Bioassay-Directed Isolation of Antibacterial Metabolites from an Arthropod-Derived Penicillium chrysogenum
Zhang, Sitian; He, Yan; Li, Fengli; Lin, Shuang; Yang, Beiye; Mo, Shuyuan; Li, Huaqiang; Wang, Jianping; Qi, Changxing; Hu, Zhengxi; Zhang, Yonghui; Journal of Natural Products  (2020) –; doi:10.1021/acs.jnatprod.0c00873

data_1559395
_publ_section_title
;
 Bioassay-Directed Isolation of Antibacterial Metabolites from an
 Arthropod-Derived Penicillium chrysogenum
;
_journal_name_full               'Journal of Natural Products'
_journal_paper_doi               10.1021/acs.jnatprod.0c00873
_journal_year                    2020
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C20 H28 O3'
_chemical_formula_sum            'C20 H28 O3'
_chemical_formula_weight         316.42
_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             2020-01-11
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 92.1346(6)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.42344(5)
_cell_length_b                   13.02017(8)
_cell_length_c                   15.78803(10)
_cell_measurement_reflns_used    35555
_cell_measurement_temperature    99.99(10)
_cell_measurement_theta_max      73.6870
_cell_measurement_theta_min      4.4050
_cell_volume                     1730.345(18)
_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  'ShelXL (Sheldrick, 2015)'
_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 0.996
_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     23.00  49.00   0.50    0.50    --    0.00  62.00-158.00   52
  2  \w     54.00  86.00   0.50    0.50    --    0.00  62.00-158.00   64
  3  \w     71.00 123.00   0.50    0.50    --   94.60  62.00-158.00  104
  4  \w     55.00 118.00   0.50    0.50    --   94.60 -62.00  63.00  126
  5  \w    -87.00 -24.00   0.50    0.50    --    0.00 -57.00 -90.00  126
  6  \w    -89.00  17.00   0.50    0.50    --    0.00 -38.00 -30.00  212
  7  \w    -83.00 -58.00   0.50    0.50    --    0.00 -38.00-180.00   50
  8  \w    -54.00  16.00   0.50    0.50    --    0.00 -38.00-180.00  140
  9  \w    -33.00  31.00   0.50    0.50    --    0.00 -82.00 150.00  128
 10  \w     43.00  82.00   0.50    0.50    --    0.00  38.00-180.00   78
 11  \w     -6.00  19.00   0.50    0.50    --    0.00  38.00-180.00   50
 12  \w    -21.00  22.00   0.50    0.50    --    0.00 -57.00 -90.00   86
 13  \w    -46.00  28.00   0.50    0.50    --    0.00 -77.00  90.00  148
 14  \w    -30.00   0.00   0.50    0.50    --    0.00 -62.00  63.00   60
 15  \w     71.00 165.00   0.50    0.50    --   94.60  61.00  90.00  188
 16  \w    118.00 176.00   0.50    0.50    --   94.60  66.00 131.37  116
 17  \w     71.00 182.00   0.50    0.50    --   94.60  61.00-120.00  222
 18  \w     66.00  95.00   0.50    0.50    --   94.60  75.00  45.59   58
 19  \w     70.00  96.00   0.50    0.50    --   94.60  66.00 131.37   52
 20  \w    113.00 184.00   0.50    0.50    --   94.60  61.00   0.00  142
 21  \w     72.00  98.00   0.50    0.50    --   94.60  55.00 -87.90   52
 22  \w     71.00 184.00   0.50    0.50    --   94.60  61.00 -60.00  226
 23  \w     72.00 105.00   0.50    0.50    --   94.60  57.00  14.25   66
 24  \w    159.00 184.00   0.50    0.50    --   94.60  66.00  38.95   50
 25  \w    126.00 158.00   0.50    0.50    --   94.60  57.00  14.25   64
 26  \w     69.00  97.00   0.50    0.50    --   94.60  67.00 -42.94   56
 27  \w     74.00 134.00   0.50    0.50    --   94.60  50.00  89.24  120
 28  \w     71.00 106.00   0.50    0.50    --   94.60  61.00-180.00   70
 29  \w      5.00  86.00   0.50    0.50    --   94.60 -77.00 -60.00  162
 30  \w     95.00 124.00   0.50    0.50    --   94.60 -77.00 -60.00   58
 31  \w     71.00 183.00   0.50    0.50    --   94.60  61.00 150.00  224
 32  \w     71.00  97.00   0.50    0.50    --   94.60  61.00 -90.00   52
 33  \w     47.00 123.00   0.50    0.50    --   94.60 -82.00  90.00  152
 34  \w    100.00 150.00   0.50    0.50    --   94.60  75.00  45.59  100
 35  \w     17.00 126.00   0.50    0.50    --   94.60 -82.00   0.00  218
 36  \w     71.00  96.00   0.50    0.50    --   94.60  61.00   0.00   50
 37  \w     70.00  96.00   0.50    0.50    --   94.60  66.00  38.95   52
 38  \w     72.00 112.00   0.50    0.50    --   94.60  58.00  29.09   80
 39  \w     73.00 108.00   0.50    0.50    --   94.60  53.00   6.79   70
 40  \w    155.00 182.00   0.50    0.50    --   94.60  69.00-150.32   54
 41  \w     71.00 183.00   0.50    0.50    --   94.60  61.00-150.00  224
 42  \w     67.00  92.00   0.50    0.50    --   94.60  73.00 151.92   50
 43  \w     67.00 101.00   0.50    0.50    --   94.60  72.00  37.07   68
 44  \w    123.00 159.00   0.50    0.50    --   94.60  73.00 -39.92   72
 45  \w    135.00 172.00   0.50    0.50    --   94.60  49.00 -89.10   74
 46  \w     74.00 126.00   0.50    0.50    --   94.60  49.00 -89.10  104
 47  \w     71.00  97.00   0.50    0.50    --   94.60  61.00 -30.00   52
 48  \w    118.00 184.00   0.50    0.50    --   94.60  61.00 -30.00  132
 49  \w     67.00  92.00   0.50    0.50    --   94.60  73.00 -84.51   50
 50  \w     69.00 113.00   0.50    0.50    --   94.60  67.00 106.87   88
 51  \w    151.00 176.00   0.50    0.50    --   94.60  67.00 106.87   50
 52  \w    119.00 144.00   0.50    0.50    --   94.60  69.00-150.32   50
 53  \w     78.00 120.00   0.50    0.50    --   94.60 -82.00 150.00   84
 54  \w     68.00  93.00   0.50    0.50    --   94.60  69.00-150.32   50
 55  \w     67.00  92.00   0.50    0.50    --   94.60  73.00 -39.92   50
 56  \w     75.00 100.00   0.50    0.50    --   94.60  45.00 150.00   50
 57  \w    158.00 183.00   0.50    0.50    --   94.60  45.00 150.00   50
 58  \w     66.00 108.00   0.50    0.50    --   94.60 -61.00-180.00   84
 59  \w     70.00  96.00   0.50    0.50    --   94.60  65.00-171.38   52
 60  \w    151.00 181.00   0.50    0.50    --   94.60  65.00-171.38   60
 61  \w     69.00  94.00   0.50    0.50    --   94.60  67.00 -82.93   50
 62  \w     66.00  91.00   0.50    0.50    --   94.60  74.00 139.95   50
 63  \w    137.00 162.00   0.50    0.50    --   94.60  55.00 -87.90   50
 64  \w     20.00 125.00   0.50    0.50    --   94.60 -82.00 -90.00  210
;
_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      0.0029961000
_diffrn_orient_matrix_UB_12      0.1028737000
_diffrn_orient_matrix_UB_13      -0.0481536000
_diffrn_orient_matrix_UB_21      0.1499551000
_diffrn_orient_matrix_UB_22      0.0321828000
_diffrn_orient_matrix_UB_23      0.0522459000
_diffrn_orient_matrix_UB_31      0.1048038000
_diffrn_orient_matrix_UB_32      -0.0488009000
_diffrn_orient_matrix_UB_33      -0.0670160000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0301
_diffrn_reflns_av_unetI/netI     0.0155
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            39988
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.004
_diffrn_reflns_theta_min         2.801
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.631
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.71153
_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    1.215
_exptl_crystal_description       block
_exptl_crystal_F_000             688
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.199
_refine_diff_density_min         -0.136
_refine_diff_density_rms         0.031
_refine_ls_abs_structure_details
;
 Flack x determined using 3222 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       0.0045(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.067
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     426
_refine_ls_number_reflns         6941
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.066
_refine_ls_R_factor_all          0.0269
_refine_ls_R_factor_gt           0.0267
_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^)+(0.0399P)^2^+0.3271P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0719
_refine_ls_wR_factor_ref         0.0720
_reflns_Friedel_coverage         0.891
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.974
_reflns_number_gt                6899
_reflns_number_total             6941
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            np0c00873_si_002.cif
_cod_data_source_block           20191224_zst1_13_1
_cod_original_cell_volume        1730.344(18)
_cod_database_code               1559395
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_max   0.911
_shelx_estimated_absorpt_t_min   0.858
_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, 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:
 C4(H4), C6(H6), C15(H15), C4A(H4A), C6A(H6A), C15A(H15A)
2.b Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B), C8(H8A,H8B), C10(H10A,H10B), C12(H12A,H12B), C13(H13A,H13B),
 C7A(H7AA,H7AB), C8A(H8AA,H8AB), C10A(H10C,H10D), C12A(H12C,H12D), C13A(H13C,
 H13D)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2A), C3(H3), C2A(H2AB), C3A(H3A)
2.d Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C), C17(H17A,H17B,H17C), C18(H18A,H18B,H18C), C19(H19A,H19B,
 H19C), C16A(H16D,H16E,H16F), C17A(H17D,H17E,H17F), C18A(H18D,H18E,H18F),
 C19A(H19D,H19E,H19F)
2.e Idealised tetrahedral OH refined as rotating group:
 O2(H2), O2A(H2AA)
;
_shelx_res_checksum              6139
_shelx_hkl_checksum              19156
_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 1.692
_oxdiff_exptl_absorpt_empirical_full_min 0.772