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_1552691
_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 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
_atom_sites_solution_primary     dual
_audit_creation_date             2018-05-09
_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                   6.19529(4)
_cell_length_b                   12.69397(8)
_cell_length_c                   22.16712(14)
_cell_measurement_reflns_used    12481
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      73.5650
_cell_measurement_theta_min      3.9780
_cell_volume                     1743.285(19)
_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 0.991
_diffrn_measured_fraction_theta_max 0.979
_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      5.00 184.00   0.50    1.50    --   94.60  -4.00  -8.00  358
  2  \w      5.00 184.00   0.50    1.50    --   94.60  -4.00  -8.00  358
  3  \w    -89.00  89.00   0.50    0.50    --    0.00   4.00 168.00  356
  4  \w    -33.00  31.00   0.50    0.50    --    0.00 -82.00  60.00  128
  5  \w    -33.00  31.00   0.50    0.50    --    0.00 -82.00 -60.00  128
  6  \w      5.00 111.00   0.50    1.50    --   94.60 -82.00  90.00  212
  7  \w      5.00 124.00   0.50    1.50    --   94.60 -77.00 -60.00  238
  8  \w      5.00 126.00   0.50    1.50    --   94.60 -82.00-180.00  242
  9  \w      5.00 111.00   0.50    1.50    --   94.60 -82.00  90.00  212
 10  \w     76.00 102.00   0.50    1.50    --   94.60 -82.00-150.00   52
 11  \w     65.00  91.00   0.50    1.50    --   94.60 -82.00-120.00   52
 12  \w     94.00 120.00   0.50    1.50    --   94.60 -82.00-120.00   52
 13  \w      5.00 109.00   0.50    1.50    --   94.60 -30.00 -60.00  208
 14  \w     70.00  95.00   0.50    1.50    --   94.60   4.00 168.00   50
;
_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      -0.0028906000
_diffrn_orient_matrix_UB_12      0.0177638000
_diffrn_orient_matrix_UB_13      -0.0687622000
_diffrn_orient_matrix_UB_21      -0.0149871000
_diffrn_orient_matrix_UB_22      0.1198264000
_diffrn_orient_matrix_UB_23      0.0102218000
_diffrn_orient_matrix_UB_31      0.2481130000
_diffrn_orient_matrix_UB_32      0.0074928000
_diffrn_orient_matrix_UB_33      -0.0001239000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0252
_diffrn_reflns_av_unetI/netI     0.0188
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.979
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            16621
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.969
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.881
_diffrn_reflns_theta_min         3.988
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.696
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.81015
_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    1.282
_exptl_crystal_description       block
_exptl_crystal_F_000             736
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.194
_refine_diff_density_min         -0.185
_refine_diff_density_rms         0.037
_refine_ls_abs_structure_details
;
 Flack x determined using 1372 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.01(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.017
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     231
_refine_ls_number_reflns         3428
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.017
_refine_ls_R_factor_all          0.0273
_refine_ls_R_factor_gt           0.0264
_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^)+(0.0406P)^2^+0.4098P] 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         0.703
_reflns_Friedel_fraction_full    0.995
_reflns_Friedel_fraction_max     0.955
_reflns_number_gt                3343
_reflns_number_total             3428
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            np9b00095_si_004.cif
_cod_data_source_block           20180509_sn4_84_23
_cod_original_cell_volume        1743.286(19)
_cod_database_code               1552691
_shelx_shelxl_version_number     2017/1
_chemical_oxdiff_usercomment     'C H O N'
_shelx_estimated_absorpt_t_max   0.966
_shelx_estimated_absorpt_t_min   0.722
_reflns_odcompleteness_completeness 98.86
_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:
 C13(H13), C2(H2A), C5(H5), C9(H9)
2.b Secondary CH2 refined with riding coordinates:
 C19(H19A,H19B), C14(H14A,H14B), C1(H1A,H1B), C6(H6A,H6B), C7(H7A,H7B),
 C15(H15A,H15B), C16(H16A,H16B), C11(H11A,H11B)
2.c Idealised Me refined as rotating group:
 C17(H17A,H17B,H17C), C18(H18A,H18B,H18C)
2.d Idealised tetrahedral OH refined as rotating group:
 O1(H1), O2(H2), O4(H4), O3(H3)
;
_shelx_res_checksum              9965
_shelx_hkl_checksum              47805
_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 1.324
_oxdiff_exptl_absorpt_empirical_full_min 0.604