#------------------------------------------------------------------------------
#$Date: 2025-08-19 13:43:10 +0300 (Tue, 19 Aug 2025) $
#$Revision: 301803 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/20/47/2204789.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_2204789
loop_
_publ_author_name
'Liangzhong Xu'
'Chongyi Zhu'
'Guodong Si'
'Yongqi Qin'
'Kai Li'
_publ_section_title
3-Anilino-1-(2-fluoro-5-methylphenyl)-3-(methylsulfanyl)-2-(1H-1,2,4-triazol-1-yl)prop-2-en-1-one
_journal_issue                   12
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2471
_journal_page_last               o2472
_journal_paper_doi               10.1107/S160053680403048X
_journal_volume                  60
_journal_year                    2004
_chemical_formula_moiety         'C19 H17 F N4 O S'
_chemical_formula_sum            'C19 H17 F N4 O S'
_chemical_formula_weight         368.43
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_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                 103.76(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   19.651(6)
_cell_length_b                   5.6123(11)
_cell_length_c                   17.187(3)
_cell_measurement_reflns_used    905
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      26.31
_cell_measurement_theta_min      2.42
_cell_volume                     1841.1(8)
_computing_cell_refinement       'SAINT (Siemens, 1996)'
_computing_data_collection       'SMART (Siemens, 1996)'
_computing_data_reduction        SAINT
_computing_molecular_graphics    'SHELXTL (Sheldrick, 1990)'
_computing_publication_material  'WinGX (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker SMART CCD area detector'
_diffrn_measurement_method       'φ and ω 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  0.0271
_diffrn_reflns_av_sigmaI/netI    0.0314
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            10219
_diffrn_reflns_theta_full        26.41
_diffrn_reflns_theta_max         26.41
_diffrn_reflns_theta_min         1.07
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 100
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.201
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.329
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    .
_exptl_crystal_description       block
_exptl_crystal_F_000             768
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.213
_refine_diff_density_min         -0.294
_refine_ls_extinction_coef       0.009(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.015
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     236
_refine_ls_number_reflns         3755
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.015
_refine_ls_R_factor_all          0.0651
_refine_ls_R_factor_gt           0.0424
_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)+(0.0643P)²+0.5510P] where P = (Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1068
_refine_ls_wR_factor_ref         0.1246
_reflns_number_gt                2690
_reflns_number_total             3755
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            rz6019.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
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 'Monoclinic' changed to 'monoclinic'
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_sg_symbol_Hall     '-P 2y bc'
_cod_original_sg_symbol_H-M      P21/c
_cod_database_code               2204789
_cod_database_fobs_code          2204789
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -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
S1 0.23960(3) 0.34227(11) 0.22303(3) 0.05184(19) Uani d . 1 S
F1 0.22987(7) -0.3556(3) -0.08229(10) 0.0734(4) Uani d . 1 F
O1 0.17321(7) 0.0647(3) -0.03601(8) 0.0542(4) Uani d . 1 O
N1 0.32573(7) 0.1432(3) 0.12732(9) 0.0333(3) Uani d . 1 N
N2 0.36603(8) 0.3433(3) 0.14501(10) 0.0436(4) Uani d . 1 N
N3 0.42512(9) 0.0181(4) 0.20105(12) 0.0584(5) Uani d . 1 N
N4 0.13847(8) 0.2649(3) 0.08581(9) 0.0439(4) Uani d . 1 N
H4 0.1263 0.1788 0.0434 0.053 Uiso calc R 1 H
C1 0.34906(10) 0.1418(4) -0.03972(11) 0.0410(4) Uani d . 1 C
H1 0.3555 0.2815 -0.0098 0.049 Uiso calc R 1 H
C2 0.39774(10) 0.0816(4) -0.08358(12) 0.0456(5) Uani d . 1 C
C3 0.46048(12) 0.2381(5) -0.08191(16) 0.0648(6) Uani d . 1 C
H3A 0.5015 0.1407 -0.0762 0.097 Uiso d R 1 H
H3B 0.4667 0.3464 -0.0376 0.097 Uiso d R 1 H
H3C 0.4531 0.3268 -0.1310 0.097 Uiso d R 1 H
C4 0.38672(12) -0.1256(4) -0.12847(13) 0.0528(6) Uani d . 1 C
H4A 0.4180 -0.1674 -0.1592 0.063 Uiso calc R 1 H
C5 0.33024(12) -0.2713(4) -0.12841(13) 0.0549(6) Uani d . 1 C
H5 0.3237 -0.4112 -0.1582 0.066 Uiso calc R 1 H
C6 0.28391(11) -0.2074(4) -0.08392(13) 0.0477(5) Uani d . 1 C
C7 0.29133(9) 0.0005(4) -0.03921(11) 0.0389(4) Uani d . 1 C
C8 0.23557(9) 0.0759(4) 0.00201(11) 0.0390(4) Uani d . 1 C
C9 0.25441(9) 0.1581(3) 0.08347(10) 0.0343(4) Uani d . 1 C
C10 0.36204(10) -0.0456(4) 0.16127(12) 0.0450(5) Uani d . 1 C
H10 0.3451 -0.2010 0.1574 0.054 Uiso calc R 1 H
C11 0.42467(10) 0.2563(5) 0.18908(13) 0.0513(5) Uani d . 1 C
H11 0.4632 0.3519 0.2106 0.062 Uiso calc R 1 H
C12 0.20653(9) 0.2501(4) 0.12322(10) 0.0360(4) Uani d . 1 C
C13 0.17343(13) 0.2477(6) 0.27233(13) 0.0719(8) Uani d . 1 C
H13A 0.1332 0.3491 0.2566 0.108 Uiso calc R 1 H
H13B 0.1914 0.2570 0.3293 0.108 Uiso calc R 1 H
H13C 0.1603 0.0862 0.2575 0.108 Uiso calc R 1 H
C14 0.08336(9) 0.3983(4) 0.10441(11) 0.0409(5) Uani d . 1 C
C15 0.01670(10) 0.3041(5) 0.08238(13) 0.0536(6) Uani d . 1 C
H15 0.0094 0.1568 0.0570 0.064 Uiso calc R 1 H
C16 -0.03955(12) 0.4288(6) 0.09805(16) 0.0736(8) Uani d . 1 C
H16 -0.0845 0.3659 0.0828 0.088 Uiso calc R 1 H
C17 -0.02862(15) 0.6439(6) 0.13599(17) 0.0807(9) Uani d . 1 C
H17 -0.0660 0.7267 0.1475 0.097 Uiso calc R 1 H
C18 0.03707(16) 0.7369(6) 0.15688(17) 0.0783(8) Uani d . 1 C
H18 0.0441 0.8831 0.1831 0.094 Uiso calc R 1 H
C19 0.09361(12) 0.6187(4) 0.13998(16) 0.0599(6) Uani d . 1 C
H19 0.1379 0.6875 0.1525 0.072 Uiso calc 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'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 '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
C12 S1 C13 103.44(11) yes
C10 N1 N2 109.55(15) ?
C10 N1 C9 129.38(16) ?
N2 N1 C9 120.92(15) ?
C11 N2 N1 101.86(17) ?
C10 N3 C11 102.61(17) ?
C12 N4 C14 130.85(17) yes
C12 N4 H4 114.6 yes
C14 N4 H4 114.6 ?
C7 C1 C2 122.23(19) yes
C7 C1 H1 118.9 ?
C2 C1 H1 118.9 ?
C4 C2 C1 118.0(2) ?
C4 C2 C3 121.2(2) ?
C1 C2 C3 120.8(2) ?
C2 C3 H3A 109.5 ?
C2 C3 H3B 109.5 ?
H3A C3 H3B 109.5 ?
C2 C3 H3C 109.5 ?
H3A C3 H3C 109.5 ?
H3B C3 H3C 109.5 ?
C5 C4 C2 121.1(2) ?
C5 C4 H4A 119.4 ?
C2 C4 H4A 119.4 ?
C6 C5 C4 119.2(2) ?
C6 C5 H5 120.4 ?
C4 C5 H5 120.4 ?
F1 C6 C5 118.7(2) ?
F1 C6 C7 119.03(18) ?
C5 C6 C7 122.3(2) ?
C6 C7 C1 117.17(18) ?
C6 C7 C8 120.47(18) ?
C1 C7 C8 122.18(17) ?
O1 C8 C9 121.39(17) ?
O1 C8 C7 118.42(16) ?
C9 C8 C7 120.19(16) ?
C12 C9 N1 117.23(15) ?
C12 C9 C8 123.49(16) ?
N1 C9 C8 119.28(15) ?
N3 C10 N1 110.62(19) ?
N3 C10 H10 124.7 ?
N1 C10 H10 124.7 ?
N2 C11 N3 115.36(19) ?
N2 C11 H11 122.3 ?
N3 C11 H11 122.3 ?
N4 C12 C9 120.17(16) ?
N4 C12 S1 122.91(14) ?
C9 C12 S1 116.92(13) ?
S1 C13 H13A 109.5 ?
S1 C13 H13B 109.5 ?
H13A C13 H13B 109.5 ?
S1 C13 H13C 109.5 ?
H13A C13 H13C 109.5 ?
H13B C13 H13C 109.5 ?
C19 C14 C15 119.8(2) ?
C19 C14 N4 122.56(19) ?
C15 C14 N4 117.61(19) ?
C14 C15 C16 120.1(3) ?
C14 C15 H15 119.9 ?
C16 C15 H15 119.9 ?
C17 C16 C15 119.8(3) ?
C17 C16 H16 120.1 ?
C15 C16 H16 120.1 ?
C18 C17 C16 119.8(2) ?
C18 C17 H17 120.1 ?
C16 C17 H17 120.1 ?
C17 C18 C19 121.3(3) ?
C17 C18 H18 119.3 ?
C19 C18 H18 119.3 ?
C14 C19 C18 119.0(2) ?
C14 C19 H19 120.5 ?
C18 C19 H19 120.5 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
S1 C12 1.7614(19) yes
S1 C13 1.793(3) yes
F1 C6 1.354(2) yes
O1 C8 1.246(2) yes
N1 C10 1.332(2) ?
N1 N2 1.366(2) ?
N1 C9 1.427(2) ?
N2 C11 1.313(3) ?
N3 C10 1.315(3) ?
N3 C11 1.352(3) ?
N4 C12 1.342(2) yes
N4 C14 1.414(2) ?
N4 H4 0.8600 ?
C1 C7 1.386(3) ?
C1 C2 1.393(3) ?
C1 H1 0.9300 ?
C2 C4 1.384(3) ?
C2 C3 1.508(3) ?
C3 H3A 0.9600 ?
C3 H3B 0.9600 ?
C3 H3C 0.9600 ?
C4 C5 1.379(3) ?
C4 H4A 0.9300 ?
C5 C6 1.369(3) ?
C5 H5 0.9300 ?
C6 C7 1.386(3) ?
C7 C8 1.500(3) ?
C8 C9 1.437(3) ?
C9 C12 1.387(2) ?
C10 H10 0.9300 ?
C11 H11 0.9300 ?
C13 H13A 0.9600 ?
C13 H13B 0.9600 ?
C13 H13C 0.9600 ?
C14 C19 1.374(3) ?
C14 C15 1.379(3) ?
C15 C16 1.388(3) ?
C15 H15 0.9300 ?
C16 C17 1.365(4) ?
C16 H16 0.9300 ?
C17 C18 1.359(4) ?
C17 H17 0.9300 ?
C18 C19 1.383(3) ?
C18 H18 0.9300 ?
C19 H19 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
_geom_hbond_publ_flag
N4 H4 O1 ? 0.86 1.93 2.606(2) 134.7 yes
C10 H10 N2 1_545 0.93 2.61 3.444(3) 149.9 yes
C11 H11 N3 2_655 0.93 2.53 3.433(3) 163.5 yes
C19 H19 S1 ? 0.93 2.84 3.275(3) 109.9 yes
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
C10 N1 N2 C11 0.1(2)
C9 N1 N2 C11 176.00(16)
C7 C1 C2 C4 0.7(3)
C7 C1 C2 C3 -179.22(19)
C1 C2 C4 C5 -1.5(3)
C3 C2 C4 C5 178.5(2)
C2 C4 C5 C6 0.9(3)
C4 C5 C6 F1 -177.9(2)
C4 C5 C6 C7 0.6(3)
F1 C6 C7 C1 177.21(18)
C5 C6 C7 C1 -1.3(3)
F1 C6 C7 C8 -7.6(3)
C5 C6 C7 C8 173.8(2)
C2 C1 C7 C6 0.6(3)
C2 C1 C7 C8 -174.42(18)
C6 C7 C8 O1 -45.1(3)
C1 C7 C8 O1 129.8(2)
C6 C7 C8 C9 134.8(2)
C1 C7 C8 C9 -50.3(3)
C10 N1 C9 C12 102.2(2)
N2 N1 C9 C12 -72.8(2)
C10 N1 C9 C8 -77.0(3)
N2 N1 C9 C8 108.0(2)
O1 C8 C9 C12 -6.0(3)
C7 C8 C9 C12 174.16(18)
O1 C8 C9 N1 173.18(18)
C7 C8 C9 N1 -6.7(3)
C11 N3 C10 N1 0.0(2)
N2 N1 C10 N3 -0.1(2)
C9 N1 C10 N3 -175.53(17)
N1 N2 C11 N3 -0.1(2)
C10 N3 C11 N2 0.0(3)
C14 N4 C12 C9 -162.9(2)
C14 N4 C12 S1 17.4(3)
N1 C9 C12 N4 -178.79(18)
C8 C9 C12 N4 0.4(3)
N1 C9 C12 S1 0.9(2)
C8 C9 C12 S1 -179.91(16)
C13 S1 C12 N4 39.1(2)
C13 S1 C12 C9 -140.61(18)
C12 N4 C14 C19 33.2(3)
C12 N4 C14 C15 -149.6(2)
C19 C14 C15 C16 -1.7(3)
N4 C14 C15 C16 -179.1(2)
C14 C15 C16 C17 -0.6(4)
C15 C16 C17 C18 1.2(4)
C16 C17 C18 C19 0.5(4)
C15 C14 C19 C18 3.4(3)
N4 C14 C19 C18 -179.4(2)
C17 C18 C19 C14 -2.8(4)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21173794
2 PubChem 139067264
