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_7160847
_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_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           11
_space_group_name_Hall           '-P 2yb'
_space_group_name_H-M_alt        'P 1 21/m 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_audit_creation_date             2020-09-14
_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                 99.933(5)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   9.4456(5)
_cell_length_b                   6.6650(3)
_cell_length_c                   10.5231(5)
_cell_measurement_reflns_used    3860
_cell_measurement_temperature    99.99(10)
_cell_measurement_theta_max      73.6160
_cell_measurement_theta_min      4.7340
_cell_volume                     652.55(6)
_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    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      99.99(10)
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.995
_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     41.00 104.00   0.50    0.50    --   95.20 -23.00 114.00  126
  2  \w    106.00 132.00   0.50    0.50    --   95.20  23.00 -80.00   52
  3  \w    135.00 162.00   0.50    0.50    --   95.20  23.00 -80.00   54
  4  \w     12.00  37.00   0.50    0.50    --   95.20 -23.00 114.00   50
  5  \w    -43.00  20.00   0.50    0.50    --    0.00 -57.00 -60.00  126
  6  \w    -28.00  31.00   0.50    0.50    --    0.00 -82.00   0.00  118
  7  \w    -19.00   6.00   0.50    0.50    --    0.00 -82.00-120.00   50
  8  \w      1.00  29.00   0.50    0.50    --    0.00 -82.00  60.00   56
  9  \w     12.00  37.00   0.50    0.50    --    0.00  23.00 -80.00   50
 10  \w    -59.00 -34.00   0.50    0.50    --    0.00 -23.00 114.00   50
 11  \w    -16.00  10.00   0.50    0.50    --    0.00  57.00-150.00   52
 12  \w    -89.00 -61.00   0.50    0.50    --    0.00 -57.00 -60.00   56
 13  \w    123.00 185.00   0.50    0.50    --   95.20  61.00  30.00  124
 14  \w    120.00 184.00   0.50    0.50    --   95.20  61.00  90.00  128
 15  \w     72.00  98.00   0.50    0.50    --   95.20  61.00  30.00   52
 16  \w     73.00  99.00   0.50    0.50    --   95.20  61.00   8.31   52
 17  \w     74.00 101.00   0.50    0.50    --   95.20  57.00 -27.96   54
 18  \w     36.00  91.00   0.50    0.50    --   95.20 -77.00  30.00  110
 19  \w      8.00 117.00   0.50    0.50    --   95.20 -61.00 -30.00  218
 20  \w     75.00 108.00   0.50    0.50    --   95.20  61.00  90.00   66
 21  \w     73.00  98.00   0.50    0.50    --   95.20  61.00   0.00   50
 22  \w     80.00 105.00   0.50    0.50    --   95.20  45.00   0.00   50
 23  \w    158.00 185.00   0.50    0.50    --   95.20  61.00  60.00   54
 24  \w     81.00 144.00   0.50    0.50    --   95.20  45.00  60.00  126
 25  \w    147.00 180.00   0.50    0.50    --   95.20  45.00  60.00   66
 26  \w    111.00 136.00   0.50    0.50    --   95.20  74.00  63.20   50
 27  \w     80.00 107.00   0.50    0.50    --   95.20  45.00 -30.00   54
 28  \w    124.00 159.00   0.50    0.50    --   95.20  45.00 -30.00   70
 29  \w     83.00 118.00   0.50    0.50    --   95.20  45.00  30.00   70
 30  \w     77.00 104.00   0.50    0.50    --   95.20  53.00   2.45   54
 31  \w     74.00 100.00   0.50    0.50    --   95.20  61.00 -60.00   52
 32  \w    119.00 144.00   0.50    0.50    --   95.20  61.00 -60.00   50
 33  \w     75.00 118.00   0.50    0.50    --   95.20 -82.00-120.00   86
 34  \w     67.00  93.00   0.50    0.50    --   95.20  74.00  63.20   52
 35  \w     73.00  98.00   0.50    0.50    --   95.20  61.00 -30.00   50
 36  \w     79.00 175.00   0.50    0.50    --   95.20  30.00   0.00  192
 37  \w     80.00 105.00   0.50    0.50    --   95.20  30.00 -30.00   50
 38  \w     33.00 107.00   0.50    0.50    --   95.20 -30.00 -60.00  148
 39  \w     72.00 103.00   0.50    0.50    --   95.20  61.00  60.00   62
;
_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      -0.1551486000
_diffrn_orient_matrix_UB_12      0.0663748000
_diffrn_orient_matrix_UB_13      -0.0528369000
_diffrn_orient_matrix_UB_21      -0.0295198000
_diffrn_orient_matrix_UB_22      0.0203190000
_diffrn_orient_matrix_UB_23      0.1389163000
_diffrn_orient_matrix_UB_31      0.0495470000
_diffrn_orient_matrix_UB_32      0.2205146000
_diffrn_orient_matrix_UB_33      0.0030197000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0572
_diffrn_reflns_av_unetI/netI     0.0250
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            6109
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        65.933
_diffrn_reflns_theta_max         65.933
_diffrn_reflns_theta_min         4.265
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    4.651
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.40851
_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    1.624
_exptl_crystal_description       block
_exptl_crystal_F_000             328
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.692
_refine_diff_density_min         -0.682
_refine_diff_density_rms         0.124
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.206
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     123
_refine_ls_number_reflns         1238
_refine_ls_number_restraints     6
_refine_ls_restrained_S_all      1.206
_refine_ls_R_factor_all          0.0993
_refine_ls_R_factor_gt           0.0981
_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^)+(0.0260P)^2^+6.9787P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2145
_refine_ls_wR_factor_ref         0.2149
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1201
_reflns_number_total             1238
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5ob01602a2.cif
_cod_data_source_block           20200911_tof-112
_cod_depositor_comments
'Adding full bibliography for 7160847--7160848.cif.'
_cod_database_code               7160847
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_max   0.801
_shelx_estimated_absorpt_t_min   0.336
_reflns_odcompleteness_completeness 99.45
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, {H9A,H9B} of C9
 At 1.5 times of:
  All O(H) groups, {H12A,H12B} of C12
2. Uiso/Uaniso restraints and constraints
Uanis(C12) \\sim Ueq: with sigma of 0.005 and sigma for terminal atoms of 0.01
3. Others
 Fixed Sof: H9A(0.5) H9B(0.5) H10(0.5) H12A(0.5) H4A(0.5) O5(0.5) H5A(0.5)
4.a Riding coordinates:
 C12(H12A,H12B)
4.b Ternary CH refined with riding coordinates:
 C10(H10), C11(H11)
4.c Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B)
4.d Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5), C7(H7)
4.e Idealised tetrahedral OH refined as rotating group:
 O4(H4A), O5(H5A)
;
_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 2.123
_oxdiff_exptl_absorpt_empirical_full_min 0.536