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_1566292
_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      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2021-01-21
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6226)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.72270(10)
_cell_length_b                   17.5115(3)
_cell_length_c                   24.9638(3)
_cell_measurement_reflns_used    15380
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      74.3420
_cell_measurement_theta_min      4.3300
_cell_volume                     2938.85(8)
_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    'SHELXS  (Sheldrick, 2008)'
_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 0.999
_diffrn_measured_fraction_theta_max 0.992
_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    -23.00  46.00   0.50    0.05    --   47.70 -37.00  30.00  138
  2  \w     36.00  63.00   0.50    0.12    --  103.25 -61.00  30.00   54
  3  \w     43.00  73.00   0.50    0.12    --  103.25 -61.00   0.00   60
  4  \w     95.00 172.00   0.50    0.12    --  103.25  13.00-164.00  154
  5  \w    -19.00  43.00   0.50    0.05    --   47.70 -37.00 -90.00  124
  6  \w     34.00  73.00   0.50    0.12    --  103.25 -61.00 -90.00   78
  7  \w     40.00 102.00   0.50    0.12    --  103.25-117.00-148.00  124
  8  \w     62.00  88.00   0.50    0.05    --   47.70-125.00-180.00   52
  9  \w     40.00 110.00   0.50    0.12    --  103.25-125.00 -60.00  140
 10  \w     82.00 111.00   0.50    0.12    --  103.25-125.00   0.00   58
 11  \w     31.00  73.00   0.50    0.12    --  103.25-125.00   0.00   84
 12  \w     33.00  71.00   0.50    0.12    --  103.25-150.00 143.00   76
 13  \w    103.00 129.00   0.50    0.12    --  103.25-150.00 143.00   52
 14  \w   -106.00 -80.00   0.50    0.12    -- -101.00 -77.00 150.00   52
 15  \w   -142.00 -91.00   0.50    0.12    -- -101.00 -45.00 120.00  102
 16  \w    -68.00 -42.00   0.50    0.12    -- -101.00  61.00 -30.00   52
 17  \w   -171.00-136.00   0.50    0.12    -- -101.00 -77.00 150.00   70
 18  \w   -114.00 -59.00   0.50    0.05    --  -47.70-161.00  60.00  110
 19  \w   -104.00 -78.00   0.50    0.05    --  -47.70-125.00  60.00   52
 20  \w   -117.00 -91.00   0.50    0.12    -- -101.00-125.00 -90.00   52
 21  \w   -170.00-136.00   0.50    0.12    -- -101.00-125.00 -90.00   68
 22  \w   -150.00-125.00   0.50    0.12    -- -101.00-117.00-148.00   50
 23  \w     64.00  89.00   0.50    0.05    --   47.95 161.00  90.00   50
 24  \w     33.00  98.50   0.50    0.05    --   47.95  57.00 -60.00  131
;
_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      0.0571900000
_diffrn_orient_matrix_UB_12      0.0850401000
_diffrn_orient_matrix_UB_13      -0.0036203000
_diffrn_orient_matrix_UB_21      0.2194007000
_diffrn_orient_matrix_UB_22      -0.0208232000
_diffrn_orient_matrix_UB_23      0.0102062000
_diffrn_orient_matrix_UB_31      0.0334188000
_diffrn_orient_matrix_UB_32      -0.0084967000
_diffrn_orient_matrix_UB_33      -0.0607558000
_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  0.0692
_diffrn_reflns_av_unetI/netI     0.0594
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            19700
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.979
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.750
_diffrn_reflns_theta_min         4.350
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'PhotonJet R (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.891
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.83478
_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    1.380
_exptl_crystal_description       plate
_exptl_crystal_F_000             1288
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.207
_refine_diff_density_min         -0.232
_refine_diff_density_rms         0.057
_refine_ls_abs_structure_details
;
 Flack x determined using 2215 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.03(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     403
_refine_ls_number_reflns         5824
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.054
_refine_ls_R_factor_all          0.0468
_refine_ls_R_factor_gt           0.0425
_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^)+(0.0718P)^2^+0.1049P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1077
_refine_ls_wR_factor_ref         0.1097
_reflns_Friedel_coverage         0.727
_reflns_Friedel_fraction_full    0.998
_reflns_Friedel_fraction_max     0.962
_reflns_number_gt                5511
_reflns_number_total             5824
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            np1c00878_si_004.cif
_cod_data_source_block           chy_b_1
_cod_database_code               1566292
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.982
_shelx_estimated_absorpt_t_min   0.706
_reflns_odcompleteness_completeness 99.84
_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), C30(H30), C13(H13), C12(H12)
2.b Secondary CH2 refined with riding coordinates:
 C21(H21A,H21B), C2(H2A,H2B), C32(H32A,H32B), C14(H14A,H14B)
2.c Aromatic/amide H refined with riding coordinates:
 C8(H8), C27(H27)
2.d Tetrahedral OH refined with riding coordinates:
 O38(H38), O41(H41)
2.e Idealised Me refined as rotating group:
 C40(H40A,H40B,H40C), C39(H39A,H39B,H39C), C44(H44A,H44B,H44C), C35(H35A,H35B,
 H35C), C43(H43A,H43B,H43C), C17(H17A,H17B,H17C)
;
_shelx_res_checksum              98520
_shelx_hkl_checksum              18826
_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 1.516
_oxdiff_exptl_absorpt_empirical_full_min 0.450