#------------------------------------------------------------------------------
#$Date: 2023-09-15 04:44:37 +0300 (Fri, 15 Sep 2023) $
#$Revision: 286350 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/02/28/2022860.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_2022860
loop_
_publ_author_name
'Maharramov, Abel'
'Shikhaliyev, Namiq Q.'
'Abdullayeva, Afaq'
'Atakishiyeva, Gulnar T.'
'Niyazova, Ayten'
'Khrustalev, Victor N.'
'Gahramanova, Shahnaz I.'
'Atioğlu, Zeliha'
'Akkurt, Mehmet'
'Bhattarai, Ajaya'
_publ_section_title
;
 Crystal structure and Hirshfeld surface analysis of
 4-azido-2-(3,5-dimethylphenyl)-5-(4-nitrophenyl)-2H-1,2,3-triazole
;
_journal_coeditor_code           ZN2031
_journal_issue                   10
_journal_name_full
'Acta Crystallographica Section E Crystallographic Communications'
_journal_paper_doi               10.1107/S2056989023007855
_journal_volume                  79
_journal_year                    2023
_chemical_formula_iupac          'C16 H13 N7 O2'
_chemical_formula_moiety         'C16 H13 N7 O2'
_chemical_formula_sum            'C16 H13 N7 O2'
_chemical_formula_weight         335.33
_chemical_name_systematic
;
4-Azido-2-(3,5-dimethylphenyl)-5-(4-nitrophenyl)-2H-1,2,3-triazole
;
_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   geom
_atom_sites_solution_primary     difmap
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2013
_cell_angle_alpha                93.071(9)
_cell_angle_beta                 105.349(10)
_cell_angle_gamma                108.879(11)
_cell_formula_units_Z            2
_cell_length_a                   7.4400(8)
_cell_length_b                   9.9200(10)
_cell_length_c                   11.5200(13)
_cell_measurement_reflns_used    1000
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      28.0
_cell_measurement_theta_min      2.1
_cell_volume                     766.71(16)
_computing_cell_refinement
;
iMosflm (Battye et al.,  2011)
;
_computing_data_collection
;
Marccd (Doyle, 2011)
;
_computing_data_reduction
;
iMosflm (Battye et al.,  2011)
;
_computing_molecular_graphics
;
ORTEP-3 for Windows (Farrugia, 2012)
;
_computing_publication_material
;
PLATON (Spek, 2020)
;
_computing_structure_refinement
;
SHELXL (Sheldrick, 2015b)
;
_computing_structure_solution
;
SHELXT (Sheldrick, 2015a)
;
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measurement_device_type  'Rayonix SX165 CCD'
_diffrn_measurement_method       '/f scan'
_diffrn_radiation_type           synchrotron
_diffrn_radiation_wavelength     0.79313
_diffrn_reflns_av_R_equivalents  0.0248
_diffrn_reflns_av_unetI/netI     0.0220
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            13293
_diffrn_reflns_theta_full        28.417
_diffrn_reflns_theta_max         31.013
_diffrn_reflns_theta_min         2.070
_exptl_absorpt_coefficient_mu    0.131
_exptl_absorpt_correction_T_max  0.990
_exptl_absorpt_correction_T_min  0.969
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SCALA; Evans, 2006)
;
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.452
_exptl_crystal_description       prism
_exptl_crystal_F_000             348
_exptl_crystal_size_max          0.09
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.273
_refine_diff_density_min         -0.217
_refine_ls_extinction_coef       0.074(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.080
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     229
_refine_ls_number_reflns         3466
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.080
_refine_ls_R_factor_all          0.0529
_refine_ls_R_factor_gt           0.0463
_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)+(0.0764P)²+0.1976P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1274
_refine_ls_wR_factor_ref         0.1333
_reflns_number_gt                2976
_reflns_number_total             3466
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            zn2031sup1.cif
_cod_data_source_block           I
_cod_database_code               2022860
_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   0.988
_shelx_estimated_absorpt_t_max   0.996
_shelxl_version_number           .2013
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
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
_atom_site_disorder_assembly
_atom_site_disorder_group
O O1 0.18207(18) 0.76197(12) 0.92289(10) 0.0446(3) Uani d 1 . .
O O2 -0.03369(17) 0.69879(12) 0.74319(11) 0.0423(3) Uani d 1 . .
N N1 0.47322(16) 0.30620(12) 0.54670(10) 0.0295(3) Uani d 1 . .
N N2 0.59776(16) 0.23870(12) 0.53829(10) 0.0280(3) Uani d 1 . .
N N3 0.74669(16) 0.25675(12) 0.64053(10) 0.0295(3) Uani d 1 . .
N N4 0.83239(17) 0.38805(13) 0.84246(10) 0.0326(3) Uani d 1 . .
N N5 0.96905(17) 0.34031(13) 0.87091(10) 0.0332(3) Uani d 1 . .
N N6 1.10029(19) 0.30585(14) 0.91074(12) 0.0387(3) Uani d 1 . .
N N7 0.11839(19) 0.69804(13) 0.81792(11) 0.0343(3) Uani d 1 . .
C C4 0.71164(19) 0.34137(14) 0.71900(12) 0.0291(3) Uani d 1 . .
C C5 0.54163(19) 0.37371(14) 0.66201(12) 0.0282(3) Uani d 1 . .
C C6 0.57495(19) 0.15443(14) 0.42750(12) 0.0279(3) Uani d 1 . .
C C7 0.41649(19) 0.14311(14) 0.32646(12) 0.0284(3) Uani d 1 . .
H H7 0.3240 0.1885 0.3323 0.034 Uiso calc 1 . .
C C8 0.3946(2) 0.06480(14) 0.21667(12) 0.0305(3) Uani d 1 . .
C C9 0.5333(2) -0.00175(14) 0.21177(13) 0.0325(3) Uani d 1 . .
H H9 0.5185 -0.0562 0.1373 0.039 Uiso calc 1 . .
C C10 0.6915(2) 0.00999(15) 0.31301(13) 0.0331(3) Uani d 1 . .
C C11 0.7126(2) 0.08921(15) 0.42256(13) 0.0323(3) Uani d 1 . .
H H11 0.8196 0.0984 0.4929 0.039 Uiso calc 1 . .
C C12 0.2269(2) 0.05374(16) 0.10597(13) 0.0361(3) Uani d 1 . .
H H12A 0.1186 -0.0385 0.0952 0.054 Uiso calc 1 . .
H H12B 0.2744 0.0595 0.0341 0.054 Uiso calc 1 . .
H H12C 0.1783 0.1330 0.1163 0.054 Uiso calc 1 . .
C C13 0.8416(2) -0.05959(18) 0.30537(15) 0.0420(4) Uani d 1 . .
H H13A 0.9732 0.0151 0.3219 0.063 Uiso calc 1 . .
H H13B 0.8026 -0.1137 0.2236 0.063 Uiso calc 1 . .
H H13C 0.8465 -0.1254 0.3657 0.063 Uiso calc 1 . .
C C14 0.43732(19) 0.45871(14) 0.70518(12) 0.0280(3) Uani d 1 . .
C C15 0.5043(2) 0.53230(15) 0.82427(12) 0.0319(3) Uani d 1 . .
H H15 0.6221 0.5286 0.8796 0.038 Uiso calc 1 . .
C C16 0.4004(2) 0.61052(15) 0.86228(12) 0.0330(3) Uani d 1 . .
H H16 0.4453 0.6600 0.9433 0.040 Uiso calc 1 . .
C C17 0.2301(2) 0.61509(14) 0.77992(12) 0.0303(3) Uani d 1 . .
C C18 0.1596(2) 0.54308(15) 0.66123(13) 0.0326(3) Uani d 1 . .
H H18 0.0421 0.5477 0.6063 0.039 Uiso calc 1 . .
C C19 0.2631(2) 0.46465(15) 0.62443(12) 0.0317(3) Uani d 1 . .
H H19 0.2160 0.4142 0.5437 0.038 Uiso calc 1 . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0047 0.0021 '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 0.0086 0.0042 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0148 0.0078 '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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
N2 N1 C5 . . 104.92(11) ?
N1 N2 N3 . . 115.31(11) ?
N1 N2 C6 . . 121.86(11) ?
N3 N2 C6 . . 122.82(11) ?
C4 N3 N2 . . 102.74(11) ?
N5 N4 C4 . . 113.98(11) ?
N6 N5 N4 . . 171.56(14) ?
O1 N7 O2 . . 123.90(12) ?
O1 N7 C17 . . 117.93(12) ?
O2 N7 C17 . . 118.17(12) ?
N3 C4 C5 . . 110.21(11) ?
N3 C4 N4 . . 122.95(12) ?
C5 C4 N4 . . 126.83(12) ?
N1 C5 C4 . . 106.82(11) ?
N1 C5 C14 . . 120.20(12) ?
C4 C5 C14 . . 132.97(12) ?
C11 C6 C7 . . 121.96(12) ?
C11 C6 N2 . . 119.59(12) ?
C7 C6 N2 . . 118.43(11) ?
C6 C7 C8 . . 119.39(12) ?
C6 C7 H7 . . 120.3 ?
C8 C7 H7 . . 120.3 ?
C7 C8 C9 . . 118.67(13) ?
C7 C8 C12 . . 120.20(12) ?
C9 C8 C12 . . 121.13(12) ?
C10 C9 C8 . . 121.71(13) ?
C10 C9 H9 . . 119.1 ?
C8 C9 H9 . . 119.1 ?
C9 C10 C11 . . 119.17(13) ?
C9 C10 C13 . . 120.99(13) ?
C11 C10 C13 . . 119.84(13) ?
C6 C11 C10 . . 119.10(13) ?
C6 C11 H11 . . 120.4 ?
C10 C11 H11 . . 120.4 ?
C8 C12 H12A . . 109.5 ?
C8 C12 H12B . . 109.5 ?
H12A C12 H12B . . 109.5 ?
C8 C12 H12C . . 109.5 ?
H12A C12 H12C . . 109.5 ?
H12B C12 H12C . . 109.5 ?
C10 C13 H13A . . 109.5 ?
C10 C13 H13B . . 109.5 ?
H13A C13 H13B . . 109.5 ?
C10 C13 H13C . . 109.5 ?
H13A C13 H13C . . 109.5 ?
H13B C13 H13C . . 109.5 ?
C15 C14 C19 . . 119.20(12) ?
C15 C14 C5 . . 122.24(12) ?
C19 C14 C5 . . 118.56(12) ?
C16 C15 C14 . . 120.60(13) ?
C16 C15 H15 . . 119.7 ?
C14 C15 H15 . . 119.7 ?
C17 C16 C15 . . 118.67(12) ?
C17 C16 H16 . . 120.7 ?
C15 C16 H16 . . 120.7 ?
C16 C17 C18 . . 122.11(13) ?
C16 C17 N7 . . 119.61(12) ?
C18 C17 N7 . . 118.28(12) ?
C19 C18 C17 . . 118.84(13) ?
C19 C18 H18 . . 120.6 ?
C17 C18 H18 . . 120.6 ?
C18 C19 C14 . . 120.58(12) ?
C18 C19 H19 . . 119.7 ?
C14 C19 H19 . . 119.7 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
O1 N7 . 1.2284(16) ?
O2 N7 . 1.2296(17) ?
N1 N2 . 1.3261(15) ?
N1 C5 . 1.3410(16) ?
N2 N3 . 1.3435(15) ?
N2 C6 . 1.4268(17) ?
N3 C4 . 1.3323(17) ?
N4 N5 . 1.2317(16) ?
N4 C4 . 1.4242(17) ?
N5 N6 . 1.1299(17) ?
N7 C17 . 1.4681(17) ?
C4 C5 . 1.4069(18) ?
C5 C14 . 1.4640(18) ?
C6 C11 . 1.3876(18) ?
C6 C7 . 1.3897(18) ?
C7 C8 . 1.3905(18) ?
C7 H7 . 0.9500 ?
C8 C9 . 1.4043(19) ?
C8 C12 . 1.4995(19) ?
C9 C10 . 1.389(2) ?
C9 H9 . 0.9500 ?
C10 C11 . 1.3944(19) ?
C10 C13 . 1.5085(19) ?
C11 H11 . 0.9500 ?
C12 H12A . 0.9800 ?
C12 H12B . 0.9800 ?
C12 H12C . 0.9800 ?
C13 H13A . 0.9800 ?
C13 H13B . 0.9800 ?
C13 H13C . 0.9800 ?
C14 C15 . 1.3996(18) ?
C14 C19 . 1.4020(18) ?
C15 C16 . 1.3866(19) ?
C15 H15 . 0.9500 ?
C16 C17 . 1.383(2) ?
C16 H16 . 0.9500 ?
C17 C18 . 1.3886(19) ?
C18 C19 . 1.3798(19) ?
C18 H18 . 0.9500 ?
C19 H19 . 0.9500 ?
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
_geom_hbond_publ_flag
C7 H7 N1 . 0.95 2.47 2.7900(18) 100 no
C12 H12A N6 2_656 0.98 2.61 3.570(2) 166 yes
C15 H15 N4 . 0.95 2.51 3.174(2) 127 no
C19 H19 N1 . 0.95 2.47 2.810(2) 101 no
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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C5 N1 N2 N3 . . . . -0.26(15) ?
C5 N1 N2 C6 . . . . -179.58(11) ?
N1 N2 N3 C4 . . . . 0.38(15) ?
C6 N2 N3 C4 . . . . 179.70(12) ?
N2 N3 C4 C5 . . . . -0.34(14) ?
N2 N3 C4 N4 . . . . 179.00(12) ?
N5 N4 C4 N3 . . . . -1.69(19) ?
N5 N4 C4 C5 . . . . 177.54(13) ?
N2 N1 C5 C4 . . . . 0.03(14) ?
N2 N1 C5 C14 . . . . -179.08(11) ?
N3 C4 C5 N1 . . . . 0.21(15) ?
N4 C4 C5 N1 . . . . -179.10(12) ?
N3 C4 C5 C14 . . . . 179.16(13) ?
N4 C4 C5 C14 . . . . -0.1(2) ?
N1 N2 C6 C11 . . . . 178.22(12) ?
N3 N2 C6 C11 . . . . -1.1(2) ?
N1 N2 C6 C7 . . . . -0.33(19) ?
N3 N2 C6 C7 . . . . -179.60(11) ?
C11 C6 C7 C8 . . . . -0.3(2) ?
N2 C6 C7 C8 . . . . 178.25(12) ?
C6 C7 C8 C9 . . . . 0.5(2) ?
C6 C7 C8 C12 . . . . -178.79(12) ?
C7 C8 C9 C10 . . . . -0.6(2) ?
C12 C8 C9 C10 . . . . 178.72(13) ?
C8 C9 C10 C11 . . . . 0.4(2) ?
C8 C9 C10 C13 . . . . -178.68(13) ?
C7 C6 C11 C10 . . . . 0.0(2) ?
N2 C6 C11 C10 . . . . -178.46(12) ?
C9 C10 C11 C6 . . . . -0.1(2) ?
C13 C10 C11 C6 . . . . 178.98(13) ?
N1 C5 C14 C15 . . . . -179.28(12) ?
C4 C5 C14 C15 . . . . 1.9(2) ?
N1 C5 C14 C19 . . . . 1.52(19) ?
C4 C5 C14 C19 . . . . -177.31(14) ?
C19 C14 C15 C16 . . . . -0.1(2) ?
C5 C14 C15 C16 . . . . -179.32(12) ?
C14 C15 C16 C17 . . . . -0.4(2) ?
C15 C16 C17 C18 . . . . 0.5(2) ?
C15 C16 C17 N7 . . . . -179.59(12) ?
O1 N7 C17 C16 . . . . 0.4(2) ?
O2 N7 C17 C16 . . . . -179.18(12) ?
O1 N7 C17 C18 . . . . -179.69(12) ?
O2 N7 C17 C18 . . . . 0.70(19) ?
C16 C17 C18 C19 . . . . -0.1(2) ?
N7 C17 C18 C19 . . . . -179.95(12) ?
C17 C18 C19 C14 . . . . -0.5(2) ?
C15 C14 C19 C18 . . . . 0.6(2) ?
C5 C14 C19 C18 . . . . 179.82(12) ?

_cod_database_fobs_code 2022860
