Asymmetric Friedel-Crafts reaction of unsaturated carbonyl-tethered heteroarenes <i>via</i> vinylogous activation of Pd<sup>0</sup>-π-Lewis base catalysis.
Jiang, Bo; Gui, Wu-Tao; Wang, Hao-Tian; Xie, Ke; Chen, Zhi-Chao; Zhu, Lei; Ouyang, Qin; Du, Wei; Chen, Ying-Chun; Chemical science 14 (2023) 10867–10874; doi:10.1039/d3sc03996j

data_1569908
_publ_section_title
;
 Asymmetric Friedel-Crafts reaction of unsaturated carbonyl-tethered
 heteroarenes <i>via</i> vinylogous activation of
 Pd<sup>0</sup>-&#x3c0;-Lewis base catalysis.
;
_journal_issue                   39
_journal_name_full               'Chemical science'
_journal_page_first              10867
_journal_page_last               10874
_journal_paper_doi               10.1039/d3sc03996j
_journal_volume                  14
_journal_year                    2023
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C32 H27 F N2 O3 S'
_chemical_formula_sum            'C32 H27 F N2 O3 S'
_chemical_formula_weight         538.61
_space_group_crystal_system      triclinic
_space_group_IT_number           1
_space_group_name_Hall           'P 1'
_space_group_name_H-M_alt        'P 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2022-01-12
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_audit_update_record
;
2023-03-27 deposited with the CCDC.	2023-09-18 downloaded from the CCDC.
;
_cell_angle_alpha                106.668(2)
_cell_angle_beta                 101.698(2)
_cell_angle_gamma                117.979(2)
_cell_formula_units_Z            1
_cell_length_a                   9.2530(5)
_cell_length_b                   9.3566(5)
_cell_length_c                   9.9037(6)
_cell_measurement_reflns_used    7730
_cell_measurement_temperature    302(2)
_cell_measurement_theta_max      27.506
_cell_measurement_theta_min      2.341
_cell_volume                     665.24(7)
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2014/7 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      302.0
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0484
_diffrn_reflns_av_unetI/netI     0.0451
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            19634
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.629
_diffrn_reflns_theta_min         2.341
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.166
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6581
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1113 before and 0.0594 after correction.
The Ratio of minimum to maximum transmission is 0.8826.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            'clear yellowish yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   yellowish
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.344
_exptl_crystal_description       block
_exptl_crystal_F_000             282
_exptl_crystal_size_max          0.41
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.17
_refine_diff_density_max         0.146
_refine_diff_density_min         -0.187
_refine_diff_density_rms         0.033
_refine_ls_abs_structure_details
;
 Flack x determined using 2104 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.01(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     358
_refine_ls_number_reflns         6078
_refine_ls_number_restraints     4
_refine_ls_restrained_S_all      1.038
_refine_ls_R_factor_all          0.0504
_refine_ls_R_factor_gt           0.0386
_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^)+(0.0466P)^2^+0.0310P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0881
_refine_ls_wR_factor_ref         0.0941
_reflns_Friedel_coverage         0.979
_reflns_Friedel_fraction_full    0.985
_reflns_Friedel_fraction_max     0.974
_reflns_number_gt                5129
_reflns_number_total             6078
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3sc03996j2.cif
_cod_data_source_block           9f
_cod_depositor_comments
'Adding full bibliography for 1569903--1569908.cif.'
_cod_database_code               1569908
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_max   0.972
_shelx_estimated_absorpt_t_min   0.935
_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. Restrained distances
 N2-H2
 0.86 with sigma of 0.01
3.a Ternary CH refined with riding coordinates:
 C9(H9)
3.b Aromatic/amide H refined with riding coordinates:
 C2(H2A), C32(H32), C6(H6), C7(H7), C11(H11), C12(H12), C15(H15), C16(H16),
 C17(H17), C18(H18), C22(H22), C23(H23), C24(H24), C25(H25), C27(H27), C28(H28),
  C29(H29), C30(H30), C31(H31)
3.c Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C), C20(H20A,H20B,H20C)
;
_shelx_res_checksum              53119
_olex2_submission_special_instructions 'No special instructions were received'