Enantioselective total syntheses of six natural and two proposed meroterpenoids from <i>Psoralea corylifolia</i>.
Chen, Xiao-Wei; Hou, Zi-Chao; Chen, Chi; Zhang, Ling-Hui; Chen, Meng-En; Zhang, Fu-Min; Chemical science 14 (2023) 5699–5704; doi:10.1039/d3sc00582h

data_1569001
_publ_section_title
;
 Enantioselective total syntheses of six natural and two proposed
 meroterpenoids from <i>Psoralea corylifolia</i>.
;
_journal_issue                   21
_journal_name_full               'Chemical science'
_journal_page_first              5699
_journal_page_last               5704
_journal_paper_doi               10.1039/d3sc00582h
_journal_volume                  14
_journal_year                    2023
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C19 H26 O2'
_chemical_formula_sum            'C19 H26 O2'
_chemical_formula_weight         286.39
_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   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2022-12-18
_audit_creation_method
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_audit_update_record
;
2022-12-18 deposited with the CCDC.	2023-05-02 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 112.787(2)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   25.3714(5)
_cell_length_b                   6.05801(10)
_cell_length_c                   23.3168(5)
_cell_measurement_reflns_used    14455
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      77.2910
_cell_measurement_theta_min      2.0750
_cell_volume                     3304.09(12)
_computing_cell_refinement       'CrysAlisPro 1.171.41.113a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.113a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.113a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (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      150.00(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 0.955
_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     35.00 111.00   0.50    0.05    --   47.57  18.00-129.00  152
  2  \w     53.00 102.00   0.50    0.05    --  107.75 -77.00-180.00   98
  3  \w     97.00 140.00   0.50    0.05    --  107.75  18.00-129.00   86
  4  \w    -15.00  37.00   0.50    0.05    --   47.57 -37.00 -90.00  104
  5  \w     35.00  61.00   0.50    0.05    --  107.75 -57.00  90.00   52
  6  \w     37.00  62.00   0.50    0.05    --  107.75 -57.00 120.00   50
  7  \w     96.00 154.00   0.50    0.05    --  107.75  57.00 150.00  116
  8  \w     37.00  63.00   0.50    0.05    --  107.75 -57.00 150.00   52
  9  \w    -26.00  -1.00   0.50    0.05    --   47.57 -18.00  62.00   50
 10  \w     66.00 104.00   0.50    0.05    --  107.75-125.00  30.00   76
 11  \w     56.00 105.00   0.50    0.05    --  107.75 -99.00 -90.00   98
 12  \w    -26.00  28.00   0.50    0.05    --  -47.57  19.00   0.00  108
 13  \w    -23.00   3.00   0.50    0.05    --  -47.57  18.00-129.00   52
 14  \w    -60.00 -34.00   0.50    0.05    -- -100.00  57.00-180.00   52
 15  \w    -69.00 -27.00   0.50    0.05    -- -100.00  57.00 -60.00   84
 16  \w    -64.00 -33.00   0.50    0.05    -- -100.00  57.00   0.00   62
 17  \w    -55.00 -30.00   0.50    0.05    -- -100.00  77.00  60.00   50
 18  \w    -68.00 -27.00   0.50    0.05    -- -100.00  57.00  60.00   82
 19  \w   -109.00 -76.00   0.50    0.05    -- -100.00  77.00  60.00   66
 20  \w    -64.00 -28.00   0.50    0.05    -- -100.00  57.00 150.00   72
 21  \w    -69.00 -43.00   0.50    0.05    -- -100.00  57.00 -30.00   52
 22  \w   -115.00 -50.00   0.50    0.05    --  -47.57 -18.00  62.00  130
 23  \w   -138.00 -79.00   0.50    0.05    -- -100.00 -77.00 -30.00  118
 24  \w   -158.00 -88.00   0.50    0.05    -- -100.00 -18.00  62.00  140
 25  \w    -18.00   8.00   0.50    0.05    --   47.57 -18.00  62.00   52
 26  \w    -74.00 -34.00   0.50    0.05    --  -47.57 -57.00 -90.00   80
 27  \w    -67.00 -37.00   0.50    0.05    --  -47.57 -37.00 -30.00   60
 28  \w    -64.00 -25.00   0.50    0.05    --  -47.57 -77.00   0.00   78
 29  \w      9.00  36.00   0.50    0.05    --   47.57 -37.00 -60.00   54
 30  \w     25.00  73.00   0.50    0.05    --   47.57  77.00 -60.00   96
 31  \w     42.00  68.00   0.50    0.05    --   47.57  57.00   0.00   52
 32  \w    -19.00   7.00   0.50    0.05    --   47.57 -19.00-150.00   52
 33  \w     35.00  66.00   0.50    0.05    --   47.57  37.00 -90.00   62
 34  \w     48.00  74.00   0.50    0.05    --   47.57  57.00  60.00   52
 35  \w   -111.00 -86.00   0.50    0.20    -- -100.00 -48.00 -91.34   50
 36  \w   -108.00 -83.00   0.50    0.20    -- -100.00 -67.00   1.37   50
 37  \w   -108.00 -82.00   0.50    0.20    -- -100.00 -65.00 -23.34   52
 38  \w   -106.00 -81.00   0.50    0.20    -- -100.00 -68.00 -56.46   50
 39  \w   -103.00 -77.00   0.50    0.20    -- -100.00 -76.00  47.12   52
 40  \w   -170.00-144.00   0.50    0.20    -- -100.00 -68.00 -56.46   52
 41  \w   -104.00 -78.00   0.50    0.20    -- -100.00 -77.00 -90.00   52
 42  \w   -108.00 -82.00   0.50    0.20    -- -100.00 -65.00 -12.91   52
 43  \w   -110.00 -84.00   0.50    0.20    -- -100.00 -59.00 -65.98   52
 44  \w   -124.00 -86.00   0.50    0.20    -- -100.00 -57.00 -38.96   76
 45  \w   -113.00 -87.00   0.50    0.20    -- -100.00 -49.00 -84.14   52
 46  \w   -165.00-139.00   0.50    0.20    -- -100.00 -71.00 -43.43   52
 47  \w   -105.00 -80.00   0.50    0.20    -- -100.00 -71.00 -43.43   50
 48  \w   -115.00 -86.00   0.50    0.20    -- -100.00 -57.00 -42.46   58
 49  \w   -106.00 -93.00   0.50    0.20    -- -100.00 -74.00 -74.62   26
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'ROD, Synergy Custom system, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0277903000
_diffrn_orient_matrix_UB_12      0.0503501000
_diffrn_orient_matrix_UB_13      0.0467379000
_diffrn_orient_matrix_UB_21      0.0581783000
_diffrn_orient_matrix_UB_22      -0.0333996000
_diffrn_orient_matrix_UB_23      0.0542736000
_diffrn_orient_matrix_UB_31      0.0135939000
_diffrn_orient_matrix_UB_32      0.2469230000
_diffrn_orient_matrix_UB_33      -0.0021760000
_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  0.0678
_diffrn_reflns_av_unetI/netI     0.0565
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.955
_diffrn_reflns_limit_h_max       31
_diffrn_reflns_limit_h_min       -31
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            19488
_diffrn_reflns_point_group_measured_fraction_full 0.939
_diffrn_reflns_point_group_measured_fraction_max 0.875
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.458
_diffrn_reflns_theta_min         2.055
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_target            Mo
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.565
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.67187
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.113a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.151
_exptl_crystal_description       block
_exptl_crystal_F_000             1248
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.176
_refine_diff_density_min         -0.252
_refine_diff_density_rms         0.050
_refine_ls_abs_structure_details
;
 Flack x determined using 2115 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.03(18)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     393
_refine_ls_number_reflns         6149
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.069
_refine_ls_R_factor_all          0.0474
_refine_ls_R_factor_gt           0.0446
_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^)+(0.0673P)^2^+0.4184P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1146
_refine_ls_wR_factor_ref         0.1169
_reflns_Friedel_coverage         0.669
_reflns_Friedel_fraction_full    0.866
_reflns_Friedel_fraction_max     0.777
_reflns_number_gt                5717
_reflns_number_total             6149
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3sc00582h2.cif
_cod_data_source_block           chenxiaow-137a_0830_auto
_cod_depositor_comments
;
Adding full bibliography for 1568996--1569002.cif.

2025-06-02
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_sum            'C38 H52 O4'
_cod_original_formula_weight         572.79
_cod_original_formula_moiety         '2(C19 H26 O2)'
_cod_original_formula_units_Z            4
_cod_original_cell_volume        3304.08(12)
_cod_database_code               1569001
_shelx_shelxl_version_number     2018/3
_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
 H2-O2
 0.86 with sigma of 0.01
3.a Ternary CH refined with riding coordinates:
 C4(H4), C5(H5), C9(H9), C48(H48), C51(H51), C53(H53)
3.b Secondary CH2 refined with riding coordinates:
 C12(H12A,H12B), C15(H15A,H15B), C57(H57A,H57B), C61(H61A,H61B)
3.c Aromatic/amide H refined with riding coordinates:
 C1(H1), C11(H11), C17(H17), C18(H18), C31(H31), C58(H58), C63(H63), C64(H64),
 C77(H77), C79(H79)
3.d X=CH2 refined with riding coordinates:
 C20(H20A,H20B), C28(H28A,H28B), C68(H68A,H68B), C74(H74A,H74B)
3.e Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C), C29(H29A,H29B,H29C), C44(H44A,H44B,H44C), C59(H59A,H59B,
 H59C), C75(H75A,H75B,H75C), C91(H91A,H91B,H91C)
;
_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 4.451
_oxdiff_exptl_absorpt_empirical_full_min 0.191