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_1566289
_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         'C2 H6 O S, C32 H34 O11'
_chemical_formula_sum            'C34 H40 O12 S'
_chemical_formula_weight         672.72
_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     direct
_audit_creation_date             2021-05-14
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 110.9770(10)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   12.36210(10)
_cell_length_b                   11.05130(10)
_cell_length_c                   13.31830(10)
_cell_measurement_reflns_used    54184
_cell_measurement_temperature    100.03(10)
_cell_measurement_theta_max      76.5570
_cell_measurement_theta_min      3.5250
_cell_volume                     1698.92(3)
_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 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.03(10)
_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 0.999
_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    0.05    --   47.75  57.00  60.00  174
  2  \w     25.00 121.00   0.50    0.05    --   47.75  77.00 -30.00  192
  3  \w     33.00 120.00   0.50    0.05    --   47.75  57.00 -30.00  174
  4  \w     25.00 121.00   0.50    0.05    --   47.75  77.00-120.00  192
  5  \w     35.00 121.00   0.50    0.05    --   47.75  37.00-150.00  172
  6  \w     34.00 105.00   0.50    0.05    --  106.69 -94.00 -30.00  142
  7  \w     34.00 106.00   0.50    0.05    --  106.69-103.00-144.00  144
  8  \w      0.00  83.00   0.50    0.05    --   47.75-103.00-144.00  166
  9  \w     34.00 105.00   0.50    0.05    --  106.69 -94.00-120.00  142
 10  \w     34.00 111.00   0.50    0.05    --  106.69-125.00  60.00  154
 11  \w     34.00 105.00   0.50    0.05    --  106.69 -94.00  90.00  142
 12  \w     34.00 105.00   0.50    0.05    --  106.69 -94.00 150.00  142
 13  \w    -27.00  30.00   0.50    0.05    --   47.75 -19.00 -30.00  114
 14  \w    -27.00  30.00   0.50    0.05    --   47.75 -19.00  30.00  114
 15  \w    -25.00  45.00   0.50    0.05    --   47.75 -37.00 -60.00  140
 16  \w     34.00 109.00   0.50    0.05    --  106.69 -77.00-120.00  150
 17  \w     34.00  75.00   0.50    0.05    --  106.69 -61.00 -60.00   82
 18  \w     91.00 178.00   0.50    0.05    --  106.69 103.00 -42.00  174
 19  \w     90.00 178.00   0.50    0.05    --  106.69  61.00 -60.00  176
 20  \w     94.00 178.00   0.50    0.05    --  106.69  45.00  30.00  168
 21  \w     93.00 178.00   0.50    0.05    --  106.69  15.00 120.00  170
 22  \w    -62.00  25.00   0.50    0.05    --  -47.75  57.00 -90.00  174
 23  \w    -23.00  28.00   0.50    0.05    --  -47.75  19.00 -30.00  102
 24  \w    -38.00  26.00   0.50    0.05    --  -47.75  37.00-120.00  128
 25  \w    -83.00   7.00   0.50    0.05    --  -47.75 103.00 -42.00  180
 26  \w   -106.00 -28.00   0.50    0.05    -- -101.00 103.00 -42.00  156
 27  \w   -120.00 -28.00   0.50    0.05    -- -101.00 137.00  -4.41  184
 28  \w   -123.00 -28.00   0.50    0.05    -- -101.00 141.00  18.03  190
 29  \w   -123.00 -28.00   0.50    0.05    -- -101.00 141.00 153.00  190
 30  \w    -68.00 -28.00   0.50    0.05    -- -101.00  61.00  30.00   80
 31  \w    -68.00 -28.00   0.50    0.05    -- -101.00  61.00 150.00   80
 32  \w    -68.00 -28.00   0.50    0.05    -- -101.00  61.00 -60.00   80
 33  \w    -68.00 -28.00   0.50    0.05    -- -101.00  61.00 -30.00   80
 34  \w    -68.00 -28.00   0.50    0.05    -- -101.00  61.00 -90.00   80
 35  \w   -102.00 -28.00   0.50    0.05    -- -101.00  77.00-120.00  148
 36  \w    -68.00 -28.00   0.50    0.05    -- -101.00  61.00-180.00   80
 37  \w   -173.00 -88.00   0.50    0.05    -- -101.00 -45.00-150.00  170
 38  \w   -173.00 -78.00   0.50    0.05    -- -101.00 -77.00 -60.00  190
 39  \w   -173.00 -78.00   0.50    0.05    -- -101.00 -77.00  30.00  190
 40  \w   -173.00 -78.00   0.50    0.05    -- -101.00 -77.00 137.34  190
 41  \w   -173.00 -78.00   0.50    0.05    -- -101.00 -77.00 120.00  190
 42  \w   -173.00 -78.00   0.50    0.05    -- -101.00 -77.00  90.00  190
 43  \w   -173.00 -79.00   0.50    0.05    -- -101.00 -74.00 -17.86  188
 44  \w   -173.00 -78.00   0.50    0.05    -- -101.00 -76.00 -88.66  190
 45  \w   -173.00 -79.00   0.50    0.05    -- -101.00 -75.00-158.92  188
 46  \w   -173.00 -83.00   0.50    0.05    -- -101.00 -64.00-158.51  180
 47  \w   -173.00 -79.00   0.50    0.05    -- -101.00 -74.00 -48.04  188
 48  \w   -173.00 -84.00   0.50    0.05    -- -101.00 -61.00-120.00  178
 49  \w   -172.00 -85.00   0.50    0.05    -- -101.00 -59.00-149.86  174
 50  \w   -172.00 -87.00   0.50    0.05    -- -101.00 -52.00 -15.08  170
 51  \w   -173.00 -80.00   0.50    0.05    -- -101.00 -72.00  63.31  186
 52  \w   -172.00 -87.00   0.50    0.05    -- -101.00 -51.00 126.11  170
 53  \w   -172.00 -87.00   0.50    0.05    -- -101.00 -51.00 145.73  170
 54  \w   -173.00 -83.00   0.50    0.05    -- -101.00 -66.00 177.77  180
 55  \w   -173.00 -80.00   0.50    0.05    -- -101.00 -73.00 103.20  186
 56  \w   -172.00 -87.00   0.50    0.05    -- -101.00 -51.00  22.72  170
 57  \w   -172.00 -87.00   0.50    0.05    -- -101.00 -50.00 -57.82  170
 58  \w   -173.00 -85.00   0.50    0.05    -- -101.00-103.00-144.00  176
 59  \w   -119.00 -74.00   0.50    0.05    --  -47.75-125.00 -90.00   90
 60  \w   -119.00 -25.00   0.50    0.05    --  -47.75 -77.00-180.00  188
 61  \w   -119.00 -25.00   0.50    0.05    --  -47.75 -77.00  60.00  188
 62  \w   -119.00 -29.00   0.50    0.05    --  -47.75 -66.00  97.55  180
 63  \w    -62.00 -37.00   0.50    0.05    --  -47.75 103.00 -42.00   50
 64  \w     17.00  42.00   0.50    0.05    --   47.75-103.00-144.00   50
 65  \w   -119.00 -25.00   0.50    0.05    --  -47.75 -77.00-120.00  188
 66  \w   -119.00 -25.00   0.50    0.05    --  -47.75 -77.00 -60.00  188
 67  \w   -119.00 -25.00   0.50    0.05    --  -47.75 -77.00 120.00  188
 68  \w   -119.00 -46.50   0.50    0.05    --  -47.75 -77.00   0.00  145
;
_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      -0.0068001000
_diffrn_orient_matrix_UB_12      0.0078758000
_diffrn_orient_matrix_UB_13      -0.1175980000
_diffrn_orient_matrix_UB_21      -0.0372811000
_diffrn_orient_matrix_UB_22      0.1334566000
_diffrn_orient_matrix_UB_23      -0.0044393000
_diffrn_orient_matrix_UB_31      0.1279919000
_diffrn_orient_matrix_UB_32      0.0394074000
_diffrn_orient_matrix_UB_33      0.0386700000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0466
_diffrn_reflns_av_unetI/netI     0.0182
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            62621
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.484
_diffrn_reflns_theta_min         3.554
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'PhotonJet R (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.377
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.62023
_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            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.315
_exptl_crystal_description       plate
_exptl_crystal_F_000             712
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.224
_refine_diff_density_min         -0.247
_refine_diff_density_rms         0.033
_refine_ls_abs_structure_details
;
 Flack x determined using 3127 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.008(4)
_refine_ls_extinction_coef       0.0024(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     436
_refine_ls_number_reflns         6897
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.059
_refine_ls_R_factor_all          0.0259
_refine_ls_R_factor_gt           0.0257
_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^)+(0.0414P)^2^+0.2580P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0692
_refine_ls_wR_factor_ref         0.0693
_reflns_Friedel_coverage         0.881
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.982
_reflns_number_gt                6796
_reflns_number_total             6897
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            np1c00878_si_012.cif
_cod_data_source_block           chy_23b_auto
_cod_database_code               1566289
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_max   0.934
_shelx_estimated_absorpt_t_min   0.576
_diffrn_oxdiff_digest_frames
;
0112496eba3478d1fcddda340dd6be6cd40978632dd
;
_diffrn_oxdiff_digest_hkl
;
014174402d938e5b1202824426d730d41031f5
;
_reflns_odcompleteness_completeness 100.00
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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), C31(H31), C16(H16), C15(H15)
2.b Secondary CH2 refined with riding coordinates:
 C21(H21A,H21B), C14(H14A,H14B), C32(H32A,H32B)
2.c Aromatic/amide H refined with riding coordinates:
 C6(H6), C13(H13), C25(H25)
2.d Idealised Me refined as rotating group:
 C47(H47A,H47B,H47C), C40(H40A,H40B,H40C), C46(H46A,H46B,H46C), C35(H35A,H35B,
 H35C), C39(H39A,H39B,H39C), C4(H4A,H4B,H4C), C3(H3A,H3B,H3C), C42(H42A,H42B,
 H42C)
2.e Idealised tetrahedral OH refined as rotating group:
 O45(H45), O44(H44), O38(H38)
;
_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 2.067
_oxdiff_exptl_absorpt_empirical_full_min 0.491