Transient hydroboration and hydroalumination of activated azo-species: avenues to NBO and NAlO-heterobicycles.
Mandal, Dipendu; Hussain, Zahid; Luo, Yong-An; Wu, Yile; Stephan, Douglas W.; Chemical communications (Cambridge, England) 59 (2023) 780–783; doi:10.1039/d2cc06207k

data_7131122
_publ_section_title
;
 Transient hydroboration and hydroalumination of activated azo-species:
 avenues to NBO and NAlO-heterobicycles.
;
_journal_issue                   6
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              780
_journal_page_last               783
_journal_paper_doi               10.1039/d2cc06207k
_journal_volume                  59
_journal_year                    2023
_chemical_formula_moiety         'C16 H7 B F10 N O2'
_chemical_formula_sum            'C16 H7 B F10 N O2'
_chemical_formula_weight         446.04
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2022-09-20
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2022-11-01 deposited with the CCDC.	2022-12-15 downloaded from the CCDC.
;
_cell_angle_alpha                97.826(2)
_cell_angle_beta                 104.572(2)
_cell_angle_gamma                112.363(2)
_cell_formula_units_Z            2
_cell_length_a                   9.4139(2)
_cell_length_b                   9.7064(3)
_cell_length_c                   10.5352(3)
_cell_measurement_reflns_used    2796
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      69.852
_cell_measurement_theta_min      4.490
_cell_volume                     832.20(4)
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XT (Sheldrick, 2015)'
_diffrn_ambient_temperature      200.0
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0411
_diffrn_reflns_av_unetI/netI     0.0463
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.981
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            7603
_diffrn_reflns_point_group_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.981
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         70.059
_diffrn_reflns_theta_min         4.490
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.741
_exptl_absorpt_correction_T_max  0.7533
_exptl_absorpt_correction_T_min  0.6287
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0948 before and 0.0507 after correction. The Ratio of minimum to maximum transmission is 0.8346. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.780
_exptl_crystal_description       block
_exptl_crystal_F_000             442
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.547
_refine_diff_density_min         -0.224
_refine_diff_density_rms         0.052
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     273
_refine_ls_number_reflns         3107
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.059
_refine_ls_R_factor_all          0.0606
_refine_ls_R_factor_gt           0.0474
_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^)+(0.0659P)^2^+0.1989P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1253
_refine_ls_wR_factor_ref         0.1337
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2380
_reflns_number_total             3107
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2cc06207k2.cif
_cod_data_source_block           l2
_cod_depositor_comments
'Adding full bibliography for 7131121--7131128.cif.'
_cod_database_code               7131122
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.818
_shelx_estimated_absorpt_t_min   0.722
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C2(H2)
2.b Idealised Me refined as rotating group:
 C3(H3A,H3B,H3C), C4(H4A,H4B,H4C)
;
_olex2_submission_special_instructions 'No special instructions were received'