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_7233414
_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_formula_moiety         'C39 H39 N O4 Si2'
_chemical_formula_sum            'C39 H39 N O4 Si2'
_chemical_formula_weight         641.89
_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     iterative
_audit_creation_date             2016-12-08
_audit_creation_method
;
Olex2 1.2
(compiled 2016.11.30 svn.r3356 for OlexSys, GUI svn.r5269)
;
_audit_update_record
;
2019-03-08 deposited with the CCDC.    2019-08-12 downloaded from the CCDC.
;
_cell_angle_alpha                95.541(5)
_cell_angle_beta                 104.025(6)
_cell_angle_gamma                112.585(8)
_cell_formula_units_Z            2
_cell_length_a                   10.0776(8)
_cell_length_b                   11.8793(10)
_cell_length_c                   16.4275(9)
_cell_measurement_reflns_used    4762
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.6890
_cell_measurement_theta_min      3.3650
_cell_volume                     1721.7(3)
_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
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_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 0.9983
_diffrn_measured_fraction_theta_max 0.8365
_diffrn_measurement_details
;
  1 omega  -87.00  -35.00   1.0000    9.0000
omega____ theta____ kappa____ phi______ frames
    -      -14.9669 -178.0000   30.0000 52

  2 omega  -25.00   24.00   1.0000    9.0000
omega____ theta____ kappa____ phi______ frames
    -      -14.9669  -99.0000  150.0000 49

  3 omega    2.00   82.00   1.0000    9.0000
omega____ theta____ kappa____ phi______ frames
    -       16.6856   57.0000  -30.0000 80

  4 omega  -35.00   31.00   1.0000    9.0000
omega____ theta____ kappa____ phi______ frames
    -       16.6856  -57.0000   60.0000 66

  5 omega   25.00   59.00   1.0000    9.0000
omega____ theta____ kappa____ phi______ frames
    -       16.6856   57.0000   30.0000 34

  6 omega  -50.00   43.00   1.0000    9.0000
omega____ theta____ kappa____ phi______ frames
    -       16.6856  -77.0000 -150.0000 93
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0575032000
_diffrn_orient_matrix_UB_12      0.0452316000
_diffrn_orient_matrix_UB_13      -0.0122380000
_diffrn_orient_matrix_UB_21      -0.0349252000
_diffrn_orient_matrix_UB_22      -0.0331051000
_diffrn_orient_matrix_UB_23      -0.0433151000
_diffrn_orient_matrix_UB_31      -0.0433191000
_diffrn_orient_matrix_UB_32      0.0351610000
_diffrn_orient_matrix_UB_33      -0.0068992000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0189
_diffrn_reflns_av_unetI/netI     0.0382
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            14009
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.372
_diffrn_reflns_theta_min         2.889
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.144
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.94699
_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_density_diffrn    1.238
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             680
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.3
_refine_diff_density_max         0.307
_refine_diff_density_min         -0.194
_refine_diff_density_rms         0.037
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     419
_refine_ls_number_reflns         7043
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.028
_refine_ls_R_factor_all          0.0649
_refine_ls_R_factor_gt           0.0451
_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^)+(0.0504P)^2^+0.3181P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1051
_refine_ls_wR_factor_ref         0.1174
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5350
_reflns_number_total             7043
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9ra05482k2.cif
_cod_data_source_block           161207_s1_wy
_cod_original_cell_volume        1721.7(2)
_cod_database_code               7233414
_chemical_oxdiff_formula         c12h12n2si2
_shelx_estimated_absorpt_t_max   0.958
_shelx_estimated_absorpt_t_min   0.951
_reflns_odcompleteness_completeness 99.83
_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:
 C10(H10)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C5(H5), C6(H6), C8(H8), C9(H9), C12(H12), C13(H13), C14(H14),
 C15(H15), C16(H16), C18(H18), C19(H19), C20(H20), C21(H21), C22(H22), C24(H24),
  C25(H25), C26(H26), C27(H27), C28(H28), C35(H35), C36(H36), C37(H37),
 C38(H38), C39(H39)
2.c Idealised Me refined as rotating group:
 C29(H29A,H29B,H29C), C31(H31A,H31B,H31C), C32(H32A,H32B,H32C), C33(H33A,H33B,
 H33C)
;
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'