# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2017

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_s100_fin
_database_code_depnum_ccdc_archive 'CCDC 1544114'
_audit_update_record             
;
2017-04-14 deposited with the CCDC.
2017-10-27 downloaded from the CCDC.
;
_audit_creation_method           SHELXL-97
_chemical_name_common            
'(E)-4-benzylidene-3,4-dihydro-2H-pyrrol-1-ium 2,2,2-trifluoroacetate'
_chemical_name_systematic        
'(E)-4-benzylidene-3,4-dihydro-2H-pyrrol-1-ium 2,2,2-trifluoroacetate'
_chemical_formula_moiety         'C13 H12 F3 N O2'
_chemical_formula_sum            'C13 H12 F3 N O2'
_chemical_formula_weight         271.24
_chemical_absolute_configuration ?
_chemical_melting_point          ?
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'
F F 0.0171 0.0103 '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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, y+1/2, -z+1/2'
3 '-x, -y, -z'
4 'x, -y-1/2, z-1/2'

_symmetry_cell_setting           monoclinic
_symmetry_int_tables_number      14
_symmetry_space_group_name_H-M   'P 21/c'
_cell_length_a                   13.578(3)
_cell_length_b                   10.2118(19)
_cell_length_c                   9.1356(17)
_cell_angle_alpha                90.00
_cell_angle_beta                 97.423(4)
_cell_angle_gamma                90.00
_cell_volume                     1256.1(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1276
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      20.70
_cell_measurement_theta_min      3.49
_exptl_absorpt_coefficient_mu    0.126
_exptl_absorpt_correction_T_max  0.9875
_exptl_absorpt_correction_T_min  0.9813
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   ?
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.434
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             560
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.10
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0710
_diffrn_reflns_av_sigmaI/netI    0.0576
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            13498
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         2.50
_diffrn_ambient_temperature      296(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          ?
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed tube'
_reflns_number_gt                1189
_reflns_number_total             2458
_reflns_threshold_expression     >2sigma(I)
_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)'
_refine_diff_density_max         0.120
_refine_diff_density_min         -0.136
_refine_diff_density_rms         0.030
_refine_ls_extinction_coef       0.0067(16)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     205
_refine_ls_number_reflns         2458
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1230
_refine_ls_R_factor_gt           0.0430
_refine_ls_restrained_S_all      1.060
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0428P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0890
_refine_ls_wR_factor_ref         0.1166
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
F1 F 0.4657(5) 0.2635(10) 0.0792(8) 0.129(3) Uani 0.689(11) 1 d P A 1
F1A F 0.341(2) 0.297(4) -0.079(3) 0.217(12) Uani 0.311(11) 1 d P A 2
F2A F 0.4794(18) 0.3607(18) -0.014(4) 0.161(8) Uani 0.311(11) 1 d P A 2
F3A F 0.428(3) 0.2297(15) 0.0934(19) 0.242(16) Uani 0.311(11) 1 d P A 2
O1 O 0.27988(16) 0.4907(2) 0.0848(2) 0.1096(8) Uani 1 1 d . . .
O2 O 0.41538(13) 0.45674(15) 0.24546(18) 0.0692(5) Uani 1 1 d . . .
C13 C 0.3885(2) 0.3285(3) 0.0297(3) 0.0685(7) Uani 1 1 d . . .
C14 C 0.3584(2) 0.4366(2) 0.1310(3) 0.0623(7) Uani 1 1 d . A .
F2 F 0.3953(10) 0.3751(5) -0.1036(7) 0.124(3) Uani 0.689(11) 1 d P A 1
F3 F 0.3171(4) 0.2396(5) 0.0052(10) 0.107(2) Uani 0.689(11) 1 d P A 1
N1 N 0.39430(16) 0.88656(18) 1.1691(2) 0.0573(5) Uani 1 1 d . . .
H1 H 0.471(2) 0.903(2) 1.209(3) 0.103(9) Uiso 1 1 d . . .
C2 C 0.34705(18) 0.9307(2) 1.0491(3) 0.0559(6) Uani 1 1 d . . .
H2 H 0.3760 0.9834 0.9835 0.067 Uiso 1 1 calc R . .
C3 C 0.24548(18) 0.89115(19) 1.0258(2) 0.0502(6) Uani 1 1 d . . .
C4 C 0.23002(17) 0.8048(2) 1.1545(2) 0.0559(6) Uani 1 1 d . . .
H41 H 0.1788 0.8401 1.2080 0.067 Uiso 1 1 calc R . .
H42 H 0.2112 0.7169 1.1215 0.067 Uiso 1 1 calc R . .
C5 C 0.33073(18) 0.8044(2) 1.2509(3) 0.0654(7) Uani 1 1 d . . .
H51 H 0.3254 0.8413 1.3474 0.079 Uiso 1 1 calc R . .
H52 H 0.3570 0.7162 1.2633 0.079 Uiso 1 1 calc R . .
C6 C 0.18383(18) 0.9321(2) 0.9077(2) 0.0566(6) Uani 1 1 d . . .
H6 H 0.2131 0.9860 0.8435 0.068 Uiso 1 1 calc R . .
C7 C 0.07922(18) 0.9059(2) 0.8639(2) 0.0552(6) Uani 1 1 d . . .
C8 C 0.0331(2) 0.9659(2) 0.7360(3) 0.0715(7) Uani 1 1 d . . .
H8 H 0.0703 1.0192 0.6814 0.086 Uiso 1 1 calc R . .
C9 C -0.0661(2) 0.9478(3) 0.6890(3) 0.0832(9) Uani 1 1 d . . .
H9 H -0.0954 0.9890 0.6035 0.100 Uiso 1 1 calc R . .
C10 C -0.1223(2) 0.8693(3) 0.7677(3) 0.0821(8) Uani 1 1 d . . .
H10 H -0.1896 0.8576 0.7361 0.098 Uiso 1 1 calc R . .
C11 C -0.0783(2) 0.8082(3) 0.8935(3) 0.0759(8) Uani 1 1 d . . .
H11 H -0.1159 0.7544 0.9468 0.091 Uiso 1 1 calc R . .
C12 C 0.02096(19) 0.8262(2) 0.9411(3) 0.0637(7) Uani 1 1 d . . .
H12 H 0.0497 0.7842 1.0264 0.076 Uiso 1 1 calc R . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C13 F1 1.272(5) . ?
C13 F1A 1.156(10) . ?
C13 F2A 1.383(11) . ?
C13 F3A 1.249(16) . ?
C13 C14 1.530(4) . ?
C13 F2 1.322(6) . ?
C13 F3 1.327(5) . ?
C14 O1 1.226(3) . ?
C14 O2 1.235(3) . ?
N1 H1 1.07(3) . ?
C2 N1 1.279(3) . ?
C2 H2 0.9300 . ?
C3 C2 1.426(3) . ?
C3 C6 1.344(3) . ?
C4 C3 1.506(3) . ?
C4 H41 0.9700 . ?
C4 H42 0.9700 . ?
C5 N1 1.474(3) . ?
C5 C4 1.528(3) . ?
C5 H51 0.9700 . ?
C5 H52 0.9700 . ?
C6 H6 0.9300 . ?
C6 C7 1.450(3) . ?
C7 C8 1.394(3) . ?
C7 C12 1.390(3) . ?
C8 H8 0.9300 . ?
C8 C9 1.372(4) . ?
C9 H9 0.9300 . ?
C9 C10 1.372(4) . ?
C10 H10 0.9300 . ?
C10 C11 1.375(4) . ?
C11 H11 0.9300 . ?
C12 C11 1.373(3) . ?
C12 H12 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
F1 C13 F2A 60.1(11) . . ?
F1 C13 C14 115.7(3) . . ?
F1 C13 F2 111.3(5) . . ?
F1 C13 F3 104.7(5) . . ?
F1A C13 F1 119.9(7) . . ?
F1A C13 F2A 103.9(14) . . ?
F1A C13 F3A 109.2(13) . . ?
F1A C13 C14 124.0(6) . . ?
F1A C13 F2 54(2) . . ?
F1A C13 F3 49(2) . . ?
F2A C13 C14 108.6(5) . . ?
F3A C13 F1 29.7(16) . . ?
F3A C13 F2A 89.0(11) . . ?
F3A C13 C14 115.6(8) . . ?
F3A C13 F2 130.1(10) . . ?
F3A C13 F3 77.6(17) . . ?
F2 C13 F2A 58.7(11) . . ?
F2 C13 C14 110.7(3) . . ?
F2 C13 F3 103.2(4) . . ?
F3 C13 F2A 140.8(5) . . ?
F3 C13 C14 110.4(3) . . ?
O1 C14 O2 129.6(2) . . ?
O1 C14 C13 113.9(2) . . ?
O2 C14 C13 116.5(2) . . ?
C2 N1 H1 126.6(13) . . ?
C2 N1 C5 111.9(2) . . ?
C5 N1 H1 121.4(13) . . ?
N1 C2 H2 123.3 . . ?
N1 C2 C3 113.3(2) . . ?
C3 C2 H2 123.3 . . ?
C2 C3 C4 106.21(19) . . ?
C6 C3 C2 121.4(2) . . ?
C6 C3 C4 132.3(2) . . ?
C3 C4 H41 110.9 . . ?
C3 C4 H42 110.9 . . ?
C3 C4 C5 104.29(18) . . ?
H42 C4 H41 108.9 . . ?
C5 C4 H41 110.9 . . ?
C5 C4 H42 110.9 . . ?
N1 C5 C4 104.21(17) . . ?
N1 C5 H51 110.9 . . ?
N1 C5 H52 110.9 . . ?
C4 C5 H51 110.9 . . ?
C4 C5 H52 110.9 . . ?
H51 C5 H52 108.9 . . ?
C3 C6 H6 114.7 . . ?
C3 C6 C7 130.6(2) . . ?
C7 C6 H6 114.7 . . ?
C8 C7 C6 118.0(2) . . ?
C12 C7 C6 124.7(2) . . ?
C12 C7 C8 117.3(2) . . ?
C7 C8 H8 119.3 . . ?
C9 C8 C7 121.3(3) . . ?
C9 C8 H8 119.3 . . ?
C8 C9 H9 119.8 . . ?
C10 C9 C8 120.3(3) . . ?
C10 C9 H9 119.8 . . ?
C9 C10 H10 120.3 . . ?
C9 C10 C11 119.4(3) . . ?
C11 C10 H10 120.3 . . ?
C10 C11 H11 119.8 . . ?
C12 C11 C10 120.5(3) . . ?
C12 C11 H11 119.8 . . ?
C7 C12 H12 119.4 . . ?
C11 C12 C7 121.1(2) . . ?
C11 C12 H12 119.4 . . ?

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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
F1 C13 C14 O1 -174.9(7) . . . . ?
F1 C13 C14 O2 5.1(8) . . . . ?
F1A C13 C14 O1 -2(3) . . . . ?
F1A C13 C14 O2 178(3) . . . . ?
F2A C13 C14 O1 120.1(18) . . . . ?
F2A C13 C14 O2 -60.0(18) . . . . ?
F3A C13 C14 O1 -142(2) . . . . ?
F3A C13 C14 O2 38(2) . . . . ?
F2 C13 C14 O1 57.4(7) . . . . ?
F2 C13 C14 O2 -122.7(7) . . . . ?
F3 C13 C14 O1 -56.2(5) . . . . ?
F3 C13 C14 O2 123.7(5) . . . . ?
N1 C5 C4 C3 -1.2(2) . . . . ?
C2 C3 C6 C7 -179.0(2) . . . . ?
C3 C2 N1 C5 0.7(3) . . . . ?
C3 C6 C7 C8 178.0(2) . . . . ?
C3 C6 C7 C12 -1.3(4) . . . . ?
C4 C3 C2 N1 -1.5(2) . . . . ?
C4 C3 C6 C7 0.0(4) . . . . ?
C4 C5 N1 C2 0.3(2) . . . . ?
C5 C4 C3 C2 1.6(2) . . . . ?
C5 C4 C3 C6 -177.6(2) . . . . ?
C6 C3 C2 N1 177.77(19) . . . . ?
C6 C7 C8 C9 -178.8(2) . . . . ?
C6 C7 C12 C11 178.8(2) . . . . ?
C7 C8 C9 C10 -0.2(4) . . . . ?
C7 C12 C11 C10 0.0(4) . . . . ?
C8 C7 C12 C11 -0.5(3) . . . . ?
C8 C9 C10 C11 -0.4(4) . . . . ?
C9 C10 C11 C12 0.5(4) . . . . ?
C12 C7 C8 C9 0.6(3) . . . . ?

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_s6_fin1
_database_code_depnum_ccdc_archive 'CCDC 1544115'
_audit_update_record             
;
2017-04-14 deposited with the CCDC.
2017-10-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
'(E)-4-(4-methoxybenzylidene)-3,4-dihydro-2H-pyrrol-1-ium 2,2,2-trifluoroacetate'
_chemical_name_common            
'(E)-4-(4-methoxybenzylidene)-3,4-dihydro-2H-pyrrol-1-ium 2,2,2-trifluoroacetate'
_chemical_formula_moiety         'C14 H14 F3 N O3'
_chemical_formula_sum            'C14 H14 F3 N O3'
_chemical_melting_point          ?

_exptl_crystal_description       prism
_exptl_crystal_colour            rose

_diffrn_ambient_temperature      296(2)
_chemical_formula_weight         301.26

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'
F F 0.0171 0.0103 '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'

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_int_tables_number      2
_chemical_absolute_configuration ?

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.961(5)
_cell_length_b                   10.047(7)
_cell_length_c                   10.047(7)
_cell_angle_alpha                115.086(7)
_cell_angle_beta                 106.138(8)
_cell_angle_gamma                90.896(8)
_cell_volume                     690.8(8)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    1951
_cell_measurement_theta_min      2.27
_cell_measurement_theta_max      29.06
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.448
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             312
_exptl_absorpt_coefficient_mu    0.128
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  0.9811
_exptl_absorpt_correction_T_max  0.9873
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;
_diffrn_radiation_probe          ?
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            6307
_diffrn_reflns_av_R_equivalents  0.0224
_diffrn_reflns_av_sigmaI/netI    0.0303
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         2.27
_diffrn_reflns_theta_max         25.99
_reflns_number_total             2698
_reflns_number_gt                1901
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'


_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0976P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2698
_refine_ls_number_parameters     194
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0777
_refine_ls_R_factor_gt           0.0560
_refine_ls_wR_factor_ref         0.1884
_refine_ls_wR_factor_gt          0.1688
_refine_ls_goodness_of_fit_ref   1.264
_refine_ls_restrained_S_all      1.264
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C6 C 0.1764(3) 1.0307(2) 0.4152(2) 0.0456(5) Uani 1 1 d . . .
H6 H 0.1098 1.0517 0.3364 0.055 Uiso 1 1 calc R . .
C7 C 0.1359(3) 0.8795(2) 0.3906(2) 0.0423(5) Uani 1 1 d . . .
O17 O 0.5435(3) 0.6636(2) 0.71662(19) 0.0727(6) Uani 1 1 d . . .
C3 C 0.2942(3) 1.1457(2) 0.5331(2) 0.0431(5) Uani 1 1 d . . .
N1 N 0.4347(3) 1.3816(2) 0.6526(2) 0.0524(5) Uani 1 1 d . . .
O13 O 0.0019(3) 0.44192(18) 0.3028(2) 0.0714(6) Uani 1 1 d . . .
C12 C 0.2144(3) 0.8225(2) 0.4944(3) 0.0498(6) Uani 1 1 d . . .
H12 H 0.2991 0.8847 0.5878 0.060 Uiso 1 1 calc R . .
F1 F 0.7417(3) 0.96881(17) 1.06939(18) 0.0966(7) Uani 1 1 d . . .
C4 C 0.4235(3) 1.1620(2) 0.6821(2) 0.0485(6) Uani 1 1 d . . .
H42 H 0.5091 1.0944 0.6622 0.058 Uiso 1 1 calc R . .
H41 H 0.3626 1.1422 0.7446 0.058 Uiso 1 1 calc R . .
C8 C 0.0092(3) 0.7817(2) 0.2531(2) 0.0482(6) Uani 1 1 d . . .
H8 H -0.0454 0.8166 0.1821 0.058 Uiso 1 1 calc R . .
C16 C 0.6143(3) 0.7289(2) 0.8590(3) 0.0503(6) Uani 1 1 d . . .
C11 C 0.1692(3) 0.6775(3) 0.4615(3) 0.0562(6) Uani 1 1 d . . .
H11 H 0.2244 0.6420 0.5317 0.067 Uiso 1 1 calc R . .
C10 C 0.0407(3) 0.5828(2) 0.3232(3) 0.0527(6) Uani 1 1 d . . .
O18 O 0.6270(3) 0.6835(2) 0.9551(2) 0.0863(7) Uani 1 1 d . . .
C2 C 0.3175(3) 1.2867(2) 0.5317(3) 0.0498(6) Uani 1 1 d . . .
H2 H 0.2539 1.3067 0.4511 0.060 Uiso 1 1 calc R . .
F3 F 0.6095(3) 0.96273(19) 0.8523(2) 0.1123(8) Uani 1 1 d . . .
C9 C -0.0388(3) 0.6357(3) 0.2178(3) 0.0523(6) Uani 1 1 d . . .
H9 H -0.1235 0.5733 0.1243 0.063 Uiso 1 1 calc R . .
C15 C 0.7002(3) 0.8880(3) 0.9181(3) 0.0552(6) Uani 1 1 d . . .
C5 C 0.5134(3) 1.3229(3) 0.7626(3) 0.0551(6) Uani 1 1 d . . .
H51 H 0.4898 1.3772 0.8598 0.066 Uiso 1 1 calc R . .
H52 H 0.6404 1.3285 0.7825 0.066 Uiso 1 1 calc R . .
F2 F 0.8524(3) 0.8891(2) 0.8876(3) 0.1124(7) Uani 1 1 d . . .
C14 C -0.1301(4) 0.3421(3) 0.1635(4) 0.0821(9) Uani 1 1 d . . .
H143 H -0.1451 0.2469 0.1630 0.123 Uiso 1 1 calc R . .
H142 H -0.0942 0.3313 0.0762 0.123 Uiso 1 1 calc R . .
H141 H -0.2400 0.3808 0.1572 0.123 Uiso 1 1 calc R . .
H1 H 0.468(4) 1.474(3) 0.672(3) 0.080(9) Uiso 1 1 d . . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C6 C3 1.344(3) . ?
C6 C7 1.447(3) . ?
C6 H6 0.9300 . ?
C7 C8 1.391(3) . ?
C7 C12 1.400(3) . ?
O17 C16 1.241(3) . ?
C3 C2 1.433(3) . ?
C3 C4 1.502(3) . ?
N1 C2 1.271(3) . ?
N1 C5 1.463(3) . ?
N1 H1 0.88(3) . ?
O13 C10 1.359(3) . ?
O13 C14 1.424(3) . ?
C12 C11 1.367(3) . ?
C12 H12 0.9300 . ?
F1 C15 1.321(3) . ?
C4 C5 1.520(3) . ?
C4 H42 0.9700 . ?
C4 H41 0.9700 . ?
C8 C9 1.374(3) . ?
C8 H8 0.9300 . ?
C16 O18 1.213(3) . ?
C16 C15 1.520(3) . ?
C11 C10 1.393(3) . ?
C11 H11 0.9300 . ?
C10 C9 1.386(3) . ?
C2 H2 0.9300 . ?
F3 C15 1.302(3) . ?
C9 H9 0.9300 . ?
C15 F2 1.331(3) . ?
C5 H51 0.9700 . ?
C5 H52 0.9700 . ?
C14 H143 0.9600 . ?
C14 H142 0.9600 . ?
C14 H141 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C3 C6 C7 130.7(2) . . ?
C3 C6 H6 114.7 . . ?
C7 C6 H6 114.7 . . ?
C8 C7 C12 116.7(2) . . ?
C8 C7 C6 117.97(19) . . ?
C12 C7 C6 125.3(2) . . ?
C6 C3 C2 121.6(2) . . ?
C6 C3 C4 132.5(2) . . ?
C2 C3 C4 105.96(19) . . ?
C2 N1 C5 112.9(2) . . ?
C2 N1 H1 125.7(19) . . ?
C5 N1 H1 121.4(19) . . ?
C10 O13 C14 117.6(2) . . ?
C11 C12 C7 121.5(2) . . ?
C11 C12 H12 119.2 . . ?
C7 C12 H12 119.2 . . ?
C3 C4 C5 104.57(18) . . ?
C3 C4 H42 110.8 . . ?
C5 C4 H42 110.8 . . ?
C3 C4 H41 110.8 . . ?
C5 C4 H41 110.8 . . ?
H42 C4 H41 108.9 . . ?
C9 C8 C7 122.8(2) . . ?
C9 C8 H8 118.6 . . ?
C7 C8 H8 118.6 . . ?
O18 C16 O17 129.6(2) . . ?
O18 C16 C15 116.6(2) . . ?
O17 C16 C15 113.86(19) . . ?
C12 C11 C10 120.3(2) . . ?
C12 C11 H11 119.9 . . ?
C10 C11 H11 119.9 . . ?
O13 C10 C9 124.6(2) . . ?
O13 C10 C11 115.9(2) . . ?
C9 C10 C11 119.6(2) . . ?
N1 C2 C3 112.6(2) . . ?
N1 C2 H2 123.7 . . ?
C3 C2 H2 123.7 . . ?
C8 C9 C10 119.1(2) . . ?
C8 C9 H9 120.4 . . ?
C10 C9 H9 120.4 . . ?
F3 C15 F1 107.6(2) . . ?
F3 C15 F2 103.9(2) . . ?
F1 C15 F2 105.1(2) . . ?
F3 C15 C16 114.7(2) . . ?
F1 C15 C16 114.46(19) . . ?
F2 C15 C16 110.1(2) . . ?
N1 C5 C4 103.93(19) . . ?
N1 C5 H51 111.0 . . ?
C4 C5 H51 111.0 . . ?
N1 C5 H52 111.0 . . ?
C4 C5 H52 111.0 . . ?
H51 C5 H52 109.0 . . ?
O13 C14 H143 109.5 . . ?
O13 C14 H142 109.5 . . ?
H143 C14 H142 109.5 . . ?
O13 C14 H141 109.5 . . ?
H143 C14 H141 109.5 . . ?
H142 C14 H141 109.5 . . ?

_diffrn_measured_fraction_theta_max 0.993
_diffrn_reflns_theta_full        25.99
_diffrn_measured_fraction_theta_full 0.993
_refine_diff_density_max         0.312
_refine_diff_density_min         -0.335
_refine_diff_density_rms         0.055

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_s5_fin
_database_code_depnum_ccdc_archive 'CCDC 1544117'
_audit_update_record             
;
2017-04-14 deposited with the CCDC.
2017-10-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
'(E)-3-benzylidene-2-(2-oxopropyl)pyrrolidin-1-ium chloride'
_chemical_name_common            
'(E)-3-benzylidene-2-(2-oxopropyl)pyrrolidin-1-ium chloride'
_chemical_formula_moiety         'C14 H17 Br Cl N O'
_chemical_formula_sum            'C14 H17 Br Cl N O'
_chemical_melting_point          ?

_exptl_crystal_description       prizm
_exptl_crystal_colour            colorless

_diffrn_ambient_temperature      296(2)
_chemical_formula_weight         330.65

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'
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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 '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'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/n'
_symmetry_int_tables_number      14
_chemical_absolute_configuration ?

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   5.038(2)
_cell_length_b                   24.005(11)
_cell_length_c                   12.287(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 99.804(6)
_cell_angle_gamma                90.00
_cell_volume                     1464.2(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    4187
_cell_measurement_theta_min      2.39
_cell_measurement_theta_max      22.71
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.500
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             672
_exptl_absorpt_coefficient_mu    2.978
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  0.5873
_exptl_absorpt_correction_T_max  0.7550
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;
_diffrn_radiation_probe          ?
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            15113
_diffrn_reflns_av_R_equivalents  0.0394
_diffrn_reflns_av_sigmaI/netI    0.0303
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -29
_diffrn_reflns_limit_k_max       29
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         1.70
_diffrn_reflns_theta_max         26.00
_reflns_number_total             2879
_reflns_number_gt                2206
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'


_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0000P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2879
_refine_ls_number_parameters     172
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0578
_refine_ls_R_factor_gt           0.0381
_refine_ls_wR_factor_ref         0.0647
_refine_ls_wR_factor_gt          0.0628
_refine_ls_goodness_of_fit_ref   1.893
_refine_ls_restrained_S_all      1.893
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.000

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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Br13 Br -0.48356(7) 1.033430(13) 0.67799(3) 0.08426(16) Uani 1 1 d . . .
Cl18 Cl 0.80837(11) 0.71670(2) 0.77088(5) 0.04981(18) Uani 1 1 d . . .
C6 C 0.2323(4) 0.84218(9) 0.89256(17) 0.0375(5) Uani 1 1 d . . .
H6 H 0.1805 0.8082 0.8591 0.045 Uiso 1 1 calc R . .
C8 C 0.1171(5) 0.94499(10) 0.8758(2) 0.0615(8) Uani 1 1 d . . .
H8 H 0.2665 0.9540 0.9283 0.074 Uiso 1 1 calc R . .
C7 C 0.0653(4) 0.88951(9) 0.84837(17) 0.0401(6) Uani 1 1 d . . .
C10 C -0.2677(5) 0.97457(10) 0.74926(19) 0.0518(7) Uani 1 1 d . . .
C9 C -0.0478(5) 0.98690(11) 0.8271(2) 0.0663(8) Uani 1 1 d . . .
H9 H -0.0095 1.0238 0.8471 0.080 Uiso 1 1 calc R . .
C11 C -0.3292(5) 0.92043(11) 0.7219(2) 0.0554(7) Uani 1 1 d . . .
H11 H -0.4814 0.9119 0.6704 0.066 Uiso 1 1 calc R . .
C14 C 0.4494(4) 0.73270(8) 0.99485(18) 0.0399(6) Uani 1 1 d . . .
H14A H 0.3131 0.7344 1.0418 0.048 Uiso 1 1 calc R . .
H14B H 0.3570 0.7292 0.9192 0.048 Uiso 1 1 calc R . .
N1 N 0.7324(5) 0.79871(9) 1.12331(17) 0.0394(5) Uani 1 1 d . . .
C3 C 0.4479(4) 0.83951(8) 0.97335(16) 0.0355(5) Uani 1 1 d . . .
C4 C 0.5771(4) 0.88602(9) 1.04691(18) 0.0453(6) Uani 1 1 d . . .
H4A H 0.4465 0.9033 1.0858 0.054 Uiso 1 1 calc R . .
H4B H 0.6495 0.9142 1.0036 0.054 Uiso 1 1 calc R . .
C5 C 0.8008(5) 0.85906(9) 1.12782(19) 0.0495(6) Uani 1 1 d . . .
H5A H 0.9744 0.8654 1.1059 0.059 Uiso 1 1 calc R . .
H5B H 0.8054 0.8737 1.2017 0.059 Uiso 1 1 calc R . .
C2 C 0.6047(4) 0.78670(9) 1.00599(16) 0.0367(5) Uani 1 1 d . . .
H2 H 0.7483 0.7839 0.9616 0.044 Uiso 1 1 calc R . .
C12 C -0.1646(4) 0.87849(9) 0.77087(18) 0.0477(6) Uani 1 1 d . . .
H12 H -0.2080 0.8417 0.7517 0.057 Uiso 1 1 calc R . .
C15 C 0.6169(5) 0.68157(9) 1.02421(18) 0.0456(6) Uani 1 1 d . . .
C16 C 0.4906(5) 0.62737(9) 0.9842(2) 0.0657(8) Uani 1 1 d . . .
H16A H 0.5108 0.6216 0.9087 0.099 Uiso 1 1 calc R . .
H16B H 0.3026 0.6281 0.9893 0.099 Uiso 1 1 calc R . .
H16C H 0.5773 0.5976 1.0289 0.099 Uiso 1 1 calc R . .
O17 O 0.8428(4) 0.68421(7) 1.07786(14) 0.0650(5) Uani 1 1 d . . .
H1A H 0.617(5) 0.7951(10) 1.1668(19) 0.058(9) Uiso 1 1 d . . .
H1B H 0.873(5) 0.7778(9) 1.1450(16) 0.037(7) Uiso 1 1 d . . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br13 C10 1.903(2) . ?
C6 C3 1.342(3) . ?
C6 C7 1.462(3) . ?
C8 C9 1.375(3) . ?
C8 C7 1.388(3) . ?
C7 C12 1.394(3) . ?
C10 C11 1.365(3) . ?
C10 C9 1.367(3) . ?
C11 C12 1.376(3) . ?
C14 C15 1.499(3) . ?
C14 C2 1.508(3) . ?
N1 C5 1.488(3) . ?
N1 C2 1.503(3) . ?
C3 C2 1.512(3) . ?
C3 C4 1.512(3) . ?
C4 C5 1.515(3) . ?
C15 O17 1.216(2) . ?
C15 C16 1.494(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C3 C6 C7 130.8(2) . . ?
C9 C8 C7 121.4(2) . . ?
C8 C7 C12 116.6(2) . . ?
C8 C7 C6 125.7(2) . . ?
C12 C7 C6 117.7(2) . . ?
C11 C10 C9 120.1(2) . . ?
C11 C10 Br13 120.38(19) . . ?
C9 C10 Br13 119.52(19) . . ?
C10 C9 C8 120.2(2) . . ?
C10 C11 C12 119.6(2) . . ?
C15 C14 C2 114.82(19) . . ?
C5 N1 C2 106.32(17) . . ?
C6 C3 C2 123.83(18) . . ?
C6 C3 C4 128.22(19) . . ?
C2 C3 C4 107.95(17) . . ?
C3 C4 C5 105.87(18) . . ?
N1 C5 C4 104.46(17) . . ?
N1 C2 C14 112.49(18) . . ?
N1 C2 C3 102.28(16) . . ?
C14 C2 C3 117.20(18) . . ?
C11 C12 C7 121.9(2) . . ?
O17 C15 C16 122.1(2) . . ?
O17 C15 C14 121.6(2) . . ?
C16 C15 C14 116.3(2) . . ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        26.00
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.519
_refine_diff_density_min         -0.387
_refine_diff_density_rms         0.053

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_shelx
_database_code_depnum_ccdc_archive 'CCDC 1544116'
_audit_update_record             
;
2017-04-14 deposited with the CCDC.
2017-10-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        
'(E)-4-(3-fluorobenzylidene)-3,4-dihydro-2H-pyrrol-1-ium 2,2,2-trifluoroacetate'
_chemical_name_common            
'(E)-4-(3-fluorobenzylidene)-3,4-dihydro-2H-pyrrol-1-ium 2,2,2-trifluoroacetate'
_chemical_formula_moiety         'C13 H11 F4 N O2'
_chemical_formula_sum            'C13 H11 F4 N O2'
_chemical_melting_point          ?

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_diffrn_ambient_temperature      296(2)
_chemical_formula_weight         289.23

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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_H-M_alt        'P n a 21'
_space_group_name_Hall           'P 2c -2n'

_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.
;

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'

_cell_length_a                   23.90(4)
_cell_length_b                   5.288(9)
_cell_length_c                   10.524(19)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1330(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    1243
_cell_measurement_theta_min      3.41
_cell_measurement_theta_max      19.77
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.444
_exptl_crystal_F_000             592
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.130
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.134
_shelx_estimated_absorpt_T_min   0.983
_shelx_estimated_absorpt_T_max   0.987
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_radiation_probe          ?
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'sealed tube'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            9514
_diffrn_reflns_av_unetI/netI     0.0568
_diffrn_reflns_av_R_equivalents  0.0544
_diffrn_reflns_limit_h_min       -29
_diffrn_reflns_limit_h_max       29
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         1.704
_diffrn_reflns_theta_max         25.989
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             2621
_reflns_number_gt                1519
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.888
_reflns_Friedel_fraction_max     0.996
_reflns_Friedel_fraction_full    0.996

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1000P)²+0.6278P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_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)
_symmetry_cell_setting           ?
_symmetry_space_group_name_h-m   ?
_symmetry_int_tables_number      ?
_chemical_absolute_configuration ?
_refine_ls_number_reflns         2621
_refine_ls_number_parameters     181
_refine_ls_number_restraints     25
_refine_ls_R_factor_all          0.1116
_refine_ls_R_factor_gt           0.0647
_refine_ls_wR_factor_ref         0.2017
_refine_ls_wR_factor_gt          0.1684
_refine_ls_goodness_of_fit_ref   0.967
_refine_ls_restrained_S_all      1.009
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

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_refinement_flags_occupancy
_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


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
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_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
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_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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
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) . . . . ?

_refine_diff_density_max         0.360
_refine_diff_density_min         -0.246
_refine_diff_density_rms         0.047

