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#$Date: 2025-08-22 17:55:42 +0300 (Fri, 22 Aug 2025) $
#$Revision: 301864 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/21/89/7218906.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_7218906
loop_
_publ_author_name
'Seth, Saikat Kumar'
'Lee, Vannajan Sanghiran'
'Yana, Janchai'
'Zain, Sharifuddin M.'
'Cunha, Anna C.'
'Ferreira, Vitor F.'
'Jordão, Alessandro K.'
'de Souza, Maria C. B. V.'
'Wardell, Solange M. S. V.'
'Wardell, James L.'
'Tiekink, Edward R. T.'
_publ_section_title
;
 Crystallographic and computational study of
 1-(arylamino)-1,2,3-triazole-4-carbohydrazides
;
_journal_issue                   11
_journal_name_full               CrystEngComm
_journal_page_first              2255
_journal_paper_doi               10.1039/C4CE02175D
_journal_volume                  17
_journal_year                    2015
_chemical_formula_moiety         'C10 H11 Br N6 O'
_chemical_formula_sum            'C10 H11 Br N6 O'
_chemical_formula_weight         311.16
_space_group_IT_number           61
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_audit_update_record
;
2013-04-15 deposited with the CCDC.
2014-11-25 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   11.3672(4)
_cell_length_b                   7.2817(2)
_cell_length_c                   30.1714(11)
_cell_measurement_reflns_used    3211
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      27.48
_cell_measurement_theta_min      1.00
_cell_volume                     2497.36(14)
_computing_cell_refinement       'DENZO (Otwinowski & Minor, 1997) & COLLECT'
_computing_data_collection       'COLLECT (Hooft, 1998)'
_computing_data_reduction        'DENZO & COLLECT'
_computing_molecular_graphics
'ORTEP-3 for Windows (Farrugia, 1997), DIAMOND (Brandenburg, 2006)'
_computing_publication_material  'publCIF (Westrip, 2010)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      120(2)
_diffrn_detector_area_resol_mean 9.091
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Enraf Nonius KappaCCD area detector'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  '10 cm confocal mirrors'
_diffrn_radiation_source         'Enraf Nonius FR591 rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0445
_diffrn_reflns_av_sigmaI/netI    0.0364
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       39
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            13981
_diffrn_reflns_theta_full        27.49
_diffrn_reflns_theta_max         27.49
_diffrn_reflns_theta_min         3.24
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    3.290
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.736348
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2007)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.655
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1248
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.368
_refine_diff_density_min         -0.583
_refine_diff_density_rms         0.071
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     176
_refine_ls_number_reflns         2856
_refine_ls_number_restraints     4
_refine_ls_restrained_S_all      1.021
_refine_ls_R_factor_all          0.0562
_refine_ls_R_factor_gt           0.0301
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0292P)²+1.5145P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0639
_refine_ls_wR_factor_ref         0.0731
_reflns_number_gt                2078
_reflns_number_total             2856
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            c4ce02175d2.cif
_cod_data_source_block           br
_cod_depositor_comments
'Adding full bibliography for 7218903--7218906.cif.'
_cod_database_code               7218906
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x+1/2, -y, z+1/2'
'-x, -y, -z'
'-x-1/2, y-1/2, z'
'x, -y-1/2, z-1/2'
'x-1/2, y, -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
Br1 Br 0.89309(3) 0.81774(4) 0.837804(8) 0.03841(10) Uani 1 1 d .
O1 O 1.17419(15) 1.0628(2) 0.52449(6) 0.0391(4) Uani 1 1 d .
N1 N 1.12186(18) 1.3962(3) 0.48636(7) 0.0347(5) Uani 1 1 d D
H1N H 1.154(2) 1.306(3) 0.4707(8) 0.042 Uiso 1 1 d D
H2N H 1.1877(15) 1.437(3) 0.4982(8) 0.042 Uiso 1 1 d D
N2 N 1.05369(18) 1.3061(3) 0.51928(6) 0.0286(4) Uani 1 1 d D
H3N H 0.9875(14) 1.360(3) 0.5265(8) 0.034 Uiso 1 1 d D
N3 N 0.89750(16) 1.1430(3) 0.57893(6) 0.0248(4) Uani 1 1 d .
N4 N 0.84167(16) 1.0360(3) 0.60654(6) 0.0253(4) Uani 1 1 d .
N5 N 0.90903(16) 0.8823(3) 0.61141(6) 0.0222(4) Uani 1 1 d .
N6 N 0.87344(16) 0.7365(3) 0.63788(6) 0.0247(4) Uani 1 1 d D
H4N H 0.8083(13) 0.687(3) 0.6285(7) 0.030 Uiso 1 1 d D
C1 C 1.0836(2) 1.1423(3) 0.53513(7) 0.0251(5) Uani 1 1 d .
C2 C 0.99944(19) 1.0588(3) 0.56653(6) 0.0212(5) Uani 1 1 d .
C3 C 1.00893(19) 0.8908(3) 0.58712(7) 0.0214(5) Uani 1 1 d .
C4 C 1.0977(2) 0.7420(3) 0.58642(8) 0.0303(5) Uani 1 1 d .
H4A H 1.0578 0.6227 0.5867 0.045 Uiso 1 1 calc R
H4B H 1.1484 0.7522 0.6126 0.045 Uiso 1 1 calc R
H4C H 1.1456 0.7525 0.5596 0.045 Uiso 1 1 calc R
C5 C 0.87567(18) 0.7658(3) 0.68405(7) 0.0207(5) Uani 1 1 d .
C6 C 0.78522(19) 0.6960(3) 0.71012(7) 0.0228(5) Uani 1 1 d .
H6 H 0.7197 0.6378 0.6965 0.027 Uiso 1 1 calc R
C7 C 0.79006(19) 0.7107(3) 0.75576(8) 0.0243(5) Uani 1 1 d .
H7 H 0.7290 0.6612 0.7736 0.029 Uiso 1 1 calc R
C8 C 0.8849(2) 0.7985(3) 0.77517(7) 0.0226(5) Uani 1 1 d .
C9 C 0.9744(2) 0.8715(3) 0.74985(8) 0.0232(5) Uani 1 1 d .
H9 H 1.0382 0.9332 0.7637 0.028 Uiso 1 1 calc R
C10 C 0.97065(19) 0.8542(3) 0.70415(7) 0.0227(5) Uani 1 1 d .
H10 H 1.0327 0.9023 0.6865 0.027 Uiso 1 1 calc R
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'
Br Br -0.2901 2.4595 '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
N2 N1 H1N 105.0(18)
N2 N1 H2N 109.6(18)
H1N N1 H2N 96(2)
C1 N2 N1 121.8(2)
C1 N2 H3N 122.3(17)
N1 N2 H3N 115.6(17)
N4 N3 C2 108.65(17)
N3 N4 N5 106.60(17)
C3 N5 N4 112.04(18)
C3 N5 N6 126.23(19)
N4 N5 N6 121.71(17)
N5 N6 C5 116.57(17)
N5 N6 H4N 112.1(16)
C5 N6 H4N 113.5(16)
O1 C1 N2 123.0(2)
O1 C1 C2 121.2(2)
N2 C1 C2 115.8(2)
N3 C2 C3 110.03(19)
N3 C2 C1 122.8(2)
C3 C2 C1 127.2(2)
N5 C3 C2 102.68(19)
N5 C3 C4 123.1(2)
C2 C3 C4 134.2(2)
C3 C4 H4A 109.5
C3 C4 H4B 109.5
H4A C4 H4B 109.5
C3 C4 H4C 109.5
H4A C4 H4C 109.5
H4B C4 H4C 109.5
C6 C5 C10 119.7(2)
C6 C5 N6 119.36(19)
C10 C5 N6 120.9(2)
C7 C6 C5 120.4(2)
C7 C6 H6 119.8
C5 C6 H6 119.8
C6 C7 C8 119.2(2)
C6 C7 H7 120.4
C8 C7 H7 120.4
C9 C8 C7 121.2(2)
C9 C8 Br1 119.19(17)
C7 C8 Br1 119.58(16)
C8 C9 C10 119.6(2)
C8 C9 H9 120.2
C10 C9 H9 120.2
C9 C10 C5 119.9(2)
C9 C10 H10 120.1
C5 C10 H10 120.1
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Br1 C8 1.897(2)
O1 C1 1.224(3)
N1 N2 1.421(3)
N1 H1N 0.886(10)
N1 H2N 0.882(10)
N2 C1 1.329(3)
N2 H3N 0.877(10)
N3 N4 1.305(3)
N3 C2 1.363(3)
N4 N5 1.364(3)
N5 C3 1.353(3)
N5 N6 1.389(3)
N6 C5 1.409(3)
N6 H4N 0.870(10)
C1 C2 1.477(3)
C2 C3 1.376(3)
C3 C4 1.481(3)
C4 H4A 0.9800
C4 H4B 0.9800
C4 H4C 0.9800
C5 C6 1.391(3)
C5 C10 1.395(3)
C6 C7 1.382(3)
C6 H6 0.9500
C7 C8 1.384(3)
C7 H7 0.9500
C8 C9 1.378(3)
C9 C10 1.385(3)
C9 H9 0.9500
C10 H10 0.9500
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
C2 N3 N4 N5 -0.3(2)
N3 N4 N5 C3 0.4(2)
N3 N4 N5 N6 -178.20(18)
C3 N5 N6 C5 110.2(2)
N4 N5 N6 C5 -71.4(2)
N1 N2 C1 O1 4.1(3)
N1 N2 C1 C2 -175.25(19)
N4 N3 C2 C3 0.0(2)
N4 N3 C2 C1 179.60(19)
O1 C1 C2 N3 -179.7(2)
N2 C1 C2 N3 -0.3(3)
O1 C1 C2 C3 -0.2(3)
N2 C1 C2 C3 179.2(2)
N4 N5 C3 C2 -0.4(2)
N6 N5 C3 C2 178.15(19)
N4 N5 C3 C4 179.98(19)
N6 N5 C3 C4 -1.5(3)
N3 C2 C3 N5 0.2(2)
C1 C2 C3 N5 -179.3(2)
N3 C2 C3 C4 179.8(2)
C1 C2 C3 C4 0.2(4)
N5 N6 C5 C6 140.4(2)
N5 N6 C5 C10 -43.4(3)
C10 C5 C6 C7 -1.2(3)
N6 C5 C6 C7 175.03(19)
C5 C6 C7 C8 1.1(3)
C6 C7 C8 C9 0.1(3)
C6 C7 C8 Br1 -179.49(16)
C7 C8 C9 C10 -1.1(3)
Br1 C8 C9 C10 178.43(16)
C8 C9 C10 C5 1.0(3)
C6 C5 C10 C9 0.1(3)
N6 C5 C10 C9 -176.04(19)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 44225257
