# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry A.
# This journal is © The Royal Society of Chemistry 2014

#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_DTBDT-C4

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
5,10-di(butyloxy)dithieno[2,3-d:2',3'-d']benzo[1,2-b:4,5-b']dithiophene
;
_chemical_name_common            ?
_chemical_melting_point          452-454
_chemical_formula_moiety         ?
_chemical_formula_sum            'C22 H20 O2 S4'
_chemical_formula_weight         444.62

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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/n

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'

_cell_length_a                   8.451(6)
_cell_length_b                   9.412(7)
_cell_length_c                   13.827(10)
_cell_angle_alpha                90.00
_cell_angle_beta                 106.097(6)
_cell_angle_gamma                90.00
_cell_volume                     1056.7(13)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    2175
_cell_measurement_theta_min      2.55
_cell_measurement_theta_max      27.08

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            YELLOW
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.14
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.397
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             464
_exptl_absorpt_coefficient_mu    0.465
_exptl_absorpt_correction_type   MULTI-SCAN
_exptl_absorpt_correction_T_min  0.903
_exptl_absorpt_correction_T_max  0.937
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            5929
_diffrn_reflns_av_R_equivalents  0.0234
_diffrn_reflns_av_sigmaI/netI    0.0255
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.55
_diffrn_reflns_theta_max         25.00
_reflns_number_total             1852
_reflns_number_gt                1486
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
;
Refinement of F² against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F², conventional R-factors R are based
on F, with F set to zero for negative F². The threshold expression of
F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F² are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0683P)²+1.0634P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    CONSTR
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         1852
_refine_ls_number_parameters     128
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0613
_refine_ls_R_factor_gt           0.0475
_refine_ls_wR_factor_ref         0.1398
_refine_ls_wR_factor_gt          0.1268
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_restrained_S_all      1.051
_refine_ls_shift/su_max          0.009
_refine_ls_shift/su_mean         0.001

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
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.6419(5) 0.1158(4) 0.7613(3) 0.0557(9) Uani 1 1 d . . .
H1 H 0.6624 0.0597 0.7107 0.067 Uiso 1 1 calc R . .
C2 C 0.6519(4) 0.0667(4) 0.8546(3) 0.0545(9) Uani 1 1 d . . .
H2 H 0.6793 -0.0261 0.8760 0.065 Uiso 1 1 calc R . .
C3 C 0.6151(4) 0.1755(3) 0.9154(2) 0.0423(7) Uani 1 1 d . . .
C4 C 0.5783(4) 0.3038(3) 0.8670(2) 0.0376(7) Uani 1 1 d . . .
C5 C 0.5369(3) 0.4137(3) 0.9275(2) 0.0339(7) Uani 1 1 d . . .
C6 C 0.5471(3) 0.3614(3) 1.0249(2) 0.0355(7) Uani 1 1 d . . .
C7 C 0.4903(3) 0.5542(3) 0.9029(2) 0.0339(7) Uani 1 1 d . . .
C8 C 0.3291(4) 0.6079(5) 0.7376(2) 0.0598(10) Uani 1 1 d . . .
H8A H 0.2616 0.6805 0.7564 0.072 Uiso 1 1 calc R . .
H8B H 0.2748 0.5169 0.7369 0.072 Uiso 1 1 calc R . .
C9 C 0.3484(5) 0.6393(5) 0.6358(3) 0.0672(12) Uani 1 1 d . . .
H9 H 0.3147 0.5745 0.5833 0.081 Uiso 1 1 calc R . .
C10 C 0.4213(6) 0.7739(5) 0.6217(3) 0.0822(14) Uani 1 1 d . . .
H10A H 0.5301 0.7802 0.6688 0.099 Uiso 1 1 calc R . .
H10B H 0.3549 0.8500 0.6373 0.099 Uiso 1 1 calc R . .
C11 C 0.4360(7) 0.7954(6) 0.5162(4) 0.1018(19) Uani 1 1 d . . .
H11A H 0.5044 0.7222 0.5008 0.153 Uiso 1 1 calc R . .
H11B H 0.4844 0.8866 0.5117 0.153 Uiso 1 1 calc R . .
H11C H 0.3286 0.7911 0.4691 0.153 Uiso 1 1 calc R . .
O1 O 0.4883(2) 0.6047(2) 0.80916(14) 0.0402(5) Uani 1 1 d . . .
S1 S 0.60452(11) 0.18218(9) 1.03947(6) 0.0451(3) Uani 1 1 d . . .
S2 S 0.58753(11) 0.29267(9) 0.74503(6) 0.0468(3) Uani 1 1 d . . .

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
C1 0.074(2) 0.046(2) 0.057(2) -0.0068(17) 0.0337(19) 0.0041(18)
C2 0.069(2) 0.0395(19) 0.062(2) 0.0024(16) 0.0302(19) 0.0116(16)
C3 0.0463(18) 0.0382(17) 0.0444(19) 0.0019(14) 0.0160(14) 0.0018(14)
C4 0.0364(16) 0.0391(17) 0.0383(17) 0.0006(13) 0.0123(13) -0.0010(13)
C5 0.0331(14) 0.0355(16) 0.0324(15) 0.0022(12) 0.0078(12) 0.0003(12)
C6 0.0374(16) 0.0318(16) 0.0358(16) 0.0046(13) 0.0078(12) 0.0011(12)
C7 0.0323(14) 0.0398(17) 0.0278(15) 0.0065(12) 0.0054(11) 0.0002(12)
C8 0.0416(18) 0.092(3) 0.0408(19) 0.017(2) 0.0027(15) -0.0051(18)
C9 0.073(3) 0.079(3) 0.038(2) 0.0112(19) -0.0027(18) -0.019(2)
C10 0.085(3) 0.081(3) 0.066(3) 0.014(2) -0.004(2) -0.005(3)
C11 0.105(4) 0.132(5) 0.066(3) 0.045(3) 0.019(3) -0.016(3)
O1 0.0408(11) 0.0484(13) 0.0312(11) 0.0105(9) 0.0093(9) 0.0017(10)
S1 0.0579(5) 0.0368(5) 0.0422(5) 0.0088(3) 0.0164(4) 0.0088(4)
S2 0.0577(5) 0.0462(5) 0.0417(5) -0.0003(4) 0.0224(4) 0.0005(4)

_geom_special_details            
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.351(5) . ?
C1 S2 1.725(4) . ?
C1 H1 0.9300 . ?
C2 C3 1.413(5) . ?
C2 H2 0.9300 . ?
C3 C4 1.374(4) . ?
C3 S1 1.743(3) . ?
C4 C5 1.434(4) . ?
C4 S2 1.712(3) . ?
C5 C7 1.395(4) . ?
C5 C6 1.413(4) . ?
C6 C7 1.379(4) 3_667 ?
C6 S1 1.752(3) . ?
C7 O1 1.376(3) . ?
C7 C6 1.379(4) 3_667 ?
C8 O1 1.432(4) . ?
C8 C9 1.492(5) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 C10 1.446(6) . ?
C9 H9 0.9300 . ?
C10 C11 1.511(6) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?

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
_geom_angle_publ_flag
C2 C1 S2 113.5(3) . . ?
C2 C1 H1 123.3 . . ?
S2 C1 H1 123.3 . . ?
C1 C2 C3 110.8(3) . . ?
C1 C2 H2 124.6 . . ?
C3 C2 H2 124.6 . . ?
C4 C3 C2 113.8(3) . . ?
C4 C3 S1 112.4(2) . . ?
C2 C3 S1 133.7(3) . . ?
C3 C4 C5 114.1(3) . . ?
C3 C4 S2 111.1(2) . . ?
C5 C4 S2 134.8(2) . . ?
C7 C5 C6 120.1(3) . . ?
C7 C5 C4 129.7(3) . . ?
C6 C5 C4 110.2(3) . . ?
C7 C6 C5 121.6(3) 3_667 . ?
C7 C6 S1 125.7(2) 3_667 . ?
C5 C6 S1 112.7(2) . . ?
O1 C7 C6 122.5(3) . 3_667 ?
O1 C7 C5 119.1(3) . . ?
C6 C7 C5 118.3(3) 3_667 . ?
O1 C8 C9 109.2(3) . . ?
O1 C8 H8A 109.8 . . ?
C9 C8 H8A 109.8 . . ?
O1 C8 H8B 109.8 . . ?
C9 C8 H8B 109.8 . . ?
H8A C8 H8B 108.3 . . ?
C10 C9 C8 117.6(4) . . ?
C10 C9 H9 121.2 . . ?
C8 C9 H9 121.2 . . ?
C9 C10 C11 113.6(4) . . ?
C9 C10 H10A 108.9 . . ?
C11 C10 H10A 108.9 . . ?
C9 C10 H10B 108.9 . . ?
C11 C10 H10B 108.9 . . ?
H10A C10 H10B 107.7 . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C7 O1 C8 114.9(2) . . ?
C3 S1 C6 90.55(14) . . ?
C4 S2 C1 90.80(16) . . ?

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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
S2 C1 C2 C3 -0.2(4) . . . . ?
C1 C2 C3 C4 0.0(4) . . . . ?
C1 C2 C3 S1 179.4(3) . . . . ?
C2 C3 C4 C5 178.6(3) . . . . ?
S1 C3 C4 C5 -1.0(4) . . . . ?
C2 C3 C4 S2 0.3(4) . . . . ?
S1 C3 C4 S2 -179.27(15) . . . . ?
C3 C4 C5 C7 -178.5(3) . . . . ?
S2 C4 C5 C7 -0.8(5) . . . . ?
C3 C4 C5 C6 0.9(4) . . . . ?
S2 C4 C5 C6 178.6(2) . . . . ?
C7 C5 C6 C7 0.8(5) . . . 3_667 ?
C4 C5 C6 C7 -178.6(3) . . . 3_667 ?
C7 C5 C6 S1 179.1(2) . . . . ?
C4 C5 C6 S1 -0.4(3) . . . . ?
C6 C5 C7 O1 177.1(2) . . . . ?
C4 C5 C7 O1 -3.5(4) . . . . ?
C6 C5 C7 C6 -0.8(4) . . . 3_667 ?
C4 C5 C7 C6 178.5(3) . . . 3_667 ?
O1 C8 C9 C10 -61.9(5) . . . . ?
C8 C9 C10 C11 179.8(4) . . . . ?
C6 C7 O1 C8 -82.6(4) 3_667 . . . ?
C5 C7 O1 C8 99.5(3) . . . . ?
C9 C8 O1 C7 -169.9(3) . . . . ?
C4 C3 S1 C6 0.6(3) . . . . ?
C2 C3 S1 C6 -178.8(4) . . . . ?
C7 C6 S1 C3 178.0(3) 3_667 . . . ?
C5 C6 S1 C3 -0.1(2) . . . . ?
C3 C4 S2 C1 -0.3(3) . . . . ?
C5 C4 S2 C1 -178.1(3) . . . . ?
C2 C1 S2 C4 0.3(3) . . . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.689
_refine_diff_density_min         -0.345
_refine_diff_density_rms         0.062
_database_code_depnum_ccdc_archive 'CCDC 906863'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_DTBDT-C8

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
5,10-Di(octyloxy)dithieno[2,3-d:2',3'-d']benzo[1,2-b:4,5-b']dithiophene
;
_chemical_name_common            ?
_chemical_melting_point          362-364
_chemical_formula_moiety         ?
_chemical_formula_sum            'C30 H38 N0 O2 S4'
_chemical_formula_weight         558.84

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'
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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/n

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'

_cell_length_a                   8.568(10)
_cell_length_b                   17.79(2)
_cell_length_c                   9.479(11)
_cell_angle_alpha                90.00
_cell_angle_beta                 99.479(12)
_cell_angle_gamma                90.00
_cell_volume                     1425(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    3159
_cell_measurement_theta_min      2.29
_cell_measurement_theta_max      28.16

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            YELLOW
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.14
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.302
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             596
_exptl_absorpt_coefficient_mu    0.360
_exptl_absorpt_correction_type   MULTI-SCAN
_exptl_absorpt_correction_T_min  0.924
_exptl_absorpt_correction_T_max  0.951
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            7566
_diffrn_reflns_av_R_equivalents  0.0354
_diffrn_reflns_av_sigmaI/netI    0.0358
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         2.29
_diffrn_reflns_theta_max         25.30
_reflns_number_total             2574
_reflns_number_gt                1961
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
;
Refinement of F² against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F², conventional R-factors R are based
on F, with F set to zero for negative F². The threshold expression of
F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F² are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0401P)²+0.8318P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    CONSTR
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2574
_refine_ls_number_parameters     164
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0580
_refine_ls_R_factor_gt           0.0391
_refine_ls_wR_factor_ref         0.1083
_refine_ls_wR_factor_gt          0.0928
_refine_ls_goodness_of_fit_ref   1.071
_refine_ls_restrained_S_all      1.071
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000

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
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.1513(4) 0.15517(16) 0.0917(3) 0.0561(8) Uani 1 1 d . . .
H1 H 0.0884 0.1752 0.0111 0.067 Uiso 1 1 calc R . .
C2 C 0.2099(3) 0.19627(15) 0.2073(3) 0.0504(7) Uani 1 1 d . . .
H2 H 0.1933 0.2476 0.2162 0.061 Uiso 1 1 calc R . .
C3 C 0.3004(3) 0.15109(13) 0.3138(3) 0.0406(6) Uani 1 1 d . . .
C4 C 0.3102(3) 0.07733(13) 0.2752(2) 0.0372(6) Uani 1 1 d . . .
C5 C 0.4038(3) 0.03145(12) 0.3811(2) 0.0342(5) Uani 1 1 d . . .
C6 C 0.4610(3) 0.07500(12) 0.5045(2) 0.0358(5) Uani 1 1 d . . .
C7 C 0.5557(3) 0.04431(12) 0.6236(2) 0.0350(5) Uani 1 1 d . . .
C8 C 0.4966(3) 0.10715(16) 0.8290(3) 0.0527(7) Uani 1 1 d . . .
H8A H 0.4465 0.0621 0.8582 0.063 Uiso 1 1 calc R . .
H8B H 0.4155 0.1377 0.7727 0.063 Uiso 1 1 calc R . .
C9 C 0.5701(4) 0.15003(16) 0.9587(3) 0.0578(8) Uani 1 1 d . . .
H9A H 0.6279 0.1922 0.9278 0.069 Uiso 1 1 calc R . .
H9B H 0.4858 0.1705 1.0041 0.069 Uiso 1 1 calc R . .
C10 C 0.6796(4) 0.10705(16) 1.0683(3) 0.0590(8) Uani 1 1 d . . .
H10A H 0.7728 0.0935 1.0281 0.071 Uiso 1 1 calc R . .
H10B H 0.6278 0.0608 1.0889 0.071 Uiso 1 1 calc R . .
C11 C 0.7324(4) 0.14887(16) 1.2084(3) 0.0538(7) Uani 1 1 d . . .
H11A H 0.7931 0.1927 1.1894 0.065 Uiso 1 1 calc R . .
H11B H 0.6393 0.1664 1.2446 0.065 Uiso 1 1 calc R . .
C12 C 0.8305(4) 0.10221(16) 1.3214(3) 0.0571(7) Uani 1 1 d . . .
H12A H 0.9236 0.0850 1.2848 0.069 Uiso 1 1 calc R . .
H12B H 0.7699 0.0581 1.3386 0.069 Uiso 1 1 calc R . .
C13 C 0.8838(4) 0.14119(16) 1.4626(3) 0.0586(8) Uani 1 1 d . . .
H13A H 0.9445 0.1853 1.4455 0.070 Uiso 1 1 calc R . .
H13B H 0.7908 0.1583 1.4993 0.070 Uiso 1 1 calc R . .
C14 C 0.9817(4) 0.09446(19) 1.5751(3) 0.0675(8) Uani 1 1 d . . .
H14A H 0.9237 0.0489 1.5883 0.081 Uiso 1 1 calc R . .
H14B H 1.0778 0.0798 1.5407 0.081 Uiso 1 1 calc R . .
C15 C 1.0262(4) 0.1317(2) 1.7167(3) 0.0851(11) Uani 1 1 d . . .
H15A H 1.0869 0.1761 1.7060 0.128 Uiso 1 1 calc R . .
H15B H 1.0883 0.0978 1.7820 0.128 Uiso 1 1 calc R . .
H15C H 0.9322 0.1453 1.7535 0.128 Uiso 1 1 calc R . .
O1 O 0.61392(19) 0.08650(9) 0.74279(17) 0.0415(4) Uani 1 1 d . . .
S1 S 0.40341(8) 0.16962(3) 0.48432(7) 0.0449(2) Uani 1 1 d . . .
S2 S 0.20390(8) 0.06153(4) 0.10728(7) 0.0494(2) Uani 1 1 d . . .

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
C1 0.0704(19) 0.0552(17) 0.0380(15) 0.0043(12) -0.0048(13) 0.0262(14)
C2 0.0659(18) 0.0441(15) 0.0389(14) 0.0040(12) 0.0016(13) 0.0189(13)
C3 0.0471(15) 0.0372(13) 0.0356(13) -0.0017(10) 0.0012(11) 0.0058(11)
C4 0.0399(14) 0.0358(13) 0.0338(13) -0.0018(10) -0.0005(10) 0.0039(10)
C5 0.0344(13) 0.0347(12) 0.0309(12) -0.0013(10) -0.0020(10) -0.0004(10)
C6 0.0398(14) 0.0292(12) 0.0366(13) -0.0027(10) 0.0004(10) 0.0006(9)
C7 0.0367(13) 0.0346(12) 0.0313(12) -0.0055(10) -0.0014(10) -0.0038(10)
C8 0.0551(17) 0.0626(18) 0.0397(14) -0.0051(13) 0.0058(13) 0.0006(14)
C9 0.080(2) 0.0523(17) 0.0409(15) -0.0052(13) 0.0095(14) 0.0067(15)
C10 0.073(2) 0.0527(17) 0.0482(16) -0.0077(13) -0.0006(15) 0.0021(14)
C11 0.0642(18) 0.0533(17) 0.0432(15) -0.0034(12) 0.0066(13) 0.0004(14)
C12 0.0639(19) 0.0569(18) 0.0482(16) -0.0071(14) 0.0024(14) -0.0009(14)
C13 0.069(2) 0.0566(18) 0.0475(16) -0.0065(14) 0.0023(14) -0.0033(15)
C14 0.065(2) 0.079(2) 0.0552(18) -0.0042(16) -0.0022(15) -0.0012(17)
C15 0.087(3) 0.108(3) 0.0542(19) -0.0079(19) -0.0084(18) 0.004(2)
O1 0.0422(10) 0.0417(9) 0.0370(9) -0.0110(7) -0.0042(7) -0.0012(7)
S1 0.0602(4) 0.0311(3) 0.0388(4) -0.0035(3) -0.0057(3) 0.0056(3)
S2 0.0584(5) 0.0492(4) 0.0349(4) -0.0058(3) -0.0095(3) 0.0144(3)

_geom_special_details            
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.344(4) . ?
C1 S2 1.726(3) . ?
C1 H1 0.9300 . ?
C2 C3 1.418(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.369(4) . ?
C3 S1 1.740(3) . ?
C4 C5 1.432(3) . ?
C4 S2 1.722(3) . ?
C5 C7 1.394(3) 3_656 ?
C5 C6 1.421(3) . ?
C6 C7 1.389(3) . ?
C6 S1 1.756(3) . ?
C7 O1 1.380(3) . ?
C7 C5 1.394(3) 3_656 ?
C8 O1 1.444(3) . ?
C8 C9 1.495(4) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 C10 1.491(4) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 C11 1.524(4) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 C12 1.499(4) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 C13 1.509(4) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 C14 1.496(4) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C14 C15 1.489(4) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?

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
_geom_angle_publ_flag
C2 C1 S2 113.4(2) . . ?
C2 C1 H1 123.3 . . ?
S2 C1 H1 123.3 . . ?
C1 C2 C3 111.1(2) . . ?
C1 C2 H2 124.5 . . ?
C3 C2 H2 124.5 . . ?
C4 C3 C2 113.8(2) . . ?
C4 C3 S1 112.70(18) . . ?
C2 C3 S1 133.5(2) . . ?
C3 C4 C5 114.3(2) . . ?
C3 C4 S2 110.94(18) . . ?
C5 C4 S2 134.80(19) . . ?
C7 C5 C6 119.9(2) 3_656 . ?
C7 C5 C4 130.0(2) 3_656 . ?
C6 C5 C4 110.1(2) . . ?
C7 C6 C5 122.1(2) . . ?
C7 C6 S1 125.57(18) . . ?
C5 C6 S1 112.35(18) . . ?
O1 C7 C6 122.4(2) . . ?
O1 C7 C5 119.6(2) . 3_656 ?
C6 C7 C5 118.0(2) . 3_656 ?
O1 C8 C9 110.9(2) . . ?
O1 C8 H8A 109.5 . . ?
C9 C8 H8A 109.5 . . ?
O1 C8 H8B 109.5 . . ?
C9 C8 H8B 109.5 . . ?
H8A C8 H8B 108.0 . . ?
C10 C9 C8 116.3(3) . . ?
C10 C9 H9A 108.2 . . ?
C8 C9 H9A 108.2 . . ?
C10 C9 H9B 108.2 . . ?
C8 C9 H9B 108.2 . . ?
H9A C9 H9B 107.4 . . ?
C9 C10 C11 114.8(3) . . ?
C9 C10 H10A 108.6 . . ?
C11 C10 H10A 108.6 . . ?
C9 C10 H10B 108.6 . . ?
C11 C10 H10B 108.6 . . ?
H10A C10 H10B 107.6 . . ?
C12 C11 C10 113.8(3) . . ?
C12 C11 H11A 108.8 . . ?
C10 C11 H11A 108.8 . . ?
C12 C11 H11B 108.8 . . ?
C10 C11 H11B 108.8 . . ?
H11A C11 H11B 107.7 . . ?
C11 C12 C13 115.6(3) . . ?
C11 C12 H12A 108.4 . . ?
C13 C12 H12A 108.4 . . ?
C11 C12 H12B 108.4 . . ?
C13 C12 H12B 108.4 . . ?
H12A C12 H12B 107.5 . . ?
C14 C13 C12 115.4(3) . . ?
C14 C13 H13A 108.4 . . ?
C12 C13 H13A 108.4 . . ?
C14 C13 H13B 108.4 . . ?
C12 C13 H13B 108.4 . . ?
H13A C13 H13B 107.5 . . ?
C15 C14 C13 115.2(3) . . ?
C15 C14 H14A 108.5 . . ?
C13 C14 H14A 108.5 . . ?
C15 C14 H14B 108.5 . . ?
C13 C14 H14B 108.5 . . ?
H14A C14 H14B 107.5 . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C7 O1 C8 114.25(19) . . ?
C3 S1 C6 90.58(11) . . ?
C4 S2 C1 90.73(12) . . ?

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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
S2 C1 C2 C3 -0.3(3) . . . . ?
C1 C2 C3 C4 1.1(4) . . . . ?
C1 C2 C3 S1 -179.3(2) . . . . ?
C2 C3 C4 C5 178.9(2) . . . . ?
S1 C3 C4 C5 -0.8(3) . . . . ?
C2 C3 C4 S2 -1.3(3) . . . . ?
S1 C3 C4 S2 178.99(13) . . . . ?
C3 C4 C5 C7 -177.2(2) . . . 3_656 ?
S2 C4 C5 C7 3.1(4) . . . 3_656 ?
C3 C4 C5 C6 1.6(3) . . . . ?
S2 C4 C5 C6 -178.1(2) . . . . ?
C7 C5 C6 C7 -0.8(4) 3_656 . . . ?
C4 C5 C6 C7 -179.8(2) . . . . ?
C7 C5 C6 S1 177.26(18) 3_656 . . . ?
C4 C5 C6 S1 -1.7(3) . . . . ?
C5 C6 C7 O1 178.9(2) . . . . ?
S1 C6 C7 O1 1.1(3) . . . . ?
C5 C6 C7 C5 0.8(4) . . . 3_656 ?
S1 C6 C7 C5 -177.02(18) . . . 3_656 ?
O1 C8 C9 C10 -68.2(3) . . . . ?
C8 C9 C10 C11 -171.1(3) . . . . ?
C9 C10 C11 C12 174.8(3) . . . . ?
C10 C11 C12 C13 -179.4(3) . . . . ?
C11 C12 C13 C14 180.0(3) . . . . ?
C12 C13 C14 C15 -176.6(3) . . . . ?
C6 C7 O1 C8 72.7(3) . . . . ?
C5 C7 O1 C8 -109.2(3) 3_656 . . . ?
C9 C8 O1 C7 177.8(2) . . . . ?
C4 C3 S1 C6 -0.2(2) . . . . ?
C2 C3 S1 C6 -179.8(3) . . . . ?
C7 C6 S1 C3 179.1(2) . . . . ?
C5 C6 S1 C3 1.10(19) . . . . ?
C3 C4 S2 C1 1.0(2) . . . . ?
C5 C4 S2 C1 -179.4(3) . . . . ?
C2 C1 S2 C4 -0.4(2) . . . . ?

_diffrn_measured_fraction_theta_max 0.990
_diffrn_reflns_theta_full        25.30
_diffrn_measured_fraction_theta_full 0.990
_refine_diff_density_max         0.265
_refine_diff_density_min         -0.248
_refine_diff_density_rms         0.049
_database_code_depnum_ccdc_archive 'CCDC 906864'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_DTBDT-C12

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
5,10-di(dodecyloxy)dithieno[2,3-d:2',3'-d']benzo[1,2-b:4,5-b']dithiophene
;
_chemical_name_common            ?
_chemical_melting_point          345-346
_chemical_formula_moiety         ?
_chemical_formula_sum            'C38 H54 O2 S4'
_chemical_formula_weight         671.06

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'
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'

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   P-1

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.507(4)
_cell_length_b                   9.506(5)
_cell_length_c                   13.155(7)
_cell_angle_alpha                81.790(6)
_cell_angle_beta                 76.147(6)
_cell_angle_gamma                89.255(6)
_cell_volume                     902.0(9)
_cell_formula_units_Z            1
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    2646
_cell_measurement_theta_min      2.80
_cell_measurement_theta_max      28.37

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.15
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.235
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             362
_exptl_absorpt_coefficient_mu    0.295
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.919
_exptl_absorpt_correction_T_max  0.957
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            6254
_diffrn_reflns_av_R_equivalents  0.0382
_diffrn_reflns_av_sigmaI/netI    0.0596
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.51
_diffrn_reflns_theta_max         25.50
_reflns_number_total             3208
_reflns_number_gt                2164
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
;
Refinement of F² against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F², conventional R-factors R are based
on F, with F set to zero for negative F². The threshold expression of
F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F² are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0000P)²+1.2919P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3208
_refine_ls_number_parameters     200
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0934
_refine_ls_R_factor_gt           0.0631
_refine_ls_wR_factor_ref         0.1592
_refine_ls_wR_factor_gt          0.1481
_refine_ls_goodness_of_fit_ref   1.292
_refine_ls_restrained_S_all      1.292
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.31752(16) 0.62669(12) 0.48683(10) 0.0517(4) Uani 1 1 d . . .
S2 S -0.10795(16) 0.79236(12) 0.35720(10) 0.0510(4) Uani 1 1 d . . .
O1 O 0.2859(4) 0.8939(3) 0.5874(3) 0.0585(10) Uani 1 1 d . . .
C5 C 0.0835(5) 0.8734(4) 0.4827(3) 0.0330(9) Uani 1 1 d . . .
C8 C 0.3747(6) 0.9606(4) 0.6528(3) 0.0415(10) Uani 1 1 d . . .
H8A H 0.2863 0.9795 0.7161 0.050 Uiso 1 1 calc R . .
H8B H 0.4318 1.0501 0.6151 0.050 Uiso 1 1 calc R . .
C7 C 0.1459(5) 0.9546(4) 0.5492(3) 0.0357(9) Uani 1 1 d . . .
C14 C 1.1052(6) 0.8143(5) 0.9667(4) 0.0497(12) Uani 1 1 d . . .
H14A H 1.1690 0.9031 0.9330 0.060 Uiso 1 1 calc R . .
H14B H 1.0174 0.8331 1.0303 0.060 Uiso 1 1 calc R . .
C11 C 0.7596(6) 0.8144(5) 0.7860(4) 0.0447(11) Uani 1 1 d . . .
H11A H 0.8480 0.7979 0.7220 0.054 Uiso 1 1 calc R . .
H11B H 0.6988 0.7241 0.8189 0.054 Uiso 1 1 calc R . .
C3 C 0.0644(6) 0.6842(4) 0.3884(3) 0.0410(10) Uani 1 1 d . . .
C6 C -0.0608(5) 0.9176(4) 0.4351(3) 0.0348(9) Uani 1 1 d . . .
C1 C 0.2655(6) 0.5075(5) 0.4107(4) 0.0542(13) Uani 1 1 d . . .
H1 H 0.3257 0.4222 0.4029 0.065 Uiso 1 1 calc R . .
C13 C 1.0014(6) 0.7634(5) 0.8921(4) 0.0487(12) Uani 1 1 d . . .
H13A H 1.0894 0.7454 0.8284 0.058 Uiso 1 1 calc R . .
H13B H 0.9391 0.6739 0.9256 0.058 Uiso 1 1 calc R . .
C4 C 0.1521(5) 0.7388(4) 0.4550(3) 0.0365(10) Uani 1 1 d . . .
C16 C 1.3495(6) 0.7574(5) 1.0721(3) 0.0471(11) Uani 1 1 d . . .
H16A H 1.4143 0.8461 1.0391 0.057 Uiso 1 1 calc R . .
H16B H 1.2637 0.7753 1.1367 0.057 Uiso 1 1 calc R . .
C15 C 1.2427(6) 0.7097(5) 0.9978(4) 0.0501(12) Uani 1 1 d . . .
H15A H 1.3295 0.6906 0.9340 0.060 Uiso 1 1 calc R . .
H15B H 1.1783 0.6210 1.0313 0.060 Uiso 1 1 calc R . .
C2 C 0.1296(6) 0.5494(5) 0.3637(4) 0.0500(12) Uani 1 1 d . . .
H2 H 0.0841 0.4969 0.3206 0.060 Uiso 1 1 calc R . .
C10 C 0.6183(5) 0.9163(4) 0.7560(3) 0.0423(11) Uani 1 1 d . . .
H10A H 0.6789 1.0063 0.7223 0.051 Uiso 1 1 calc R . .
H10B H 0.5299 0.9335 0.8198 0.051 Uiso 1 1 calc R . .
C17 C 1.4855(6) 0.6497(5) 1.0998(4) 0.0480(11) Uani 1 1 d . . .
H17A H 1.5681 0.6303 1.0346 0.058 Uiso 1 1 calc R . .
H17B H 1.4192 0.5619 1.1335 0.058 Uiso 1 1 calc R . .
C9 C 0.5168(5) 0.8614(4) 0.6816(3) 0.0413(10) Uani 1 1 d . . .
H9A H 0.6052 0.8456 0.6174 0.050 Uiso 1 1 calc R . .
H9B H 0.4581 0.7706 0.7150 0.050 Uiso 1 1 calc R . .
C12 C 0.8618(6) 0.8660(5) 0.8611(4) 0.0465(11) Uani 1 1 d . . .
H12A H 0.9238 0.9556 0.8278 0.056 Uiso 1 1 calc R . .
H12B H 0.7732 0.8836 0.9246 0.056 Uiso 1 1 calc R . .
C19 C 1.7291(8) 0.5774(6) 1.1976(5) 0.0752(17) Uani 1 1 d . . .
H19A H 1.6602 0.4922 1.2321 0.113 Uiso 1 1 calc R . .
H19B H 1.7971 0.6086 1.2438 0.113 Uiso 1 1 calc R . .
H19C H 1.8125 0.5584 1.1336 0.113 Uiso 1 1 calc R . .
C18 C 1.5991(6) 0.6920(5) 1.1714(4) 0.0545(13) Uani 1 1 d . . .
H18A H 1.5178 0.7128 1.2366 0.065 Uiso 1 1 calc R . .
H18B H 1.6694 0.7780 1.1374 0.065 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 0.0487(7) 0.0504(7) 0.0636(9) -0.0149(6) -0.0254(6) 0.0171(6)
S2 0.0580(8) 0.0481(7) 0.0626(8) -0.0239(6) -0.0363(6) 0.0144(6)
O1 0.065(2) 0.0531(19) 0.081(2) -0.0293(18) -0.053(2) 0.0227(17)
C5 0.033(2) 0.035(2) 0.031(2) -0.0003(18) -0.0088(18) 0.0020(17)
C8 0.042(2) 0.045(2) 0.043(3) -0.010(2) -0.018(2) 0.004(2)
C7 0.036(2) 0.037(2) 0.037(2) -0.0005(19) -0.0170(19) 0.0058(18)
C14 0.041(3) 0.054(3) 0.059(3) -0.009(2) -0.022(2) 0.005(2)
C11 0.040(2) 0.049(3) 0.048(3) -0.005(2) -0.019(2) 0.005(2)
C3 0.042(2) 0.040(2) 0.042(3) -0.008(2) -0.010(2) 0.003(2)
C6 0.038(2) 0.036(2) 0.033(2) -0.0033(18) -0.0151(19) 0.0007(18)
C1 0.059(3) 0.044(3) 0.064(3) -0.019(2) -0.018(3) 0.016(2)
C13 0.042(3) 0.052(3) 0.059(3) -0.007(2) -0.024(2) 0.006(2)
C4 0.034(2) 0.040(2) 0.036(2) -0.0042(19) -0.0097(19) 0.0028(18)
C16 0.046(3) 0.054(3) 0.046(3) -0.010(2) -0.020(2) 0.007(2)
C15 0.045(3) 0.054(3) 0.057(3) -0.009(2) -0.023(2) 0.006(2)
C2 0.056(3) 0.045(3) 0.054(3) -0.017(2) -0.016(2) 0.007(2)
C10 0.037(2) 0.049(3) 0.044(3) -0.006(2) -0.017(2) 0.004(2)
C17 0.047(3) 0.054(3) 0.050(3) -0.013(2) -0.023(2) 0.005(2)
C9 0.036(2) 0.046(2) 0.045(3) -0.006(2) -0.017(2) 0.0051(19)
C12 0.041(2) 0.050(3) 0.053(3) -0.008(2) -0.020(2) 0.004(2)
C19 0.090(4) 0.071(4) 0.091(4) -0.032(3) -0.061(4) 0.023(3)
C18 0.060(3) 0.055(3) 0.060(3) -0.017(2) -0.033(3) 0.010(2)

_geom_special_details            
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 C4 1.715(4) . ?
S1 C1 1.721(5) . ?
S2 C3 1.732(4) . ?
S2 C6 1.767(4) . ?
O1 C7 1.358(4) . ?
O1 C8 1.424(4) . ?
C5 C7 1.407(5) . ?
C5 C6 1.408(5) . ?
C5 C4 1.436(5) . ?
C8 C9 1.495(5) . ?
C7 C6 1.384(5) 2_576 ?
C14 C15 1.510(6) . ?
C14 C13 1.522(6) . ?
C11 C10 1.511(5) . ?
C11 C12 1.522(5) . ?
C3 C4 1.372(5) . ?
C3 C2 1.420(5) . ?
C6 C7 1.384(5) 2_576 ?
C1 C2 1.342(6) . ?
C13 C12 1.510(5) . ?
C16 C17 1.506(5) . ?
C16 C15 1.522(6) . ?
C10 C9 1.525(5) . ?
C17 C18 1.510(6) . ?
C19 C18 1.511(6) . ?

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
_geom_angle_publ_flag
C4 S1 C1 90.7(2) . . ?
C3 S2 C6 91.07(19) . . ?
C7 O1 C8 122.6(3) . . ?
C7 C5 C6 122.2(3) . . ?
C7 C5 C4 126.5(3) . . ?
C6 C5 C4 111.3(3) . . ?
O1 C8 C9 107.4(3) . . ?
O1 C7 C6 129.8(4) . 2_576 ?
O1 C7 C5 113.2(3) . . ?
C6 C7 C5 117.0(3) 2_576 . ?
C15 C14 C13 113.8(4) . . ?
C10 C11 C12 114.1(3) . . ?
C4 C3 C2 113.2(4) . . ?
C4 C3 S2 112.7(3) . . ?
C2 C3 S2 134.0(3) . . ?
C7 C6 C5 120.8(3) 2_576 . ?
C7 C6 S2 127.9(3) 2_576 . ?
C5 C6 S2 111.3(3) . . ?
C2 C1 S1 113.6(3) . . ?
C12 C13 C14 114.6(4) . . ?
C3 C4 C5 113.6(3) . . ?
C3 C4 S1 111.3(3) . . ?
C5 C4 S1 135.1(3) . . ?
C17 C16 C15 113.0(4) . . ?
C14 C15 C16 115.2(4) . . ?
C1 C2 C3 111.1(4) . . ?
C11 C10 C9 113.0(3) . . ?
C16 C17 C18 115.7(4) . . ?
C8 C9 C10 113.4(3) . . ?
C13 C12 C11 114.2(3) . . ?
C17 C18 C19 112.6(4) . . ?

_diffrn_measured_fraction_theta_max 0.956
_diffrn_reflns_theta_full        25.50
_diffrn_measured_fraction_theta_full 0.956
_refine_diff_density_max         0.475
_refine_diff_density_min         -0.347
_refine_diff_density_rms         0.056
_database_code_depnum_ccdc_archive 'CCDC 906862'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_DTBDT-SiMe3

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
5,10-bis(trimethylsilylethynyl)dithieno[2,3-d:2',3'-d']benzo[1,2-b:4,5-b']di-
thiophene
;
_chemical_name_common            ?
_chemical_melting_point          559-561
_chemical_formula_moiety         ?
_chemical_formula_sum            'C24 H22 S4 Si2'
_chemical_formula_weight         494.84

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'
Si Si 0.0817 0.0704 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/c

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'

_cell_length_a                   6.330(4)
_cell_length_b                   21.410(14)
_cell_length_c                   9.618(7)
_cell_angle_alpha                90.00
_cell_angle_beta                 103.021(7)
_cell_angle_gamma                90.00
_cell_volume                     1270.0(15)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    1972
_cell_measurement_theta_min      2.37
_cell_measurement_theta_max      24.39

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            YELLOW
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.14
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.294
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             516
_exptl_absorpt_coefficient_mu    0.478
_exptl_absorpt_correction_type   MULTI-SCAN
_exptl_absorpt_correction_T_min  0.866
_exptl_absorpt_correction_T_max  0.935
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            8668
_diffrn_reflns_av_R_equivalents  0.0617
_diffrn_reflns_av_sigmaI/netI    0.0654
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         2.37
_diffrn_reflns_theta_max         25.30
_reflns_number_total             2313
_reflns_number_gt                1462
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
;
Refinement of F² against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F², conventional R-factors R are based
on F, with F set to zero for negative F². The threshold expression of
F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F² are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0000P)²+2.7867P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    CONSTR
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2313
_refine_ls_number_parameters     139
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1166
_refine_ls_R_factor_gt           0.0657
_refine_ls_wR_factor_ref         0.1412
_refine_ls_wR_factor_gt          0.1178
_refine_ls_goodness_of_fit_ref   1.197
_refine_ls_restrained_S_all      1.197
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.4251(2) 0.61167(7) 0.94169(16) 0.0557(4) Uani 1 1 d . . .
S2 S 0.6694(2) 0.47502(7) 0.71178(15) 0.0541(4) Uani 1 1 d . . .
Si1 Si 1.2756(3) 0.31287(7) 0.62691(18) 0.0543(5) Uani 1 1 d . . .
C4 C 0.5939(8) 0.5566(2) 0.8934(5) 0.0399(12) Uani 1 1 d . . .
C6 C 0.8646(8) 0.4865(2) 0.8699(5) 0.0383(12) Uani 1 1 d . . .
C7 C 1.0576(8) 0.4536(2) 0.9078(5) 0.0395(12) Uani 1 1 d . . .
C5 C 0.8008(8) 0.5321(2) 0.9581(5) 0.0384(12) Uani 1 1 d . . .
C3 C 0.5014(9) 0.5314(2) 0.7630(6) 0.0486(13) Uani 1 1 d . . .
C8 C 1.1200(8) 0.4079(2) 0.8169(5) 0.0447(13) Uani 1 1 d . . .
C9 C 1.1749(9) 0.3696(2) 0.7399(6) 0.0504(14) Uani 1 1 d . . .
C2 C 0.2957(9) 0.5550(3) 0.7009(6) 0.0573(15) Uani 1 1 d . . .
H2 H 0.2117 0.5425 0.6130 0.069 Uiso 1 1 calc R . .
C1 C 0.2363(9) 0.5984(3) 0.7866(6) 0.0632(16) Uani 1 1 d . . .
H1 H 0.1042 0.6193 0.7634 0.076 Uiso 1 1 calc R . .
C12 C 1.5362(11) 0.2825(3) 0.7307(8) 0.089(2) Uani 1 1 d . . .
H12A H 1.6422 0.3153 0.7460 0.133 Uiso 1 1 calc R . .
H12B H 1.5845 0.2490 0.6790 0.133 Uiso 1 1 calc R . .
H12C H 1.5177 0.2672 0.8211 0.133 Uiso 1 1 calc R . .
C10 C 1.3170(13) 0.3551(3) 0.4672(7) 0.095(2) Uani 1 1 d . . .
H10A H 1.2060 0.3862 0.4400 0.142 Uiso 1 1 calc R . .
H10B H 1.3098 0.3261 0.3902 0.142 Uiso 1 1 calc R . .
H10C H 1.4565 0.3750 0.4887 0.142 Uiso 1 1 calc R . .
C11 C 1.0713(11) 0.2502(3) 0.5779(9) 0.103(3) Uani 1 1 d . . .
H11A H 1.0454 0.2312 0.6629 0.154 Uiso 1 1 calc R . .
H11B H 1.1238 0.2192 0.5219 0.154 Uiso 1 1 calc R . .
H11C H 0.9385 0.2676 0.5233 0.154 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 0.0564(9) 0.0442(8) 0.0739(10) -0.0010(7) 0.0305(8) 0.0080(7)
S2 0.0584(9) 0.0535(9) 0.0544(8) -0.0134(7) 0.0213(7) -0.0014(7)
Si1 0.0587(10) 0.0446(9) 0.0668(10) -0.0196(8) 0.0291(8) 0.0003(8)
C4 0.047(3) 0.032(3) 0.047(3) 0.000(2) 0.023(2) -0.005(2)
C6 0.046(3) 0.035(3) 0.042(3) -0.011(2) 0.025(2) -0.009(2)
C7 0.044(3) 0.024(2) 0.059(3) -0.005(2) 0.032(3) -0.002(2)
C5 0.043(3) 0.031(3) 0.050(3) -0.004(2) 0.029(2) -0.005(2)
C3 0.048(3) 0.047(3) 0.055(3) 0.000(3) 0.023(3) -0.005(3)
C8 0.045(3) 0.041(3) 0.055(3) -0.004(3) 0.024(3) -0.002(2)
C9 0.054(3) 0.046(3) 0.058(3) -0.008(3) 0.025(3) 0.005(3)
C2 0.053(4) 0.064(4) 0.057(4) 0.003(3) 0.018(3) -0.002(3)
C1 0.046(3) 0.063(4) 0.081(4) 0.008(3) 0.014(3) 0.009(3)
C12 0.081(5) 0.068(5) 0.119(6) -0.019(4) 0.024(4) 0.019(4)
C10 0.125(6) 0.100(6) 0.066(4) -0.013(4) 0.036(4) -0.003(5)
C11 0.096(6) 0.081(5) 0.144(7) -0.060(5) 0.053(5) -0.023(4)

_geom_special_details            
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 C1 1.712(6) . ?
S1 C4 1.724(5) . ?
S2 C6 1.747(5) . ?
S2 C3 1.751(5) . ?
Si1 C9 1.838(5) . ?
Si1 C12 1.844(7) . ?
Si1 C11 1.850(7) . ?
Si1 C10 1.851(7) . ?
C4 C3 1.370(7) . ?
C4 C5 1.418(7) . ?
C6 C7 1.386(7) . ?
C6 C5 1.410(6) . ?
C7 C8 1.426(6) . ?
C7 C5 1.428(7) 3_767 ?
C5 C7 1.428(7) 3_767 ?
C3 C2 1.399(7) . ?
C8 C9 1.207(6) . ?
C2 C1 1.351(8) . ?

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
_geom_angle_publ_flag
C1 S1 C4 90.3(3) . . ?
C6 S2 C3 90.8(2) . . ?
C9 Si1 C12 107.5(3) . . ?
C9 Si1 C11 108.3(3) . . ?
C12 Si1 C11 111.8(3) . . ?
C9 Si1 C10 107.5(3) . . ?
C12 Si1 C10 110.2(4) . . ?
C11 Si1 C10 111.4(4) . . ?
C3 C4 C5 114.7(4) . . ?
C3 C4 S1 110.7(4) . . ?
C5 C4 S1 134.6(4) . . ?
C7 C6 C5 123.2(4) . . ?
C7 C6 S2 124.5(4) . . ?
C5 C6 S2 112.2(4) . . ?
C6 C7 C8 122.4(5) . . ?
C6 C7 C5 117.8(4) . 3_767 ?
C8 C7 C5 119.8(5) . 3_767 ?
C6 C5 C4 110.7(4) . . ?
C6 C5 C7 119.0(4) . 3_767 ?
C4 C5 C7 130.3(4) . 3_767 ?
C4 C3 C2 114.5(5) . . ?
C4 C3 S2 111.6(4) . . ?
C2 C3 S2 134.0(5) . . ?
C9 C8 C7 179.3(6) . . ?
C8 C9 Si1 176.5(5) . . ?
C1 C2 C3 110.4(5) . . ?
C2 C1 S1 114.2(5) . . ?

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        25.30
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.289
_refine_diff_density_min         -0.350
_refine_diff_density_rms         0.069


_database_code_depnum_ccdc_archive 'CCDC 906865'
