Synthesis of NBN-Type Zigzag-Edged Polycyclic Aromatic Hydrocarbons: 1,9-Diaza-9a-boraphenalene as a Structural Motif.
Wang, Xinyang; Zhang, Fan; Schellhammer, Karl Sebastian; Machata, Peter; Ortmann, Frank; Cuniberti, Gianaurelio; Fu, Yubin; Hunger, Jens; Tang, Ruizhi; Popov, Alexey A.; Berger, Reinhard; Müllen, Klaus; Feng, Xinliang; Journal of the American Chemical Society 138 (2016) 11606–11615; doi:10.1021/jacs.6b04445

data_4125226
_publ_section_title
;
 Synthesis of NBN-Type Zigzag-Edged Polycyclic Aromatic Hydrocarbons:
 1,9-Diaza-9a-boraphenalene as a Structural Motif.
;
_journal_issue                   36
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              11606
_journal_page_last               11615
_journal_paper_doi               10.1021/jacs.6b04445
_journal_volume                  138
_journal_year                    2016
_chemical_absolute_configuration unk
_chemical_formula_moiety         'C30 H37 B N2'
_chemical_formula_sum            'C30 H37 B N2'
_chemical_formula_weight         436.43
_space_group_crystal_system      monoclinic
_space_group_IT_number           9
_space_group_name_Hall           'C -2yc'
_space_group_name_H-M_alt        'C 1 c 1'
_symmetry_space_group_name_Hall  'C -2yc'
_symmetry_space_group_name_H-M   'C 1 c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2014
_cell_angle_alpha                90
_cell_angle_beta                 96.896(2)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   23.6678(15)
_cell_length_b                   21.4340(13)
_cell_length_c                   9.9370(6)
_cell_measurement_reflns_used    5208
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      20.94
_cell_measurement_theta_min      2.34
_cell_volume                     5004.5(5)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      200(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0662
_diffrn_reflns_av_unetI/netI     0.0889
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       29
_diffrn_reflns_limit_h_min       -29
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            40573
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         26.372
_diffrn_reflns_theta_min         1.286
_exptl_absorpt_coefficient_mu    0.066
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.9529
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   'SADABS 2014/5'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.158
_exptl_crystal_description       needle
_exptl_crystal_F_000             1888
_exptl_crystal_size_max          0.272
_exptl_crystal_size_mid          0.144
_exptl_crystal_size_min          0.054
_refine_diff_density_max         0.332
_refine_diff_density_min         -0.188
_refine_diff_density_rms         0.031
_refine_ls_abs_structure_details
;
 Refined as an inversion twin.
;
_refine_ls_extinction_coef       0.00121(11)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   0.836
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     643
_refine_ls_number_reflns         9873
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      0.836
_refine_ls_R_factor_all          0.0884
_refine_ls_R_factor_gt           0.0395
_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^)+(0.0248P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0648
_refine_ls_wR_factor_ref         0.0747
_reflns_Friedel_coverage         0.997
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     1.000
_reflns_number_gt                5692
_reflns_number_total             9873
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja6b04445_si_002.cif
_cod_data_source_block           wxy1507072
_cod_depositor_comments
'Adding full bibliography for 4125225--4125226.cif.'
_cod_database_code               4125226
_shelxl_version_number           2013-4
_shelx_res_checksum              74502
_shelx_hkl_checksum              18865