Generation of two novel furanosteroids <i>via</i> heterologous expression of demethoxyviridin biosynthetic genes in a wortmannin-producing strain.
Jiang, Wei; Li, Lin-Huan; Zhang, Lin-Min; Zhao, Huan; Li, Shao-Yang; Wang, Gao-Qian; Chen, Guo-Dong; Lv, Jian-Ming; Hu, Dan; Gao, Hao; Organic & biomolecular chemistry 23 (2025) 6683–6686; doi:10.1039/d5ob00856e

data_7160591
_publ_section_title
;
 Generation of two novel furanosteroids <i>via</i> heterologous expression
 of demethoxyviridin biosynthetic genes in a wortmannin-producing strain.
;
_journal_issue                   28
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              6683
_journal_page_last               6686
_journal_paper_doi               10.1039/d5ob00856e
_journal_volume                  23
_journal_year                    2025
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C21 H20 O6, H2 O'
_chemical_formula_sum            'C21 H22 O7'
_chemical_formula_weight         386.38
_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     direct
_audit_creation_date             2025-06-04
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2025-06-04 deposited with the CCDC.	2025-06-12 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 91.6252(9)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   9.6221(2)
_cell_length_b                   8.1595(2)
_cell_length_c                   11.5469(3)
_cell_measurement_reflns_used    9973
_cell_measurement_temperature    153(2)
_cell_measurement_theta_max      68.222
_cell_measurement_theta_min      5.904
_cell_volume                     906.20(4)
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_reduction        'SAINT V8.40B (?, 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    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      153.15
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'B ruler D8 venture'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0471
_diffrn_reflns_av_unetI/netI     0.0224
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            34765
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         68.248
_diffrn_reflns_theta_min         3.830
_exptl_absorpt_coefficient_mu    0.889
_exptl_absorpt_correction_T_max  0.7531
_exptl_absorpt_correction_T_min  0.6474
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1023 before and 0.0622 after correction. The Ratio of minimum to maximum transmission is 0.8596. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.416
_exptl_crystal_description       needle
_exptl_crystal_F_000             408
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.238
_refine_diff_density_min         -0.408
_refine_diff_density_rms         0.058
_refine_ls_abs_structure_details
;
 Flack x determined using 1486 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.08(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.102
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     259
_refine_ls_number_reflns         3292
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.102
_refine_ls_R_factor_all          0.0359
_refine_ls_R_factor_gt           0.0355
_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^)+(0.0581P)^2^+0.2832P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0940
_refine_ls_wR_factor_ref         0.0944
_reflns_Friedel_coverage         0.850
_reflns_Friedel_fraction_full    0.991
_reflns_Friedel_fraction_max     0.990
_reflns_number_gt                3252
_reflns_number_total             3292
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5ob00856e2.cif
_cod_data_source_block           26942_d_0m
_cod_depositor_comments          'Adding full bibliography for 7160591.cif.'
_cod_database_code               7160591
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_max   0.908
_shelx_estimated_absorpt_t_min   0.878
_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,H) groups
2.a Free rotating group:
 O7(H7A,H7B)
2.b Ternary CH refined with riding coordinates:
 C1(H1), C14(H14)
2.c Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C16(H16A,H16B), C15(H15A,H15B)
2.d Aromatic/amide H refined with riding coordinates:
 C20(H20), C11(H11), C12(H12)
2.e Idealised Me refined as rotating group:
 C19(H19A,H19B,H19C), C18(H18A,H18B,H18C), C21(H21A,H21B,H21C)
;
_shelx_res_checksum              41339
_olex2_submission_special_instructions 'No special instructions were received'