Divergent Synthesis of Silicon-Containing Peptides via Pd-Catalyzed Post-Assembly γ-C(sp3)–H Silylation
Zhan, Bei-Bei; Fan, Jun; Jin, Liang; Shi, Bing-Feng; ACS Catalysis 9 (2019) 3298–; doi:10.1021/acscatal.9b00544

data_4514736
_publ_section_title
;
 Divergent Synthesis of Silicon-Containing Peptides via Pd-Catalyzed
 Post-Assembly \g-C(sp3)--H Silylation
;
_journal_issue                   4
_journal_name_full               'ACS Catalysis'
_journal_page_first              3298
_journal_paper_doi               10.1021/acscatal.9b00544
_journal_volume                  9
_journal_year                    2019
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C22 H37 N3 O4 Si'
_chemical_formula_sum            'C22 H37 N3 O4 Si'
_chemical_formula_weight         435.63
_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'
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2018-04-25
_audit_creation_method
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5381)
;
_cell_angle_alpha                90
_cell_angle_beta                 96.443(4)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   9.1154(3)
_cell_length_b                   9.7854(3)
_cell_length_c                   14.6304(5)
_cell_measurement_reflns_used    3884
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      66.7835
_cell_measurement_theta_min      4.5149
_cell_volume                     1296.76(7)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_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    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      293.15
_diffrn_detector_area_resol_mean 10.3592
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_details
;
  1 omega   90.00  116.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       41.6938   38.0000  150.0000 26

  2 omega    9.00   94.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       41.6938 -125.0000  -30.0000 85

  3 omega   18.00   86.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       41.6938   38.0000  150.0000 68

  4 omega   15.00  108.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       41.6938   38.0000   60.0000 93

  5 omega   89.00  116.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -92.0000  167.0000 27

  6 omega   23.00   76.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -45.0000  150.0000 53

  7 omega    9.00   58.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -90.0000  -14.0000 49

  8 omega    9.00   67.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -92.0000  167.0000 58

  9 omega   20.00   76.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -45.0000 -120.0000 56

 10 omega   23.00   75.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -45.0000   60.0000 52

 11 omega    7.00  175.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000    0.0000  120.0000 168

 12 omega   21.00   74.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -45.0000  -30.0000 53

 13 omega   78.00  112.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -90.0000  -14.0000 34

 14 omega   24.00  131.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -92.0000 -111.0000 107

 15 omega   33.00   58.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -45.0000  -60.0000 25

 16 omega   28.00  128.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -93.0000   81.0000 100
;
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0023834000
_diffrn_orient_matrix_UB_12      0.1549894000
_diffrn_orient_matrix_UB_13      -0.0179866000
_diffrn_orient_matrix_UB_21      -0.1300410000
_diffrn_orient_matrix_UB_22      -0.0155417000
_diffrn_orient_matrix_UB_23      -0.0760284000
_diffrn_orient_matrix_UB_31      -0.1092151000
_diffrn_orient_matrix_UB_32      0.0221578000
_diffrn_orient_matrix_UB_33      0.0718880000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0397
_diffrn_reflns_av_unetI/netI     0.0373
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            8634
_diffrn_reflns_point_group_measured_fraction_full 0.976
_diffrn_reflns_point_group_measured_fraction_max 0.976
_diffrn_reflns_theta_full        66.895
_diffrn_reflns_theta_max         66.895
_diffrn_reflns_theta_min         4.882
_diffrn_source                   'Enhance Ultra (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.034
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.66762
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'light yellow'
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.116
_exptl_crystal_description       block
_exptl_crystal_F_000             472
_exptl_crystal_size_max          0.48
_exptl_crystal_size_mid          0.46
_exptl_crystal_size_min          0.38
_refine_diff_density_max         0.131
_refine_diff_density_min         -0.302
_refine_diff_density_rms         0.046
_refine_ls_abs_structure_details
;
 Flack x determined using 1598 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.00(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     279
_refine_ls_number_reflns         4503
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.039
_refine_ls_R_factor_all          0.0593
_refine_ls_R_factor_gt           0.0526
_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^)+(0.0919P)^2^+0.0682P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1367
_refine_ls_wR_factor_ref         0.1478
_reflns_Friedel_coverage         0.852
_reflns_Friedel_fraction_full    0.960
_reflns_Friedel_fraction_max     0.960
_reflns_number_gt                3949
_reflns_number_total             4503
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            cs9b00544_si_003.cif
_cod_data_source_block           180425_zbb_7_16_6
_cod_original_cell_volume        1296.75(8)
_cod_database_code               4514736
_shelx_shelxl_version_number     2016/6
_chemical_oxdiff_formula         'c h n o'
_shelx_estimated_absorpt_t_max   0.695
_shelx_estimated_absorpt_t_min   0.637
_reflns_odcompleteness_completeness 99.96
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     64.99
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, {H11A,H11B,H11C} of C11, {H10A,H10B,H10C} of C10, All C(H,
  H) groups, All N(H) groups
 At 1.5 times of:
  {H14A,H14B,H14C} of C14, {H12A,H12B,H12C} of C12, {H18A,H18B,H18C} of C18,
  {H20A,H20B,H20C} of C20, {H21A,H21B,H21C} of C21, {H22A,H22B,H22C} of C22
2.a Ternary CH refined with riding coordinates:
 C7(H7), C8(H8), C16(H16)
2.b Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B), C13(H13A,H13B)
2.c Aromatic/amide H refined with riding coordinates:
 N2(H2), N3(H3), C1(H1), C2(H2A), C3(H3A), C4(H4)
2.d Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C), C11(H11A,H11B,H11C), C12(H12A,H12B,H12C), C14(H14A,H14B,
 H14C), C18(H18A,H18B,H18C), C20(H20A,H20B,H20C), C21(H21A,H21B,H21C), C22(H22A,
 H22B,H22C)
;
_shelx_res_checksum              38508
_shelx_hkl_checksum              79349
_olex2_submission_special_instructions 'No special instructions were received'