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_1555054
_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, C H4 O'
_chemical_formula_sum            'C21 H22 O10'
_chemical_formula_weight         434.38
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_audit_creation_date             2018-09-20
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2018-11-29 deposited with the CCDC.	2019-08-01 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 92.0160(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.89350(10)
_cell_length_b                   14.43300(10)
_cell_length_c                   15.74510(10)
_cell_measurement_reflns_used    19089
_cell_measurement_temperature    286(5)
_cell_measurement_theta_max      73.5790
_cell_measurement_theta_min      2.7780
_cell_volume                     2019.79(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    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      286(5)
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.990
_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  10.00   0.50    0.50    --    0.00  36.00   6.00   52
  2  \w     27.00  81.00   0.50    0.50    --    0.00  36.00   6.00  108
  3  \w     77.00 124.00   0.50    0.50    --   94.60  36.00   6.00   94
  4  \w    134.00 160.00   0.50    0.50    --   94.60  36.00   6.00   52
  5  \w     29.00  62.00   0.50    0.50    --    0.00  38.00 150.00   66
  6  \w     20.00  88.00   0.50    0.50    --    0.00  19.00-180.00  136
  7  \w    -17.00  15.00   0.50    0.50    --    0.00  19.00-180.00   64
  8  \w    -31.00  31.00   0.50    0.50    --    0.00 -82.00 -60.00  124
  9  \w    -33.00  30.00   0.50    0.50    --    0.00 -82.00-180.00  126
 10  \w    -56.00 -28.00   0.50    0.50    --    0.00 -36.00-150.00   56
 11  \w    149.00 175.00   0.50    0.50    --   94.60  65.00  93.94   52
 12  \w     67.00  93.00   0.50    0.50    --   94.60  71.00 106.74   52
 13  \w     70.00 114.00   0.50    0.50    --   94.60  65.00  93.94   88
 14  \w     77.00 167.00   0.50    0.50    --   94.60  45.00-180.00  180
 15  \w    119.00 145.00   0.50    0.50    --   94.60  82.00-180.00   52
 16  \w    155.00 180.00   0.50    0.50    --   94.60  71.00 106.74   50
 17  \w     72.00  98.00   0.50    0.50    --   94.60  58.00 120.44   52
 18  \w     74.00 100.00   0.50    0.50    --   94.60  54.00  86.88   52
 19  \w     73.00 176.00   0.50    0.50    --   94.60  15.00 -30.00  206
 20  \w      5.00 110.00   0.50    0.50    --   94.60 -61.00  60.00  210
 21  \w     71.00  96.00   0.50    0.50    --   94.60  61.00  90.00   50
 22  \w     79.00 184.00   0.50    0.50    --   94.60  15.00 -90.00  210
 23  \w     75.00 102.00   0.50    0.50    --   94.60  45.00  60.00   54
 24  \w     69.00  95.00   0.50    0.50    --   94.60  72.00 111.51   52
 25  \w     75.00 174.00   0.50    0.50    --   94.60  45.00  90.00  198
 26  \w     75.00 101.00   0.50    0.50    --   94.60  45.00 133.01   52
 27  \w     71.00  97.00   0.50    0.50    --   94.60  61.00 150.00   52
 28  \w    148.00 174.00   0.50    0.50    --   94.60  82.00-180.00   52
 29  \w     80.00 119.00   0.50    0.50    --   94.60  30.00  90.00   78
 30  \w     71.00  97.00   0.50    0.50    --   94.60  61.00  60.00   52
 31  \w      7.00 109.00   0.50    0.50    --   94.60 -45.00  60.00  204
 32  \w     76.00 101.00   0.50    0.50    --   94.60 -36.00-150.00   50
 33  \w     78.00 161.00   0.50    0.50    --   94.60  30.00 150.00  166
 34  \w     86.00 111.00   0.50    0.50    --   94.60 -30.00  60.00   50
 35  \w     76.00 183.00   0.50    0.50    --   94.60  42.00 160.53  214
 36  \w     13.00  71.00   0.50    0.50    --   94.60 -36.00-150.00  116
;
_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      0.0831360000
_diffrn_orient_matrix_UB_12      0.0178896000
_diffrn_orient_matrix_UB_13      0.0859579000
_diffrn_orient_matrix_UB_21      -0.1297799000
_diffrn_orient_matrix_UB_22      -0.0462820000
_diffrn_orient_matrix_UB_23      0.0464895000
_diffrn_orient_matrix_UB_31      0.0792411000
_diffrn_orient_matrix_UB_32      -0.0944831000
_diffrn_orient_matrix_UB_33      -0.0064708000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0183
_diffrn_reflns_av_unetI/netI     0.0089
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            26904
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.831
_diffrn_reflns_theta_min         4.156
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.979
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.61823
_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    1.428
_exptl_crystal_description       block
_exptl_crystal_F_000             912
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: Methanol'
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.211
_refine_diff_density_min         -0.300
_refine_diff_density_rms         0.084
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.083
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     300
_refine_ls_number_reflns         4034
_refine_ls_number_restraints     15
_refine_ls_restrained_S_all      1.082
_refine_ls_R_factor_all          0.0425
_refine_ls_R_factor_gt           0.0413
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0615P)^2^+0.4591P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1123
_refine_ls_wR_factor_ref         0.1134
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3832
_reflns_number_total             4034
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9qo00820a2.cif
_cod_data_source_block           20180918_zy_pc_59-66
_cod_database_code               1555054
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_max   0.892
_shelx_estimated_absorpt_t_min   0.726
_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, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All C(H,H,H,H,H,H) groups, All O(H) groups
2. Restrained distances
 O10-H10 = O11-H11
 0.85 with sigma of 0.02
 O10-C21 \\sim O11-C21
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(O10) \\sim Ueq, Uanis(O11) \\sim Ueq: with sigma of 0.1 and sigma for
terminal atoms of 0.2
4. Others
 Fixed Sof: O10(0.5) H21D(0.5) H21E(0.5) H21F(0.5) H21A(0.5) H21B(0.5)
 H21C(0.5) O11(0.5) H11(0.5) H10(0.5)
5.a Ternary CH refined with riding coordinates:
 C15(H15)
5.b Secondary CH2 refined with riding coordinates:
 C16(H16A,H16B), C7(H7A,H7B)
5.c Aromatic/amide H refined with riding coordinates:
 C9(H9), C13(H13)
5.d Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C10(H10A,H10B,H10C), C20(H20A,H20B,H20C), C21(H21D,H21E,
 H21F), C21(H21A,H21B,H21C)
5.e Idealised tetrahedral OH refined as rotating group:
 O6(H6), O8(H8), O11(H11)
;
_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 1.506
_oxdiff_exptl_absorpt_empirical_full_min 0.722