Brønsted Acid Catalyzed 1,2-Silyl Shift in Propargyl Silanes: Synthesis of Silyl Dienes and Silyl Indenes.
Puriņš, Mikus; Mishnev, Anatoly; Turks, Ma Ris; The Journal of organic chemistry 84 (2019) 3595–3611; doi:10.1021/acs.joc.8b02735

data_4033892
_publ_section_title
;
 Br\/onsted Acid Catalyzed 1,2-Silyl Shift in Propargyl Silanes: Synthesis
 of Silyl Dienes and Silyl Indenes.
;
_journal_issue                   6
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              3595
_journal_page_last               3611
_journal_paper_doi               10.1021/acs.joc.8b02735
_journal_volume                  84
_journal_year                    2019
_chemical_absolute_configuration rm
_chemical_formula_moiety         'C21 H32 O2 Si'
_chemical_formula_sum            'C21 H32 O2 Si'
_chemical_formula_weight         344.55
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2017/1
_cell_angle_alpha                90
_cell_angle_beta                 110.361(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   10.7686(3)
_cell_length_b                   6.6244(2)
_cell_length_c                   15.1218(5)
_cell_measurement_reflns_used    6485
_cell_measurement_temperature    190(2)
_cell_measurement_theta_max      27.485
_cell_measurement_theta_min      0.998
_cell_volume                     1011.32(5)
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_diffrn_ambient_temperature      190(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       CCD
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0353
_diffrn_reflns_av_unetI/netI     0.0730
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            6713
_diffrn_reflns_point_group_measured_fraction_full 0.962
_diffrn_reflns_point_group_measured_fraction_max 0.939
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.501
_diffrn_reflns_theta_min         2.855
_exptl_absorpt_coefficient_mu    0.126
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.131
_exptl_crystal_description       block
_exptl_crystal_F_000             376
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.178
_refine_diff_density_min         -0.212
_refine_diff_density_rms         0.046
_refine_ls_abs_structure_details
;
 Flack x determined using 1216 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.04(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     224
_refine_ls_number_reflns         4388
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.037
_refine_ls_R_factor_all          0.0684
_refine_ls_R_factor_gt           0.0472
_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^)+(0.0254P)^2^+0.1667P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0840
_refine_ls_wR_factor_ref         0.0920
_reflns_Friedel_coverage         0.741
_reflns_Friedel_fraction_full    0.918
_reflns_Friedel_fraction_max     0.875
_reflns_number_gt                3544
_reflns_number_total             4388
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo8b02735_si_001.cif
_cod_data_source_block           mip_368a
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               4033892
_shelx_shelxl_version_number     2017/1
_shelx_res_checksum              93478
_shelx_hkl_checksum              79628