Eremophilane and cadinane sesquiterpenoids from the fruits of <i>Alpinia oxyphylla</i> and their anti-inflammatory activities.
Dong, Jie; Zhou, Mi; Pan, Da-Bo; Qin, Qian-Yu; Li, Ting; Yao, Xin-Sheng; Li, Hai-Bo; Yu, Yang; Food & function 14 (2023) 9755–9766; doi:10.1039/d3fo01221b

data_1569929
_publ_section_title
;
 Eremophilane and cadinane sesquiterpenoids from the fruits of <i>Alpinia
 oxyphylla</i> and their anti-inflammatory activities.
;
_journal_issue                   21
_journal_name_full               'Food &amp; function'
_journal_page_first              9755
_journal_page_last               9766
_journal_paper_doi               10.1039/d3fo01221b
_journal_volume                  14
_journal_year                    2023
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C15 H20 O2'
_chemical_formula_sum            'C15 H20 O2'
_chemical_formula_weight         232.31
_chemical_name_systematic
(3S,4S,5R,7R)-eremophila-3,4-epoxy-1(10),11-dien-2-one
_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             2023-08-25
_audit_creation_method
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_audit_update_record
;
2023-08-25 deposited with the CCDC.	2023-09-22 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.12559(16)
_cell_length_b                   9.43073(17)
_cell_length_c                   14.8426(3)
_cell_measurement_reflns_used    7764
_cell_measurement_temperature    170.0(2)
_cell_measurement_theta_max      73.6070
_cell_measurement_theta_min      2.9330
_cell_volume                     1277.37(4)
_computing_cell_refinement       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      170.0(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.993
_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   -115.00 -16.00   1.00    1.00    --  -40.73 -38.00 -90.00   99
  2  \w    -69.00  32.00   1.00    1.00    --  -40.73  57.00  60.00  101
  3  \w    -96.00  -2.00   1.00    1.00    --  -40.73 125.00-180.00   94
  4  \w   -111.00 -16.00   1.00    1.00    --  -40.73 -57.00 150.00   95
  5  \w     26.00  86.00   1.00    1.00    --   40.73-125.00 -30.00   60
  6  \w    -20.00  62.00   1.00    1.00    --   40.73 -38.00 -30.00   82
  7  \w     65.00 109.00   1.00    1.22    --  107.58 -94.00-180.00   44
  8  \w     31.00 129.00   1.00    1.22    --  107.58 -77.00-120.00   98
  9  \w     36.00 125.00   1.00    1.22    --  107.58 -45.00  90.00   89
 10  \w     59.00  84.00   1.00    1.22    --  107.58 -94.00 150.00   25
 11  \w     40.00 122.00   1.00    1.22    --  107.58-125.00  60.00   82
 12  \w     81.00 173.00   1.00    1.22    --  107.58  30.00-180.00   92
 13  \w     38.00 115.00   1.00    1.22    --  107.58 -45.00   0.00   77
 14  \w    120.00 147.00   1.00    1.22    --  107.58 -15.00 150.00   27
 15  \w     33.00 116.00   1.00    1.22    --  107.58 -15.00 150.00   83
 16  \w     77.00 119.00   1.00    1.22    --  107.58-125.00 120.00   42
 17  \w     96.00 122.00   1.00    1.22    --  107.58 125.00-150.00   26
 18  \w    148.00 174.00   1.00    1.22    --  107.58 125.00-150.00   26
 19  \w     57.00 132.00   1.00    1.22    --  107.58 -30.00-150.00   75
 20  \w   -117.00  -8.00   1.00    2.00    --  -40.98 -77.00 -90.00  109
 21  \w   -117.00 -76.00   1.00    2.00    --  -40.98 -77.00   0.00   41
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1332872000
_diffrn_orient_matrix_UB_12      -0.1001243000
_diffrn_orient_matrix_UB_13      0.0022077000
_diffrn_orient_matrix_UB_21      -0.0941074000
_diffrn_orient_matrix_UB_22      0.1193252000
_diffrn_orient_matrix_UB_23      0.0409813000
_diffrn_orient_matrix_UB_31      -0.0434908000
_diffrn_orient_matrix_UB_32      0.0491129000
_diffrn_orient_matrix_UB_33      -0.0953277000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0442
_diffrn_reflns_av_unetI/netI     0.0279
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            10532
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.863
_diffrn_reflns_theta_min         5.558
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.617
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.71957
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.208
_exptl_crystal_description       block
_exptl_crystal_F_000             504
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.166
_refine_diff_density_min         -0.147
_refine_diff_density_rms         0.034
_refine_ls_abs_structure_details
;
 Flack x determined using 977 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.05(14)
_refine_ls_extinction_coef       0.0053(9)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2019/2 (Sheldrick 2019)'
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     166
_refine_ls_number_reflns         2551
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.037
_refine_ls_R_factor_all          0.0345
_refine_ls_R_factor_gt           0.0323
_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^)+(0.0513P)^2^+0.1162P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0856
_refine_ls_wR_factor_ref         0.0872
_reflns_Friedel_coverage         0.705
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.970
_reflns_number_gt                2451
_reflns_number_total             2551
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3fo01221b2.cif
_cod_data_source_block           ao4e4i2
_cod_depositor_comments
'Adding full bibliography for 1569929--1569930.cif.'
_cod_database_code               1569929
_shelx_shelxl_version_number     2019/3
_shelx_estimated_absorpt_t_max   0.941
_shelx_estimated_absorpt_t_min   0.913
_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
2.a Ternary CH refined with riding coordinates:
 C7(H7), C3(H3)
2.b Secondary CH2 refined with riding coordinates:
 C6(H6A,H6B), C8(H8A,H8B), C9(H9A,H9B)
2.c Aromatic/amide H refined with riding coordinates:
 C1(H1)
2.d Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C), C14(H14A,H14B,H14C), C15(H15A,H15B,H15C)
;
_shelx_res_checksum              5097
_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 1.577
_oxdiff_exptl_absorpt_empirical_full_min 0.686