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_1566290
_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                 91.8150(10)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   7.93210(10)
_cell_length_b                   10.03480(10)
_cell_length_c                   18.6923(2)
_cell_measurement_reflns_used    22125
_cell_measurement_temperature    100.1(2)
_cell_measurement_theta_max      74.4520
_cell_measurement_theta_min      4.6970
_cell_volume                     1487.11(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      100.1(2)
_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 0.995
_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     36.00 121.00   0.50    0.05    --   47.95  37.00 -30.00  170
  2  \w     36.00 121.00   0.50    0.05    --   47.95  37.00  60.00  170
  3  \w     24.00 120.00   0.50    0.05    --   47.95  79.00-155.00  192
  4  \w     81.00 176.00   0.50    0.07    --  103.25  77.00-180.00  190
  5  \w     80.00 176.00   0.50    0.07    --  103.25  79.00-155.00  192
  6  \w     91.00 178.00   0.50    0.07    --  103.25  30.00 -90.00  174
  7  \w     91.00 178.00   0.50    0.07    --  103.25  30.00 -30.00  174
  8  \w     87.00 176.00   0.50    0.07    --  103.25  61.00 120.00  178
  9  \w    -26.00  30.00   0.50    0.05    --   47.95 -19.00 -90.00  112
 10  \w    -26.00  30.00   0.50    0.05    --   47.95 -19.00  60.00  112
 11  \w    -24.00  72.00   0.50    0.05    --   47.95 -79.00  79.00  192
 12  \w    -25.00  46.00   0.50    0.05    --   47.95 -37.00 120.00  142
 13  \w     80.00 176.00   0.50    0.07    --  103.25 125.00-120.00  192
 14  \w    -23.00  28.00   0.50    0.05    --  -47.95  19.00-180.00  102
 15  \w    -72.00  25.00   0.50    0.05    --  -47.95  79.00-155.00  194
 16  \w     31.00 111.00   0.50    0.07    --  103.25-125.00 -30.00  160
 17  \w     31.00 106.00   0.50    0.07    --  103.25 -94.00  30.00  150
 18  \w     31.00 127.00   0.50    0.07    --  103.25 -79.00  79.00  192
 19  \w     31.00  75.00   0.50    0.07    --  103.25 -61.00 120.00   88
 20  \w     31.00  75.00   0.50    0.07    --  103.25 -61.00  90.00   88
 21  \w     31.00  75.00   0.50    0.07    --  103.25 -61.00-120.00   88
 22  \w     31.00  75.00   0.50    0.07    --  103.25 -61.00-150.00   88
 23  \w   -119.00 -33.00   0.50    0.05    --  -47.95 -57.00 150.00  172
 24  \w   -120.00 -24.00   0.50    0.05    --  -47.95 -79.00  79.00  192
 25  \w   -120.00 -25.00   0.50    0.05    --  -47.95 -77.00   0.00  190
 26  \w   -120.00 -25.00   0.50    0.05    --  -47.95 -77.00 -60.00  190
 27  \w   -120.00 -25.00   0.50    0.05    --  -47.95 -77.00 -90.00  190
 28  \w   -112.00 -28.00   0.50    0.07    -- -101.00 125.00 -30.00  168
 29  \w   -112.00 -28.00   0.50    0.07    -- -101.00 125.00 150.00  168
 30  \w   -120.00 -25.00   0.50    0.05    --  -47.95 -77.00 150.00  190
 31  \w   -173.00 -84.00   0.50    0.07    -- -101.00 -94.00 120.00  178
 32  \w   -173.00 -78.00   0.50    0.07    -- -101.00 -77.00 150.00  190
 33  \w   -173.00 -77.00   0.50    0.07    -- -101.00 -79.00  79.00  192
 34  \w   -173.00 -78.00   0.50    0.07    -- -101.00 -77.00 120.00  190
 35  \w   -173.00 -78.00   0.50    0.07    -- -101.00 -77.00   0.00  190
 36  \w   -120.00 -74.00   0.50    0.05    --  -47.95-125.00-120.00   92
 37  \w   -120.00 -74.00   0.50    0.05    --  -47.95-125.00-150.00   92
 38  \w   -173.00 -84.00   0.50    0.07    -- -101.00 -61.00-180.00  178
 39  \w   -173.00 -84.00   0.50    0.07    -- -101.00 -61.00 -90.00  178
;
_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      -0.1438996000
_diffrn_orient_matrix_UB_12      0.1032041000
_diffrn_orient_matrix_UB_13      -0.0045242000
_diffrn_orient_matrix_UB_21      -0.0981480000
_diffrn_orient_matrix_UB_22      -0.0805869000
_diffrn_orient_matrix_UB_23      0.0550880000
_diffrn_orient_matrix_UB_31      0.0861001000
_diffrn_orient_matrix_UB_32      0.0802323000
_diffrn_orient_matrix_UB_33      0.0611673000
_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  0.0800
_diffrn_reflns_av_unetI/netI     0.0382
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            31764
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.976
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.500
_diffrn_reflns_theta_min         4.734
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'PhotonJet R (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.881
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.43523
_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    1.364
_exptl_crystal_description       block
_exptl_crystal_F_000             644
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.141
_refine_diff_density_min         -0.192
_refine_diff_density_rms         0.040
_refine_ls_abs_structure_details
;
 Flack x determined using 2472 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.07(8)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.070
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     405
_refine_ls_number_reflns         5851
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.070
_refine_ls_R_factor_all          0.0347
_refine_ls_R_factor_gt           0.0334
_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^)+(0.0509P)^2^+0.0910P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0865
_refine_ls_wR_factor_ref         0.0874
_reflns_Friedel_coverage         0.853
_reflns_Friedel_fraction_full    0.986
_reflns_Friedel_fraction_max     0.956
_reflns_number_gt                5630
_reflns_number_total             5851
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            np1c00878_si_003.cif
_cod_data_source_block           chy_2
_cod_database_code               1566290
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.925
_shelx_estimated_absorpt_t_min   0.810
_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:
 C13(H13), C31(H31), C12(H12), C30(H30)
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:
 C27(H27), C8(H8)
2.d Idealised Me refined as rotating group:
 C44(H44A,H44B,H44C), C39(H39A,H39B,H39C), C43(H43A,H43B,H43C), C17(H17A,H17B,
 H17C), C40(H40A,H40B,H40C), C35(H35A,H35B,H35C)
2.e Idealised tetrahedral OH refined as rotating group:
 O42(H42), O38(H38)
;
_shelx_res_checksum              26198
_shelx_hkl_checksum              95689
_shelx_fab_checksum              16199
_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 2.159
_oxdiff_exptl_absorpt_empirical_full_min 0.621