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_1568999
_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 unk
_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             2022-08-31
_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                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.02770(10)
_cell_length_b                   10.7851(2)
_cell_length_c                   25.2404(4)
_cell_measurement_reflns_used    6096
_cell_measurement_temperature    149.99(10)
_cell_measurement_theta_max      77.1900
_cell_measurement_theta_min      3.4910
_cell_volume                     1640.86(5)
_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      149.99(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.995
_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    -19.00   6.00   0.50    0.18    --   47.57 -19.00 -30.00   50
  2  \w     35.00  60.00   0.50    0.74    --  107.75 -57.00-150.00   50
  3  \w     38.00  63.00   0.50    0.74    --  107.75 -57.00 -60.00   50
  4  \w    -11.00  14.00   0.50    0.18    --   47.57  -8.00  39.00   50
  5  \w     72.00  97.00   0.50    0.18    --   47.57 131.00  60.00   50
  6  \w     35.00  64.00   0.50    0.74    --  107.75-125.00 -60.00   58
  7  \w     82.00 111.00   0.50    0.74    --  107.75-125.00 -60.00   58
  8  \w     73.00 110.00   0.50    0.74    --  107.75-125.00   0.00   74
  9  \w     39.00  69.00   0.50    0.74    --  107.75-125.00   0.00   60
 10  \w     42.00  70.00   0.50    0.74    --  107.75-125.00  30.00   56
 11  \w     87.00 112.00   0.50    0.74    --  107.75-125.00  30.00   50
 12  \w   -116.00 -31.00   0.50    0.18    --  -47.57  -8.00  39.00  170
 13  \w   -156.00 -84.00   0.50    0.74    -- -100.00  -8.00  39.00  144
 14  \w    -85.00 -41.00   0.50    0.18    --  -47.57 125.00 -90.00   88
 15  \w    -69.00 -36.00   0.50    0.74    -- -100.00  57.00 -90.00   66
 16  \w   -169.00-143.00   0.50    0.74    -- -100.00-125.00 150.00   52
 17  \w   -134.00-105.00   0.50    0.74    -- -100.00-125.00 150.00   58
 18  \w    -99.00 -64.00   0.50    0.74    -- -100.00-151.00  92.00   70
 19  \w   -154.00-104.00   0.50    0.74    -- -100.00-151.00  92.00  100
 20  \w   -167.00 -78.00   0.50    0.74    -- -100.00-131.00 -10.00  178
;
_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      0.0167347000
_diffrn_orient_matrix_UB_12      0.0592821000
_diffrn_orient_matrix_UB_13      0.0553882000
_diffrn_orient_matrix_UB_21      -0.0219231000
_diffrn_orient_matrix_UB_22      -0.1291018000
_diffrn_orient_matrix_UB_23      0.0255817000
_diffrn_orient_matrix_UB_31      0.2540714000
_diffrn_orient_matrix_UB_32      -0.0151334000
_diffrn_orient_matrix_UB_33      -0.0014936000
_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  0.0874
_diffrn_reflns_av_unetI/netI     0.0730
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.955
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            8138
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.932
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.421
_diffrn_reflns_theta_min         3.502
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.569
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.14061
_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    1.159
_exptl_crystal_description       block
_exptl_crystal_F_000             624
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.447
_refine_diff_density_min         -0.524
_refine_diff_density_rms         0.107
_refine_ls_abs_structure_details
;
 Flack x determined using 1142 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   1.068
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     194
_refine_ls_number_reflns         3260
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.068
_refine_ls_R_factor_all          0.0814
_refine_ls_R_factor_gt           0.0792
_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^)+(0.1538P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1914
_refine_ls_wR_factor_ref         0.1933
_reflns_Friedel_coverage         0.670
_reflns_Friedel_fraction_full    0.988
_reflns_Friedel_fraction_max     0.898
_reflns_number_gt                3072
_reflns_number_total             3260
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3sc00582h2.cif
_cod_data_source_block           chenxiaow-137-b_0830_auto
_cod_depositor_comments
'Adding full bibliography for 1568996--1569002.cif.'
_cod_database_code               1568999
_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:
 C003(H003), C005(H005), C006(H006)
2.b Secondary CH2 refined with riding coordinates:
 C00G(H00I,H00J), C00H(H00K,H00L)
2.c Aromatic/amide H refined with riding coordinates:
 C00A(H00A), C00B(H00B), C00C(H00C), C00D(H00D), C00E(H00E)
2.d X=CH2 refined with riding coordinates:
 C00I(H00M,H00N), C00K(H00R,H00S)
2.e Idealised Me refined as rotating group:
 C00F(H00F,H00G,H00H), C00J(H00O,H00P,H00Q), C00L(H00T,H00U,H00V)
2.f Idealised tetrahedral OH refined as rotating group:
 O001(H001)
;
_shelx_res_checksum              30008
_shelx_hkl_checksum              35872
_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 5.795
_oxdiff_exptl_absorpt_empirical_full_min 0.124