Asymmetric retro-[1,4]-Brook rearrangement of 3-silyl allyloxysilanes via chirality transfer from silicon to carbon
Wu, Ya; Chen, Hua; Yang, Wenyu; Fan, Yu; Gao, Lu; Su, Zhishan; Hu, Changwei; Song, Zhenlei; RSC Advances 9 (2019) 26209–; doi:10.1039/C9RA05482K

data_7233415
_publ_section_title
;
 Asymmetric retro-[1,4]-Brook rearrangement of 3-silyl allyloxysilanes via
 chirality transfer from silicon to carbon
;
_journal_issue                   45
_journal_name_full               'RSC Advances'
_journal_page_first              26209
_journal_paper_doi               10.1039/C9RA05482K
_journal_volume                  9
_journal_year                    2019
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C32 H36 O Si2'
_chemical_formula_sum            'C32 H36 O Si2'
_chemical_formula_weight         492.79
_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'
_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     dual
_audit_creation_date             2017-04-07
_audit_creation_method
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5335)
;
_audit_update_record
;
2019-03-08 deposited with the CCDC.    2019-08-12 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.5099(2)
_cell_length_b                   14.8311(3)
_cell_length_c                   18.2540(3)
_cell_measurement_reflns_used    17374
_cell_measurement_temperature    293
_cell_measurement_theta_max      71.7840
_cell_measurement_theta_min      3.8330
_cell_volume                     2845.31(9)
_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  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XT (Sheldrick, 2015)'
_diffrn_ambient_temperature      293
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0356
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_details
;
  1 omega   18.00   91.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       37.7849 -125.0000  -60.0000 73

  2 omega   18.00   91.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       37.7849 -125.0000 -150.0000 73

  3 omega    8.00  109.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       37.7849   19.0000 -120.0000 101

  4 omega  -31.00   57.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       37.7849  -37.0000  150.0000 88

  5 omega   18.00   91.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       37.7849 -125.0000  120.0000 73

  6 omega   21.00  105.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       37.7849   57.0000  -30.0000 84

  7 omega  -29.00   55.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       37.7849  -57.0000 -150.0000 84

  8 omega  -30.00   65.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       37.7849  -77.0000   90.0000 95

  9 omega   37.00  146.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -15.0000  -30.0000 109

 10 omega   39.00  109.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000 -150.0000 70

 11 omega   40.00  135.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -77.0000   30.0000 95

 12 omega   38.00   90.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000  150.0000 52

 13 omega   38.00   90.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000  -60.0000 52

 14 omega   40.00  135.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -77.0000  -90.0000 95

 15 omega  100.00  178.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  111.0000   90.0000 78

 16 omega   40.00   98.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000 -150.0000 58

 17 omega   81.00  176.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000  150.0000 95

 18 omega   11.00  105.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       37.7849   77.0000   30.0000 94

 19 omega  -31.00   57.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       37.7849  -37.0000  -60.0000 88

 20 omega   -3.00   23.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       37.7849  102.0000 -142.7209 26

 21 omega   11.00  105.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       37.7849   77.0000  -60.0000 94

 22 omega   -1.00   26.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       37.7849   98.0000  150.7571 27

 23 omega   11.00  105.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       37.7849   77.0000   90.0000 94

 24 omega   21.00  105.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       37.7849   57.0000 -180.0000 84

 25 omega   21.00  105.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       37.7849   57.0000  -90.0000 84

 26 omega   91.00  176.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   45.0000  120.0000 85

 27 omega   91.00  176.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   45.0000    0.0000 85

 28 omega   81.00  176.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000  -90.0000 95

 29 omega   87.00  178.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   30.0000 -120.0000 91

 30 omega   70.00  178.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   15.0000   90.0000 108

 31 omega   38.00   84.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -111.0000  120.0000 46

 32 omega   91.00  176.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   45.0000  -30.0000 85
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.1110214000
_diffrn_orient_matrix_UB_12      -0.0091141000
_diffrn_orient_matrix_UB_13      0.0546058000
_diffrn_orient_matrix_UB_21      -0.0828598000
_diffrn_orient_matrix_UB_22      0.0423802000
_diffrn_orient_matrix_UB_23      0.0605121000
_diffrn_orient_matrix_UB_31      -0.0479409000
_diffrn_orient_matrix_UB_32      -0.0943801000
_diffrn_orient_matrix_UB_33      0.0219075000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0287
_diffrn_reflns_av_unetI/netI     0.0149
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            33976
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         71.851
_diffrn_reflns_theta_min         4.845
_diffrn_source                   'Enhance (Cu) X-ray Source'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.286
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.64840
_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            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.150
_exptl_crystal_description       block
_exptl_crystal_F_000             1056
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.3
_refine_diff_density_max         0.213
_refine_diff_density_min         -0.207
_refine_diff_density_rms         0.049
_refine_ls_abs_structure_details
;
 Flack x determined using 2267 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.014(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     320
_refine_ls_number_reflns         5527
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.059
_refine_ls_R_factor_all          0.0365
_refine_ls_R_factor_gt           0.0352
_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^)+(0.0727P)^2^+0.1820P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0991
_refine_ls_wR_factor_ref         0.1009
_reflns_Friedel_coverage         0.770
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.988
_reflns_number_gt                5350
_reflns_number_total             5527
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9ra05482k2.cif
_cod_data_source_block           s
_cod_database_code               7233415
_shelx_shelxl_version_number     2014/7
_reflns_odcompleteness_completeness 99.90
_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
2.a Ternary CH refined with riding coordinates:
 C00H(H00H)
2.b Secondary CH2 refined with riding coordinates:
 C00L(H00F,H00L)
2.c Aromatic/amide H refined with riding coordinates:
 C007(H007), C008(H008), C009(H009), C00A(H00A), C00B(H00B), C00C(H00C),
 C00D(H00D), C00E(H00E), C00G(H00G), C00I(H00I), C00J(H00J), C00K(H00K),
 C00M(H00M), C00N(H00N), C00O(H00O), C00P(H00P), C00Q(H00Q), C00S(H00U),
 C00T(H00V), C00U(H00W), C00V(H00X)
2.d Idealised Me refined as rotating group:
 C00R(H00R,H00S,H00T), C00X(H00Y,H,HA), C00Y(H00Z,HB,HC), C00Z(H00,HD,HE)
;
_olex2_submission_special_instructions 'No special instructions were received'