Canescones A–E: aromatic polyketide dimers with PTP1B inhibitory activity from Penicillium canescens
Zang, Yi; Gong, Yi-Hua; Li, Xu-Wen; Li, Xiao-Nian; Liu, Jun-Jun; Chen, Chun-Mei; Zhou, Yuan; Gu, Liang-Hu; Luo, Zeng-Wei; Wang, Jian-Ping; Sun, Wei-Guang; Zhu, Hu-Cheng; Zhang, Yong-Hui; Organic Chemistry Frontiers 6 (2019) 3274–; doi:10.1039/C9QO00820A

data_1555056
_publ_section_title
;
 Canescones A--E: aromatic polyketide dimers with PTP1B inhibitory
 activity from Penicillium canescens
;
_journal_issue                   18
_journal_name_full               'Organic Chemistry Frontiers'
_journal_page_first              3274
_journal_paper_doi               10.1039/C9QO00820A
_journal_volume                  6
_journal_year                    2019
_chemical_absolute_configuration rmad
_chemical_compound_source        fungus
_chemical_formula_moiety         'C20 H18 O10, C H4 O'
_chemical_formula_sum            'C21 H22 O11'
_chemical_formula_weight         450.38
_space_group_crystal_system      orthorhombic
_space_group_IT_number           29
_space_group_name_Hall           'P 2c -2ac'
_space_group_name_H-M_alt        'P c a 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2018-12-18
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2018-12-18 deposited with the CCDC.	2019-08-01 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.33914(3)
_cell_length_b                   13.29606(5)
_cell_length_c                   18.06836(8)
_cell_measurement_reflns_used    36688
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      73.6720
_cell_measurement_theta_min      3.3210
_cell_volume                     2003.378(14)
_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 1.000
_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    -14.00  13.00   0.50    0.50    --    0.00  29.00  61.00   54
  2  \w     23.00  59.00   0.50    0.50    --   94.60 -29.00 -99.00   72
  3  \w    141.00 168.00   0.50    0.50    --   94.60  29.00  61.00   54
  4  \w     78.00 134.00   0.50    0.50    --   94.60  29.00  61.00  112
  5  \w      5.00  41.00   0.50    0.50    --    0.00  57.00 -90.00   72
  6  \w     44.00  70.00   0.50    0.50    --    0.00  38.00-150.00   52
  7  \w    -30.00  22.00   0.50    0.50    --    0.00 -82.00-180.00  104
  8  \w     25.00  50.00   0.50    0.50    --    0.00  29.00  61.00   50
  9  \w    -29.00  31.00   0.50    0.50    --    0.00 -82.00 120.00  120
 10  \w     44.00  88.00   0.50    0.50    --    0.00  57.00 -90.00   88
 11  \w    -15.00  40.00   0.50    0.50    --    0.00  38.00-150.00  110
 12  \w    -17.00  69.00   0.50    0.50    --    0.00  38.00 -90.00  172
 13  \w    -22.00  22.00   0.50    0.50    --    0.00  57.00 -30.00   88
 14  \w    -61.00 -36.00   0.50    0.50    --    0.00 -29.00 -99.00   50
 15  \w     31.00  83.00   0.50    0.50    --    0.00  57.00 -30.00  104
 16  \w    -17.00  80.00   0.50    0.50    --    0.00  38.00 120.00  194
 17  \w     66.00  92.00   0.50    0.50    --   94.60  75.00  81.38   52
 18  \w     67.00  93.00   0.50    0.50    --   94.60  72.00 -82.76   52
 19  \w    107.00 132.00   0.50    0.50    --   94.60  45.00 -30.00   50
 20  \w    111.00 137.00   0.50    0.50    --   94.60  61.00   8.36   52
 21  \w     72.00 108.00   0.50    0.50    --   94.60  61.00   8.36   72
 22  \w     75.00 100.00   0.50    0.50    --   94.60  45.00 -30.00   50
 23  \w     66.00 184.00   0.50    0.50    --   94.60  75.00 -97.79  236
 24  \w     67.00  93.00   0.50    0.50    --   94.60  72.00  61.40   52
 25  \w     71.00  97.00   0.50    0.50    --   94.60  61.00 -30.00   52
 26  \w     66.00  95.00   0.50    0.50    --   94.60  75.00-154.41   58
 27  \w     67.00 183.00   0.50    0.50    --   94.60  71.00-133.83  232
 28  \w      6.00 126.00   0.50    0.50    --   94.60 -82.00 -30.00  240
 29  \w     71.00  96.00   0.50    0.50    --   94.60  60.00  51.29   50
 30  \w    142.00 167.00   0.50    0.50    --   94.60  60.00  51.29   50
 31  \w     73.00 127.00   0.50    0.50    --   94.60  61.00 113.35  108
 32  \w     71.00 102.00   0.50    0.50    --   94.60  61.00-180.00   62
 33  \w     71.00 152.00   0.50    0.50    --   94.60  61.00-150.00  162
 34  \w     46.00  74.00   0.50    0.50    --   94.60 -82.00-150.00   56
 35  \w     71.00  97.00   0.50    0.50    --   94.60  63.00-105.77   52
 36  \w    138.00 174.00   0.50    0.50    --   94.60  61.00  30.00   72
 37  \w    137.00 183.00   0.50    0.50    --   94.60  75.00 107.78   92
 38  \w    148.00 174.00   0.50    0.50    --   94.60  72.00-175.15   52
 39  \w     71.00  99.00   0.50    0.50    --   94.60  61.00   0.00   56
 40  \w     71.00  97.00   0.50    0.50    --   94.60  61.00  30.00   52
 41  \w     71.00  97.00   0.50    0.50    --   94.60  61.00 -90.00   52
 42  \w     71.00 154.00   0.50    0.50    --   94.60  61.00  90.00  166
 43  \w     67.00  92.00   0.50    0.50    --   94.60  71.00 -25.73   50
 44  \w     67.00 150.00   0.50    0.50    --   94.60  71.00 137.73  166
 45  \w    158.00 184.00   0.50    0.50    --   94.60  71.00 137.73   52
 46  \w     67.00  93.00   0.50    0.50    --   94.60  71.00 -36.30   52
 47  \w     99.00 183.00   0.50    0.50    --   94.60  71.00 -36.30  168
 48  \w     68.00  94.00   0.50    0.50    --   94.60  74.00  89.84   52
 49  \w     66.00  92.00   0.50    0.50    --   94.60  75.00 107.78   52
 50  \w     67.00 147.00   0.50    0.50    --   94.60  71.00 152.18  160
 51  \w    107.00 172.00   0.50    0.50    --   94.60  71.00 -73.78  130
 52  \w     67.00 100.00   0.50    0.50    --   94.60  71.00 -73.78   66
 53  \w      6.00  75.00   0.50    0.50    --   94.60 -77.00-120.00  138
 54  \w     88.00 123.00   0.50    0.50    --   94.60 -77.00-120.00   70
 55  \w     70.00 144.00   0.50    0.50    --   94.60  64.00-171.76  148
 56  \w     79.00 112.00   0.50    0.50    --   94.60 -82.00-150.00   66
 57  \w     13.00 120.00   0.50    0.50    --   94.60 -82.00  90.00  214
 58  \w     71.00 183.00   0.50    0.50    --   94.60  61.00  60.00  224
 59  \w     20.00  72.00   0.50    0.50    --   94.60 -82.00  30.00  104
 60  \w     93.00 125.00   0.50    0.50    --   94.60 -82.00  30.00   64
 61  \w     68.00  94.00   0.50    0.50    --   94.60  70.00 124.55   52
 62  \w      6.00 123.00   0.50    0.50    --   94.60 -82.00-180.00  234
 63  \w     67.00  93.00   0.50    0.50    --   94.60  72.00-175.15   52
;
_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      -0.1291556000
_diffrn_orient_matrix_UB_12      -0.0720050000
_diffrn_orient_matrix_UB_13      0.0301836000
_diffrn_orient_matrix_UB_21      -0.1280893000
_diffrn_orient_matrix_UB_22      0.0822760000
_diffrn_orient_matrix_UB_23      -0.0105066000
_diffrn_orient_matrix_UB_31      -0.0323810000
_diffrn_orient_matrix_UB_32      -0.0383627000
_diffrn_orient_matrix_UB_33      -0.0790326000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0295
_diffrn_reflns_av_unetI/netI     0.0125
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_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       21
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            45175
_diffrn_reflns_point_group_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.971
_diffrn_reflns_theta_min         3.324
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.047
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.83060
_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    1.493
_exptl_crystal_description       block
_exptl_crystal_F_000             944
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: Methanol'
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.149
_refine_diff_density_min         -0.198
_refine_diff_density_rms         0.041
_refine_ls_abs_structure_details
;
 Flack x determined using 1882 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.02(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.067
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     297
_refine_ls_number_reflns         4006
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.067
_refine_ls_R_factor_all          0.0219
_refine_ls_R_factor_gt           0.0218
_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^)+(0.0341P)^2^+0.3520P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0559
_refine_ls_wR_factor_ref         0.0559
_reflns_Friedel_coverage         0.902
_reflns_Friedel_fraction_full    0.978
_reflns_Friedel_fraction_max     0.968
_reflns_number_gt                3989
_reflns_number_total             4006
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9qo00820a2.cif
_cod_data_source_block           20181128_zy-pc-46-55
_cod_original_cell_volume        2003.377(13)
_cod_database_code               1555056
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.902
_shelx_estimated_absorpt_t_min   0.780
_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 Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B)
2.b Aromatic/amide H refined with riding coordinates:
 C7(H7), C14(H14)
2.c Idealised Me refined as rotating group:
 C21(H21A,H21B,H21C), C22(H22A,H22B,H22C), C23(H23A,H23B,H23C), C24(H24A,H24B,
 H24C), C25(H25A,H25B,H25C)
2.d Idealised tetrahedral OH refined as rotating group:
 O3(H3), O5(H5), O10(H10)
;
_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 1.332
_oxdiff_exptl_absorpt_empirical_full_min 0.681