Two-Dimensional π-Expanded Quinoidal Terthiophenes Terminated with Dicyanomethylenes as n-Type Semiconductors for High-Performance Organic Thin-Film Transistors.
Zhang, Cheng; Zang, Yaping; Gann, Eliot; McNeill, Christopher R.; Zhu, Xiaozhang; Di, Chong-An; Zhu, Daoben; Journal of the American Chemical Society  (2014) 141106072905001–; doi:10.1021/ja510003y

data_4122892
_publ_section_title
;
 Two-Dimensional \p-Expanded Quinoidal Terthiophenes Terminated with
 Dicyanomethylenes as n-Type Semiconductors for High-Performance Organic
 Thin-Film Transistors.
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              141106072905001
_journal_paper_doi               10.1021/ja510003y
_journal_year                    2014
_chemical_formula_moiety         'C44.50 H44 Cl N5 O2 S5'
_chemical_formula_sum            'C44.5 H44 Cl N5 O2 S5'
_chemical_formula_weight         876.60
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_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                 109.57(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   13.212(3)
_cell_length_b                   37.811(8)
_cell_length_c                   10.198(2)
_cell_measurement_reflns_used    5206
_cell_measurement_temperature    113(2)
_cell_measurement_theta_max      27.09
_cell_measurement_theta_min      1.72
_cell_volume                     4800(2)
_computing_cell_refinement       CrystalClear
_computing_data_collection       'CrystalClear (Rigaku Inc., 2008)'
_computing_data_reduction        CrystalClear
_computing_molecular_graphics    'CrystalStructure 4.0'
_computing_publication_material  'CrystalStructure 4.0 (Rigaku, 2009)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      113(2)
_diffrn_detector_area_resol_mean 7.314
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Rigaku Saturn70 CCD'
_diffrn_measurement_method       \w
_diffrn_radiation_monochromator  multilayer
_diffrn_radiation_source         'rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0683
_diffrn_reflns_av_sigmaI/netI    0.0495
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       44
_diffrn_reflns_limit_k_min       -44
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            22428
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         1.72
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.337
_exptl_absorpt_correction_T_max  0.9867
_exptl_absorpt_correction_T_min  0.9176
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Jacobson, R. (1998) Private communication'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.213
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1836
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.04
_refine_diff_density_max         1.061
_refine_diff_density_min         -0.717
_refine_diff_density_rms         0.160
_refine_ls_extinction_coef       0.017(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.808
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     246
_refine_ls_number_reflns         4224
_refine_ls_number_restraints     38
_refine_ls_restrained_S_all      1.816
_refine_ls_R_factor_all          0.1704
_refine_ls_R_factor_gt           0.1514
_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^)+(0.2000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.4288
_refine_ls_wR_factor_ref         0.4522
_reflns_number_gt                3113
_reflns_number_total             4224
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja510003y_si_002.cif
_cod_data_source_block           shelxl
_cod_original_cell_volume        4800.2(16)
_cod_original_formula_sum        'C44.50 H44 Cl N5 O2 S5'
_cod_database_code               4122892