##############################################################################
#                                                                            #
# This CIF contains the data for a data article accepted for                 #
# publication in IUCrData. It conforms to the requirements of                #
# Notes for Authors for IUCrData, and has been                               #
# peer reviewed under the auspices of IUCrData.                              #
#                                                                            #
# Full details of the Crystallographic Information File format               #
# are given in the paper "The Crystallographic Information File (CIF):       #
# a New Standard Archive File for Crystallography" by S. R. Hall, F. H.      #
# Allen and I. D. Brown [Acta Cryst. (1991), A47, 655-685].                  #
#                                                                            #
# The current version of the core CIF dictionary is obtainable from          #
# ftp://ftp.iucr.org/pub/cif_core.dic.                                       #
#                                                                            #
# Software is freely available for graphical display of the structure(s)     #
# in this CIF. For information consult the CIF software page                 #
# http://www.iucr.org/resources/cif/software.                                #
#                                                                            #
# This file may be used for bona fide research purposes within the           #
# scientific community so long as proper attribution is given to the data    # 
# article from which it was obtained.                                        #
#                                                                            #
##############################################################################
data_global
_audit_creation_method     CRYSTALS_ver_14.61
data_New_Global_Publ_Block
_journal_data_validation_number     ?
_journal_date_recd_electronic     2016-10-25
_journal_date_accepted     2016-11-13
_journal_name_full     'IUCrData'
_journal_year     2016
_journal_volume     1
_journal_issue     11
_journal_page_first     0
_journal_page_last     0
_journal_paper_category     HI
_journal_paper_doi     10.1107/S2414314616018204
_journal_coeditor_code     BH4018
_publ_contact_author_name     'Khaled Boukebbous'
_publ_contact_author_address
;
Department of Chemistry
University of Constantine
BP 325
Route de Ain El Bey
Constantine 25017
Algeria
;
_publ_contact_author_email     boukebbous.khaled@gmail.com
_publ_contact_author_fax     '+213 31811177'
_publ_contact_author_phone     '+213 666158851'
_publ_section_title
;
4,5-Dichloro-3H-1,2-dithiol-3-one
;
_publ_section_title_footnote     .
loop_
    _publ_author_name
    _publ_author_footnote
    _publ_author_address
    "Boukebbous, Khaled" .
;
Department of Chemistry
University of Constantine
BP 325
Route de Ain El Bey
Constantine 25017
Algeria
;
    "Laifa, El Adoui" .
;
Department of Chemistry
University of Constantine
BP 325
Route de Ain El Bey
Constantine 25017
Algeria
;
    "De Mallmann, Aimery" .
;
C2P2 (CNRS-UMR 5265)
COMS group
Lyon 1 University
ESCPE Lyon
43 Boulevard du 11 Novembre 1918
Villeurbanne 69626
France
;
    "Taoufik, Mostafa" .
;
C2P2 (CNRS-UMR 5265)
COMS group
Lyon 1 University
ESCPE Lyon
43 Boulevard du 11 Novembre 1918
Villeurbanne 69626
France
;
_publ_section_synopsis
;
The title compound belongs to the family of 1,2-dithiol-3-one derivatives,
which contains bioactive compounds. Understanding the crystal structure of
these compounds is the driving force behind this study.
;
data_I
_chemical_name_systematic
;
4,5-Dichloro-3H-1,2-dithiol-3-one
;
_chemical_formula_moiety     'C3 Cl2 O1 S2'
_chemical_formula_sum     'C3 Cl2 O1 S2'
_chemical_formula_weight     187.07
_chemical_melting_point     ?
_symmetry_cell_setting     monoclinic
_symmetry_space_group_name_H-M     'P 1 21/n 1'
_symmetry_space_group_name_Hall     '-P 2yn'
loop_
    _symmetry_equiv_pos_as_xyz
    'x,y,z'
    '-x,-y,-z'
    '-x+1/2,y+1/2,-z+1/2'
    'x+1/2,-y+1/2,z+1/2'
_cell_length_a     8.678(2)
_cell_length_b     7.9332(14)
_cell_length_c     8.7340(18)
_cell_angle_alpha     90
_cell_angle_beta     98.62(2)
_cell_angle_gamma     90
_cell_volume     594.5(2)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     1441
_cell_measurement_theta_min     3.5080
_cell_measurement_theta_max     28.4070
_cell_measurement_temperature     150
_exptl_crystal_description     plate
_exptl_crystal_colour     'light yellow'
_exptl_crystal_size_max     0.507
_exptl_crystal_size_mid     0.185
_exptl_crystal_size_min     0.148
_exptl_crystal_density_diffrn     2.090
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     368
_exptl_absorpt_coefficient_mu     1.673
_exptl_absorpt_correction_type     analytical
_exptl_absorpt_process_details
;
(CrysAlis PRO; Rigaku OD, 2015)
;
_exptl_absorpt_correction_T_min     0.603
_exptl_absorpt_correction_T_max     0.822
_exptl_special_details
;
The crystal was placed in the cold stream of an Oxford
Cryosystems open-flow nitrogen cryostat with a nominal
stability of 0.1 K.
;
_diffrn_ambient_temperature     150
_diffrn_radiation_type     'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator     graphite
_diffrn_measurement_device_type     'Agilent Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_device     'four-circle diffractometer'
_diffrn_measurement_method     ω
_diffrn_detector_area_resol_mean     10.4685
_diffrn_reflns_number     2973
_diffrn_reflns_av_R_equivalents     0.036
_diffrn_reflns_theta_min     3.487
_diffrn_reflns_theta_max     28.678
_diffrn_reflns_theta_full     26.592
_diffrn_measured_fraction_theta_max     0.897
_diffrn_measured_fraction_theta_full     0.997
_diffrn_reflns_limit_h_min     -6
_diffrn_reflns_limit_h_max     11
_diffrn_reflns_limit_k_min     -10
_diffrn_reflns_limit_k_max     10
_diffrn_reflns_limit_l_min     -11
_diffrn_reflns_limit_l_max     11
_diffrn_standards_number     0
_diffrn_standards_interval_count     .
_diffrn_standards_interval_time     .
_diffrn_standards_decay_%     ?
_refine_special_details     ?
_reflns_number_total     1377
_reflns_number_gt     1228
_reflns_threshold_expression     I>2.0σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0359
_refine_ls_R_factor_gt     0.0320
_refine_ls_wR_factor_all     0.0938
_refine_ls_wR_factor_gt     0.0858
_refine_ls_wR_factor_ref     0.0938
_refine_ls_goodness_of_fit_ref     0.9920
_refine_ls_number_reflns     1373
_refine_ls_number_parameters     74
_refine_ls_number_restraints     0
_refine_ls_number_constraints     0
_refine_ls_hydrogen_treatment     undef
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
;
[weight] = 1/[A₀*T₀(x)+A₁*T₁(x) ... +Aₙ₋₁]*Tₙ₋₁(x)]
where Ai are Chebychev coefficients and x= Fcalc/Fmax;
w = [weight]*[1-(deltaF/6*sigmaF)²]²
Ai coefficient are:
0.248E+04 0.417E+04 0.267E+04 0.120E+04 299.
;
_atom_sites_solution_hydrogens     .
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary     difmap
_refine_ls_shift/su_max     0.0004321
_refine_ls_shift/su_mean     0.0000351
_refine_diff_density_max     0.45
_refine_diff_density_min     -0.41
_refine_ls_extinction_method     'Larson, Equation 22'
_refine_ls_extinction_coef     17(4)
loop_
    _atom_type_symbol
    _atom_type_scat_Cromer_Mann_a1
    _atom_type_scat_Cromer_Mann_a2
    _atom_type_scat_Cromer_Mann_a3
    _atom_type_scat_Cromer_Mann_a4
    _atom_type_scat_Cromer_Mann_b1
    _atom_type_scat_Cromer_Mann_b2
    _atom_type_scat_Cromer_Mann_b3
    _atom_type_scat_Cromer_Mann_b4
    _atom_type_scat_Cromer_Mann_c
    _atom_type_scat_dispersion_real
    _atom_type_scat_dispersion_imag
    _atom_type_scat_source
    C 2.3100 1.0200 1.5886 0.8650 20.8439 10.2075 0.5687 51.6512 0.2156 0.0033
                                                                          0.0016
                                'International Tables Vol C 4.2.6.8 and 6.1.1.4'
    H 0.4930 0.3229 0.1402 0.0408 10.5109 26.1257 3.1424 57.7998 0.0030 0.0000
                                                                          0.0000
                                'International Tables Vol C 4.2.6.8 and 6.1.1.4'
    S 6.9053 5.2034 1.4379 1.5863 1.4679 22.2151 0.2536 56.1720 0.8669 0.1246
                                                                          0.1234
                                'International Tables Vol C 4.2.6.8 and 6.1.1.4'
    O 3.0485 2.2868 1.5463 0.8670 13.2771 5.7011 0.3239 32.9089 0.2508 0.0106
                                                                          0.0060
                                'International Tables Vol C 4.2.6.8 and 6.1.1.4'
    Cl 11.4604 7.1964 6.2556 1.6455 0.0104 1.1662 18.5194 47.7784 -9.5574 0.1484
                                                                          0.1585
                                'International Tables Vol C 4.2.6.8 and 6.1.1.4'
_computing_data_collection
;
CrysAlis PRO (Rigaku OD, 2015)
;
_computing_cell_refinement
;
CrysAlis PRO (Rigaku OD, 2015)
;
_computing_data_reduction
;
CrysAlis PRO (Rigaku OD, 2015)
;
_computing_structure_solution
;
SIR97 (Altomare et al.,  1999)
;
_computing_structure_refinement
;
CRYSTALS (Betteridge et al.,  2003)
;
_computing_molecular_graphics
;
Mercury (Macrae et al.,  2008)
;
_computing_publication_material
;
CRYSTALS (Betteridge et al.,  2003)
;
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_occupancy
    _atom_site_disorder_assembly
    _atom_site_disorder_group
    S S1 0.65286(6) 0.53082(7) 0.38502(6) 0.0173 Uani 1.0000 . .
    S S2 0.59380(7) 0.28367(7) 0.33822(7) 0.0182 Uani 1.0000 . .
    C C3 0.4325(2) 0.3208(3) 0.1897(2) 0.0161 Uani 1.0000 . .
    C C4 0.4052(2) 0.4996(3) 0.1666(2) 0.0145 Uani 1.0000 . .
    C C5 0.5024(2) 0.6089(3) 0.2519(2) 0.0145 Uani 1.0000 . .
    Cl Cl6 0.48670(7) 0.82139(7) 0.23385(7) 0.0207 Uani 1.0000 . .
    Cl Cl7 0.25439(6) 0.56383(7) 0.03087(6) 0.0195 Uani 1.0000 . .
    O O8 0.3614(2) 0.2041(2) 0.1230(2) 0.0232 Uani 1.0000 . .
loop_
    _atom_site_aniso_label
    _atom_site_aniso_U_11
    _atom_site_aniso_U_22
    _atom_site_aniso_U_33
    _atom_site_aniso_U_12
    _atom_site_aniso_U_13
    _atom_site_aniso_U_23
    S1 0.0155(3) 0.0155(3) 0.0199(3) 0.00018(18) -0.0002(2) -0.00018(19)
    S2 0.0196(3) 0.0133(3) 0.0210(3) 0.00319(19) 0.0008(2) 0.00174(19)
    C3 0.0178(10) 0.0132(10) 0.0175(10) 0.0016(8) 0.0032(8) -0.0001(8)
    C4 0.0151(9) 0.0133(9) 0.0149(10) 0.0020(8) 0.0018(8) -0.0007(8)
    C5 0.0152(9) 0.0131(10) 0.0156(10) 0.0022(7) 0.0039(8) 0.0008(8)
    Cl6 0.0220(3) 0.0111(3) 0.0280(3) -0.00152(18) 0.0007(2) -0.00077(19)
    Cl7 0.0199(3) 0.0157(3) 0.0207(3) 0.00089(19) -0.0038(2) 0.00105(19)
    O8 0.0283(9) 0.0126(8) 0.0270(9) -0.0034(6) -0.0018(7) -0.0025(6)
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
    S1 S2 . . 2.0521(8) n
    S1 C5 . . 1.728(2) n
    S2 C3 . . 1.785(2) n
    C3 C4 . . 1.447(3) n
    C3 O8 . . 1.212(3) n
    C4 C5 . . 1.353(3) n
    C4 Cl7 . . 1.707(2) n
    C5 Cl6 . . 1.696(2) n
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
    S2 S1 C5 . . . 93.88(8) n
    S1 S2 C3 . . . 97.60(8) n
    S2 C3 C4 . . . 110.94(16) n
    S2 C3 O8 . . . 120.71(17) n
    C4 C3 O8 . . . 128.3(2) n
    C3 C4 C5 . . . 118.4(2) n
    C3 C4 Cl7 . . . 118.83(17) n
    C5 C4 Cl7 . . . 122.75(18) n
    S1 C5 C4 . . . 119.11(18) n
    S1 C5 Cl6 . . . 117.45(13) n
    C4 C5 Cl6 . . . 123.43(17) n
_iucr_refine_instructions_details
;
#
# Punched on 25/07/16 at 11:31:53
#
#LIST     12
BLOCK SCALE X'S  U'S
CONT EXTPARAM
END
#
# Punched on 25/07/16 at 11:31:53
#
#LIST     16
NO
REM   HREST   START (DO NOT REMOVE THIS LINE)
REM   HREST   END (DO NOT REMOVE THIS LINE)
END
;
