Antinociceptive Grayanane Diterpenoids from the Leaves of <i>Pieris japonica</i>.
Zheng, Guijuan; Zhou, Junfei; Huang, Lang; Zhang, Hao; Sun, Na; Zhang, Hanqi; Jin, Pengfei; Yue, Mingbo; Meng, Lingkui; Yao, Guangmin; Journal of natural products 82 (2019) 3330–3339; doi:10.1021/acs.jnatprod.9b00569

data_1556567
_publ_section_title
;
 Antinociceptive Grayanane Diterpenoids from the Leaves of <i>Pieris
 japonica</i>.
;
_journal_issue                   12
_journal_name_full               'Journal of natural products'
_journal_page_first              3330
_journal_page_last               3339
_journal_paper_doi               10.1021/acs.jnatprod.9b00569
_journal_volume                  82
_journal_year                    2019
_chemical_absolute_configuration ad
_chemical_formula_sum            'C20 H32 O3'
_chemical_formula_weight         320.45
_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   mixed
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            6
_cell_length_a                   6.3628(3)
_cell_length_b                   11.7561(4)
_cell_length_c                   35.3232(13)
_cell_measurement_reflns_used    9997
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      65.89
_cell_measurement_theta_min      2.50
_cell_volume                     2642.24(18)
_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-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.960
_diffrn_measured_fraction_theta_max 0.960
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0585
_diffrn_reflns_av_unetI/netI     0.0684
_diffrn_reflns_Laue_measured_fraction_full 0.960
_diffrn_reflns_Laue_measured_fraction_max 0.960
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       39
_diffrn_reflns_limit_l_min       -41
_diffrn_reflns_number            24522
_diffrn_reflns_point_group_measured_fraction_full 0.962
_diffrn_reflns_point_group_measured_fraction_max 0.962
_diffrn_reflns_theta_full        64.961
_diffrn_reflns_theta_max         64.961
_diffrn_reflns_theta_min         2.502
_exptl_absorpt_coefficient_mu    0.620
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.208
_exptl_crystal_description       block
_exptl_crystal_F_000             1056
_exptl_crystal_size_max          0.120
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.100
_refine_diff_density_max         0.271
_refine_diff_density_min         -0.288
_refine_diff_density_rms         0.059
_refine_ls_abs_structure_details
; 
 Flack x determined using 3490 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   -0.03(15)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     659
_refine_ls_number_reflns         8301
_refine_ls_number_restraints     10
_refine_ls_restrained_S_all      1.033
_refine_ls_R_factor_all          0.0551
_refine_ls_R_factor_gt           0.0541
_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^)+(0.0974P)^2^+0.6768P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1445
_refine_ls_wR_factor_ref         0.1451
_reflns_Friedel_coverage         0.900
_reflns_Friedel_fraction_full    0.963
_reflns_Friedel_fraction_max     0.963
_reflns_number_gt                8111
_reflns_number_total             8301
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            np9b00569_si_007.cif
_cod_data_source_block           cu_170518h_0m
_cod_depositor_comments
'Adding full bibliography for 1556567--1556572.cif.'
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               1556567
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.929
_shelx_estimated_absorpt_t_max   0.941
_shelx_res_checksum              78837
_shelx_hkl_checksum              66690