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_4514878
_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_absolute_configuration ad
_chemical_formula_moiety         'C30 H32 O S Si'
_chemical_formula_sum            'C30 H32 O S Si'
_chemical_formula_weight         468.70
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2018-07-02
_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
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.8692(3)
_cell_length_b                   13.9222(4)
_cell_length_c                   17.5154(5)
_cell_measurement_reflns_used    10824
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      29.3710
_cell_measurement_theta_min      2.9203
_cell_volume                     2650.49(13)
_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 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_details
;
  1 omega  -15.00   78.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       11.7808   38.0000  -60.0000 93

  2 omega  -22.00   64.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       11.7808   77.0000  120.0000 86

  3 omega  -67.00   40.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       11.7808  -77.0000    0.0000 107

  4 omega  -87.00  -58.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -11.4683  -38.0000   90.0000 29

  5 omega  -90.00  -16.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -11.4683  156.0000 -131.0000 74

  6 omega  -38.00   64.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -11.4683   39.0000 -168.0000 102

  7 omega  -22.00   90.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       11.7808   77.0000   60.0000 112

  8 omega  -17.00   49.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       11.7808  -88.0000  110.0000 66
;
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0614996000
_diffrn_orient_matrix_UB_12      0.0134461000
_diffrn_orient_matrix_UB_13      0.0083133000
_diffrn_orient_matrix_UB_21      -0.0096973000
_diffrn_orient_matrix_UB_22      -0.0448484000
_diffrn_orient_matrix_UB_23      0.0182439000
_diffrn_orient_matrix_UB_31      0.0195520000
_diffrn_orient_matrix_UB_32      0.0200824000
_diffrn_orient_matrix_UB_33      0.0351865000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0503
_diffrn_reflns_av_unetI/netI     0.0256
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            40215
_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         25.346
_diffrn_reflns_theta_min         2.926
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.187
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.97585
_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            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.175
_exptl_crystal_description       block
_exptl_crystal_F_000             1000
_exptl_crystal_size_max          0.49
_exptl_crystal_size_mid          0.46
_exptl_crystal_size_min          0.39
_refine_diff_density_max         0.163
_refine_diff_density_min         -0.176
_refine_diff_density_rms         0.031
_refine_ls_abs_structure_details
;
 Flack x determined using 1573 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.06(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     304
_refine_ls_number_reflns         4838
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.035
_refine_ls_R_factor_all          0.0515
_refine_ls_R_factor_gt           0.0402
_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^)+(0.0508P)^2^+0.5079P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0977
_refine_ls_wR_factor_ref         0.1055
_reflns_Friedel_coverage         0.768
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     1.000
_reflns_number_gt                4102
_reflns_number_total             4838
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            cs8b04870_si_004.cif
_cod_data_source_block           180702_zs_3_35_2
_cod_database_code               4514878
_shelx_shelxl_version_number     2016/6
_chemical_oxdiff_formula         'c h n o s'
_shelx_estimated_absorpt_t_max   0.931
_shelx_estimated_absorpt_t_min   0.914
_reflns_odcompleteness_completeness 99.67
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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:
 C22(H22), C25(H25), C28(H28)
2.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C11(H11), C12(H12), C15(H15), C16(H16),
 C17(H17), C18(H18), C19(H19)
2.c Idealised Me refined as rotating group:
 C23(H23A,H23B,H23C), C24(H24A,H24B,H24C), C26(H26A,H26B,H26C), C27(H27A,H27B,
 H27C), C29(H29A,H29B,H29C), C30(H30A,H30B,H30C)
;
_shelx_res_checksum              70633
_shelx_hkl_checksum              57234
_olex2_submission_special_instructions 'No special instructions were received'