Cascade reaction of 2-bromo-2H-azirine-2-carboxylate with malonic esters: facile access to highly substituted pyrrolinones
Pradhan, Priyankar; Shaikh Sumaiya, A.; Jagadeesh Babu, N.; Sudhakar, Gangarajula; New Journal of Chemistry 49 (2025) 15573–15577; doi:10.1039/D5NJ02356D

data_7063971
_publ_section_title
;
 Cascade reaction of 2-bromo-2H-azirine-2-carboxylate with malonic esters:
 facile access to highly substituted pyrrolinones
;
_journal_issue                   36
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              15573
_journal_page_last               15577
_journal_paper_doi               10.1039/D5NJ02356D
_journal_volume                  49
_journal_year                    2025
_chemical_formula_moiety         'C27 H23 N O6'
_chemical_formula_sum            'C27 H23 N O6'
_chemical_formula_weight         457.46
_chemical_name_systematic
'3-benzyl 4-methyl 3-(benzyloxy)-2-oxo-5-phenyl-2,3-dihydro-1H-pyrrole-3,4-dicarboxylate'
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2019/3
_audit_update_record
;
2025-04-27 deposited with the CCDC.	2025-08-25 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 115.853(8)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   14.616(4)
_cell_length_b                   11.710(3)
_cell_length_c                   15.622(4)
_cell_measurement_reflns_used    7295
_cell_measurement_temperature    294(2)
_cell_measurement_theta_max      25.839
_cell_measurement_theta_min      2.263
_cell_volume                     2406.2(11)
_computing_cell_refinement       'SAINT V8.41 (Bruker AXS LLC, 2019)'
_computing_data_collection       'Bruker APEX5 v2023.9-0'
_computing_data_reduction        'SAINT V8.41 (Bruker AXS LLC, 2019)'
_computing_structure_refinement  'SHELXL-2019/2 (Sheldrick, 2019)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      294(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker D8 VENTURE PHOTON C14 HPAD'
_diffrn_measurement_method       '\w and \f'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0434
_diffrn_reflns_av_unetI/netI     0.0286
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            34120
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.429
_diffrn_reflns_theta_min         2.263
_diffrn_source                   microfocus
_exptl_absorpt_coefficient_mu    0.090
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.6813
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;
_exptl_crystal_density_diffrn    1.263
_exptl_crystal_description       BLOCK
_exptl_crystal_F_000             960
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: Dichloroform and Pentane'
_exptl_crystal_size_max          0.240
_exptl_crystal_size_mid          0.162
_exptl_crystal_size_min          0.124
_refine_diff_density_max         0.299
_refine_diff_density_min         -0.339
_refine_diff_density_rms         0.036
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     331
_refine_ls_number_reflns         4936
_refine_ls_number_restraints     252
_refine_ls_restrained_S_all      1.070
_refine_ls_R_factor_all          0.0749
_refine_ls_R_factor_gt           0.0502
_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^)+(0.0781P)^2^+0.6191P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1375
_refine_ls_wR_factor_ref         0.1600
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3379
_reflns_number_total             4936
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5nj02356d2.cif
_cod_data_source_block           mo_VA146_0m
_cod_depositor_comments
'Adding full bibliography for 7063970--7063971.cif.'
_cod_original_cell_volume        2406.3(10)
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               7063971
_shelx_shelxl_version_number     2019/3
_shelx_estimated_absorpt_t_min   0.979
_shelx_estimated_absorpt_t_max   0.989
_shelx_res_checksum              59144