A general asymmetric synthesis of artificial aliphatic and perfluoroalkylated α-amino acids by Luche's cross-electrophile coupling reaction.
Gugkaeva, Zalina T.; Smol'yakov, Alexander F.; Maleev, Victor I.; Larionov, Vladimir A.; Organic & biomolecular chemistry 19 (2021) 5327–5332; doi:10.1039/d1ob00805f

data_1562757
_publ_section_title
;
 A general asymmetric synthesis of artificial aliphatic and
 perfluoroalkylated \a-amino acids by Luche's cross-electrophile coupling
 reaction.
;
_journal_issue                   24
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              5327
_journal_page_last               5332
_journal_paper_doi               10.1039/d1ob00805f
_journal_volume                  19
_journal_year                    2021
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C31 H33 N3 Ni O3'
_chemical_formula_sum            'C31 H33 N3 Ni O3'
_chemical_formula_weight         554.31
_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             2021-03-11
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2021-03-11 deposited with the CCDC.	2021-05-20 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.1084(4)
_cell_length_b                   12.8143(5)
_cell_length_c                   21.4068(9)
_cell_measurement_reflns_used    9887
_cell_measurement_temperature    120
_cell_measurement_theta_max      30.45
_cell_measurement_theta_min      2.48
_cell_volume                     2772.87(19)
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      120
_diffrn_detector_area_resol_mean 8
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker SMART APEX CCD area detector'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0267
_diffrn_reflns_av_unetI/netI     0.0231
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            50870
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.489
_diffrn_reflns_theta_min         1.852
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.736
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.6278
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2008/1 (Bruker,2008) was used for absorption correction. wR2(int) was 0.0839 before and 0.0547 after correction. The Ratio of minimum to maximum transmission is 0.8414. The \l/2 correction factor is 0.0015.'
_exptl_crystal_colour            red
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.328
_exptl_crystal_description       prism
_exptl_crystal_F_000             1168
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.474
_refine_diff_density_min         -0.219
_refine_diff_density_rms         0.055
_refine_ls_abs_structure_details
;
 Flack x determined using 3355 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.004(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     345
_refine_ls_number_reflns         8450
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.033
_refine_ls_R_factor_all          0.0314
_refine_ls_R_factor_gt           0.0280
_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^)+(0.0391P)^2^+0.6395P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0709
_refine_ls_wR_factor_ref         0.0730
_reflns_Friedel_coverage         0.793
_reflns_Friedel_fraction_full    0.996
_reflns_Friedel_fraction_max     0.997
_reflns_number_gt                7907
_reflns_number_total             8450
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1ob00805f2.cif
_cod_data_source_block           a_CCDC1
_cod_depositor_comments
'Adding full bibliography for 1562756--1562757.cif.'
_cod_database_code               1562757
_shelxl_version_number           2014/6
_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:
 C2(H2), C4(H4), C21(H21)
2.b Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B), C22(H22A,H22B), C23(H23A,H23B), C24(H24A,H24B), C25(H25A,H25B)
2.c Aromatic/amide H refined with riding coordinates:
 C9(H9), C10(H10), C11(H11), C12(H12), C13(H13), C15(H15), C16(H16), C17(H17),
 C18(H18), C27(H27), C28(H28), C29(H29), C30(H30), C31(H31)
2.d Idealised Me refined as rotating group:
 C5(H5A,H5B,H5C), C6(H6A,H6B,H6C)
;
_shelx_res_checksum              94666
_olex2_submission_special_instructions 'No special instructions were received'