#------------------------------------------------------------------------------
#$Date: 2016-02-18 17:37:37 +0200 (Thu, 18 Feb 2016) $
#$Revision: 176729 $
#$URL: svn://www.crystallography.net/cod/cif/1/50/67/1506770.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_1506770
loop_
_publ_author_name
'Okamoto, Toshihiro'
'Kudoh, Kenichi'
'Wakamiya, Atsushi'
'Yamaguchi, Shigehiro'
_publ_section_title
;
 General synthesis of thiophene and selenophene-based heteroacenes.
;
_journal_issue                   23
_journal_name_full               'Organic letters'
_journal_page_first              5301
_journal_page_last               5304
_journal_paper_doi               10.1021/ol0523650
_journal_volume                  7
_journal_year                    2005
_chemical_formula_sum            'C16 H8 S3'
_chemical_formula_weight         296.40
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           62
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ac 2n'
_symmetry_space_group_name_H-M   'P n m a'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.933(4)
_cell_length_b                   26.589(15)
_cell_length_c                   5.906(3)
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      27.4835
_cell_measurement_theta_min      3.0631
_cell_volume                     1245.8(11)
_computing_molecular_graphics    'ORTEP 3 for windows'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71070
_diffrn_reflns_av_R_equivalents  0.0247
_diffrn_reflns_av_sigmaI/netI    0.0187
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       31
_diffrn_reflns_limit_k_min       -31
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_limit_l_min       -6
_diffrn_reflns_number            6907
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         3.06
_exptl_absorpt_coefficient_mu    0.573
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.8763
_exptl_absorpt_correction_type   empirical
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.580
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             608
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.403
_refine_diff_density_min         -0.256
_refine_diff_density_rms         0.056
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.218
_refine_ls_hydrogen_treatment    none
_refine_ls_matrix_type           full
_refine_ls_number_parameters     88
_refine_ls_number_reflns         1110
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.218
_refine_ls_R_factor_all          0.0422
_refine_ls_R_factor_gt           0.0417
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0287P)²+1.7021P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0913
_refine_ls_wR_factor_ref         0.0915
_reflns_number_gt                1099
_reflns_number_total             1110
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol0523650si20050930_092023.cif
_cod_data_source_block           compound_3a
_cod_original_cell_volume        1245.9(11)
_cod_original_sg_symbol_H-M      Pnma
_cod_database_code               1506770
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z+1/2'
'-x, y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'-x-1/2, y-1/2, z-1/2'
'x, -y-1/2, z'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
S1 S 0.39821(11) 0.2500 0.22768(14) 0.0222(2) Uani 1 2 d S
C1 C 0.3267(3) 0.29626(8) 0.4119(4) 0.0190(5) Uani 1 1 d .
C2 C 0.2530(3) 0.27669(8) 0.6040(4) 0.0189(5) Uani 1 1 d .
S2 S 0.18460(8) 0.32233(2) 0.79145(10) 0.0239(2) Uani 1 1 d .
C3 C 0.2612(3) 0.36916(9) 0.6115(4) 0.0212(5) Uani 1 1 d .
C4 C 0.3343(3) 0.35025(9) 0.4107(4) 0.0202(5) Uani 1 1 d .
C5 C 0.4040(3) 0.38430(9) 0.2536(4) 0.0229(5) Uani 1 1 d .
H1 H 0.4538 0.3724 0.1175 0.027 Uiso 1 1 calc R
C6 C 0.3989(3) 0.43488(9) 0.2998(4) 0.0293(6) Uani 1 1 d .
H2 H 0.4467 0.4579 0.1949 0.035 Uiso 1 1 calc R
C7 C 0.3247(3) 0.45324(9) 0.4979(5) 0.0303(6) Uani 1 1 d .
H3 H 0.3226 0.4885 0.5250 0.036 Uiso 1 1 calc R
C8 C 0.2544(3) 0.42091(9) 0.6551(4) 0.0273(6) Uani 1 1 d .
H4 H 0.2030 0.4334 0.7890 0.033 Uiso 1 1 calc R
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
S1 0.0271(5) 0.0200(4) 0.0196(4) 0.000 0.0053(3) 0.000
C1 0.0167(11) 0.0216(12) 0.0186(12) -0.0006(9) -0.0010(9) 0.0007(9)
C2 0.0155(11) 0.0233(12) 0.0177(11) -0.0014(9) -0.0004(9) 0.0002(9)
S2 0.0295(4) 0.0216(3) 0.0205(4) -0.0012(2) 0.0055(2) 0.0018(2)
C3 0.0186(11) 0.0235(12) 0.0215(12) 0.0016(10) -0.0025(9) 0.0016(9)
C4 0.0176(11) 0.0220(12) 0.0209(12) -0.0005(9) -0.0033(10) 0.0008(9)
C5 0.0187(12) 0.0271(12) 0.0228(12) 0.0015(10) 0.0003(10) 0.0007(10)
C6 0.0296(14) 0.0257(13) 0.0325(15) 0.0075(11) -0.0020(12) -0.0022(11)
C7 0.0344(14) 0.0197(12) 0.0370(15) 0.0017(11) -0.0050(12) 0.0011(11)
C8 0.0289(13) 0.0250(12) 0.0280(13) -0.0030(10) -0.0026(11) 0.0045(11)
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'
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_site_symmetry_1
_geom_angle_site_symmetry_3
C1 S1 C1 90.15(16) . 8_565
C2 C1 C4 113.5(2) . .
C2 C1 S1 112.75(17) . .
C4 C1 S1 133.68(18) . .
C1 C2 C2 112.17(13) . 8_565
C1 C2 S2 113.28(17) . .
C2 C2 S2 134.54(8) 8_565 .
C2 S2 C3 90.08(12) . .
C8 C3 C4 121.3(2) . .
C8 C3 S2 125.1(2) . .
C4 C3 S2 113.59(18) . .
C5 C4 C3 119.0(2) . .
C5 C4 C1 131.4(2) . .
C3 C4 C1 109.5(2) . .
C6 C5 C4 119.1(2) . .
C5 C6 C7 121.4(2) . .
C8 C7 C6 121.0(2) . .
C7 C8 C3 118.2(2) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
S1 C1 1.737(2) .
S1 C1 1.737(2) 8_565
C1 C2 1.378(3) .
C1 C4 1.437(3) .
C2 C2 1.419(4) 8_565
C2 S2 1.730(2) .
S2 C3 1.746(2) .
C3 C8 1.401(3) .
C3 C4 1.413(3) .
C4 C5 1.409(3) .
C5 C6 1.373(4) .
C6 C7 1.398(4) .
C7 C8 1.383(4) .
