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_1552689
_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 unk
_chemical_formula_moiety         'C20 H32 O5'
_chemical_formula_sum            'C20 H32 O5'
_chemical_formula_weight         352.45
_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
_atom_sites_solution_primary     dual
_audit_creation_date             2018-05-10
_audit_creation_method
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5492)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.46660(10)
_cell_length_b                   9.33390(10)
_cell_length_c                   24.8537(2)
_cell_measurement_reflns_used    11431
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      73.5390
_cell_measurement_theta_min      3.5590
_cell_volume                     1732.12(3)
_computing_cell_refinement       'CrysAlisPro 1.171.39.28b (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.39.28b (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.39.28b (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)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.988
_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    -26.00  89.00   0.50    0.70    --    0.00  70.00 172.00  230
  2  \w    -89.00  20.00   0.50    0.70    --    0.00 -51.00-136.00  218
  3  \w      5.00 121.00   0.50    3.60    --   94.60 -70.00  40.00  232
  4  \w     74.00 184.00   0.50    3.60    --   94.60  51.00   9.00  220
  5  \w      5.00 115.00   0.50    3.60    --   94.60 -51.00-136.00  220
  6  \w     68.00 184.00   0.50    3.60    --   94.60  70.00 172.00  232
  7  \w    -33.00  31.00   0.50    0.70    --    0.00 -82.00-180.00  128
  8  \w    -33.00  31.00   0.50    0.70    --    0.00 -82.00 -30.00  128
  9  \w      5.00 114.00   0.50    3.60    --   94.60 -45.00  30.00  218
 10  \w      5.00 118.00   0.50    3.60    --   94.60 -15.00  90.00  226
 11  \w      6.00 110.00   0.50    3.60    --   94.60 -30.00-120.00  208
 12  \w     88.00 114.00   0.50    3.60    --   94.60  30.00  90.00   52
 13  \w    120.00 180.00   0.50    3.60    --   94.60  30.00  90.00  120
 14  \w     16.00 110.00   0.50    3.60    --   94.60 -30.00  30.00  188
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RINC): Kappa single'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0451697000
_diffrn_orient_matrix_UB_12      -0.1544505000
_diffrn_orient_matrix_UB_13      -0.0170626000
_diffrn_orient_matrix_UB_21      0.1556249000
_diffrn_orient_matrix_UB_22      -0.0564205000
_diffrn_orient_matrix_UB_23      0.0347298000
_diffrn_orient_matrix_UB_31      -0.1278832000
_diffrn_orient_matrix_UB_32      -0.0141028000
_diffrn_orient_matrix_UB_33      0.0483907000
_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     0.0205
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            16932
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.981
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.818
_diffrn_reflns_theta_min         3.557
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.771
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.50088
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.28b (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.352
_exptl_crystal_description       block
_exptl_crystal_F_000             768
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.216
_refine_diff_density_min         -0.163
_refine_diff_density_rms         0.036
_refine_ls_abs_structure_details
;
 Flack x determined using 1371 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.04(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     262
_refine_ls_number_reflns         3434
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.048
_refine_ls_R_factor_all          0.0275
_refine_ls_R_factor_gt           0.0265
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0402P)^2^+0.3332P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0690
_refine_ls_wR_factor_ref         0.0695
_reflns_Friedel_coverage         0.709
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.971
_reflns_number_gt                3332
_reflns_number_total             3434
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            np9b00095_si_005.cif
_cod_data_source_block           20180509_sn4_61_2
_cod_database_code               1552689
_shelx_shelxl_version_number     2017/1
_shelx_estimated_absorpt_t_max   0.977
_shelx_estimated_absorpt_t_min   0.861
_reflns_odcompleteness_completeness 99.95
_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:
 C00A(H00E), C00D(H00F), C00J(H00M)
2.b Secondary CH2 refined with riding coordinates:
 C007(H00A,H00B), C009(H00D,H00C), C00I(H00L,H00K), C00K(H00N,H00O)
2.c Idealised Me refined as rotating group:
 C00M(H00P,H00Q,H00R), C00N(H00S,H00T,H00U), C00O(H00V,H00W,H00X)
2.d Idealised tetrahedral OH refined as rotating group:
 O001(H001), O002(H002), O003(H003), O004(H004), O005(H005)
;
_shelx_res_checksum              79479
_shelx_hkl_checksum              10013
_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 1.795
_oxdiff_exptl_absorpt_empirical_full_min 0.645