Anti-inflammatory Labdane Diterpenoids from Lagopsis supina.
Li, Hui; Li, Man-Man; Su, Xiao-Qin; Sun, Jing; Gu, Yu-Fan; Zeng, Ke-Wu; Zhang, Qian; Zhao, Yun-Fang; Ferreira, Daneel; Zjawiony, Jordan K.; Li, Jun; Tu, Peng-Fei; Journal of natural products 77 (2014) 1047–1053; doi:10.1021/np5001329

data_1514262
_publ_section_title
;
 Anti-inflammatory Labdane Diterpenoids from Lagopsis supina.
;
_journal_issue                   4
_journal_name_full               'Journal of natural products'
_journal_page_first              1047
_journal_page_last               1053
_journal_paper_doi               10.1021/np5001329
_journal_volume                  77
_journal_year                    2014
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C22 H34 O5'
_chemical_formula_sum            'C22 H34 O5'
_chemical_formula_weight         378.49
_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     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2013-09-04
_audit_creation_method
;
  Olex2 1.1
  (compiled 2011.02.15 svn.r1672, GUI svn.r3494)
;
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   10.48171(11)
_cell_length_b                   13.11257(16)
_cell_length_c                   30.7357(4)
_cell_measurement_reflns_used    8463
_cell_measurement_temperature    99.3
_cell_measurement_theta_max      71.7393
_cell_measurement_theta_min      3.3677
_cell_volume                     4224.38(9)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_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-97 (Sheldrick, 1997)'
_computing_structure_solution
'A short history of SHELX (Sheldrick, 2007)/Bruker'
_diffrn_ambient_temperature      99.3
_diffrn_detector_area_resol_mean 16.0971
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_details
;
  1 omega   -3.00   22.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -        0.0000   77.0000   60.0000 25

  2 omega  -27.00   36.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -        0.0000   77.0000 -156.0000 63

  3 omega  -57.00   20.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -42.5000   77.0000   60.0000 77

  4 omega   37.00  112.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       56.0000   77.0000 -120.0000 75

  5 omega   26.00  122.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       56.0000   77.0000  120.0000 96

  6 omega   87.00  175.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   77.0000 -180.0000 88

  7 omega  101.00  167.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   77.0000  150.0000 66

  8 omega   85.00  173.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   77.0000  -60.0000 88

  9 omega  129.00  161.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   77.0000   90.0000 32

 10 omega  106.00  176.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   77.0000   23.0000 70

 11 omega   90.00  116.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   77.0000   90.0000 26

 12 omega   93.00  174.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   77.0000   60.0000 81

 13 omega  105.00  163.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   77.0000  120.0000 58
;
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0156686000
_diffrn_orient_matrix_UB_12      -0.0760030000
_diffrn_orient_matrix_UB_13      -0.0378723000
_diffrn_orient_matrix_UB_21      0.1133189000
_diffrn_orient_matrix_UB_22      -0.0627099000
_diffrn_orient_matrix_UB_23      0.0174620000
_diffrn_orient_matrix_UB_31      -0.0922381000
_diffrn_orient_matrix_UB_32      -0.0640058000
_diffrn_orient_matrix_UB_33      0.0278125000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.5418
_diffrn_reflns_av_R_equivalents  0.0239
_diffrn_reflns_av_unetI/netI     0.0350
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       37
_diffrn_reflns_limit_l_min       -37
_diffrn_reflns_number            15627
_diffrn_reflns_theta_full        71.88
_diffrn_reflns_theta_max         71.88
_diffrn_reflns_theta_min         3.66
_diffrn_source                   'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.667
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.89638
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.190
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1648
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.260
_refine_diff_density_min         -0.217
_refine_diff_density_rms         0.042
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.09(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.017
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     501
_refine_ls_number_reflns         8123
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.017
_refine_ls_R_factor_all          0.0372
_refine_ls_R_factor_gt           0.0357
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0554P)^2^+0.6031P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0911
_refine_ls_wR_factor_ref         0.0925
_reflns_number_gt                7839
_reflns_number_total             8123
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            np5001329_si_002.cif
_cod_data_source_block           exp_1521
_cod_depositor_comments          'Adding full bibliography for 1514262.cif.'
_cod_original_cell_volume        4224.38(8)
_cod_database_code               1514262
_reflns_odcompleteness_completeness 99.95
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97