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_7132207
_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_formula_sum            'C19 H27 N O4'
_chemical_formula_weight         333.41
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2023-02-28 deposited with the CCDC.	2023-10-11 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 112.952(8)
_cell_angle_gamma                90
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_cell_length_b                   14.599(3)
_cell_length_c                   10.4681(18)
_cell_measurement_reflns_used    9696
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      67.93
_cell_measurement_theta_min      3.54
_cell_volume                     3692.5(12)
_computing_cell_refinement       'APEX3/SAINT (Bruker, 2016)'
_computing_data_collection       'APEX3(Bruker, 2016)'
_computing_data_reduction        'SAINT/XPREP (Bruker, 2016)'
_computing_molecular_graphics    'ORTEP3 (Farrugia, 2012)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker D8 Venture Diffractometer'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0495
_diffrn_reflns_av_unetI/netI     0.0201
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       31
_diffrn_reflns_limit_h_min       -31
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            50618
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.245
_diffrn_reflns_theta_min         3.537
_diffrn_source                   'micro focus sealed tube'
_exptl_absorpt_coefficient_mu    0.675
_exptl_absorpt_correction_T_max  0.7531
_exptl_absorpt_correction_T_min  0.6279
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS-2016/2 - Bruker AXS'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.200
_exptl_crystal_description       block
_exptl_crystal_F_000             1440
_exptl_crystal_size_max          0.206
_exptl_crystal_size_mid          0.198
_exptl_crystal_size_min          0.112
_refine_diff_density_max         0.243
_refine_diff_density_min         -0.241
_refine_diff_density_rms         0.032
_refine_ls_extinction_coef       0.00084(12)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.078
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     235
_refine_ls_number_reflns         3387
_refine_ls_number_restraints     52
_refine_ls_restrained_S_all      1.091
_refine_ls_R_factor_all          0.0557
_refine_ls_R_factor_gt           0.0453
_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^)+(0.0706P)^2^+1.3513P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1286
_refine_ls_wR_factor_ref         0.1419
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2724
_reflns_number_total             3387
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3cc03810f2.cif
_cod_data_source_block           shelx
_cod_original_cell_volume        3692.3(11)
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               7132207
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_min   0.873
_shelx_estimated_absorpt_t_max   0.928
_shelx_res_checksum              89599
_shelx_hkl_checksum              16337