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_1555055
_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_compound_source        fungus
_chemical_formula_moiety         'C20 H18 O9, H2 O'
_chemical_formula_sum            'C20 H20 O10'
_chemical_formula_weight         420.36
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2018-11-08
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.18 svn.r3508 for OlexSys, GUI svn.r5497)
;
_audit_update_record
;
2018-11-29 deposited with the CCDC.	2019-08-01 downloaded from the CCDC.
;
_cell_angle_alpha                93.717(2)
_cell_angle_beta                 90.826(2)
_cell_angle_gamma                92.317(2)
_cell_formula_units_Z            2
_cell_length_a                   9.0160(2)
_cell_length_b                   9.3778(2)
_cell_length_c                   10.6360(2)
_cell_measurement_reflns_used    10882
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      73.5380
_cell_measurement_theta_min      4.1660
_cell_volume                     896.52(3)
_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      100.01(10)
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.980
_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      0.00  26.00   0.50    0.50    --    0.00  38.00-180.00   52
  2  \w    -16.00  34.00   0.50    0.50    --    0.00  38.00 150.00  100
  3  \w    -21.00  54.00   0.50    0.50    --    0.00  57.00  60.00  150
  4  \w    -15.00  89.00   0.50    0.50    --    0.00  38.00 -30.00  208
  5  \w    -21.00  13.00   0.50    0.50    --    0.00  57.00-120.00   68
  6  \w     21.00  81.00   0.50    0.50    --    0.00  57.00-120.00  120
  7  \w     52.00  88.00   0.50    0.50    --    0.00  38.00-180.00   72
  8  \w     41.00  79.00   0.50    0.50    --    0.00  38.00 150.00   76
  9  \w     67.00  95.00   0.50    1.50    --   94.60  73.00  81.03   56
 10  \w    139.00 178.00   0.50    1.50    --   94.60  69.00-175.89   78
 11  \w    142.00 168.00   0.50    1.50    --   94.60  61.00 126.14   52
 12  \w     72.00 107.00   0.50    1.50    --   94.60  61.00 158.57   70
 13  \w     67.00  94.00   0.50    1.50    --   94.60  72.00-132.97   54
 14  \w    140.00 167.00   0.50    1.50    --   94.60  72.00-132.97   54
 15  \w    147.00 178.00   0.50    1.50    --   94.60  75.00 -90.47   62
 16  \w     68.00  96.00   0.50    1.50    --   94.60  69.00-175.89   56
 17  \w    152.00 178.00   0.50    1.50    --   94.60  70.00 161.12   52
 18  \w     73.00 176.00   0.50    1.50    --   94.60  52.00 -86.18  206
 19  \w     71.00 113.00   0.50    1.50    --   94.60  61.00 126.14   84
 20  \w     79.00 178.00   0.50    1.50    --   94.60  30.00-180.00  198
 21  \w     69.00  95.00   0.50    1.50    --   94.60  70.00 161.12   52
 22  \w     74.00 123.00   0.50    1.50    --   94.60  61.00-180.00   98
 23  \w     72.00  98.00   0.50    1.50    --   94.60  61.00  60.00   52
 24  \w     61.00  87.00   0.50    1.50    --   94.60 -82.00-180.00   52
 25  \w     82.00 149.00   0.50    1.50    --   94.60  45.00-120.00  134
 26  \w    154.00 183.00   0.50    1.50    --   94.60  45.00-120.00   58
 27  \w     12.00  62.00   0.50    1.50    --   94.60 -82.00 -30.00  100
 28  \w     65.00 126.00   0.50    1.50    --   94.60 -82.00 -30.00  122
 29  \w     72.00  97.00   0.50    1.50    --   94.60  61.00   4.08   50
 30  \w     71.00 166.00   0.50    1.50    --   94.60  61.00 -30.00  190
 31  \w     69.00 184.00   0.50    1.50    --   94.60  66.00 -52.22  230
 32  \w     71.00  97.00   0.50    1.50    --   94.60  61.00-150.00   52
 33  \w     78.00 171.00   0.50    1.50    --   94.60  45.00  90.00  186
 34  \w    155.00 180.00   0.50    1.50    --   94.60  70.00 104.83   50
 35  \w     72.00  98.00   0.50    1.50    --   94.60  61.00 -90.00   52
 36  \w     72.00  98.00   0.50    1.50    --   94.60  61.00 -60.00   52
 37  \w     72.00 135.00   0.50    1.50    --   94.60  61.00  30.00  126
 38  \w     72.00  98.00   0.50    1.50    --   94.60  61.00  90.00   52
 39  \w      6.00 124.00   0.50    1.50    --   94.60 -82.00 -60.00  236
 40  \w      6.00 126.00   0.50    1.50    --   94.60 -82.00 120.00  240
 41  \w     68.00 111.00   0.50    1.50    --   94.60  70.00 104.83   86
 42  \w     75.00 127.00   0.50    1.50    --   94.60  45.00 -90.00  104
 43  \w    133.00 158.00   0.50    1.50    --   94.60  73.00  81.03   50
 44  \w     69.00  94.00   0.50    1.50    --   94.60  68.00   9.90   50
 45  \w     66.00  92.00   0.50    1.50    --   94.60  75.00 -90.47   52
 46  \w     71.00  97.00   0.50    1.50    --   94.60  61.00 150.00   52
 47  \w     70.00 179.00   0.50    1.50    --   94.60  64.00  38.38  218
 48  \w     29.00 122.00   0.50    1.50    --   94.60 -82.00-150.00  186
 49  \w      9.00  78.00   0.50    1.50    --   94.60 -82.00  30.00  138
 50  \w     85.00 122.00   0.50    1.50    --   94.60 -82.00  30.00   74
 51  \w     74.00 182.00   0.50    1.50    --   94.60  49.00  11.19  216
;
_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      0.0238021000
_diffrn_orient_matrix_UB_12      0.0363309000
_diffrn_orient_matrix_UB_13      0.1423837000
_diffrn_orient_matrix_UB_21      -0.0075134000
_diffrn_orient_matrix_UB_22      0.1604622000
_diffrn_orient_matrix_UB_23      -0.0214517000
_diffrn_orient_matrix_UB_31      -0.1692031000
_diffrn_orient_matrix_UB_32      -0.0089195000
_diffrn_orient_matrix_UB_33      0.0184745000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0313
_diffrn_reflns_av_unetI/netI     0.0223
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.980
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            18581
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.980
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.821
_diffrn_reflns_theta_min         4.166
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.082
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.73450
_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            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.557
_exptl_crystal_description       block
_exptl_crystal_F_000             440
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: Methanol'
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.243
_refine_diff_density_min         -0.243
_refine_diff_density_rms         0.043
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     291
_refine_ls_number_reflns         3560
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.050
_refine_ls_R_factor_all          0.0357
_refine_ls_R_factor_gt           0.0326
_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^)+(0.0355P)^2^+0.4720P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0822
_refine_ls_wR_factor_ref         0.0840
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3256
_reflns_number_total             3560
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9qo00820a2.cif
_cod_data_source_block           20181102_zy_pc_35
_cod_database_code               1555055
_shelx_shelxl_version_number     2017/1
_shelx_estimated_absorpt_t_max   0.968
_shelx_estimated_absorpt_t_min   0.813
_reflns_odcompleteness_completeness 99.69
_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. Restrained distances
 O008-H008
 0.82 with sigma of 0.01
3.a Secondary CH2 refined with riding coordinates:
 C00O(H00A,H00B), C00T(H00J,H00K)
3.b Aromatic/amide H refined with riding coordinates:
 C00G(H00G), C00Q(H00Q)
3.c Idealised Me refined as rotating group:
 C00R(H00C,H00D,H00E), C00S(H00F,H00H,H00I), C00U(H00L,H00N,H00O)
3.d Idealised tetrahedral OH refined as rotating group:
 O003(H003)
;
_shelx_res_checksum              64640
_shelx_hkl_checksum              44615
_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 1.350
_oxdiff_exptl_absorpt_empirical_full_min 0.830