Regiochemical Effects of Sulfur Oxidation on the Electronic and Solid-State Properties of Planarized Oligothiophenes Containing Thieno[3,2-b]thiophene Units
Lidaris San Miguel; Adam J. Matzger; Journal of Organic Chemistry 73 (2008) 7882–7888; doi:10.1021/jo801619q

data_4023766
_publ_contact_author_address
;Department of Chemistry
930 N. University Ave.
Ann Arbor, MI 48109
;
_publ_contact_author_email       matzger@umich.edu
_publ_contact_author_name        'Adam J. Matzger'
_publ_section_title
;
 Regiochemical Effects of Sulfur Oxidation on the Electronic
 and Solid-State Properties of Planarized Oligothiophenes
 Containing Thieno[3,2-b]thiophene Units
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              7882
_journal_page_last               7888
_journal_paper_doi               10.1021/jo801619q
_journal_volume                  73
_journal_year                    2008
_chemical_formula_moiety         'C12 H6 O4 S4'
_chemical_formula_sum            'C12 H6 O4 S4'
_chemical_formula_weight         342.41
_chemical_name_common            T2O2-O2T2
_chemical_name_systematic
; 
2,2'-bithieno[3,2-b]thiophene 1,1,1',1'-tetraoxide 
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      14
_symmetry_space_group_name_Hall  '-P 2yab'
_symmetry_space_group_name_H-M   'P 1 21/a 1'
_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                 102.879(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   6.09905(15)
_cell_length_b                   16.4375(6)
_cell_length_c                   6.54633(18)
_cell_measurement_reflns_used    8272
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      66.6
_cell_measurement_theta_min      6.9
_cell_volume                     639.78(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
_computing_structure_solution    SIR2004'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 10.00
_diffrn_measured_fraction_theta_full 0.981
_diffrn_measured_fraction_theta_max 0.982
_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  0.0479
_diffrn_reflns_av_sigmaI/netI    0.0280
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_number            10639
_diffrn_reflns_theta_full        66.59
_diffrn_reflns_theta_max         66.59
_diffrn_reflns_theta_min         6.94
_exptl_absorpt_coefficient_mu    6.933
_exptl_absorpt_correction_T_max  0.6892
_exptl_absorpt_correction_T_min  0.2961
_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    1.777
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       chunk
_exptl_crystal_F_000             348
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.361
_refine_diff_density_min         -0.402
_refine_diff_density_rms         0.076
_refine_ls_extinction_coef       none
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.084
_refine_ls_hydrogen_treatment    riding
_refine_ls_matrix_type           full
_refine_ls_number_parameters     93
_refine_ls_number_reflns         1110
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.084
_refine_ls_R_factor_all          0.0349
_refine_ls_R_factor_gt           0.0333
_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^)+(0.0288P)^2^+1.2717P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0809
_refine_ls_wR_factor_ref         0.0819
_reflns_number_gt                1038
_reflns_number_total             1110
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo801619q_si_003.cif
_cod_data_source_block           T2O2-O2T2_compound_3
_cod_original_sg_symbol_H-M      'P 21/a '
_cod_database_code               4023766