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_1563593
_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 H46 O5'
_chemical_formula_sum            'C38 H46 O5'
_chemical_formula_weight         582.75
_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   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2021-05-10
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2021-05-10 deposited with the CCDC.	2021-06-18 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 92.505(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   18.0938(10)
_cell_length_b                   7.0743(4)
_cell_length_c                   24.2239(14)
_cell_measurement_reflns_used    9934
_cell_measurement_temperature    170
_cell_measurement_theta_max      74.653
_cell_measurement_theta_min      3.653
_cell_volume                     3097.7(3)
_computing_cell_refinement       'SAINT V8.40A (?, 2016)'
_computing_data_reduction        'SAINT V8.40A (?, 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    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      170.0
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'Bruker D8 VENTURE'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0567
_diffrn_reflns_av_unetI/netI     0.0550
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            19994
_diffrn_reflns_point_group_measured_fraction_full 0.956
_diffrn_reflns_point_group_measured_fraction_max 0.947
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         72.103
_diffrn_reflns_theta_min         1.825
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.641
_exptl_absorpt_correction_T_max  0.7538
_exptl_absorpt_correction_T_min  0.5890
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1475 before and 0.0761 after correction. The Ratio of minimum to maximum transmission is 0.7814. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.250
_exptl_crystal_description       block
_exptl_crystal_F_000             1256
_exptl_crystal_size_max          0.09
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.351
_refine_diff_density_min         -0.228
_refine_diff_density_rms         0.069
_refine_ls_abs_structure_details
;
 Flack x determined using 2073 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.13(12)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.087
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     417
_refine_ls_number_reflns         5765
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.087
_refine_ls_R_factor_all          0.0563
_refine_ls_R_factor_gt           0.0516
_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^)+(0.0849P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1218
_refine_ls_wR_factor_ref         0.1279
_reflns_Friedel_coverage         0.759
_reflns_Friedel_fraction_full    0.912
_reflns_Friedel_fraction_max     0.895
_reflns_number_gt                5256
_reflns_number_total             5765
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1sc02710g3.cif
_cod_data_source_block           cu_2021574_0m
_cod_database_code               1563593
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.975
_shelx_estimated_absorpt_t_min   0.945
_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. Others
 Fixed Sof: C26(0.5) H26A(0.5) H26B(0.5) O017(0.5) H017(0.5) O5(0.5) H5A(0.5)
 C26A(0.5) H26C(0.5) H26D(0.5)
3.a Ternary CH refined with riding coordinates:
 C5(H5), C22(H22), C9(H9), C20(H20), C17(H17), C23(H23)
3.b Secondary CH2 refined with riding coordinates:
 C15(H15A,H15B), C6(H6A,H6B), C16(H16A,H16B), C1(H1A,H1B), C30(H30A,H30B),
 C26(H26A,H26B), C26A(H26C,H26D)
3.c Aromatic/amide H refined with riding coordinates:
 C11(H11), C2(H2), C12(H12), C1'(H1'), C2'(H2'), C4'(H4'), C24(H24), C8'(H8'),
 C6'(H6'), C5'(H5'), C7'(H7')
3.d Idealised Me refined as rotating group:
 C29(H29A,H29B,H29C), C28(H28A,H28B,H28C), C18(H18A,H18B,H18C), C19(H19A,H19B,
 H19C), C27(H27A,H27B,H27C)
3.e Idealised tetrahedral OH refined as rotating group:
 O017(H017), O5(H5A)
;
_olex2_submission_special_instructions 'No special instructions were received'