Synthesis of Triphenylene Derivatives by Rhodium-Catalyzed [2 + 2 + 2] Cycloaddition: Application to the Synthesis of Highly Fluorescent Triphenylene-Based Long Ladder Molecules
Koichi Murayama; Yayoi Sawada; Keiichi Noguchi; Ken Tanaka; Journal of Organic Chemistry 78 (2013) 6202–6210; doi:10.1021/jo4008892

data_4028377
_publ_contact_author_address
;
Department of Applied Chemistry
Graduate School of Engineering
Tokyo University of Agriculture and Technology
Koganei
Tokyo 184-8588
Japan
;
_publ_contact_author_email       tanaka-k@cc.tuat.ac.jp
_publ_contact_author_fax         +81-42-388-7037
_publ_contact_author_phone       +81-42-388-7037
_publ_section_title
;
 Synthesis of Triphenylene Derivatives by Rhodium-Catalyzed [2 + 2 + 2]
 Cycloaddition: Application to the Synthesis of Highly Fluorescent
 Triphenylene-Based Long Ladder Molecules
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              6202
_journal_page_last               6210
_journal_paper_doi               10.1021/jo4008892
_journal_volume                  78
_journal_year                    2013
_chemical_formula_moiety         'C60 H58'
_chemical_formula_sum            'C60 H58'
_chemical_formula_weight         779.06
_space_group_IT_number           61
_symmetry_cell_setting           orthorhombic
_symmetry_Int_Tables_number      61
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   16.6507(3)
_cell_length_b                   8.32790(10)
_cell_length_c                   30.7761(5)
_cell_measurement_reflns_used    45518
_cell_measurement_temperature    193(2)
_cell_measurement_theta_max      68.25
_cell_measurement_theta_min      3.02
_cell_volume                     4267.58(12)
_computing_cell_refinement       'RAPID AUTO'
_computing_data_collection       'RAPID AUTO (Rigaku, 2004)'
_computing_data_reduction        'RAPID AUTO'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'Il Milione (Burla, et al., 2007)'
_diffrn_ambient_temperature      193(2)
_diffrn_detector_area_resol_mean 10.000
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID'
_diffrn_measurement_method       \w
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'rotating anode'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54187
_diffrn_reflns_av_R_equivalents  0.0342
_diffrn_reflns_av_sigmaI/netI    0.0185
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       37
_diffrn_reflns_limit_l_min       -36
_diffrn_reflns_number            64340
_diffrn_reflns_theta_full        68.25
_diffrn_reflns_theta_max         68.25
_diffrn_reflns_theta_min         3.91
_exptl_absorpt_coefficient_mu    0.509
_exptl_absorpt_correction_T_max  0.980
_exptl_absorpt_correction_T_min  0.905
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   'NUMABS (Rigaku, 1999)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.213
_exptl_crystal_description       block
_exptl_crystal_F_000             1672
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.176
_refine_diff_density_min         -0.185
_refine_diff_density_rms         0.041
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.106
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     273
_refine_ls_number_reflns         3883
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.106
_refine_ls_R_factor_all          0.0561
_refine_ls_R_factor_gt           0.0432
_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^)+(0.0546P)^2^+0.9342P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1069
_refine_ls_wR_factor_ref         0.1181
_reflns_number_gt                2987
_reflns_number_total             3883
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo4008892_si_001.cif
_cod_data_source_block           I
_cod_database_code               4028377