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_1552693
_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 s
_chemical_formula_moiety         'C34 H41 N O4, C H4 O'
_chemical_formula_sum            'C35 H45 N O5'
_chemical_formula_weight         559.72
_space_group_crystal_system      monoclinic
_space_group_IT_number           5
_space_group_name_Hall           'C 2y'
_space_group_name_H-M_alt        'C 1 2 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2017-04-05
_audit_creation_method
;
Olex2 1.2
(compiled 2016.11.07 svn.r3352 for OlexSys, GUI svn.r5261)
;
_cell_angle_alpha                90
_cell_angle_beta                 91.3900(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   20.94020(10)
_cell_length_b                   7.07810(10)
_cell_length_c                   20.56140(10)
_cell_measurement_reflns_used    18186
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      70.5550
_cell_measurement_theta_min      4.7730
_cell_volume                     3046.65(5)
_computing_cell_refinement       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_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    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
--------------------------------------------------------------------------
  1  \w    -95.00  -2.00   1.00    1.00    --  -41.45 125.00 -30.00   93
  2  \w   -115.00 -13.00   1.00    1.00    --  -41.45 -57.00 120.00  102
  3  \w      9.00 118.00   1.00    1.00    --   41.45  77.00 -30.00  109
  4  \w      9.00 118.00   1.00    1.00    --   41.45  77.00-120.00  109
  5  \w     23.00  97.00   1.00    1.00    --   41.45-125.00-180.00   74
  6  \w     17.00 116.00   1.00    1.00    --   41.45  38.00-180.00   99
  7  \w     68.00 177.00   1.00    1.15    --  100.58  77.00 150.00  109
  8  \w     71.00 173.00   1.00    1.15    --  100.58  61.00-120.00  102
  9  \w     28.00 126.00   1.00    1.15    --  100.58 -45.00 150.00   98
 10  \w     68.00 177.00   1.00    1.15    --  100.58  77.00-120.00  109
 11  \w     71.00 173.00   1.00    1.15    --  100.58  61.00-150.00  102
 12  \w     68.00 177.00   1.00    1.15    --  100.58  77.00-150.00  109
 13  \w     71.00 173.00   1.00    1.15    --  100.58  61.00 -60.00  102
 14  \w     68.00 177.00   1.00    1.15    --  100.58  77.00 -90.00  109
 15  \w     71.00 173.00   1.00    1.15    --  100.58  61.00 -90.00  102
 16  \w     68.00 177.00   1.00    1.15    --  100.58  77.00-180.00  109
 17  \w     71.00 173.00   1.00    1.15    --  100.58  61.00-180.00  102
 18  \w     94.00 174.00   1.00    1.15    --  100.58 125.00   0.00   80
 19  \w     68.00 177.00   1.00    1.15    --  100.58  77.00 -60.00  109
 20  \w     94.00 173.00   1.00    1.15    --  100.58 125.00  60.00   79
 21  \w     80.00 107.00   1.00    1.15    --  100.58-102.00-152.00   27
 22  \w    112.00 161.00   1.00    1.15    --  100.58  45.00-150.00   49
 23  \w     76.00 103.00   1.00    1.15    --  100.58  45.00-120.00   27
 24  \w     76.00 103.00   1.00    1.15    --  100.58  45.00 -90.00   27
 25  \w     76.00 103.00   1.00    1.15    --  100.58  45.00-150.00   27
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0131800000
_diffrn_orient_matrix_UB_12      0.0195744000
_diffrn_orient_matrix_UB_13      -0.0730733000
_diffrn_orient_matrix_UB_21      0.0690869000
_diffrn_orient_matrix_UB_22      0.0611684000
_diffrn_orient_matrix_UB_23      0.0164904000
_diffrn_orient_matrix_UB_31      0.0215793000
_diffrn_orient_matrix_UB_32      -0.2080571000
_diffrn_orient_matrix_UB_33      -0.0020089000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0487
_diffrn_reflns_av_unetI/netI     0.0362
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            20239
_diffrn_reflns_point_group_measured_fraction_full 0.970
_diffrn_reflns_point_group_measured_fraction_max 0.956
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         70.671
_diffrn_reflns_theta_min         4.224
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.639
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.33247
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.220
_exptl_crystal_description       block
_exptl_crystal_F_000             1208
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.38
_exptl_crystal_size_min          0.34
_refine_diff_density_max         0.277
_refine_diff_density_min         -0.254
_refine_diff_density_rms         0.051
_refine_ls_abs_structure_details
;
 Flack x determined using 2328 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.04(12)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.073
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     379
_refine_ls_number_reflns         5621
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.073
_refine_ls_R_factor_all          0.0436
_refine_ls_R_factor_gt           0.0434
_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^)+(0.0721P)^2^+1.4282P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1143
_refine_ls_wR_factor_ref         0.1145
_reflns_Friedel_coverage         0.770
_reflns_Friedel_fraction_full    0.934
_reflns_Friedel_fraction_max     0.910
_reflns_number_gt                5580
_reflns_number_total             5621
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            np8b00918_si_002.cif
_cod_data_source_block           02264
_cod_database_code               1552693
_chemical_oxdiff_formula         'C20 H20 O6'
_chemical_oxdiff_usercomment     SK4-X
_reflns_odcompleteness_completeness 99.96
_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.a Ternary CH refined with riding coordinates:
 C14(H14), C20(H20), C25(H25), C26(H26), C32(H32), C34(H34), C35(H35),
 C36(H36), C39(H39)
2.b Secondary CH2 refined with riding coordinates:
 C13(H13A,H13B), C31(H31A,H31B), C37(H37A,H37B)
2.c Aromatic/amide H refined with riding coordinates:
 N5(H5), C9(H9), C15(H15), C21(H21), C22(H22), C23(H23), C33(H33)
2.d Idealised Me refined as rotating group:
 C17(H17A,H17B,H17C), C24(H24A,H24B,H24C), C27(H27A,H27B,H27C), C30(H30A,H30B,
 H30C), C40(H40A,H40B,H40C), C41(H41A,H41B,H41C), C38(H38A,H38B,H38C)
2.e Idealised tetrahedral OH refined as rotating group:
 O3(H3), O8(H8)
;
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.315
_oxdiff_exptl_absorpt_empirical_full_min 0.658