Penicichrysol A: an unprecedented polyketide produced by <i>Penicillium chrysogenum</i>.
Mo, Shuyuan; Huang, Zhihong; Zeng, Hanxiao; Wang, Jianping; Zhang, Yonghui; Hu, Zhengxi; Organic & biomolecular chemistry 23 (2025) 608–613; doi:10.1039/d4ob01742k

data_1573313
_publ_section_title
;
 Penicichrysol A: an unprecedented polyketide produced by <i>Penicillium
 chrysogenum</i>.
;
_journal_issue                   3
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              608
_journal_page_last               613
_journal_paper_doi               10.1039/d4ob01742k
_journal_volume                  23
_journal_year                    2025
_chemical_formula_moiety         'C18 H18 O8'
_chemical_formula_sum            'C18 H18 O8'
_chemical_formula_weight         362.32
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2021-07-26
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2024-10-26 deposited with the CCDC.	2024-11-27 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 99.4910(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.88840(10)
_cell_length_b                   13.43880(10)
_cell_length_c                   11.52040(10)
_cell_measurement_reflns_used    25372
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      73.7180
_cell_measurement_theta_min      3.8670
_cell_volume                     1662.67(2)
_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    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.991
_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    -16.00  60.00   0.50    0.50    --    8.00  67.00 -78.79  152
  2  \w     20.00  48.00   0.50    0.50    --   28.00 -53.00-123.69   56
  3  \w    -61.00  17.00   0.50    0.50    --   28.00 -53.00-123.69  156
  4  \w     85.00 112.00   0.50    0.50    --   36.00  72.00-118.24   54
  5  \w      9.00  68.00   0.50    0.50    --   36.00  72.00-118.24  118
  6  \w     17.00  60.00   0.50    0.50    --   44.00  72.00 -40.68   86
  7  \w     18.00  50.00   0.50    0.50    --   44.00  72.00  39.47   64
  8  \w     94.00 133.00   0.50    0.50    --   44.00  72.00 -40.68   78
  9  \w     28.00  71.00   0.50    0.50    --   52.00  73.00  91.52   86
 10  \w     80.00 106.00   0.50    0.50    --   52.00  73.00  91.52   52
 11  \w     29.00  55.00   0.50    0.50    --   56.00  71.00 175.61   52
 12  \w     33.00  85.00   0.50    0.50    --   60.00  74.00  29.24  104
 13  \w     96.00 152.00   0.50    0.50    --   64.00  74.00-136.26  112
 14  \w     36.00  68.00   0.50    0.50    --   64.00  74.00-136.26   64
 15  \w     37.00  79.00   0.50    0.50    --   64.00  74.00-177.65   84
 16  \w     41.00  74.00   0.50    0.50    --   68.00  75.00   5.13   66
 17  \w     40.00  79.00   0.50    0.50    --   68.00  75.00 -33.84   78
 18  \w     40.00  71.00   0.50    0.50    --   68.00  74.00 107.42   62
 19  \w    129.00 161.00   0.50    0.50    --   72.00  71.00 -64.38   64
 20  \w     44.00  70.00   0.50    0.50    --   72.00  75.00 144.41   52
 21  \w     45.00  87.00   0.50    0.50    --   72.00  71.00 -64.38   84
 22  \w     50.00  82.00   0.50    0.50    --   72.00  73.00-115.08   64
 23  \w    128.00 161.00   0.50    0.50    --   72.00  75.00 144.41   66
 24  \w     44.00  76.00   0.50    0.50    --   72.00  75.00  57.54   64
 25  \w     85.00 126.00   0.50    0.50    --   94.60 -82.00  90.00   82
 26  \w    148.00 174.00   0.50    0.50    --   94.60  75.00-154.94   52
 27  \w      5.00  49.00   0.50    0.50    --   94.60 -82.00  90.00   88
 28  \w    122.00 180.00   0.50    0.50    --   94.60  61.00   0.00  116
 29  \w     66.00 128.00   0.50    0.50    --   94.60  75.00-154.94  124
 30  \w     71.00 116.00   0.50    0.50    --   94.60  61.00   0.00   90
 31  \w     15.00 107.00   0.50    0.50    --   94.60 -61.00-180.00  184
 32  \w      5.00 121.00   0.50    0.50    --   94.60 -82.00-180.00  232
 33  \w     66.00 120.00   0.50    0.50    --   94.60  74.00 178.27  108
 34  \w      5.00 126.00   0.50    0.50    --   94.60 -82.00  30.00  242
 35  \w    149.00 181.00   0.50    0.50    --   94.60  56.00 114.78   64
 36  \w     67.00 173.00   0.50    0.50    --   94.60  73.00 -71.68  212
 37  \w     71.00 125.00   0.50    0.50    --   94.60  61.00-180.00  108
 38  \w     71.00 165.00   0.50    0.50    --   94.60  61.00 -93.44  188
 39  \w     72.00 179.00   0.50    0.50    --   94.60  56.00  82.41  214
 40  \w     55.00 113.00   0.50    0.50    --   94.60 -61.00  30.00  116
 41  \w      6.00  42.00   0.50    0.50    --   94.60 -61.00  30.00   72
 42  \w     73.00  99.00   0.50    0.50    --   94.60  56.00 114.78   52
 43  \w    145.00 181.00   0.50    0.50    --   94.60  66.00 122.87   72
 44  \w     73.00 134.00   0.50    0.50    --   94.60  61.00-120.00  122
 45  \w     73.00 123.00   0.50    0.50    --   94.60  66.00 122.87  100
 46  \w     71.00 148.00   0.50    0.50    --   94.60  61.00 -30.00  154
 47  \w     72.00 184.00   0.50    0.50    --   94.60  61.00  60.00  224
 48  \w     68.00 168.00   0.50    0.50    --   94.60  69.00  14.45  200
 49  \w     72.00 148.00   0.50    0.50    --   94.60  61.00 150.00  152
 50  \w     68.00 108.00   0.50    0.50    --   94.60  71.00 -78.93   80
 51  \w     14.00 103.00   0.50    0.50    --   94.60 -82.00 -30.00  178
 52  \w     88.00 127.00   0.50    0.50    --   96.00 -82.00-125.84   78
;
_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      -0.0378640000
_diffrn_orient_matrix_UB_12      0.1063487000
_diffrn_orient_matrix_UB_13      0.0293891000
_diffrn_orient_matrix_UB_21      0.0234462000
_diffrn_orient_matrix_UB_22      0.0358870000
_diffrn_orient_matrix_UB_23      -0.1214735000
_diffrn_orient_matrix_UB_31      -0.1363564000
_diffrn_orient_matrix_UB_32      -0.0233572000
_diffrn_orient_matrix_UB_33      -0.0525315000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0357
_diffrn_reflns_av_unetI/netI     0.0143
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            37259
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.896
_diffrn_reflns_theta_min         5.097
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.977
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.65168
_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            colorless
_exptl_crystal_density_diffrn    1.447
_exptl_crystal_description       plate
_exptl_crystal_F_000             760
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.303
_refine_diff_density_min         -0.258
_refine_diff_density_rms         0.050
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     241
_refine_ls_number_reflns         3341
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.036
_refine_ls_R_factor_all          0.0362
_refine_ls_R_factor_gt           0.0353
_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^)+(0.0533P)^2^+0.7163P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0960
_refine_ls_wR_factor_ref         0.0968
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3222
_reflns_number_total             3341
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4ob01742k2.cif
_cod_data_source_block           20210630_msy4-16
_cod_depositor_comments
'Adding full bibliography for 1573312--1573313.cif.'
_cod_database_code               1573313
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_max   0.953
_shelx_estimated_absorpt_t_min   0.829
_reflns_odcompleteness_completeness 99.97
_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 Aromatic/amide H refined with riding coordinates:
 C009(H009), C00J(H00J), C00L(H00L), C00M(H00M)
2.b Idealised Me refined as rotating group:
 C00N(H00a,H00b,H00c), C00O(H00d,H00e,H00f), C00P(H00g,H00h,H00i), C00Q(H00k,
 H00n,H00o)
2.c Idealised tetrahedral OH refined as rotating group:
 O004(H004), O005(H005)
;
_shelx_res_checksum              67087
_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 1.975
_oxdiff_exptl_absorpt_empirical_full_min 0.624