Mantis-shaped chiral pyridine-N-oxides: a new class of ligands in asymmetric palladium(ii)-catalysed Friedel–Crafts alkylation
Yang, Lan-Lan; Pan, Di-Cheng; Zhu, Xian-Qiao; Liu, De-Wu; Tang, Xing-Zhou; Cen, Hong-Xing; Peng, Li-Jun; Liu, Xiong-Li; New Journal of Chemistry 49 (2025) 5346–5351; doi:10.1039/D5NJ00294J

data_7063684
_publ_section_title
;
 Mantis-shaped chiral pyridine-N-oxides: a new class of ligands in
 asymmetric palladium(ii)-catalysed Friedel--Crafts alkylation
;
_journal_issue                   13
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              5346
_journal_page_last               5351
_journal_paper_doi               10.1039/D5NJ00294J
_journal_volume                  49
_journal_year                    2025
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C21 H23 N3 O2, H2 O'
_chemical_formula_sum            'C21 H25 N3 O3'
_chemical_formula_weight         367.44
_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   mixed
_atom_sites_solution_primary     direct
_audit_creation_date             2024-12-16
_audit_creation_method
;
Olex2 1.5-beta
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6439)
;
_audit_update_record
;
2024-12-23 deposited with the CCDC.	2025-02-27 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.1170(3)
_cell_length_b                   16.0841(7)
_cell_length_c                   16.6316(7)
_cell_measurement_reflns_used    9989
_cell_measurement_temperature    150.00
_cell_measurement_theta_max      68.230
_cell_measurement_theta_min      3.821
_cell_volume                     1903.83(14)
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS  (Sheldrick, 2008)'
_diffrn_ambient_temperature      150.00
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  Bruker
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0874
_diffrn_reflns_av_unetI/netI     0.0370
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            39237
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.708
_diffrn_reflns_theta_min         3.823
_diffrn_source_current           1.0
_diffrn_source_power             0.05
_diffrn_source_voltage           50.0
_exptl_absorpt_coefficient_mu    0.701
_exptl_absorpt_correction_T_max  0.7531
_exptl_absorpt_correction_T_min  0.6591
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1402 before and 0.0773 after correction.
The Ratio of minimum to maximum transmission is 0.8752.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.282
_exptl_crystal_description       block
_exptl_crystal_F_000             784
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.234
_refine_diff_density_min         -0.224
_refine_diff_density_rms         0.051
_refine_ls_abs_structure_details
;
 Flack x determined using 1283 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.05(9)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.151
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     247
_refine_ls_number_reflns         3504
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.151
_refine_ls_R_factor_all          0.0510
_refine_ls_R_factor_gt           0.0477
_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^)+(0.0659P)^2^+0.6162P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1211
_refine_ls_wR_factor_ref         0.1232
_reflns_Friedel_coverage         0.729
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.991
_reflns_number_gt                3243
_reflns_number_total             3504
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5nj00294j2.cif
_cod_data_source_block           py_y1_2
_cod_depositor_comments          'Adding full bibliography for 7063684.cif.'
_cod_database_code               7063684
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.940
_shelx_estimated_absorpt_t_min   0.896
_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 O(H,H) groups
2.a Free rotating group:
 O3(H3C,H3D)
2.b Ternary CH refined with riding coordinates:
 C1(H1), C6(H6), C8(H8), C10(H10)
2.c Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C3(H3A,H3B), C4(H4A,H4B), C5(H5A,H5B), C7(H7A,H7B)
2.d Aromatic/amide H refined with riding coordinates:
 C12(H12), C13(H13), C14(H14), C15(H15), C17(H17), C18(H18), C19(H19),
 C20(H20), C21(H21)
;
_shelx_res_checksum              80924
_shelx_hkl_checksum              942
_olex2_submission_special_instructions 'No special instructions were received'