#------------------------------------------------------------------------------
#$Date: 2025-08-19 13:43:10 +0300 (Tue, 19 Aug 2025) $
#$Revision: 301803 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/20/37/2203778.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_2203778
loop_
_publ_author_name
'Ling Xu'
'Guo-Cong Guo'
'Bing Liu'
'Ming-Lai Fu'
'Jin-Shun Huang'
_publ_section_title
;
 3-(1H-1,2,4-Triazol-4-yl)phenol
;
_journal_issue                   6
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1060
_journal_page_last               o1062
_journal_paper_doi               10.1107/S1600536804012152
_journal_volume                  60
_journal_year                    2004
_chemical_formula_iupac          'C8 H7 N3 O'
_chemical_formula_moiety         'C8 H7 N3 O'
_chemical_formula_sum            'C8 H7 N3 O'
_chemical_formula_weight         161.17
_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
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            16
_cell_length_a                   10.099(5)
_cell_length_b                   16.315(7)
_cell_length_c                   18.593(8)
_cell_measurement_reflns_used    6856
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      28.3
_cell_measurement_theta_min      1.1
_cell_volume                     3063(2)
_computing_cell_refinement       CrystalClear
_computing_data_collection       'CrystalClear (Rigaku, 2002)'
_computing_data_reduction        CrystalClear
_computing_molecular_graphics    SHELXTL
_computing_publication_material  SHELXTL
_computing_structure_refinement  SHELXTL
_computing_structure_solution    'SHELXTL (Siemens 1994)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Rigaku Mercury CCD'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'rotating-anode generator'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0385
_diffrn_reflns_av_sigmaI/netI    0.0191
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            18275
_diffrn_reflns_theta_full        25.02
_diffrn_reflns_theta_max         25.02
_diffrn_reflns_theta_min         3.23
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.098
_exptl_absorpt_correction_T_max  0.988
_exptl_absorpt_correction_T_min  0.915
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SPHERE in CrystalClear; Rigaku, 2002)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.398
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1344
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.134
_refine_diff_density_min         -0.156
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.271
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     225
_refine_ls_number_reflns         2686
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.271
_refine_ls_R_factor_all          0.0594
_refine_ls_R_factor_gt           0.0546
_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)+(0.0431P)²+0.89P] where P = (Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1167
_refine_ls_wR_factor_ref         0.1190
_reflns_number_gt                2523
_reflns_number_total             2685
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            lh6207.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Orthorhombic' changed to 'orthorhombic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 

The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Orthorhombic' changed to
'orthorhombic' according to
/home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_cell_volume        3064(2)
_cod_database_code               2203778
_cod_database_fobs_code          2203778
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'-x-1/2, y-1/2, z'
'x, -y-1/2, z-1/2'
loop_
_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_type_symbol
O1 -0.02044(18) 0.19717(10) 0.09482(8) 0.0625(5) Uani d . 1 O
N11 0.0420(2) 0.25930(12) 0.45849(9) 0.0594(5) Uani d . 1 N
N12 0.0032(2) 0.18024(11) 0.44348(9) 0.0555(5) Uani d . 1 N
N13 0.07312(16) 0.23740(9) 0.34389(8) 0.0378(4) Uani d . 1 N
C11 0.0824(2) 0.29160(13) 0.39847(11) 0.0550(6) Uani d . 1 C
H11B 0.1136 0.3450 0.3938 0.066 Uiso calc R 1 H
C12 0.0223(2) 0.16975(12) 0.37498(11) 0.0474(5) Uani d . 1 C
H12B 0.0032 0.1215 0.3504 0.057 Uiso calc R 1 H
C13 0.10784(18) 0.25023(11) 0.26964(9) 0.0346(4) Uani d . 1 C
C14 0.21739(19) 0.29700(12) 0.25349(11) 0.0429(5) Uani d . 1 C
H14A 0.2691 0.3197 0.2897 0.051 Uiso calc R 1 H
C15 0.2482(2) 0.30919(13) 0.18183(11) 0.0470(5) Uani d . 1 C
H15A 0.3218 0.3406 0.1698 0.056 Uiso calc R 1 H
C16 0.1720(2) 0.27559(12) 0.12783(11) 0.0458(5) Uani d . 1 C
H16A 0.1946 0.2838 0.0799 0.055 Uiso calc R 1 H
C17 0.0615(2) 0.22946(11) 0.14545(10) 0.0407(5) Uani d . 1 C
C18 0.02910(19) 0.21583(11) 0.21709(9) 0.0384(4) Uani d . 1 C
H18A -0.0441 0.1842 0.2293 0.046 Uiso calc R 1 H
O2 0.78949(15) 0.06705(9) 0.27278(8) 0.0503(4) Uani d . 1 O
N21 0.8752(2) 0.03846(12) -0.07209(9) 0.0602(5) Uani d . 1 N
N22 0.8041(2) -0.03057(12) -0.09034(9) 0.0580(5) Uani d . 1 N
N23 0.76772(16) -0.00472(10) 0.02365(8) 0.0405(4) Uani d . 1 N
C21 0.8505(3) 0.05165(14) -0.00456(12) 0.0577(6) Uani d . 1 C
H21B 0.8860 0.0951 0.0215 0.069 Uiso calc R 1 H
C22 0.7428(3) -0.05468(15) -0.03280(11) 0.0596(6) Uani d . 1 C
H22B 0.6885 -0.1006 -0.0306 0.072 Uiso calc R 1 H
C23 0.71322(19) -0.00898(11) 0.09492(9) 0.0378(4) Uani d . 1 C
C24 0.5947(2) -0.05014(12) 0.10597(11) 0.0452(5) Uani d . 1 C
H24A 0.5514 -0.0760 0.0681 0.054 Uiso calc R 1 H
C25 0.5425(2) -0.05176(12) 0.17466(11) 0.0477(5) Uani d . 1 C
H25A 0.4634 -0.0794 0.1829 0.057 Uiso calc R 1 H
C26 0.60544(19) -0.01318(11) 0.23130(10) 0.0422(5) Uani d . 1 C
H26A 0.5683 -0.0144 0.2771 0.051 Uiso calc R 1 H
C27 0.72396(19) 0.02730(11) 0.21965(9) 0.0376(4) Uani d . 1 C
C28 0.77903(19) 0.02906(12) 0.15105(9) 0.0386(4) Uani d . 1 C
H28A 0.8592 0.0555 0.1430 0.046 Uiso calc R 1 H
H2O 0.749(3) 0.0575(16) 0.3143(15) 0.073(8) Uiso d . 1 H
H1O 0.007(3) 0.2124(18) 0.0481(17) 0.093(9) Uiso d . 1 H
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_publ_flag
C17 O1 H1O 110.8(18) ?
C11 N11 N12 107.17(17) ?
C12 N12 N11 106.25(17) ?
C12 N13 C11 103.92(16) y
C12 N13 C13 128.55(16) y
C11 N13 C13 127.51(16) y
N11 C11 N13 110.99(19) ?
N11 C11 H11B 124.5 ?
N13 C11 H11B 124.5 ?
N12 C12 N13 111.66(18) ?
N12 C12 H12B 124.2 ?
N13 C12 H12B 124.2 ?
C14 C13 C18 122.28(17) ?
C14 C13 N13 119.04(16) ?
C18 C13 N13 118.67(16) ?
C13 C14 C15 118.09(18) ?
C13 C14 H14A 121.0 ?
C15 C14 H14A 121.0 ?
C16 C15 C14 121.22(19) ?
C16 C15 H15A 119.4 ?
C14 C15 H15A 119.4 ?
C15 C16 C17 119.59(18) ?
C15 C16 H16A 120.2 ?
C17 C16 H16A 120.2 ?
O1 C17 C16 122.49(18) ?
O1 C17 C18 117.27(18) ?
C16 C17 C18 120.23(18) ?
C13 C18 C17 118.57(18) ?
C13 C18 H18A 120.7 ?
C17 C18 H18A 120.7 ?
C27 O2 H2O 109.1(17) ?
C21 N21 N22 105.89(18) ?
C22 N22 N21 107.06(17) ?
C21 N23 C22 102.96(17) y
C21 N23 C23 128.98(16) y
C22 N23 C23 127.99(18) y
N21 C21 N23 112.45(19) ?
N21 C21 H21B 123.8 ?
N23 C21 H21B 123.8 ?
N22 C22 N23 111.6(2) ?
N22 C22 H22B 124.2 ?
N23 C22 H22B 124.2 ?
C28 C23 C24 121.30(17) ?
C28 C23 N23 119.33(17) ?
C24 C23 N23 119.37(16) ?
C25 C24 C23 118.35(18) ?
C25 C24 H24A 120.8 ?
C23 C24 H24A 120.8 ?
C26 C25 C24 121.37(19) ?
C26 C25 H25A 119.3 ?
C24 C25 H25A 119.3 ?
C25 C26 C27 119.72(18) ?
C25 C26 H26A 120.1 ?
C27 C26 H26A 120.1 ?
O2 C27 C26 122.47(17) ?
O2 C27 C28 117.60(17) ?
C26 C27 C28 119.92(17) ?
C23 C28 C27 119.33(18) ?
C23 C28 H28A 120.3 ?
C27 C28 H28A 120.3 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
O1 C17 1.360(2) ?
O1 H1O 0.95(3) ?
N11 C11 1.300(3) y
N11 N12 1.377(3) y
N12 C12 1.299(3) y
N13 C12 1.347(2) y
N13 C11 1.349(2) y
N13 C13 1.440(2) y
C11 H11B 0.9300 ?
C12 H12B 0.9300 ?
C13 C14 1.377(3) ?
C13 C18 1.379(3) ?
C14 C15 1.383(3) ?
C14 H14A 0.9300 ?
C15 C16 1.379(3) ?
C15 H15A 0.9300 ?
C16 C17 1.385(3) ?
C16 H16A 0.9300 ?
C17 C18 1.389(3) ?
C18 H18A 0.9300 ?
O2 C27 1.354(2) ?
O2 H2O 0.89(3) ?
N21 C21 1.298(3) y
N21 N22 1.378(3) y
N22 C22 1.297(3) y
N23 C21 1.349(3) y
N23 C22 1.353(3) y
N23 C23 1.436(2) y
C21 H21B 0.9300 ?
C22 H22B 0.9300 ?
C23 C28 1.384(3) ?
C23 C24 1.388(3) ?
C24 C25 1.382(3) ?
C24 H24A 0.9300 ?
C25 C26 1.382(3) ?
C25 H25A 0.9300 ?
C26 C27 1.384(3) ?
C26 H26A 0.9300 ?
C27 C28 1.392(3) ?
C28 H28A 0.9300 ?
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
O2 H2O N22 2_655 0.89(3) 1.91(3) 2.779(2) 169(3)
O1 H1O N11 8_565 0.95(3) 1.76(3) 2.707(2) 174(3)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21686402
2 PubChem 139066751
