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_1566284
_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      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
_atom_sites_solution_primary     dual
_audit_creation_date             2021-03-12
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6226)
;
_cell_angle_alpha                90
_cell_angle_beta                 113.339(3)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   14.3066(3)
_cell_length_b                   7.58650(10)
_cell_length_c                   14.8171(3)
_cell_measurement_reflns_used    11338
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      73.6030
_cell_measurement_theta_min      3.6000
_cell_volume                     1476.62(6)
_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(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.974
_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     89.00 173.00   0.50    0.54    --  103.25  61.00   0.00  168
  2  \w     90.00 167.00   0.50    0.54    --  103.25  61.00 120.00  154
  3  \w    151.00 176.00   0.50    0.54    --  103.25  61.00-120.00   50
  4  \w    131.00 171.00   0.50    0.54    --  103.25  77.00-150.00   80
  5  \w     81.00 122.00   0.50    0.54    --  103.25  77.00-150.00   82
  6  \w     94.00 138.00   0.50    0.54    --  103.25  61.00-120.00   88
  7  \w    -23.00   2.00   0.50    0.13    --  -47.70  19.00   0.00   50
  8  \w    -67.00 -29.00   0.50    0.54    -- -101.00  61.00-120.00   76
  9  \w    -68.00 -28.00   0.50    0.54    -- -101.00  61.00 -30.00   80
 10  \w   -102.00 -38.00   0.50    0.54    -- -101.00  77.00   0.00  128
 11  \w    -55.00 -28.00   0.50    0.54    -- -101.00 125.00  90.00   54
 12  \w   -109.00 -83.00   0.50    0.54    -- -101.00 125.00  90.00   52
 13  \w   -102.00 -37.00   0.50    0.54    -- -101.00 125.00 -30.00  130
 14  \w   -112.00 -84.00   0.50    0.54    -- -101.00 125.00 -60.00   56
 15  \w   -110.00 -82.00   0.50    0.54    -- -101.00 125.00-150.00   56
 16  \w    -62.00 -28.00   0.50    0.54    -- -101.00 125.00-150.00   68
 17  \w    -72.00 -15.00   0.50    0.13    --  -47.70 113.00 154.00  114
 18  \w   -107.00 -43.00   0.50    0.54    -- -101.00 113.00 154.00  128
 19  \w   -118.00 -38.00   0.50    0.13    --  -47.70 -77.00   0.00  160
 20  \w   -173.00-145.00   0.50    0.54    -- -101.00 -45.00 -90.00   56
 21  \w   -138.00-111.00   0.50    0.54    -- -101.00 -45.00 -90.00   54
 22  \w   -174.00-138.00   0.50    0.54    -- -101.00 -15.00-120.00   72
 23  \w   -131.00 -89.00   0.50    0.54    -- -101.00 -61.00 -60.00   84
 24  \w   -123.00 -91.00   0.50    0.54    -- -101.00 -61.00 150.00   64
 25  \w   -172.00-130.00   0.50    0.54    -- -101.00 -61.00 150.00   84
 26  \w   -110.00 -74.00   0.50    0.13    --  -47.70-125.00 -30.00   72
 27  \w   -118.00 -78.00   0.50    0.13    --  -47.70-125.00-150.00   80
 28  \w   -108.00 -79.00   0.50    0.13    --  -47.70-125.00-180.00   58
 29  \w   -118.00 -85.00   0.50    0.13    --  -47.70-125.00 120.00   66
 30  \w   -118.00 -74.00   0.50    0.13    --  -47.70-125.00 150.00   88
 31  \w   -131.00 -95.00   0.50    0.54    -- -101.00-113.00  62.00   72
 32  \w     34.00  97.00   0.50    0.54    --  103.25 -77.00  60.00  126
 33  \w     47.00  75.00   0.50    0.54    --  103.25 -61.00 120.00   56
 34  \w     36.00  75.00   0.50    0.54    --  103.25 -61.00  90.00   78
 35  \w    107.00 132.00   0.50    0.54    --  103.25 113.00 154.00   50
 36  \w    -24.00  28.00   0.50    0.13    --   47.70 -19.00 120.00  104
 37  \w     31.00  68.00   0.50    0.54    --  103.25 -61.00 -60.00   74
 38  \w     37.00 110.00   0.50    0.54    --  103.25-125.00-120.00  146
 39  \w     72.00 110.00   0.50    0.54    --  103.25-125.00 -30.00   76
 40  \w     19.00  86.00   0.50    0.13    --   47.70-113.00  62.00  134
 41  \w     50.00 109.00   0.50    0.54    --  103.25-113.00  62.00  118
 42  \w     26.00  51.00   0.50    0.13    --   47.95-113.00  62.00   50
 43  \w   -119.00 -33.00   0.50    0.13    --  -47.95 -57.00 150.00  172
 44  \w   -119.00 -33.00   0.50    0.13    --  -47.95 -57.00  30.00  172
 45  \w   -120.00 -25.00   0.50    0.13    --  -47.95 -77.00-120.00  190
 46  \w   -120.00-101.00   0.50    0.13    --  -47.95 -77.00 120.00   38
;
_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      0.1069265000
_diffrn_orient_matrix_UB_12      -0.0616357000
_diffrn_orient_matrix_UB_13      0.0117143000
_diffrn_orient_matrix_UB_21      0.0396793000
_diffrn_orient_matrix_UB_22      0.1901023000
_diffrn_orient_matrix_UB_23      0.0246251000
_diffrn_orient_matrix_UB_31      0.0275252000
_diffrn_orient_matrix_UB_32      -0.0360282000
_diffrn_orient_matrix_UB_33      0.1098275000
_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  0.0598
_diffrn_reflns_av_unetI/netI     0.0462
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.974
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            20789
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.952
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.384
_diffrn_reflns_theta_min         3.364
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'PhotonJet R (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.887
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.81046
_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    1.373
_exptl_crystal_description       block
_exptl_crystal_F_000             644
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.205
_refine_diff_density_min         -0.219
_refine_diff_density_rms         0.044
_refine_ls_abs_structure_details
;
 Flack x determined using 2233 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.01(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     405
_refine_ls_number_reflns         5827
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.050
_refine_ls_R_factor_all          0.0406
_refine_ls_R_factor_gt           0.0365
_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^)+(0.0497P)^2^+0.2613P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0917
_refine_ls_wR_factor_ref         0.0958
_reflns_Friedel_coverage         0.811
_reflns_Friedel_fraction_full    0.990
_reflns_Friedel_fraction_max     0.925
_reflns_number_gt                5394
_reflns_number_total             5827
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            np1c00878_si_005.cif
_cod_data_source_block           chy_21_auto
_cod_database_code               1566284
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.974
_shelx_estimated_absorpt_t_min   0.747
_reflns_odcompleteness_completeness 99.86
_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:
 C30(H30), C13(H13), C31(H31), C12(H12)
2.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C32(H32A,H32B), C21(H21A,H21B), C14(H14A,H14B)
2.c Aromatic/amide H refined with riding coordinates:
 C8(H8), C25(H25)
2.d Idealised Me refined as rotating group:
 C39(H39A,H39B,H39C), C35(H35A,H35B,H35C), C17(H17A,H17B,H17C), C43(H43A,H43B,
 H43C), C44(H44A,H44B,H44C), C40(H40A,H40B,H40C)
2.e Idealised tetrahedral OH refined as rotating group:
 O42(H42), O38(H38)
;
_shelx_res_checksum              10941
_shelx_hkl_checksum              95377
_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 2.019
_oxdiff_exptl_absorpt_empirical_full_min 0.539