Synthesis, Structural Characterization, and Unusual Field-Effect Behavior of Organic Transistor Semiconductor Oligomers: Inferiority of Oxadiazole Compared with Other Electron-Withdrawing Subunits
Taegweon Lee; Chad A. Landis; Bal Mukund Dhar; Byung Jun Jung; Jia Sun; Amy Sarjeant; Ho-Jin Lee; Howard E. Katz; Journal of the American Chemical Society 131 (2009) 1692–1705; doi:10.1021/ja807219x

data_4103875
_publ_section_title
;
 Synthesis, Structural Characterization, and Unusual Field-Effect Behavior
 of Organic Transistor Semiconductor Oligomers: Inferiority of Oxadiazole
 Compared with Other Electron-Withdrawing Subunits
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              1692
_journal_page_last               1705
_journal_paper_doi               10.1021/ja807219x
_journal_volume                  131
_journal_year                    2009
_chemical_formula_moiety         'C42 H20 F6 N6 O2 S2'
_chemical_formula_sum            'C42 H20 F6 N6 O2 S2'
_chemical_formula_weight         818.76
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_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
;
'Fri Mar 21 09:56:37 2008'
;
_audit_creation_method           SHELXL-97
_cell_angle_alpha                98.387(4)
_cell_angle_beta                 98.331(4)
_cell_angle_gamma                93.949(4)
_cell_formula_units_Z            2
_cell_length_a                   7.0932(3)
_cell_length_b                   11.9357(5)
_cell_length_c                   20.7406(9)
_cell_measurement_reflns_used    3413
_cell_measurement_temperature    110
_cell_measurement_theta_max      26.4999
_cell_measurement_theta_min      3.7142
_cell_volume                     1711.56(13)
_computing_cell_refinement       'Oxford Diffraction CrysAlis RED'
_computing_data_collection       'Oxford Diffraction CrysAlis CCD'
_computing_data_reduction        'Oxford Diffraction CrysAlis RED'
_computing_molecular_graphics    'Sheldrick, G.M. (2000). SHELXTL v6.10.'
_computing_publication_material  'Sheldrick, G.M. (2000). SHELXTL v6.10.'
_computing_structure_refinement  'Sheldrick, G.M. (2000). SHELXTL v6.10.'
_computing_structure_solution    'Sheldrick, G.M. (2000). SHELXTL v6.10.'
_diffrn_ambient_temperature      110
_diffrn_detector_area_resol_mean 15.9890
_diffrn_measured_fraction_theta_full 0.937
_diffrn_measured_fraction_theta_max 0.937
_diffrn_measurement_details      'see scan set'
_diffrn_measurement_device       Kappa
_diffrn_measurement_device_type  Xcalibur3
_diffrn_measurement_method       ' phi omega scans'
_diffrn_orient_matrix_UB_11      0.0841822495
_diffrn_orient_matrix_UB_12      0.0368362873
_diffrn_orient_matrix_UB_13      0.0020713758
_diffrn_orient_matrix_UB_21      -0.0340055706
_diffrn_orient_matrix_UB_22      0.0400558424
_diffrn_orient_matrix_UB_23      0.0233259654
_diffrn_orient_matrix_UB_31      0.0451972537
_diffrn_orient_matrix_UB_32      -0.0259697130
_diffrn_orient_matrix_UB_33      0.0260428519
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0813
_diffrn_reflns_av_sigmaI/netI    0.1542
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            14535
_diffrn_reflns_resolution_max    0.79
_diffrn_reflns_theta_full        26.61
_diffrn_reflns_theta_max         26.61
_diffrn_reflns_theta_min         3.72
_diffrn_source_current           40
_diffrn_source_power             2
_diffrn_source_voltage           50
_exptl_absorpt_coefficient_mu    0.239
_exptl_absorpt_correction_T_max  0.993
_exptl_absorpt_correction_T_min  0.961
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.32.5 (release 08-05-2007 CrysAlis171 .NET)
(compiled May  8 2007,13:10:02)
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            orange
_exptl_crystal_density_diffrn    1.589
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             832
_exptl_crystal_size_max          0.2245
_exptl_crystal_size_mid          0.1430
_exptl_crystal_size_min          0.0370
_refine_diff_density_max         0.815
_refine_diff_density_min         -0.423
_refine_diff_density_rms         0.092
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     523
_refine_ls_number_reflns         6693
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.022
_refine_ls_R_factor_all          0.1777
_refine_ls_R_factor_gt           0.0846
_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^)+(0.0413P)^2^+4.4492P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1388
_refine_ls_wR_factor_ref         0.1757
_reflns_number_gt                3384
_reflns_number_total             6693
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja807219x_si_002.cif
_cod_data_source_block           x0440
_cod_original_sg_symbol_H-M      'P -1 '
_cod_database_code               4103875
_audit_creation_method_reference
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.32.5 (release 08-05-2007 CrysAlis171 .NET)
(compiled May  8 2007,13:10:02)
;
_computing_data_collection_reference
;
CrysAlis CCD, Oxford Diffraction Ltd.,
Version 1.171.32.5 (release 08-05-2007 CrysAlis171 .NET)
(compiled May  8 2007,13:10:02)
;
_computing_cell_refinment_reference
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.32.5 (release 08-05-2007 CrysAlis171 .NET)
(compiled May  8 2007,13:10:02)
;
_computing_data_reduction_reference
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.32.5 (release 08-05-2007 CrysAlis171 .NET)
(compiled May  8 2007,13:10:02)
;
_cell_measurement_resolution_max 0.80
_jhu_your_name_here              'Dr. Amy A Sarjeant'
_jhu_your_lab_here               'NCB 240'
_jhu_your_phone_number_here      x6-8569
_jhu_your_email_here             xray@jhu.edu
_jhu_institutional_source        'Katz Lab'
_jhu_submitting_scientist        'Taegweon Lee'
_jhu_scientist_phone             x6-0799
_jhu_scientist_email             tlee56@jhu.edu
_jhu_identifying_number          x0440
_jhu_xray_labbook                II-113
_jhu_crystalization_labbook
;
;
_jhu_crystalization_solvent
;
;
_jhu_crystalization_method
;
;
_jhu_diffraction_detector_distance 50
_jhu_quality_factor              3