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_1568996
_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 H24 O2, 0.5(H2 O)'
_chemical_formula_sum            'C18 H25 O2.5'
_chemical_formula_weight         281.38
_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             2022-08-31
_audit_creation_method
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_audit_update_record
;
2022-12-15 deposited with the CCDC.	2023-05-02 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 106.418(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   17.9138(6)
_cell_length_b                   6.1604(2)
_cell_length_c                   15.2956(6)
_cell_measurement_reflns_used    4066
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      76.9340
_cell_measurement_theta_min      2.9850
_cell_volume                     1619.14(10)
_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 2018/2 (Sheldrick, 2018)'
_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 0.967
_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     40.00 119.00   0.50    0.05    --   47.45  39.00 -64.00  158
  2  \w    108.00 173.00   0.50    0.05    --  107.75  37.00-150.00  130
  3  \w    114.00 164.00   0.50    0.05    --  107.75  39.00 -64.00  100
  4  \w    135.00 172.00   0.50    0.05    --  107.75  37.00  60.00   74
  5  \w     96.00 122.00   0.50    0.05    --  107.75  37.00  60.00   52
  6  \w      7.00  34.00   0.50    0.05    --   47.45 -39.00 141.00   54
  7  \w    -24.00  21.00   0.50    0.05    --   47.45 -19.00 -60.00   90
  8  \w    -23.00  18.00   0.50    0.05    --   47.45 -19.00   0.00   82
  9  \w     37.00 112.00   0.50    0.05    --  107.75-125.00-150.00  150
 10  \w     87.00 112.00   0.50    0.05    --  107.75-125.00  30.00   50
 11  \w     35.00  73.00   0.50    0.05    --  107.75-125.00  30.00   76
 12  \w     35.00  60.00   0.50    0.05    --  107.75 -57.00 -30.00   50
 13  \w     36.00  62.00   0.50    0.05    --  107.75 -57.00-180.00   52
 14  \w     35.00  63.00   0.50    0.05    --  107.75 -57.00-150.00   56
 15  \w     35.00  60.00   0.50    0.05    --  107.75 -57.00-120.00   50
 16  \w     35.00  60.00   0.50    0.05    --  107.75 -57.00 -60.00   50
 17  \w     35.00  61.00   0.50    0.05    --  107.75 -57.00  60.00   52
 18  \w     35.00  60.00   0.50    0.05    --  107.75 -57.00 120.00   50
 19  \w     37.00  62.00   0.50    0.05    --  107.75 -57.00 150.00   50
 20  \w    -41.00 -10.00   0.50    0.05    --  -47.45  39.00 -64.00   62
 21  \w    -62.00 -35.00   0.50    0.05    -- -100.00  57.00  30.00   54
 22  \w    -68.00 -28.00   0.50    0.05    -- -100.00  57.00  60.00   80
 23  \w    -68.00 -32.00   0.50    0.05    -- -100.00  57.00 120.00   72
 24  \w    -54.00 -28.00   0.50    0.05    -- -100.00  57.00 150.00   52
 25  \w    -88.00 -46.00   0.50    0.05    --  -47.45 -39.00 141.00   84
 26  \w   -154.00-129.00   0.50    0.05    -- -100.00 -39.00 141.00   50
 27  \w     95.00 121.00   0.50    0.20    --  107.75  39.00 -64.00   52
 28  \w    -78.00 -37.00   0.50    0.05    --  -47.57 -57.00   0.00   82
 29  \w    -42.00 -15.00   0.50    0.05    --  -47.57  37.00 120.00   54
 30  \w    -97.00 -36.00   0.50    0.05    --  -47.57 -57.00  60.00  122
 31  \w     -2.00  25.00   0.50    0.05    --  -47.57  37.00 120.00   54
 32  \w      3.00  28.00   0.50    0.05    --  -47.57  19.00 -60.00   50
 33  \w     87.00 112.00   0.50    0.05    --   47.57  37.00 -30.00   50
 34  \w   -107.00 -81.00   0.50    0.20    -- -100.00 -69.00  58.42   52
 35  \w   -105.00 -77.00   0.50    0.20    -- -100.00 -77.00  30.00   56
 36  \w   -166.00 -84.00   0.50    0.20    -- -100.00 -61.00  24.39  164
 37  \w   -138.00-114.00   0.50    0.20    -- -100.00 -56.00 -12.05   48
;
_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      0.0421840000
_diffrn_orient_matrix_UB_12      0.0976341000
_diffrn_orient_matrix_UB_13      -0.0657428000
_diffrn_orient_matrix_UB_21      -0.0785796000
_diffrn_orient_matrix_UB_22      0.0774987000
_diffrn_orient_matrix_UB_23      -0.0630511000
_diffrn_orient_matrix_UB_31      0.0091545000
_diffrn_orient_matrix_UB_32      0.2168089000
_diffrn_orient_matrix_UB_33      0.0522036000
_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  0.0811
_diffrn_reflns_av_unetI/netI     0.0806
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.967
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            7068
_diffrn_reflns_point_group_measured_fraction_full 0.905
_diffrn_reflns_point_group_measured_fraction_max 0.849
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.151
_diffrn_reflns_theta_min         3.012
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_target            Mo
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.592
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.50231
_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    1.154
_exptl_crystal_description       block
_exptl_crystal_F_000             612
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.24
_refine_diff_density_max         0.313
_refine_diff_density_min         -0.265
_refine_diff_density_rms         0.061
_refine_ls_abs_structure_details
;
 Flack x determined using 860 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.0(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     193
_refine_ls_number_reflns         2909
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.041
_refine_ls_R_factor_all          0.0626
_refine_ls_R_factor_gt           0.0562
_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^)+(0.0851P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1412
_refine_ls_wR_factor_ref         0.1477
_reflns_Friedel_coverage         0.602
_reflns_Friedel_fraction_full    0.788
_reflns_Friedel_fraction_max     0.707
_reflns_number_gt                2579
_reflns_number_total             2909
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3sc00582h2.cif
_cod_data_source_block           chenxiaow-138_0830_auto
_cod_depositor_comments
'Adding full bibliography for 1568996--1569002.cif.'
_cod_original_formula_sum        'C18 H25 O2.50'
_cod_database_code               1568996
_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, All O(H,H) groups
2. Others
 Fixed Sof: H3A(0.5) H3B(0.5)
3.a Free rotating group:
 O3(H3A,H3B)
3.b Ternary CH refined with riding coordinates:
 C6(H6), C7(H7), C10(H10)
3.c Secondary CH2 refined with riding coordinates:
 C13(H13A,H13B), C14(H14A,H14B)
3.d Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), C9(H9), C11(H11)
3.e X=CH2 refined with riding coordinates:
 C17(H17A,H17B), C18(H18A,H18B)
3.f Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C), C16(H16A,H16B,H16C)
3.g Idealised tetrahedral OH refined as rotating group:
 O1(H1), O2(H2)
;
_shelx_res_checksum              13274
_shelx_hkl_checksum              19416
_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 4.948
_oxdiff_exptl_absorpt_empirical_full_min 0.224