Enantio- and diastereoselective boron conjugate addition to α-alkyl α,β-unsaturated esters.
Li, Meng; Peng, Guang-Rui; Yang, Xuan; Ma, Zhen-Ning; Xie, Jian-Bo; Organic & biomolecular chemistry 21 (2022) 53–58; doi:10.1039/d2ob01928k

data_7159026
_publ_section_title
;
 Enantio- and diastereoselective boron conjugate addition to &#x3b1;-alkyl
 &#x3b1;,&#x3b2;-unsaturated esters.
;
_journal_issue                   1
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              53
_journal_page_last               58
_journal_paper_doi               10.1039/d2ob01928k
_journal_volume                  21
_journal_year                    2022
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C23 H29 B F N O3'
_chemical_formula_sum            'C23 H29 B F N O3'
_chemical_formula_weight         397.28
_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   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2021-04-23
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2022-05-09 deposited with the CCDC.	2022-11-25 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 93.034(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   10.0208(5)
_cell_length_b                   9.4096(5)
_cell_length_c                   12.1630(7)
_cell_measurement_reflns_used    9726
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      53.96
_cell_measurement_theta_min      5.104
_cell_volume                     1145.26(11)
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'XT (Sheldrick, 2015)'
_diffrn_ambient_temperature      150.0
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           GaK\a
_diffrn_radiation_wavelength     1.34139
_diffrn_reflns_av_R_equivalents  0.0479
_diffrn_reflns_av_unetI/netI     0.0281
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            36956
_diffrn_reflns_point_group_measured_fraction_full 0.983
_diffrn_reflns_point_group_measured_fraction_max 0.981
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         54.101
_diffrn_reflns_theta_min         5.110
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.416
_exptl_absorpt_correction_T_max  0.7506
_exptl_absorpt_correction_T_min  0.5772
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1505 before and 0.0714 after correction. The Ratio of minimum to maximum transmission is 0.7690. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.152
_exptl_crystal_description       block
_exptl_crystal_F_000             424
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.699
_refine_diff_density_min         -0.231
_refine_diff_density_rms         0.052
_refine_ls_abs_structure_details
;
 Flack x determined using 1653 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.02(6)
_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     308
_refine_ls_number_reflns         4152
_refine_ls_number_restraints     100
_refine_ls_restrained_S_all      1.139
_refine_ls_R_factor_all          0.0609
_refine_ls_R_factor_gt           0.0577
_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^)+(0.1135P)^2^+0.3158P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1624
_refine_ls_wR_factor_ref         0.1659
_reflns_Friedel_coverage         0.864
_reflns_Friedel_fraction_full    0.977
_reflns_Friedel_fraction_max     0.974
_reflns_number_gt                3897
_reflns_number_total             4152
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2ob01928k2.cif
_cod_data_source_block           20210423bl_0m_a
_cod_depositor_comments          'Adding full bibliography for 7159026.cif.'
_cod_database_code               7159026
_shelx_shelxl_version_number     2016/6
_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. Rigid bond restraints
 B1, O2, O3, C21, C22, C21A, C22A, C23, C24, C25, C24A, C25A
 with sigma for 1-2 distances of 0.005 and sigma for 1-3 distances of 0.005
3. Uiso/Uaniso restraints and constraints
B1 \\sim O2 \\sim O3 \\sim C21 \\sim C22 \\sim C21A \\sim C22A \\sim C23 \\sim
C24 \\sim C25 \\sim C24A \\sim C25A: within 2A with sigma of 0.005 and sigma
for terminal atoms of 0.01
Uanis(C21) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
4. Others
 Sof(C21)=Sof(H21A)=Sof(H21B)=Sof(H21C)=Sof(C22)=Sof(H22A)=Sof(H22B)=Sof(H22C)=
 Sof(C24A)=Sof(H24D)=Sof(H24E)=Sof(H24F)=Sof(C25A)=Sof(H25D)=Sof(H25E)=
 Sof(H25F)=1-FVAR(1)
 Sof(C21A)=Sof(H21D)=Sof(H21E)=Sof(H21F)=Sof(C22A)=Sof(H22D)=Sof(H22E)=
 Sof(H22F)=Sof(C24)=Sof(H24A)=Sof(H24B)=Sof(H24C)=Sof(C25)=Sof(H25A)=Sof(H25B)=
 Sof(H25C)=FVAR(1)
5.a Ternary CH refined with riding coordinates:
 C3(H3), C13(H13)
5.b Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B)
5.c Aromatic/amide H refined with riding coordinates:
 N2(H2), C8(H8), C9(H9), C10(H10), C11(H11), C12(H12), C15(H15), C16(H16),
 C17(H17), C18(H18)
5.d Idealised Me refined as rotating group:
 C4(H4A,H4B,H4C), C21(H21A,H21B,H21C), C22(H22A,H22B,H22C), C21A(H21D,H21E,
 H21F), C22A(H22D,H22E,H22F), C24(H24A,H24B,H24C), C25(H25A,H25B,H25C),
 C24A(H24D,H24E,H24F), C25A(H25D,H25E,H25F)
;
_shelx_res_checksum              31399
_olex2_submission_special_instructions 'No special instructions were received'