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_1569930
_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 UNKNOWN
_chemical_formula_moiety         'C15 H24 O2, 1/3(C H4 O)'
_chemical_formula_sum            'C15.33333 H25.33333 O2.33333'
_chemical_formula_weight         247.02
_chemical_name_systematic
(2R,4R,5S,7S,9R)-eremophila-1(10),11-dien-2,9-diol
_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            12
_cell_length_a                   8.1552(6)
_cell_length_b                   20.429(2)
_cell_length_c                   27.192(3)
_cell_measurement_reflns_used    7890
_cell_measurement_temperature    150.15
_cell_measurement_theta_max      99
_cell_measurement_theta_min      3
_cell_volume                     4530.3(7)
_computing_cell_refinement       'CrysAlisPro 1.171.42.59a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.59a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.59a (Rigaku OD, 2022)'
_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_temperature      150.15
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.970
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0727
_diffrn_reflns_av_unetI/netI     0.1223
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.970
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_number            12357
_diffrn_reflns_point_group_measured_fraction_full 0.899
_diffrn_reflns_point_group_measured_fraction_max 0.858
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.687
_diffrn_reflns_theta_min         2.705
_diffrn_source                   'Rotating-anode X-ray tube'
_exptl_absorpt_coefficient_mu    0.557
_exptl_absorpt_correction_T_max  0.999
_exptl_absorpt_correction_T_min  0.666
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 1996)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.087
_exptl_crystal_description       BLOCK
_exptl_crystal_F_000             1632
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.253
_refine_diff_density_min         -0.300
_refine_diff_density_rms         0.057
_refine_ls_abs_structure_details
;
 Flack x determined using 1237 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.2(3)
_refine_ls_extinction_coef       0.00109(15)
_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   1.005
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     517
_refine_ls_number_reflns         7861
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.005
_refine_ls_R_factor_all          0.1099
_refine_ls_R_factor_gt           0.0726
_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^)+(0.0647P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1600
_refine_ls_wR_factor_ref         0.1909
_reflns_Friedel_coverage         0.576
_reflns_Friedel_fraction_full    0.769
_reflns_Friedel_fraction_max     0.714
_reflns_number_gt                5210
_reflns_number_total             7861
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3fo01221b2.cif
_cod_data_source_block           f5e1-2
_cod_depositor_comments
;
Adding full bibliography for 1569929--1569930.cif.

2025-06-02
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_sum            'C46 H76 O7'
_cod_original_formula_weight         741.06
_cod_original_formula_moiety         '3(C15 H24 O2), C H4 O'
_cod_original_formula_units_Z            4
_cod_database_code               1569930
_shelx_shelxl_version_number     2019/3
_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. Restrained distances
 O1M-H1M
 0.96 with sigma of 0.02
 O1A_$1-H1A_$1
 0.96 with sigma of 0.02
3.a Ternary CH refined with riding coordinates:
 C2A(H2AA), C4A(H4A), C7A(H7A), C9A(H9A), C2B(H2BA), C4B(H4B), C7B(H7B),
 C9B(H9B), C2C(H2CA), C4C(H4C), C7C(H7C), C9C(H9C)
3.b Secondary CH2 refined with riding coordinates:
 C3A(H3AA,H3AB), C6A(H6AA,H6AB), C8A(H8AA,H8AB), C3B(H3BA,H3BB), C6B(H6BA,
 H6BB), C8B(H8BA,H8BB), C3C(H3CA,H3CB), C6C(H6CA,H6CB), C8C(H8CA,H8CB)
3.c Aromatic/amide H refined with riding coordinates:
 C1A(H1AA), C1B(H1BA), C1C(H1CA)
3.d X=CH2 refined with riding coordinates:
 C12A(H12A,H12B), C12B(H12C,H12D), C12C(H12E,H12F)
3.e Idealised Me refined as rotating group:
 C13A(H13A,H13B,H13C), C14A(H14A,H14B,H14C), C15A(H15A,H15B,H15C), C13B(H13D,
 H13E,H13F), C14B(H14D,H14E,H14F), C15B(H15D,H15E,H15F), C13C(H13G,H13H,H13I),
 C14C(H14G,H14H,H14I), C15C(H15G,H15H,H15I), C1M(H1MA,H1MB,H1MC)
;
_shelx_res_checksum              31351
_olex2_submission_special_instructions 'No special instructions were received'