Supplementary Material (ESI) for Journal of Materials Chemistry
This journal is © The Royal Society of Chemistry 2003

data_global
_journal_name_full               J.Mater.Chem.

_journal_coden_Cambridge         1145

loop_
_publ_author_name
'Pierre Frere'
'Magali Allain'
'Philippe Leriche'
'Vincent Monroche'
'Jean-Manuel Raimundo'
'J. Roncali'
;
S.Francois Xavier
;
'Peter Skabara'
'Mathieu Turbiez'

_publ_contact_author_name        'Prof Pierre Frere'
_publ_contact_author_address     
;
Laboratoire IMMO
Univerite d'Angers
2 Bd Lavoisier
Angers
F-49045
FRANCE
;

_publ_contact_author_email       PIERRE.FRERE@UNIV-ANGERS.FR

_publ_section_title              
;
Linearly extended tetrathiafulvalene analogues with fused 
thiophene units as pi-conjugated spacers
;

data_pfe134
_database_code_CSD               187825

_audit_creation_date             2003-01-23T10:17:13-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

#------------------ CHEMICAL INFORMATION ------------------------------------#

_chemical_formula_moiety         'C9 H8 Cl1 O4 S5'
_chemical_formula_sum            'C9 H8 Cl O4 S5'
_chemical_formula_weight         375.9

#------------------ UNIT CELL INFORMATION -----------------------------------#

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P n m a'
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z+1/2'
'-x, y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'-x-1/2, y-1/2, z-1/2'
'x, -y-1/2, z'

_cell_length_a                   20.223(2)
_cell_length_b                   7.0107(5)
_cell_length_c                   19.581(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2776.1(4)
_cell_formula_units_Z            8
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    4371
_cell_measurement_theta_min      2.25
_cell_measurement_theta_max      25.7

#------------------ CRYSTAL INFORMATION -------------------------------------#

_exptl_crystal_description       needle
_exptl_crystal_colour            black
_exptl_crystal_size_max          0.57
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.06
_exptl_crystal_density_diffrn    1.799
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1528
_exptl_absorpt_coefficient_mu    1.031
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8029
_exptl_absorpt_correction_T_max  0.8524

#------------------ DATA COLLECTION INFORMATION -----------------------------#

_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_measurement_device_type  'STOE IPDS'
_diffrn_measurement_method       'Oscillation Phi Incr 1.1 deg'
_diffrn_detector_area_resol_mean 6.66
_diffrn_reflns_number            15663
_diffrn_reflns_av_R_equivalents  0.1571
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         2.08
_diffrn_reflns_theta_max         25.82
_diffrn_reflns_theta_full        25.82
_diffrn_measured_fraction_theta_max 0.949
_diffrn_measured_fraction_theta_full 0.949
_reflns_number_total             2764
_reflns_number_gt                1284
_reflns_threshold_expression     >2sigma(I)

#------------------ COMPUTER PROGRAMS USED ----------------------------------#

_computing_data_collection       'EXPOSE, STOE IPDS'
_computing_cell_refinement       'SELECT,CELL, STOE IPDS'
_computing_data_reduction        'INTEGRATE, STOE IPDS'
_computing_structure_solution    'Direct methods (Sir92,Altomare et al.,1993)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'DIAMOND 2.1e (Crystal Impact gbr 2001)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'

#------------------ REFINEMENT INFORMATION ----------------------------------#

_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^)+(0.0443P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_number_reflns         2764
_refine_ls_number_parameters     169
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1226
_refine_ls_R_factor_gt           0.0502
_refine_ls_wR_factor_gt          0.0947
_refine_ls_wR_factor_ref         0.1117
_refine_ls_goodness_of_fit_ref   0.798
_refine_ls_restrained_S_all      0.798
_refine_ls_shift/su_max          0
_refine_diff_density_max         0.412
_refine_diff_density_min         -0.383

#------------------ ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS --------#

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 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.006 '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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_group
_atom_site_disorder_assembly
C1 C 0.5724(4) 0.25 -0.3539(3) 0.0363(18) Uiso 1 d S . .
C2 C 0.5915(4) 0.25 -0.2855(3) 0.0364(19) Uiso 1 d S . .
H2 H 0.6368 0.25 -0.2772 0.044 Uiso 1 calc SR . .
C3 C 0.5511(3) 0.25 -0.2283(3) 0.0341(17) Uiso 1 d S . .
C4 C 0.5764(3) 0.25 -0.1585(3) 0.0325(17) Uiso 1 d S . .
H4 H 0.6208 0.25 -0.1463 0.039 Uiso 1 calc SR . .
C5 C 0.5242(3) 0.25 -0.1135(3) 0.0284(16) Uiso 1 d S . .
C6 C 0.4598(3) 0.25 -0.1440(3) 0.0323(17) Uiso 1 d S . .
C7 C 0.4078(4) 0.25 -0.0997(3) 0.0369(19) Uiso 1 d S . .
H7 H 0.3634 0.25 -0.1122 0.044 Uiso 1 calc SR . .
C8 C 0.4322(4) 0.25 -0.0303(3) 0.0342(17) Uiso 1 d S . .
C9 C 0.3903(4) 0.25 0.0245(3) 0.0388(19) Uiso 1 d S . .
H9 H 0.3453 0.25 0.0144 0.047 Uiso 1 calc SR . .
C10 C 0.4068(4) 0.25 0.0948(3) 0.0388(19) Uiso 1 d S . .
C11 C 0.5135(4) 0.25 -0.4696(3) 0.0354(18) Uiso 1 d S . .
C12 C 0.5791(4) 0.25 -0.4841(3) 0.0357(18) Uiso 1 d S . .
C13 C 0.3783(5) 0.25 -0.4878(5) 0.067(3) Uiso 1 d S . .
H13A H 0.342 0.25 -0.5194 0.1 Uiso 1 calc SR . .
H13B H 0.376 0.3618 -0.4596 0.1 Uiso 0.5 calc PR . .
H13C H 0.376 0.1382 -0.4596 0.1 Uiso 0.5 calc PR . .
C14 C 0.6954(4) 0.25 -0.5597(4) 0.056(2) Uiso 1 d S . .
H14A H 0.7154 0.25 -0.6042 0.084 Uiso 1 calc SR . .
H14B H 0.7091 0.1382 -0.5352 0.084 Uiso 0.5 calc PR . .
H14C H 0.7091 0.3618 -0.5352 0.084 Uiso 0.5 calc PR . .
C15 C 0.3930(4) 0.25 0.2244(3) 0.0344(17) Uiso 1 d S . .
C16 C 0.4584(4) 0.25 0.2140(3) 0.0344(18) Uiso 1 d S . .
C17 C 0.2707(5) 0.25 0.2894(4) 0.065(3) Uiso 1 d S . .
H17A H 0.2469 0.25 0.3318 0.098 Uiso 1 calc SR . .
H17B H 0.2592 0.1382 0.2637 0.098 Uiso 0.5 calc PR . .
H17C H 0.2592 0.3618 0.2637 0.098 Uiso 0.5 calc PR . .
C18 C 0.5951(4) 0.25 0.2414(4) 0.054(2) Uiso 1 d S . .
H18A H 0.6288 0.25 0.276 0.081 Uiso 1 calc SR . .
H18B H 0.5997 0.3618 0.2135 0.081 Uiso 0.5 calc PR . .
H18C H 0.5997 0.1382 0.2135 0.081 Uiso 0.5 calc PR . .
O1 O 0.2276(4) 0.25 -0.2998(4) 0.213(8) Uani 1 d S . .
O2 O 0.3120(4) 0.25 -0.2269(3) 0.114(3) Uani 1 d S . .
O3 O 0.3188(4) 0.0916(11) -0.3276(3) 0.145(3) Uani 1 d . . .
O4 O 0.6654(4) 0.25 -0.0332(3) 0.160(6) Uani 1 d S . .
O5 O 0.6398(3) 0.25 0.0817(3) 0.098(3) Uani 1 d S . .
O6 O 0.7314(3) 0.4125(10) 0.0433(3) 0.107(2) Uani 1 d . . .
S1 S 0.46521(9) 0.25 -0.23205(9) 0.0435(6) Uani 1 d S . .
S2 S 0.49346(9) 0.25 -0.38422(8) 0.0421(6) Uani 1 d S . .
S3 S 0.63204(10) 0.25 -0.41557(9) 0.0484(7) Uani 1 d S . .
S4 S 0.45405(10) 0.25 -0.53372(9) 0.0475(6) Uani 1 d S . .
S5 S 0.60659(11) 0.25 -0.56834(9) 0.0610(8) Uani 1 d S . .
S6 S 0.51854(10) 0.25 -0.02562(8) 0.0426(6) Uani 1 d S . .
S7 S 0.34430(10) 0.25 0.15287(8) 0.0538(7) Uani 1 d S . .
S8 S 0.48413(9) 0.25 0.12949(9) 0.0380(5) Uani 1 d S . .
S9 S 0.35788(11) 0.25 0.30616(9) 0.0564(8) Uani 1 d S . .
S10 S 0.51430(10) 0.25 0.28166(9) 0.0472(6) Uani 1 d S . .
Cl1 Cl 0.29287(11) 0.25 -0.29535(10) 0.0564(7) Uani 1 d S . .
Cl2 Cl 0.69173(11) 0.25 0.03294(10) 0.0666(8) Uani 1 d S . .

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
O1 0.054(6) 0.50(3) 0.086(6) 0 -0.023(4) 0
O2 0.110(7) 0.185(11) 0.046(4) 0 -0.022(4) 0
O3 0.230(8) 0.110(7) 0.096(4) -0.027(4) 0.010(4) 0.051(6)
O4 0.076(6) 0.365(18) 0.040(4) 0 -0.008(4) 0
O5 0.055(4) 0.187(10) 0.051(4) 0 0.016(3) 0
O6 0.086(4) 0.107(6) 0.128(4) -0.001(4) 0.014(3) -0.025(4)
S1 0.0383(12) 0.0654(19) 0.0267(8) 0 0.0008(7) 0
S2 0.0347(12) 0.0632(18) 0.0285(9) 0 0.0048(8) 0
S3 0.0364(12) 0.079(2) 0.0294(9) 0 0.0018(8) 0
S4 0.0399(12) 0.068(2) 0.0344(9) 0 -0.0055(8) 0
S5 0.0440(13) 0.113(3) 0.0261(9) 0 0.0052(8) 0
S6 0.0350(12) 0.0660(19) 0.0269(9) 0 -0.0011(7) 0
S7 0.0302(12) 0.104(2) 0.0277(9) 0 0.0009(8) 0
S8 0.0284(10) 0.0584(16) 0.0273(8) 0 0.0005(7) 0
S9 0.0483(15) 0.093(2) 0.0276(9) 0 0.0053(8) 0
S10 0.0400(12) 0.074(2) 0.0273(9) 0 -0.0066(8) 0
Cl1 0.0447(14) 0.084(2) 0.0408(11) 0 -0.0026(9) 0
Cl2 0.0380(14) 0.117(3) 0.0445(12) 0 -0.0029(9) 0

#------------------ MOLECULAR GEOMETRY --------------------------------------#

_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 1.395(9) . ?
C1 S2 1.702(7) . ?
C1 S3 1.707(7) . ?
C2 C3 1.386(9) . ?
C3 C4 1.459(9) . ?
C3 S1 1.738(7) . ?
C4 C5 1.374(9) . ?
C5 C6 1.433(9) . ?
C5 S6 1.724(6) . ?
C6 C7 1.363(10) . ?
C6 S1 1.728(6) . ?
C7 C8 1.446(9) . ?
C8 C9 1.368(9) . ?
C8 S6 1.749(7) . ?
C9 C10 1.415(9) . ?
C10 S7 1.700(7) . ?
C10 S8 1.706(8) . ?
C11 C12 1.357(10) . ?
C11 S2 1.720(7) . ?
C11 S4 1.738(7) . ?
C12 S3 1.717(7) . ?
C12 S5 1.741(7) . ?
C13 S4 1.776(9) . ?
C14 S5 1.804(9) . ?
C15 C16 1.338(10) . ?
C15 S7 1.711(7) . ?
C15 S9 1.751(7) . ?
C16 S8 1.735(6) . ?
C16 S10 1.742(7) . ?
C17 S9 1.794(10) . ?
C18 S10 1.815(8) . ?
O1 Cl1 1.322(9) . ?
O2 Cl1 1.395(6) . ?
O3 Cl1 1.381(6) . ?
O4 Cl2 1.400(6) . ?
O5 Cl2 1.420(6) . ?
O6 Cl2 1.408(6) . ?
Cl1 O3 1.381(6) 8_565 ?
Cl2 O6 1.408(6) 8_565 ?

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 126.5(6) . . ?
C2 C1 S3 118.9(6) . . ?
S2 C1 S3 114.6(4) . . ?
C3 C2 C1 127.8(7) . . ?
C2 C3 C4 123.4(6) . . ?
C2 C3 S1 123.7(5) . . ?
C4 C3 S1 112.9(5) . . ?
C5 C4 C3 109.4(6) . . ?
C4 C5 C6 115.5(5) . . ?
C4 C5 S6 133.7(5) . . ?
C6 C5 S6 110.8(5) . . ?
C7 C6 C5 115.9(5) . . ?
C7 C6 S1 133.1(6) . . ?
C5 C6 S1 111.0(5) . . ?
C6 C7 C8 109.5(7) . . ?
C9 C8 C7 121.7(7) . . ?
C9 C8 S6 125.3(5) . . ?
C7 C8 S6 113.0(5) . . ?
C8 C9 C10 128.1(7) . . ?
C9 C10 S7 118.4(6) . . ?
C9 C10 S8 127.1(6) . . ?
S7 C10 S8 114.5(4) . . ?
C12 C11 S2 115.7(5) . . ?
C12 C11 S4 121.7(5) . . ?
S2 C11 S4 122.7(4) . . ?
C11 C12 S3 116.5(5) . . ?
C11 C12 S5 120.7(5) . . ?
S3 C12 S5 122.8(4) . . ?
C16 C15 S7 116.4(5) . . ?
C16 C15 S9 122.6(5) . . ?
S7 C15 S9 121.0(4) . . ?
C15 C16 S8 116.2(5) . . ?
C15 C16 S10 121.8(5) . . ?
S8 C16 S10 122.0(4) . . ?
C6 S1 C3 91.2(3) . . ?
C1 S2 C11 96.8(3) . . ?
C1 S3 C12 96.4(3) . . ?
C11 S4 C13 103.3(4) . . ?
C12 S5 C14 103.3(4) . . ?
C5 S6 C8 90.8(3) . . ?
C10 S7 C15 96.9(3) . . ?
C10 S8 C16 96.0(3) . . ?
C15 S9 C17 103.3(4) . . ?
C16 S10 C18 104.8(4) . . ?
O1 Cl1 O3 110.4(4) . . ?
O1 Cl1 O3 110.4(4) . 8_565 ?
O3 Cl1 O3 107.1(7) . 8_565 ?
O1 Cl1 O2 109.9(5) . . ?
O3 Cl1 O2 109.5(3) . . ?
O3 Cl1 O2 109.5(3) 8_565 . ?
O4 Cl2 O6 110.5(3) . 8_565 ?
O4 Cl2 O6 110.5(3) . . ?
O6 Cl2 O6 108.0(6) 8_565 . ?
O4 Cl2 O5 109.9(4) . . ?
O6 Cl2 O5 108.9(3) 8_565 . ?
O6 Cl2 O5 108.9(3) . . ?