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_1569905
_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         'C36 H24 N2 O4, C H Cl3'
_chemical_formula_sum            'C37 H25 Cl3 N2 O4'
_chemical_formula_weight         667.94
_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'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2022-04-25
_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                90
_cell_angle_beta                 94.6260(10)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   13.2537(4)
_cell_length_b                   8.0062(2)
_cell_length_c                   15.7406(5)
_cell_measurement_reflns_used    9319
_cell_measurement_temperature    273(2)
_cell_measurement_theta_max      24.608
_cell_measurement_theta_min      2.596
_cell_volume                     1664.82(8)
_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      273.15
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.997
_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  0.0619
_diffrn_reflns_av_unetI/netI     0.0484
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            35129
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.532
_diffrn_reflns_theta_min         2.094
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.318
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6242
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1204 before and 0.0693 after correction.
The Ratio of minimum to maximum transmission is 0.8372.
The \l/2 correction factor is Not present.
;
_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    1.332
_exptl_crystal_description       block
_exptl_crystal_F_000             688
_exptl_crystal_size_max          0.43
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.13
_refine_diff_density_max         0.401
_refine_diff_density_min         -0.478
_refine_diff_density_rms         0.056
_refine_ls_abs_structure_details
;
 Flack x determined using 1836 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.05(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     398
_refine_ls_number_reflns         7649
_refine_ls_number_restraints     13
_refine_ls_restrained_S_all      1.043
_refine_ls_R_factor_all          0.1003
_refine_ls_R_factor_gt           0.0667
_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^)+(0.1053P)^2^+0.5758P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1763
_refine_ls_wR_factor_ref         0.2034
_reflns_Friedel_coverage         0.865
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.997
_reflns_number_gt                5230
_reflns_number_total             7649
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3sc03996j2.cif
_cod_data_source_block           6c
_cod_depositor_comments
'Adding full bibliography for 1569903--1569908.cif.'
_cod_database_code               1569905
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_max   0.960
_shelx_estimated_absorpt_t_min   0.875
_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. Uiso/Uaniso restraints and constraints
Uanis(C14) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
Uanis(C1) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
Uanis(C14) = Uanis(C2)
3.a Ternary CH refined with riding coordinates:
 C8(H8), C36(H36)
3.b Secondary CH2 refined with riding coordinates:
 C5(H5A,H5B)
3.c Aromatic/amide H refined with riding coordinates:
 C10(H10), C11(H11), C15(H15), C14(H14), C1(H1), C2(H2), C3(H3), C18(H18),
 C24(H24), C25(H25), C26(H26), C27(H27), C28(H28), C29(H29), C31(H31), C32(H32),
  C33(H33), C34(H34)
3.d Fitted hexagon refined as free rotating group:
 C15(C14,C1,C2,C3,C37)
3.e Idealised Me refined as rotating group:
 C20(H20A,H20B,H20C)
;
_shelx_res_checksum              92045
_olex2_submission_special_instructions 'No special instructions were received'