New PKS-NRPS tetramic acids and pyridinone from an Australian marine-derived fungus, Chaunopycnis sp.
Shang, Zhuo; Li, Li; Espósito, Breno P; Salim, Angela A.; Khalil, Zeinab G.; Quezada, Michelle; Bernhardt, Paul V.; Capon, Robert J.; Organic & biomolecular chemistry 13 (2015) 7795–7802; doi:10.1039/c5ob01058f

data_7154535
_publ_section_title
;
 New PKS-NRPS tetramic acids and pyridinone from an Australian
 marine-derived fungus, Chaunopycnis sp.
;
_journal_issue                   28
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              7795
_journal_page_last               7802
_journal_paper_doi               10.1039/c5ob01058f
_journal_volume                  13
_journal_year                    2015
_chemical_absolute_configuration ad
_chemical_compound_source        'fungus Chaunopycnis sp.'
_chemical_formula_moiety         'C21 H25 N O4, C H4 O'
_chemical_formula_sum            'C22 H29 N O5'
_chemical_formula_weight         387.46
_chemical_name_systematic        'chaunolidine C'
_space_group_IT_number           1
_symmetry_cell_setting           triclinic
_symmetry_Int_Tables_number      1
_symmetry_space_group_name_Hall  'P 1'
_symmetry_space_group_name_H-M   'P 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4
_audit_creation_date             2015-05-13T12:22:54-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_update_record
;
2015-06-05 deposited with the CCDC.
2015-06-18 downloaded from the CCDC.
;
_cell_angle_alpha                84.197(5)
_cell_angle_beta                 84.853(5)
_cell_angle_gamma                85.592(5)
_cell_formula_units_Z            2
_cell_length_a                   6.6012(4)
_cell_length_b                   8.1654(6)
_cell_length_c                   19.8307(13)
_cell_measurement_reflns_used    2757
_cell_measurement_temperature    190(2)
_cell_measurement_theta_max      60.154
_cell_measurement_theta_min      5.444
_cell_measurement_wavelength     0.71073
_cell_volume                     1056.66(12)
_computing_cell_refinement
;
        CrysAlisPro, Agilent Technologies,
        Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
        (compiled Aug 13 2014,18:06:01)
;
_computing_data_collection
;
        CrysAlisPro, Agilent Technologies,
        Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
        (compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction
;
        CrysAlisPro, Agilent Technologies,
        Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
        (compiled Aug 13 2014,18:06:01)
;
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SIR92 (Giacovazzo et al, 1993)'
_diffrn_ambient_temperature      190(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0696
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Sapphire3, Gemini ultra'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0833232
_diffrn_orient_matrix_UB_12      -0.1298132
_diffrn_orient_matrix_UB_13      0.0543477
_diffrn_orient_matrix_UB_21      0.1294599
_diffrn_orient_matrix_UB_22      -0.0876288
_diffrn_orient_matrix_UB_23      -0.056031
_diffrn_orient_matrix_UB_31      0.1773733
_diffrn_orient_matrix_UB_32      0.107718
_diffrn_orient_matrix_UB_33      0.0067948
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0506
_diffrn_reflns_av_unetI/netI     0.0656
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            13470
_diffrn_reflns_theta_full        62.47
_diffrn_reflns_theta_max         62.47
_diffrn_reflns_theta_min         4.5
_diffrn_source                   'sealed X-ray tube'
_exptl_absorpt_coefficient_mu    0.698
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_correction_T_min  0.84915
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
        CrysAlisPro, Agilent Technologies,
        Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
        (compiled Aug 13 2014,18:06:01)
        Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.218
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       triclinic
_exptl_crystal_F_000             416
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: MeOH'
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.273
_refine_diff_density_min         -0.235
_refine_diff_density_rms         0.056
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.1(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     513
_refine_ls_number_reflns         6294
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.03
_refine_ls_R_factor_all          0.092
_refine_ls_R_factor_gt           0.0658
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.1032P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1664
_refine_ls_wR_factor_ref         0.1858
_reflns_number_gt                4465
_reflns_number_total             6294
_reflns_threshold_expression     >2\s(I)
_cod_data_source_file            c5ob01058f2.cif
_cod_data_source_block           1302az7
_cod_depositor_comments          'Adding full bibliography for 7154535.cif.'
_cod_database_code               7154535