Anti-inflammatory Eudesmane Sesquiterpenoids from <i>Artemisia hedinii</i>.
Wang, Xing; Peng, Xia; Tang, Chunping; Zhou, Shuaizhen; Ke, Chang-Qiang; Liu, Yueling; Yao, Sheng; Ai, Jing; Ye, Yang; Journal of natural products 84 (2021) 1626–1637; doi:10.1021/acs.jnatprod.1c00177

data_1562751
_publ_section_title
;
 Anti-inflammatory Eudesmane Sesquiterpenoids from <i>Artemisia
 hedinii</i>.
;
_journal_issue                   5
_journal_name_full               'Journal of natural products'
_journal_page_first              1626
_journal_page_last               1637
_journal_paper_doi               10.1021/acs.jnatprod.1c00177
_journal_volume                  84
_journal_year                    2021
_chemical_absolute_configuration rmad
_chemical_formula_moiety         'C17 H22 O5, H2 O'
_chemical_formula_sum            'C17 H24 O6'
_chemical_formula_weight         324.36
_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             2020-08-17
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.64130(10)
_cell_length_b                   14.8419(3)
_cell_length_c                   16.7613(3)
_cell_measurement_reflns_used    9734
_cell_measurement_temperature    140
_cell_measurement_theta_max      74.517
_cell_measurement_theta_min      2.636
_cell_volume                     1652.15(5)
_computing_cell_refinement       'SAINT V8.40A (?, 2016)'
_computing_data_reduction        'SAINT V8.40A (?, 2016)'
_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    'XT (Sheldrick, 2015)'
_diffrn_ambient_temperature      140.0
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.993
_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  0.0380
_diffrn_reflns_av_unetI/netI     0.0212
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            23113
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         74.508
_diffrn_reflns_theta_min         3.978
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.815
_exptl_absorpt_correction_T_max  0.7538
_exptl_absorpt_correction_T_min  0.6668
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1375 before and 0.0581 after correction. The Ratio of minimum to maximum transmission is 0.8846. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.304
_exptl_crystal_description       block
_exptl_crystal_F_000             696
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.179
_refine_diff_density_min         -0.149
_refine_diff_density_rms         0.031
_refine_ls_abs_structure_details
;
 Flack x determined using 1369 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.08(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.084
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     226
_refine_ls_number_reflns         3375
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.084
_refine_ls_R_factor_all          0.0292
_refine_ls_R_factor_gt           0.0282
_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^)+(0.0354P)^2^+0.2678P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0712
_refine_ls_wR_factor_ref         0.0722
_reflns_Friedel_coverage         0.728
_reflns_Friedel_fraction_full    0.998
_reflns_Friedel_fraction_max     0.995
_reflns_number_gt                3291
_reflns_number_total             3375
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            np1c00177_si_006.cif
_cod_data_source_block           22020327d1c6e2a_0m
_cod_depositor_comments
'Adding full bibliography for 1562743--1562751.cif.'
_cod_database_code               1562751
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.945
_shelx_estimated_absorpt_t_min   0.867
_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,H) groups
2. Restrained distances
 O5-H5
 0.87 with sigma of 0.02
3.a Free rotating group:
 O6(H6C,H6D)
3.b Ternary CH refined with riding coordinates:
 C9(H9), C7(H7)
3.c Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B), C2(H2A,H2B), C1(H1A,H1B), C6(H6A,H6B)
3.d Idealised Me refined as rotating group:
 C2'(H2'A,H2'B,H2'C), C14(H14A,H14B,H14C), C15(H15A,H15B,H15C)
;
_olex2_submission_special_instructions 'No special instructions were received'