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_1508297
_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         'C40 H48 F2 S2 Si2'
_chemical_formula_sum            'C40 H48 F2 S2 Si2'
_chemical_formula_weight         687.08
_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             2012-06-20
_audit_creation_method
;
  Olex2 1.2
  (compiled 2012.05.09 svn.r2324, GUI svn.r4230)
;
_cell_angle_alpha                100.990(7)
_cell_angle_beta                 92.320(7)
_cell_angle_gamma                98.594(8)
_cell_formula_units_Z            1
_cell_length_a                   7.5855(7)
_cell_length_b                   8.1701(8)
_cell_length_c                   16.2295(12)
_cell_measurement_reflns_used    2718
_cell_measurement_temperature    172.9
_cell_measurement_theta_max      73.2068
_cell_measurement_theta_min      5.5631
_cell_volume                     973.81(15)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_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      172.9
_diffrn_detector_area_resol_mean 10.6144
_diffrn_measured_fraction_theta_full 0.965
_diffrn_measured_fraction_theta_max 0.965
_diffrn_measurement_details
;
  1 omega  -50.00   23.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -41.1678   38.0000   90.0000 73

  2 omega  -78.00   -3.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -41.1678  125.0000   60.0000 75

  3 omega  -43.00   25.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -41.1678   38.0000 -120.0000 68

  4 omega  -47.00    9.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -41.1678   38.0000  -30.0000 56

  5 omega  -22.00   29.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -41.1678   38.0000    0.0000 51

  6 omega   48.00   92.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       41.1678 -125.0000  -30.0000 44

  7 omega  101.00  177.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      107.6436  125.0000  150.0000 76

  8 omega   61.00  178.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      107.6436   15.0000  -90.0000 117

  9 omega   29.00   68.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      107.6436  -77.0000 -120.0000 39

 10 omega   67.00  141.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      107.6436  -77.0000   90.0000 74

 11 omega   57.00   98.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      107.6436  -45.0000 -150.0000 41

 12 omega   35.00   84.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      107.6436  -45.0000   90.0000 49

 13 omega   93.00  172.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      107.6436   45.0000  -30.0000 79

 14 omega   67.00   97.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      107.6436  -45.0000  -90.0000 30

 15 omega   47.00   93.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      107.6436  -45.0000   30.0000 46

 16 omega   88.00  120.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      107.6436  -77.0000 -120.0000 32

 17 omega   71.00  119.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      107.6436 -125.0000  126.0000 48

 18 omega  101.00  150.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      107.6436  125.0000 -180.0000 49

 19 omega   91.00  116.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      107.6436 -114.0000 -163.0000 25

 20 omega   73.00  110.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      107.6436 -115.0000  -70.0000 37
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.1430173000
_diffrn_orient_matrix_UB_12      0.1165400000
_diffrn_orient_matrix_UB_13      0.0081163000
_diffrn_orient_matrix_UB_21      -0.1452894000
_diffrn_orient_matrix_UB_22      -0.1526297000
_diffrn_orient_matrix_UB_23      0.0015092000
_diffrn_orient_matrix_UB_31      0.0289746000
_diffrn_orient_matrix_UB_32      0.0314765000
_diffrn_orient_matrix_UB_33      0.0965897000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.5418
_diffrn_reflns_av_R_equivalents  0.0236
_diffrn_reflns_av_unetI/netI     0.0379
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            6377
_diffrn_reflns_theta_full        73.37
_diffrn_reflns_theta_max         73.37
_diffrn_reflns_theta_min         5.57
_diffrn_source                   'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.105
_exptl_absorpt_correction_T_max  0.800
_exptl_absorpt_correction_T_min  0.680
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
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    1.172
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             366
_exptl_crystal_recrystallization_method 'crystallized from DCM and Acetone'
_exptl_crystal_size_max          0.2756
_exptl_crystal_size_mid          0.1834
_exptl_crystal_size_min          0.1503
_refine_diff_density_max         0.521
_refine_diff_density_min         -0.461
_refine_diff_density_rms         0.061
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.070
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     215
_refine_ls_number_reflns         3776
_refine_ls_number_restraints     11
_refine_ls_restrained_S_all      1.076
_refine_ls_R_factor_all          0.0823
_refine_ls_R_factor_gt           0.0712
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.1039P)^2^+0.6812P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1944
_refine_ls_wR_factor_ref         0.2083
_reflns_number_gt                3126
_reflns_number_total             3776
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol301503k_si_002.cif
_cod_data_source_block           syn-2b
_cod_depositor_comments
'Adding full bibliography for 1508296--1508298.cif.'
_cod_database_code               1508297
_chemical_oxdiff_formula         'C40 H48 F2 S2 Si2'
_reflns_odcompleteness_completeness 99.83
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97