# Supplementary Material (ESI) for Chemical Communications
# This journal is © The Royal Society of Chemistry 2005



data_global

_journal_name_full               Chem.Commun.

_journal_coden_Cambridge         0182

_publ_contact_author_name        'Dr. Yoshiro Yamashita'
_publ_contact_author_address     
;
Department of Electronic Chemistry
Interdisciplinary Graduate School of Science and Engineering
Tokyo Institute of Technology
Nagatsuta, Midori-ku, Yokohama 226-8502, Japan
;

_publ_contact_author_phone       +81-45-924-5571
_publ_contact_author_fax         +81-45-924-5489
_publ_contact_author_email       yoshiro@echem.titech.ac.jp

_publ_section_title              
;
Syntheis, Characterization, and FET Properties of
Novel Dithiazolylbenzothiadiazole Derivatives
;
_journal_volume                  ?
_journal_page_first              ?
_journal_page_last               ?
_journal_year                    ?
_ccdc_journal_depnumber          ?
loop_
_publ_author_name
Md.Akhtaruzzman
N.Kamata
J.-i.Nishida
S.Ando
H.Tada
M.Tomura
;
Y.Yamashita
;

#------------------------------------------------------------------------------
data_1
_database_code_depnum_ccdc_archive 'CCDC 265881'
#------------------------------------------------------------------------------
# CHEMICAL DATA
_chemical_formula_sum            'C12 H6 N4 S3 '
_chemical_formula_moiety         'C12 H6 N4 S3 '
_chemical_formula_weight         302.39
_chemical_melting_point          ?
#------------------------------------------------------------------------------
# CRYSTAL DATA
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_symmetry_Int_Tables_number      14
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x,1/2+y,1/2-z
-x,-y,-z
x,1/2-y,1/2+z
_cell_length_a                   4.941(6)
_cell_length_b                   17.81(2)
_cell_length_c                   13.56(2)
_cell_angle_alpha                90
_cell_angle_beta                 90.62(5)
_cell_angle_gamma                90
_cell_volume                     1193(9)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9106
_cell_measurement_theta_min      3.0
_cell_measurement_theta_max      27.5
_cell_measurement_temperature    93.2
#------------------------------------------------------------------------------
_exptl_crystal_description       platelet
_exptl_crystal_colour            red
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.070
_exptl_crystal_size_rad          ?
_exptl_crystal_density_diffrn    1.683
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_absorpt_coefficient_mu    0.609
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(Higashi, 1995)'
_exptl_absorpt_correction_T_min  0.710
_exptl_absorpt_correction_T_max  0.958
#------------------------------------------------------------------------------
# EXPERIMENTAL DATA
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_measurement_device_type  'Rigaku RAXIS-RAPID Imaging Plate'
_diffrn_measurement_method       \w
_diffrn_detector_area_resol_mean 10.00
_diffrn_reflns_number            10939
_diffrn_reflns_av_R_equivalents  0.037
_diffrn_reflns_theta_max         27.49
_diffrn_measured_fraction_theta_max 0.9716
_diffrn_reflns_theta_full        27.49
_diffrn_measured_fraction_theta_full 0.9716
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
#------------------------------------------------------------------------------
# REFINEMENT DATA
_refine_special_details          
;
Refinement using reflections with F^2^ > 0.0 sigma(F^2^). The weighted
R-factor (wR) and goodness of fit (S) are based on F^2^. R-factor (gt) are
based on F. The threshold expression of F^2^ > 2.0 sigma(F^2^) is used only
for calculating R-factor (gt).
;
_reflns_number_total             2667
_reflns_number_gt                1845
_reflns_threshold_expression     F^2^>2.0\s(F^2^)
_refine_ls_structure_factor_coef Fsqd
_refine_ls_R_factor_gt           0.0354
_refine_ls_wR_factor_ref         0.0841
_refine_ls_hydrogen_treatment    noref
_refine_ls_number_reflns         2542
_refine_ls_number_parameters     172
_refine_ls_goodness_of_fit_ref   0.811
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[\s^2^(Fo^2^) + (0.04500(Max(Fo^2^,0) + 2Fc^2^)/3)^2^]'
_refine_ls_shift/su_max          0.0003
_refine_diff_density_max         0.51
_refine_diff_density_min         -0.36
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details ?
_refine_ls_abs_structure_Flack   ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.003 0.002
;International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1)
;
H H 0.000 0.000
;International Tables for Crystallography
(1992, Vol. C, Table 6.1.1.2)
;
N N 0.006 0.003
;International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1)
;
S S 0.125 0.123
;International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1)
;
#------------------------------------------------------------------------------
# ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS
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_assembly
_atom_site_disorder_group
S(1) S 0.0199(1) 0.16641(4) 0.39464(4) 0.0229(2) Uani 1.00 d . . .
S(2) S 0.6537(1) 0.33508(4) 0.47340(4) 0.0203(2) Uani 1.00 d . . .
S(3) S -0.3856(1) 0.02204(4) 0.61895(5) 0.0243(2) Uani 1.00 d . . .
N(1) N 0.2496(4) 0.2193(1) 0.4443(1) 0.0204(5) Uani 1.00 d . . .
N(2) N -0.0996(4) 0.1246(1) 0.4908(1) 0.0203(5) Uani 1.00 d . . .
N(3) N 0.7722(4) 0.3277(1) 0.6584(1) 0.0204(5) Uani 1.00 d . . .
N(4) N -0.2445(4) 0.0620(1) 0.7937(1) 0.0208(6) Uani 1.00 d . . .
C(1) C 0.0412(5) 0.1521(1) 0.5692(2) 0.0175(6) Uani 1.00 d . . .
C(2) C 0.0039(5) 0.1313(1) 0.6696(2) 0.0164(6) Uani 1.00 d . . .
C(3) C 0.1686(5) 0.1669(1) 0.7377(2) 0.0182(6) Uani 1.00 d . . .
C(4) C 0.3649(5) 0.2202(1) 0.7109(2) 0.0179(6) Uani 1.00 d . . .
C(5) C 0.4078(4) 0.2422(1) 0.6148(2) 0.0162(6) Uani 1.00 d . . .
C(6) C 0.2408(5) 0.2064(1) 0.5418(2) 0.0176(6) Uani 1.00 d . . .
C(7) C 0.6092(5) 0.2986(1) 0.5913(2) 0.0162(6) Uani 1.00 d . . .
C(8) C 0.9398(5) 0.3796(1) 0.6167(2) 0.0216(7) Uani 1.00 d . . .
C(9) C 0.9062(5) 0.3918(1) 0.5189(2) 0.0224(7) Uani 1.00 d . . .
C(10) C -0.1944(5) 0.0760(1) 0.7002(2) 0.0177(6) Uani 1.00 d . . .
C(11) C -0.4399(5) 0.0081(1) 0.8025(2) 0.0221(7) Uani 1.00 d . . .
C(12) C -0.5366(5) -0.0206(2) 0.7167(2) 0.0236(7) Uani 1.00 d . . .
H(1) H 0.1485 0.1548 0.8060 0.0235 Uiso 1.00 calc . . .
H(2) H 0.4749 0.2426 0.7623 0.0235 Uiso 1.00 calc . . .
H(3) H 1.0750 0.4055 0.6553 0.0277 Uiso 1.00 calc . . .
H(4) H 1.0096 0.4270 0.4804 0.0274 Uiso 1.00 calc . . .
H(5) H -0.5031 -0.0085 0.8653 0.0273 Uiso 1.00 calc . . .
H(6) H -0.6715 -0.0596 0.7118 0.0299 Uiso 1.00 calc . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
S(1) 0.0272(3) 0.0277(4) 0.0137(3) -0.0046(3) -0.0014(2) -0.0005(3)
S(2) 0.0205(3) 0.0251(4) 0.0152(3) -0.0025(3) 0.0008(2) 0.0017(2)
S(3) 0.0285(4) 0.0259(4) 0.0185(3) -0.0057(3) -0.0011(3) -0.0021(3)
N(1) 0.021(1) 0.024(1) 0.0154(10) 0.0003(9) 0.0013(8) -0.0012(9)
N(2) 0.020(1) 0.025(1) 0.0158(10) 0.0002(9) 0.0005(8) -0.0001(9)
N(3) 0.020(1) 0.023(1) 0.0180(10) 0.0006(9) -0.0018(8) -0.0020(9)
N(4) 0.022(1) 0.024(1) 0.017(1) -0.0002(9) 0.0003(9) 0.0014(9)
C(1) 0.016(1) 0.021(1) 0.016(1) 0.005(1) 0.0011(9) -0.0031(10)
C(2) 0.015(1) 0.018(1) 0.016(1) 0.004(1) 0.0033(9) -0.0001(9)
C(3) 0.018(1) 0.023(1) 0.014(1) 0.003(1) 0.0017(9) 0.0013(10)
C(4) 0.016(1) 0.023(1) 0.014(1) 0.004(1) 0.0009(9) -0.0022(10)
C(5) 0.014(1) 0.019(1) 0.016(1) 0.0030(10) 0.0007(9) -0.0004(9)
C(6) 0.019(1) 0.020(1) 0.014(1) 0.004(1) -0.0009(10) -0.0014(9)
C(7) 0.017(1) 0.018(1) 0.014(1) 0.0037(10) 0.0019(9) 0.0017(9)
C(8) 0.020(1) 0.021(1) 0.024(1) 0.001(1) -0.002(1) -0.004(1)
C(9) 0.023(1) 0.020(1) 0.024(1) 0.000(1) 0.002(1) -0.002(1)
C(10) 0.018(1) 0.019(1) 0.016(1) 0.004(1) -0.0013(10) -0.0018(10)
C(11) 0.023(1) 0.022(1) 0.021(1) 0.000(1) 0.002(1) 0.004(1)
C(12) 0.021(1) 0.025(1) 0.025(1) -0.006(1) 0.005(1) 0.003(1)
#------------------------------------------------------------------------------
_computing_data_collection       PROCESS-AUTO
_computing_cell_refinement       PROCESS-AUTO
_computing_data_reduction        'teXsan Ver. 1.11'
_computing_structure_solution    SIR97
_computing_structure_refinement  'teXsan Ver. 1.10'
_computing_publication_material  'teXsan Ver. 1.11'
_computing_molecular_graphics    ?
#------------------------------------------------------------------------------
_geom_special_details            
;
?
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S(1) N(1) 1.617(2) . . yes
S(1) N(2) 1.619(2) . . yes
S(2) C(7) 1.742(2) . . yes
S(2) C(9) 1.715(3) . . yes
S(3) C(10) 1.735(2) . . yes
S(3) C(12) 1.707(3) . . yes
N(1) C(6) 1.343(3) . . yes
N(2) C(1) 1.355(3) . . yes
N(3) C(7) 1.315(3) . . yes
N(3) C(8) 1.368(3) . . yes
N(4) C(10) 1.318(3) . . yes
N(4) C(11) 1.368(3) . . yes
C(1) C(2) 1.425(3) . . yes
C(1) C(6) 1.433(4) . . yes
C(2) C(3) 1.379(3) . . yes
C(2) C(10) 1.453(4) . . yes
C(3) C(4) 1.408(4) . . yes
C(4) C(5) 1.379(3) . . yes
C(5) C(6) 1.432(3) . . yes
C(5) C(7) 1.451(3) . . yes
C(8) C(9) 1.352(3) . . yes
C(11) C(12) 1.353(3) . . yes
#------------------------------------------------------------------------------
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_2
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N(1) S(1) N(2) 101.1(1) . . . yes
C(7) S(2) C(9) 89.3(1) . . . yes
C(10) S(3) C(12) 89.6(1) . . . yes
S(1) N(1) C(6) 106.3(2) . . . yes
S(1) N(2) C(1) 106.1(2) . . . yes
C(7) N(3) C(8) 110.5(2) . . . yes
C(10) N(4) C(11) 110.9(2) . . . yes
N(2) C(1) C(2) 125.8(2) . . . yes
N(2) C(1) C(6) 112.9(2) . . . yes
C(2) C(1) C(6) 121.3(2) . . . yes
C(1) C(2) C(3) 116.0(2) . . . yes
C(1) C(2) C(10) 123.0(2) . . . yes
C(3) C(2) C(10) 121.0(2) . . . yes
C(2) C(3) C(4) 122.7(2) . . . yes
C(3) C(4) C(5) 123.3(2) . . . yes
C(4) C(5) C(6) 115.7(2) . . . yes
C(4) C(5) C(7) 121.1(2) . . . yes
C(6) C(5) C(7) 123.2(2) . . . yes
N(1) C(6) C(1) 113.6(2) . . . yes
N(1) C(6) C(5) 125.4(2) . . . yes
C(1) C(6) C(5) 120.9(2) . . . yes
S(2) C(7) N(3) 113.9(2) . . . yes
S(2) C(7) C(5) 123.6(2) . . . yes
N(3) C(7) C(5) 122.5(2) . . . yes
N(3) C(8) C(9) 116.4(2) . . . yes
S(2) C(9) C(8) 109.9(2) . . . yes
S(3) C(10) N(4) 113.5(2) . . . yes
S(3) C(10) C(2) 123.9(2) . . . yes
N(4) C(10) C(2) 122.5(2) . . . yes
N(4) C(11) C(12) 115.7(2) . . . yes
S(3) C(12) C(11) 110.2(2) . . . yes
#------------------------------------------------------------------------------
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
S(1) N(1) C(6) C(1) 0.3(2) . . . . yes
S(1) N(1) C(6) C(5) -179.1(2) . . . . yes
S(1) N(2) C(1) C(2) 179.9(2) . . . . yes
S(1) N(2) C(1) C(6) -0.3(2) . . . . yes
S(2) C(7) N(3) C(8) -0.6(3) . . . . yes
S(2) C(7) C(5) C(4) -174.1(2) . . . . yes
S(2) C(7) C(5) C(6) 5.4(3) . . . . yes
S(2) C(9) C(8) N(3) -0.7(3) . . . . yes
S(3) C(10) N(4) C(11) -0.6(3) . . . . yes
S(3) C(10) C(2) C(1) 6.7(3) . . . . yes
S(3) C(10) C(2) C(3) -173.4(2) . . . . yes
S(3) C(12) C(11) N(4) -1.3(3) . . . . yes
N(1) S(1) N(2) C(1) 0.4(2) . . . . yes
N(1) C(6) C(1) N(2) 0.0(3) . . . . yes
N(1) C(6) C(1) C(2) 179.8(2) . . . . yes
N(1) C(6) C(5) C(4) -179.8(2) . . . . yes
N(1) C(6) C(5) C(7) 0.6(4) . . . . yes
N(2) S(1) N(1) C(6) -0.4(2) . . . . yes
N(2) C(1) C(2) C(3) -179.5(2) . . . . yes
N(2) C(1) C(2) C(10) 0.4(4) . . . . yes
N(2) C(1) C(6) C(5) 179.4(2) . . . . yes
N(3) C(7) S(2) C(9) 0.3(2) . . . . yes
N(3) C(7) C(5) C(4) 4.7(4) . . . . yes
N(3) C(7) C(5) C(6) -175.8(2) . . . . yes
N(4) C(10) S(3) C(12) -0.1(2) . . . . yes
N(4) C(10) C(2) C(1) -173.7(2) . . . . yes
N(4) C(10) C(2) C(3) 6.3(4) . . . . yes
C(1) C(2) C(3) C(4) -0.7(4) . . . . yes
C(1) C(6) C(5) C(4) 0.8(3) . . . . yes
C(1) C(6) C(5) C(7) -178.8(2) . . . . yes
C(2) C(1) C(6) C(5) -0.7(3) . . . . yes
C(2) C(3) C(4) C(5) 0.8(4) . . . . yes
C(2) C(10) S(3) C(12) 179.6(2) . . . . yes
C(2) C(10) N(4) C(11) 179.7(2) . . . . yes
C(3) C(2) C(1) C(6) 0.6(3) . . . . yes
C(3) C(4) C(5) C(6) -0.8(3) . . . . yes
C(3) C(4) C(5) C(7) 178.7(2) . . . . yes
C(4) C(3) C(2) C(10) 179.3(2) . . . . yes
C(5) C(7) S(2) C(9) 179.1(2) . . . . yes
C(5) C(7) N(3) C(8) -179.5(2) . . . . yes
C(6) C(1) C(2) C(10) -179.4(2) . . . . yes
C(7) S(2) C(9) C(8) 0.2(2) . . . . yes
C(7) N(3) C(8) C(9) 0.9(3) . . . . yes
C(10) S(3) C(12) C(11) 0.8(2) . . . . yes
C(10) N(4) C(11) C(12) 1.3(3) . . . . yes
C(10) N(4) C(11) C(12) 1.3(3) . . . . yes
#------------------------------------------------------------------------------
loop_
_geom_contact_atom_site_label_1
_geom_contact_atom_site_label_2
_geom_contact_distance
_geom_contact_site_symmetry_1
_geom_contact_site_symmetry_2
_geom_contact_publ_flag
S(1) N(3) 3.420(2) . 4_454 ?
S(2) N(4) 3.095(2) . 4_654 ?
S(3) S(3) 3.497(1) . 3_456 ?
N(1) C(4) 3.398(3) . 4_554 ?
N(1) C(3) 3.477(3) . 4_554 ?
N(3) C(12) 3.402(3) . 2_556 ?
N(3) C(5) 3.545(4) . 1_655 ?
N(3) C(6) 3.550(4) . 1_655 ?
N(3) C(4) 3.564(4) . 1_655 ?
N(4) C(9) 3.243(3) . 4_455 ?
N(4) C(3) 3.526(4) . 1_455 ?
N(4) C(4) 3.589(3) . 1_455 ?
C(1) C(7) 3.385(4) . 1_455 ?
C(1) C(5) 3.576(4) . 1_455 ?
C(2) C(4) 3.582(5) . 1_455 ?
C(2) C(12) 3.586(4) . 1_655 ?
C(3) C(11) 3.533(4) . 1_655 ?
C(3) C(10) 3.581(5) . 1_655 ?
C(4) C(10) 3.371(4) . 1_655 ?
C(5) C(8) 3.368(4) . 1_455 ?
C(6) C(8) 3.577(4) . 1_455 ?
C(6) C(7) 3.596(4) . 1_455 ?
C(8) C(12) 3.510(4) . 2_556 ?
C(8) C(11) 3.533(4) . 2_656 ?
C(8) C(11) 3.549(4) . 2_556 ?

#===END

#------------------------------------------------------------------------------
# END of CIF
#------------------------------------------------------------------------------