B2N2-Dibenzo[a,e]pentalenes: Effect of the BN Orientation Pattern on Antiaromaticity and Optoelectronic Properties.
Wang, Xiao-Ye; Narita, Akimitsu; Feng, Xinliang; Müllen, Klaus; Journal of the American Chemical Society 137 (2015) 7668–7671; doi:10.1021/jacs.5b05056

data_4123814
_publ_section_title
;
 B2N2-Dibenzo[a,e]pentalenes: Effect of the BN Orientation Pattern on
 Antiaromaticity and Optoelectronic Properties.
;
_journal_issue                   24
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              7668
_journal_page_last               7671
_journal_paper_doi               10.1021/jacs.5b05056
_journal_volume                  137
_journal_year                    2015
_chemical_formula_moiety         'C21 H20 B Br N2'
_chemical_formula_sum            'C21 H20 B Br N2'
_chemical_formula_weight         391.11
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.8983(6)
_cell_length_b                   14.4390(8)
_cell_length_c                   16.3846(9)
_cell_measurement_reflns_used    19272
_cell_measurement_temperature    193(2)
_cell_measurement_theta_max      68.11
_cell_measurement_theta_min      2.70
_cell_volume                     1868.6(2)
_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 0.977
_diffrn_measured_fraction_theta_max 0.977
_diffrn_measurement_details      ' 493 frames, detector distance = 40 mm'
_diffrn_measurement_device       '2-circle goniometer'
_diffrn_measurement_device_type  'STOE IPDS 2T'
_diffrn_measurement_method       'rotation method'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0230
_diffrn_reflns_av_unetI/netI     0.0183
_diffrn_reflns_Laue_measured_fraction_full 0.977
_diffrn_reflns_Laue_measured_fraction_max 0.977
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            8476
_diffrn_reflns_point_group_measured_fraction_full 0.972
_diffrn_reflns_point_group_measured_fraction_max 0.970
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         67.847
_diffrn_reflns_theta_min         4.081
_diffrn_source                   'Incoatec microSource Cu'
_exptl_absorpt_coefficient_mu    3.016
_exptl_absorpt_correction_T_max  0.5745
_exptl_absorpt_correction_T_min  0.3165
_exptl_absorpt_correction_type   integration
_exptl_absorpt_process_details   X-RED
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.390
_exptl_crystal_description       block
_exptl_crystal_F_000             800
_exptl_crystal_size_max          0.430
_exptl_crystal_size_mid          0.230
_exptl_crystal_size_min          0.230
_refine_diff_density_max         0.246
_refine_diff_density_min         -0.718
_refine_diff_density_rms         0.072
_refine_ls_abs_structure_details
;
 Flack x determined using 1290 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.023(11)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.118
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     229
_refine_ls_number_reflns         3296
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.118
_refine_ls_R_factor_all          0.0433
_refine_ls_R_factor_gt           0.0409
_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^)+(0.0587P)^2^+1.0685P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1057
_refine_ls_wR_factor_ref         0.1126
_reflns_Friedel_coverage         0.722
_reflns_Friedel_fraction_full    0.964
_reflns_Friedel_fraction_max     0.961
_reflns_number_gt                3191
_reflns_number_total             3296
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja5b05056_si_003.cif
_cod_data_source_block           mesnbn
_cod_depositor_comments
'Adding full bibliography for 4123812--4123815.cif.'
_cod_database_code               4123814
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.357
_shelx_estimated_absorpt_t_max   0.544
_shelx_res_checksum              2958
_shelx_hkl_checksum              43380