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#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/89/2228986.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_2228986
loop_
_publ_author_name
'Zhao, Xi-Zai'
'Jia, Jing-Jing'
'Ou-Yang, Miao'
'Huang, Fu-Ping'
'Jiang, Yi-Min'
_publ_section_title
;
 1-[2-(Pyrazin-2-ylsulfanyl)ethyl]pyrazine-2(1H)-thione
;
_journal_coeditor_code           BV2167
_journal_issue                   2
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o418
_journal_paper_doi               10.1107/S1600536811001474
_journal_volume                  67
_journal_year                    2011
_chemical_formula_iupac          'C10 H10 N4 S2'
_chemical_formula_moiety         'C10 H10 N4 S2'
_chemical_formula_sum            'C10 H10 N4 S2'
_chemical_formula_weight         250.34
_chemical_name_systematic
;
1-[2-(Pyrazin-2-ylsulfanyl)ethyl]pyrazine-2(1H)-thione
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 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                 92.628(9)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.762(7)
_cell_length_b                   11.737(9)
_cell_length_c                   10.129(8)
_cell_measurement_reflns_used    3231
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      27.91
_cell_measurement_theta_min      2.66
_cell_volume                     1159.3(15)
_computing_cell_refinement       'SAINT (Bruker, 1997)'
_computing_data_collection       'SMART (Bruker, 1997)'
_computing_data_reduction        'SAINT (Bruker, 1997)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker SMART CCD area-detector'
_diffrn_measurement_method       'φ and 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  0.0239
_diffrn_reflns_av_sigmaI/netI    0.0245
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            6280
_diffrn_reflns_theta_full        25.50
_diffrn_reflns_theta_max         25.50
_diffrn_reflns_theta_min         2.66
_exptl_absorpt_coefficient_mu    0.436
_exptl_absorpt_correction_T_max  0.9660
_exptl_absorpt_correction_T_min  0.8731
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 1997)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.434
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             520
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.222
_refine_diff_density_min         -0.224
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     145
_refine_ls_number_reflns         2160
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.060
_refine_ls_R_factor_all          0.0372
_refine_ls_R_factor_gt           0.0320
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0390P)²+0.3470P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0816
_refine_ls_wR_factor_ref         0.0850
_reflns_number_gt                1879
_reflns_number_total             2160
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            bv2167.cif
_cod_data_source_block           I
_cod_original_cell_volume        1159.2(15)
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2228986
_cod_database_fobs_code          2228986
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -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
_atom_site_disorder_assembly
_atom_site_disorder_group
C C1 0.86032(16) 0.00044(13) 0.30816(17) 0.0373(4) Uani d . 1 . .
C C2 0.83823(17) -0.05822(14) 0.42873(18) 0.0418(4) Uani d . 1 . .
H H2 0.8326 -0.1372 0.4242 0.050 Uiso calc R 1 . .
C C3 0.83014(18) 0.10299(16) 0.54879(19) 0.0464(4) Uani d . 1 . .
H H3 0.8205 0.1393 0.6295 0.056 Uiso calc R 1 . .
C C4 0.84852(16) 0.16689(14) 0.44097(18) 0.0413(4) Uani d . 1 . .
H H4 0.8502 0.2459 0.4481 0.050 Uiso calc R 1 . .
C C5 0.8960(2) 0.18947(15) 0.20807(19) 0.0460(4) Uani d . 1 . .
H H5A 0.8572 0.2646 0.2203 0.055 Uiso calc R 1 . .
H H5B 0.8538 0.1572 0.1280 0.055 Uiso calc R 1 . .
C C6 1.0492(2) 0.20010(15) 0.19297(18) 0.0479(4) Uani d . 1 . .
H H6A 1.0649 0.2399 0.1111 0.058 Uiso calc R 1 . .
H H6B 1.0879 0.1243 0.1861 0.058 Uiso calc R 1 . .
C C7 1.08904(17) 0.41615(14) 0.29421(17) 0.0373(4) Uani d . 1 . .
C C8 1.1302(2) 0.49827(17) 0.3863(2) 0.0593(5) Uani d . 1 . .
H H8 1.1800 0.4757 0.4623 0.071 Uiso calc R 1 . .
C C9 1.0294(2) 0.63363(17) 0.2595(2) 0.0587(5) Uani d . 1 . .
H H9 1.0053 0.7093 0.2443 0.070 Uiso calc R 1 . .
C C10 0.99020(19) 0.55385(15) 0.1681(2) 0.0494(5) Uani d . 1 . .
H H10 0.9419 0.5771 0.0915 0.059 Uiso calc R 1 . .
N N1 0.86480(13) 0.11696(11) 0.32118(14) 0.0366(3) Uani d . 1 . .
N N2 0.82515(15) -0.01237(13) 0.54431(15) 0.0464(4) Uani d . 1 . .
N N3 1.01858(15) 0.44304(12) 0.18458(15) 0.0435(4) Uani d . 1 . .
N N4 1.1012(2) 0.60692(15) 0.3698(2) 0.0706(5) Uani d . 1 . .
S S2 1.13825(5) 0.27417(4) 0.32673(5) 0.04440(15) Uani d . 1 . .
S S1 0.87993(6) -0.06784(4) 0.16546(5) 0.05616(17) Uani d . 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'
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
N1 C1 C2 . . 113.79(15) ?
N1 C1 S1 . . 123.76(13) ?
C2 C1 S1 . . 122.45(14) ?
N2 C2 C1 . . 126.58(17) ?
N2 C2 H2 . . 116.7 ?
C1 C2 H2 . . 116.7 ?
C4 C3 N2 . . 122.43(17) ?
C4 C3 H3 . . 118.8 ?
N2 C3 H3 . . 118.8 ?
C3 C4 N1 . . 120.59(16) ?
C3 C4 H4 . . 119.7 ?
N1 C4 H4 . . 119.7 ?
N1 C5 C6 . . 111.51(15) ?
N1 C5 H5A . . 109.3 ?
C6 C5 H5A . . 109.3 ?
N1 C5 H5B . . 109.3 ?
C6 C5 H5B . . 109.3 ?
H5A C5 H5B . . 108.0 ?
C5 C6 S2 . . 114.12(13) ?
C5 C6 H6A . . 108.7 ?
S2 C6 H6A . . 108.7 ?
C5 C6 H6B . . 108.7 ?
S2 C6 H6B . . 108.7 ?
H6A C6 H6B . . 107.6 ?
N3 C7 C8 . . 121.60(17) ?
N3 C7 S2 . . 120.77(13) ?
C8 C7 S2 . . 117.60(15) ?
N4 C8 C7 . . 122.3(2) ?
N4 C8 H8 . . 118.9 ?
C7 C8 H8 . . 118.9 ?
N4 C9 C10 . . 122.09(19) ?
N4 C9 H9 . . 119.0 ?
C10 C9 H9 . . 119.0 ?
N3 C10 C9 . . 122.29(19) ?
N3 C10 H10 . . 118.9 ?
C9 C10 H10 . . 118.9 ?
C4 N1 C1 . . 120.57(14) ?
C4 N1 C5 . . 118.78(15) ?
C1 N1 C5 . . 120.53(14) ?
C2 N2 C3 . . 116.02(16) ?
C7 N3 C10 . . 115.77(16) ?
C8 N4 C9 . . 115.98(18) ?
C7 S2 C6 . . 101.42(9) ?
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
C1 N1 . 1.374(2) ?
C1 C2 . 1.427(3) ?
C1 S1 . 1.671(2) ?
C2 N2 . 1.300(2) ?
C2 H2 . 0.9300 ?
C3 C4 . 1.344(3) ?
C3 N2 . 1.356(3) ?
C3 H3 . 0.9300 ?
C4 N1 . 1.363(2) ?
C4 H4 . 0.9300 ?
C5 N1 . 1.470(2) ?
C5 C6 . 1.515(3) ?
C5 H5A . 0.9700 ?
C5 H5B . 0.9700 ?
C6 S2 . 1.800(2) ?
C6 H6A . 0.9700 ?
C6 H6B . 0.9700 ?
C7 N3 . 1.317(2) ?
C7 C8 . 1.388(3) ?
C7 S2 . 1.761(2) ?
C8 N4 . 1.315(3) ?
C8 H8 . 0.9300 ?
C9 N4 . 1.328(3) ?
C9 C10 . 1.359(3) ?
C9 H9 . 0.9300 ?
C10 N3 . 1.339(2) ?
C10 H10 . 0.9300 ?
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
C4 H4 N4 3_766 0.93 2.56 3.298(3) 137
C2 H2 S2 3_756 0.93 2.99 3.544(3) 119
C3 H3 S2 4_566 0.93 2.92 3.741(3) 148
C8 H8 S1 4_666 0.93 2.97 3.738(3) 140
C9 H9 S1 1_565 0.93 2.98 3.897(3) 169
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
N1 C1 C2 N2 . . . . -1.3(3) ?
S1 C1 C2 N2 . . . . 178.29(14) ?
N2 C3 C4 N1 . . . . -0.8(3) ?
N1 C5 C6 S2 . . . . -65.89(18) ?
N3 C7 C8 N4 . . . . 0.2(3) ?
S2 C7 C8 N4 . . . . 178.53(18) ?
N4 C9 C10 N3 . . . . 1.5(3) ?
C3 C4 N1 C1 . . . . 1.1(2) ?
C3 C4 N1 C5 . . . . -175.01(16) ?
C2 C1 N1 C4 . . . . -0.2(2) ?
S1 C1 N1 C4 . . . . -179.72(12) ?
C2 C1 N1 C5 . . . . 175.90(15) ?
S1 C1 N1 C5 . . . . -3.6(2) ?
C6 C5 N1 C4 . . . . 92.37(18) ?
C6 C5 N1 C1 . . . . -83.77(19) ?
C1 C2 N2 C3 . . . . 1.6(3) ?
C4 C3 N2 C2 . . . . -0.5(3) ?
C8 C7 N3 C10 . . . . 0.2(3) ?
S2 C7 N3 C10 . . . . -178.07(13) ?
C9 C10 N3 C7 . . . . -1.0(3) ?
C7 C8 N4 C9 . . . . 0.2(3) ?
C10 C9 N4 C8 . . . . -1.0(3) ?
N3 C7 S2 C6 . . . . -7.14(16) ?
C8 C7 S2 C6 . . . . 174.49(16) ?
C5 C6 S2 C7 . . . . -74.03(14) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30656454
