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_1554592
_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 unk
_chemical_formula_moiety         'C15 H12 O6, H2 O'
_chemical_formula_sum            'C15 H14 O7'
_chemical_formula_weight         306.26
_chemical_name_common            'Agnestin B'
_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   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2018-04-20
_audit_creation_method
;
Olex2 1.2
(compiled 2018.04.18 svn.r3501 for OlexSys, GUI svn.r5488)
;
_audit_update_record
;
2018-04-23 deposited with the CCDC.
2018-11-23 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 102.455(4)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   7.1336(12)
_cell_length_b                   7.3556(13)
_cell_length_c                   13.246(2)
_cell_measurement_reflns_used    9948
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      65.91
_cell_measurement_theta_min      6.35
_cell_volume                     678.7(2)
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_collection       'Bruker Apex suite'
_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    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'Bruker Pt135 CCD area detector'
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 0.980
_diffrn_measured_fraction_theta_max 0.979
_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  0.0409
_diffrn_reflns_av_unetI/netI     0.0297
_diffrn_reflns_Laue_measured_fraction_full 0.980
_diffrn_reflns_Laue_measured_fraction_max 0.979
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            11998
_diffrn_reflns_point_group_measured_fraction_full 0.893
_diffrn_reflns_point_group_measured_fraction_max 0.893
_diffrn_reflns_theta_full        66.072
_diffrn_reflns_theta_max         66.072
_diffrn_reflns_theta_min         6.354
_diffrn_source                   'micro-focus rotating anode'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.027
_exptl_absorpt_correction_T_max  0.7527
_exptl_absorpt_correction_T_min  0.6306
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.499
_exptl_crystal_description       block
_exptl_crystal_F_000             320
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.470
_refine_diff_density_min         -0.289
_refine_diff_density_rms         0.076
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.094
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     205
_refine_ls_number_reflns         2118
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.094
_refine_ls_R_factor_all          0.0493
_refine_ls_R_factor_gt           0.0491
_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^)+(0.0926P)^2^+0.4044P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1336
_refine_ls_wR_factor_ref         0.1338
_reflns_Friedel_coverage         0.678
_reflns_Friedel_fraction_full    0.790
_reflns_Friedel_fraction_max     0.790
_reflns_number_gt                2099
_reflns_number_total             2118
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8sc03778g2.cif
_cod_data_source_block           testm1
_cod_database_code               1554592
_shelx_shelxl_version_number     2017/1
_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, All O(H,H) groups
2.a Free rotating group:
 O7(H7A,H7B)
2.b Ternary CH refined with riding coordinates:
 C13(H13), C14(H14)
2.c Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B)
2.d Aromatic/amide H refined with riding coordinates:
 C4(H4A), C3(H3), C2(H2)
2.e Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C)
2.f Idealised tetrahedral OH refined as rotating group:
 O1(H1), O4(H4)
;
_shelx_res_checksum              97364
_olex2_submission_special_instructions 'No special instructions were received'