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_4129767
_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 H56 I2 O, C H2 Cl2'
_chemical_formula_sum            'C63 H58 Cl2 I2 O'
_chemical_formula_weight         1155.79
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 92.935(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   14.2394(4)
_cell_length_b                   26.1832(7)
_cell_length_c                   15.1396(4)
_cell_measurement_reflns_used    27499
_cell_measurement_temperature    193(2)
_cell_measurement_theta_max      28.20
_cell_measurement_theta_min      2.06
_cell_volume                     5637.1(3)
_computing_cell_refinement       'STOE X-AREA'
_computing_data_collection       'STOE X-AREA'
_computing_data_reduction        'STOE X-RED'
_computing_structure_refinement  'SHELXL-2014/7 (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 0.995
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_details      ' 138 frames, detector distance = 90 mm'
_diffrn_measurement_device       '2-circle goniometer'
_diffrn_measurement_device_type  'STOE IPDS 2T'
_diffrn_measurement_method       'rotation method'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0292
_diffrn_reflns_av_unetI/netI     0.0426
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       33
_diffrn_reflns_limit_k_min       -34
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            32973
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.195
_diffrn_reflns_theta_min         2.058
_diffrn_source
'sealed X-ray tube, 12 x 0.4 mm long-fine focus'
_exptl_absorpt_coefficient_mu    1.250
_exptl_absorpt_correction_T_max  0.9142
_exptl_absorpt_correction_T_min  0.7988
_exptl_absorpt_correction_type   integration
_exptl_absorpt_process_details   X-Red
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.362
_exptl_crystal_description       needle
_exptl_crystal_F_000             2336
_exptl_crystal_size_max          0.210
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.060
_platon_squeeze_details
;
TITL 7bistddq in P 21/c
CELL   14.2394   26.1832   15.1396     90.00     92.93     90.00
SPGR P21/c
C101 0.261 0.314 0.395 !       1.81 eA-3
Q102 0.406 0.363 0.159 !       1.36 eA-3
Q103 0.894 0.474 0.206 !       1.03 eA-3
C104 0.850 0.798 0.250 !       1.01 eA-3
Q105 0.478 0.117 0.667 !       1.01 eA-3
Q106 0.124 0.413 0.289 !       0.95 eA-3
Q107 0.468 0.361 0.130 !       0.94 eA-3
Q108 0.055 0.980 0.187 !       0.82 eA-3
Q109 0.956 0.913 0.302 !       0.78 eA-3
Q110 0.557 0.882 0.375 !       0.75 eA-3
Q111 0.371 0.305 0.844 !       0.74 eA-3
Q112 0.495 0.719 0.184 !       0.70 eA-3
Q113 0.152 0.784 0.264 !       0.69 eA-3
C114 0.248 0.259 0.361 !       0.68 eA-3
C115 0.223 0.298 0.246 !       0.66 eA-3
Q116 0.347 0.162 0.296 !       0.66 eA-3
Q117 0.328 0.959 0.634 !       0.63 eA-3
Q118 0.466 0.384 0.236 !       0.61 eA-3
Q119 0.610 0.781 0.566 !       0.60 eA-3
Q120 0.642 0.113 0.240 !       0.60 eA-3
C121 0.229 0.331 0.303 !       0.60 eA-3
C122 0.766 0.775 0.295 !       0.59 eA-3
Q123 0.529 0.346 0.122 !       0.58 eA-3
Q124 0.123 0.329 0.216 !       0.57 eA-3
C125 0.755 0.765 0.191 !       0.57 eA-3
Q126 0.510 0.721 0.075 !       0.56 eA-3
C127 0.749 0.795 0.176 !       0.55 eA-3
C128 0.691 0.832 0.103 !       0.55 eA-3
Q129 0.667 0.768 0.278 !       0.55 eA-3
Q130 0.972 0.954 0.233 !       0.55 eA-3
Q131 0.159 0.095 0.325 !       0.54 eA-3
Q132 0.815 0.593 0.455 !       0.53 eA-3
Q133 0.365 0.299 0.344 !       0.53 eA-3
Q134 0.304 0.617 0.200 !       0.53 eA-3
Q135 0.184 0.186 0.440 !       0.53 eA-3
C136 0.729 0.749 0.342 !       0.53 eA-3
Q137 0.316 0.807 0.373 !       0.53 eA-3
C138 0.188 0.201 0.800 !       0.52 eA-3
Q139 0.582 0.651 0.767 !       0.52 eA-3
Q140 0.144 0.337 0.548 !       0.51 eA-3
Q141 0.707 0.352 0.077 !       0.51 eA-3
Q142 0.362 0.236 0.276 !       0.51 eA-3
C143 0.234 0.247 0.749 !       0.51 eA-3
Q144 0.313 0.321 0.189 !       0.50 eA-3
Q145 0.666 1.003 0.489 !       0.50 eA-3
C146 0.891 0.773 0.287 !       0.50 eA-3
;
_refine_diff_density_max         0.882
_refine_diff_density_min         -1.249
_refine_diff_density_rms         0.095
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     692
_refine_ls_number_reflns         13768
_refine_ls_number_restraints     99
_refine_ls_restrained_S_all      1.037
_refine_ls_R_factor_all          0.0841
_refine_ls_R_factor_gt           0.0496
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0793P)^2^+3.1428P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1271
_refine_ls_wR_factor_ref         0.1484
_reflns_Friedel_coverage         0.000
_reflns_number_gt                9088
_reflns_number_total             13768
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja5b10399_si_005.cif
_cod_data_source_block           4
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               4129767
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.779
_shelx_estimated_absorpt_t_max   0.929
_shelx_res_checksum              59184
_shelx_hkl_checksum              51265
_platon_squeeze_void_probe_radius 1.20
_shelx_fab_checksum              39575