l-Phenylalanine Alters the Privileged Secondary Metabolite Production in the Marine-Derived Fungus Trichoderma erinaceum F1-1
Guo, Yong-Wei; Gong, Ben-Qiang; Yuan, Jie; Li, Hou-Jin; Mahmud, Taifo; Huang, Yun; Li, Jian-Feng; Yang, De-Po; Lan, Wen-Jian; Journal of Natural Products  (2019) –; doi:10.1021/acs.jnatprod.9b00710

data_1556850
_publ_section_title
;
 l-Phenylalanine Alters the Privileged Secondary Metabolite Production in
 the Marine-Derived Fungus Trichoderma erinaceum F1-1
;
_journal_name_full               'Journal of Natural Products'
_journal_paper_doi               10.1021/acs.jnatprod.9b00710
_journal_year                    2019
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C20 H28 O3'
_chemical_formula_sum            'C20 H28 O3'
_chemical_formula_weight         316.42
_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   geom
_atom_sites_solution_primary     direct
_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                 98.2546(9)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   8.26597(8)
_cell_length_b                   9.64323(9)
_cell_length_c                   10.64668(11)
_cell_measurement_reflns_used    12973
_cell_measurement_temperature    100
_cell_measurement_theta_max      75.8710
_cell_measurement_theta_min      4.1710
_cell_volume                     839.862(14)
_computing_cell_refinement       'CrysAlisPro 1.171.38.41r (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.41r (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41r (Rigaku OD, 2015)'
_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    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      100
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.2417
_diffrn_detector_type            Onyx
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.996
_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   -114.00 -18.00   1.00    1.00    --  -43.93 -57.00 -90.00   96
  2  \w   -118.00 -73.00   1.00    1.00    --  -43.93-125.00 -60.00   45
  3  \w     20.00 116.00   1.00    1.00    --   43.93  37.00-180.00   96
  4  \w     73.00 118.00   1.00    1.00    --   43.93 125.00 120.00   45
  5  \w     73.00 118.00   1.00    1.00    --   43.93 125.00   0.00   45
  6  \w     73.00 118.00   1.00    1.00    --   43.93 125.00-120.00   45
  7  \w     18.00 114.00   1.00    1.00    --   43.93  57.00  60.00   96
  8  \w     84.00 178.00   1.00    2.00    --  108.00  45.00 120.00   94
  9  \w     81.00 178.00   1.00    2.00    --  108.00  61.00  90.00   97
 10  \w     81.00 178.00   1.00    2.00    --  108.00  61.00  60.00   97
 11  \w     25.00 109.00   1.00    2.00    --  108.00 -94.00-120.00   84
 12  \w     34.00 121.00   1.00    2.00    --  108.00-125.00-120.00   87
 13  \w     76.00 178.00   1.00    2.00    --  108.00  77.00 150.00  102
 14  \w     84.00 178.00   1.00    2.00    --  108.00  45.00  90.00   94
 15  \w     76.00 178.00   1.00    2.00    --  108.00  77.00  30.00  102
 16  \w     34.00 121.00   1.00    2.00    --  108.00-125.00 120.00   87
 17  \w     81.00 178.00   1.00    2.00    --  108.00  61.00 -60.00   97
 18  \w     81.00 178.00   1.00    2.00    --  108.00  61.00 120.00   97
 19  \w     38.00 134.00   1.00    2.00    --  108.00 -60.00-145.00   96
 20  \w     82.00 178.00   1.00    2.00    --  108.00  60.00  -6.00   96
 21  \w     76.00 178.00   1.00    2.00    --  108.00  77.00  90.00  102
 22  \w     35.00 135.00   1.00    2.00    --  108.00 -30.00   0.00  100
 23  \w     18.00 114.00   1.00    1.00    --   43.93  57.00-120.00   96
 24  \w      2.00  97.00   1.00    1.00    --   43.93-125.00   0.00   95
 25  \w      2.00  97.00   1.00    1.00    --   43.93-125.00-150.00   95
 26  \w     12.00 118.00   1.00    1.00    --   43.93  77.00 120.00  106
 27  \w     12.00 118.00   1.00    1.00    --   43.93  77.00 -60.00  106
 28  \w     76.00 178.00   1.00    2.00    --  108.00  77.00-120.00  102
 29  \w     81.00 178.00   1.00    2.00    --  108.00  30.00-120.00   97
 30  \w     76.00 178.00   1.00    2.00    --  108.00  77.00-180.00  102
 31  \w     81.00 178.00   1.00    2.00    --  108.00  61.00 -30.00   97
 32  \w     34.00 140.00   1.00    2.00    --  108.00 -77.00   0.00  106
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Onyx, Nova'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1831816000
_diffrn_orient_matrix_UB_12      0.0276326000
_diffrn_orient_matrix_UB_13      -0.0020601000
_diffrn_orient_matrix_UB_21      0.0436683000
_diffrn_orient_matrix_UB_22      -0.1093159000
_diffrn_orient_matrix_UB_23      0.1048747000
_diffrn_orient_matrix_UB_31      0.0024380000
_diffrn_orient_matrix_UB_32      -0.1131796000
_diffrn_orient_matrix_UB_33      -0.1018499000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0408
_diffrn_reflns_av_unetI/netI     0.0257
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            16354
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.016
_diffrn_reflns_theta_min         4.196
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'Nova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.650
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.22624
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.41r (Rigaku Oxford Diffraction, 2015)
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    1.251
_exptl_crystal_description       block
_exptl_crystal_F_000             344
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.200
_refine_diff_density_min         -0.146
_refine_diff_density_rms         0.033
_refine_ls_abs_structure_details
;
 Flack x determined using 1548 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.03(8)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     214
_refine_ls_number_reflns         3460
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.048
_refine_ls_R_factor_all          0.0298
_refine_ls_R_factor_gt           0.0290
_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^)+(0.0439P)^2^+0.1019P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0757
_refine_ls_wR_factor_ref         0.0767
_reflns_Friedel_coverage         0.870
_reflns_Friedel_fraction_full    0.998
_reflns_Friedel_fraction_max     0.982
_reflns_number_gt                3384
_reflns_number_total             3460
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            np9b00710_si_001.cif
_cod_data_source_block           gyw_4-5_180809
_cod_original_cell_volume        839.861(14)
_cod_database_code               1556850
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.938
_shelx_estimated_absorpt_t_min   0.781
_reflns_odcompleteness_completeness 99.77
_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
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C14(H14), C5(H5), C2(H2A), C15(H15)
2.b Secondary CH2 refined with riding coordinates:
 C12(H12A,H12B), C8(H8A,H8B), C7(H7A,H7B), C4(H4A,H4B)
2.c Idealised Me refined as rotating group:
 C17(H17A,H17B,H17C), C20(H20A,H20B,H20C), C16(H16A,H16B,H16C), C19(H19A,H19B,
 H19C), C18(H18A,H18B,H18C)
2.d Idealised tetrahedral OH refined as rotating group:
 O2(H2)
;
_shelx_res_checksum              75555
_shelx_hkl_checksum              44966
_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 4.601
_oxdiff_exptl_absorpt_empirical_full_min 0.454