Grayanane Diterpenoids from the Leaves of <i>Rhododendron auriculatum</i> and Their Analgesic Activities.
Sun, Na; Zheng, Guijuan; He, Meijun; Feng, Yuanyuan; Liu, Junjun; Wang, Meicheng; Zhang, Hanqi; Zhou, Junfei; Yao, Guangmin; Journal of natural products 82 (2019) 1849–1860; doi:10.1021/acs.jnatprod.9b00095

data_1552687
_publ_section_title
;
 Grayanane Diterpenoids from the Leaves of <i>Rhododendron auriculatum</i>
 and Their Analgesic Activities.
;
_journal_issue                   7
_journal_name_full               'Journal of natural products'
_journal_page_first              1849
_journal_page_last               1860
_journal_paper_doi               10.1021/acs.jnatprod.9b00095
_journal_volume                  82
_journal_year                    2019
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C20 H32 O4'
_chemical_formula_sum            'C20 H32 O4'
_chemical_formula_weight         336.45
_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'
_atom_sites_solution_hydrogens   mixed
_audit_creation_date             2017-06-24
_audit_creation_method
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.18422(8)
_cell_length_b                   9.88369(10)
_cell_length_c                   24.9753(3)
_cell_measurement_reflns_used    6617
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      73.3270
_cell_measurement_theta_min      5.3590
_cell_volume                     1773.41(3)
_computing_cell_refinement       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
--------------------------------------------------------------------------
  1  \w   -117.00 -14.00   1.00    1.00    --  -40.46 -37.00  90.00  103
  2  \w   -117.00 -14.00   1.00    1.00    --  -40.46 -37.00-150.00  103
  3  \w      1.00  82.00   1.00    1.00    --   40.46 -99.00-180.00   81
  4  \w     23.00 109.00   1.00    1.00    --  107.48 -94.00 -60.00   86
  5  \w     23.00 109.00   1.00    1.00    --  107.48 -94.00  90.00   86
  6  \w     30.00 138.00   1.00    1.00    --  107.48 -30.00 120.00  108
  7  \w     29.00 141.00   1.00    1.00    --  107.48 -77.00 150.00  112
  8  \w    100.00 171.00   1.00    1.00    --  107.48 111.00  90.00   71
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0148147000
_diffrn_orient_matrix_UB_12      -0.0631441000
_diffrn_orient_matrix_UB_13      -0.0562233000
_diffrn_orient_matrix_UB_21      0.0655482000
_diffrn_orient_matrix_UB_22      0.1369938000
_diffrn_orient_matrix_UB_23      -0.0226170000
_diffrn_orient_matrix_UB_31      0.2036210000
_diffrn_orient_matrix_UB_32      -0.0394650000
_diffrn_orient_matrix_UB_33      0.0114089000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0180
_diffrn_reflns_av_unetI/netI     0.0210
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            7630
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.976
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.508
_diffrn_reflns_theta_min         3.539
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.685
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.67666
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.260
_exptl_crystal_description       block
_exptl_crystal_F_000             736
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.179
_refine_diff_density_min         -0.190
_refine_diff_density_rms         0.050
_refine_ls_abs_structure_details
;
 Flack x determined using 1379 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.05(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.077
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     235
_refine_ls_number_reflns         3473
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.077
_refine_ls_R_factor_all          0.0316
_refine_ls_R_factor_gt           0.0311
_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^)+(0.0481P)^2^+0.2325P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0786
_refine_ls_wR_factor_ref         0.0789
_reflns_Friedel_coverage         0.706
_reflns_Friedel_fraction_full    0.996
_reflns_Friedel_fraction_max     0.963
_reflns_number_gt                3439
_reflns_number_total             3473
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            np9b00095_si_003.cif
_cod_data_source_block           sn4-28-7
_cod_database_code               1552687
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_max   0.929
_shelx_estimated_absorpt_t_min   0.887
_reflns_odcompleteness_completeness 99.89
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C6(H6), C1(H1A), C3(H3A), C9(H9), C13(H13)
2.b Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B), C15(H15A,H15B), C14(H14A,H14B), C11(H11A,H11B), C12(H12A,H12B),
 C2(H2A,H2B)
2.c Idealised Me refined as rotating group:
 C18(H18A,H18B,H18C), C19(H19A,H19B,H19C), C17(H17A,H17B,H17C)
2.d Idealised tetrahedral OH refined as rotating group:
 O2(H2), O1(H1), O4(H4)
;
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.634
_oxdiff_exptl_absorpt_empirical_full_min 0.438