Practical asymmetric amine nucleophilic approach for the modular construction of protected α-quaternary amino acids
Liu, Teng; Ni, Shaofei; Guo, Wusheng; Chemical Science  (2022) –; doi:10.1039/D2SC02318K

data_1567071
_publ_section_title
;
 Practical asymmetric amine nucleophilic approach for the modular
 construction of protected \a-quaternary amino acids
;
_journal_name_full               'Chemical Science'
_journal_paper_doi               10.1039/D2SC02318K
_journal_year                    2022
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C17 H15 N O2'
_chemical_formula_sum            'C17 H15 N O2'
_chemical_formula_weight         265.30
_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   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2021-03-11
_audit_creation_method
;
Olex2 1.3-alpha
(compiled 2020.09.11 svn.r3730fd0d for OlexSys, GUI svn.r6159)
;
_audit_update_record
;
2021-06-28 deposited with the CCDC.	2022-05-16 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90.6825(8)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   9.65133(9)
_cell_length_b                   11.74209(11)
_cell_length_c                   25.3227(2)
_cell_measurement_reflns_used    20682
_cell_measurement_temperature    149.99(10)
_cell_measurement_theta_max      73.7260
_cell_measurement_theta_min      3.4560
_cell_volume                     2869.54(4)
_computing_cell_refinement       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 1.3-alpha (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3-alpha (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      149.99(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.979
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w   -115.00 -16.00   1.00    1.00    --  -40.73 -38.00-150.00   99
  2  \w   -117.00  -8.00   1.00    1.00    --  -40.73 -77.00 120.00  109
  3  \w   -117.00  -8.00   1.00    1.00    --  -40.73 -77.00 -90.00  109
  4  \w   -115.00 -16.00   1.00    1.00    --  -40.73 -38.00 150.00   99
  5  \w   -117.00  -8.00   1.00    1.00    --  -40.73 -77.00 -30.00  109
  6  \w   -117.00  -8.00   1.00    1.00    --  -40.73 -77.00  30.00  109
  7  \w   -115.00 -16.00   1.00    1.00    --  -40.73 -38.00 -30.00   99
  8  \w    -34.00  65.00   1.00    1.00    --   40.73 -38.00-120.00   99
  9  \w      4.00  78.00   1.00    1.35    --   40.73-102.00-127.00   74
 10  \w     63.00  91.00   1.00    1.35    --  107.58 -94.00 -60.00   28
 11  \w    114.00 140.00   1.00    1.35    --  107.58  61.00-120.00   26
 12  \w     76.00 101.00   1.00    1.35    --  107.58  77.00   0.00   25
 13  \w     78.00 104.00   1.00    1.35    --  107.58  61.00 -60.00   26
 14  \w     35.00 113.00   1.00    1.35    --  107.58 -45.00-150.00   78
 15  \w     78.00 104.00   1.00    1.35    --  107.58  61.00-120.00   26
 16  \w     75.00 101.00   1.00    1.35    --  107.58  77.00 -60.00   26
 17  \w    151.00 177.00   1.00    1.35    --  107.58  77.00 -30.00   26
 18  \w     75.00 101.00   1.00    1.35    --  107.58  77.00-150.00   26
 19  \w     75.00 101.00   1.00    1.35    --  107.58  77.00 -30.00   26
 20  \w    136.00 178.00   1.00    1.35    --  107.58  61.00   0.00   42
 21  \w     79.00 106.00   1.00    1.35    --  107.58  61.00 -30.00   27
 22  \w     82.00 163.00   1.00    1.35    --  107.58  45.00 -90.00   81
 23  \w     78.00 105.00   1.00    1.35    --  107.58  61.00 -90.00   27
 24  \w     75.00 101.00   1.00    1.35    --  107.58  77.00 -90.00   26
 25  \w     82.00 112.00   1.00    1.35    --  107.58  45.00 -30.00   30
 26  \w     83.00 134.00   1.00    1.35    --  107.58  45.00   0.00   51
 27  \w     82.00 129.00   1.00    1.35    --  107.58  45.00-120.00   47
 28  \w     85.00 176.00   1.00    1.35    --  107.58  45.00 -60.00   91
 29  \w     75.00 101.00   1.00    1.35    --  107.58  77.00-120.00   26
 30  \w     78.00 104.00   1.00    1.35    --  107.58  61.00   0.00   26
 31  \w     25.00  92.00   1.00    1.35    --  107.58 -94.00   0.00   67
 32  \w     19.00 128.00   1.00    1.35    --  107.58   0.00-180.00  109
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1532376000
_diffrn_orient_matrix_UB_12      0.0235804000
_diffrn_orient_matrix_UB_13      -0.0138367000
_diffrn_orient_matrix_UB_21      -0.0409431000
_diffrn_orient_matrix_UB_22      -0.0326687000
_diffrn_orient_matrix_UB_23      0.0566174000
_diffrn_orient_matrix_UB_31      0.0182101000
_diffrn_orient_matrix_UB_32      0.1248947000
_diffrn_orient_matrix_UB_33      0.0173746000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0236
_diffrn_reflns_av_unetI/netI     0.0235
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.979
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            30634
_diffrn_reflns_point_group_measured_fraction_full 0.943
_diffrn_reflns_point_group_measured_fraction_max 0.917
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.894
_diffrn_reflns_theta_min         3.491
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.647
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.89519
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.228
_exptl_crystal_description       block
_exptl_crystal_F_000             1120
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.195
_refine_diff_density_min         -0.217
_refine_diff_density_rms         0.041
_refine_ls_abs_structure_details
;
 Flack x determined using 4292 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.08(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     741
_refine_ls_number_reflns         10645
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.046
_refine_ls_R_factor_all          0.0348
_refine_ls_R_factor_gt           0.0333
_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^)+(0.0500P)^2^+0.2540P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0838
_refine_ls_wR_factor_ref         0.0853
_reflns_Friedel_coverage         0.782
_reflns_Friedel_fraction_full    0.885
_reflns_Friedel_fraction_max     0.848
_reflns_number_gt                10229
_reflns_number_total             10645
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2sc02318k2.cif
_cod_data_source_block           9761
_cod_database_code               1567071
_shelx_shelxl_version_number     2018/3
_reflns_odcompleteness_completeness 99.58
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C6(H6), C13(H13), C14(H14), C15(H15),
 C16(H16), C17(H17), C19(H19), C20(H20), C21(H21), C22(H22), C23(H23), C30(H30),
  C31(H31), C32(H32), C33(H33), C34(H34), C36(H36), C37(H37), C38(H38),
 C39(H39), C40(H40), C47(H47), C48(H48), C49(H49), C50(H50), C51(H51), C53(H53),
  C54(H54), C55(H55), C56(H56), C57(H57), C64(H64), C65(H65), C66(H66),
 C67(H67), C68(H68)
2.b Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C), C26(H26A,H26B,H26C), C45(H45A,H45B,H45C), C62(H62A,H62B,
 H62C)
2.c :
 C9(H9), C28(H28), C43(H43), C60(H60)
;
_shelx_res_checksum              43014
_shelx_hkl_checksum              89019
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.230
_oxdiff_exptl_absorpt_empirical_full_min 0.777