Novel anthraquinone derivatives as inhibitors of protein tyrosine phosphatases and indoleamine 2,3-dioxygenase 1 from the deep-sea derived fungus Alternaria tenuissima DFFSCS013
Pan, Dongyan; Zhang, Xuexia; Zheng, Haizhou; Zheng, Zhihui; Nong, Xuhua; Liang, Xiao; Ma, Xuan; Qi, Shuhua; Organic Chemistry Frontiers 6 (2019) 3252–; doi:10.1039/C9QO00775J

data_1555043
_publ_section_title
;
 Novel anthraquinone derivatives as inhibitors of protein tyrosine
 phosphatases and indoleamine 2,3-dioxygenase 1 from the deep-sea derived
 fungus Alternaria tenuissima DFFSCS013
;
_journal_issue                   18
_journal_name_full               'Organic Chemistry Frontiers'
_journal_page_first              3252
_journal_paper_doi               10.1039/C9QO00775J
_journal_volume                  6
_journal_year                    2019
_chemical_absolute_configuration unk
_chemical_formula_moiety         'C25 H28 O10'
_chemical_formula_sum            'C25 H28 O10'
_chemical_formula_weight         488.49
_space_group_crystal_system      monoclinic
_space_group_IT_number           5
_space_group_name_Hall           'I 2y'
_space_group_name_H-M_alt        'I 1 2 1'
_symmetry_Int_Tables_number      5
_audit_creation_date             2018-07-05
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2018-07-12 deposited with the CCDC.	2019-08-05 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 100.124(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.9189(4)
_cell_length_b                   6.5987(2)
_cell_length_c                   26.7335(10)
_cell_measurement_reflns_used    7548
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      73.4340
_cell_measurement_theta_min      3.8600
_cell_volume                     2069.83(12)
_computing_cell_refinement       'CrysAlisPro 1.171.39.33c (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.33c (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.33c (Rigaku OD, 2017)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine (Bourhis et al., 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 0.9575
_diffrn_measured_fraction_theta_max 0.9575
_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    -17.00  22.00   0.50    2.80    --    0.00 -57.00 -30.00   78
  2  \w    -58.00 -31.00   0.50    2.80    --    0.00 -19.00  30.00   54
  3  \w    -23.00   2.00   0.50    2.80    --    0.00 -19.00  30.00   50
  4  \w    -89.00 -24.00   0.50    2.80    --    0.00 -57.00 -30.00  130
  5  \w    -30.00  31.00   0.50    2.80    --    0.00 -82.00  30.00  122
  6  \w    -25.00   5.00   0.50    2.80    --    0.00 -82.00-150.00   60
  7  \w      6.00  31.00   0.50   25.36    --   94.60 -82.00 -30.00   50
  8  \w    136.00 183.00   0.50   25.36    --   94.60   0.00 -60.00   94
  9  \w      6.00 115.00   0.50   25.36    --   94.60 -61.00  90.00  218
 10  \w      5.00 100.00   0.50   25.36    --   94.60 -30.00-150.00  190
 11  \w      9.00 106.00   0.50   25.36    --   94.60 -30.00 120.00  194
 12  \w     64.00 123.00   0.50   25.36    --   94.60 -82.00-180.00  118
 13  \w      8.00 116.00   0.50   25.36    --   94.60 -61.00 -30.00  216
 14  \w     96.00 123.00   0.50   25.36    --   94.60  30.00 -30.00   54
 15  \w    141.00 183.00   0.50   25.36    --   94.60  30.00 -30.00   84
 16  \w     53.00 121.00   0.50   25.36    --   94.60 -82.00 -30.00  136
 17  \w      7.00 125.00   0.50   25.36    --   94.60 -82.00  90.00  236
 18  \w      5.00 108.00   0.50   25.36    --   94.60   0.00 -60.00  206
 19  \w     39.00  64.00   0.50   25.36    --   94.60 -61.00-180.00   50
 20  \w     67.00 118.00   0.50   25.36    --   94.60 -61.00-180.00  102
 21  \w     91.00 118.00   0.50   25.36    --   94.60 -82.00 -60.00   54
 22  \w     87.00 114.00   0.50   25.36    --   94.60 -82.00  60.00   54
 23  \w     89.00 116.00   0.50   25.36    --   94.60 -82.00-124.97   54
;
_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      0.0112845000
_diffrn_orient_matrix_UB_12      0.2312972000
_diffrn_orient_matrix_UB_13      0.0070148000
_diffrn_orient_matrix_UB_21      0.0070015000
_diffrn_orient_matrix_UB_22      0.0238222000
_diffrn_orient_matrix_UB_23      -0.0566787000
_diffrn_orient_matrix_UB_31      -0.1306357000
_diffrn_orient_matrix_UB_32      0.0212824000
_diffrn_orient_matrix_UB_33      -0.0127748000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0250
_diffrn_reflns_av_unetI/netI     0.0240
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_number            9974
_diffrn_reflns_theta_full        73.8672
_diffrn_reflns_theta_max         73.87
_diffrn_reflns_theta_min         3.85
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.025
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.91061
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.33c (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear yellowish yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   yellowish
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.5675
_exptl_crystal_description       plate
_exptl_crystal_F_000             1035.9094
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.2334
_refine_diff_density_min         -0.1984
_refine_diff_density_rms         0.0452
_refine_ls_abs_structure_details
'Flack, H. D. (1983). Acta Cryst. A39, 876-881.'
_refine_ls_abs_structure_Flack   -0.01(11)
_refine_ls_d_res_high            0.8025
_refine_ls_d_res_low             11.4942
_refine_ls_goodness_of_fit_ref   1.0239
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_constraints    44
_refine_ls_number_parameters     326
_refine_ls_number_reflns         4013
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.0239
_refine_ls_R_factor_all          0.0344
_refine_ls_R_factor_gt           0.0329
_refine_ls_shift/su_max          0.0002
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0596P)^2^+1.0297P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0901
_refine_ls_wR_factor_ref         0.0909
_reflns_Friedel_coverage         0.929
_reflns_limit_h_max              14
_reflns_limit_h_min              -14
_reflns_limit_k_max              8
_reflns_limit_k_min              -8
_reflns_limit_l_max              32
_reflns_limit_l_min              -32
_reflns_number_gt                3819
_reflns_number_total             4013
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            c9qo00775j2.cif
_cod_data_source_block           pdy-dp-25_collect
_cod_original_sg_symbol_Hall     ' C 2y (x,y,-x+z)'
_cod_database_code               1555043
_chemical_oxdiff_formula         'C H O'
_reflns_odcompleteness_completeness 99.70
_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 Ternary CH refined with riding coordinates:
 C17(H17), C7(H7), C14(H14), C18(H18)
2.b Secondary CH2 refined with riding coordinates:
 C5(H5a,H5b), C16(H16a,H16b), C19(H19a,H19b), C8(H8a,H8b), C11(H11a,H11b),
 C13(H13a,H13b)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2a)
2.d Idealised Me refined as rotating group:
 C21(H21a,H21b,H21c), C20(H20a,H20b,H20c)
2.e Idealised tetrahedral OH refined as rotating group:
 O2(H2), O4(H4), O3(H3), O6(H6)
;
_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 1.454
_oxdiff_exptl_absorpt_empirical_full_min 0.532