Tandem intramolecular cyclisation/1,3-aryl shift in N-(4,4-diethoxybutyl)-1-arylmethanimines (Kazan reaction): synthesis of 3-benzylidene-1-pyrrolines
Smolobochkin, A. V.; Gazizov, A. S.; Melyashova, A. S.; Voronina, J. K.; Strelnik, A. G.; Vatsadze, S. Z.; Burilov, A. R.; Pudovik, M. A.; Fedorova, O. A.; Sinyashin, O. G.; RSC Advances 7 (2017) 50955–; doi:10.1039/C7RA11216E

data_7229465
_publ_section_title
;
 Tandem intramolecular cyclisation/1,3-aryl shift in
 N-(4,4-diethoxybutyl)-1-arylmethanimines (Kazan reaction): synthesis of
 3-benzylidene-1-pyrrolines
;
_journal_issue                   80
_journal_name_full               'RSC Advances'
_journal_page_first              50955
_journal_paper_doi               10.1039/C7RA11216E
_journal_volume                  7
_journal_year                    2017
_chemical_formula_moiety         'C14 H17 Br Cl N O'
_chemical_formula_sum            'C14 H17 Br Cl N O'
_chemical_formula_weight         330.65
_chemical_name_common
'(E)-3-benzylidene-2-(2-oxopropyl)pyrrolidin-1-ium chloride'
_chemical_name_systematic
'(E)-3-benzylidene-2-(2-oxopropyl)pyrrolidin-1-ium chloride'
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      14
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_audit_update_record
;
2017-04-14 deposited with the CCDC.
2017-10-27 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 99.804(6)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   5.038(2)
_cell_length_b                   24.005(11)
_cell_length_c                   12.287(6)
_cell_measurement_reflns_used    4187
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      22.71
_cell_measurement_theta_min      2.39
_cell_volume                     1464.3(11)
_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-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0394
_diffrn_reflns_av_sigmaI/netI    0.0303
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       29
_diffrn_reflns_limit_k_min       -29
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            15113
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         1.70
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    2.978
_exptl_absorpt_correction_T_max  0.7550
_exptl_absorpt_correction_T_min  0.5873
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.500
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prizm
_exptl_crystal_F_000             672
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.519
_refine_diff_density_min         -0.387
_refine_diff_density_rms         0.053
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.893
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     172
_refine_ls_number_reflns         2879
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.893
_refine_ls_R_factor_all          0.0578
_refine_ls_R_factor_gt           0.0381
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0628
_refine_ls_wR_factor_ref         0.0647
_reflns_number_gt                2206
_reflns_number_total             2879
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c7ra11216e2.cif
_cod_data_source_block           s5_fin
_cod_original_cell_volume        1464.2(11)
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               7229465