Reduced band gap dithieno[3,2-b:2',3'-d]pyrroles: new n-type organic materials via unexpected reactivity.
Pappenfus, Ted M.; Hermanson, Bethany J.; Helland, Tyler J.; Lee, Garett G. W.; Drew, Steven M.; Mann, Kent R.; McGee, Kari A.; Rasmussen, Seth C.; Organic letters 10 (2008) 1553–1556; doi:10.1021/ol8002018

data_1504599
_publ_section_title
;
 Reduced band gap dithieno[3,2-b:2',3'-d]pyrroles: new n-type organic
 materials via unexpected reactivity.
;
_journal_issue                   8
_journal_name_full               'Organic letters'
_journal_page_first              1553
_journal_page_last               1556
_journal_paper_doi               10.1021/ol8002018
_journal_volume                  10
_journal_year                    2008
_chemical_formula_moiety         'C26 H19 N5 S2'
_chemical_formula_sum            'C26 H19 N5 S2'
_chemical_formula_weight         465.58
_chemical_name_common            07278a
_chemical_name_systematic
; 
 ? 
;
_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_method           SHELXL-97
_cell_angle_alpha                80.0060(10)
_cell_angle_beta                 79.873(2)
_cell_angle_gamma                71.976(2)
_cell_formula_units_Z            2
_cell_length_a                   6.8734(6)
_cell_length_b                   10.4761(9)
_cell_length_c                   16.9087(15)
_cell_measurement_reflns_used    3019
_cell_measurement_temperature    173(2)
_cell_volume                     1130.48(17)
_computing_cell_refinement       'SAINT, Bruker'
_computing_data_collection       'SMART, Bruker'
_computing_data_reduction        'SAINT, Bruker'
_computing_molecular_graphics    'SHELXTL, Bruker'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker SMART Platform CCD'
_diffrn_measurement_method       'area detector, omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'normal-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0532
_diffrn_reflns_av_sigmaI/netI    0.0704
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            12353
_diffrn_reflns_theta_full        26.38
_diffrn_reflns_theta_max         26.38
_diffrn_reflns_theta_min         1.23
_exptl_absorpt_coefficient_mu    0.261
_exptl_absorpt_correction_T_max  0.9948
_exptl_absorpt_correction_T_min  0.9377
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS, R. Blessing, 1995'
_exptl_crystal_colour            purple
_exptl_crystal_density_diffrn    1.368
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             484
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.373
_refine_diff_density_min         -0.420
_refine_diff_density_rms         0.115
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_hydrogen_treatment    riding
_refine_ls_matrix_type           full
_refine_ls_number_parameters     298
_refine_ls_number_reflns         4609
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.028
_refine_ls_R_factor_all          0.0829
_refine_ls_R_factor_gt           0.0454
_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^)+(0.0658P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1051
_refine_ls_wR_factor_ref         0.1275
_reflns_number_gt                3146
_reflns_number_total             4609
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol8002018-file002.cif
_cod_data_source_block           DTP-Q
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               1504599