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#$Date: 2016-03-21 18:50:35 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178826 $
#$URL: svn://www.crystallography.net/cod/cif/4/10/80/4108097.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_4108097
loop_
_publ_author_name
'Joseph A. Letizia'
'Michael R. Salata'
'Caitlin M. Tribout'
'Antonio Facchetti'
'Mark A. Ratner'
'Tobin J. Marks'
_publ_contact_author_address
;Department of Chemistry
Northwestern University
Evanston, IL 60201
;
_publ_contact_author_email       t-marks@northwestern.edu
_publ_contact_author_name        'Tobin Marks'
_publ_section_title
;
 n-Channel Polymers by Design: Optimizing the Interplay of Solubilizing
 Substituents, Crystal Packing, and Field-Effect Transistor
 Characteristics in Polymeric Bithiophene-Imide Semiconductors
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              9679
_journal_page_last               9694
_journal_paper_doi               10.1021/ja710815a
_journal_volume                  130
_journal_year                    2008
_chemical_formula_moiety         'C24 H12 N O2 S4'
_chemical_formula_sum            'C24 H12 N O2 S4'
_chemical_formula_weight         474.59
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           148
_symmetry_cell_setting           trigonal
_symmetry_space_group_name_Hall  '-R 3'
_symmetry_space_group_name_H-M   'R -3 :H'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                120.00
_cell_formula_units_Z            18
_cell_length_a                   40.173(2)
_cell_length_b                   40.173(2)
_cell_length_c                   7.1602(6)
_cell_measurement_reflns_used    31579
_cell_measurement_temperature    153(2)
_cell_measurement_theta_max      28.91
_cell_measurement_theta_min      1.01
_cell_volume                     10007.5(11)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      153(2)
_diffrn_measured_fraction_theta_full 0.946
_diffrn_measured_fraction_theta_max 0.946
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1233
_diffrn_reflns_av_sigmaI/netI    0.0611
_diffrn_reflns_limit_h_max       54
_diffrn_reflns_limit_h_min       -53
_diffrn_reflns_limit_k_max       51
_diffrn_reflns_limit_k_min       -51
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            31579
_diffrn_reflns_theta_full        28.91
_diffrn_reflns_theta_max         28.91
_diffrn_reflns_theta_min         1.01
_exptl_absorpt_coefficient_mu    0.449
_exptl_absorpt_correction_T_max  0.97251
_exptl_absorpt_correction_T_min  0.86116
_exptl_absorpt_correction_type   integration
_exptl_absorpt_process_details   'Bruker-AXS, 2003'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.417
_exptl_crystal_description       needle
_exptl_crystal_F_000             4374
_exptl_crystal_size_max          0.780
_exptl_crystal_size_mid          0.116
_exptl_crystal_size_min          0.096
_refine_diff_density_max         1.575
_refine_diff_density_min         -0.724
_refine_diff_density_rms         0.144
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     278
_refine_ls_number_reflns         5554
_refine_ls_number_restraints     5
_refine_ls_restrained_S_all      1.084
_refine_ls_R_factor_all          0.0856
_refine_ls_R_factor_gt           0.0692
_refine_ls_shift/su_max          0.005
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.1366P)²+21.7159P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1971
_refine_ls_wR_factor_ref         0.2132
_reflns_number_gt                4256
_reflns_number_total             5554
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja710815a-file003.cif
_cod_data_source_block           ss35face
_cod_original_cell_volume        10007.4(12)
_cod_original_sg_symbol_H-M      'R -3'
_cod_database_code               4108097
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-y, x-y, z'
'-x+y, -x, z'
'x+2/3, y+1/3, z+1/3'
'-y+2/3, x-y+1/3, z+1/3'
'-x+y+2/3, -x+1/3, z+1/3'
'x+1/3, y+2/3, z+2/3'
'-y+1/3, x-y+2/3, z+2/3'
'-x+y+1/3, -x+2/3, z+2/3'
'-x, -y, -z'
'y, -x+y, -z'
'x-y, x, -z'
'-x+2/3, -y+1/3, -z+1/3'
'y+2/3, -x+y+1/3, -z+1/3'
'x-y+2/3, x+1/3, -z+1/3'
'-x+1/3, -y+2/3, -z+2/3'
'y+1/3, -x+y+2/3, -z+2/3'
'x-y+1/3, x+2/3, -z+2/3'
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
C1 C 0.73850(9) -0.00973(9) 1.2536(4) 0.0254(6) Uani 1 1 d .
H1 H 0.7359 -0.0238 1.3647 0.030 Uiso 1 1 calc R
C2 C 0.71542(9) 0.00464(9) 1.2089(4) 0.0261(6) Uani 1 1 d .
H2 H 0.6952 0.0020 1.2874 0.031 Uiso 1 1 calc R
C3 C 0.72426(8) 0.02449(8) 1.0307(4) 0.0206(6) Uani 1 1 d .
H3 H 0.7108 0.0360 0.9771 0.025 Uiso 1 1 calc R
C4 C 0.75638(8) 0.02389(8) 0.9490(4) 0.0200(6) Uani 1 1 d .
C5 C 0.77485(8) 0.04117(8) 0.7730(4) 0.0207(6) Uani 1 1 d .
C6 C 0.80470(8) 0.04064(8) 0.6850(4) 0.0212(6) Uani 1 1 d .
H6 H 0.8170 0.0275 0.7337 0.025 Uiso 1 1 calc R
C7 C 0.79324(8) 0.07775(8) 0.4720(4) 0.0192(6) Uani 1 1 d .
C8 C 0.81580(8) 0.06148(8) 0.5134(4) 0.0204(6) Uani 1 1 d .
C9 C 0.84675(9) 0.06118(9) 0.4055(4) 0.0246(6) Uani 1 1 d .
C10 C 0.85339(9) 0.10532(9) 0.1298(4) 0.0230(6) Uani 1 1 d .
C11 C 0.81932(8) 0.10941(8) 0.1602(4) 0.0202(6) Uani 1 1 d .
C12 C 0.79422(8) 0.09863(8) 0.3088(4) 0.0188(5) Uani 1 1 d .
C13 C 0.81027(8) 0.12840(8) 0.0188(4) 0.0214(6) Uani 1 1 d .
H13 H 0.8248 0.1379 -0.0929 0.026 Uiso 1 1 calc R
C14 C 0.77878(8) 0.13180(8) 0.0580(4) 0.0194(6) Uani 1 1 d .
C15 C 0.76146(8) 0.14910(8) -0.0543(4) 0.0199(6) Uani 1 1 d .
C16 C 0.72926(9) 0.15233(9) -0.0125(4) 0.0252(6) Uani 1 1 d .
H16 H 0.7146 0.1427 0.0985 0.030 Uiso 1 1 calc R
C17 C 0.72106(9) 0.17171(9) -0.1563(5) 0.0282(7) Uani 1 1 d .
H17 H 0.7003 0.1767 -0.1509 0.034 Uiso 1 1 calc R
C18 C 0.74607(9) 0.18238(9) -0.3026(4) 0.0252(6) Uani 1 1 d .
H18 H 0.7447 0.1955 -0.4102 0.030 Uiso 1 1 calc R
C19 C 0.89839(9) 0.08282(10) 0.1789(5) 0.0298(7) Uani 1 1 d .
H19A H 0.9109 0.0775 0.2851 0.036 Uiso 1 1 calc R
H19B H 0.9172 0.1081 0.1260 0.036 Uiso 1 1 calc R
C20 C 0.88773(13) 0.05202(15) 0.0306(6) 0.0549(12) Uani 1 1 d .
H20A H 0.8707 0.0264 0.0861 0.066 Uiso 1 1 calc R
H20B H 0.8735 0.0561 -0.0713 0.066 Uiso 1 1 calc R
C21 C 0.9233(2) 0.0531(3) -0.0488(9) 0.106(3) Uani 1 1 d D
C22 C 0.9323(5) 0.0616(8) -0.222(2) 0.243(7) Uani 0.749(7) 1 d PD
C23 C 0.9655(5) 0.0566(8) -0.295(2) 0.243(7) Uani 0.749(7) 1 d PD
C24 C 0.9833(5) 0.0822(7) -0.469(2) 0.243(7) Uani 0.749(7) 1 d PD
C25 C 0.9413(14) 0.0339(18) 0.063(5) 0.243(7) Uani 0.251(7) 1 d PD
C26 C 0.9631(16) 0.022(2) -0.077(7) 0.243(7) Uani 0.251(7) 1 d PD
C27 C 1.0152(16) 0.0354(15) 0.018(10) 0.243(7) Uani 0.251(7) 1 d P
N1 N 0.86431(7) 0.08435(7) 0.2480(3) 0.0219(5) Uani 1 1 d .
O1 O 0.85876(7) 0.04027(8) 0.4595(4) 0.0397(6) Uani 1 1 d .
O2 O 0.87327(7) 0.12088(8) -0.0072(3) 0.0370(6) Uani 1 1 d .
S1 S 0.77277(2) 0.00010(2) 1.08897(11) 0.0257(2) Uani 1 1 d .
S2 S 0.75939(2) 0.06754(2) 0.64442(10) 0.0221(2) Uani 1 1 d .
S3 S 0.76009(2) 0.11222(2) 0.27490(10) 0.0217(2) Uani 1 1 d .
S4 S 0.78029(2) 0.16937(2) -0.26948(10) 0.0238(2) Uani 1 1 d .
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'
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
C2 C1 S1 112.6(2) . .
C1 C2 C3 114.3(3) . .
C4 C3 C2 109.0(3) . .
C3 C4 C5 126.7(3) . .
C3 C4 S1 111.7(2) . .
C5 C4 S1 121.6(2) . .
C6 C5 C4 129.6(3) . .
C6 C5 S2 110.5(2) . .
C4 C5 S2 119.9(2) . .
C5 C6 C8 114.1(3) . .
C8 C7 C12 128.2(3) . .
C8 C7 S2 110.9(2) . .
C12 C7 S2 120.8(2) . .
C7 C8 C6 111.9(3) . .
C7 C8 C9 130.2(3) . .
C6 C8 C9 117.7(3) . .
O1 C9 N1 117.9(3) . .
O1 C9 C8 117.8(3) . .
N1 C9 C8 124.2(3) . .
O2 C10 N1 118.0(3) . .
O2 C10 C11 117.9(3) . .
N1 C10 C11 124.2(3) . .
C12 C11 C13 112.0(3) . .
C12 C11 C10 130.8(3) . .
C13 C11 C10 117.1(3) . .
C11 C12 C7 128.1(3) . .
C11 C12 S3 111.3(2) . .
C7 C12 S3 120.5(2) . .
C14 C13 C11 113.9(3) . .
C13 C14 C15 128.6(3) . .
C13 C14 S3 110.6(2) . .
C15 C14 S3 120.8(2) . .
C16 C15 C14 128.0(3) . .
C16 C15 S4 110.8(2) . .
C14 C15 S4 121.2(2) . .
C15 C16 C17 112.0(3) . .
C18 C17 C16 113.0(3) . .
C17 C18 S4 112.0(2) . .
N1 C19 C20 112.1(3) . .
C21 C20 C19 111.1(5) . .
C22 C21 C20 120.3(8) . .
C22 C21 C25 119.8(16) . .
C20 C21 C25 118.0(14) . .
C21 C22 C23 116.3(13) . .
C22 C23 C24 109.3(14) . .
C21 C25 C26 107(3) . .
C27 C26 C25 113(7) 12_545 .
C27 C26 C27 38(5) 12_545 2_645
C25 C26 C27 109(3) . 2_645
C27 C26 C27 29(5) 12_545 .
C25 C26 C27 112(4) . .
C27 C26 C27 67(3) 2_645 .
C26 C27 C27 114(8) 11_665 12_545
C26 C27 C27 129(10) 11_665 11_665
C27 C27 C27 116(4) 12_545 11_665
C26 C27 C26 109(6) 11_665 3_765
C27 C27 C26 134(5) 12_545 3_765
C27 C27 C26 28(3) 11_665 3_765
C26 C27 C26 99(6) 11_665 .
C27 C27 C26 21(5) 12_545 .
C27 C27 C26 130(6) 11_665 .
C26 C27 C26 137(4) 3_765 .
C9 N1 C10 132.3(3) . .
C9 N1 C19 114.0(2) . .
C10 N1 C19 113.2(2) . .
C1 S1 C4 92.44(15) . .
C7 S2 C5 92.55(14) . .
C12 S3 C14 92.12(14) . .
C18 S4 C15 92.20(15) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 C2 1.353(5) .
C1 S1 1.702(3) .
C2 C3 1.452(4) .
C3 C4 1.428(4) .
C4 C5 1.451(4) .
C4 S1 1.727(3) .
C5 C6 1.364(4) .
C5 S2 1.736(3) .
C6 C8 1.427(4) .
C7 C8 1.389(4) .
C7 C12 1.428(4) .
C7 S2 1.727(3) .
C8 C9 1.469(4) .
C9 O1 1.222(4) .
C9 N1 1.407(4) .
C10 O2 1.221(4) .
C10 N1 1.410(4) .
C10 C11 1.474(4) .
C11 C12 1.379(4) .
C11 C13 1.420(4) .
C12 S3 1.728(3) .
C13 C14 1.368(4) .
C14 C15 1.448(4) .
C14 S3 1.733(3) .
C15 C16 1.396(4) .
C15 S4 1.730(3) .
C16 C17 1.425(4) .
C17 C18 1.364(4) .
C18 S4 1.714(3) .
C19 N1 1.486(4) .
C19 C20 1.520(5) .
C20 C21 1.518(6) .
C21 C22 1.288(13) .
C21 C25 1.52(2) .
C22 C23 1.538(14) .
C23 C24 1.543(16) .
C25 C26 1.55(2) .
C26 C27 0.95(8) 12_545
C26 C27 1.87(9) 2_645
C26 C27 2.00(9) .
C27 C26 0.95(8) 11_665
C27 C27 1.26(6) 12_545
C27 C27 1.26(6) 11_665
C27 C26 1.87(9) 3_765
