# Supplementary Material (ESI) for Journal of Materials Chemistry
# This journal is (C) The Royal Society of Chemistry 2010


data_global

_journal_coden_Cambridge         1145
_journal_volume                  ?
_journal_page_first              ?
_journal_year                    ?

loop_
_publ_author_name
'Skabara, Peter'
'McEntee, Greg'
'Vilela, Filipe'
'Anthopoulos, Thomas'
'Labram, John'
'Tierney, Steve'
'Harrington, Ross'
'Clegg, W.'

_publ_contact_author_name        'Skabara, Peter'
_publ_contact_author_email       peter.skabara@strath.ac.uk

_publ_section_title              
;
Self-assembly and charge transport properties
of a benzobisthiazole end-capped with dihexylthienothiophene units
;

# Attachment '- SSI1013.CIF'

data_ssi1013
_database_code_depnum_ccdc_archive 'CCDC 788178'
#TrackingRef '- SSI1013.CIF'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C44 H56 N2 S6'
_chemical_formula_sum            'C44 H56 N2 S6'
_chemical_formula_weight         805.27

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 0.1002 0.1169 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/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                   13.180(8)
_cell_length_b                   21.194(13)
_cell_length_c                   7.735(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 95.299(7)
_cell_angle_gamma                90.00
_cell_volume                     2151(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    950
_cell_measurement_theta_min      3.65
_cell_measurement_theta_max      25.78

_exptl_crystal_description       'block cut from needle'
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.08
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.02
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.243
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             860
_exptl_absorpt_coefficient_mu    0.321
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.975
_exptl_absorpt_correction_T_max  0.995
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     0.6889
_diffrn_radiation_type           synchrotron
_diffrn_radiation_source         'Diamond beamline I19'
_diffrn_radiation_monochromator  'double-crystal Si'
_diffrn_measurement_device_type  'Crystal Logics kappa and Rigaku Saturn 724+'
_diffrn_measurement_method       'thick-slice \w scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_interval_time  .
_diffrn_standards_decay_%        .
_diffrn_reflns_number            16755
_diffrn_reflns_av_R_equivalents  0.0481
_diffrn_reflns_av_sigmaI/netI    0.0399
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       6
_diffrn_reflns_theta_min         2.73
_diffrn_reflns_theta_max         24.20
_reflns_number_total             3763
_reflns_number_gt                2764
_reflns_threshold_expression     I>2\s(I)

_computing_data_collection       'Rigaku CrystalClear'
_computing_cell_refinement       'Bruker APEX2'
_computing_data_reduction        'Bruker APEX2'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'Bruker SHELXTL'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL and local programs'

_refine_special_details          
;
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ 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/[\s^2^(Fo^2^)+(0.0590P)^2^+2.3376P] where P=(Fo^2^+2Fc^2^)/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         3763
_refine_ls_number_parameters     235
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0723
_refine_ls_R_factor_gt           0.0499
_refine_ls_wR_factor_ref         0.1338
_refine_ls_wR_factor_gt          0.1219
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_restrained_S_all      1.032
_refine_ls_shift/su_max          0.001
_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 0.36647(6) 0.56922(4) 0.21071(11) 0.0387(2) Uani 1 1 d . . .
S2 S 0.60405(6) 0.60837(4) -0.14174(10) 0.0317(2) Uani 1 1 d . . .
S3 S 0.39946(6) 0.70508(4) -0.48606(11) 0.0387(2) Uani 1 1 d . . .
N1 N 0.5635(2) 0.55121(12) 0.1953(3) 0.0395(7) Uani 1 1 d . . .
C1 C 0.4819(2) 0.57664(13) 0.1111(4) 0.0314(7) Uani 1 1 d . . .
C2 C 0.5373(2) 0.52418(14) 0.3513(4) 0.0342(7) Uani 1 1 d . . .
C3 C 0.4335(2) 0.53025(14) 0.3816(4) 0.0340(7) Uani 1 1 d . . .
C4 C 0.3950(2) 0.50609(14) 0.5297(4) 0.0356(7) Uani 1 1 d . . .
H4 H 0.3250 0.5103 0.5479 0.043 Uiso 1 1 calc R . .
C5 C 0.4858(2) 0.60849(13) -0.0534(4) 0.0311(7) Uani 1 1 d . . .
C6 C 0.4101(2) 0.63891(13) -0.1576(4) 0.0327(7) Uani 1 1 d . . .
C7 C 0.4500(2) 0.66176(13) -0.3096(4) 0.0317(7) Uani 1 1 d . . .
C8 C 0.5526(2) 0.64909(13) -0.3219(4) 0.0306(7) Uani 1 1 d . . .
C9 C 0.5916(2) 0.67327(13) -0.4762(4) 0.0321(7) Uani 1 1 d . . .
C10 C 0.5158(2) 0.70411(14) -0.5727(4) 0.0378(8) Uani 1 1 d . . .
H10 H 0.5260 0.7237 -0.6802 0.045 Uiso 1 1 calc R . .
C11 C 0.3004(2) 0.64859(14) -0.1255(4) 0.0360(7) Uani 1 1 d . . .
H11A H 0.2763 0.6889 -0.1795 0.043 Uiso 1 1 calc R . .
H11B H 0.2956 0.6521 0.0011 0.043 Uiso 1 1 calc R . .
C12 C 0.2300(2) 0.59505(15) -0.1977(4) 0.0377(8) Uani 1 1 d . . .
H12A H 0.2302 0.5936 -0.3256 0.045 Uiso 1 1 calc R . .
H12B H 0.2566 0.5543 -0.1505 0.045 Uiso 1 1 calc R . .
C13 C 0.1210(2) 0.60381(17) -0.1512(5) 0.0440(8) Uani 1 1 d . . .
H13A H 0.1200 0.5993 -0.0240 0.053 Uiso 1 1 calc R . .
H13B H 0.0985 0.6472 -0.1826 0.053 Uiso 1 1 calc R . .
C14 C 0.0453(2) 0.55733(16) -0.2407(5) 0.0432(8) Uani 1 1 d . . .
H14A H 0.0463 0.5617 -0.3680 0.052 Uiso 1 1 calc R . .
H14B H 0.0674 0.5139 -0.2089 0.052 Uiso 1 1 calc R . .
C15 C -0.0631(3) 0.56673(18) -0.1939(5) 0.0497(9) Uani 1 1 d . . .
H15A H -0.0650 0.5596 -0.0677 0.060 Uiso 1 1 calc R . .
H15B H -0.0837 0.6110 -0.2187 0.060 Uiso 1 1 calc R . .
C16 C -0.1393(3) 0.52311(19) -0.2917(6) 0.0604(11) Uani 1 1 d . . .
H16A H -0.2076 0.5315 -0.2566 0.091 Uiso 1 1 calc R . .
H16B H -0.1207 0.4792 -0.2650 0.091 Uiso 1 1 calc R . .
H16C H -0.1389 0.5304 -0.4167 0.091 Uiso 1 1 calc R . .
C17 C 0.6981(2) 0.66302(15) -0.5245(4) 0.0356(7) Uani 1 1 d . . .
H17A H 0.7106 0.6171 -0.5315 0.043 Uiso 1 1 calc R . .
H17B H 0.7466 0.6802 -0.4310 0.043 Uiso 1 1 calc R . .
C18 C 0.7198(2) 0.69331(17) -0.6963(4) 0.0439(8) Uani 1 1 d . . .
H18A H 0.6636 0.6827 -0.7854 0.053 Uiso 1 1 calc R . .
H18B H 0.7207 0.7397 -0.6820 0.053 Uiso 1 1 calc R . .
C19 C 0.8203(3) 0.67259(18) -0.7617(5) 0.0489(9) Uani 1 1 d . . .
H19A H 0.8205 0.6260 -0.7700 0.059 Uiso 1 1 calc R . .
H19B H 0.8235 0.6895 -0.8804 0.059 Uiso 1 1 calc R . .
C20 C 0.9159(3) 0.69309(17) -0.6510(5) 0.0456(9) Uani 1 1 d . . .
H20A H 0.9148 0.6753 -0.5329 0.055 Uiso 1 1 calc R . .
H20B H 0.9164 0.7397 -0.6408 0.055 Uiso 1 1 calc R . .
C21 C 1.0130(3) 0.6716(2) -0.7280(6) 0.0586(10) Uani 1 1 d . . .
H21A H 1.0117 0.6250 -0.7389 0.070 Uiso 1 1 calc R . .
H21B H 1.0134 0.6894 -0.8462 0.070 Uiso 1 1 calc R . .
C22 C 1.1106(3) 0.6908(2) -0.6217(6) 0.0672(12) Uani 1 1 d . . .
H22A H 1.1693 0.6760 -0.6793 0.101 Uiso 1 1 calc R . .
H22B H 1.1123 0.6721 -0.5057 0.101 Uiso 1 1 calc R . .
H22C H 1.1132 0.7369 -0.6116 0.101 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 0.0346(4) 0.0422(5) 0.0399(5) 0.0015(4) 0.0062(4) -0.0020(3)
S2 0.0297(4) 0.0326(4) 0.0329(4) 0.0011(3) 0.0036(3) 0.0003(3)
S3 0.0337(4) 0.0367(4) 0.0450(5) 0.0065(4) -0.0007(4) 0.0023(3)
N1 0.0628(19) 0.0300(14) 0.0259(15) -0.0032(11) 0.0055(13) -0.0144(13)
C1 0.0323(16) 0.0291(15) 0.0327(18) -0.0047(13) 0.0023(13) -0.0009(12)
C2 0.0383(17) 0.0326(16) 0.0326(18) -0.0084(13) 0.0074(14) -0.0083(13)
C3 0.0345(17) 0.0304(16) 0.0367(19) -0.0055(13) 0.0017(14) -0.0028(13)
C4 0.0294(16) 0.0381(17) 0.040(2) -0.0095(14) 0.0075(14) -0.0045(13)
C5 0.0321(16) 0.0288(15) 0.0330(18) -0.0026(13) 0.0069(13) -0.0026(13)
C6 0.0356(17) 0.0271(15) 0.0360(19) -0.0064(13) 0.0065(14) -0.0036(13)
C7 0.0312(16) 0.0261(14) 0.0374(19) -0.0011(13) 0.0009(13) -0.0017(12)
C8 0.0300(16) 0.0272(15) 0.0343(18) -0.0011(13) 0.0017(13) -0.0016(12)
C9 0.0345(17) 0.0280(15) 0.0334(18) 0.0000(13) 0.0012(14) -0.0037(12)
C10 0.0379(18) 0.0360(17) 0.040(2) 0.0047(14) 0.0043(15) -0.0021(14)
C11 0.0307(16) 0.0354(16) 0.043(2) -0.0046(14) 0.0061(14) -0.0012(13)
C12 0.0335(17) 0.0389(17) 0.041(2) -0.0034(14) 0.0069(14) -0.0037(13)
C13 0.0346(18) 0.051(2) 0.047(2) -0.0072(17) 0.0087(15) -0.0060(15)
C14 0.0360(18) 0.0421(18) 0.051(2) -0.0012(16) 0.0030(16) -0.0033(14)
C15 0.0379(19) 0.055(2) 0.057(2) -0.0010(18) 0.0082(17) -0.0056(16)
C16 0.037(2) 0.057(2) 0.087(3) -0.005(2) 0.005(2) -0.0052(17)
C17 0.0347(17) 0.0335(16) 0.0392(19) 0.0040(14) 0.0064(14) -0.0006(13)
C18 0.0360(18) 0.055(2) 0.041(2) 0.0057(16) 0.0049(15) -0.0025(15)
C19 0.046(2) 0.059(2) 0.042(2) 0.0033(17) 0.0096(17) -0.0014(17)
C20 0.0419(19) 0.0433(19) 0.053(2) 0.0042(17) 0.0099(16) -0.0026(15)
C21 0.045(2) 0.070(3) 0.062(3) 0.004(2) 0.0156(19) 0.0037(19)
C22 0.043(2) 0.070(3) 0.090(3) 0.013(2) 0.011(2) -0.001(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 C1 1.775(3) . ?
S1 C3 1.731(3) . ?
S2 C5 1.758(3) . ?
S2 C8 1.724(3) . ?
S3 C7 1.727(3) . ?
S3 C10 1.730(3) . ?
N1 C1 1.319(4) . ?
N1 C2 1.407(4) . ?
C1 C5 1.446(4) . ?
C2 C3 1.415(4) . ?
C2 C4 1.380(5) 3_666 ?
C3 C4 1.393(5) . ?
C4 C2 1.380(5) 3_666 ?
C5 C6 1.383(4) . ?
C6 C7 1.417(4) . ?
C6 C11 1.504(4) . ?
C7 C8 1.391(4) . ?
C8 C9 1.438(4) . ?
C9 C10 1.358(4) . ?
C9 C17 1.500(4) . ?
C11 C12 1.538(4) . ?
C12 C13 1.524(4) . ?
C13 C14 1.522(4) . ?
C14 C15 1.520(5) . ?
C15 C16 1.515(5) . ?
C17 C18 1.527(5) . ?
C18 C19 1.526(5) . ?
C19 C20 1.519(5) . ?
C20 C21 1.530(5) . ?
C21 C22 1.517(5) . ?

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 C3 88.61(15) . . ?
C5 S2 C8 90.97(15) . . ?
C7 S3 C10 90.51(16) . . ?
C1 N1 C2 109.7(3) . . ?
S1 C1 N1 116.2(2) . . ?
S1 C1 C5 121.7(2) . . ?
N1 C1 C5 122.1(3) . . ?
N1 C2 C3 115.0(3) . . ?
N1 C2 C4 124.6(3) . 3_666 ?
C3 C2 C4 120.5(3) . 3_666 ?
S1 C3 C2 110.5(2) . . ?
S1 C3 C4 127.2(3) . . ?
C2 C3 C4 122.3(3) . . ?
C2 C4 C3 117.2(3) 3_666 . ?
S2 C5 C1 116.5(2) . . ?
S2 C5 C6 113.1(2) . . ?
C1 C5 C6 130.4(3) . . ?
C5 C6 C7 109.9(3) . . ?
C5 C6 C11 128.4(3) . . ?
C7 C6 C11 121.8(3) . . ?
S3 C7 C6 133.8(2) . . ?
S3 C7 C8 110.8(2) . . ?
C6 C7 C8 115.4(3) . . ?
S2 C8 C7 110.7(2) . . ?
S2 C8 C9 134.9(2) . . ?
C7 C8 C9 114.4(3) . . ?
C8 C9 C10 109.1(3) . . ?
C8 C9 C17 124.7(3) . . ?
C10 C9 C17 126.2(3) . . ?
S3 C10 C9 115.2(3) . . ?
C6 C11 C12 113.4(2) . . ?
C11 C12 C13 112.0(3) . . ?
C12 C13 C14 113.9(3) . . ?
C13 C14 C15 113.4(3) . . ?
C14 C15 C16 113.3(3) . . ?
C9 C17 C18 114.3(3) . . ?
C17 C18 C19 114.0(3) . . ?
C18 C19 C20 115.5(3) . . ?
C19 C20 C21 112.1(3) . . ?
C20 C21 C22 114.0(4) . . ?

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
C2 N1 C1 S1 -0.9(3) . . . . ?
C2 N1 C1 C5 179.4(3) . . . . ?
C3 S1 C1 N1 1.3(2) . . . . ?
C3 S1 C1 C5 -179.0(3) . . . . ?
C1 N1 C2 C3 -0.1(4) . . . . ?
C1 N1 C2 C4 -179.7(3) . . . 3_666 ?
N1 C2 C3 S1 1.1(3) . . . . ?
N1 C2 C3 C4 179.9(3) . . . . ?
C4 C2 C3 S1 -179.3(2) 3_666 . . . ?
C4 C2 C3 C4 -0.4(5) 3_666 . . . ?
C1 S1 C3 C2 -1.2(2) . . . . ?
C1 S1 C3 C4 180.0(3) . . . . ?
S1 C3 C4 C2 179.1(2) . . . 3_666 ?
C2 C3 C4 C2 0.4(5) . . . 3_666 ?
S1 C1 C5 S2 -176.64(16) . . . . ?
S1 C1 C5 C6 2.0(4) . . . . ?
N1 C1 C5 S2 3.0(4) . . . . ?
N1 C1 C5 C6 -178.3(3) . . . . ?
C8 S2 C5 C1 178.5(2) . . . . ?
C8 S2 C5 C6 -0.4(2) . . . . ?
S2 C5 C6 C7 0.1(3) . . . . ?
S2 C5 C6 C11 -179.9(2) . . . . ?
C1 C5 C6 C7 -178.6(3) . . . . ?
C1 C5 C6 C11 1.4(5) . . . . ?
C5 C6 C7 S3 -177.6(2) . . . . ?
C5 C6 C7 C8 0.3(4) . . . . ?
C11 C6 C7 S3 2.4(5) . . . . ?
C11 C6 C7 C8 -179.7(3) . . . . ?
C10 S3 C7 C6 178.7(3) . . . . ?
C10 S3 C7 C8 0.8(2) . . . . ?
S3 C7 C8 S2 177.78(15) . . . . ?
S3 C7 C8 C9 -1.1(3) . . . . ?
C6 C7 C8 S2 -0.5(3) . . . . ?
C6 C7 C8 C9 -179.4(2) . . . . ?
C5 S2 C8 C7 0.5(2) . . . . ?
C5 S2 C8 C9 179.0(3) . . . . ?
S2 C8 C9 C10 -177.7(3) . . . . ?
S2 C8 C9 C17 4.8(5) . . . . ?
C7 C8 C9 C10 0.8(4) . . . . ?
C7 C8 C9 C17 -176.6(3) . . . . ?
C8 C9 C10 S3 -0.2(3) . . . . ?
C17 C9 C10 S3 177.2(2) . . . . ?
C7 S3 C10 C9 -0.4(3) . . . . ?
C5 C6 C11 C12 -90.0(4) . . . . ?
C7 C6 C11 C12 90.0(4) . . . . ?
C6 C11 C12 C13 175.7(3) . . . . ?
C11 C12 C13 C14 171.8(3) . . . . ?
C12 C13 C14 C15 -179.8(3) . . . . ?
C13 C14 C15 C16 176.4(3) . . . . ?
C8 C9 C17 C18 179.5(3) . . . . ?
C10 C9 C17 C18 2.5(5) . . . . ?
C9 C17 C18 C19 -169.0(3) . . . . ?
C17 C18 C19 C20 -66.2(4) . . . . ?
C18 C19 C20 C21 -178.8(3) . . . . ?
C19 C20 C21 C22 -179.9(3) . . . . ?

_diffrn_measured_fraction_theta_max 0.989
_diffrn_reflns_theta_full        24.20
_diffrn_measured_fraction_theta_full 0.989
_refine_diff_density_max         1.197
_refine_diff_density_min         -0.382
_refine_diff_density_rms         0.059

#===END