Pro-Apoptotic and Immunostimulatory Tetrahydroxanthone Dimers from the Endophytic Fungus Phomopsis longicolla
David Rönsberg; Abdessamad Debbab; Attila Mándi; Vera Vasylyeva; Philip Böhler; Björn Stork; Laura Engelke; Alexandra Hamacher; Richard Sawadogo; Marc Diederich; Victor Wray; WenHan Lin; Matthias U. Kassack; Christoph Janiak; Stefanie Scheu; Sebastian Wesselborg; Tibor Kurtán; Amal H. Aly; Peter Proksch; Journal of Organic Chemistry 78 (2013) 12409–12425; doi:10.1021/jo402066b

data_4028851
_publ_section_title
;
 Pro-Apoptotic and Immunostimulatory Tetrahydroxanthone Dimers from the
 Endophytic Fungus Phomopsis longicolla
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              12409
_journal_page_last               12425
_journal_paper_doi               10.1021/jo402066b
_journal_volume                  78
_journal_year                    2013
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C38 H38 O16'
_chemical_formula_sum            'C38 H38 O16'
_chemical_formula_weight         750.68
_chemical_name_common            'Phomoxanthone A'
_chemical_name_systematic
; 
Phomoxanthone A hemi(ethyl acetate) hemi-hydrate
;
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 98.518(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   10.6741(8)
_cell_length_b                   12.3578(9)
_cell_length_c                   15.4377(11)
_cell_measurement_reflns_used    7467
_cell_measurement_temperature    123(2)
_cell_measurement_theta_max      64.25
_cell_measurement_theta_min      2.89
_cell_volume                     2013.9(3)
_computing_cell_refinement       'SAINT (Bruker, 2009)'
_computing_data_collection       'APEX2 (Bruker, 2011)'
_computing_data_reduction        'SAINT (Bruker, 2009)'
_computing_molecular_graphics    'DIAMOND (Crystal Impact, 2009)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      123(2)
_diffrn_measured_fraction_theta_full 0.912
_diffrn_measured_fraction_theta_max 0.912
_diffrn_measurement_device_type  'Bruker Kappa APEX-II CCD area detector'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  'multilayer mirror'
_diffrn_radiation_source         'I\mS CuK\a'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0250
_diffrn_reflns_av_sigmaI/netI    0.0373
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            9025
_diffrn_reflns_theta_full        63.98
_diffrn_reflns_theta_max         63.98
_diffrn_reflns_theta_min         2.89
_exptl_absorpt_coefficient_mu    0.825
_exptl_absorpt_correction_T_max  0.9025
_exptl_absorpt_correction_T_min  0.8877
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(<i>SADABS</i>; Sheldrick, 1996)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.238
_exptl_crystal_description       block
_exptl_crystal_F_000             788
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.13
_platon_squeeze_details
;
The unit cell contains one ethyl acetate and one water molecules which have 
been treated as a diffuse contribution to the overall scattering without 
specific atom positions by SQUEEZE/PLATON (Spek, A. L. (2009)).
;
_refine_diff_density_max         0.371
_refine_diff_density_min         -0.188
_refine_diff_density_rms         0.052
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.05(19)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.079
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     519
_refine_ls_number_reflns         5338
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.080
_refine_ls_R_factor_all          0.0470
_refine_ls_R_factor_gt           0.0461
_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^)+(0.0658P)^2^+1.3725P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1263
_refine_ls_wR_factor_ref         0.1271
_reflns_number_gt                5232
_reflns_number_total             5338
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo402066b_si_002.cif
_cod_data_source_block           p21p
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               4028851