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_1569000
_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         'C18 H26 O3, 0.5(C H4 O)'
_chemical_formula_sum            'C18.5 H28 O3.5'
_chemical_formula_weight         306.40
_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             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                 101.0819(18)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   15.3362(3)
_cell_length_b                   6.95130(12)
_cell_length_c                   16.3195(3)
_cell_measurement_reflns_used    13795
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      77.0600
_cell_measurement_theta_min      2.7310
_cell_volume                     1707.32(6)
_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 1.000
_diffrn_measured_fraction_theta_max 0.960
_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      6.00 112.00   0.50    0.05    --   47.57   7.00 -46.00  212
  2  \w    118.00 175.00   0.50    0.10    --  107.75  37.00-180.00  114
  3  \w     70.00 175.00   0.50    0.10    --  107.75   7.00 -46.00  210
  4  \w    148.00 174.00   0.50    0.10    --  107.75  57.00   0.00   52
  5  \w     94.00 125.00   0.50    0.10    --  107.75  57.00   0.00   62
  6  \w   -106.00 -32.00   0.50    0.10    -- -100.00  77.00  60.00  148
  7  \w    -64.00 -35.00   0.50    0.10    -- -100.00  57.00 150.00   58
  8  \w    -63.00 -37.00   0.50    0.10    -- -100.00 125.00  30.00   52
  9  \w   -112.00 -70.00   0.50    0.10    -- -100.00 125.00  30.00   84
 10  \w    -69.00 -29.00   0.50    0.10    -- -100.00  57.00-150.00   80
 11  \w    -75.00 -50.00   0.50    0.10    -- -100.00 125.00-150.00   50
 12  \w   -112.00 -86.00   0.50    0.10    -- -100.00 125.00-150.00   52
 13  \w    -88.00 -47.00   0.50    0.05    --  -47.57 125.00   0.00   82
 14  \w   -117.00 -34.00   0.50    0.05    --  -47.57  -7.00 138.00  166
 15  \w   -140.00-104.00   0.50    0.10    -- -100.00  -7.00 138.00   72
 16  \w    -13.00  13.00   0.50    0.05    --   47.57  -7.00 138.00   52
 17  \w     38.00  63.00   0.50    0.10    --  107.75 -57.00  60.00   50
 18  \w     35.00  61.00   0.50    0.10    --  107.75 -57.00 -90.00   52
 19  \w     35.00  62.00   0.50    0.10    --  107.75 -57.00 -60.00   54
 20  \w     80.00 105.00   0.50    0.10    --  107.75 -99.00  60.00   50
 21  \w     45.00 104.00   0.50    0.10    --  107.75 -99.00 120.00  118
 22  \w     36.00  62.00   0.50    0.10    --  107.75 -99.00  60.00   52
 23  \w   -126.00 -88.00   0.50    0.10    -- -100.00  -7.00 138.00   76
 24  \w    -61.00 -34.00   0.50    0.05    --  -47.57 -53.00  94.89   54
 25  \w    -80.00 -37.00   0.50    0.05    --  -47.57 -19.00  60.00   86
 26  \w     25.00  53.00   0.50    0.05    --   47.57  77.00   0.00   56
 27  \w     27.00  76.00   0.50    0.05    --   47.57  77.00  90.00   98
 28  \w     39.00  65.00   0.50    0.05    --   47.57  37.00  30.00   52
 29  \w     25.00  63.00   0.50    0.05    --   47.57  77.00  60.00   76
 30  \w     35.00  70.00   0.50    0.05    --   47.57  37.00  90.00   70
 31  \w     35.00  62.00   0.50    0.05    --   47.57  37.00  60.00   54
 32  \w   -167.00-141.00   0.50    0.10    -- -100.00 -78.00   0.51   52
 33  \w   -107.00 -79.00   0.50    0.10    -- -100.00 -73.00  80.64   56
 34  \w   -104.00 -79.00   0.50    0.10    -- -100.00 -72.00  50.05   50
 35  \w   -164.00-138.00   0.50    0.10    -- -100.00 -70.00 102.44   52
 36  \w   -105.00 -80.00   0.50    0.10    -- -100.00 -70.00 102.44   50
 37  \w   -104.00 -78.00   0.50    0.10    -- -100.00 -76.00  12.22   52
 38  \w   -167.00-158.50   0.50    0.10    -- -100.00 -61.00 117.59   17
;
_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      0.1002726000
_diffrn_orient_matrix_UB_12      0.0158299000
_diffrn_orient_matrix_UB_13      0.0359187000
_diffrn_orient_matrix_UB_21      0.0187779000
_diffrn_orient_matrix_UB_22      0.0159073000
_diffrn_orient_matrix_UB_23      -0.0891402000
_diffrn_orient_matrix_UB_31      -0.0084319000
_diffrn_orient_matrix_UB_32      0.2205089000
_diffrn_orient_matrix_UB_33      0.0039291000
_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  0.0500
_diffrn_reflns_av_unetI/netI     0.0468
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.960
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            16825
_diffrn_reflns_point_group_measured_fraction_full 0.904
_diffrn_reflns_point_group_measured_fraction_max 0.846
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.169
_diffrn_reflns_theta_min         2.759
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.643
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.45746
_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    1.192
_exptl_crystal_description       block
_exptl_crystal_F_000             668
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.223
_refine_diff_density_min         -0.226
_refine_diff_density_rms         0.044
_refine_ls_abs_structure_details
;
 Flack x determined using 2099 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.22(13)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     445
_refine_ls_number_reflns         6125
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.060
_refine_ls_R_factor_all          0.0421
_refine_ls_R_factor_gt           0.0401
_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^)+(0.0713P)^2^+0.0277P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1058
_refine_ls_wR_factor_ref         0.1075
_reflns_Friedel_coverage         0.623
_reflns_Friedel_fraction_full    0.790
_reflns_Friedel_fraction_max     0.710
_reflns_number_gt                5784
_reflns_number_total             6125
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3sc00582h2.cif
_cod_data_source_block           chenxiaowei_0426_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            'C37 H56 O7'
_cod_original_formula_weight         612.81
_cod_original_formula_moiety         '2(C18 H26 O3), C H4 O'
_cod_original_formula_units_Z            2
_cod_original_cell_volume        1707.32(5)
_cod_database_code               1569000
_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, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C19(H19), C20(H20), C30(H30), C18(H18), C26(H26), C37(H37)
2.b Secondary CH2 refined with riding coordinates:
 C15(H15A,H15B), C33(H33A,H33B), C21(H21A,H21B), C36(H36A,H36B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2A), C5(H5A), C22(H22), C28(H28), C32(H32), C6(H6A), C8(H8), C12(H12),
 C16(H16), C23(H23)
2.d Idealised Me refined as rotating group:
 C3(H3A,H3B,H3C), C7(H7A,H7B,H7C), C17(H17A,H17B,H17C), C13(H13A,H13B,H13C),
 C27(H27A,H27B,H27C), C29(H29A,H29B,H29C), C35(H35A,H35B,H35C)
2.e Idealised tetrahedral OH refined as rotating group:
 O1(H1)
;
_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 2.045
_oxdiff_exptl_absorpt_empirical_full_min 0.308