Stereoselective synthesis of functionalized perhydropyrrolo[1,2-b]isoxazoles based on (3+2)-annulation of donor-acceptor cyclopropanes and isoxazolines
Potapov, Konstantin V.; Novikov, Maxim A.; Kozmenko, Yaroslav V.; Solyev, Pavel N.; Volodin, Alexander D.; Korlyukov, Alexander; Novikov, Roman A.; Tomilov, Yury; Organic & Biomolecular Chemistry  (2025) –; doi:10.1039/D5OB01604E

data_7160880
_publ_section_title
;
 Stereoselective synthesis of functionalized
 perhydropyrrolo[1,2-b]isoxazoles based on (3+2)-annulation of
 donor-acceptor cyclopropanes and isoxazolines
;
_journal_name_full               'Organic &amp; Biomolecular Chemistry'
_journal_paper_doi               10.1039/D5OB01604E
_journal_year                    2025
_chemical_formula_moiety         'C21 H22 N2 O9'
_chemical_formula_sum            'C21 H22 N2 O9'
_chemical_formula_weight         446.40
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_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_block_doi                 10.5517/ccdc.csd.cc2pmm54
_audit_creation_date             2025-09-24
_audit_creation_method
;
Olex2 1.5
(compiled 2025.07.13 svn.rb7424aed for OlexSys, GUI svn.r7314)
;
_audit_update_record
;
2025-09-25 deposited with the CCDC.	2025-11-27 downloaded from the CCDC.
;
_cell_angle_alpha                71.30(3)
_cell_angle_beta                 80.52(3)
_cell_angle_gamma                76.20(3)
_cell_formula_units_Z            2
_cell_length_a                   8.598(6)
_cell_length_b                   10.180(6)
_cell_length_c                   12.966(12)
_cell_measurement_reflns_used    64
_cell_measurement_temperature    120
_cell_measurement_theta_max      15.64
_cell_measurement_theta_min      2.45
_cell_volume                     1039.1(14)
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'XT  (Sheldrick, 2015)'
_diffrn_ambient_temperature      120
_diffrn_detector_area_resol_mean 8
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0497
_diffrn_reflns_av_unetI/netI     0.0816
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            16774
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.697
_diffrn_reflns_theta_min         1.666
_diffrn_source                   'sealed tube'
_diffrn_source_current           30.0
_diffrn_source_power             1.5
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.113
_exptl_absorpt_correction_T_max  0.7463
_exptl_absorpt_correction_T_min  0.6799
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0779 before and 0.0439 after correction.
The Ratio of minimum to maximum transmission is 0.9110.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.427
_exptl_crystal_description       block
_exptl_crystal_F_000             468
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.560
_refine_diff_density_min         -0.299
_refine_diff_density_rms         0.060
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     293
_refine_ls_number_reflns         5364
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.048
_refine_ls_R_factor_all          0.1040
_refine_ls_R_factor_gt           0.0580
_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^)+(0.0614P)^2^+0.3510P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1372
_refine_ls_wR_factor_ref         0.1544
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3358
_reflns_number_total             5364
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5ob01604e2.cif
_cod_data_source_block           kb1523102
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               7160880
_shelxl_version_number           2014/6
_shelx_estimated_absorpt_t_max   0.993
_shelx_estimated_absorpt_t_min   0.987
_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
2.a Ternary CH refined with riding coordinates:
 C3(H3), C17(H17)
2.b Secondary CH2 refined with riding coordinates:
 C15(H15A,H15B), C18(H18A,H18B)
2.c Aromatic/amide H refined with riding coordinates:
 C11(H11), C13(H13), C12(H12), C10(H10)
2.d Idealised Me refined as rotating group:
 C20(H20A,H20B,H20C), C28(H28A,H28B,H28C), C32(H32A,H32B,H32C), C24(H24A,H24B,
 H24C)
;
_shelx_res_checksum              40049
_olex2_submission_special_instructions 'No special instructions were received'