# Supplementary Material (ESI) for Chemical Communications
# This journal is (c) The Royal Society of Chemistry 2006

data_global
_journal_name_full               Chem.Commun.

_journal_coden_Cambridge         0182

_publ_contact_author_name        'Yunqi Liu'
_publ_contact_author_address     
;
Institute of Chemistry, Chinese Academy of Sciences
P.O.Box 2709
Beijing
100080
CHINA
;

_publ_contact_author_email       LIUYQ@MAIL.ICCAS.AC.CN

_publ_section_title              
;
A facile synthesis of linear benzene-fused
bis(tetrathiafulvalenes) compounds and their application for organic
field-effect transistors
;
loop_
_publ_author_name
'Yunqi Liu'
'Xike Gao'
'Wenfeng Qiu'
'Xiaobo Sun'
'Weiping Wu'
'Gui Yu'
;
Daoben Zhu
;

data_60301c
_database_code_depnum_ccdc_archive 'CCDC 601019'

_audit_creation_method           SHELXL-97

_chemical_name_systematic        
;

?

;

_chemical_name_common            ?

_chemical_melting_point          ?

_chemical_formula_moiety         ?

_chemical_formula_sum            'C30 H38 S12'

_chemical_formula_weight         783.32

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           Triclinic

_symmetry_space_group_name_H-M   P-1

loop_

_symmetry_equiv_pos_as_xyz

'x, y, z'
'-x, -y, -z'

_cell_length_a                   5.3630(17)

_cell_length_b                   8.920(3)

_cell_length_c                   19.406(6)

_cell_angle_alpha                78.674(5)

_cell_angle_beta                 86.600(6)

_cell_angle_gamma                85.002(5)

_cell_volume                     905.9(5)

_cell_formula_units_Z            1

_cell_measurement_temperature    294(2)

_cell_measurement_reflns_used    2013

_cell_measurement_theta_min      2.34

_cell_measurement_theta_max      26.24

_exptl_crystal_description       ?

_exptl_crystal_colour            ?

_exptl_crystal_size_max          0.30

_exptl_crystal_size_mid          0.08

_exptl_crystal_size_min          0.04

_exptl_crystal_density_meas      NONE

_exptl_crystal_density_diffrn    1.436

_exptl_crystal_density_method    'not measured'

_exptl_crystal_F_000             410

_exptl_absorpt_coefficient_mu    0.745

_exptl_absorpt_correction_type   MULTI-SCAN

_exptl_absorpt_correction_T_min  0.535724

_exptl_absorpt_correction_T_max  1.000000

_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;

?

;

_diffrn_ambient_temperature      294(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_type  'CCD area detector'

_diffrn_measurement_method       'phi and omega scans'

_diffrn_detector_area_resol_mean ?

_diffrn_standards_number         .

_diffrn_standards_interval_count .

_diffrn_standards_interval_time  .

_diffrn_standards_decay_%        .

_diffrn_reflns_number            4569

_diffrn_reflns_av_R_equivalents  0.0240

_diffrn_reflns_av_sigmaI/netI    0.0492

_diffrn_reflns_limit_h_min       -6

_diffrn_reflns_limit_h_max       5

_diffrn_reflns_limit_k_min       -10

_diffrn_reflns_limit_k_max       9

_diffrn_reflns_limit_l_min       -23

_diffrn_reflns_limit_l_max       11

_diffrn_reflns_theta_min         2.34

_diffrn_reflns_theta_max         25.01

_reflns_number_total             3164

_reflns_number_gt                2242

_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'

_computing_cell_refinement       'Bruker SMART'

_computing_data_reduction        'Bruker SAINT'

_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'

_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'

_computing_molecular_graphics    'Bruker SHELXTL'

_computing_publication_material  'Bruker SHELXTL'

_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^)+(0.0393P)^2^+0.7676P] 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    CONSTR

_refine_ls_extinction_method     none

_refine_ls_extinction_coef       ?

_refine_ls_number_reflns         3164

_refine_ls_number_parameters     192

_refine_ls_number_restraints     0

_refine_ls_R_factor_all          0.0702

_refine_ls_R_factor_gt           0.0443

_refine_ls_wR_factor_ref         0.1098

_refine_ls_wR_factor_gt          0.0954

_refine_ls_goodness_of_fit_ref   1.019

_refine_ls_restrained_S_all      1.019

_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 0.53982(16) 0.46984(9) 0.10762(5) 0.0360(2) Uani 1 1 d . . .
S2 S 0.66985(17) 0.78203(10) 0.03769(5) 0.0402(3) Uani 1 1 d . . .
S3 S 0.21137(17) 0.92954(10) 0.12381(5) 0.0416(3) Uani 1 1 d . . .
S4 S 0.07172(16) 0.61993(9) 0.18930(5) 0.0370(2) Uani 1 1 d . . .
S5 S -0.20378(18) 1.08481(10) 0.20065(5) 0.0441(3) Uani 1 1 d . . .
S6 S -0.35200(17) 0.73749(11) 0.27769(5) 0.0437(3) Uani 1 1 d . . .
C1 C 0.9345(6) 0.3529(4) 0.03157(17) 0.0302(7) Uani 1 1 d . . .
H1 H 0.8901 0.2550 0.0521 0.036 Uiso 1 1 calc R . .
C2 C 0.7998(6) 0.4803(4) 0.04775(17) 0.0303(8) Uani 1 1 d . . .
C3 C 0.8627(6) 0.6275(4) 0.01569(17) 0.0308(8) Uani 1 1 d . . .
C4 C 0.4726(6) 0.6692(4) 0.09812(17) 0.0317(8) Uani 1 1 d . . .
C5 C 0.2822(6) 0.7309(4) 0.13323(17) 0.0318(8) Uani 1 1 d . . .
C6 C -0.0336(6) 0.9157(4) 0.18846(18) 0.0338(8) Uani 1 1 d . . .
C7 C -0.0951(6) 0.7745(4) 0.21851(17) 0.0321(8) Uani 1 1 d . . .
C8 C 0.0359(7) 1.1934(4) 0.2245(2) 0.0487(10) Uani 1 1 d . . .
H8A H 0.1690 1.2005 0.1882 0.058 Uiso 1 1 calc R . .
H8B H -0.0356 1.2967 0.2255 0.058 Uiso 1 1 calc R . .
C9 C 0.1487(8) 1.1278(5) 0.2946(2) 0.0540(11) Uani 1 1 d . . .
H9A H 0.0147 1.1064 0.3301 0.065 Uiso 1 1 calc R . .
H9B H 0.2437 1.0314 0.2916 0.065 Uiso 1 1 calc R . .
C10 C 0.3185(8) 1.2339(5) 0.3173(3) 0.0619(12) Uani 1 1 d . . .
H10A H 0.4487 1.2583 0.2809 0.074 Uiso 1 1 calc R . .
H10B H 0.2219 1.3288 0.3219 0.074 Uiso 1 1 calc R . .
C11 C 0.4392(11) 1.1675(7) 0.3856(3) 0.0988(19) Uani 1 1 d . . .
H11A H 0.3118 1.1449 0.4222 0.148 Uiso 1 1 calc R . .
H11B H 0.5437 1.2403 0.3972 0.148 Uiso 1 1 calc R . .
H11C H 0.5393 1.0751 0.3812 0.148 Uiso 1 1 calc R . .
C12 C -0.2208(8) 0.5804(4) 0.3425(2) 0.0518(11) Uani 1 1 d . . .
H12A H -0.3522 0.5469 0.3772 0.062 Uiso 1 1 calc R . .
H12B H -0.1678 0.4953 0.3193 0.062 Uiso 1 1 calc R . .
C13 C -0.0009(8) 0.6157(5) 0.3806(2) 0.0636(12) Uani 1 1 d . . .
H13A H 0.0706 0.5207 0.4082 0.076 Uiso 1 1 calc R . .
H13B H 0.1265 0.6557 0.3459 0.076 Uiso 1 1 calc R . .
C14 C -0.0635(10) 0.7267(7) 0.4277(3) 0.0845(16) Uani 1 1 d . . .
H14A H -0.1911 0.6873 0.4624 0.101 Uiso 1 1 calc R . .
H14B H -0.1330 0.8224 0.4002 0.101 Uiso 1 1 calc R . .
C15 C 0.1623(11) 0.7581(8) 0.4653(3) 0.108(2) Uani 1 1 d . . .
H15A H 0.2349 0.6634 0.4915 0.162 Uiso 1 1 calc R . .
H15B H 0.1098 0.8265 0.4968 0.162 Uiso 1 1 calc R . .
H15C H 0.2842 0.8042 0.4313 0.162 Uiso 1 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 0.0351(5) 0.0319(5) 0.0399(6) -0.0066(4) 0.0092(4) -0.0041(4)
S2 0.0431(6) 0.0309(5) 0.0440(6) -0.0055(4) 0.0129(4) -0.0020(4)
S3 0.0429(6) 0.0307(5) 0.0489(6) -0.0051(4) 0.0147(4) -0.0061(4)
S4 0.0384(5) 0.0280(5) 0.0441(6) -0.0078(4) 0.0103(4) -0.0059(4)
S5 0.0412(6) 0.0332(5) 0.0578(7) -0.0127(4) 0.0048(5) 0.0018(4)
S6 0.0317(5) 0.0518(6) 0.0432(6) -0.0017(4) 0.0085(4) -0.0036(4)
C1 0.0338(19) 0.0294(17) 0.0277(19) -0.0045(14) 0.0000(14) -0.0077(14)
C2 0.0299(18) 0.0345(18) 0.0268(19) -0.0062(14) 0.0012(14) -0.0050(14)
C3 0.0328(19) 0.0302(17) 0.0300(19) -0.0074(14) -0.0026(15) -0.0008(14)
C4 0.0339(19) 0.0326(18) 0.0282(19) -0.0042(14) 0.0003(15) -0.0054(14)
C5 0.0320(19) 0.0296(17) 0.033(2) -0.0054(14) 0.0029(15) -0.0037(14)
C6 0.0314(19) 0.0316(18) 0.038(2) -0.0085(15) 0.0046(15) -0.0024(14)
C7 0.0323(19) 0.0349(18) 0.0292(19) -0.0074(15) 0.0027(15) -0.0039(15)
C8 0.056(3) 0.031(2) 0.062(3) -0.0169(18) 0.004(2) -0.0056(17)
C9 0.054(3) 0.050(2) 0.059(3) -0.017(2) 0.004(2) -0.003(2)
C10 0.058(3) 0.059(3) 0.076(3) -0.036(2) -0.001(2) 0.004(2)
C11 0.089(4) 0.118(5) 0.095(5) -0.025(4) -0.022(4) -0.015(4)
C12 0.059(3) 0.048(2) 0.044(3) 0.0000(19) 0.010(2) -0.0077(19)
C13 0.056(3) 0.078(3) 0.049(3) 0.004(2) 0.000(2) 0.000(2)
C14 0.073(4) 0.104(4) 0.082(4) -0.029(3) -0.004(3) -0.012(3)
C15 0.093(5) 0.149(6) 0.092(5) -0.032(4) -0.024(4) -0.030(4)

_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 1.758(3) . ?
S1 C4 1.759(3) . ?
S2 C4 1.756(3) . ?
S2 C3 1.756(3) . ?
S3 C5 1.755(3) . ?
S3 C6 1.757(3) . ?
S4 C7 1.747(3) . ?
S4 C5 1.750(3) . ?
S5 C6 1.743(3) . ?
S5 C8 1.808(4) . ?
S6 C7 1.752(3) . ?
S6 C12 1.812(4) . ?
C1 C2 1.372(4) . ?
C1 C3 1.381(4) 2_765 ?
C1 H1 0.9300 . ?
C2 C3 1.399(4) . ?
C3 C1 1.381(4) 2_765 ?
C4 C5 1.333(5) . ?
C6 C7 1.341(4) . ?
C8 C9 1.511(5) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 C10 1.510(5) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 C11 1.501(7) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C12 C13 1.515(6) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 C14 1.480(7) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C14 C15 1.525(7) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?

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 C4 95.74(15) . . ?
C4 S2 C3 95.69(16) . . ?
C5 S3 C6 95.19(15) . . ?
C7 S4 C5 95.49(15) . . ?
C6 S5 C8 102.18(17) . . ?
C7 S6 C12 101.51(17) . . ?
C2 C1 C3 118.8(3) . 2_765 ?
C2 C1 H1 120.6 . . ?
C3 C1 H1 120.6 2_765 . ?
C1 C2 C3 120.7(3) . . ?
C1 C2 S1 123.0(2) . . ?
C3 C2 S1 116.4(2) . . ?
C1 C3 C2 120.5(3) 2_765 . ?
C1 C3 S2 122.7(2) 2_765 . ?
C2 C3 S2 116.8(2) . . ?
C5 C4 S2 122.1(3) . . ?
C5 C4 S1 122.5(3) . . ?
S2 C4 S1 115.39(19) . . ?
C4 C5 S4 122.6(3) . . ?
C4 C5 S3 123.0(3) . . ?
S4 C5 S3 114.29(19) . . ?
C7 C6 S5 124.6(3) . . ?
C7 C6 S3 117.1(3) . . ?
S5 C6 S3 117.76(18) . . ?
C6 C7 S4 117.4(3) . . ?
C6 C7 S6 123.8(3) . . ?
S4 C7 S6 118.41(18) . . ?
C9 C8 S5 115.0(3) . . ?
C9 C8 H8A 108.5 . . ?
S5 C8 H8A 108.5 . . ?
C9 C8 H8B 108.5 . . ?
S5 C8 H8B 108.5 . . ?
H8A C8 H8B 107.5 . . ?
C10 C9 C8 113.0(3) . . ?
C10 C9 H9A 109.0 . . ?
C8 C9 H9A 109.0 . . ?
C10 C9 H9B 109.0 . . ?
C8 C9 H9B 109.0 . . ?
H9A C9 H9B 107.8 . . ?
C11 C10 C9 113.5(4) . . ?
C11 C10 H10A 108.9 . . ?
C9 C10 H10A 108.9 . . ?
C11 C10 H10B 108.9 . . ?
C9 C10 H10B 108.9 . . ?
H10A C10 H10B 107.7 . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C13 C12 S6 115.6(3) . . ?
C13 C12 H12A 108.4 . . ?
S6 C12 H12A 108.4 . . ?
C13 C12 H12B 108.4 . . ?
S6 C12 H12B 108.4 . . ?
H12A C12 H12B 107.4 . . ?
C14 C13 C12 114.6(4) . . ?
C14 C13 H13A 108.6 . . ?
C12 C13 H13A 108.6 . . ?
C14 C13 H13B 108.6 . . ?
C12 C13 H13B 108.6 . . ?
H13A C13 H13B 107.6 . . ?
C13 C14 C15 112.9(5) . . ?
C13 C14 H14A 109.0 . . ?
C15 C14 H14A 109.0 . . ?
C13 C14 H14B 109.0 . . ?
C15 C14 H14B 109.0 . . ?
H14A C14 H14B 107.8 . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?

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

C3 C1 C2 C3 1.6(5) 2_765 . . . ?
C3 C1 C2 S1 -179.5(2) 2_765 . . . ?
C4 S1 C2 C1 -178.8(3) . . . . ?
C4 S1 C2 C3 0.2(3) . . . . ?
C1 C2 C3 C1 -1.6(6) . . . 2_765 ?
S1 C2 C3 C1 179.4(3) . . . 2_765 ?
C1 C2 C3 S2 177.5(3) . . . . ?
S1 C2 C3 S2 -1.5(4) . . . . ?
C4 S2 C3 C1 -178.9(3) . . . 2_765 ?
C4 S2 C3 C2 2.0(3) . . . . ?
C3 S2 C4 C5 179.5(3) . . . . ?
C3 S2 C4 S1 -1.8(2) . . . . ?
C2 S1 C4 C5 179.9(3) . . . . ?
C2 S1 C4 S2 1.1(2) . . . . ?
S2 C4 C5 S4 175.74(18) . . . . ?
S1 C4 C5 S4 -2.9(5) . . . . ?
S2 C4 C5 S3 -0.9(5) . . . . ?
S1 C4 C5 S3 -179.51(18) . . . . ?
C7 S4 C5 C4 175.8(3) . . . . ?
C7 S4 C5 S3 -7.3(2) . . . . ?
C6 S3 C5 C4 -176.2(3) . . . . ?
C6 S3 C5 S4 7.0(2) . . . . ?
C8 S5 C6 C7 128.8(3) . . . . ?
C8 S5 C6 S3 -60.0(3) . . . . ?
C5 S3 C6 C7 -3.7(3) . . . . ?
C5 S3 C6 S5 -175.7(2) . . . . ?
S5 C6 C7 S4 170.5(2) . . . . ?
S3 C6 C7 S4 -0.9(4) . . . . ?
S5 C6 C7 S6 -2.4(5) . . . . ?
S3 C6 C7 S6 -173.75(19) . . . . ?
C5 S4 C7 C6 5.0(3) . . . . ?
C5 S4 C7 S6 178.3(2) . . . . ?
C12 S6 C7 C6 -138.8(3) . . . . ?
C12 S6 C7 S4 48.3(2) . . . . ?
C6 S5 C8 C9 -67.0(3) . . . . ?
S5 C8 C9 C10 -171.3(3) . . . . ?
C8 C9 C10 C11 -177.9(4) . . . . ?
C7 S6 C12 C13 61.0(3) . . . . ?
S6 C12 C13 C14 67.3(5) . . . . ?
C12 C13 C14 C15 179.6(4) . . . . ?

_diffrn_measured_fraction_theta_max 0.988

_diffrn_reflns_theta_full        25.01

_diffrn_measured_fraction_theta_full 0.988

_refine_diff_density_max         0.348

_refine_diff_density_min         -0.363

_refine_diff_density_rms         0.062