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_1555058
_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_formula_moiety         'C22 H23 N O9'
_chemical_formula_sum            'C22 H23 N O9'
_chemical_formula_weight         445.41
_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             2018-12-06
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2018-12-06 deposited with the CCDC.	2019-08-01 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 102.3917(6)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.26703(5)
_cell_length_b                   13.79202(8)
_cell_length_c                   17.73644(10)
_cell_measurement_reflns_used    25467
_cell_measurement_temperature    99.99(10)
_cell_measurement_theta_max      73.6880
_cell_measurement_theta_min      3.1860
_cell_volume                     1975.18(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      99.99(10)
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.995
_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     51.00  82.00   0.50    0.50    --    0.00  57.00-120.00   62
  2  \w    -22.00   7.00   0.50    0.50    --    0.00  57.00-120.00   58
  3  \w      6.00  46.00   0.50    0.50    --    0.00  38.00  60.00   80
  4  \w    -37.00  10.00   0.50    0.50    --    0.00 -38.00  60.00   94
  5  \w     20.00  89.00   0.50    0.50    --    0.00  38.00 -30.00  138
  6  \w     -5.00  26.00   0.50    0.50    --    0.00  57.00  90.00   62
  7  \w    -16.00  77.00   0.50    0.50    --    0.00  19.00 120.00  186
  8  \w    -17.00  61.00   0.50    0.50    --    0.00  57.00-180.00  156
  9  \w     38.00  88.00   0.50    0.50    --    0.00  57.00  90.00  100
 10  \w    -30.00   7.00   0.50    0.50    --    0.00 -82.00 -30.00   74
 11  \w     18.00  44.00   0.50    0.50    --    0.00  57.00-120.00   52
 12  \w    -17.00  16.00   0.50    0.50    --    0.00  38.00 -30.00   66
 13  \w     69.00  95.00   0.50    0.60    --   94.60  73.00  53.29   52
 14  \w     68.00 184.00   0.50    0.60    --   94.60  70.00-174.62  232
 15  \w     69.00  95.00   0.50    0.60    --   94.60  68.00  25.71   52
 16  \w    143.00 169.00   0.50    0.60    --   94.60  67.00 -98.93   52
 17  \w     69.00 129.00   0.50    0.60    --   94.60  67.00 -98.93  120
 18  \w    131.00 157.00   0.50    0.60    --   94.60  70.00 -51.85   52
 19  \w     66.00  91.00   0.50    0.60    --   94.60  74.00   0.40   50
 20  \w     68.00 178.00   0.50    0.60    --   94.60  69.00 105.10  220
 21  \w     69.00  95.00   0.50    0.60    --   94.60  73.00 123.44   52
 22  \w    145.00 174.00   0.50    0.60    --   94.60  69.00  72.83   58
 23  \w     68.00 119.00   0.50    0.60    --   94.60  69.00 170.02  102
 24  \w    123.00 184.00   0.50    0.60    --   94.60  69.00 170.02  122
 25  \w     67.00  93.00   0.50    0.60    --   94.60  73.00  92.26   52
 26  \w     69.00 100.00   0.50    0.60    --   94.60  66.00  91.65   62
 27  \w     70.00 184.00   0.50    0.60    --   94.60  65.00 123.22  228
 28  \w     30.00 110.00   0.50    0.60    --   94.60 -82.00  90.00  160
 29  \w      6.00 126.00   0.50    0.60    --   94.60 -82.00 -90.00  240
 30  \w     71.00 112.00   0.50    0.60    --   94.60  61.00 -71.56   82
 31  \w    108.00 183.00   0.50    0.60    --   94.60  65.00-136.48  150
 32  \w     68.00 137.00   0.50    0.60    --   94.60  69.00  72.83  138
 33  \w     68.00  96.00   0.50    0.60    --   94.60  70.00 -51.85   56
 34  \w      5.00 124.00   0.50    0.60    --   94.60 -77.00 120.00  238
 35  \w     70.00  96.00   0.50    0.60    --   94.60  65.00-136.48   52
 36  \w     71.00 184.00   0.50    0.60    --   94.60  61.00   0.00  226
 37  \w     71.00 184.00   0.50    0.60    --   94.60  61.00 -60.00  226
 38  \w     71.00  97.00   0.50    0.60    --   94.60  61.00-150.00   52
 39  \w     71.00  97.00   0.50    0.60    --   94.60  63.00-113.10   52
 40  \w     51.00  78.00   0.50    0.60    --   94.60 -82.00 -60.00   54
 41  \w     92.00 123.00   0.50    0.60    --   94.60 -82.00 -60.00   62
 42  \w     71.00  97.00   0.50    0.60    --   94.60  61.00-120.00   52
 43  \w     70.00 132.00   0.50    0.60    --   94.60  65.00-108.84  124
 44  \w     70.00 183.00   0.50    0.60    --   94.60  65.00  60.56  226
 45  \w     76.00 102.00   0.50    0.60    --   94.60  45.00-120.00   52
 46  \w     71.00 129.00   0.50    0.60    --   94.60  61.00 -30.00  116
 47  \w    138.00 165.00   0.50    0.60    --   94.60  61.00 -30.00   54
 48  \w     90.00 122.00   0.50    0.60    --   94.60 -82.00   0.00   64
 49  \w     45.00  79.00   0.50    0.60    --   94.60 -82.00   0.00   68
 50  \w    101.00 126.00   0.50    0.60    --   94.60  71.00  36.71   50
 51  \w     47.00 125.00   0.50    0.60    --   94.60 -82.00-180.00  156
 52  \w     67.00  93.00   0.50    0.60    --   94.60  71.00  36.71   52
 53  \w    147.00 172.00   0.50    0.60    --   94.60  68.00  25.71   50
 54  \w     66.00  91.00   0.50    0.60    --   94.60  75.00 151.85   50
 55  \w     70.00 178.00   0.50    0.60    --   94.60  63.00 -19.63  216
 56  \w     68.00  94.00   0.50    0.60    --   94.60  70.00 143.68   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      -0.1735227000
_diffrn_orient_matrix_UB_12      -0.0235014000
_diffrn_orient_matrix_UB_13      -0.0484954000
_diffrn_orient_matrix_UB_21      -0.0402503000
_diffrn_orient_matrix_UB_22      -0.0569609000
_diffrn_orient_matrix_UB_23      0.0684322000
_diffrn_orient_matrix_UB_31      -0.0684681000
_diffrn_orient_matrix_UB_32      0.0931364000
_diffrn_orient_matrix_UB_33      0.0295488000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0284
_diffrn_reflns_av_unetI/netI     0.0127
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            44113
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.957
_diffrn_reflns_theta_min         4.097
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.993
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.74429
_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    1.498
_exptl_crystal_description       block
_exptl_crystal_F_000             936
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: methanol'
_exptl_crystal_size_max          0.29
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.241
_refine_diff_density_min         -0.224
_refine_diff_density_rms         0.039
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     295
_refine_ls_number_reflns         3987
_refine_ls_number_restraints     7
_refine_ls_restrained_S_all      1.065
_refine_ls_R_factor_all          0.0351
_refine_ls_R_factor_gt           0.0331
_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^)+(0.0476P)^2^+0.7808P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0899
_refine_ls_wR_factor_ref         0.0913
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3765
_reflns_number_total             3987
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9qo00820a2.cif
_cod_data_source_block           20181203_zy-pc-25
_cod_database_code               1555058
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_max   0.890
_shelx_estimated_absorpt_t_min   0.762
_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. Rigid bond restraints
 O27, C16
 with sigma for 1-2 distances of 0.005 and sigma for 1-3 distances of 0.005
3. Uiso/Uaniso restraints and constraints
C16 \\sim O27: within 2A with sigma of 0.005 and sigma for terminal atoms of
0.01
4.a Ternary CH refined with riding coordinates:
 C18(H18)
4.b Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B), C24(H24A,H24B), C25(H25A,H25B)
4.c Aromatic/amide H refined with riding coordinates:
 C14(H14), C7(H7)
4.d Idealised Me refined as rotating group:
 C26(H26A,H26B,H26C), C22(H22A,H22B,H22C), C21(H21A,H21B,H21C), C23(H23A,H23B,
 H23C)
4.e Idealised tetrahedral OH refined as rotating group:
 O29(H29), O26(H26)
;
_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 1.439
_oxdiff_exptl_absorpt_empirical_full_min 0.743