Phaeosphaones: Tyrosinase Inhibitory Thiodiketopiperazines from an Endophytic Phaeosphaeria fuckelii
Zhai, Yi-Jie; Huo, Guang-Ming; Zhang, Qiang; Li, Ding; Wang, Da-Cheng; Qi, Jian-Zhao; Han, Wen-Bo; Gao, Jin-Ming; Journal of Natural Products  (2020) –; doi:10.1021/acs.jnatprod.0c00046

data_1557938
_publ_section_title
;
 Phaeosphaones: Tyrosinase Inhibitory Thiodiketopiperazines from an
 Endophytic Phaeosphaeria fuckelii
;
_journal_name_full               'Journal of Natural Products'
_journal_paper_doi               10.1021/acs.jnatprod.0c00046
_journal_year                    2020
_chemical_absolute_configuration syn
_chemical_formula_moiety         'C17 H19 N3 O3 S2'
_chemical_formula_sum            'C17 H19 N3 O3 S2'
_chemical_formula_weight         377.47
_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     iterative
_audit_creation_date             2019-04-04
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 93.931(5)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   6.2397(5)
_cell_length_b                   10.6635(10)
_cell_length_c                   12.6809(11)
_cell_measurement_reflns_used    8943
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      74.802
_cell_measurement_theta_min      3.494
_cell_volume                     841.76(13)
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_reduction        'SAINT v8.37A (Bruker, 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
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0750
_diffrn_reflns_av_unetI/netI     0.0584
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            14366
_diffrn_reflns_point_group_measured_fraction_full 0.976
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         67.061
_diffrn_reflns_theta_min         3.494
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    3.068
_exptl_absorpt_correction_T_max  0.7538
_exptl_absorpt_correction_T_min  0.4076
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1536 before and 0.1122 after correction. The Ratio of minimum to maximum transmission is 0.5407. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.489
_exptl_crystal_description       block
_exptl_crystal_F_000             396
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.05
_refine_diff_density_max         1.204
_refine_diff_density_min         -0.450
_refine_diff_density_rms         0.103
_refine_ls_abs_structure_details
;
 Flack x determined using 1214 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   0.162(14)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     230
_refine_ls_number_reflns         2979
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.061
_refine_ls_R_factor_all          0.0623
_refine_ls_R_factor_gt           0.0592
_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^)+(0.1076P)^2^+0.6518P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1538
_refine_ls_wR_factor_ref         0.1568
_reflns_Friedel_coverage         0.865
_reflns_Friedel_fraction_full    0.962
_reflns_Friedel_fraction_max     0.971
_reflns_number_gt                2809
_reflns_number_total             2979
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            np0c00046_si_002.cif
_cod_data_source_block           cu_0403_13_0m
_cod_database_code               1557938
_shelxl_version_number           2013-4
_shelx_estimated_absorpt_t_max   0.862
_shelx_estimated_absorpt_t_min   0.710
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(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:
 C5(H5), C12(H12)
2.b Aromatic/amide H refined with riding coordinates:
 N1(H1), N3(H3), C9(H9), C10(H10), C11(H11), C14(H14), C16(H16)
2.c Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C), C15(H15A,H15B,H15C), C17(H17A,H17B,H17C)
2.d Idealised tetrahedral OH refined as rotating group:
 O2(H2)
;
_shelx_res_checksum              66656
_shelx_hkl_checksum              14915
_olex2_submission_special_instructions 'No special instructions were received'