Highly Enantioselective Cross-Electrophile Aryl-Alkenylation of Unactivated Alkenes.
Tian, Zhi-Xiong; Qiao, Jin-Bao; Xu, Guang-Li; Pang, Xiaobo; Qi, Liangliang; Ma, Wei-Yuan; Zhao, Zhen-Zhen; Duan, Jicheng; Du, Yun-Fei; Su, Peifeng; Liu, Xue-Yuan; Shu, Xing-Zhong; Journal of the American Chemical Society 141 (2019) 7637–7643; doi:10.1021/jacs.9b03863

data_4128688
_publ_section_title
;
 Highly Enantioselective Cross-Electrophile Aryl-Alkenylation of
 Unactivated Alkenes.
;
_journal_issue                   18
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              7637
_journal_page_last               7643
_journal_paper_doi               10.1021/jacs.9b03863
_journal_volume                  141
_journal_year                    2019
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C28 H29 N O3 S'
_chemical_formula_sum            'C28 H30 N O3 S'
_chemical_formula_weight         460.59
_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'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2018-10-19
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.5255(6)
_cell_length_b                   10.9187(9)
_cell_length_c                   26.122(3)
_cell_measurement_reflns_used    1888
_cell_measurement_temperature    295.6(2)
_cell_measurement_theta_max      68.7870
_cell_measurement_theta_min      6.5930
_cell_volume                     2431.6(4)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_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      295.6(2)
_diffrn_detector_area_resol_mean 16.0733
_diffrn_measured_fraction_theta_full 0.969
_diffrn_measured_fraction_theta_max 0.969
_diffrn_measurement_details
;
  1 omega  -46.00  -14.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  -57.0000 -180.0000 32

  2 omega  -30.00   57.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       -8.5000   57.0000   30.0000 87

  3 omega  -15.00   61.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000  -57.0000 -120.0000 76

  4 omega  -15.00   62.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000  -57.0000  -30.0000 77

  5 omega   75.00  114.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -111.0000 -120.0000 39

  6 omega  129.00  165.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  111.0000  120.0000 36

  7 omega  102.00  131.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  178.0000 -150.0000 29

  8 omega   47.00   90.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -38.0000 -150.0000 43

  9 omega   36.00   94.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -25.0000  -60.0000 58

 10 omega   58.00  126.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -63.0000  120.0000 68

 11 omega   34.00   83.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -25.0000    0.0000 49

 12 omega   85.00  137.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   50.0000  -30.0000 52

 13 omega   63.00  117.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  178.0000 -120.0000 54

 14 omega   65.00   90.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  178.0000 -150.0000 25

 15 omega   34.00   92.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -25.0000  150.0000 58
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0293214000
_diffrn_orient_matrix_UB_12      -0.0947926000
_diffrn_orient_matrix_UB_13      0.0425897000
_diffrn_orient_matrix_UB_21      0.0018177000
_diffrn_orient_matrix_UB_22      -0.1035973000
_diffrn_orient_matrix_UB_23      -0.0400549000
_diffrn_orient_matrix_UB_31      0.1783130000
_diffrn_orient_matrix_UB_32      -0.0145392000
_diffrn_orient_matrix_UB_33      0.0074046000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0426
_diffrn_reflns_av_unetI/netI     0.0706
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            7508
_diffrn_reflns_theta_full        66.59
_diffrn_reflns_theta_max         66.59
_diffrn_reflns_theta_min         4.39
_diffrn_source                   'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.413
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.72024
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.258
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             980
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.219
_refine_diff_density_min         -0.575
_refine_diff_density_rms         0.060
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.07(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.121
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     300
_refine_ls_number_reflns         4101
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.121
_refine_ls_R_factor_all          0.1101
_refine_ls_R_factor_gt           0.0730
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.1131P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1894
_refine_ls_wR_factor_ref         0.2606
_reflns_number_gt                2546
_reflns_number_total             4101
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja9b03863_si_002.cif
_cod_data_source_block           tianzhx_1015
_cod_original_cell_volume        2431.7(4)
_cod_database_code               4128688
_reflns_odcompleteness_completeness 96.67
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C14(H14a,H14b), C16(H16a,H16b), C19(H19a,H19b), C20(H20a,H20b), C21(H21a,H21b)
2.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C5(H5), C8(H8), C9(H9), C12(H12), C18(H18),
 C23(H23), C24(H24), C26(H26), C27(H27)
2.c Idealised Me refined as rotating group:
 C15(H15a,H15b,H15c), C28(H28a,H28b,H28c)
;
_olex2_date_sample_data_collection 2018-10-15
_olex2_submission_special_instructions 'No special instructions were received'