Reaction of Dilithio Reagents with PhSiH3: Formation of Siloles and 3-Silacyclopentenes.
Wei, Baosheng; Li, Heng; Yin, Jianhao; Zhang, Wen-Xiong; Xi, Zhenfeng; The Journal of organic chemistry 80 (2015) 8758–8762; doi:10.1021/acs.joc.5b01595

data_4031354
_publ_section_title
;
 Reaction of Dilithio Reagents with PhSiH3: Formation of Siloles and
 3-Silacyclopentenes.
;
_journal_issue                   17
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              8758
_journal_page_last               8762
_journal_paper_doi               10.1021/acs.joc.5b01595
_journal_volume                  80
_journal_year                    2015
_chemical_formula_moiety         'C28 H36 Si3'
_chemical_formula_sum            'C28 H36 Si3'
_chemical_formula_weight         456.84
_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             2015-05-16
_audit_creation_method
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_cell_angle_alpha                70.176(5)
_cell_angle_beta                 72.274(6)
_cell_angle_gamma                76.538(5)
_cell_formula_units_Z            2
_cell_length_a                   9.6233(7)
_cell_length_b                   10.8425(5)
_cell_length_c                   14.8348(11)
_cell_measurement_reflns_used    3668
_cell_measurement_temperature    180.00(10)
_cell_measurement_theta_max      27.8660
_cell_measurement_theta_min      3.8590
_cell_volume                     1372.44(17)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_reduction
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CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_diffrn_ambient_temperature      180.00(10)
_diffrn_detector_area_resol_mean 10.3914
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details
;
  1 omega   -9.00   84.00   1.0000   10.2300
omega____ theta____ kappa____ phi______ frames
    -       10.7017   57.0000   90.0000 93

  2 omega  -68.00   38.00   1.0000   10.2300
omega____ theta____ kappa____ phi______ frames
    -       10.7017  -77.0000  -30.0000 106

  3 omega   -5.00   22.00   1.0000   10.2300
omega____ theta____ kappa____ phi______ frames
    -       10.7017   79.0000 -172.0000 27

  4 omega   35.00   63.00   1.0000   10.2300
omega____ theta____ kappa____ phi______ frames
    -       10.7017  178.0000  -30.0000 28

  5 omega  -18.00    8.00   1.0000   10.2300
omega____ theta____ kappa____ phi______ frames
    -      -11.5610  -99.0000 -120.0000 26

  6 omega  -25.00   14.00   1.0000   10.2300
omega____ theta____ kappa____ phi______ frames
    -      -11.5610   79.0000 -172.0000 39

  7 omega -100.00  -75.00   1.0000   10.2300
omega____ theta____ kappa____ phi______ frames
    -      -11.5610  178.0000  120.0000 25

  8 omega  -83.00  -56.00   1.0000   10.2300
omega____ theta____ kappa____ phi______ frames
    -      -11.5610  -77.0000   30.0000 27
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0440212000
_diffrn_orient_matrix_UB_12      -0.0126447000
_diffrn_orient_matrix_UB_13      -0.0256184000
_diffrn_orient_matrix_UB_21      -0.0641821000
_diffrn_orient_matrix_UB_22      0.0129701000
_diffrn_orient_matrix_UB_23      0.0365921000
_diffrn_orient_matrix_UB_31      -0.0076398000
_diffrn_orient_matrix_UB_32      0.0679030000
_diffrn_orient_matrix_UB_33      -0.0274770000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0330
_diffrn_reflns_av_unetI/netI     0.0505
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            11830
_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         26.022
_diffrn_reflns_theta_min         2.997
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.186
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.61595
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear whiteish colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   whiteish
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.105
_exptl_crystal_description
;
;
_exptl_crystal_F_000             492
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.428
_refine_diff_density_min         -0.404
_refine_diff_density_rms         0.049
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     286
_refine_ls_number_reflns         5403
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.040
_refine_ls_R_factor_all          0.0748
_refine_ls_R_factor_gt           0.0478
_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^)+(0.0415P)^2^+0.7892P]
 where P=(Fo^2^+2Fc^2^)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1065
_refine_ls_wR_factor_ref         0.1231
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3943
_reflns_number_total             5403
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo5b01595_si_002.cif
_cod_data_source_block           exp_3856
_cod_depositor_comments          'Adding full bibliography for 4031354.cif.'
_cod_original_cell_volume        1372.45(17)
_cod_database_code               4031354
_shelxl_version_number           2013-2
_chemical_oxdiff_formula         'C25 H30 Si3'
_reflns_odcompleteness_completeness 99.82
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     25.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All Si(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 Si1(H1), C1(H1A), C4(H4)
2.b Aromatic/amide H refined with riding coordinates:
 C6(H6), C10(H10), C12(H12), C8(H8), C16(H16), C9(H9), C7(H7), C24(H24),
 C13(H13), C26(H26), C28(H28), C15(H15), C14(H14), C27(H27), C25(H25)
2.c Idealised Me refined as rotating group:
 C21(H21A,H21B,H21C), C19(H19A,H19B,H19C), C22(H22A,H22B,H22C), C20(H20A,H20B,
 H20C), C17(H17A,H17B,H17C), C18(H18A,H18B,H18C)
;
_olex2_date_sample_data_collection 2014-07-10
_olex2_submission_special_instructions 'No special instructions were received'