#------------------------------------------------------------------------------
#$Date: 2016-02-21 02:03:34 +0200 (Sun, 21 Feb 2016) $
#$Revision: 176798 $
#$URL: svn://www.crystallography.net/cod/cif/2/23/98/2239863.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_2239863
loop_
_publ_author_name
'Assoumatine, Tokouré'
'Stoeckli-Evans, Helen'
_publ_section_title
;
 Crystal structure of 2,3,5,6-tetrakis[(methylsulfanyl)methyl]pyrazine
;
_journal_issue                   9
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o887
_journal_page_last               o888
_journal_paper_doi               10.1107/S1600536814011246
_journal_volume                  70
_journal_year                    2014
_chemical_formula_iupac          'C12 H20 N2 S4'
_chemical_formula_moiety         'C12 H20 N2 S4'
_chemical_formula_sum            'C12 H20 N2 S4'
_chemical_formula_weight         320.54
_chemical_name_systematic
;
2,3,5,6-Tetrakis[(methylsulfanyl)methyl]pyrazine
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_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-2013
_cell_angle_alpha                102.635(6)
_cell_angle_beta                 107.539(5)
_cell_angle_gamma                99.462(9)
_cell_formula_units_Z            1
_cell_length_a                   6.6773(6)
_cell_length_b                   6.9433(4)
_cell_length_c                   9.5135(5)
_cell_measurement_reflns_used    33
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      18.80
_cell_measurement_theta_min      14.15
_cell_volume                     397.61(5)
_computing_cell_refinement       'STADI4 (Stoe & Cie, 1997)'
_computing_data_collection       'STADI4 (Stoe & Cie, 1997)'
_computing_data_reduction        'X-RED (Stoe & Cie, 1997)'
_computing_molecular_graphics    'Mercury (Macrae et al., 2008)'
_computing_publication_material
;
SHELXL2013 (Sheldrick, 2008), PLATON (Spek, 2009) and publCIF
(Westrip, 2010)
;
_computing_structure_refinement  'SHELXL2013 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Stoe AED2 four-circle'
_diffrn_measurement_method       2θ/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  0.0175
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            2960
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.493
_diffrn_reflns_theta_min         2.343
_diffrn_standards_decay_%        1
_diffrn_standards_interval_time  60
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.583
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.339
_exptl_crystal_description       plate
_exptl_crystal_F_000             170
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.23
_refine_diff_density_max         0.237
_refine_diff_density_min         -0.204
_refine_ls_extinction_coef       0.064(11)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL2013 (Sheldrick, 2008)'
_refine_ls_goodness_of_fit_ref   1.083
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     85
_refine_ls_number_reflns         1478
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.083
_refine_ls_R_factor_all          0.0383
_refine_ls_R_factor_gt           0.0321
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0451P)²+0.1143P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0831
_refine_ls_wR_factor_ref         0.0880
_reflns_number_gt                1283
_reflns_number_total             1478
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            hb0006sup1.cif
_cod_data_source_block           I
_cod_database_code               2239863
_cod_database_fobs_code          2239863
#BEGIN Tags that were not found in dictionaries:
_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.
;
_shelx_estimated_absorpt_t_min   0.800
_shelx_estimated_absorpt_t_max   0.878
_shelxl_version_number           2.013
#END Tags that were not found in dictionaries
loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 x,y,z
2 -x,-y,-z
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_thermal_displace_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
S S1 0.10172(10) 0.33963(9) 0.10899(6) 0.0509(2) Uani d . 1.000
S S2 0.37011(9) 0.28482(9) 0.80525(6) 0.0515(2) Uani d . 1.000
N N1 -0.0169(2) 0.2930(2) 0.44718(16) 0.0326(4) Uani d . 1.000
C C1 -0.0580(3) 0.4056(3) 0.34870(19) 0.0311(5) Uani d . 1.000
C C2 0.0402(3) 0.3854(3) 0.59786(19) 0.0313(5) Uani d . 1.000
C C3 -0.1194(3) 0.2955(3) 0.1806(2) 0.0390(6) Uani d . 1.000
C C4 0.2772(5) 0.2016(4) 0.2027(3) 0.0684(10) Uani d . 1.000
C C5 0.0843(3) 0.2519(3) 0.7029(2) 0.0376(6) Uani d . 1.000
C C6 0.4534(4) 0.1829(4) 0.6484(3) 0.0665(9) Uani d . 1.000
H H3A -0.23980 0.33950 0.12120 0.0470 Uiso c RU 1.000
H H3B -0.16800 0.15040 0.16540 0.0470 Uiso c RU 1.000
H H4A 0.33380 0.26610 0.31160 0.1030 Uiso c RU 1.000
H H4B 0.39480 0.20040 0.16450 0.1030 Uiso c RU 1.000
H H4C 0.19730 0.06420 0.18230 0.1030 Uiso c RU 1.000
H H5A 0.02160 0.11060 0.64270 0.0450 Uiso c RU 1.000
H H5B 0.01290 0.28160 0.77720 0.0450 Uiso c RU 1.000
H H6A 0.36700 0.04660 0.59450 0.1000 Uiso c RU 1.000
H H6B 0.60330 0.18130 0.68720 0.1000 Uiso c RU 1.000
H H6C 0.43450 0.26620 0.57940 0.1000 Uiso c RU 1.000
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'
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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C3 S1 C4 . . 101.45(13) no
C5 S2 C6 . . 100.09(11) no
C1 N1 C2 . . 118.31(16) no
N1 C1 C3 . . 116.40(17) no
N1 C1 C2 . 2_566 120.78(15) no
C2 C1 C3 2_566 . 122.82(17) no
N1 C2 C5 . . 116.03(17) no
N1 C2 C1 . 2_566 120.91(17) no
C1 C2 C5 2_566 . 123.05(15) no
S1 C3 C1 . . 113.18(14) no
S2 C5 C2 . . 113.56(15) no
S1 C3 H3A . . 109.00 no
S1 C3 H3B . . 109.00 no
C1 C3 H3A . . 109.00 no
C1 C3 H3B . . 109.00 no
H3A C3 H3B . . 108.00 no
S1 C4 H4A . . 109.00 no
S1 C4 H4B . . 109.00 no
S1 C4 H4C . . 109.00 no
H4A C4 H4B . . 109.00 no
H4A C4 H4C . . 109.00 no
H4B C4 H4C . . 109.00 no
S2 C5 H5A . . 109.00 no
S2 C5 H5B . . 109.00 no
C2 C5 H5A . . 109.00 no
C2 C5 H5B . . 109.00 no
H5A C5 H5B . . 108.00 no
S2 C6 H6A . . 109.00 no
S2 C6 H6B . . 109.00 no
S2 C6 H6C . . 109.00 no
H6A C6 H6B . . 110.00 no
H6A C6 H6C . . 109.00 no
H6B C6 H6C . . 109.00 no
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 C3 . 1.813(2) no
S1 C4 . 1.789(3) no
S2 C5 . 1.812(2) no
S2 C6 . 1.790(3) no
N1 C1 . 1.342(2) no
N1 C2 . 1.342(2) no
C1 C3 . 1.509(2) no
C1 C2 2_566 1.401(3) no
C2 C5 . 1.504(3) no
C3 H3A . 0.9700 no
C3 H3B . 0.9700 no
C4 H4A . 0.9600 no
C4 H4B . 0.9600 no
C4 H4C . 0.9600 no
C5 H5A . 0.9700 no
C5 H5B . 0.9700 no
C6 H6A . 0.9600 no
C6 H6B . 0.9600 no
C6 H6C . 0.9600 no
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
C3 H3A S2 2_566 0.97 2.89 3.589(2) 130
C5 H5B S1 1_556 0.97 2.95 3.7395(19) 139
C5 H5B S1 2_566 0.97 2.93 3.614(2) 128
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_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C4 S1 C3 C1 . . . 70.47(18) no
C6 S2 C5 C2 . . . -67.65(17) no
C2 N1 C1 C3 . . . 179.41(18) no
C2 N1 C1 C2 . . 2_566 0.4(3) no
C1 N1 C2 C5 . . . 179.98(18) no
C1 N1 C2 C1 . . 2_566 -0.4(3) no
N1 C1 C3 S1 . . . -101.84(19) no
C2 C1 C3 S1 2_566 . . 77.1(2) no
N1 C1 C2 N1 . 2_566 2_566 -0.5(3) no
N1 C1 C2 C5 . 2_566 2_566 -180.00(19) no
C3 C1 C2 N1 . 2_566 2_566 -179.35(18) no
C3 C1 C2 C5 . 2_566 2_566 1.1(3) no
N1 C2 C5 S2 . . . 103.98(18) no
C1 C2 C5 S2 2_566 . . -75.6(2) no
