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_1552686
_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 O6'
_chemical_formula_sum            'C20 H32 O6'
_chemical_formula_weight         368.46
_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   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2017-11-22
_audit_creation_method
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337)
;
_cell_angle_alpha                90.00
_cell_angle_beta                 100.3517(16)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   7.21196(13)
_cell_length_b                   11.84870(16)
_cell_length_c                   11.19881(17)
_cell_measurement_reflns_used    12299
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      72.3520
_cell_measurement_theta_min      3.7190
_cell_volume                     941.39(3)
_computing_cell_refinement       'CrysAlisPro 1.171.39.33c (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.33c (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.33c (Rigaku OD, 2017)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      293.15
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0355
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_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    -32.00  52.00   1.00    1.00    --   35.24 -57.00  30.00   84
  2  \w     19.00 103.00   1.00    1.00    --   35.24  57.00   0.00   84
  3  \w    -34.00  54.00   1.00    1.00    --   35.24 -37.00-150.00   88
  4  \w    -32.00  52.00   1.00    1.00    --   35.24 -57.00   0.00   84
  5  \w     18.00  89.00   1.00    1.00    --   35.24-125.00-180.00   71
  6  \w      9.00 103.00   1.00    1.00    --   35.24  77.00-120.00   94
  7  \w    -36.00  65.00   1.00    1.00    --   35.24 -19.00  60.00  101
  8  \w     -8.00  72.00   1.00    1.00    --   35.24 -95.00 -18.00   80
  9  \w     57.00 150.00   1.00    1.00    --  108.00 178.00 -30.00   93
 10  \w    100.00 178.00   1.00    1.00    --  108.00 111.00  60.00   78
 11  \w     38.00 116.00   1.00    1.00    --  108.00-111.00  60.00   78
 12  \w     40.00 135.00   1.00    1.00    --  108.00 -77.00-120.00   95
 13  \w     38.00 129.00   1.00    1.00    --  108.00 -30.00  60.00   91
 14  \w     40.00 135.00   1.00    1.00    --  108.00 -77.00  60.00   95
 15  \w     38.00 116.00   1.00    1.00    --  108.00-111.00-150.00   78
 16  \w     91.00 176.00   1.00    1.00    --  108.00  45.00-180.00   85
 17  \w     41.00 126.00   1.00    1.00    --  108.00 -61.00   0.00   85
 18  \w     90.00 175.00   1.00    1.00    --  108.00  61.00-150.00   85
 19  \w     38.00 129.00   1.00    1.00    --  108.00 -30.00-120.00   91
 20  \w     39.00 177.00   1.00    1.00    --  108.00   0.00 -60.00  138
 21  \w     16.00 104.00   1.00    1.00    --   35.24  37.00 120.00   88
 22  \w      9.00 103.00   1.00    1.00    --   35.24  77.00 -60.00   94
 23  \w      9.00 103.00   1.00    1.00    --   35.24  77.00  30.00   94
 24  \w    -32.00  62.00   1.00    1.00    --   35.24 -77.00-150.00   94
 25  \w      9.00 103.00   1.00    1.00    --   35.24  77.00-180.00   94
 26  \w     19.00 103.00   1.00    1.00    --   35.24  57.00-180.00   84
 27  \w      9.00 103.00   1.00    1.00    --   35.24  77.00 120.00   94
 28  \w     81.00 176.00   1.00    1.00    --  108.00  77.00  60.00   95
 29  \w     81.00 176.00   1.00    1.00    --  108.00  77.00-120.00   95
 30  \w     81.00 176.00   1.00    1.00    --  108.00  77.00 -90.00   95
 31  \w     81.00 176.00   1.00    1.00    --  108.00  77.00 120.00   95
 32  \w     81.00 176.00   1.00    1.00    --  108.00  77.00 -30.00   95
 33  \w     90.00 175.00   1.00    1.00    --  108.00  61.00 -30.00   85
 34  \w     81.00 176.00   1.00    1.00    --  108.00  77.00 -60.00   95
 35  \w     91.00 176.00   1.00    1.00    --  108.00  45.00-150.00   85
 36  \w     87.00 178.00   1.00    1.00    --  108.00  30.00 120.00   91
 37  \w     81.00 176.00   1.00    1.00    --  108.00  77.00   0.00   95
 38  \w     87.00 178.00   1.00    1.00    --  108.00  30.00-180.00   91
 39  \w     81.00 176.00   1.00    1.00    --  108.00  77.00  30.00   95
 40  \w     81.00 176.00   1.00    1.00    --  108.00  77.00  90.00   95
 41  \w     70.00 178.00   1.00    1.00    --  108.00  15.00  60.00  108
 42  \w    -32.00  52.00   1.00    1.00    --   35.24 -57.00 -90.00   84
 43  \w     19.00 103.00   1.00    1.00    --   35.24  57.00-150.00   84
 44  \w     19.00 103.00   1.00    1.00    --   35.24  57.00 120.00   84
 45  \w      9.00 103.00   1.00    1.00    --   35.24  77.00   0.00   94
 46  \w     -2.00  23.00   1.00    1.00    --   35.74  96.00  31.04   25
 47  \w     43.00  69.00   1.00    1.00    --   35.74  77.00 -90.00   26
 48  \w     87.00 113.00   1.00    1.00    --  108.00  30.00 -60.00   26
 49  \w     87.00 113.00   1.00    1.00    --  108.00  30.00 150.00   26
 50  \w     90.00 115.00   1.00    1.00    --  108.00  61.00  30.00   25
 51  \w     79.00 105.00   1.00    1.00    --  108.00 -94.00 -60.00   26
 52  \w    141.00 167.00   1.00    1.00    --  108.00  77.00-180.00   26
 53  \w     90.00 116.00   1.00    1.00    --  108.00  61.00  60.00   26
 54  \w     81.00 107.00   1.00    1.00    --  108.00  77.00-150.00   26
 55  \w     82.00 108.00   1.00    1.00    --  108.00  77.00 150.00   26
 56  \w     90.00 116.00   1.00    1.00    --  108.00  61.00-120.00   26
 57  \w     90.00 115.00   1.00    1.00    --  108.00  61.00   0.00   25
 58  \w     84.00 110.00   1.00    1.00    --  108.00  77.00-180.00   26
 59  \w     91.00 117.00   1.00    1.00    --  108.00  61.00 -90.00   26
 60  \w     92.00 118.00   1.00    1.00    --  108.00  30.00  90.00   26
 61  \w     90.00 116.00   1.00    1.00    --  108.00  61.00 150.00   26
 62  \w     87.00 112.00   1.00    1.00    --  108.00  30.00   0.00   25
 63  \w     71.00  97.00   1.00    1.00    --  108.00  15.00 -60.00   26
 64  \w     90.00 116.00   1.00    1.00    --  108.00  30.00 -30.00   26
 65  \w     90.00 115.00   1.00    1.00    --  108.00  61.00-180.00   25
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1046144000
_diffrn_orient_matrix_UB_12      0.1005517000
_diffrn_orient_matrix_UB_13      0.0445306000
_diffrn_orient_matrix_UB_21      0.0210831000
_diffrn_orient_matrix_UB_22      0.0668370000
_diffrn_orient_matrix_UB_23      -0.1148289000
_diffrn_orient_matrix_UB_31      -0.1891069000
_diffrn_orient_matrix_UB_32      -0.0481871000
_diffrn_orient_matrix_UB_33      -0.0662828000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0295
_diffrn_reflns_av_unetI/netI     0.0153
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            18702
_diffrn_reflns_theta_full        66.60
_diffrn_reflns_theta_max         66.60
_diffrn_reflns_theta_min         4.01
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.774
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.51973
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.33c (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear whiteish white'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   whiteish
_exptl_crystal_colour_primary    white
_exptl_crystal_density_diffrn    1.300
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             400
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.21
_refine_diff_density_max         0.264
_refine_diff_density_min         -0.211
_refine_diff_density_rms         0.045
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.01(15)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     250
_refine_ls_number_reflns         3345
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.044
_refine_ls_R_factor_all          0.0404
_refine_ls_R_factor_gt           0.0401
_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^)+(0.0834P)^2^+0.0981P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1067
_refine_ls_wR_factor_ref         0.1071
_reflns_number_gt                3309
_reflns_number_total             3345
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            np9b00095_si_008.cif
_cod_data_source_block           171120_ygm_sn4_61_6
_cod_database_code               1552686
_chemical_oxdiff_formula         'C H O'
_reflns_odcompleteness_completeness 100.00
_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:
 C3(H3A), C1(H1A), C2(H2A), C6(H6A), C9(H9)
2.b Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B), C15(H15A,H15B), C14(H14A,H14B), C11(H11A,H11B), C12(H12A,H12B)
2.c X=CH2 refined with riding coordinates:
 C20(H20A,H20B)
2.d Idealised Me refined as rotating group:
 C19(H19A,H19B,H19C), C18(H18A,H18B,H18C), C17(H17A,H17B,H17C)
2.e Idealised tetrahedral OH refined as rotating group:
 O1(H1), O3(H3), O6(H6), O4(H4)
;
_olex2_date_sample_data_collection 2017-11-20
_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 1.992
_oxdiff_exptl_absorpt_empirical_full_min 0.636