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_1556568
_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_moiety         'C20 H34 O6'
_chemical_formula_sum            'C20 H34 O6'
_chemical_formula_weight         370.47
_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
_atom_sites_solution_primary     dual
_audit_creation_date             2018-04-24
_audit_creation_method
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_cell_angle_alpha                90
_cell_angle_beta                 90.9660(10)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   12.76150(10)
_cell_length_b                   23.2559(2)
_cell_length_c                   12.86880(10)
_cell_measurement_reflns_used    23788
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      73.5800
_cell_measurement_theta_min      3.4530
_cell_volume                     3818.66(5)
_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 0.999
_diffrn_measured_fraction_theta_max 0.985
_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    -24.00  20.00   0.50    0.50    --    0.00 -82.00 150.00   88
  2  \w    -31.00  31.00   0.50    0.50    --    0.00 -82.00  60.00  124
  3  \w      8.00  58.00   0.50    0.50    --    0.00  38.00-120.00  100
  4  \w     14.00  41.00   0.50    0.50    --    0.00  38.00   0.00   54
  5  \w    -44.00 -17.00   0.50    0.50    --    0.00 -77.00 150.00   54
  6  \w     -3.00  29.00   0.50    0.50    --    0.00 -77.00 150.00   64
  7  \w    -44.00  27.00   0.50    0.50    --    0.00 -77.00-120.00  142
  8  \w      8.00 126.00   0.50    1.00    --   94.60 -82.00 -30.00  236
  9  \w     34.00  88.00   0.50    1.00    --   94.60 -45.00-150.00  108
 10  \w     16.00 118.00   0.50    1.00    --   94.60 -61.00 -30.00  204
 11  \w      5.00  30.00   0.50    1.00    --   94.60 -61.00-150.00   50
 12  \w     44.00 108.00   0.50    1.00    --   94.60 -61.00-150.00  128
 13  \w     88.00 162.00   0.50    1.00    --   94.60  61.00 -30.00  148
 14  \w     89.00 114.00   0.50    1.00    --   94.60 -82.00-120.00   50
 15  \w     97.00 123.00   0.50    1.00    --   94.60 -82.00  90.00   52
 16  \w     80.00 116.00   0.50    1.00    --   94.60 -15.00 -30.00   72
 17  \w     15.00 118.00   0.50    1.00    --   94.60 -61.00 120.00  206
 18  \w     93.00 119.00   0.50    1.00    --   94.60 -82.00  30.00   52
 19  \w     90.00 115.00   0.50    1.00    --   94.60 -82.00-180.00   50
 20  \w     71.00 178.00   0.50    1.00    --   94.60  15.00  90.00  214
 21  \w     75.00 168.00   0.50    1.00    --   94.60  45.00-150.00  186
 22  \w      6.00 125.00   0.50    1.00    --   94.60 -82.00 120.00  238
 23  \w     71.00  96.00   0.50    1.00    --   94.60 -82.00 -90.00   50
 24  \w     83.00 181.00   0.50    1.00    --   94.60  15.00 120.00  196
;
_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      0.0943771000
_diffrn_orient_matrix_UB_12      -0.0375529000
_diffrn_orient_matrix_UB_13      -0.0293791000
_diffrn_orient_matrix_UB_21      0.0551543000
_diffrn_orient_matrix_UB_22      0.0532565000
_diffrn_orient_matrix_UB_23      -0.0447567000
_diffrn_orient_matrix_UB_31      0.0512768000
_diffrn_orient_matrix_UB_32      0.0119802000
_diffrn_orient_matrix_UB_33      0.1070629000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0301
_diffrn_reflns_av_unetI/netI     0.0340
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            42822
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.969
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.930
_diffrn_reflns_theta_min         3.435
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.763
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.57503
_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_density_diffrn    1.289
_exptl_crystal_description       block
_exptl_crystal_F_000             1616
_exptl_crystal_size_max          0.10
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.446
_refine_diff_density_min         -0.218
_refine_diff_density_rms         0.042
_refine_ls_abs_structure_details
;
 Flack x determined using 6416 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.03(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1004
_refine_ls_number_reflns         14959
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.059
_refine_ls_R_factor_all          0.0336
_refine_ls_R_factor_gt           0.0315
_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^)+(0.0390P)^2^+0.8070P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0790
_refine_ls_wR_factor_ref         0.0800
_reflns_Friedel_coverage         0.917
_reflns_Friedel_fraction_full    0.991
_reflns_Friedel_fraction_max     0.951
_reflns_number_gt                14232
_reflns_number_total             14959
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            np9b00569_si_004.cif
_cod_data_source_block           20180424_1
_cod_depositor_comments
;
Adding full bibliography for 1556567--1556572.cif.

2022-05-28
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_moiety     '4(C20 H34 O6)'
_cod_original_formula_sum        'C80 H136 O24'
_cod_original_formula_units_Z    2
_cod_original_formula_weight     1481.88
_cod_database_code               1556568
_shelx_shelxl_version_number     2014/7
_reflns_odcompleteness_completeness 99.97
_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:
 C00S(H00S), C00U(H00U), C00W(H00W), C00Z(H00Z), C014(H014), C017(H017),
 C01A(H01Z), C01B(H01P), C01J(H01T), C01P(H1AA), C01Q(H01W), C01R(H9AA),
 C01U(H0BA), C01X(H1BA), C025(H025), C027(H027)
2.b Secondary CH2 refined with riding coordinates:
 C011(H01L,H01M), C012(H01N,H01O), C015(H01X,H01Y), C019(H01A,H01B), C01F(H01,
 HB), C01G(H01C,H01D), C01K(H0AA,HC), C01O(H01U,H01V), C01S(H01E,H01F),
 C01V(H01G,H01H), C01Y(H2BA,HF), C01Z(H3AA,HG), C020(H3BA,HH), C021(H02N,H02O),
 C026(H02P,H02Q), C028(H02D,H02E), C029(H4BA,HI), C02C(H02,HJ), C02G(H02X,H02Y),
  C02I(H5BA,HM), C02J(H5AA,HN), C02Q(H8BA,HU), C02T(H9BA,HX), C02W(H02L,H02M)
2.c Idealised Me refined as rotating group:
 C01D(H8AA,H,HA), C01H(H01Q,H01R,H01S), C01T(H2AA,HD,HE), C01W(H01I,H01J,H01K),
  C024(H02A,H02B,H02C), C02D(H02R,H02S,H02T), C02E(H02U,H02V,H02W), C02H(H4AA,
 HK,HL), C02K(H02F,H02G,H02H), C02L(H6BA,HO,HP), C02N(H6AA,HQ,HR), C02P(H7BA,HS,
 HT), C02S(H7AA,HV,HW), C02U(H02Z,HY,HZ), C02V(H02I,H02J,H02K), C02X(H0CA,H1CA,
 H2CA)
2.d Idealised tetrahedral OH refined as rotating group:
 O001(H001), O003(H003), O006(H006), O007(H007), O008(H008), O009(H009),
 O00A(H00A), O00B(H00B), O00D(H00D), O00F(H00F), O00G(H00G), O00H(H00H),
 O00K(H00K), O00N(H00N), O00P(H00P)
;
_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 1.658
_oxdiff_exptl_absorpt_empirical_full_min 0.628