# Supplementary Material (ESI) for New Journal of Chemistry
# This journal is (c) The Royal Society of Chemistry and The Centre National de la Recherche Scientifique, 2010

data_global
_journal_name_full               'New J.Chem.'

_journal_coden_Cambridge         0440

_publ_contact_author_name        'Porzio, William'
_publ_contact_author_email       w.porzio@ismac.cnr.it

_publ_section_title              
;
Synthesis and characterisations of
fluorenone-thiophene based donor-acceptor oligomers:
role of moiety sequence onto packing and electronic
properties
;
loop_
_publ_author_name
W.Porzio
S.Destri
M.Pasini
U.Giovanella
G.Scavia
M.Ragazzi
;
D.Kotowski
;
G.Zotti
B.Vercelli

# Attachment '- TFTcif.cif'

data_shelxl
_database_code_depnum_ccdc_archive 'CCDC 736650'
#TrackingRef '- TFTcif.cif'

_audit_update_record             
;
2009-06-11 # Formatted by publCIF
;

_audit_creation_method           SHELXL
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_formula_moiety         ?
_chemical_formula_structural     ?
_chemical_formula_analytical     ?
_chemical_formula_sum            'C21 H12 O S2'
_chemical_formula_weight         344.43
_chemical_melting_point          ?
_chemical_compound_source        ?

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
S S 0.1246 0.1234 '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'
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'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   P21/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                   14.862(2)
_cell_length_b                   5.888(2)
_cell_length_c                   18.100(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 93.090(10)
_cell_angle_gamma                90.00
_cell_volume                     1581.5(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.07
_exptl_crystal_density_meas      1.43
_exptl_crystal_density_diffrn    1.447
_exptl_crystal_density_method    flotation
_exptl_crystal_F_000             712
_exptl_absorpt_coefficient_mu    0.340
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      293(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       ?
_diffrn_measurement_method       ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            3558
_diffrn_reflns_av_R_equivalents  0.0438
_diffrn_reflns_av_sigmaI/netI    0.1406
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         3.46
_diffrn_reflns_theta_max         26.97
_reflns_number_total             3442
_reflns_number_observed          1457
_reflns_observed_criterion       >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-93 (Sheldrick, 1993)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
Refinement on F^2^ for ALL reflections except for 0 with very negative F^2^
or flagged by the user for potential systematic errors. Weighted R-factors
wR and all goodnesses 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 observed criterion
of F^2^ > 2sigma(F^2^) is used only for calculating _R_factor_obs 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 w=1/[\s^2^(Fo^2^)+(0.0828P)^2^+0.5400P] 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    ?
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3442
_refine_ls_number_parameters     229
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.2126
_refine_ls_R_factor_obs          0.0564
_refine_ls_wR_factor_all         0.1853
_refine_ls_wR_factor_obs         0.1357
_refine_ls_goodness_of_fit_all   1.007
_refine_ls_goodness_of_fit_obs   1.185
_refine_ls_restrained_S_all      1.007
_refine_ls_restrained_S_obs      1.185
_refine_ls_shift/su_max          0.000

_refine_ls_shift/esd_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_thermal_displace_type
_atom_site_occupancy
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_group
S1 S 0.84907(9) 0.0774(3) 0.50080(9) 0.0795(5) Uani 1 d . .
S23 S 0.12358(10) -0.2097(3) 0.73750(8) 0.0804(5) Uani 1 d . .
O O 0.4191(2) -0.3974(5) 0.5704(2) 0.0513(8) Uani 1 d . .
C2 C 0.9012(3) -0.1084(10) 0.4466(3) 0.0716(15) Uani 1 d . .
H2 H 0.9582(3) -0.0850(10) 0.4292(3) 0.088(17) Uiso 1 calc R .
C3 C 0.8513(3) -0.2931(10) 0.4315(3) 0.0666(14) Uani 1 d . .
H3 H 0.8696(3) -0.4104(10) 0.4014(3) 0.088(19) Uiso 1 calc R .
C4 C 0.7676(2) -0.2933(8) 0.4657(2) 0.0435(10) Uani 1 d . .
H4 H 0.7259(2) -0.4111(8) 0.4621(2) 0.074(16) Uiso 1 calc R .
C5 C 0.7561(3) -0.0915(8) 0.5057(2) 0.0451(10) Uani 1 d . .
C6 C 0.6784(3) -0.0233(7) 0.5477(2) 0.0406(10) Uani 1 d . .
C7 C 0.6775(3) 0.1789(7) 0.5873(2) 0.0456(10) Uani 1 d . .
H7 H 0.7278(3) 0.2729(7) 0.5874(2) 0.050(12) Uiso 1 calc R .
C8 C 0.6047(3) 0.2462(7) 0.6268(2) 0.0454(10) Uani 1 d . .
H8 H 0.6060(3) 0.3829(7) 0.6526(2) 0.036(10) Uiso 1 calc R .
C9 C 0.5304(2) 0.1069(7) 0.6272(2) 0.0371(9) Uani 1 d . .
C10 C 0.5310(2) -0.0984(7) 0.5880(2) 0.0369(9) Uani 1 d . .
C11 C 0.6021(2) -0.1636(7) 0.5484(2) 0.0402(10) Uani 1 d . .
H11 H 0.6001(2) -0.2995(7) 0.5222(2) 0.037(11) Uiso 1 calc R .
C12 C 0.4439(3) -0.2175(7) 0.5973(2) 0.0388(9) Uani 1 d . .
C13 C 0.3929(3) -0.0726(7) 0.6481(2) 0.0392(9) Uani 1 d . .
C14 C 0.4441(3) 0.1216(7) 0.6645(2) 0.0385(9) Uani 1 d . .
C15 C 0.4100(3) 0.2840(7) 0.7114(2) 0.0462(10) Uani 1 d . .
H15 H 0.4420(3) 0.4165(7) 0.7223(2) 0.048(12) Uiso 1 calc R .
C16 C 0.3286(3) 0.2459(7) 0.7411(2) 0.0476(11) Uani 1 d . .
H16 H 0.3063(3) 0.3546(7) 0.7725(2) 0.073(15) Uiso 1 calc R .
C17 C 0.2778(3) 0.0505(7) 0.7261(2) 0.0412(10) Uani 1 d . .
C18 C 0.3111(3) -0.1111(8) 0.6777(2) 0.0435(10) Uani 1 d . .
H18 H 0.2784(3) -0.2420(8) 0.6659(2) 0.048(12) Uiso 1 calc R .
C19 C 0.1929(3) 0.0115(8) 0.7629(2) 0.0465(10) Uani 1 d . .
C20 C 0.1590(3) 0.1352(9) 0.8239(2) 0.0506(12) Uani 1 d . .
H20 H 0.1856(3) 0.2620(9) 0.8466(2) 0.063(15) Uiso 1 calc R .
C21 C 0.0778(3) 0.0303(10) 0.8436(3) 0.071(2) Uani 1 d . .
H21 H 0.0452(3) 0.0837(10) 0.8825(3) 0.087(17) Uiso 1 calc R .
C22 C 0.0507(4) -0.1496(10) 0.8033(3) 0.072(2) Uani 1 d . .
H22 H -0.0017(4) -0.2313(10) 0.8105(3) 0.116(22) Uiso 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 0.0627(8) 0.0844(11) 0.0937(10) -0.0200(9) 0.0243(7) -0.0272(8)
S23 0.0804(9) 0.0789(10) 0.0853(10) -0.0143(9) 0.0364(8) -0.0188(8)
O 0.053(2) 0.042(2) 0.059(2) -0.016(2) 0.0102(14) -0.0101(14)
C2 0.053(3) 0.095(4) 0.069(3) -0.011(3) 0.021(2) -0.012(3)
C3 0.060(3) 0.072(4) 0.069(3) -0.013(3) 0.015(3) 0.005(3)
C4 0.031(2) 0.052(3) 0.049(2) -0.008(2) 0.012(2) -0.006(2)
C5 0.043(2) 0.053(3) 0.039(2) 0.008(2) 0.000(2) -0.009(2)
C6 0.041(2) 0.042(2) 0.038(2) 0.003(2) -0.001(2) -0.005(2)
C7 0.046(2) 0.042(3) 0.049(2) 0.000(2) 0.005(2) -0.011(2)
C8 0.057(3) 0.032(2) 0.047(2) -0.009(2) -0.004(2) -0.008(2)
C9 0.045(2) 0.032(2) 0.034(2) -0.001(2) -0.003(2) 0.002(2)
C10 0.039(2) 0.037(2) 0.035(2) 0.001(2) 0.001(2) -0.002(2)
C11 0.046(2) 0.036(2) 0.038(2) -0.004(2) -0.002(2) 0.001(2)
C12 0.043(2) 0.036(2) 0.037(2) -0.002(2) -0.001(2) 0.002(2)
C13 0.045(2) 0.035(2) 0.037(2) -0.002(2) -0.003(2) 0.001(2)
C14 0.046(2) 0.034(2) 0.035(2) -0.005(2) -0.001(2) 0.004(2)
C15 0.055(3) 0.037(2) 0.047(2) -0.003(2) -0.001(2) -0.007(2)
C16 0.061(3) 0.042(3) 0.040(2) -0.007(2) 0.007(2) 0.007(2)
C17 0.048(2) 0.041(3) 0.035(2) 0.001(2) 0.000(2) 0.006(2)
C18 0.044(2) 0.043(2) 0.044(2) -0.002(2) 0.002(2) 0.001(2)
C19 0.046(2) 0.053(3) 0.041(2) 0.005(2) -0.001(2) 0.008(2)
C20 0.038(2) 0.067(3) 0.047(2) 0.003(2) 0.012(2) 0.004(2)
C21 0.066(3) 0.094(4) 0.055(3) -0.009(3) 0.020(3) 0.016(3)
C22 0.065(3) 0.086(4) 0.067(3) 0.008(3) 0.028(3) -0.001(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
S1 C2 1.686(5) . ?
S1 C5 1.709(4) . ?
S23 C22 1.690(5) . ?
S23 C19 1.709(5) . ?
O C12 1.214(5) . ?
C2 C3 1.337(7) . ?
C3 C4 1.419(6) . ?
C4 C5 1.407(6) . ?
C5 C6 1.471(5) . ?
C6 C7 1.390(6) . ?
C6 C11 1.404(5) . ?
C7 C8 1.387(5) . ?
C8 C9 1.375(5) . ?
C9 C10 1.401(5) . ?
C9 C14 1.483(5) . ?
C10 C11 1.364(5) . ?
C10 C12 1.491(5) . ?
C12 C13 1.491(5) . ?
C13 C18 1.375(5) . ?
C13 C14 1.397(5) . ?
C14 C15 1.392(5) . ?
C15 C16 1.368(6) . ?
C16 C17 1.394(6) . ?
C17 C18 1.400(5) . ?
C17 C19 1.477(5) . ?
C19 C20 1.437(6) . ?
C20 C21 1.418(6) . ?
C21 C22 1.336(7) . ?

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 S1 C5 92.9(2) . . ?
C22 S23 C19 92.9(3) . . ?
C3 C2 S1 112.3(4) . . ?
C2 C3 C4 113.7(5) . . ?
C5 C4 C3 111.0(4) . . ?
C4 C5 C6 128.1(4) . . ?
C4 C5 S1 110.1(3) . . ?
C6 C5 S1 121.8(3) . . ?
C7 C6 C11 117.9(4) . . ?
C7 C6 C5 122.0(4) . . ?
C11 C6 C5 120.0(4) . . ?
C8 C7 C6 122.7(4) . . ?
C9 C8 C7 118.7(4) . . ?
C8 C9 C10 119.0(3) . . ?
C8 C9 C14 132.9(4) . . ?
C10 C9 C14 108.1(3) . . ?
C11 C10 C9 122.4(4) . . ?
C11 C10 C12 129.0(4) . . ?
C9 C10 C12 108.7(3) . . ?
C10 C11 C6 119.2(4) . . ?
O C12 C10 127.7(4) . . ?
O C12 C13 126.4(4) . . ?
C10 C12 C13 105.9(3) . . ?
C18 C13 C14 122.4(4) . . ?
C18 C13 C12 129.5(4) . . ?
C14 C13 C12 108.1(3) . . ?
C15 C14 C13 118.6(4) . . ?
C15 C14 C9 132.1(4) . . ?
C13 C14 C9 109.3(3) . . ?
C16 C15 C14 119.1(4) . . ?
C15 C16 C17 122.6(4) . . ?
C16 C17 C18 118.5(4) . . ?
C16 C17 C19 120.4(4) . . ?
C18 C17 C19 121.0(4) . . ?
C13 C18 C17 118.8(4) . . ?
C20 C19 C17 127.8(4) . . ?
C20 C19 S23 111.2(3) . . ?
C17 C19 S23 121.0(3) . . ?
C21 C20 C19 108.1(4) . . ?
C22 C21 C20 116.3(4) . . ?
C21 C22 S23 111.4(4) . . ?

_refine_diff_density_max         0.270
_refine_diff_density_min         -0.308
_refine_diff_density_rms         0.058