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_1517406
_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         'C19 H20 O6'
_chemical_formula_sum            'C19 H20 O6'
_chemical_formula_weight         344.35
_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             2013-11-22
_audit_creation_method
;
Olex2 1.2
(compiled 2013.09.17 svn.r2790 for OlexSys, GUI svn.r4601)
;
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   7.97730(10)
_cell_length_b                   20.0228(3)
_cell_length_c                   20.8545(3)
_cell_measurement_reflns_used    10083
_cell_measurement_temperature    119.99(18)
_cell_measurement_theta_max      67.1160
_cell_measurement_theta_min      3.0450
_cell_volume                     3331.05(8)
_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
'Sheldrick, G.M. (2008). Acta Cryst. A64, 112-122'
_computing_structure_solution
'Sheldrick, G.M. (2008). Acta Cryst. A64, 112-122'
_diffrn_ambient_temperature      119.99(18)
_diffrn_detector_area_resol_mean 10.5095
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details
;
  1 omega   15.00   91.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       39.9089   38.0000 -180.0000 76

  2 omega   18.00  104.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       39.9089   38.0000   90.0000 86

  3 omega   67.00  102.00   1.0000   50.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -61.0000    0.0000 35

  4 omega   35.00   61.00   1.0000   50.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -30.0000 -180.0000 26

  5 omega   17.00   63.00   1.0000   50.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -30.0000  120.0000 46

  6 omega   99.00  125.00   1.0000   50.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -77.0000  120.0000 26

  7 omega   20.00   74.00   1.0000   50.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -45.0000 -120.0000 54

  8 omega   20.00   62.00   1.0000   50.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -61.0000 -120.0000 42

  9 omega   48.00   76.00   1.0000   50.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -45.0000   30.0000 28

 10 omega   14.00   46.00   1.0000   50.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -94.0000  -30.0000 32

 11 omega   65.00  107.00   1.0000   50.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000   30.0000  150.0000 42

 12 omega   19.00   65.00   1.0000   50.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -77.0000  120.0000 46

 13 omega   36.00   69.00   1.0000   50.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -30.0000  -90.0000 33

 14 omega   17.00   61.00   1.0000   50.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -30.0000  -30.0000 44

 15 omega   18.00   49.00   1.0000   50.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -30.0000 -120.0000 31

 16 omega   80.00  117.00   1.0000   50.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -61.0000 -120.0000 37

 17 omega  114.00  150.00   1.0000   50.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  157.0000  -94.0000 36

 18 omega   33.00   58.00   1.0000   50.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -30.0000    0.0000 25

 19 omega   10.00   35.00   1.0000   50.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -94.0000 -120.0000 25

 20 omega   51.00   76.00   1.0000   50.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -94.0000   30.0000 25

 21 omega   49.00   82.00   1.0000   50.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -94.0000  120.0000 33

 22 omega   51.00   76.00   1.0000   50.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000 -125.0000  150.0000 25

 23 omega   61.00   86.00   1.0000   50.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -53.0000  178.6385 25

 24 omega  134.00  160.00   1.0000   50.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000   30.0000  150.0000 26

 25 omega   61.00  127.00   1.0000   50.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -91.0000    1.6936 66
;
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0186821000
_diffrn_orient_matrix_UB_12      0.0713071000
_diffrn_orient_matrix_UB_13      0.0267713000
_diffrn_orient_matrix_UB_21      0.0327014000
_diffrn_orient_matrix_UB_22      -0.0264144000
_diffrn_orient_matrix_UB_23      0.0682457000
_diffrn_orient_matrix_UB_31      0.1894126000
_diffrn_orient_matrix_UB_32      0.0116710000
_diffrn_orient_matrix_UB_33      -0.0091558000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0362
_diffrn_reflns_av_unetI/netI     0.0326
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            20601
_diffrn_reflns_theta_full        67.07
_diffrn_reflns_theta_max         67.07
_diffrn_reflns_theta_min         3.06
_diffrn_source                   'Enhance Ultra (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.851
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.86034
_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    1.373
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description
;
;
_exptl_crystal_F_000             1456
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.133
_refine_diff_density_min         -0.163
_refine_diff_density_rms         0.034
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.02(11)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     467
_refine_ls_number_reflns         5942
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.036
_refine_ls_R_factor_all          0.0335
_refine_ls_R_factor_gt           0.0303
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0359P)^2^+0.4326P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0704
_refine_ls_wR_factor_ref         0.0725
_reflns_number_gt                5564
_reflns_number_total             5942
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            np500340y_si_001.cif
_cod_data_source_block           zxmbc2
_cod_depositor_comments
'Adding full bibliography for 1517403--1517406.cif.'
_cod_original_formula_sum        C19H20O6
_cod_database_code               1517406
_chemical_oxdiff_formula         'C1 O1'
_reflns_odcompleteness_completeness 99.88
_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
2.a Ternary CH refined with riding coordinates:
 C28(H28), C13(H13)
2.b Secondary CH2 refined with riding coordinates:
 C34(H34A,H34B), C27(H27A,H27B), C14(H14A,H14B), C7(H7A,H7B)
2.c Aromatic/amide H refined with riding coordinates:
 C19(H19), C38(H38), C22(H22), C3(H3)
2.d Idealised Me refined as rotating group:
 C20(H20A,H20B,H20C), C9(H9A,H9B,H9C), C30(H30A,H30B,H30C), C33(H33A,H33B,
 H33C), C11(H11A,H11B,H11C), C31(H31A,H31B,H31C), C12(H12A,H12B,H12C), C1(H1A,
 H1B,H1C)
;