Gamma-Silylboronates in the chiral Bronsted acid-catalysed allylboration of aldehydes
Pablo Barrio; Elsa Rodriguez; Kodai Saito; Santos Fustero; Takahiko Akiyama; Chem.Commun. 51 (2015) 5246–; doi:10.1039/C4cc08598A

data_7116762
_publ_section_title
;
 Gamma-Silylboronates in the chiral Bronsted acid-catalysed allylboration
 of aldehydes
;
_journal_name_full               Chem.Commun.
_journal_page_first              5246
_journal_paper_doi               10.1039/C4cc08598A
_journal_volume                  51
_journal_year                    2015
_chemical_absolute_configuration ad
_chemical_compound_source        'synthesis as described'
_chemical_formula_moiety         'C13 H19 N1 O3 S1'
_chemical_formula_sum            'C13 H19 N O3 S'
_chemical_formula_weight         269.35
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_Int_Tables_number      19
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2014-10-20T11:22:34-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_update_record
;
2014-10-30 deposited with the CCDC.
2014-11-26 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   11.3743(2)
_cell_length_b                   14.0235(2)
_cell_length_c                   18.6496(3)
_cell_measurement_reflns_used    17568
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      76.261
_cell_measurement_theta_min      3.905
_cell_measurement_wavelength     1.54184
_cell_volume                     2974.75(8)
_computing_cell_refinement       'CrysAlis Pro (Oxford Diffraction Ltd., 2011)'
_computing_data_collection       'CrysAlis Pro (Oxford Diffraction Ltd., 2011)'
_computing_data_reduction        'CrysAlis Pro (Oxford Diffraction Ltd., 2011)'
_computing_molecular_graphics    'Diamond v.3.2f (Crystal Impact GbR, 2008)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'OLEX2 (Dolomanov et al, 2009)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2012
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details
;
  1 omega  -27.00   50.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       40.8256  -37.0000  -90.0000 77

  2 omega   81.00  112.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       40.8256  162.0000   -7.0000 31

  3 omega   -4.00   83.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       40.8256  -99.0000   60.0000 87

  4 omega  -33.00   -8.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      -83.0000   45.0000 -120.0000 25

  5 omega   36.00   69.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -30.0000  -90.0000 33

  6 omega   91.00  140.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   45.0000  -60.0000 49

  7 omega   35.00   63.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -30.0000  -30.0000 28

  8 omega   35.00   69.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -30.0000 -120.0000 34

  9 omega   93.00  147.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   30.0000 -120.0000 54

 10 omega   42.00   69.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -45.0000 -150.0000 27

 11 omega   81.00  148.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  111.0000    0.0000 67

 12 omega   97.00  158.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   30.0000   90.0000 61

 13 omega   34.00  144.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -77.0000 -150.0000 110

 14 omega   39.00   65.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -30.0000  -60.0000 26

 15 omega  -34.00   58.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       40.8256  -37.0000   60.0000 92

 16 omega  -17.00   10.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       40.8256  -57.0000  -60.0000 27

 17 omega   11.00   37.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       40.8256  -99.0000  -90.0000 26

 18 omega   19.00  112.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       40.8256   57.0000 -150.0000 93

 19 omega   44.00   82.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       40.8256  -99.0000  -90.0000 38

 20 omega  -50.00   -8.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      -83.0000   30.0000   60.0000 42

 21 omega  126.00  156.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   45.0000    0.0000 30

 22 omega   88.00  115.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000 -111.0000  -60.0000 27

 23 omega   35.00   60.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -30.0000  150.0000 25

 24 omega   74.00  101.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -94.0000   90.0000 27

 25 omega   99.00  126.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -77.0000  -60.0000 27

 26 omega   96.00  122.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   45.0000    0.0000 26

 27 omega   41.00   66.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -30.0000  120.0000 25

 28 omega   40.00  100.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -61.0000  120.0000 60

 29 omega   42.00   69.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -30.0000 -150.0000 27

 30 omega   82.00  158.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   30.0000  150.0000 76

 31 omega  118.00  143.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -61.0000  120.0000 25

 32 omega   46.00   83.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -77.0000  -60.0000 37

 33 omega   54.00  116.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000 -111.0000   30.0000 62

 34 omega   68.00  113.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000 -111.0000 -180.0000 45

 35 omega   50.00  138.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -61.0000    0.0000 88

;
_diffrn_measurement_device       '\k-geometry diffractometer'
_diffrn_measurement_device_type  'Agilent SuperNova'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0390817
_diffrn_orient_matrix_UB_12      -0.0278747
_diffrn_orient_matrix_UB_13      -0.0762178
_diffrn_orient_matrix_UB_21      0.0499939
_diffrn_orient_matrix_UB_22      -0.0943313
_diffrn_orient_matrix_UB_23      0.0290997
_diffrn_orient_matrix_UB_31      -0.1198383
_diffrn_orient_matrix_UB_32      -0.0486946
_diffrn_orient_matrix_UB_33      -0.0128008
_diffrn_radiation_monochromator  'Multilayer optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_source         'Nova (Cu) X-ray micro-source'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0573
_diffrn_reflns_av_unetI/netI     0.0361
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            26822
_diffrn_reflns_theta_full        70.98
_diffrn_reflns_theta_max         70.98
_diffrn_reflns_theta_min         3.94
_diffrn_source_current           0.8
_diffrn_source_power             0.04
_diffrn_source_voltage           50
_exptl_absorpt_coefficient_mu    1.946
_exptl_absorpt_correction_T_max  0.849
_exptl_absorpt_correction_T_min  0.6
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
        CrysAlisPro, Agilent Technologies,
        Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET)
        (compiled Dec  3 2012,18:21:49)
Analytical numeric absorption correction using a multifaceted crystal
                        model based on expressions derived by R.C. Clark & J.S.
        (Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.203
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1152
_exptl_crystal_size_max          0.4831
_exptl_crystal_size_mid          0.1261
_exptl_crystal_size_min          0.1021
_refine_diff_density_max         0.346
_refine_diff_density_min         -0.435
_refine_diff_density_rms         0.06
_refine_ls_abs_structure_details
;
The Friedel pair coverage of the experiment is almost complete (100%).
Analysis of the absolute structure using likelihood methods
(Hooft, Straver & Spek, 2008) was performed using PLATON (Spek, 2011).
 The results indicated that the absolute structure had been correctly
 assigned. The method calculated that the probability that the structure 
is inverted is smaller than 10-99. The absolute structure parameter y 
(Hooft, Straver & Spek, 2008) was calculated using PLATON (Spek,
2010). The resulting value was y=0.160(7), which together with Flack parameter 
value, indicate that the absolute structure has sureley been determined 
correctly.

Flack, H. D. (1983), Acta Cryst. A39, 876-881
Flack & G. Bernardinelli, Acta Cryst. 1999, A55, 908-915; 
H. D. Flack & G. Bernardinelli, J. Appl. Cryst. 2000, 33, 1143-1148.

R. W. W. Hooft, L. H. Straver & A. L. Spek, J. Appl. Cryst. 2008, 41, 96-103
A. L. Spek (2010) PLATON, Utrecht, The Netherlands; 
A. L. Spek, J. Appl. Cryst. 2003, 36, 7-13
A. L. Thompson & D. J. Watkin, Tetrahedron: Asymmetry 2009, 20, 712--717

;
_refine_ls_abs_structure_Flack   0.154(14)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.06
_refine_ls_hydrogen_treatment    noref
_refine_ls_matrix_type           full
_refine_ls_number_parameters     349
_refine_ls_number_reflns         5729
_refine_ls_number_restraints     4
_refine_ls_restrained_S_all      1.064
_refine_ls_R_factor_all          0.0393
_refine_ls_R_factor_gt           0.0386
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0804P)^2^+0.3357P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1124
_refine_ls_wR_factor_ref         0.1139
_reflns_number_gt                5603
_reflns_number_total             5729
_reflns_threshold_expression     >2\s(I)
_cod_data_source_file            c4cc08598a2-1.cif
_cod_data_source_block           a2014296_er1249
_cod_database_code               7116762