# 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. 
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data_d1752a_a
_database_code_depnum_ccdc_archive 'CCDC 1842528'
_audit_update_record             
;
2018-05-10 deposited with the CCDC.
2019-01-14 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        
'3-(4-benzophenone)-N-(3-((3,5-bistrifluoromethyl)    phenyl)sulfonamido)propyl-N,N-dimethylpropan-1-aminium bromide'
_chemical_name_common            ?
_chemical_melting_point          454
_chemical_formula_moiety         'C29 H31 Br F6 N2 O4 S'
_chemical_formula_sum            'C29 H31 Br F6 N2 O4 S'
_chemical_formula_weight         697.53

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'
Br Br -0.2901 2.4595 '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                   18.9666(14)
_cell_length_b                   10.0908(7)
_cell_length_c                   16.3242(12)
_cell_angle_alpha                90
_cell_angle_beta                 106.387(2)
_cell_angle_gamma                90
_cell_volume                     2997.3(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    7143
_cell_measurement_theta_min      2.31
_cell_measurement_theta_max      23.18

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.546
_exptl_crystal_F_000             1424
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.290
_exptl_crystal_size_mid          0.270
_exptl_crystal_size_min          0.060
_exptl_absorpt_coefficient_mu    1.516
_shelx_estimated_absorpt_T_min   0.668
_shelx_estimated_absorpt_T_max   0.915
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6537
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   'SADABS (Bruker, 2014)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed tube with Bruker Triumph monochromator'
_diffrn_measurement_device_type  'Bruker Kappa APEX-DUO CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            42105
_diffrn_reflns_av_unetI/netI     0.0649
_diffrn_reflns_av_R_equivalents  0.0781
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         2.239
_diffrn_reflns_theta_max         27.548
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             6888
_reflns_number_gt                4530
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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       'APEX2 (Bruker, 2014)'
_computing_cell_refinement       APEX2
_computing_data_reduction        'SAINT (Bruker, 2014)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015a)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2015b)'
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_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)+(0.0143P)²+4.9938P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         6888
_refine_ls_number_parameters     399
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0925
_refine_ls_R_factor_gt           0.0462
_refine_ls_wR_factor_ref         0.0962
_refine_ls_wR_factor_gt          0.0845
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_restrained_S_all      1.050
_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
Br1 Br 0.42559(2) 0.82022(7) 0.33601(3) 0.0426(2) Uani 0.939(3) 1 d . . P . .
Br1A Br 0.4408(9) 0.743(2) 0.3586(11) 0.128(6) Uiso 0.061(3) 1 d . . P . .
S1 S 0.28442(4) 0.94943(7) 0.48017(4) 0.01936(17) Uani 1 1 d . . . . .
F1 F 0.08655(13) 0.6290(3) 0.54340(12) 0.0712(9) Uani 1 1 d . . . . .
F2 F 0.07419(13) 0.4665(2) 0.45720(17) 0.0643(7) Uani 1 1 d . . . . .
F3 F 0.00915(10) 0.6375(2) 0.42094(13) 0.0470(6) Uani 1 1 d . . . . .
F4 F 0.13635(10) 0.5711(2) 0.17746(11) 0.0428(5) Uani 1 1 d . . . . .
F5 F 0.24791(11) 0.5215(2) 0.23734(11) 0.0392(5) Uani 1 1 d . . . . .
F6 F 0.22043(15) 0.7149(2) 0.18603(12) 0.0574(7) Uani 1 1 d . . . . .
O1 O 0.69342(11) 0.5427(2) 0.48031(13) 0.0257(5) Uani 1 1 d . . . . .
O2 O 0.84497(15) 0.8094(2) 0.22378(15) 0.0449(7) Uani 1 1 d . . . . .
O3 O 0.26703(11) 0.9765(2) 0.55829(12) 0.0256(5) Uani 1 1 d . . . . .
O4 O 0.27621(11) 1.0513(2) 0.41701(12) 0.0251(5) Uani 1 1 d . . . . .
N1 N 0.36885(13) 0.9019(3) 0.50266(16) 0.0204(6) Uani 1 1 d . . . . .
H1N H 0.3841(17) 0.895(3) 0.457(2) 0.026(9) Uiso 1 1 d . . . . .
N2 N 0.57866(13) 0.6751(3) 0.70673(14) 0.0216(6) Uani 1 1 d . . . . .
C1 C 0.39248(16) 0.7886(3) 0.56034(18) 0.0237(7) Uani 1 1 d . . . . .
H1A H 0.3745 0.7050 0.5298 0.028 Uiso 1 1 calc R U . . .
H1B H 0.3718 0.7961 0.6095 0.028 Uiso 1 1 calc R U . . .
C2 C 0.47623(16) 0.7877(3) 0.59171(18) 0.0236(7) Uani 1 1 d . . . . .
H2A H 0.4969 0.7814 0.5426 0.028 Uiso 1 1 calc R U . . .
H2B H 0.4942 0.8707 0.6230 0.028 Uiso 1 1 calc R U . . .
C3 C 0.50026(15) 0.6696(3) 0.65018(18) 0.0214(7) Uani 1 1 d . . . . .
H3A H 0.4670 0.6615 0.6870 0.026 Uiso 1 1 calc R U . . .
H3B H 0.4943 0.5885 0.6147 0.026 Uiso 1 1 calc R U . . .
C4 C 0.63376(16) 0.6932(3) 0.65620(18) 0.0219(7) Uani 1 1 d . . . . .
H4A H 0.6836 0.6945 0.6969 0.026 Uiso 1 1 calc R U . . .
H4B H 0.6252 0.7812 0.6282 0.026 Uiso 1 1 calc R U . . .
C5 C 0.63277(16) 0.5899(3) 0.58824(18) 0.0238(7) Uani 1 1 d . . . . .
H5A H 0.6460 0.5016 0.6145 0.029 Uiso 1 1 calc R U . . .
H5B H 0.5835 0.5845 0.5467 0.029 Uiso 1 1 calc R U . . .
C6 C 0.68927(18) 0.6362(3) 0.54490(19) 0.0268(7) Uani 1 1 d . . . . .
H6A H 0.6752 0.7243 0.5188 0.032 Uiso 1 1 calc R U . . .
H6B H 0.7379 0.6443 0.5876 0.032 Uiso 1 1 calc R U . . .
C7 C 0.73533(16) 0.5818(3) 0.42786(18) 0.0210(7) Uani 1 1 d . . . . .
C8 C 0.73643(17) 0.4951(3) 0.36231(19) 0.0259(7) Uani 1 1 d . . . . .
H8A H 0.7109 0.4132 0.3569 0.031 Uiso 1 1 calc R U . . .
C9 C 0.77494(17) 0.5285(3) 0.30474(19) 0.0250(7) Uani 1 1 d . . . . .
H9A H 0.7761 0.4682 0.2605 0.030 Uiso 1 1 calc R U . . .
C10 C 0.81200(16) 0.6490(3) 0.31055(18) 0.0209(7) Uani 1 1 d . . . . .
C11 C 0.80890(16) 0.7358(3) 0.37597(18) 0.0226(7) Uani 1 1 d . . . . .
H11A H 0.8325 0.8196 0.3799 0.027 Uiso 1 1 calc R U . . .
C12 C 0.77213(16) 0.7025(3) 0.43547(18) 0.0223(7) Uani 1 1 d . . . . .
H12A H 0.7721 0.7613 0.4809 0.027 Uiso 1 1 calc R U . . .
C13 C 0.84917(18) 0.6928(3) 0.24553(19) 0.0274(7) Uani 1 1 d . . . . .
C14 C 0.89292(16) 0.5997(3) 0.20962(19) 0.0235(7) Uani 1 1 d . . . . .
C15 C 0.92212(17) 0.4821(3) 0.25083(19) 0.0266(7) Uani 1 1 d . . . . .
H15A H 0.9111 0.4558 0.3017 0.032 Uiso 1 1 calc R U . . .
C16 C 0.96723(17) 0.4042(4) 0.2169(2) 0.0341(8) Uani 1 1 d . . . . .
H16A H 0.9874 0.3245 0.2449 0.041 Uiso 1 1 calc R U . . .
C17 C 0.98289(19) 0.4421(4) 0.1426(2) 0.0410(9) Uani 1 1 d . . . . .
H17A H 1.0141 0.3885 0.1199 0.049 Uiso 1 1 calc R U . . .
C18 C 0.95373(19) 0.5569(4) 0.1012(2) 0.0392(9) Uani 1 1 d . . . . .
H18A H 0.9641 0.5815 0.0496 0.047 Uiso 1 1 calc R U . . .
C19 C 0.90937(18) 0.6362(4) 0.1345(2) 0.0311(8) Uani 1 1 d . . . . .
H19A H 0.8899 0.7161 0.1063 0.037 Uiso 1 1 calc R U . . .
C20 C 0.59260(18) 0.5497(3) 0.7586(2) 0.0316(8) Uani 1 1 d . . . . .
H20A H 0.5869 0.4732 0.7203 0.047 Uiso 1 1 calc R U . . .
H20B H 0.5573 0.5431 0.7922 0.047 Uiso 1 1 calc R U . . .
H20C H 0.6427 0.5511 0.7971 0.047 Uiso 1 1 calc R U . . .
C21 C 0.58817(17) 0.7894(3) 0.76757(19) 0.0305(8) Uani 1 1 d . . . . .
H21A H 0.6373 0.7859 0.8081 0.046 Uiso 1 1 calc R U . . .
H21B H 0.5511 0.7841 0.7988 0.046 Uiso 1 1 calc R U . . .
H21C H 0.5823 0.8728 0.7356 0.046 Uiso 1 1 calc R U . . .
C22 C 0.22871(15) 0.8134(3) 0.43115(16) 0.0171(6) Uani 1 1 d . . . . .
C23 C 0.17775(15) 0.7588(3) 0.46723(17) 0.0184(6) Uani 1 1 d . . . . .
H23A H 0.1730 0.7914 0.5200 0.022 Uiso 1 1 calc R U . . .
C24 C 0.13377(15) 0.6561(3) 0.42584(18) 0.0213(7) Uani 1 1 d . . . . .
C25 C 0.13956(16) 0.6080(3) 0.34821(18) 0.0219(7) Uani 1 1 d . . . . .
H25A H 0.1088 0.5380 0.3198 0.026 Uiso 1 1 calc R U . . .
C26 C 0.19118(15) 0.6641(3) 0.31293(17) 0.0184(6) Uani 1 1 d . . . . .
C27 C 0.23707(15) 0.7651(3) 0.35479(17) 0.0168(6) Uani 1 1 d . . . . .
H27A H 0.2737 0.8006 0.3315 0.020 Uiso 1 1 calc R U . . .
C28 C 0.07651(18) 0.5969(4) 0.4625(2) 0.0318(8) Uani 1 1 d . . . . .
C29 C 0.19861(17) 0.6177(3) 0.22871(18) 0.0218(7) 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
Br1 Br1A 0.88(2) . ?
S1 O3 1.431(2) . ?
S1 O4 1.433(2) . ?
S1 N1 1.612(2) . ?
S1 C22 1.779(3) . ?
F1 C28 1.320(4) . ?
F2 C28 1.319(4) . ?
F3 C28 1.331(4) . ?
F4 C29 1.326(3) . ?
F5 C29 1.327(3) . ?
F6 C29 1.335(3) . ?
O1 C7 1.380(3) . ?
O1 C6 1.434(3) . ?
O2 C13 1.225(4) . ?
N1 C1 1.469(4) . ?
N1 H1N 0.87(3) . ?
N2 C21 1.499(4) . ?
N2 C20 1.504(4) . ?
N2 C3 1.514(3) . ?
N2 C4 1.514(3) . ?
C1 C2 1.525(4) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C2 C3 1.515(4) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 C5 1.519(4) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 C6 1.515(4) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 C8 1.387(4) . ?
C7 C12 1.392(4) . ?
C8 C9 1.385(4) . ?
C8 H8A 0.9500 . ?
C9 C10 1.395(4) . ?
C9 H9A 0.9500 . ?
C10 C11 1.395(4) . ?
C10 C13 1.497(4) . ?
C11 C12 1.388(4) . ?
C11 H11A 0.9500 . ?
C12 H12A 0.9500 . ?
C13 C14 1.480(4) . ?
C14 C19 1.397(4) . ?
C14 C15 1.398(4) . ?
C15 C16 1.387(4) . ?
C15 H15A 0.9500 . ?
C16 C17 1.382(5) . ?
C16 H16A 0.9500 . ?
C17 C18 1.376(5) . ?
C17 H17A 0.9500 . ?
C18 C19 1.380(5) . ?
C18 H18A 0.9500 . ?
C19 H19A 0.9500 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C22 C23 1.381(4) . ?
C22 C27 1.389(4) . ?
C23 C24 1.381(4) . ?
C23 H23A 0.9500 . ?
C24 C25 1.390(4) . ?
C24 C28 1.504(4) . ?
C25 C26 1.389(4) . ?
C25 H25A 0.9500 . ?
C26 C27 1.388(4) . ?
C26 C29 1.496(4) . ?
C27 H27A 0.9500 . ?

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
O3 S1 O4 119.91(13) . . ?
O3 S1 N1 108.53(13) . . ?
O4 S1 N1 106.06(13) . . ?
O3 S1 C22 106.94(13) . . ?
O4 S1 C22 107.45(12) . . ?
N1 S1 C22 107.40(13) . . ?
C7 O1 C6 115.4(2) . . ?
C1 N1 S1 118.8(2) . . ?
C1 N1 H1N 112(2) . . ?
S1 N1 H1N 112(2) . . ?
C21 N2 C20 107.8(2) . . ?
C21 N2 C3 110.3(2) . . ?
C20 N2 C3 107.4(2) . . ?
C21 N2 C4 107.2(2) . . ?
C20 N2 C4 111.7(2) . . ?
C3 N2 C4 112.5(2) . . ?
N1 C1 C2 108.7(2) . . ?
N1 C1 H1A 110.0 . . ?
C2 C1 H1A 110.0 . . ?
N1 C1 H1B 110.0 . . ?
C2 C1 H1B 110.0 . . ?
H1A C1 H1B 108.3 . . ?
C3 C2 C1 108.4(2) . . ?
C3 C2 H2A 110.0 . . ?
C1 C2 H2A 110.0 . . ?
C3 C2 H2B 110.0 . . ?
C1 C2 H2B 110.0 . . ?
H2A C2 H2B 108.4 . . ?
N2 C3 C2 115.1(2) . . ?
N2 C3 H3A 108.5 . . ?
C2 C3 H3A 108.5 . . ?
N2 C3 H3B 108.5 . . ?
C2 C3 H3B 108.5 . . ?
H3A C3 H3B 107.5 . . ?
N2 C4 C5 116.5(2) . . ?
N2 C4 H4A 108.2 . . ?
C5 C4 H4A 108.2 . . ?
N2 C4 H4B 108.2 . . ?
C5 C4 H4B 108.2 . . ?
H4A C4 H4B 107.3 . . ?
C6 C5 C4 105.4(2) . . ?
C6 C5 H5A 110.7 . . ?
C4 C5 H5A 110.7 . . ?
C6 C5 H5B 110.7 . . ?
C4 C5 H5B 110.7 . . ?
H5A C5 H5B 108.8 . . ?
O1 C6 C5 109.5(2) . . ?
O1 C6 H6A 109.8 . . ?
C5 C6 H6A 109.8 . . ?
O1 C6 H6B 109.8 . . ?
C5 C6 H6B 109.8 . . ?
H6A C6 H6B 108.2 . . ?
O1 C7 C8 115.8(3) . . ?
O1 C7 C12 123.9(3) . . ?
C8 C7 C12 120.3(3) . . ?
C9 C8 C7 119.7(3) . . ?
C9 C8 H8A 120.1 . . ?
C7 C8 H8A 120.1 . . ?
C8 C9 C10 121.2(3) . . ?
C8 C9 H9A 119.4 . . ?
C10 C9 H9A 119.4 . . ?
C9 C10 C11 118.0(3) . . ?
C9 C10 C13 122.6(3) . . ?
C11 C10 C13 119.2(3) . . ?
C12 C11 C10 121.4(3) . . ?
C12 C11 H11A 119.3 . . ?
C10 C11 H11A 119.3 . . ?
C11 C12 C7 119.2(3) . . ?
C11 C12 H12A 120.4 . . ?
C7 C12 H12A 120.4 . . ?
O2 C13 C14 119.6(3) . . ?
O2 C13 C10 118.9(3) . . ?
C14 C13 C10 121.5(3) . . ?
C19 C14 C15 119.3(3) . . ?
C19 C14 C13 118.0(3) . . ?
C15 C14 C13 122.6(3) . . ?
C16 C15 C14 119.6(3) . . ?
C16 C15 H15A 120.2 . . ?
C14 C15 H15A 120.2 . . ?
C17 C16 C15 120.2(3) . . ?
C17 C16 H16A 119.9 . . ?
C15 C16 H16A 119.9 . . ?
C18 C17 C16 120.6(3) . . ?
C18 C17 H17A 119.7 . . ?
C16 C17 H17A 119.7 . . ?
C17 C18 C19 120.0(3) . . ?
C17 C18 H18A 120.0 . . ?
C19 C18 H18A 120.0 . . ?
C18 C19 C14 120.3(3) . . ?
C18 C19 H19A 119.8 . . ?
C14 C19 H19A 119.8 . . ?
N2 C20 H20A 109.5 . . ?
N2 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
N2 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
N2 C21 H21A 109.5 . . ?
N2 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
N2 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C23 C22 C27 120.9(3) . . ?
C23 C22 S1 121.0(2) . . ?
C27 C22 S1 118.1(2) . . ?
C22 C23 C24 119.3(3) . . ?
C22 C23 H23A 120.3 . . ?
C24 C23 H23A 120.3 . . ?
C23 C24 C25 121.0(3) . . ?
C23 C24 C28 120.5(3) . . ?
C25 C24 C28 118.4(3) . . ?
C26 C25 C24 118.8(3) . . ?
C26 C25 H25A 120.6 . . ?
C24 C25 H25A 120.6 . . ?
C27 C26 C25 120.8(3) . . ?
C27 C26 C29 118.3(3) . . ?
C25 C26 C29 120.9(3) . . ?
C26 C27 C22 119.0(3) . . ?
C26 C27 H27A 120.5 . . ?
C22 C27 H27A 120.5 . . ?
F2 C28 F1 107.7(3) . . ?
F2 C28 F3 105.3(3) . . ?
F1 C28 F3 106.4(3) . . ?
F2 C28 C24 112.6(3) . . ?
F1 C28 C24 112.6(3) . . ?
F3 C28 C24 111.8(3) . . ?
F4 C29 F5 106.4(2) . . ?
F4 C29 F6 106.5(2) . . ?
F5 C29 F6 106.3(3) . . ?
F4 C29 C26 113.1(2) . . ?
F5 C29 C26 112.2(2) . . ?
F6 C29 C26 111.9(2) . . ?

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
O3 S1 N1 C1 55.5(3) . . . . ?
O4 S1 N1 C1 -174.4(2) . . . . ?
C22 S1 N1 C1 -59.7(2) . . . . ?
S1 N1 C1 C2 -163.9(2) . . . . ?
N1 C1 C2 C3 -179.2(2) . . . . ?
C21 N2 C3 C2 63.7(3) . . . . ?
C20 N2 C3 C2 -179.2(2) . . . . ?
C4 N2 C3 C2 -55.9(3) . . . . ?
C1 C2 C3 N2 -162.9(2) . . . . ?
C21 N2 C4 C5 -178.4(3) . . . . ?
C20 N2 C4 C5 63.8(3) . . . . ?
C3 N2 C4 C5 -57.1(3) . . . . ?
N2 C4 C5 C6 176.7(2) . . . . ?
C7 O1 C6 C5 171.4(2) . . . . ?
C4 C5 C6 O1 178.8(2) . . . . ?
C6 O1 C7 C8 -176.6(3) . . . . ?
C6 O1 C7 C12 0.3(4) . . . . ?
O1 C7 C8 C9 177.7(3) . . . . ?
C12 C7 C8 C9 0.6(5) . . . . ?
C7 C8 C9 C10 -1.0(5) . . . . ?
C8 C9 C10 C11 -0.3(5) . . . . ?
C8 C9 C10 C13 -175.1(3) . . . . ?
C9 C10 C11 C12 2.0(4) . . . . ?
C13 C10 C11 C12 176.9(3) . . . . ?
C10 C11 C12 C7 -2.3(4) . . . . ?
O1 C7 C12 C11 -175.9(3) . . . . ?
C8 C7 C12 C11 1.0(4) . . . . ?
C9 C10 C13 O2 140.3(3) . . . . ?
C11 C10 C13 O2 -34.5(4) . . . . ?
C9 C10 C13 C14 -42.0(4) . . . . ?
C11 C10 C13 C14 143.3(3) . . . . ?
O2 C13 C14 C19 -19.0(5) . . . . ?
C10 C13 C14 C19 163.3(3) . . . . ?
O2 C13 C14 C15 156.6(3) . . . . ?
C10 C13 C14 C15 -21.1(5) . . . . ?
C19 C14 C15 C16 0.4(4) . . . . ?
C13 C14 C15 C16 -175.2(3) . . . . ?
C14 C15 C16 C17 -0.4(5) . . . . ?
C15 C16 C17 C18 -0.3(5) . . . . ?
C16 C17 C18 C19 1.0(5) . . . . ?
C17 C18 C19 C14 -1.0(5) . . . . ?
C15 C14 C19 C18 0.3(5) . . . . ?
C13 C14 C19 C18 176.0(3) . . . . ?
O3 S1 C22 C23 3.0(3) . . . . ?
O4 S1 C22 C23 -127.0(2) . . . . ?
N1 S1 C22 C23 119.3(2) . . . . ?
O3 S1 C22 C27 -178.1(2) . . . . ?
O4 S1 C22 C27 52.0(3) . . . . ?
N1 S1 C22 C27 -61.7(2) . . . . ?
C27 C22 C23 C24 -1.1(4) . . . . ?
S1 C22 C23 C24 177.9(2) . . . . ?
C22 C23 C24 C25 -0.6(4) . . . . ?
C22 C23 C24 C28 -178.5(3) . . . . ?
C23 C24 C25 C26 0.7(4) . . . . ?
C28 C24 C25 C26 178.6(3) . . . . ?
C24 C25 C26 C27 1.0(4) . . . . ?
C24 C25 C26 C29 -178.8(3) . . . . ?
C25 C26 C27 C22 -2.6(4) . . . . ?
C29 C26 C27 C22 177.2(3) . . . . ?
C23 C22 C27 C26 2.7(4) . . . . ?
S1 C22 C27 C26 -176.3(2) . . . . ?
C23 C24 C28 F2 -137.9(3) . . . . ?
C25 C24 C28 F2 44.2(4) . . . . ?
C23 C24 C28 F1 -15.9(4) . . . . ?
C25 C24 C28 F1 166.2(3) . . . . ?
C23 C24 C28 F3 103.8(3) . . . . ?
C25 C24 C28 F3 -74.1(4) . . . . ?
C27 C26 C29 F4 -151.0(3) . . . . ?
C25 C26 C29 F4 28.8(4) . . . . ?
C27 C26 C29 F5 88.6(3) . . . . ?
C25 C26 C29 F5 -91.6(3) . . . . ?
C27 C26 C29 F6 -30.7(4) . . . . ?
C25 C26 C29 F6 149.1(3) . . . . ?

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
N1 H1N Br1A 0.87(3) 2.66(4) 3.431(16) 148(3) .

_refine_diff_density_max         0.424
_refine_diff_density_min         -0.597
_refine_diff_density_rms         0.073


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Acetonitrile'
####################################################################### 
# 
# 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_d16120_a
_database_code_depnum_ccdc_archive 'CCDC 1842659'
_audit_update_record             
;
2018-05-10 deposited with the CCDC.
2019-01-14 downloaded from the CCDC.
;
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/c'
_symmetry_Int_Tables_number      14
_space_group_name_Hall           '-P 2ybc'
loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 x,y,z
2 -x,1/2+y,1/2-z
3 -x,-y,-z
4 x,1/2-y,1/2+z
_cell_length_a                   13.6666(4)
_cell_length_b                   8.9679(3)
_cell_length_c                   18.7028(6)
_cell_angle_alpha                90
_cell_angle_beta                 101.2030(10)
_cell_angle_gamma                90
_cell_volume                     2248.55
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
S1 S 1.02200(2) 0.53152(3) 0.83027(2)
O1 O 1.09768(7) 0.64242(11) 0.85081(5)
O2 O 1.05305(7) 0.38061(10) 0.82227(5)
O3 O 0.72064(8) 0.51962(11) 0.52984(5)
O4 O 0.35931(8) 0.35271(13) 0.27767(6)
N1 N 0.95891(8) 0.58186(13) 0.75147(6)
C1 C 0.74788(10) 0.45886(14) 0.60187(7)
H1A H 0.7686 0.3534 0.5998
H1B H 0.6909 0.4638 0.6273
C2 C 0.83342(10) 0.55245(14) 0.64103(7)
H2A H 0.8119 0.6578 0.6417
H2B H 0.8894 0.5474 0.6145
C3 C 0.86867(10) 0.49854(15) 0.71868(7)
H3A H 0.8158 0.5148 0.7473
H3B H 0.8836 0.3905 0.7188
C4 C 0.93756(9) 0.53421(13) 0.89213(7)
C5 C 0.89685(10) 0.40200(14) 0.91458(7)
C6 C 0.82631(10) 0.41548(16) 0.95905(7)
H6A H 0.7978 0.3272 0.9743
C7 C 0.79602(10) 0.55143(16) 0.98195(8)
C8 C 0.83822(10) 0.67910(15) 0.95946(8)
H8A H 0.8187 0.7733 0.9753
C9 C 0.90835(10) 0.67458(15) 0.91440(7)
C10 C 0.92321(12) 0.24530(15) 0.89609(9)
H10A H 0.8806 0.1744 0.9156
H10B H 0.9933 0.2254 0.9176
H10C H 0.9130 0.2342 0.8430
C11 C 0.71953(11) 0.56066(19) 1.02987(9)
H11A H 0.7045 0.6655 1.0378
H11B H 0.7458 0.5130 1.0768
H11C H 0.6585 0.5095 1.0061
C12 C 0.94799(15) 0.82266(16) 0.89412(10)
H12A H 0.9110 0.9037 0.9119
H12B H 0.9398 0.8295 0.8410
H12C H 1.0189 0.8309 0.9163
C13 C 0.64387(10) 0.45367(15) 0.48325(7)
C14 C 0.59169(10) 0.33037(15) 0.50049(7)
H14A H 0.6066 0.2886 0.5480
C15 C 0.51755(10) 0.26883(16) 0.44748(7)
H15A H 0.4832 0.1825 0.4587
C16 C 0.49261(10) 0.33117(16) 0.37826(7)
C17 C 0.54384(11) 0.45827(15) 0.36284(8)
H17A H 0.5260 0.5043 0.3164
C18 C 0.61955(11) 0.51738(16) 0.41387(8)
H18A H 0.6555 0.6016 0.4021
C19 C 0.41259(10) 0.26950(17) 0.32029(7)
C20 C 0.40043(11) 0.10438(18) 0.31310(7)
C21 C 0.30797(13) 0.0466(2) 0.27880(9)
H21A H 0.2532 0.1114 0.2626
C22 C 0.29717(15) -0.1072(3) 0.26866(10)
H22A H 0.2341 -0.1469 0.2465
C23 C 0.37649(17) -0.2018(2) 0.29032(10)
H23A H 0.3684 -0.3060 0.2820
C24 C 0.46708(16) -0.14617(19) 0.32393(9)
H24A H 0.5216 -0.2119 0.3393
C25 C 0.47947(12) 0.00651(18) 0.33559(8)
H25A H 0.5425 0.0443 0.3591
H1N H 0.9556(11) 0.672(2) 0.7468(8)

#END
_chemical_name_systematic        
N-(3-(4-benzoylphenoxy)propyl)-2,4,6-trimethylbenzenesulfonamide
####################################################################### 
# 
# 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_d16119
_database_code_depnum_ccdc_archive 'CCDC 1842536'
_audit_update_record             
;
2018-05-10 deposited with the CCDC.
2019-01-14 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        
N-(3-bromopropyl)-2,4,6-trimethylbenzenesulfonamide
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C12 H18 Br N O2 S'
_chemical_formula_sum            'C12 H18 Br N O2 S'
_chemical_formula_weight         320.24

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'
S S 0.1246 0.1234 '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'

_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                   12.2036(9)
_cell_length_b                   5.3788(4)
_cell_length_c                   20.7873(17)
_cell_angle_alpha                90
_cell_angle_beta                 99.006(3)
_cell_angle_gamma                90
_cell_volume                     1347.67(18)
_cell_formula_units_Z            4
_cell_measurement_temperature    147(2)
_cell_measurement_reflns_used    6873
_cell_measurement_theta_min      3.18
_cell_measurement_theta_max      26.99

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.578
_exptl_crystal_F_000             656
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.180
_exptl_crystal_size_mid          0.110
_exptl_crystal_size_min          0.060
_exptl_absorpt_coefficient_mu    3.195
_shelx_estimated_absorpt_T_min   0.597
_shelx_estimated_absorpt_T_max   0.831
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6556
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   'SADABS (Bruker, 2014)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      147(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed tube with Bruker Triumph monochromator'
_diffrn_measurement_device_type  'Bruker Kappa APEX-DUO CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            25560
_diffrn_reflns_av_unetI/netI     0.0307
_diffrn_reflns_av_R_equivalents  0.0466
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_theta_min         1.820
_diffrn_reflns_theta_max         27.600
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             3100
_reflns_number_gt                2515
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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       'APEX2 (Bruker, 2014)'
_computing_cell_refinement       APEX2
_computing_data_reduction        'SAINT (Bruker, 2014)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015a)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2015b)'
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_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)+(0.0236P)²+0.6932P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3100
_refine_ls_number_parameters     161
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0408
_refine_ls_R_factor_gt           0.0265
_refine_ls_wR_factor_ref         0.0569
_refine_ls_wR_factor_gt          0.0529
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_restrained_S_all      1.026
_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
Br1 Br 0.40081(2) 0.19271(4) 0.03451(2) 0.02761(8) Uani 1 1 d . . . . .
S1 S 0.11408(4) 0.13661(8) 0.18731(2) 0.01494(11) Uani 1 1 d . . . . .
O1 O 0.15924(11) 0.1358(2) 0.25525(7) 0.0203(3) Uani 1 1 d . . . . .
O2 O 0.11331(11) -0.0915(2) 0.15163(7) 0.0221(3) Uani 1 1 d . . . . .
N1 N 0.18674(13) 0.3332(3) 0.15303(8) 0.0166(4) Uani 1 1 d . . . . .
C1 C 0.36107(16) 0.4949(4) 0.07827(10) 0.0209(4) Uani 1 1 d . . . . .
H1A H 0.3786 0.4708 0.1260 0.025 Uiso 1 1 calc R U . . .
H1B H 0.4067 0.6349 0.0665 0.025 Uiso 1 1 calc R U . . .
C2 C 0.23986(16) 0.5617(4) 0.06051(10) 0.0218(4) Uani 1 1 d . . . . .
H2A H 0.2224 0.5780 0.0126 0.026 Uiso 1 1 calc R U . . .
H2B H 0.2279 0.7265 0.0795 0.026 Uiso 1 1 calc R U . . .
C3 C 0.15880(16) 0.3789(4) 0.08271(10) 0.0194(4) Uani 1 1 d . . . . .
H3A H 0.0826 0.4464 0.0727 0.023 Uiso 1 1 calc R U . . .
H3B H 0.1612 0.2203 0.0588 0.023 Uiso 1 1 calc R U . . .
C4 C -0.02444(15) 0.2538(3) 0.17790(9) 0.0141(4) Uani 1 1 d . . . . .
C5 C -0.10767(16) 0.1624(4) 0.12857(9) 0.0172(4) Uani 1 1 d . . . . .
C6 C -0.21249(16) 0.2722(4) 0.12273(10) 0.0202(4) Uani 1 1 d . . . . .
H6A H -0.2698 0.2109 0.0904 0.024 Uiso 1 1 calc R U . . .
C7 C -0.23664(16) 0.4661(4) 0.16195(10) 0.0204(4) Uani 1 1 d . . . . .
C8 C -0.15328(16) 0.5505(4) 0.20975(10) 0.0203(4) Uani 1 1 d . . . . .
H8A H -0.1694 0.6825 0.2372 0.024 Uiso 1 1 calc R U . . .
C9 C -0.04695(15) 0.4508(4) 0.21948(9) 0.0160(4) Uani 1 1 d . . . . .
C10 C -0.09377(17) -0.0418(4) 0.08077(10) 0.0247(5) Uani 1 1 d . . . . .
H10A H -0.0345 0.0032 0.0561 0.037 Uiso 1 1 calc R U . . .
H10B H -0.1634 -0.0640 0.0507 0.037 Uiso 1 1 calc R U . . .
H10C H -0.0744 -0.1972 0.1045 0.037 Uiso 1 1 calc R U . . .
C11 C -0.34996(17) 0.5858(5) 0.15204(11) 0.0300(5) Uani 1 1 d . . . . .
H11A H -0.3773 0.5953 0.1939 0.045 Uiso 1 1 calc R U . . .
H11B H -0.4012 0.4861 0.1214 0.045 Uiso 1 1 calc R U . . .
H11C H -0.3448 0.7537 0.1345 0.045 Uiso 1 1 calc R U . . .
C12 C 0.03562(16) 0.5592(4) 0.27400(10) 0.0221(5) Uani 1 1 d . . . . .
H12A H 0.1053 0.5954 0.2579 0.033 Uiso 1 1 calc R U . . .
H12B H 0.0495 0.4396 0.3099 0.033 Uiso 1 1 calc R U . . .
H12C H 0.0056 0.7131 0.2895 0.033 Uiso 1 1 calc R U . . .
H1N H 0.2043(17) 0.448(4) 0.1754(11) 0.020(6) 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
Br1 C1 1.9603(19) . ?
S1 O2 1.4331(14) . ?
S1 O1 1.4334(14) . ?
S1 N1 1.6155(17) . ?
S1 C4 1.7860(19) . ?
N1 C3 1.469(2) . ?
N1 H1N 0.78(2) . ?
C1 C2 1.511(3) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C2 C3 1.517(3) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 C5 1.414(3) . ?
C4 C9 1.421(3) . ?
C5 C6 1.397(3) . ?
C5 C10 1.508(3) . ?
C6 C7 1.384(3) . ?
C6 H6A 0.9500 . ?
C7 C8 1.383(3) . ?
C7 C11 1.510(3) . ?
C8 C9 1.389(3) . ?
C8 H8A 0.9500 . ?
C9 C12 1.511(3) . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?

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 S1 O1 118.54(9) . . ?
O2 S1 N1 106.96(9) . . ?
O1 S1 N1 106.47(9) . . ?
O2 S1 C4 108.44(9) . . ?
O1 S1 C4 108.68(8) . . ?
N1 S1 C4 107.23(9) . . ?
C3 N1 S1 119.38(14) . . ?
C3 N1 H1N 117.4(16) . . ?
S1 N1 H1N 111.8(16) . . ?
C2 C1 Br1 112.82(14) . . ?
C2 C1 H1A 109.0 . . ?
Br1 C1 H1A 109.0 . . ?
C2 C1 H1B 109.0 . . ?
Br1 C1 H1B 109.0 . . ?
H1A C1 H1B 107.8 . . ?
C1 C2 C3 115.56(17) . . ?
C1 C2 H2A 108.4 . . ?
C3 C2 H2A 108.4 . . ?
C1 C2 H2B 108.4 . . ?
C3 C2 H2B 108.4 . . ?
H2A C2 H2B 107.5 . . ?
N1 C3 C2 110.52(16) . . ?
N1 C3 H3A 109.5 . . ?
C2 C3 H3A 109.5 . . ?
N1 C3 H3B 109.5 . . ?
C2 C3 H3B 109.5 . . ?
H3A C3 H3B 108.1 . . ?
C5 C4 C9 121.01(17) . . ?
C5 C4 S1 121.11(14) . . ?
C9 C4 S1 117.80(14) . . ?
C6 C5 C4 117.40(18) . . ?
C6 C5 C10 116.51(18) . . ?
C4 C5 C10 126.08(18) . . ?
C7 C6 C5 122.96(19) . . ?
C7 C6 H6A 118.5 . . ?
C5 C6 H6A 118.5 . . ?
C8 C7 C6 118.05(18) . . ?
C8 C7 C11 120.87(19) . . ?
C6 C7 C11 121.07(19) . . ?
C7 C8 C9 122.90(19) . . ?
C7 C8 H8A 118.5 . . ?
C9 C8 H8A 118.5 . . ?
C8 C9 C4 117.67(17) . . ?
C8 C9 C12 117.27(17) . . ?
C4 C9 C12 125.06(17) . . ?
C5 C10 H10A 109.5 . . ?
C5 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C5 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C7 C11 H11A 109.5 . . ?
C7 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C7 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C9 C12 H12A 109.5 . . ?
C9 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C9 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 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
O2 S1 N1 C3 53.44(16) . . . . ?
O1 S1 N1 C3 -178.90(14) . . . . ?
C4 S1 N1 C3 -62.71(16) . . . . ?
Br1 C1 C2 C3 65.6(2) . . . . ?
S1 N1 C3 C2 -177.91(13) . . . . ?
C1 C2 C3 N1 53.7(2) . . . . ?
O2 S1 C4 C5 -15.57(18) . . . . ?
O1 S1 C4 C5 -145.69(15) . . . . ?
N1 S1 C4 C5 99.60(16) . . . . ?
O2 S1 C4 C9 167.55(14) . . . . ?
O1 S1 C4 C9 37.43(17) . . . . ?
N1 S1 C4 C9 -77.29(16) . . . . ?
C9 C4 C5 C6 -0.4(3) . . . . ?
S1 C4 C5 C6 -177.16(14) . . . . ?
C9 C4 C5 C10 178.87(18) . . . . ?
S1 C4 C5 C10 2.1(3) . . . . ?
C4 C5 C6 C7 1.2(3) . . . . ?
C10 C5 C6 C7 -178.15(18) . . . . ?
C5 C6 C7 C8 -1.3(3) . . . . ?
C5 C6 C7 C11 177.51(19) . . . . ?
C6 C7 C8 C9 0.6(3) . . . . ?
C11 C7 C8 C9 -178.18(19) . . . . ?
C7 C8 C9 C4 0.1(3) . . . . ?
C7 C8 C9 C12 -179.38(19) . . . . ?
C5 C4 C9 C8 -0.2(3) . . . . ?
S1 C4 C9 C8 176.65(14) . . . . ?
C5 C4 C9 C12 179.21(18) . . . . ?
S1 C4 C9 C12 -3.9(3) . . . . ?

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
C2 H2B O2 0.99 2.41 3.220(2) 138.3 1_565
N1 H1N O1 0.78(2) 2.26(2) 2.949(2) 147(2) 2

_refine_diff_density_max         0.355
_refine_diff_density_min         -0.372
_refine_diff_density_rms         0.066

####################################################################### 
# 
# 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_d1712_a
_database_code_depnum_ccdc_archive 'CCDC 1842645'
_audit_update_record             
;
2018-05-10 deposited with the CCDC.
2019-01-14 downloaded from the CCDC.
;
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/c'
_symmetry_Int_Tables_number      14
_space_group_name_Hall           '-P 2ybc'
loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 x,y,z
2 -x,1/2+y,1/2-z
3 -x,-y,-z
4 x,1/2-y,1/2+z
_cell_length_a                   14.0175(11)
_cell_length_b                   7.9234(6)
_cell_length_c                   14.6173(11)
_cell_angle_alpha                90
_cell_angle_beta                 116.149(2)
_cell_angle_gamma                90
_cell_volume                     1457.33
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
S1 S 0.27267(3) 0.26597(5) 0.68605(3)
F1 F 0.5938(3) 0.2809(8) 0.4640(2)
F2 F 0.6957(4) 0.1659(5) 0.5974(4)
F3 F 0.6852(5) 0.4300(6) 0.5892(6)
O1 O 0.31220(9) 0.32894(18) 0.78810(8)
O2 O 0.22589(9) 0.10129(15) 0.66146(9)
N1 N 0.18519(10) 0.39548(17) 0.61058(10)
N2 N -0.06027(10) 0.72644(17) 0.59838(10)
C1 C 0.20890(12) 0.5771(2) 0.61862(13)
H1A H 0.2482 0.6048 0.5785
H1B H 0.2546 0.6068 0.6907
C2 C 0.10649(13) 0.6799(2) 0.57921(13)
H2A H 0.1238 0.8014 0.5810
H2B H 0.0606 0.6487 0.5075
C3 C 0.04632(12) 0.6502(2) 0.64248(12)
H3A H 0.0395 0.5272 0.6497
H3B H 0.0882 0.6973 0.7115
C4 C -0.11699(15) 0.6697(3) 0.65613(15)
H4A H -0.1224 0.5463 0.6533
H4B H -0.1885 0.7189 0.6266
H4C H -0.0782 0.7059 0.7272
C5 C -0.05387(15) 0.9105(2) 0.60156(16)
H5A H -0.0167 0.9490 0.5622
H5B H -0.0148 0.9479 0.6724
H5C H -0.1258 0.9581 0.5722
C6 C 0.38139(11) 0.26871(19) 0.65454(11)
C7 C 0.37067(12) 0.1870(2) 0.56673(12)
H7A H 0.3077 0.1255 0.5268
C8 C 0.45178(13) 0.1950(2) 0.53732(12)
H8A H 0.4445 0.1411 0.4765
C9 C 0.54392(12) 0.2826(2) 0.59759(12)
C10 C 0.55606(13) 0.3613(2) 0.68672(13)
H10A H 0.6203 0.4185 0.7282
C11 C 0.47369(12) 0.3559(2) 0.71508(12)
H11A H 0.4805 0.4114 0.7753
C12 C 0.63164(13) 0.2931(2) 0.56540(14)
H1N H 0.1500(16) 0.354(3) 0.5504(16)
F1A F 0.6255(6) 0.1905(10) 0.4959(8)
F2A F 0.7274(3) 0.2725(13) 0.6437(4)
F3A F 0.6398(5) 0.4409(6) 0.5350(5)

#END
_chemical_name_systematic        
N-(3-(dimethylamino)propyl)-4-(trifluoromethyl)benzenesulfonamide
_exptl_crystal_colour            Off-white
_chemical_melting_point          342
