Supplementary Material (ESI) for Journal of Materials Chemistry
This journal is (c) The Royal Society of Chemistry 2006


data_global

_journal_coden_Cambridge         1145

loop_
_publ_author_name
'Peter Skabara'
'Avni A. Argun'
'Rory Berridge'
'William Clegg'
'Aubrey Dyer'
'Ross W. Harrington'
'John R. Reynolds'
'Tim Steckler'
'Shaun P. Wright'

_publ_contact_author_name        'Peter Skabara'
_publ_contact_author_address     
;
Department of Pure and Applied Chemistry
The University of Strathclyde
295, Cathedral Street
Glasgow
G1 1XL
UNITED KINGDOM
;

_publ_contact_author_email       PETER.SKABARA@STRATH.AC.UK

_publ_requested_journal          'Journal of Materials Chemistry'

_publ_section_title              
;
Electrochromic properties of a fast switching, dual
colour polythiophene bearing non-planar dithiinoquinoxaline units
;

# Attachment 'SSC0432.CIF'

data_ssc0432_compound_6a
_database_code_depnum_ccdc_archive 'CCDC 624603'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C20 H10 N2 S5'
_chemical_formula_sum            'C20 H10 N2 S5'
_chemical_formula_weight         438.60

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 0.1246 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   '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                   3.8496(11)
_cell_length_b                   41.040(11)
_cell_length_c                   11.262(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 95.590(4)
_cell_angle_gamma                90.00
_cell_volume                     1770.8(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    2864
_cell_measurement_theta_min      2.27
_cell_measurement_theta_max      28.07

_exptl_crystal_description       needle
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.05
_exptl_crystal_size_mid          0.00
_exptl_crystal_size_min          0.00
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.645
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             896
_exptl_absorpt_coefficient_mu    0.663
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     0.6896
_diffrn_radiation_type           synchrotron
_diffrn_radiation_source         'Daresbury SRS station 9.8'
_diffrn_radiation_monochromator  'silicon 111'
_diffrn_measurement_device_type  'Bruker SMART 1K CCD diffractometer'
_diffrn_measurement_method       'thin-slice \w scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        15
_diffrn_reflns_number            12015
_diffrn_reflns_av_R_equivalents  0.0699
_diffrn_reflns_av_sigmaI/netI    0.0752
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_k_min       -51
_diffrn_reflns_limit_k_max       50
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         1.76
_diffrn_reflns_theta_max         25.52
_reflns_number_total             3585
_reflns_number_gt                2800
_reflns_threshold_expression     I>2\s(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_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^)+(0.0000P)^2^+14.4300P] 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     SHELXL
_refine_ls_extinction_coef       0.0041(8)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_number_reflns         3585
_refine_ls_number_parameters     268
_refine_ls_number_restraints     107
_refine_ls_R_factor_all          0.1155
_refine_ls_R_factor_gt           0.0900
_refine_ls_wR_factor_ref         0.1683
_refine_ls_wR_factor_gt          0.1606
_refine_ls_goodness_of_fit_ref   1.261
_refine_ls_restrained_S_all      1.242
_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 0.3861(4) 0.36825(4) 0.28397(14) 0.0146(4) Uani 1 1 d . . .
S2 S 0.6374(4) 0.40693(4) 0.53657(14) 0.0137(4) Uani 1 1 d . . .
S3 S 0.2281(4) 0.31222(4) 0.59345(14) 0.0135(4) Uani 1 1 d . . .
S4 S -0.0785(15) 0.30311(11) 0.2138(5) 0.0163(10) Uani 0.631(8) 1 d PDU A 1
S5 S 0.6633(5) 0.39213(4) 0.81895(16) 0.0218(4) Uani 1 1 d . . .
N1 N 0.1001(14) 0.42404(12) 0.2175(5) 0.0141(11) Uani 1 1 d . . .
N2 N 0.3382(13) 0.45729(12) 0.4291(4) 0.0116(11) Uani 1 1 d . . .
C1 C 0.2714(17) 0.40929(15) 0.3084(5) 0.0132(13) Uani 1 1 d . . .
C2 C 0.3904(16) 0.42595(14) 0.4160(5) 0.0125(13) Uani 1 1 d . . .
C3 C 0.1622(16) 0.47345(15) 0.3345(5) 0.0128(13) Uani 1 1 d . . .
C4 C 0.1040(17) 0.50703(15) 0.3443(6) 0.0157(13) Uani 1 1 d . . .
H4 H 0.1878 0.5185 0.4147 0.019 Uiso 1 1 calc R . .
C5 C -0.0765(18) 0.52315(15) 0.2504(6) 0.0189(14) Uani 1 1 d . . .
H5 H -0.1200 0.5458 0.2568 0.023 Uiso 1 1 calc R . .
C6 C -0.1961(18) 0.50671(16) 0.1462(6) 0.0216(15) Uani 1 1 d . . .
H6 H -0.3189 0.5183 0.0823 0.026 Uiso 1 1 calc R . .
C7 C -0.1388(19) 0.47393(15) 0.1348(6) 0.0195(15) Uani 1 1 d . . .
H7 H -0.2215 0.4628 0.0636 0.023 Uiso 1 1 calc R . .
C8 C 0.0436(17) 0.45700(15) 0.2296(6) 0.0148(13) Uani 1 1 d . . .
C9 C 0.3423(17) 0.35119(14) 0.4258(5) 0.0134(13) Uani 1 1 d . . .
C10 C 0.4492(16) 0.36783(14) 0.5333(5) 0.0116(12) Uani 1 1 d . . .
C11 C 0.4044(16) 0.35012(14) 0.6344(5) 0.0113(12) Uani 1 1 d . . .
C12 C 0.2071(16) 0.32078(14) 0.4421(5) 0.0121(13) Uani 1 1 d . A .
C13 C 0.0584(16) 0.29645(14) 0.3579(5) 0.0148(13) Uani 1 1 d DU . .
C14 C -0.016(12) 0.2643(6) 0.390(3) 0.014(4) Uani 0.631(8) 1 d PDU A 1
H14 H 0.0371 0.2560 0.4681 0.017 Uiso 0.631(8) 1 calc PR A 1
C15 C -0.173(4) 0.2454(3) 0.2963(13) 0.021(3) Uani 0.631(8) 1 d PDU A 1
H15 H -0.2310 0.2230 0.3020 0.025 Uiso 0.631(8) 1 calc PR A 1
C16 C -0.231(4) 0.2635(3) 0.1979(10) 0.015(3) Uani 0.631(8) 1 d PDU A 1
H16 H -0.3452 0.2553 0.1254 0.018 Uiso 0.631(8) 1 calc PR A 1
C17 C 0.4692(16) 0.35696(15) 0.7610(6) 0.0131(13) Uani 1 1 d . . .
C18 C 0.3817(15) 0.33611(14) 0.8551(5) 0.0093(12) Uani 1 1 d . . .
H18 H 0.2719 0.3155 0.8436 0.011 Uiso 1 1 calc R . .
C19 C 0.4794(18) 0.35016(17) 0.9667(6) 0.0215(15) Uani 1 1 d . . .
H19 H 0.4398 0.3398 1.0397 0.026 Uiso 1 1 calc R . .
C20 C 0.637(2) 0.38002(18) 0.9620(6) 0.0256(16) Uani 1 1 d . . .
H20 H 0.7203 0.3924 1.0301 0.031 Uiso 1 1 calc R . .
S4X S 0.002(7) 0.2578(3) 0.3979(14) 0.022(3) Uani 0.369(8) 1 d PDU A 2
C14X C -0.080(13) 0.3014(9) 0.239(3) 0.025(10) Uiso 0.369(8) 1 d PDU A 2
H14X H -0.0818 0.3221 0.2006 0.029 Uiso 0.369(8) 1 calc PR A 2
C15X C -0.214(7) 0.2730(5) 0.1817(16) 0.016(6) Uiso 0.369(8) 1 d PDU A 2
H15X H -0.3035 0.2716 0.1002 0.020 Uiso 0.369(8) 1 calc PR A 2
C16X C -0.196(8) 0.2484(5) 0.2593(17) 0.016(6) Uiso 0.369(8) 1 d PDU A 2
H16X H -0.2860 0.2273 0.2393 0.020 Uiso 0.369(8) 1 calc PR A 2

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 0.0210(9) 0.0117(7) 0.0118(8) -0.0014(6) 0.0046(6) 0.0019(6)
S2 0.0169(8) 0.0089(7) 0.0146(8) 0.0011(6) -0.0020(6) -0.0023(6)
S3 0.0184(8) 0.0080(7) 0.0142(8) 0.0001(6) 0.0026(6) -0.0011(6)
S4 0.0216(19) 0.0130(16) 0.0138(19) -0.0043(14) -0.0014(17) -0.0009(10)
S5 0.0251(10) 0.0196(8) 0.0205(9) -0.0021(7) 0.0016(7) -0.0023(7)
N1 0.016(3) 0.013(3) 0.014(3) 0.002(2) 0.004(2) -0.002(2)
N2 0.011(3) 0.012(2) 0.013(3) 0.001(2) 0.005(2) -0.001(2)
C1 0.018(3) 0.014(3) 0.008(3) 0.003(2) 0.004(2) -0.002(3)
C2 0.011(3) 0.015(3) 0.011(3) 0.003(2) -0.001(2) -0.001(2)
C3 0.013(3) 0.013(3) 0.014(3) 0.005(2) 0.009(3) -0.004(2)
C4 0.016(3) 0.014(3) 0.018(3) 0.000(3) 0.007(3) -0.002(3)
C5 0.024(4) 0.008(3) 0.025(4) -0.001(3) 0.004(3) 0.000(3)
C6 0.016(4) 0.019(3) 0.028(4) 0.011(3) -0.005(3) 0.001(3)
C7 0.028(4) 0.015(3) 0.014(3) 0.003(3) -0.004(3) 0.003(3)
C8 0.013(3) 0.014(3) 0.019(3) -0.001(3) 0.007(3) -0.003(2)
C9 0.023(4) 0.008(3) 0.008(3) 0.001(2) 0.000(3) 0.004(3)
C10 0.010(3) 0.006(3) 0.019(3) -0.001(2) 0.002(2) 0.001(2)
C11 0.012(3) 0.007(3) 0.015(3) -0.002(2) 0.000(2) 0.003(2)
C12 0.011(3) 0.013(3) 0.014(3) 0.002(2) 0.006(2) 0.001(2)
C13 0.010(3) 0.012(3) 0.022(3) -0.003(2) 0.002(3) 0.001(2)
C14 0.011(8) 0.011(9) 0.021(7) 0.000(6) 0.003(6) 0.001(10)
C15 0.024(7) 0.010(5) 0.028(8) -0.004(4) 0.002(7) -0.003(4)
C16 0.023(6) 0.007(6) 0.016(5) -0.009(5) 0.006(4) -0.006(5)
C17 0.007(3) 0.013(3) 0.020(3) 0.001(2) 0.002(2) 0.004(2)
C18 0.009(3) 0.009(3) 0.010(3) -0.001(2) 0.003(2) 0.002(2)
C19 0.022(4) 0.032(4) 0.012(3) 0.005(3) 0.005(3) 0.010(3)
C20 0.028(4) 0.029(4) 0.020(4) -0.007(3) -0.001(3) 0.003(3)
S4X 0.030(5) 0.009(4) 0.028(5) -0.001(3) 0.004(3) 0.000(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 1.769(6) . ?
S1 C9 1.767(6) . ?
S2 C2 1.762(6) . ?
S2 C10 1.760(6) . ?
S3 C11 1.741(6) . ?
S3 C12 1.734(6) . ?
S4 C13 1.680(8) . ?
S4 C16 1.732(13) . ?
S5 C17 1.724(6) . ?
S5 C20 1.698(7) . ?
N1 C1 1.311(8) . ?
N1 C8 1.379(8) . ?
N2 C2 1.312(8) . ?
N2 C3 1.376(8) . ?
C1 C2 1.427(8) . ?
C3 C4 1.402(9) . ?
C3 C8 1.398(9) . ?
C4 C5 1.377(9) . ?
C5 C6 1.392(10) . ?
C6 C7 1.371(9) . ?
C7 C8 1.404(9) . ?
C9 C10 1.415(8) . ?
C9 C12 1.371(8) . ?
C10 C11 1.376(9) . ?
C11 C17 1.452(9) . ?
C12 C13 1.455(8) . ?
C13 C14 1.40(2) . ?
C13 S4X 1.669(10) . ?
C13 C14X 1.41(3) . ?
C14 C15 1.40(3) . ?
C15 C16 1.334(16) . ?
C17 C18 1.428(8) . ?
C18 C19 1.400(9) . ?
C19 C20 1.370(10) . ?
S4X C16X 1.714(18) . ?
C14X C15X 1.41(3) . ?
C15X C16X 1.334(19) . ?

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 C9 100.9(3) . . ?
C2 S2 C10 101.4(3) . . ?
C11 S3 C12 93.4(3) . . ?
C13 S4 C16 91.1(5) . . ?
C17 S5 C20 92.8(3) . . ?
C1 N1 C8 116.6(5) . . ?
C2 N2 C3 117.1(5) . . ?
S1 C1 N1 115.6(5) . . ?
S1 C1 C2 121.6(5) . . ?
N1 C1 C2 122.5(6) . . ?
S2 C2 N2 115.1(5) . . ?
S2 C2 C1 123.1(5) . . ?
N2 C2 C1 121.7(5) . . ?
N2 C3 C4 118.9(6) . . ?
N2 C3 C8 121.1(5) . . ?
C4 C3 C8 120.0(6) . . ?
C3 C4 C5 118.9(6) . . ?
C4 C5 C6 121.0(6) . . ?
C5 C6 C7 120.8(6) . . ?
C6 C7 C8 119.2(6) . . ?
N1 C8 C3 121.0(6) . . ?
N1 C8 C7 118.8(6) . . ?
C3 C8 C7 120.1(6) . . ?
S1 C9 C10 122.4(5) . . ?
S1 C9 C12 123.5(5) . . ?
C10 C9 C12 114.0(5) . . ?
S2 C10 C9 122.9(5) . . ?
S2 C10 C11 123.3(5) . . ?
C9 C10 C11 113.8(5) . . ?
S3 C11 C10 109.3(4) . . ?
S3 C11 C17 117.3(5) . . ?
C10 C11 C17 133.4(6) . . ?
S3 C12 C9 109.5(5) . . ?
S3 C12 C13 118.6(4) . . ?
C9 C12 C13 131.9(6) . . ?
S4 C13 C12 125.8(5) . . ?
S4 C13 C14 110.3(13) . . ?
C12 C13 C14 123.8(14) . . ?
C12 C13 S4X 122.0(7) . . ?
C12 C13 C14X 127.5(16) . . ?
S4X C13 C14X 110.4(12) . . ?
C13 C14 C15 114(2) . . ?
C14 C15 C16 110.0(14) . . ?
S4 C16 C15 114.1(10) . . ?
S5 C17 C11 124.1(5) . . ?
S5 C17 C18 110.2(5) . . ?
C11 C17 C18 125.7(6) . . ?
C17 C18 C19 110.9(6) . . ?
C18 C19 C20 114.5(6) . . ?
S5 C20 C19 111.5(5) . . ?
C13 S4X C16X 91.5(8) . . ?
C13 C14X C15X 114(2) . . ?
C14X C15X C16X 109.6(18) . . ?
S4X C16X C15X 114.6(15) . . ?

_diffrn_measured_fraction_theta_max 0.990
_diffrn_reflns_theta_full        25.52
_diffrn_measured_fraction_theta_full 0.990
_refine_diff_density_max         0.548
_refine_diff_density_min         -0.608
_refine_diff_density_rms         0.149

#===END