Fungal Polyketides with Three Distinctive Ring Skeletons from the Fungus <i>Penicillium canescens</i> Uncovered by OSMAC and Molecular Networking Strategies.
Zang, Yi; Gong, Yihua; Gong, Jiaojiao; Liu, Junjun; Chen, Chunmei; Gu, Lianghu; Zhou, Yuan; Wang, Jianping; Zhu, Hucheng; Zhang, Yonghui; The Journal of organic chemistry 85 (2020) 4973–4980; doi:10.1021/acs.joc.0c00147

data_4038066
_publ_section_title
;
 Fungal Polyketides with Three Distinctive Ring Skeletons from the Fungus
 <i>Penicillium canescens</i> Uncovered by OSMAC and Molecular Networking
 Strategies.
;
_journal_issue                   7
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              4973
_journal_page_last               4980
_journal_paper_doi               10.1021/acs.joc.0c00147
_journal_volume                  85
_journal_year                    2020
_chemical_absolute_configuration rmad
_chemical_formula_moiety         'C17 H20 O6'
_chemical_formula_sum            'C17 H20 O6'
_chemical_formula_weight         320.33
_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   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2018-12-12
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 95.7545(4)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   8.26368(3)
_cell_length_b                   7.69518(4)
_cell_length_c                   12.43341(5)
_cell_measurement_reflns_used    13856
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      73.6200
_cell_measurement_theta_min      3.6020
_cell_volume                     786.662(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  '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 0.999
_diffrn_measured_fraction_theta_max 0.994
_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    -45.00 -19.00   0.50    0.50    --    0.00 -77.00 -90.00   52
  2  \w     34.00  89.00   0.50    0.50    --    0.00  38.00  90.00  110
  3  \w     -2.00  42.00   0.50    0.50    --    0.00  57.00 -90.00   88
  4  \w    -41.00 -15.00   0.50    0.50    --    0.00 -77.00 -30.00   52
  5  \w    -12.00  41.00   0.50    0.50    --    0.00  38.00  30.00  106
  6  \w      9.00  70.00   0.50    0.50    --    0.00  57.00-180.00  122
  7  \w     -2.00  29.00   0.50    0.50    --    0.00  38.00  90.00   62
  8  \w     47.00  88.00   0.50    0.50    --    0.00  57.00 -90.00   82
  9  \w     -7.00  29.00   0.50    0.50    --    0.00 -77.00 -30.00   72
 10  \w     -2.00  23.00   0.50    0.50    --    0.00 -77.00 -90.00   50
 11  \w    -21.00   4.00   0.50    0.50    --    0.00  57.00-180.00   50
 12  \w     49.00  88.00   0.50    0.50    --    0.00  38.00  30.00   78
 13  \w     69.00  94.00   0.50    0.50    --   94.60  68.00 -62.26   50
 14  \w     67.00 100.00   0.50    0.50    --   94.60  72.00-162.58   66
 15  \w    159.00 184.00   0.50    0.50    --   94.60  57.00 110.31   50
 16  \w     68.00 161.00   0.50    0.50    --   94.60  74.00-154.39  186
 17  \w    106.00 179.00   0.50    0.50    --   94.60  69.00   3.66  146
 18  \w     72.00  97.00   0.50    0.50    --   94.60  57.00 110.31   50
 19  \w    121.00 168.00   0.50    0.50    --   94.60  66.00 162.67   94
 20  \w     67.00 120.00   0.50    0.50    --   94.60  72.00  57.80  106
 21  \w     66.00  94.00   0.50    0.50    --   94.60  74.00 -16.75   56
 22  \w     68.00 103.00   0.50    0.50    --   94.60  69.00   3.66   70
 23  \w    133.00 184.00   0.50    0.50    --   94.60  72.00  57.80  102
 24  \w      5.00 122.00   0.50    0.50    --   94.60 -82.00  90.00  234
 25  \w     78.00 111.00   0.50    0.50    --   94.60  45.00 150.00   66
 26  \w     66.00 105.00   0.50    0.50    --   94.60 -82.00-120.00   78
 27  \w     66.00 102.00   0.50    0.50    --   94.60  74.00-107.67   72
 28  \w      6.00 126.00   0.50    0.50    --   94.60 -82.00-180.00  240
 29  \w     71.00  96.00   0.50    0.50    --   94.60  61.00 150.00   50
 30  \w    143.00 171.00   0.50    0.50    --   94.60  73.00  70.92   56
 31  \w    130.00 156.00   0.50    0.50    --   94.60  68.00-174.63   52
 32  \w    124.00 169.00   0.50    0.50    --   94.60  72.00-122.37   90
 33  \w     67.00 119.00   0.50    0.50    --   94.60  73.00  70.92  104
 34  \w     71.00 138.00   0.50    0.50    --   94.60  61.00  30.00  134
 35  \w    159.00 184.00   0.50    0.50    --   94.60  72.00 -43.53   50
 36  \w     70.00  97.00   0.50    0.50    --   94.60  68.00-174.63   54
 37  \w    142.00 180.00   0.50    0.50    --   94.60  61.00  30.00   76
 38  \w      9.00  69.00   0.50    0.50    --   94.60 -77.00 120.00  120
 39  \w     99.00 124.00   0.50    0.50    --   94.60 -77.00 120.00   50
 40  \w     73.00 167.00   0.50    0.50    --   94.60  61.00-180.00  188
 41  \w     72.00  98.00   0.50    0.50    --   94.60  61.00  60.00   52
 42  \w     73.00 127.00   0.50    0.50    --   94.60  61.00 -42.24  108
 43  \w     70.00 119.00   0.50    0.50    --   94.60  63.00 -13.31   98
 44  \w     71.00  96.00   0.50    0.50    --   94.60  61.00 120.00   50
 45  \w     67.00  93.00   0.50    0.50    --   94.60  72.00 -43.53   52
 46  \w     75.00 115.00   0.50    0.50    --   94.60  45.00 120.00   80
 47  \w      5.00 115.00   0.50    0.50    --   94.60 -82.00 -30.00  220
 48  \w     71.00 112.00   0.50    0.50    --   94.60  61.00-120.00   82
 49  \w     71.00 101.00   0.50    0.50    --   94.60  62.00 -82.73   60
 50  \w     71.00  97.00   0.50    0.50    --   94.60  67.00  29.86   52
 51  \w     67.00  92.00   0.50    0.50    --   94.60  72.00-122.37   50
 52  \w      6.00 101.00   0.50    0.50    --   94.60 -61.00 -30.00  190
 53  \w     69.00 113.00   0.50    0.50    --   94.60  66.00 162.67   88
 54  \w     77.00 181.00   0.50    0.50    --   94.60  38.00 -42.23  208
;
_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      0.1510314000
_diffrn_orient_matrix_UB_12      0.0567947000
_diffrn_orient_matrix_UB_13      -0.0543627000
_diffrn_orient_matrix_UB_21      -0.1102258000
_diffrn_orient_matrix_UB_22      0.0568994000
_diffrn_orient_matrix_UB_23      -0.1011399000
_diffrn_orient_matrix_UB_31      -0.0125221000
_diffrn_orient_matrix_UB_32      0.1833508000
_diffrn_orient_matrix_UB_33      0.0481501000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0176
_diffrn_reflns_av_unetI/netI     0.0103
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            15165
_diffrn_reflns_point_group_measured_fraction_full 0.985
_diffrn_reflns_point_group_measured_fraction_max 0.967
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.843
_diffrn_reflns_theta_min         3.573
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.856
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.72711
_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    1.352
_exptl_crystal_description       block
_exptl_crystal_F_000             340
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.29
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.186
_refine_diff_density_min         -0.238
_refine_diff_density_rms         0.058
_refine_ls_abs_structure_details
;
 Flack x determined using 1373 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.03(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.112
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     217
_refine_ls_number_reflns         3097
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.112
_refine_ls_R_factor_all          0.0265
_refine_ls_R_factor_gt           0.0265
_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^)+(0.0430P)^2^+0.1600P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0705
_refine_ls_wR_factor_ref         0.0706
_reflns_Friedel_coverage         0.805
_reflns_Friedel_fraction_full    0.967
_reflns_Friedel_fraction_max     0.936
_reflns_number_gt                3095
_reflns_number_total             3097
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo0c00147_si_001.cif
_cod_data_source_block           20181206_zy-pc-43
_cod_depositor_comments
'Adding full bibliography for 4038066--4038067.cif.'
_cod_database_code               4038066
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_max   0.912
_shelx_estimated_absorpt_t_min   0.754
_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
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C6(H6), C4(H4), C7(H7), C12(H12), C13(H13)
2.b Aromatic/amide H refined with riding coordinates:
 C1(H1A), C9(H9), C11(H11), C10(H10), C8(H8)
2.c Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C), C17(H17A,H17B,H17C)
2.d Idealised tetrahedral OH refined as rotating group:
 O2(H2), O5(H5), O3(H3)
;
_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 1.498
_oxdiff_exptl_absorpt_empirical_full_min 0.549