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_1566285
_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      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     dual
_audit_creation_date             2021-03-12
_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                   7.4273(2)
_cell_length_b                   17.5037(3)
_cell_length_c                   25.5651(4)
_cell_measurement_reflns_used    13761
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      74.9170
_cell_measurement_theta_min      3.4430
_cell_volume                     3323.60(12)
_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      100.00(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 0.975
_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     34.00  67.00   0.50    2.37    --  103.25 -61.00   0.00   66
  2  \w     36.00  72.00   0.50    2.37    --  103.25 -61.00 -30.00   72
  3  \w     47.00  74.00   0.50    2.37    --  103.25 -61.00 -60.00   54
  4  \w     35.00  62.00   0.50    2.37    --  103.25 -61.00-120.00   54
  5  \w     62.00 102.00   0.50    2.37    --  103.25 -77.00  90.00   80
  6  \w     31.00 107.00   0.50    2.37    --  103.25 -77.00 150.00  152
  7  \w     -7.00  25.00   0.50    0.59    --   47.70 -19.00 150.00   64
  8  \w     33.00  58.00   0.50    2.37    --  103.25 -94.00 -60.00   50
  9  \w     35.00  99.00   0.50    2.37    --  103.25-125.00-120.00  128
 10  \w     69.00  95.00   0.50    2.37    --  103.25 -94.00 -60.00   52
 11  \w     79.00 105.00   0.50    2.37    --  103.25 -99.00  71.00   52
 12  \w    -81.00  -2.00   0.50    0.59    --  -47.70 103.00 -88.00  158
 13  \w   -107.00 -68.00   0.50    2.37    -- -101.00 125.00 -30.00   78
 14  \w    -92.00 -47.00   0.50    2.37    -- -101.00 103.00 -88.00   90
 15  \w    -66.00 -40.00   0.50    2.37    -- -101.00  61.00   0.00   52
 16  \w    -64.00 -29.00   0.50    2.37    -- -101.00  61.00  90.00   70
 17  \w    -62.00 -28.00   0.50    2.37    -- -101.00  61.00 120.00   68
 18  \w   -118.00 -84.00   0.50    0.59    --  -47.70-125.00-120.00   68
 19  \w   -101.00 -74.00   0.50    0.59    --  -47.70-125.00-180.00   54
 20  \w   -163.00 -87.00   0.50    2.37    -- -101.00 -15.00-180.00  152
 21  \w   -135.00 -88.00   0.50    2.37    -- -101.00 -32.00 -90.00   94
 22  \w   -119.00 -74.00   0.50    0.59    --  -47.70-125.00  90.00   90
 23  \w     17.00  42.00   0.50    0.59    --   47.95-103.00 169.00   50
 24  \w   -119.00 -33.00   0.50    0.59    --  -47.95 -57.00-150.00  172
 25  \w   -120.00 -25.00   0.50    0.59    --  -47.95 -77.00 -30.00  190
 26  \w   -120.00-102.50   0.50    0.59    --  -47.95 -77.00 120.00   35
;
_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      0.1524158000
_diffrn_orient_matrix_UB_12      0.0475948000
_diffrn_orient_matrix_UB_13      0.0247052000
_diffrn_orient_matrix_UB_21      0.1287607000
_diffrn_orient_matrix_UB_22      -0.0685497000
_diffrn_orient_matrix_UB_23      -0.0050829000
_diffrn_orient_matrix_UB_31      0.0566690000
_diffrn_orient_matrix_UB_32      0.0278944000
_diffrn_orient_matrix_UB_33      -0.0547459000
_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  0.0610
_diffrn_reflns_av_unetI/netI     0.0516
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.975
_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       21
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            23411
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.956
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.162
_diffrn_reflns_theta_min         3.458
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'PhotonJet R (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.905
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.34120
_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    1.396
_exptl_crystal_description       block
_exptl_crystal_F_000             1480
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.486
_refine_diff_density_min         -0.295
_refine_diff_density_rms         0.050
_refine_ls_abs_structure_details
;
 Flack x determined using 2281 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.01(9)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     463
_refine_ls_number_reflns         6564
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.043
_refine_ls_R_factor_all          0.0544
_refine_ls_R_factor_gt           0.0419
_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^)+(0.0598P)^2^+1.2434P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1040
_refine_ls_wR_factor_ref         0.1105
_reflns_Friedel_coverage         0.731
_reflns_Friedel_fraction_full    0.995
_reflns_Friedel_fraction_max     0.931
_reflns_number_gt                6001
_reflns_number_total             6564
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            np1c00878_si_010.cif
_cod_data_source_block           chy_10a_auto
_cod_database_code               1566285
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.973
_shelx_estimated_absorpt_t_min   0.761
_reflns_odcompleteness_completeness 99.88
_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:
 C32(H32), C13(H13), C14(H14), C31(H31)
2.b Secondary CH2 refined with riding coordinates:
 C12(H12A,H12B), C33(H33A,H33B), C22(H22A,H22B), C48(H48A,H48B)
2.c Aromatic/amide H refined with riding coordinates:
 C26(H26), C8(H8)
2.d Idealised Me refined as rotating group:
 C44(H44A,H44B,H44C), C41(H41A,H41B,H41C), C40(H40A,H40B,H40C), C16(H16A,H16B,
 H16C), C19(H19A,H19B,H19C), C36(H36A,H36B,H36C), C50(H50A,H50B,H50C), C49(H49A,
 H49B,H49C)
2.e Idealised tetrahedral OH refined as rotating group:
 O43(H43), O18(H18), O39(H39), O17(H17)
;
_shelx_res_checksum              77212
_shelx_hkl_checksum              67242
_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 1.741
_oxdiff_exptl_absorpt_empirical_full_min 0.496