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_1566291
_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             2021-01-08
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6226)
;
_cell_angle_alpha                90
_cell_angle_beta                 100.5780(10)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   8.08670(10)
_cell_length_b                   10.26000(10)
_cell_length_c                   17.8397(2)
_cell_measurement_reflns_used    35690
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      74.7940
_cell_measurement_theta_min      4.3660
_cell_volume                     1455.00(3)
_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    'SHELXT 2014/5 (Sheldrick, 2014)'
_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 0.991
_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     24.00 120.00   0.50    0.05    --   47.70  80.00  19.00  192
  2  \w     87.00 176.00   0.50    0.05    --  103.25  61.00 -60.00  178
  3  \w     79.00 176.00   0.50    0.05    --  103.25  80.00  19.00  194
  4  \w     91.00 178.00   0.50    0.05    --  103.25  30.00   0.00  174
  5  \w     91.00 175.00   0.50    0.05    --  103.25  45.00  60.00  168
  6  \w     90.00 178.00   0.50    0.05    --  103.25  15.00 120.00  176
  7  \w     91.00 178.00   0.50    0.05    --  103.25  30.00 150.00  174
  8  \w     90.00 178.00   0.50    0.05    --  103.25  15.00 150.00  176
  9  \w    -23.00  28.00   0.50    0.05    --  -47.70  19.00   0.00  102
 10  \w    -39.00  26.00   0.50    0.05    --  -47.70  37.00   0.00  130
 11  \w    -72.00  25.00   0.50    0.05    --  -47.70  80.00  19.00  194
 12  \w    -23.00  28.00   0.50    0.05    --  -47.70  19.00 150.00  102
 13  \w   -125.00 -28.00   0.50    0.05    -- -101.00  80.00  19.00  194
 14  \w    -68.00 -28.00   0.50    0.05    -- -101.00  61.00  90.00   80
 15  \w    -68.00 -28.00   0.50    0.05    -- -101.00  61.00 -30.00   80
 16  \w    -68.00 -28.00   0.50    0.05    -- -101.00  61.00-120.00   80
 17  \w   -102.00 -28.00   0.50    0.05    -- -101.00  77.00-150.00  148
 18  \w   -174.00 -88.00   0.50    0.05    -- -101.00 -30.00 -60.00  172
 19  \w   -173.00 -77.00   0.50    0.05    -- -101.00 -80.00-104.00  192
 20  \w   -119.00 -24.00   0.50    0.05    --  -47.70 -80.00-104.00  190
 21  \w   -173.00 -88.00   0.50    0.05    -- -101.00 -45.00 120.00  170
 22  \w   -119.00 -25.00   0.50    0.05    --  -47.70 -77.00 150.00  188
 23  \w   -119.00 -74.00   0.50    0.05    --  -47.70-125.00 120.00   90
 24  \w   -119.00 -74.00   0.50    0.05    --  -47.70-125.00  60.00   90
 25  \w   -173.00 -74.00   0.50    0.05    -- -101.00-125.00   0.00  198
 26  \w   -173.00 -84.00   0.50    0.05    -- -101.00 -94.00-150.00  178
 27  \w   -119.00 -74.00   0.50    0.05    --  -47.70-125.00-120.00   90
 28  \w    -24.00  72.00   0.50    0.05    --   47.70 -80.00-104.00  192
 29  \w     31.00  75.00   0.50    0.05    --  103.25 -61.00 -30.00   88
 30  \w     31.00 127.00   0.50    0.05    --  103.25 -80.00-104.00  192
 31  \w    -27.00  30.00   0.50    0.05    --   47.70 -19.00-120.00  114
 32  \w     31.00  75.00   0.50    0.05    --  103.25 -61.00  30.00   88
 33  \w     31.00  75.00   0.50    0.05    --  103.25 -61.00  90.00   88
 34  \w     31.00  75.00   0.50    0.05    --  103.25 -61.00  60.00   88
 35  \w     31.00 111.00   0.50    0.05    --  103.25-125.00 -30.00  160
 36  \w     31.00 111.00   0.50    0.05    --  103.25-125.00 -90.00  160
 37  \w     31.00 111.00   0.50    0.05    --  103.25-125.00  60.00  160
 38  \w    -48.00 -23.00   0.50    0.05    --  -47.95  80.00  18.00   50
 39  \w     86.00 111.00   0.50    0.05    --  103.25-125.00   0.00   50
 40  \w    133.00 169.00   0.50    0.05    --  103.25  45.00-150.00   72
 41  \w    112.00 138.00   0.50    0.05    --  103.25  45.00-180.00   52
 42  \w     33.00  59.00   0.50    0.05    --  103.25-125.00   0.00   52
 43  \w   -119.00 -33.00   0.50    0.05    --  -47.95 -57.00  60.00  172
 44  \w   -119.00 -33.00   0.50    0.05    --  -47.95 -57.00 -90.00  172
 45  \w   -119.00 -33.00   0.50    0.05    --  -47.95 -57.00-180.00  172
 46  \w     33.00 119.00   0.50    0.05    --   47.95  57.00-120.00  172
 47  \w     25.00 120.00   0.50    0.05    --   47.95  77.00 -60.00  190
 48  \w      0.00  25.00   0.50    0.05    --   47.95 -80.00-104.00   50
 49  \w     25.00 120.00   0.50    0.05    --   47.95  77.00 -30.00  190
 50  \w     36.00 121.00   0.50    0.05    --   47.95  37.00   0.00  170
 51  \w     25.00 110.00   0.50    0.05    --   47.95  77.00 120.00  170
 52  \w     25.00 120.00   0.50    0.05    --   47.95  77.00  90.00  190
 53  \w   -149.00-124.00   0.50    0.05    -- -101.00 -80.00-104.00   50
 54  \w   -119.00 -33.00   0.50    0.05    --  -47.95 -57.00 120.00  172
 55  \w   -121.00 -35.00   0.50    0.05    --  -47.95 -37.00-150.00  172
 56  \w     36.00 121.00   0.50    0.05    --   47.95  37.00-120.00  170
 57  \w     25.00 120.00   0.50    0.05    --   47.95  77.00-180.00  190
 58  \w     33.00 119.00   0.50    0.05    --   47.95  57.00 -60.00  172
 59  \w    -26.00  30.00   0.50    0.05    --   47.95 -19.00 120.00  112
 60  \w     25.00 120.00   0.50    0.05    --   47.95  77.00-150.00  190
 61  \w     25.00  72.50   0.50    0.05    --   47.95  77.00   0.00   95
;
_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      -0.1492120000
_diffrn_orient_matrix_UB_12      -0.0946661000
_diffrn_orient_matrix_UB_13      -0.0038630000
_diffrn_orient_matrix_UB_21      -0.0751169000
_diffrn_orient_matrix_UB_22      0.0878411000
_diffrn_orient_matrix_UB_23      0.0552654000
_diffrn_orient_matrix_UB_31      -0.0982541000
_diffrn_orient_matrix_UB_32      0.0766101000
_diffrn_orient_matrix_UB_33      -0.0681674000
_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  0.1148
_diffrn_reflns_av_unetI/netI     0.0418
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            42427
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.974
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.091
_diffrn_reflns_theta_min         4.994
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'PhotonJet R (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.900
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.84978
_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    1.394
_exptl_crystal_description       block
_exptl_crystal_F_000             644
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.194
_refine_diff_density_min         -0.207
_refine_diff_density_rms         0.045
_refine_ls_abs_structure_details
;
 Flack x determined using 2561 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.01(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.084
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     405
_refine_ls_number_reflns         5845
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.084
_refine_ls_R_factor_all          0.0368
_refine_ls_R_factor_gt           0.0363
_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^)+(0.0623P)^2^+0.1344P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0984
_refine_ls_wR_factor_ref         0.0989
_reflns_Friedel_coverage         0.857
_reflns_Friedel_fraction_full    0.997
_reflns_Friedel_fraction_max     0.955
_reflns_number_gt                5715
_reflns_number_total             5845
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            np1c00878_si_002.cif
_cod_data_source_block           chy_1
_cod_database_code               1566291
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.900
_shelx_estimated_absorpt_t_min   0.744
_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
2.a Ternary CH refined with riding coordinates:
 C31(H31), C12(H12), C13(H13), C30(H30)
2.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C21(H21A,H21B), C32(H32A,H32B), C14(H14A,H14B)
2.c Aromatic/amide H refined with riding coordinates:
 C27(H27), C8(H8)
2.d Idealised Me refined as rotating group:
 C44(H44A,H44B,H44C), C40(H40A,H40B,H40C), C39(H39A,H39B,H39C), C43(H43A,H43B,
 H43C), C35(H35A,H35B,H35C), C17(H17A,H17B,H17C)
2.e Idealised tetrahedral OH refined as rotating group:
 O41(H41), O38(H38)
;
_shelx_res_checksum              11546
_shelx_hkl_checksum              28650
_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 1.637
_oxdiff_exptl_absorpt_empirical_full_min 0.608