#------------------------------------------------------------------------------
#$Date: 2017-10-13 08:09:21 +0200 (vie 13 de oct de 2017) $
#$Revision: 201973 $
#$URL: svn://www.crystallography.net/cod/cif/2/20/02/2200211.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_2200211
loop_
_publ_author_name
'Tomura, Masaaki'
'Yamashita, Yoshiro'
_publ_section_title
;
 Tetrathiafulvalene with a fused pyrazine ring
;
_journal_issue                   4
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o307
_journal_page_last               o308
_journal_paper_doi               10.1107/S1600536801003701
_journal_volume                  57
_journal_year                    2001
_chemical_formula_iupac          'C8 H4 N2 S4'
_chemical_formula_moiety         'C8 H4 N2 S4'
_chemical_formula_sum            'C8 H4 N2 S4'
_chemical_formula_weight         256.37
_chemical_melting_point          182
_chemical_name_common
;
pyrazinotetrathiafulvalene
;
_chemical_name_systematic
;
2-(1,3-dithiol-2-ylidene)-2,3-dihydro-1,3-dithia-4,7-diazaindene
;
_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'
_cell_angle_alpha                90.00
_cell_angle_beta                 96.89(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.481(2)
_cell_length_b                   9.1928(9)
_cell_length_c                   12.8980(14)
_cell_measurement_reflns_used    24
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      42.75
_cell_measurement_theta_min      9.66
_cell_volume                     998.3(3)
_computing_cell_refinement       'CAD-4 EXPRESS'
_computing_data_collection       'CAD-4 EXPRESS (Enraf-Nonius, 1992)'
_computing_data_reduction        'HELENA (Spek, 1997)'
_computing_molecular_graphics    'ORTEPII (Johnson, 1976)'
_computing_publication_material  SHELXL97
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full .996
_diffrn_measured_fraction_theta_max .996
_diffrn_measurement_device_type  'Enraf-Nonius CAD-4'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  .0841
_diffrn_reflns_av_sigmaI/netI    .1940
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            2060
_diffrn_reflns_theta_full        74.21
_diffrn_reflns_theta_max         74.21
_diffrn_reflns_theta_min         5.93
_diffrn_standards_decay_%        4.9
_diffrn_standards_interval_time  120
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    8.393
_exptl_absorpt_correction_T_max  .6790
_exptl_absorpt_correction_T_min  .1342
_exptl_absorpt_correction_type   '\y scan'
_exptl_absorpt_process_details   '(North et al., 1968)'
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.706
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             520
_exptl_crystal_size_max          .40
_exptl_crystal_size_mid          .05
_exptl_crystal_size_min          .05
_refine_diff_density_max         .472
_refine_diff_density_min         -.620
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.072
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     127
_refine_ls_number_reflns         2026
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.072
_refine_ls_R_factor_all          .2738
_refine_ls_R_factor_gt           .0794
_refine_ls_shift/su_max          <0.001
_refine_ls_shift/su_mean         <0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
calc w = 1/[σ²(Fo²)+(0.0473P)²] where P = (Fo²+2Fc²)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         .1984
_reflns_number_gt                663
_reflns_number_total             2026
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            ob6031.cif
_cod_data_source_block           I
_cod_original_cell_volume        998.4(3)
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2200211
_cod_database_fobs_code          2200211
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_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
S1 .6493(3) .1589(3) .0282(2) .0674(10) Uani d . 1 . . S
S2 .8472(3) .3437(3) -.0918(2) .0654(10) Uani d . 1 . . S
S3 .7875(3) -.1295(3) -.0841(2) .0624(9) Uani d . 1 . . S
S4 .9782(4) .0714(3) -.2010(2) .0691(10) Uani d . 1 . . S
N1 .9250(10) -.3509(10) -.1734(7) .066(3) Uani d . 1 . . N
N2 1.1014(9) -.1626(10) -.2882(6) .057(2) Uani d . 1 . . N
C1 .7889(11) .1682(12) -.0620(7) .050(3) Uani d . 1 . . C
C2 .6431(15) .3437(12) .0447(9) .079(4) Uani d . 1 . . C
H2 .5781 .3828 .0908 .095 Uiso calc R 1 . . H
C3 .7305(15) .4331(13) -.0079(10) .082(4) Uani d . 1 . . C
H3 .7293 .5337 -.0005 .098 Uiso calc R 1 . . H
C4 .8439(11) .0490(13) -.1063(7) .053(3) Uani d . 1 . . C
C5 .9170(12) -.2081(13) -.1663(8) .052(3) Uani d . 1 . . C
C6 1.0049(12) -.1131(11) -.2221(8) .056(3) Uani d . 1 . . C
C7 1.0256(13) -.3999(13) -.2385(9) .070(4) Uani d . 1 . . C
H7 1.0386 -.4996 -.2465 .084 Uiso calc R 1 . . H
C8 1.1105(13) -.3038(15) -.2941(9) .069(4) Uani d . 1 . . C
H8 1.1782 -.3430 -.3384 .083 Uiso calc R 1 . . H
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
S1 .068(2) .084(2) .0552(19) .0057(18) .0270(16) .0009(17)
S2 .069(2) .061(2) .069(2) .0031(17) .0229(18) -.0044(18)
S3 .067(2) .0610(19) .066(2) -.0009(16) .0368(16) .0047(16)
S4 .072(2) .0667(19) .077(2) -.0049(17) .0468(18) .0043(18)
N1 .054(6) .067(7) .076(7) .002(6) .004(5) -.004(6)
N2 .049(5) .075(7) .049(6) .012(5) .018(4) -.015(5)
C1 .037(6) .079(8) .033(6) -.002(6) .005(5) -.001(6)
C2 .102(10) .086(9) .052(8) .048(8) .020(7) -.012(7)
C3 .098(11) .067(8) .082(10) .028(8) .021(8) -.011(8)
C4 .040(6) .079(8) .040(7) -.003(6) .004(5) -.002(6)
C5 .051(7) .064(8) .043(7) .005(6) .014(5) .000(6)
C6 .047(7) .065(7) .059(7) .017(6) .015(6) -.010(6)
C7 .063(9) .073(8) .079(10) .004(7) .025(7) -.018(7)
C8 .051(8) .092(10) .060(8) .022(7) -.010(6) -.026(8)
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C .0181 .0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H .0000 .0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N .0311 .0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S .3331 .5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_diffrn_standard_refln_index_h
_diffrn_standard_refln_index_k
_diffrn_standard_refln_index_l
-2 0 6
0 -4 1
-2 0 -2
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
C2 S1 C1 93.8(6) no
C3 S2 C1 95.8(5) no
C5 S3 C4 94.8(5) no
C6 S4 C4 95.8(5) no
C7 N1 C5 114.8(10) no
C8 N2 C6 115.1(10) no
C4 C1 S2 122.6(7) no
C4 C1 S1 122.5(8) no
S2 C1 S1 115.0(6) no
C3 C2 S1 121.1(9) no
C3 C2 H2 119.4 no
S1 C2 H2 119.4 no
C2 C3 S2 114.3(9) no
C2 C3 H3 122.9 no
S2 C3 H3 122.9 no
C1 C4 S3 125.6(7) no
C1 C4 S4 118.7(8) no
S3 C4 S4 115.7(6) no
N1 C5 C6 123.3(9) no
N1 C5 S3 119.3(8) no
C6 C5 S3 117.4(8) no
N2 C6 C5 121.4(9) no
N2 C6 S4 122.4(8) no
C5 C6 S4 116.1(8) no
N1 C7 C8 121.0(11) no
N1 C7 H7 119.5 no
C8 C7 H7 119.5 no
N2 C8 C7 124.3(11) no
N2 C8 H8 117.8 no
C7 C8 H8 117.8 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 C2 . 1.714(11) no
S1 C1 . 1.760(9) no
S2 C3 . 1.756(11) no
S2 C1 . 1.744(10) no
S3 C5 . 1.769(10) no
S3 C4 . 1.743(11) no
S4 C6 . 1.737(10) no
S4 C4 . 1.779(9) no
N1 C7 . 1.345(12) no
N1 C5 . 1.318(11) no
N2 C8 . 1.304(12) no
N2 C6 . 1.330(11) no
C1 C4 . 1.345(13) no
C2 C3 . 1.343(14) no
C2 H2 . .9300 no
C3 H3 . .9300 no
C5 C6 . 1.402(13) no
C7 C8 . 1.391(14) no
C7 H7 . .9300 no
C8 H8 . .9300 no
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21132933
