Gneyulins A and B, stilbene trimers, and noidesols A and B, dihydroflavonol-C-glucosides, from the bark of Gnetum gnemonoides.
Shimokawa, Yoko; Akao, Yusuke; Hirasawa, Yusuke; Awang, Khalijah; Hadi, A Hamid A; Sato, Seizo; Aoyama, Chihiro; Takeo, Jiro; Shiro, Motoo; Morita, Hiroshi; Journal of natural products 73 (2010) 763–767; doi:10.1021/np9007987

data_1502833
_publ_section_title
;
 Gneyulins A and B, stilbene trimers, and noidesols A and B,
 dihydroflavonol-C-glucosides, from the bark of Gnetum gnemonoides.
;
_journal_issue                   4
_journal_name_full               'Journal of natural products'
_journal_page_first              763
_journal_page_last               767
_journal_paper_doi               10.1021/np9007987
_journal_volume                  73
_journal_year                    2010
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C22 H24 O12, C H4 O '
_chemical_formula_sum            'C23 H28 O13'
_chemical_formula_weight         512.47
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_Int_Tables_number      19
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_cell_angle_alpha                90.0000
_cell_angle_beta                 90.0000
_cell_angle_gamma                90.0000
_cell_formula_units_Z            4
_cell_length_a                   9.31894(17)
_cell_length_b                   11.1351(2)
_cell_length_c                   22.5910(7)
_cell_measurement_reflns_used    15369
_cell_measurement_temperature    93.1
_cell_measurement_theta_max      68.2
_cell_measurement_theta_min      5.1
_cell_volume                     2344.21(9)
_computing_cell_refinement       'PROCESS-AUTO (Rigaku, 1998)'
_computing_data_collection       'PROCESS-AUTO (Rigaku, 1998)'
_computing_data_reduction        'CrystalStructure (Rigaku & RAC 2007)'
_computing_molecular_graphics    'ORTEP (Johnson, 1976)'
_computing_publication_material  'CrystalStructure (Rigaku & RAC 2007)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_detector_area_resol_mean 10.00
_diffrn_measured_fraction_theta_full 0.983
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measurement_device_type  'Rigaku RAXIS-RAPID'
_diffrn_measurement_method       \w
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54187
_diffrn_reflns_av_R_equivalents  0.070
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            18110
_diffrn_reflns_theta_full        68.24
_diffrn_reflns_theta_max         68.24
_exptl_absorpt_coefficient_mu    1.034
_exptl_absorpt_correction_T_max  0.980
_exptl_absorpt_correction_T_min  0.892
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
    Higashi, T. (1995). Program for Absorption Correction.
    Rigaku Corporation, Tokyo, Japan.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.452
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       platelet
_exptl_crystal_F_000             1080.00
_exptl_crystal_size_max          0.10
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.25
_refine_diff_density_min         -0.25
_refine_ls_abs_structure_details
'Flack, H. D. (1983), Acta Cryst. A39, 876-881.  1788 Friedel Pairs'
_refine_ls_abs_structure_Flack   -0.1(2)
_refine_ls_extinction_coef       0.0022(2)
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   0.902
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_parameters     338
_refine_ls_number_reflns         4210
_refine_ls_R_factor_gt           0.0471
_refine_ls_shift/su_max          0.0060
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[\s^2^(Fo^2^)+(0.0395P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.1000
_reflns_number_gt                2624
_reflns_number_total             4210
_reflns_threshold_expression     F^2^>2.0\s(F^2^)
_cod_data_source_file            np9007987_si_001.cif
_cod_data_source_block           '_GNE-1'
_cod_original_formula_sum        'C23 H28 O13 '
_cod_database_code               1502833