Bioactive Anthraquinone Derivatives from the Mangrove-Derived Fungus Stemphylium sp. 33231.
Zhou, Xue-Ming; Zheng, Cai-Juan; Chen, Guang-Ying; Song, Xiao-Ping; Han, Chang-Ri; Li, Gao-Nan; Fu, Yan-Hui; Chen, Wen-Hao; Niu, Zhi-Gang; Journal of natural products 77 (2014) 2021–2028; doi:10.1021/np500340y

data_1517405
_publ_section_title
;
 Bioactive Anthraquinone Derivatives from the Mangrove-Derived Fungus
 Stemphylium sp. 33231.
;
_journal_issue                   9
_journal_name_full               'Journal of natural products'
_journal_page_first              2021
_journal_page_last               2028
_journal_paper_doi               10.1021/np500340y
_journal_volume                  77
_journal_year                    2014
_chemical_absolute_configuration rmad
_chemical_formula_moiety         'C17 H20 O10'
_chemical_formula_sum            'C17 H20 O10'
_chemical_formula_weight         384.33
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_audit_creation_date             2013-10-15
_audit_creation_method
;
  Olex2 1.2-ac2
  (compiled 2012.03.27 svn.r2268, GUI svn.r4156)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.16471(7)
_cell_length_b                   11.40078(15)
_cell_length_c                   23.0795(3)
_cell_measurement_reflns_used    6772
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      67.0670
_cell_measurement_theta_min      3.8100
_cell_volume                     1622.09(4)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_molecular_graphics
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement
;
SHELXL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution
;
SHELXS, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 10.5095
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details
;
  1 omega   12.00   86.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       40.0339   57.0000   90.0000 74

  2 omega   23.00  104.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       40.0339   38.0000 -180.0000 81

  3 omega   16.00   72.00   1.0000   35.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -22.0000 -149.0000 56

  4 omega   20.00   47.00   1.0000   35.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -30.0000   90.0000 27

  5 omega   21.00   46.00   1.0000   35.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -77.0000   30.0000 25

  6 omega   80.00  105.00   1.0000   35.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -77.0000   30.0000 25

  7 omega   73.00  113.00   1.0000   35.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  125.0000  -30.0000 40

  8 omega   25.00   63.00   1.0000   35.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -61.0000    0.0000 38

  9 omega   25.00   50.00   1.0000   35.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000 -125.0000 -150.0000 25

 10 omega   52.00   79.00   1.0000   35.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000 -125.0000 -150.0000 27

 11 omega   16.00   49.00   1.0000   35.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -30.0000   60.0000 33

 12 omega   11.00   36.00   1.0000   35.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -94.0000  150.0000 25

 13 omega   55.00   83.00   1.0000   35.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -94.0000  150.0000 28

 14 omega   33.00   58.00   1.0000   35.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -45.0000  -60.0000 25

 15 omega   31.00   68.00   1.0000   35.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -45.0000  -90.0000 37

 16 omega   21.00   75.00   1.0000   35.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -45.0000   30.0000 54

 17 omega   75.00  101.00   1.0000   35.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -61.0000    0.0000 26

 18 omega   56.00   83.00   1.0000   35.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -94.0000    0.0000 27

 19 omega   83.00  113.00   1.0000   35.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000   15.0000 -150.0000 30

 20 omega  142.00  168.00   1.0000   35.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000   15.0000 -150.0000 26

 21 omega   43.00   87.00   1.0000   35.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000 -103.0000   75.0000 44

 22 omega   17.00   46.00   1.0000   35.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -94.0000   60.0000 29

 23 omega   38.00   79.00   1.0000   35.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -94.0000  120.0000 41
;
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0269663000
_diffrn_orient_matrix_UB_12      -0.0773034000
_diffrn_orient_matrix_UB_13      0.0542679000
_diffrn_orient_matrix_UB_21      -0.0658710000
_diffrn_orient_matrix_UB_22      0.1043385000
_diffrn_orient_matrix_UB_23      0.0385801000
_diffrn_orient_matrix_UB_31      -0.2395844000
_diffrn_orient_matrix_UB_32      -0.0374194000
_diffrn_orient_matrix_UB_33      -0.0044962000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.5418
_diffrn_reflns_av_R_equivalents  0.0219
_diffrn_reflns_av_unetI/netI     0.0299
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            8631
_diffrn_reflns_point_group_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         67.022
_diffrn_reflns_theta_min         3.831
_diffrn_source                   'Enhance Ultra (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.130
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.86594
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour
;
;
_exptl_crystal_density_diffrn    1.574
_exptl_crystal_description
;
;
_exptl_crystal_F_000             808
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.156
_refine_diff_density_min         -0.173
_refine_diff_density_rms         0.039
_refine_ls_abs_structure_details
;
 Flack x determined using 1151 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   0.02(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     262
_refine_ls_number_reflns         2903
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.044
_refine_ls_R_factor_all          0.0283
_refine_ls_R_factor_gt           0.0265
_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^)+(0.0420P)^2^+0.1494P]
 where P=(Fo^2^+2Fc^2^)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0653
_refine_ls_wR_factor_ref         0.0672
_reflns_Friedel_coverage         0.701
_reflns_Friedel_fraction_full    0.987
_reflns_Friedel_fraction_max     0.999
_reflns_number_gt                2807
_reflns_number_total             2903
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            np500340y_si_004.cif
_cod_data_source_block           ZXM1008
_cod_depositor_comments
'Adding full bibliography for 1517403--1517406.cif.'
_cod_database_code               1517405
_chemical_oxdiff_formula         'C1 O1'
_reflns_odcompleteness_completeness 99.77
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(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:
 C9(H9), C11(H11), C8(H8A)
2.b Aromatic/amide H refined with riding coordinates:
 C15(H15), C3(H3)
2.c Idealised Me refined as rotating group:
 C17(H17A,H17B,H17C), C16(H16A,H16B,H16C), C1(H1A,H1B,H1C)
2.d Idealised tetrahedral OH refined as rotating group:
 O7(H7), O8(H8), O2(H2)
;
_shelx_estimated_absorpt_t_max   0.840
_shelx_estimated_absorpt_t_min   0.773
_shelxl_version_number           2013-2