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_7063970
_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         'C19 H19 N O9'
_chemical_formula_sum            'C19 H19 N O9'
_chemical_formula_weight         405.35
_chemical_name_systematic
'dimethyl 2-(1,3-dimethoxy-1,3-dioxopropan-2-yl)-5-oxo-3-phenyl-2,5-dihydro-1H-pyrrole-2,4-dicarboxylate'
_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
_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                69.679(3)
_cell_angle_beta                 88.609(3)
_cell_angle_gamma                85.821(3)
_cell_formula_units_Z            2
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_cell_length_b                   9.3887(8)
_cell_length_c                   12.4254(11)
_cell_measurement_reflns_used    5489
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      26.604
_cell_measurement_theta_min      2.313
_cell_volume                     963.36(14)
_computing_cell_refinement       '<i>SAINT</i> (Bruker, 2016)'
_computing_data_collection       '<i>APEX3</i> (Bruker, 2016)'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_refinement  'SHELXL-2019/2 (Sheldrick, 2019)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker D8 QUEST PHOTON III C7 HPAD'
_diffrn_measurement_method       '\w and \f'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0437
_diffrn_reflns_av_unetI/netI     0.0534
_diffrn_reflns_Laue_measured_fraction_full 0.997
_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       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            17815
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.500
_diffrn_reflns_theta_min         2.313
_diffrn_source                   microfocus
_exptl_absorpt_coefficient_mu    0.113
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.6427
_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    1.397
_exptl_crystal_description       NEEDLE
_exptl_crystal_F_000             424
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: Chloroform and hexane'
_exptl_crystal_size_max          0.220
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.160
_refine_diff_density_max         0.722
_refine_diff_density_min         -0.443
_refine_diff_density_rms         0.071
_refine_ls_extinction_method     none
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_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     414
_refine_ls_number_reflns         4422
_refine_ls_number_restraints     527
_refine_ls_restrained_S_all      1.035
_refine_ls_R_factor_all          0.1082
_refine_ls_R_factor_gt           0.0730
_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^)+(0.1342P)^2^+0.4136P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2087
_refine_ls_wR_factor_ref         0.2366
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2884
_reflns_number_total             4422
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5nj02356d2.cif
_cod_data_source_block           KB1617_0m
_cod_depositor_comments
'Adding full bibliography for 7063970--7063971.cif.'
_cod_database_code               7063970
_shelx_shelxl_version_number     2019/3
_shelx_estimated_absorpt_t_min   0.976
_shelx_estimated_absorpt_t_max   0.982
_shelx_res_checksum              10646