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_1504598
_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         'C30 H19 N7 S2, C7 H8'
_chemical_formula_sum            'C37 H27 N7 S2'
_chemical_formula_weight         633.78
_chemical_name_common            05274
_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                98.738(2)
_cell_angle_beta                 95.006(2)
_cell_angle_gamma                104.636(2)
_cell_formula_units_Z            2
_cell_length_a                   8.0559(7)
_cell_length_b                   10.0180(9)
_cell_length_c                   21.3683(19)
_cell_measurement_reflns_used    2487
_cell_measurement_temperature    173(2)
_cell_volume                     1634.9(3)
_computing_cell_refinement       'SAINT, Bruker'
_computing_data_collection       'SMART, 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 0.995
_diffrn_measured_fraction_theta_max 0.995
_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  0.0306
_diffrn_reflns_av_sigmaI/netI    0.0349
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            16011
_diffrn_reflns_theta_full        25.05
_diffrn_reflns_theta_max         25.05
_diffrn_reflns_theta_min         0.97
_exptl_absorpt_coefficient_mu    0.201
_exptl_absorpt_correction_T_max  0.990000
_exptl_absorpt_correction_T_min  0.851242
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS, R. Blessing, 1995'
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.287
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             660
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.928
_refine_diff_density_min         -0.369
_refine_diff_density_rms         0.089
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.088
_refine_ls_hydrogen_treatment    riding
_refine_ls_matrix_type           full
_refine_ls_number_parameters     416
_refine_ls_number_reflns         5762
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.088
_refine_ls_R_factor_all          0.0743
_refine_ls_R_factor_gt           0.0503
_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^)+(0.0719P)^2^+1.4591P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1294
_refine_ls_wR_factor_ref         0.1525
_reflns_number_gt                4354
_reflns_number_total             5762
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol8002018-file002.cif
_cod_data_source_block           BTCV-DTP
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               1504598