Tunable Low-LUMO Boron-Doped Polycyclic Aromatic Hydrocarbons by General One-Pot C-H Borylations.
Farrell, Jeffrey M.; Mützel, Carina; Bialas, David; Rudolf, Maximilian; Menekse, Kaan; Krause, Ana-Maria; Stolte, Matthias; Würthner, Frank; Journal of the American Chemical Society 141 (2019) 9096–9104; doi:10.1021/jacs.9b04675

data_4127547
_publ_section_title
;
 Tunable Low-LUMO Boron-Doped Polycyclic Aromatic Hydrocarbons by General
 One-Pot C-H Borylations.
;
_journal_issue                   22
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              9096
_journal_page_last               9104
_journal_paper_doi               10.1021/jacs.9b04675
_journal_volume                  141
_journal_year                    2019
_chemical_formula_moiety         'C30 H10 B2 F10 O2, 2.247(C2 H6 O S)'
_chemical_formula_sum            'C68.99 H46.97 B4 F20 O8.5 S4.5'
_chemical_formula_weight         1579.19
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                74.5203(18)
_cell_angle_beta                 87.2248(19)
_cell_angle_gamma                86.8565(18)
_cell_formula_units_Z            2
_cell_length_a                   14.7128(5)
_cell_length_b                   14.9182(5)
_cell_length_c                   16.4821(6)
_cell_measurement_reflns_used    9786
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      72.39
_cell_measurement_theta_min      2.78
_cell_volume                     3479.0(2)
_computing_cell_refinement       'Bruker SAINT'
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_computing_publication_material  'Bruker SHELXTL'
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_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  Bruker-Kappa-D8Quest_Photon100
_diffrn_measurement_method       omega_and_phi_scan
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0540
_diffrn_reflns_av_unetI/netI     0.0401
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       18
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_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -17
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_diffrn_reflns_limit_l_min       -20
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_diffrn_reflns_point_group_measured_fraction_full 0.998
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_diffrn_reflns_theta_max         72.665
_diffrn_reflns_theta_min         2.783
_diffrn_source                   Cu/K(alpha)_ImuS_Microsource
_exptl_absorpt_coefficient_mu    2.373
_exptl_absorpt_correction_T_max  0.7536
_exptl_absorpt_correction_T_min  0.4856
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   Bruker-SADABS
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.507
_exptl_crystal_description       needle
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_exptl_crystal_size_mid          0.027
_exptl_crystal_size_min          0.027
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_refine_diff_density_rms         0.101
_refine_ls_extinction_method     none
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_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1077
_refine_ls_number_reflns         13706
_refine_ls_number_restraints     61
_refine_ls_restrained_S_all      1.049
_refine_ls_R_factor_all          0.0871
_refine_ls_R_factor_gt           0.0758
_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^)+(0.1198P)^2^+5.3773P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2050
_refine_ls_wR_factor_ref         0.2149
_reflns_Friedel_coverage         0.000
_reflns_number_gt                11470
_reflns_number_total             13706
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja9b04675_si_004.cif
_cod_data_source_block           498_JF186_K24_sq
_cod_original_formula_sum        'C68.99 H46.97 B4 F20 O8.50 S4.50'
_cod_database_code               4127547
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.377
_shelx_estimated_absorpt_t_max   0.939
_shelx_res_checksum              57389
_shelx_hkl_checksum              9827
_shelx_fab_checksum              43171