Resorcylic acid lactone derivatives with immunosuppressive activity from the endophytic <i>Podospora</i> sp. G214.
Li, Wanpeng; Gao, Ying; Ruan, Hanli; Organic & biomolecular chemistry 23 (2025) 10771–10778; doi:10.1039/d5ob01602a

data_7160848
_publ_section_title
;
 Resorcylic acid lactone derivatives with immunosuppressive activity from
 the endophytic <i>Podospora</i> sp. G214.
;
_journal_issue                   47
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              10771
_journal_page_last               10778
_journal_paper_doi               10.1039/d5ob01602a
_journal_volume                  23
_journal_year                    2025
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C13 H12 Cl2 O5'
_chemical_formula_sum            'C13 H12 Cl2 O5'
_chemical_formula_weight         319.13
_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             2020-12-10
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2025-10-09 deposited with the CCDC.	2025-11-11 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 92.0783(5)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   4.36335(3)
_cell_length_b                   25.31599(12)
_cell_length_c                   11.98481(7)
_cell_measurement_reflns_used    22005
_cell_measurement_temperature    99.99(10)
_cell_measurement_theta_max      73.6280
_cell_measurement_theta_min      3.4970
_cell_volume                     1323.002(13)
_computing_cell_refinement       'CrysAlisPro 1.171.39.28b (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.39.28b (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.39.28b (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XM (Sheldrick, 2008)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      99.99(10)
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.987
_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     -9.00  36.00   0.50    0.50    --   16.00  70.00  -9.29   90
  2  \w     45.00 101.00   0.50    0.50    --   16.00  70.00  -9.29  112
  3  \w      6.00  37.00   0.50    0.50    --   32.00  71.00-132.25   62
  4  \w    -46.00   2.00   0.50    0.50    --   40.00 -41.00-111.99   96
  5  \w      7.00  58.00   0.50    0.50    --   40.00 -41.00-111.99  102
  6  \w     28.00  58.00   0.50    0.50    --   44.00  73.00  -5.80   60
  7  \w     96.00 123.00   0.50    0.50    --   44.00  73.00  -5.80   54
  8  \w     31.00  58.00   0.50    0.50    --   52.00  74.00  60.96   54
  9  \w     36.00  62.00   0.50    0.50    --   56.00  74.00-141.55   52
 10  \w     31.00  71.00   0.50    0.50    --   56.00  74.00  11.74   80
 11  \w    123.00 149.00   0.50    0.50    --   60.00  75.00 -60.40   52
 12  \w     34.00  77.00   0.50    0.50    --   60.00  70.00 166.92   86
 13  \w     32.00  75.00   0.50    0.50    --   60.00  75.00 -60.40   86
 14  \w     40.00 102.00   0.50    0.50    --   64.00  72.00-177.39  124
 15  \w     39.00  64.00   0.50    0.50    --   64.00  75.00  82.39   50
 16  \w    117.00 153.00   0.50    0.50    --   68.00  74.00 -97.80   72
 17  \w     40.00  82.00   0.50    0.50    --   68.00  74.00 -97.80   84
 18  \w     45.00  77.00   0.50    0.50    --   72.00  75.00  98.22   64
 19  \w     48.00  78.00   0.50    0.50    --   76.00  75.00-120.84   60
 20  \w     48.00 109.00   0.50    0.50    --   76.00  74.00  83.65  122
 21  \w     70.00 130.00   0.50    0.50    --   94.60  65.00 113.74  120
 22  \w    115.00 184.00   0.50    0.50    --   94.60  75.00  -5.26  138
 23  \w    136.00 182.00   0.50    0.50    --   94.60  71.00 160.76   92
 24  \w     91.00 126.00   0.50    0.50    --   94.60 -82.00 -30.00   70
 25  \w     66.00 106.00   0.50    0.50    --   94.60  75.00  -5.26   80
 26  \w      5.00  88.00   0.50    0.50    --   94.60 -82.00 -30.00  166
 27  \w     26.00 126.00   0.50    0.50    --   94.60 -82.00 120.00  200
 28  \w     74.00 142.00   0.50    0.50    --   94.60  61.00  52.26  136
 29  \w    148.00 176.00   0.50    0.50    --   94.60  61.00  52.26   56
 30  \w    140.00 183.00   0.50    0.50    --   94.60  60.00 -94.93   86
 31  \w     67.00 128.00   0.50    0.50    --   94.60  71.00 160.76  122
 32  \w     80.00 126.00   0.50    0.50    --   94.60 -82.00-150.00   92
 33  \w     46.00  72.00   0.50    0.50    --   94.60 -82.00-150.00   52
 34  \w     71.00 136.00   0.50    0.50    --   94.60  60.00 -94.93  130
 35  \w     52.00 118.00   0.50    0.50    --   94.60 -82.00  60.00  132
 36  \w    150.00 184.00   0.50    0.50    --   94.60  55.00 -58.54   68
 37  \w     21.00  47.00   0.50    0.50    --   94.60 -82.00  60.00   52
 38  \w     67.00 125.00   0.50    0.50    --   94.60  71.00 -21.51  116
 39  \w     74.00 134.00   0.50    0.50    --   94.60  55.00 -58.54  120
 40  \w     84.00 109.00   0.50    0.50    --   94.60 -82.00 -90.00   50
 41  \w      5.00  74.00   0.50    0.50    --   94.60 -82.00 -90.00  138
 42  \w    129.00 155.00   0.50    0.50    --   94.60  56.00-132.32   52
 43  \w     71.00 182.00   0.50    0.50    --   94.60  61.00-150.00  222
 44  \w     75.00 101.00   0.50    0.50    --   94.60  61.00 -30.00   52
 45  \w    112.00 183.00   0.50    0.50    --   94.60  61.00 -30.00  142
 46  \w     78.00 152.00   0.50    0.50    --   94.60  61.00  60.00  148
 47  \w     67.00 113.00   0.50    0.50    --   94.60  72.00  21.45   92
 48  \w     71.00 175.00   0.50    0.50    --   94.60  61.00 150.00  208
 49  \w    135.00 168.00   0.50    0.50    --   94.60  65.00 113.74   66
 50  \w     76.00 122.00   0.50    0.50    --   94.60  56.00-132.32   92
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RINC): Kappa single'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1120766000
_diffrn_orient_matrix_UB_12      0.0512140000
_diffrn_orient_matrix_UB_13      -0.0547434000
_diffrn_orient_matrix_UB_21      -0.0575472000
_diffrn_orient_matrix_UB_22      0.0305843000
_diffrn_orient_matrix_UB_23      0.1083641000
_diffrn_orient_matrix_UB_31      0.3300680000
_diffrn_orient_matrix_UB_32      -0.0120519000
_diffrn_orient_matrix_UB_33      0.0424769000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0234
_diffrn_reflns_av_unetI/netI     0.0163
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       31
_diffrn_reflns_limit_k_min       -31
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            26037
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.970
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.030
_diffrn_reflns_theta_min         3.492
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    4.589
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.62668
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.28b (Rigaku Oxford Diffraction, 2015)
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    1.602
_exptl_crystal_description       block
_exptl_crystal_F_000             656
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.151
_refine_diff_density_min         -0.215
_refine_diff_density_rms         0.041
_refine_ls_abs_structure_details
;
 Flack x determined using 2470 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.000(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     367
_refine_ls_number_reflns         5243
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.044
_refine_ls_R_factor_all          0.0192
_refine_ls_R_factor_gt           0.0191
_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^)+(0.0344P)^2^+0.2183P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0523
_refine_ls_wR_factor_ref         0.0523
_reflns_Friedel_coverage         0.920
_reflns_Friedel_fraction_full    0.995
_reflns_Friedel_fraction_max     0.952
_reflns_number_gt                5223
_reflns_number_total             5243
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5ob01602a2.cif
_cod_data_source_block           20201127_tof-112-1
_cod_depositor_comments
'Adding full bibliography for 7160847--7160848.cif.'
_cod_original_cell_volume        1323.002(12)
_cod_database_code               7160848
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_max   0.657
_shelx_estimated_absorpt_t_min   0.393
_reflns_odcompleteness_completeness 99.96
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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:
 C10(H10), C11(H11), C10B(H10B), C11B(H11B)
2.b Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B), C9B(H9BA,H9BB)
2.c Aromatic/amide H refined with riding coordinates:
 C4(H4A), C5(H5A), C7(H7), C4B(H4BA), C5B(H5BA), C7B(H7B)
2.d Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C), C12B(H12D,H12E,H12F)
2.e Idealised tetrahedral OH refined as rotating group:
 O4(H4), O5(H5), O4B(H4B), O5B(H5B)
;
_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 1.796
_oxdiff_exptl_absorpt_empirical_full_min 0.711