#------------------------------------------------------------------------------
#$Date: 2025-08-19 01:52:38 +0300 (Tue, 19 Aug 2025) $
#$Revision: 301791 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/00/20/2002099.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_2002099
loop_
_publ_author_name
'Rodier, N.'
'Robert, J.-M.'
'Le Baut, G.'
_publ_section_title
4-(4,6-Diméthylpyrid-2-yl)-5-éthyl-3-(furan-2-yl)-4H-1,2,4-triazole
_journal_issue                   1
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              161
_journal_page_last               163
_journal_paper_doi               10.1107/S0108270192008631
_journal_volume                  49
_journal_year                    1993
_chemical_formula_sum            'C15 H16 N4 O'
_chemical_formula_weight         268.32
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_type_scat_source           'IntTabIV '
_cell_angle_alpha                90
_cell_angle_beta                 99.810(10)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   16.220(4)
_cell_length_b                   9.7630(7)
_cell_length_c                   18.325(2)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    293
_cell_measurement_theta_max      39.56
_cell_measurement_theta_min      15.36
_cell_volume                     2859.4(8)
_diffrn_measurement_device       'Enraf-Nonius CAD-4'
_diffrn_measurement_method       θ/2θ
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.5418
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            2076
_diffrn_reflns_theta_max         60
_diffrn_standards_decay_%        'non significative                      '
_diffrn_standards_interval_time  120
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.624
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            Incolore
_exptl_crystal_density_diffrn    1.246
_exptl_crystal_description       Parallélépipèdique
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.22
_refine_diff_density_max         0.25(4)
_refine_diff_density_min         -0.19(4)
_refine_ls_extinction_coef       'g = 2.09E-6(6)'
_refine_ls_extinction_method     'Stout & Jensen (1968)'
_refine_ls_goodness_of_fit_obs   1.43
_refine_ls_hydrogen_treatment    refxyz
_refine_ls_number_parameters     20
_refine_ls_number_reflns         1983
_refine_ls_R_factor_obs          0.052
_refine_ls_shift/esd_max         0.05
_refine_ls_structure_factor_coef F
_refine_ls_weighting_scheme      exp(sin\q/\l)^2^
_refine_ls_wR_factor_obs         0.046
_reflns_number_observed          1983
_reflns_number_total             2076
_reflns_observed_criterion       I>3\s(I)
_cod_data_source_file            pa1016.cif
_cod_data_source_block           pa1016_structure_1_of_1
_cod_original_cell_volume        2859.0(10)
_cod_database_code               2002099
loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
N(1) .65390(10) .1348(2) .70500(10)
C(2) .5924(2) .1490(2) .64690(10)
C(3) .5513(2) .2678(3) .6245(2)
C(4) .5743(2) .3848(3) .6659(2)
C(5) .6375(2) .3729(3) .7266(2)
C(6) .6761(2) .2482(3) .74410(10)
N(7) .56860(10) .0244(2) .60700(10)
C(8) .6135(2) -.0503(2) .56510(10)
N(9) .57300(10) -.1619(2) .53990(10)
N(10) .49730(10) -.1608(2) .56770(10)
C(11) .4955(2) -.0506(3) .60690(10)
C(12) .6937(2) -.0115(2) .54860(10)
O(13) .73270(10) -.1109(2) .51450(10)
C(14) .8085(2) -.0552(3) .5037(2)
C(15) .8168(2) .0703(3) .5295(2)
C(16) .7432(2) .1001(3) .5586(2)
C(17) .7459(2) .2340(4) .8091(2)
C(18) .5315(2) .5195(3) .6448(2)
C(19) .4279(2) -.0050(3) .6461(2)
C(20) .3713(2) -.1181(4) .6596(3)
H(3) .509(2) .267(3) .578(2)
H(5) .655(2) .450(3) .759(2)
H(14) .841(2) -.120(4) .475(2)
H(15) .857(2) .137(4) .524(2)
H(16) .734(2) .183(3) .579(2)
H(17) .724(2) .238(4) .854(2)
H(17') .758(2) .149(4) .814(2)
H(17") .783(2) .298(4) .809(2)
H(18) .473(2) .512(4) .650(2)
H(18') .536(2) .543(4) .600(2)
H(18") .548(2) .589(4) .677(2)
H(19) .397(2) .066(4) .617(2)
H(19') .452(2) .036(4) .694(2)
H(20) .339(3) -.084(5) .695(2)
H(20') .417(3) -.170(5) .704(2)
H(20") .378(3) -.196(5) .647(2)
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
N(1) N(1) C(6) 116.1(2) yes
N(1) C(2) C(3) 125.9(2) yes
N(1) C(2) N(7) 114.7(2) yes
C(3) C(2) N(7) 119.4(2) yes
C(2) C(3) C(4) 117.6(2) yes
C(3) C(4) C(5) 117.6(2) yes
C(3) C(4) C(18) 120.6(2) yes
C(5) C(4) C(18) 121.8(2) yes
C(4) C(5) C(6) 120.4(2) yes
N(1) C(6) C(5) 122.4(2) yes
N(1) C(6) C(17) 116.6(2) yes
C(5) C(6) C(17) 121.1(2) yes
C(2) N(7) C(8) 128.3(2) yes
C(2) N(7) C(11) 126.8(2) yes
C(8) N(7) C(11) 104.8(2) yes
N(7) C(8) N(9) 111.1(2) yes
N(7) C(8) C(12) 124.7(2) yes
N(9) C(8) C(12) 124.2(2) yes
C(8) N(9) N(10) 106.3(2) yes
N(9) N(10) C(11) 108.1(2) yes
N(7) C(11) N(10) 109.7(2) yes
N(7) C(11) C(19) 123.0(2) yes
N(10) C(11) C(19) 127.4(2) yes
C(8) C(12) O(13) 114.5(2) yes
C(8) C(12) C(16) 136.4(2) yes
O(13) C(12) C(16) 109.0(2) yes
C(12) O(13) C(14) 106.0(2) yes
O(13) C(14) C(15) 110.7(3) yes
C(14) C(15) C(16) 106.6(3) yes
C(12) C(16) C(15) 107.6(2) yes
C(11) C(19) C(20) 112.9(3) yes
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
N(1) C(2) 1.335(3) no
N(1) C(6) 1.334(3) no
C(2) C(3) 1.366(3) no
C(2) N(7) 1.438(3) no
C(3) C(4) 1.387(4) no
C(4) C(5) 1.383(4) no
C(4) C(18) 1.506(4) no
C(5) C(6) 1.381(4) no
C(6) C(17) 1.503(4) no
N(7) C(8) 1.357(3) no
N(7) C(11) 1.393(3) yes
C(8) N(9) 1.314(3) yes
C(8) C(12) 1.437(4) yes
N(9) N(10) 1.406(3) yes
N(10) C(11) 1.297(3) yes
C(11) C(19) 1.478(4) yes
C(12) O(13) 1.367(3) yes
C(12) C(16) 1.346(4) yes
O(13) C(14) 1.388(4) yes
C(14) C(15) 1.312(4) yes
C(15) C(16) 1.419(4) yes
C(19) C(20) 1.483(5) yes
C(3) H(3) 0.99(3) no
C(5) H(5) 0.97(3) no
C(14) H(14) 1.03(4) no
C(15) H(15) 0.93(4) no
C(16) H(16) 0.91(3) no
C(17) H(17) 0.96(4) no
C(17) H(17') 0.85(4) no
C(17) H(17") 0.87(4) no
C(18) H(18) 0.96(4) no
C(18) H(18') 0.87(4) no
C(18) H(18") 0.91(4) no
C(19) H(19) 0.96(3) no
C(19) H(19') 0.98(3) no
C(20) H(20) 0.96(5) no
C(20) H(20') 1.12(4) no
C(20) H(20") 0.81(5) no
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 10516038
