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_4121968
_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            'C48 H70 N2 O6 S4 Si4'
_chemical_formula_weight         1011.66
_chemical_name_common            cmpd4
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 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                 90.6910(19)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   6.8915(8)
_cell_length_b                   23.793(3)
_cell_length_c                   16.7203(19)
_cell_measurement_reflns_used    8728
_cell_measurement_temperature    123(2)
_cell_measurement_theta_max      31.5050
_cell_measurement_theta_min      2.1016
_cell_volume                     2741.4(6)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      123(2)
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_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  0.0290
_diffrn_reflns_av_sigmaI/netI    0.0260
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            17964
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.10
_exptl_absorpt_coefficient_mu    0.306
_exptl_absorpt_correction_T_max  0.9137
_exptl_absorpt_correction_T_min  0.8873
_exptl_absorpt_process_details   'Jacobsen, R. (1998)  Private communication'
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.226
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1080
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.30
_refine_diff_density_max         0.784
_refine_diff_density_min         -0.307
_refine_diff_density_rms         0.054
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.073
_refine_ls_hydrogen_treatment    none
_refine_ls_matrix_type           full
_refine_ls_number_parameters     369
_refine_ls_number_reflns         4810
_refine_ls_number_restraints     8
_refine_ls_restrained_S_all      1.073
_refine_ls_R_factor_all          0.0458
_refine_ls_R_factor_gt           0.0418
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0586P)^2^+1.8762P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1103
_refine_ls_wR_factor_ref         0.1135
_reflns_number_gt                4418
_reflns_number_total             4810
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja503499n_si_003.cif
_cod_data_source_block           ho-3so22
_cod_depositor_comments
'Adding full bibliography for 4121966--4121969.cif.'
_cod_original_cell_volume        2741.4(5)
_cod_original_sg_symbol_H-M      P21/c
_cod_database_code               4121968