Bisthiadiazole-Fused Tetraazapentacenequinone: An Air-Stable Solution-Processable n-Type Organic Semiconductor.
Cortizo-Lacalle, Diego; Gozalvez, Cristian; Olano, Mikel; Sun, Xiangnan; Melle-Franco, Manuel; Hueso, Luis E.; Mateo-Alonso, Aurelio; Organic letters 17 (2015) 5902–5905; doi:10.1021/acs.orglett.5b03099

data_1555454
_publ_section_title
;
 Bisthiadiazole-Fused Tetraazapentacenequinone: An Air-Stable
 Solution-Processable n-Type Organic Semiconductor.
;
_journal_issue                   23
_journal_name_full               'Organic letters'
_journal_page_first              5902
_journal_page_last               5905
_journal_paper_doi               10.1021/acs.orglett.5b03099
_journal_volume                  17
_journal_year                    2015
_chemical_compound_source        'synthesis as described'
_chemical_formula_moiety         'C62 H84 N8 O2 S2 Si4'
_chemical_formula_sum            'C62 H84 N8 O2 S2 Si4'
_chemical_formula_weight         1149.85
_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_cell_setting           triclinic
_symmetry_Int_Tables_number      2
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2015-10-02T14:07:20-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                80.640(3)
_cell_angle_beta                 82.824(3)
_cell_angle_gamma                75.922(4)
_cell_formula_units_Z            1
_cell_length_a                   8.2413(4)
_cell_length_b                   12.7682(6)
_cell_length_c                   15.6926(6)
_cell_measurement_reflns_used    4249
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      76.135
_cell_measurement_theta_min      3.572
_cell_measurement_wavelength     1.54184
_cell_volume                     1574.06(13)
_computing_cell_refinement       'CrysAlis Pro (Oxford Diffraction Ltd., 2011)'
_computing_data_collection       'CrysAlis Pro (Oxford Diffraction Ltd., 2011)'
_computing_data_reduction        'CrysAlis Pro (Oxford Diffraction Ltd., 2011)'
_computing_molecular_graphics    'Diamond v.3.2f (Crystal Impact GbR, 2008)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'OLEX2 (Dolomanov et al, 2009)'
_diffrn_ambient_temperature      100.01(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2012
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details
;
  1 omega -113.00  -24.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.9506  -57.0000  150.0000 89

  2 omega -114.00  -11.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.9506  -57.0000   60.0000 103

  3 omega    3.00   98.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       40.9506 -125.0000  -60.0000 95

  4 omega -132.00  -76.00   1.0000   24.0000
omega____ theta____ kappa____ phi______ frames
    -      -83.0000  -77.0000 -150.0000 56

  5 omega -138.00  -85.00   1.0000   24.0000
omega____ theta____ kappa____ phi______ frames
    -      -83.0000 -111.0000 -180.0000 53

  6 omega -149.00 -122.00   1.0000   24.0000
omega____ theta____ kappa____ phi______ frames
    -      -83.0000 -111.0000  -60.0000 27

  7 omega -161.00 -119.00   1.0000   24.0000
omega____ theta____ kappa____ phi______ frames
    -      -83.0000 -111.0000  -90.0000 42

  8 omega   99.00  140.00   1.0000   24.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -77.0000    0.0000 41

  9 omega   51.00   81.00   1.0000   24.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -77.0000    0.0000 30

 10 omega   35.00   62.00   1.0000   24.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000 -111.0000 -150.0000 27

 11 omega   36.00  114.00   1.0000   24.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000 -111.0000    0.0000 78

 12 omega   86.00  149.00   1.0000   24.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   61.0000   30.0000 63

 13 omega   98.00  154.00   1.0000   24.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   61.0000  150.0000 56

 14 omega   39.00  114.00   1.0000   24.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000 -111.0000   90.0000 75

 15 omega   90.00  125.00   1.0000   24.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   61.0000   90.0000 35

 16 omega   40.00   92.00   1.0000   24.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -61.0000 -180.0000 52

 17 omega   88.00  114.00   1.0000   24.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000 -111.0000  -60.0000 26

 18 omega  125.00  157.00   1.0000   24.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   61.0000    0.0000 32

 19 omega   29.00   99.00   1.0000   24.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -94.0000  150.0000 70

 20 omega  108.00  149.00   1.0000   24.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   61.0000  -60.0000 41

 21 omega   93.00  151.00   1.0000   24.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   61.0000 -120.0000 58

 22 omega   86.00  158.00   1.0000   24.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   61.0000  -90.0000 72

 23 omega   83.00  112.00   1.0000   24.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   61.0000    0.0000 29

 24 omega   40.00   65.00   1.0000   24.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -77.0000 -180.0000 25

 25 omega   93.00  147.00   1.0000   24.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -77.0000 -180.0000 54

 26 omega   83.00  110.00   1.0000   24.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000 -111.0000 -150.0000 27
;
_diffrn_measurement_device       '\k-geometry diffractometer'
_diffrn_measurement_device_type  'Agilent SuperNova'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.185489
_diffrn_orient_matrix_UB_12      -0.0072875
_diffrn_orient_matrix_UB_13      0.0152433
_diffrn_orient_matrix_UB_21      -0.0187174
_diffrn_orient_matrix_UB_22      0.0338146
_diffrn_orient_matrix_UB_23      -0.0977247
_diffrn_orient_matrix_UB_31      0.0517885
_diffrn_orient_matrix_UB_32      -0.1207262
_diffrn_orient_matrix_UB_33      -0.014012
_diffrn_radiation_monochromator  'Multilayer optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_source         'Nova (Cu) X-ray micro-source'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0568
_diffrn_reflns_av_unetI/netI     0.1074
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            12745
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        67.496
_diffrn_reflns_theta_max         67.496
_diffrn_reflns_theta_min         2.865
_diffrn_source                   'SuperNova (Cu) X-ray Source'
_diffrn_source_current           0.8
_diffrn_source_power             0.04
_diffrn_source_voltage           50
_exptl_absorpt_coefficient_mu    1.847
_exptl_absorpt_correction_T_max  0.951
_exptl_absorpt_correction_T_min  0.799
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
        CrysAlisPro, Agilent Technologies,
        Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET)
        (compiled Dec  3 2012,18:21:49)
Analytical numeric absorption correction using a multifaceted crystal
                        model based on expressions derived by R.C. Clark & J.S.
        (Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
;
_exptl_crystal_colour            black
_exptl_crystal_density_diffrn    1.213
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             616
_exptl_crystal_size_max          0.2033
_exptl_crystal_size_mid          0.046
_exptl_crystal_size_min          0.0279
_refine_diff_density_max         0.395
_refine_diff_density_min         -0.298
_refine_diff_density_rms         0.056
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.982
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     364
_refine_ls_number_reflns         5644
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.982
_refine_ls_R_factor_all          0.0671
_refine_ls_R_factor_gt           0.0424
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0154P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0833
_refine_ls_wR_factor_ref         0.0929
_reflns_number_gt                4211
_reflns_number_total             5644
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol5b03099_si_002.cif
_cod_data_source_block           a20150382_dc97_1
_cod_original_cell_volume        1574.06(12)
_cod_database_code               1555454