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_1569904
_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         'C58 H44 N2 O8 S2'
_chemical_formula_sum            'C58 H44 N2 O8 S2'
_chemical_formula_weight         961.07
_space_group_crystal_system      monoclinic
_space_group_IT_number           5
_space_group_name_Hall           'C 2y'
_space_group_name_H-M_alt        'C 1 2 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2022-11-15
_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                 98.963(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   32.1431(8)
_cell_length_b                   7.1890(2)
_cell_length_c                   11.8007(3)
_cell_measurement_reflns_used    8392
_cell_measurement_temperature    302(2)
_cell_measurement_theta_max      24.506
_cell_measurement_theta_min      2.323
_cell_volume                     2693.57(12)
_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 0.966
_diffrn_measured_fraction_theta_max 0.966
_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  0.0453
_diffrn_reflns_av_unetI/netI     0.0315
_diffrn_reflns_Laue_measured_fraction_full 0.966
_diffrn_reflns_Laue_measured_fraction_max 0.966
_diffrn_reflns_limit_h_max       38
_diffrn_reflns_limit_h_min       -38
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            22880
_diffrn_reflns_point_group_measured_fraction_full 0.973
_diffrn_reflns_point_group_measured_fraction_max 0.973
_diffrn_reflns_theta_full        24.999
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_min         2.905
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.153
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6388
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0845 before and 0.0543 after correction.
The Ratio of minimum to maximum transmission is 0.8568.
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    1.185
_exptl_crystal_description       block
_exptl_crystal_F_000             1004
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.289
_refine_diff_density_min         -0.165
_refine_diff_density_rms         0.041
_refine_ls_abs_structure_details
;
 Flack x determined using 1502 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.07(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     317
_refine_ls_number_reflns         4626
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.066
_refine_ls_R_factor_all          0.0554
_refine_ls_R_factor_gt           0.0425
_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^)+(0.0698P)^2^+0.0382P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1046
_refine_ls_wR_factor_ref         0.1151
_reflns_Friedel_coverage         0.853
_reflns_Friedel_fraction_full    0.982
_reflns_Friedel_fraction_max     0.982
_reflns_number_gt                3803
_reflns_number_total             4626
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3sc03996j2.cif
_cod_data_source_block           21
_cod_depositor_comments
'Adding full bibliography for 1569903--1569908.cif.'
_cod_database_code               1569904
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_max   0.985
_shelx_estimated_absorpt_t_min   0.970
_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 Ternary CH refined with riding coordinates:
 C8(H8)
2.b Secondary CH2 refined with riding coordinates:
 C13(H13A,H13B)
2.c Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C11(H11), C12(H12), C14(H14), C15(H15), C16(H16), C17(H17),
 C19(H19), C20(H20), C21(H21), C22(H22), C23(H23), C26(H26), C27(H27), C28(H28)
2.d Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C)
;
_shelx_res_checksum              13901
_olex2_submission_special_instructions 'No special instructions were received'