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_1552690
_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      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   geom
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.0243(2)
_cell_length_b                   10.7505(3)
_cell_length_c                   24.3048(7)
_cell_measurement_reflns_used    5113
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      66.67
_cell_measurement_theta_min      3.64
_cell_volume                     1835.37(9)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.983
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0377
_diffrn_reflns_av_unetI/netI     0.0435
_diffrn_reflns_Laue_measured_fraction_full 0.983
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            7404
_diffrn_reflns_point_group_measured_fraction_full 0.949
_diffrn_reflns_point_group_measured_fraction_max 0.948
_diffrn_reflns_theta_full        66.660
_diffrn_reflns_theta_max         66.660
_diffrn_reflns_theta_min         3.637
_diffrn_source                   'sealed tube'
_exptl_absorpt_coefficient_mu    0.794
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.333
_exptl_crystal_description       block
_exptl_crystal_F_000             814
_exptl_crystal_size_max          0.05
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.228
_refine_diff_density_min         -0.184
_refine_diff_density_rms         0.045
_refine_ls_abs_structure_details
;
 Flack x determined using 1042 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.08(12)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     245
_refine_ls_number_reflns         3084
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.064
_refine_ls_R_factor_all          0.0425
_refine_ls_R_factor_gt           0.0371
_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^)+(0.0300P)^2^+0.8015P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0847
_refine_ls_wR_factor_ref         0.0879
_reflns_Friedel_coverage         0.654
_reflns_Friedel_fraction_full    0.900
_reflns_Friedel_fraction_max     0.900
_reflns_number_gt                2810
_reflns_number_total             3084
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            np9b00095_si_006.cif
_cod_data_source_block           a
_cod_original_formula_sum        ' C20 H32 O6'
_cod_database_code               1552690
_shelx_shelxl_version_number     2014/7
_shelx_res_checksum              92055
_shelx_hkl_checksum              11234