Heterologous expression of an <i>in planta</i>-upregulated gene cluster in the wheat pathogen <i>Parastagonospora nodorum</i> establishes the biosynthesis of methylene-bridged depsides.
Nguyen, Hera T.; Sbaraini, Nicolau; Bracegirdle, Joe; Smithers, Luke; Moggach, Stephen A.; Vuong, Daniel; Lacey, Ernest; Solomon, Peter S.; Haywood, Joel; Piggott, Andrew M.; Chooi, Yit-Heng; Chemical science 16 (2025) 21852–21861; doi:10.1039/d5sc05442g

data_1576018
_publ_section_title
;
 Heterologous expression of an <i>in planta</i>-upregulated gene cluster
 in the wheat pathogen <i>Parastagonospora nodorum</i> establishes the
 biosynthesis of methylene-bridged depsides.
;
_journal_issue                   46
_journal_name_full               'Chemical science'
_journal_page_first              21852
_journal_page_last               21861
_journal_paper_doi               10.1039/d5sc05442g
_journal_volume                  16
_journal_year                    2025
_chemical_formula_moiety         'C40 H52 O6 S4 Si4'
_chemical_formula_sum            'C40 H52 O6 S4 Si4'
_chemical_formula_weight         869.41
_chemical_melting_point          348.0(5)
_chemical_name_systematic
octakis(3-(p-tolylthio)propyl)octasilsesquioxane
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_block_doi                 10.5517/ccdc.csd.cc1ptjst
_audit_creation_date             2017-07-11
_audit_creation_method
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337)
;
_audit_update_record
;
2017-09-11 deposited with the CCDC.	2025-10-14 downloaded from the CCDC.
;
_cell_angle_alpha                97.723(3)
_cell_angle_beta                 93.763(2)
_cell_angle_gamma                105.157(2)
_cell_formula_units_Z            2
_cell_length_a                   9.8628(6)
_cell_length_b                   14.8091(11)
_cell_length_c                   15.4382(11)
_cell_measurement_reflns_used    9657
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.19
_cell_measurement_theta_min      2.61
_cell_volume                     2144.7(3)
_computing_cell_refinement       'SAINT V8.35A (?, 2016)'
_computing_data_reduction        'SAINT V8.35A (?, 2016)'
_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_temperature      100
_diffrn_detector                 'Bruker D8 VENTURE area detector'
_diffrn_detector_area_resol_mean 10.4167
_diffrn_detector_type            'CMOS PHOTON100 area detector'
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Bruker D8 VENTURE area detector'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_radiation_monochromator  'HELIOS mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0428
_diffrn_reflns_av_unetI/netI     0.0224
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            77574
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         26.999
_diffrn_reflns_theta_min         2.609
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\ms'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.378
_exptl_absorpt_correction_T_max  0.4302
_exptl_absorpt_correction_T_min  0.3601
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2014/5 (Bruker,2014/5) was used for absorption correction. wR2(int) was 0.1407 before and 0.0733 after correction. The Ratio of minimum to maximum transmission is 0.8371. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            ' colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.346
_exptl_crystal_description       needle
_exptl_crystal_F_000             920
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: THF-methanol '
_exptl_crystal_size_max          0.99
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.13
_refine_diff_density_max         0.545
_refine_diff_density_min         -0.596
_refine_diff_density_rms         0.057
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     491
_refine_ls_number_reflns         9322
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.047
_refine_ls_R_factor_all          0.0298
_refine_ls_R_factor_gt           0.0274
_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^)+(0.0326P)^2^+1.3583P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0714
_refine_ls_wR_factor_ref         0.0730
_reflns_Friedel_coverage         0.000
_reflns_number_gt                8656
_reflns_number_total             9322
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5sc05442g2.cif
_cod_data_source_block           mo_b0487_0m
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_chemical_melting_point' value '347.5-348.5' was changed
to '348.0(5)' -- the average value was taken and precision was
estimated.

Automatic conversion script
Id: cif_fix_values 8170 2020-07-09 18:12:32Z antanas 

 Adding full bibliography for 1576015--1576018.cif.
;
_cod_database_code               1576018
_shelx_shelxl_version_number     2014/7
_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
2.a Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C2(H2A,H2B), C3(H3A,H3B), C11(H11A,H11B), C12(H12A,H12B),
 C13(H13A,H13B), C21(H21A,H21B), C22(H22A,H22B), C23(H23A,H23B), C31(H31A,H31B),
  C32(H32A,H32B), C33(H33A,H33B)
2.b Aromatic/amide H refined with riding coordinates:
 C5(H5), C6(H6), C8(H8), C9(H9), C15(H15), C16(H16), C18(H18), C19(H19),
 C25(H25), C26(H26), C28(H28), C29(H29), C35(H35), C36(H36), C38(H38), C39(H39)
2.c Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C), C20(H20A,H20B,H20C), C30(H30A,H30B,H30C), C40(H40A,H40B,
 H40C)
;
_olex2_submission_special_instructions 'No special instructions were received'