Catalytic enantioselective construction of two N-stereogenic centers of <i>ethano</i>- and <i>propano</i>-Tröger's bases.
Guan, Chun-Yan; Lu, Tao; Li, Ya; Liu, Chao-Hua; Xiao, Xiao; Mei, Guang-Jian; Chemical science 16 (2025) 19683–19693; doi:10.1039/d5sc05846e

data_1575872
_publ_section_title
;
 Catalytic enantioselective construction of two N-stereogenic centers of
 <i>ethano</i>- and <i>propano</i>-Tr&#xf6;ger's bases.
;
_journal_issue                   42
_journal_name_full               'Chemical science'
_journal_page_first              19683
_journal_page_last               19693
_journal_paper_doi               10.1039/d5sc05846e
_journal_volume                  16
_journal_year                    2025
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C24 H32 N2 O'
_chemical_formula_sum            'C24 H32 N2 O'
_chemical_formula_weight         364.51
_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             2024-09-27
_audit_creation_method
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_audit_update_record
;
2024-10-11 deposited with the CCDC.	2025-09-24 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   10.72230(10)
_cell_length_b                   13.6952(2)
_cell_length_c                   27.6926(3)
_cell_measurement_reflns_used    10379
_cell_measurement_temperature    99.99(10)
_cell_measurement_theta_max      76.9010
_cell_measurement_theta_min      3.6390
_cell_volume                     4066.49(8)
_computing_cell_refinement       'CrysAlisPro 1.171.42.93a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.93a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.93a (Rigaku OD, 2023)'
_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_environment      N~2~
_diffrn_ambient_temperature      99.99(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.944
_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     35.00 117.00   0.50    0.27    --   45.89  47.00-158.00  164
  2  \w     41.00  66.00   0.50    1.09    --  106.55 -57.00 -90.00   50
  3  \w     51.00  83.00   0.50    1.09    --  106.55 -74.00-105.00   64
  4  \w     70.00 110.00   0.50    1.09    --  106.55-122.00-175.00   80
  5  \w   -170.00-137.00   0.50    1.09    -- -104.00 -47.00  52.00   66
  6  \w   -172.00-126.00   0.50    1.09    -- -104.00 -19.00   0.00   92
  7  \w   -124.00 -99.00   0.50    1.09    -- -104.00 -19.00   0.00   50
  8  \w   -130.00 -94.00   0.50    1.09    -- -104.00 -47.00  52.00   72
  9  \w    -22.00  22.00   0.50    0.27    --  -45.89  19.00   0.00   88
 10  \w    -56.00 -31.00   0.50    1.09    -- -104.00  57.00 150.00   50
 11  \w    -66.00 -31.00   0.50    1.09    -- -104.00  74.00  22.00   70
 12  \w    -58.00 -31.00   0.50    1.09    -- -104.00  57.00   0.00   54
 13  \w    -64.00 -34.00   0.50    1.09    -- -104.00  57.00  30.00   60
 14  \w    -35.00  13.00   0.50    0.27    --  -45.89  38.00  30.00   96
 15  \w    -60.00 -33.00   0.50    1.09    -- -104.00  57.00-150.00   54
 16  \w    -64.00 -34.00   0.50    1.09    -- -104.00  57.00-180.00   60
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RINC): Kappa single'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0885480000
_diffrn_orient_matrix_UB_12      0.0390825000
_diffrn_orient_matrix_UB_13      -0.0393194000
_diffrn_orient_matrix_UB_21      -0.0776034000
_diffrn_orient_matrix_UB_22      -0.0524385000
_diffrn_orient_matrix_UB_23      -0.0389718000
_diffrn_orient_matrix_UB_31      -0.0823453000
_diffrn_orient_matrix_UB_32      0.0915100000
_diffrn_orient_matrix_UB_33      -0.0055265000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0369
_diffrn_reflns_av_unetI/netI     0.0441
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.944
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_number            16268
_diffrn_reflns_point_group_measured_fraction_full 0.943
_diffrn_reflns_point_group_measured_fraction_max 0.872
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         77.577
_diffrn_reflns_theta_min         3.600
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.556
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.81157
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.93a (Rigaku Oxford Diffraction, 2023)
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    1.191
_exptl_crystal_description       block
_exptl_crystal_F_000             1584
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.19
_refine_diff_density_max         0.197
_refine_diff_density_min         -0.190
_refine_diff_density_rms         0.038
_refine_ls_abs_structure_details
;
 Flack x determined using 2582 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.10(13)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     495
_refine_ls_number_reflns         7554
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.058
_refine_ls_R_factor_all          0.0418
_refine_ls_R_factor_gt           0.0363
_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^)+(0.0460P)^2^+0.8492P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0935
_refine_ls_wR_factor_ref         0.0963
_reflns_Friedel_coverage         0.655
_reflns_Friedel_fraction_full    0.872
_reflns_Friedel_fraction_max     0.782
_reflns_number_gt                7008
_reflns_number_total             7554
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5sc05846e2.cif
_cod_data_source_block           a
_cod_depositor_comments
'Adding full bibliography for 1575872--1575873.cif.'
_cod_database_code               1575872
_shelx_shelxl_version_number     2019/2
_chemical_oxdiff_formula         CHON
_chemical_oxdiff_usercomment     CHON
_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, All O(H) groups
2.a Riding coordinates:
 O1(H1), O2(H2)
2.b Ternary CH refined with riding coordinates:
 C3(H3), C12(H12), C22(H22), C27(H27), C36(H36), C46(H46)
2.c Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C2(H2A,H2B), C4(H4A,H4B), C5(H5A,H5B), C15(H15A,H15B), C25(H25A,
 H25B), C26(H26A,H26B), C28(H28A,H28B), C29(H29A,H29B), C39(H39A,H39B)
2.d Aromatic/amide H refined with riding coordinates:
 C8(H8), C10(H10), C11(H11), C18(H18), C20(H20), C21(H21), C32(H32), C34(H34),
 C35(H35), C42(H42), C44(H44), C45(H45)
2.e Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C), C14(H14A,H14B,H14C), C23(H23A,H23B,H23C), C24(H24A,H24B,
 H24C), C37(H37A,H37B,H37C), C38(H38A,H38B,H38C), C47(H47A,H47B,H47C), C48(H48A,
 H48B,H48C)
;
_shelx_res_checksum              35351
_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 1.250
_oxdiff_exptl_absorpt_empirical_full_min 0.800