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_1568998
_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         286.40
_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   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2022-09-09
_audit_creation_method
;
Olex2 1.3-ac4
(compiled 2019.04.23 svn.r3594 for Rigaku Oxford Diffraction, GUI svn.r5739)
;
_audit_update_record
;
2022-12-15 deposited with the CCDC.	2023-05-02 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.1934(2)
_cell_length_b                   13.5942(4)
_cell_length_c                   20.6761(6)
_cell_measurement_reflns_used    4905
_cell_measurement_temperature    149.99(10)
_cell_measurement_theta_max      77.3710
_cell_measurement_theta_min      3.9080
_cell_volume                     1740.81(9)
_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 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      149.99(10)
_diffrn_detector                 'Image Plate'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            'Rigaku IP'
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.953
_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    -12.00  25.00   0.50    1.63    --  -47.45  19.00 178.00   74
  2  \w   -175.00 -87.00   0.50    6.52    -- -100.00 -19.00  10.00  176
  3  \w   -148.00-122.00   0.50    6.52    -- -100.00-107.00-152.00   52
  4  \w    134.00 172.00   0.50    6.52    --  107.75 125.00  26.00   76
  5  \w     82.00 116.00   0.50    6.52    --  107.75 125.00  26.00   68
  6  \w    -82.00 -23.00   0.50    1.63    --  -47.45 125.00  60.00  118
  7  \w    -22.00  21.00   0.50    1.63    --   47.45 -19.00  10.00   86
  8  \w    -26.00  39.00   0.50    1.63    --   47.45 -37.00 -60.00  130
  9  \w    -69.00 -44.00   0.50    6.52    -- -100.00  57.00 -90.00   50
 10  \w   -137.00 -92.00   0.50    6.52    -- -100.00 -37.00-120.00   90
 11  \w    -60.00 -34.00   0.50    6.52    -- -100.00  57.00 -30.00   52
 12  \w     82.00 112.00   0.50    6.52    --  107.75-125.00-120.00   60
 13  \w     35.00 112.00   0.50    6.52    --  107.75-125.00   0.00  154
 14  \w     35.00  72.00   0.50    6.52    --  107.75-125.00-120.00   74
 15  \w     35.00  60.00   0.50    6.52    --  107.75 -57.00   0.00   50
 16  \w     36.00  61.00   0.50    6.52    --  107.75 -57.00  30.00   50
 17  \w     35.00  60.00   0.50    6.52    --  107.75 -57.00 -90.00   50
 18  \w     35.00  61.00   0.50    6.52    --  107.75 -57.00-150.00   52
 19  \w     49.00  74.00   0.50    6.52    --  107.75 -77.00-120.00   50
 20  \w     38.00  63.00   0.50    6.52    --  107.75 -57.00-180.00   50
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Rigaku R-AXIS SPIDER IP'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0027658000
_diffrn_orient_matrix_UB_12      -0.1106145000
_diffrn_orient_matrix_UB_13      -0.0162659000
_diffrn_orient_matrix_UB_21      -0.0616956000
_diffrn_orient_matrix_UB_22      0.0236680000
_diffrn_orient_matrix_UB_23      -0.0705036000
_diffrn_orient_matrix_UB_31      0.2408517000
_diffrn_orient_matrix_UB_32      0.0073029000
_diffrn_orient_matrix_UB_33      -0.0178324000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0619
_diffrn_reflns_av_unetI/netI     0.0610
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.953
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            8246
_diffrn_reflns_point_group_measured_fraction_full 0.982
_diffrn_reflns_point_group_measured_fraction_max 0.918
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.811
_diffrn_reflns_theta_min         3.892
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_target            Mo
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.536
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.62327
_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    1.093
_exptl_crystal_description       needle
_exptl_crystal_F_000             624
_exptl_crystal_size_max          0.11
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.260
_refine_diff_density_min         -0.233
_refine_diff_density_rms         0.058
_refine_ls_abs_structure_details
;
 Flack x determined using 1066 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.1(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.103
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     194
_refine_ls_number_reflns         3406
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.103
_refine_ls_R_factor_all          0.0615
_refine_ls_R_factor_gt           0.0519
_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^)+(0.0807P)^2^+0.3881P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1406
_refine_ls_wR_factor_ref         0.1477
_reflns_Friedel_coverage         0.661
_reflns_Friedel_fraction_full    0.963
_reflns_Friedel_fraction_max     0.870
_reflns_number_gt                3011
_reflns_number_total             3406
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3sc00582h2.cif
_cod_data_source_block           chenxiaowei88-zhfm_0908-1_auto
_cod_depositor_comments
'Adding full bibliography for 1568996--1569002.cif.'
_cod_database_code               1568998
_shelx_shelxl_version_number     2018/3
_reflns_odcompleteness_completeness 99.57
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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:
 C2(H2A), C3(H3), C5(H5)
2.b Secondary CH2 refined with riding coordinates:
 C13(H13A,H13B), C16(H16A,H16B)
2.c Aromatic/amide H refined with riding coordinates:
 C6(H6), C7(H7), C8(H8), C10(H10), C11(H11)
2.d X=CH2 refined with riding coordinates:
 C17(H17A,H17B), C18(H18A,H18B)
2.e Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C), C15(H15A,H15B,H15C), C19(H19A,H19B,H19C)
2.f Idealised tetrahedral OH refined as rotating group:
 O2(H2)
;
_shelx_res_checksum              6520
_shelx_hkl_checksum              89609
_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 3.313
_oxdiff_exptl_absorpt_empirical_full_min 0.321