# Supplementary Material (ESI) for Journal of Materials Chemistry
# This journal is (C) The Royal Society of Chemistry 2008


data_global

_journal_coden_Cambridge         1145
_journal_volume                  ?
_journal_page_first              ?
_journal_year                    ?

loop_
_publ_author_name
'Wei Xu.'
'Wei Hong.'
'Wenping Hu.'
'Quanrui Wang.'
'Zhongming Wei.'
'Hongxia Xi.'
'Daoben Zhu.'

_publ_contact_author_name        'Dr Wei Xu'
_publ_contact_author_email       WXU@ICCAS.AC.CN

_publ_section_title              
;
6H-Pyrrolo[3,2-b:4,5-b']bis[1,4]benzothiazines:
Facilely Synthesized Semiconductors for Organic Field-effect Transistors
;

# Attachment 'r080409a.cif'

data_r080409a
_database_code_depnum_ccdc_archive 'CCDC 690390'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C16 H9 N3 S2'
_chemical_formula_weight         307.38

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'
N N 0.0061 0.0033 '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   P2(1)/n

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                   4.7896(10)
_cell_length_b                   23.389(5)
_cell_length_c                   11.493(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 97.35(3)
_cell_angle_gamma                90.00
_cell_volume                     1276.9(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    113(2)
_cell_measurement_reflns_used    2732
_cell_measurement_theta_min      1.741
_cell_measurement_theta_max      27.868

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.10
_exptl_crystal_size_mid          0.02
_exptl_crystal_size_min          0.02
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.599
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             632
_exptl_absorpt_coefficient_mu    0.411
_exptl_absorpt_correction_type   MULTI-SCAN
_exptl_absorpt_correction_T_min  0.9600
_exptl_absorpt_correction_T_max  0.9918
_exptl_absorpt_process_details   crystalclear

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      113(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'rotating anode'
_diffrn_radiation_monochromator  confocal
_diffrn_measurement_device_type  'rigaku saturn'
_diffrn_measurement_method       '\w scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0
_diffrn_reflns_number            9590
_diffrn_reflns_av_R_equivalents  0.1019
_diffrn_reflns_av_sigmaI/netI    0.0827
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         1.74
_diffrn_reflns_theta_max         25.02
_reflns_number_total             2249
_reflns_number_gt                1734
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       crystalclear
_computing_cell_refinement       crystalclear
_computing_data_reduction        crystalclear
_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^)+(0.0608P)^2^+0.5464P] 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         2249
_refine_ls_number_parameters     190
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0926
_refine_ls_R_factor_gt           0.0668
_refine_ls_wR_factor_ref         0.1503
_refine_ls_wR_factor_gt          0.1370
_refine_ls_goodness_of_fit_ref   1.128
_refine_ls_restrained_S_all      1.128
_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 0.1977(2) 0.99794(4) 0.87928(9) 0.0206(3) Uani 1 1 d . . .
S2 S 0.6677(2) 0.87815(4) 0.93068(9) 0.0213(3) Uani 1 1 d . . .
N1 N 0.2636(7) 1.02313(13) 0.6093(3) 0.0178(8) Uani 1 1 d . . .
N2 N 0.5884(6) 0.94792(13) 0.6188(3) 0.0171(7) Uani 1 1 d . . .
H2 H 0.6287 0.9507 0.5482 0.021 Uiso 1 1 calc R . .
N3 N 0.8826(7) 0.87002(13) 0.6763(3) 0.0192(8) Uani 1 1 d . . .
C1 C 0.0226(8) 1.04864(15) 0.7819(3) 0.0161(9) Uani 1 1 d . . .
C2 C -0.1720(8) 1.08354(16) 0.8287(4) 0.0201(9) Uani 1 1 d . . .
H2A H -0.2035 1.0788 0.9063 0.024 Uiso 1 1 calc R . .
C3 C -0.3170(8) 1.12478(16) 0.7608(4) 0.0218(10) Uani 1 1 d . . .
H3 H -0.4442 1.1483 0.7926 0.026 Uiso 1 1 calc R . .
C4 C -0.2729(8) 1.13131(16) 0.6438(4) 0.0201(9) Uani 1 1 d . . .
H4 H -0.3737 1.1585 0.5967 0.024 Uiso 1 1 calc R . .
C5 C -0.0787(8) 1.09703(16) 0.5986(4) 0.0205(9) Uani 1 1 d . . .
H5 H -0.0488 1.1020 0.5209 0.025 Uiso 1 1 calc R . .
C6 C 0.0736(8) 1.05539(15) 0.6655(4) 0.0178(9) Uani 1 1 d . . .
C7 C 0.4028(8) 0.98247(15) 0.6663(4) 0.0167(9) Uani 1 1 d . . .
C8 C 0.3987(8) 0.96373(15) 0.7876(3) 0.0178(9) Uani 1 1 d . . .
C9 C 0.5795(8) 0.91911(15) 0.8071(3) 0.0169(9) Uani 1 1 d . . .
C10 C 0.7019(8) 0.90811(16) 0.6991(4) 0.0191(9) Uani 1 1 d . . .
C11 C 0.9839(8) 0.83172(16) 0.7660(4) 0.0214(10) Uani 1 1 d . . .
C12 C 1.1804(8) 0.79146(16) 0.7375(4) 0.0229(10) Uani 1 1 d . . .
H12 H 1.2327 0.7916 0.6623 0.027 Uiso 1 1 calc R . .
C13 C 1.2991(9) 0.75154(17) 0.8177(4) 0.0252(10) Uani 1 1 d . . .
H13 H 1.4273 0.7250 0.7960 0.030 Uiso 1 1 calc R . .
C14 C 1.2261(9) 0.75134(17) 0.9304(4) 0.0267(11) Uani 1 1 d . . .
H14 H 1.3070 0.7248 0.9849 0.032 Uiso 1 1 calc R . .
C15 C 1.0326(9) 0.79055(17) 0.9620(4) 0.0252(10) Uani 1 1 d . . .
H15 H 0.9834 0.7902 1.0376 0.030 Uiso 1 1 calc R . .
C16 C 0.9108(8) 0.83076(16) 0.8806(4) 0.0208(10) Uani 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 0.0199(6) 0.0232(5) 0.0189(6) 0.0025(4) 0.0029(4) 0.0036(4)
S2 0.0229(6) 0.0206(5) 0.0195(6) 0.0032(4) -0.0004(4) 0.0006(4)
N1 0.0162(18) 0.0166(16) 0.021(2) -0.0012(14) 0.0031(15) 0.0007(14)
N2 0.0148(18) 0.0215(17) 0.0149(18) 0.0010(14) 0.0019(15) 0.0024(14)
N3 0.0206(19) 0.0198(17) 0.0162(18) -0.0006(14) -0.0016(15) 0.0029(14)
C1 0.011(2) 0.0184(19) 0.017(2) -0.0017(16) -0.0055(17) 0.0003(16)
C2 0.020(2) 0.023(2) 0.017(2) -0.0014(17) 0.0041(18) -0.0039(17)
C3 0.018(2) 0.018(2) 0.029(3) -0.0048(19) 0.0013(19) -0.0029(18)
C4 0.018(2) 0.0171(19) 0.023(2) 0.0001(17) -0.0059(18) 0.0019(16)
C5 0.015(2) 0.025(2) 0.021(2) 0.0003(18) -0.0010(18) -0.0019(17)
C6 0.014(2) 0.0164(19) 0.022(2) -0.0020(17) -0.0016(18) -0.0027(16)
C7 0.015(2) 0.0151(19) 0.020(2) -0.0010(16) 0.0007(18) -0.0023(16)
C8 0.015(2) 0.018(2) 0.020(2) -0.0011(17) -0.0012(18) -0.0037(17)
C9 0.016(2) 0.0175(19) 0.016(2) 0.0002(16) -0.0027(18) -0.0008(16)
C10 0.016(2) 0.0156(19) 0.024(2) 0.0012(17) -0.0036(18) -0.0035(16)
C11 0.017(2) 0.020(2) 0.025(2) 0.0004(18) -0.0035(19) -0.0045(17)
C12 0.019(2) 0.020(2) 0.028(2) -0.0057(18) -0.002(2) 0.0012(18)
C13 0.023(2) 0.021(2) 0.030(3) -0.0026(18) -0.005(2) 0.0015(17)
C14 0.019(2) 0.019(2) 0.039(3) 0.0017(19) -0.009(2) -0.0011(17)
C15 0.024(2) 0.025(2) 0.024(2) 0.0034(19) -0.007(2) -0.0079(19)
C16 0.014(2) 0.019(2) 0.027(2) 0.0006(17) -0.0045(19) -0.0013(16)

_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 C8 1.713(4) . ?
S1 C1 1.767(4) . ?
S2 C9 1.721(4) . ?
S2 C16 1.757(4) . ?
N1 C7 1.291(5) . ?
N1 C6 1.402(5) . ?
N2 C7 1.366(5) . ?
N2 C10 1.373(5) . ?
N2 H2 0.8600 . ?
N3 C10 1.292(5) . ?
N3 C11 1.404(5) . ?
C1 C2 1.397(5) . ?
C1 C6 1.399(6) . ?
C2 C3 1.372(5) . ?
C2 H2A 0.9300 . ?
C3 C4 1.396(6) . ?
C3 H3 0.9300 . ?
C4 C5 1.379(6) . ?
C4 H4 0.9300 . ?
C5 C6 1.389(5) . ?
C5 H5 0.9300 . ?
C7 C8 1.465(6) . ?
C8 C9 1.356(5) . ?
C9 C10 1.461(6) . ?
C11 C12 1.399(6) . ?
C11 C16 1.405(6) . ?
C12 C13 1.382(6) . ?
C12 H12 0.9300 . ?
C13 C14 1.384(6) . ?
C13 H13 0.9300 . ?
C14 C15 1.385(6) . ?
C14 H14 0.9300 . ?
C15 C16 1.400(6) . ?
C15 H15 0.9300 . ?

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
C8 S1 C1 100.53(19) . . ?
C9 S2 C16 100.6(2) . . ?
C7 N1 C6 119.1(4) . . ?
C7 N2 C10 110.8(3) . . ?
C7 N2 H2 124.6 . . ?
C10 N2 H2 124.6 . . ?
C10 N3 C11 117.9(4) . . ?
C2 C1 C6 120.6(4) . . ?
C2 C1 S1 115.8(3) . . ?
C6 C1 S1 123.7(3) . . ?
C3 C2 C1 120.4(4) . . ?
C3 C2 H2A 119.8 . . ?
C1 C2 H2A 119.8 . . ?
C2 C3 C4 119.8(4) . . ?
C2 C3 H3 120.1 . . ?
C4 C3 H3 120.1 . . ?
C5 C4 C3 119.4(4) . . ?
C5 C4 H4 120.3 . . ?
C3 C4 H4 120.3 . . ?
C4 C5 C6 122.1(4) . . ?
C4 C5 H5 119.0 . . ?
C6 C5 H5 119.0 . . ?
C5 C6 C1 117.7(4) . . ?
C5 C6 N1 116.6(4) . . ?
C1 C6 N1 125.7(4) . . ?
N1 C7 N2 123.6(4) . . ?
N1 C7 C8 129.4(4) . . ?
N2 C7 C8 107.0(3) . . ?
C9 C8 C7 107.5(4) . . ?
C9 C8 S1 131.0(3) . . ?
C7 C8 S1 121.5(3) . . ?
C8 C9 C10 108.2(3) . . ?
C8 C9 S2 130.4(3) . . ?
C10 C9 S2 121.4(3) . . ?
N3 C10 N2 123.3(4) . . ?
N3 C10 C9 130.2(4) . . ?
N2 C10 C9 106.5(3) . . ?
C12 C11 N3 115.9(4) . . ?
C12 C11 C16 117.6(4) . . ?
N3 C11 C16 126.4(4) . . ?
C13 C12 C11 122.0(4) . . ?
C13 C12 H12 119.0 . . ?
C11 C12 H12 119.0 . . ?
C12 C13 C14 119.6(4) . . ?
C12 C13 H13 120.2 . . ?
C14 C13 H13 120.2 . . ?
C13 C14 C15 120.0(4) . . ?
C13 C14 H14 120.0 . . ?
C15 C14 H14 120.0 . . ?
C14 C15 C16 120.4(4) . . ?
C14 C15 H15 119.8 . . ?
C16 C15 H15 119.8 . . ?
C15 C16 C11 120.3(4) . . ?
C15 C16 S2 116.2(3) . . ?
C11 C16 S2 123.5(3) . . ?

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
C8 S1 C1 C2 177.8(3) . . . . ?
C8 S1 C1 C6 -3.4(4) . . . . ?
C6 C1 C2 C3 0.3(6) . . . . ?
S1 C1 C2 C3 179.2(3) . . . . ?
C1 C2 C3 C4 1.0(6) . . . . ?
C2 C3 C4 C5 -1.5(6) . . . . ?
C3 C4 C5 C6 0.8(6) . . . . ?
C4 C5 C6 C1 0.5(6) . . . . ?
C4 C5 C6 N1 179.7(3) . . . . ?
C2 C1 C6 C5 -1.1(5) . . . . ?
S1 C1 C6 C5 -179.9(3) . . . . ?
C2 C1 C6 N1 179.9(3) . . . . ?
S1 C1 C6 N1 1.1(6) . . . . ?
C7 N1 C6 C5 -177.5(4) . . . . ?
C7 N1 C6 C1 1.6(6) . . . . ?
C6 N1 C7 N2 178.7(3) . . . . ?
C6 N1 C7 C8 -1.0(6) . . . . ?
C10 N2 C7 N1 -179.1(4) . . . . ?
C10 N2 C7 C8 0.6(4) . . . . ?
N1 C7 C8 C9 179.6(4) . . . . ?
N2 C7 C8 C9 -0.2(4) . . . . ?
N1 C7 C8 S1 -2.2(6) . . . . ?
N2 C7 C8 S1 178.1(3) . . . . ?
C1 S1 C8 C9 -178.4(4) . . . . ?
C1 S1 C8 C7 3.8(3) . . . . ?
C7 C8 C9 C10 -0.3(4) . . . . ?
S1 C8 C9 C10 -178.3(3) . . . . ?
C7 C8 C9 S2 -179.6(3) . . . . ?
S1 C8 C9 S2 2.4(6) . . . . ?
C16 S2 C9 C8 179.9(4) . . . . ?
C16 S2 C9 C10 0.7(3) . . . . ?
C11 N3 C10 N2 179.8(3) . . . . ?
C11 N3 C10 C9 0.4(6) . . . . ?
C7 N2 C10 N3 179.7(4) . . . . ?
C7 N2 C10 C9 -0.8(4) . . . . ?
C8 C9 C10 N3 -179.8(4) . . . . ?
S2 C9 C10 N3 -0.5(6) . . . . ?
C8 C9 C10 N2 0.6(4) . . . . ?
S2 C9 C10 N2 -180.0(3) . . . . ?
C10 N3 C11 C12 -179.6(3) . . . . ?
C10 N3 C11 C16 -0.8(6) . . . . ?
N3 C11 C12 C13 179.4(4) . . . . ?
C16 C11 C12 C13 0.5(6) . . . . ?
C11 C12 C13 C14 -0.8(6) . . . . ?
C12 C13 C14 C15 0.7(6) . . . . ?
C13 C14 C15 C16 -0.3(6) . . . . ?
C14 C15 C16 C11 -0.1(6) . . . . ?
C14 C15 C16 S2 179.8(3) . . . . ?
C12 C11 C16 C15 0.0(6) . . . . ?
N3 C11 C16 C15 -178.9(4) . . . . ?
C12 C11 C16 S2 -179.9(3) . . . . ?
N3 C11 C16 S2 1.3(6) . . . . ?
C9 S2 C16 C15 179.1(3) . . . . ?
C9 S2 C16 C11 -1.1(4) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N2 H2 N1 0.86 2.04 2.882(5) 166.7 3_676

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        25.02
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.392
_refine_diff_density_min         -0.343
_refine_diff_density_rms         0.084