# Supplementary Material (ESI) for Chemical Communications
# This journal is (c) The Royal Society of Chemistry 2010

data_global
_journal_name_full               Chem.Commun.

_journal_coden_Cambridge         0182
_journal_volume                  ?
_journal_page_first              ?
_journal_year                    ?

_publ_contact_author_name        'Singh, Kamaljit'
_publ_contact_author_email       kamaljit19in@yahoo.co.in

_publ_section_title              
;
New Sulphur Bridged Neutral Annulenes. Structure,
Physical Properties and Applications in Organic Field-Effect Transistors
;
loop_
_publ_author_name
K.Singh
A.Sharma
J.Zhang
W.Xu
D.Zhu

# Attachment '- gnu040.cif'

data_gnu040
_database_code_depnum_ccdc_archive 'CCDC 747545'
#TrackingRef '- gnu040.cif'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C34 H22 S4'
_chemical_formula_weight         558.76

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 0.0000 0.0000 '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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   'C 2/m'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z'
'-x, -y, -z'
'x, -y, z'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z'

_cell_length_a                   10.8683(3)
_cell_length_b                   20.9734(5)
_cell_length_c                   5.9459(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 98.702(3)
_cell_angle_gamma                90.00
_cell_volume                     1339.74(7)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    3169
_cell_measurement_theta_min      3.4579
_cell_measurement_theta_max      32.6400

_exptl_crystal_description       block
_exptl_crystal_colour            black
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.13
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.385
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             580
_exptl_absorpt_coefficient_mu    0.378
_exptl_absorpt_correction_T_min  0.9181
_exptl_absorpt_correction_T_max  0.9525
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.31.7 (release 18-10-2006 CrysAlis171 .NET)
(compiled Oct 18 2006,16:28:17)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'OXFORD DIFFRACTION XCALIBUR-S'
_diffrn_measurement_method       \w/q-scan
_diffrn_detector_area_resol_mean 15.9948
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            4668
_diffrn_reflns_av_R_equivalents  0.0271
_diffrn_reflns_av_sigmaI/netI    0.0268
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_theta_min         3.47
_diffrn_reflns_theta_max         25.00
_reflns_number_total             1214
_reflns_number_gt                1026
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrysAlis CCD, Oxford Diffraction Ltd.,'
_computing_cell_refinement       'CrysAlis RED, Oxford Diffraction Ltd.,'
_computing_data_reduction        'CrysAlis RED, Oxford Diffraction Ltd.,'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    Ortep3
_computing_publication_material  Shelx97

_refine_special_details          
;
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness 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 threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) 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
_refine_ls_weighting_details     
'calc w=1/[\s^2^(Fo^2^)+(0.0411P)^2^+0.2463P] 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    riding
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         1214
_refine_ls_number_parameters     92
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0391
_refine_ls_R_factor_gt           0.0295
_refine_ls_wR_factor_ref         0.0714
_refine_ls_wR_factor_gt          0.0695
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_restrained_S_all      1.055
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_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_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.91151(4) 0.07413(2) 0.27848(7) 0.02245(16) Uani 1 1 d . . .
C1 C 0.76907(17) 0.03305(8) -0.1355(3) 0.0244(4) Uani 1 1 d . . .
C2 C 0.81943(16) 0.08149(8) 0.0128(3) 0.0215(4) Uani 1 1 d . . .
C3 C 0.80300(17) 0.14676(8) -0.0397(3) 0.0247(4) Uani 1 1 d . . .
H3 H 0.7550 0.1614 -0.1769 0.030 Uiso 1 1 calc R . .
C4 C 0.86149(16) 0.18731(8) 0.1222(3) 0.0235(4) Uani 1 1 d . . .
H4 H 0.8571 0.2324 0.1073 0.028 Uiso 1 1 calc R . .
C5 C 0.92881(16) 0.15663(8) 0.3129(3) 0.0211(4) Uani 1 1 d . . .
C6 C 1.0000 0.18674(11) 0.5000 0.0209(5) Uani 1 2 d S . .
C7 C 1.0000 0.25816(11) 0.5000 0.0206(5) Uani 1 2 d S . .
C8 C 1.07740(18) 0.29213(9) 0.3781(3) 0.0293(4) Uani 1 1 d . . .
H8 H 1.1314 0.2698 0.2939 0.035 Uiso 1 1 calc R . .
C9 C 1.07697(19) 0.35815(9) 0.3774(3) 0.0324(5) Uani 1 1 d . . .
H9 H 1.1299 0.3808 0.2921 0.039 Uiso 1 1 calc R . .
C10 C 1.0000 0.39097(12) 0.5000 0.0282(6) Uani 1 2 d S . .
H10 H 1.0000 0.4363 0.5000 0.034 Uiso 1 2 calc SR . .
H1 H 0.7215(17) 0.0506(8) -0.270(3) 0.024(5) Uiso 1 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
S1 0.0268(3) 0.0147(2) 0.0236(2) 0.00026(19) -0.00361(17) 0.00074(19)
C1 0.0251(10) 0.0232(9) 0.0225(9) 0.0022(8) -0.0044(7) 0.0014(8)
C2 0.0214(9) 0.0197(9) 0.0227(9) 0.0012(7) 0.0012(7) 0.0020(7)
C3 0.0282(10) 0.0210(10) 0.0232(9) 0.0044(7) -0.0011(8) 0.0021(7)
C4 0.0273(10) 0.0157(9) 0.0270(9) 0.0029(7) 0.0031(8) 0.0020(7)
C5 0.0230(10) 0.0165(9) 0.0243(9) 0.0012(7) 0.0052(8) 0.0012(7)
C6 0.0208(13) 0.0197(13) 0.0230(12) 0.000 0.0054(10) 0.000
C7 0.0249(13) 0.0161(12) 0.0194(12) 0.000 -0.0016(10) 0.000
C8 0.0341(11) 0.0223(10) 0.0333(10) -0.0036(8) 0.0108(8) -0.0020(8)
C9 0.0374(12) 0.0216(10) 0.0390(11) 0.0026(8) 0.0085(9) -0.0081(8)
C10 0.0310(15) 0.0153(13) 0.0350(15) 0.000 -0.0060(12) 0.000

_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 1.7442(18) . ?
S1 C5 1.7492(18) . ?
C1 C1 1.386(3) 6 ?
C1 C2 1.401(2) . ?
C1 H1 0.959(19) . ?
C2 C3 1.409(2) . ?
C3 C4 1.367(2) . ?
C3 H3 0.9500 . ?
C4 C5 1.409(2) . ?
C4 H4 0.9500 . ?
C5 C6 1.405(2) . ?
C6 C5 1.405(2) 2_756 ?
C6 C7 1.498(3) . ?
C7 C8 1.388(2) 2_756 ?
C7 C8 1.388(2) . ?
C8 C9 1.385(3) . ?
C8 H8 0.9500 . ?
C9 C10 1.375(2) . ?
C9 H9 0.9500 . ?
C10 C9 1.375(2) 2_756 ?
C10 H10 0.9500 . ?

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 93.16(8) . . ?
C1 C1 C2 136.48(10) 6 . ?
C1 C1 H1 112.6(11) 6 . ?
C2 C1 H1 110.9(11) . . ?
C1 C2 C3 122.72(16) . . ?
C1 C2 S1 128.44(13) . . ?
C3 C2 S1 108.83(13) . . ?
C4 C3 C2 114.73(16) . . ?
C4 C3 H3 122.6 . . ?
C2 C3 H3 122.6 . . ?
C3 C4 C5 114.35(16) . . ?
C3 C4 H4 122.8 . . ?
C5 C4 H4 122.8 . . ?
C6 C5 C4 126.07(17) . . ?
C6 C5 S1 125.01(15) . . ?
C4 C5 S1 108.91(13) . . ?
C5 C6 C5 126.6(2) . 2_756 ?
C5 C6 C7 116.71(12) . . ?
C5 C6 C7 116.71(12) 2_756 . ?
C8 C7 C8 118.2(2) 2_756 . ?
C8 C7 C6 120.90(11) 2_756 . ?
C8 C7 C6 120.90(11) . . ?
C9 C8 C7 120.86(17) . . ?
C9 C8 H8 119.6 . . ?
C7 C8 H8 119.6 . . ?
C10 C9 C8 120.09(18) . . ?
C10 C9 H9 120.0 . . ?
C8 C9 H9 120.0 . . ?
C9 C10 C9 119.9(2) 2_756 . ?
C9 C10 H10 120.1 2_756 . ?
C9 C10 H10 120.1 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C1 C1 C2 C3 179.33(10) 6 . . . ?
C1 C1 C2 S1 0.8(2) 6 . . . ?
C5 S1 C2 C1 177.75(16) . . . . ?
C5 S1 C2 C3 -0.98(13) . . . . ?
C1 C2 C3 C4 -178.31(16) . . . . ?
S1 C2 C3 C4 0.51(19) . . . . ?
C2 C3 C4 C5 0.4(2) . . . . ?
C3 C4 C5 C6 178.07(13) . . . . ?
C3 C4 C5 S1 -1.13(19) . . . . ?
C2 S1 C5 C6 -178.02(13) . . . . ?
C2 S1 C5 C4 1.19(13) . . . . ?
C4 C5 C6 C5 -177.48(18) . . . 2_756 ?
S1 C5 C6 C5 1.60(8) . . . 2_756 ?
C4 C5 C6 C7 2.52(18) . . . . ?
S1 C5 C6 C7 -178.40(8) . . . . ?
C5 C6 C7 C8 98.17(12) . . . 2_756 ?
C5 C6 C7 C8 -81.83(12) 2_756 . . 2_756 ?
C5 C6 C7 C8 -81.83(12) . . . . ?
C5 C6 C7 C8 98.17(12) 2_756 . . . ?
C8 C7 C8 C9 -0.27(14) 2_756 . . . ?
C6 C7 C8 C9 179.73(14) . . . . ?
C7 C8 C9 C10 0.5(3) . . . . ?
C8 C9 C10 C9 -0.26(14) . . . 2_756 ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.251
_refine_diff_density_min         -0.228
_refine_diff_density_rms         0.046