# Supplementary Material (ESI) for New Journal of Chemistry
# This journal is © The Royal Society of Chemistry and 
# The Centre National de la Recherche Scientifique, 2008

data_global

_journal_coden_Cambridge         440
_journal_volume                  ?
_journal_page_first              ?
_journal_year                    ?

loop_
_publ_author_name
'Pierre Frere'
'Magali Allain'
'Philippe Blanchard'
'Noemie Hergue'
'Philippe Leriche'
'J Roncali'

_publ_contact_author_name        'Pierre Frere'
_publ_contact_author_email       PIERRE.FRERE@UNIV-ANGERS.FR

_publ_section_title              
;
Evidences for the contribution of sulfur -
bromine intramolecular interactions to the
self-rigidification of thiophene-based pi-conjugated systems
;

# Attachment 'B802313A_Rev_Compound_2.cif'

#\#CIF_1.1

# CIF produced by WinGX routine CIF_UPDATE
# Created on 2008-03-10 at 16:24:06
# Using CIFtbx version 2.6.2 16 Jun 1998

# Dictionary name : cif_core.dic
# Dictionary vers : 2.3
# Request file : c:\program files\wingx\files\cifdoc.dat
# CIF files read : nh933 absorb struct

#------------------ SECTION 1. GLOBAL INFORMATION ---------------------------#

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

data_nh933
_database_code_depnum_ccdc_archive 'CCDC 683797'

_audit_creation_date             2008-03-10T16:24:06-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

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

_chemical_formula_moiety         'C10 H7 Br1 O2 S2'
_chemical_formula_sum            'C10 H7 Br O2 S2'
_chemical_formula_weight         303.19
_chemical_absolute_configuration ad

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

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'

_cell_length_a                   4.1115(4)
_cell_length_b                   14.688(1)
_cell_length_c                   17.247(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1041.54(17)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    5571
_cell_measurement_theta_min      2.4
_cell_measurement_theta_max      25.95

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

_exptl_crystal_description       needle
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.77
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.14
_exptl_crystal_density_diffrn    1.933
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             600
_exptl_absorpt_coefficient_mu    4.32
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_correction_T_min  0.3902
_exptl_absorpt_correction_T_max  0.5689
_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  'STOE IPDS'
_diffrn_measurement_method       'Oscillation Phi Incr 1.3 deg'
_diffrn_detector_area_resol_mean 6.66
_diffrn_reflns_number            6104
_diffrn_reflns_av_R_equivalents  0.0427
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         2.36
_diffrn_reflns_theta_max         26.02
_diffrn_reflns_theta_full        26.02
_diffrn_measured_fraction_theta_max 0.975
_diffrn_measured_fraction_theta_full 0.975
_reflns_number_total             1988
_reflns_number_gt                1737
_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 3.1 (Crystal Impact GbR 2005)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'

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

_refine_special_details          
;
The restraints with DFIX command have been applied to two C-H distances in the
molecule. In fact, the H were found by Fourier difference synthesis and the
C1-H1 distance was equal to 0.84(2)Angstrom and the C8-H8 distance was equal
to 1.13(2)Angstrom during refinement: the C1-H1 and C8-H8 distances were
constrained to dC-H=0.93(2)Angstrom to be in agreement with calculated values.
;
_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^)+(0.0474P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     none
_refine_ls_number_reflns         1988
_refine_ls_number_parameters     164
_refine_ls_number_restraints     2
_refine_ls_R_factor_gt           0.0292
_refine_ls_wR_factor_ref         0.0721
_refine_ls_goodness_of_fit_ref   0.978
_refine_ls_restrained_S_all      0.978
_refine_ls_shift/su_max          0
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.020(11)
_refine_diff_density_max         0.477
_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'
Br Br -0.2901 2.4595 '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 0.9197(12) 0.6080(3) 0.5529(2) 0.0500(9) Uani 1 d D . .
C2 C 0.8769(12) 0.5183(3) 0.5616(2) 0.0471(9) Uani 1 d . . .
C3 C 0.7053(9) 0.4801(2) 0.4982(2) 0.0422(7) Uani 1 d . . .
C4 C 0.6144(10) 0.5413(2) 0.44178(18) 0.0360(7) Uani 1 d . . .
C5 C 0.4402(9) 0.5298(2) 0.36949(19) 0.0355(8) Uani 1 d . . .
C6 C 0.3621(10) 0.5957(2) 0.31663(19) 0.0372(7) Uani 1 d . . .
C7 C 0.1913(10) 0.5631(3) 0.2507(2) 0.0425(9) Uani 1 d . . .
C8 C 0.1387(12) 0.4724(3) 0.2528(2) 0.0475(9) Uani 1 d D . .
C9 C 0.2544(14) 0.7434(3) 0.2735(2) 0.0468(9) Uani 1 d . . .
C10 C 0.2513(15) 0.7057(3) 0.1934(2) 0.0534(10) Uani 1 d . . .
O1 O 0.4441(7) 0.68536(16) 0.32530(15) 0.0451(6) Uani 1 d . . .
O2 O 0.0905(8) 0.61903(19) 0.19176(15) 0.0524(7) Uani 1 d . . .
S1 S 0.7545(3) 0.64903(6) 0.46874(5) 0.0442(2) Uani 1 d . . .
S2 S 0.2906(3) 0.42548(6) 0.33673(6) 0.0457(2) Uani 1 d . . .
Br Br 0.61021(11) 0.35458(2) 0.49612(2) 0.05363(14) Uani 1 d . . .
H1 H 1.037(11) 0.648(3) 0.583(2) 0.074(15) Uiso 1 d D . .
H2 H 0.970(10) 0.480(3) 0.603(2) 0.041(11) Uiso 1 d . . .
H8 H 0.031(12) 0.437(3) 0.215(2) 0.084(18) Uiso 1 d D . .
H9A H 0.376(11) 0.799(3) 0.273(2) 0.044(11) Uiso 1 d . . .
H9B H 0.045(13) 0.746(3) 0.295(3) 0.050(13) Uiso 1 d . . .
H10A H 0.445(12) 0.690(3) 0.179(3) 0.052(14) Uiso 1 d . . .
H10B H 0.113(13) 0.747(3) 0.156(3) 0.068(15) Uiso 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 0.057(3) 0.052(2) 0.0409(17) -0.0066(16) -0.0021(18) -0.001(2)
C2 0.055(3) 0.046(2) 0.0402(18) -0.0001(15) -0.0036(17) 0.001(2)
C3 0.045(2) 0.0387(16) 0.0425(16) 0.0028(16) 0.0090(18) 0.0025(14)
C4 0.037(2) 0.0303(16) 0.0407(16) -0.0016(12) 0.0092(15) 0.0025(15)
C5 0.036(2) 0.0265(15) 0.0439(16) -0.0040(12) 0.0089(14) -0.0022(15)
C6 0.039(2) 0.0309(16) 0.0413(16) 0.0008(13) 0.0018(14) -0.0005(14)
C7 0.041(2) 0.0420(19) 0.0441(18) -0.0004(15) 0.0025(15) -0.0024(17)
C8 0.051(3) 0.043(2) 0.0484(19) -0.0074(16) -0.0010(18) -0.0057(18)
C9 0.052(3) 0.0310(19) 0.057(2) 0.0096(15) 0.002(2) 0.0000(19)
C10 0.063(3) 0.044(2) 0.054(2) 0.0107(18) -0.002(2) -0.002(2)
O1 0.0571(18) 0.0288(12) 0.0493(14) 0.0050(10) -0.0047(12) -0.0041(12)
O2 0.0626(19) 0.0434(14) 0.0512(13) 0.0061(11) -0.0133(14) -0.0020(14)
S1 0.0530(5) 0.0330(4) 0.0468(4) -0.0031(3) -0.0001(4) -0.0021(4)
S2 0.0556(7) 0.0297(4) 0.0518(5) -0.0027(4) 0.0016(4) -0.0043(4)
Br 0.0721(3) 0.03393(19) 0.0549(2) 0.00712(18) 0.0038(2) 0.00078(17)

#------------------ 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 1.338(6) . ?
C1 S1 1.712(4) . ?
C1 H1 0.921(19) . ?
C2 C3 1.417(6) . ?
C2 H2 0.99(4) . ?
C3 C4 1.377(5) . ?
C3 Br 1.885(3) . ?
C4 C5 1.448(5) . ?
C4 S1 1.746(4) . ?
C5 C6 1.368(5) . ?
C5 S2 1.745(3) . ?
C6 O1 1.368(4) . ?
C6 C7 1.420(5) . ?
C7 C8 1.350(6) . ?
C7 O2 1.371(5) . ?
C8 S2 1.721(4) . ?
C8 H8 0.95(2) . ?
C9 O1 1.461(5) . ?
C9 C10 1.489(6) . ?
C9 H9A 0.96(5) . ?
C9 H9B 0.94(5) . ?
C10 O2 1.434(5) . ?
C10 H10A 0.87(5) . ?
C10 H10B 1.05(5) . ?

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 113.0(3) . . ?
C2 C1 H1 130(3) . . ?
S1 C1 H1 117(3) . . ?
C1 C2 C3 111.6(4) . . ?
C1 C2 H2 126(2) . . ?
C3 C2 H2 122(2) . . ?
C4 C3 C2 115.0(3) . . ?
C4 C3 Br 124.7(3) . . ?
C2 C3 Br 120.3(3) . . ?
C3 C4 C5 131.8(3) . . ?
C3 C4 S1 108.3(3) . . ?
C5 C4 S1 119.9(2) . . ?
C6 C5 C4 127.4(3) . . ?
C6 C5 S2 108.8(3) . . ?
C4 C5 S2 123.8(3) . . ?
C5 C6 O1 123.4(3) . . ?
C5 C6 C7 114.3(3) . . ?
O1 C6 C7 122.3(3) . . ?
C8 C7 O2 124.3(4) . . ?
C8 C7 C6 113.0(3) . . ?
O2 C7 C6 122.8(3) . . ?
C7 C8 S2 111.1(3) . . ?
C7 C8 H8 127(4) . . ?
S2 C8 H8 122(4) . . ?
O1 C9 C10 110.7(4) . . ?
O1 C9 H9A 103(3) . . ?
C10 C9 H9A 108(2) . . ?
O1 C9 H9B 106(3) . . ?
C10 C9 H9B 112(3) . . ?
H9A C9 H9B 117(4) . . ?
O2 C10 C9 110.7(3) . . ?
O2 C10 H10A 100(3) . . ?
C9 C10 H10A 111(3) . . ?
O2 C10 H10B 104(3) . . ?
C9 C10 H10B 111(3) . . ?
H10A C10 H10B 118(4) . . ?
C6 O1 C9 111.3(3) . . ?
C7 O2 C10 112.2(3) . . ?
C1 S1 C4 92.15(19) . . ?
C8 S2 C5 92.80(19) . . ?