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_7159915
_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         'C40 H40 B Cu F2 O2 P2'
_chemical_formula_sum            'C40 H40 B Cu F2 O2 P2'
_chemical_formula_weight         727.02
_space_group_crystal_system      orthorhombic
_space_group_IT_number           29
_space_group_name_Hall           'P 2c -2ac'
_space_group_name_H-M_alt        'P c a 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     difmap
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2013
_audit_update_record
;
2023-09-29 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                   22.02359(16)
_cell_length_b                   9.06591(6)
_cell_length_c                   18.14329(10)
_cell_measurement_reflns_used    26871
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      79.426
_cell_measurement_theta_min      4.688
_cell_volume                     3622.56(4)
_computing_cell_refinement       'CrysAlisPro 1.171.41.117a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.117a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.117a (Rigaku OD, 2021)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2015)'
_computing_publication_material  'SHELXTL (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       '\f and \w'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0328
_diffrn_reflns_av_unetI/netI     0.0242
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_h_min       -28
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            30742
_diffrn_reflns_point_group_measured_fraction_full 0.713
_diffrn_reflns_point_group_measured_fraction_max 0.695
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         79.884
_diffrn_reflns_theta_min         4.014
_diffrn_source                   'micro-focus sealed X-ray tube'
_exptl_absorpt_coefficient_mu    2.043
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.675
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.117a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.333
_exptl_crystal_description       prism
_exptl_crystal_F_000             1512
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.22
_refine_diff_density_max         0.300
_refine_diff_density_min         -0.424
_refine_diff_density_rms         0.049
_refine_ls_abs_structure_details
;
 Flack x determined using 1414 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   -0.001(15)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     435
_refine_ls_number_reflns         5494
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.032
_refine_ls_R_factor_all          0.0278
_refine_ls_R_factor_gt           0.0275
_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^)+(0.0475P)^2^+1.2008P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0738
_refine_ls_wR_factor_ref         0.0741
_reflns_Friedel_coverage         0.358
_reflns_Friedel_fraction_full    0.404
_reflns_Friedel_fraction_max     0.379
_reflns_number_gt                5437
_reflns_number_total             5494
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4ob00291a3.cif
_cod_data_source_block           NK1
_cod_depositor_comments
'Adding full bibliography for 7159912--7159916.cif.'
_cod_database_code               7159915
_shelx_estimated_absorpt_t_min   0.579
_shelx_estimated_absorpt_t_max   0.662
_shelxl_version_number           2013-4
_shelx_res_checksum              36942