Anti-inflammatory Ursane- and Oleanane-Type Triterpenoids from Vitex negundo var. cannabifolia.
Li, Man-Man; Su, Xiao-Qin; Sun, Jing; Gu, Yu-Fan; Huang, Zheng; Zeng, Ke-Wu; Zhang, Qian; Zhao, Yun-Fang; Ferreira, Daneel; Zjawiony, Jordan K.; Li, Jun; Tu, Peng-Fei; Journal of natural products 77 (2014) 2248–2254; doi:10.1021/np500509q

data_1517804
_publ_section_title
;
 Anti-inflammatory Ursane- and Oleanane-Type Triterpenoids from Vitex
 negundo var. cannabifolia.
;
_journal_issue                   10
_journal_name_full               'Journal of natural products'
_journal_page_first              2248
_journal_page_last               2254
_journal_paper_doi               10.1021/np500509q
_journal_volume                  77
_journal_year                    2014
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C30 H46 O6, H2 O'
_chemical_formula_sum            'C30 H48 O7'
_chemical_formula_weight         520.68
_space_group_crystal_system      triclinic
_space_group_IT_number           1
_space_group_name_Hall           'P 1'
_space_group_name_H-M_alt        'P 1'
_symmetry_space_group_name_Hall  'P 1'
_symmetry_space_group_name_H-M   'P 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2013-10-10
_audit_creation_method
;
  Olex2 1.1
  (compiled 2011.02.15 svn.r1672, GUI svn.r3494)
;
_cell_angle_alpha                89.616(3)
_cell_angle_beta                 73.336(3)
_cell_angle_gamma                78.252(3)
_cell_formula_units_Z            4
_cell_length_a                   12.9465(4)
_cell_length_b                   14.7156(5)
_cell_length_c                   15.0171(5)
_cell_measurement_reflns_used    18502
_cell_measurement_temperature    97.5
_cell_measurement_theta_max      71.8527
_cell_measurement_theta_min      3.0739
_cell_volume                     2679.35(16)
_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      97.5
_diffrn_detector_area_resol_mean 16.0971
_diffrn_measured_fraction_theta_full 0.983
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measurement_details
;
  1 omega  -11.00   27.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  -77.0000  120.0000 38

  2 omega   26.00   68.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -        0.0000   77.0000 -120.0000 42

  3 omega  -28.00   22.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -        0.0000   77.0000 -120.0000 50

  4 omega   -9.00   67.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -        0.0000   77.0000   60.0000 76

  5 omega  -61.00  -12.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  -77.0000  120.0000 49

  6 omega  -34.00    0.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       22.0000  125.0000  -87.0000 34

  7 omega  -25.00    0.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       34.0000  127.0000  120.0000 25

  8 omega    1.00   26.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       42.0000   97.0000   42.0000 25

  9 omega  -23.00    3.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -42.5000  125.0000 -120.0000 26

 10 omega  -76.00    3.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -42.5000  125.0000  120.0000 79

 11 omega  -50.00   23.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -42.5000   45.0000  -90.0000 73

 12 omega  -89.00  -44.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -42.5000  125.0000 -120.0000 45

 13 omega   10.00   35.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       46.0000   88.0000 -131.0000 25

 14 omega    9.00   35.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       46.0000   89.0000  148.0000 26

 15 omega   15.00   40.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       50.0000   85.0000  -74.0000 25

 16 omega   15.00   40.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       50.0000   85.0000  -36.0000 25

 17 omega   15.00   40.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       50.0000   85.0000    8.0000 25

 18 omega   20.00   45.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       54.0000   84.0000   68.0000 25

 19 omega   22.00   47.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       54.0000   80.0000  -71.0000 25

 20 omega   20.00   45.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       54.0000   84.0000   32.0000 25

 21 omega   24.00   49.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       56.0000   80.0000  111.0000 25

 22 omega  -14.00   81.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       56.0000  -77.0000   60.0000 95

 23 omega    3.00   84.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       56.0000  -77.0000  -60.0000 81

 24 omega   28.00   64.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       58.0000   77.0000   11.0000 36

 25 omega   71.00  125.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       58.0000   77.0000  128.0000 54

 26 omega   28.00   55.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       58.0000   77.0000  128.0000 27

 27 omega   27.00  119.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       58.0000   78.0000   85.0000 92

 28 omega   91.00  128.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       58.0000   74.0000  158.0000 37

 29 omega   32.00   57.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       58.0000   74.0000  158.0000 25

 30 omega  101.00  127.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       58.0000   70.0000  -57.0000 26

 31 omega   67.00  104.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       58.0000   77.0000   11.0000 37

 32 omega   30.00   55.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       58.0000   75.0000 -169.0000 25

 33 omega   37.00   76.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       58.0000   70.0000  -57.0000 39

 34 omega   27.00  127.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       58.0000   79.0000 -112.0000 100

 35 omega   39.00  129.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       62.0000   66.0000  -62.0000 90

 36 omega   38.00  110.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       62.0000   67.0000 -150.0000 72

 37 omega   76.00  107.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       62.0000   66.0000   39.0000 31

 38 omega   39.00   74.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       62.0000   66.0000   39.0000 35

 39 omega   90.00  117.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   45.0000  150.0000 27

 40 omega   89.00  123.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   45.0000  -90.0000 34

 41 omega   82.00  149.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   77.0000  150.0000 67

 42 omega   82.00  108.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   77.0000 -120.0000 26

 43 omega  133.00  174.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   77.0000  -90.0000 41

 44 omega   89.00  172.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   45.0000  -30.0000 83

 45 omega   43.00  105.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -96.0000  -34.0000 62

 46 omega   82.00  150.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   77.0000 -150.0000 68

 47 omega   56.00  108.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -95.0000  156.0000 52

 48 omega   41.00  104.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000 -100.0000 -104.0000 63

 49 omega  123.00  178.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  111.0000  150.0000 55

 50 omega   43.00  122.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000 -127.0000  126.0000 79

 51 omega   82.00  164.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   77.0000    0.0000 82

 52 omega   82.00  108.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   77.0000  -60.0000 26

 53 omega   82.00  108.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   77.0000  -30.0000 26

 54 omega   83.00  108.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   77.0000  -90.0000 25

 55 omega   82.00  155.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   77.0000   60.0000 73

 56 omega   82.00  178.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   77.0000 -180.0000 96

 57 omega  123.00  175.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   77.0000 -120.0000 52

 58 omega   50.00   75.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000 -100.0000  133.0000 25

 59 omega   82.00  160.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   77.0000   90.0000 78

 60 omega   83.00  167.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   30.0000  -45.0000 84

 61 omega   82.00  166.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   77.0000   30.0000 84

 62 omega   89.00  121.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   45.0000    0.0000 32

 63 omega   55.00   97.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -45.0000 -150.0000 42

 64 omega   41.00   98.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -45.0000  120.0000 57

 65 omega  115.00  178.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   77.0000  120.0000 63

 66 omega   82.00  108.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   77.0000  120.0000 26
;
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0843914000
_diffrn_orient_matrix_UB_12      -0.0243954000
_diffrn_orient_matrix_UB_13      -0.0968307000
_diffrn_orient_matrix_UB_21      -0.0920739000
_diffrn_orient_matrix_UB_22      0.0336601000
_diffrn_orient_matrix_UB_23      -0.0460739000
_diffrn_orient_matrix_UB_31      0.0232804000
_diffrn_orient_matrix_UB_32      0.0986062000
_diffrn_orient_matrix_UB_33      -0.0018605000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.5418
_diffrn_reflns_av_R_equivalents  0.0319
_diffrn_reflns_av_unetI/netI     0.0403
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            36807
_diffrn_reflns_theta_full        71.99
_diffrn_reflns_theta_max         71.99
_diffrn_reflns_theta_min         3.08
_diffrn_source                   'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.725
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.91534
_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    1.291
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1136
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.50
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.772
_refine_diff_density_min         -0.617
_refine_diff_density_rms         0.072
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.01(11)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1373
_refine_ls_number_reflns         18200
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.027
_refine_ls_R_factor_all          0.0635
_refine_ls_R_factor_gt           0.0625
_refine_ls_shift/su_max          0.008
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.1221P)^2^+1.3249P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1654
_refine_ls_wR_factor_ref         0.1672
_reflns_number_gt                17731
_reflns_number_total             18200
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            np500509q_si_002.cif
_cod_data_source_block           exp_1579
_cod_depositor_comments          'Adding full bibliography for 1517804.cif.'
_cod_original_cell_volume        2679.36(15)
_cod_database_code               1517804
_reflns_odcompleteness_completeness 99.94
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97