Determination of the Absolute Configuration of Khellactone Esters from Peucedanum japonicum Roots.
Hong, Min Jee; Kim, Jinwoong; Journal of natural products 80 (2017) 1354–1360; doi:10.1021/acs.jnatprod.6b00947

data_1545738
_publ_section_title
;
 Determination of the Absolute Configuration of Khellactone Esters from
 Peucedanum japonicum Roots.
;
_journal_issue                   5
_journal_name_full               'Journal of natural products'
_journal_page_first              1354
_journal_page_last               1360
_journal_paper_doi               10.1021/acs.jnatprod.6b00947
_journal_volume                  80
_journal_year                    2017
_chemical_absolute_configuration unk
_chemical_formula_moiety         'C21 H22 O7'
_chemical_formula_sum            'C21 H22 O7'
_chemical_formula_weight         386.38
_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'
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2016-04-15
_audit_creation_method
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_cell_angle_alpha                90
_cell_angle_beta                 103.8888(13)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   9.68785(12)
_cell_length_b                   6.62844(9)
_cell_length_c                   15.2024(2)
_cell_measurement_reflns_used    10652
_cell_measurement_temperature    100.0(2)
_cell_measurement_theta_max      76.2990
_cell_measurement_theta_min      4.6770
_cell_volume                     947.69(2)
_computing_cell_refinement       'CrysAlisPro 1.171.38.41r (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.41r (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41r (Rigaku OD, 2015)'
_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      100.0(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2262
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.992
_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    -69.00  32.00   1.00    1.00    --  -41.24  57.00  90.00  101
  2  \w    -69.00  32.00   1.00    1.00    --  -41.24  57.00-150.00  101
  3  \w     23.00  97.00   1.00    1.00    --   41.24-125.00-180.00   74
  4  \w      1.00  82.00   1.00    1.00    --   41.24 -99.00-150.00   81
  5  \w     39.00 138.00   1.00    1.00    --  112.00 -45.00 -90.00   99
  6  \w     36.00 116.00   1.00    1.00    --  112.00-111.00 -60.00   80
  7  \w     86.00 178.00   1.00    1.00    --  112.00  45.00-150.00   92
  8  \w     36.00 140.00   1.00    1.00    --  112.00 -30.00  30.00  104
  9  \w     86.00 178.00   1.00    1.00    --  112.00  45.00-120.00   92
 10  \w    100.00 178.00   1.00    1.00    --  112.00 111.00  90.00   78
 11  \w    100.00 178.00   1.00    1.00    --  112.00 111.00  60.00   78
 12  \w     36.00 116.00   1.00    1.00    --  112.00-111.00  30.00   80
 13  \w     29.00 109.00   1.00    1.00    --  112.00 -94.00  90.00   80
 14  \w     40.00 141.00   1.00    1.00    --  112.00 -61.00  60.00  101
 15  \w   -113.00 -13.00   1.00    1.00    --  -41.24 -57.00 -60.00  100
 16  \w   -113.00 -13.00   1.00    1.00    --  -41.24 -57.00 120.00  100
 17  \w      9.00  94.00   1.00    1.00    --   41.24  77.00  60.00   85
 18  \w     17.00  42.00   1.00    2.10    --   50.00  80.00 -45.70   25
 19  \w     24.00  75.00   1.00    2.10    --   54.00  77.00 -21.40   51
 20  \w    120.00 146.00   1.00    1.59    --  112.00 -15.00 -30.00   26
 21  \w    153.00 178.00   1.00    1.59    --  112.00  77.00 -60.00   25
 22  \w     83.00 123.00   1.00    1.59    --  112.00  61.00 -90.00   40
 23  \w     81.00 120.00   1.00    1.59    --  112.00  77.00 -30.00   39
 24  \w     79.00 105.00   1.00    1.59    --  112.00  77.00-120.00   26
 25  \w     87.00 127.00   1.00    1.59    --  112.00  45.00 -30.00   40
 26  \w     81.00 107.00   1.00    1.59    --  112.00  77.00 -90.00   26
 27  \w    142.00 168.00   1.00    1.59    --  112.00  77.00 -30.00   26
 28  \w     44.00  70.00   1.00    1.59    --  112.00 -94.00  60.00   26
 29  \w     84.00 110.00   1.00    1.59    --  112.00  61.00 -30.00   26
 30  \w     84.00 110.00   1.00    1.59    --  112.00  61.00-120.00   26
 31  \w     85.00 113.00   1.00    1.59    --  112.00  61.00 -60.00   28
 32  \w     79.00 104.00   1.00    1.59    --  112.00  77.00 -60.00   25
 33  \w     88.00 123.00   1.00    1.59    --  112.00  45.00 -90.00   35
 34  \w     88.00 163.00   1.00    1.59    --  112.00  45.00 -60.00   75
 35  \w     31.00  57.00   1.00    1.59    --  112.00 -15.00 -30.00   26
 36  \w     40.00  66.00   1.00    2.10    --   62.00  75.00 -87.04   26
 37  \w     42.00  68.00   1.00    2.10    --   70.00  71.00  27.96   26
 38  \w     23.00  98.00   1.00    2.10    --   41.49-125.00   0.00   75
 39  \w     11.00  38.00   1.00    2.10    --   46.00  84.00 174.08   27
 40  \w     12.00  45.00   1.00    2.10    --   46.00  82.00-113.96   33
 41  \w     20.00  46.00   1.00    2.10    --   54.00  81.00 -76.91   26
 42  \w     20.00  46.00   1.00    2.10    --   54.00  81.00-170.94   26
 43  \w     20.00  46.00   1.00    2.10    --   54.00  81.00  85.00   26
 44  \w     30.00 137.00   1.00    2.10    --   62.00  75.00-144.57  107
 45  \w     34.00 141.00   1.00    2.10    --   66.00  75.00  92.32  107
 46  \w     39.00 144.00   1.00    2.10    --   70.00  71.00  27.96  105
 47  \w     42.00 150.00   1.00    2.10    --   74.00  76.00 167.39  108
 48  \w     83.00 178.00   1.00    1.59    --  112.00  61.00 150.00   95
 49  \w     36.00 116.00   1.00    1.59    --  112.00-111.00-120.00   80
 50  \w     59.00 178.00   1.00    1.59    --  112.00  15.00 150.00  119
 51  \w     79.00 118.00   1.00    1.59    --  112.00  77.00  30.00   39
 52  \w     86.00 178.00   1.00    1.59    --  112.00  45.00  30.00   92
 53  \w     44.00  70.00   1.00    2.10    --   74.00  70.00 -18.99   26
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1562154000
_diffrn_orient_matrix_UB_12      -0.0431339000
_diffrn_orient_matrix_UB_13      -0.0480658000
_diffrn_orient_matrix_UB_21      0.0211600000
_diffrn_orient_matrix_UB_22      0.1071066000
_diffrn_orient_matrix_UB_23      -0.0856955000
_diffrn_orient_matrix_UB_31      0.0446478000
_diffrn_orient_matrix_UB_32      -0.2016789000
_diffrn_orient_matrix_UB_33      -0.0352874000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0347
_diffrn_reflns_av_unetI/netI     0.0220
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            19091
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.976
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.494
_diffrn_reflns_theta_min         4.702
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.851
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.59257
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.41r (Rigaku Oxford Diffraction, 2015)
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    1.354
_exptl_crystal_description       block
_exptl_crystal_F_000             408
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.059
_exptl_crystal_size_min          0.024
_refine_diff_density_max         0.166
_refine_diff_density_min         -0.199
_refine_diff_density_rms         0.038
_refine_ls_abs_structure_details
;
 Flack x determined using 1630 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.03(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     258
_refine_ls_number_reflns         3883
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.062
_refine_ls_R_factor_all          0.0287
_refine_ls_R_factor_gt           0.0276
_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^)+(0.0412P)^2^+0.0772P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0705
_refine_ls_wR_factor_ref         0.0715
_reflns_Friedel_coverage         0.804
_reflns_Friedel_fraction_full    0.984
_reflns_Friedel_fraction_max     0.956
_reflns_number_gt                3759
_reflns_number_total             3883
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            np6b00947_si_002.cif
_cod_data_source_block           isosamidin
_cod_depositor_comments          'Adding full bibliography for 1545738.cif.'
_cod_database_code               1545738
_chemical_oxdiff_formula         C21H22O7
_reflns_odcompleteness_completeness 99.91
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     74.33
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C3'(H3'), C4'(H4')
2.b Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5), C6(H6), C3(H3), C2"'(H2"')
2.c Idealised Me refined as rotating group:
 C6'(H6'A,H6'B,H6'C), C5"'(H5"A,H5"B,H5"C), C4"'(H4"A,H4"B,H4"C), C2"(H2"A,
 H2"B,H2"C), C5'(H5'A,H5'B,H5'C)
;
_shelx_shelxl_version_number     2014/7
_olex2_date_sample_data_collection 2016-04-14
_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 1.548
_oxdiff_exptl_absorpt_empirical_full_min 0.574