#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/50/2225061.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_2225061
loop_
_publ_author_name
'Chen, Sheng-Hui'
'Zhang, Gao-Yong'
'Dong, Jin-Feng'
_publ_section_title
;
 2,2'-(4-Amino-4H-1,2,4-triazole-3,5-diyl)diphenol
;
_journal_coeditor_code           NC2167
_journal_issue                   2
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o330
_journal_paper_doi               10.1107/S1600536809055536
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C14 H12 N4 O2'
_chemical_formula_moiety         'C14 H12 N4 O2'
_chemical_formula_sum            'C14 H12 N4 O2'
_chemical_formula_weight         268.28
_chemical_name_systematic
;
2,2'-(4-Amino-4H-1,2,4-triazole-3,5-diyl)diphenol
;
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.262(2)
_cell_length_b                   9.384(3)
_cell_length_c                   15.919(4)
_cell_measurement_reflns_used    2036
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      24.62
_cell_measurement_theta_min      2.35
_cell_volume                     1234.2(6)
_computing_cell_refinement       'SAINT (Bruker, 1997)'
_computing_data_collection       'SMART (Bruker, 1997)'
_computing_data_reduction        'SAINT (Bruker, 1999)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker SMART CCD area-detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0429
_diffrn_reflns_av_sigmaI/netI    0.0382
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            6343
_diffrn_reflns_theta_full        25.04
_diffrn_reflns_theta_max         25.04
_diffrn_reflns_theta_min         2.52
_diffrn_standards_decay_%        0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.101
_exptl_absorpt_correction_T_max  0.9920
_exptl_absorpt_correction_T_min  0.9800
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.444
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             560
_exptl_crystal_size_max          0.10
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.182
_refine_diff_density_min         -0.167
_refine_ls_extinction_coef       0.011(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL97 (Sheldrick, 2008)'
_refine_ls_goodness_of_fit_ref   1.099
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     192
_refine_ls_number_reflns         1276
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.099
_refine_ls_R_factor_all          0.0471
_refine_ls_R_factor_gt           0.0411
_refine_ls_shift/su_max          0.005
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0693P)²+0.0780P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1074
_refine_ls_wR_factor_ref         0.1120
_reflns_number_gt                1143
_reflns_number_total             1276
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            nc2167.cif
_cod_data_source_block           I
_cod_database_code               2225061
_cod_database_fobs_code          2225061
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -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_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C C1 0.5404(4) 0.5286(4) 0.49447(17) 0.0385(7) Uani d . 1 . .
C C2 0.4539(4) 0.4330(4) 0.54359(19) 0.0449(8) Uani d . 1 . .
H H2 0.3416 0.4386 0.5450 0.054 Uiso calc R 1 . .
C C3 0.5310(4) 0.3309(4) 0.5899(2) 0.0457(8) Uani d . 1 . .
H H3 0.4711 0.2671 0.6220 0.055 Uiso calc R 1 . .
C C4 0.6981(4) 0.3225(4) 0.5890(2) 0.0479(8) Uani d . 1 . .
H H4 0.7509 0.2536 0.6208 0.057 Uiso calc R 1 . .
C C5 0.7861(4) 0.4166(3) 0.5408(2) 0.0442(8) Uani d . 1 . .
H H5 0.8985 0.4103 0.5406 0.053 Uiso calc R 1 . .
C C6 0.7108(4) 0.5211(3) 0.49212(17) 0.0339(7) Uani d . 1 . .
C C7 0.7987(4) 0.6149(3) 0.43411(18) 0.0339(7) Uani d . 1 . .
C C8 0.9790(3) 0.7037(3) 0.34798(17) 0.0333(7) Uani d . 1 . .
C C9 1.1311(3) 0.7234(3) 0.30083(17) 0.0345(7) Uani d . 1 . .
C C10 1.1826(4) 0.8612(3) 0.2823(2) 0.0422(8) Uani d . 1 . .
H H10 1.1286 0.9388 0.3055 0.051 Uiso calc R 1 . .
C C11 1.3126(4) 0.8838(4) 0.2298(2) 0.0521(9) Uani d . 1 . .
H H11 1.3482 0.9759 0.2186 0.062 Uiso calc R 1 . .
C C12 1.3895(4) 0.7686(4) 0.1941(2) 0.0586(10) Uani d . 1 . .
H H12 1.4744 0.7837 0.1568 0.070 Uiso calc R 1 . .
C C13 1.3427(4) 0.6316(4) 0.2127(2) 0.0482(9) Uani d . 1 . .
H H13 1.3981 0.5550 0.1894 0.058 Uiso calc R 1 . .
C C14 1.2130(4) 0.6075(3) 0.26611(18) 0.0371(7) Uani d . 1 . .
N N1 0.7263(3) 0.7099(3) 0.38646(15) 0.0388(6) Uani d . 1 . .
N N2 0.8404(3) 0.7657(3) 0.33109(15) 0.0395(6) Uani d . 1 . .
N N3 0.9594(3) 0.6108(3) 0.41328(15) 0.0335(6) Uani d . 1 . .
N N4 1.0844(3) 0.5384(4) 0.45696(19) 0.0427(7) Uani d . 1 . .
O O1 0.4530(3) 0.6247(3) 0.44960(15) 0.0554(7) Uani d . 1 . .
H H1 0.5143 0.6734 0.4210 0.083 Uiso calc R 1 . .
O O2 1.1615(3) 0.4745(2) 0.28606(13) 0.0458(6) Uani d . 1 . .
H H2A 1.1785 0.4206 0.2465 0.069 Uiso calc R 1 . .
H H4A 1.167(7) 0.605(5) 0.471(3) 0.097(16) Uiso d . 1 . .
H H4B 1.131(5) 0.486(4) 0.419(2) 0.059(12) Uiso 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 0.0033 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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
O1 C1 C2 . . 116.8(3) ?
O1 C1 C6 . . 123.4(3) ?
C2 C1 C6 . . 119.8(3) ?
C3 C2 C1 . . 121.1(3) ?
C3 C2 H2 . . 119.4 ?
C1 C2 H2 . . 119.4 ?
C2 C3 C4 . . 120.0(3) ?
C2 C3 H3 . . 120.0 ?
C4 C3 H3 . . 120.0 ?
C5 C4 C3 . . 119.8(3) ?
C5 C4 H4 . . 120.1 ?
C3 C4 H4 . . 120.1 ?
C4 C5 C6 . . 121.6(3) ?
C4 C5 H5 . . 119.2 ?
C6 C5 H5 . . 119.2 ?
C5 C6 C1 . . 117.7(3) ?
C5 C6 C7 . . 123.3(3) ?
C1 C6 C7 . . 118.7(3) ?
N1 C7 N3 . . 108.7(2) ?
N1 C7 C6 . . 123.0(3) ?
N3 C7 C6 . . 128.0(3) ?
N2 C8 N3 . . 109.6(3) ?
N2 C8 C9 . . 125.7(3) ?
N3 C8 C9 . . 124.6(3) ?
C10 C9 C14 . . 119.4(3) ?
C10 C9 C8 . . 119.0(3) ?
C14 C9 C8 . . 121.2(3) ?
C11 C10 C9 . . 120.6(3) ?
C11 C10 H10 . . 119.7 ?
C9 C10 H10 . . 119.7 ?
C12 C11 C10 . . 119.3(3) ?
C12 C11 H11 . . 120.3 ?
C10 C11 H11 . . 120.3 ?
C13 C12 C11 . . 121.0(3) ?
C13 C12 H12 . . 119.5 ?
C11 C12 H12 . . 119.5 ?
C12 C13 C14 . . 120.1(3) ?
C12 C13 H13 . . 119.9 ?
C14 C13 H13 . . 119.9 ?
O2 C14 C13 . . 122.4(3) ?
O2 C14 C9 . . 118.2(3) ?
C13 C14 C9 . . 119.4(3) ?
C7 N1 N2 . . 108.2(2) ?
C8 N2 N1 . . 107.1(2) ?
C8 N3 C7 . . 106.4(2) ?
C8 N3 N4 . . 126.3(2) ?
C7 N3 N4 . . 126.9(2) ?
N3 N4 H4A . . 109(3) ?
N3 N4 H4B . . 105(3) ?
H4A N4 H4B . . 103(4) ?
C1 O1 H1 . . 109.5 ?
C14 O2 H2A . . 109.5 ?
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
C1 O1 . 1.358(4) ?
C1 C2 . 1.388(4) ?
C1 C6 . 1.410(5) ?
C2 C3 . 1.366(5) ?
C2 H2 . 0.9300 ?
C3 C4 . 1.383(5) ?
C3 H3 . 0.9300 ?
C4 C5 . 1.377(5) ?
C4 H4 . 0.9300 ?
C5 C6 . 1.396(4) ?
C5 H5 . 0.9300 ?
C6 C7 . 1.468(4) ?
C7 N1 . 1.314(4) ?
C7 N3 . 1.368(4) ?
C8 N2 . 1.312(4) ?
C8 N3 . 1.366(4) ?
C8 C9 . 1.475(4) ?
C9 C10 . 1.393(4) ?
C9 C14 . 1.395(4) ?
C10 C11 . 1.377(5) ?
C10 H10 . 0.9300 ?
C11 C12 . 1.376(5) ?
C11 H11 . 0.9300 ?
C12 C13 . 1.375(5) ?
C12 H12 . 0.9300 ?
C13 C14 . 1.386(4) ?
C13 H13 . 0.9300 ?
C14 O2 . 1.356(4) ?
N1 N2 . 1.393(3) ?
N3 N4 . 1.419(3) ?
N4 H4A . 0.95(5) ?
N4 H4B . 0.87(4) ?
O1 H1 . 0.8200 ?
O2 H2A . 0.8200 ?
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
N4 H4A O1 1_655 0.95(5) 2.39(6) 3.153(4) 136(4)
O1 H1 N1 . 0.82 1.87 2.598(3) 147.7
O2 H2A N2 3_745 0.82 1.91 2.705(3) 161.8
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 10219225
