Synthesis of fused B,N-heterocycles by alkyne cleavage, NHC ring-expansion and C-H activation at a diboryne
Brueckner, Tobias; Arrowsmith, Merle; Heß, Merlin; Hammond, Kai; Müller, Marcel; Braunschweig, Holger; Chemical Communications  (2019) –; doi:10.1039/C9CC02657F

data_7123463
_publ_section_title
;
 Synthesis of fused B,N-heterocycles by alkyne cleavage, NHC
 ring-expansion and C-H activation at a diboryne
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/C9CC02657F
_journal_year                    2019
_chemical_formula_moiety         'C66 H82 B2 N6, C6 H6'
_chemical_formula_sum            'C72 H88 B2 N6'
_chemical_formula_weight         1059.10
_chemical_properties_physical    Air-sensitive,Moisture-sensitive
_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
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2019-04-01 deposited with the CCDC.    2019-05-14 downloaded from the CCDC.
;
_cell_angle_alpha                88.333(2)
_cell_angle_beta                 82.473(2)
_cell_angle_gamma                76.374(2)
_cell_formula_units_Z            4
_cell_length_a                   10.9162(6)
_cell_length_b                   20.7562(13)
_cell_length_c                   28.3310(17)
_cell_measurement_reflns_used    7610
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      21.32
_cell_measurement_theta_min      2.27
_cell_volume                     6184.8(6)
_computing_cell_refinement       'Saint+ ver. V8.38A (Bruker AXS)'
_computing_data_collection       'APEX2 ver. 2014.9 (Bruker AXS)'
_computing_data_reduction        'Saint+ ver. V8.38A (Bruker AXS)'
_computing_molecular_graphics    'ShelXLe (Huebschle et all, 2011)'
_computing_publication_material  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT (Sheldrick, 2014)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'CCD area detector (Apex2)'
_diffrn_detector_area_resol_mean 8.333
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker X8-APEX II'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  'multi-layer mirror'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0867
_diffrn_reflns_av_unetI/netI     0.1090
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_number            89694
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         26.022
_diffrn_reflns_theta_min         1.450
_diffrn_source                   'rotating-anode (Nonius FR-591)'
_exptl_absorpt_coefficient_mu    0.066
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.6869
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SadAbs 2016/2 (Bruker AXS)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.137
_exptl_crystal_description       block
_exptl_crystal_F_000             2288
_exptl_crystal_size_max          0.399
_exptl_crystal_size_mid          0.242
_exptl_crystal_size_min          0.222
_refine_diff_density_max         0.369
_refine_diff_density_min         -0.290
_refine_diff_density_rms         0.058
_refine_ls_extinction_coef       0.0028(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   0.999
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1611
_refine_ls_number_reflns         24378
_refine_ls_number_restraints     300
_refine_ls_restrained_S_all      1.003
_refine_ls_R_factor_all          0.1542
_refine_ls_R_factor_gt           0.0682
_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^)+(0.0914P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1544
_refine_ls_wR_factor_ref         0.1951
_reflns_Friedel_coverage         0.000
_reflns_number_gt                12415
_reflns_number_total             24378
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9cc02657f2.cif
_cod_data_source_block           ToBr037_a
_cod_database_code               7123463
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_min   0.974
_shelx_estimated_absorpt_t_max   0.986
_shelx_res_checksum              98617