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_1517404
_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 ad
_chemical_formula_moiety         'C16 H20 O7'
_chemical_formula_sum            'C16 H20 O7'
_chemical_formula_weight         324.32
_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   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2013-07-05
_audit_creation_method
;
  Olex2 1.2
  (compiled Apr 23 2013 17:54:37, GUI svn.r4466)
;
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   5.66941(19)
_cell_length_b                   10.8760(4)
_cell_length_c                   23.9077(7)
_cell_measurement_reflns_used    5024
_cell_measurement_temperature    110.02(10)
_cell_measurement_theta_max      67.1120
_cell_measurement_theta_min      3.6770
_cell_volume                     1474.16(9)
_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-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      110.02(10)
_diffrn_detector_area_resol_mean 10.5095
_diffrn_measured_fraction_theta_full 0.9981
_diffrn_measured_fraction_theta_max 0.9966
_diffrn_measurement_details
;
  1 omega   46.00   97.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       40.0339   19.0000  -30.0000 51

  2 omega   17.00  111.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       40.0339   38.0000   30.0000 94

  3 omega   16.00   65.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -30.0000  -90.0000 49

  4 omega   31.00   66.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -30.0000  150.0000 35

  5 omega   45.00   80.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000 -125.0000  -30.0000 35

  6 omega   21.00   67.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -30.0000   60.0000 46

  7 omega   19.00   49.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -45.0000  -90.0000 30

  8 omega   21.00   47.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -30.0000    0.0000 26

  9 omega   40.00   78.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -61.0000   90.0000 38

 10 omega   84.00  123.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -61.0000   90.0000 39

 11 omega   24.00   57.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -45.0000  -30.0000 33

 12 omega   54.00  103.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -61.0000  -90.0000 49

 13 omega   22.00   77.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -45.0000    0.0000 55

 14 omega  101.00  156.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000   30.0000  -30.0000 55

 15 omega   16.00   57.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -30.0000   30.0000 41

 16 omega   41.00   66.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -45.0000  120.0000 25

 17 omega   87.00  113.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000   15.0000  -60.0000 26

 18 omega   50.00   76.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -45.0000 -150.0000 26
;
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0782071000
_diffrn_orient_matrix_UB_12      -0.1069613000
_diffrn_orient_matrix_UB_13      0.0380329000
_diffrn_orient_matrix_UB_21      -0.0776448000
_diffrn_orient_matrix_UB_22      -0.0927987000
_diffrn_orient_matrix_UB_23      -0.0451442000
_diffrn_orient_matrix_UB_31      0.2480730000
_diffrn_orient_matrix_UB_32      0.0047515000
_diffrn_orient_matrix_UB_33      -0.0259594000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.5418
_diffrn_reflns_av_R_equivalents  0.0286
_diffrn_reflns_av_unetI/netI     0.0361
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            6945
_diffrn_reflns_theta_full        67.09
_diffrn_reflns_theta_max         67.09
_diffrn_reflns_theta_min         3.70
_diffrn_source                   'Enhance Ultra (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.971
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.77722
_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    1.461
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description
;
;
_exptl_crystal_F_000             688
_refine_diff_density_max         0.333
_refine_diff_density_min         -0.225
_refine_diff_density_rms         0.044
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.03(15)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.020
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     221
_refine_ls_number_reflns         2623
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.020
_refine_ls_R_factor_all          0.0330
_refine_ls_R_factor_gt           0.0313
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0420P)^2^+0.3328P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0765
_refine_ls_wR_factor_ref         0.0779
_reflns_number_gt                2514
_reflns_number_total             2623
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            np500340y_si_003.cif
_cod_data_source_block           9_3zxm4
_cod_depositor_comments
'Adding full bibliography for 1517403--1517406.cif.'
_cod_original_cell_volume        1474.16(8)
_cod_database_code               1517404
_chemical_oxdiff_formula         'C1 O1'
_reflns_odcompleteness_completeness 99.81
_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:
 C15(H15), C14(H14), C13(H13), C3(H3A), C5(H5A)
2.b Secondary CH2 refined with riding coordinates:
 C4(H4A,H4B)
2.c Aromatic/amide H refined with riding coordinates:
 C11(H11), C9(H9)
2.d Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C16(H16A,H16B,H16C)
2.e Idealised tetrahedral OH refined as rotating group:
 O1(H1), O5(H5), O2(H2)
;