Unexpected Scholl Reaction of 6,7,13,14-Tetraarylbenzo[k]tetraphene: Selective Formation of Five-Membered Rings in Polycyclic Aromatic Hydrocarbons.
Liu, Junzhi; Narita, Akimitsu; Osella, Silvio; Zhang, Wen; Schollmeyer, Dieter; Beljonne, David; Feng, Xinliang; Müllen, Klaus; Journal of the American Chemical Society 138 (2016) 2602–2608; doi:10.1021/jacs.5b10399

data_4129768
_publ_section_title
;
 Unexpected Scholl Reaction of 6,7,13,14-Tetraarylbenzo[k]tetraphene:
 Selective Formation of Five-Membered Rings in Polycyclic Aromatic
 Hydrocarbons.
;
_journal_issue                   8
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              2602
_journal_page_last               2608
_journal_paper_doi               10.1021/jacs.5b10399
_journal_volume                  138
_journal_year                    2016
_chemical_formula_moiety         'C62 H58 O'
_chemical_formula_sum            'C62 H58 O'
_chemical_formula_weight         819.08
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014
_cell_angle_alpha                90
_cell_angle_beta                 109.770(5)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   21.3286(15)
_cell_length_b                   10.7441(10)
_cell_length_c                   25.2843(15)
_cell_measurement_reflns_used    13732
_cell_measurement_temperature    193(2)
_cell_measurement_theta_max      27.25
_cell_measurement_theta_min      2.03
_cell_volume                     5452.6(7)
_computing_cell_refinement       'STOE X-AREA'
_computing_data_collection       'STOE X-AREA'
_computing_data_reduction        'STOE X-RED'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_structure_solution    SIR-2004
_diffrn_ambient_temperature      193(2)
_diffrn_detector                 'image plate (34 cm diameter)'
_diffrn_detector_area_resol_mean 6.67
_diffrn_detector_type            STOE
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.978
_diffrn_measurement_device       '2-circle goniometer'
_diffrn_measurement_device_type  'STOE IPDS 2T'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0934
_diffrn_reflns_av_unetI/netI     0.1361
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.978
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_number            29655
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.978
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.524
_diffrn_reflns_theta_min         2.029
_diffrn_source
'sealed X-ray tube, 12 x 0.4 mm long-fine focus'
_exptl_absorpt_coefficient_mu    0.057
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    0.998
_exptl_crystal_description       needle
_exptl_crystal_F_000             1752
_exptl_crystal_size_max          0.600
_exptl_crystal_size_mid          0.160
_exptl_crystal_size_min          0.030
_platon_squeeze_details
;
TITL 7bist1_a.res in P2(1)/n ohne Loesungsmittel
CELL   21.3286   10.7441   25.2843     90.00    109.77     90.00
SPGR P21/n
C101 0.184 0.670 0.382 !       2.34 eA-3
C102 0.321 0.264 0.133 !       2.05 eA-3
C103 0.174 0.581 0.376 !       1.98 eA-3
C104 0.317 0.235 0.101 !       1.89 eA-3
C105 0.336 0.939 0.125 !       1.73 eA-3
C106 0.165 0.918 0.390 !       1.66 eA-3
C107 0.341 0.465 0.124 !       1.64 eA-3
C108 0.344 0.511 0.133 !       1.53 eA-3
C109 0.321 0.874 0.142 !       0.99 eA-3
C110 0.293 0.327 0.142 !       0.95 eA-3
C111 0.208 0.580 0.340 !       0.86 eA-3
C112 0.364 0.361 0.125 !       0.78 eA-3
C113 0.305 0.904 0.155 !       0.75 eA-3
C114 0.185 0.474 0.321 !       0.75 eA-3
C115 0.380 0.425 0.109 !       0.63 eA-3
C116 0.880 0.561 0.671 !       0.62 eA-3
C117 0.221 0.670 0.437 !       0.60 eA-3
C118 0.304 0.044 0.194 !       0.56 eA-3
Q119 0.235 0.482 0.454 !       0.56 eA-3
C120 0.208 0.075 0.390 !       0.55 eA-3
C121 0.168 0.417 0.432 !       0.54 eA-3
C122 0.399 0.452 0.179 !       0.53 eA-3
C123 0.114 0.811 0.345 !       0.52 eA-3
Q124 0.416 0.893 0.117 !       0.52 eA-3
Q125 0.081 0.106 0.322 !       0.51 eA-3
;
_refine_diff_density_max         0.200
_refine_diff_density_min         -0.192
_refine_diff_density_rms         0.049
_refine_ls_extinction_coef       0.0042(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   0.928
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     718
_refine_ls_number_reflns         13553
_refine_ls_number_restraints     786
_refine_ls_restrained_S_all      0.913
_refine_ls_R_factor_all          0.2417
_refine_ls_R_factor_gt           0.0908
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1290P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2146
_refine_ls_wR_factor_ref         0.3095
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3948
_reflns_number_total             13553
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja5b10399_si_004.cif
_cod_data_source_block           3
_cod_original_cell_volume        5452.5(7)
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               4129768
_shelx_estimated_absorpt_t_min   0.966
_shelx_estimated_absorpt_t_max   0.998
_shelxl_version_number           2014-3
_shelx_res_checksum              67944
_shelx_hkl_checksum              75558
_platon_squeeze_void_probe_radius 1.20
_shelx_fab_checksum              75459