Ethanol-assisted mechanochemical asymmetric cross-dehydrogenative coupling reaction with recoverable chiral amine/NaCl for accessing chiral α-alkyl α-glycine derivatives
Yu, Jingbo; Chen, Hong; Zhang, Ziwen; Fang, Yuxin; Ying, Tao; Su, Weike; Green Chemistry 26 (2024) 6570–6577; doi:10.1039/D4GC00947A

data_7248512
_publ_section_title
;
 Ethanol-assisted mechanochemical asymmetric cross-dehydrogenative
 coupling reaction with recoverable chiral amine/NaCl for accessing chiral
 \a-alkyl \a-glycine derivatives
;
_journal_issue                   11
_journal_name_full               'Green Chemistry'
_journal_page_first              6570
_journal_page_last               6577
_journal_paper_doi               10.1039/D4GC00947A
_journal_volume                  26
_journal_year                    2024
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C25 H33 N O4'
_chemical_formula_sum            'C25 H33 N O4'
_chemical_formula_weight         411.52
_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     dual
_audit_creation_date             2023-05-20
_audit_creation_method
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_audit_update_record
;
2023-05-20 deposited with the CCDC.	2024-04-19 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.82470(10)
_cell_length_b                   15.1975(3)
_cell_length_c                   20.6745(4)
_cell_measurement_reflns_used    9962
_cell_measurement_temperature    170.00
_cell_measurement_theta_max      74.58
_cell_measurement_theta_min      3.61
_cell_volume                     2144.33(7)
_computing_cell_refinement       'SAINT V8.40B (Bruker Nano, Inc., 2019)'
_computing_data_collection       'Bruker Instrument Service vV6.2.14'
_computing_data_reduction        'SAINT V8.40B (Bruker Nano, Inc., 2019)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/2 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      170.00
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'zju Bruker D8 Venture'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0621
_diffrn_reflns_av_unetI/netI     0.0384
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_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       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            22064
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         74.568
_diffrn_reflns_theta_min         3.609
_diffrn_source_current           1.1
_diffrn_source_power             0.05500000000000001
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.682
_exptl_absorpt_correction_T_max  0.7538
_exptl_absorpt_correction_T_min  0.5667
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1409 before and 0.0806 after correction.
The Ratio of minimum to maximum transmission is 0.7518.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.275
_exptl_crystal_description       block
_exptl_crystal_F_000             888
_exptl_crystal_size_max          0.48
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.248
_refine_diff_density_min         -0.215
_refine_diff_density_rms         0.041
_refine_ls_abs_structure_details
;
 Flack x determined using 1620 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.12(12)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     275
_refine_ls_number_reflns         4363
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.032
_refine_ls_R_factor_all          0.0464
_refine_ls_R_factor_gt           0.0407
_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^)+(0.0628P)^2^+0.2586P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1041
_refine_ls_wR_factor_ref         0.1077
_reflns_Friedel_coverage         0.734
_reflns_Friedel_fraction_full    0.992
_reflns_Friedel_fraction_max     0.989
_reflns_number_gt                4025
_reflns_number_total             4363
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4gc00947a2.cif
_cod_data_source_block           cu_230519_ch_3ka_0m
_cod_depositor_comments          'Adding full bibliography for 7248512.cif.'
_cod_database_code               7248512
_shelx_shelxl_version_number     2019/2
_shelx_estimated_absorpt_t_max   0.876
_shelx_estimated_absorpt_t_min   0.735
_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. Restrained distances
 N1-H1
 0.88 with sigma of 0.02
3.a Ternary CH refined with riding coordinates:
 C6(H6), C7(H7), C11(H11), C13(H13), C16(H16)
3.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C3(H3A,H3B), C4(H4A,H4B), C5(H5A,H5B), C10(H10A,H10B), C12(H12A,
 H12B), C14(H14A,H14B), C15(H15A,H15B), C17(H17A,H17B), C18(H18A,H18B)
3.c Aromatic/amide H refined with riding coordinates:
 C20(H20), C21(H21), C23(H23), C24(H24)
3.d Idealised Me refined as rotating group:
 C25(H25A,H25B,H25C)
;
_shelx_res_checksum              13017
_shelx_hkl_checksum              26147
_olex2_submission_special_instructions 'No special instructions were received'