Supplementary Material (ESI) for Organic & Biomolecular Chemistry
  This journal is (c) The Royal Society of Chemistry 2007



data_global

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

_audit_creation_date             2007-03-16
_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             ?

#------------------ SUBMISSION DETAILS --------------------------------------#

# Name and address of author for correspondence

_publ_contact_author_name        'Pierre Frere'
_publ_contact_author_address     
;
Laboratoire CIMMA UMR CNRS 6200
2, bd Lavoisier
49045 Angers cedex
France

;
_publ_contact_author_email       pierre.frere@univ-angers.fr
_publ_contact_author_fax         33(0)241735405
_publ_contact_author_phone       33(0)241735063

_journal_coden_Cambridge         177

_publ_requested_journal          'Organic & Biomolecular Chemistry'

_publ_requested_coeditor_name    ?
_publ_contact_letter             # Include date of submission
;
Date of submission ?

Please consider this CIF submission for publication
;
_publ_requested_category         ?

#------------------ PROCESSING SUMMARY (JOURNAL OFFICE ONLY) ----------------#

_journal_name_full               ?
_journal_year                    ?
_journal_volume                  ?
_journal_issue                   ?
_journal_page_first              ?
_journal_page_last               ?

#------------------ TITLE AND AUTHOR LIST------------------------------------#

_publ_section_title              
;
Efficient synthesis of
3,4-alkoxythieno[2,3-b]thiophene derivatives. The first block copolymer
associating 3,4-ethylenedioxythieno[2,3-b]thiophene (EDOThT) and
3,4-ethylenedioxythiophene (EDOT) moieties.
;

_publ_section_title_footnote     
;
?
;

loop_
_publ_author_name
_publ_author_address
'Frere, Pierre'
;
Laboratoire CIMMA UMR CNRS 6200
2, bd Lavoisier
49045 Angers cedex
France
;
'Noemie Hergue' .

#------------------ TEXT ----------------------------------------------------#

_publ_section_synopsis           
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# Insert blank lines between paragraphs
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_publ_section_abstract           
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# Insert blank lines between paragraphs
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_publ_section_comment            
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# Insert blank lines between paragraphs
?
;

_publ_section_exptl_prep         
;
?
;

_publ_section_exptl_refinement   
;
?
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# 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.,
Garci\'ia-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 G\"ottingen, Germany.

Sheldrick, G.M. (1997) SHELXL97. Program for crystal structure
refinement. University of G\"ottingen, 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 G\"ottingen, 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_nannyall
_database_code_depnum_ccdc_archive 'CCDC 656589'

_audit_creation_date             2007-03-16T11:30:45-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

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

_chemical_formula_moiety         'C14 H14 O6 S2'
_chemical_formula_sum            'C14 H14 O6 S2'
_chemical_formula_weight         342.37

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

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
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                   5.0980(10)
_cell_length_b                   14.076(2)
_cell_length_c                   20.831(7)
_cell_angle_alpha                90
_cell_angle_beta                 92.82(2)
_cell_angle_gamma                90
_cell_volume                     1493.0(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    4021
_cell_measurement_theta_min      3.27
_cell_measurement_theta_max      26.01

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

_exptl_crystal_description       plate
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.44
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.01
_exptl_crystal_density_diffrn    1.523
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             712
_exptl_absorpt_coefficient_mu    0.383
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_correction_T_min  0.926
_exptl_absorpt_correction_T_max  0.9962
_exptl_absorpt_process_details   
;
PLATON-ABSGAUSS : Spek, A.L. (2003), J.Appl.Cryst. 36, 7-13
;

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

_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_probe          x-ray
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       CCD
_diffrn_detector_area_resol_mean 9
_diffrn_reflns_number            23632
_diffrn_reflns_av_R_equivalents  0.1745
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         3.27
_diffrn_reflns_theta_max         26.01
_diffrn_reflns_theta_full        26.01
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measured_fraction_theta_full 0.986
_reflns_number_total             2905
_reflns_number_gt                1522
_reflns_threshold_expression     >2sigma(I)

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

_computing_data_collection       'Collect (Nonius BV, 1997-2000)'
_computing_cell_refinement       'Dirax/lsq (Duisenberg & Schreurs, 1989-2000)'
_computing_data_reduction        'EvalCCD (Duisenberg & Schreurs 1990-2000)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'DIAMOND 3.1d (Crystal Impact GbR 2005)'
_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^)+(0.0000P)^2^+4.0451P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         2905
_refine_ls_number_parameters     201
_refine_ls_number_restraints     0
_refine_ls_R_factor_gt           0.0851
_refine_ls_wR_factor_ref         0.1718
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_restrained_S_all      1.064
_refine_ls_shift/su_max          0
_refine_diff_density_max         0.491
_refine_diff_density_min         -0.415

#------------------ 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
C1 C 0.2694(10) 0.1402(4) 0.0229(3) 0.0339(14) Uani 1 d . . .
C2 C 0.2860(10) 0.2353(4) 0.0387(2) 0.0315(13) Uani 1 d . . .
C3 C 0.0930(10) 0.2905(4) 0.0030(3) 0.0340(14) Uani 1 d . . .
C4 C -0.0539(10) 0.2359(4) -0.0400(3) 0.0341(14) Uani 1 d . . .
C5 C -0.2641(11) 0.2692(5) -0.0852(3) 0.0437(16) Uani 1 d . . .
C6 C -0.5532(15) 0.2260(6) -0.1729(4) 0.097(3) Uani 1 d . . .
H6A H -0.7195 0.229 -0.1522 0.117 Uiso 1 calc R . .
H6B H -0.5159 0.2888 -0.1892 0.117 Uiso 1 calc R . .
C7 C -0.574(3) 0.1672(10) -0.2204(5) 0.187(7) Uani 1 d . . .
H7A H -0.4194 0.1704 -0.2447 0.281 Uiso 1 calc R . .
H7B H -0.7251 0.1836 -0.2477 0.281 Uiso 1 calc R . .
H7C H -0.5946 0.1038 -0.2043 0.281 Uiso 1 calc R . .
C8 C 0.4907(10) 0.2519(4) 0.0872(2) 0.0340(13) Uani 1 d . . .
C9 C 0.6140(10) 0.1698(4) 0.1072(3) 0.0370(14) Uani 1 d . . .
C10 C 0.8329(11) 0.1615(5) 0.1553(3) 0.0421(15) Uani 1 d . . .
C11 C 1.1029(14) 0.0475(6) 0.2124(4) 0.073(2) Uani 1 d . . .
H11A H 1.1784 -0.0132 0.2012 0.088 Uiso 1 calc R . .
H11B H 1.2373 0.0957 0.2087 0.088 Uiso 1 calc R . .
C12 C 1.0246(16) 0.0437(7) 0.2790(4) 0.107(3) Uani 1 d . . .
H12A H 0.9537 0.1041 0.2907 0.16 Uiso 1 calc R . .
H12B H 1.175 0.0292 0.3068 0.16 Uiso 1 calc R . .
H12C H 0.8938 -0.0047 0.2831 0.16 Uiso 1 calc R . .
C13 C 0.1657(11) 0.4257(4) 0.0687(3) 0.0499(17) Uani 1 d . . .
H13A H 0.0918 0.3938 0.105 0.06 Uiso 1 calc R . .
H13B H 0.1146 0.492 0.0704 0.06 Uiso 1 calc R . .
C14 C 0.4562(12) 0.4195(4) 0.0757(3) 0.0548(18) Uani 1 d . . .
H14A H 0.525 0.4182 0.0331 0.066 Uiso 1 calc R . .
H14B H 0.5217 0.4768 0.0969 0.066 Uiso 1 calc R . .
O1 O 0.0539(7) 0.3843(3) 0.00991(18) 0.0425(10) Uani 1 d . . .
O2 O 0.5593(7) 0.3382(3) 0.11142(18) 0.0440(10) Uani 1 d . . .
O3 O -0.3531(9) 0.3483(3) -0.0872(2) 0.0612(13) Uani 1 d . . .
O4 O -0.3466(8) 0.1992(3) -0.1251(2) 0.0655(14) Uani 1 d . . .
O5 O 0.9569(9) 0.2254(3) 0.1790(2) 0.0673(14) Uani 1 d . . .
O6 O 0.8818(8) 0.0690(3) 0.1671(2) 0.0567(12) Uani 1 d . . .
S1 S 0.0391(3) 0.11559(10) -0.03772(8) 0.0421(4) Uani 1 d . . .
S2 S 0.4843(3) 0.06939(10) 0.06737(8) 0.0409(4) 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
C1 0.038(3) 0.033(4) 0.031(3) 0.002(3) -0.005(2) 0.002(2)
C2 0.036(3) 0.029(3) 0.029(3) 0.000(3) -0.001(2) -0.001(2)
C3 0.038(3) 0.029(3) 0.035(3) -0.001(3) -0.005(3) 0.004(3)
C4 0.035(3) 0.032(3) 0.033(3) -0.002(3) -0.007(3) 0.004(2)
C5 0.044(4) 0.047(4) 0.040(4) -0.004(3) -0.005(3) 0.006(3)
C6 0.079(6) 0.097(7) 0.109(7) -0.053(6) -0.072(5) 0.033(5)
C7 0.199(13) 0.244(16) 0.108(9) -0.057(10) -0.091(9) 0.136(12)
C8 0.040(3) 0.036(4) 0.025(3) -0.001(3) -0.004(2) -0.007(3)
C9 0.042(3) 0.032(3) 0.036(3) 0.003(3) -0.007(3) 0.001(3)
C10 0.042(4) 0.041(4) 0.043(4) 0.002(3) 0.000(3) 0.007(3)
C11 0.066(5) 0.083(6) 0.069(6) 0.021(4) -0.024(4) 0.022(4)
C12 0.094(6) 0.167(10) 0.057(6) 0.031(6) -0.018(5) 0.000(6)
C13 0.065(4) 0.033(3) 0.049(4) -0.014(3) -0.016(3) 0.008(3)
C14 0.062(4) 0.029(4) 0.071(5) -0.004(3) -0.026(3) 0.004(3)
O1 0.057(2) 0.027(2) 0.041(3) -0.0047(19) -0.0170(19) 0.0089(19)
O2 0.050(2) 0.036(2) 0.044(3) -0.004(2) -0.0175(19) -0.0004(19)
O3 0.069(3) 0.047(3) 0.064(3) -0.005(2) -0.027(2) 0.017(2)
O4 0.066(3) 0.065(3) 0.061(3) -0.025(3) -0.036(2) 0.014(2)
O5 0.066(3) 0.061(3) 0.071(3) 0.006(3) -0.031(3) -0.011(3)
O6 0.059(3) 0.052(3) 0.056(3) 0.008(2) -0.020(2) 0.012(2)
S1 0.0429(9) 0.0349(9) 0.0468(10) -0.0074(8) -0.0134(7) 0.0031(7)
S2 0.0438(9) 0.0308(9) 0.0469(10) 0.0009(7) -0.0091(7) 0.0031(7)

#------------------ 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 1.380(7) . ?
C1 S1 1.716(5) . ?
C1 S2 1.719(5) . ?
C2 C3 1.433(7) . ?
C2 C8 1.436(7) . ?
C3 O1 1.345(6) . ?
C3 C4 1.374(7) . ?
C4 C5 1.468(7) . ?
C4 S1 1.758(5) . ?
C5 O3 1.201(7) . ?
C5 O4 1.343(7) . ?
C6 C7 1.292(12) . ?
C6 O4 1.462(7) . ?
C8 O2 1.354(6) . ?
C8 C9 1.370(7) . ?
C9 C10 1.467(8) . ?
C9 S2 1.752(6) . ?
C10 O5 1.193(7) . ?
C10 O6 1.346(7) . ?
C11 C12 1.462(10) . ?
C11 O6 1.467(7) . ?
C13 O1 1.448(6) . ?
C13 C14 1.484(8) . ?
C14 O2 1.450(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 C1 S1 113.8(4) . . ?
C2 C1 S2 113.8(4) . . ?
S1 C1 S2 132.4(3) . . ?
C1 C2 C3 111.7(4) . . ?
C1 C2 C8 111.1(5) . . ?
C3 C2 C8 137.2(5) . . ?
O1 C3 C4 122.7(5) . . ?
O1 C3 C2 125.3(5) . . ?
C4 C3 C2 111.9(5) . . ?
C3 C4 C5 126.6(5) . . ?
C3 C4 S1 112.5(4) . . ?
C5 C4 S1 120.9(4) . . ?
O3 C5 O4 123.5(5) . . ?
O3 C5 C4 125.5(6) . . ?
O4 C5 C4 111.0(5) . . ?
C7 C6 O4 112.8(7) . . ?
O2 C8 C9 122.5(4) . . ?
O2 C8 C2 125.0(5) . . ?
C9 C8 C2 112.5(5) . . ?
C8 C9 C10 126.6(5) . . ?
C8 C9 S2 112.3(4) . . ?
C10 C9 S2 121.1(4) . . ?
O5 C10 O6 124.3(5) . . ?
O5 C10 C9 126.4(6) . . ?
O6 C10 C9 109.2(5) . . ?
C12 C11 O6 112.4(6) . . ?
O1 C13 C14 114.1(5) . . ?
O2 C14 C13 115.5(5) . . ?
C3 O1 C13 115.6(4) . . ?
C8 O2 C14 115.9(4) . . ?
C5 O4 C6 115.2(5) . . ?
C10 O6 C11 116.6(5) . . ?
C1 S1 C4 90.0(3) . . ?
C1 S2 C9 90.2(3) . . ?