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_1552692
_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         'C34 H41 N O4'
_chemical_formula_sum            'C34 H41 N O4'
_chemical_formula_weight         527.68
_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   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2018-01-30
_audit_creation_method
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            12
_cell_length_a                   12.1967(2)
_cell_length_b                   16.4091(3)
_cell_length_c                   47.1373(10)
_cell_measurement_reflns_used    22057
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      73.7730
_cell_measurement_theta_min      3.7110
_cell_volume                     9433.9(3)
_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_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device_type  'multiwire proportional'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0745
_diffrn_reflns_av_unetI/netI     0.0543
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       57
_diffrn_reflns_limit_l_min       -55
_diffrn_reflns_number            88841
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.982
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         74.220
_diffrn_reflns_theta_min         3.743
_exptl_absorpt_coefficient_mu    0.569
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.115
_exptl_crystal_description       block
_exptl_crystal_F_000             3408
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.38
_exptl_crystal_size_min          0.34
_refine_diff_density_max         0.218
_refine_diff_density_min         -0.200
_refine_diff_density_rms         0.041
_refine_ls_abs_structure_details
;
 Flack x determined using 5248 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.28(9)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.016
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1072
_refine_ls_number_reflns         18890
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.016
_refine_ls_R_factor_all          0.0731
_refine_ls_R_factor_gt           0.0563
_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^)+(0.0590P)^2^+2.9938P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1312
_refine_ls_wR_factor_ref         0.1392
_reflns_Friedel_coverage         0.813
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.974
_reflns_number_gt                14948
_reflns_number_total             18890
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            np8b00918_si_003.cif
_cod_data_source_block           a
_cod_depositor_comments
;

2022-05-28
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_moiety     '3(C34 H41 N O4)'
_cod_original_formula_sum        'C102 H123 N3 O12'
_cod_original_formula_units_Z    4
_cod_original_formula_weight     1583.03
_cod_database_code               1552692
_shelx_shelxl_version_number     2014/7
_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
2. Rigid bond restraints
 N30, C77
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
3.a Ternary CH refined with riding coordinates:
 C11(H11), C14(H14), C16(H16), C17(H17), C25(H25), C26(H26), C29(H29),
 C38(H38), C63(H63), C64(H64), C71(H71), C9(H9), C23(H23), C27(H27), C31(H31),
 C32(H32), C49(H49), C50(H50), C62(H62), C67(H67), C85(H85), C88(H88), C41(H41),
  C44(H44), C59(H59), C60(H60), C65(H65), C73(H73), C87(H87), C94(H94),
 C95(H95), C108(H108), C120(H120)
3.b Secondary CH2 refined with riding coordinates:
 C15(H15A,H15B), C36(H36A,H36B), C91(H91A,H91B), C68(H68A,H68B), C75(H75A,
 H75B), C98(H98A,H98B), C78(H78A,H78B), C84(H84A,H84B), C106(H10J,H10K)
3.c Aromatic/amide H refined with riding coordinates:
 C18(H18), C35(H35), C40(H40), N48(H48), C56(H56), C66(H66), N30(H30),
 C43(H43), C61(H61), C81(H81), C83(H83), C93(H93), N51(H51), C86(H86),
 C101(H101), C105(H105), C112(H112), C113(H113)
3.d Idealised Me refined as rotating group:
 C69(H69A,H69B,H69C), C74(H74A,H74B,H74C), C92(H92A,H92B,H92C), C100(H10A,H10B,
 H10C), C102(H10D,H10E,H10F), C114(H11A,H11B,H11C), C76(H76A,H76B,H76C),
 C79(H79A,H79B,H79C), C82(H82A,H82B,H82C), C89(H89A,H89B,H89C), C90(H90A,H90B,
 H90C), C96(H96A,H96B,H96C), C99(H99A,H99B,H99C), C103(H10G,H10H,H10I),
 C107(H10L,H10M,H10N), C117(H11D,H11E,H11F), C119(H11G,H11H,H11I), C124(H12A,
 H12B,H12C)
;
_shelx_res_checksum              92686
_shelx_hkl_checksum              27386
_shelx_fab_checksum              25411
_olex2_submission_special_instructions 'No special instructions were received'