Amine adducts of triallylborane as highly reactive allylborating agents for Cu(I)-catalyzed allylation of chiral sulfinylimines.
Alexeev, Michael S.; Strelkova, Tatiana V.; Ilyin, Michael M.; Nelyubina, Yulia V.; Bespalov, Ivan A.; Medvedev, Michael G.; Khrustalev, Victor N.; Kuznetsov, Nikolai Yu; Organic & biomolecular chemistry 22 (2024) 4680–4696; doi:10.1039/d4ob00291a

data_7159913
_publ_section_title
;
 Amine adducts of triallylborane as highly reactive allylborating agents
 for Cu(I)-catalyzed allylation of chiral sulfinylimines.
;
_journal_issue                   23
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              4680
_journal_page_last               4696
_journal_paper_doi               10.1039/d4ob00291a
_journal_volume                  22
_journal_year                    2024
_chemical_absolute_configuration unk
_chemical_formula_moiety         'C15 H27 B N2'
_chemical_formula_sum            'C15 H27 B N2'
_chemical_formula_weight         246.19
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2023-08-14
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_audit_update_record
;
2023-08-16 deposited with the CCDC.	2024-04-17 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.6952(2)
_cell_length_b                   10.1193(2)
_cell_length_c                   17.1397(4)
_cell_measurement_reflns_used    5580
_cell_measurement_temperature    100
_cell_measurement_theta_max      28.84
_cell_measurement_theta_min      2.34
_cell_volume                     1508.11(6)
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2014/4 (Sheldrick, 2014)'
_diffrn_ambient_temperature      100
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker Quest D8'
_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  0.0452
_diffrn_reflns_av_unetI/netI     0.0352
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            20204
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.993
_diffrn_reflns_theta_min         2.337
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.062
_exptl_absorpt_correction_T_max  0.4330
_exptl_absorpt_correction_T_min  0.3775
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1112 before and 0.0442 after correction.
The Ratio of minimum to maximum transmission is 0.8718.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.084
_exptl_crystal_description       needle
_exptl_crystal_F_000             544
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.208
_refine_diff_density_min         -0.183
_refine_diff_density_rms         0.037
_refine_ls_abs_structure_details
;
 Flack x determined using 1409 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -1.4(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     180
_refine_ls_number_reflns         4000
_refine_ls_number_restraints     6
_refine_ls_restrained_S_all      1.080
_refine_ls_R_factor_all          0.0557
_refine_ls_R_factor_gt           0.0485
_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^)+(0.0608P)^2^+0.2999P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1193
_refine_ls_wR_factor_ref         0.1240
_reflns_Friedel_coverage         0.749
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     1.000
_reflns_number_gt                3582
_reflns_number_total             4000
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4ob00291a3.cif
_cod_data_source_block           TABDABCO
_cod_depositor_comments
'Adding full bibliography for 7159912--7159916.cif.'
_cod_database_code               7159913
_shelxl_version_number           2014/6
_shelx_estimated_absorpt_t_max   0.997
_shelx_estimated_absorpt_t_min   0.978
_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
 C14-C13 \\sim C14'-C13'
 with sigma of 0.02
 C13'-B1 \\sim C13-B1
 with sigma of 0.02
 C10'-B1 \\sim C10-B1
 with sigma of 0.02
 C11'-C10' \\sim C11-C10
 with sigma of 0.02
 C12'-C11' \\sim C12-C11
 with sigma of 0.02
 C14-C15 \\sim C14'-C15
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(C13) = Uanis(C13')
Uanis(C14) = Uanis(C14')
Uanis(C10') = Uanis(C10)
Uanis(C11) = Uanis(C11')
Uanis(C12') = Uanis(C12)
4. Others
 Sof(H15C)=Sof(H15D)=Sof(C13')=Sof(H13C)=Sof(H13D)=Sof(C14')=Sof(H14')=1-FVAR(1)
 Sof(H15A)=Sof(H15B)=Sof(C13)=Sof(H13A)=Sof(H13B)=Sof(C14)=Sof(H14)=FVAR(1)
 Sof(C10')=Sof(H10C)=Sof(H10D)=Sof(C11')=Sof(H11')=Sof(C12')=Sof(H12C)=
 Sof(H12D)=1-FVAR(2)
 Sof(C10)=Sof(H10A)=Sof(H10B)=Sof(C11)=Sof(H11)=Sof(C12)=Sof(H12A)=Sof(H12B)=
 FVAR(2)
5.a Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C2(H2A,H2B), C3(H3A,H3B), C4(H4A,H4B), C5(H5A,H5B), C6(H6A,H6B),
 C7(H7A,H7B), C10(H10A,H10B), C13(H13A,H13B), C10'(H10C,H10D), C13'(H13C,H13D)
5.b Aromatic/amide H refined with riding coordinates:
 C8(H8), C11(H11), C14(H14), C11'(H11'), C14'(H14')
5.c X=CH2 refined with riding coordinates:
 C9(H9A,H9B), C15(H15A,H15B), C15(H15C,H15D), C12(H12A,H12B), C12'(H12C,H12D)
;
_shelx_res_checksum              81653
_olex2_submission_special_instructions 'No special instructions were received'