Bioactive Nonanolide Derivatives Isolated from the Endophytic Fungus Cytosporasp.
Shan Lu; Peng Sun; Tiejun Li; Tibor Kurtán; Attila Mándi; Sándor Antus; Karsten Krohn; Siegfried Draeger; Barbara Schulz; Yanghua Yi; Ling Li; Wen Zhang; Journal of Organic Chemistry 76 (2011) 9699–9710; doi:10.1021/jo201755v

data_4026761
_publ_section_title
;
 Bioactive Nonanolide Derivatives Isolated from the Endophytic Fungus
 Cytosporasp.
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              9699
_journal_page_last               9710
_journal_paper_doi               10.1021/jo201755v
_journal_volume                  76
_journal_year                    2011
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C15 H26 O5'
_chemical_formula_sum            'C15 H26 O5'
_chemical_formula_weight         286.36
_chemical_melting_point          409(1)
_chemical_name_common            'cytospolide M'
_chemical_name_systematic
; 
 (1S,2R,5R,6S,7R,8R)-6,7-dihydroxy-5,8-dimethyl-2-
pentyl-3,11-dioxa-bicyclo[6.2.1]undecan-4-one
;
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_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_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   5.3240(1)
_cell_length_b                   12.6918(3)
_cell_length_c                   23.0937(6)
_cell_measurement_reflns_used    587
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      57.50
_cell_measurement_theta_min      3.97
_cell_volume                     1560.47(6)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'SHELXL-97 (Sheldrick, 1997)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.964
_diffrn_measured_fraction_theta_max 0.965
_diffrn_measurement_device_type  'Bruker SMART APEX-II'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0388
_diffrn_reflns_av_sigmaI/netI    0.0412
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            4890
_diffrn_reflns_theta_full        67.40
_diffrn_reflns_theta_max         67.40
_diffrn_reflns_theta_min         3.83
_exptl_absorpt_coefficient_mu    0.740
_exptl_absorpt_correction_T_max  0.9640
_exptl_absorpt_correction_T_min  0.9297
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.219
_exptl_crystal_description       prism
_exptl_crystal_F_000             624
_exptl_crystal_size_max          0.10
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.181
_refine_diff_density_min         -0.160
_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   -0.2(5)
_refine_ls_extinction_coef       0.0032(8)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     182
_refine_ls_number_reflns         2552
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.049
_refine_ls_R_factor_all          0.0994
_refine_ls_R_factor_gt           0.0568
_refine_ls_shift/su_max          0.007
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0911P)^2^+0.0242P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1510
_refine_ls_wR_factor_ref         0.1810
_reflns_number_gt                1492
_reflns_number_total             2552
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo201755v_si_001.cif
_cod_data_source_block           s111
_cod_database_code               4026761