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_1566283
_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, H2 O, C H4 O'
_chemical_formula_sum            'C33 H40 O14'
_chemical_formula_weight         660.65
_space_group_crystal_system      triclinic
_space_group_IT_number           1
_space_group_name_Hall           'P 1'
_space_group_name_H-M_alt        'P 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_audit_creation_date             2021-01-08
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6226)
;
_cell_angle_alpha                85.062(2)
_cell_angle_beta                 88.911(2)
_cell_angle_gamma                86.614(2)
_cell_formula_units_Z            1
_cell_length_a                   7.2806(2)
_cell_length_b                   9.8268(3)
_cell_length_c                   11.0309(3)
_cell_measurement_reflns_used    21867
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      73.6300
_cell_measurement_theta_min      3.9900
_cell_volume                     784.83(4)
_computing_cell_refinement       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_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    'SHELXS  (Sheldrick, 2008)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.01(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.964
_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     35.00 121.00   0.50    0.05    --   47.45  37.00 -30.00  172
  2  \w     25.00 120.00   0.50    0.05    --   47.45  77.00-150.00  190
  3  \w     35.00 121.00   0.50    0.05    --   47.45  37.00-120.00  172
  4  \w     25.00 120.00   0.50    0.05    --   47.45  77.00 -60.00  190
  5  \w     25.00 120.00   0.50    0.05    --   47.45  77.00 -30.00  190
  6  \w     25.00 120.00   0.50    0.05    --   47.45  77.00 150.00  190
  7  \w     16.00  42.00   0.50    0.05    --   40.00  81.00  37.05   52
  8  \w    -18.00  18.00   0.50    0.05    --   16.00 101.00  54.59   72
  9  \w    -41.00 -10.00   0.50    0.05    --    4.00 120.00  42.91   62
 10  \w     -9.00  22.00   0.50    0.05    --   24.00  99.00  75.17   62
 11  \w      7.00  42.00   0.50    0.05    --   36.00  90.00 123.37   70
 12  \w     28.00 125.00   0.50    0.05    --   52.00  79.00-111.49  194
 13  \w     29.00 125.00   0.50    0.05    --   52.00  77.00 -28.98  192
 14  \w     81.00 176.00   0.50    0.09    --  103.25  77.00  30.00  190
 15  \w     37.00 132.00   0.50    0.05    --   60.00  78.00 152.10  190
 16  \w     29.00 125.00   0.50    0.05    --   52.00  78.00 117.24  192
 17  \w     43.00 137.00   0.50    0.05    --   64.00  72.00  79.54  188
 18  \w     30.00 125.00   0.50    0.05    --   52.00  76.00  60.27  190
 19  \w     52.00  77.00   0.50    0.05    --   72.00  73.00 -75.19   50
 20  \w     92.00 176.00   0.50    0.09    --  103.25 101.00-138.00  168
 21  \w     74.00  99.00   0.50    0.09    --  103.25 -77.00 120.00   50
 22  \w     31.00  73.00   0.50    0.09    --  103.25 -77.00 120.00   84
 23  \w    -26.00  46.00   0.50    0.05    --   47.45 -37.00 150.00  144
 24  \w     34.00  74.00   0.50    0.09    --  103.25 -61.00  30.00   80
 25  \w     32.00  72.00   0.50    0.09    --  103.25 -61.00 -30.00   80
 26  \w     31.00  74.00   0.50    0.09    --  103.25 -61.00 -60.00   86
 27  \w     39.00  73.00   0.50    0.09    --  103.25 -94.00 -90.00   68
 28  \w     33.00 111.00   0.50    0.09    --  103.25-125.00-120.00  156
 29  \w     33.00 105.00   0.50    0.09    --  103.25-125.00 -90.00  144
 30  \w     48.00  74.00   0.50    0.09    --  103.25-125.00  30.00   52
 31  \w     77.00 107.00   0.50    0.09    --  103.25-125.00  30.00   60
 32  \w     31.00 106.00   0.50    0.09    --  103.25-101.00 116.00  150
 33  \w    -11.00  82.00   0.50    0.05    --   47.45-101.00 116.00  186
 34  \w   -106.00 -28.00   0.50    0.09    -- -101.00 101.00-138.00  156
 35  \w   -110.00 -61.00   0.50    0.09    -- -101.00 125.00 -90.00   98
 36  \w   -104.00 -70.00   0.50    0.09    -- -101.00 125.00  30.00   68
 37  \w    -56.00 -29.00   0.50    0.09    -- -101.00 125.00  30.00   54
 38  \w   -112.00 -28.00   0.50    0.09    -- -101.00 125.00   0.00  168
 39  \w    -82.00  18.00   0.50    0.05    --  -47.45 101.00-138.00  200
 40  \w    -65.00 -28.00   0.50    0.09    -- -101.00  61.00 -60.00   74
 41  \w    -67.00 -29.00   0.50    0.09    -- -101.00  61.00-150.00   76
 42  \w    -57.00 -29.00   0.50    0.09    -- -101.00  61.00-180.00   56
 43  \w    -68.00 -31.00   0.50    0.09    -- -101.00  61.00  60.00   74
 44  \w   -121.00 -35.00   0.50    0.05    --  -47.45 -37.00  60.00  172
 45  \w   -137.00 -40.00   0.50    0.05    --  -64.00 -80.00 175.17  194
 46  \w    -87.00 -61.00   0.50    0.09    --  -84.00 -80.00  54.22   52
 47  \w   -113.00 -79.00   0.50    0.09    -- -101.00 -80.00 141.00   68
 48  \w   -149.00-124.00   0.50    0.09    --  -84.00 -80.00  54.22   50
 49  \w   -154.00-121.00   0.50    0.09    -- -101.00 -79.00  68.33   66
 50  \w   -144.00-117.00   0.50    0.09    -- -101.00 -80.00 141.00   54
 51  \w   -116.00 -77.00   0.50    0.09    -- -101.00 -79.00  68.33   78
 52  \w   -132.00 -36.00   0.50    0.05    --  -60.00 -80.00  15.21  192
 53  \w   -123.00 -80.00   0.50    0.09    -- -101.00 -78.00 -19.28   86
 54  \w   -150.00-124.00   0.50    0.09    -- -101.00 -78.00 -19.28   52
 55  \w   -137.00 -45.00   0.50    0.05    --  -68.00 -77.00  82.24  184
 56  \w   -121.00 -77.00   0.50    0.09    -- -101.00 -80.00 -56.29   88
 57  \w   -167.00-125.00   0.50    0.09    -- -101.00 -80.00 -56.29   84
 58  \w   -160.00-117.00   0.50    0.09    --  -88.00 -76.00 -26.11   86
 59  \w   -171.00 -79.00   0.50    0.09    -- -101.00 -78.00-174.22  184
 60  \w    -82.00 -56.00   0.50    0.09    --  -76.00 -76.00-166.65   52
 61  \w   -132.00 -38.00   0.50    0.05    --  -60.00 -75.00-139.00  188
 62  \w    -93.00 -66.00   0.50    0.09    --  -88.00 -76.00 -26.11   54
 63  \w    -87.00 -60.00   0.50    0.09    --  -80.00 -74.00 -52.15   54
 64  \w    -91.00 -62.00   0.50    0.09    --  -84.00 -75.00 122.90   58
 65  \w    -94.00 -62.00   0.50    0.09    --  -84.00 -75.00 156.12   64
 66  \w   -104.00 -71.00   0.50    0.09    --  -92.00 -75.00 178.42   66
 67  \w    -96.00 -63.00   0.50    0.09    --  -84.00 -73.00 141.32   66
 68  \w   -173.00 -80.00   0.50    0.09    -- -101.00 -75.00 148.28  186
 69  \w    -81.00 -55.00   0.50    0.09    --  -76.00 -73.00 -37.73   52
 70  \w   -111.00 -63.00   0.50    0.09    --  -84.00 -73.00-115.69   96
 71  \w   -111.00 -80.00   0.50    0.09    -- -101.00 -72.00-139.91   62
 72  \w   -157.00 -80.00   0.50    0.09    -- -101.00 -73.00-151.61  154
 73  \w   -156.00-115.00   0.50    0.09    -- -101.00 -72.00-139.91   82
 74  \w   -140.00-114.00   0.50    0.05    --  -72.00 -73.00-166.02   52
 75  \w    -77.00 -51.00   0.50    0.05    --  -72.00 -73.00-166.02   52
 76  \w    -96.00 -63.00   0.50    0.09    --  -84.00 -72.00 -70.96   66
 77  \w   -122.00 -73.00   0.50    0.09    --  -92.00 -69.00   9.18   98
 78  \w    -95.00 -59.00   0.50    0.09    --  -80.00 -72.00  82.64   72
 79  \w   -107.00 -72.00   0.50    0.09    --  -92.00 -70.00  72.12   70
 80  \w   -137.00 -43.00   0.50    0.05    --  -64.00 -72.00 134.48  188
 81  \w   -143.00 -83.00   0.50    0.09    -- -101.00 -69.00 155.57  120
 82  \w   -138.00 -83.00   0.50    0.09    -- -101.00 -68.00  88.77  110
 83  \w    -77.00 -50.00   0.50    0.05    --  -68.00 -67.00  95.13   54
 84  \w   -139.00 -81.00   0.50    0.09    -- -101.00 -69.00  21.59  116
 85  \w    -80.00 -53.00   0.50    0.05    --  -72.00 -68.00 -17.71   54
 86  \w    -80.00 -53.00   0.50    0.05    --  -72.00 -68.00 -34.95   54
 87  \w    -88.00 -58.00   0.50    0.09    --  -76.00 -66.00 -90.25   60
 88  \w   -122.00 -97.00   0.50    0.05    --  -68.00 -66.00-108.36   50
 89  \w   -140.00 -49.00   0.50    0.05    --  -68.00 -67.00-147.78  182
 90  \w    -79.00 -52.00   0.50    0.05    --  -68.00 -66.00-108.36   54
 91  \w   -125.00 -83.00   0.50    0.09    -- -101.00 -66.00-126.03   84
 92  \w   -136.00 -78.00   0.50    0.09    --  -96.00 -65.00 -55.71  116
 93  \w   -104.00 -75.00   0.50    0.09    --  -92.00 -62.00-110.67   58
 94  \w   -100.00 -66.00   0.50    0.09    --  -84.00 -64.00   4.45   68
 95  \w    -95.00 -70.00   0.50    0.09    --  -88.00 -64.00  17.20   50
 96  \w   -153.00-115.00   0.50    0.09    --  -88.00 -64.00  17.20   76
 97  \w   -167.00-141.00   0.50    0.09    -- -101.00 -61.00  90.00   52
 98  \w   -122.00 -84.00   0.50    0.09    -- -101.00 -61.00  90.00   76
 99  \w   -168.00 -79.00   0.50    0.09    --  -96.00 -63.00  -4.66  178
100  \w   -160.00-117.00   0.50    0.09    --  -92.00 -62.00-110.67   86
101  \w   -108.00 -81.00   0.50    0.09    --  -96.00 -59.00-145.22   54
102  \w    -96.00 -70.00   0.50    0.09    --  -84.00 -59.00 162.21   52
103  \w   -173.00 -85.00   0.50    0.09    -- -101.00-101.00 116.00  176
104  \w     27.00  53.00   0.50    0.05    --   47.95  77.00  30.00   52
105  \w     32.00  58.00   0.50    0.05    --   56.00  80.00  76.82   52
106  \w    -76.00 -50.00   0.50    0.05    --  -68.00 -69.00 -75.94   52
107  \w    -80.00 -54.00   0.50    0.09    --  -76.00 -74.00  26.06   52
108  \w    -93.00 -67.00   0.50    0.09    --  -84.00 -63.00-142.05   52
109  \w   -164.00-138.00   0.50    0.09    --  -96.00 -80.00  77.46   52
110  \w   -104.00 -78.00   0.50    0.09    --  -96.00 -64.00-161.99   52
111  \w    -98.00 -72.00   0.50    0.09    --  -96.00 -80.00  77.46   52
112  \w   -155.00-129.00   0.50    0.09    --  -96.00 -64.00-161.99   52
113  \w   -140.00-114.00   0.50    0.09    -- -101.00 -45.00   0.00   52
114  \w   -170.00-144.00   0.50    0.09    -- -101.00 -45.00   0.00   52
115  \w    -83.00 -37.00   0.50    0.09    -- -101.00  77.00 150.00   92
116  \w   -107.00 -81.00   0.50    0.09    -- -101.00 -71.00-114.33   52
117  \w   -168.00-124.00   0.50    0.09    -- -101.00 -71.00-114.33   88
118  \w     36.00 129.00   0.50    0.05    --   56.00  71.00  -4.88  186
119  \w   -140.00 -48.00   0.50    0.05    --  -68.00 -69.00 -75.94  184
120  \w   -140.00 -48.00   0.50    0.05    --  -68.00 -69.00-134.94  184
121  \w   -140.00 -48.00   0.50    0.05    --  -68.00 -70.00  84.37  184
122  \w   -145.00 -53.00   0.50    0.05    --  -72.00 -67.00  30.57  184
123  \w    -56.00 -31.00   0.50    0.05    --  -47.95 101.00-139.00   50
124  \w   -120.00  24.00   0.50    0.05    --  -47.95   0.00-180.00  288
125  \w   -120.00  24.00   0.50    0.05    --  -47.95   0.00-120.00  288
126  \w   -120.00  24.00   0.50    0.05    --  -47.95   0.00 -90.00  288
127  \w   -120.00  24.00   0.50    0.05    --  -47.95   0.00-150.00  288
128  \w   -120.00  10.00   0.50    0.05    --  -47.95   0.00  60.00  260
129  \w   -120.00  24.00   0.50    0.05    --  -47.95   0.00   0.00  288
130  \w   -120.00  24.00   0.50    0.05    --  -47.95   0.00 -30.00  288
131  \w   -120.00  24.00   0.50    0.05    --  -47.95   0.00 -60.00  288
132  \w   -120.00  24.00   0.50    0.05    --  -47.95   0.00  30.00  288
133  \w    -24.00 120.00   0.50    0.05    --   47.95   0.00-150.00  288
134  \w    -24.00 120.00   0.50    0.05    --   47.95   0.00  30.00  288
135  \w    -24.00 120.00   0.50    0.05    --   47.95   0.00   0.00  288
136  \w    -24.00 120.00   0.50    0.05    --   47.95   0.00  60.00  288
137  \w    -24.00 120.00   0.50    0.05    --   47.95   0.00  90.00  288
138  \w    -24.00 120.00   0.50    0.05    --   47.95   0.00-180.00  288
139  \w     25.00 120.00   0.50    0.05    --   47.95  77.00 -90.00  190
140  \w    -24.00   4.00   0.50    0.05    --   47.95   0.00 -30.00   56
;
_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      -0.0502786000
_diffrn_orient_matrix_UB_12      0.0320614000
_diffrn_orient_matrix_UB_13      0.1312247000
_diffrn_orient_matrix_UB_21      -0.2052817000
_diffrn_orient_matrix_UB_22      -0.0108131000
_diffrn_orient_matrix_UB_23      -0.0267905000
_diffrn_orient_matrix_UB_31      0.0164610000
_diffrn_orient_matrix_UB_32      -0.1539437000
_diffrn_orient_matrix_UB_33      0.0414294000
_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  0.0743
_diffrn_reflns_av_unetI/netI     0.0328
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.964
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            44671
_diffrn_reflns_point_group_measured_fraction_full 0.977
_diffrn_reflns_point_group_measured_fraction_max 0.924
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.337
_diffrn_reflns_theta_min         4.023
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'PhotonJet R (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.924
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.60719
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.84a (Rigaku Oxford Diffraction, 2020)
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    1.398
_exptl_crystal_description       plate
_exptl_crystal_F_000             350
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.258
_refine_diff_density_min         -0.251
_refine_diff_density_rms         0.049
_refine_ls_abs_structure_details
;
 Flack x determined using 2556 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.08(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     441
_refine_ls_number_reflns         6013
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.046
_refine_ls_R_factor_all          0.0423
_refine_ls_R_factor_gt           0.0399
_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^)+(0.0786P)^2^+0.0387P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1072
_refine_ls_wR_factor_ref         0.1091
_reflns_Friedel_coverage         0.916
_reflns_Friedel_fraction_full    0.956
_reflns_Friedel_fraction_max     0.883
_reflns_number_gt                5673
_reflns_number_total             6013
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            np1c00878_si_006.cif
_cod_data_source_block           chy_3
_cod_database_code               1566283
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.964
_shelx_estimated_absorpt_t_min   0.823
_reflns_odcompleteness_completeness 99.93
_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, All O(H,H) groups
2.a Free rotating group:
 O45(H45A,H45B)
2.b Ternary CH refined with riding coordinates:
 C17(H17), C16(H16), C3(H3), C2(H2)
2.c Secondary CH2 refined with riding coordinates:
 C18(H18A,H18B), C4(H4A,H4B)
2.d Aromatic/amide H refined with riding coordinates:
 C26(H26), C12(H12)
2.e Idealised Me refined as rotating group:
 C35(H35A,H35B,H35C), C36(H36A,H36B,H36C), C44(H44A,H44B,H44C), C30(H30A,H30B,
 H30C), C43(H43A,H43B,H43C), C38(H38A,H38B,H38C), C47(H47A,H47B,H47C)
2.f Idealised tetrahedral OH refined as rotating group:
 O33(H33), O39(H39), O31(H31), O42(H42), O34(H34), O40(H40), O46(H46)
;
_shelx_res_checksum              60497
_shelx_hkl_checksum              5384
_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 2.439
_oxdiff_exptl_absorpt_empirical_full_min 0.532