Structurally diverse diketopiperazine alkaloids from the marine-derived fungus Aspergillus versicolor SCSIO 41016
Luo, Xiaowei; Chen, Chunmei; Tao, Huaming; Lin, Xiuping; Yang, Bin; Zhou, Xuefeng; Liu, Yonghong; Organic Chemistry Frontiers 6 (2019) 736–; doi:10.1039/C8QO01147H

data_1554520
_publ_section_title
;
 Structurally diverse diketopiperazine alkaloids from the marine-derived
 fungus Aspergillus versicolor SCSIO 41016
;
_journal_issue                   6
_journal_name_full               'Organic Chemistry Frontiers'
_journal_page_first              736
_journal_paper_doi               10.1039/C8QO01147H
_journal_volume                  6
_journal_year                    2019
_chemical_absolute_configuration ad
_chemical_compound_source
'Marine Sponge-Derived Fungus Aspergillus versicolor SCSIO 41016'
_chemical_formula_moiety         'C23 H25 N3 O3'
_chemical_formula_sum            'C23 H25 N3 O3'
_chemical_formula_weight         391.47
_chemical_name_common
(1R,4R)-4-benzyl-1-((S)-sec-butyl)-1-methoxy-1,2-dihydro-6H-pyrazino[2,1-b]quinazoline-3,6(4H)-dione
_chemical_name_systematic        'Brevianamide Y'
_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     dual
_audit_creation_date             2018-04-04
_audit_creation_method
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_audit_update_record
;
2018-08-22 deposited with the CCDC.
2019-01-30 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   11.8106(4)
_cell_length_b                   12.5767(4)
_cell_length_c                   26.9924(10)
_cell_measurement_reflns_used    10419
_cell_measurement_temperature    100.0(3)
_cell_measurement_theta_max      67.3950
_cell_measurement_theta_min      4.9630
_cell_volume                     4009.4(2)
_computing_cell_refinement       'CrysAlisPro 1.171.39.33c (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.33c (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.33c (Rigaku OD, 2017)'
_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    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.0(3)
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_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    -30.00  30.00   0.50   11.34    --    0.00 -82.00  30.00  120
  2  \w    -32.00  27.00   0.50   11.34    --    0.00 -82.00-180.00  118
  3  \w    -30.00  -4.00   0.50   11.34    --    0.00 -82.00 -90.00   52
  4  \w     79.00 128.00   0.50   52.38    --   94.60  45.00 -60.00   98
  5  \w     75.00 172.00   0.50   52.38    --   94.60  45.00   0.00  194
  6  \w      6.00 113.00   0.50   52.38    --   94.60 -61.00  90.00  214
  7  \w    101.00 140.00   0.50   52.38    --   94.60  82.00  90.00   78
  8  \w    143.00 178.00   0.50   52.38    --   94.60  45.00 -60.00   70
  9  \w     76.00 184.00   0.50   52.38    --   94.60  45.00 -30.00  216
 10  \w     82.00 163.00   0.50   52.38    --   94.60  61.00-150.00  162
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RINC): Kappa single'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0960829000
_diffrn_orient_matrix_UB_12      0.0770392000
_diffrn_orient_matrix_UB_13      -0.0140947000
_diffrn_orient_matrix_UB_21      0.0294047000
_diffrn_orient_matrix_UB_22      -0.0140590000
_diffrn_orient_matrix_UB_23      -0.0552125000
_diffrn_orient_matrix_UB_31      -0.0831766000
_diffrn_orient_matrix_UB_32      -0.0941859000
_diffrn_orient_matrix_UB_33      -0.0033132000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0460
_diffrn_reflns_av_unetI/netI     0.0486
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_number            18067
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        67.064
_diffrn_reflns_theta_max         67.064
_diffrn_reflns_theta_min         3.878
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.688
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.80159
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.33c (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear yellowish yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   yellowish
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.295
_exptl_crystal_description       block
_exptl_crystal_F_000             1664
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: MeOH/CHCl3'
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.383
_refine_diff_density_min         -0.243
_refine_diff_density_rms         0.050
_refine_ls_abs_structure_details
;
 Flack x determined using 2159 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.05(12)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     529
_refine_ls_number_reflns         7112
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.029
_refine_ls_R_factor_all          0.0630
_refine_ls_R_factor_gt           0.0501
_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^)+(0.0980P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1333
_refine_ls_wR_factor_ref         0.1414
_reflns_Friedel_coverage         0.778
_reflns_Friedel_fraction_full    0.991
_reflns_Friedel_fraction_max     0.991
_reflns_number_gt                5908
_reflns_number_total             7112
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8qo01147h2.cif
_cod_data_source_block           luoxiaowei_th31_collect
_cod_depositor_comments
;

2022-09-15
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_sum            'C184 H204 N28 O20'
_cod_original_formula_weight         3127.74
_cod_original_formula_moiety         '8(C23 H25 N3 O3)'
_cod_original_formula_units_Z            1
_cod_database_code               1554520
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         'C184 H204 N28 O20 '
_shelx_estimated_absorpt_t_max   0.934
_shelx_estimated_absorpt_t_min   0.875
_reflns_odcompleteness_completeness 99.75
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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.a Ternary CH refined with riding coordinates:
 C15(H15), C16(H16), C16'(H16'), C15'(H15')
2.b Secondary CH2 refined with riding coordinates:
 C17(H17A,H17B), C20(H20A,H20B), C20'(H20C,H20D), C17'(H17C,H17D)
2.c Aromatic/amide H refined with riding coordinates:
 N2'(H2'), N2(H2), C11(H11), C9'(H9'), C22'(H22'), C10'(H10'), C11'(H11'),
 C8(H8), C24'(H24'), C10(H10), C9(H9), C8'(H8'), C26'(H26'), C23'(H23'),
 C25'(H25'), C22(H22), C26(H26), C24(H24), C23(H23), C25(H25)
2.d Idealised Me refined as rotating group:
 C18'(H18D,H18E,H18F), C18(H18A,H18B,H18C), C27'(H27D,H27E,H27F), C27(H27A,
 H27B,H27C), C19'(H19D,H19E,H19F), C19(H19A,H19B,H19C)
;
_shelx_res_checksum              97480
_shelx_hkl_checksum              70392
_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
- B-factor correction
;
_oxdiff_exptl_absorpt_empirical_full_max 3.897
_oxdiff_exptl_absorpt_empirical_full_min 0.210