#------------------------------------------------------------------------------
#$Date: 2025-08-19 16:18:28 +0300 (Tue, 19 Aug 2025) $
#$Revision: 301805 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/58/2225863.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_2225863
loop_
_publ_author_name
'Hemamalini, Madhukar'
'Fun, Hoong-Kun'
_publ_section_title
;
 5,6-Di-2-thienyl-2,3-dihydropyrazine
;
_journal_coeditor_code           HB5396
_journal_issue                   5
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1062
_journal_paper_doi               10.1107/S1600536810012705
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C12 H10 N2 S2'
_chemical_formula_moiety         'C12 H10 N2 S2'
_chemical_formula_sum            'C12 H10 N2 S2'
_chemical_formula_weight         246.34
_chemical_name_systematic
;
5,6-Di-2-thienyl-2,3-dihydropyrazine
;
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL97
_cell_angle_alpha                90.00
_cell_angle_beta                 97.902(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   5.5006(9)
_cell_length_b                   7.5246(12)
_cell_length_c                   14.116(2)
_cell_measurement_reflns_used    5014
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      34.77
_cell_measurement_theta_min      2.91
_cell_volume                     578.71(16)
_computing_cell_refinement       'SAINT (Bruker, 2009)'
_computing_data_collection       'APEX2 (Bruker, 2009)'
_computing_data_reduction        'SAINT (Bruker, 2009)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material
;
SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009)
;
_computing_structure_refinement  'SHELXTL (Sheldrick, 2008)'
_computing_structure_solution    'SHELXTL (Sheldrick, 2008)'
_diffrn_ambient_temperature      100.00(10)
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'Bruker APEX DUO CCD area-detector'
_diffrn_measurement_method       'φ and ω scans'
_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  0.0220
_diffrn_reflns_av_sigmaI/netI    0.0317
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            9583
_diffrn_reflns_theta_full        35.13
_diffrn_reflns_theta_max         35.13
_diffrn_reflns_theta_min         1.46
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.431
_exptl_absorpt_correction_T_max  0.965
_exptl_absorpt_correction_T_min  0.875
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2009)'
_exptl_crystal_colour            brown
_exptl_crystal_density_diffrn    1.414
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             256
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.617
_refine_diff_density_min         -0.467
_refine_ls_abs_structure_details 'Flack (1983), with 1899 Friedel pairs'
_refine_ls_abs_structure_Flack   0.07(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.204
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     145
_refine_ls_number_reflns         4603
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.204
_refine_ls_R_factor_all          0.0384
_refine_ls_R_factor_gt           0.0323
_refine_ls_shift/su_max_lt       0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w = 1/[σ²(Fo²)+(0.0632P)²+0.0559P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0882
_refine_ls_wR_factor_ref         0.1146
_reflns_number_gt                4295
_reflns_number_total             4603
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            hb5396.cif
_cod_data_source_block           I
_cod_original_cell_volume        578.73(16)
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               2225863
_cod_database_fobs_code          2225863
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -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_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S S1 0.53730(6) 0.88379(6) 0.15567(3) 0.02249(9) Uani d . 1 . .
S S2 -0.08370(7) 0.37500(7) 0.39261(3) 0.02435(10) Uani d . 1 . .
N N1 -0.1511(2) 0.42753(19) 0.18646(9) 0.0176(2) Uani d . 1 . .
N N2 0.2016(2) 0.58341(19) 0.08083(8) 0.0167(2) Uani d . 1 . .
C C1 0.5372(3) 1.0745(3) 0.22117(12) 0.0256(3) Uani d . 1 . .
H H1A 0.6518 1.1651 0.2206 0.031 Uiso calc R 1 . .
C C2 0.3468(3) 1.0777(2) 0.27490(12) 0.0225(3) Uani d . 1 . .
H H2A 0.3166 1.1719 0.3143 0.027 Uiso calc R 1 . .
C C3 0.2025(3) 0.9222(2) 0.26367(10) 0.0176(2) Uani d . 1 . .
H H3A 0.0665 0.9026 0.2948 0.021 Uiso calc R 1 . .
C C4 0.2854(2) 0.8021(2) 0.20133(9) 0.0141(2) Uani d . 1 . .
C C5 0.1765(2) 0.6334(2) 0.16622(10) 0.0141(2) Uani d . 1 . .
C C6 0.0602(3) 0.4259(2) 0.04601(10) 0.0199(3) Uani d . 1 . .
H H6A 0.1494 0.3194 0.0686 0.024 Uiso calc R 1 . .
H H6B 0.0373 0.4245 -0.0234 0.024 Uiso calc R 1 . .
C C7 -0.1875(3) 0.4280(2) 0.08163(10) 0.0192(3) Uani d . 1 . .
H H7A -0.2783 0.5333 0.0582 0.023 Uiso calc R 1 . .
H H7B -0.2817 0.3244 0.0579 0.023 Uiso calc R 1 . .
C C8 0.0286(2) 0.5231(2) 0.22635(9) 0.0136(2) Uani d . 1 . .
C C9 0.0980(3) 0.5061(2) 0.32993(9) 0.0148(2) Uani d . 1 . .
C C10 0.3080(3) 0.5582(2) 0.38767(10) 0.0199(3) Uani d . 1 . .
H H10A 0.4286 0.6292 0.3670 0.024 Uiso calc R 1 . .
C C11 0.3203(4) 0.4914(3) 0.48252(11) 0.0272(3) Uani d . 1 . .
H H11A 0.4496 0.5144 0.5307 0.033 Uiso calc R 1 . .
C C12 0.1220(4) 0.3904(3) 0.49497(11) 0.0296(4) Uani d . 1 . .
H H12A 0.1007 0.3360 0.5524 0.036 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'
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
C1 S1 C4 . . 92.13(8) ?
C12 S2 C9 . . 91.82(8) ?
C8 N1 C7 . . 115.50(12) ?
C5 N2 C6 . . 115.48(12) ?
C2 C1 S1 . . 111.76(12) ?
C2 C1 H1A . . 124.1 ?
S1 C1 H1A . . 124.1 ?
C1 C2 C3 . . 112.51(15) ?
C1 C2 H2A . . 123.7 ?
C3 C2 H2A . . 123.7 ?
C4 C3 C2 . . 112.59(13) ?
C4 C3 H3A . . 123.7 ?
C2 C3 H3A . . 123.7 ?
C3 C4 C5 . . 128.94(12) ?
C3 C4 S1 . . 110.99(11) ?
C5 C4 S1 . . 119.83(10) ?
N2 C5 C4 . . 118.67(13) ?
N2 C5 C8 . . 120.18(13) ?
C4 C5 C8 . . 121.10(11) ?
N2 C6 C7 . . 109.89(12) ?
N2 C6 H6A . . 109.7 ?
C7 C6 H6A . . 109.7 ?
N2 C6 H6B . . 109.7 ?
C7 C6 H6B . . 109.7 ?
H6A C6 H6B . . 108.2 ?
N1 C7 C6 . . 109.29(12) ?
N1 C7 H7A . . 109.8 ?
C6 C7 H7A . . 109.8 ?
N1 C7 H7B . . 109.8 ?
C6 C7 H7B . . 109.8 ?
H7A C7 H7B . . 108.3 ?
N1 C8 C9 . . 117.84(12) ?
N1 C8 C5 . . 120.25(12) ?
C9 C8 C5 . . 121.61(12) ?
C10 C9 C8 . . 130.47(13) ?
C10 C9 S2 . . 110.85(10) ?
C8 C9 S2 . . 118.02(10) ?
C9 C10 C11 . . 112.61(15) ?
C9 C10 H10A . . 123.7 ?
C11 C10 H10A . . 123.7 ?
C12 C11 C10 . . 112.55(15) ?
C12 C11 H11A . . 123.7 ?
C10 C11 H11A . . 123.7 ?
C11 C12 S2 . . 112.16(12) ?
C11 C12 H12A . . 123.9 ?
S2 C12 H12A . . 123.9 ?
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
S1 C1 . 1.707(2) ?
S1 C4 . 1.7201(14) ?
S2 C12 . 1.7124(19) ?
S2 C9 . 1.7317(14) ?
N1 C8 . 1.2874(18) ?
N1 C7 . 1.4658(19) ?
N2 C5 . 1.2880(18) ?
N2 C6 . 1.465(2) ?
C1 C2 . 1.375(3) ?
C1 H1A . 0.9300 ?
C2 C3 . 1.411(2) ?
C2 H2A . 0.9300 ?
C3 C4 . 1.382(2) ?
C3 H3A . 0.9300 ?
C4 C5 . 1.461(2) ?
C5 C8 . 1.5040(19) ?
C6 C7 . 1.516(2) ?
C6 H6A . 0.9700 ?
C6 H6B . 0.9700 ?
C7 H7A . 0.9700 ?
C7 H7B . 0.9700 ?
C8 C9 . 1.4652(19) ?
C9 C10 . 1.376(2) ?
C10 C11 . 1.423(2) ?
C10 H10A . 0.9300 ?
C11 C12 . 1.361(3) ?
C11 H11A . 0.9300 ?
C12 H12A . 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
_geom_hbond_publ_flag
C1 H1A N1 1_665 0.93 2.33 3.235(3) 163 yes
C2 H2A Cg2 1_565 0.93 2.85 3.7737(18) 171 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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C4 S1 C1 C2 . . . . -1.31(14) ?
S1 C1 C2 C3 . . . . 0.95(19) ?
C1 C2 C3 C4 . . . . 0.1(2) ?
C2 C3 C4 C5 . . . . -175.19(14) ?
C2 C3 C4 S1 . . . . -1.03(16) ?
C1 S1 C4 C3 . . . . 1.33(12) ?
C1 S1 C4 C5 . . . . 176.10(12) ?
C6 N2 C5 C4 . . . . -172.06(13) ?
C6 N2 C5 C8 . . . . 5.4(2) ?
C3 C4 C5 N2 . . . . 147.03(16) ?
S1 C4 C5 N2 . . . . -26.69(19) ?
C3 C4 C5 C8 . . . . -30.4(2) ?
S1 C4 C5 C8 . . . . 155.92(11) ?
C5 N2 C6 C7 . . . . 37.17(19) ?
C8 N1 C7 C6 . . . . 38.97(19) ?
N2 C6 C7 N1 . . . . -60.13(17) ?
C7 N1 C8 C9 . . . . -170.61(13) ?
C7 N1 C8 C5 . . . . 3.3(2) ?
N2 C5 C8 N1 . . . . -29.3(2) ?
C4 C5 C8 N1 . . . . 148.07(15) ?
N2 C5 C8 C9 . . . . 144.36(15) ?
C4 C5 C8 C9 . . . . -38.3(2) ?
N1 C8 C9 C10 . . . . 163.90(16) ?
C5 C8 C9 C10 . . . . -9.9(2) ?
N1 C8 C9 S2 . . . . -5.87(19) ?
C5 C8 C9 S2 . . . . -179.66(11) ?
C12 S2 C9 C10 . . . . -0.12(14) ?
C12 S2 C9 C8 . . . . 171.56(13) ?
C8 C9 C10 C11 . . . . -170.37(16) ?
S2 C9 C10 C11 . . . . -0.03(18) ?
C9 C10 C11 C12 . . . . 0.2(2) ?
C10 C11 C12 S2 . . . . -0.3(2) ?
C9 S2 C12 C11 . . . . 0.26(17) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 24744840
2 PubChem 90700695
