Phylogeny-directed discovery and mutagenesis of a tricyclic gersemiane synthase.
Chen, Xiaochen; Chen, Bao; Xu, Baofu; Organic & biomolecular chemistry 23 (2025) 9635–9643; doi:10.1039/d5ob01208b

data_7160770
_publ_section_title
;
 Phylogeny-directed discovery and mutagenesis of a tricyclic gersemiane
 synthase.
;
_journal_issue                   42
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              9635
_journal_page_last               9643
_journal_paper_doi               10.1039/d5ob01208b
_journal_volume                  23
_journal_year                    2025
_chemical_absolute_configuration rmad
_chemical_formula_moiety         'C15 H3 Ag3 F18 N6, 2(C20 H32 O)'
_chemical_formula_sum            'C55 H67 Ag3 F18 N6 O2'
_chemical_formula_weight         1509.75
_space_group_crystal_system      triclinic
_space_group_IT_number           1
_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_creation_date             2025-07-22
_audit_creation_method
;
Olex2 1.5
(compiled 2025.07.13 svn.rb7424aed for OlexSys, GUI svn.r7308)
;
_audit_update_record
;
2025-07-22 deposited with the CCDC.	2025-10-02 downloaded from the CCDC.
;
_cell_angle_alpha                84.639(2)
_cell_angle_beta                 71.705(2)
_cell_angle_gamma                85.554(2)
_cell_formula_units_Z            2
_cell_length_a                   12.0210(5)
_cell_length_b                   15.3300(6)
_cell_length_c                   17.4835(7)
_cell_measurement_reflns_used    9471
_cell_measurement_temperature    170(2)
_cell_measurement_theta_max      63.75
_cell_measurement_theta_min      2.67
_cell_volume                     3041.7(2)
_computing_cell_refinement       'SAINT V8.40A (Bruker, 2019)'
_computing_data_reduction        'SAINT V8.40A (Bruker, 2019)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_diffrn_ambient_temperature      170(2)
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0703
_diffrn_reflns_av_unetI/netI     0.1006
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            30119
_diffrn_reflns_point_group_measured_fraction_full 0.836
_diffrn_reflns_point_group_measured_fraction_max 0.836
_diffrn_reflns_theta_full        63.806
_diffrn_reflns_theta_max         63.806
_diffrn_reflns_theta_min         2.669
_diffrn_source_current           1.2
_diffrn_source_power             0.06
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    8.561
_exptl_absorpt_correction_T_max  0.7524
_exptl_absorpt_correction_T_min  0.3144
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1602 before and 0.1063 after correction.
The Ratio of minimum to maximum transmission is 0.4179.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.648
_exptl_crystal_description       block
_exptl_crystal_F_000             1516
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.05
_refine_diff_density_max         2.007
_refine_diff_density_min         -0.542
_refine_diff_density_rms         0.207
_refine_ls_abs_structure_details
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.052(9)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.084
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1530
_refine_ls_number_reflns         16776
_refine_ls_number_restraints     5
_refine_ls_restrained_S_all      1.084
_refine_ls_R_factor_all          0.0932
_refine_ls_R_factor_gt           0.0857
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1414P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2115
_refine_ls_wR_factor_ref         0.2266
_reflns_Friedel_coverage         0.684
_reflns_Friedel_fraction_full    0.679
_reflns_Friedel_fraction_max     0.679
_reflns_number_gt                14372
_reflns_number_total             16776
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5ob01208b2.cif
_cod_data_source_block           cu_20240489_0m
_cod_depositor_comments          'Adding full bibliography for 7160770.cif.'
_cod_original_sg_symbol_H-M      P1
_cod_database_code               7160770
_shelx_shelxl_version_number     2019/3
_shelx_estimated_absorpt_t_max   0.674
_shelx_estimated_absorpt_t_min   0.380
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.948(9)
 0.052(9)
2. 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
3. Rigid bond restraints
 C95, C101
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.02
 N5, N9
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.02
4.a Ternary CH refined with riding coordinates:
 C31(H31), C32(H32), C62(H62), C83(H83), C56(H56), C65(H65), C72(H72),
 C78(H78), C16(H16), C20(H20), C60(H60), C71(H71), C1(H1), C8(H8), C29(H29),
 C48(H48)
4.b Secondary CH2 refined with riding coordinates:
 C74(H74A,H74B), C80(H80A,H80B), C90(H90A,H90B), C91(H91A,H91B), C94(H94A,
 H94B), C95(H95A,H95B), C101(H10A,H10B), C2(H2A,H2B), C23(H23A,H23B), C64(H64A,
 H64B), C96(H96A,H96B), C99(H99A,H99B), C104(H10H,H10I), C105(H10J,H10K),
 C33(H33B,H33A), C43(H43A,H43B), C45(H45A,H45B), C67(H67A,H67B), C88(H88A,H88B),
  C107(H10L,H10M), C108(H10N,H10O), C27(H27A,H27B), C35(H35A,H35B), C49(H49A,
 H49B), C50(H50A,H50B), C52(H52A,H52B), C54(H54A,H54B), C89(H89A,H89B)
4.c Aromatic/amide H refined with riding coordinates:
 C55(H55), C59(H59), C87(H87), C5(H5), C12(H12), C81(H81)
4.d X=CH2 refined with riding coordinates:
 C106(H10F,H10G), C63(H63A,H63B), C44(H44A,H44B), C4(H4A,H4B)
4.e Idealised Me refined as rotating group:
 C24(H24A,H24B,H24C), C58(H58A,H58B,H58C), C76(H76A,H76B,H76C), C103(H10C,H10D,
 H10E), C40(H40A,H40B,H40C), C53(H53A,H53B,H53C), C69(H69A,H69B,H69C), C92(H92A,
 H92B,H92C), C7(H7A,H7B,H7C), C41(H41A,H41B,H41C), C61(H61A,H61B,H61C),
 C98(H98A,H98B,H98C), C14(H14A,H14B,H14C), C28(H28A,H28B,H28C), C47(H47A,H47B,
 H47C), C77(H77A,H77B,H77C)
;
_shelx_res_checksum              50174
_olex2_submission_special_instructions 'No special instructions were received'