#------------------------------------------------------------------------------
#$Date: 2017-11-02 08:47:25 +0200 (Thu, 02 Nov 2017) $
#$Revision: 202514 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/22/94/7229466.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7229466
loop_
_publ_author_name
'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.'
_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       'φ and ω 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/[σ²(Fo²)+(0.1000P)²+0.6278P] where P=(Fo²+2Fc²)/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 > 2σ(I)'
_cod_data_source_file            c7ra11216e2.cif
_cod_data_source_block           shelx
_cod_database_code               7229466
_shelx_shelxl_version_number     2014/7
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_min   0.983
_shelx_estimated_absorpt_t_max   0.987
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'-x+1/2, y+1/2, z+1/2'
'x+1/2, -y+1/2, z'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_disorder_assembly
_atom_site_disorder_group
F1 F 0.4952(3) 0.8874(11) 0.2047(6) 0.133(2) Uani 1 1 d . U A 1
O2 O 0.7043(2) 0.1309(11) 0.3267(5) 0.0828(16) Uani 1 1 d . . B 1
C6 C 0.3681(3) 0.2169(13) 0.3131(6) 0.0624(18) Uani 1 1 d . . A 1
H6 H 0.3662 0.1930 0.2257 0.075 Uiso 1 1 calc R U A 1
N1 N 0.2721(2) -0.2533(10) 0.4009(5) 0.0575(13) Uani 1 1 d . . A 1
H1 H 0.2494 -0.3712 0.3784 0.069 Uiso 1 1 calc R U A 1
C14 C 0.6785(3) 0.2212(14) 0.4176(6) 0.0606(17) Uani 1 1 d . . B 1
C5 C 0.2821(3) -0.1835(13) 0.5320(7) 0.0658(17) Uani 1 1 d . . A 1
H51 H 0.2975 -0.3244 0.5794 0.079 Uiso 1 1 calc R U A 1
H52 H 0.2477 -0.1292 0.5727 0.079 Uiso 1 1 calc R U A 1
C4 C 0.3245(3) 0.0370(12) 0.5239(6) 0.0597(16) Uani 1 1 d . . A 1
H42 H 0.3089 0.1910 0.5594 0.072 Uiso 1 1 calc R U A 1
H41 H 0.3588 -0.0040 0.5686 0.072 Uiso 1 1 calc R U A 1
C3 C 0.3350(3) 0.0650(13) 0.3814(6) 0.0544(15) Uani 1 1 d . . A 1
C7 C 0.4072(3) 0.4158(13) 0.3544(6) 0.0578(16) Uani 1 1 d . . A 1
C8 C 0.4338(3) 0.5611(14) 0.2620(7) 0.074(2) Uani 1 1 d . . A 1
H8 H 0.4267 0.5317 0.1763 0.089 Uiso 1 1 calc R U A 1
C9 C 0.4704(3) 0.7473(16) 0.2974(8) 0.079(2) Uani 1 1 d . . A 1
C10 C 0.4834(3) 0.8006(15) 0.4200(9) 0.079(2) Uani 1 1 d . . A 1
H10 H 0.5084 0.9287 0.4407 0.094 Uiso 1 1 calc R U A 1
C2 C 0.3005(3) -0.1218(13) 0.3219(6) 0.0614(17) Uani 1 1 d . . A 1
H2 H 0.2990 -0.1454 0.2344 0.074 Uiso 1 1 calc R U A 1
C12 C 0.4204(3) 0.4656(15) 0.4815(7) 0.0688(18) Uani 1 1 d . . A 1
H12 H 0.4040 0.3700 0.5457 0.083 Uiso 1 1 calc R U A 1
C11 C 0.4577(3) 0.6561(14) 0.5127(8) 0.074(2) Uani 1 1 d . . A 1
H11 H 0.4657 0.6875 0.5977 0.088 Uiso 1 1 calc R U A 1
C13 C 0.6314(3) 0.4077(18) 0.3831(7) 0.077(2) Uani 1 1 d . . B 1
O1 O 0.6863(3) 0.1898(12) 0.5303(5) 0.107(2) Uani 1 1 d . . B 1
F2 F 0.6264(3) 0.5985(12) 0.4614(6) 0.137(2) Uani 1 1 d . U B 1
F3 F 0.6383(3) 0.5212(16) 0.2742(6) 0.158(3) Uani 1 1 d . U B 1
F4 F 0.5837(3) 0.3046(17) 0.3904(12) 0.214(5) Uani 1 1 d . U B 1
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C3 C6 C7 130.3(6)
C3 C6 H6 114.9
C7 C6 H6 114.9
C2 N1 C5 113.1(6)
C2 N1 H1 123.4
C5 N1 H1 123.4
O1 C14 O2 128.8(7)
O1 C14 C13 115.6(7)
O2 C14 C13 115.5(6)
N1 C5 C4 104.3(5)
N1 C5 H51 110.9
C4 C5 H51 110.9
N1 C5 H52 110.9
C4 C5 H52 110.9
H51 C5 H52 108.9
C3 C4 C5 103.6(5)
C3 C4 H42 111.0
C5 C4 H42 111.0
C3 C4 H41 111.0
C5 C4 H41 111.0
H42 C4 H41 109.0
C6 C3 C2 121.4(6)
C6 C3 C4 133.0(6)
C2 C3 C4 105.6(5)
C8 C7 C12 117.4(6)
C8 C7 C6 118.5(6)
C12 C7 C6 124.0(6)
C9 C8 C7 119.9(7)
C9 C8 H8 120.1
C7 C8 H8 120.1
C10 C9 F1 117.9(7)
C10 C9 C8 123.7(7)
F1 C9 C8 118.4(8)
C9 C10 C11 117.0(7)
C9 C10 H10 121.5
C11 C10 H10 121.5
N1 C2 C3 113.4(6)
N1 C2 H2 123.3
C3 C2 H2 123.3
C11 C12 C7 120.6(7)
C11 C12 H12 119.7
C7 C12 H12 119.7
C10 C11 C12 121.4(7)
C10 C11 H11 119.3
C12 C11 H11 119.3
F4 C13 F3 111.5(9)
F4 C13 F2 102.2(8)
F3 C13 F2 102.2(8)
F4 C13 C14 111.6(8)
F3 C13 C14 114.1(6)
F2 C13 C14 114.3(7)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
F1 C9 1.361(9)
O2 C14 1.235(8)
C6 C3 1.338(9)
C6 C7 1.472(10)
C6 H6 0.9300
N1 C2 1.279(8)
N1 C5 1.448(9)
N1 H1 0.8600
C14 O1 1.212(8)
C14 C13 1.540(11)
C5 C4 1.549(9)
C5 H51 0.9700
C5 H52 0.9700
C4 C3 1.527(10)
C4 H42 0.9700
C4 H41 0.9700
C3 C2 1.431(9)
C7 C8 1.393(10)
C7 C12 1.399(10)
C8 C9 1.369(11)
C8 H8 0.9300
C9 C10 1.357(12)
C10 C11 1.383(11)
C10 H10 0.9300
C2 H2 0.9300
C12 C11 1.385(10)
C12 H12 0.9300
C11 H11 0.9300
C13 F4 1.266(10)
C13 F3 1.304(10)
C13 F2 1.309(10)
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
C2 N1 C5 C4 1.0(8)
N1 C5 C4 C3 -1.0(7)
C7 C6 C3 C2 -178.7(7)
C7 C6 C3 C4 0.0(13)
C5 C4 C3 C6 -178.2(7)
C5 C4 C3 C2 0.6(7)
C3 C6 C7 C8 -175.0(7)
C3 C6 C7 C12 6.4(11)
C12 C7 C8 C9 -1.2(11)
C6 C7 C8 C9 -179.9(7)
C7 C8 C9 C10 0.6(13)
C7 C8 C9 F1 -179.4(7)
F1 C9 C10 C11 -180.0(7)
C8 C9 C10 C11 0.0(13)
C5 N1 C2 C3 -0.7(9)
C6 C3 C2 N1 179.0(6)
C4 C3 C2 N1 0.0(8)
C8 C7 C12 C11 1.2(10)
C6 C7 C12 C11 179.9(6)
C9 C10 C11 C12 0.0(11)
C7 C12 C11 C10 -0.6(11)
O1 C14 C13 F4 -80.5(11)
O2 C14 C13 F4 101.9(10)
O1 C14 C13 F3 151.9(9)
O2 C14 C13 F3 -25.7(11)
O1 C14 C13 F2 34.8(11)
O2 C14 C13 F2 -142.8(8)
