(N-Heterocyclic Carbene)2-Pd(0)-Catalyzed Silaboration of Internal and Terminal Alkynes: Scope and Mechanistic Studies
Ansell, Melvyn B.; Spencer, John; Navarro, Oscar; ACS Catalysis 6 (2016) 2192–; doi:10.1021/acscatal.6b00127

data_4513827
_publ_section_title
;
 (N-Heterocyclic Carbene)2-Pd(0)-Catalyzed Silaboration of Internal and
 Terminal Alkynes: Scope and Mechanistic Studies
;
_journal_issue                   4
_journal_name_full               'ACS Catalysis'
_journal_page_first              2192
_journal_paper_doi               10.1021/acscatal.6b00127
_journal_volume                  6
_journal_year                    2016
_chemical_formula_moiety         'C28 H47 B N4 O2 Pd Si'
_chemical_formula_sum            'C28 H47 B N4 O2 Pd Si'
_chemical_formula_weight         616.99
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2015-09-25
_audit_creation_method
;
Olex2 1.2
(compiled 2014.09.19 svn.r3010 for OlexSys, GUI svn.r4874)
;
_cell_angle_alpha                90
_cell_angle_beta                 113.454(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.9381(3)
_cell_length_b                   17.8318(3)
_cell_length_c                   14.8311(4)
_cell_measurement_reflns_used    12890
_cell_measurement_temperature    173
_cell_measurement_theta_max      61.1290
_cell_measurement_theta_min      4.4380
_cell_volume                     3138.98(14)
_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, 2008)'
_computing_structure_solution    'ShelXT (Sheldrick, 2008)'
_diffrn_ambient_temperature      173
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.1033
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_details
;
  1 omega    1.00   84.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       36.8763 -115.0000  166.0000 83

  2 omega   22.00   89.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       36.8763   38.0000    0.0000 67

  3 omega   48.00   91.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       36.8763   57.0000   30.0000 43

  4 omega   70.00  105.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       36.8763 -178.0000   60.0000 35

  5 omega  -35.00   62.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       36.8763  -19.0000 -180.0000 97

  6 omega   45.00   71.00   1.0000   22.5000
omega____ theta____ kappa____ phi______ frames
    -       86.5000  -92.0000   44.7431 26

  7 omega   27.00  108.00   1.0000   22.5000
omega____ theta____ kappa____ phi______ frames
    -       86.5000  -93.0000  131.6971 81

  8 omega   17.00  114.00   1.0000   22.5000
omega____ theta____ kappa____ phi______ frames
    -       86.5000  -92.0000  -63.1315 97

  9 omega   50.00  115.00   1.0000   22.5000
omega____ theta____ kappa____ phi______ frames
    -       86.5000   15.0000 -180.0000 65

 10 omega  101.00  150.00   1.0000   22.5000
omega____ theta____ kappa____ phi______ frames
    -       86.5000   45.0000 -120.0000 49

 11 omega   29.00   75.00   1.0000   22.5000
omega____ theta____ kappa____ phi______ frames
    -       86.5000  -45.0000  -30.0000 46

 12 omega   58.00   89.00   1.0000   22.5000
omega____ theta____ kappa____ phi______ frames
    -       86.5000  -61.0000  150.0000 31

 13 omega   34.00   62.00   1.0000   22.5000
omega____ theta____ kappa____ phi______ frames
    -       86.5000  -30.0000 -120.0000 28

 14 omega   49.00   74.00   1.0000   22.5000
omega____ theta____ kappa____ phi______ frames
    -       86.5000  -45.0000   30.0000 25

 15 omega   86.00  116.00   1.0000   22.5000
omega____ theta____ kappa____ phi______ frames
    -       86.5000  -93.0000    7.0916 30

 16 omega   49.00   96.00   1.0000   22.5000
omega____ theta____ kappa____ phi______ frames
    -       86.5000   15.0000   30.0000 47

 17 omega   19.00   94.00   1.0000   22.5000
omega____ theta____ kappa____ phi______ frames
    -       86.5000  -77.0000  150.0000 75

 18 omega   80.00  105.00   1.0000   22.5000
omega____ theta____ kappa____ phi______ frames
    -       86.5000  -61.0000 -120.0000 25

 19 omega  107.00  158.00   1.0000   22.5000
omega____ theta____ kappa____ phi______ frames
    -       86.5000   15.0000   30.0000 51

 20 omega   21.00   63.00   1.0000   22.5000
omega____ theta____ kappa____ phi______ frames
    -       86.5000  -30.0000  120.0000 42

 21 omega   69.00  150.00   1.0000   22.5000
omega____ theta____ kappa____ phi______ frames
    -       86.5000   45.0000  -90.0000 81

 22 omega   23.00   63.00   1.0000   22.5000
omega____ theta____ kappa____ phi______ frames
    -       86.5000 -111.0000  120.0000 40

 23 omega   70.00   95.00   1.0000   22.5000
omega____ theta____ kappa____ phi______ frames
    -       86.5000   61.0000  120.0000 25

 24 omega   38.00   67.00   1.0000   22.5000
omega____ theta____ kappa____ phi______ frames
    -       86.5000 -111.0000  -60.0000 29

 25 omega   60.00   86.00   1.0000   22.5000
omega____ theta____ kappa____ phi______ frames
    -       86.5000   77.0000  -30.0000 26

 26 omega  120.00  150.00   1.0000   22.5000
omega____ theta____ kappa____ phi______ frames
    -       86.5000   30.0000  -60.0000 30

 27 omega   27.00   81.00   1.0000   22.5000
omega____ theta____ kappa____ phi______ frames
    -       86.5000  -77.0000   60.0000 54

 28 omega   24.00   69.00   1.0000   22.5000
omega____ theta____ kappa____ phi______ frames
    -       86.5000  -45.0000  -60.0000 45

 29 omega   70.00  108.00   1.0000   22.5000
omega____ theta____ kappa____ phi______ frames
    -       86.5000   61.0000 -150.0000 38

 30 omega  128.00  153.00   1.0000   22.5000
omega____ theta____ kappa____ phi______ frames
    -       86.5000   61.0000 -150.0000 25

 31 omega   69.00  116.00   1.0000   22.5000
omega____ theta____ kappa____ phi______ frames
    -       86.5000   45.0000    0.0000 47

 32 omega   93.00  120.00   1.0000   22.5000
omega____ theta____ kappa____ phi______ frames
    -       86.5000  -92.0000   44.7431 27

 33 omega   44.00   70.00   1.0000   22.5000
omega____ theta____ kappa____ phi______ frames
    -       86.5000  -93.0000    7.0916 26

 34 omega   76.00  101.00   1.0000   22.5000
omega____ theta____ kappa____ phi______ frames
    -       86.5000  -92.0000 -169.6762 25

 35 omega  127.00  154.00   1.0000   22.5000
omega____ theta____ kappa____ phi______ frames
    -       86.5000   45.0000  -30.0000 27

 36 omega   93.00  140.00   1.0000   22.5000
omega____ theta____ kappa____ phi______ frames
    -       86.5000   30.0000   60.0000 47

 37 omega   65.00   92.00   1.0000   22.5000
omega____ theta____ kappa____ phi______ frames
    -       86.5000   77.0000  150.0000 27

 38 omega   56.00   90.00   1.0000   22.5000
omega____ theta____ kappa____ phi______ frames
    -       86.5000 -111.0000  -90.0000 34

 39 omega   18.00   43.00   1.0000   22.5000
omega____ theta____ kappa____ phi______ frames
    -       86.5000 -111.0000  150.0000 25

 40 omega   94.00  121.00   1.0000   22.5000
omega____ theta____ kappa____ phi______ frames
    -       86.5000  111.0000  -30.0000 27

 41 omega   74.00  112.00   1.0000   22.5000
omega____ theta____ kappa____ phi______ frames
    -       86.5000  -77.0000  -30.0000 38

 42 omega   38.00   64.00   1.0000   22.5000
omega____ theta____ kappa____ phi______ frames
    -       86.5000  -92.0000 -169.6762 26
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini ultra'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0550988000
_diffrn_orient_matrix_UB_12      -0.0730866000
_diffrn_orient_matrix_UB_13      -0.0143924000
_diffrn_orient_matrix_UB_21      -0.0591805000
_diffrn_orient_matrix_UB_22      -0.0438486000
_diffrn_orient_matrix_UB_23      0.0553901000
_diffrn_orient_matrix_UB_31      -0.1015065000
_diffrn_orient_matrix_UB_32      -0.0141209000
_diffrn_orient_matrix_UB_33      -0.0977163000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0510
_diffrn_reflns_av_unetI/netI     0.0297
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            30277
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        61.190
_diffrn_reflns_theta_max         61.190
_diffrn_reflns_theta_min         3.846
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'Enhance Ultra (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    5.360
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.54539
_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            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.306
_exptl_crystal_description       block
_exptl_crystal_F_000             1296
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.948
_refine_diff_density_min         -0.647
_refine_diff_density_rms         0.063
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     348
_refine_ls_number_reflns         4815
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.044
_refine_ls_R_factor_all          0.0404
_refine_ls_R_factor_gt           0.0350
_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^)+(0.0371P)^2^+4.3510P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0840
_refine_ls_wR_factor_ref         0.0880
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4288
_reflns_number_total             4815
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            cs6b00127_si_003.cif
_cod_data_source_block           pdsib1
_cod_depositor_comments
'Adding full bibliography for 4513825--4513827.cif.'
_cod_original_cell_volume        3138.99(13)
_cod_database_code               4513827
_chemical_oxdiff_formula         C28H47O2N4BSiPd
_reflns_odcompleteness_completeness 85.93
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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 Aromatic/amide H refined with riding coordinates:
 C00O(H00S), C00S(H00), C00V(H1AA), C00X(H3AA), C00Z(H5AA)
2.b Idealised Me refined as rotating group:
 C00I(H00A,H00B,H00C), C00J(H00D,H00E,H00F), C00K(H00G,H00H,H00I), C00L(H00J,
 H00K,H00L), C00M(H00M,H00N,H00O), C00N(H00P,H00Q,H00R), C00P(H00T,H00U,H00V),
 C00Q(H00W,H00X,H00Y), C00R(H00Z,H,HA), C00U(H0AA,HB,HC), C00W(H2AA,HD,HE),
 C00Y(H4AA,HF,HG), C010(H01A,H01B,H01C), C011(H01D,H01E,H01F)
;
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'