Antifungal Macrocyclic Trichothecenes from the Insect-Associated Fungus <i>Myrothecium roridum</i>.
Li, Tian-Xiao; Xiong, Ya-Mei; Chen, Xin; Yang, Ya-Nan; Wang, Ying; Jia, Xue-Wei; Yang, Xue-Peng; Tan, Lan-Lan; Xu, Chun-Ping; Journal of agricultural and food chemistry 67 (2019) 13033–13039; doi:10.1021/acs.jafc.9b04507

data_1552919
_publ_section_title
;
 Antifungal Macrocyclic Trichothecenes from the Insect-Associated Fungus
 <i>Myrothecium roridum</i>.
;
_journal_issue                   47
_journal_name_full               'Journal of agricultural and food chemistry'
_journal_page_first              13033
_journal_page_last               13039
_journal_paper_doi               10.1021/acs.jafc.9b04507
_journal_volume                  67
_journal_year                    2019
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C29 H38 O10, 2(C H Cl3)'
_chemical_formula_sum            'C31 H40 Cl6 O10'
_chemical_formula_weight         785.33
_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     iterative
_audit_creation_date             2018-10-18
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 90.1069(15)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.18909(10)
_cell_length_b                   29.7457(5)
_cell_length_c                   15.1177(3)
_cell_measurement_reflns_used    9259
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      70.6680
_cell_measurement_theta_min      4.1620
_cell_volume                     3682.52(11)
_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    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve (Bourhis et al., 2015)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.2312
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_details
;
  1 omega  -32.00   37.00   0.5000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      -33.5000   37.0000 -120.0000 138

  2 omega   57.00  109.00   0.5000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  178.0000 -150.0000 104

  3 omega   41.00  104.00   0.5000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734   57.0000  150.0000 126

  4 omega   19.00   55.00   0.5000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  -57.0000    0.0000 72

  5 omega   64.00  110.00   0.5000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  178.0000   30.0000 92

  6 omega   57.00  107.00   0.5000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  178.0000  -60.0000 100

  7 omega  -24.00    2.00   0.5000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  -57.0000    0.0000 52

  8 omega   57.00   82.00   0.5000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  178.0000  -30.0000 50

  9 omega   15.00   55.00   0.5000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  -37.0000 -150.0000 80

 10 omega  -22.00    4.00   0.5000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  -37.0000 -150.0000 52

 11 omega   38.00   95.00   0.5000   25.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000 -120.0000 114

 12 omega   42.00   92.00   0.5000   25.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -36.0000    7.0000 100

 13 omega   70.00  106.00   0.5000   25.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000   60.0000 72

 14 omega   42.00   92.00   0.5000   25.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000 -150.0000 100

 15 omega   37.00   78.00   0.5000   18.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000   90.0000 82

 16 omega   87.00  117.00   0.5000   18.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -61.0000  -90.0000 60

 17 omega  103.00  140.00   0.5000   18.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  111.0000 -180.0000 74

 18 omega   38.00   95.00   0.5000   18.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000   30.0000 114

 19 omega   72.00   97.00   0.5000   18.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000  120.0000 50

 20 omega   39.00   98.00   0.5000   18.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000  -90.0000 118

 21 omega   61.00   87.00   0.5000   18.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000   30.0000 52

 22 omega   56.00   82.00   0.5000   18.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -61.0000  -90.0000 52

 23 omega   51.00  127.00   0.5000   18.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -61.0000   30.0000 152

 24 omega   47.00   91.00   0.5000   18.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000  -90.0000 88

 25 omega   68.00   96.00   0.5000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  178.0000  120.0000 56

 26 omega   64.00   92.00   0.5000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  178.0000  -90.0000 56

 27 omega   17.00   43.00   0.5000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734   77.0000  -90.0000 52

 28 omega   77.00  104.00   0.5000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734   77.0000  -90.0000 54

 29 omega   37.00   62.00   0.5000   18.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000 -180.0000 50

 30 omega   65.00   91.00   0.5000   18.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000 -150.0000 52

 31 omega   61.00   86.00   0.5000   18.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000 -150.0000 50

 32 omega   72.00   98.00   0.5000   18.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000 -180.0000 52

 33 omega   77.00  111.00   0.5000   18.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   15.0000 -180.0000 68

 34 omega  -75.00  -42.00   0.5000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      -33.5000  178.0000  -60.0000 66

 35 omega  -85.00  -59.00   0.5000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      -33.5000  -77.0000  -60.0000 52

 36 omega  -31.00   -5.00   0.5000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      -33.5000  -77.0000  -60.0000 52

 37 omega  -24.00    5.00   0.5000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  -57.0000  150.0000 58

 38 omega   25.00   51.00   0.5000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  -57.0000  150.0000 52

 39 omega   71.00   99.00   0.5000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734   77.0000 -120.0000 56

 40 omega   38.00   75.00   0.5000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  -99.0000  120.0000 74

 41 omega  -34.00    8.00   0.5000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  -37.0000 -180.0000 84

 42 omega   58.00   92.00   0.5000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734   57.0000    0.0000 68

 43 omega   22.00   77.00   0.5000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734   57.0000   60.0000 110

 44 omega   47.00   73.00   0.5000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  -99.0000  -60.0000 52

 45 omega   35.00   62.00   0.5000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734   77.0000 -120.0000 54

 46 omega   88.00  114.00   0.5000   18.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -111.0000 -180.0000 52

 47 omega   82.00  173.00   0.5000   18.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   30.0000   60.0000 182

 48 omega   38.00   65.00   0.5000   18.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000 -180.0000 54

 49 omega   59.00  107.00   0.5000   18.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000    0.0000 96

 50 omega   72.00  108.00   0.5000   18.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -111.0000  -30.0000 72

 51 omega  108.00  149.00   0.5000   18.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   30.0000  -60.0000 82
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0098151000
_diffrn_orient_matrix_UB_12      0.0376846000
_diffrn_orient_matrix_UB_13      -0.0696937000
_diffrn_orient_matrix_UB_21      -0.0955655000
_diffrn_orient_matrix_UB_22      0.0295217000
_diffrn_orient_matrix_UB_23      0.0657146000
_diffrn_orient_matrix_UB_31      0.1617654000
_diffrn_orient_matrix_UB_32      0.0197505000
_diffrn_orient_matrix_UB_33      0.0347948000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_unetI/netI     0.0432
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       36
_diffrn_reflns_limit_k_min       -36
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            12808
_diffrn_reflns_point_group_measured_fraction_full 0.981
_diffrn_reflns_point_group_measured_fraction_max 0.968
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         70.860
_diffrn_reflns_theta_min         4.170
_diffrn_source                   'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    4.703
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.54388
_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            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.416
_exptl_crystal_description       prism
_exptl_crystal_F_000             1632
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.685
_refine_diff_density_min         -0.351
_refine_diff_density_rms         0.052
_refine_ls_abs_structure_details
;
 Flack x determined using 3853 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.026(8)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     888
_refine_ls_number_reflns         12808
_refine_ls_number_restraints     22
_refine_ls_restrained_S_all      1.049
_refine_ls_R_factor_all          0.0698
_refine_ls_R_factor_gt           0.0619
_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^)+(0.1130P)^2^+0.5999P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1724
_refine_ls_wR_factor_ref         0.1832
_reflns_Friedel_coverage         0.907
_reflns_Friedel_fraction_full    0.962
_reflns_Friedel_fraction_max     0.940
_reflns_number_gt                11011
_reflns_number_total             12808
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jf9b04507_si_002.cif
_cod_data_source_block           201810406_tw
_cod_depositor_comments          'Adding full bibliography for 1552919.cif.'
_cod_original_cell_volume        3682.51(11)
_cod_database_code               1552919
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         C15H15O3N2
_shelx_estimated_absorpt_t_max   0.734
_shelx_estimated_absorpt_t_min   0.453
_reflns_odcompleteness_completeness 99.93
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.8906(17)
 0.1094(17)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
3. Restrained distances
 C19-Cl8
 1.75 with sigma of 0.02
 Cl9-C19
 1.75 with sigma of 0.02
 C20-Cl1A
 1.75 with sigma of 0.02
 C20-Cl10
 1.75 with sigma of 0.02
 Cl10-Cl1A
 2.5 with sigma of 0.02
 Cl2A-Cl1A
 2.55 with sigma of 0.02
 Cl4A-Cl5A
 2.55 with sigma of 0.02
 Cl5-C18
 1.76 with sigma of 0.02
 C18-Cl6A
 1.76 with sigma of 0.02
 C18-Cl4A
 1.76 with sigma of 0.02
 Cl6A-Cl5A
 2.56 with sigma of 0.02
 C18-Cl5A
 1.75 with sigma of 0.02
 O10A-H10D
 0.9 with sigma of 0.02
 Cl8-C19
 1.72 with sigma of 0.02
 C19-Cl7A
 1.62 with sigma of 0.02
 C19-Cl9A
 1.72 with sigma of 0.02
 Cl7A-Cl9A
 2.54 with sigma of 0.02
 Cl8A-C19
 1.75 with sigma of 0.02
 C14'-C13'
 1.55 with sigma of 0.02
 C13B-C14B
 1.55 with sigma of 0.02
 C5-C4
 1.55 with sigma of 0.02
4. Uiso/Uaniso restraints and constraints
Uanis(Cl4) = Uanis(Cl4A)
Uanis(Cl6) = Uanis(Cl6A)
Uanis(Cl12) = Uanis(Cl10)
Uanis(Cl11) = Uanis(Cl1A)
Uanis(Cl0A) = Uanis(Cl2A)
Uanis(Cl5) = Uanis(Cl5A)
Uanis(Cl9) = Uanis(Cl9A)
Uanis(Cl8) = Uanis(Cl8A)
Uanis(Cl7) = Uanis(Cl7A)
5. Others
 Sof(H18A)=Sof(Cl4A)=Sof(Cl5A)=Sof(Cl6A)=1-FVAR(1)
 Sof(H18)=Sof(Cl4)=Sof(Cl5)=Sof(Cl6)=FVAR(1)
 Sof(H20A)=Sof(Cl10)=Sof(Cl1A)=Sof(Cl2A)=1-FVAR(2)
 Sof(H20)=Sof(Cl0A)=Sof(Cl11)=Sof(Cl12)=FVAR(2)
 Sof(H19A)=Sof(Cl9A)=Sof(Cl8A)=Sof(Cl7A)=1-FVAR(3)
 Sof(H19)=Sof(Cl7)=Sof(Cl8)=Sof(Cl9)=FVAR(3)
6.a Riding coordinates:
 O10(H10A)
6.b Ternary CH refined with riding coordinates:
 C2(H2), C2'(H2'), C4(H4), C11(H11), C12'(H12'), C2A(H2A), C2A'(H2A'),
 C4A(H4A), C11A(H11A), C12B(H12B), C17(H17), C18(H18), C18(H18A), C19(H19),
 C19(H19A), C20(H20A), C20(H20)
6.c Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B), C4'(H4'A,H4'B), C5'(H5'A,H5'B), C7(H7A,H7B), C7'(H7'A,H7'B),
 C8(H8A,H8B), C8'(H8'A,H8'B), C13(H13A,H13B), C13'(H13C,H13D), C15(H15A,H15B),
 C3A(H3AA,H3AB), C4A'(H4AA,H4AB), C5A'(H5AA,H5AB), C7A(H7AA,H7AB), C7A'(H7AC,
 H7AD), C8A(H8AA,H8AB), C8A'(H8AC,H8AD), C13A(H13E,H13F), C13B(H13G,H13H),
 C15A(H15C,H15D)
6.d Aromatic/amide H refined with riding coordinates:
 C9'(H9'), C10(H10), C10'(H10'), C9A'(H9A'), C10A(H10B), C10B(H10C)
6.e Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C), C14'(H14D,H14E,H14F), C16(H16A,H16B,H16C), C14A(H14G,
 H14H,H14I), C14B(H14J,H14K,H14L), C16A(H16D,H16E,H16F)
;
_olex2_submission_special_instructions 'No special instructions were received'