Facile and scalable synthesis of the fused-ring heterocycles thieno[3,2-b]thiophene and thieno[3,2-b]furan.
Henssler, John T.; Matzger, Adam J.; Organic letters 11 (2009) 3144–3147; doi:10.1021/ol9010745

data_1504005
_publ_section_title
;
 Facile and scalable synthesis of the fused-ring heterocycles
 thieno[3,2-b]thiophene and thieno[3,2-b]furan.
;
_journal_issue                   14
_journal_name_full               'Organic letters'
_journal_page_first              3144
_journal_page_last               3147
_journal_paper_doi               10.1021/ol9010745
_journal_volume                  11
_journal_year                    2009
_chemical_formula_moiety         'C10 H6 O S2'
_chemical_formula_sum            'C10 H6 O S2'
_chemical_formula_weight         206.27
_chemical_name_common            T-FT
_chemical_name_systematic
; 

2-(thiophen-2-yl)thieno[3,2-b]furan

;
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_Int_Tables_number      19
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.43737(10)
_cell_length_b                   16.8839(3)
_cell_length_c                   5.68402(10)
_cell_measurement_reflns_used    6227
_cell_measurement_temperature    95(2)
_cell_measurement_theta_max      66.7
_cell_measurement_theta_min      7.0
_cell_volume                     905.69(2)
_computing_cell_refinement       PROCESS-AUTO
_computing_data_collection       PROCESS-AUTO
_computing_data_reduction        'CrystalStructure 3.8'
_computing_publication_material  'CrystalStructure 3.8'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    SIR2004
_diffrn_ambient_temperature      95(2)
_diffrn_detector_area_resol_mean 10.00
_diffrn_measured_fraction_theta_full 0.944
_diffrn_measured_fraction_theta_max 0.944
_diffrn_measurement_device_type  'Rigaku RAXIS-Spider'
_diffrn_measurement_method       \w
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54187
_diffrn_reflns_av_R_equivalents  0.0313
_diffrn_reflns_av_sigmaI/netI    0.0286
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       6
_diffrn_reflns_limit_l_min       -5
_diffrn_reflns_number            6125
_diffrn_reflns_theta_full        66.52
_diffrn_reflns_theta_max         66.52
_diffrn_reflns_theta_min         7.04
_exptl_absorpt_coefficient_mu    4.923
_exptl_absorpt_correction_T_max  0.4393
_exptl_absorpt_correction_T_min  0.4393
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;

    Higashi, T. (1995). Program for Absorption Correction.

    Rigaku Corporation, Tokyo, Japan.

;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.513
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             424
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.34
_exptl_crystal_size_min          0.31
_refine_diff_density_max         0.701
_refine_diff_density_min         -0.297
_refine_diff_density_rms         0.109
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.05(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.160
_refine_ls_hydrogen_treatment    riding
_refine_ls_matrix_type           full
_refine_ls_number_parameters     119
_refine_ls_number_reflns         1496
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.160
_refine_ls_R_factor_all          0.0496
_refine_ls_R_factor_gt           0.0491
_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^)+(0.0726P)^2^+1.5557P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1320
_refine_ls_wR_factor_ref         0.1325
_reflns_number_gt                1470
_reflns_number_total             1496
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol9010745_si_001.cif
_cod_data_source_block           T-FT
_cod_database_code               1504005