Characterisation of the biosynthetic pathway to agnestins A and B reveals the reductive route to chrysophanol in fungi.
Szwalbe, Agnieszka J.; Williams, Katherine; Song, Zhongshu; de Mattos-Shipley, Kate; Vincent, Jason L.; Bailey, Andrew M.; Willis, Christine L.; Cox, Russell J.; Simpson, Thomas J.; Chemical science 10 (2019) 233–238; doi:10.1039/c8sc03778g

data_1554593
_publ_section_title
;
 Characterisation of the biosynthetic pathway to agnestins A and B reveals
 the reductive route to chrysophanol in fungi.
;
_journal_issue                   1
_journal_name_full               'Chemical science'
_journal_page_first              233
_journal_page_last               238
_journal_paper_doi               10.1039/c8sc03778g
_journal_volume                  10
_journal_year                    2019
_chemical_absolute_configuration abs
_chemical_formula_moiety         'C15 H12 O6, 0.5(H2 O)'
_chemical_formula_sum            'C15 H13 O6.5'
_chemical_formula_weight         297.25
_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   mixed
_atom_sites_solution_primary     direct
_audit_creation_date             2013-09-11
_audit_creation_method
;
  Olex2 1.2
  (compiled Apr 23 2013 17:59:47, GUI svn.r4466)
;
_audit_update_record
;
2018-04-23 deposited with the CCDC.
2018-11-23 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   7.4082(14)
_cell_length_b                   7.9771(15)
_cell_length_c                   43.956(8)
_cell_measurement_reflns_used    9890
_cell_measurement_temperature    173.15
_cell_measurement_theta_max      65.91
_cell_measurement_theta_min      5.63
_cell_volume                     2597.6(8)
_computing_data_reduction        'SAINT v7.68A (Bruker, 2009)'
_computing_molecular_graphics
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement
;
XL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution
;
XS, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_diffrn_ambient_temperature      173.15
_diffrn_detector                 'Bruker Proteum CCD'
_diffrn_detector_type            'Bruker Proteum CCD'
_diffrn_measured_fraction_theta_full 0.947
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device       'Bruker Mircostar Rotating anode'
_diffrn_measurement_device_type  'Rotating anode'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0648
_diffrn_reflns_av_unetI/netI     0.0331
_diffrn_reflns_Laue_measured_fraction_full 0.947
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       51
_diffrn_reflns_limit_l_min       -50
_diffrn_reflns_number            32711
_diffrn_reflns_point_group_measured_fraction_full 0.934
_diffrn_reflns_point_group_measured_fraction_max 0.977
_diffrn_reflns_theta_full        68.500
_diffrn_reflns_theta_max         66.403
_diffrn_reflns_theta_min         4.023
_diffrn_source                   'micro-focus rotating anode'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.026
_exptl_absorpt_correction_T_max  0.7528
_exptl_absorpt_correction_T_min  0.4421
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
wR2(int) was 0.1332 before and 0.0681 after correction.
The Ratio of minimum to maximum transmission is 0.5873.
The \l/2 correction factor is 0.0015.
;
_exptl_crystal_colour            'clear whitish colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   whitish
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.520
_exptl_crystal_description       plate
_exptl_crystal_F_000             1240
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.204
_refine_diff_density_min         -0.198
_refine_diff_density_rms         0.040
_refine_ls_abs_structure_details
;
 Flack x determined using 1808 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   -0.01(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     399
_refine_ls_number_reflns         4450
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.069
_refine_ls_R_factor_all          0.0288
_refine_ls_R_factor_gt           0.0287
_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^)+(0.0449P)^2^+0.6535P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0773
_refine_ls_wR_factor_ref         0.0775
_reflns_Friedel_coverage         0.689
_reflns_Friedel_fraction_full    0.915
_reflns_Friedel_fraction_max     0.961
_reflns_number_gt                4432
_reflns_number_total             4450
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8sc03778g2.cif
_cod_data_source_block           Agnestin_A
_cod_depositor_comments
;

2022-05-28
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_sg_symbol_Hall     P
_cod_original_sg_symbol_H-M      P
_cod_original_formula_moiety     '2(C15 H12 O6), H2 O'
_cod_original_formula_sum        'C30 H26 O13'
_cod_original_formula_units_Z    4
_cod_original_formula_weight     594.51
_cod_database_code               1554593
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All O(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H,H) groups
2.a Free rotating group:
 O13(H13A,H13B)
2.b Ternary CH refined with riding coordinates:
 C9(H9), C10(H10), C24(H24), C25(H25)
2.c Aromatic/amide H refined with riding coordinates:
 C12(H12), C4(H4), C2(H2A), C3(H3), C27(H27), C18(H18), C19(H19), C17(H17)
2.d Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C), C30(H30A,H30B,H30C)
2.e Idealised tetrahedral OH refined as rotating group:
 O2(H2), O6(H6), O5(H5), O11(H11), O8(H8), O12O(H12O)
;
_shelx_res_checksum              66728
_shelxl_version_number           2013-3