#------------------------------------------------------------------------------
#$Date: 2017-10-13 09:09:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201973 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/20/20/2202018.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_2202018
loop_
_publ_author_name
'Crundwell, Guy'
'Sayers, David'
'Herron, Steven R.'
'Kantardjieff, Katherine A.'
_publ_section_title
;
 2,3-Dithien-2-ylquinoxaline
;
_journal_issue                   3
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o314
_journal_page_last               o315
_journal_paper_doi               10.1107/S1600536803002976
_journal_volume                  59
_journal_year                    2003
_chemical_formula_iupac          'C16 H10 N2 S2'
_chemical_formula_moiety         'C16 H10 N2 S2'
_chemical_formula_sum            'C16 H10 N2 S2'
_chemical_formula_weight         294.38
_chemical_melting_point          145
_chemical_name_common
;
 2,3-Di-(2-Thienyl)Quinoxaline
;
_chemical_name_systematic
;
2,3-Dithien-2-ylquinoxaline
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.00
_cell_angle_beta                 103.681(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.521(3)
_cell_length_b                   5.2071(14)
_cell_length_c                   22.745(7)
_cell_measurement_reflns_used    11758
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      28.3
_cell_measurement_theta_min      2.1
_cell_volume                     1325.8(6)
_computing_cell_refinement       'SAINT (Bruker, 2001)'
_computing_data_collection       'SMART (Bruker, 2001)'
_computing_data_reduction        'SHELXTL (Bruker, 2001)'
_computing_molecular_graphics    SHELXL97
_computing_publication_material  SHELXL97
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device       'Bruker SMART P3/512CCD'
_diffrn_measurement_method       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  0.049
_diffrn_reflns_av_sigmaI/netI    0.039
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            10027
_diffrn_reflns_theta_full        26.01
_diffrn_reflns_theta_max         26.0
_diffrn_reflns_theta_min         1.8
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.390
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.753
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.475
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             608
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.240
_refine_diff_density_min         -0.290
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.188
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     181
_refine_ls_number_reflns         2617
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.188
_refine_ls_R_factor_all          0.084
_refine_ls_R_factor_gt           0.061
_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)+(0.0403P)²+1.0471P] where P = (Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.115
_refine_ls_wR_factor_ref         0.122
_reflns_number_gt                2103
_reflns_number_total             2617
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            lh6035.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2202018
_cod_database_fobs_code          2202018
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
loop_
_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
_atom_site_type_symbol
N1 0.3645(2) 0.3248(5) -0.06163(11) 0.0342(6) Uani d . 1 . . N
C1 0.2844(2) 0.1437(6) -0.06298(12) 0.0298(6) Uani d . 1 . . C
N2 0.2168(2) 0.1568(5) -0.17120(10) 0.0339(6) Uani d . 1 . . N
C2 0.2089(2) 0.0560(6) -0.11919(12) 0.0295(6) Uani d . 1 . . C
C3 0.2986(3) 0.3467(6) -0.16997(13) 0.0346(7) Uani d . 1 . . C
C4 0.3094(3) 0.4609(7) -0.22448(15) 0.0476(9) Uani d . 1 . . C
H4A 0.2614 0.4051 -0.2610 0.057 Uiso calc R 1 . . H
C5 0.3896(3) 0.6520(7) -0.22394(16) 0.0512(9) Uani d . 1 . . C
H5A 0.3955 0.7282 -0.2601 0.061 Uiso calc R 1 . . H
C6 0.4640(3) 0.7355(7) -0.16904(16) 0.0481(9) Uani d . 1 . . C
H6A 0.5191 0.8660 -0.1692 0.058 Uiso calc R 1 . . H
C7 0.4562(3) 0.6274(6) -0.11584(15) 0.0422(8) Uani d . 1 . . C
H7A 0.5056 0.6839 -0.0797 0.051 Uiso calc R 1 . . H
C8 0.3733(2) 0.4296(6) -0.11548(13) 0.0330(7) Uani d . 1 . . C
C9 0.2743(2) 0.0475(6) -0.00336(13) 0.0323(7) Uani d . 1 . . C
C10 0.3374(3) -0.1392(6) 0.03159(13) 0.0391(8) Uani d . 1 . . C
H10A 0.3982 -0.2326 0.0210 0.047 Uiso calc R 1 . . H
C11 0.3004(3) -0.1768(7) 0.08615(14) 0.0446(8) Uani d . 1 . . C
H11A 0.3340 -0.2986 0.1151 0.053 Uiso calc R 1 . . H
C12 0.2121(3) -0.0183(6) 0.09152(14) 0.0424(8) Uani d . 1 . . C
H12A 0.1773 -0.0171 0.1245 0.051 Uiso calc R 1 . . H
S1 0.17130(8) 0.18052(17) 0.03086(4) 0.0460(3) Uani d . 1 . . S
C13 0.1193(2) -0.1475(5) -0.12294(12) 0.0294(6) Uani d . 1 . . C
C14 0.0945(3) -0.3165(6) -0.08138(13) 0.0345(7) Uani d . 1 . . C
H14A 0.1354 -0.3183 -0.0409 0.041 Uiso calc R 1 . . H
C15 0.0012(3) -0.4866(6) -0.10608(14) 0.0357(7) Uani d . 1 . . C
H15A -0.0257 -0.6135 -0.0837 0.043 Uiso calc R 1 . . H
C16 -0.0453(3) -0.4470(6) -0.16547(14) 0.0395(7) Uani d . 1 . . C
H16A -0.1079 -0.5420 -0.1887 0.047 Uiso calc R 1 . . H
S2 0.02454(7) -0.20146(17) -0.19284(3) 0.0425(2) Uani d . 1 . . S
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
_geom_angle_publ_flag
C1 N1 C8 117.8(2) yes
N1 C1 C2 121.4(3) yes
N1 C1 C9 115.4(2) yes
C2 C1 C9 123.1(3) yes
C2 N2 C3 117.8(2) yes
N2 C2 C1 121.0(3) yes
N2 C2 C13 115.7(2) yes
C1 C2 C13 123.3(3) yes
N2 C3 C8 121.3(3) yes
N2 C3 C4 119.6(3) yes
C8 C3 C4 119.1(3) yes
C5 C4 C3 120.3(3) yes
C5 C4 H4A 119.8 no
C3 C4 H4A 119.8 no
C4 C5 C6 120.4(3) yes
C4 C5 H5A 119.8 no
C6 C5 H5A 119.8 no
C7 C6 C5 120.6(3) yes
C7 C6 H6A 119.7 no
C5 C6 H6A 119.7 no
C6 C7 C8 119.8(3) yes
C6 C7 H7A 120.1 no
C8 C7 H7A 120.1 no
N1 C8 C3 120.7(3) yes
N1 C8 C7 119.5(3) yes
C3 C8 C7 119.8(3) yes
C10 C9 C1 129.5(3) yes
C10 C9 S1 110.9(2) yes
C1 C9 S1 119.6(2) yes
C9 C10 C11 112.5(3) yes
C9 C10 H10A 123.7 no
C11 C10 H10A 123.7 no
C12 C11 C10 112.8(3) yes
C12 C11 H11A 123.6 no
C10 C11 H11A 123.6 no
C11 C12 S1 111.8(2) yes
C11 C12 H12A 124.1 no
S1 C12 H12A 124.1 no
C12 S1 C9 91.96(16) yes
C14 C13 C2 133.0(3) yes
C14 C13 S2 110.0(2) yes
C2 C13 S2 117.0(2) yes
C13 C14 C15 113.2(3) yes
C13 C14 H14A 123.4 no
C15 C14 H14A 123.4 no
C16 C15 C14 113.0(3) yes
C16 C15 H15A 123.5 no
C14 C15 H15A 123.5 no
C15 C16 S2 111.8(2) yes
C15 C16 H16A 124.1 no
S2 C16 H16A 124.1 no
C16 S2 C13 92.06(15) yes
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
N1 C1 . 1.314(4) yes
N1 C8 . 1.366(4) yes
C1 C2 . 1.440(4) yes
C1 C9 . 1.476(4) yes
N2 C2 . 1.317(4) yes
N2 C3 . 1.361(4) yes
C2 C13 . 1.468(4) yes
C3 C8 . 1.400(4) yes
C3 C4 . 1.407(4) yes
C4 C5 . 1.356(5) yes
C4 H4A . 0.9300 no
C5 C6 . 1.406(5) yes
C5 H5A . 0.9300 no
C6 C7 . 1.356(4) yes
C6 H6A . 0.9300 no
C7 C8 . 1.406(4) yes
C7 H7A . 0.9300 no
C9 C10 . 1.353(4) yes
C9 S1 . 1.712(3) yes
C10 C11 . 1.417(4) yes
C10 H10A . 0.9300 no
C11 C12 . 1.338(5) yes
C11 H11A . 0.9300 no
C12 S1 . 1.700(3) yes
C12 H12A . 0.9300 no
C13 C14 . 1.370(4) yes
C13 S2 . 1.726(3) yes
C14 C15 . 1.404(4) yes
C14 H14A . 0.9300 no
C15 C16 . 1.346(4) yes
C15 H15A . 0.9300 no
C16 S2 . 1.705(3) yes
C16 H16A . 0.9300 no
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 3560642
