Substituted l-tryptophan-l-phenyllactic acid conjugates produced by an endophytic fungus Aspergillus aculeatus using an OSMAC approach
Wang, Hao; Eze, Peter M.; Höfert, Simon-Patrick; Janiak, Christoph; Hartmann, Rudolf; Okoye, Festus B. C.; Esimone, Charles O.; Orfali, Raha S.; Dai, Haofu; Liu, Zhen; Proksch, Peter; RSC Advances 8 (2018) 7863–; doi:10.1039/C8RA00200B

data_7230177
_publ_section_title
;
 Substituted l-tryptophan-l-phenyllactic acid conjugates produced by an
 endophytic fungus Aspergillus aculeatus using an OSMAC approach
;
_journal_issue                   14
_journal_name_full               'RSC Advances'
_journal_page_first              7863
_journal_paper_doi               10.1039/C8RA00200B
_journal_volume                  8
_journal_year                    2018
_chemical_absolute_configuration ad
_chemical_compound_source        'Endophytic Fungus Aspergillus aculeatus'
_chemical_formula_moiety         'C21 H22 N2 O4, C H4 O'
_chemical_formula_sum            'C22 H26 N2 O5'
_chemical_formula_weight         398.45
_chemical_name_common            'Aculeatine A'
_space_group_crystal_system      monoclinic
_space_group_IT_number           5
_space_group_name_Hall           'C 2y'
_space_group_name_H-M_alt        'C 1 2 1'
_symmetry_space_group_name_Hall  'C 2y'
_symmetry_space_group_name_H-M   'C 1 2 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2017/1
_audit_update_record
;
2017-12-08 deposited with the CCDC.
2018-02-12 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 112.574(17)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   23.52(2)
_cell_length_b                   5.994(5)
_cell_length_c                   15.843(13)
_cell_measurement_reflns_used    9974
_cell_measurement_temperature    140(2)
_cell_measurement_theta_max      67.530
_cell_measurement_theta_min      5.871
_cell_volume                     2062(3)
_computing_cell_refinement       'SAINT (Bruker, 2012)'
_computing_data_collection       'APEX2 (Bruker, 2012)'
_computing_data_reduction        'SAINT (Bruker, 2012)'
_computing_molecular_graphics    'DIAMOND 4.3.1 (Brandenburg, 1999)'
_computing_publication_material  'SHELXL-2017/1 (Sheldrick, 2015b)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2015b)'
_computing_structure_solution    'SHELXT-2015 (Sheldrick 2015a)'
_diffrn_ambient_temperature      140(2)
_diffrn_measured_fraction_theta_full 0.974
_diffrn_measured_fraction_theta_max 0.973
_diffrn_measurement_device_type  'Bruker Kappa APEX-II CCD area detector'
_diffrn_measurement_method       '\w scans, \f scans'
_diffrn_radiation_monochromator  'multilayer mirror'
_diffrn_radiation_source         'microfocus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0269
_diffrn_reflns_av_unetI/netI     0.0365
_diffrn_reflns_Laue_measured_fraction_full 0.974
_diffrn_reflns_Laue_measured_fraction_max 0.973
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            11796
_diffrn_reflns_point_group_measured_fraction_full 0.959
_diffrn_reflns_point_group_measured_fraction_max 0.958
_diffrn_reflns_theta_full        65.556
_diffrn_reflns_theta_max         65.556
_diffrn_reflns_theta_min         5.854
_exptl_absorpt_coefficient_mu    0.749
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.9168
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(<i>SADABS</i>; Sheldrick, 1996)'
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_density_diffrn    1.283
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             848
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: methanol'
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.050
_refine_diff_density_max         0.192
_refine_diff_density_min         -0.205
_refine_diff_density_rms         0.053
_refine_ls_abs_structure_details
;
 Flack x determined using 1433 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.00(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.089
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     276
_refine_ls_number_reflns         3416
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.089
_refine_ls_R_factor_all          0.0408
_refine_ls_R_factor_gt           0.0250
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0393P)^2^+0.5585P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0658
_refine_ls_wR_factor_ref         0.0667
_reflns_Friedel_coverage         0.783
_reflns_Friedel_fraction_full    0.941
_reflns_Friedel_fraction_max     0.940
_reflns_number_gt                3283
_reflns_number_total             3416
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8ra00200b2.cif
_cod_data_source_block           Compound_2
_cod_original_cell_volume        2063(3)
_cod_database_code               7230177
_shelx_shelxl_version_number     2017/1
_shelx_estimated_absorpt_t_min   0.865
_shelx_estimated_absorpt_t_max   0.964
_shelx_res_checksum              33634