Ascomylactams A-C, Cytotoxic 12- or 13-Membered-Ring Macrocyclic Alkaloids Isolated from the Mangrove Endophytic Fungus <i>Didymella</i> sp. CYSK-4, and Structure Revisions of Phomapyrrolidones A and C.
Chen, Yan; Liu, Zhaoming; Huang, Yun; Liu, Lan; He, Jianguo; Wang, Lan; Yuan, Jie; She, Zhigang; Journal of natural products 82 (2019) 1752–1758; doi:10.1021/acs.jnatprod.8b00918

data_1552694
_publ_section_title
;
 Ascomylactams A-C, Cytotoxic 12- or 13-Membered-Ring Macrocyclic
 Alkaloids Isolated from the Mangrove Endophytic Fungus <i>Didymella</i>
 sp. CYSK-4, and Structure Revisions of Phomapyrrolidones A and C.
;
_journal_issue                   7
_journal_name_full               'Journal of natural products'
_journal_page_first              1752
_journal_page_last               1758
_journal_paper_doi               10.1021/acs.jnatprod.8b00918
_journal_volume                  82
_journal_year                    2019
_chemical_absolute_configuration ad
_chemical_formula_moiety         '0.67(C35 H45 N O5), 0.07(H O)'
_chemical_formula_sum            'C23.33 H30.07 N0.67 O3.4'
_chemical_formula_weight         374.28
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_audit_creation_date             2018-02-02
_audit_creation_method
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_cell_angle_alpha                90
_cell_angle_beta                 100.3180(10)
_cell_angle_gamma                90
_cell_formula_units_Z            3
_cell_length_a                   11.69230(10)
_cell_length_b                   7.05580(10)
_cell_length_c                   19.0143(2)
_cell_measurement_reflns_used    12068
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      66.7770
_cell_measurement_theta_min      3.8210
_cell_volume                     1543.28(3)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'XS (Sheldrick, 2008)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.5058
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_details
;
  1 omega  -99.00  -19.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.7938  126.0000 -180.0000 80

  2 omega  -99.00  -19.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.7938  126.0000  150.0000 80

  3 omega   14.00  117.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       40.7938   38.0000  -60.0000 103

  4 omega   -2.00   97.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       40.7938 -126.0000  -30.0000 99

  5 omega   11.00  115.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       40.7938   57.0000   60.0000 104

  6 omega   19.00  124.00   1.0000    3.6250
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -61.0000  -30.0000 105

  7 omega   10.00   84.00   1.0000    3.6250
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -95.0000 -120.0000 74

  8 omega   66.00  168.00   1.0000    3.6250
omega____ theta____ kappa____ phi______ frames
    -       93.5000   45.0000  -90.0000 102

  9 omega   66.00  168.00   1.0000    3.6250
omega____ theta____ kappa____ phi______ frames
    -       93.5000   45.0000  -60.0000 102

 10 omega   60.00  172.00   1.0000    3.6250
omega____ theta____ kappa____ phi______ frames
    -       93.5000   77.0000  120.0000 112

 11 omega   63.00  168.00   1.0000    3.6250
omega____ theta____ kappa____ phi______ frames
    -       93.5000   61.0000 -150.0000 105

 12 omega   10.00   84.00   1.0000    3.6250
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -95.0000  -30.0000 74

 13 omega   10.00   84.00   1.0000    3.6250
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -95.0000  120.0000 74

 14 omega    8.00  132.00   1.0000    3.6250
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -91.0000 -175.1612 124

 15 omega   60.00  172.00   1.0000    3.6250
omega____ theta____ kappa____ phi______ frames
    -       93.5000   77.0000  150.0000 112

 16 omega   60.00  172.00   1.0000    3.6250
omega____ theta____ kappa____ phi______ frames
    -       93.5000   77.0000   30.0000 112

 17 omega   19.00   77.00   1.0000    3.6250
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -45.0000   90.0000 58

 18 omega   10.00   84.00   1.0000    3.6250
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -95.0000    0.0000 74

 19 omega    9.00  133.00   1.0000    3.6250
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -92.0000   46.1606 124

 20 omega -120.00   -7.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.7938  -77.0000 -150.0000 113

 21 omega    7.00  120.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       40.7938   77.0000  -30.0000 113

 22 omega    7.00  120.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       40.7938   77.0000   60.0000 113

 23 omega    7.00  120.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       40.7938   77.0000  150.0000 113
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0044843000
_diffrn_orient_matrix_UB_12      -0.1289301000
_diffrn_orient_matrix_UB_13      -0.0658385000
_diffrn_orient_matrix_UB_21      0.0566498000
_diffrn_orient_matrix_UB_22      0.1577739000
_diffrn_orient_matrix_UB_23      -0.0380623000
_diffrn_orient_matrix_UB_31      0.1212721000
_diffrn_orient_matrix_UB_32      -0.0783970000
_diffrn_orient_matrix_UB_33      0.0316095000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0365
_diffrn_reflns_av_unetI/netI     0.0267
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            21061
_diffrn_reflns_point_group_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        66.988
_diffrn_reflns_theta_max         66.988
_diffrn_reflns_theta_min         3.843
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'Enhance Ultra (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.635
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.47064
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.208
_exptl_crystal_description
;
;
_exptl_crystal_F_000             606
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.115
_refine_diff_density_min         -0.145
_refine_diff_density_rms         0.034
_refine_ls_abs_structure_details
;
 Flack x determined using 2218 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.12(9)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     394
_refine_ls_number_reflns         5447
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.037
_refine_ls_R_factor_all          0.0348
_refine_ls_R_factor_gt           0.0323
_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^)+(0.0476P)^2^+0.1292P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0790
_refine_ls_wR_factor_ref         0.0814
_reflns_Friedel_coverage         0.828
_reflns_Friedel_fraction_full    0.983
_reflns_Friedel_fraction_max     0.983
_reflns_number_gt                5161
_reflns_number_total             5447
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            np8b00918_si_001.cif
_cod_data_source_block           04201b
_cod_original_formula_sum        'C23.33 H30.07 N0.67 O3.40'
_cod_database_code               1552694
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         'C20 H20 O6'
_chemical_oxdiff_usercomment     'SK4-18 block colorless 0.39 0.35 0.24 150K'
_shelx_estimated_absorpt_t_max   0.884
_shelx_estimated_absorpt_t_min   0.785
_reflns_odcompleteness_completeness 99.97
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     64.99
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2. Restrained distances
 H27-H0AA
 2.5 with sigma of 0.01
3. Others
 Fixed Sof: O0AA(0.1) H0AA(0.1)
4.a Free rotating group:
 O0AA(H0AA)
4.b Ternary CH refined with riding coordinates:
 C10(H10), C14(H14), C15(H15), C20(H20), C22(H22), C26(H26), C27(H27),
 C28(H28), C34(H34), C37(H37)
4.c Secondary CH2 refined with riding coordinates:
 C29(H29A,H29B), C36(H36A,H36B), C39(H39A,H39B)
4.d Aromatic/amide H refined with riding coordinates:
 C7(H7), N11(H11), C16(H16), C19(H19), C23(H23), C33(H33)
4.e Idealised Me refined as rotating group:
 C17(H17A,H17B,H17C), C18(H18A,H18B,H18C), C24(H24A,H24B,H24C), C35(H35A,H35B,
 H35C), C38(H38A,H38B,H38C), C40(H40A,H40B,H40C), C41(H41A,H41B,H41C)
4.f Idealised tetrahedral OH refined as rotating group:
 O1(H1)
;
_shelx_res_checksum              99721
_shelx_hkl_checksum              54876
_olex2_submission_special_instructions 'No special instructions were received'