Isomerically Pure Anthra[2,3-b:6,7-b']-difuran (anti-ADF), -dithiophene (anti-ADT), and -diselenophene (anti-ADS): Selective Synthesis, Electronic Structures, and Application to Organic Field-Effect Transistors
Masahiro Nakano; Kazuki Niimi; Eigo Miyazaki; Itaru Osaka; Kazuo Takimiya; Journal of Organic Chemistry 77 (2012) 8099–8111; doi:10.1021/jo301438t

data_4027521
_publ_section_title
;
 Isomerically Pure Anthra[2,3-b:6,7-b']-difuran (anti-ADF), -dithiophene
 (anti-ADT), and -diselenophene (anti-ADS): Selective Synthesis,
 Electronic Structures, and Application to Organic Field-Effect
 Transistors
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              8099
_journal_page_last               8111
_journal_paper_doi               10.1021/jo301438t
_journal_volume                  77
_journal_year                    2012
_chemical_formula_moiety         'C24 H24 I2 S2 Si2'
_chemical_formula_sum            'C24 H24 I2 S2 Si2'
_chemical_formula_weight         686.53
_chemical_name_common            ADT-TMSI
_chemical_name_systematic
; 
ADT-TMSI
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_Int_Tables_number      2
_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                88.615(18)
_cell_angle_beta                 79.423(17)
_cell_angle_gamma                75.950(19)
_cell_formula_units_Z            1
_cell_length_a                   6.6086(15)
_cell_length_b                   7.6941(18)
_cell_length_c                   13.414(3)
_cell_measurement_reflns_used    2102
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      29.10
_cell_measurement_theta_min      3.14
_cell_volume                     650.3(3)
_computing_cell_refinement       CRYSTALCLEAR
_computing_data_collection       CRYSTALCLEAR
_computing_data_reduction        CRYSTALCLEAR
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 14.71
_diffrn_measured_fraction_theta_full 0.840
_diffrn_measured_fraction_theta_max 0.840
_diffrn_measurement_device_type  'Rigaku/MSC Mercury CCD'
_diffrn_measurement_method       \w
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71069
_diffrn_reflns_av_R_equivalents  0.0000
_diffrn_reflns_av_sigmaI/netI    0.0031
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            6187
_diffrn_reflns_theta_full        28.89
_diffrn_reflns_theta_max         28.89
_diffrn_reflns_theta_min         3.09
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.681
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            Red
_exptl_crystal_density_diffrn    1.753
_exptl_crystal_description       Block
_exptl_crystal_F_000             334
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.715
_refine_diff_density_min         -1.007
_refine_diff_density_rms         0.152
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.174
_refine_ls_hydrogen_treatment    noref
_refine_ls_matrix_type           full
_refine_ls_number_parameters     137
_refine_ls_number_reflns         6187
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.174
_refine_ls_R_factor_all          0.0686
_refine_ls_R_factor_gt           0.0673
_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^)+(0.0819P)^2^+2.4717P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1870
_refine_ls_wR_factor_ref         0.1882
_reflns_number_gt                6030
_reflns_number_total             6187
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo301438t_si_002.cif
_cod_data_source_block           ADT-TMSI
_cod_original_cell_volume        650.3(2)
_cod_database_code               4027521