 1
C C8 0.9303(3) 0.52577(10) 0.34520(8) 0.0304(3) Uani d 1
H H8 1.098(4) 0.5242(14) 0.3302(11) 0.057(6) Uiso d 1
C C9 0.8188(3) 0.47873(9) 0.39500(7) 0.0275(3) Uani d 1
C C10 0.9266(3) 0.40447(10) 0.44536(9) 0.0386(4) Uani d 1
H H10A 0.865(4) 0.4130(14) 0.4933(11) 0.052(5) Uiso d 1
H H10B 1.120(4) 0.4052(14) 0.4484(11) 0.055(6) Uiso d 1
C C11 0.9143(3) 0.25572(10) 0.37299(8) 0.0331(3) Uani d 1
H H11 1.051(3) 0.2804(12) 0.3460(9) 0.038(4) Uiso d 1
C C12 0.6362(3) 0.17317(10) 0.41504(7) 0.0283(3) Uani d 1
C C13 0.4702(3) 0.10355(11) 0.43167(9) 0.0366(4) Uani d 1
H H13 0.455(4) 0.0418(14) 0.4059(10) 0.048(5) Uiso d 1
C C14 0.3266(3) 0.12212(13) 0.48488(9) 0.0449(4) Uani d 1
H H14 0.209(4) 0.0736(15) 0.4972(11) 0.055(6) Uiso d 1
C C15 0.3451(3) 0.20763(14) 0.52117(9) 0.0468(4) Uani d 1
H H15 0.243(4) 0.2214(15) 0.5597(11) 0.059(6) Uiso d 1
C C16 0.5087(3) 0.27775(12) 0.50617(8) 0.0376(4) Uani d 1
H H16 0.528(4) 0.3390(15) 0.5321(11) 0.056(6) Uiso d 1
C C17 0.6542(3) 0.25882(9) 0.45272(7) 0.0278(3) 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'
N N 0.0311 0.0180 '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
C8 N1 N2 110.57(11)
C8 N1 C7 129.36(12)
N2 N1 C7 120.03(12)
N3 N2 N1 107.45(11)
N2 N3 C9 108.41(11)
C11 N4 C17 106.63(12)
C11 N4 C10 126.47(13)
C17 N4 C10 126.90(13)
C11 N5 C12 104.06(12)
C6 C1 C2 119.09(14)
C6 C1 C7 121.34(13)
C2 C1 C7 119.56(14)
C1 C2 C3 120.01(15)
C1 C2 H2 115.8(10)
C3 C2 H2 124.1(10)
C4 C3 C2 120.65(14)
C4 C3 H3 120.6(12)
C2 C3 H3 118.8(12)
C3 C4 C5 119.56(15)
C3 C4 H4 121.5(12)
C5 C4 H4 119.0(12)
C4 C5 C6 120.22(15)
C4 C5 H5 118.9(12)
C6 C5 H5 120.9(12)
C5 C6 C1 120.47(14)
C5 C6 H6 118.9(11)
C1 C6 H6 120.7(11)
N1 C7 C1 112.61(12)
N1 C7 H7A 106.8(11)
C1 C7 H7A 110.3(11)
N1 C7 H7B 103.3(11)
C1 C7 H7B 112.0(11)
H7A C7 H7B 111.5(15)
N1 C8 C9 105.16(12)
N1 C8 H8 120.7(12)
C9 C8 H8 134.1(12)
N3 C9 C8 108.42(12)
N3 C9 C10 122.53(14)
C8 C9 C10 129.04(14)
N4 C10 C9 112.66(12)
N4 C10 H10A 102.7(11)
C9 C10 H10A 110.8(11)
N4 C10 H10B 108.6(11)
C9 C10 H10B 109.3(11)
H10A C10 H10B 112.7(16)
N5 C11 N4 114.34(13)
N5 C11 H11 126.6(10)
N4 C11 H11 119.1(10)
C13 C12 N5 130.10(13)
C13 C12 C17 119.86(14)
N5 C12 C17 110.04(12)
C14 C13 C12 117.79(15)
C14 C13 H13 120.8(11)
C12 C13 H13 121.4(11)
C13 C14 C15 121.59(16)
C13 C14 H14 118.7(12)
C15 C14 H14 119.7(12)
C16 C15 C14 121.96(15)
C16 C15 H15 116.0(13)
C14 C15 H15 122.1(13)
C15 C16 C17 116.42(15)
C15 C16 H16 123.4(12)
C17 C16 H16 120.2(12)
N4 C17 C16 132.69(14)
N4 C17 C12 104.93(12)
C16 C17 C12 122.38(14)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
N1 C8 1.3416(18)
N1 N2 1.3420(16)
N1 C7 1.4684(18)
N2 N3 1.3163(17)
N3 C9 1.3592(18)
N4 C11 1.3585(19)
N4 C17 1.3784(18)
N4 C10 1.4638(18)
N5 C11 1.3102(19)
N5 C12 1.3927(18)
C1 C6 1.388(2)
C1 C2 1.392(2)
C1 C7 1.510(2)
C2 C3 1.393(2)
C2 H2 0.977(18)
C3 C4 1.374(3)
C3 H3 0.98(2)
C4 C5 1.387(2)
C4 H4 0.97(2)
C5 C6 1.388(2)
C5 H5 1.00(2)
C6 H6 0.992(19)
C7 H7A 1.025(19)
C7 H7B 1.01(2)
C8 C9 1.363(2)
C8 H8 0.98(2)
C9 C10 1.492(2)
C10 H10A 1.02(2)
C10 H10B 1.03(2)
C11 H11 1.011(18)
C12 C13 1.392(2)
C12 C17 1.4100(19)
C13 C14 1.378(2)
C13 H13 1.00(2)
C14 C15 1.395(3)
C14 H14 0.98(2)
C15 C16 1.379(3)
C15 H15 0.99(2)
C16 C17 1.389(2)
C16 H16 1.00(2)
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
C7 H7A N5 2_655 1.025(19) 2.59(2) 3.602(2) 170.2(15)
C7 H7B N5 2_755 1.01(2) 2.66(2) 3.5076(19) 142.4(14)
C8 H8 N2 1_655 0.98(2) 2.44(2) 3.3228(18) 151.1(17)
C16 H16 N3 3_666 1.00(2) 2.69(2) 3.652(2) 161.2(16)
C15 H15 Cg3 3_666 0.99(2) 2.77(2) 3.6216(18) 143.9(16)
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
C8 N1 N2 N3 -0.05(15)
C7 N1 N2 N3 -178.06(12)
N1 N2 N3 C9 0.14(15)
C6 C1 C2 C3 -0.1(2)
C7 C1 C2 C3 -179.06(13)
C1 C2 C3 C4 -0.8(2)
C2 C3 C4 C5 0.8(2)
C3 C4 C5 C6 0.1(2)
C4 C5 C6 C1 -1.0(2)
C2 C1 C6 C5 1.1(2)
C7 C1 C6 C5 179.97(13)
C8 N1 C7 C1 -94.48(17)
N2 N1 C7 C1 83.11(16)
C6 C1 C7 N1 62.58(18)
C2 C1 C7 N1 -118.51(15)
N2 N1 C8 C9 -0.06(15)
C7 N1 C8 C9 177.71(13)
N2 N3 C9 C8 -0.18(16)
N2 N3 C9 C10 -179.41(12)
N1 C8 C9 N3 0.14(16)
N1 C8 C9 C10 179.30(13)
C11 N4 C10 C9 76.8(2)
C17 N4 C10 C9 -102.42(17)
N3 C9 C10 N4 74.92(19)
C8 C9 C10 N4 -104.13(18)
C12 N5 C11 N4 -0.66(17)
C17 N4 C11 N5 -0.01(18)
C10 N4 C11 N5 -179.34(13)
C11 N5 C12 C13 -178.60(15)
C11 N5 C12 C17 1.07(16)
N5 C12 C13 C14 -179.81(15)
C17 C12 C13 C14 0.5(2)
C12 C13 C14 C15 0.1(2)
C13 C14 C15 C16 -0.4(3)
C14 C15 C16 C17 0.2(2)
C11 N4 C17 C16 -179.96(15)
C10 N4 C17 C16 -0.6(2)
C11 N4 C17 C12 0.66(15)
C10 N4 C17 C12 179.99(13)
C15 C16 C17 N4 -178.83(15)
C15 C16 C17 C12 0.5(2)
C13 C12 C17 N4 178.63(13)
N5 C12 C17 N4 -1.09(15)
C13 C12 C17 C16 -0.8(2)
N5 C12 C17 C16 179.45(13)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 129841592
