Anti-inflammatory Dimeric Tetrahydroxanthones from an Endophytic <i>Muyocopron laterale</i>.
Cao, Hai-Yan; Yi, Cheng; Sun, Sen-Feng; Li, Yong; Liu, Yun-Bao; Journal of natural products 85 (2022) 148–161; doi:10.1021/acs.jnatprod.1c00878

data_1566287
_publ_section_title
;
 Anti-inflammatory Dimeric Tetrahydroxanthones from an Endophytic
 <i>Muyocopron laterale</i>.
;
_journal_issue                   1
_journal_name_full               'Journal of natural products'
_journal_page_first              148
_journal_page_last               161
_journal_paper_doi               10.1021/acs.jnatprod.1c00878
_journal_volume                  85
_journal_year                    2022
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C32 H34 O12'
_chemical_formula_sum            'C32 H34 O12'
_chemical_formula_weight         610.59
_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   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2021-03-26
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6226)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.83460(10)
_cell_length_b                   15.3938(2)
_cell_length_c                   24.8916(3)
_cell_measurement_reflns_used    11707
_cell_measurement_temperature    100.00(12)
_cell_measurement_theta_max      75.0290
_cell_measurement_theta_min      3.3450
_cell_volume                     3002.03(7)
_computing_cell_refinement       'CrysAlisPro 1.171.41.95a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.95a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.95a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(12)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.986
_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     33.00 120.00   0.50    3.02    --   47.70  58.00  92.00  174
  2  \w    -24.00  68.00   0.50    3.02    --   47.70 -71.00 175.00  184
  3  \w     31.00 105.00   0.50   12.10    --  103.25 -96.00  80.00  148
  4  \w     83.00 176.00   0.50   12.10    --  103.25  71.00 -53.00  186
  5  \w     31.00  71.00   0.50   12.10    --  103.25 -58.00 -48.00   80
  6  \w   -119.00 -74.00   0.50    3.02    --  -47.70-125.00 -30.00   90
  7  \w    -23.00  28.00   0.50    3.02    --  -47.70  19.00 -30.00  102
  8  \w   -119.00 -74.00   0.50    3.02    --  -47.70-125.00-150.00   90
  9  \w    -68.00 -28.00   0.50   12.10    -- -101.00  61.00 -60.00   80
 10  \w    -68.00 -28.00   0.50   12.10    -- -101.00  61.00  30.00   80
 11  \w     31.00 111.00   0.50   12.10    --  103.25-125.00-120.00  160
 12  \w     91.00 178.00   0.50   12.10    --  103.25  30.00 -90.00  174
 13  \w     31.00  75.00   0.50   12.10    --  103.25 -61.00 120.00   88
 14  \w     81.00 176.00   0.50   12.10    --  103.25  77.00-180.00  190
 15  \w     31.00  75.00   0.50   12.10    --  103.25 -61.00 150.00   88
 16  \w     31.00  75.00   0.50   12.10    --  103.25 -61.00 -30.00   88
 17  \w     31.00  75.00   0.50   12.10    --  103.25 -61.00  90.00   88
 18  \w     91.00 178.00   0.50   12.10    --  103.25  30.00-120.00  174
 19  \w     25.00  50.00   0.50    3.02    --   47.70  77.00 -30.00   50
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0766289000
_diffrn_orient_matrix_UB_12      0.0656701000
_diffrn_orient_matrix_UB_13      0.0400071000
_diffrn_orient_matrix_UB_21      0.1370700000
_diffrn_orient_matrix_UB_22      -0.0669838000
_diffrn_orient_matrix_UB_23      0.0159816000
_diffrn_orient_matrix_UB_31      0.1182844000
_diffrn_orient_matrix_UB_32      0.0349892000
_diffrn_orient_matrix_UB_33      -0.0444154000
_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  0.0419
_diffrn_reflns_av_unetI/netI     0.0334
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            23838
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.973
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.313
_diffrn_reflns_theta_min         3.376
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'PhotonJet R (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.872
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.75380
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.95a (Rigaku Oxford Diffraction, 2021)
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    1.351
_exptl_crystal_description       block
_exptl_crystal_F_000             1288
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.252
_refine_diff_density_min         -0.192
_refine_diff_density_rms         0.046
_refine_ls_abs_structure_details
;
 Flack x determined using 2076 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.13(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     407
_refine_ls_number_reflns         6043
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.060
_refine_ls_R_factor_all          0.0477
_refine_ls_R_factor_gt           0.0407
_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^)+(0.0526P)^2^+0.6960P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0999
_refine_ls_wR_factor_ref         0.1036
_reflns_Friedel_coverage         0.741
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.957
_reflns_number_gt                5387
_reflns_number_total             6043
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            np1c00878_si_008.cif
_cod_data_source_block           chy_14a_auto
_cod_database_code               1566287
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.974
_shelx_estimated_absorpt_t_min   0.918
_reflns_odcompleteness_completeness 99.90
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     67.79
_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) groups
2.a Ternary CH refined with riding coordinates:
 C26(H26), C2(H2), C27(H27), C3(H3)
2.b Secondary CH2 refined with riding coordinates:
 C28(H28A,H28B), C4(H4A,H4B), C17(H17A,H17B)
2.c Aromatic/amide H refined with riding coordinates:
 C12(H12), C23(H23)
2.d Idealised Me refined as rotating group:
 C36(H36A,H36B,H36C), C44(H44A,H44B,H44C), C43(H43A,H43B,H43C), C31(H31A,H31B,
 H31C), C35(H35A,H35B,H35C), C38(H38A,H38B,H38C)
2.e Idealised tetrahedral OH refined as rotating group:
 O34(H34), O40(H40), O39(H39), O41(H41)
;
_shelx_res_checksum              98951
_shelx_hkl_checksum              24862
_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 1.421
_oxdiff_exptl_absorpt_empirical_full_min 0.761