One-pot catalytic asymmetric borylation of unsaturated aldehyde-derived imines; functionalisation to homoallylic boronate carboxylate ester derivatives.
Pujol, Alba; Calow, Adam D. J.; Batsanov, Andrei S.; Whiting, Andrew; Organic & biomolecular chemistry 13 (2015) 5122–5130; doi:10.1039/c4ob02657h

data_7154382
_publ_section_title
;
 One-pot catalytic asymmetric borylation of unsaturated aldehyde-derived
 imines; functionalisation to homoallylic boronate carboxylate ester
 derivatives.
;
_journal_issue                   18
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              5122
_journal_page_last               5130
_journal_paper_doi               10.1039/c4ob02657h
_journal_volume                  13
_journal_year                    2015
_chemical_formula_moiety         'C23 H21 N O'
_chemical_formula_sum            'C23 H21 N O'
_chemical_formula_weight         327.41
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_block_doi                 10.5517/cc13xm2q
_audit_creation_date             2014-10-27
_audit_creation_method
;
Olex2 1.2-beta
(compiled 2014.10.22 svn.r3046 for OlexSys, GUI svn.r4928)
;
_audit_update_record
;
2014-12-19 deposited with the CCDC.
2015-03-24 downloaded from the CCDC.
;
_cell_angle_alpha                89.082(3)
_cell_angle_beta                 80.227(5)
_cell_angle_gamma                76.501(5)
_cell_formula_units_Z            2
_cell_length_a                   6.1174(4)
_cell_length_b                   11.8050(4)
_cell_length_c                   12.9211(4)
_cell_measurement_reflns_used    7879
_cell_measurement_temperature    120
_cell_measurement_theta_max      31.7250
_cell_measurement_theta_min      1.7830
_cell_volume                     893.89(8)
_computing_cell_refinement
; CrysAlisPro, Agilent Technologies, Version 1.171.37.31 
(release 14-01-2014 CrysAlis171 .NET) (compiled Jan 14 
2014,18:38:05)
;
_computing_data_collection
; CrysAlisPro, Agilent Technologies, Version 1.171.37.31 
(release 14-01-2014 CrysAlis171 .NET) (compiled Jan 14 
2014,18:38:05)
;
_computing_data_reduction
; CrysAlisPro, Agilent Technologies, Version 1.171.37.31 
(release 14-01-2014 CrysAlis171 .NET) (compiled Jan 14 
2014,18:38:05)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement
'SHELXL 2014/7 multi-CPU version (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      120
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.15
_diffrn_detector_type            'Sapphire3 CCD area detector'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.935
_diffrn_measurement_details
;
  1 omega   -3.00   94.20   0.3000    7.5000
omega____ theta____ kappa____ phi______ frames
    -       25.4133   77.0000 -120.0000 324

  2 omega   35.00   98.00   0.3000    7.5000
omega____ theta____ kappa____ phi______ frames
    -       25.4133  178.0000   60.0000 210

  3 omega   -3.00   94.20   0.3000    7.5000
omega____ theta____ kappa____ phi______ frames
    -       25.4133   77.0000  150.0000 324

  4 omega  -44.00   53.20   0.3000    7.5000
omega____ theta____ kappa____ phi______ frames
    -       25.4133  -77.0000  -60.0000 324

  5 omega   -3.00   94.20   0.3000    7.5000
omega____ theta____ kappa____ phi______ frames
    -       25.4133   77.0000   60.0000 324

  6 omega  -44.00   53.20   0.3000    7.5000
omega____ theta____ kappa____ phi______ frames
    -       25.4133  -77.0000   30.0000 324

  7 omega  -88.00   -7.00   0.3000    7.5000
omega____ theta____ kappa____ phi______ frames
    -      -24.7883  139.0000   97.0000 270

  8 omega  -43.00   44.00   0.3000    7.5000
omega____ theta____ kappa____ phi______ frames
    -      -24.7883   57.0000 -180.0000 290

  9 omega   35.00   98.00   0.3000    7.5000
omega____ theta____ kappa____ phi______ frames
    -       25.4133  178.0000 -150.0000 210

 10 omega   35.00   98.00   0.3000    7.5000
omega____ theta____ kappa____ phi______ frames
    -       25.4133  178.0000  -30.0000 210

 11 omega    7.00   94.00   0.3000    7.5000
omega____ theta____ kappa____ phi______ frames
    -       25.4133   57.0000   30.0000 290

 12 omega    7.00   94.00   0.3000    7.5000
omega____ theta____ kappa____ phi______ frames
    -       25.4133   57.0000  -30.0000 290

 13 omega  -47.00   46.00   0.3000    7.5000
omega____ theta____ kappa____ phi______ frames
    -      -24.7883   38.0000  120.0000 310

 14 omega  -95.00   -3.80   0.3000    7.5000
omega____ theta____ kappa____ phi______ frames
    -      -24.7883  -38.0000   30.0000 304

 15 omega  -24.00   66.00   0.3000    7.5000
omega____ theta____ kappa____ phi______ frames
    -       25.4133 -100.0000   60.0000 300

 16 omega   -3.00   19.50   0.3000    7.5000
omega____ theta____ kappa____ phi______ frames
    -       25.4133   77.0000  -60.0000 75
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type
'Agilent Technologies, Gemini S Ultra kappa-diffractometer'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0134251000
_diffrn_orient_matrix_UB_12      0.0566722000
_diffrn_orient_matrix_UB_13      0.0213650000
_diffrn_orient_matrix_UB_21      -0.0186445000
_diffrn_orient_matrix_UB_22      -0.0217010000
_diffrn_orient_matrix_UB_23      0.0514549000
_diffrn_orient_matrix_UB_31      0.1188190000
_diffrn_orient_matrix_UB_32      -0.0117421000
_diffrn_orient_matrix_UB_33      0.0007980000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0460
_diffrn_reflns_av_unetI/netI     0.0336
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.935
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            29862
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.935
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         32.306
_diffrn_reflns_theta_min         1.600
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.074
_exptl_absorpt_correction_T_max  0.8623
_exptl_absorpt_correction_T_min  0.6608
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2009/1 (Bruker,2010) was used for absorption correction. 
wR2(int) was 0.0954 before and 0.0689 after correction. The Ratio 
of minimum to maximum transmission is 0.7663. The \l/2 correction 
factor is 0.0015.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.216
_exptl_crystal_description       lathe
_exptl_crystal_F_000             348
_exptl_crystal_size_max          0.7739
_exptl_crystal_size_mid          0.2708
_exptl_crystal_size_min          0.0951
_refine_diff_density_max         0.405
_refine_diff_density_min         -0.216
_refine_diff_density_rms         0.046
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.020
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     227
_refine_ls_number_reflns         5955
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.020
_refine_ls_R_factor_all          0.0662
_refine_ls_R_factor_gt           0.0512
_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^)+(0.0680P)^2^+0.2220P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1310
_refine_ls_wR_factor_ref         0.1452
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4775
_reflns_number_total             5955
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c4ob02657h2.cif
_cod_data_source_block           2b
_cod_depositor_comments
'Adding full bibliography for 7154381--7154385.cif.'
_cod_database_code               7154382
_reflns_odcompleteness_completeness 100.00
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C1(H1)
2.b Aromatic/amide H refined with riding coordinates:
 C4(H4), C3(H3), C6(H6), C7(H7), C2(H2), C12(H12), C10(H10), C9(H9), C13(H13),
 C14(H14), C15(H15), C16(H16), C21(H21), C22(H22), C18(H18), C19(H19), C20(H20)
2.c Idealised Me refined as rotating group:
 C24(H24A,H24B,H24C)
;
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'