Thiophene-Fused Bisdehydro[12]annulene That Undergoes Transannular Alkyne Cycloaddition by Either Light or Heat
Aiko Fukazawa; Hiroya Oshima; Yoshihito Shiota; Shouya Takahashi; Kazunari Yoshizawa; Shigehiro Yamaguchi; Journal of the American Chemical Society 135 (2013) 1731–1734; doi:10.1021/ja3126849

data_4119309
_publ_contact_author_address
;Department of Chemistry
Graduate School of Science, Nagoya University
Chikusa, Nagoya 464-8602 Japan
;
_publ_contact_author_email       yamaguchi@chem.nagoya-u.ac.jp
_publ_contact_author_fax         81(52)7895947
_publ_contact_author_name        'Shigehiro Yamaguchi'
_publ_contact_author_phone       81(52)7892291
_publ_section_title
;
 Thiophene-Fused Bisdehydro[12]annulene That Undergoes Transannular Alkyne
 Cycloaddition by Either Light or Heat
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              1731
_journal_page_last               1734
_journal_paper_doi               10.1021/ja3126849
_journal_volume                  135
_journal_year                    2013
_chemical_formula_moiety         'C44 H64 S4 Si4'
_chemical_formula_sum            'C44 H64 S4 Si4'
_chemical_formula_weight         833.58
_chemical_melting_point          463
_chemical_name_common
;
thiophene-fused bisdehydro[12]annulene
;
_chemical_name_systematic
; 
 tetrakis[5-(t-butyldimethylsilyl)thieno]bisdehydro[12]annulene 
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_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
_cell_angle_alpha                106.591(5)
_cell_angle_beta                 98.874(4)
_cell_angle_gamma                109.146(5)
_cell_formula_units_Z            2
_cell_length_a                   11.497(5)
_cell_length_b                   13.961(6)
_cell_length_c                   16.959(7)
_cell_measurement_reflns_used    6434
_cell_measurement_temperature    123(2)
_cell_measurement_theta_max      31.5050
_cell_measurement_theta_min      1.3027
_cell_volume                     2370.3(18)
_computing_cell_refinement       'CrystalClear 1.3.6 (Rigaku Co., Ltd.)'
_computing_data_collection       'CrystalClear 1.3.6 (Rigaku Co., Ltd.)'
_computing_data_reduction        'CrystalClear 1.3.6 (Rigaku Co., Ltd.)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      123(2)
_diffrn_measured_fraction_theta_full 0.980
_diffrn_measured_fraction_theta_max 0.980
_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  0.0454
_diffrn_reflns_av_sigmaI/netI    0.0799
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            16053
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         1.70
_exptl_absorpt_coefficient_mu    0.330
_exptl_absorpt_correction_T_max  0.9902
_exptl_absorpt_correction_T_min  0.9677
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Jacobsen, R. (1998)  Private communication'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.168
_exptl_crystal_description       block
_exptl_crystal_F_000             896
_exptl_crystal_size_max          0.10
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.625
_refine_diff_density_min         -0.392
_refine_diff_density_rms         0.079
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.104
_refine_ls_hydrogen_treatment    none
_refine_ls_matrix_type           full
_refine_ls_number_parameters     489
_refine_ls_number_reflns         8192
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.104
_refine_ls_R_factor_all          0.0981
_refine_ls_R_factor_gt           0.0718
_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^)+(0.0397P)^2^+4.5917P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1329
_refine_ls_wR_factor_ref         0.1476
_reflns_number_gt                6245
_reflns_number_total             8192
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja3126849_si_002.cif
_cod_data_source_block           T4BD12A
_cod_database_code               4119309