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_7131126
_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         'C28 H48 B2 N4 O2'
_chemical_formula_sum            'C28 H48 B2 N4 O2'
_chemical_formula_weight         494.32
_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'
_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                90
_cell_angle_beta                 117.552(12)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   19.545(2)
_cell_length_b                   9.5232(9)
_cell_length_c                   16.5656(17)
_cell_measurement_reflns_used    5110
_cell_measurement_temperature    150.00
_cell_measurement_theta_max      23.98
_cell_measurement_theta_min      3.07
_cell_volume                     2733.7(6)
_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 0.997
_diffrn_measured_fraction_theta_max 0.997
_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  0.1168
_diffrn_reflns_av_unetI/netI     0.1029
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            21652
_diffrn_reflns_point_group_measured_fraction_full 0.983
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_theta_full        24.997
_diffrn_reflns_theta_max         24.997
_diffrn_reflns_theta_min         3.797
_diffrn_source_current           30.0
_diffrn_source_power             1.5
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.074
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.201
_exptl_crystal_description       PLATE
_exptl_crystal_F_000             1080
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.226
_refine_diff_density_min         -0.234
_refine_diff_density_rms         0.057
_refine_ls_abs_structure_details
;
 Flack x determined using 1520 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.2(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     335
_refine_ls_number_reflns         4737
_refine_ls_number_restraints     4
_refine_ls_restrained_S_all      1.041
_refine_ls_R_factor_all          0.0737
_refine_ls_R_factor_gt           0.0539
_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^)+(0.0559P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1185
_refine_ls_wR_factor_ref         0.1308
_reflns_Friedel_coverage         0.970
_reflns_Friedel_fraction_full    0.969
_reflns_Friedel_fraction_max     0.969
_reflns_number_gt                3847
_reflns_number_total             4737
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2cc06207k2.cif
_cod_data_source_block           1_CCDC2
_cod_depositor_comments
'Adding full bibliography for 7131121--7131128.cif.'
_cod_database_code               7131126
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.992
_shelx_estimated_absorpt_t_min   0.990
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All C(H,H,H,H) groups
2. Restrained distances
 C26-C2 \\sim C26-C2A
 with sigma of 0.02
 C30-C2 \\sim C30-C2A
 with sigma of 0.02
3. Others
 Sof(H26C)=Sof(H26D)=Sof(H30C)=Sof(H30D)=Sof(C2A)=Sof(H2AA)=Sof(H2AB)=1-FVAR(1)
 Sof(H26A)=Sof(H26B)=Sof(H30A)=Sof(H30B)=Sof(C2)=Sof(H2A)=Sof(H2B)=FVAR(1)
4.a Ternary CH refined with riding coordinates:
 C9(H9), C11(H11), C13(H13), C18(H18)
4.b Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B), C12(H12A,H12B), C14(H14A,H14B), C15(H15A,H15B), C16(H16A,
 H16B), C17(H17A,H17B), C19(H19A,H19B), C20(H20A,H20B), C21(H21A,H21B),
 C22(H22A,H22B), C24(H24A,H24B), C25(H25A,H25B), C26(H26A,H26B), C26(H26C,H26D),
  C28(H28A,H28B), C29(H29A,H29B), C30(H30A,H30B), C30(H30C,H30D), C31(H31A,
 H31B), C32(H32A,H32B), C33(H33A,H33B), C35(H35A,H35B), C1(H1A,H1B), C2(H2A,
 H2B), C2A(H2AA,H2AB)
;
_shelx_res_checksum              45978
_shelx_hkl_checksum              6035
_olex2_submission_special_instructions 'No special instructions were received'