# Supplementary Material (ESI) for Chemical Communications
# This journal is © The Royal Society of Chemistry 2005

data_global

#------------------ AUDIT DETAILS -------------------------------------------#

_audit_creation_date             2005-07-04
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.3
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic
_audit_update_record             ?

_journal_coden_Cambridge         182

loop_
_publ_author_name
'Philippe Leriche'
'Philippe Blanchard'
'Pierre Frere'
'Eric Levillain'
'Gilles Mabon'
'J. Roncali'

_publ_contact_author_name        'Philippe Leriche'
_publ_contact_author_address     
;
Groupe Systemes Conjugues Lineaires, CIMMA UMR CNRS 6200
Universite d'Angers
UFR Sciences,
2, Bd Lavoisier
Angers
49045
FRANCE
;

_publ_contact_author_email       PHILIPPE.LERICHE@UNIV-ANGERS.FR

_publ_requested_journal          'Chemical Communications'

_publ_section_title              
;
3,4-Vinylenedioxythiophene (VDOT):
a new building block for thiophene-based pi-conjugated systems
;

# Insert blank lines between references

_publ_section_references         
;
Allen, F.H., Kennard, O. & Taylor, R. (1983).
Acc. Chem. Res. 16, 146-153.

Altomare, A., Cascarano, G., Giacovazzo, C. & Guagliardi, A.
(1993) J. Appl. Cryst. 26, 343-350.

Altomare, A. Burla, M. C., Camalli, M., Cascarano, G. L.,
Giacovazzo, C., Guagliardi, A., Moliterni, A. G. G., Polidori, G.
& Spagna, R. (1999) J. Appl. Cryst. 32, 115-119.

Blessing, R. H. (1995) Acta Cryst., A51, 33-38.

Blessing, R. H. (1987) Cryst. Rev. 1, 3-58.

Blessing, R. H. (1989) J. Appl. Cryst. 22, 396-397.

Beurskens, P.T., Beurskens, G., de Gelder, R.,
Garciia-Granda, S., Gould, R.O., Israel, R. & Smits, J.M.M.
(1999) The DIRDIF-99 program system,
Technical Report of the Crystallography Laboratory,
University of Nijmegen, The Netherlands.

Cremer, D. & Pople, J.A. (1975). J. Am. Chem. Soc. 97, 1354-1358.

Enraf-Nonius (1994). CAD4Express Software. Enraf-Nonius, Delft,
The Netherlands.

Farrugia, L. J. (1997) ORTEP-3 for Windows, J. Appl. Cryst. 30, 565.

Farrugia, L. J. (1999) WinGX, J. Appl. Cryst. 32, 837-838.

Flack, H.D. (1983). Acta Cryst. A39, 876-881.

Harms, K. & Wocadlo, S. (1995) XCAD-4. Program for Processing CAD-4
Diffractometer Data. University of Marburg, Germany.

Johnson, C.K. (1965). ORTEP. Report ORNL-3794. Oak Ridge National
Laboratory, Tennessee, USA.

Lehman, M. S. and Larsen, F. K. (1974) Acta. Cryst. A30, 580

LePage, Y. (1987). J. Appl. Cryst. 20, 264-269.

North, A. C. T., Phillips, D. C. & Mathews, F. S. (1968) Acta Cryst,
A24, 351-359

Orpen, A. G., Brammer, L., Allen, F. H., Kennard, O., Watson, D. G.,
& Taylor, R. (1992). International Tables for Crystallography,
Volume C.

Sheldrick, G.M. (1993) SHELXL93. Program for crystal structure
refinement. University of Gottingen, Germany.

Sheldrick, G.M. (1997) SHELXL97. Program for crystal structure
refinement. University of Gottingen, Germany.

Sheldrick, G.M. (1985). SHELXS86. In Crystallographic Computing 3,
edited by G. M. Sheldrick, C. Kruger & R. Goddard, pp. 175-189.
Oxford University Press.

Sheldrick, G.M. (1997) SHELXS97. Program for Crystal Structure solution.
University of Gottingen, Germany.

Spek, A.L. (1990). Acta Cryst. A46, C34

Streltsov, V. A. & Zavodnik, V. E. (1989) Sov. Phys. Crystallogr.
34, 824-828

Streltsov, V. A. & Zavodnik, V. E. (1990) Sov. Phys. Crystallogr.
35, 281.

Walker, N. & Stuart, D. (1983). Acta Cryst., A39, 158 - 166.

Wilson, A.J.C. (1992) Ed. International Tables for Crystallography,
Volume C, Kluwer Academic Publishers, Dordrecht, The Netherlands.
;
_publ_section_figure_captions    
;
Figure 1. View of (I) (50% probability displacement ellipsoids)
;
_publ_section_acknowledgements   
;
?
;
_publ_section_table_legends      
;
Table 1. Fractional atomic coordinates and equivalent
isotropic displacement parameters (\%A^2^)

Table 2. Selected geometric parameters (\%A ,\% )
;

#------------------ SECTION 2. COMPOUND(S) DETAILS -------------------------#

data_plng16
_database_code_depnum_ccdc_archive 'CCDC 285541'

_audit_creation_date             2005-07-04T13:46:45-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

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

_chemical_formula_moiety         'C6 H3 O2 S1'
_chemical_formula_sum            'C6 H3 O2 S'
_chemical_formula_weight         139.14

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

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_symmetry_space_group_name_Hall  '-P 2yn'
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                   7.0000(10)
_cell_length_b                   4.8894(6)
_cell_length_c                   15.815(3)
_cell_angle_alpha                90
_cell_angle_beta                 94.88(2)
_cell_angle_gamma                90
_cell_volume                     539.32(14)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    3548
_cell_measurement_theta_min      2.6
_cell_measurement_theta_max      25.85

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

_exptl_crystal_description       needle
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.78
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.05
_exptl_crystal_density_diffrn    1.714
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             284
_exptl_absorpt_coefficient_mu    0.495
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8165
_exptl_absorpt_correction_T_max  0.8812
_exptl_absorpt_process_details   
;
[c.f. r.h. blessing, acta cryst. (1995), a51, 33-38]
;

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

_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_probe          x-ray
_diffrn_measurement_device_type  'STOE IPDS'
_diffrn_measurement_method       'Oscillation Phi Incr 1.5 deg'
_diffrn_detector_area_resol_mean 6.66
_diffrn_reflns_number            4988
_diffrn_reflns_av_R_equivalents  0.0789
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.59
_diffrn_reflns_theta_max         26.01
_diffrn_reflns_theta_full        26.01
_diffrn_measured_fraction_theta_max 0.941
_diffrn_measured_fraction_theta_full 0.941
_reflns_number_total             997
_reflns_number_gt                712
_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    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'DIAMOND 3.0d (Crystal Impact GbR 2004)'
_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^)+(0.0479P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     none
_refine_ls_number_reflns         997
_refine_ls_number_parameters     94
_refine_ls_number_restraints     0
_refine_ls_R_factor_gt           0.0446
_refine_ls_wR_factor_ref         0.0963
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_restrained_S_all      1.058
_refine_ls_shift/su_max          0
_refine_diff_density_max         0.276
_refine_diff_density_min         -0.252

#------------------ 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'

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
H04 H 0.792(5) 0.350(7) 0.709(2) 0.046(9) Uiso 1 d . . .
H05 H 0.197(4) 0.805(8) 0.691(2) 0.039(9) Uiso 1 d . . .
H06 H 0.041(5) 0.583(7) 0.572(2) 0.041(9) Uiso 1 d . . .
C01 C 0.5279(3) 0.0826(6) 0.53691(17) 0.0276(6) Uani 1 d . . .
C02 C 0.4233(3) 0.2738(6) 0.57548(17) 0.0277(7) Uani 1 d . . .
C03 C 0.5209(4) 0.3981(7) 0.64687(17) 0.0298(7) Uani 1 d . . .
C04 C 0.6999(4) 0.3014(7) 0.6640(2) 0.0363(7) Uani 1 d . . .
C05 C 0.2527(4) 0.6617(8) 0.6610(2) 0.0383(8) Uani 1 d . . .
C06 C 0.1626(4) 0.5465(7) 0.5948(2) 0.0386(8) Uani 1 d . . .
O01 O 0.4385(3) 0.5978(5) 0.69391(13) 0.0379(5) Uani 1 d . . .
O02 O 0.2381(3) 0.3431(5) 0.54669(14) 0.0379(6) Uani 1 d . . .
S01 S 0.75309(10) 0.05704(18) 0.59217(5) 0.0353(3) Uani 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
C01 0.0255(12) 0.0246(18) 0.0324(14) 0.0006(12) 0.0012(10) -0.0012(11)
C02 0.0261(13) 0.0293(19) 0.0275(14) 0.0024(12) 0.0014(10) -0.0005(11)
C03 0.0335(13) 0.027(2) 0.0284(15) -0.0010(12) 0.0025(11) -0.0019(11)
C04 0.0355(15) 0.036(2) 0.0350(17) -0.0038(14) -0.0080(12) 0.0001(13)
C05 0.0393(15) 0.035(2) 0.0418(18) -0.0022(15) 0.0090(13) 0.0078(14)
C06 0.0313(14) 0.041(2) 0.0443(18) -0.0039(16) 0.0056(13) 0.0090(14)
O01 0.0399(11) 0.0359(15) 0.0374(11) -0.0127(10) 0.0008(9) 0.0040(9)
O02 0.0284(10) 0.0398(15) 0.0441(12) -0.0117(10) -0.0045(8) 0.0106(8)
S01 0.0282(3) 0.0344(5) 0.0418(4) -0.0047(4) -0.0061(3) 0.0061(3)

#------------------ 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
C01 C02 1.363(4) . ?
C01 C01 1.446(6) 3_656 ?
C01 S01 1.740(2) . ?
C02 O02 1.379(3) . ?
C02 C03 1.407(4) . ?
C03 C04 1.346(4) . ?
C03 O01 1.383(4) . ?
C04 S01 1.711(3) . ?
C04 H04 0.95(3) . ?
C05 C06 1.302(5) . ?
C05 O01 1.395(3) . ?
C05 H05 0.95(4) . ?
C06 O02 1.385(4) . ?
C06 H06 0.91(3) . ?

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
C02 C01 C01 128.7(3) . 3_656 ?
C02 C01 S01 108.8(2) . . ?
C01 C01 S01 122.4(3) 3_656 . ?
C01 C02 O02 123.1(2) . . ?
C01 C02 C03 114.4(2) . . ?
O02 C02 C03 122.5(3) . . ?
C04 C03 O01 124.3(3) . . ?
C04 C03 C02 112.9(3) . . ?
O01 C03 C02 122.7(2) . . ?
C03 C04 S01 111.3(2) . . ?
C03 C04 H04 128(2) . . ?
S01 C04 H04 120(2) . . ?
C06 C05 O01 125.1(3) . . ?
C06 C05 H05 122.3(19) . . ?
O01 C05 H05 112.6(19) . . ?
C05 C06 O02 124.8(3) . . ?
C05 C06 H06 127(2) . . ?
O02 C06 H06 108(2) . . ?
C03 O01 C05 112.0(2) . . ?
C02 O02 C06 112.8(2) . . ?
C04 S01 C01 92.54(14) . . ?