Synthesis of oxygen-substituted hexa-peri-hexabenzocoronenes through Ir-catalyzed direct borylation.
Yamaguchi, Ryuichi; Hiroto, Satoru; Shinokubo, Hiroshi; Organic letters 14 (2012) 2472–2475; doi:10.1021/ol300743f

data_1507676
_publ_section_title
;
 Synthesis of oxygen-substituted hexa-peri-hexabenzocoronenes through
 Ir-catalyzed direct borylation.
;
_journal_issue                   10
_journal_name_full               'Organic letters'
_journal_page_first              2472
_journal_page_last               2475
_journal_paper_doi               10.1021/ol300743f
_journal_volume                  14
_journal_year                    2012
_chemical_formula_sum            'C94 H65 Cl16 O8'
_chemical_formula_weight         1889.66
_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
_audit_creation_method           SHELXL-97
_audit_update_record
;
2012-04-30 # Formatted by publCIF
;
_cell_angle_alpha                68.827(7)
_cell_angle_beta                 84.940(8)
_cell_angle_gamma                80.653(7)
_cell_formula_units_Z            2
_cell_length_a                   14.851(5)
_cell_length_b                   16.799(6)
_cell_length_c                   17.678(6)
_cell_measurement_reflns_used    5382
_cell_measurement_temperature    93(2)
_cell_measurement_theta_max      0.00
_cell_measurement_theta_min      0.00
_cell_volume                     4056(2)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      93(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0258
_diffrn_reflns_av_sigmaI/netI    0.0694
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            23711
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         1.24
_exptl_absorpt_coefficient_mu    0.603
_exptl_absorpt_correction_T_max  0.9177
_exptl_absorpt_correction_T_min  0.8446
_exptl_absorpt_correction_type   empirical
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.547
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1930
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.20
_platon_squeeze_details
;
;
_refine_diff_density_max         0.487
_refine_diff_density_min         -0.328
_refine_diff_density_rms         0.084
_refine_ls_extinction_method     none
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_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     863
_refine_ls_number_reflns         14281
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.966
_refine_ls_R_factor_all          0.1448
_refine_ls_R_factor_gt           0.1005
_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^)+(0.1835P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2798
_refine_ls_wR_factor_ref         0.3037
_reflns_number_gt                6753
_reflns_number_total             14281
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol300743f_si_004.cif
_cod_data_source_block           shelxl
_cod_depositor_comments
'Adding full bibliography for 1507674--1507676.cif.'
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               1507676