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_1566286
_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, C4 H8 O2'
_chemical_formula_sum            'C36 H42 O14'
_chemical_formula_weight         698.69
_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             2021-02-24
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6226)
;
_cell_angle_alpha                90
_cell_angle_beta                 95.4350(10)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   10.03660(10)
_cell_length_b                   10.75830(10)
_cell_length_c                   15.9163(2)
_cell_measurement_reflns_used    20381
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      75.0420
_cell_measurement_theta_min      4.0860
_cell_volume                     1710.86(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 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 1.000
_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     26.00 120.00   0.50    0.05    --   47.70  77.00   0.00  188
  2  \w     78.00 119.00   0.50    0.05    --   47.70  57.00-180.00   82
  3  \w     45.00  71.00   0.50    0.05    --   47.70  57.00-180.00   52
  4  \w    -19.00  13.00   0.50    0.05    --  -47.70  19.00   0.00   64
  5  \w   -101.00 -28.00   0.50    0.13    -- -101.00  77.00   0.00  146
  6  \w    -68.00 -28.00   0.50    0.13    -- -101.00  61.00  60.00   80
  7  \w    -64.00 -29.00   0.50    0.13    -- -101.00  61.00  90.00   70
  8  \w    -22.00  22.00   0.50    0.05    --  -47.70  19.00  60.00   88
  9  \w     92.00 117.00   0.50    0.13    --  103.25  15.00-150.00   50
 10  \w     83.00 108.00   0.50    0.13    --  103.25  77.00  30.00   50
 11  \w     94.00 175.00   0.50    0.13    --  103.25  45.00  90.00  162
 12  \w     97.00 169.00   0.50    0.13    --  103.25  45.00 120.00  144
 13  \w     90.00 118.00   0.50    0.13    --  103.25  15.00  30.00   56
 14  \w    135.00 169.00   0.50    0.13    --  103.25  15.00  30.00   68
 15  \w    135.00 171.00   0.50    0.13    --  103.25  15.00-150.00   72
 16  \w     32.00  74.00   0.50    0.13    --  103.25 -61.00-180.00   84
 17  \w     55.00  95.00   0.50    0.05    --   47.70-125.00 -90.00   80
 18  \w     80.00 109.00   0.50    0.13    --  103.25-125.00-120.00   58
 19  \w     37.00  74.00   0.50    0.13    --  103.25-125.00-120.00   74
 20  \w     42.00  70.00   0.50    0.13    --  103.25-125.00-150.00   56
 21  \w     75.00 106.00   0.50    0.13    --  103.25-125.00-150.00   62
 22  \w     84.00 109.00   0.50    0.13    --  103.25-125.00  30.00   50
 23  \w     68.00  93.00   0.50    0.13    --  103.25 -99.00  -1.00   50
 24  \w     50.00  76.00   0.50    0.13    --  103.25-125.00  30.00   52
 25  \w     39.00 111.00   0.50    0.13    --  103.25-125.00 150.00  144
 26  \w     11.00  38.00   0.50    0.05    --   47.70 -99.00  -1.00   54
 27  \w    121.00 152.00   0.50    0.13    --  103.25  99.00 104.00   62
 28  \w     88.00 162.00   0.50    0.13    --  103.25 125.00 150.00  148
 29  \w     75.00 106.00   0.50    0.13    --  103.25 -94.00 -90.00   62
 30  \w     38.00  64.00   0.50    0.13    --  103.25 -94.00 -90.00   52
 31  \w   -161.00-123.00   0.50    0.13    -- -101.00 -77.00  60.00   76
 32  \w   -105.00 -79.00   0.50    0.13    -- -101.00 -77.00  60.00   52
 33  \w   -114.00 -83.00   0.50    0.13    -- -101.00 -67.00  53.35   62
 34  \w   -169.00-108.00   0.50    0.13    -- -101.00 -45.00  30.00  122
 35  \w   -171.00 -85.00   0.50    0.13    -- -101.00 -61.00 -60.00  172
 36  \w   -170.00 -88.00   0.50    0.13    -- -101.00 -45.00 -90.00  164
 37  \w   -154.00-129.00   0.50    0.13    -- -101.00 -99.00  -1.00   50
 38  \w   -115.00 -89.00   0.50    0.05    --  -47.70-125.00  60.00   52
 39  \w   -108.00 -74.00   0.50    0.05    --  -47.70-125.00-120.00   68
 40  \w   -117.00 -82.00   0.50    0.05    --  -47.70-125.00-180.00   70
 41  \w    -67.00  22.00   0.50    0.05    --  -47.70  99.00 104.00  178
 42  \w   -112.00 -43.00   0.50    0.13    -- -101.00 125.00  30.00  138
 43  \w    -99.00 -73.00   0.50    0.13    -- -101.00 125.00  60.00   52
 44  \w    -72.00 -30.00   0.50    0.13    -- -101.00 125.00  60.00   84
 45  \w    -64.00 -39.00   0.50    0.13    -- -101.00  99.00 104.00   50
 46  \w      8.00  33.00   0.50    0.05    --   47.95 -99.00  -1.00   50
 47  \w     49.00  75.00   0.50    0.13    --  103.25 -61.00-180.00   52
 48  \w    -91.00 -66.00   0.50    0.13    -- -101.00  99.00 104.00   50
 49  \w   -121.00 -35.00   0.50    0.05    --  -47.95 -37.00  90.00  172
 50  \w   -121.00 -35.00   0.50    0.05    --  -47.95 -37.00-120.00  172
 51  \w   -121.00 -74.00   0.50    0.05    --  -47.95 -37.00 150.00   94
 52  \w     25.00 120.00   0.50    0.05    --   47.95  77.00-150.00  190
 53  \w     33.00 119.00   0.50    0.05    --   47.95  57.00   0.00  172
 54  \w    -26.00  30.00   0.50    0.05    --   47.95 -19.00-150.00  112
 55  \w     25.00  99.00   0.50    0.05    --   47.95  77.00 150.00  148
;
_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      0.0404684000
_diffrn_orient_matrix_UB_12      0.0849323000
_diffrn_orient_matrix_UB_13      -0.0711986000
_diffrn_orient_matrix_UB_21      0.0309818000
_diffrn_orient_matrix_UB_22      0.1056794000
_diffrn_orient_matrix_UB_23      0.0642938000
_diffrn_orient_matrix_UB_31      0.1454615000
_diffrn_orient_matrix_UB_32      -0.0462182000
_diffrn_orient_matrix_UB_33      0.0158438000
_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  0.0576
_diffrn_reflns_av_unetI/netI     0.0381
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.974
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            28806
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.955
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.329
_diffrn_reflns_theta_min         4.425
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'PhotonJet R (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.879
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.61698
_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    1.356
_exptl_crystal_description       plate
_exptl_crystal_F_000             740
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.719
_refine_diff_density_min         -0.223
_refine_diff_density_rms         0.047
_refine_ls_abs_structure_details
;
 Flack x determined using 2869 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.00(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     463
_refine_ls_number_reflns         6783
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.064
_refine_ls_R_factor_all          0.0382
_refine_ls_R_factor_gt           0.0364
_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^)+(0.0572P)^2^+0.3031P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0972
_refine_ls_wR_factor_ref         0.0986
_reflns_Friedel_coverage         0.859
_reflns_Friedel_fraction_full    0.996
_reflns_Friedel_fraction_max     0.934
_reflns_number_gt                6461
_reflns_number_total             6783
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            np1c00878_si_009.cif
_cod_data_source_block           chy_19_auto
_cod_database_code               1566286
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.957
_shelx_estimated_absorpt_t_min   0.778
_reflns_odcompleteness_completeness 99.97
_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:
 C2(H2), C3(H3), C27(H27), C26(H26)
2.b Secondary CH2 refined with riding coordinates:
 C16(H16A,H16B), C4(H4A,H4B), C48(H48A,H48B), C28(H28A,H28B)
2.c Aromatic/amide H refined with riding coordinates:
 C12(H12), C22(H22)
2.d Idealised Me refined as rotating group:
 C36(H36A,H36B,H36C), C44(H44A,H44B,H44C), C35(H35A,H35B,H35C), C38(H38A,H38B,
 H38C), C43(H43A,H43B,H43C), C50(H50A,H50B,H50C), C49(H49A,H49B,H49C), C31(H31A,
 H31B,H31C)
2.e Idealised tetrahedral OH refined as rotating group:
 O33(H33), O42(H42), O39(H39), O40(H40)
;
_shelx_res_checksum              75279
_shelx_hkl_checksum              42654
_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 2.006
_oxdiff_exptl_absorpt_empirical_full_min 0.577