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_7229466
_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         'C13 H11 F4 N O2'
_chemical_formula_sum            'C13 H11 F4 N O2'
_chemical_formula_weight         289.23
_chemical_name_common
'(E)-4-(3-fluorobenzylidene)-3,4-dihydro-2H-pyrrol-1-ium 2,2,2-trifluoroacetate'
_chemical_name_systematic
'(E)-4-(3-fluorobenzylidene)-3,4-dihydro-2H-pyrrol-1-ium 2,2,2-trifluoroacetate'
_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_Hall           'P 2c -2n'
_space_group_name_H-M_alt        'P n a 21'
_symmetry_space_group_name_Hall  'P 2c -2n'
_symmetry_space_group_name_H-M   'P n a 21'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2017-04-14 deposited with the CCDC.
2017-10-27 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   23.90(4)
_cell_length_b                   5.288(9)
_cell_length_c                   10.524(19)
_cell_measurement_reflns_used    1243
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      19.77
_cell_measurement_theta_min      3.41
_cell_volume                     1330(4)
_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 0.998
_diffrn_measured_fraction_theta_max 0.999
_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  0.0544
_diffrn_reflns_av_unetI/netI     0.0568
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       29
_diffrn_reflns_limit_h_min       -29
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            9514
_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         25.989
_diffrn_reflns_theta_min         1.704
_diffrn_source                   'sealed tube'
_exptl_absorpt_coefficient_mu    0.134
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.444
_exptl_crystal_description       prism
_exptl_crystal_F_000             592
_exptl_crystal_size_max          0.130
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.100
_refine_diff_density_max         0.360
_refine_diff_density_min         -0.246
_refine_diff_density_rms         0.047
_refine_ls_abs_structure_details
;
 Flack x determined using 550 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.4(9)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.967
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     181
_refine_ls_number_reflns         2621
_refine_ls_number_restraints     25
_refine_ls_restrained_S_all      1.009
_refine_ls_R_factor_all          0.1116
_refine_ls_R_factor_gt           0.0647
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1000P)^2^+0.6278P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1684
_refine_ls_wR_factor_ref         0.2017
_reflns_Friedel_coverage         0.888
_reflns_Friedel_fraction_full    0.996
_reflns_Friedel_fraction_max     0.996
_reflns_number_gt                1519
_reflns_number_total             2621
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c7ra11216e2.cif
_cod_data_source_block           shelx
_cod_database_code               7229466
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.983
_shelx_estimated_absorpt_t_max   0.987
_shelx_res_checksum              51519