Diastereoselective Synthesis of Triterpenoid 1,2,4-Trioxolanes by Griesbaum Co-ozonolysis.
Kazakova, Oxana B.; Khusnutdinova, Elmira F.; Petrova, Anastasiya V.; Yamansarov, Emil Yu; Lobov, Alexander N.; Fedorova, Alexandra A.; Suponitsky, Kyrill Yu; Journal of natural products 82 (2019) 2550–2558; doi:10.1021/acs.jnatprod.9b00393

data_1552705
_publ_section_title
;
 Diastereoselective Synthesis of Triterpenoid 1,2,4-Trioxolanes by
 Griesbaum Co-ozonolysis.
;
_journal_issue                   9
_journal_name_full               'Journal of natural products'
_journal_page_first              2550
_journal_page_last               2558
_journal_paper_doi               10.1021/acs.jnatprod.9b00393
_journal_volume                  82
_journal_year                    2019
_chemical_absolute_configuration syn
_chemical_formula_moiety         'C31 H51 N O2'
_chemical_formula_sum            'C31 H51 N O2'
_chemical_formula_weight         469.72
_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     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2014/6
_cell_angle_alpha                76.7130(10)
_cell_angle_beta                 85.6870(10)
_cell_angle_gamma                65.1230(10)
_cell_formula_units_Z            1
_cell_length_a                   6.4002(3)
_cell_length_b                   7.3244(4)
_cell_length_c                   15.8163(9)
_cell_measurement_reflns_used    5032
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      29.62
_cell_measurement_theta_min      2.65
_cell_volume                     654.44(6)
_computing_cell_refinement       'SAINT (Bruker, 2009)'
_computing_data_collection       'APEX (Bruker, 2009)'
_computing_data_reduction        'SAINT (Bruker, 2009)'
_computing_molecular_graphics    'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_publication_material
'SHELXL-2014/6 (Sheldrick, 2014) and PLATON (Spek, 2009)'
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXL-2014/6 (Sheldrick, 2014)'
_diffrn_ambient_temperature      120(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0299
_diffrn_reflns_av_unetI/netI     0.0438
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            16795
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.867
_diffrn_reflns_theta_min         2.647
_diffrn_source                   'sealed tube'
_exptl_absorpt_coefficient_mu    0.072
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.192
_exptl_crystal_description       prizm
_exptl_crystal_F_000             260
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.322
_refine_diff_density_min         -0.193
_refine_diff_density_rms         0.045
_refine_ls_abs_structure_details
;
 Flack x determined using 2861 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.6(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     315
_refine_ls_number_reflns         7462
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.038
_refine_ls_R_factor_all          0.0513
_refine_ls_R_factor_gt           0.0429
_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^)+(0.0636P)^2^+0.0115P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1055
_refine_ls_wR_factor_ref         0.1125
_reflns_Friedel_coverage         0.985
_reflns_Friedel_fraction_full    0.989
_reflns_Friedel_fraction_max     0.981
_reflns_number_gt                6542
_reflns_number_total             7462
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            np9b00393_si_002.cif
_cod_data_source_block           3noch3
_cod_database_code               1552705
_shelxl_version_number           2014/6
_shelx_res_checksum              60735
_shelx_hkl_checksum              196