Brønsted acid-catalyzed annulation reaction of hydroxamic acids: synthesis of cyclopentane-fused isoxazolidines and their benzilic amide rearrangement
Mondal, Swati Lekha; Bhajammanavar, Vinod; Ramakrishna, Isai; Baidya, Mahiuddin; Chemical Communications  (2023) –; doi:10.1039/D3CC03810F

data_7132206
_publ_section_title
;
 Br\/onsted acid-catalyzed annulation reaction of hydroxamic acids:
 synthesis of cyclopentane-fused isoxazolidines and their benzilic amide
 rearrangement
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/D3CC03810F
_journal_year                    2023
_chemical_absolute_configuration unk
_chemical_formula_moiety         'C18 N O4'
_chemical_formula_sum            'C18 N O4'
_chemical_formula_weight         317.388
_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_Hall           'P 2c -2n'
_space_group_name_H-M_alt        'P n a 21'
_symmetry_Int_Tables_number      33
_audit_creation_date             2023-02-18
_audit_creation_method
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_audit_update_record
;
2023-02-21 deposited with the CCDC.	2023-10-11 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.2934(5)
_cell_length_b                   14.3475(5)
_cell_length_c                   9.7444(4)
_cell_measurement_reflns_used    5048
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      22.08
_cell_measurement_theta_min      2.53
_cell_volume                     1718.71(12)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine 1.5 (Bourhis et al., 2015)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      296.15
_diffrn_measured_fraction_theta_full 1.0000
_diffrn_measured_fraction_theta_max 1.0000
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0231
_diffrn_reflns_av_unetI/netI     0.0230
_diffrn_reflns_Laue_measured_fraction_full 1.0000
_diffrn_reflns_Laue_measured_fraction_max 1.0000
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            11670
_diffrn_reflns_point_group_measured_fraction_full 0.9964
_diffrn_reflns_point_group_measured_fraction_max 0.9964
_diffrn_reflns_theta_full        24.9916
_diffrn_reflns_theta_max         24.99
_diffrn_reflns_theta_min         2.18
_exptl_absorpt_coefficient_mu    0.086
_exptl_absorpt_correction_T_max  0.991
_exptl_absorpt_correction_T_min  0.979
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2014/5(Bruker AXS.Inc)'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.227
_exptl_crystal_description       Block
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_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.4459
_refine_diff_density_min         -0.2402
_refine_diff_density_rms         0.0643
_refine_ls_abs_structure_details
'Hooft, R.W.W., Straver, L.H., Spek, A.L. (2010). J. Appl. Cryst., 43, 665-668.'
_refine_ls_abs_structure_Flack   0.2(4)
_refine_ls_d_res_high            0.8411
_refine_ls_d_res_low             9.3353
_refine_ls_extinction_coef       0.011(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_goodness_of_fit_ref   1.6691
_refine_ls_hydrogen_treatment    undef
_refine_ls_matrix_type           full
_refine_ls_number_constraints    0
_refine_ls_number_parameters     209
_refine_ls_number_reflns         3028
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.6691
_refine_ls_R_factor_all          0.0755
_refine_ls_R_factor_gt           0.0672
_refine_ls_shift/su_max          0.1093
_refine_ls_shift/su_mean         0.0175
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0609P)^2^+0.2627P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1701
_refine_ls_wR_factor_ref         0.1746
_reflns_Friedel_coverage         0.992
_reflns_limit_h_max              14
_reflns_limit_h_min              -14
_reflns_limit_k_max              17
_reflns_limit_k_min              -16
_reflns_limit_l_max              11
_reflns_limit_l_min              -11
_reflns_number_gt                2591
_reflns_number_total             3028
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            d3cc03810f2.cif
_cod_data_source_block           1442
_cod_original_sg_symbol_Hall     ' P 2c -2n'
_cod_database_code               7132206
_olex2_refinement_description
;
;
_olex2_submission_special_instructions 'No special instructions were received'