Atroposelective synthesis of N-aryl peptoid atropisomers via a palladium(ii)-catalyzed asymmetric C‒H alkynylation strategy
Wu, Yong-Jie; Xie, Pei-Pei; Zhou, Gang; Yao, Qi-Jun; Hong, Xin; Shi, Bing-Feng; Chemical Science  (2021) –; doi:10.1039/D1SC01130H

data_1563603
_publ_section_title
;
 Atroposelective synthesis of N-aryl peptoid atropisomers via a
 palladium(ii)-catalyzed asymmetric C--H alkynylation strategy
;
_journal_name_full               'Chemical Science'
_journal_paper_doi               10.1039/D1SC01130H
_journal_year                    2021
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C24 H25 N3 O6'
_chemical_formula_sum            'C24 H25 N3 O6'
_chemical_formula_weight         451.47
_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     dual
_audit_creation_date             2020-10-21
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2020-10-24 deposited with the CCDC.	2021-06-02 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.3386(3)
_cell_length_b                   10.3729(3)
_cell_length_c                   24.4089(7)
_cell_measurement_reflns_used    9836
_cell_measurement_temperature    170(2)
_cell_measurement_theta_max      68.25
_cell_measurement_theta_min      3.62
_cell_volume                     2364.45(12)
_computing_cell_refinement       'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_data_collection       'Bruker Instrument Service vV6.2.10'
_computing_data_reduction        'SAINT V8.38A (Bruker AXS Inc., 2017)'
_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 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'zju Bruker D8 Venture Ims3.0'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0239
_diffrn_reflns_av_unetI/netI     0.0147
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            28511
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.241
_diffrn_reflns_theta_min         3.621
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.764
_exptl_absorpt_correction_T_max  0.7531
_exptl_absorpt_correction_T_min  0.6760
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1432 before and 0.0400 after correction.
The Ratio of minimum to maximum transmission is 0.8976.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.268
_exptl_crystal_description       block
_exptl_crystal_F_000             952
_exptl_crystal_size_max          0.39
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.196
_refine_diff_density_min         -0.240
_refine_diff_density_rms         0.044
_refine_ls_abs_structure_details
;
 Flack x determined using 1831 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   1.071
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     322
_refine_ls_number_reflns         4334
_refine_ls_number_restraints     45
_refine_ls_restrained_S_all      1.075
_refine_ls_R_factor_all          0.0288
_refine_ls_R_factor_gt           0.0287
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0430P)^2^+0.3698P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0733
_refine_ls_wR_factor_ref         0.0734
_reflns_Friedel_coverage         0.744
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.998
_reflns_number_gt                4312
_reflns_number_total             4334
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1sc01130h2.cif
_cod_data_source_block           cu_201020_wyj_5_135_l_0m
_cod_database_code               1563603
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.894
_shelx_estimated_absorpt_t_min   0.755
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 O6-C23 \\sim O6A-C23
 with sigma of 0.02
 O6-C24 \\sim O6A-C24A
 with sigma of 0.02
 C23-C24 \\sim C23-C24A
 with sigma of 0.04
3. Uiso/Uaniso restraints and constraints
C23 \\sim O6 \\sim C24 \\sim O6A \\sim C24A: within 1.7A with sigma of 0.02 and
sigma for terminal atoms of 0.04
4. Others
 Sof(O6A)=Sof(C24A)=Sof(H24D)=Sof(H24E)=Sof(H24F)=1-FVAR(1)
 Sof(O6)=Sof(C24)=Sof(H24A)=Sof(H24B)=Sof(H24C)=FVAR(1)
5.a Ternary CH refined with riding coordinates:
 C9(H9)
5.b Secondary CH2 refined with riding coordinates:
 C20(H20A,H20B), C22(H22A,H22B)
5.c Aromatic/amide H refined with riding coordinates:
 N3(H3), C3(H3A), C4(H4), C5(H5), C14(H14), C15(H15), C17(H17)
5.d Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C), C11(H11A,H11B,H11C), C19(H19A,H19B,H19C), C24(H24A,H24B,
 H24C), C24A(H24D,H24E,H24F)
5.e :
 C8(H8)
;
_shelx_res_checksum              63714
_shelx_hkl_checksum              19828
_olex2_submission_special_instructions 'No special instructions were received'