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_4129770
_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'
_chemical_formula_sum            'C62 H58'
_chemical_formula_weight         803.08
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014
_cell_angle_alpha                90.659(6)
_cell_angle_beta                 106.259(6)
_cell_angle_gamma                105.609(6)
_cell_formula_units_Z            2
_cell_length_a                   10.474(2)
_cell_length_b                   15.073(3)
_cell_length_c                   18.188(4)
_cell_measurement_reflns_used    2836
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      21.54
_cell_measurement_theta_min      2.34
_cell_volume                     2643.2(9)
_computing_cell_refinement       'APEX II Suite'
_computing_data_collection       'APEX II Suite'
_computing_data_reduction        'APEX II Suite'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXT-2014 (Sheldrick, 2014)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device_type  'SMART APEX II'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1836
_diffrn_reflns_av_unetI/netI     0.3620
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            32134
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.089
_diffrn_reflns_theta_min         1.746
_diffrn_source                   'sealed tube'
_exptl_absorpt_coefficient_mu    0.057
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.009
_exptl_crystal_description       needle
_exptl_crystal_F_000             860
_exptl_crystal_size_max          0.440
_exptl_crystal_size_mid          0.090
_exptl_crystal_size_min          0.050
_platon_squeeze_details
;
TITL ha7 in P-1
CELL   10.4740   15.0730   18.1880     90.66    106.26    105.61
SPGR P-1
C101 0.979 1.003 0.017 !       2.05 eA-3
C102 0.372 1.004 0.376 !       1.87 eA-3
C103 1.002 0.010 0.126 !       1.80 eA-3
C104 0.252 0.052 0.284 !       1.78 eA-3
C105 0.051 0.048 0.202 !       1.73 eA-3
C106 0.699 0.952 0.674 !       1.70 eA-3
C107 0.086 0.014 0.254 !       1.70 eA-3
C108 0.041 0.024 0.110 !       1.69 eA-3
C109 0.034 0.995 0.063 !       1.66 eA-3
C110 0.152 0.023 0.299 !       1.58 eA-3
C111 0.069 1.007 0.176 !       1.54 eA-3
C112 0.455 0.047 0.436 !       1.41 eA-3
C113 0.468 0.969 0.467 !       1.40 eA-3
C114 0.741 0.997 0.691 !       1.39 eA-3
C115 0.474 0.060 0.500 !       1.35 eA-3
C116 0.079 0.982 0.034 !       1.34 eA-3
C117 0.020 0.975 0.135 !       1.34 eA-3
C118 0.415 0.964 0.437 !       1.30 eA-3
C119 1.015 0.980 0.226 !       1.23 eA-3
C120 0.365 0.922 0.372 !       1.22 eA-3
C121 0.445 0.893 0.448 !       1.18 eA-3
C122 0.225 0.026 0.343 !       1.17 eA-3
C123 0.645 0.985 0.572 !       1.11 eA-3
C124 0.941 0.891 0.786 !       1.08 eA-3
C125 0.993 0.902 0.095 !       1.07 eA-3
Q126 0.814 0.118 0.546 !       1.06 eA-3
C127 0.088 0.966 0.098 !       1.05 eA-3
C128 0.289 0.935 0.343 !       1.04 eA-3
C129 0.118 0.020 0.971 !       1.03 eA-3
C130 0.087 0.098 0.128 !       0.96 eA-3
C131 0.328 0.846 0.362 !       0.95 eA-3
C132 0.117 0.134 0.190 !       0.93 eA-3
C133 0.047 0.942 0.732 !       0.92 eA-3
C134 0.902 0.952 0.217 !       0.91 eA-3
C135 0.132 0.138 0.250 !       0.90 eA-3
C136 0.992 0.160 0.012 !       0.90 eA-3
C137 0.341 0.113 0.357 !       0.90 eA-3
C138 0.189 0.098 0.321 !       0.88 eA-3
C139 0.318 0.094 0.258 !       0.88 eA-3
C140 0.231 1.000 0.410 !       0.87 eA-3
C141 0.980 0.937 0.250 !       0.85 eA-3
C142 0.062 0.923 0.125 !       0.85 eA-3
C143 0.136 0.983 0.003 !       0.85 eA-3
C144 0.046 0.962 0.285 !       0.84 eA-3
C145 0.936 0.089 0.045 !       0.84 eA-3
C146 0.209 0.094 0.245 !       0.83 eA-3
C147 0.332 0.920 0.394 !       0.83 eA-3
C148 0.040 0.094 0.043 !       0.82 eA-3
C149 1.005 0.933 0.182 !       0.81 eA-3
C150 0.165 0.964 0.347 !       0.80 eA-3
C151 0.360 0.089 0.330 !       0.80 eA-3
Q152 0.029 0.895 0.140 !       0.80 eA-3
Q153 0.308 0.150 0.343 !       0.80 eA-3
C154 1.008 0.135 0.185 !       0.79 eA-3
Q155 0.177 0.128 0.044 !       0.79 eA-3
C156 0.255 0.061 0.392 !       0.79 eA-3
C157 0.300 0.999 0.251 !       0.79 eA-3
C158 0.120 0.922 0.235 !       0.78 eA-3
Q159 0.037 0.887 0.266 !       0.78 eA-3
C160 0.129 0.967 0.211 !       0.77 eA-3
Q161 0.713 0.173 0.375 !       0.77 eA-3
Q162 0.811 0.973 0.219 !       0.76 eA-3
Q163 0.155 0.780 0.343 !       0.75 eA-3
C164 0.032 0.110 0.283 !       0.74 eA-3
Q165 0.845 0.111 0.128 !       0.74 eA-3
C166 1.005 0.876 0.045 !       0.73 eA-3
C167 0.914 0.998 0.192 !       0.73 eA-3
Q168 0.628 0.206 0.486 !       0.73 eA-3
Q169 0.400 0.949 0.235 !       0.73 eA-3
C170 0.871 0.939 0.263 !       0.72 eA-3
C171 0.020 0.119 0.140 !       0.72 eA-3
Q172 0.126 0.893 0.156 !       0.72 eA-3
C173 0.316 0.894 0.313 !       0.72 eA-3
Q174 0.061 0.372 0.345 !       0.71 eA-3
Q175 0.776 0.690 0.093 !       0.71 eA-3
C176 0.848 0.982 0.128 !       0.71 eA-3
C177 0.371 0.981 0.488 !       0.71 eA-3
C178 0.537 0.860 0.472 !       0.71 eA-3
Q179 0.103 0.876 0.359 !       0.71 eA-3
C180 0.410 0.097 0.450 !       0.70 eA-3
C181 0.785 0.169 0.687 !       0.70 eA-3
Q182 0.400 0.870 0.549 !       0.70 eA-3
C183 0.932 0.085 0.985 !       0.69 eA-3
Q184 0.684 0.955 0.344 !       0.69 eA-3
C185 0.511 0.095 0.405 !       0.69 eA-3
Q186 0.088 0.188 0.218 !       0.69 eA-3
Q187 0.999 0.815 0.424 !       0.69 eA-3
C188 0.850 0.076 0.077 !       0.69 eA-3
Q189 0.666 0.886 0.313 !       0.68 eA-3
Q190 0.686 0.968 0.031 !       0.68 eA-3
C191 0.101 0.126 0.953 !       0.68 eA-3
Q192 0.497 0.892 0.342 !       0.68 eA-3
Q193 0.942 0.745 0.424 !       0.68 eA-3
C194 0.775 0.918 0.798 !       0.68 eA-3
C195 0.911 0.018 0.623 !       0.67 eA-3
C196 0.062 0.875 0.046 !       0.67 eA-3
C197 0.879 0.998 0.281 !       0.67 eA-3
Q198 0.564 0.232 0.595 !       0.67 eA-3
Q199 0.404 0.955 0.547 !       0.67 eA-3
;
_refine_diff_density_max         0.285
_refine_diff_density_min         -0.249
_refine_diff_density_rms         0.054
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.885
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     595
_refine_ls_number_reflns         12702
_refine_ls_number_restraints     65
_refine_ls_restrained_S_all      0.888
_refine_ls_R_factor_all          0.3213
_refine_ls_R_factor_gt           0.0948
_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^)+(0.1034P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2003
_refine_ls_wR_factor_ref         0.2929
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3181
_reflns_number_total             12702
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja5b10399_si_003.cif
_cod_data_source_block           2
_cod_original_cell_volume        2643.1(10)
_cod_database_code               4129770
_shelx_estimated_absorpt_t_min   0.975
_shelx_estimated_absorpt_t_max   0.997
_shelxl_version_number           2014-3
_shelx_res_checksum              11092
_shelx_hkl_checksum              1253
_platon_squeeze_void_probe_radius 1.20
_shelx_fab_checksum              64806