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_4127546
_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         'C32 H20 B2 O2, 4(C4 H8 O2)'
_chemical_formula_sum            'C48 H52 B2 O10'
_chemical_formula_weight         810.51
_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   mixed
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                80.086(3)
_cell_angle_beta                 89.946(3)
_cell_angle_gamma                85.751(3)
_cell_formula_units_Z            1
_cell_length_a                   5.6393(4)
_cell_length_b                   12.8559(8)
_cell_length_c                   14.1348(9)
_cell_measurement_reflns_used    7438
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      72.51
_cell_measurement_theta_min      3.17
_cell_volume                     1006.60(12)
_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-2018/1 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.984
_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  0.0451
_diffrn_reflns_av_unetI/netI     0.0506
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            13395
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         72.723
_diffrn_reflns_theta_min         3.174
_diffrn_source                   Cu/K(alpha)_ImuS_Microsource
_exptl_absorpt_coefficient_mu    0.742
_exptl_absorpt_correction_T_max  0.7536
_exptl_absorpt_correction_T_min  0.5790
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   Bruker_SADABS
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.337
_exptl_crystal_description       needle
_exptl_crystal_F_000             430
_exptl_crystal_size_max          0.272
_exptl_crystal_size_mid          0.053
_exptl_crystal_size_min          0.022
_refine_diff_density_max         0.293
_refine_diff_density_min         -0.253
_refine_diff_density_rms         0.056
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     341
_refine_ls_number_reflns         3919
_refine_ls_number_restraints     8
_refine_ls_restrained_S_all      1.056
_refine_ls_R_factor_all          0.0653
_refine_ls_R_factor_gt           0.0570
_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^)+(0.0899P)^2^+0.3466P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1559
_refine_ls_wR_factor_ref         0.1655
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3323
_reflns_number_total             3919
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja9b04675_si_006.cif
_cod_data_source_block           CM016_dioxan_ab
_cod_database_code               4127546
_shelx_shelxl_version_number     2014/7
_shelx_res_checksum              97940
_shelx_hkl_checksum              11511