#------------------------------------------------------------------------------
#$Date: 2025-08-19 13:43:10 +0300 (Tue, 19 Aug 2025) $
#$Revision: 301803 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/20/83/2208313.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_2208313
loop_
_publ_author_name
'Zhi-Yi Wang'
'Jun Wan'
'Xue-Mei Li'
'Chun-Li Li'
'Shu-Sheng Zhang'
_publ_section_title
;
 1-(4-Chlorobenzoyl)-2-(1H-1,2,4-triazol-1-yl)ethyl
 morpholine-4-carbodithioate
;
_journal_coeditor_code           ER6039
_journal_issue                   3
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1081
_journal_page_last               o1083
_journal_paper_doi               10.1107/S1600536806005162
_journal_volume                  62
_journal_year                    2006
_chemical_formula_iupac          'C16 H17 Cl N4 O2 S2'
_chemical_formula_moiety         'C16 H17 Cl N4 O2 S2'
_chemical_formula_sum            'C16 H17 Cl N4 O2 S2'
_chemical_formula_weight         396.91
_chemical_name_systematic
;
1-(4-Chlorobenzoyl)-2-(1H-1,2,4-triazol-1-yl)ethyl
morpholine-4-carbodithioate)
;
_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                 97.1710(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   16.8253(15)
_cell_length_b                   7.4853(7)
_cell_length_c                   14.8743(13)
_cell_measurement_reflns_used    3432
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      24.1
_cell_measurement_theta_min      2.4
_cell_volume                     1858.7(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 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Siemens SMART 1kCCD 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  0.0242
_diffrn_reflns_av_sigmaI/netI    0.0258
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            11068
_diffrn_reflns_theta_full        26.01
_diffrn_reflns_theta_max         26.01
_diffrn_reflns_theta_min         2.44
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.448
_exptl_absorpt_correction_T_max  0.9780
_exptl_absorpt_correction_T_min  0.8925
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            'pale yellow'
_exptl_crystal_density_diffrn    1.418
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             824
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.433
_refine_diff_density_min         -0.297
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     226
_refine_ls_number_reflns         3648
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.022
_refine_ls_R_factor_all          0.0534
_refine_ls_R_factor_gt           0.0429
_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)+(0.0501P)²+0.6924P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1008
_refine_ls_wR_factor_ref         0.1076
_reflns_number_gt                2997
_reflns_number_total             3648
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            er6039.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_H-M      'P 21/c'
_cod_database_code               2208313
_cod_database_fobs_code          2208313
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_type_symbol
_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
Cl Cl1 -0.10571(5) 0.26262(11) 1.12226(6) 0.0902(3) Uani d . 1
S S1 0.27092(3) 0.07266(7) 0.96262(4) 0.04784(17) Uani d . 1
S S2 0.34633(4) 0.33692(7) 1.10056(4) 0.05376(18) Uani d . 1
O O1 0.13254(10) 0.2254(3) 0.79620(11) 0.0669(5) Uani d . 1
O O2 0.50878(10) -0.2610(2) 1.13711(13) 0.0668(5) Uani d . 1
N N1 0.26898(10) 0.5024(2) 0.79557(12) 0.0455(4) Uani d . 1
N N2 0.29997(12) 0.6589(3) 0.83016(14) 0.0590(5) Uani d . 1
N N3 0.22370(14) 0.7050(3) 0.69629(14) 0.0656(6) Uani d . 1
N N4 0.38657(10) -0.0051(2) 1.08983(12) 0.0445(4) Uani d . 1
C C1 0.00892(14) 0.2170(3) 0.90611(17) 0.0566(6) Uani d . 1
H H1A -0.0037 0.1868 0.8454 0.068 Uiso calc R 1
C C2 -0.05047(14) 0.2195(4) 0.96183(19) 0.0637(7) Uani d . 1
H H2B -0.1031 0.1924 0.9389 0.076 Uiso calc R 1
C C3 -0.03126(14) 0.2621(3) 1.05111(18) 0.0557(6) Uani d . 1
C C4 0.04564(14) 0.3050(3) 1.08640(16) 0.0566(6) Uani d . 1
H H4A 0.0576 0.3344 1.1473 0.068 Uiso calc R 1
C C5 0.10493(13) 0.3039(3) 1.03018(15) 0.0508(6) Uani d . 1
H H5A 0.1571 0.3334 1.0535 0.061 Uiso calc R 1
C C6 0.08772(12) 0.2593(3) 0.93933(14) 0.0431(5) Uani d . 1
C C7 0.14912(13) 0.2557(3) 0.87609(14) 0.0443(5) Uani d . 1
C C8 0.23743(12) 0.2863(3) 0.91337(14) 0.0415(5) Uani d . 1
H H8A 0.2418 0.3792 0.9602 0.050 Uiso calc R 1
C C9 0.28949(13) 0.3332(3) 0.84014(16) 0.0507(5) Uani d . 1
H H9A 0.3450 0.3374 0.8671 0.061 Uiso calc R 1
H H9B 0.2846 0.2391 0.7949 0.061 Uiso calc R 1
C C10 0.27041(17) 0.7733(4) 0.76769(18) 0.0664(7) Uani d . 1
H H10A 0.2813 0.8949 0.7728 0.080 Uiso calc R 1
C C11 0.22446(14) 0.5338(3) 0.71678(16) 0.0560(6) Uani d . 1
H H11A 0.1974 0.4460 0.6808 0.067 Uiso calc R 1
C C12 0.34157(11) 0.1321(3) 1.05723(13) 0.0374(4) Uani d . 1
C C13 0.44120(14) 0.0085(3) 1.17450(15) 0.0563(6) Uani d . 1
H H13A 0.4171 -0.0478 1.2232 0.068 Uiso calc R 1
H H13B 0.4505 0.1333 1.1900 0.068 Uiso calc R 1
C C14 0.51919(14) -0.0806(4) 1.16435(18) 0.0614(7) Uani d . 1
H H14A 0.5455 -0.0163 1.1198 0.074 Uiso calc R 1
H H14B 0.5536 -0.0754 1.2217 0.074 Uiso calc R 1
C C15 0.46083(14) -0.2700(3) 1.05231(17) 0.0570(6) Uani d . 1
H H15A 0.4550 -0.3939 1.0336 0.068 Uiso calc R 1
H H15B 0.4875 -0.2070 1.0076 0.068 Uiso calc R 1
C C16 0.37884(13) -0.1898(3) 1.05524(16) 0.0475(5) Uani d . 1
H H16A 0.3493 -0.1900 0.9949 0.057 Uiso calc R 1
H H16B 0.3493 -0.2611 1.0943 0.057 Uiso calc R 1
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'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 '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 C8 103.96(9) ?
C15 O2 C14 109.77(18) ?
C11 N1 N2 109.22(19) ?
C11 N1 C9 129.2(2) ?
N2 N1 C9 121.46(18) ?
C10 N2 N1 101.6(2) ?
C11 N3 C10 101.5(2) ?
C12 N4 C13 121.74(18) ?
C12 N4 C16 125.08(17) ?
C13 N4 C16 112.52(17) ?
C2 C1 C6 121.0(2) ?
C2 C1 H1A 119.5 ?
C6 C1 H1A 119.5 ?
C3 C2 C1 119.2(2) ?
C3 C2 H2B 120.4 ?
C1 C2 H2B 120.4 ?
C2 C3 C4 121.6(2) ?
C2 C3 Cl1 119.47(19) ?
C4 C3 Cl1 118.9(2) ?
C3 C4 C5 119.0(2) ?
C3 C4 H4A 120.5 ?
C5 C4 H4A 120.5 ?
C4 C5 C6 120.9(2) ?
C4 C5 H5A 119.6 ?
C6 C5 H5A 119.6 ?
C5 C6 C1 118.3(2) ?
C5 C6 C7 123.06(19) ?
C1 C6 C7 118.6(2) ?
O1 C7 C6 122.3(2) ?
O1 C7 C8 118.5(2) ?
C6 C7 C8 119.18(18) ?
C9 C8 C7 113.15(17) yes
C9 C8 S1 108.31(14) yes
C7 C8 S1 104.56(14) yes
C9 C8 H8A 110.2 ?
C7 C8 H8A 110.2 ?
S1 C8 H8A 110.2 ?
N1 C9 C8 113.78(17) ?
N1 C9 H9A 108.8 ?
C8 C9 H9A 108.8 ?
N1 C9 H9B 108.8 ?
C8 C9 H9B 108.8 ?
H9A C9 H9B 107.7 ?
N2 C10 N3 116.4(2) ?
N2 C10 H10A 121.8 ?
N3 C10 H10A 121.8 ?
N3 C11 N1 111.3(2) ?
N3 C11 H11A 124.3 ?
N1 C11 H11A 124.3 ?
N4 C12 S2 124.97(15) ?
N4 C12 S1 112.84(14) ?
S2 C12 S1 122.15(11) ?
N4 C13 C14 110.23(19) ?
N4 C13 H13A 109.6 ?
C14 C13 H13A 109.6 ?
N4 C13 H13B 109.6 ?
C14 C13 H13B 109.6 ?
H13A C13 H13B 108.1 ?
O2 C14 C13 112.1(2) ?
O2 C14 H14A 109.2 ?
C13 C14 H14A 109.2 ?
O2 C14 H14B 109.2 ?
C13 C14 H14B 109.2 ?
H14A C14 H14B 107.9 ?
O2 C15 C16 112.18(19) ?
O2 C15 H15A 109.2 ?
C16 C15 H15A 109.2 ?
O2 C15 H15B 109.2 ?
C16 C15 H15B 109.2 ?
H15A C15 H15B 107.9 ?
N4 C16 C15 109.97(19) ?
N4 C16 H16A 109.7 ?
C15 C16 H16A 109.7 ?
N4 C16 H16B 109.7 ?
C15 C16 H16B 109.7 ?
H16A C16 H16B 108.2 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
Cl1 C3 1.738(2) yes
S1 C12 1.781(2) yes
S1 C8 1.819(2) yes
S2 C12 1.661(2) yes
O1 C7 1.208(2) yes
O2 C15 1.411(3) ?
O2 C14 1.414(3) ?
N1 C11 1.331(3) ?
N1 N2 1.357(3) ?
N1 C9 1.451(3) ?
N2 C10 1.315(3) ?
N3 C11 1.317(3) ?
N3 C10 1.341(3) ?
N4 C12 1.331(2) ?
N4 C13 1.467(3) ?
N4 C16 1.475(3) ?
C1 C2 1.376(4) ?
C1 C6 1.392(3) ?
C1 H1A 0.9300 ?
C2 C3 1.365(4) ?
C2 H2B 0.9300 ?
C3 C4 1.372(3) ?
C4 C5 1.379(3) ?
C4 H4A 0.9300 ?
C5 C6 1.387(3) ?
C5 H5A 0.9300 ?
C6 C7 1.482(3) ?
C7 C8 1.537(3) yes
C8 C9 1.522(3) yes
C8 H8A 0.9800 ?
C9 H9A 0.9700 ?
C9 H9B 0.9700 ?
C10 H10A 0.9300 ?
C11 H11A 0.9300 ?
C13 C14 1.496(3) ?
C13 H13A 0.9700 ?
C13 H13B 0.9700 ?
C14 H14A 0.9700 ?
C14 H14B 0.9700 ?
C15 C16 1.510(3) ?
C15 H15A 0.9700 ?
C15 H15B 0.9700 ?
C16 H16A 0.9700 ?
C16 H16B 0.9700 ?
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
C4 H4A O1 4_566 0.93 2.45 3.285(3) 150 yes
C9 H9A O2 3_657 0.97 2.53 3.412(3) 150 yes
C13 H13A Cg1 4_566 0.97 2.89 3.656(3) 137 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
C11 N1 N2 C10 0.2(2)
C9 N1 N2 C10 176.5(2)
C6 C1 C2 C3 -0.7(4)
C1 C2 C3 C4 0.9(4)
C1 C2 C3 Cl1 -179.1(2)
C2 C3 C4 C5 -0.4(4)
Cl1 C3 C4 C5 179.69(19)
C3 C4 C5 C6 -0.4(4)
C4 C5 C6 C1 0.5(3)
C4 C5 C6 C7 -179.9(2)
C2 C1 C6 C5 0.0(3)
C2 C1 C6 C7 -179.6(2)
C5 C6 C7 O1 -176.2(2)
C1 C6 C7 O1 3.4(3)
C5 C6 C7 C8 5.6(3)
C1 C6 C7 C8 -174.83(19)
O1 C7 C8 C9 18.7(3)
C6 C7 C8 C9 -163.07(18)
O1 C7 C8 S1 -99.0(2)
C6 C7 C8 S1 79.3(2)
C12 S1 C8 C9 92.80(16)
C12 S1 C8 C7 -146.28(13)
C11 N1 C9 C8 -98.5(3)
N2 N1 C9 C8 86.0(2)
C7 C8 C9 N1 64.9(2)
S1 C8 C9 N1 -179.71(15)
N1 N2 C10 N3 -0.2(3)
C11 N3 C10 N2 0.2(3)
C10 N3 C11 N1 0.0(3)
N2 N1 C11 N3 -0.1(3)
C9 N1 C11 N3 -176.0(2)
C13 N4 C12 S2 5.7(3)
C16 N4 C12 S2 175.73(16)
C13 N4 C12 S1 -171.94(16)
C16 N4 C12 S1 -1.9(3)
C8 S1 C12 N4 -165.30(15)
C8 S1 C12 S2 16.95(15)
C12 N4 C13 C14 -137.8(2)
C16 N4 C13 C14 51.0(3)
C15 O2 C14 C13 60.8(3)
N4 C13 C14 O2 -56.2(3)
C14 O2 C15 C16 -60.1(3)
C12 N4 C16 C15 139.0(2)
C13 N4 C16 C15 -50.3(2)
O2 C15 C16 N4 54.8(3)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139069144
