Regiochemical Effects of Furan Substitution on the Electronic Properties and Solid-State Structure of Partial Fused-Ring Oligothiophenes
John T. Henssler; Adam J. Matzger; Journal of Organic Chemistry 77 (2012) 9298–9303; doi:10.1021/jo301744s

data_4027610
_publ_contact_author_address
;Department of Chemistry and the Macromolecular Science and Engineering Program
University of Michigan 
930 North University Avenue
Ann Arbor, MI 48109-1055
;
_publ_contact_author_email       matzger@umich.edu
_publ_contact_author_name        'Adam J. Matzger'
_publ_contact_author_phone       734.615.6627
_publ_section_title
;
 Regiochemical Effects of Furan Substitution on the Electronic Properties
 and Solid-State Structure of Partial Fused-Ring Oligothiophenes
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              9298
_journal_page_last               9303
_journal_paper_doi               10.1021/jo301744s
_journal_volume                  77
_journal_year                    2012
_chemical_formula_moiety         'C12 H6 O2 S2'
_chemical_formula_sum            'C12 H6 O2 S2'
_chemical_formula_weight         246.29
_chemical_name_common            TF-FT
_chemical_name_systematic
; 
2,2'-bithieno[3,2-b]furan 
;
_space_group_IT_number           61
_symmetry_cell_setting           orthorhombic
_symmetry_Int_Tables_number      61
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_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                   10.22625(10)
_cell_length_b                   5.79315(10)
_cell_length_c                   16.6887(3)
_cell_measurement_reflns_used    3472
_cell_measurement_temperature    95(2)
_cell_measurement_theta_max      68.2
_cell_measurement_theta_min      6.8
_cell_volume                     988.68(3)
_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 0.971
_diffrn_measured_fraction_theta_max 0.972
_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  0.0214
_diffrn_reflns_av_sigmaI/netI    0.0182
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            3738
_diffrn_reflns_theta_full        68.16
_diffrn_reflns_theta_max         68.16
_diffrn_reflns_theta_min         6.85
_exptl_absorpt_coefficient_mu    4.706
_exptl_absorpt_correction_T_max  0.7988
_exptl_absorpt_correction_T_min  0.5587
_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    1.655
_exptl_crystal_description       Prism
_exptl_crystal_F_000             504
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.410
_refine_diff_density_min         -0.192
_refine_diff_density_rms         0.064
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.128
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     74
_refine_ls_number_reflns         883
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.128
_refine_ls_R_factor_all          0.0315
_refine_ls_R_factor_gt           0.0299
_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^)+(0.0449P)^2^+0.5363P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0793
_refine_ls_wR_factor_ref         0.0806
_reflns_number_gt                819
_reflns_number_total             883
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo301744s_si_004.cif
_cod_data_source_block           TF-FT
_cod_database_code               4027610