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_7131124
_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         'C15 H2 B Cl3 F10 N O2'
_chemical_formula_sum            'C15 H2 B Cl3 F10 N O2'
_chemical_formula_weight         535.34
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_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                90
_cell_angle_beta                 102.294(6)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.4303(11)
_cell_length_b                   15.7714(15)
_cell_length_c                   11.0532(9)
_cell_measurement_reflns_used    2016
_cell_measurement_temperature    150.00
_cell_measurement_theta_max      24.11
_cell_measurement_theta_min      3.20
_cell_volume                     1776.6(3)
_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)'
_computing_structure_solution    'XT  (Sheldrick, 2015)'
_diffrn_ambient_temperature      150.00
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.986
_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  0.0742
_diffrn_reflns_av_unetI/netI     0.0767
_diffrn_reflns_Laue_measured_fraction_full 0.986
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            12157
_diffrn_reflns_point_group_measured_fraction_full 0.986
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_theta_full        24.998
_diffrn_reflns_theta_max         24.998
_diffrn_reflns_theta_min         2.286
_diffrn_source_current           30.0
_diffrn_source_power             1.5
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.634
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    2.002
_exptl_crystal_description       block
_exptl_crystal_F_000             1044
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.930
_refine_diff_density_min         -0.337
_refine_diff_density_rms         0.077
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.020
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     326
_refine_ls_number_reflns         3090
_refine_ls_number_restraints     16
_refine_ls_restrained_S_all      1.024
_refine_ls_R_factor_all          0.0883
_refine_ls_R_factor_gt           0.0506
_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^)+(0.0431P)^2^+2.7226P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1104
_refine_ls_wR_factor_ref         0.1310
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2083
_reflns_number_total             3090
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2cc06207k2.cif
_cod_data_source_block           1
_cod_depositor_comments
'Adding full bibliography for 7131121--7131128.cif.'
_cod_database_code               7131124
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.939
_shelx_estimated_absorpt_t_min   0.917
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H,H,H,H) groups
2. Restrained distances
 C30-C32 \\sim C30-C32A
 with sigma of 0.02
 C30-Cl2 \\sim C30-Cl2A
 with sigma of 0.04
 C32-Cl1 \\sim C32A-Cl1A
 with sigma of 0.02
 C32-Cl3 \\sim C32A-Cl3A
 with sigma of 0.02
 C32-Cl2 \\sim C32A-Cl2A
 with sigma of 0.02
 Cl1-Cl3 \\sim Cl1A-Cl3A
 with sigma of 0.04
 Cl3-Cl2 \\sim Cl3A-Cl2A
 with sigma of 0.04
 Cl1-Cl2 \\sim Cl1A-Cl2A
 with sigma of 0.04
 C30-Cl1 \\sim C30-Cl1A
 with sigma of 0.04
 C30-Cl3 \\sim C30-Cl3A
 with sigma of 0.04
3. Uiso/Uaniso restraints and constraints
Uanis(C32A) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
4. Others
 Sof(H30C)=Sof(H30D)=Sof(Cl2A)=Sof(C32A)=Sof(Cl3A)=Sof(Cl1A)=1-FVAR(1)
 Sof(H30A)=Sof(H30B)=Sof(C32)=Sof(Cl1)=Sof(Cl3)=Sof(Cl2)=FVAR(1)
5.a Secondary CH2 refined with riding coordinates:
 C30(H30A,H30B), C30(H30C,H30D)
;
_shelx_res_checksum              80436
_shelx_hkl_checksum              83842
_olex2_submission_special_instructions 'No special instructions were received'