#------------------------------------------------------------------------------
#$Date: 2016-03-21 03:41:24 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178438 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/59/4025958.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_4025958
loop_
_publ_author_name
'Francisco Otón'
'Raphael Pfattner'
'Neil S. Oxtoby'
'Marta Mas-Torrent'
'Klaus Wurst'
'Xavier Fontrodona'
'Yoann Olivier'
'Jérôme Cornil'
'Jaume Veciana'
'Concepció Rovira'
_publ_section_title
;
 Benzodicarbomethoxytetrathiafulvalene Derivatives as Soluble Organic
 Semiconductors
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              154
_journal_page_last               163
_journal_paper_doi               10.1021/jo101817j
_journal_volume                  76
_journal_year                    2011
_chemical_formula_sum            'C14 H10 O4 S4'
_chemical_formula_weight         370.46
_chemical_name_systematic
; 
 ? 
;
_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                 95.085(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   8.3891(4)
_cell_length_b                   10.8253(3)
_cell_length_c                   34.158(1)
_cell_measurement_reflns_used    20757
_cell_measurement_temperature    233(2)
_cell_measurement_theta_max      25.0
_cell_measurement_theta_min      1.0
_cell_volume                     3089.83(19)
_computing_cell_refinement       'SCALEPACK (Otwinowski & Minor, 1997)'
_computing_data_collection       'COLLECT (Nonius, 1998)'
_computing_data_reduction
;
 DENZO (Otwinowski & Minor, 1997) and SCALEPACK 
;
_computing_molecular_graphics    'SHELXTL (Sheldrick, 1997)'
_computing_publication_material  SHELXL97
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      233(2)
_diffrn_measured_fraction_theta_full 0.948
_diffrn_measured_fraction_theta_max 0.948
_diffrn_measurement_device_type  'Nonius KappaCCD'
_diffrn_measurement_method       'phi- and omega-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  0.0482
_diffrn_reflns_av_sigmaI/netI    0.0632
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       40
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_number            12232
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         1.97
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.628
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.593
_exptl_crystal_description       plate
_exptl_crystal_F_000             1520
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.375
_refine_diff_density_min         -0.327
_refine_diff_density_rms         0.064
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     401
_refine_ls_number_reflns         5159
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.058
_refine_ls_R_factor_all          0.0923
_refine_ls_R_factor_gt           0.0461
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0489P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0986
_refine_ls_wR_factor_ref         0.1116
_reflns_number_gt                3268
_reflns_number_total             5159
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo101817j_si_006.cif
_cod_data_source_block           no139
_cod_database_code               4025958
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_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 0.69065(10) 0.53478(7) 0.23621(2) 0.0327(2) Uani 1 1 d .
S2 S 0.53915(10) 0.29195(7) 0.24944(2) 0.0342(2) Uani 1 1 d .
S3 S 0.54471(11) 0.53276(7) 0.14603(3) 0.0416(3) Uani 1 1 d .
S4 S 0.39025(10) 0.29037(7) 0.15824(3) 0.0393(2) Uani 1 1 d .
S5 S 0.26137(10) 1.03869(7) 0.23091(2) 0.0343(2) Uani 1 1 d .
S6 S 0.40555(9) 0.79303(7) 0.21815(2) 0.0320(2) Uani 1 1 d .
S7 S 0.09652(10) 1.03902(7) 0.14255(2) 0.0357(2) Uani 1 1 d .
S8 S 0.24082(11) 0.79641(7) 0.12805(2) 0.0409(2) Uani 1 1 d .
O1 O 0.3579(4) 0.4879(2) 0.03777(8) 0.0713(8) Uani 1 1 d .
O2 O 0.4962(3) 0.6376(2) 0.07077(6) 0.0482(6) Uani 1 1 d .
O3 O 0.1218(3) 0.3117(2) 0.07165(8) 0.0635(8) Uani 1 1 d .
O4 O 0.3394(3) 0.1944(2) 0.06726(7) 0.0543(7) Uani 1 1 d .
O5 O -0.1981(3) 0.9509(2) 0.05157(8) 0.0587(7) Uani 1 1 d .
O6 O -0.1421(3) 1.1237(2) 0.08626(7) 0.0467(6) Uani 1 1 d .
O7 O 0.0872(4) 0.7696(3) 0.03099(9) 0.0827(9) Uani 1 1 d .
O8 O -0.0605(3) 0.6682(2) 0.07203(7) 0.0619(8) Uani 1 1 d .
C1 C 0.5714(3) 0.4116(3) 0.21640(9) 0.0290(7) Uani 1 1 d .
C2 C 0.7316(3) 0.4681(3) 0.28285(9) 0.0271(7) Uani 1 1 d .
C3 C 0.8283(4) 0.5233(3) 0.31314(9) 0.0331(8) Uani 1 1 d .
H3 H 0.8722 0.6019 0.3096 0.040 Uiso 1 1 calc .
C4 C 0.8591(4) 0.4618(3) 0.34829(10) 0.0376(8) Uani 1 1 d .
H4 H 0.9265 0.4982 0.3685 0.045 Uiso 1 1 calc .
C5 C 0.7925(4) 0.3478(3) 0.35414(9) 0.0360(8) Uani 1 1 d .
H5 H 0.8152 0.3069 0.3783 0.043 Uiso 1 1 calc .
C6 C 0.6922(4) 0.2930(3) 0.32470(9) 0.0333(8) Uani 1 1 d .
H6 H 0.6451 0.2159 0.3289 0.040 Uiso 1 1 calc .
C7 C 0.6620(3) 0.3537(3) 0.28881(9) 0.0284(7) Uani 1 1 d .
C8 C 0.5109(3) 0.4118(3) 0.17876(9) 0.0314(8) Uani 1 1 d .
C9 C 0.4320(4) 0.4646(3) 0.10586(9) 0.0349(8) Uani 1 1 d .
C10 C 0.3623(4) 0.3559(3) 0.11195(9) 0.0337(8) Uani 1 1 d .
C11 C 0.4219(4) 0.5291(3) 0.06751(11) 0.0422(9) Uani 1 1 d .
C12 C 0.4959(5) 0.7113(3) 0.03516(10) 0.0620(11) Uani 1 1 d .
H12A H 0.5660 0.7819 0.0400 0.093 Uiso 1 1 calc R
H12B H 0.3880 0.7398 0.0275 0.093 Uiso 1 1 calc R
H12C H 0.5334 0.6614 0.0143 0.093 Uiso 1 1 calc R
C13 C 0.2576(5) 0.2870(3) 0.08089(10) 0.0402(9) Uani 1 1 d .
C14 C 0.2542(5) 0.1180(4) 0.03699(11) 0.0723(13) Uani 1 1 d .
H14A H 0.3287 0.0613 0.0263 0.108 Uiso 1 1 calc R
H14B H 0.2064 0.1705 0.0161 0.108 Uiso 1 1 calc R
H14C H 0.1710 0.0716 0.0484 0.108 Uiso 1 1 calc R
C15 C 0.2836(3) 0.9143(2) 0.19887(9) 0.0291(7) Uani 1 1 d .
C16 C 0.3661(4) 0.9692(3) 0.27173(9) 0.0296(8) Uani 1 1 d .
C17 C 0.3884(4) 1.0252(3) 0.30836(10) 0.0357(8) Uani 1 1 d .
H17 H 0.3432 1.1031 0.3125 0.043 Uiso 1 1 calc .
C18 C 0.4775(4) 0.9656(3) 0.33877(9) 0.0405(9) Uani 1 1 d .
H18 H 0.4932 1.0033 0.3636 0.049 Uiso 1 1 calc .
C19 C 0.5434(4) 0.8512(3) 0.33287(10) 0.0391(8) Uani 1 1 d .
H19 H 0.6033 0.8115 0.3538 0.047 Uiso 1 1 calc .
C20 C 0.5225(3) 0.7947(3) 0.29682(9) 0.0316(8) Uani 1 1 d .
H20 H 0.5680 0.7167 0.2931 0.038 Uiso 1 1 calc .
C21 C 0.4338(3) 0.8530(3) 0.26579(9) 0.0285(7) Uani 1 1 d .
C22 C 0.2158(3) 0.9161(2) 0.16189(9) 0.0296(7) Uani 1 1 d .
C23 C 0.0108(4) 0.9520(3) 0.10267(9) 0.0315(8) Uani 1 1 d .
C24 C 0.0769(4) 0.8419(3) 0.09631(9) 0.0353(8) Uani 1 1 d .
C25 C -0.1218(4) 1.0057(3) 0.07720(10) 0.0364(8) Uani 1 1 d .
C26 C -0.2579(5) 1.1933(3) 0.06120(12) 0.0691(12) Uani 1 1 d .
H26A H -0.2668 1.2761 0.0716 0.104 Uiso 1 1 calc R
H26B H -0.3612 1.1526 0.0603 0.104 Uiso 1 1 calc R
H26C H -0.2233 1.1977 0.0349 0.104 Uiso 1 1 calc R
C27 C 0.0348(4) 0.7582(3) 0.06225(11) 0.0448(9) Uani 1 1 d .
C28 C -0.0984(5) 0.5742(3) 0.04213(13) 0.0850(15) Uani 1 1 d .
H28A H -0.1731 0.5153 0.0516 0.128 Uiso 1 1 calc R
H28B H -0.0011 0.5318 0.0366 0.128 Uiso 1 1 calc R
H28C H -0.1461 0.6131 0.0183 0.128 Uiso 1 1 calc R
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'
O O 0.0106 0.0060 '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
C2 S1 C1 95.52(14)
C7 S2 C1 95.64(14)
C9 S3 C8 94.46(15)
C10 S4 C8 94.82(14)
C16 S5 C15 95.34(14)
C21 S6 C15 95.63(14)
C23 S7 C22 93.78(14)
C24 S8 C22 93.84(15)
C11 O2 C12 116.7(3)
C13 O4 C14 116.2(3)
C25 O6 C26 117.1(3)
C27 O8 C28 115.9(3)
C8 C1 S2 123.5(2)
C8 C1 S1 121.4(2)
S2 C1 S1 115.19(17)
C3 C2 C7 119.8(3)
C3 C2 S1 123.6(2)
C7 C2 S1 116.6(2)
C4 C3 C2 119.6(3)
C5 C4 C3 120.8(3)
C4 C5 C6 120.4(3)
C5 C6 C7 119.2(3)
C2 C7 C6 120.1(3)
C2 C7 S2 116.9(2)
C6 C7 S2 123.0(2)
C1 C8 S3 122.8(2)
C1 C8 S4 122.3(2)
S3 C8 S4 114.87(17)
C10 C9 C11 124.1(3)
C10 C9 S3 117.4(2)
C11 C9 S3 118.5(2)
C9 C10 C13 124.0(3)
C9 C10 S4 118.5(2)
C13 C10 S4 117.5(2)
O1 C11 O2 125.0(3)
O1 C11 C9 124.3(3)
O2 C11 C9 110.7(3)
O3 C13 O4 126.4(3)
O3 C13 C10 124.1(3)
O4 C13 C10 109.5(3)
C22 C15 S5 121.1(2)
C22 C15 S6 123.3(2)
S5 C15 S6 115.48(18)
C17 C16 C21 119.9(3)
C17 C16 S5 123.2(2)
C21 C16 S5 116.8(2)
C18 C17 C16 119.5(3)
C19 C18 C17 120.4(3)
C20 C19 C18 120.7(3)
C19 C20 C21 119.9(3)
C20 C21 C16 119.5(3)
C20 C21 S6 124.1(2)
C16 C21 S6 116.4(2)
C15 C22 S7 123.1(2)
C15 C22 S8 122.9(2)
S7 C22 S8 114.02(17)
C24 C23 C25 123.9(3)
C24 C23 S7 117.1(2)
C25 C23 S7 118.9(2)
C23 C24 C27 126.4(3)
C23 C24 S8 117.7(2)
C27 C24 S8 115.6(2)
O5 C25 O6 125.2(3)
O5 C25 C23 124.4(3)
O6 C25 C23 110.4(3)
O7 C27 O8 125.5(3)
O7 C27 C24 123.5(3)
O8 C27 C24 110.9(3)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
S1 C2 1.755(3)
S1 C1 1.765(3)
S2 C7 1.752(3)
S2 C1 1.755(3)
S3 C9 1.758(3)
S3 C8 1.761(3)
S4 C10 1.730(3)
S4 C8 1.766(3)
S5 C16 1.751(3)
S5 C15 1.756(3)
S6 C21 1.749(3)
S6 C15 1.756(3)
S7 C23 1.757(3)
S7 C22 1.758(3)
S8 C24 1.745(3)
S8 C22 1.761(3)
O1 C11 1.193(4)
O2 C11 1.330(4)
O2 C12 1.454(4)
O3 C13 1.185(4)
O4 C13 1.323(4)
O4 C14 1.460(4)
O5 C25 1.195(4)
O6 C25 1.328(4)
O6 C26 1.448(4)
O7 C27 1.197(4)
O8 C27 1.322(4)
O8 C28 1.457(4)
C1 C8 1.340(4)
C2 C3 1.391(4)
C2 C7 1.393(4)
C3 C4 1.377(4)
C4 C5 1.377(4)
C5 C6 1.386(4)
C6 C7 1.394(4)
C9 C10 1.339(4)
C9 C11 1.480(4)
C10 C13 1.513(4)
C15 C22 1.339(4)
C16 C17 1.388(4)
C16 C21 1.402(4)
C17 C18 1.385(4)
C18 C19 1.378(4)
C19 C20 1.372(4)
C20 C21 1.391(4)
C23 C24 1.341(4)
C23 C25 1.470(4)
C24 C27 1.493(4)
