#------------------------------------------------------------------------------
#$Date: 2025-08-19 01:52:38 +0300 (Tue, 19 Aug 2025) $
#$Revision: 301791 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/00/70/2007050.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_2007050
loop_
_publ_author_name
'Wang, Zuoxiang'
'Bai, Zhiping'
'Yang, Jiaxiang'
'Okamoto, Ken-ichi'
'You, Xiaozeng'
_publ_contact_author
;
Dr. Zhiping Bai
Coordination Chemistry Institute &
State Key Laboratory of Coordination Chemistry
Nanjing University
Nanjing 210093
People's Republic of China
;
_publ_section_title
;
 3,5-Bis(2-pyridyl)-4-p-chlorophenyl-4H-1,2,4-triazole
;
_journal_issue                   3
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              438
_journal_page_last               439
_journal_paper_doi               10.1107/S0108270197014625
_journal_volume                  54
_journal_year                    1998
_chemical_formula_moiety         'C18 H12 Cl N5 '
_chemical_formula_sum            'C18 H12 Cl N5'
_chemical_formula_weight         333.78
_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           'from TEXRAY.INF file'
_cell_angle_alpha                97.890(10)
_cell_angle_beta                 110.715(9)
_cell_angle_gamma                100.44(2)
_cell_formula_units_Z            2
_cell_length_a                   8.949(2)
_cell_length_b                   11.593(2)
_cell_length_c                   8.6175(9)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    296.2
_cell_measurement_theta_max      14.9
_cell_measurement_theta_min      14.4
_cell_volume                     802.4(3)
_computing_cell_refinement       'Rigaku/AFC Diffractometer Control Software'
_computing_data_collection
; Rigaku/AFC Diffractometer Control Software (Molecular Structure Corporation,
1995a)
;
_computing_data_reduction
'TEXSAN (Molecular Structure Corporation, 1995b)'
_computing_molecular_graphics    'SHELXTL (Siemens, 1994)'
_computing_publication_material  TEXSAN
_computing_structure_refinement  TEXSAN
_computing_structure_solution    'DIRDIF92 (Beuskens, 1992)'
_diffrn_ambient_temperature      296.2
_diffrn_measurement_device       'Rigaku AFC7S'
_diffrn_measurement_method       ω-2θ
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Rigaku sealed tube'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_reflns_av_R_equivalents  2.26
_diffrn_reflns_av_sigmaI/netI    0.074
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            3910
_diffrn_reflns_reduction_process 'Lp corrections applied'
_diffrn_reflns_theta_max         27.49
_diffrn_reflns_theta_min         2.51
_diffrn_standards_decay_%        2.43
_diffrn_standards_interval_count 150
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.24
_exptl_absorpt_correction_T_max  0.998
_exptl_absorpt_correction_T_min  0.949
_exptl_absorpt_correction_type   '\y scans (North, Phillips & Mathews, 1968)'
_exptl_crystal_colour            white
_exptl_crystal_density_diffrn    1.381
_exptl_crystal_density_meas      ?
_exptl_crystal_description       block
_exptl_crystal_F_000             334
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.13
_refine_diff_density_max         0.150
_refine_diff_density_min         -0.180
_refine_ls_extinction_coef       0.039(6)
_refine_ls_extinction_method     'Zachariasen (1967) type 2 Gaussian isotropic'
_refine_ls_goodness_of_fit_obs   1.282
_refine_ls_hydrogen_treatment    'H atoms included but not refined'
_refine_ls_matrix_type           full
_refine_ls_number_constraints    0
_refine_ls_number_parameters     218
_refine_ls_number_reflns         2228
_refine_ls_number_restraints     0
_refine_ls_R_factor_obs          .0380
_refine_ls_shift/esd_max         0.006
_refine_ls_shift/esd_mean        0.001
_refine_ls_structure_factor_coef F
_refine_ls_weighting_details     'w = 1/[σ²(Fo) + 0.00063|Fo|²]'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_obs         .0515
_reflns_number_observed          2228
_reflns_number_total             3906
_reflns_observed_criterion       >1.5sigma(I)
_cod_data_source_file            ab1519.cif
_cod_data_source_block           bpct
_cod_depositor_comments
;
The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'not measured' was changed to '?'
- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas 

The following automatic conversions were performed:

'_refine_ls_weighting_scheme' value 'w = 1/[\s^2^(Fo) +
0.00063|Fo|^2^]' 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) + 0.00063|Fo|^2^]'.

Automatic conversion script
Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas 
;
_cod_original_cell_volume        802.5(3)
_cod_original_sg_symbol_H-M      'P -1 '
_cod_original_formula_sum        'C18 H12 Cl N5 '
_cod_database_code               2007050
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_calc_attached_atom
_atom_site_refinement_flags
_atom_site_occupancy
Cl(1) .18026(10) .46836(6) .33178(9) .0787(2) Uani d . . 1.00
N(1) .2246(3) .9978(2) .4849(3) .0648(6) Uani d . . 1.00
N(2) -.0785(2) .89200(10) .1798(2) .0474(5) Uani d . . 1.00
N(3) -.0894(3) 1.0776(2) .1609(3) .0634(6) Uani d . . 1.00
N(4) -.2399(3) 1.0025(2) .0537(3) .0638(6) Uani d . . 1.00
N(5) -.3426(2) .6807(2) -.0564(3) .0647(6) Uani d . . 1.00
C(1) .3741(4) 1.0450(3) .6060(3) .0796(9) Uani d . . 1.00
C(2) .4745(4) 1.1517(3) .6149(4) .0950(10) Uani d . . 1.00
C(3) .4187(4) 1.2149(3) .4916(5) .0940(10) Uani d . . 1.00
C(4) .2655(4) 1.1693(2) .3646(3) .0692(8) Uani d . . 1.00
C(5) .1730(3) 1.0601(2) .3655(3) .0538(6) Uani d . . 1.00
C(6) .0054(3) 1.0108(2) .2353(3) .0507(6) Uani d . . 1.00
C(7) -.2318(3) .8920(2) .0673(3) .0517(6) Uani d . . 1.00
C(8) -.3736(3) .7877(2) -.0217(3) .0526(6) Uani d . . 1.00
C(9) -.5316(3) .8039(2) -.0687(3) .0655(8) Uani d . . 1.00
C(10) -.6629(3) .7070(3) -.1537(4) .0761(9) Uani d . . 1.00
C(11) -.6331(3) .5966(3) -.1898(3) .0779(9) Uani d . . 1.00
C(12) -.4727(3) .5883(2) -.1386(4) .0740(8) Uani d . . 1.00
C(13) -.0146(2) .7891(2) .2188(3) .0426(5) Uani d . . 1.00
C(14) -.0243(3) .7442(2) .3553(3) .0534(6) Uani d . . 1.00
C(15) .0374(3) .6458(2) .3915(3) .0541(6) Uani d . . 1.00
C(16) .1060(3) .5939(2) .2894(3) .0494(6) Uani d . . 1.00
C(17) .1157(3) .6386(2) .1522(3) .0500(6) Uani d . . 1.00
C(18) .0559(3) .7382(2) .1174(3) .0490(6) Uani d . . 1.00
H(1) .4136 1.0018 .6917 .0955 Uiso calc . . 1.00
H(2) .5803 1.1815 .7043 .1140 Uiso calc . . 1.00
H(3) .4856 1.2894 .4945 .1129 Uiso calc . . 1.00
H(4) .2238 1.2114 .2781 .0830 Uiso calc . . 1.00
H(5) -.5487 .8815 -.0421 .0787 Uiso calc . . 1.00
H(6) -.7726 .7159 -.1871 .0913 Uiso calc . . 1.00
H(7) -.7216 .5275 -.2490 .0936 Uiso calc . . 1.00
H(8) -.4534 .5113 -.1636 .0888 Uiso calc . . 1.00
H(9) -.0730 .7806 .4242 .0641 Uiso calc . . 1.00
H(10) .0325 .6144 .4863 .0649 Uiso calc . . 1.00
H(11) .1629 .6015 .0822 .0600 Uiso calc . . 1.00
H(12) .0634 .7710 .0246 .0588 Uiso calc . . 1.00
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C 0.003 0.002
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1)
;
H 0.000 0.000
;
International Tables for Crystallography
(1992, Vol. C, Table 6.1.1.2)
;
N 0.006 0.003
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1)
;
Cl 0.148 0.159
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1)
;
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_2
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C(1) N(1) C(5) 1_555 1_555 1_555 116.6(2) ?
C(6) N(2) C(7) 1_555 1_555 1_555 104.7(2) yes
C(6) N(2) C(13) 1_555 1_555 1_555 127.5(2) ?
C(7) N(2) C(13) 1_555 1_555 1_555 127.5(2) ?
N(4) N(3) C(6) 1_555 1_555 1_555 107.9(2) yes
N(3) N(4) C(7) 1_555 1_555 1_555 107.3(2) yes
C(8) N(5) C(12) 1_555 1_555 1_555 116.5(2) ?
N(1) C(1) C(2) 1_555 1_555 1_555 124.2(3) ?
N(1) C(1) H(1) 1_555 1_555 1_555 117.9(3) no
C(2) C(1) H(1) 1_555 1_555 1_555 117.9(3) no
C(1) C(2) C(3) 1_555 1_555 1_555 118.4(3) ?
C(1) C(2) H(2) 1_555 1_555 1_555 120.8(4) no
C(3) C(2) H(2) 1_555 1_555 1_555 120.8(4) no
C(2) C(3) C(4) 1_555 1_555 1_555 119.2(3) ?
C(2) C(3) H(3) 1_555 1_555 1_555 120.4(4) no
C(4) C(3) H(3) 1_555 1_555 1_555 120.4(4) no
C(3) C(4) C(5) 1_555 1_555 1_555 118.2(3) ?
C(3) C(4) H(4) 1_555 1_555 1_555 120.9(3) no
C(5) C(4) H(4) 1_555 1_555 1_555 120.9(3) no
N(1) C(5) C(4) 1_555 1_555 1_555 123.4(2) ?
N(1) C(5) C(6) 1_555 1_555 1_555 116.8(2) ?
C(4) C(5) C(6) 1_555 1_555 1_555 119.7(2) ?
N(2) C(6) N(3) 1_555 1_555 1_555 109.9(2) yes
N(2) C(6) C(5) 1_555 1_555 1_555 126.4(2) yes
N(3) C(6) C(5) 1_555 1_555 1_555 123.6(2) yes
N(2) C(7) N(4) 1_555 1_555 1_555 110.1(2) yes
N(2) C(7) C(8) 1_555 1_555 1_555 127.1(2) yes
N(4) C(7) C(8) 1_555 1_555 1_555 122.7(2) yes
N(5) C(8) C(7) 1_555 1_555 1_555 117.7(2) ?
N(5) C(8) C(9) 1_555 1_555 1_555 122.9(2) ?
C(7) C(8) C(9) 1_555 1_555 1_555 119.4(2) ?
C(8) C(9) C(10) 1_555 1_555 1_555 119.2(2) ?
C(8) C(9) H(5) 1_555 1_555 1_555 120.4(3) no
C(10) C(9) H(5) 1_555 1_555 1_555 120.4(3) no
C(9) C(10) C(11) 1_555 1_555 1_555 118.6(2) ?
C(9) C(10) H(6) 1_555 1_555 1_555 120.7(3) no
C(11) C(10) H(6) 1_555 1_555 1_555 120.7(3) no
C(10) C(11) C(12) 1_555 1_555 1_555 118.5(3) ?
C(10) C(11) H(7) 1_555 1_555 1_555 120.7(3) no
C(12) C(11) H(7) 1_555 1_555 1_555 120.7(3) no
N(5) C(12) C(11) 1_555 1_555 1_555 124.3(3) ?
N(5) C(12) H(8) 1_555 1_555 1_555 117.8(3) no
C(11) C(12) H(8) 1_555 1_555 1_555 117.8(3) no
N(2) C(13) C(14) 1_555 1_555 1_555 120.0(2) ?
N(2) C(13) C(18) 1_555 1_555 1_555 118.7(2) ?
C(14) C(13) C(18) 1_555 1_555 1_555 121.3(2) ?
C(13) C(14) C(15) 1_555 1_555 1_555 119.5(2) ?
C(13) C(14) H(9) 1_555 1_555 1_555 120.3(2) no
C(15) C(14) H(9) 1_555 1_555 1_555 120.2(2) no
C(14) C(15) C(16) 1_555 1_555 1_555 119.3(2) ?
C(14) C(15) H(10) 1_555 1_555 1_555 120.3(2) no
C(16) C(15) H(10) 1_555 1_555 1_555 120.3(2) no
Cl(1) C(16) C(15) 1_555 1_555 1_555 119.6(2) ?
Cl(1) C(16) C(17) 1_555 1_555 1_555 119.1(2) ?
C(15) C(16) C(17) 1_555 1_555 1_555 121.3(2) ?
C(16) C(17) C(18) 1_555 1_555 1_555 119.3(2) ?
C(16) C(17) H(11) 1_555 1_555 1_555 120.4(2) no
C(18) C(17) H(11) 1_555 1_555 1_555 120.4(2) no
C(13) C(18) C(17) 1_555 1_555 1_555 119.3(2) ?
C(13) C(18) H(12) 1_555 1_555 1_555 120.3(2) no
C(17) C(18) H(12) 1_555 1_555 1_555 120.4(2) no
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
Cl(1) C(16) 1_555 1_555 1.737(2) yes
N(1) C(1) 1_555 1_555 1.330(3) ?
N(1) C(5) 1_555 1_555 1.335(3) ?
N(2) C(6) 1_555 1_555 1.372(2) yes
N(2) C(7) 1_555 1_555 1.371(3) yes
N(2) C(13) 1_555 1_555 1.444(2) yes
N(3) N(4) 1_555 1_555 1.378(3) yes
N(3) C(6) 1_555 1_555 1.311(3) yes
N(4) C(7) 1_555 1_555 1.316(3) yes
N(5) C(8) 1_555 1_555 1.337(3) ?
N(5) C(12) 1_555 1_555 1.327(3) ?
C(1) C(2) 1_555 1_555 1.366(4) ?
C(2) C(3) 1_555 1_555 1.374(4) ?
C(3) C(4) 1_555 1_555 1.369(4) ?
C(4) C(5) 1_555 1_555 1.384(3) ?
C(5) C(6) 1_555 1_555 1.469(3) ?
C(7) C(8) 1_555 1_555 1.470(3) ?
C(8) C(9) 1_555 1_555 1.382(3) ?
C(9) C(10) 1_555 1_555 1.367(4) ?
C(10) C(11) 1_555 1_555 1.370(4) ?
C(11) C(12) 1_555 1_555 1.370(4) ?
C(13) C(14) 1_555 1_555 1.372(3) ?
C(13) C(18) 1_555 1_555 1.375(3) ?
C(14) C(15) 1_555 1_555 1.381(3) ?
C(15) C(16) 1_555 1_555 1.373(3) ?
C(16) C(17) 1_555 1_555 1.378(3) ?
C(17) C(18) 1_555 1_555 1.383(3) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 86192505
