Eutypellazines A‒M, thiodiketopiperazine-type alkaloids from deep sea derived fungus Eutypella sp. MCCC 3A00281
Niu, Siwen; Liu, Dong; Shao, Zongze; Proksch, Peter; Lin, Wenhan; RSC Adv. 7 (2017) 33580–; doi:10.1039/C7RA05774A

data_7228624
_publ_section_title
;
 Eutypellazines A--M, thiodiketopiperazine-type alkaloids from deep sea
 derived fungus Eutypella sp. MCCC 3A00281
;
_journal_issue                   53
_journal_name_full               'RSC Adv.'
_journal_page_first              33580
_journal_paper_doi               10.1039/C7RA05774A
_journal_volume                  7
_journal_year                    2017
_chemical_absolute_configuration ad
_chemical_formula_moiety
'C20 H22 N2 O5 S2, 0.210687(C1 H4 O1), 0.19912(O)'
_chemical_formula_sum            'C20.21 H22.84 N2 O5.4 S2'
_chemical_formula_weight         444.37
_chemical_name_systematic
;
 ? 
;
_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'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2015-05-13
_audit_creation_method
;
  Olex2 1.1
  (compiled 2011.02.15 svn.r1672, GUI svn.r3494)
;
_audit_update_record
;
2015-08-03 deposited with the CCDC.
2017-06-27 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            12
_cell_length_a                   14.08776(18)
_cell_length_b                   15.89161(19)
_cell_length_c                   27.9520(4)
_cell_measurement_reflns_used    19150
_cell_measurement_temperature    99.9
_cell_measurement_theta_max      70.9627
_cell_measurement_theta_min      3.1349
_cell_volume                     6257.82(14)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_molecular_graphics
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution
'A short history of SHELX (Sheldrick, 2007)/Bruker'
_diffrn_ambient_temperature      99.9
_diffrn_detector_area_resol_mean 16.0971
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_details
;
  1 omega    5.00   43.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       -8.5000    0.0000  -60.0000 38

  2 omega  -20.00    6.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       -8.5000  111.0000  120.0000 26

  3 omega  -78.00  -51.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       -8.5000    0.0000  -60.0000 27

  4 omega  -31.00   42.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       36.7919  -37.0000   60.0000 73

  5 omega   16.00   65.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       36.7919 -107.0000 -164.0000 49

  6 omega    4.00   79.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       36.7919 -107.0000   66.0000 75

  7 omega   30.00   90.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       36.7919   37.0000    0.0000 60

  8 omega   85.00  113.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -107.0000   15.0000 28

  9 omega   48.00   92.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000 -120.0000 44

 10 omega   42.00   98.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000    0.0000 56

 11 omega  121.00  147.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  111.0000 -150.0000 26

 12 omega   48.00   97.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000   90.0000 49

 13 omega  125.00  178.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  111.0000  150.0000 53

 14 omega  131.00  177.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   15.0000  150.0000 46

 15 omega   94.00  120.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   15.0000  150.0000 26

 16 omega  119.00  172.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   45.0000 -180.0000 53

 17 omega   45.00   72.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000   60.0000 27

 18 omega  140.00  174.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000  120.0000 34

 19 omega   84.00  121.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000  120.0000 37

 20 omega   32.00   58.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       -8.5000   37.0000  -90.0000 26

 21 omega  -73.00  -47.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       -8.5000  -45.0000  -60.0000 26

 22 omega  -20.00    6.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       -8.5000   37.0000  -90.0000 26

 23 omega  -23.00    8.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       -8.5000  -45.0000  -60.0000 31

 24 omega   52.00  105.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       35.8017   37.0000 -120.0000 53

 25 omega   35.00   76.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       35.8017 -107.0000 -113.0000 41

 26 omega  -31.00   10.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       35.8017  -77.0000 -180.0000 41

 27 omega   26.00   52.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       35.8017  -77.0000  -60.0000 26

 28 omega    1.00   32.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       35.8017  -37.0000  -30.0000 31

 29 omega  -21.00   18.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       35.8017  -77.0000  -60.0000 39

 30 omega   40.00   79.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000 -150.0000 39

 31 omega  106.00  132.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  111.0000  -30.0000 26

 32 omega   65.00   91.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -108.0000  100.0000 26

 33 omega   67.00   98.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000  120.0000 31

 34 omega  136.00  162.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   45.0000   60.0000 26

 35 omega   65.00  121.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -77.0000  150.0000 56

 36 omega  111.00  140.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  111.0000  -60.0000 29

 37 omega   94.00  122.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   45.0000   60.0000 28

 38 omega  108.00  134.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  111.0000   90.0000 26

 39 omega  151.00  176.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  111.0000   60.0000 25

 40 omega  108.00  134.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  111.0000   60.0000 26

 41 omega   57.00   87.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -107.0000   15.0000 30

 42 omega   91.00  117.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   45.0000 -120.0000 26
;
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0553359000
_diffrn_orient_matrix_UB_12      -0.0732381000
_diffrn_orient_matrix_UB_13      0.0230830000
_diffrn_orient_matrix_UB_21      0.0486050000
_diffrn_orient_matrix_UB_22      0.0182271000
_diffrn_orient_matrix_UB_23      0.0482943000
_diffrn_orient_matrix_UB_31      -0.0808199000
_diffrn_orient_matrix_UB_32      0.0608493000
_diffrn_orient_matrix_UB_33      0.0132314000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.5418
_diffrn_reflns_av_R_equivalents  0.0396
_diffrn_reflns_av_unetI/netI     0.0352
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_number            42403
_diffrn_reflns_theta_full        71.07
_diffrn_reflns_theta_max         71.07
_diffrn_reflns_theta_min         3.20
_diffrn_source                   'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.639
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.54740
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.415
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             2800
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.997
_refine_diff_density_min         -0.525
_refine_diff_density_rms         0.063
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.015(12)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.073
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     826
_refine_ls_number_reflns         11963
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.073
_refine_ls_R_factor_all          0.0463
_refine_ls_R_factor_gt           0.0449
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0623P)^2^+4.6690P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1163
_refine_ls_wR_factor_ref         0.1175
_reflns_number_gt                11611
_reflns_number_total             11963
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c7ra05774a2.cif
_cod_data_source_block           exp_3148
_cod_original_formula_sum        'C20.21 H22.84 N2 O5.40 S2'
_cod_database_code               7228624
_reflns_odcompleteness_completeness 99.95
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97