l-Tryptophan Induces a Marine-Derived <i>Fusarium</i> sp. to Produce Indole Alkaloids with Activity against the Zika Virus.
Guo, Yong-Wei; Liu, Xiao-Jing; Yuan, Jie; Li, Hou-Jin; Mahmud, Taifo; Hong, Ming-Jun; Yu, Jian-Chen; Lan, Wen-Jian; Journal of natural products 83 (2020) 3372–3380; doi:10.1021/acs.jnatprod.0c00717

data_1559509
_publ_section_title
;
 l-Tryptophan Induces a Marine-Derived <i>Fusarium</i> sp. to Produce
 Indole Alkaloids with Activity against the Zika Virus.
;
_journal_issue                   11
_journal_name_full               'Journal of natural products'
_journal_page_first              3372
_journal_page_last               3380
_journal_paper_doi               10.1021/acs.jnatprod.0c00717
_journal_volume                  83
_journal_year                    2020
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C28 H37 N O4'
_chemical_formula_sum            'C28 H37 N O4'
_chemical_formula_weight         451.58
_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             2019-07-09
_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
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.32712(4)
_cell_length_b                   17.39284(13)
_cell_length_c                   21.08445(16)
_cell_measurement_reflns_used    18313
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      76.7510
_cell_measurement_theta_min      3.2860
_cell_volume                     2320.27(3)
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_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      100.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.993
_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    -61.00  26.00   0.50    0.05    --  -46.62  50.00 146.00  174
  2  \w   -173.00 -85.00   0.50    0.25    -- -100.00 -50.00   0.00  176
  3  \w     34.00 129.00   0.50    0.25    --  107.00 -72.00 170.00  190
  4  \w     50.00 160.00   0.50    0.25    --  107.00 164.00 164.00  220
  5  \w   -119.00 -71.00   0.50    0.05    --  -46.62-125.00  90.00   96
  6  \w   -119.00 -71.00   0.50    0.05    --  -46.62-125.00  60.00   96
  7  \w    -61.00  27.00   0.50    0.05    --  -46.62  38.00 -90.00  176
  8  \w   -115.00 -25.00   0.50    0.25    -- -100.00  30.00 -30.00  180
  9  \w     31.00 125.00   0.50    0.25    --  107.00 -15.00 -30.00  188
 10  \w     34.00 117.00   0.50    0.25    --  107.00-125.00-180.00  166
 11  \w     35.00 122.00   0.50    0.25    --  107.00 -45.00 120.00  174
 12  \w     76.00 178.00   0.50    0.25    --  107.00 125.00-120.00  204
 13  \w     34.00 109.00   0.50    0.25    --  107.00 -94.00-180.00  150
 14  \w     31.00 125.00   0.50    0.25    --  107.00 -15.00 150.00  188
 15  \w   -119.00 -23.00   0.50    0.05    --  -46.62 -77.00  60.00  192
 16  \w   -119.00 -68.00   0.50    0.05    --  -46.62 -57.00 -90.00  102
 17  \w   -119.00 -25.00   0.50    0.05    --  -46.62 -72.00 170.00  188
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0428865000
_diffrn_orient_matrix_UB_12      -0.0402480000
_diffrn_orient_matrix_UB_13      0.0638374000
_diffrn_orient_matrix_UB_21      -0.1435141000
_diffrn_orient_matrix_UB_22      -0.0586235000
_diffrn_orient_matrix_UB_23      -0.0338386000
_diffrn_orient_matrix_UB_31      0.1919361000
_diffrn_orient_matrix_UB_32      -0.0527832000
_diffrn_orient_matrix_UB_33      -0.0110095000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0371
_diffrn_reflns_av_unetI/netI     0.0251
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            23647
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.912
_diffrn_reflns_theta_min         3.294
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.678
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.85990
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
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    1.293
_exptl_crystal_description       needle
_exptl_crystal_F_000             976
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.155
_refine_diff_density_min         -0.195
_refine_diff_density_rms         0.033
_refine_ls_abs_structure_details
;
 Flack x determined using 1900 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.01(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     303
_refine_ls_number_reflns         4788
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.053
_refine_ls_R_factor_all          0.0308
_refine_ls_R_factor_gt           0.0293
_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^)+(0.0411P)^2^+0.3698P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0752
_refine_ls_wR_factor_ref         0.0773
_reflns_Friedel_coverage         0.722
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.970
_reflns_number_gt                4615
_reflns_number_total             4788
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            np0c00717_si_001.cif
_cod_data_source_block           guoyw_181227
_cod_depositor_comments          'Adding full bibliography for 1559509.cif.'
_cod_database_code               1559509
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.935
_shelx_estimated_absorpt_t_min   0.823
_reflns_odcompleteness_completeness 100.00
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     71.98
_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:
 C13(H13), C16(H16), C8(H8), C10(H10)
2.b Secondary CH2 refined with riding coordinates:
 C6(H6A,H6B), C7(H7A,H7B), C11(H11A,H11B), C15(H15A,H15B), C14(H14A,H14B),
 C17(H17A,H17B)
2.c Aromatic/amide H refined with riding coordinates:
 N1(H1), C27(H27), C23(H23), C20(H20), C21(H21), C22(H22)
2.d Idealised Me refined as rotating group:
 C25(H25A,H25B,H25C), C26(H26A,H26B,H26C), C0AA(H0AA,H0AB,H0AC), C30(H30A,H30B,
 H30C), C29(H29A,H29B,H29C)
;
_shelx_res_checksum              81840
_shelx_hkl_checksum              78803
_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 1.210
_oxdiff_exptl_absorpt_empirical_full_min 0.856