Silyl-Group-Directed Linear-Selective Allylation of Carbonyl Compounds with Trisubstituted Allylboronates Using a Copper(I) Catalyst
Iwamoto, Hiroaki; Hayashi, Yuta; Ozawa, Yu; Ito, Hajime; ACS Catalysis  (2020) 2471–; doi:10.1021/acscatal.9b05408

data_4517382
_publ_section_title
;
 Silyl-Group-Directed Linear-Selective Allylation of Carbonyl Compounds
 with Trisubstituted Allylboronates Using a Copper(I) Catalyst
;
_journal_name_full               'ACS Catalysis'
_journal_page_first              2471
_journal_paper_doi               10.1021/acscatal.9b05408
_journal_year                    2020
_chemical_formula_moiety         'C20 H23 F3 O Si'
_chemical_formula_sum            'C20 H23 F3 O Si'
_chemical_formula_weight         364.47
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2018-12-15
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 94.714(2)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   13.3534(2)
_cell_length_b                   19.2873(3)
_cell_length_c                   14.6810(2)
_cell_measurement_reflns_used    13959
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      73.2450
_cell_measurement_theta_min      3.3070
_cell_volume                     3768.32(10)
_computing_cell_refinement       'CrysAlisPro 1.171.39.43a (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.43a (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.43a (Rigaku OD, 2018)'
_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    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'PLATUS 200K area detector'
_diffrn_detector_area_resol_mean 5.811
_diffrn_detector_type            'HPC area detector'
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.963
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
--------------------------------------------------------------------------
  1  \w    -14.00  12.00   0.50    1.32    --    5.00  58.00 118.00   52
  2  \w   -119.00 -53.00   0.50    1.32    --  -96.30  58.00 118.00  132
  3  \w    -89.00  65.00   0.50    0.50    --    0.00  14.00   0.00  308
  4  \w   -163.00  -9.00   0.50    1.32    --  -96.30  57.00  90.00  308
  5  \w   -182.00  -9.00   0.50    1.32    --  -96.30  60.00  30.00  346
  6  \w   -186.00 -10.00   0.50    1.32    --  -96.30   0.00-120.00  352
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Rigaku XtaLAB P200'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0747299000
_diffrn_orient_matrix_UB_12      0.0591632000
_diffrn_orient_matrix_UB_13      0.0139493000
_diffrn_orient_matrix_UB_21      0.0249443000
_diffrn_orient_matrix_UB_22      0.0327482000
_diffrn_orient_matrix_UB_23      -0.0910912000
_diffrn_orient_matrix_UB_31      -0.0847484000
_diffrn_orient_matrix_UB_32      -0.0426469000
_diffrn_orient_matrix_UB_33      -0.0508166000
_diffrn_radiation_monochromator  'multi-layer mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0336
_diffrn_reflns_av_unetI/netI     0.0292
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.963
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            19153
_diffrn_reflns_point_group_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.963
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.658
_diffrn_reflns_theta_min         3.321
_diffrn_source                   'rotating anode X-ray generator'
_diffrn_source_type              micromax007
_exptl_absorpt_coefficient_mu    1.397
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.65811
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.43a (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'metallic light colourless'
_exptl_crystal_colour_lustre     metallic
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.285
_exptl_crystal_description       block
_exptl_crystal_F_000             1536
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.332
_refine_diff_density_min         -0.745
_refine_diff_density_rms         0.084
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.114
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     458
_refine_ls_number_reflns         7329
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.118
_refine_ls_R_factor_all          0.0552
_refine_ls_R_factor_gt           0.0516
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1206P)^2^+0.7485P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1733
_refine_ls_wR_factor_ref         0.1793
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6523
_reflns_number_total             7329
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            cs9b05408_si_002.cif
_cod_data_source_block           hys-360-1
_cod_database_code               4517382
_shelx_shelxl_version_number     2018/1
_chemical_oxdiff_formula         'C H Si O F'
_shelx_estimated_absorpt_t_max   0.873
_shelx_estimated_absorpt_t_min   0.572
_reflns_odcompleteness_completeness 98.95
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C00J(H00H,H00I), C00O(H00B,H00C)
2.b Aromatic/amide H refined with riding coordinates:
 C00C(H00G), C00K(H00K), C00L(H00L), C00M(H00M), C00P(H00P), C00Q(H00Q),
 C00V(H00V), C00W(H00W), C00X(H00X), C00Y(H00Y), C00Z(H00Z), C010(H010),
 C011(H011), C012(H012), C013(H013), C014(H014), C015(H015), C016(H016),
 C01A(H01D), C01B(H01P), C01C(H01E), C01E(H01I)
2.c Tetrahedral OH refined with riding coordinates:
 O009(H009)
2.d Idealised Me refined as rotating group:
 C00R(H00D,H00E,H00F), C00S(H00J,H00N,H00O), C017(H01A,H01B,H01C), C018(H01J,
 H01K,H01L), C019(H01M,H01N,H01O), C01D(H01F,H01G,H01H)
2.e Idealised tetrahedral OH refined as rotating group:
 O00A(H00A)
;
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.173
_oxdiff_exptl_absorpt_empirical_full_min 0.257