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_1556571
_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            'C23 H38 O8'
_chemical_formula_weight         442.53
_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                 100.9240(10)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   6.5625(2)
_cell_length_b                   17.9101(5)
_cell_length_c                   9.5523(3)
_cell_measurement_reflns_used    9922
_cell_measurement_temperature    297(2)
_cell_measurement_theta_max      70.93
_cell_measurement_theta_min      4.71
_cell_volume                     1102.39(6)
_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      297(2)
_diffrn_measured_fraction_theta_full 0.965
_diffrn_measured_fraction_theta_max 0.965
_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  0.0224
_diffrn_reflns_av_unetI/netI     0.0219
_diffrn_reflns_Laue_measured_fraction_full 0.965
_diffrn_reflns_Laue_measured_fraction_max 0.965
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            15749
_diffrn_reflns_point_group_measured_fraction_full 0.965
_diffrn_reflns_point_group_measured_fraction_max 0.965
_diffrn_reflns_theta_full        64.990
_diffrn_reflns_theta_max         64.990
_diffrn_reflns_theta_min         4.715
_exptl_absorpt_coefficient_mu    0.821
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.333
_exptl_crystal_description       block
_exptl_crystal_F_000             480
_exptl_crystal_size_max          0.150
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.100
_refine_diff_density_max         0.166
_refine_diff_density_min         -0.140
_refine_diff_density_rms         0.029
_refine_ls_abs_structure_details
; 
 Flack x determined using 1738 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   0.11(2)
_refine_ls_extinction_coef       0.0123(12)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.075
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     298
_refine_ls_number_reflns         3623
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.074
_refine_ls_R_factor_all          0.0268
_refine_ls_R_factor_gt           0.0268
_refine_ls_shift/su_max          0.006
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0445P)^2^+0.1415P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0724
_refine_ls_wR_factor_ref         0.0725
_reflns_Friedel_coverage         0.932
_reflns_Friedel_fraction_full    0.966
_reflns_Friedel_fraction_max     0.966
_reflns_number_gt                3618
_reflns_number_total             3623
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            np9b00569_si_006.cif
_cod_data_source_block           cu_170628F_0m
_cod_depositor_comments
'Adding full bibliography for 1556567--1556572.cif.'
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               1556571
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.887
_shelx_estimated_absorpt_t_max   0.922
_shelx_res_checksum              30670
_shelx_hkl_checksum              22646