# Supplementary Information (SI) for Journal of Materials Chemistry A.
# This journal is © The Royal Society of Chemistry 2026

####################################################################### 
# 
# 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_HPhTz(F)
_database_code_depnum_ccdc_archive 'CCDC 2448941'
loop_
_audit_author_name
_audit_author_address
'Andrea Rossin'
;CNR ICCOM
Italy
;
_audit_update_record             
;
2025-05-06 deposited with the CCDC.	2026-02-24 downloaded from the CCDC.
;

_audit_creation_date             2024-03-06T14:32:35-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_formula_sum            'C11 H11 Br F N O3 S'
_chemical_formula_moiety         'C11 H9 F N O2 S, Br, H2 O'
_chemical_formula_weight         336.18

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/c'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_Int_Tables_number      14
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   13.6968(6)
_cell_length_b                   12.6423(6)
_cell_length_c                   7.7593(3)
_cell_angle_alpha                90
_cell_angle_beta                 100.0900(10)
_cell_angle_gamma                90
_cell_volume                     1322.81(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.07
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.04
_exptl_crystal_density_diffrn    1.688
_exptl_crystal_F_000             672

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    5.851
_exptl_absorpt_correction_type   none
_shelx_estimated_absorpt_T_min   0.067
_shelx_estimated_absorpt_T_max   0.158

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_reflns_av_R_equivalents  0.0528
_diffrn_reflns_av_unetI/netI     0.0314
_diffrn_reflns_number            20869
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         3.277
_diffrn_reflns_theta_max         72.318
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_reflns_Friedel_coverage         0
_reflns_number_total             2601
_reflns_number_gt                2568
_reflns_threshold_expression     'I > 2σ(I)'

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION                                       #
#----------------------------------------------------------------------------#

_atom_sites_solution_hydrogens   mixed

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_shelx_SHELXL_version_number     2018/3
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0877P)²+6.8557P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_number_reflns         2601
_refine_ls_number_parameters     158
_refine_ls_number_restraints     6
_refine_ls_R_factor_all          0.0618
_refine_ls_R_factor_gt           0.0608
_refine_ls_wR_factor_ref         0.167
_refine_ls_wR_factor_gt          0.1663
_refine_ls_goodness_of_fit_ref   1.177
_refine_ls_restrained_S_all      1.176
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_diff_density_max         4.154
_refine_diff_density_min         -1.541
_refine_diff_density_rms         0.182

#----------------------------------------------------------------------------#
#                   CONSTRAINTS AND RESTRAINTS                               #
#----------------------------------------------------------------------------#


#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.6763 1.2805 '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'
N N 0.0311 0.018 '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'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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
C1 C 0.6261(3) 0.3018(4) 0.1291(6) 0.0165(9) Uani 1 1 d . . . . .
C2 C 0.5286(3) 0.3525(4) 0.1435(6) 0.0150(9) Uani 1 1 d . . . . .
C3 C 0.4424(4) 0.2992(4) 0.0662(7) 0.0239(10) Uani 1 1 d . . . . .
H3 H 0.445452 0.232357 0.011363 0.029 Uiso 1 1 calc R U . . .
C4 C 0.3527(4) 0.3475(4) 0.0726(7) 0.0234(10) Uani 1 1 d . . . . .
C5 C 0.3432(3) 0.4438(4) 0.1504(6) 0.0162(9) Uani 1 1 d . . . . .
C6 C 0.4305(3) 0.4947(3) 0.2285(5) 0.0094(5) Uani 1 1 d . . . . .
H6 H 0.426889 0.561107 0.284399 0.011 Uiso 1 1 calc R U . . .
C7 C 0.5223(3) 0.4488(4) 0.2251(6) 0.0181(9) Uani 1 1 d . . . . .
H7 H 0.581159 0.483895 0.27905 0.022 Uiso 1 1 calc R U . . .
C8 C 0.2426(3) 0.4954(4) 0.1444(6) 0.0184(9) Uani 1 1 d . . . . .
H8A H 0.250272 0.573234 0.142175 0.022 Uiso 1 1 calc R U . . .
H8B H 0.197997 0.473987 0.035545 0.022 Uiso 1 1 calc R U . . .
C9 C 0.1340(4) 0.3855(4) 0.2944(6) 0.0173(9) Uani 1 1 d . . . . .
H9 H 0.11687 0.339461 0.197046 0.021 Uiso 1 1 calc R U . . .
C10 C 0.1554(3) 0.4812(3) 0.5842(5) 0.0094(5) Uani 1 1 d . . . . .
H10 H 0.155909 0.506821 0.699451 0.011 Uiso 1 1 calc R U . . .
C11 C 0.2115(3) 0.5218(3) 0.4505(5) 0.0094(5) Uani 1 1 d . . . . .
H11 H 0.253606 0.581863 0.46976 0.011 Uiso 1 1 calc R U . . .
Br1 Br 1.00641(3) 0.12468(3) 0.34838(6) 0.0155(2) Uani 1 1 d . . . . .
F1 F 0.2693(2) 0.2964(3) -0.0049(6) 0.0473(10) Uani 1 1 d . . . . .
N1 N 0.1974(3) 0.4653(3) 0.2969(5) 0.0147(8) Uani 1 1 d . . . . .
O1 O 0.6325(3) 0.2125(3) 0.0790(6) 0.0279(8) Uani 1 1 d . . . . .
O2 O 0.7018(2) 0.3663(3) 0.1770(5) 0.0186(7) Uani 1 1 d . . . . .
H2 H 0.754649 0.335532 0.165467 0.028 Uiso 1 1 calc R U . . .
O3 O 0.8690(3) 0.3001(4) 0.1261(7) 0.0476(14) Uani 1 1 d . U . . .
H1 H 0.904(8) 0.337(9) 0.062(14) 0.071 Uiso 1 1 d . U . . .
H12 H 0.901(8) 0.261(9) 0.183(14) 0.071 Uiso 1 1 d . U . . .
S1 S 0.08728(11) 0.37365(10) 0.47744(18) 0.0275(3) Uani 1 1 d . . . . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_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
C1 O1 1.202(6) . ?
C1 O2 1.320(6) . ?
C1 C2 1.503(6) . ?
C2 C7 1.383(7) . ?
C2 C3 1.400(7) . ?
C3 C4 1.380(7) . ?
C3 H3 0.95 . ?
C4 F1 1.358(6) . ?
C4 C5 1.375(7) . ?
C5 C6 1.399(6) . ?
C5 C8 1.518(6) . ?
C6 C7 1.390(6) . ?
C6 H6 0.95 . ?
C7 H7 0.95 . ?
C8 N1 1.478(5) . ?
C8 H8A 0.99 . ?
C8 H8B 0.99 . ?
C9 N1 1.330(6) . ?
C9 S1 1.663(5) . ?
C9 H9 0.95 . ?
C10 C11 1.486(5) . ?
C10 S1 1.770(4) . ?
C10 H10 0.95 . ?
C11 N1 1.373(6) . ?
C11 H11 0.95 . ?
O2 H2 0.84 . ?
O3 H1 0.89(12) . ?
O3 H12 0.75(11) . ?

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
O1 C1 O2 125.0(4) . . ?
O1 C1 C2 122.7(4) . . ?
O2 C1 C2 112.3(4) . . ?
C7 C2 C3 120.3(4) . . ?
C7 C2 C1 122.4(4) . . ?
C3 C2 C1 117.2(4) . . ?
C4 C3 C2 117.4(5) . . ?
C4 C3 H3 121.3 . . ?
C2 C3 H3 121.3 . . ?
F1 C4 C5 118.6(4) . . ?
F1 C4 C3 117.3(5) . . ?
C5 C4 C3 124.1(4) . . ?
C4 C5 C6 117.3(4) . . ?
C4 C5 C8 121.5(4) . . ?
C6 C5 C8 121.1(4) . . ?
C7 C6 C5 120.5(4) . . ?
C7 C6 H6 119.8 . . ?
C5 C6 H6 119.8 . . ?
C2 C7 C6 120.3(4) . . ?
C2 C7 H7 119.8 . . ?
C6 C7 H7 119.8 . . ?
N1 C8 C5 111.7(4) . . ?
N1 C8 H8A 109.3 . . ?
C5 C8 H8A 109.3 . . ?
N1 C8 H8B 109.3 . . ?
C5 C8 H8B 109.3 . . ?
H8A C8 H8B 107.9 . . ?
N1 C9 S1 113.8(4) . . ?
N1 C9 H9 123.1 . . ?
S1 C9 H9 123.1 . . ?
C11 C10 S1 103.5(3) . . ?
C11 C10 H10 128.3 . . ?
S1 C10 H10 128.3 . . ?
N1 C11 C10 114.6(3) . . ?
N1 C11 H11 122.7 . . ?
C10 C11 H11 122.7 . . ?
C9 N1 C11 113.5(4) . . ?
C9 N1 C8 123.2(4) . . ?
C11 N1 C8 123.1(4) . . ?
C1 O2 H2 109.5 . . ?
H1 O3 H12 111(10) . . ?
C9 S1 C10 94.6(2) . . ?

# The following lines are used to test the character set of files sent by
# network email or other means. They are not part of the CIF data set
# abcdefghijklmnopqrstuvwxyzABCDEFGHIJKLMNOPQRSTUVWXYZ0123456789
# !@#$%^&*()_+{}:"~<>?|\-=[];'`,./

# END of CIF
_chemical_name_systematic        
'3-(4-carboxy-2-fluorobenzyl)thiazol-3-ium bromide'
_chemical_name_common            HPhTz_F
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: water, methanol'
####################################################################### 
# 
# 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_HPhTzCF3
_database_code_depnum_ccdc_archive 'CCDC 2448942'
loop_
_audit_author_name
_audit_author_address
'Andrea Rossin'
;CNR ICCOM
Italy
;
_audit_update_record             
;
2025-05-06 deposited with the CCDC.	2026-02-24 downloaded from the CCDC.
;

_audit_creation_date             2024-05-30T13:42:07-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_formula_sum            'C12 H11 Br F3 N O3 S'
_chemical_formula_moiety         'C12 H9 F3 N O2 S, Br, H2 O'
_chemical_formula_weight         386.19

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/c'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_Int_Tables_number      14
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   12.6925(12)
_cell_length_b                   8.1562(5)
_cell_length_c                   14.9774(13)
_cell_angle_alpha                90
_cell_angle_beta                 108.615(3)
_cell_angle_gamma                90
_cell_volume                     1469.4(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9917
_cell_measurement_theta_min      2.8363
_cell_measurement_theta_max      36.3612

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.07
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.04
_exptl_crystal_density_diffrn    1.746
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             768
_exptl_special_details           
;
;

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    2.98
_exptl_absorpt_correction_type   Multi-Scan
_exptl_absorpt_process_details   
;
Krause, L., Herbst-Irmer, R., Sheldrick, G. M., Stalke, D. (2015).
"Comparison of silver and molybdenum microfocus X-ray sources for
        single-crystal structure determination"
        J. Appl. Cryst. 48, 3-10.
        doi:10.1107/S1600576714022985
;

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_detector_area_resol_mean 7.391
_diffrn_reflns_av_R_equivalents  0.0679
_diffrn_reflns_av_unetI/netI     0.059
_diffrn_reflns_number            33785
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.829
_diffrn_reflns_theta_max         36.359
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_reflns_Friedel_coverage         0
_reflns_number_total             7130
_reflns_number_gt                5582
_reflns_threshold_expression     'I > 2σ(I)'

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_cell_refinement       'SAINT V8.40B (Bruker AXS LLC, 2019)'
_computing_data_reduction        'SAINT V8.40B (Bruker AXS LLC, 2019)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'shelXle (C.B. Huebschle, rev 1503)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION                                       #
#----------------------------------------------------------------------------#

_atom_sites_solution_hydrogens   mixed

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_shelx_SHELXL_version_number     2018/3
_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)+(0.0456P)²+0.3748P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_number_reflns         7130
_refine_ls_number_parameters     198
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0554
_refine_ls_R_factor_gt           0.0385
_refine_ls_wR_factor_ref         0.1022
_refine_ls_wR_factor_gt          0.095
_refine_ls_goodness_of_fit_ref   1.06
_refine_ls_restrained_S_all      1.06
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.89
_refine_diff_density_min         -1.124
_refine_diff_density_rms         0.121

#----------------------------------------------------------------------------#
#                   CONSTRAINTS AND RESTRAINTS                               #
#----------------------------------------------------------------------------#


#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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 0 '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'
F F 0.0171 0.0103 '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 0.006 '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'

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
C1 C 0.34311(12) 0.75242(18) 0.45694(10) 0.0144(2) Uani 1 1 d . . . . .
C2 C 0.45477(12) 0.71297(17) 0.52595(10) 0.0125(2) Uani 1 1 d . . . . .
C3 C 0.46593(12) 0.61070(16) 0.60329(11) 0.0128(2) Uani 1 1 d . . . . .
H3 H 0.402215 0.559956 0.611379 0.015 Uiso 1 1 calc R U . . .
C4 C 0.57052(12) 0.58326(17) 0.66848(10) 0.0122(2) Uani 1 1 d . . . . .
C5 C 0.66587(12) 0.65505(18) 0.65606(10) 0.0125(2) Uani 1 1 d . . . . .
C6 C 0.65342(13) 0.75220(19) 0.57678(10) 0.0151(2) Uani 1 1 d . . . . .
H6 H 0.717327 0.797824 0.566292 0.018 Uiso 1 1 calc R U . . .
C7 C 0.54848(12) 0.78337(18) 0.51263(10) 0.0148(2) Uani 1 1 d . . . . .
H7 H 0.540994 0.852554 0.459935 0.018 Uiso 1 1 calc R U . . .
C8 C 0.57831(13) 0.47828(19) 0.75342(11) 0.0162(3) Uani 1 1 d . . . . .
C9 C 0.78229(12) 0.63526(18) 0.72534(11) 0.0143(2) Uani 1 1 d . . . . .
H9A H 0.789672 0.525154 0.754527 0.017 Uiso 1 1 calc R U . . .
H9B H 0.837281 0.643919 0.691269 0.017 Uiso 1 1 calc R U . . .
C10 C 0.84802(12) 0.72819(18) 0.89183(10) 0.0143(2) Uani 1 1 d . . . . .
H10 H 0.863601 0.620091 0.916085 0.017 Uiso 1 1 calc R U . . .
C11 C 0.79272(13) 0.92908(19) 0.78098(11) 0.0160(3) Uani 1 1 d . . . . .
H11 H 0.765242 0.973115 0.719135 0.019 Uiso 1 1 calc R U . . .
C12 C 0.82396(12) 1.02393(19) 0.86205(10) 0.0159(3) Uani 1 1 d . . . . .
H12 H 0.820556 1.140185 0.863939 0.019 Uiso 1 1 calc R U . . .
Br1 Br 0.01756(2) 1.12060(2) 0.37045(2) 0.01758(5) Uani 1 1 d . . . . .
F1 F 0.62861(9) 0.55826(15) 0.83489(7) 0.0257(2) Uani 1 1 d . . . . .
F2 F 0.63812(11) 0.34159(14) 0.75635(9) 0.0326(3) Uani 1 1 d . . . . .
F3 F 0.47877(9) 0.43166(15) 0.75684(8) 0.0286(3) Uani 1 1 d . . . . .
N1 N 0.80609(10) 0.76272(15) 0.80035(9) 0.0128(2) Uani 1 1 d . . . . .
O1 O 0.26135(10) 0.66172(16) 0.46728(9) 0.0220(2) Uani 1 1 d . . . . .
H1 H 0.1968(19) 0.687(2) 0.4209(18) 0.033 Uiso 1 1 calc R U . . .
O2 O 0.33067(11) 0.85905(16) 0.39820(10) 0.0262(3) Uani 1 1 d . . . . .
O3 O 0.06967(10) 0.73193(16) 0.35119(9) 0.0204(2) Uani 1 1 d . . . . .
H100 H 0.068(2) 0.841(3) 0.3487(19) 0.031 Uiso 1 1 d . U . . .
H101 H 0.051(2) 0.704(3) 0.2990(19) 0.031 Uiso 1 1 d . U . . .
S1 S 0.87021(4) 0.89656(5) 0.95936(3) 0.01804(8) Uani 1 1 d . . . . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_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
C1 O2 1.2110(19) . ?
C1 O1 1.3232(19) . ?
C1 C2 1.498(2) . ?
C2 C7 1.391(2) . ?
C2 C3 1.398(2) . ?
C3 C4 1.392(2) . ?
C3 H3 0.95 . ?
C4 C5 1.409(2) . ?
C4 C8 1.510(2) . ?
C5 C6 1.394(2) . ?
C5 C9 1.519(2) . ?
C6 C7 1.395(2) . ?
C6 H6 0.95 . ?
C7 H7 0.95 . ?
C8 F3 1.3359(19) . ?
C8 F2 1.3416(19) . ?
C8 F1 1.3508(19) . ?
C9 N1 1.4891(19) . ?
C9 H9A 0.99 . ?
C9 H9B 0.99 . ?
C10 N1 1.3321(19) . ?
C10 S1 1.6752(16) . ?
C10 H10 0.95 . ?
C11 N1 1.3866(19) . ?
C11 C12 1.387(2) . ?
C11 H11 0.95 . ?
C12 S1 1.7325(15) . ?
C12 H12 0.95 . ?
O1 H1 0.91(3) . ?
O3 H100 0.89(3) . ?
O3 H101 0.78(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
O2 C1 O1 124.15(14) . . ?
O2 C1 C2 122.04(14) . . ?
O1 C1 C2 113.81(13) . . ?
C7 C2 C3 120.00(13) . . ?
C7 C2 C1 118.44(13) . . ?
C3 C2 C1 121.55(13) . . ?
C4 C3 C2 119.93(14) . . ?
C4 C3 H3 120 . . ?
C2 C3 H3 120 . . ?
C3 C4 C5 120.49(13) . . ?
C3 C4 C8 118.24(13) . . ?
C5 C4 C8 121.25(13) . . ?
C6 C5 C4 118.69(13) . . ?
C6 C5 C9 117.61(13) . . ?
C4 C5 C9 123.69(13) . . ?
C5 C6 C7 120.94(14) . . ?
C5 C6 H6 119.5 . . ?
C7 C6 H6 119.5 . . ?
C2 C7 C6 119.88(13) . . ?
C2 C7 H7 120.1 . . ?
C6 C7 H7 120.1 . . ?
F3 C8 F2 107.12(13) . . ?
F3 C8 F1 106.43(13) . . ?
F2 C8 F1 105.81(13) . . ?
F3 C8 C4 112.66(12) . . ?
F2 C8 C4 112.51(14) . . ?
F1 C8 C4 111.85(12) . . ?
N1 C9 C5 111.10(11) . . ?
N1 C9 H9A 109.4 . . ?
C5 C9 H9A 109.4 . . ?
N1 C9 H9B 109.4 . . ?
C5 C9 H9B 109.4 . . ?
H9A C9 H9B 108 . . ?
N1 C10 S1 112.50(11) . . ?
N1 C10 H10 123.8 . . ?
S1 C10 H10 123.8 . . ?
N1 C11 C12 112.40(13) . . ?
N1 C11 H11 123.8 . . ?
C12 C11 H11 123.8 . . ?
C11 C12 S1 109.12(11) . . ?
C11 C12 H12 125.4 . . ?
S1 C12 H12 125.4 . . ?
C10 N1 C11 113.84(13) . . ?
C10 N1 C9 123.13(12) . . ?
C11 N1 C9 122.93(12) . . ?
C1 O1 H1 109.5 . . ?
H100 O3 H101 105(3) . . ?
C10 S1 C12 92.13(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
C9 H9A Br1 0.99 3.1 3.7218(14) 122.4 4_676 yes
C9 H9A F2 0.99 2.44 3.137(2) 126.6 . yes
C9 H9B Br1 0.99 3 3.8477(16) 143.8 3_676 yes
C10 H10 Br1 0.95 3.07 3.5326(15) 111.7 2_646 yes
C10 H10 Br1 0.95 3 3.6422(15) 126.3 4_676 yes
C11 H11 O2 0.95 2.25 3.1557(19) 158.3 3_676 yes
O1 H1 O3 0.91 1.66 2.5631(17) 170.2 . yes
O3 H100 Br1 0.89(3) 2.42(3) 3.2699(13) 160(2) . yes
O3 H101 Br1 0.78(3) 2.50(3) 3.2747(14) 177(3) 2_545 yes

# The following lines are used to test the character set of files sent by
# network email or other means. They are not part of the CIF data set
# abcdefghijklmnopqrstuvwxyzABCDEFGHIJKLMNOPQRSTUVWXYZ0123456789
# !@#$%^&*()_+{}:"~<>?|\-=[];'`,./

# END of CIF
_chemical_name_systematic        
'3-(4-carboxy-2-(trifluoromethyl)benzyl)thiazol-3-ium bromide'
_chemical_name_common            HPhTz_CF3
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: water, methanol'
