# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2019

####################################################################### 
# 
# 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_8A
_database_code_depnum_ccdc_archive 'CCDC 1955342'
loop_
_audit_author_name
_audit_author_address
'Muhammad Nawaz Tahir'
;Department of Physics University of Sargodha Sargodha Pakistan
Pakistan
;
_audit_update_record             
;
2019-11-05 deposited with the CCDC.	2019-11-08 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_absolute_configuration .
_chemical_name_systematic        
"(2E,2'E)-N,N'-(cyclohexane-1,2-diyl)bis(1-methylpyridin-2(1H)-iminium) di-trifluoromethanesulfonate"
_chemical_formula_moiety         'C18 H26 N4, 2(C F3 O3 S)'
_chemical_formula_sum            'C20 H26 F6 N4 O6 S2'
_chemical_formula_iupac          'C20 H26 F6 N4 O6 S2'
_chemical_formula_weight         596.57

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           60
_space_group_name_H-M_alt        'P b c n'
_space_group_name_Hall           '-P 2n 2ab'

_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+1/2, -y+1/2, -z'
'-x, y, -z+1/2'
'-x+1/2, -y+1/2, z+1/2'
'-x, -y, -z'
'-x-1/2, y-1/2, z'
'x, -y, z-1/2'
'x-1/2, y-1/2, -z-1/2'

_cell_length_a                   15.5634(3)
_cell_length_b                   12.4382(2)
_cell_length_c                   12.8282(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2483.29(9)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1935
_cell_measurement_theta_min      4.441
_cell_measurement_theta_max      68.305
_cell_measurement_temperature    100(2)
_exptl_crystal_description       plate
_exptl_crystal_colour            'Brown solid'
_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.04
_exptl_crystal_density_diffrn    1.596
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1232
_exptl_absorpt_coefficient_mu    2.780
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2005)'
_exptl_absorpt_correction_T_min  0.630
_exptl_absorpt_correction_T_max  0.910
_exptl_special_details           
;
;
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker Kappa APEXII CCD'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 7.70
_diffrn_reflns_number            36806
_diffrn_reflns_av_unetI/netI     0.0229
_diffrn_reflns_av_R_equivalents  0.0771
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         4.551
_diffrn_reflns_theta_max         68.305
_diffrn_reflns_theta_full        68.305
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?

_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 >
σ(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.
;
_reflns_number_total             2282
_reflns_number_gt                1935
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0627
_refine_ls_R_factor_gt           0.0524
_refine_ls_wR_factor_ref         0.1299
_refine_ls_wR_factor_gt          0.1235
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_restrained_S_all      1.085
_refine_ls_number_reflns         2282
_refine_ls_number_parameters     180
_refine_ls_number_restraints     12
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0533P)²+6.5861P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_computing_data_collection       'APEX2 (Bruker, 2007)'
_computing_cell_refinement       'SAINT (Bruker, 2007)'
_computing_data_reduction        'SAINT (Bruker, 2007)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2018/3  (Sheldrick, 2015)'
_computing_molecular_graphics    
'ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2009)'
_computing_publication_material  
;
WinGX (Farrugia, 1999) and PLATON (Spek, 2009)
;


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
N1 N 0.12321(15) 0.14594(19) 0.32400(18) 0.0162(5) Uani 1 1 d . . . . .
N2 N 0.08723(14) -0.03357(18) 0.29975(18) 0.0135(5) Uani 1 1 d . . . . .
H2A H 0.138704 -0.041296 0.272365 0.016 Uiso 1 1 calc R U . . .
C1 C 0.1068(2) 0.2473(2) 0.3597(3) 0.0230(7) Uani 1 1 d . . . . .
H1 H 0.148167 0.302352 0.349072 0.028 Uiso 1 1 calc R U . . .
C2 C 0.0328(2) 0.2707(3) 0.4100(3) 0.0265(7) Uani 1 1 d . . . . .
H2 H 0.021147 0.341826 0.432933 0.032 Uiso 1 1 calc R U . . .
C3 C -0.02627(19) 0.1880(3) 0.4274(2) 0.0211(7) Uani 1 1 d . . . . .
H3 H -0.078808 0.203049 0.462212 0.025 Uiso 1 1 calc R U . . .
C4 C -0.00900(18) 0.0857(2) 0.3948(2) 0.0156(6) Uani 1 1 d . . . . .
H4 H -0.048549 0.029400 0.409188 0.019 Uiso 1 1 calc R U . . .
C5 C 0.06746(17) 0.0635(2) 0.3399(2) 0.0126(6) Uani 1 1 d . . . . .
C6 C 0.20285(18) 0.1281(2) 0.2650(3) 0.0215(7) Uani 1 1 d . . . . .
H6A H 0.188805 0.100317 0.195565 0.032 Uiso 1 1 calc R U . . .
H6B H 0.238858 0.075895 0.301935 0.032 Uiso 1 1 calc R U . . .
H6C H 0.234005 0.196204 0.258110 0.032 Uiso 1 1 calc R U . . .
C7 C 0.03014(16) -0.1274(2) 0.2979(2) 0.0129(6) Uani 1 1 d . . . . .
H7 H -0.005510 -0.127560 0.362743 0.016 Uiso 1 1 calc R U . . .
C8 C 0.08571(18) -0.2286(2) 0.2961(2) 0.0170(6) Uani 1 1 d . . . . .
H8A H 0.123784 -0.228921 0.357915 0.020 Uiso 1 1 calc R U . . .
H8B H 0.122449 -0.227717 0.233103 0.020 Uiso 1 1 calc R U . . .
C9 C 0.03103(19) -0.3306(2) 0.2960(2) 0.0207(7) Uani 1 1 d . . . . .
H9A H 0.068917 -0.394427 0.291735 0.025 Uiso 1 1 calc R U . . .
H9B H -0.001846 -0.335119 0.361955 0.025 Uiso 1 1 calc R U . . .
S1 S 0.24428(4) 0.39603(6) 0.07667(5) 0.0172(2) Uani 1 1 d . . . . .
F1 F 0.17883(12) 0.59186(15) 0.08756(16) 0.0317(5) Uani 1 1 d D . . . .
F2A F 0.08885(15) 0.4704(2) 0.0611(4) 0.0722(16) Uani 0.843(6) 1 d D . P A 1
F3A F 0.1710(3) 0.5180(3) -0.0640(2) 0.0689(16) Uani 0.843(6) 1 d D . P A 1
F2B F 0.1008(11) 0.4791(14) -0.0060(13) 0.0689(16) Uani 0.157(6) 1 d D . P A 2
F3B F 0.2196(9) 0.5467(13) -0.0473(15) 0.0722(16) Uani 0.157(6) 1 d D . P A 2
O1 O 0.2344(2) 0.3898(2) 0.1870(2) 0.0498(8) Uani 1 1 d . . . . .
O2 O 0.32528(15) 0.4425(2) 0.0475(3) 0.0459(8) Uani 1 1 d . . . . .
O3 O 0.21958(14) 0.30548(18) 0.0158(2) 0.0316(6) Uani 1 1 d . . . . .
C10 C 0.1691(2) 0.5008(3) 0.0368(3) 0.0286(8) Uani 1 1 d 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
N1 C5 1.359(4) . ?
N1 C1 1.365(4) . ?
N1 C6 1.469(4) . ?
N2 C5 1.348(4) . ?
N2 C7 1.467(3) . ?
N2 H2A 0.8800 . ?
C1 C2 1.352(5) . ?
C1 H1 0.9500 . ?
C2 C3 1.397(5) . ?
C2 H2 0.9500 . ?
C3 C4 1.367(4) . ?
C3 H3 0.9500 . ?
C4 C5 1.410(4) . ?
C4 H4 0.9500 . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?
C7 C8 1.528(4) . ?
C7 C7 1.546(5) 3 ?
C7 H7 1.0000 . ?
C8 C9 1.528(4) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 C9 1.526(6) 3 ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
S1 O3 1.424(2) . ?
S1 O1 1.425(3) . ?
S1 O2 1.436(3) . ?
S1 C10 1.824(3) . ?
F1 C10 1.315(4) . ?
F2A C10 1.342(4) . ?
F3A C10 1.312(4) . ?
F2B C10 1.227(14) . ?
F3B C10 1.452(15) . ?

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
C5 N1 C1 121.8(2) . . ?
C5 N1 C6 120.2(2) . . ?
C1 N1 C6 118.0(2) . . ?
C5 N2 C7 125.5(2) . . ?
C5 N2 H2A 117.3 . . ?
C7 N2 H2A 117.3 . . ?
C2 C1 N1 121.2(3) . . ?
C2 C1 H1 119.4 . . ?
N1 C1 H1 119.4 . . ?
C1 C2 C3 118.6(3) . . ?
C1 C2 H2 120.7 . . ?
C3 C2 H2 120.7 . . ?
C4 C3 C2 120.5(3) . . ?
C4 C3 H3 119.8 . . ?
C2 C3 H3 119.8 . . ?
C3 C4 C5 120.1(3) . . ?
C3 C4 H4 120.0 . . ?
C5 C4 H4 120.0 . . ?
N2 C5 N1 118.2(2) . . ?
N2 C5 C4 124.0(3) . . ?
N1 C5 C4 117.8(2) . . ?
N1 C6 H6A 109.5 . . ?
N1 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
N1 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
N2 C7 C8 108.2(2) . . ?
N2 C7 C7 112.37(19) . 3 ?
C8 C7 C7 109.37(19) . 3 ?
N2 C7 H7 108.9 . . ?
C8 C7 H7 108.9 . . ?
C7 C7 H7 108.9 3 . ?
C7 C8 C9 111.7(2) . . ?
C7 C8 H8A 109.3 . . ?
C9 C8 H8A 109.3 . . ?
C7 C8 H8B 109.3 . . ?
C9 C8 H8B 109.3 . . ?
H8A C8 H8B 107.9 . . ?
C9 C9 C8 110.7(2) 3 . ?
C9 C9 H9A 109.5 3 . ?
C8 C9 H9A 109.5 . . ?
C9 C9 H9B 109.5 3 . ?
C8 C9 H9B 109.5 . . ?
H9A C9 H9B 108.1 . . ?
O3 S1 O1 118.21(17) . . ?
O3 S1 O2 114.36(16) . . ?
O1 S1 O2 112.0(2) . . ?
O3 S1 C10 103.79(14) . . ?
O1 S1 C10 104.35(16) . . ?
O2 S1 C10 101.70(16) . . ?
F2B C10 F1 120.7(9) . . ?
F3A C10 F1 110.2(3) . . ?
F3A C10 F2A 107.2(4) . . ?
F1 C10 F2A 103.6(3) . . ?
F2B C10 F3B 102.9(10) . . ?
F1 C10 F3B 88.1(8) . . ?
F2B C10 S1 121.6(8) . . ?
F3A C10 S1 112.3(3) . . ?
F1 C10 S1 113.8(2) . . ?
F2A C10 S1 109.3(3) . . ?
F3B C10 S1 98.2(6) . . ?

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
C5 N1 C1 C2 -2.0(5) . . . . ?
C6 N1 C1 C2 176.6(3) . . . . ?
N1 C1 C2 C3 1.7(5) . . . . ?
C1 C2 C3 C4 0.4(5) . . . . ?
C2 C3 C4 C5 -2.2(4) . . . . ?
C7 N2 C5 N1 -171.9(2) . . . . ?
C7 N2 C5 C4 6.1(4) . . . . ?
C1 N1 C5 N2 178.2(3) . . . . ?
C6 N1 C5 N2 -0.4(4) . . . . ?
C1 N1 C5 C4 0.2(4) . . . . ?
C6 N1 C5 C4 -178.5(3) . . . . ?
C3 C4 C5 N2 -176.0(3) . . . . ?
C3 C4 C5 N1 1.9(4) . . . . ?
C5 N2 C7 C8 -153.4(3) . . . . ?
C5 N2 C7 C7 85.8(3) . . . 3 ?
N2 C7 C8 C9 179.0(2) . . . . ?
C7 C7 C8 C9 -58.3(3) 3 . . . ?
C7 C8 C9 C9 56.7(4) . . . 3 ?
O3 S1 C10 F2B 19.7(11) . . . . ?
O1 S1 C10 F2B -104.7(11) . . . . ?
O2 S1 C10 F2B 138.7(11) . . . . ?
O3 S1 C10 F3A -56.5(4) . . . . ?
O1 S1 C10 F3A 179.1(3) . . . . ?
O2 S1 C10 F3A 62.5(4) . . . . ?
O3 S1 C10 F1 177.5(3) . . . . ?
O1 S1 C10 F1 53.1(3) . . . . ?
O2 S1 C10 F1 -63.5(3) . . . . ?
O3 S1 C10 F2A 62.3(3) . . . . ?
O1 S1 C10 F2A -62.1(3) . . . . ?
O2 S1 C10 F2A -178.7(3) . . . . ?
O3 S1 C10 F3B -90.9(8) . . . . ?
O1 S1 C10 F3B 144.7(8) . . . . ?
O2 S1 C10 F3B 28.0(8) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N2 H2A O1 0.88 2.42 3.272(4) 164.6 6_655 yes
C1 H1 F3A^a 0.95 2.52 3.237(4) 132.1 7_566 yes
C1 H1 F3B^b 0.95 2.56 3.328(17) 138.6 7_566 yes
C2 H2 F2A^a 0.95 2.34 3.145(4) 141.7 3 yes
C2 H2 F2B^b 0.95 2.72 3.544(19) 145.5 3 yes
C4 H4 O2 0.95 2.31 3.220(4) 160.5 8_556 yes
C6 H6B F3A^a 0.98 2.51 3.460(5) 163.8 4 yes
C6 H6B F3B^b 0.98 2.55 3.462(18) 155.4 4 yes
C6 H6C O1 0.98 2.58 3.441(4) 147.3 . yes

_refine_diff_density_max         1.162
_refine_diff_density_min         -0.718
_refine_diff_density_rms         0.077

_chemical_melting_point          '232 ?C'
####################################################################### 
# 
# 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_dsaqaun
_database_code_depnum_ccdc_archive 'CCDC 1955344'
loop_
_audit_author_name
_audit_author_address
'Muhammad Nawaz Tahir'
;Department of Physics University of Sargodha Sargodha Pakistan
Pakistan
;
_audit_update_record             
;
2019-11-05 deposited with the CCDC.	2019-11-08 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_absolute_configuration .
_chemical_name_systematic        
;
2,2'-(Ethane-1,2-diylbis(azanediyl))bis(1-ethylpyridin-1-ium) chloride
;
_chemical_formula_moiety         'C16 H24 N4, 2(I)'
_chemical_formula_sum            'C16 H24 I2 N4'
_chemical_formula_iupac          'C16 H24 I2 N4'
_chemical_formula_weight         526.19

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'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      trigonal
_space_group_IT_number           148
_space_group_name_H-M_alt        'R -3 :H'
_space_group_name_Hall           '-R 3'

_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'
'-y, x-y, z'
'-x+y, -x, z'
'x+2/3, y+1/3, z+1/3'
'-y+2/3, x-y+1/3, z+1/3'
'-x+y+2/3, -x+1/3, z+1/3'
'x+1/3, y+2/3, z+2/3'
'-y+1/3, x-y+2/3, z+2/3'
'-x+y+1/3, -x+2/3, z+2/3'
'-x, -y, -z'
'y, -x+y, -z'
'x-y, x, -z'
'-x+2/3, -y+1/3, -z+1/3'
'y+2/3, -x+y+1/3, -z+1/3'
'x-y+2/3, x+1/3, -z+1/3'
'-x+1/3, -y+2/3, -z+2/3'
'y+1/3, -x+y+2/3, -z+2/3'
'x-y+1/3, x+2/3, -z+2/3'

_cell_length_a                   25.3399(9)
_cell_length_b                   25.3399(9)
_cell_length_c                   8.0684(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_volume                     4486.7(3)
_cell_formula_units_Z            9
_cell_measurement_reflns_used    1694
_cell_measurement_theta_min      2.690
_cell_measurement_theta_max      27.000
_cell_measurement_temperature    296(2)
_exptl_crystal_description       prism
_exptl_crystal_colour            'Fawn yellow solid'
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.24
_exptl_crystal_density_diffrn    1.753
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             2286
_exptl_absorpt_coefficient_mu    3.157
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2005)'
_exptl_absorpt_correction_T_min  0.850
_exptl_absorpt_correction_T_max  0.910
_exptl_special_details           
;
;


_diffrn_ambient_temperature      296(2)
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker Kappa APEXII CCD'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 7.83
_diffrn_reflns_number            6081
_diffrn_reflns_av_unetI/netI     0.0413
_diffrn_reflns_av_R_equivalents  0.0387
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_k_min       -32
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         2.690
_diffrn_reflns_theta_max         27.000
_diffrn_reflns_theta_full        27.000
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measured_fraction_theta_full 0.991
_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?

_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 >
σ(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.
;
_reflns_number_total             2153
_reflns_number_gt                1694
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0497
_refine_ls_R_factor_gt           0.0373
_refine_ls_wR_factor_ref         0.0992
_refine_ls_wR_factor_gt          0.0913
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_restrained_S_all      1.042
_refine_ls_number_reflns         2153
_refine_ls_number_parameters     103
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0396P)²+12.5789P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_computing_data_collection       'APEX2 (Bruker, 2007)'
_computing_cell_refinement       'SAINT (Bruker, 2007)'
_computing_data_reduction        'SAINT (Bruker, 2007)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2018/3  (Sheldrick, 2015)'
_computing_molecular_graphics    
'ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2009)'
_computing_publication_material  
;
WinGX (Farrugia, 1999) and PLATON (Spek, 2009)
;


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
N1 N 0.11119(16) 0.26018(16) 0.2327(5) 0.0651(9) Uani 1 1 d . . . . .
H1 H 0.118300 0.230357 0.234422 0.078 Uiso 1 1 calc R U . . .
N2 N 0.00854(17) 0.18805(19) 0.2134(6) 0.0768(12) Uani 1 1 d . . . . .
C1 C 0.16313(19) 0.3223(2) 0.2454(5) 0.0608(10) Uani 1 1 d . . . . .
H1A H 0.156755 0.349151 0.173082 0.073 Uiso 1 1 calc R U . . .
H1B H 0.200005 0.322806 0.210252 0.073 Uiso 1 1 calc R U . . .
C2 C 0.05365(18) 0.24735(18) 0.2186(5) 0.0540(9) Uani 1 1 d . . . . .
C3 C 0.03666(19) 0.2917(2) 0.2055(5) 0.0583(10) Uani 1 1 d . . . . .
H3 H 0.066345 0.332573 0.213135 0.070 Uiso 1 1 calc R U . . .
C4 C -0.0223(2) 0.2763(2) 0.1819(6) 0.0675(12) Uani 1 1 d . . . . .
H4 H -0.032816 0.306445 0.171033 0.081 Uiso 1 1 calc R U . . .
C5 C -0.0665(2) 0.2158(3) 0.1741(6) 0.0762(14) Uani 1 1 d . . . . .
H5 H -0.107136 0.204550 0.157851 0.091 Uiso 1 1 calc R U . . .
C6 C -0.0504(2) 0.1739(3) 0.1901(7) 0.0858(16) Uani 1 1 d . . . . .
H6 H -0.080489 0.133093 0.185398 0.103 Uiso 1 1 calc R U . . .
C7A C 0.0269(8) 0.1418(7) 0.180(2) 0.112(2) Uani 0.533(8) 1 d D . P A 1
H7A H 0.010874 0.122585 0.073184 0.135 Uiso 0.533(8) 1 calc R U P A 1
H7B H 0.071003 0.161273 0.175573 0.135 Uiso 0.533(8) 1 calc R U P A 1
C8A C 0.0033(7) 0.0958(6) 0.3107(17) 0.112(2) Uani 0.533(8) 1 d D . P A 1
H8A H 0.032460 0.108309 0.399062 0.168 Uiso 0.533(8) 1 calc R U P A 1
H8B H -0.003909 0.057539 0.266801 0.168 Uiso 0.533(8) 1 calc R U P A 1
H8C H -0.034233 0.091352 0.352186 0.168 Uiso 0.533(8) 1 calc R U P A 1
C7B C 0.0216(10) 0.1382(8) 0.289(2) 0.112(2) Uani 0.467(8) 1 d D . P A 2
H7C H 0.060187 0.156782 0.347866 0.135 Uiso 0.467(8) 1 calc R U P A 2
H7D H -0.010699 0.111223 0.363974 0.135 Uiso 0.467(8) 1 calc R U P A 2
C8B C 0.0234(8) 0.1056(7) 0.1392(19) 0.112(2) Uani 0.467(8) 1 d D . P A 2
H8D H 0.047436 0.134679 0.055409 0.168 Uiso 0.467(8) 1 calc R U P A 2
H8E H -0.017335 0.080112 0.098580 0.168 Uiso 0.467(8) 1 calc R U P A 2
H8F H 0.041095 0.080950 0.166052 0.168 Uiso 0.467(8) 1 calc R U P A 2
I1 I 0.20299(2) 0.19160(2) 0.29278(4) 0.07055(16) Uani 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
N1 C2 1.331(5) . ?
N1 C1 1.465(6) . ?
N1 H1 0.8600 . ?
N2 C2 1.360(5) . ?
N2 C6 1.363(6) . ?
N2 C7A 1.488(15) . ?
N2 C7B 1.580(17) . ?
C1 C1 1.503(9) 16 ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C2 C3 1.393(6) . ?
C3 C4 1.357(6) . ?
C3 H3 0.9300 . ?
C4 C5 1.375(7) . ?
C4 H4 0.9300 . ?
C5 C6 1.320(8) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C7A C8A 1.462(14) . ?
C7A H7A 0.9700 . ?
C7A H7B 0.9700 . ?
C8A H8A 0.9600 . ?
C8A H8B 0.9600 . ?
C8A H8C 0.9600 . ?
C7B C8B 1.479(15) . ?
C7B H7C 0.9700 . ?
C7B H7D 0.9700 . ?
C8B H8D 0.9600 . ?
C8B H8E 0.9600 . ?
C8B H8F 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
C2 N1 C1 123.7(4) . . ?
C2 N1 H1 118.2 . . ?
C1 N1 H1 118.2 . . ?
C2 N2 C6 120.0(4) . . ?
C2 N2 C7A 117.1(7) . . ?
C6 N2 C7A 120.1(8) . . ?
C2 N2 C7B 118.3(8) . . ?
C6 N2 C7B 118.9(8) . . ?
N1 C1 C1 110.0(5) . 16 ?
N1 C1 H1A 109.7 . . ?
C1 C1 H1A 109.7 16 . ?
N1 C1 H1B 109.7 . . ?
C1 C1 H1B 109.7 16 . ?
H1A C1 H1B 108.2 . . ?
N1 C2 N2 119.1(4) . . ?
N1 C2 C3 123.5(4) . . ?
N2 C2 C3 117.4(4) . . ?
C4 C3 C2 121.3(4) . . ?
C4 C3 H3 119.3 . . ?
C2 C3 H3 119.3 . . ?
C3 C4 C5 119.5(5) . . ?
C3 C4 H4 120.3 . . ?
C5 C4 H4 120.3 . . ?
C6 C5 C4 119.0(5) . . ?
C6 C5 H5 120.5 . . ?
C4 C5 H5 120.5 . . ?
C5 C6 N2 122.8(5) . . ?
C5 C6 H6 118.6 . . ?
N2 C6 H6 118.6 . . ?
C8A C7A N2 109.3(12) . . ?
C8A C7A H7A 109.8 . . ?
N2 C7A H7A 109.8 . . ?
C8A C7A H7B 109.8 . . ?
N2 C7A H7B 109.8 . . ?
H7A C7A H7B 108.3 . . ?
C7A C8A H8A 109.5 . . ?
C7A C8A H8B 109.5 . . ?
H8A C8A H8B 109.5 . . ?
C7A C8A H8C 109.5 . . ?
H8A C8A H8C 109.5 . . ?
H8B C8A H8C 109.5 . . ?
C8B C7B N2 101.8(13) . . ?
C8B C7B H7C 111.4 . . ?
N2 C7B H7C 111.4 . . ?
C8B C7B H7D 111.4 . . ?
N2 C7B H7D 111.4 . . ?
H7C C7B H7D 109.3 . . ?
C7B C8B H8D 109.5 . . ?
C7B C8B H8E 109.5 . . ?
H8D C8B H8E 109.5 . . ?
C7B C8B H8F 109.5 . . ?
H8D C8B H8F 109.5 . . ?
H8E C8B H8F 109.5 . . ?

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 C1 C1 82.2(6) . . . 16 ?
C1 N1 C2 N2 -177.7(4) . . . . ?
C1 N1 C2 C3 3.5(7) . . . . ?
C6 N2 C2 N1 -176.5(5) . . . . ?
C7A N2 C2 N1 -15.6(9) . . . . ?
C7B N2 C2 N1 22.6(9) . . . . ?
C6 N2 C2 C3 2.3(7) . . . . ?
C7A N2 C2 C3 163.2(8) . . . . ?
C7B N2 C2 C3 -158.6(8) . . . . ?
N1 C2 C3 C4 176.2(4) . . . . ?
N2 C2 C3 C4 -2.6(7) . . . . ?
C2 C3 C4 C5 1.4(7) . . . . ?
C3 C4 C5 C6 0.1(7) . . . . ?
C4 C5 C6 N2 -0.3(9) . . . . ?
C2 N2 C6 C5 -0.9(9) . . . . ?
C7A N2 C6 C5 -161.3(8) . . . . ?
C7B N2 C6 C5 159.9(8) . . . . ?
C2 N2 C7A C8A 125.8(11) . . . . ?
C6 N2 C7A C8A -73.3(15) . . . . ?
C2 N2 C7B C8B -110.5(12) . . . . ?
C6 N2 C7B C8B 88.4(13) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N1 H1 I1 0.86 2.81 3.565(4) 147.3 . yes
C6 H6 I1 0.93 3.08 3.964(5) 158.8 2 yes
C7A^a H7B^a I1 0.97 3.18 4.087(18) 156.6 . yes
C7B^b H7C^b I1 0.97 3.30 4.09(2) 140.3 . yes

_refine_diff_density_max         0.638
_refine_diff_density_min         -0.717
_refine_diff_density_rms         0.078

_chemical_melting_point          '304 \oC'
####################################################################### 
# 
# 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_srm2bqau
_database_code_depnum_ccdc_archive 'CCDC 1955343'
loop_
_audit_author_name
_audit_author_address
'Muhammad Nawaz Tahir'
;Department of Physics University of Sargodha Sargodha Pakistan
Pakistan
;
_audit_update_record             
;
2019-11-05 deposited with the CCDC.	2019-11-08 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_absolute_configuration .
_chemical_name_systematic        
"(2E,2'E)-N,N'-(ethane-1,2-diyl)bis(1-methylpyridin-2(1H)-iminium) di-trifluoromethanesulfonate"
_chemical_formula_moiety         '	C14 H20 N4, 2(C F3 O3 S)'
_chemical_formula_sum            'C16 H20 F6 N4 O6 S2'
_chemical_formula_iupac          'C16 H20 F6 N4 O6 S2'
_chemical_formula_weight         542.48

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'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_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+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   6.7528(5)
_cell_length_b                   20.0716(17)
_cell_length_c                   8.2927(9)
_cell_angle_alpha                90
_cell_angle_beta                 104.010(3)
_cell_angle_gamma                90
_cell_volume                     1090.55(17)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2027
_cell_measurement_theta_min      2.727
_cell_measurement_theta_max      27.865
_cell_measurement_temperature    296(2)
_exptl_crystal_description       prism
_exptl_crystal_colour            'brown solid'
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.22
_exptl_crystal_density_diffrn    1.652
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             556
_exptl_absorpt_coefficient_mu    0.338
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2005)'
_exptl_absorpt_correction_T_min  0.850
_exptl_absorpt_correction_T_max  0.910
_exptl_special_details           
;
;


_diffrn_ambient_temperature      296(2)
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker Kappa APEXII CCD'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 7.60
_diffrn_reflns_number            7473
_diffrn_reflns_av_unetI/netI     0.0405
_diffrn_reflns_av_R_equivalents  0.0355
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         2.727
_diffrn_reflns_theta_max         27.865
_diffrn_reflns_theta_full        27.865
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measured_fraction_theta_full 0.991
_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?

_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 >
σ(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.
;
_reflns_number_total             2574
_reflns_number_gt                2027
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0581
_refine_ls_R_factor_gt           0.0446
_refine_ls_wR_factor_ref         0.1259
_refine_ls_wR_factor_gt          0.1162
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_restrained_S_all      1.050
_refine_ls_number_reflns         2574
_refine_ls_number_parameters     155
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0600P)²+0.3247P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_computing_data_collection       'APEX2 (Bruker, 2007)'
_computing_cell_refinement       'SAINT (Bruker, 2007)'
_computing_data_reduction        'SAINT (Bruker, 2007)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2018/3  (Sheldrick, 2015)'
_computing_molecular_graphics    
'ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2009)'
_computing_publication_material  
;
WinGX (Farrugia, 1999) and PLATON (Spek, 2009)
;


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
N1 N 0.3811(2) 0.05236(8) 0.6380(2) 0.0392(4) Uani 1 1 d . . . . .
H1 H 0.289599 0.034674 0.680809 0.047 Uiso 1 1 calc R U . . .
N2 N 0.2361(2) 0.15499(8) 0.67009(19) 0.0395(4) Uani 1 1 d . . . . .
C1 C 0.5319(3) 0.00878(9) 0.5916(2) 0.0379(4) Uani 1 1 d . . . . .
H1A H 0.545991 -0.031708 0.657311 0.045 Uiso 1 1 calc R U . . .
H1B H 0.663348 0.030966 0.615350 0.045 Uiso 1 1 calc R U . . .
C2 C 0.3789(3) 0.11846(9) 0.6169(2) 0.0331(4) Uani 1 1 d . . . . .
C3 C 0.5203(3) 0.15284(10) 0.5482(2) 0.0402(4) Uani 1 1 d . . . . .
H3 H 0.617018 0.129104 0.508608 0.048 Uiso 1 1 calc R U . . .
C4 C 0.5170(4) 0.22059(11) 0.5390(3) 0.0510(5) Uani 1 1 d . . . . .
H4 H 0.612710 0.242998 0.495304 0.061 Uiso 1 1 calc R U . . .
C5 C 0.3694(4) 0.25641(11) 0.5956(3) 0.0601(6) Uani 1 1 d . . . . .
H5 H 0.366513 0.302699 0.590591 0.072 Uiso 1 1 calc R U . . .
C6 C 0.2318(4) 0.22292(11) 0.6571(3) 0.0517(5) Uani 1 1 d . . . . .
H6 H 0.131136 0.246546 0.691848 0.062 Uiso 1 1 calc R U . . .
C7 C 0.0895(3) 0.12132(13) 0.7462(3) 0.0552(6) Uani 1 1 d . . . . .
H7A H 0.011794 0.089885 0.668896 0.083 Uiso 1 1 calc R U . . .
H7B H -0.000838 0.153641 0.775147 0.083 Uiso 1 1 calc R U . . .
H7C H 0.161317 0.098328 0.844535 0.083 Uiso 1 1 calc R U . . .
S1 S 0.93018(8) 0.10975(3) 0.24778(6) 0.04219(18) Uani 1 1 d . . . . .
F1 F 0.7333(3) 0.13805(8) -0.05705(17) 0.0744(5) Uani 1 1 d . . . . .
F2 F 0.5584(2) 0.08317(10) 0.07742(19) 0.0792(5) Uani 1 1 d . . . . .
F3 F 0.7917(3) 0.03476(9) -0.0122(2) 0.0921(6) Uani 1 1 d . . . . .
O1 O 0.8609(3) 0.17254(10) 0.2965(2) 0.0759(6) Uani 1 1 d . . . . .
O2 O 0.9085(3) 0.05512(10) 0.3534(2) 0.0762(6) Uani 1 1 d . . . . .
O3 O 1.1197(2) 0.11238(10) 0.2003(2) 0.0689(5) Uani 1 1 d . . . . .
C8 C 0.7446(3) 0.08993(11) 0.0550(2) 0.0468(5) Uani 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
N1 C2 1.338(2) . ?
N1 C1 1.463(2) . ?
N1 H1 0.8600 . ?
N2 C2 1.367(2) . ?
N2 C6 1.368(3) . ?
N2 C7 1.462(3) . ?
C1 C1 1.517(4) 3_656 ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C2 C3 1.406(3) . ?
C3 C4 1.362(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.399(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.344(3) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
S1 O3 1.4282(17) . ?
S1 O2 1.4326(16) . ?
S1 O1 1.4360(19) . ?
S1 C8 1.820(2) . ?
F1 C8 1.330(2) . ?
F2 C8 1.322(3) . ?
F3 C8 1.313(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
C2 N1 C1 123.02(15) . . ?
C2 N1 H1 118.5 . . ?
C1 N1 H1 118.5 . . ?
C2 N2 C6 120.84(18) . . ?
C2 N2 C7 119.72(17) . . ?
C6 N2 C7 119.42(18) . . ?
N1 C1 C1 110.83(19) . 3_656 ?
N1 C1 H1A 109.5 . . ?
C1 C1 H1A 109.5 3_656 . ?
N1 C1 H1B 109.5 . . ?
C1 C1 H1B 109.5 3_656 . ?
H1A C1 H1B 108.1 . . ?
N1 C2 N2 118.43(16) . . ?
N1 C2 C3 123.56(17) . . ?
N2 C2 C3 117.97(17) . . ?
C4 C3 C2 120.60(19) . . ?
C4 C3 H3 119.7 . . ?
C2 C3 H3 119.7 . . ?
C3 C4 C5 119.9(2) . . ?
C3 C4 H4 120.1 . . ?
C5 C4 H4 120.1 . . ?
C6 C5 C4 119.0(2) . . ?
C6 C5 H5 120.5 . . ?
C4 C5 H5 120.5 . . ?
C5 C6 N2 121.7(2) . . ?
C5 C6 H6 119.2 . . ?
N2 C6 H6 119.2 . . ?
N2 C7 H7A 109.5 . . ?
N2 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
N2 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
O3 S1 O2 115.31(12) . . ?
O3 S1 O1 114.84(12) . . ?
O2 S1 O1 114.29(13) . . ?
O3 S1 C8 103.78(11) . . ?
O2 S1 C8 102.66(10) . . ?
O1 S1 C8 103.70(11) . . ?
F3 C8 F2 108.0(2) . . ?
F3 C8 F1 107.17(18) . . ?
F2 C8 F1 106.09(18) . . ?
F3 C8 S1 111.78(15) . . ?
F2 C8 S1 112.01(14) . . ?
F1 C8 S1 111.46(16) . . ?

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 C1 C1 -83.7(3) . . . 3_656 ?
C1 N1 C2 N2 -177.59(16) . . . . ?
C1 N1 C2 C3 0.1(3) . . . . ?
C6 N2 C2 N1 177.58(17) . . . . ?
C7 N2 C2 N1 -0.7(2) . . . . ?
C6 N2 C2 C3 -0.2(2) . . . . ?
C7 N2 C2 C3 -178.44(17) . . . . ?
N1 C2 C3 C4 -176.14(19) . . . . ?
N2 C2 C3 C4 1.5(3) . . . . ?
C2 C3 C4 C5 -1.2(3) . . . . ?
C3 C4 C5 C6 -0.5(3) . . . . ?
C4 C5 C6 N2 1.8(3) . . . . ?
C2 N2 C6 C5 -1.5(3) . . . . ?
C7 N2 C6 C5 176.7(2) . . . . ?
O3 S1 C8 F3 56.38(19) . . . . ?
O2 S1 C8 F3 -64.04(19) . . . . ?
O1 S1 C8 F3 176.70(18) . . . . ?
O3 S1 C8 F2 177.76(16) . . . . ?
O2 S1 C8 F2 57.35(19) . . . . ?
O1 S1 C8 F2 -61.91(19) . . . . ?
O3 S1 C8 F1 -63.54(18) . . . . ?
O2 S1 C8 F1 176.05(16) . . . . ?
O1 S1 C8 F1 56.79(18) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N1 H1 O2 0.86 2.22 2.924(2) 138.8 3_656 yes
C7 H7A O2 0.96 2.63 3.456(3) 143.9 1_455 yes
C7 H7B F1 0.96 2.54 3.234(3) 129.0 1_456 yes

_refine_diff_density_max         0.336
_refine_diff_density_min         -0.293
_refine_diff_density_rms         0.050

_chemical_melting_point          '232 ?C'
####################################################################### 
# 
# 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_2CLPYET
_database_code_depnum_ccdc_archive 'CCDC 1961686'
loop_
_audit_author_name
_audit_author_address
'Muhammad Nawaz Tahir'
;Department of Physics University of Sargodha Sargodha Pakistan
Pakistan
;
_audit_update_record             
;
2019-11-05 deposited with the CCDC.	2019-11-08 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_absolute_configuration .
_chemical_name_systematic        
;
1-Ethyl-2-iodopyridin-1-ium iodide
;
_chemical_formula_moiety         'C7 H9 I N, I'
_chemical_formula_sum            'C7 H9 I2 N'
_chemical_formula_iupac          'C7 H9 I2 N'
_chemical_formula_weight         360.95

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'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           62
_space_group_name_H-M_alt        'P n m a'
_space_group_name_Hall           '-P 2ac 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+1/2, -y, z+1/2'
'-x, y+1/2, -z'
'x+1/2, -y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z'
'-x-1/2, y-1/2, z-1/2'

_cell_length_a                   16.0537(15)
_cell_length_b                   7.2941(6)
_cell_length_c                   8.9376(9)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1046.57(17)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1160
_cell_measurement_theta_min      2.537
_cell_measurement_theta_max      27.000
_cell_measurement_temperature    296(2)
_exptl_crystal_description       needle
_exptl_crystal_colour            'Royal yellow solid'
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.18
_exptl_crystal_density_diffrn    2.291
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             656
_exptl_absorpt_coefficient_mu    5.949
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2005)'
_exptl_absorpt_correction_T_min  0.220
_exptl_absorpt_correction_T_max  0.450
_exptl_special_details           
;
;


_diffrn_ambient_temperature      296(2)
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker Kappa APEXII CCD'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 7.83
_diffrn_reflns_number            11825
_diffrn_reflns_av_unetI/netI     0.0151
_diffrn_reflns_av_R_equivalents  0.0255
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         2.537
_diffrn_reflns_theta_max         27.000
_diffrn_reflns_theta_full        27.000
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measured_fraction_theta_full 0.989
_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?

_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 >
σ(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.
;
_reflns_number_total             1225
_reflns_number_gt                1160
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0210
_refine_ls_R_factor_gt           0.0189
_refine_ls_wR_factor_ref         0.0455
_refine_ls_wR_factor_gt          0.0440
_refine_ls_goodness_of_fit_ref   1.086
_refine_ls_restrained_S_all      1.086
_refine_ls_number_reflns         1225
_refine_ls_number_parameters     62
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0181P)²+1.0559P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_computing_data_collection       'APEX2 (Bruker, 2007)'
_computing_cell_refinement       'SAINT (Bruker, 2007)'
_computing_data_reduction        'SAINT (Bruker, 2007)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2018/3  (Sheldrick, 2015)'
_computing_molecular_graphics    
'ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2009)'
_computing_publication_material  
;
WinGX (Farrugia, 1999) and PLATON (Spek, 2009)
;


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
I1 I 0.20790(2) 0.750000 0.00903(3) 0.04842(10) Uani 1 2 d S T P . .
N1 N 0.09226(19) 0.750000 0.2806(3) 0.0379(6) Uani 1 2 d S T P . .
C1 C 0.0943(2) 0.750000 0.1297(4) 0.0409(8) Uani 1 2 d S T P . .
C2 C 0.0214(3) 0.750000 0.0492(5) 0.0537(10) Uani 1 2 d S T P . .
H2 H 0.023261 0.750000 -0.054776 0.064 Uiso 1 2 calc R U P . .
C3 C -0.0546(3) 0.750000 0.1213(5) 0.0649(13) Uani 1 2 d S T P . .
H3 H -0.104026 0.750000 0.067067 0.078 Uiso 1 2 calc R U P . .
C4 C -0.0556(3) 0.750000 0.2749(5) 0.0621(12) Uani 1 2 d S T P . .
H4 H -0.105939 0.750000 0.326335 0.075 Uiso 1 2 calc R U P . .
C5 C 0.0182(3) 0.750000 0.3517(5) 0.0519(10) Uani 1 2 d S T P . .
H5 H 0.017169 0.750000 0.455727 0.062 Uiso 1 2 calc R U P . .
C6 C 0.1714(2) 0.750000 0.3697(4) 0.0455(8) Uani 1 2 d S T P . .
H6A H 0.203562 0.857188 0.341749 0.055 Uiso 0.5 1 calc R U P . .
H6B H 0.203562 0.642812 0.341749 0.055 Uiso 0.5 1 calc R U P . .
C7 C 0.1612(3) 0.750000 0.5367(5) 0.0666(13) Uani 1 2 d S T P . .
H7A H 0.215022 0.750000 0.583365 0.100 Uiso 1 2 calc R U P . .
H7B H 0.130959 0.857462 0.566780 0.100 Uiso 0.5 1 calc R U P . .
H7C H 0.130959 0.642538 0.566780 0.100 Uiso 0.5 1 calc R U P . .
I2 I 0.11429(2) 0.250000 0.29768(3) 0.04434(9) Uani 1 2 d S T P . .


_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
I1 C1 2.119(4) . ?
N1 C5 1.348(5) . ?
N1 C1 1.349(5) . ?
N1 C6 1.499(4) . ?
C1 C2 1.374(5) . ?
C2 C3 1.379(6) . ?
C2 H2 0.9300 . ?
C3 C4 1.373(7) . ?
C3 H3 0.9300 . ?
C4 C5 1.368(6) . ?
C4 H4 0.9300 . ?
C5 H5 0.9300 . ?
C6 C7 1.501(6) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 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
C5 N1 C1 119.5(3) . . ?
C5 N1 C6 119.8(3) . . ?
C1 N1 C6 120.7(3) . . ?
N1 C1 C2 120.2(3) . . ?
N1 C1 I1 122.0(3) . . ?
C2 C1 I1 117.8(3) . . ?
C1 C2 C3 120.6(4) . . ?
C1 C2 H2 119.7 . . ?
C3 C2 H2 119.7 . . ?
C4 C3 C2 118.5(4) . . ?
C4 C3 H3 120.7 . . ?
C2 C3 H3 120.7 . . ?
C5 C4 C3 119.4(4) . . ?
C5 C4 H4 120.3 . . ?
C3 C4 H4 120.3 . . ?
N1 C5 C4 121.8(4) . . ?
N1 C5 H5 119.1 . . ?
C4 C5 H5 119.1 . . ?
N1 C6 C7 115.8(4) . . ?
N1 C6 H6A 108.3 . . ?
C7 C6 H6A 108.3 . . ?
N1 C6 H6B 108.3 . . ?
C7 C6 H6B 108.3 . . ?
H6A C6 H6B 107.4 . . ?
C6 C7 H7A 109.5 . . ?
C6 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C6 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?

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
C5 N1 C1 C2 0.000(0) . . . . ?
C6 N1 C1 C2 180.000(0) . . . . ?
C5 N1 C1 I1 180.000(0) . . . . ?
C6 N1 C1 I1 0.000(0) . . . . ?
N1 C1 C2 C3 0.000(0) . . . . ?
I1 C1 C2 C3 180.000(0) . . . . ?
C1 C2 C3 C4 0.000(0) . . . . ?
C2 C3 C4 C5 0.000(0) . . . . ?
C1 N1 C5 C4 0.000(0) . . . . ?
C6 N1 C5 C4 180.000(0) . . . . ?
C3 C4 C5 N1 0.000(0) . . . . ?
C5 N1 C6 C7 0.000(0) . . . . ?
C1 N1 C6 C7 180.000(0) . . . . ?

_refine_diff_density_max         0.431
_refine_diff_density_min         -0.493
_refine_diff_density_rms         0.068

_chemical_melting_point          '156 \oC'
####################################################################### 
# 
# 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_17012
_database_code_depnum_ccdc_archive 'CCDC 1955349'
loop_
_audit_author_name
_audit_author_address
'Muhammad Nawaz Tahir'
;Department of Physics University of Sargodha Sargodha Pakistan
Pakistan
;
_audit_update_record             
;
2019-11-05 deposited with the CCDC.	2019-11-08 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_absolute_configuration .
_chemical_name_systematic        
;
2-Chloro-1-methylpyridin-1-ium trifluoromethanesulfonate
;
_chemical_formula_moiety         'C6 H7 Cl N, C F3 O3 S'
_chemical_formula_sum            'C7 H7 Cl F3 N O3 S'
_chemical_formula_iupac          'C7 H7 Cl F3 N O3 S'
_chemical_formula_weight         277.65

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'
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'
S S 0.1246 0.1234 '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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_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+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   6.6961(5)
_cell_length_b                   9.9947(10)
_cell_length_c                   16.1264(14)
_cell_angle_alpha                90
_cell_angle_beta                 99.272(8)
_cell_angle_gamma                90
_cell_volume                     1065.17(16)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1846
_cell_measurement_theta_min      3.141
_cell_measurement_theta_max      27.00
_cell_measurement_temperature    293(2)
_exptl_crystal_description       needle
_exptl_crystal_colour            'colorless solid'
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.18
_exptl_crystal_density_diffrn    1.731
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             560
_exptl_absorpt_coefficient_mu    0.588
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2005)'
_exptl_absorpt_correction_T_min  0.805
_exptl_absorpt_correction_T_max  0.920
_exptl_special_details           
;
;


_diffrn_ambient_temperature      293(2)
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker Kappa APEXII CCD'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 7.70
_diffrn_reflns_number            5036
_diffrn_reflns_av_unetI/netI     0.0309
_diffrn_reflns_av_R_equivalents  0.0251
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         3.141
_diffrn_reflns_theta_max         27.000
_diffrn_reflns_theta_full        27.000
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.996
_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?

_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 >
σ(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.
;
_reflns_number_total             2325
_reflns_number_gt                1846
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0536
_refine_ls_R_factor_gt           0.0405
_refine_ls_wR_factor_ref         0.1076
_refine_ls_wR_factor_gt          0.0966
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_restrained_S_all      1.027
_refine_ls_number_reflns         2325
_refine_ls_number_parameters     147
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0459P)²+0.3872P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_extinction_coef       0.057(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_computing_data_collection       'APEX2 (Bruker, 2007)'
_computing_cell_refinement       'SAINT (Bruker, 2007)'
_computing_data_reduction        'SAINT (Bruker, 2007)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2018/3  (Sheldrick, 2015)'
_computing_molecular_graphics    
'ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2009)'
_computing_publication_material  
;
WinGX (Farrugia, 1999) and PLATON (Spek, 2009)
;


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
Cl1 Cl 0.36189(10) 0.41039(9) 0.07604(5) 0.0789(3) Uani 1 1 d . . . . .
N1 N 0.6162(3) 0.21843(18) 0.12686(10) 0.0418(4) Uani 1 1 d . . . . .
C1 C 0.5907(3) 0.3520(2) 0.12242(13) 0.0444(5) Uani 1 1 d . . . . .
C2 C 0.7444(4) 0.4372(3) 0.15417(15) 0.0544(6) Uani 1 1 d . . . . .
H2 H 0.726187 0.529311 0.149858 0.065 Uiso 1 1 calc R U . . .
C3 C 0.9253(4) 0.3851(3) 0.19235(15) 0.0587(7) Uani 1 1 d . . . . .
H3 H 1.030909 0.441627 0.214313 0.070 Uiso 1 1 calc R U . . .
C4 C 0.9495(4) 0.2491(3) 0.19796(15) 0.0576(7) Uani 1 1 d . . . . .
H4 H 1.070986 0.212675 0.224413 0.069 Uiso 1 1 calc R U . . .
C5 C 0.7947(4) 0.1681(3) 0.16461(14) 0.0500(6) Uani 1 1 d . . . . .
H5 H 0.812075 0.075874 0.167839 0.060 Uiso 1 1 calc R U . . .
C6 C 0.4518(4) 0.1246(3) 0.09291(17) 0.0641(7) Uani 1 1 d . . . . .
H6A H 0.503478 0.034852 0.095778 0.096 Uiso 1 1 calc R U . . .
H6B H 0.401368 0.147113 0.035485 0.096 Uiso 1 1 calc R U . . .
H6C H 0.344195 0.131126 0.125484 0.096 Uiso 1 1 calc R U . . .
S1 S 0.48924(8) 0.31188(6) 0.34283(3) 0.0416(2) Uani 1 1 d . . . . .
F1 F 0.1683(2) 0.2621(2) 0.41000(12) 0.0887(6) Uani 1 1 d . . . . .
F2 F 0.4328(3) 0.1644(2) 0.47057(11) 0.0910(6) Uani 1 1 d . . . . .
F3 F 0.3945(4) 0.3736(2) 0.48780(12) 0.1211(9) Uani 1 1 d . . . . .
O1 O 0.3891(3) 0.43067(18) 0.30861(12) 0.0661(5) Uani 1 1 d . . . . .
O2 O 0.4456(3) 0.19655(19) 0.29102(12) 0.0701(5) Uani 1 1 d . . . . .
O3 O 0.6965(2) 0.3291(2) 0.37935(12) 0.0694(6) Uani 1 1 d . . . . .
C7 C 0.3662(4) 0.2762(3) 0.43181(15) 0.0558(6) Uani 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
Cl1 C1 1.697(2) . ?
N1 C1 1.346(3) . ?
N1 C5 1.348(3) . ?
N1 C6 1.482(3) . ?
C1 C2 1.370(3) . ?
C2 C3 1.370(4) . ?
C2 H2 0.9300 . ?
C3 C4 1.370(4) . ?
C3 H3 0.9300 . ?
C4 C5 1.356(4) . ?
C4 H4 0.9300 . ?
C5 H5 0.9300 . ?
C6 H6A 0.9600 . ?
C6 H6B 0.9600 . ?
C6 H6C 0.9600 . ?
S1 O2 1.4261(18) . ?
S1 O3 1.4279(17) . ?
S1 O1 1.4297(18) . ?
S1 C7 1.802(2) . ?
F1 C7 1.322(3) . ?
F2 C7 1.322(3) . ?
F3 C7 1.320(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
C1 N1 C5 119.3(2) . . ?
C1 N1 C6 121.9(2) . . ?
C5 N1 C6 118.9(2) . . ?
N1 C1 C2 121.0(2) . . ?
N1 C1 Cl1 117.53(17) . . ?
C2 C1 Cl1 121.4(2) . . ?
C3 C2 C1 119.2(2) . . ?
C3 C2 H2 120.4 . . ?
C1 C2 H2 120.4 . . ?
C4 C3 C2 119.6(2) . . ?
C4 C3 H3 120.2 . . ?
C2 C3 H3 120.2 . . ?
C5 C4 C3 119.4(2) . . ?
C5 C4 H4 120.3 . . ?
C3 C4 H4 120.3 . . ?
N1 C5 C4 121.5(2) . . ?
N1 C5 H5 119.3 . . ?
C4 C5 H5 119.3 . . ?
N1 C6 H6A 109.5 . . ?
N1 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
N1 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
O2 S1 O3 115.66(12) . . ?
O2 S1 O1 113.95(12) . . ?
O3 S1 O1 115.02(12) . . ?
O2 S1 C7 103.27(12) . . ?
O3 S1 C7 103.55(11) . . ?
O1 S1 C7 103.05(12) . . ?
F3 C7 F2 107.4(2) . . ?
F3 C7 F1 106.7(2) . . ?
F2 C7 F1 106.5(2) . . ?
F3 C7 S1 111.38(18) . . ?
F2 C7 S1 112.40(19) . . ?
F1 C7 S1 112.11(18) . . ?

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
C5 N1 C1 C2 1.3(3) . . . . ?
C6 N1 C1 C2 180.0(2) . . . . ?
C5 N1 C1 Cl1 -178.82(15) . . . . ?
C6 N1 C1 Cl1 -0.1(3) . . . . ?
N1 C1 C2 C3 -1.2(3) . . . . ?
Cl1 C1 C2 C3 178.86(17) . . . . ?
C1 C2 C3 C4 0.1(4) . . . . ?
C2 C3 C4 C5 0.9(4) . . . . ?
C1 N1 C5 C4 -0.2(3) . . . . ?
C6 N1 C5 C4 -179.0(2) . . . . ?
C3 C4 C5 N1 -0.8(3) . . . . ?
O2 S1 C7 F3 179.0(2) . . . . ?
O3 S1 C7 F3 58.0(2) . . . . ?
O1 S1 C7 F3 -62.2(2) . . . . ?
O2 S1 C7 F2 58.4(2) . . . . ?
O3 S1 C7 F2 -62.6(2) . . . . ?
O1 S1 C7 F2 177.26(17) . . . . ?
O2 S1 C7 F1 -61.5(2) . . . . ?
O3 S1 C7 F1 177.5(2) . . . . ?
O1 S1 C7 F1 57.4(2) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
C4 H4 O2 0.93 2.57 3.458(3) 159.9 1_655 yes
C5 H5 S1 0.93 2.97 3.853(3) 158.5 2_645 yes
C5 H5 O1 0.93 2.45 3.163(3) 133.4 2_645 yes
C5 H5 O3 0.93 2.58 3.464(3) 159.3 2_645 yes

_refine_diff_density_max         0.240
_refine_diff_density_min         -0.310
_refine_diff_density_rms         0.047

_chemical_melting_point          '161 \oC'
