##############################################################################
#                                                                            #
# 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.                                        #
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data_global
_audit_creation_method     'SHELXL-2016/6'
_journal_date_recd_electronic     2017-06-30
_journal_date_accepted     2017-07-10
_journal_name_full     'IUCrData'
_journal_year     2017
_journal_volume     2
_journal_issue      7
_journal_page_first     0
_journal_page_last     0
_journal_paper_category     HI
_journal_paper_doi     10.1107/S2414314617010239
_journal_coeditor_code     WM4053
_publ_contact_author_name     'Tomura, Masaaki'
_publ_contact_author_address
;
Institute for Molecular Science
Myodaiji, Okazaki 444-8585, Japan
;
_publ_contact_author_email     tomura@ims.ac.jp
_publ_contact_author_fax     '+81-564-54-2254'
_publ_contact_author_phone     '+81-564-55-7486'
_publ_section_title
;
2-Sulfanylidene-1,3-dithiolo[4,5-b]pyrazine-5,6-dicarbonitrile
;
loop_
    _publ_author_name
    _publ_author_address
    'Tomura, Masaaki'
;
Institute for Molecular Science
Myodaiji
Okazaki 444-8585
Japan
;
_publ_section_synopsis
;
The title 1,3-dithiolo[4,5-b]pyrazine-5,6-dicarbonitrile molecule is
essentially planar, with an r.m.s deviation of 0.042(3) Å from the
least-squares plane.
;
data_I
_chemical_name_systematic
;
2-Sulfanylidene-1,3-dithiolo[4,5-b]pyrazine-5,6-dicarbonitrile
;
_chemical_name_common
;
;
_chemical_formula_moiety     'C7 N4 S3'
_chemical_formula_sum     'C7 N4 S3'
_chemical_formula_iupac     'C7 N4 S3'
_chemical_formula_weight     236.29
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system     orthorhombic
_space_group_name_H-M_alt     'P 21 21 21'
_space_group_name_Hall     'P 2ac 2ab'
loop_
    _space_group_symop_operation_xyz
    'x, y, z'
    '-x+1/2, -y, z+1/2'
    'x+1/2, -y+1/2, -z'
    '-x, y+1/2, -z+1/2'
_cell_length_a     6.1657(15)
_cell_length_b     7.0875(19)
_cell_length_c     20.883(6)
_cell_angle_alpha     90
_cell_angle_beta     90
_cell_angle_gamma     90
_cell_volume     912.6(4)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     3015
_cell_measurement_theta_min     2.0
_cell_measurement_theta_max     30.7
_cell_measurement_temperature     173(2)
_exptl_crystal_description     'Prism'
_exptl_crystal_colour     'Orange'
_exptl_crystal_size_max     0.300
_exptl_crystal_size_mid     0.300
_exptl_crystal_size_min     0.050
_exptl_crystal_density_diffrn     1.720
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     472
_exptl_absorpt_coefficient_mu     0.769
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details
;
(ABSCOR; Higashi, 1995)
;
_shelx_estimated_absorpt_T_min     0.802
_shelx_estimated_absorpt_T_max     0.963
_exptl_absorpt_correction_T_min     0.8249
_exptl_absorpt_correction_T_max     1.0000
_diffrn_ambient_temperature     173(2)
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator     'Graphite Monochromator'
_diffrn_measurement_device_type     'Rigaku/MSC Mercury CCD'
_diffrn_measurement_method     'φ & ω scans'
_diffrn_detector_area_resol_mean     14.7059
_diffrn_reflns_number     8289
_diffrn_reflns_av_R_equivalents     0.0307
_diffrn_reflns_theta_min     1.950
_diffrn_reflns_theta_max     30.819
_diffrn_reflns_theta_full     25.000
_diffrn_measured_fraction_theta_max     0.924
_diffrn_measured_fraction_theta_full     0.999
_diffrn_reflns_limit_h_min     -8
_diffrn_reflns_limit_h_max     6
_diffrn_reflns_limit_k_min     -9
_diffrn_reflns_limit_k_max     8
_diffrn_reflns_limit_l_min     -23
_diffrn_reflns_limit_l_max     28
_refine_special_details
;
Refinement of F² against ALL reflections.  The weighted R-factor wR and
goodness of fit S are based on F², conventional R-factors R are based
on F, with F set to zero for negative F². The threshold expression of
F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement.  R-factors based
on F² are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;
_reflns_number_total     2561
_reflns_number_gt     2314
_reflns_threshold_expression     'I > 2σ(I)'
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0463
_refine_ls_R_factor_gt     0.0406
_refine_ls_wR_factor_gt     0.0975
_refine_ls_wR_factor_ref     0.1030
_refine_ls_goodness_of_fit_ref     1.114
_refine_ls_restrained_S_all     1.114
_refine_ls_number_reflns     2561
_refine_ls_number_parameters     127
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     undef
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
              'w=1/[σ²(Fo²)+(0.0486P)²+0.1364P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens     .
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary     difmap
_refine_ls_shift/su_max     0.000
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.285
_refine_diff_density_min     -0.346
_refine_ls_extinction_method     none
_refine_ls_extinction_coef     .
_refine_ls_abs_structure_details
;
Flack x determined using 803 quotients [(I+)-(I-)]/[(I+)+(I-)]
(Parsons et al.,  2013)
;
_refine_ls_abs_structure_Flack     0.07(4)
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'
    'N' 'N' 0.0061 0.0033
                         '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'
_computing_data_collection
;
CrystalClear (Rigaku/MSC, 2006)
;
_computing_cell_refinement
;
CrystalClear (Rigaku/MSC, 2006)
;
_computing_data_reduction
;
CrystalClear (Rigaku/MSC, 2006)
;
_computing_structure_solution
;
SIR2014 (Burla et al.,  2015)
;
_computing_structure_refinement
;
SHELXL2016 (Sheldrick, 2015)
;
_computing_molecular_graphics
;
PLATON (Spek, 2009) and Mercury (Macrae et al.,  2008)
;
_computing_publication_material
;
SHELXL2016 (Sheldrick, 2015)
;
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_occupancy
    _atom_site_disorder_assembly
    _atom_site_disorder_group
    S S1 -0.17153(16) 0.55587(14) -0.06252(4) 0.0479(3) Uani d 1 . .
    S S2 -0.21351(14) 0.62442(14) 0.07652(4) 0.0434(2) Uani d 1 . .
    S S3 0.17499(14) 0.43326(12) 0.02606(4) 0.0410(2) Uani d 1 . .
    N N1 -0.0522(4) 0.5875(4) 0.19453(13) 0.0339(6) Uani d 1 . .
    N N2 0.3228(4) 0.4055(4) 0.14587(13) 0.0334(6) Uani d 1 . .
    N N3 0.0894(5) 0.6018(5) 0.35380(15) 0.0451(7) Uani d 1 . .
    N N4 0.6025(5) 0.3496(4) 0.28648(16) 0.0445(7) Uani d 1 . .
    C C1 -0.0756(6) 0.5386(5) 0.00956(17) 0.0394(7) Uani d 1 . .
    C C2 -0.0230(5) 0.5554(5) 0.13276(16) 0.0338(6) Uani d 1 . .
    C C3 0.1080(5) 0.5255(4) 0.23255(15) 0.0309(6) Uani d 1 . .
    C C4 0.2925(5) 0.4362(4) 0.20854(15) 0.0318(6) Uani d 1 . .
    C C5 0.1642(5) 0.4634(4) 0.10837(15) 0.0314(6) Uani d 1 . .
    C C6 0.0915(5) 0.5664(5) 0.30048(17) 0.0359(7) Uani d 1 . .
    C C7 0.4656(5) 0.3844(5) 0.25174(16) 0.0344(7) Uani d 1 . .
_geom_special_details
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
    _geom_bond_atom_site_label_1
    _geom_bond_atom_site_label_2
    _geom_bond_site_symmetry_2
    _geom_bond_distance
    _geom_bond_publ_flag
    S1 C1 . 1.622(4) ?
    S2 C2 . 1.732(3) ?
    S2 C1 . 1.746(4) ?
    S3 C5 . 1.733(3) ?
    S3 C1 . 1.750(4) ?
    N1 C2 . 1.322(4) ?
    N1 C3 . 1.341(4) ?
    N2 C5 . 1.319(4) ?
    N2 C4 . 1.340(4) ?
    N3 C6 . 1.141(4) ?
    N4 C7 . 1.140(4) ?
    C2 C5 . 1.420(4) ?
    C3 C4 . 1.395(4) ?
    C3 C6 . 1.452(5) ?
    C4 C7 . 1.445(4) ?
loop_
    _geom_contact_atom_site_label_1
    _geom_contact_atom_site_label_2
    _geom_contact_distance
    _geom_contact_site_symmetry_1
    _geom_contact_site_symmetry_2
    _geom_contact_publ_flag
    S1 N4 3.251(4) . 2_564 yes
    S1 N3 3.308(3) . 2_464 yes
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_3
    _geom_angle
    _geom_angle_publ_flag
    C2 S2 C1 . . 96.57(17) ?
    C5 S3 C1 . . 96.24(16) ?
    C2 N1 C3 . . 114.9(3) ?
    C5 N2 C4 . . 115.2(3) ?
    S1 C1 S2 . . 122.6(2) ?
    S1 C1 S3 . . 122.5(2) ?
    S2 C1 S3 . . 114.9(2) ?
    N1 C2 C5 . . 122.6(3) ?
    N1 C2 S2 . . 121.4(2) ?
    C5 C2 S2 . . 116.0(2) ?
    N1 C3 C4 . . 122.4(3) ?
    N1 C3 C6 . . 117.5(3) ?
    C4 C3 C6 . . 120.0(3) ?
    N2 C4 C3 . . 122.6(3) ?
    N2 C4 C7 . . 117.7(3) ?
    C3 C4 C7 . . 119.6(3) ?
    N2 C5 C2 . . 122.2(3) ?
    N2 C5 S3 . . 121.5(2) ?
    C2 C5 S3 . . 116.3(2) ?
    N3 C6 C3 . . 176.4(4) ?
    N4 C7 C4 . . 177.7(4) ?
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_site_symmetry_1
    _geom_torsion_site_symmetry_2
    _geom_torsion_site_symmetry_3
    _geom_torsion_site_symmetry_4
    _geom_torsion
    _geom_torsion_publ_flag
    C2 S2 C1 S1 . . . . 179.2(2) ?
    C2 S2 C1 S3 . . . . -1.0(2) ?
    C5 S3 C1 S1 . . . . -179.3(2) ?
    C5 S3 C1 S2 . . . . 1.0(2) ?
    C3 N1 C2 C5 . . . . -0.4(5) ?
    C3 N1 C2 S2 . . . . 179.7(2) ?
    C1 S2 C2 N1 . . . . -179.4(3) ?
    C1 S2 C2 C5 . . . . 0.7(3) ?
    C2 N1 C3 C4 . . . . 0.8(4) ?
    C2 N1 C3 C6 . . . . 176.4(3) ?
    C5 N2 C4 C3 . . . . -0.9(4) ?
    C5 N2 C4 C7 . . . . -177.0(3) ?
    N1 C3 C4 N2 . . . . -0.2(5) ?
    C6 C3 C4 N2 . . . . -175.7(3) ?
    N1 C3 C4 C7 . . . . 175.8(3) ?
    C6 C3 C4 C7 . . . . 0.3(4) ?
    C4 N2 C5 C2 . . . . 1.3(4) ?
    C4 N2 C5 S3 . . . . -179.4(2) ?
    N1 C2 C5 N2 . . . . -0.7(5) ?
    S2 C2 C5 N2 . . . . 179.2(2) ?
    N1 C2 C5 S3 . . . . -180.0(3) ?
    S2 C2 C5 S3 . . . . -0.1(3) ?
    C1 S3 C5 N2 . . . . -179.8(3) ?
    C1 S3 C5 C2 . . . . -0.6(3) ?
