Antimicrobial polyketides and sesquiterpene lactones from the deep-sea cold-seep-derived fungus <i>Talaromyces minioluteus</i> CS-113 triggered by the histone deacetylase inhibitor SAHA.
Yang, Sui-Qun; Song, Qi; Li, Xiao-Ming; Li, Xin; Li, Hong-Lei; Meng, Ling-Hong; Wang, Bin-Gui; Organic & biomolecular chemistry 21 (2023) 2575–2585; doi:10.1039/d3ob00058c

data_7159213
_publ_section_title
;
 Antimicrobial polyketides and sesquiterpene lactones from the deep-sea
 cold-seep-derived fungus <i>Talaromyces minioluteus</i> CS-113 triggered
 by the histone deacetylase inhibitor SAHA.
;
_journal_issue                   12
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              2575
_journal_page_last               2585
_journal_paper_doi               10.1039/d3ob00058c
_journal_volume                  21
_journal_year                    2023
_chemical_absolute_configuration ab
_chemical_formula_moiety         'C22 H33 N O7, H2 O'
_chemical_formula_sum            'C22 H35 N O8'
_chemical_formula_weight         441.51
_chemical_melting_point          165.0(10)
_chemical_name_common            'miniluteumide E'
_chemical_name_systematic        1
_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   mixed
_atom_sites_solution_primary     iterative
_audit_creation_date             2022-03-14
_audit_creation_method           SHELXL-97;
_audit_update_record
;
2022-03-15 deposited with the CCDC.	2023-03-01 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.1470(3)
_cell_length_b                   12.3817(3)
_cell_length_c                   18.7861(5)
_cell_measurement_reflns_used    6475
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      62.4410
_cell_measurement_theta_min      4.2660
_cell_volume                     2360.23(11)
_computing_cell_refinement       'CrysAlisPro 1.171.41.89a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.41.89a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.41.89a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve (Bourhis et al., 2015)'
_diffrn_ambient_temperature      293
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.988
_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     19.00 107.00   0.50    0.50    --   42.30  82.00-150.00  176
  2  \w    -12.00  17.00   0.50    0.50    --   42.30 -82.00  30.00   58
  3  \w    -46.00   6.00   0.50    0.50    --   42.30 -77.00-150.00  104
  4  \w    -43.00   7.00   0.50    0.50    --   42.30 -82.00 -60.00  100
  5  \w     18.00  66.00   0.50    0.50    --   42.30  65.00 -60.00   96
  6  \w     44.00  70.00   0.50    0.50    --   42.30 -82.00 -30.00   52
  7  \w     26.00  52.00   0.50    0.50    --   42.30 -77.00  90.00   52
  8  \w    -40.00   1.00   0.50    0.50    --   42.30 -77.00  90.00   82
  9  \w    -45.00  16.00   0.50    0.50    --   42.30 -82.00 120.00  122
 10  \w     22.00  66.00   0.50    0.50    --   42.30 -82.00 -60.00   88
 11  \w     76.00 106.00   0.50    0.50    --   42.30  65.00 -60.00   60
 12  \w    -13.00  36.00   0.50    0.50    --   42.30 -82.00 -30.00   98
 13  \w      6.00  70.00   0.50    0.50    --   42.30 -54.00  30.00  128
 14  \w    -45.00 -11.00   0.50    0.50    --   42.30 -54.00  30.00   68
 15  \w     98.00 125.00   0.50    0.50    --   42.30  82.00 -30.00   54
 16  \w     15.00  82.00   0.50    0.50    --   42.30  82.00 -30.00  134
 17  \w     39.00  70.00   0.50    0.50    --   42.30 -82.00 120.00   62
 18  \w     37.00  68.00   0.50    0.50    --   42.30 -77.00-150.00   62
 19  \w     82.00 108.00   0.50    0.50    --   42.30  43.00-150.00   52
 20  \w     14.00  47.00   0.50    0.50    --   42.30  43.00-150.00   66
 21  \w     32.00  70.00   0.50    0.50    --   42.30 -82.00  30.00   76
 22  \w      5.00 109.00   0.50    0.50    --   93.70 -82.00   0.00  208
 23  \w     17.00  91.00   0.50    0.50    --   93.70 -82.00  60.00  148
 24  \w    144.00 183.00   0.50    0.50    --   93.70 -17.00-180.00   78
 25  \w      5.00  94.00   0.50    0.50    --   93.70 -82.00-180.00  178
 26  \w     79.00 114.00   0.50    0.50    --   93.70 -42.00 -90.00   70
 27  \w     90.00 128.00   0.50    0.50    --   93.70 -17.00-180.00   76
 28  \w     27.00  59.00   0.50    0.50    --   93.70 -82.00 120.00   64
 29  \w     22.00  77.00   0.50    0.50    --   93.70 -82.00 -90.00  110
 30  \w     69.00  96.00   0.50    0.50    --   93.70 -82.00 150.00   54
 31  \w     32.00  73.00   0.50    0.50    --   93.70 -42.00 -90.00   82
 32  \w      5.00 183.00   0.50    0.50    --   93.70 -17.00 -60.00  356
 33  \w     34.00 103.00   0.50    0.50    --   93.70 -82.00  90.00  138
 34  \w      5.00  58.50   0.50    0.50    --   93.70 -82.00-150.00  107
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Pro II 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      0.0210326000
_diffrn_orient_matrix_UB_12      0.0750690000
_diffrn_orient_matrix_UB_13      -0.0643962000
_diffrn_orient_matrix_UB_21      0.1492176000
_diffrn_orient_matrix_UB_22      -0.0223699000
_diffrn_orient_matrix_UB_23      0.0028568000
_diffrn_orient_matrix_UB_31      -0.0182724000
_diffrn_orient_matrix_UB_32      -0.0966623000
_diffrn_orient_matrix_UB_33      -0.0507272000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0449
_diffrn_reflns_av_unetI/netI     0.0371
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            16035
_diffrn_reflns_point_group_measured_fraction_full 0.966
_diffrn_reflns_point_group_measured_fraction_max 0.962
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         68.189
_diffrn_reflns_theta_min         4.276
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.781
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.78702
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.89a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.242
_exptl_crystal_description       block
_exptl_crystal_F_000             952
_exptl_crystal_size_max          0.07
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.160
_refine_diff_density_min         -0.129
_refine_diff_density_rms         0.039
_refine_ls_abs_structure_details
;
 Flack x determined using 1215 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.02(12)
_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-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     295
_refine_ls_number_reflns         4156
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.069
_refine_ls_R_factor_all          0.0497
_refine_ls_R_factor_gt           0.0417
_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^)+(0.0581P)^2^+0.0018P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1004
_refine_ls_wR_factor_ref         0.1086
_reflns_Friedel_coverage         0.709
_reflns_Friedel_fraction_full    0.933
_reflns_Friedel_fraction_max     0.927
_reflns_number_gt                3509
_reflns_number_total             4156
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3ob00058c2.cif
_cod_data_source_block           87-1_auto
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_chemical_melting_point' value '164-166' was changed to
'165.0(10)' -- the average value was taken and precision was
estimated.

Automatic conversion script
Id: cif_fix_values 7556 2019-12-06 15:28:31Z antanas 

 Adding full bibliography for 7159211--7159213.cif.
;
_cod_original_cell_volume        2360.25(11)
_cod_database_code               7159213
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.962
_shelx_estimated_absorpt_t_min   0.947
_diffrn_oxdiff_digest_frames
;
01a80d32756013f1b479335c590564079200030c6da
;
_diffrn_oxdiff_digest_hkl
;
015f94353e205c523015f12ab07ff2247fa861
;
_reflns_odcompleteness_completeness 99.13
_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, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups, All O(H,H) groups
2. Restrained distances
 O31-H31A = O31-H31B
 0.85 with sigma of 0.02
 H31A-H31B
 1.34 with sigma of 0.04
3.a Ternary CH refined with riding coordinates:
 C16(H16), C5(H5), C9(H9), C12(H12), C3(H3), C21(H21)
3.b Secondary CH2 refined with riding coordinates:
 C4(H4A,H4B), C7(H7A,H7B), C8(H8A,H8B)
3.c Aromatic/amide H refined with riding coordinates:
 N17(H17)
3.d Idealised Me refined as rotating group:
 C30(H30A,H30B,H30C), C29(H29A,H29B,H29C), C28(H28A,H28B,H28C), C23(H23A,H23B,
 H23C), C22(H22A,H22B,H22C), C20(H20A,H20B,H20C)
3.e Idealised tetrahedral OH refined as rotating group:
 O27(H27), O25(H25)
;
_shelx_res_checksum              3677
_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 1.594
_oxdiff_exptl_absorpt_empirical_full_min 0.778