Isomerically pure syn-anthradithiophenes: synthesis, properties, and FET performance.
Lehnherr, Dan; Waterloo, Andreas R.; Goetz, Katelyn P.; Payne, Marcia M.; Hampel, Frank; Anthony, John E.; Jurchescu, Oana D.; Tykwinski, Rik R.; Organic letters 14 (2012) 3660–3663; doi:10.1021/ol301503k

data_1508296
_publ_section_title
;
 Isomerically pure syn-anthradithiophenes: synthesis, properties, and FET
 performance.
;
_journal_issue                   14
_journal_name_full               'Organic letters'
_journal_page_first              3660
_journal_page_last               3663
_journal_paper_doi               10.1021/ol301503k
_journal_volume                  14
_journal_year                    2012
_chemical_formula_moiety         'C34 H36 F2 S2 Si2'
_chemical_formula_sum            'C34 H36 F2 S2 Si2'
_chemical_formula_weight         602.93
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2012-04-16
_audit_creation_method
;
  Olex2 1.2-beta
  (compiled 2012.03.20 svn.r2253, GUI svn.r4124)
;
_cell_angle_alpha                87.014(13)
_cell_angle_beta                 84.846(15)
_cell_angle_gamma                63.64(2)
_cell_formula_units_Z            1
_cell_length_a                   7.0493(17)
_cell_length_b                   7.9236(15)
_cell_length_c                   16.025(2)
_cell_measurement_reflns_used    878
_cell_measurement_temperature    153.05(10)
_cell_measurement_theta_max      54.1691
_cell_measurement_theta_min      6.3202
_cell_volume                     798.7(3)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
(compiled Jan 23 2012,18:06:46)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
(compiled Jan 23 2012,18:06:46)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
(compiled Jan 23 2012,18:06:46)
;
_computing_molecular_graphics
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement
;
SHELXL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution
;
SHELXS, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_diffrn_ambient_temperature      153.05(10)
_diffrn_detector_area_resol_mean 10.6144
_diffrn_measured_fraction_theta_full 0.701
_diffrn_measured_fraction_theta_max 0.701
_diffrn_measurement_details
;
  1 omega  -67.00  -37.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -        0.0000 -178.0000  150.0000 30

  2 omega  -99.00  -69.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -        0.0000 -178.0000  150.0000 30

  3 omega -117.00  -79.00   1.0000    4.0400
omega____ theta____ kappa____ phi______ frames
    -      -55.4492  -99.0000  -90.0000 38

  4 omega -140.00  -85.00   1.0000    4.0400
omega____ theta____ kappa____ phi______ frames
    -      -55.4492  -99.0000    0.0000 55

  5 omega -148.00 -121.00   1.0000    4.0400
omega____ theta____ kappa____ phi______ frames
    -      -55.4492  -99.0000  -90.0000 27

  6 omega  105.00  151.00   1.0000    4.0400
omega____ theta____ kappa____ phi______ frames
    -       55.4492   82.0000   50.0000 46

  7 omega  -61.00   15.00   1.0000    4.0400
omega____ theta____ kappa____ phi______ frames
    -      -70.5000   50.0000   30.0000 76

  8 omega  -48.00   22.00   1.0000    4.0400
omega____ theta____ kappa____ phi______ frames
    -      -70.5000   38.0000 -120.0000 70

  9 omega   37.00   93.00   1.0000    4.0400
omega____ theta____ kappa____ phi______ frames
    -      110.8984  -38.0000   60.0000 56

 10 omega  133.00  166.00   1.0000    4.0400
omega____ theta____ kappa____ phi______ frames
    -      110.8984  111.0000  150.0000 33

 11 omega   29.00  104.00   1.0000    4.0400
omega____ theta____ kappa____ phi______ frames
    -      110.8984  -77.0000   60.0000 75

 12 omega   35.00   92.00   1.0000    4.0400
omega____ theta____ kappa____ phi______ frames
    -      110.8984  -25.0000  120.0000 57

 13 omega  104.00  131.00   1.0000    4.0400
omega____ theta____ kappa____ phi______ frames
    -      110.8984  111.0000  150.0000 27

 14 omega   17.00   82.00   1.0000    4.0400
omega____ theta____ kappa____ phi______ frames
    -      110.8984  -25.0000    0.0000 65

 15 omega   74.00  162.00   1.0000    4.0400
omega____ theta____ kappa____ phi______ frames
    -      110.8984   38.0000  -90.0000 88
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0413003000
_diffrn_orient_matrix_UB_12      -0.1130480000
_diffrn_orient_matrix_UB_13      0.0830832000
_diffrn_orient_matrix_UB_21      -0.1744311000
_diffrn_orient_matrix_UB_22      -0.0596536000
_diffrn_orient_matrix_UB_23      -0.0149171000
_diffrn_orient_matrix_UB_31      0.1663930000
_diffrn_orient_matrix_UB_32      -0.1753640000
_diffrn_orient_matrix_UB_33      -0.0468418000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.5418
_diffrn_reflns_av_R_equivalents  0.0217
_diffrn_reflns_av_unetI/netI     0.0295
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            1809
_diffrn_reflns_theta_full        54.23
_diffrn_reflns_theta_max         54.23
_diffrn_reflns_theta_min         7.03
_diffrn_source                   'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.498
_exptl_absorpt_correction_T_max  0.908
_exptl_absorpt_correction_T_min  0.747
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
(compiled Jan 23 2012,18:06:46)
Analytical numeric absorption correction using a multifaceted crystal
            model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
;
_exptl_crystal_colour            'clear dark red'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   dark
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.253
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             318
_exptl_crystal_recrystallization_method 'crystallized from n-pentane'
_exptl_crystal_size_max          0.1914
_exptl_crystal_size_mid          0.0899
_exptl_crystal_size_min          0.0342
_refine_diff_density_max         0.174
_refine_diff_density_min         -0.213
_refine_diff_density_rms         0.038
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     197
_refine_ls_number_reflns         1371
_refine_ls_number_restraints     5
_refine_ls_restrained_S_all      1.052
_refine_ls_R_factor_all          0.0476
_refine_ls_R_factor_gt           0.0382
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0609P)^2^+0.3313P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0970
_refine_ls_wR_factor_ref         0.1042
_reflns_number_gt                1173
_reflns_number_total             1371
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol301503k_si_002.cif
_cod_data_source_block           syn-2a
_cod_depositor_comments
'Adding full bibliography for 1508296--1508298.cif.'
_cod_database_code               1508296
_chemical_oxdiff_formula         'C34 H36 F2 S2 Si2'
_reflns_odcompleteness_completeness 69.91
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     54.18