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_1553299
_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 rmad
_chemical_formula_moiety         'C14 H20 O5, H2 O'
_chemical_formula_sum            'C14 H22 O6'
_chemical_formula_weight         286.31
_chemical_name_common            'Pestalotioprolide B hydrate'
_space_group_crystal_system      triclinic
_space_group_IT_number           1
_space_group_name_Hall           'P 1'
_space_group_name_H-M_alt        'P 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2013
_cell_angle_alpha                88.911(4)
_cell_angle_beta                 85.044(4)
_cell_angle_gamma                77.888(5)
_cell_formula_units_Z            1
_cell_length_a                   6.3082(4)
_cell_length_b                   7.5108(5)
_cell_length_c                   8.1100(5)
_cell_measurement_reflns_used    2459
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      64.551
_cell_measurement_theta_min      5.475
_cell_volume                     374.29(4)
_computing_cell_refinement       'SAINT (Bruker, 2014)'
_computing_data_collection       'APEX2 (Bruker, 2014)'
_computing_data_reduction        'SAINT (Bruker, 2014)'
_computing_molecular_graphics    'DIAMOND 3.2 (Crystal Impact, 2009)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    'SHELXL2014 (Sheldrick, 2008)'
_diffrn_ambient_temperature      120(2)
_diffrn_measured_fraction_theta_full 0.829
_diffrn_measured_fraction_theta_max 0.868
_diffrn_measurement_device_type  'Bruker Kappa APEX-II CCD area detector'
_diffrn_measurement_method       '\w 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  0.0449
_diffrn_reflns_av_unetI/netI     0.0521
_diffrn_reflns_Laue_measured_fraction_full 0.829
_diffrn_reflns_Laue_measured_fraction_max 0.868
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -6
_diffrn_reflns_number            3068
_diffrn_reflns_point_group_measured_fraction_full 0.603
_diffrn_reflns_point_group_measured_fraction_max 0.632
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         65.332
_diffrn_reflns_theta_min         5.475
_exptl_absorpt_coefficient_mu    0.827
_exptl_absorpt_correction_T_max  0.7526
_exptl_absorpt_correction_T_min  0.6664
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(<i>SADABS</i>; Sheldrick, 2012)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.270
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             154
_exptl_crystal_size_max          0.110
_exptl_crystal_size_mid          0.090
_exptl_crystal_size_min          0.050
_refine_diff_density_max         0.167
_refine_diff_density_min         -0.173
_refine_diff_density_rms         0.045
_refine_ls_abs_structure_details
;
 Flack x determined using 492 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   -0.03(19)
_refine_ls_extinction_coef       0.017(3)
_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   1.026
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     195
_refine_ls_number_reflns         1630
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.025
_refine_ls_R_factor_all          0.0349
_refine_ls_R_factor_gt           0.0342
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 w=1/[\s^2^(Fo^2^)+(0.0537P)^2^+0.0464P]
 where P=(Fo^2^+2Fc^2^)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0869
_refine_ls_wR_factor_ref         0.0878
_reflns_Friedel_coverage         0.455
_reflns_Friedel_fraction_full    0.378
_reflns_Friedel_fraction_max     0.395
_reflns_number_gt                1594
_reflns_number_total             1630
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            np6b00473_si_002.cif
_cod_data_source_block           Co45232
_cod_database_code               1553299
_shelx_estimated_absorpt_t_min   0.914
_shelx_estimated_absorpt_t_max   0.960
_shelxl_version_number           2013-2
_shelx_res_checksum              5259
_shelx_hkl_checksum              37002