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_7159914
_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 ad
_chemical_formula_moiety         'C14 H22 N2 O S'
_chemical_formula_sum            'C14 H22 N2 O S'
_chemical_formula_weight         266.39
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   mixed
_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                 108.897(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   10.7916(4)
_cell_length_b                   6.2242(2)
_cell_length_c                   11.7768(4)
_cell_measurement_reflns_used    5319
_cell_measurement_temperature    100
_cell_measurement_theta_max      30.60
_cell_measurement_theta_min      3.11
_cell_volume                     748.40(5)
_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 0.999
_diffrn_measured_fraction_theta_max 0.999
_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  0.0347
_diffrn_reflns_av_unetI/netI     0.0446
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            9895
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.997
_diffrn_reflns_theta_min         1.995
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.208
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.6473
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1129 before and 0.0536 after correction.
The Ratio of minimum to maximum transmission is 0.8676.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.182
_exptl_crystal_description       needle
_exptl_crystal_F_000             288
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.288
_refine_diff_density_min         -0.195
_refine_diff_density_rms         0.040
_refine_ls_abs_structure_details
;
 Flack x determined using 1589 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.03(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     167
_refine_ls_number_reflns         3943
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.039
_refine_ls_R_factor_all          0.0347
_refine_ls_R_factor_gt           0.0316
_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^)+(0.0358P)^2^+0.0575P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0750
_refine_ls_wR_factor_ref         0.0767
_reflns_Friedel_coverage         0.823
_reflns_Friedel_fraction_full    0.987
_reflns_Friedel_fraction_max     0.980
_reflns_number_gt                3721
_reflns_number_total             3943
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4ob00291a3.cif
_cod_data_source_block           Org
_cod_depositor_comments
'Adding full bibliography for 7159912--7159916.cif.'
_cod_database_code               7159914
_shelxl_version_number           2014/6
_shelx_estimated_absorpt_t_max   0.990
_shelx_estimated_absorpt_t_min   0.950
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Riding coordinates:
 N1(H1)
2.b Ternary CH refined with riding coordinates:
 C1(H1A)
2.c Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B)
2.d Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), C9(H9)
2.e X=CH2 refined with riding coordinates:
 C10(H10A,H10B)
2.f Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C), C12(H12A,H12B,H12C), C13(H13A,H13B,H13C), C14(H14A,H14B,H14C)
;
_shelx_res_checksum              36759
_olex2_submission_special_instructions 'No special instructions were received'