Cytotoxic 14-Membered Macrolides from a Mangrove-Derived Endophytic Fungus, Pestalotiopsis microspora.
Liu, Shuai; Dai, Haofu; Makhloufi, Gamall; Heering, Christian; Janiak, Christoph; Hartmann, Rudolf; Mándi, Attila; Kurtán, Tibor; Müller, Werner E G; Kassack, Matthias U.; Lin, Wenhan; Liu, Zhen; Proksch, Peter; Journal of natural products 79 (2016) 2332–2340; doi:10.1021/acs.jnatprod.6b00473

data_1553300
_publ_section_title
;
 Cytotoxic 14-Membered Macrolides from a Mangrove-Derived Endophytic
 Fungus, Pestalotiopsis microspora.
;
_journal_issue                   9
_journal_name_full               'Journal of natural products'
_journal_page_first              2332
_journal_page_last               2340
_journal_paper_doi               10.1021/acs.jnatprod.6b00473
_journal_volume                  79
_journal_year                    2016
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C14 H24 O4'
_chemical_formula_sum            'C14 H24 O4'
_chemical_formula_weight         256.33
_chemical_name_common            'Pestalotioprolide C'
_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'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   36.533(4)
_cell_length_b                   4.9693(6)
_cell_length_c                   7.6479(9)
_cell_measurement_reflns_used    9690
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      67.614
_cell_measurement_theta_min      2.419
_cell_volume                     1388.4(3)
_computing_cell_refinement       'SAINT (Bruker, 2015)'
_computing_data_collection       'APEX2 (Bruker, 2014)'
_computing_data_reduction        'SAINT (Bruker, 2015)'
_computing_molecular_graphics    'DIAMOND 3.2 (Crystal Impact, 2015)'
_computing_publication_material  'SHELXL-2014 (Sheldrick, 2015)'
_computing_structure_refinement
'SHELXL-2014/7 (Sheldrick, 2015); PLATON (Spek, 2009)'
_computing_structure_solution    'SHELXL-2014 (Sheldrick, 2015)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.979
_diffrn_measured_fraction_theta_max 0.909
_diffrn_measurement_device_type  'Bruker Kappa APEX-II CCD area detector'
_diffrn_measurement_method       '\w scans, \p scans'
_diffrn_radiation_monochromator  'multilayer mirror'
_diffrn_radiation_source         'microfocus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0668
_diffrn_reflns_av_unetI/netI     0.0483
_diffrn_reflns_Laue_measured_fraction_full 0.979
_diffrn_reflns_Laue_measured_fraction_max 0.909
_diffrn_reflns_limit_h_max       43
_diffrn_reflns_limit_h_min       -43
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -3
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            17343
_diffrn_reflns_point_group_measured_fraction_full 0.959
_diffrn_reflns_point_group_measured_fraction_max 0.886
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         71.949
_diffrn_reflns_theta_min         2.419
_exptl_absorpt_coefficient_mu    0.717
_exptl_absorpt_correction_T_max  0.7530
_exptl_absorpt_correction_T_min  0.6124
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(<i>SADABS</i>; Sheldrick, 2012)'
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.226
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       pillar
_exptl_crystal_F_000             560
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.080
_exptl_crystal_size_min          0.040
_refine_diff_density_max         0.432
_refine_diff_density_min         -0.413
_refine_diff_density_rms         0.093
_refine_ls_abs_structure_details
;
 Flack x determined using 823 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
 
 While refining the dataset shelxl gives the following warning:
 
 Flack x =   -0.040(943) by classical fit to all intensities
 ** Warning: Friedel differences statistically dubious - Flack x unreliable **
              0.248(150) from 823 selected quotients (Parsons' method)
 
 The refinement as a 2-component inversion twin using the TWIN/BASF instructions
 in SHELXL leads to a Flack parameter of 0.00, a negative BASF and 
 continuing errors.
 
 Therefore the structure parameter y was determined using PLATON:
 
 Analysis of the absolute structure using likelihood methods (Hooft,
 Straver & Spek, 2008) was performed using PLATON (Spek, 2009). The results
 indicated that the absolute structure had been correctly assigned. 
 The absolute structure parameter y (Hooft, Straver & Spek, 2008) was
 calculated using PLATON (Spek, 2009). The resulting value was y=0.17(12)
 indicates that the absolute structure has probably been determined 
 correctly.
 
 The method calculated the probability that the absolute structure of the 
 model is correct as 1.00 P2(true) for a pure enantiomer.
 
 The method calculated the probability that the absolute structure is properly
 described as 0.950 P3(true) for a one-to-one racemic twin. The method
 calculated that the probability  that the structure is inverted is
 smaller than 0.7E-10 P3(false).
;
_refine_ls_abs_structure_Flack   0.25(15)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.161
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     170
_refine_ls_number_reflns         2418
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.161
_refine_ls_R_factor_all          0.0931
_refine_ls_R_factor_gt           0.0867
_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^)+(0.0527P)^2^+5.8504P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2354
_refine_ls_wR_factor_ref         0.2408
_reflns_Friedel_coverage         0.613
_reflns_Friedel_fraction_full    0.928
_reflns_Friedel_fraction_max     0.851
_reflns_number_gt                2309
_reflns_number_total             2418
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            np6b00473_si_003.cif
_cod_data_source_block           FO-5-1-1
_cod_database_code               1553300
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.814
_shelx_estimated_absorpt_t_max   0.972
_shelx_res_checksum              83479
_shelx_hkl_checksum              39036