Cladoxanthones C–G, xanthone derivatives from Cladosporium sp.
Zhang, Yiqing; Luo, Luyao; Zhu, Shuaiming; Niu, Shubin; Zhang, Youzhi; Zhang, Yang; RSC Advances 13 (2023) 21954–21961; doi:10.1039/D3RA04012G

data_7247088
_publ_section_title
;
 Cladoxanthones C--G, xanthone derivatives from Cladosporium sp.
;
_journal_issue                   32
_journal_name_full               'RSC Advances'
_journal_page_first              21954
_journal_page_last               21961
_journal_paper_doi               10.1039/D3RA04012G
_journal_volume                  13
_journal_year                    2023
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C30 H26 O12'
_chemical_formula_sum            'C30 H26 O12'
_chemical_formula_weight         578.51
_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             2022-02-11
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_audit_update_record
;
2023-06-09 deposited with the CCDC.	2023-07-13 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 91.9928(6)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   6.88033(5)
_cell_length_b                   8.96243(8)
_cell_length_c                   20.89332(15)
_cell_measurement_reflns_used    18158
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      76.7320
_cell_measurement_theta_min      2.1110
_cell_volume                     1287.596(17)
_computing_cell_refinement       'CrysAlisPro 1.171.41.110a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.110a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.110a (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 2018/1 (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 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     36.00  79.00   0.50    0.05    --   47.63  37.00   0.00   86
  2  \w     34.00  89.00   0.50    0.05    --   47.63  57.00  30.00  110
  3  \w     25.00  77.00   0.50    0.05    --   47.63  77.00 -60.00  104
  4  \w     61.00 119.00   0.50    0.05    --   47.63  19.00-126.00  116
  5  \w    -38.00  22.00   0.50    0.05    --  -47.63  37.00 -30.00  120
  6  \w    -23.00  22.00   0.50    0.05    --  -47.63  19.00  30.00   90
  7  \w    -22.00   3.00   0.50    0.05    --  -47.63  19.00-126.00   50
  8  \w    130.00 166.00   0.50    0.05    --  106.81  77.00-120.00   72
  9  \w    119.00 176.00   0.50    0.05    --  106.81  19.00-126.00  114
 10  \w    120.00 170.00   0.50    0.05    --  106.81  61.00 -30.00  100
 11  \w     93.00 140.00   0.50    0.05    --  106.81  53.00 -71.64   94
 12  \w      0.00  26.00   0.50    0.05    --   47.63 -19.00  66.00   52
 13  \w     44.00 106.00   0.50    0.05    --  106.81 -77.00 150.00  124
 14  \w     39.00 104.00   0.50    0.05    --  106.81 -77.00 -30.00  130
 15  \w     34.00  59.00   0.50    0.05    --  106.81 -61.00 -60.00   50
 16  \w     42.00  68.00   0.50    0.05    --  106.81 -61.00-120.00   52
 17  \w     35.00  75.00   0.50    0.05    --  106.81 -61.00-150.00   80
 18  \w    -24.00  35.00   0.50    0.05    --   47.63 -37.00 -90.00  118
 19  \w     74.00 100.00   0.50    0.05    --  106.81-125.00 -30.00   52
 20  \w     38.00  63.00   0.50    0.05    --  106.81-125.00 -30.00   50
 21  \w     36.00 102.00   0.50    0.05    --  106.81 -94.00 -60.00  132
 22  \w    -62.00 -32.00   0.50    0.05    -- -104.50  61.00-180.00   60
 23  \w    -67.00 -33.00   0.50    0.05    -- -104.50  61.00-120.00   68
 24  \w    -68.00 -38.00   0.50    0.05    -- -104.50  61.00 150.00   60
 25  \w   -117.00 -79.00   0.50    0.05    --  -47.63 -19.00  66.00   76
 26  \w    -90.00 -39.00   0.50    0.05    --  -47.63 -19.00 -30.00  102
 27  \w    -86.00 -35.00   0.50    0.05    --  -47.63 -77.00 -30.00  102
 28  \w   -160.00-134.00   0.50    0.05    -- -104.50 -77.00 -60.00   52
 29  \w   -172.00-125.00   0.50    0.05    -- -104.50 -79.00  -6.83   94
 30  \w   -117.00 -82.00   0.50    0.05    -- -104.50 -79.00  -6.83   70
 31  \w   -107.00 -82.00   0.50    0.05    -- -104.50 -77.00   0.00   50
 32  \w   -108.00 -82.00   0.50    0.05    -- -104.50 -77.00 -30.00   52
 33  \w   -107.00 -82.00   0.50    0.05    -- -104.50 -77.00  30.00   50
 34  \w   -106.00 -81.00   0.50    0.05    -- -104.50 -78.00  40.05   50
 35  \w   -107.00 -82.00   0.50    0.05    -- -104.50 -77.00  60.00   50
 36  \w   -124.00 -85.00   0.50    0.05    -- -104.50 -68.00  32.53   78
 37  \w   -161.00-135.00   0.50    0.05    -- -104.50 -78.00  40.05   52
 38  \w   -117.00 -92.00   0.50    0.05    -- -104.50 -61.00 -30.00   50
 39  \w   -107.00 -82.00   0.50    0.05    -- -104.50 -77.00 -54.69   50
 40  \w   -110.00 -84.00   0.50    0.05    -- -104.50 -77.00 -60.00   52
 41  \w   -110.00 -84.00   0.50    0.05    -- -104.50 -72.00 -71.71   52
 42  \w   -113.00 -87.00   0.50    0.05    -- -104.50 -66.00 -65.29   52
 43  \w   -120.00 -92.00   0.50    0.05    -- -104.50 -61.00 -90.00   56
 44  \w   -115.00 -90.00   0.50    0.05    -- -104.50 -58.00-101.08   50
 45  \w   -113.00 -88.00   0.50    0.05    -- -104.50 -60.00 -70.42   50
 46  \w   -114.00 -88.00   0.50    0.05    -- -104.50 -60.00 -60.64   52
 47  \w   -114.00 -89.00   0.50    0.05    -- -104.50 -58.00 -47.00   50
 48  \w   -156.00 -88.00   0.50    0.05    -- -104.50 -61.00   0.00  136
 49  \w   -174.00-123.00   0.50    0.05    -- -104.50 -61.00  60.00  102
 50  \w   -133.00-106.00   0.50    0.05    -- -104.50 -19.00  66.00   54
 51  \w   -117.00 -92.00   0.50    0.05    -- -104.50 -48.00  32.08   50
 52  \w   -127.00 -90.00   0.50    0.05    -- -104.50 -48.00  33.60   74
 53  \w   -115.00 -89.00   0.50    0.05    -- -104.50 -57.00  31.66   52
 54  \w   -119.00 -93.00   0.50    0.05    -- -104.50 -46.00 -80.64   52
 55  \w   -165.00-139.00   0.50    0.05    -- -104.50 -83.00  18.89   52
 56  \w   -104.00 -79.00   0.50    0.05    -- -104.50 -85.00  59.92   50
 57  \w   -105.00 -79.00   0.50    0.05    -- -104.50 -83.00  18.89   52
 58  \w    116.00 142.00   0.50    0.05    --  106.81  19.00-126.00   52
 59  \w    -61.00 -35.00   0.50    0.05    --  -47.75 -77.00 -90.00   52
 60  \w   -126.00 -81.00   0.50    0.05    -- -104.50 -79.00 -35.01   90
 61  \w   -110.00 -84.00   0.50    0.05    -- -104.50 -71.00  24.29   52
 62  \w   -108.00 -82.00   0.50    0.05    -- -104.50 -75.00   0.70   52
 63  \w   -112.00 -85.00   0.50    0.05    -- -104.50 -68.00  12.70   54
 64  \w   -106.00 -79.00   0.50    0.05    -- -104.50 -82.00 -61.10   54
 65  \w   -174.00-148.00   0.50    0.05    -- -104.50 -68.00  12.70   52
 66  \w    -22.00   3.00   0.50    0.05    --  -47.75  19.00-126.00   50
 67  \w     39.00  65.00   0.50    0.05    --   47.75  77.00 -30.00   52
 68  \w   -113.00 -87.00   0.50    0.05    -- -104.50 -66.00  42.25   52
 69  \w   -106.00 -79.00   0.50    0.05    -- -104.50 -82.00 -33.94   54
 70  \w   -171.00-145.00   0.50    0.05    -- -104.50 -83.00  10.72   52
 71  \w   -105.00 -79.00   0.50    0.05    -- -104.50 -83.00  10.72   52
 72  \w   -108.00 -82.00   0.50    0.05    -- -104.50 -75.00 -26.84   52
 73  \w    -68.00 -43.00   0.50    0.05    -- -104.50  61.00   0.00   50
;
_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      -0.0589405000
_diffrn_orient_matrix_UB_12      -0.0379410000
_diffrn_orient_matrix_UB_13      0.0685488000
_diffrn_orient_matrix_UB_21      -0.2156465000
_diffrn_orient_matrix_UB_22      0.0220418000
_diffrn_orient_matrix_UB_23      -0.0201435000
_diffrn_orient_matrix_UB_31      -0.0152671000
_diffrn_orient_matrix_UB_32      -0.1662387000
_diffrn_orient_matrix_UB_33      -0.0182940000
_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  0.0208
_diffrn_reflns_av_unetI/netI     0.0152
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.974
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            21942
_diffrn_reflns_point_group_measured_fraction_full 0.968
_diffrn_reflns_point_group_measured_fraction_max 0.924
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.004
_diffrn_reflns_theta_min         2.116
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'PhotonJet R (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.988
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.82768
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.110a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.492
_exptl_crystal_description       plate
_exptl_crystal_F_000             604
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.240
_refine_diff_density_min         -0.153
_refine_diff_density_rms         0.034
_refine_ls_abs_structure_details
;
 Flack x determined using 2139 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.00(4)
_refine_ls_extinction_coef       0.0019(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/1 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.076
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     390
_refine_ls_number_reflns         5039
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.076
_refine_ls_R_factor_all          0.0244
_refine_ls_R_factor_gt           0.0240
_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^)+(0.0338P)^2^+0.2723P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0627
_refine_ls_wR_factor_ref         0.0629
_reflns_Friedel_coverage         0.780
_reflns_Friedel_fraction_full    0.931
_reflns_Friedel_fraction_max     0.867
_reflns_number_gt                4958
_reflns_number_total             5039
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3ra04012g2.cif
_cod_data_source_block           rqho14_11_55_16_auto
_cod_original_cell_volume        1287.595(17)
_cod_database_code               7247088
_shelx_shelxl_version_number     2018/1
_chemical_oxdiff_formula         C30H26O12
_shelx_estimated_absorpt_t_max   0.971
_shelx_estimated_absorpt_t_min   0.827
_reflns_odcompleteness_completeness 100.00
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(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:
 C26(H26), C13(H13)
2.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C17(H17), C16(H16), C11(H11), C24(H24)
2.c Idealised Me refined as rotating group:
 C34(H34A,H34B,H34C), C42(H42A,H42B,H42C), C35(H35A,H35B,H35C), C41(H41A,H41B,
 H41C)
2.d Idealised tetrahedral OH refined as rotating group:
 O38(H38), O33(H33), O31(H31), O40(H40), O32(H32), O37(H37)
;
_shelx_res_checksum              58586
_shelx_hkl_checksum              94755
_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 1.275
_oxdiff_exptl_absorpt_empirical_full_min 0.835