Discovery of artemargyins A-E: rare 9'-nor-dibenzylbutane lignans and a lignan-coumarin hybrid with antihepatic fibrosis activities from Artemisia argyi var. gracilis
Wu, Ying; Ma, Ze; Huang, Yong-Xiang; Li, Tian-Ze; Wang, Yong-Cui; Chen, Ji-Jun; Organic & Biomolecular Chemistry  (2025) –; doi:10.1039/D6OB00214E

data_7161094
_publ_section_title
;
 Discovery of artemargyins A-E: rare 9'-<i>nor</i>-dibenzylbutane lignans
 and a lignan-coumarin hybrid with anti-hepatic fibrosis activities from
 <i>Artemisia argyi</i> var<i>. gracilis</i>.
;
_journal_issue                   16
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              3496
_journal_page_last               3505
_journal_paper_doi               10.1039/d6ob00214e
_journal_volume                  24
_journal_year                    2026
_chemical_absolute_configuration unk
_chemical_formula_moiety         'C19 H20 O6'
_chemical_formula_sum            'C19 H20 O6'
_chemical_formula_weight         344.35
_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   geom
_audit_update_record
;
2026-01-30 deposited with the CCDC.	2026-03-20 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 104.2890(10)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   10.4759(2)
_cell_length_b                   5.47890(10)
_cell_length_c                   15.0364(3)
_cell_measurement_reflns_used    9985
_cell_measurement_temperature    150.(2)
_cell_measurement_theta_max      69.9376
_cell_measurement_theta_min      3.0328
_cell_volume                     836.34(3)
_computing_cell_refinement       'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_data_collection       'Bruker Instrument Service vV6.2.15'
_computing_data_reduction        'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_molecular_graphics    'shelXle (C.B. Huebschle, rev 882)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      150.(2)
_diffrn_detector_area_resol_mean 7.3910
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker D8 QUEST PHOTON II'
_diffrn_radiation_monochromator  'Helixos MX multilayer Optic'
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0554
_diffrn_reflns_av_unetI/netI     0.0388
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            14587
_diffrn_reflns_theta_full        69.93
_diffrn_reflns_theta_max         69.93
_diffrn_reflns_theta_min         3.03
_diffrn_source                   'Ius Diamond'
_diffrn_source_type              Microfocus
_exptl_absorpt_coefficient_mu    0.848
_exptl_absorpt_correction_T_max  0.90
_exptl_absorpt_correction_T_min  0.76
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 - Bruker AXS area detector scaling and absorption correction
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_density_diffrn    1.367
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             364
_exptl_crystal_size_max          0.330
_exptl_crystal_size_mid          0.210
_exptl_crystal_size_min          0.130
_refine_diff_density_max         0.235
_refine_diff_density_min         -0.247
_refine_ls_abs_structure_details
;

Flack x determined using 1191 quotients [(I+)-(I-)]/[(I+)+(I-)]
(Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.23(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     228
_refine_ls_number_reflns         3103
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.032
_refine_ls_R_factor_all          0.0388
_refine_ls_R_factor_gt           0.0364
_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^)+(0.0488P)^2^+0.1478P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0938
_refine_ls_wR_factor_ref         0.0964
_reflns_number_gt                2937
_reflns_number_total             3103
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d6ob00214e3.cif
_cod_data_source_block           jk63392
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_exptl_absorpt_correction_type' value 'Multi-Scan' was
changed to 'multi-scan' in accordance with the
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 8170 2020-07-09 18:12:32Z antanas 

 Adding full bibliography for 7161094.cif.
;
_cod_database_code               7161094
_shelx_res_checksum              98080