Anti-inflammatory Labdane Diterpenoids from Leonurus macranthus.
Huang, Zheng; Zhu, Zhi-Xiang; Li, Yue-Ting; Pang, Dao-Ran; Zheng, Jiao; Zhang, Qian; Zhao, Yun-Fang; Ferreira, Daneel; Zjawiony, Jordan K.; Tu, Peng-Fei; Li, Jun; Journal of natural products 78 (2015) 2276–2285; doi:10.1021/acs.jnatprod.5b00635

data_1530687
_publ_section_title
;
 Anti-inflammatory Labdane Diterpenoids from Leonurus macranthus.
;
_journal_issue                   9
_journal_name_full               'Journal of natural products'
_journal_page_first              2276
_journal_page_last               2285
_journal_paper_doi               10.1021/acs.jnatprod.5b00635
_journal_volume                  78
_journal_year                    2015
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C26 H40 O9'
_chemical_formula_sum            'C26 H40 O9'
_chemical_formula_weight         496.58
_chemical_melting_point          159
_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             2014-10-20
_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            4
_cell_length_a                   7.9069(4)
_cell_length_b                   8.1826(3)
_cell_length_c                   38.9732(16)
_cell_measurement_reflns_used    3999
_cell_measurement_temperature    103.5
_cell_measurement_theta_max      70.8093
_cell_measurement_theta_min      4.5351
_cell_volume                     2521.53(19)
_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      103.5
_diffrn_detector_area_resol_mean 16.0971
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_details
;
  1 omega  -47.00  -19.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       -3.5000  111.0000  -60.0000 28

  2 omega   24.00   80.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       36.8122   73.0000 -124.0000 56

  3 omega   18.00  102.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       36.8122   77.0000   30.0000 84

  4 omega  -28.00   42.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       36.8122  -37.0000 -120.0000 70

  5 omega  -21.00   32.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       36.8122  -77.0000 -120.0000 53

  6 omega   94.00  120.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   45.0000 -150.0000 26

  7 omega   84.00  142.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   72.0000  113.0000 58

  8 omega  104.00  176.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   45.0000  -30.0000 72

  9 omega   40.00   69.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000  120.0000 29

 10 omega   40.00   80.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000 -120.0000 40

 11 omega   91.00  126.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   45.0000 -120.0000 35

 12 omega  132.00  159.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   45.0000 -120.0000 27

 13 omega  100.00  172.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  111.0000 -180.0000 72

 14 omega   87.00  172.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000  -90.0000 85
;
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0547386000
_diffrn_orient_matrix_UB_12      -0.1505579000
_diffrn_orient_matrix_UB_13      0.0210807000
_diffrn_orient_matrix_UB_21      0.1535142000
_diffrn_orient_matrix_UB_22      -0.0236358000
_diffrn_orient_matrix_UB_23      -0.0238442000
_diffrn_orient_matrix_UB_31      0.1068293000
_diffrn_orient_matrix_UB_32      0.1104727000
_diffrn_orient_matrix_UB_33      0.0234796000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.5418
_diffrn_reflns_av_R_equivalents  0.0237
_diffrn_reflns_av_unetI/netI     0.0340
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       47
_diffrn_reflns_limit_l_min       -46
_diffrn_reflns_number            8605
_diffrn_reflns_theta_full        70.92
_diffrn_reflns_theta_max         70.92
_diffrn_reflns_theta_min         4.54
_diffrn_source                   'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.809
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.90043
_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_colour            colorless
_exptl_crystal_density_diffrn    1.308
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             1072
_exptl_crystal_size_max          0.55
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.25
_refine_diff_density_max         0.226
_refine_diff_density_min         -0.300
_refine_diff_density_rms         0.052
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.02(14)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     324
_refine_ls_number_reflns         4743
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.042
_refine_ls_R_factor_all          0.0380
_refine_ls_R_factor_gt           0.0367
_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^)+(0.0571P)^2^+0.3027P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0935
_refine_ls_wR_factor_ref         0.0947
_reflns_number_gt                4584
_reflns_number_total             4743
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            np5b00635_si_002.cif
_cod_data_source_block           exp_2437
_cod_depositor_comments          'Adding full bibliography for 1530687.cif.'
_cod_original_cell_volume        2521.52(19)
_cod_database_code               1530687
_reflns_odcompleteness_completeness 99.89
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97