Chiral crotyl geminal bis(silane): a useful reagent for asymmetric Sakurai allylation by selective desilylation-enabled chirality transfer.
Chu, Zhiwen; Wang, Kai; Gao, Lu; Song, Zhenlei; Chemical communications (Cambridge, England) 53 (2017) 3078–3081; doi:10.1039/c7cc00632b

data_7119705
_publ_section_title
;
 Chiral crotyl geminal bis(silane): a useful reagent for asymmetric
 Sakurai allylation by selective desilylation-enabled chirality transfer.
;
_journal_issue                   21
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              3078
_journal_page_last               3081
_journal_paper_doi               10.1039/c7cc00632b
_journal_volume                  53
_journal_year                    2017
_chemical_absolute_configuration unk
_chemical_formula_moiety         'C16 H25 Br O2 Si'
_chemical_formula_sum            'C16 H25 Br O2 Si'
_chemical_formula_weight         357.36
_chemical_name_systematic        170109_s3_zzw
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_audit_creation_date             2017-01-09
_audit_creation_method
;
Olex2 1.2
(compiled 2017.01.04 svn.r3372 for OlexSys, GUI svn.r5289)
;
_audit_update_record
;
2017-01-19 deposited with the CCDC.
2017-02-22 downloaded from the CCDC.
;
_cell_angle_alpha                90.0
_cell_angle_beta                 90.0
_cell_angle_gamma                90.0
_cell_formula_units_Z            4
_cell_length_a                   8.1374(5)
_cell_length_b                   14.2620(9)
_cell_length_c                   16.0081(12)
_cell_measurement_reflns_used    1188
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      21.9570
_cell_measurement_theta_min      3.5560
_cell_volume                     1857.8(2)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_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    'olex2.solve (Bourhis et al., 2015)'
_diffrn_ambient_temperature      293.15
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0874
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_details
;
  1 omega  -16.00   24.00   0.8000   32.5000
omega____ theta____ kappa____ phi______ frames
    -      -14.9669  -99.0000  150.0000 50

  2 omega    0.00   59.20   0.8000   32.5000
omega____ theta____ kappa____ phi______ frames
    -       16.6856   57.0000  -30.0000 74

  3 omega  -51.00   -1.40   0.8000   32.5000
omega____ theta____ kappa____ phi______ frames
    -       16.6856  -77.0000    0.0000 62
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0172053000
_diffrn_orient_matrix_UB_12      -0.0088736000
_diffrn_orient_matrix_UB_13      0.0427235000
_diffrn_orient_matrix_UB_21      -0.0240282000
_diffrn_orient_matrix_UB_22      0.0463499000
_diffrn_orient_matrix_UB_23      0.0102092000
_diffrn_orient_matrix_UB_31      -0.0820234000
_diffrn_orient_matrix_UB_32      -0.0155895000
_diffrn_orient_matrix_UB_33      0.0059597000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0348
_diffrn_reflns_av_unetI/netI     0.0715
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            5907
_diffrn_reflns_point_group_measured_fraction_full 0.910
_diffrn_reflns_point_group_measured_fraction_max 0.901
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.371
_diffrn_reflns_theta_min         2.918
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    2.277
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.61875
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.278
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             744
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: EtOAc/Hexane'
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.25
_refine_diff_density_max         0.268
_refine_diff_density_min         -0.256
_refine_diff_density_rms         0.045
_refine_ls_abs_structure_details
;
 Flack x determined using 485 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.007(12)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     187
_refine_ls_number_reflns         3429
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.031
_refine_ls_R_factor_all          0.1189
_refine_ls_R_factor_gt           0.0536
_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^)+(0.0407P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0945
_refine_ls_wR_factor_ref         0.1184
_reflns_Friedel_coverage         0.578
_reflns_Friedel_fraction_full    0.794
_reflns_Friedel_fraction_max     0.773
_reflns_number_gt                1936
_reflns_number_total             3429
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c7cc00632b2.cif
_cod_data_source_block           170109_s3_zzw
_cod_depositor_comments          'Adding full bibliography for 7119705.cif.'
_cod_database_code               7119705
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         c12h12n2o3br1si1
_cell_oxdiff_angle_alpha         90.031(9)
_cell_oxdiff_angle_beta          90.014(7)
_cell_oxdiff_angle_gamma         90.163(10)
_cell_oxdiff_length_a            8.1356(8)
_cell_oxdiff_length_b            14.272(2)
_cell_oxdiff_length_c            16.0009(13)
_cell_oxdiff_measurement_reflns_used 1188
_cell_oxdiff_volume              1857.8(3)
_shelx_estimated_absorpt_t_max   0.600
_shelx_estimated_absorpt_t_min   0.503
_reflns_odcompleteness_completeness 99.46
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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 Ternary CH refined with riding coordinates:
 C7(H7), C8(H8)
2.b Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B), C12(H12A,H12B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2A), C3(H3), C5(H5), C6(H6), C9(H9)
2.d Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C), C14(H14A,H14B,H14C), C15(H15A,H15B,H15C), C16(H16A,H16B,
 H16C)
2.e Idealised tetrahedral OH refined as rotating group:
 O1(H1), O2(H2)
;
_olex2_submission_special_instructions 'No special instructions were received'