Discovery of Four Modified Classes of Triterpenoids Delineated a Metabolic Cascade: Compound Characterization and Biomimetic Synthesis
Zhou, Bin; Gao, Xinhua; Zhang, Minmin; Zheng, Chengyu; Liu, Hongchun; Yue, Jian-Min; Chemical Science  (2021) –; doi:10.1039/D1SC02710G

data_1563591
_publ_section_title
;
 Discovery of Four Modified Classes of Triterpenoids Delineated a
 Metabolic Cascade: Compound Characterization and Biomimetic Synthesis
;
_journal_name_full               'Chemical Science'
_journal_paper_doi               10.1039/D1SC02710G
_journal_year                    2021
_chemical_absolute_configuration rmad
_chemical_formula_moiety         'C38 H48 O5'
_chemical_formula_sum            'C38 H48 O5'
_chemical_formula_weight         584.76
_space_group_crystal_system      monoclinic
_space_group_IT_number           5
_space_group_name_Hall           'C 2y'
_space_group_name_H-M_alt        'C 1 2 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2019-12-20
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2020-06-19 deposited with the CCDC.	2021-06-18 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 96.1270(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   46.6254(9)
_cell_length_b                   6.72390(10)
_cell_length_c                   10.3609(2)
_cell_measurement_reflns_used    9890
_cell_measurement_temperature    170(2)
_cell_measurement_theta_max      54.910
_cell_measurement_theta_min      3.318
_cell_volume                     3229.63(10)
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_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      169.98
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           GaK\a
_diffrn_radiation_wavelength     1.34139
_diffrn_reflns_av_R_equivalents  0.0467
_diffrn_reflns_av_unetI/netI     0.0396
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       56
_diffrn_reflns_limit_h_min       -56
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            21379
_diffrn_reflns_point_group_measured_fraction_full 0.983
_diffrn_reflns_point_group_measured_fraction_max 0.979
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         54.885
_diffrn_reflns_theta_min         3.318
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.396
_exptl_absorpt_correction_T_max  0.7508
_exptl_absorpt_correction_T_min  0.5801
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1377 before and 0.0771 after correction. The Ratio of minimum to maximum transmission is 0.7726. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.203
_exptl_crystal_description       block
_exptl_crystal_F_000             1264
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.319
_refine_diff_density_min         -0.353
_refine_diff_density_rms         0.041
_refine_ls_abs_structure_details
;
 Flack x determined using 1976 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.04(13)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     395
_refine_ls_number_reflns         6014
_refine_ls_number_restraints     19
_refine_ls_restrained_S_all      1.092
_refine_ls_R_factor_all          0.0647
_refine_ls_R_factor_gt           0.0554
_refine_ls_shift/su_max          0.005
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0830P)^2^+1.3430P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1416
_refine_ls_wR_factor_ref         0.1514
_reflns_Friedel_coverage         0.811
_reflns_Friedel_fraction_full    0.974
_reflns_Friedel_fraction_max     0.965
_reflns_number_gt                5208
_reflns_number_total             6014
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1sc02710g2.cif
_cod_data_source_block           mj19799_0m
_cod_database_code               1563591
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_max   0.969
_shelx_estimated_absorpt_t_min   0.954
_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
2. Uiso/Uaniso restraints and constraints
C25 \\sim C27 \\sim C26 \\sim O5: within 2A with sigma of 0.005 and sigma for
terminal atoms of 0.01
3.a Ternary CH refined with riding coordinates:
 C5(H5A), C7(H7), C9(H9), C17(H17), C20(H20), C22(H22), C23(H23)
3.b Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C6(H6A,H6B), C15(H15A,H15B), C16(H16A,H16B), C26(H26A,H26B),
 C30(H30A,H30B)
3.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C11(H11), C12(H12), C24(H24), C1'(H1'), C2'(H2'), C4'(H4'), C5'(H5'),
 C6'(H6'), C7'(H7'), C8'(H8')
3.d Tetrahedral OH refined with riding coordinates:
 O5(H5)
3.e Idealised Me refined as rotating group:
 C18(H18A,H18B,H18C), C19(H19A,H19B,H19C), C27(H27A,H27B,H27C), C28(H28A,H28B,
 H28C), C29(H29A,H29B,H29C)
3.f Idealised tetrahedral OH refined as rotating group:
 O1(H1), O4(H4)
;
_shelx_res_checksum              61175
_shelx_hkl_checksum              62166
_olex2_submission_special_instructions 'No special instructions were received'