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_1575873
_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         'C20 H22 N2'
_chemical_formula_sum            'C20 H22 N2'
_chemical_formula_weight         290.39
_space_group_crystal_system      monoclinic
_space_group_IT_number           5
_space_group_name_Hall           'C 2y'
_space_group_name_H-M_alt        'C 1 2 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2025-01-09
_audit_creation_method
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_audit_update_record
;
2025-04-23 deposited with the CCDC.	2025-09-24 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 104.6430(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   22.9846(4)
_cell_length_b                   6.25910(10)
_cell_length_c                   11.5085(2)
_cell_measurement_reflns_used    7077
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      76.5760
_cell_measurement_theta_min      3.9580
_cell_volume                     1601.87(5)
_computing_cell_refinement       'CrysAlisPro 1.171.43.140a (Rigaku OD, 2024)'
_computing_data_collection       'CrysAlisPro 1.171.43.140a (Rigaku OD, 2024)'
_computing_data_reduction        'CrysAlisPro 1.171.43.140a (Rigaku OD, 2024)'
_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      100.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.963
_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     35.00 113.00   0.50    0.05    --   45.74  53.00 -78.00  156
  2  \w     39.00 111.00   0.50    0.05    --   45.74  38.00  30.00  144
  3  \w     45.00  84.00   0.50    0.05    --   45.74  57.00  60.00   78
  4  \w     86.00 112.00   0.50    0.05    --  106.45  77.00   0.00   52
  5  \w    132.00 165.00   0.50    0.05    --  106.45  77.00   0.00   66
  6  \w    142.00 167.00   0.50    0.05    --  106.45  53.00 -78.00   50
  7  \w    108.00 138.00   0.50    0.05    --  106.45  53.00 -78.00   60
  8  \w    -25.00  28.00   0.50    0.05    --   45.74 -19.00 -30.00  106
  9  \w     36.00  61.00   0.50    0.05    --  106.45 -57.00 120.00   50
 10  \w     34.00  59.00   0.50    0.05    --  106.45 -53.00 137.00   50
 11  \w     30.00  60.00   0.50    0.05    --   45.74 -53.00 137.00   60
 12  \w     35.00  65.00   0.50    0.05    --  106.45 -57.00 -30.00   60
 13  \w     35.00  66.00   0.50    0.05    --  106.45 -57.00-120.00   62
 14  \w     40.00 101.00   0.50    0.05    --  106.45 -99.00-150.00  122
 15  \w     73.00 103.00   0.50    0.05    --  106.45-125.00-150.00   60
 16  \w     40.00 111.00   0.50    0.05    --  106.45-125.00 -60.00  142
 17  \w     46.00 104.00   0.50    0.05    --  106.45 -99.00  60.00  116
 18  \w     62.00 106.00   0.50    0.05    --  106.45 -99.00 120.00   88
 19  \w    -63.00 -31.00   0.50    0.05    -- -104.00  57.00  60.00   64
 20  \w    -64.00 -32.00   0.50    0.05    -- -104.00  57.00   0.00   64
 21  \w    -63.00 -32.00   0.50    0.05    -- -104.00  57.00 -30.00   62
 22  \w    -58.00 -33.00   0.50    0.05    -- -104.00  53.00 -78.00   50
 23  \w    -55.00 -13.00   0.50    0.05    --  -45.74  53.00 -78.00   84
 24  \w    -64.00 -33.00   0.50    0.05    -- -104.00  57.00  90.00   62
 25  \w    -62.00 -32.00   0.50    0.05    -- -104.00  57.00 120.00   60
 26  \w    -59.00 -32.00   0.50    0.05    -- -104.00  57.00 150.00   54
 27  \w   -175.00-149.00   0.50    0.05    -- -104.00 -77.00  90.00   52
 28  \w   -161.00-136.00   0.50    0.05    -- -104.00 -77.00  60.00   50
 29  \w   -136.00 -82.00   0.50    0.05    -- -104.00 -77.00  90.00  108
 30  \w   -106.00 -81.00   0.50    0.05    -- -104.00 -77.00  60.00   50
 31  \w   -106.00 -81.00   0.50    0.05    -- -104.00 -77.00  30.00   50
 32  \w   -168.00 -92.00   0.50    0.05    -- -104.00 -60.00  -0.15  152
 33  \w   -169.00-143.00   0.50    0.05    -- -104.00 -57.00  90.00   52
 34  \w   -172.00-132.00   0.50    0.05    -- -104.00 -53.00 137.00   80
 35  \w   -138.00 -96.00   0.50    0.05    -- -104.00 -57.00  90.00   84
 36  \w   -116.00 -91.00   0.50    0.05    -- -104.00 -57.00  60.00   50
 37  \w   -130.00 -90.00   0.50    0.05    -- -104.00 -57.00  30.00   80
 38  \w   -117.00 -92.00   0.50    0.05    -- -104.00 -47.00  52.73   50
 39  \w   -166.00-140.00   0.50    0.05    -- -104.00 -45.00  38.72   52
 40  \w   -159.00 -92.00   0.50    0.05    -- -104.00 -47.00   5.53  134
 41  \w   -116.00 -91.00   0.50    0.05    -- -104.00 -46.00  10.87   50
 42  \w   -119.00 -93.00   0.50    0.05    -- -104.00 -45.00  38.72   52
 43  \w   -120.00 -94.00   0.50    0.05    -- -104.00 -44.00  30.98   52
 44  \w   -123.00 -91.00   0.50    0.05    -- -104.00 -38.00  90.00   64
 45  \w   -100.00 -33.00   0.50    0.05    --  -45.74 -53.00 137.00  134
 46  \w   -123.00 -98.00   0.50    0.05    -- -104.00 -38.00-150.00   50
 47  \w   -175.00-150.00   0.50    0.05    -- -104.00 -38.00-150.00   50
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1103674000
_diffrn_orient_matrix_UB_12      -0.1392738000
_diffrn_orient_matrix_UB_13      -0.0275214000
_diffrn_orient_matrix_UB_21      0.0606970000
_diffrn_orient_matrix_UB_22      -0.0771885000
_diffrn_orient_matrix_UB_23      -0.0489467000
_diffrn_orient_matrix_UB_31      0.0568680000
_diffrn_orient_matrix_UB_32      -0.1876637000
_diffrn_orient_matrix_UB_33      0.0405562000
_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  0.0354
_diffrn_reflns_av_unetI/netI     0.0317
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.963
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            10019
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.943
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         77.793
_diffrn_reflns_theta_min         3.970
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.539
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.77198
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.43.140a (Rigaku Oxford Diffraction, 2024)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.204
_exptl_crystal_description       plate
_exptl_crystal_F_000             624
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.162
_refine_diff_density_min         -0.188
_refine_diff_density_rms         0.041
_refine_ls_abs_structure_details
;
 Flack x determined using 1282 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.1(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     201
_refine_ls_number_reflns         3223
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.051
_refine_ls_R_factor_all          0.0375
_refine_ls_R_factor_gt           0.0359
_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^)+(0.0566P)^2^+0.2280P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0925
_refine_ls_wR_factor_ref         0.0940
_reflns_Friedel_coverage         0.791
_reflns_Friedel_fraction_full    0.992
_reflns_Friedel_fraction_max     0.920
_reflns_number_gt                3069
_reflns_number_total             3223
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5sc05846e2.cif
_cod_data_source_block           a_CCDC1
_cod_depositor_comments
'Adding full bibliography for 1575872--1575873.cif.'
_cod_database_code               1575873
_shelx_shelxl_version_number     2019/2
_chemical_oxdiff_formula         CHN
_chemical_oxdiff_usercomment     CHN
_shelx_estimated_absorpt_t_max   0.919
_shelx_estimated_absorpt_t_min   0.905
_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 Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B), C12(H12A,H12B), C13(H13A,H13B), C8(H8A,H8B)
2.b Aromatic/amide H refined with riding coordinates:
 C4(H4), C16(H16), C19(H19), C3(H3), C17(H17), C7(H7)
2.c X=CH2 refined with riding coordinates:
 C11(H11A,H11B)
2.d Idealised Me refined as rotating group:
 C20(H20A,H20B,H20C), C1(H1A,H1B,H1C)
;
_shelx_res_checksum              46901
_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 1.675
_oxdiff_exptl_absorpt_empirical_full_min 0.638