#------------------------------------------------------------------------------
#$Date: 2025-08-19 01:52:38 +0300 (Tue, 19 Aug 2025) $
#$Revision: 301791 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/00/67/2006767.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_2006767
loop_
_publ_author_name
'Nieuwenhuyzen, M. '
'Keyes, T. E. '
'Gallagher, J. F. '
'Vos, J. G. '
_publ_section_title
;
 A 2:1 Co-Crystal of Hydroquinone and 3,5-Bis(2-pyridyl)-1,2,4-triazole
;
_journal_issue                   12
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              1873
_journal_page_last               1875
_journal_paper_doi               10.1107/S0108270197009670
_journal_volume                  53
_journal_year                    1997
_chemical_formula_iupac          '2C12 H9 N5, C6 H6 O2'
_chemical_formula_structural     '2C12 H9 N5, C6 H6 O2'
_chemical_formula_sum            'C30 H24 N10 O2'
_chemical_formula_weight         556.59
_chemical_melting_point          472.6(10)
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_audit_creation_method           SHELXL
_cell_angle_alpha                105.062(9)
_cell_angle_beta                 92.139(8)
_cell_angle_gamma                110.002(9)
_cell_formula_units_Z            1
_cell_length_a                   7.3223(7)
_cell_length_b                   7.6708(6)
_cell_length_c                   13.2160(10)
_cell_measurement_reflns_used    35
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      12.5
_cell_measurement_theta_min      5.0
_cell_volume                     667.03(11)
_computing_cell_refinement       XSCANS
_computing_data_collection       'XSCANS (Fait, 1993)'
_computing_data_reduction        XSCANS
_computing_molecular_graphics    'SHELXTL/PC (Sheldrick, 1990b)'
_computing_publication_material  SHELXTL/PC
_computing_structure_refinement  'SHELXL93 (Sheldrick, 1993)'
_computing_structure_solution    'SHELXS86 (Sheldrick, 1990a)'
_diffrn_ambient_temperature      120(2)
_diffrn_measurement_device       'Siemens P4'
_diffrn_measurement_method       ω
_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  0.015
_diffrn_reflns_av_sigmaI/netI    0.0333
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            2513
_diffrn_reflns_theta_max         25
_diffrn_reflns_theta_min         2.92
_diffrn_standards_decay_%        1
_diffrn_standards_interval_count 97
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.093
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            'Light tan'
_exptl_crystal_density_diffrn    1.386
_exptl_crystal_density_method    'Not measured'
_exptl_crystal_description       Needle
_exptl_crystal_F_000             290
_exptl_crystal_size_max          0.65
_exptl_crystal_size_mid          0.34
_exptl_crystal_size_min          0.19
_refine_diff_density_max         0.16
_refine_diff_density_min         -0.22
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_all   1.036
_refine_ls_goodness_of_fit_obs   1.083
_refine_ls_hydrogen_treatment
'H atoms were located from \DF synthesis and refined using a riding model'
_refine_ls_matrix_type           full
_refine_ls_number_parameters     190
_refine_ls_number_reflns         2312
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.036
_refine_ls_restrained_S_obs      1.083
_refine_ls_R_factor_all          0.076
_refine_ls_R_factor_obs          .048
_refine_ls_shift/esd_max         <0.001
_refine_ls_shift/esd_mean        0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[σ²(Fo²)+(0.0587P)²+0.1659P] where P = (Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.123
_refine_ls_wR_factor_obs         .107
_reflns_number_observed          1642
_reflns_number_total             2312
_reflns_observed_criterion       >2sigma(I)
_cod_data_source_file            bm1161.cif
_cod_data_source_block           bptdub
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
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:

'_chemical_melting_point' value '198.5 - 200.5\% C' was changed to
'472.6(10)' - it was converted from degrees Celsius(C) to Kelvins(K),
the average value was taken and precision was estimated.

Automatic conversion script
Id: cif_fix_values 1646 2011-03-28 12:23:43Z adriana 

The following automatic conversions were performed:

'_chemical_melting_point' value '198.5 - 200.5\% C' was changed to
'472.6(10)' - it was converted from degrees Celsius(C) to Kelvins(K),
the average value was taken and precision was
estimated.

'_symmetry_cell_setting' value 'Triclinic' changed to
'triclinic' 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 

The following automatic conversions were performed:

'_refine_ls_weighting_scheme' value 'calc w =
1/[\s^2^(Fo^2^)+(0.0587P)^2^+0.1659P] where P = (Fo^2^+2Fc^2^)/3' was
changed to 'calc'. New tag '_refine_ls_weighting_details' was
created. The value of the new tag was set to 'w =
1/[\s^2^(Fo^2^)+(0.0587P)^2^+0.1659P] where P = (Fo^2^+2Fc^2^)/3'.

Automatic conversion script
Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas 
;
_cod_original_cell_volume        667.03(14)
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               2006767
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_thermal_displace_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_group
_atom_site_type_symbol
C1 .1395(3) .5512(3) .3898(2) .0450(6) Uani d . 1 . C
H1 .1307(3) .5914(3) .4794(2) .054 Uiso d R 1 . H
C2 .0898(4) .3582(3) .3325(2) .0546(7) Uani d . 1 . C
H2 .0339(4) .2509(3) .3806(2) .066 Uiso d R 1 . H
C3 .1104(4) .3140(4) .2272(2) .0589(7) Uani d . 1 . C
H3 .0690(4) .1605(4) .1802(2) .071 Uiso d R 1 . H
C4 .1727(4) .4632(4) .1818(2) .0581(7) Uani d . 1 . C
H4 .1900(4) .4360(4) .1020(2) .070 Uiso d R 1 . H
N5 .2191(3) .6510(3) .2348(2) .0473(5) Uani d . 1 . N
C6 .2040(3) .6922(3) .3385(2) .0370(5) Uani d . 1 . C
C7 .2629(3) .8978(3) .3987(2) .0366(5) Uani d . 1 . C
N8 .3607(3) 1.0410(3) .35978(14) .0437(5) Uani d . 1 . N
N9 .2269(3) .9554(2) .49938(14) .0397(5) Uani d . 1 . N
N10 .3874(3) 1.2002(3) .44254(14) .0421(5) Uani d . 1 . N
H10 .4550(3) 1.3341(3) .44166(14) .051 Uiso d R 1 . H
C11 .3073(3) 1.1471(3) .5247(2) .0371(5) Uani d . 1 . C
C12 .3079(3) 1.2819(3) .6260(2) .0370(5) Uani d . 1 . C
N13 .3830(3) 1.4726(3) .63427(15) .0435(5) Uani d . 1 . N
C14 .3818(4) 1.5948(3) .7269(2) .0508(7) Uani d . 1 . C
H14 .4317(4) 1.7439(3) .7402(2) .061 Uiso d R 1 . H
C15 .3093(4) 1.5360(4) .8125(2) .0498(6) Uani d . 1 . C
H15 .3068(4) 1.6434(4) .8810(2) .060 Uiso d R 1 . H
C16 .2336(4) 1.3412(4) .8027(2) .0486(6) Uani d . 1 . C
H16 .1941(4) 1.2966(4) .8806(2) .058 Uiso d R 1 . H
C17 .2330(3) 1.2111(3) .7080(2) .0455(6) Uani d . 1 . C
H17 .1733(3) 1.0498(3) .7012(2) .055 Uiso d R 1 . H
C1S .5118(4) .9118(3) .0774(2) .0471(6) Uani d . 1 . C
H1S .5305(4) .8534(3) .1382(2) .057 Uiso d R 1 . H
C2S .3407(4) .9395(3) .0537(2) .0425(6) Uani d . 1 . C
C3S .3289(4) 1.0287(3) -.0237(2) .0471(6) Uani d . 1 . C
H3S .1965(4) 1.0447(3) -.0385(2) .057 Uiso d R 1 . H
O4S .1790(3) .8798(3) .10323(14) .0580(5) Uani d . 1 . O
H4S .2136(3) .8181(3) .16042(14) .070 Uiso d R 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_site_symmetry_3
_geom_angle
C6 C1 C2 . 119.0(2)
C3 C2 C1 . 118.9(2)
C2 C3 C4 . 118.4(2)
N5 C4 C3 . 124.1(2)
C6 N5 C4 . 116.7(2)
N5 C6 C1 . 122.9(2)
N5 C6 C7 . 117.4(2)
C1 C6 C7 . 119.7(2)
N8 C7 N9 . 114.9(2)
N8 C7 C6 . 122.7(2)
N9 C7 C6 . 122.4(2)
C7 N8 N10 . 101.9(2)
C11 N9 C7 . 103.2(2)
C11 N10 N8 . 110.3(2)
N9 C11 N10 . 109.7(2)
N9 C11 C12 . 125.6(2)
N10 C11 C12 . 124.7(2)
N13 C12 C17 . 123.0(2)
N13 C12 C11 . 117.1(2)
C17 C12 C11 . 119.8(2)
C14 N13 C12 . 116.8(2)
N13 C14 C15 . 123.8(2)
C16 C15 C14 . 118.7(2)
C15 C16 C17 . 119.0(2)
C16 C17 C12 . 118.8(2)
C2S C1S C3S 2_675 120.6(2)
O4S C2S C1S . 122.5(2)
O4S C2S C3S . 118.2(2)
C1S C2S C3S . 119.3(2)
C2S C3S C1S 2_675 120.1(2)
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 C6 . 1.381(3) ?
C1 C2 . 1.388(3) ?
C2 C3 . 1.371(4) ?
C3 C4 . 1.378(4) ?
C4 N5 . 1.344(3) ?
N5 C6 . 1.343(3) ?
C6 C7 . 1.471(3) ?
C7 N8 . 1.329(3) ?
C7 N9 . 1.355(3) ?
N8 N10 . 1.361(2) ?
N9 C11 . 1.326(3) ?
N10 C11 . 1.342(3) ?
C11 C12 . 1.463(3) ?
C12 N13 . 1.348(3) ?
C12 C17 . 1.385(3) ?
N13 C14 . 1.337(3) ?
C14 C15 . 1.382(3) ?
C15 C16 . 1.372(3) ?
C16 C17 . 1.382(3) ?
C1S C2S . 1.378(3) ?
C1S C3S 2_675 1.392(3) ?
C2S O4S . 1.372(3) ?
C2S C3S . 1.386(3) ?
C3S C1S 2_675 1.392(3) ?
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_4
_geom_torsion
C6 C1 C2 C3 . . 1.4(4)
C1 C2 C3 C4 . . -2.5(4)
C2 C3 C4 N5 . . 1.6(4)
C3 C4 N5 C6 . . 0.5(4)
C4 N5 C6 C1 . . -1.6(3)
C4 N5 C6 C7 . . 177.2(2)
C2 C1 C6 N5 . . 0.7(4)
C2 C1 C6 C7 . . -178.2(2)
N5 C6 C7 N8 . . -12.2(3)
C1 C6 C7 N8 . . 166.8(2)
N5 C6 C7 N9 . . 169.9(2)
C1 C6 C7 N9 . . -11.2(3)
N9 C7 N8 N10 . . 0.0(3)
C6 C7 N8 N10 . . -178.1(2)
N8 C7 N9 C11 . . 0.1(3)
C6 C7 N9 C11 . . 178.1(2)
C7 N8 N10 C11 . . 0.0(2)
C7 N9 C11 N10 . . -0.1(2)
C7 N9 C11 C12 . . 179.4(2)
N8 N10 C11 N9 . . 0.0(3)
N8 N10 C11 C12 . . -179.4(2)
N9 C11 C12 N13 . . -174.7(2)
N10 C11 C12 N13 . . 4.6(3)
N9 C11 C12 C17 . . 5.2(3)
N10 C11 C12 C17 . . -175.5(2)
C17 C12 N13 C14 . . -0.3(3)
C11 C12 N13 C14 . . 179.6(2)
C12 N13 C14 C15 . . 0.1(4)
N13 C14 C15 C16 . . -0.1(4)
C14 C15 C16 C17 . . 0.2(4)
C15 C16 C17 C12 . . -0.4(4)
N13 C12 C17 C16 . . 0.4(4)
C11 C12 C17 C16 . . -179.4(2)
C3S C1S C2S O4S 2_675 . 178.7(2)
C3S C1S C2S C3S 2_675 . -0.5(4)
O4S C2S C3S C1S . 2_675 -178.8(2)
C1S C2S C3S C1S . 2_675 0.5(4)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139055800
