Eremophilane-Type Sesquiterpenoids with Diverse Skeletons from Ligularia sagitta.
Chen, Jian-Jun; Chen, Chao-Jun; Yao, Xiao-Jun; Jin, Xiao-Jie; Gao, Kun; Journal of natural products 77 (2014) 1329–1335; doi:10.1021/np5003302

data_1516596
_publ_section_title
;
 Eremophilane-Type Sesquiterpenoids with Diverse Skeletons from Ligularia
 sagitta.
;
_journal_issue                   6
_journal_name_full               'Journal of natural products'
_journal_page_first              1329
_journal_page_last               1335
_journal_paper_doi               10.1021/np5003302
_journal_volume                  77
_journal_year                    2014
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C19 H26 O6'
_chemical_formula_sum            'C19 H26 O6'
_chemical_formula_weight         350.40
_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'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
_audit_creation_date             2013-01-28
_audit_creation_method
;
  Olex2 1.2
  (compiled Dec  5 2012 16:20:19, GUI svn.r4385)
;
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.1403(2)
_cell_length_b                   12.3986(3)
_cell_length_c                   15.0582(4)
_cell_measurement_reflns_used    7077
_cell_measurement_temperature    292.11(10)
_cell_measurement_theta_max      72.6290
_cell_measurement_theta_min      4.8060
_cell_volume                     1706.50(7)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET)
(compiled Dec  3 2012,18:21:49)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET)
(compiled Dec  3 2012,18:21:49)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET)
(compiled Dec  3 2012,18:21:49)
;
_computing_molecular_graphics
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement
;
SHELXL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution    'SUPERFLIP, J. Appl. Cryst. (2007) 40, 786-790'
_diffrn_ambient_temperature      292.11(10)
_diffrn_detector_area_resol_mean 16.0733
_diffrn_measured_fraction_theta_full 0.9679
_diffrn_measured_fraction_theta_max 0.9906
_diffrn_measurement_details
;
  1 omega   -9.00   67.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000   57.0000 -150.0000 76

  2 omega  -20.00   15.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000   57.0000 -180.0000 35

  3 omega  -70.00   13.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -58.0000   57.0000  -90.0000 83

  4 omega  -96.00  -11.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -58.0000  125.0000  -60.0000 85

  5 omega   87.00  129.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       58.0000   77.0000 -180.0000 42

  6 omega   26.00   51.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       58.0000   77.0000 -180.0000 25

  7 omega -138.00  -71.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -64.5000  -38.0000  120.0000 67

  8 omega   41.00   78.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      116.0000  -25.0000 -120.0000 37

  9 omega   64.00   90.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      116.0000  -25.0000 -180.0000 26

 10 omega   46.00   74.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      116.0000  -25.0000  -90.0000 28

 11 omega   53.00   78.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      116.0000  -91.0000  150.0000 25

 12 omega   42.00   73.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      116.0000 -111.0000    0.0000 31

 13 omega   89.00  116.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      116.0000 -111.0000    0.0000 27

 14 omega   50.00   86.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      116.0000  -77.0000  -30.0000 36

 15 omega  123.00  174.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      116.0000   50.0000  -30.0000 51

 16 omega   45.00   97.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      116.0000  -77.0000    0.0000 52

 17 omega   84.00  113.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      116.0000 -111.0000 -120.0000 29

 18 omega   83.00  177.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      116.0000   77.0000 -150.0000 94

 19 omega   79.00  107.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      116.0000 -111.0000  150.0000 28

 20 omega  111.00  137.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      116.0000  -77.0000    0.0000 26

 21 omega  140.00  166.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      116.0000   50.0000   60.0000 26

 22 omega   91.00  116.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      116.0000 -111.0000   60.0000 25

 23 omega   44.00   74.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      116.0000 -111.0000  150.0000 30

 24 omega  130.00  155.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      116.0000  -91.0000  150.0000 25

 25 omega  102.00  128.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      116.0000  178.0000  120.0000 26

 26 omega   57.00   82.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      116.0000  -24.0000   61.2978 25

 27 omega  102.00  136.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      116.0000  111.0000 -180.0000 34

 28 omega   66.00   91.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      116.0000  -38.0000 -150.0000 25

 29 omega  135.00  174.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      116.0000  111.0000    0.0000 39

 30 omega   50.00   76.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      116.0000  -38.0000  150.0000 26

 31 omega   42.00   68.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      116.0000  -10.0000 -123.0000 26

 32 omega  111.00  137.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      116.0000  -10.0000 -123.0000 26

 33 omega  125.00  150.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      116.0000  178.0000   90.0000 25

 34 omega  -82.00  -34.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  178.0000   30.0000 48

 35 omega  -71.00   24.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  -57.0000   60.0000 95

 36 omega  -91.00   14.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -58.0000   77.0000  150.0000 105

 37 omega -129.00  -34.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -58.0000  -57.0000   30.0000 95

 38 omega -130.00  -55.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -58.0000  -77.0000  -30.0000 75
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0199789000
_diffrn_orient_matrix_UB_12      0.1032558000
_diffrn_orient_matrix_UB_13      0.0557386000
_diffrn_orient_matrix_UB_21      -0.0149689000
_diffrn_orient_matrix_UB_22      0.0690551000
_diffrn_orient_matrix_UB_23      -0.0846966000
_diffrn_orient_matrix_UB_31      -0.1664884000
_diffrn_orient_matrix_UB_32      0.0061582000
_diffrn_orient_matrix_UB_33      0.0141659000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.5418
_diffrn_reflns_av_R_equivalents  0.0152
_diffrn_reflns_av_unetI/netI     0.0137
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            10415
_diffrn_reflns_theta_full        72.00
_diffrn_reflns_theta_max         72.54
_diffrn_reflns_theta_min         5.66
_diffrn_source                   'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.832
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.77461
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET)
(compiled Dec  3 2012,18:21:49)
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    1.364
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             752
_exptl_crystal_size_max          0.39
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.28
_refine_diff_density_max         0.276
_refine_diff_density_min         -0.187
_refine_diff_density_rms         0.034
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.05(16)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     240
_refine_ls_number_reflns         3358
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.045
_refine_ls_R_factor_all          0.0350
_refine_ls_R_factor_gt           0.0344
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0643P)^2^+0.2313P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0954
_refine_ls_wR_factor_ref         0.0962
_reflns_number_gt                3288
_reflns_number_total             3358
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            np5003302_si_002.cif
_cod_data_source_block           chengjj0125
_cod_depositor_comments          'Adding full bibliography for 1516596.cif.'
_cod_database_code               1516596
_reflns_odcompleteness_completeness 96.79
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     74.33
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  H1A of C1, {H2A,H2B} of C2, {H3A,H3B} of C3, H4 of C4, H6 of C6, {H9A,H9B}
  of C9, H12 of C12, {H16A,H16B} of C16, {H19B,H19A,H19D,H19C} of C19
 At 1.5 times of:
  H6B of O6B, H1 of O1, H2 of O2, H6A of O6A, {H13A,H13B,H13C} of C13, {H14A,
  H14B,H14C} of C14, {H15A,H15B,H15C} of C15
2. Others
 Fixed Sof: O6A(0.56) H6A(0.56) O6B(0.44) H6B(0.44) H19B(0.56) H19A(0.56)
 H19D(0.44) H19C(0.44)
3.a Ternary CH refined with riding coordinates:
 C1(H1A), C4(H4), C6(H6), C12(H12)
3.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C3(H3A,H3B), C9(H9A,H9B), C16(H16A,H16B), C19(H19B,H19A),
 C19(H19D,H19C)
3.c Tetrahedral OH refined with riding coordinates:
 O6A(H6A), O6B(H6B)
3.d Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C), C14(H14A,H14B,H14C), C15(H15A,H15B,H15C)
3.e Idealised tetrahedral OH refined as rotating group:
 O1(H1), O2(H2)
;