Enantioselective Synthesis of Atropisomeric Anilides via Pd(II)-Catalyzed Asymmetric C-H Olefination.
Yao, Qi-Jun; Xie, Pei-Pei; Wu, Yong-Jie; Feng, Ya-Lan; Teng, Ming-Ya; Hong, Xin; Shi, Bing-Feng; Journal of the American Chemical Society 142 (2020) 18266–18276; doi:10.1021/jacs.0c09400

data_4135281
_publ_section_title
;
 Enantioselective Synthesis of Atropisomeric Anilides via Pd(II)-Catalyzed
 Asymmetric C-H Olefination.
;
_journal_issue                   42
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              18266
_journal_page_last               18276
_journal_paper_doi               10.1021/jacs.0c09400
_journal_volume                  142
_journal_year                    2020
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C31 H26 N2 O5'
_chemical_formula_sum            'C31 H26 N2 O5'
_chemical_formula_weight         506.54
_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             2019-04-03
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 97.2170(10)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   7.7185(2)
_cell_length_b                   19.1801(6)
_cell_length_c                   8.9140(3)
_cell_measurement_reflns_used    9987
_cell_measurement_temperature    170(2)
_cell_measurement_theta_max      68.21
_cell_measurement_theta_min      5.00
_cell_volume                     1309.19(7)
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_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      170.0
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0232
_diffrn_reflns_av_unetI/netI     0.0271
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            12760
_diffrn_reflns_point_group_measured_fraction_full 0.987
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.205
_diffrn_reflns_theta_min         4.611
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.713
_exptl_absorpt_correction_T_max  0.7530
_exptl_absorpt_correction_T_min  0.6368
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1391 before and 0.0421 after correction.
The Ratio of minimum to maximum transmission is 0.8457.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.285
_exptl_crystal_description       block
_exptl_crystal_F_000             532
_exptl_crystal_size_max          0.506
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.244
_refine_diff_density_max         0.109
_refine_diff_density_min         -0.188
_refine_diff_density_rms         0.040
_refine_ls_abs_structure_details
;
 Flack x determined using 2243 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.03(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     345
_refine_ls_number_reflns         4734
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.064
_refine_ls_R_factor_all          0.0287
_refine_ls_R_factor_gt           0.0287
_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^)+(0.0398P)^2^+0.1866P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0731
_refine_ls_wR_factor_ref         0.0732
_reflns_Friedel_coverage         0.913
_reflns_Friedel_fraction_full    0.973
_reflns_Friedel_fraction_max     0.973
_reflns_number_gt                4726
_reflns_number_total             4734
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja0c09400_si_003.cif
_cod_data_source_block           190401_yqj_h_103_5_2_0m
_cod_depositor_comments
'Adding full bibliography for 4135280--4135281.cif.'
_cod_database_code               4135281
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_max   0.845
_shelx_estimated_absorpt_t_min   0.714
_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:
 C7(H7A,H7B)
2.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C9(H9), C10(H10), C11(H11), C12(H12),
 C13(H13), C16(H16), C17(H17), C21(H21), C22(H22), C23(H23), C24(H24), C25(H25),
  C28(H28), C29(H29)
2.c Idealised Me refined as rotating group:
 C27(H27A,H27B,H27C), C31(H31A,H31B,H31C)
;
_shelx_res_checksum              23064
_shelx_hkl_checksum              90272
_olex2_submission_special_instructions 'No special instructions were received'