Dearomatization-induced transannular cyclization: synthesis of electron-accepting thiophene-s,s-dioxide-fused biphenylene.
Fukazawa, Aiko; Oshima, Hiroya; Shimizu, Soji; Kobayashi, Nagao; Yamaguchi, Shigehiro; Journal of the American Chemical Society 136 (2014) 8738–8745; doi:10.1021/ja503499n

data_4121969
_publ_section_title
;
 Dearomatization-induced transannular cyclization: synthesis of
 electron-accepting thiophene-s,s-dioxide-fused biphenylene.
;
_journal_issue                   24
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              8738
_journal_page_last               8745
_journal_paper_doi               10.1021/ja503499n
_journal_volume                  136
_journal_year                    2014
_chemical_formula_sum            'C44 H64 O8 S4 Si4'
_chemical_formula_weight         961.55
_chemical_name_common            cmpd3
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_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                 93.306(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   13.746(5)
_cell_length_b                   12.472(4)
_cell_length_c                   14.807(5)
_cell_measurement_reflns_used    4889
_cell_measurement_temperature    123(2)
_cell_measurement_theta_max      31.5050
_cell_measurement_theta_min      1.3777
_cell_volume                     2534.3(15)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      123(2)
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_device_type
;
Saturn70 CCD (4x4 bin mode) with MicroMax-007
;
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71070
_diffrn_reflns_av_R_equivalents  0.0934
_diffrn_reflns_av_sigmaI/netI    0.0946
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            16767
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         1.38
_exptl_absorpt_coefficient_mu    0.329
_exptl_absorpt_correction_T_max  0.9934
_exptl_absorpt_correction_T_min  0.9370
_exptl_absorpt_process_details   'Jacobsen, R. (1998)  Private communication'
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.260
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1024
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.846
_refine_diff_density_min         -0.679
_refine_diff_density_rms         0.203
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.178
_refine_ls_hydrogen_treatment    none
_refine_ls_matrix_type           full
_refine_ls_number_parameters     289
_refine_ls_number_reflns         4404
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.178
_refine_ls_R_factor_all          0.1297
_refine_ls_R_factor_gt           0.0872
_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^)+(0.1471P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2207
_refine_ls_wR_factor_ref         0.2736
_reflns_number_gt                3210
_reflns_number_total             4404
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja503499n_si_002.cif
_cod_data_source_block           cd-ox
_cod_depositor_comments
'Adding full bibliography for 4121966--4121969.cif.'
_cod_original_cell_volume        2534.2(15)
_cod_original_sg_symbol_H-M      P21/a
_cod_database_code               4121969