Oxidative cyclization of active methylene amides: efficient synthesis of functionalized 3-azabicyclo[<i>n</i>.1.0]alkanes.
Nemichand, ?; Waghmode, Amol G.; Awchar, Vilas M.; Baskaran, Sundarababu; Chemical communications (Cambridge, England)  (2025) –; doi:10.1039/d5cc05248c

data_7135185
_publ_section_title
;
 Oxidative cyclization of active methylene amides: efficient synthesis of
 functionalized 3-azabicyclo[<i>n</i>.1.0]alkanes.
;
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_paper_doi               10.1039/d5cc05248c
_journal_year                    2025
_chemical_formula_sum            'C22 H21 Cl2 N O3'
_chemical_formula_weight         418.30
_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   geom
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2025-07-25 deposited with the CCDC.	2025-11-17 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 97.157(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   5.9876(4)
_cell_length_b                   29.771(2)
_cell_length_c                   11.4497(7)
_cell_measurement_reflns_used    2855
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      21.74
_cell_measurement_theta_min      2.73
_cell_volume                     2025.1(2)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0371
_diffrn_reflns_av_unetI/netI     0.0398
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       34
_diffrn_reflns_limit_k_min       -35
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            14097
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        24.991
_diffrn_reflns_theta_max         24.991
_diffrn_reflns_theta_min         1.919
_exptl_absorpt_coefficient_mu    0.344
_exptl_absorpt_correction_T_max  0.966
_exptl_absorpt_correction_T_min  0.941
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2014/5(Bruker AXS.Inc)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.372
_exptl_crystal_description       Block
_exptl_crystal_F_000             872
_exptl_crystal_size_max          0.180
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.100
_refine_diff_density_max         0.225
_refine_diff_density_min         -0.335
_refine_diff_density_rms         0.044
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     254
_refine_ls_number_reflns         3532
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.022
_refine_ls_R_factor_all          0.0766
_refine_ls_R_factor_gt           0.0436
_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^)+(0.0378P)^2^+1.0757P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0919
_refine_ls_wR_factor_ref         0.1088
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2379
_reflns_number_total             3532
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5cc05248c2.cif
_cod_data_source_block           502
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               7135185
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.941
_shelx_estimated_absorpt_t_max   0.966
_shelx_res_checksum              72421
_shelx_hkl_checksum              55268