#------------------------------------------------------------------------------
#$Date: 2025-08-19 13:43:10 +0300 (Tue, 19 Aug 2025) $
#$Revision: 301803 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/20/78/2207899.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_2207899
loop_
_publ_author_name
'Shu-Sheng Zhang'
'Jun Wan'
'Chun-Li Li'
'Xue-Mei Li'
'Ping-Kai Ouyang'
_publ_section_title
;
 2-(2-Fluoro-5-methylphenyl)-2-oxo-1-(1H-1,2,4-triazol-1-yl)ethyl
 morpholine-4-carbodithioate
;
_journal_coeditor_code           SJ6189
_journal_issue                   1
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o358
_journal_page_last               o359
_journal_paper_doi               10.1107/S1600536805042029
_journal_volume                  62
_journal_year                    2006
_chemical_formula_iupac          'C16 H17 F N4 O2 S2'
_chemical_formula_moiety         'C16 H17 F N4 O2 S2'
_chemical_formula_sum            'C16 H17 F N4 O2 S2'
_chemical_formula_weight         380.46
_chemical_name_systematic
;
2-(2-Fluoro-5-methylphenyl)-2-oxo-1-(1H-1,2,4-triazol-1-yl)ethyl
morpholine-4-carbodithioate
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                98.200(3)
_cell_angle_beta                 92.649(4)
_cell_angle_gamma                109.900(3)
_cell_formula_units_Z            2
_cell_length_a                   6.7311(13)
_cell_length_b                   7.7910(15)
_cell_length_c                   18.107(4)
_cell_measurement_reflns_used    1446
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25.9
_cell_measurement_theta_min      2.3
_cell_volume                     879.1(3)
_computing_cell_refinement       'SAINT (Siemens, 1996)'
_computing_data_collection       'SMART (Siemens, 1996)'
_computing_data_reduction        SAINT
_computing_molecular_graphics    SHELXTL
_computing_publication_material
;
SHELXTL, PARST (Nardelli, 1995) and PLATON (Spek, 2003)
;
_computing_structure_refinement  SHELXTL
_computing_structure_solution    'SHELXTL (Sheldrick, 1997)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 8.33
_diffrn_measured_fraction_theta_full 0.973
_diffrn_measured_fraction_theta_max 0.973
_diffrn_measurement_device_type  'Siemens SMART 1000 CCD area-detector'
_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  0.0139
_diffrn_reflns_av_sigmaI/netI    0.0324
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            4955
_diffrn_reflns_theta_full        26.03
_diffrn_reflns_theta_max         26.03
_diffrn_reflns_theta_min         2.28
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.331
_exptl_absorpt_correction_T_max  0.9708
_exptl_absorpt_correction_T_min  0.9102
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.437
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             396
_exptl_crystal_size_max          0.29
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.330
_refine_diff_density_min         -0.176
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     226
_refine_ls_number_reflns         3385
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.057
_refine_ls_R_factor_all          0.0756
_refine_ls_R_factor_gt           0.0545
_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)+(0.0636P)²+0.3536P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1244
_refine_ls_wR_factor_ref         0.1383
_reflns_number_gt                2534
_reflns_number_total             3385
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            sj6189.cif
_cod_data_source_block           I
_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:

'_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 
;
_cod_database_code               2207899
_cod_database_fobs_code          2207899
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_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_type_symbol
S1 0.17311(13) 0.60830(11) 0.24119(4) 0.0525(2) Uani d . 1 S
S2 0.39342(16) 0.41709(12) 0.13363(4) 0.0658(3) Uani d . 1 S
F1 0.6179(3) 0.5610(3) 0.32055(10) 0.0689(5) Uani d . 1 F
O1 0.0206(3) 0.4158(4) 0.39562(11) 0.0704(7) Uani d . 1 O
O2 0.1976(4) 0.9085(3) 0.00547(13) 0.0714(7) Uani d . 1 O
N1 0.2772(4) 0.7009(3) 0.11157(12) 0.0440(6) Uani d . 1 N
N2 -0.0098(4) 0.2475(3) 0.25445(12) 0.0468(6) Uani d . 1 N
N3 -0.0062(4) 0.0810(4) 0.26668(18) 0.0681(8) Uani d . 1 N
N4 -0.3260(5) 0.0512(5) 0.21260(18) 0.0834(10) Uani d . 1 N
C1 0.5869(5) 0.6355(4) 0.38979(17) 0.0491(7) Uani d . 1 C
C2 0.7643(5) 0.7462(4) 0.4363(2) 0.0616(9) Uani d . 1 C
H2A 0.8988 0.7686 0.4203 0.074 Uiso calc R 1 H
C3 0.7403(5) 0.8238(4) 0.50711(19) 0.0607(8) Uani d . 1 C
H3B 0.8604 0.8978 0.5390 0.073 Uiso calc R 1 H
C4 0.5407(5) 0.7942(4) 0.53199(16) 0.0501(7) Uani d . 1 C
C5 0.3666(5) 0.6785(4) 0.48332(15) 0.0454(7) Uani d . 1 C
H5A 0.2320 0.6546 0.4994 0.054 Uiso calc R 1 H
C6 0.3834(4) 0.5962(4) 0.41141(15) 0.0420(6) Uani d . 1 C
C7 0.1833(4) 0.4699(4) 0.36642(15) 0.0444(6) Uani d . 1 C
C8 0.1770(4) 0.4112(4) 0.28149(14) 0.0424(6) Uani d . 1 C
H8A 0.3056 0.3846 0.2702 0.051 Uiso calc R 1 H
C9 0.2876(4) 0.5796(4) 0.15465(14) 0.0414(6) Uani d . 1 C
C10 0.3925(5) 0.7235(5) 0.04465(16) 0.0543(8) Uani d . 1 C
H10A 0.4244 0.6126 0.0281 0.065 Uiso calc R 1 H
H10B 0.5260 0.8266 0.0571 0.065 Uiso calc R 1 H
C11 0.2647(6) 0.7582(5) -0.01740(17) 0.0650(9) Uani d . 1 C
H11A 0.3494 0.7834 -0.0591 0.078 Uiso calc R 1 H
H11B 0.1412 0.6478 -0.0346 0.078 Uiso calc R 1 H
C12 0.0693(5) 0.8718(5) 0.06493(19) 0.0630(9) Uani d . 1 C
H12A -0.0534 0.7603 0.0484 0.076 Uiso calc R 1 H
H12B 0.0187 0.9735 0.0788 0.076 Uiso calc R 1 H
C13 0.1891(5) 0.8476(4) 0.13196(17) 0.0526(7) Uani d . 1 C
H13A 0.3034 0.9630 0.1518 0.063 Uiso calc R 1 H
H13B 0.0948 0.8157 0.1707 0.063 Uiso calc R 1 H
C14 -0.2013(6) 0.2258(6) 0.22357(19) 0.0699(10) Uani d . 1 C
H14A -0.2419 0.3219 0.2113 0.084 Uiso calc R 1 H
C15 -0.1994(6) -0.0296(5) 0.2400(2) 0.0760(11) Uani d . 1 C
H15A -0.2452 -0.1564 0.2402 0.091 Uiso calc R 1 H
C16 0.5139(6) 0.8809(5) 0.60898(18) 0.0685(9) Uani d . 1 C
H16A 0.3656 0.8439 0.6159 0.103 Uiso calc R 1 H
H16B 0.5732 1.0133 0.6139 0.103 Uiso calc R 1 H
H16C 0.5860 0.8407 0.6462 0.103 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
C9 S1 C8 102.84(12) ?
C11 O2 C12 109.9(2) ?
C9 N1 C13 124.7(2) ?
C9 N1 C10 121.5(2) ?
C13 N1 C10 112.7(2) ?
C14 N2 N3 109.1(3) ?
C14 N2 C8 132.4(3) ?
N3 N2 C8 118.3(2) ?
C15 N3 N2 101.8(3) ?
C14 N4 C15 101.9(3) ?
F1 C1 C2 117.0(3) ?
F1 C1 C6 120.3(3) ?
C2 C1 C6 122.6(3) ?
C1 C2 C3 118.9(3) ?
C1 C2 H2A 120.5 ?
C3 C2 H2A 120.5 ?
C2 C3 C4 121.6(3) ?
C2 C3 H3B 119.2 ?
C4 C3 H3B 119.2 ?
C5 C4 C3 117.1(3) ?
C5 C4 C16 121.1(3) ?
C3 C4 C16 121.7(3) ?
C4 C5 C6 123.2(3) ?
C4 C5 H5A 118.4 ?
C6 C5 H5A 118.4 ?
C1 C6 C5 116.5(3) ?
C1 C6 C7 126.3(3) ?
C5 C6 C7 117.2(2) ?
O1 C7 C6 120.6(2) ?
O1 C7 C8 118.5(2) ?
C6 C7 C8 120.8(2) ?
N2 C8 C7 110.2(2) yes
N2 C8 S1 112.22(18) yes
C7 C8 S1 105.23(18) yes
N2 C8 H8A 109.7 ?
C7 C8 H8A 109.7 ?
S1 C8 H8A 109.7 ?
N1 C9 S2 125.4(2) ?
N1 C9 S1 112.52(19) ?
S2 C9 S1 122.11(15) ?
N1 C10 C11 111.0(2) ?
N1 C10 H10A 109.4 ?
C11 C10 H10A 109.4 ?
N1 C10 H10B 109.4 ?
C11 C10 H10B 109.4 ?
H10A C10 H10B 108.0 ?
O2 C11 C10 112.0(3) ?
O2 C11 H11A 109.2 ?
C10 C11 H11A 109.2 ?
O2 C11 H11B 109.2 ?
C10 C11 H11B 109.2 ?
H11A C11 H11B 107.9 ?
O2 C12 C13 111.5(2) ?
O2 C12 H12A 109.3 ?
C13 C12 H12A 109.3 ?
O2 C12 H12B 109.3 ?
C13 C12 H12B 109.3 ?
H12A C12 H12B 108.0 ?
N1 C13 C12 110.4(3) ?
N1 C13 H13A 109.6 ?
C12 C13 H13A 109.6 ?
N1 C13 H13B 109.6 ?
C12 C13 H13B 109.6 ?
H13A C13 H13B 108.1 ?
N4 C14 N2 111.2(3) ?
N4 C14 H14A 124.4 ?
N2 C14 H14A 124.4 ?
N3 C15 N4 115.9(3) ?
N3 C15 H15A 122.0 ?
N4 C15 H15A 122.0 ?
C4 C16 H16A 109.5 ?
C4 C16 H16B 109.5 ?
H16A C16 H16B 109.5 ?
C4 C16 H16C 109.5 ?
H16A C16 H16C 109.5 ?
H16B C16 H16C 109.5 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
S1 C9 1.797(3) yes
S1 C8 1.799(3) yes
S2 C9 1.660(3) yes
F1 C1 1.361(3) yes
O1 C7 1.208(3) yes
O2 C11 1.409(4) ?
O2 C12 1.411(4) ?
N1 C9 1.326(3) ?
N1 C13 1.468(3) ?
N1 C10 1.469(3) ?
N2 C14 1.327(4) ?
N2 N3 1.355(3) ?
N2 C8 1.457(4) ?
N3 C15 1.314(4) ?
N4 C14 1.314(5) ?
N4 C15 1.336(5) ?
C1 C2 1.370(4) ?
C1 C6 1.386(4) ?
C2 C3 1.379(5) ?
C2 H2A 0.9300 ?
C3 C4 1.391(4) ?
C3 H3B 0.9300 ?
C4 C5 1.386(4) ?
C4 C16 1.506(4) ?
C5 C6 1.394(4) ?
C5 H5A 0.9300 ?
C6 C7 1.488(4) ?
C7 C8 1.535(4) ?
C8 H8A 0.9800 ?
C10 C11 1.494(4) ?
C10 H10A 0.9700 ?
C10 H10B 0.9700 ?
C11 H11A 0.9700 ?
C11 H11B 0.9700 ?
C12 C13 1.496(4) ?
C12 H12A 0.9700 ?
C12 H12B 0.9700 ?
C13 H13A 0.9700 ?
C13 H13B 0.9700 ?
C14 H14A 0.9300 ?
C15 H15A 0.9300 ?
C16 H16A 0.9600 ?
C16 H16B 0.9600 ?
C16 H16C 0.9600 ?
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
C12 H12B O2 2_575 0.97 2.53 3.207(4) 127 yes
C13 H13A N4 1_665 0.97 2.50 3.267(5) 135 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
C14 N2 N3 C15 1.2(4)
C8 N2 N3 C15 176.2(3)
F1 C1 C2 C3 -179.7(3)
C6 C1 C2 C3 -0.8(5)
C1 C2 C3 C4 -0.8(5)
C2 C3 C4 C5 1.9(5)
C2 C3 C4 C16 -179.2(3)
C3 C4 C5 C6 -1.5(4)
C16 C4 C5 C6 179.5(3)
F1 C1 C6 C5 180.0(2)
C2 C1 C6 C5 1.1(4)
F1 C1 C6 C7 2.4(4)
C2 C1 C6 C7 -176.5(3)
C4 C5 C6 C1 0.1(4)
C4 C5 C6 C7 177.9(2)
C1 C6 C7 O1 164.7(3)
C5 C6 C7 O1 -12.9(4)
C1 C6 C7 C8 -17.6(4)
C5 C6 C7 C8 164.8(2)
C14 N2 C8 C7 96.0(4)
N3 N2 C8 C7 -77.5(3)
C14 N2 C8 S1 -20.9(4)
N3 N2 C8 S1 165.6(2)
O1 C7 C8 N2 -20.0(4)
C6 C7 C8 N2 162.3(2)
O1 C7 C8 S1 101.2(3)
C6 C7 C8 S1 -76.5(3)
C9 S1 C8 N2 -85.9(2)
C9 S1 C8 C7 154.19(18)
C13 N1 C9 S2 -178.0(2)
C10 N1 C9 S2 -10.4(4)
C13 N1 C9 S1 1.9(4)
C10 N1 C9 S1 169.4(2)
C8 S1 C9 N1 172.7(2)
C8 S1 C9 S2 -7.4(2)
C9 N1 C10 C11 142.5(3)
C13 N1 C10 C11 -48.6(4)
C12 O2 C11 C10 -60.4(4)
N1 C10 C11 O2 53.9(4)
C11 O2 C12 C13 61.6(4)
C9 N1 C13 C12 -142.0(3)
C10 N1 C13 C12 49.5(3)
O2 C12 C13 N1 -56.0(4)
C15 N4 C14 N2 1.2(4)
N3 N2 C14 N4 -1.6(4)
C8 N2 C14 N4 -175.5(3)
N2 N3 C15 N4 -0.6(4)
C14 N4 C15 N3 -0.3(4)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 10603994
2 PubChem 139068927
