Antinociceptive Diterpenoids from the Leaves and Twigs of Rhododendron decorum.
Zhu, Yu-Xun; Zhang, Zhao-Xin; Yan, Hui-Min; Lu, Di; Zhang, Huan-Ping; Li, Li; Liu, Yun-Bao; Li, Yong; Journal of natural products 81 (2018) 1183–1192; doi:10.1021/acs.jnatprod.7b00941

data_1553327
_publ_section_title
;
 Antinociceptive Diterpenoids from the Leaves and Twigs of Rhododendron
 decorum.
;
_journal_issue                   5
_journal_name_full               'Journal of natural products'
_journal_page_first              1183
_journal_page_last               1192
_journal_paper_doi               10.1021/acs.jnatprod.7b00941
_journal_volume                  81
_journal_year                    2018
_chemical_formula_moiety         'C20 H32 O4, H2 O'
_chemical_formula_sum            'C20 H34 O5'
_chemical_formula_weight         354.47
_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'
_atom_sites_solution_hydrogens   mixed
_audit_creation_date             2017-04-25
_audit_creation_method
;
  Olex2 1.1
  (compiled 2011.02.15 svn.r1672, GUI svn.r3494)
;
_cell_angle_alpha                90
_cell_angle_beta                 112.565(10)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   6.6038(6)
_cell_length_b                   20.8285(14)
_cell_length_c                   7.1958(6)
_cell_measurement_reflns_used    3300
_cell_measurement_temperature    105.5
_cell_measurement_theta_max      71.2463
_cell_measurement_theta_min      4.2424
_cell_volume                     913.99(14)
_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-2014/7 (Sheldrick, 2014)'
_computing_structure_solution
'A short history of SHELX (Sheldrick, 2007)/Bruker'
_diffrn_ambient_temperature      105.5
_diffrn_detector_area_resol_mean 16.0971
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measurement_details
;
  1 omega    6.00   60.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       -8.5000   45.0000   90.0000 54

  2 omega   19.00  103.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       36.7919   77.0000  -90.0000 84

  3 omega   13.00   78.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       36.7919 -109.0000   84.0000 65

  4 omega  -27.00   64.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       36.7919  -77.0000  150.0000 91

  5 omega  -28.00   18.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       36.7919  -37.0000   30.0000 46

  6 omega   22.00   47.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       36.7919  -37.0000   30.0000 25

  7 omega  -10.00   18.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       36.7919  -37.0000 -180.0000 28

  8 omega   12.00  101.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       36.7919   77.0000    0.0000 89

  9 omega   56.00   81.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -77.0000    0.0000 25

 10 omega  147.00  175.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  111.0000  -30.0000 28

 11 omega   51.00   96.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000 -150.0000 45

 12 omega   51.00   98.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000  120.0000 47

 13 omega   46.00   92.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000   30.0000 46

 14 omega   48.00  144.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -15.0000 -120.0000 96

 15 omega  119.00  145.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  111.0000 -150.0000 26

 16 omega   73.00  132.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -77.0000 -150.0000 59

 17 omega  124.00  176.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   45.0000 -150.0000 52

 18 omega   38.00  115.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -109.0000  178.0000 77

 19 omega   38.00  142.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -15.0000   60.0000 104

 20 omega   38.00  101.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -109.0000   84.0000 63

 21 omega   40.00   98.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000  -60.0000 58

 22 omega   45.00   77.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000 -180.0000 32

 23 omega  103.00  152.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   45.0000  -90.0000 49

 24 omega   85.00  113.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -108.0000  -56.0000 28
;
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.1548198000
_diffrn_orient_matrix_UB_12      0.0502309000
_diffrn_orient_matrix_UB_13      0.1403620000
_diffrn_orient_matrix_UB_21      -0.1791449000
_diffrn_orient_matrix_UB_22      0.0516022000
_diffrn_orient_matrix_UB_23      -0.0843620000
_diffrn_orient_matrix_UB_31      -0.0887291000
_diffrn_orient_matrix_UB_32      -0.0165509000
_diffrn_orient_matrix_UB_33      0.1637392000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.5418
_diffrn_reflns_av_R_equivalents  0.0258
_diffrn_reflns_av_unetI/netI     0.0368
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -5
_diffrn_reflns_number            5732
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.969
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         71.406
_diffrn_reflns_theta_min         4.245
_diffrn_source                   'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.731
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.88117
_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    1.288
_exptl_crystal_F_000             388
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.350
_exptl_crystal_size_min          0.250
_refine_diff_density_max         0.239
_refine_diff_density_min         -0.264
_refine_diff_density_rms         0.070
_refine_ls_abs_structure_details
;
 Flack x determined using 1556 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.08(13)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.076
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     239
_refine_ls_number_reflns         3442
_refine_ls_number_restraints     4
_refine_ls_restrained_S_all      1.076
_refine_ls_R_factor_all          0.0386
_refine_ls_R_factor_gt           0.0381
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0696P)^2^+0.0387P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1001
_refine_ls_wR_factor_ref         0.1012
_reflns_Friedel_coverage         0.913
_reflns_Friedel_fraction_full    0.991
_reflns_Friedel_fraction_max     0.953
_reflns_number_gt                3395
_reflns_number_total             3442
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            np7b00941_si_002.cif
_cod_data_source_block           exp_4910
_cod_database_code               1553327
_reflns_odcompleteness_completeness 99.94
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_shelx_estimated_absorpt_t_max   0.838
_shelx_estimated_absorpt_t_min   0.759
_shelx_hkl_checksum              27507
_shelx_res_checksum              41909
_shelx_shelxl_version_number     2014/7