Isolation, Structure Elucidition, and Immunosuppressive Activity of Diterpenoids from Ligularia fischeri.
Gobu, Fekadu-Roge; Chen, Jian-Jun; Zeng, Jun; Wei, Wen-Jun; Wang, Wei-Feng; Lin, Chang-Jun; Gao, Kun; Journal of natural products 80 (2017) 2263–2268; doi:10.1021/acs.jnatprod.7b00198

data_1546954
_publ_section_title
;
 Isolation, Structure Elucidition, and Immunosuppressive Activity of
 Diterpenoids from Ligularia fischeri.
;
_journal_issue                   8
_journal_name_full               'Journal of natural products'
_journal_page_first              2263
_journal_page_last               2268
_journal_paper_doi               10.1021/acs.jnatprod.7b00198
_journal_volume                  80
_journal_year                    2017
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C18 H30 O2, C H4 O'
_chemical_formula_sum            'C19 H34 O3'
_chemical_formula_weight         310.46
_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   mixed
_atom_sites_solution_primary     direct
_audit_creation_date             2017-03-07
_audit_creation_method
;
Olex2 1.2
(compiled 2017.03.02 svn.r3394 for OlexSys, GUI svn.r5324)
;
_cell_angle_alpha                90
_cell_angle_beta                 92.726(6)
_cell_angle_gamma                90
_cell_formula_units_Z            6
_cell_length_a                   10.4703(8)
_cell_length_b                   8.0849(10)
_cell_length_c                   33.511(2)
_cell_measurement_reflns_used    2009
_cell_measurement_temperature    273.77(10)
_cell_measurement_theta_max      64.2760
_cell_measurement_theta_min      4.2130
_cell_volume                     2833.5(4)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_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    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      273.77(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0733
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.976
_diffrn_measured_fraction_theta_max 0.966
_diffrn_measurement_details
;
  1 omega   75.00  124.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -63.0000   60.0000 49

  2 omega   75.00  100.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   25.0000  -60.0000 25

  3 omega   82.00  178.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   38.0000  -60.0000 96

  4 omega  145.00  176.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   63.0000  -90.0000 31

  5 omega  119.00  178.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000 -150.0000 59

  6 omega  118.00  178.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000 -120.0000 60

  7 omega  116.00  178.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000 -180.0000 62

  8 omega   97.00  122.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000   57.0000  -60.0000 25

  9 omega   87.00  116.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000   77.0000 -120.0000 29

 10 omega   79.00  120.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000   77.0000  -90.0000 41

 11 omega   72.00  123.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000   57.0000    0.0000 51

 12 omega   85.00  111.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   48.0000 -101.3600 26

 13 omega   92.00  118.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   50.0000  -90.0000 26

 14 omega   89.00  116.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   50.0000 -150.0000 27

 15 omega   92.00  119.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   50.0000 -180.0000 27

 16 omega   86.00  113.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   63.0000 -150.0000 27

 17 omega   86.00  112.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   63.0000 -180.0000 26

 18 omega   85.00  111.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   66.0000 -162.4204 26

 19 omega   89.00  116.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   38.0000 -150.0000 27

 20 omega   86.00  113.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   63.0000  -90.0000 27

 21 omega   86.00  112.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   63.0000 -120.0000 26

 22 omega   86.00  115.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   44.0000 -111.1461 29

 23 omega   83.00  108.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   38.0000 -120.0000 25

 24 omega   82.00  108.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   38.0000  -90.0000 26

 25 omega   78.00  104.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000 -150.0000 26

 26 omega   78.00  105.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000 -120.0000 27

 27 omega   83.00  110.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   38.0000 -180.0000 27

 28 omega   78.00  104.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000 -180.0000 26

 29 omega   50.00   77.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000   57.0000  -60.0000 27

 30 omega   35.00   68.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000   38.0000  -30.0000 33

 31 omega   82.00  108.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   38.0000  150.0000 26

 32 omega   87.00  113.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   63.0000  150.0000 26

 33 omega  127.00  178.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000  150.0000 51

 34 omega  127.00  177.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   75.0000  133.7798 50

 35 omega  117.00  175.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000  120.0000 58

 36 omega   90.00  117.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   63.0000  120.0000 27

 37 omega   79.00  105.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   75.0000  133.7798 26

 38 omega   78.00  104.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000  150.0000 26

 39 omega   78.00  104.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000  120.0000 26

 40 omega   25.00   50.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000   77.0000  150.0000 25

 41 omega  -20.00   54.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000   57.0000   60.0000 74

 42 omega  -24.00   29.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000   38.0000  -30.0000 53

 43 omega   25.00   57.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000   77.0000 -120.0000 32

 44 omega   29.00   56.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000   77.0000 -180.0000 27

 45 omega   33.00   95.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000   57.0000 -180.0000 62

 46 omega   27.00  119.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000   77.0000 -150.0000 92

 47 omega   40.00   93.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -50.0000 -180.0000 53

 48 omega   57.00   82.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -111.0000 -120.0000 25
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0932407000
_diffrn_orient_matrix_UB_12      -0.0456592000
_diffrn_orient_matrix_UB_13      0.0352433000
_diffrn_orient_matrix_UB_21      0.1085016000
_diffrn_orient_matrix_UB_22      -0.0202458000
_diffrn_orient_matrix_UB_23      -0.0290797000
_diffrn_orient_matrix_UB_31      0.0350358000
_diffrn_orient_matrix_UB_32      0.1839068000
_diffrn_orient_matrix_UB_33      0.0055240000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0332
_diffrn_reflns_av_unetI/netI     0.0441
_diffrn_reflns_Laue_measured_fraction_full 0.976
_diffrn_reflns_Laue_measured_fraction_max 0.966
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       40
_diffrn_reflns_limit_l_min       -40
_diffrn_reflns_number            21927
_diffrn_reflns_point_group_measured_fraction_full 0.851
_diffrn_reflns_point_group_measured_fraction_max 0.837
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         69.913
_diffrn_reflns_theta_min         3.962
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.560
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.84191
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
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    1.092
_exptl_crystal_description       block
_exptl_crystal_F_000             1032
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.118
_refine_diff_density_min         -0.119
_refine_diff_density_rms         0.024
_refine_ls_abs_structure_details
;
 Flack x determined using 761 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.27(15)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.906
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     625
_refine_ls_number_reflns         8985
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.906
_refine_ls_R_factor_all          0.1313
_refine_ls_R_factor_gt           0.0454
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0645P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1200
_refine_ls_wR_factor_ref         0.1809
_reflns_Friedel_coverage         0.611
_reflns_Friedel_fraction_full    0.704
_reflns_Friedel_fraction_max     0.688
_reflns_number_gt                2720
_reflns_number_total             8985
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            np7b00198_si_003.cif
_cod_data_source_block           flf15b_4
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_absolute_configuration' value 'AD' changed to 'ad'
according to
/home/data/users/saulius/crontab/automatic-downloads/current/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 4973 2017-02-22 13:04:09Z antanas 
;
_cod_database_code               1546954
_shelx_shelxl_version_number     2014/7
_reflns_odcompleteness_completeness 97.62
_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:
 C21(H21), C26(H26), C28(H28), C3(H3A), C8(H8), C10(H10), C39(H39), C44(H44),
 C46(H46)
2.b Secondary CH2 refined with riding coordinates:
 C0AA(H0AA,H0AB), C1AA(H1AA,H1AB), C24(H24A,H24B), C25(H25A,H25B), C29(H29A,
 H29B), C30(H30A,H30B), C32(H32A,H32B), C1(H1A,H1B), C2(H2A,H2B), C6(H6A,H6B),
 C7(H7A,H7B), C11(H11A,H11B), C12(H12A,H12B), C14(H14A,H14B), C37(H37A,H37B),
 C38(H38A,H38B), C42(H42A,H42B), C43(H43A,H43B), C47(H47A,H47B), C48(H48A,H48B),
  C50(H50A,H50B)
2.c X=CH2 refined with riding coordinates:
 C34(H34A,H34B), C18(H18A,H18B), C52(H52A,H52B)
2.d Idealised Me refined as rotating group:
 C33(H33A,H33B,H33C), C35(H35A,H35B,H35C), C36(H36A,H36B,H36C), C17(H17A,H17B,
 H17C), C19(H19A,H19B,H19C), C20(H20A,H20B,H20C), C51(H51A,H51B,H51C), C53(H53A,
 H53B,H53C), C54(H54A,H54B,H54C), C55(H55A,H55B,H55C), C56(H56A,H56B,H56C),
 C57(H57A,H57B,H57C)
2.e Idealised tetrahedral OH refined as rotating group:
 O2(H2), O3(H3), O4(H4), O5(H5), O7(H7), O8(H8A)
;
_olex2_submission_special_instructions 'No special instructions were received'