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_7131125
_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         'C20 H7 B F10 N O2, 0.4(O)'
_chemical_formula_sum            'C20 H7 B F10 N O2.4'
_chemical_formula_weight         500.48
_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
_audit_creation_date             2022-11-02
_audit_creation_method
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_audit_update_record
;
2022-11-02 deposited with the CCDC.	2022-12-15 downloaded from the CCDC.
;
_cell_angle_alpha                100.785(8)
_cell_angle_beta                 110.992(7)
_cell_angle_gamma                95.161(8)
_cell_formula_units_Z            2
_cell_length_a                   9.3567(11)
_cell_length_b                   9.9389(13)
_cell_length_c                   11.9720(14)
_cell_measurement_reflns_used    3505
_cell_measurement_temperature    150.00
_cell_measurement_theta_max      24.21
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_cell_volume                     1006.0(2)
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_diffrn_ambient_temperature      150.00
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0805
_diffrn_reflns_av_unetI/netI     0.0719
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.994
_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       14
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            16370
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         25.000
_diffrn_reflns_theta_min         3.436
_diffrn_source_current           30.0
_diffrn_source_power             1.5
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.170
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.652
_exptl_crystal_description       PLATE
_exptl_crystal_F_000             496
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.345
_refine_diff_density_min         -0.387
_refine_diff_density_rms         0.062
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     316
_refine_ls_number_reflns         3527
_refine_ls_number_restraints     6
_refine_ls_restrained_S_all      1.028
_refine_ls_R_factor_all          0.1082
_refine_ls_R_factor_gt           0.0582
_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^)+(0.0599P)^2^+1.4029P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1344
_refine_ls_wR_factor_ref         0.1676
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2172
_reflns_number_total             3527
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2cc06207k2.cif
_cod_data_source_block           1_CCDC1
_cod_depositor_comments
'Adding full bibliography for 7131121--7131128.cif.'
_cod_original_formula_sum        'C20 H7 B F10 N O2.40'
_cod_database_code               7131125
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.982
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_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2. Uiso/Uaniso restraints and constraints
C26 \\sim F15: within 2A with sigma of 0.01 and sigma for terminal atoms of
0.02 within 2A
3. Others
 Fixed Sof: O3(0.4)
4.a Secondary CH2 refined with riding coordinates:
 C27(H27A,H27B)
4.b Aromatic/amide H refined with riding coordinates:
 C20(H20), C29(H29), C31(H31), C33(H33), C34(H34)
;
_shelx_res_checksum              8282
_shelx_hkl_checksum              6117
_olex2_submission_special_instructions 'No special instructions were received'