Enantioselective Synthesis of Atropisomers Featuring Pentatomic Heteroaromatics by Pd-Catalyzed C‒H Alkynylation
Zhang, Shuo; Yao, Qi-Jun; Liao, Gang; Li, Xin; Li, Han; Chen, Hao-Ming; Hong, Xin; Shi, Bing-Feng; ACS Catalysis 9 (2019) 1956–; doi:10.1021/acscatal.8b04870

data_4514877
_publ_section_title
;
 Enantioselective Synthesis of Atropisomers Featuring Pentatomic
 Heteroaromatics by Pd-Catalyzed C--H Alkynylation
;
_journal_issue                   3
_journal_name_full               'ACS Catalysis'
_journal_page_first              1956
_journal_paper_doi               10.1021/acscatal.8b04870
_journal_volume                  9
_journal_year                    2019
_chemical_formula_moiety         'C27 H31 O2 Si'
_chemical_formula_sum            'C27 H31 O2 Si'
_chemical_formula_weight         415.61
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2018-07-03
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 90.427(3)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   27.6888(8)
_cell_length_b                   8.4150(3)
_cell_length_c                   21.6977(7)
_cell_measurement_reflns_used    8306
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      66.8868
_cell_measurement_theta_min      3.1896
_cell_volume                     5055.5(3)
_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    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean 10.3592
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_details
;
  1 omega   -2.00   96.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       41.6938 -125.0000  -90.0000 98

  2 omega   24.00   69.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       41.6938   38.0000   90.0000 45

  3 omega    9.00  120.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       41.6938   77.0000  120.0000 111

  4 omega  -75.00  -49.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      -83.0000  -77.0000   60.0000 26

  5 omega  -76.00  -50.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      -83.0000  -73.0000   94.0000 26

  6 omega  -76.00  -50.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      -83.0000  -74.0000   32.0000 26

  7 omega  -76.00  -50.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      -83.0000  -76.0000   79.0000 26

  8 omega   65.00  148.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000   77.0000    0.0000 83

  9 omega   62.00   98.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000   77.0000   60.0000 36

 10 omega   12.00   75.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -99.0000   41.0000 63

 11 omega   66.00  172.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000   77.0000  -30.0000 106

 12 omega   60.00  166.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000   77.0000   30.0000 106

 13 omega  102.00  168.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000   77.0000   60.0000 66

 14 omega   96.00  168.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  125.0000 -150.0000 72

 15 omega  121.00  170.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000   77.0000  120.0000 49

 16 omega   60.00   85.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000   77.0000  120.0000 25

 17 omega   62.00  168.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000   77.0000   90.0000 106

 18 omega   79.00  152.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  125.0000 -180.0000 73

 19 omega   44.00   76.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -45.0000   60.0000 32

 20 omega    8.00  120.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       41.6938   77.0000  -90.0000 112

 21 omega    8.00  120.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       41.6938   77.0000  -30.0000 112

 22 omega   15.00  118.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       41.6938   38.0000 -120.0000 103

 23 omega -160.00  -50.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      -83.0000  -72.0000  127.0000 110

 24 omega   15.00  127.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -77.0000 -180.0000 112

 25 omega   73.00  168.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  125.0000   90.0000 95

 26 omega   66.00  168.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000   45.0000 -150.0000 102

 27 omega   60.00  172.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000   77.0000 -120.0000 112

 28 omega   66.00  168.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000   45.0000  -60.0000 102
;
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0037606000
_diffrn_orient_matrix_UB_12      -0.0277774000
_diffrn_orient_matrix_UB_13      0.0700400000
_diffrn_orient_matrix_UB_21      -0.0525948000
_diffrn_orient_matrix_UB_22      -0.0596498000
_diffrn_orient_matrix_UB_23      0.0005446000
_diffrn_orient_matrix_UB_31      0.0177261000
_diffrn_orient_matrix_UB_32      -0.1708975000
_diffrn_orient_matrix_UB_33      -0.0116000000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0555
_diffrn_reflns_av_unetI/netI     0.0213
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       32
_diffrn_reflns_limit_h_min       -32
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            33243
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        66.998
_diffrn_reflns_theta_max         66.998
_diffrn_reflns_theta_min         3.192
_diffrn_source                   'Enhance Ultra (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.954
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.47602
_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            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.092
_exptl_crystal_description       block
_exptl_crystal_F_000             1784
_exptl_crystal_size_max          0.48
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.23
_refine_diff_density_max         0.441
_refine_diff_density_min         -0.253
_refine_diff_density_rms         0.042
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     278
_refine_ls_number_reflns         4461
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.032
_refine_ls_R_factor_all          0.0830
_refine_ls_R_factor_gt           0.0662
_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^)+(0.1206P)^2^+2.5429P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1942
_refine_ls_wR_factor_ref         0.2152
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3339
_reflns_number_total             4461
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            cs8b04870_si_003.cif
_cod_data_source_block           180702_zs_2_198_3
_cod_database_code               4514877
_shelx_shelxl_version_number     2016/6
_chemical_oxdiff_formula         'c o h n si'
_shelx_estimated_absorpt_t_max   0.811
_shelx_estimated_absorpt_t_min   0.658
_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
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C19(H19), C22(H22)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C11(H11), C12(H12), C13(H13), C14(H14), C15(H15)
2.c Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C), C20(H20A,H20B,H20C), C21(H21A,H21B,H21C), C23(H23A,H23B,
 H23C), C24(H24A,H24B,H24C), C26(H26A,H26B,H26C), C27(H27B,H27A,H27C)
;
_shelx_res_checksum              20576
_shelx_hkl_checksum              52961
_olex2_submission_special_instructions 'No special instructions were received'