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_4127548
_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 H12 F10'
_chemical_formula_sum            'C30 H12 F10'
_chemical_formula_weight         562.40
_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'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 98.4482(13)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.5878(4)
_cell_length_b                   7.1239(2)
_cell_length_c                   22.9259(7)
_cell_measurement_reflns_used    9929
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      72.13
_cell_measurement_theta_min      3.29
_cell_volume                     2195.10(11)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX3'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_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  0.0638
_diffrn_reflns_av_unetI/netI     0.0366
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            23328
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         72.126
_diffrn_reflns_theta_min         3.288
_diffrn_source                   Cu/K(alpha)_ImuS_Microsource
_exptl_absorpt_coefficient_mu    1.400
_exptl_absorpt_correction_T_max  0.7536
_exptl_absorpt_correction_T_min  0.5185
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   Bruker-SADABS
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.702
_exptl_crystal_description       needle
_exptl_crystal_F_000             1128
_exptl_crystal_size_max          0.534
_exptl_crystal_size_mid          0.055
_exptl_crystal_size_min          0.034
_refine_diff_density_max         0.884
_refine_diff_density_min         -0.418
_refine_diff_density_rms         0.086
_refine_ls_extinction_method     none
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_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     361
_refine_ls_number_reflns         4325
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.083
_refine_ls_R_factor_all          0.0647
_refine_ls_R_factor_gt           0.0600
_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^)+(0.0748P)^2^+3.4335P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1643
_refine_ls_wR_factor_ref         0.1684
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3914
_reflns_number_total             4325
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja9b04675_si_002.cif
_cod_data_source_block           499_JF_Edukt
_cod_database_code               4127548
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.522
_shelx_estimated_absorpt_t_max   0.954
_shelx_res_checksum              49861
_shelx_hkl_checksum              35483