# Supplementary Material (ESI) for Chemical Communications
# This journal is (c) The Royal Society of Chemistry 2007


data_global

_journal_coden_Cambridge         182

loop_
_publ_author_name
'John Reynolds'
'Khalil Abboud'
'Matt Craps'
'Andrew G. Rinzler'
'Tim Steckler'

_publ_contact_author_name        'John Reynolds'
_publ_contact_author_address     
;
Chemistry Department
University of Florida
Box 117200
Gainesville
FI
32611
UNITED STATES OF AMERICA
;

_publ_contact_author_email       REYNOLDS@CHEM.UFL.EDU

_publ_requested_journal          'Chemical Communications'

_publ_section_title              
;
Low Band Gap EDOT-Benzobis(thiadiazole) Hybrid Polymer
Characterized on Near-IR Transmissive Single Walled Carbon
;

data_stec1
_database_code_depnum_ccdc_archive 'CCDC 649009'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C18 H10 N4 O4 S4'
_chemical_formula_weight         474.54

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'
O O 0.0106 0.0060 '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                   6.2143(7)
_cell_length_b                   10.8663(12)
_cell_length_c                   14.9797(16)
_cell_angle_alpha                69.407(2)
_cell_angle_beta                 81.976(2)
_cell_angle_gamma                75.468(2)
_cell_volume                     915.13(17)
_cell_formula_units_Z            2
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    73
_cell_measurement_theta_min      2.0
_cell_measurement_theta_max      28.0

_exptl_crystal_description       needles
_exptl_crystal_colour            brown
_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.04
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.722
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             484
_exptl_absorpt_coefficient_mu    0.557
_exptl_absorpt_correction_type   integration
_exptl_absorpt_correction_T_min  0.9419
_exptl_absorpt_correction_T_max  0.9794
_exptl_absorpt_process_details   
'based on measured indexed crystal faces, Bruker SHELXTL v6.12 (Bruker 1998)'

_diffrn_ambient_temperature      173(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  'SMART CCD area detector'
_diffrn_measurement_method       '\w scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        1
_diffrn_reflns_number            6248
_diffrn_reflns_av_R_equivalents  0.0325
_diffrn_reflns_av_sigmaI/netI    0.0448
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         1.45
_diffrn_reflns_theta_max         27.49
_reflns_number_total             4090
_reflns_number_gt                3205
_reflns_threshold_expression     I>2\s(I)

_computing_data_collection       'Bruker SMART v5.624 (Bruker 1998)'
_computing_cell_refinement       
'Bruker SMART v5.624 & SAINT 6.36a (Bruker 1998)'
_computing_data_reduction        'Bruker SHELXTL v6.14 (Bruker 2000)'
_computing_structure_solution    'Bruker SHELXTL v6.14'
_computing_structure_refinement  'Bruker SHELXTL v6.14'
_computing_molecular_graphics    'Bruker SHELXTL v6.14'
_computing_publication_material  'Bruker SHELXTL v6.14'

_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.

The asymmetric unit consists of two half molecules (each located on an
inversion center). One of the molecules has a disorder in the C18-C19 unit
and
was refined in two parts (minor part is labeled C18?-C19?. Their site
occupation factors were dependently refined.
;

_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^)+(0.0525P)^2^+0.0440P] 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         4090
_refine_ls_number_parameters     270
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0518
_refine_ls_R_factor_gt           0.0374
_refine_ls_wR_factor_ref         0.0980
_refine_ls_wR_factor_gt          0.0923
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_restrained_S_all      1.031
_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 0.04601(10) 0.92397(5) 0.24113(4) 0.02793(15) Uani 1 1 d . . .
S2 S 0.46763(9) 1.20476(6) 0.00647(4) 0.02805(15) Uani 1 1 d . . .
O1 O 0.2519(3) 1.57905(15) -0.14148(11) 0.0308(4) Uani 1 1 d . . .
O2 O -0.0512(2) 1.41270(14) -0.13679(10) 0.0264(3) Uani 1 1 d . . .
N1 N -0.0577(3) 0.84890(17) 0.18842(12) 0.0243(4) Uani 1 1 d . . .
N2 N 0.1239(3) 1.04278(17) 0.15341(12) 0.0246(4) Uani 1 1 d . . .
C1 C -0.0335(3) 0.91592(19) 0.09281(14) 0.0205(4) Uani 1 1 d . . .
C2 C 0.0705(3) 1.02865(19) 0.07271(14) 0.0208(4) Uani 1 1 d . . .
C3 C 0.1061(3) 1.11617(19) -0.02066(14) 0.0200(4) Uani 1 1 d . . .
C4 C 0.2144(3) 1.2286(2) -0.04012(14) 0.0202(4) Uani 1 1 d . . .
C5 C 0.1448(3) 1.3619(2) -0.09285(14) 0.0197(4) Uani 1 1 d . . .
C6 C 0.2922(3) 1.4431(2) -0.09342(14) 0.0229(4) Uani 1 1 d . . .
C7 C 0.4747(4) 1.3717(2) -0.04334(15) 0.0294(5) Uani 1 1 d . . .
H7A H 0.5914 1.4094 -0.0368 0.035 Uiso 1 1 calc R . .
C8 C 0.0201(4) 1.6330(2) -0.16096(18) 0.0342(5) Uani 1 1 d . . .
H8A H 0.0022 1.7257 -0.2071 0.041 Uiso 1 1 calc R . .
H8B H -0.0668 1.6378 -0.1012 0.041 Uiso 1 1 calc R . .
C9 C -0.0694(4) 1.5489(2) -0.20068(17) 0.0323(5) Uani 1 1 d . . .
H9A H -0.2279 1.5902 -0.2138 0.039 Uiso 1 1 calc R . .
H9B H 0.0129 1.5478 -0.2620 0.039 Uiso 1 1 calc R . .
S11 S 0.53679(10) 1.14674(5) 0.25539(4) 0.02762(15) Uani 1 1 d . . .
S12 S 0.02009(9) 0.77932(6) 0.52892(4) 0.02759(14) Uani 1 1 d . A .
O11 O 0.2554(3) 0.55752(15) 0.36855(10) 0.0293(4) Uani 1 1 d . . .
O12 O 0.5588(2) 0.72018(14) 0.37153(10) 0.0258(3) Uani 1 1 d . . .
N11 N 0.6271(3) 1.18573(17) 0.33505(12) 0.0250(4) Uani 1 1 d . . .
N12 N 0.4300(3) 1.02089(17) 0.31814(12) 0.0242(4) Uani 1 1 d . . .
C11 C 0.5744(3) 1.09644(19) 0.42079(14) 0.0198(4) Uani 1 1 d . . .
C12 C 0.4630(3) 1.0000(2) 0.41136(14) 0.0196(4) Uani 1 1 d . . .
C13 C 0.3876(3) 0.90063(19) 0.48944(14) 0.0193(4) Uani 1 1 d . . .
C14 C 0.2801(3) 0.8033(2) 0.47705(13) 0.0198(4) Uani 1 1 d . . .
C15 C 0.3567(3) 0.72444(19) 0.42075(13) 0.0197(4) Uani 1 1 d . A .
C16 C 0.2081(3) 0.6443(2) 0.41974(14) 0.0220(4) Uani 1 1 d . A .
C17 C 0.0176(4) 0.6649(2) 0.47418(15) 0.0270(5) Uani 1 1 d . . .
H17A H -0.1018 0.6216 0.4811 0.032 Uiso 1 1 calc R A .
C18 C 0.4903(6) 0.5310(4) 0.3381(3) 0.0286(10) Uiso 0.646(8) 1 d P A 1
H18A H 0.5116 0.4881 0.2882 0.034 Uiso 0.646(8) 1 calc PR A 1
H18B H 0.5769 0.4675 0.3930 0.034 Uiso 0.646(8) 1 calc PR A 1
C19 C 0.5764(6) 0.6591(4) 0.2991(3) 0.0267(10) Uiso 0.646(8) 1 d P A 1
H19A H 0.7340 0.6386 0.2759 0.032 Uiso 0.646(8) 1 calc PR A 1
H19B H 0.4895 0.7229 0.2444 0.032 Uiso 0.646(8) 1 calc PR A 1
C18' C 0.4360(11) 0.5795(8) 0.3000(6) 0.0273(19) Uiso 0.354(8) 1 d P A 2
H18C H 0.3814 0.6557 0.2426 0.033 Uiso 0.354(8) 1 calc PR A 2
H18D H 0.4929 0.4984 0.2806 0.033 Uiso 0.354(8) 1 calc PR A 2
C19' C 0.6240(11) 0.6095(8) 0.3360(6) 0.0242(18) Uiso 0.354(8) 1 d P A 2
H19C H 0.6920 0.5283 0.3876 0.029 Uiso 0.354(8) 1 calc PR A 2
H19D H 0.7393 0.6291 0.2834 0.029 Uiso 0.354(8) 1 calc PR A 2

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 0.0429(3) 0.0222(3) 0.0199(3) -0.0059(2) -0.0080(2) -0.0075(2)
S2 0.0243(3) 0.0274(3) 0.0336(3) -0.0104(2) -0.0085(2) -0.0035(2)
O1 0.0346(9) 0.0215(8) 0.0364(9) -0.0068(7) 0.0013(7) -0.0122(7)
O2 0.0259(8) 0.0182(7) 0.0325(8) -0.0031(6) -0.0085(6) -0.0044(6)
N1 0.0316(10) 0.0199(9) 0.0209(9) -0.0059(7) -0.0060(7) -0.0036(7)
N2 0.0342(10) 0.0190(9) 0.0212(9) -0.0070(7) -0.0083(7) -0.0027(7)
C1 0.0225(10) 0.0154(10) 0.0221(10) -0.0063(8) -0.0029(8) -0.0007(8)
C2 0.0230(10) 0.0164(10) 0.0240(10) -0.0087(8) -0.0070(8) 0.0001(8)
C3 0.0217(10) 0.0166(10) 0.0223(10) -0.0079(8) -0.0037(8) -0.0019(8)
C4 0.0219(10) 0.0212(10) 0.0197(10) -0.0089(8) -0.0030(8) -0.0044(8)
C5 0.0211(10) 0.0204(10) 0.0198(10) -0.0094(8) -0.0002(8) -0.0048(8)
C6 0.0269(11) 0.0226(11) 0.0222(10) -0.0102(9) 0.0037(8) -0.0095(9)
C7 0.0255(12) 0.0349(13) 0.0332(12) -0.0139(10) 0.0016(9) -0.0140(10)
C8 0.0356(13) 0.0214(12) 0.0433(14) -0.0107(10) 0.0005(10) -0.0037(10)
C9 0.0342(13) 0.0197(11) 0.0378(13) -0.0046(10) -0.0062(10) -0.0012(9)
S11 0.0387(3) 0.0258(3) 0.0185(3) -0.0064(2) -0.0043(2) -0.0072(2)
S12 0.0227(3) 0.0274(3) 0.0363(3) -0.0166(2) 0.0055(2) -0.0068(2)
O11 0.0353(9) 0.0296(9) 0.0323(8) -0.0185(7) 0.0027(7) -0.0136(7)
O12 0.0247(8) 0.0296(8) 0.0306(8) -0.0184(7) 0.0065(6) -0.0110(6)
N11 0.0307(10) 0.0238(9) 0.0213(9) -0.0083(7) -0.0006(7) -0.0064(8)
N12 0.0310(10) 0.0235(9) 0.0191(8) -0.0093(7) -0.0044(7) -0.0031(7)
C11 0.0197(10) 0.0172(10) 0.0222(10) -0.0079(8) -0.0029(8) -0.0006(8)
C12 0.0192(10) 0.0208(10) 0.0205(10) -0.0112(8) -0.0037(7) 0.0002(8)
C13 0.0190(10) 0.0187(10) 0.0211(10) -0.0096(8) -0.0023(7) -0.0008(8)
C14 0.0208(10) 0.0192(10) 0.0196(10) -0.0060(8) -0.0023(8) -0.0050(8)
C15 0.0199(10) 0.0205(10) 0.0189(10) -0.0061(8) -0.0024(8) -0.0044(8)
C16 0.0268(11) 0.0188(10) 0.0229(10) -0.0082(8) -0.0039(8) -0.0062(8)
C17 0.0248(11) 0.0242(11) 0.0363(12) -0.0121(9) -0.0010(9) -0.0102(9)

_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 N1 1.6009(18) . ?
S1 N2 1.6032(18) . ?
S2 C7 1.711(2) . ?
S2 C4 1.734(2) . ?
O1 C6 1.371(2) . ?
O1 C8 1.441(3) . ?
O2 C5 1.361(2) . ?
O2 C9 1.439(2) . ?
N1 C1 1.366(3) . ?
N2 C2 1.365(2) . ?
C1 C3 1.405(3) 2_575 ?
C1 C2 1.447(3) . ?
C2 C3 1.412(3) . ?
C3 C1 1.405(3) 2_575 ?
C3 C4 1.462(3) . ?
C4 C5 1.373(3) . ?
C5 C6 1.420(3) . ?
C6 C7 1.355(3) . ?
C8 C9 1.493(3) . ?
S11 N12 1.6034(18) . ?
S11 N11 1.6063(18) . ?
S12 C17 1.717(2) . ?
S12 C14 1.732(2) . ?
O11 C16 1.368(2) . ?
O11 C18' 1.418(6) . ?
O11 C18 1.455(4) . ?
O12 C15 1.364(2) . ?
O12 C19' 1.428(6) . ?
O12 C19 1.438(4) . ?
N11 C11 1.365(3) . ?
N12 C12 1.370(2) . ?
C11 C13 1.410(3) 2_676 ?
C11 C12 1.447(3) . ?
C12 C13 1.402(3) . ?
C13 C11 1.410(3) 2_676 ?
C13 C14 1.459(3) . ?
C14 C15 1.365(3) . ?
C15 C16 1.424(3) . ?
C16 C17 1.357(3) . ?
C18 C19 1.510(6) . ?
C18' C19' 1.501(10) . ?

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
N1 S1 N2 102.42(9) . . ?
C7 S2 C4 92.80(10) . . ?
C6 O1 C8 111.39(16) . . ?
C5 O2 C9 112.91(16) . . ?
C1 N1 S1 106.27(14) . . ?
C2 N2 S1 106.05(14) . . ?
N1 C1 C3 124.88(19) . 2_575 ?
N1 C1 C2 112.46(18) . . ?
C3 C1 C2 122.63(18) 2_575 . ?
N2 C2 C3 124.18(18) . . ?
N2 C2 C1 112.80(18) . . ?
C3 C2 C1 123.00(18) . . ?
C1 C3 C2 114.36(18) 2_575 . ?
C1 C3 C4 123.16(18) 2_575 . ?
C2 C3 C4 122.46(18) . . ?
C5 C4 C3 129.48(18) . . ?
C5 C4 S2 109.52(15) . . ?
C3 C4 S2 121.00(14) . . ?
O2 C5 C4 123.43(18) . . ?
O2 C5 C6 123.03(18) . . ?
C4 C5 C6 113.47(18) . . ?
C7 C6 O1 124.61(19) . . ?
C7 C6 C5 112.90(19) . . ?
O1 C6 C5 122.48(19) . . ?
C6 C7 S2 111.30(17) . . ?
O1 C8 C9 111.88(18) . . ?
O2 C9 C8 112.42(18) . . ?
N12 S11 N11 102.64(9) . . ?
C17 S12 C14 92.59(10) . . ?
C16 O11 C18' 113.0(3) . . ?
C16 O11 C18 111.8(2) . . ?
C18' O11 C18 27.6(3) . . ?
C15 O12 C19' 112.9(3) . . ?
C15 O12 C19 112.35(19) . . ?
C19' O12 C19 26.7(3) . . ?
C11 N11 S11 105.79(14) . . ?
C12 N12 S11 106.01(14) . . ?
N11 C11 C13 124.68(19) . 2_676 ?
N11 C11 C12 113.07(18) . . ?
C13 C11 C12 122.18(18) 2_676 . ?
N12 C12 C13 123.93(18) . . ?
N12 C12 C11 112.48(18) . . ?
C13 C12 C11 123.52(18) . . ?
C12 C13 C11 114.28(18) . 2_676 ?
C12 C13 C14 121.94(17) . . ?
C11 C13 C14 123.78(18) 2_676 . ?
C15 C14 C13 127.01(18) . . ?
C15 C14 S12 109.78(15) . . ?
C13 C14 S12 123.10(15) . . ?
O12 C15 C14 123.33(18) . . ?
O12 C15 C16 122.85(17) . . ?
C14 C15 C16 113.81(18) . . ?
C17 C16 O11 124.79(19) . . ?
C17 C16 C15 112.45(18) . . ?
O11 C16 C15 122.76(18) . . ?
C16 C17 S12 111.36(16) . . ?
O11 C18 C19 111.3(3) . . ?
O12 C19 C18 110.7(3) . . ?
O11 C18' C19' 113.3(6) . . ?
O12 C19' C18' 114.0(6) . . ?

_diffrn_measured_fraction_theta_max 0.977
_diffrn_reflns_theta_full        27.49
_diffrn_measured_fraction_theta_full 0.977
_refine_diff_density_max         0.422
_refine_diff_density_min         -0.311
_refine_diff_density_rms         0.066

# Formatted by publCIF