Synthesis of Nonaphenylenes and Dodecaphenylenes Using Electron-Transfer Oxidation of Lipshutz Cuprates and Formation of Nanostructural Materials from Hexadodecyloxynonaphenylene
M. Jalilur Rahman; Jun Yamakawa; Aoi Matsumoto; Hideo Enozawa; Tohru Nishinaga; Kenji Kamada; Masahiko Iyoda; Journal of Organic Chemistry 73 (2008) 5542–5548; doi:10.1021/jo800787u

data_4023553
_publ_section_title
;
 Synthesis of Nonaphenylenes and Dodecaphenylenes Using
 Electron-Transfer Oxidation of Lipshutz Cuprates and Formation of
 Nanostructural Materials from Hexadodecyloxynonaphenylene
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              5542
_journal_page_last               5548
_journal_paper_doi               10.1021/jo800787u
_journal_volume                  73
_journal_year                    2008
_chemical_formula_sum            'C66 H60'
_chemical_formula_weight         853.14
_space_group_IT_number           167
_symmetry_cell_setting           trigonal
_symmetry_space_group_name_Hall  '-R 3 2"c'
_symmetry_space_group_name_H-M   'R -3 c :H'
_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                 90.00
_cell_angle_gamma                120.00
_cell_formula_units_Z            6
_cell_length_a                   17.9043(18)
_cell_length_b                   17.9043(18)
_cell_length_c                   28.214(4)
_cell_measurement_temperature    298(2)
_cell_volume                     7832.7(15)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71069
_diffrn_reflns_av_R_equivalents  0.0568
_diffrn_reflns_av_sigmaI/netI    0.0524
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       0
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       36
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            3994
_diffrn_reflns_theta_full        27.49
_diffrn_reflns_theta_max         27.49
_diffrn_reflns_theta_min         3.00
_exptl_absorpt_coefficient_mu    0.061
_exptl_absorpt_correction_T_max  0.9909
_exptl_absorpt_correction_T_min  0.9790
_exptl_crystal_density_diffrn    1.085
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             2736
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.214
_refine_diff_density_min         -0.195
_refine_diff_density_rms         0.045
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.007
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     101
_refine_ls_number_reflns         2010
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.007
_refine_ls_R_factor_all          0.1523
_refine_ls_R_factor_gt           0.0542
_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^)+(0.1000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1612
_refine_ls_wR_factor_ref         0.1985
_reflns_number_gt                867
_reflns_number_total             2010
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo800787u-File002.cif
_cod_data_source_block           etnona
_cod_original_sg_symbol_H-M      'R -3 c'
_cod_database_code               4023553