# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry C.
# This journal is © The Royal Society of Chemistry 2024

####################################################################### 
# 
# 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_Benz_d_CF3_H2O
_audit_block_doi                 10.5517/ccdc.csd.cc2j821y
_database_code_depnum_ccdc_archive 'CCDC 2331449'
loop_
_citation_id
_citation_doi
_citation_year
1 10.1039/D4TC00643G 2024
loop_
_audit_author_name
_audit_author_address
'Oiyao Appun Pegu'
;Indian Institute of Technology Guwahati
India
;
_audit_update_record             
;
2024-02-07 deposited with the CCDC.	2024-04-17 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C22 H14 F6 N4 O'
_chemical_formula_weight         464.37

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      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                   7.1823(6)
_cell_length_b                   28.182(2)
_cell_length_c                   10.1273(9)
_cell_angle_alpha                90
_cell_angle_beta                 91.871(2)
_cell_angle_gamma                90
_cell_volume                     2048.8(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    295(2)
_cell_measurement_reflns_used    9983
_cell_measurement_theta_min      2.93
_cell_measurement_theta_max      26.35

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.506
_exptl_crystal_F_000             944
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.15
_exptl_absorpt_coefficient_mu    0.133
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      295(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            47401
_diffrn_reflns_av_unetI/netI     0.0127
_diffrn_reflns_av_R_equivalents  0.0291
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -33
_diffrn_reflns_limit_k_max       33
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.928
_diffrn_reflns_theta_max         24.998
_diffrn_reflns_theta_full        24.998
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measured_fraction_theta_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_point_group_measured_fraction_full 0.991
_reflns_number_total             3575
_reflns_number_gt                3059
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.1428P)²+2.4388P] 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         3575
_refine_ls_number_parameters     310
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0918
_refine_ls_R_factor_gt           0.0813
_refine_ls_wR_factor_ref         0.2509
_refine_ls_wR_factor_gt          0.2321
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_restrained_S_all      1.035
_refine_ls_shift/su_max          0.000
_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
N2 N 0.6950(3) 0.50835(8) 0.6365(2) 0.0346(5) Uani 1 1 d . . . . .
N3 N 0.7730(3) 0.43844(9) 0.5313(2) 0.0398(6) Uani 1 1 d . . . . .
N4 N 0.6877(4) 0.43862(8) 0.7557(2) 0.0418(6) Uani 1 1 d . . . . .
N1 N 0.7023(3) 0.58075(8) 0.5435(2) 0.0426(6) Uani 1 1 d . . . . .
C14 C 0.7170(4) 0.45907(9) 0.6449(3) 0.0343(6) Uani 1 1 d . . . . .
O1 O -0.0087(5) 0.35467(11) 0.5219(4) 0.0916(11) Uani 1 1 d D . . . .
C7 C 0.7269(3) 0.53522(10) 0.5247(3) 0.0356(6) Uani 1 1 d . . . . .
C15 C 0.6985(4) 0.38885(10) 0.7652(3) 0.0402(7) Uani 1 1 d . . . . .
C8 C 0.7819(4) 0.51104(10) 0.4065(3) 0.0376(7) Uani 1 1 d . . . . .
C5 C 0.6465(4) 0.54018(9) 0.7354(3) 0.0359(6) Uani 1 1 d . . . . .
C13 C 0.8044(4) 0.46202(10) 0.4133(3) 0.0378(7) Uani 1 1 d . . . . .
C20 C 0.5780(4) 0.35904(10) 0.6942(3) 0.0448(7) Uani 1 1 d . . . . .
H20 H 0.491856 0.371723 0.633391 0.054 Uiso 1 1 calc R U . . .
C6 C 0.6511(4) 0.58464(10) 0.6749(3) 0.0399(7) Uani 1 1 d . . . . .
C16 C 0.8237(5) 0.36932(12) 0.8569(3) 0.0524(8) Uani 1 1 d . . . . .
H16 H 0.903613 0.388914 0.906174 0.063 Uiso 1 1 calc R U . . .
C4 C 0.6055(4) 0.53464(10) 0.8672(3) 0.0433(7) Uani 1 1 d . . . . .
H4 H 0.604947 0.504945 0.907236 0.052 Uiso 1 1 calc R U . . .
C19 C 0.5861(5) 0.31044(11) 0.7140(3) 0.0515(8) Uani 1 1 d . . . . .
C1 C 0.6109(5) 0.62544(11) 0.7464(3) 0.0531(8) Uani 1 1 d . . . . .
H1 H 0.613267 0.655288 0.707316 0.064 Uiso 1 1 calc R U . . .
C18 C 0.7125(5) 0.29099(11) 0.8038(4) 0.0590(9) Uani 1 1 d . . . . .
H18 H 0.718291 0.258307 0.815975 0.071 Uiso 1 1 calc R U . . .
C12 C 0.8577(4) 0.43693(12) 0.3028(3) 0.0478(8) Uani 1 1 d . . . . .
H12 H 0.871704 0.404150 0.306752 0.057 Uiso 1 1 calc R U . . .
C9 C 0.8135(4) 0.53478(12) 0.2880(3) 0.0474(7) Uani 1 1 d . . . . .
H9 H 0.797400 0.567469 0.282539 0.057 Uiso 1 1 calc R U . . .
C3 C 0.5655(5) 0.57555(12) 0.9361(3) 0.0517(8) Uani 1 1 d . . . . .
H3 H 0.536417 0.573203 1.024639 0.062 Uiso 1 1 calc R U . . .
C17 C 0.8299(5) 0.32057(13) 0.8752(4) 0.0606(9) Uani 1 1 d . . . . .
C2 C 0.5674(5) 0.61992(11) 0.8773(4) 0.0562(9) Uani 1 1 d . . . . .
H2 H 0.538860 0.646533 0.927052 0.067 Uiso 1 1 calc R U . . .
C10 C 0.8683(5) 0.50966(13) 0.1797(3) 0.0543(9) Uani 1 1 d . . . . .
H10 H 0.890960 0.525407 0.101091 0.065 Uiso 1 1 calc R U . . .
F5 F 0.4367(9) 0.28929(17) 0.5165(4) 0.194(3) Uani 1 1 d . . . . .
C11 C 0.8897(5) 0.46091(14) 0.1875(3) 0.0543(9) Uani 1 1 d . . . . .
H11 H 0.926288 0.444124 0.113654 0.065 Uiso 1 1 calc R U . . .
F4 F 0.4863(8) 0.23621(10) 0.6471(6) 0.216(3) Uani 1 1 d . . . . .
C22 C 0.4567(7) 0.27911(13) 0.6369(5) 0.0731(12) Uani 1 1 d . . . . .
F6 F 0.2880(6) 0.2845(2) 0.6686(6) 0.217(3) Uani 1 1 d . . . . .
F3 F 1.1361(6) 0.3098(2) 0.9502(6) 0.185(2) Uani 1 1 d . . . . .
F1 F 0.9538(10) 0.3193(2) 1.0898(5) 0.219(3) Uani 1 1 d . . . . .
F2 F 0.9562(9) 0.25671(14) 0.9908(7) 0.258(4) Uani 1 1 d . . . . .
C21 C 0.9626(8) 0.30011(17) 0.9766(7) 0.0971(17) Uani 1 1 d . . . . .
H3N H 0.807(5) 0.4061(14) 0.537(4) 0.056(10) Uiso 1 1 d . . . . .
H2O H 0.089(6) 0.3726(19) 0.516(6) 0.13(2) Uiso 1 1 d D . . . .
H1O H -0.008(11) 0.320(3) 0.534(8) 0.18(3) 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
N2 C7 1.387(3) . ?
N2 C5 1.397(3) . ?
N2 C14 1.400(3) . ?
N3 C14 1.361(4) . ?
N3 C13 1.392(4) . ?
N4 C14 1.285(4) . ?
N4 C15 1.408(4) . ?
N1 C7 1.310(4) . ?
N1 C6 1.396(4) . ?
C7 C8 1.444(4) . ?
C15 C16 1.385(4) . ?
C15 C20 1.390(4) . ?
C8 C13 1.392(4) . ?
C8 C9 1.399(4) . ?
C5 C4 1.385(4) . ?
C5 C6 1.396(4) . ?
C13 C12 1.388(4) . ?
C20 C19 1.385(4) . ?
C6 C1 1.394(4) . ?
C16 C17 1.387(5) . ?
C4 C3 1.383(4) . ?
C19 C18 1.378(5) . ?
C19 C22 1.485(5) . ?
C1 C2 1.381(5) . ?
C18 C17 1.374(5) . ?
C12 C11 1.375(5) . ?
C9 C10 1.374(5) . ?
C3 C2 1.385(5) . ?
C17 C21 1.494(6) . ?
C10 C11 1.385(5) . ?
F5 C22 1.256(6) . ?
F4 C22 1.231(5) . ?
C22 F6 1.273(6) . ?
F3 C21 1.312(8) . ?
F1 C21 1.271(8) . ?
F2 C21 1.233(6) . ?

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
C7 N2 C5 106.6(2) . . ?
C7 N2 C14 124.7(2) . . ?
C5 N2 C14 128.6(2) . . ?
C14 N3 C13 125.6(2) . . ?
C14 N4 C15 119.8(2) . . ?
C7 N1 C6 104.8(2) . . ?
N4 C14 N3 127.4(3) . . ?
N4 C14 N2 118.4(2) . . ?
N3 C14 N2 114.1(2) . . ?
N1 C7 N2 112.9(2) . . ?
N1 C7 C8 128.6(2) . . ?
N2 C7 C8 118.4(2) . . ?
C16 C15 C20 119.1(3) . . ?
C16 C15 N4 118.4(3) . . ?
C20 C15 N4 122.3(3) . . ?
C13 C8 C9 119.7(3) . . ?
C13 C8 C7 117.4(2) . . ?
C9 C8 C7 122.8(3) . . ?
C4 C5 C6 122.3(3) . . ?
C4 C5 N2 133.2(3) . . ?
C6 C5 N2 104.6(2) . . ?
C12 C13 N3 120.4(3) . . ?
C12 C13 C8 120.0(3) . . ?
N3 C13 C8 119.7(2) . . ?
C19 C20 C15 120.0(3) . . ?
C1 C6 C5 120.2(3) . . ?
C1 C6 N1 128.7(3) . . ?
C5 C6 N1 111.1(2) . . ?
C15 C16 C17 120.0(3) . . ?
C3 C4 C5 116.5(3) . . ?
C18 C19 C20 120.8(3) . . ?
C18 C19 C22 119.9(3) . . ?
C20 C19 C22 119.3(3) . . ?
C2 C1 C6 117.6(3) . . ?
C17 C18 C19 119.1(3) . . ?
C11 C12 C13 119.5(3) . . ?
C10 C9 C8 119.8(3) . . ?
C4 C3 C2 122.1(3) . . ?
C18 C17 C16 120.9(3) . . ?
C18 C17 C21 119.6(3) . . ?
C16 C17 C21 119.4(3) . . ?
C1 C2 C3 121.3(3) . . ?
C9 C10 C11 120.0(3) . . ?
C12 C11 C10 121.0(3) . . ?
F4 C22 F5 108.6(5) . . ?
F4 C22 F6 105.0(5) . . ?
F5 C22 F6 97.9(5) . . ?
F4 C22 C19 115.8(4) . . ?
F5 C22 C19 115.1(4) . . ?
F6 C22 C19 112.4(4) . . ?
F2 C21 F1 108.3(7) . . ?
F2 C21 F3 105.6(6) . . ?
F1 C21 F3 99.8(5) . . ?
F2 C21 C17 116.0(4) . . ?
F1 C21 C17 114.0(5) . . ?
F3 C21 C17 111.6(5) . . ?

_refine_diff_density_max         0.850
_refine_diff_density_min         -0.545
_refine_diff_density_rms         0.066


# start Validation Reply Form
_vrf_PLAT213_Benz_d_CF3_H2O      
;
PROBLEM: Atom F2              has ADP max/min Ratio .....        4.1 prolat
RESPONSE: Significant disorder observed in the F2 atom leading to this 
particular alert, which is commonly prevalent in -CF3 units. However 
we tried to grow better crystals, although, the results were similar. 
;
# end Validation Reply Form

####################################################################### 
# 
# 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_Benz_m_CF3
_database_code_depnum_ccdc_archive 'CCDC 2331458'
loop_
_audit_author_name
_audit_author_address
'Oiyao Appun Pegu'
;Indian Institute of Technology Guwahati
India
;
_audit_update_record             
;
2024-02-07 deposited with the CCDC.	2024-04-17 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C21 H13 F3 N4'
_chemical_formula_weight         378.35

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 '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                   11.5464(14)
_cell_length_b                   12.6424(16)
_cell_length_c                   12.9082(15)
_cell_angle_alpha                90
_cell_angle_beta                 112.572(3)
_cell_angle_gamma                90
_cell_volume                     1739.9(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    9248
_cell_measurement_theta_min      2.35
_cell_measurement_theta_max      26.15

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.444
_exptl_crystal_F_000             776
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.15
_exptl_absorpt_coefficient_mu    0.111
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            38995
_diffrn_reflns_av_unetI/netI     0.0191
_diffrn_reflns_av_R_equivalents  0.0451
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.348
_diffrn_reflns_theta_max         24.998
_diffrn_reflns_theta_full        24.998
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_point_group_measured_fraction_full 0.993
_reflns_number_total             3042
_reflns_number_gt                2411
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1000P)²+0.5098P] 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         3042
_refine_ls_number_parameters     257
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0742
_refine_ls_R_factor_gt           0.0589
_refine_ls_wR_factor_ref         0.2014
_refine_ls_wR_factor_gt          0.1706
_refine_ls_goodness_of_fit_ref   1.213
_refine_ls_restrained_S_all      1.213
_refine_ls_shift/su_max          0.000
_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
N2 N 0.43097(19) 0.63501(15) 0.93179(14) 0.0582(5) Uani 1 1 d . . . . .
N3 N 0.51048(19) 0.72695(16) 0.81863(15) 0.0589(5) Uani 1 1 d . . . . .
N4 N 0.3263(2) 0.62193(17) 0.74161(15) 0.0634(6) Uani 1 1 d . . . . .
N1 N 0.5026(2) 0.64859(17) 1.11921(15) 0.0678(6) Uani 1 1 d . . . . .
F2 F -0.0338(2) 0.6323(2) 0.3245(2) 0.1501(11) Uani 1 1 d . . . . .
C14 C 0.4195(2) 0.65983(18) 0.82256(17) 0.0544(6) Uani 1 1 d . . . . .
F3 F -0.0094(2) 0.7776(2) 0.3985(2) 0.1424(10) Uani 1 1 d . . . . .
C20 C 0.3983(2) 0.60071(19) 0.58672(18) 0.0560(6) Uani 1 1 d . . . . .
H20 H 0.475895 0.576337 0.636091 0.067 Uiso 1 1 calc R U . . .
C19 C 0.3723(2) 0.6024(2) 0.47323(19) 0.0585(6) Uani 1 1 d . . . . .
H19 H 0.431921 0.578299 0.446733 0.070 Uiso 1 1 calc R U . . .
C15 C 0.3102(2) 0.63495(18) 0.62837(17) 0.0549(6) Uani 1 1 d . . . . .
C7 C 0.5203(2) 0.67612(19) 1.02869(17) 0.0592(6) Uani 1 1 d . . . . .
C18 C 0.2592(2) 0.6393(2) 0.39902(19) 0.0615(6) Uani 1 1 d . . . . .
H18 H 0.241896 0.640953 0.322492 0.074 Uiso 1 1 calc R U . . .
F1 F 0.0525(2) 0.7516(3) 0.2676(2) 0.1890(17) Uani 1 1 d . . . . .
C16 C 0.1961(2) 0.6715(2) 0.55362(19) 0.0607(6) Uani 1 1 d . . . . .
H16 H 0.135634 0.694480 0.579674 0.073 Uiso 1 1 calc R U . . .
C6 C 0.3954(3) 0.5852(2) 1.08159(19) 0.0642(7) Uani 1 1 d . . . . .
C13 C 0.6080(2) 0.76886(18) 0.91173(17) 0.0553(6) Uani 1 1 d . . . . .
C8 C 0.6157(2) 0.7434(2) 1.01935(18) 0.0594(6) Uani 1 1 d . . . . .
C12 C 0.6951(2) 0.8366(2) 0.8970(2) 0.0638(7) Uani 1 1 d . . . . .
H12 H 0.689648 0.854008 0.825301 0.077 Uiso 1 1 calc R U . . .
C5 C 0.3477(3) 0.5754(2) 0.96501(19) 0.0619(6) Uani 1 1 d . . . . .
C17 C 0.1714(2) 0.6739(2) 0.43965(19) 0.0608(6) Uani 1 1 d . . . . .
C10 C 0.7979(3) 0.8529(2) 1.0979(2) 0.0751(8) Uani 1 1 d . . . . .
H10 H 0.861921 0.881470 1.160045 0.090 Uiso 1 1 calc R U . . .
C9 C 0.7121(3) 0.7868(2) 1.1122(2) 0.0721(7) Uani 1 1 d . . . . .
H9 H 0.717794 0.770384 1.184217 0.086 Uiso 1 1 calc R U . . .
C11 C 0.7896(3) 0.8778(2) 0.9900(2) 0.0711(7) Uani 1 1 d . . . . .
H11 H 0.848691 0.922761 0.980737 0.085 Uiso 1 1 calc R U . . .
C1 C 0.3343(3) 0.5367(2) 1.1430(2) 0.0800(9) Uani 1 1 d . . . . .
H1 H 0.365158 0.542840 1.220683 0.096 Uiso 1 1 calc R U . . .
C4 C 0.2409(3) 0.5174(2) 0.9072(2) 0.0756(8) Uani 1 1 d . . . . .
H4 H 0.209824 0.510528 0.829594 0.091 Uiso 1 1 calc R U . . .
C2 C 0.2284(3) 0.4800(3) 1.0870(3) 0.0879(9) Uani 1 1 d . . . . .
H2 H 0.186273 0.447429 1.126966 0.106 Uiso 1 1 calc R U . . .
C21 C 0.0479(3) 0.7101(3) 0.3582(3) 0.0910(10) Uani 1 1 d . . . . .
C3 C 0.1826(3) 0.4700(3) 0.9713(3) 0.0893(9) Uani 1 1 d . . . . .
H3 H 0.110466 0.430321 0.935416 0.107 Uiso 1 1 calc R U . . .
H3N H 0.506(3) 0.749(2) 0.752(3) 0.077(8) 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
N2 C7 1.381(3) . ?
N2 C14 1.400(3) . ?
N2 C5 1.411(3) . ?
N3 C14 1.367(3) . ?
N3 C13 1.398(3) . ?
N4 C14 1.271(3) . ?
N4 C15 1.411(3) . ?
N1 C7 1.309(3) . ?
N1 C6 1.395(4) . ?
F2 C21 1.316(4) . ?
F3 C21 1.305(4) . ?
C20 C19 1.378(3) . ?
C20 C15 1.390(3) . ?
C19 C18 1.371(3) . ?
C15 C16 1.380(3) . ?
C7 C8 1.432(4) . ?
C18 C17 1.378(3) . ?
F1 C21 1.302(4) . ?
C16 C17 1.387(3) . ?
C6 C1 1.389(4) . ?
C6 C5 1.395(3) . ?
C13 C12 1.388(4) . ?
C13 C8 1.395(3) . ?
C8 C9 1.398(4) . ?
C12 C11 1.377(4) . ?
C5 C4 1.381(4) . ?
C17 C21 1.482(4) . ?
C10 C9 1.361(4) . ?
C10 C11 1.395(4) . ?
C1 C2 1.361(4) . ?
C4 C3 1.387(4) . ?
C2 C3 1.386(4) . ?

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
C7 N2 C14 125.2(2) . . ?
C7 N2 C5 106.55(19) . . ?
C14 N2 C5 127.8(2) . . ?
C14 N3 C13 125.5(2) . . ?
C14 N4 C15 122.8(2) . . ?
C7 N1 C6 105.3(2) . . ?
N4 C14 N3 128.6(2) . . ?
N4 C14 N2 117.8(2) . . ?
N3 C14 N2 113.6(2) . . ?
C19 C20 C15 120.9(2) . . ?
C18 C19 C20 120.6(2) . . ?
C16 C15 C20 118.57(19) . . ?
C16 C15 N4 118.3(2) . . ?
C20 C15 N4 122.7(2) . . ?
N1 C7 N2 112.9(2) . . ?
N1 C7 C8 128.5(2) . . ?
N2 C7 C8 118.6(2) . . ?
C19 C18 C17 119.0(2) . . ?
C15 C16 C17 120.1(2) . . ?
C1 C6 C5 120.0(3) . . ?
C1 C6 N1 129.1(3) . . ?
C5 C6 N1 110.9(2) . . ?
C12 C13 C8 120.4(2) . . ?
C12 C13 N3 120.2(2) . . ?
C8 C13 N3 119.4(2) . . ?
C13 C8 C9 119.2(3) . . ?
C13 C8 C7 117.6(2) . . ?
C9 C8 C7 123.1(2) . . ?
C11 C12 C13 119.2(2) . . ?
C4 C5 C6 122.0(2) . . ?
C4 C5 N2 133.7(2) . . ?
C6 C5 N2 104.3(2) . . ?
C18 C17 C16 121.0(2) . . ?
C18 C17 C21 118.4(2) . . ?
C16 C17 C21 120.6(2) . . ?
C9 C10 C11 119.9(2) . . ?
C10 C9 C8 120.4(2) . . ?
C12 C11 C10 120.8(3) . . ?
C2 C1 C6 118.6(3) . . ?
C5 C4 C3 116.4(3) . . ?
C1 C2 C3 120.9(3) . . ?
F1 C21 F3 107.2(3) . . ?
F1 C21 F2 106.0(3) . . ?
F3 C21 F2 102.2(3) . . ?
F1 C21 C17 113.7(3) . . ?
F3 C21 C17 114.6(3) . . ?
F2 C21 C17 112.1(3) . . ?
C2 C3 C4 122.1(3) . . ?

_refine_diff_density_max         0.411
_refine_diff_density_min         -0.348
_refine_diff_density_rms         0.038

####################################################################### 
# 
# 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_Benz_d_CF3_DMSO
_audit_block_doi                 10.5517/ccdc.csd.cc2j8230
_database_code_depnum_ccdc_archive 'CCDC 2331451'
loop_
_citation_id
_citation_doi
_citation_year
1 10.1039/D4TC00643G 2024
loop_
_audit_author_name
_audit_author_address
'Oiyao Appun Pegu'
;Indian Institute of Technology Guwahati
India
;
_audit_update_record             
;
2024-02-07 deposited with the CCDC.	2024-04-17 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C24 H18 F6 N4 O S'
_chemical_formula_weight         524.48

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'
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 0.0060 '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'

_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                   15.3037(6)
_cell_length_b                   10.3312(4)
_cell_length_c                   16.3311(7)
_cell_angle_alpha                90
_cell_angle_beta                 114.1120(10)
_cell_angle_gamma                90
_cell_volume                     2356.75(17)
_cell_formula_units_Z            4
_cell_measurement_temperature    297(2)
_cell_measurement_reflns_used    9554
_cell_measurement_theta_min      2.45
_cell_measurement_theta_max      26.32

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.478
_exptl_crystal_F_000             1072
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.15
_exptl_absorpt_coefficient_mu    0.210
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      297(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            52338
_diffrn_reflns_av_unetI/netI     0.0240
_diffrn_reflns_av_R_equivalents  0.0533
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.399
_diffrn_reflns_theta_max         25.000
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             4133
_reflns_number_gt                3104
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.0982P)²+9.4270P] 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         4133
_refine_ls_number_parameters     335
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1183
_refine_ls_R_factor_gt           0.0946
_refine_ls_wR_factor_ref         0.2520
_refine_ls_wR_factor_gt          0.2246
_refine_ls_goodness_of_fit_ref   0.915
_refine_ls_restrained_S_all      0.915
_refine_ls_shift/su_max          0.002
_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
S1 S 0.14643(11) 0.51039(18) 0.08222(11) 0.0838(5) Uani 1 1 d . . . . .
N3 N 0.4085(3) 0.5345(4) 0.3163(3) 0.0477(9) Uani 1 1 d . . . . .
N2 N 0.5361(2) 0.6321(3) 0.4312(2) 0.0442(8) Uani 1 1 d . . . . .
N4 N 0.4000(2) 0.7516(4) 0.3582(3) 0.0518(9) Uani 1 1 d . . . . .
N1 N 0.6697(2) 0.5280(4) 0.5229(3) 0.0541(10) Uani 1 1 d . . . . .
C14 C 0.4415(3) 0.6429(4) 0.3655(3) 0.0441(10) Uani 1 1 d . . . . .
F1 F 0.2331(3) 1.0692(5) 0.1201(3) 0.1197(16) Uani 1 1 d . . . . .
F3 F 0.0895(3) 1.0624(5) 0.1046(4) 0.143(2) Uani 1 1 d . . . . .
C7 C 0.5872(3) 0.5163(4) 0.4539(3) 0.0450(10) Uani 1 1 d . . . . .
C15 C 0.3033(3) 0.7669(4) 0.3000(3) 0.0475(10) Uani 1 1 d . . . . .
C16 C 0.2799(3) 0.8608(5) 0.2340(3) 0.0520(11) Uani 1 1 d . . . . .
H16 H 0.328165 0.905612 0.225337 0.062 Uiso 1 1 calc R U . . .
C13 C 0.4565(3) 0.4168(4) 0.3299(3) 0.0470(10) Uani 1 1 d . . . . .
C5 C 0.5925(3) 0.7261(5) 0.4915(3) 0.0472(10) Uani 1 1 d . . . . .
C8 C 0.5470(3) 0.4044(4) 0.3999(3) 0.0475(10) Uani 1 1 d . . . . .
C20 C 0.2306(3) 0.7015(5) 0.3126(3) 0.0500(11) Uani 1 1 d . . . . .
H20 H 0.245262 0.638391 0.356824 0.060 Uiso 1 1 calc R U . . .
C17 C 0.1850(3) 0.8880(5) 0.1809(3) 0.0533(11) Uani 1 1 d . . . . .
C19 C 0.1357(3) 0.7310(5) 0.2587(3) 0.0535(11) Uani 1 1 d . . . . .
C18 C 0.1123(3) 0.8242(5) 0.1931(3) 0.0581(12) Uani 1 1 d . . . . .
H18 H 0.048581 0.843660 0.157610 0.070 Uiso 1 1 calc R U . . .
C6 C 0.6748(3) 0.6576(5) 0.5474(3) 0.0504(11) Uani 1 1 d . . . . .
F2 F 0.1387(5) 0.9429(5) 0.0302(3) 0.159(2) Uani 1 1 d . . . . .
C4 C 0.5805(3) 0.8566(5) 0.5013(3) 0.0582(12) Uani 1 1 d . . . . .
H4 H 0.525867 0.900767 0.463740 0.070 Uiso 1 1 calc R U . . .
C9 C 0.5949(4) 0.2853(5) 0.4148(4) 0.0598(12) Uani 1 1 d . . . . .
C2 C 0.7362(4) 0.8531(6) 0.6271(4) 0.0697(15) Uani 1 1 d . . . . .
H2 H 0.784027 0.898024 0.673026 0.084 Uiso 1 1 calc R U . . .
C12 C 0.4157(4) 0.3115(5) 0.2737(3) 0.0588(12) Uani 1 1 d . . . . .
H12 H 0.356078 0.319595 0.225973 0.071 Uiso 1 1 calc R U . . .
C22 C 0.0577(4) 0.6600(7) 0.2717(4) 0.0716(16) Uani 1 1 d . . . . .
F4 F 0.0822(3) 0.5746(8) 0.3290(6) 0.229(5) Uani 1 1 d . . . . .
C1 C 0.7476(3) 0.7228(6) 0.6166(3) 0.0641(14) Uani 1 1 d . . . . .
H1 H 0.802338 0.679481 0.654785 0.077 Uiso 1 1 calc R U . . .
C3 C 0.6551(4) 0.9184(6) 0.5706(4) 0.0691(14) Uani 1 1 d . . . . .
H3 H 0.650200 1.006589 0.579298 0.083 Uiso 1 1 calc R U . . .
O1 O 0.2416(4) 0.5123(6) 0.1556(3) 0.135(2) Uani 1 1 d . . . . .
C11 C 0.4643(4) 0.1954(5) 0.2892(4) 0.0677(14) Uani 1 1 d . . . . .
H11 H 0.436779 0.125208 0.251882 0.081 Uiso 1 1 calc R U . . .
C10 C 0.5539(4) 0.1816(5) 0.3600(4) 0.0681(14) Uani 1 1 d . . . . .
H10 H 0.585731 0.102656 0.369961 0.082 Uiso 1 1 calc R U . . .
F6 F -0.0075(4) 0.6199(10) 0.2046(4) 0.220(4) Uani 1 1 d . . . . .
C21 C 0.1614(4) 0.9909(6) 0.1101(4) 0.0757(16) Uani 1 1 d . . . . .
F5 F 0.0091(6) 0.7324(7) 0.3008(7) 0.224(4) Uani 1 1 d . . . . .
C23 C 0.1304(7) 0.3578(7) 0.0330(6) 0.124(3) Uani 1 1 d . . . . .
H23A H 0.187917 0.332335 0.027052 0.186 Uiso 1 1 calc R U . . .
H23B H 0.078330 0.360660 -0.025281 0.186 Uiso 1 1 calc R U . . .
H23C H 0.116264 0.296381 0.069916 0.186 Uiso 1 1 calc R U . . .
C24 C 0.1574(7) 0.5959(9) -0.0062(6) 0.129(3) Uani 1 1 d . . . . .
H24A H 0.173568 0.684386 0.011307 0.194 Uiso 1 1 calc R U . . .
H24B H 0.097706 0.592634 -0.058175 0.194 Uiso 1 1 calc R U . . .
H24C H 0.206764 0.557282 -0.020067 0.194 Uiso 1 1 calc R U . . .
H3N H 0.356(3) 0.536(4) 0.276(3) 0.041(12) Uiso 1 1 d . . . . .
H9 H 0.656(4) 0.281(5) 0.463(3) 0.054(13) 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
S1 O1 1.460(5) . ?
S1 C23 1.741(7) . ?
S1 C24 1.758(9) . ?
N3 C14 1.351(6) . ?
N3 C13 1.391(6) . ?
N2 C7 1.394(5) . ?
N2 C5 1.401(6) . ?
N2 C14 1.411(5) . ?
N4 C14 1.271(6) . ?
N4 C15 1.404(5) . ?
N1 C7 1.309(5) . ?
N1 C6 1.391(6) . ?
F1 C21 1.318(7) . ?
F3 C21 1.297(7) . ?
C7 C8 1.432(6) . ?
C15 C20 1.387(6) . ?
C15 C16 1.383(6) . ?
C16 C17 1.383(6) . ?
C13 C8 1.396(6) . ?
C13 C12 1.396(7) . ?
C5 C4 1.378(7) . ?
C5 C6 1.408(6) . ?
C8 C9 1.402(7) . ?
C20 C19 1.390(6) . ?
C17 C18 1.376(7) . ?
C17 C21 1.502(7) . ?
C19 C18 1.375(7) . ?
C19 C22 1.488(7) . ?
C6 C1 1.394(7) . ?
F2 C21 1.304(8) . ?
C4 C3 1.392(7) . ?
C9 C10 1.372(8) . ?
C2 C1 1.376(8) . ?
C2 C3 1.382(8) . ?
C12 C11 1.379(7) . ?
C22 F4 1.229(7) . ?
C22 F6 1.215(7) . ?
C22 F5 1.275(8) . ?
C11 C10 1.394(8) . ?

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 S1 C23 107.2(4) . . ?
O1 S1 C24 105.6(4) . . ?
C23 S1 C24 96.8(4) . . ?
C14 N3 C13 125.8(4) . . ?
C7 N2 C5 106.9(3) . . ?
C7 N2 C14 124.1(4) . . ?
C5 N2 C14 128.7(4) . . ?
C14 N4 C15 120.8(4) . . ?
C7 N1 C6 104.9(4) . . ?
N4 C14 N3 128.7(4) . . ?
N4 C14 N2 117.4(4) . . ?
N3 C14 N2 113.9(4) . . ?
N1 C7 N2 112.9(4) . . ?
N1 C7 C8 128.6(4) . . ?
N2 C7 C8 118.4(4) . . ?
C20 C15 C16 119.3(4) . . ?
C20 C15 N4 122.1(4) . . ?
C16 C15 N4 118.2(4) . . ?
C17 C16 C15 120.1(4) . . ?
N3 C13 C8 119.6(4) . . ?
N3 C13 C12 120.7(4) . . ?
C8 C13 C12 119.7(4) . . ?
C4 C5 N2 133.4(4) . . ?
C4 C5 C6 122.8(4) . . ?
N2 C5 C6 103.8(4) . . ?
C13 C8 C9 119.8(5) . . ?
C13 C8 C7 117.6(4) . . ?
C9 C8 C7 122.7(4) . . ?
C15 C20 C19 119.5(4) . . ?
C18 C17 C16 121.1(4) . . ?
C18 C17 C21 119.8(4) . . ?
C16 C17 C21 119.2(5) . . ?
C18 C19 C20 121.3(4) . . ?
C18 C19 C22 119.1(4) . . ?
C20 C19 C22 119.6(5) . . ?
C17 C18 C19 118.7(4) . . ?
N1 C6 C1 129.2(4) . . ?
N1 C6 C5 111.5(4) . . ?
C1 C6 C5 119.3(5) . . ?
C5 C4 C3 116.1(5) . . ?
C10 C9 C8 120.3(5) . . ?
C1 C2 C3 121.2(5) . . ?
C11 C12 C13 119.6(5) . . ?
F4 C22 F6 109.0(8) . . ?
F4 C22 F5 100.4(7) . . ?
F6 C22 F5 98.5(7) . . ?
F4 C22 C19 116.7(5) . . ?
F6 C22 C19 116.8(5) . . ?
F5 C22 C19 112.8(6) . . ?
C2 C1 C6 118.3(5) . . ?
C4 C3 C2 122.2(5) . . ?
C12 C11 C10 121.0(5) . . ?
C9 C10 C11 119.6(5) . . ?
F2 C21 F3 106.0(6) . . ?
F2 C21 F1 103.0(6) . . ?
F3 C21 F1 107.4(6) . . ?
F2 C21 C17 112.5(5) . . ?
F3 C21 C17 112.7(5) . . ?
F1 C21 C17 114.4(5) . . ?

_refine_diff_density_max         1.196
_refine_diff_density_min         -0.680
_refine_diff_density_rms         0.074

####################################################################### 
# 
# 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_Benz_m_CF3_dep_Benz_m_CF3_TBA
_audit_block_doi                 10.5517/ccdc.csd.cc2j82lh
_database_code_depnum_ccdc_archive 'CCDC 2331466'
loop_
_citation_id
_citation_doi
_citation_year
1 10.1039/D4TC00643G 2024
loop_
_audit_author_name
_audit_author_address
'Oiyao Appun Pegu'
;Indian Institute of Technology Guwahati
India
;
_audit_update_record             
;
2024-02-07 deposited with the CCDC.	2024-04-17 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C58 H61 F6 N9'
_chemical_formula_weight         998.15

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.7718(6)
_cell_length_b                   13.5532(10)
_cell_length_c                   22.6964(16)
_cell_angle_alpha                90.310(2)
_cell_angle_beta                 100.163(2)
_cell_angle_gamma                98.003(2)
_cell_volume                     2628.8(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    297(2)
_cell_measurement_reflns_used    9879
_cell_measurement_theta_min      2.34
_cell_measurement_theta_max      25.59

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.261
_exptl_crystal_F_000             1052
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.15
_exptl_absorpt_coefficient_mu    0.091
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      297(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            62132
_diffrn_reflns_av_unetI/netI     0.0246
_diffrn_reflns_av_R_equivalents  0.0350
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_theta_min         1.747
_diffrn_reflns_theta_max         24.996
_diffrn_reflns_theta_full        24.996
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.994
_reflns_number_total             9196
_reflns_number_gt                6809
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.1131P)²+1.7983P] 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         9196
_refine_ls_number_parameters     666
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0989
_refine_ls_R_factor_gt           0.0762
_refine_ls_wR_factor_ref         0.2363
_refine_ls_wR_factor_gt          0.2068
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_restrained_S_all      1.046
_refine_ls_shift/su_max          0.000
_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
N3 N 0.5004(3) 0.53898(17) 0.88151(11) 0.0532(6) Uani 1 1 d . . . . .
N2 N 0.4684(2) 0.37144(16) 0.90345(10) 0.0503(5) Uani 1 1 d . . . . .
N1 N 0.3177(3) 0.30215(18) 0.96709(11) 0.0603(6) Uani 1 1 d . . . . .
N3A N 0.7692(3) 0.98247(17) 0.77867(11) 0.0594(6) Uani 1 1 d . . . . .
N1A N 0.5464(3) 0.70311(17) 0.80503(11) 0.0604(6) Uani 1 1 d . . . . .
N4A N 0.5927(3) 0.96731(18) 0.68548(11) 0.0620(6) Uani 1 1 d . . . . .
N2A N 0.5905(3) 0.83610(16) 0.74872(10) 0.0545(6) Uani 1 1 d . . . . .
N4 N 0.6291(3) 0.42350(17) 0.83691(11) 0.0634(6) Uani 1 1 d . . . . .
N5 N 0.1496(3) 0.1510(2) 0.68981(12) 0.0694(7) Uani 1 1 d . . . . .
C14 C 0.5395(3) 0.44717(19) 0.87144(12) 0.0509(6) Uani 1 1 d . . . . .
C7 C 0.3645(3) 0.3843(2) 0.94173(11) 0.0511(6) Uani 1 1 d . . . . .
C15A C 0.6226(3) 1.0670(2) 0.67129(14) 0.0564(7) Uani 1 1 d . . . . .
C7A C 0.6295(3) 0.7903(2) 0.80194(12) 0.0541(7) Uani 1 1 d . . . . .
C15 C 0.7160(3) 0.4979(2) 0.80815(14) 0.0583(7) Uani 1 1 d . . . . .
C8 C 0.3248(3) 0.4821(2) 0.94894(11) 0.0518(6) Uani 1 1 d . . . . .
C14A C 0.6539(3) 0.9352(2) 0.73731(13) 0.0555(7) Uani 1 1 d . . . . .
C6 C 0.3957(3) 0.2304(2) 0.94569(13) 0.0591(7) Uani 1 1 d . . . . .
C5 C 0.4904(3) 0.2715(2) 0.90605(12) 0.0549(7) Uani 1 1 d . . . . .
C13 C 0.3955(3) 0.5589(2) 0.91781(11) 0.0502(6) Uani 1 1 d . . . . .
C13A C 0.8170(3) 0.9377(2) 0.83189(13) 0.0551(7) Uani 1 1 d . . . . .
C9 C 0.2210(3) 0.5036(3) 0.98588(13) 0.0637(8) Uani 1 1 d . . . . .
H9 H 0.173559 0.452886 1.006808 0.076 Uiso 1 1 calc R U . . .
C34 C 0.0717(3) 0.2116(3) 0.72892(15) 0.0699(8) Uani 1 1 d . . . . .
H34A H 0.018406 0.166216 0.754075 0.084 Uiso 1 1 calc R U . . .
H34B H -0.007498 0.242562 0.703171 0.084 Uiso 1 1 calc R U . . .
C8A C 0.7504(3) 0.8421(2) 0.84644(12) 0.0550(7) Uani 1 1 d . . . . .
C20A C 0.6559(3) 1.1488(2) 0.71111(16) 0.0640(8) Uani 1 1 d . . . . .
H20A H 0.666521 1.138739 0.752042 0.077 Uiso 1 1 calc R U . . .
C16A C 0.6044(4) 1.0865(3) 0.61089(15) 0.0682(8) Uani 1 1 d . . . . .
H16A H 0.577838 1.033298 0.583219 0.082 Uiso 1 1 calc R U . . .
C16 C 0.6799(4) 0.5062(2) 0.74685(14) 0.0626(7) Uani 1 1 d . . . . .
H16 H 0.593316 0.466379 0.724993 0.075 Uiso 1 1 calc R U . . .
C4 C 0.5829(4) 0.2161(2) 0.87994(15) 0.0696(8) Uani 1 1 d . . . . .
H4 H 0.645144 0.243886 0.853393 0.083 Uiso 1 1 calc R U . . .
C9A C 0.8027(4) 0.8020(2) 0.90221(13) 0.0655(8) Uani 1 1 d . . . . .
H9A H 0.757349 0.739411 0.911809 0.079 Uiso 1 1 calc R U . . .
C6A C 0.4434(3) 0.6897(2) 0.74976(14) 0.0597(7) Uani 1 1 d . . . . .
C12 C 0.3619(3) 0.6552(2) 0.92399(14) 0.0622(7) Uani 1 1 d . . . . .
H12 H 0.408900 0.706790 0.903538 0.075 Uiso 1 1 calc R U . . .
C12A C 0.9357(4) 0.9892(2) 0.87497(15) 0.0664(8) Uani 1 1 d . . . . .
H12A H 0.981184 1.052691 0.866893 0.080 Uiso 1 1 calc R U . . .
F3 F 0.5970(4) 0.5400(4) 0.62754(13) 0.1739(16) Uani 1 1 d . . . . .
C17 C 0.7721(4) 0.5736(2) 0.71785(15) 0.0707(9) Uani 1 1 d . . . . .
C5A C 0.4690(3) 0.7706(2) 0.71367(13) 0.0572(7) Uani 1 1 d . . . . .
F2 F 0.8247(5) 0.5373(4) 0.62476(13) 0.195(2) Uani 1 1 d . . . . .
C20 C 0.8480(4) 0.5560(2) 0.83960(15) 0.0701(8) Uani 1 1 d . . . . .
H20 H 0.874754 0.549876 0.880788 0.084 Uiso 1 1 calc R U . . .
C11 C 0.2591(4) 0.6741(3) 0.96032(15) 0.0709(8) Uani 1 1 d . . . . .
H11 H 0.236361 0.738555 0.964103 0.085 Uiso 1 1 calc R U . . .
C22 C 0.2670(4) 0.0946(3) 0.72820(16) 0.0772(10) Uani 1 1 d . . . . .
H22A H 0.314781 0.056780 0.701865 0.093 Uiso 1 1 calc R U . . .
H22B H 0.349082 0.142761 0.750663 0.093 Uiso 1 1 calc R U . . .
C10 C 0.1889(4) 0.5985(3) 0.99139(15) 0.0727(9) Uani 1 1 d . . . . .
H10 H 0.119837 0.612307 1.016026 0.087 Uiso 1 1 calc R U . . .
C19A C 0.6735(4) 1.2445(3) 0.6906(2) 0.0809(10) Uani 1 1 d . . . . .
H19A H 0.694686 1.297954 0.718086 0.097 Uiso 1 1 calc R U . . .
C10A C 0.9201(4) 0.8553(3) 0.94219(14) 0.0727(9) Uani 1 1 d . . . . .
H10A H 0.955875 0.828734 0.978909 0.087 Uiso 1 1 calc R U . . .
C4A C 0.3834(4) 0.7750(3) 0.65710(15) 0.0722(8) Uani 1 1 d . . . . .
H4A H 0.401169 0.829157 0.633020 0.087 Uiso 1 1 calc R U . . .
C30 C 0.2391(4) 0.2175(3) 0.65029(17) 0.0827(10) Uani 1 1 d . . . . .
H30A H 0.324650 0.259043 0.675817 0.099 Uiso 1 1 calc R U . . .
H30B H 0.284692 0.175535 0.625477 0.099 Uiso 1 1 calc R U . . .
C19 C 0.9396(4) 0.6225(3) 0.81060(18) 0.0820(10) Uani 1 1 d . . . . .
H19 H 1.027471 0.661300 0.832355 0.098 Uiso 1 1 calc R U . . .
C1A C 0.3281(4) 0.6105(2) 0.72990(16) 0.0726(9) Uani 1 1 d . . . . .
H1A H 0.310143 0.556420 0.754061 0.087 Uiso 1 1 calc R U . . .
C18 C 0.9028(4) 0.6322(3) 0.74999(18) 0.0812(10) Uani 1 1 d . . . . .
H18 H 0.964828 0.677691 0.730533 0.097 Uiso 1 1 calc R U . . .
C1 C 0.3936(4) 0.1308(2) 0.96007(16) 0.0772(9) Uani 1 1 d . . . . .
H1 H 0.331620 0.102248 0.986503 0.093 Uiso 1 1 calc R U . . .
C11A C 0.9860(4) 0.9492(3) 0.92791(15) 0.0744(9) Uani 1 1 d . . . . .
H11A H 1.066150 0.985088 0.955287 0.089 Uiso 1 1 calc R U . . .
C17A C 0.6242(4) 1.1821(3) 0.59033(18) 0.0811(10) Uani 1 1 d . . . . .
C3 C 0.5783(5) 0.1175(3) 0.89519(18) 0.0839(10) Uani 1 1 d . . . . .
H3 H 0.639469 0.077960 0.878666 0.101 Uiso 1 1 calc R U . . .
C26 C 0.0193(4) 0.0801(3) 0.65279(18) 0.0826(10) Uani 1 1 d . . . . .
H26A H -0.049694 0.119079 0.627710 0.099 Uiso 1 1 calc R U . . .
H26B H -0.040996 0.043839 0.679758 0.099 Uiso 1 1 calc R U . . .
C3A C 0.2684(4) 0.6941(3) 0.63765(17) 0.0853(10) Uani 1 1 d . . . . .
H3A H 0.208396 0.694006 0.599526 0.102 Uiso 1 1 calc R U . . .
C2A C 0.2413(4) 0.6135(3) 0.67388(18) 0.0820(10) Uani 1 1 d . . . . .
H2A H 0.163004 0.560998 0.659804 0.098 Uiso 1 1 calc R U . . .
C18A C 0.6602(4) 1.2626(3) 0.6305(2) 0.0909(13) Uani 1 1 d . . . . .
H18A H 0.675189 1.327427 0.617181 0.109 Uiso 1 1 calc R U . . .
C35 C 0.1789(4) 0.2930(3) 0.76928(19) 0.0895(11) Uani 1 1 d . . . . .
H35A H 0.249371 0.262640 0.799266 0.107 Uiso 1 1 calc R U . . .
H35B H 0.241526 0.335176 0.745460 0.107 Uiso 1 1 calc R U . . .
C23 C 0.2017(5) 0.0245(3) 0.7715(2) 0.1025(14) Uani 1 1 d . . . . .
H23A H 0.195989 0.062015 0.807332 0.123 Uiso 1 1 calc R U . . .
H23B H 0.096037 -0.004379 0.753647 0.123 Uiso 1 1 calc R U . . .
C36 C 0.0841(5) 0.3563(3) 0.80007(18) 0.0872(11) Uani 1 1 d . . . . .
H36A H 0.154342 0.411441 0.821764 0.105 Uiso 1 1 calc R U . . .
H36B H 0.010924 0.384117 0.769777 0.105 Uiso 1 1 calc R U . . .
F1 F 0.7450(8) 0.6701(3) 0.63383(16) 0.242(3) Uani 1 1 d . . . . .
C2 C 0.4852(5) 0.0758(3) 0.93433(18) 0.0885(11) Uani 1 1 d . . . . .
H2 H 0.484885 0.008985 0.943379 0.106 Uiso 1 1 calc R U . . .
C37 C -0.0052(5) 0.2998(3) 0.84279(19) 0.0981(12) Uani 1 1 d . . . . .
H37A H -0.088974 0.253623 0.820703 0.147 Uiso 1 1 calc R U . . .
H37B H -0.047619 0.345696 0.865616 0.147 Uiso 1 1 calc R U . . .
H37C H 0.063667 0.264033 0.869397 0.147 Uiso 1 1 calc R U . . .
C31 C 0.1462(5) 0.2845(4) 0.60991(19) 0.0987(12) Uani 1 1 d . . . . .
H31A H 0.067752 0.243931 0.580903 0.118 Uiso 1 1 calc R U . . .
H31B H 0.092506 0.323060 0.633679 0.118 Uiso 1 1 calc R U . . .
F2A F 0.7117(7) 1.1670(6) 0.50226(19) 0.305(4) Uani 1 1 d . . . . .
C24 C 0.2930(5) -0.0548(3) 0.7881(2) 0.1047(13) Uani 1 1 d . . . . .
H24A H 0.395031 -0.024664 0.809101 0.126 Uiso 1 1 calc R U . . .
H24B H 0.309090 -0.085671 0.751426 0.126 Uiso 1 1 calc R U . . .
C21 C 0.7343(6) 0.5816(4) 0.6522(2) 0.1006(13) Uani 1 1 d . . . . .
F1A F 0.6060(10) 1.2867(4) 0.5094(2) 0.267(3) Uani 1 1 d . . . . .
C27 C 0.0692(6) 0.0051(4) 0.6131(2) 0.1238(17) Uani 1 1 d . . . . .
H27A H 0.145711 -0.031059 0.636472 0.149 Uiso 1 1 calc R U . . .
H27B H 0.116359 0.038997 0.581776 0.149 Uiso 1 1 calc R U . . .
F3A F 0.4862(8) 1.1589(5) 0.49460(18) 0.252(3) Uani 1 1 d . . . . .
C25 C 0.2337(7) -0.1350(4) 0.8253(3) 0.1275(18) Uani 1 1 d . . . . .
H25A H 0.261565 -0.114175 0.866735 0.191 Uiso 1 1 calc R U . . .
H25B H 0.279085 -0.193855 0.818967 0.191 Uiso 1 1 calc R U . . .
H25C H 0.121917 -0.149315 0.814369 0.191 Uiso 1 1 calc R U . . .
C21A C 0.6127(7) 1.1982(5) 0.5260(3) 0.128(2) Uani 1 1 d . . . . .
C32 C 0.2490(7) 0.3541(4) 0.5776(2) 0.1309(18) Uani 1 1 d . . . . .
H32A H 0.307153 0.315328 0.555819 0.157 Uiso 1 1 calc R U . . .
H32B H 0.323879 0.396739 0.606733 0.157 Uiso 1 1 calc R U . . .
C28 C -0.0823(8) -0.0699(6) 0.5844(3) 0.202(4) Uani 1 1 d D . . . .
H28A H -0.136160 -0.094061 0.616446 0.242 Uiso 1 1 calc R U . . .
H28B H -0.151647 -0.032643 0.558174 0.242 Uiso 1 1 calc R U . . .
C33 C 0.1585(9) 0.4188(5) 0.5340(3) 0.166(3) Uani 1 1 d . . . . .
H33A H 0.094995 0.377742 0.501713 0.249 Uiso 1 1 calc R U . . .
H33B H 0.230571 0.467065 0.518274 0.249 Uiso 1 1 calc R U . . .
H33C H 0.092736 0.452519 0.554387 0.249 Uiso 1 1 calc R U . . .
C29 C -0.0589(11) -0.1516(7) 0.5521(5) 0.237(4) Uani 1 1 d D . . . .
H29A H 0.006897 -0.130024 0.523678 0.356 Uiso 1 1 calc R U . . .
H29B H -0.157828 -0.184643 0.531305 0.356 Uiso 1 1 calc R U . . .
H29C H -0.009444 -0.196961 0.578963 0.356 Uiso 1 1 calc R U . . .
H3N H 0.534(4) 0.587(2) 0.8579(15) 0.072(9) Uiso 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N3 C14 1.364(3) . ?
N3 C13 1.391(3) . ?
N2 C7 1.392(3) . ?
N2 C5 1.395(3) . ?
N2 C14 1.400(3) . ?
N1 C7 1.304(3) . ?
N1 C6 1.395(4) . ?
N3A C14A 1.339(4) . ?
N3A C13A 1.379(4) . ?
N1A C7A 1.308(4) . ?
N1A C6A 1.406(4) . ?
N4A C14A 1.307(4) . ?
N4A C15A 1.391(4) . ?
N2A C7A 1.372(4) . ?
N2A C5A 1.409(4) . ?
N2A C14A 1.424(3) . ?
N4 C14 1.272(3) . ?
N4 C15 1.412(4) . ?
N5 C26 1.511(4) . ?
N5 C34 1.514(4) . ?
N5 C30 1.514(4) . ?
N5 C22 1.521(4) . ?
C7 C8 1.432(4) . ?
C15A C16A 1.383(4) . ?
C15A C20A 1.392(4) . ?
C7A C8A 1.430(4) . ?
C15 C16 1.380(4) . ?
C15 C20 1.385(4) . ?
C8 C13 1.396(4) . ?
C8 C9 1.400(4) . ?
C6 C1 1.389(4) . ?
C6 C5 1.396(4) . ?
C5 C4 1.381(4) . ?
C13 C12 1.390(4) . ?
C13A C12A 1.399(4) . ?
C13A C8A 1.412(4) . ?
C9 C10 1.364(5) . ?
C34 C35 1.529(5) . ?
C8A C9A 1.407(4) . ?
C20A C19A 1.377(5) . ?
C16A C17A 1.379(5) . ?
C16 C17 1.382(4) . ?
C4 C3 1.379(5) . ?
C9A C10A 1.364(5) . ?
C6A C1A 1.382(4) . ?
C6A C5A 1.389(4) . ?
C12 C11 1.372(4) . ?
C12A C11A 1.349(5) . ?
F3 C21 1.285(5) . ?
C17 C18 1.387(5) . ?
C17 C21 1.477(5) . ?
C5A C4A 1.375(4) . ?
F2 C21 1.295(6) . ?
C20 C19 1.372(5) . ?
C11 C10 1.383(5) . ?
C22 C23 1.501(5) . ?
C19A C18A 1.376(6) . ?
C10A C11A 1.387(5) . ?
C4A C3A 1.394(5) . ?
C30 C31 1.510(5) . ?
C19 C18 1.368(5) . ?
C1A C2A 1.366(5) . ?
C1 C2 1.367(5) . ?
C17A C18A 1.383(6) . ?
C17A C21A 1.464(7) . ?
C3 C2 1.381(5) . ?
C26 C27 1.513(6) . ?
C3A C2A 1.389(5) . ?
C35 C36 1.521(5) . ?
C23 C24 1.441(5) . ?
C36 C37 1.500(6) . ?
F1 C21 1.269(5) . ?
C31 C32 1.498(6) . ?
F2A C21A 1.221(6) . ?
C24 C25 1.474(6) . ?
F1A C21A 1.265(7) . ?
C27 C28 1.593(8) . ?
F3A C21A 1.256(7) . ?
C32 C33 1.518(7) . ?
C28 C29 1.383(8) . ?

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
C14 N3 C13 125.2(2) . . ?
C7 N2 C5 106.4(2) . . ?
C7 N2 C14 125.2(2) . . ?
C5 N2 C14 128.3(2) . . ?
C7 N1 C6 104.9(2) . . ?
C14A N3A C13A 120.3(2) . . ?
C7A N1A C6A 104.5(2) . . ?
C14A N4A C15A 121.3(3) . . ?
C7A N2A C5A 106.4(2) . . ?
C7A N2A C14A 123.7(2) . . ?
C5A N2A C14A 129.5(2) . . ?
C14 N4 C15 120.4(2) . . ?
C26 N5 C34 106.0(2) . . ?
C26 N5 C30 111.2(3) . . ?
C34 N5 C30 111.2(3) . . ?
C26 N5 C22 111.1(3) . . ?
C34 N5 C22 110.5(3) . . ?
C30 N5 C22 107.0(2) . . ?
N4 C14 N3 128.2(2) . . ?
N4 C14 N2 118.0(2) . . ?
N3 C14 N2 113.9(2) . . ?
N1 C7 N2 113.0(2) . . ?
N1 C7 C8 128.9(2) . . ?
N2 C7 C8 118.1(2) . . ?
C16A C15A N4A 115.9(3) . . ?
C16A C15A C20A 117.1(3) . . ?
N4A C15A C20A 126.8(3) . . ?
N1A C7A N2A 113.7(3) . . ?
N1A C7A C8A 128.4(3) . . ?
N2A C7A C8A 117.8(2) . . ?
C16 C15 C20 118.9(3) . . ?
C16 C15 N4 119.9(3) . . ?
C20 C15 N4 120.8(3) . . ?
C13 C8 C9 119.2(3) . . ?
C13 C8 C7 117.6(2) . . ?
C9 C8 C7 123.1(3) . . ?
N4A C14A N3A 128.2(3) . . ?
N4A C14A N2A 114.0(3) . . ?
N3A C14A N2A 117.8(3) . . ?
C1 C6 N1 129.2(3) . . ?
C1 C6 C5 119.6(3) . . ?
N1 C6 C5 111.1(2) . . ?
C4 C5 N2 133.2(3) . . ?
C4 C5 C6 122.2(3) . . ?
N2 C5 C6 104.6(2) . . ?
C12 C13 N3 120.4(3) . . ?
C12 C13 C8 119.7(3) . . ?
N3 C13 C8 120.0(2) . . ?
N3A C13A C12A 119.4(3) . . ?
N3A C13A C8A 123.5(3) . . ?
C12A C13A C8A 117.1(3) . . ?
C10 C9 C8 120.4(3) . . ?
N5 C34 C35 116.4(3) . . ?
C9A C8A C13A 120.4(3) . . ?
C9A C8A C7A 123.1(3) . . ?
C13A C8A C7A 116.5(3) . . ?
C19A C20A C15A 120.8(3) . . ?
C17A C16A C15A 122.2(4) . . ?
C15 C16 C17 120.2(3) . . ?
C3 C4 C5 116.7(3) . . ?
C10A C9A C8A 119.9(3) . . ?
C1A C6A C5A 120.6(3) . . ?
C1A C6A N1A 128.5(3) . . ?
C5A C6A N1A 110.9(2) . . ?
C11 C12 C13 119.8(3) . . ?
C11A C12A C13A 121.7(3) . . ?
C16 C17 C18 120.3(3) . . ?
C16 C17 C21 120.1(3) . . ?
C18 C17 C21 119.6(3) . . ?
C4A C5A C6A 122.0(3) . . ?
C4A C5A N2A 133.4(3) . . ?
C6A C5A N2A 104.6(2) . . ?
C19 C20 C15 120.7(3) . . ?
C12 C11 C10 120.9(3) . . ?
C23 C22 N5 115.6(3) . . ?
C9 C10 C11 120.0(3) . . ?
C18A C19A C20A 121.4(4) . . ?
C9A C10A C11A 119.8(3) . . ?
C5A C4A C3A 116.6(3) . . ?
C31 C30 N5 116.2(3) . . ?
C18 C19 C20 120.6(3) . . ?
C2A C1A C6A 118.3(3) . . ?
C19 C18 C17 119.3(3) . . ?
C2 C1 C6 118.3(3) . . ?
C12A C11A C10A 121.1(3) . . ?
C16A C17A C18A 120.0(4) . . ?
C16A C17A C21A 119.9(5) . . ?
C18A C17A C21A 120.0(4) . . ?
C4 C3 C2 121.8(3) . . ?
N5 C26 C27 116.1(3) . . ?
C2A C3A C4A 121.6(3) . . ?
C1A C2A C3A 120.9(3) . . ?
C19A C18A C17A 118.4(3) . . ?
C36 C35 C34 110.9(3) . . ?
C24 C23 C22 113.4(3) . . ?
C37 C36 C35 113.6(4) . . ?
C1 C2 C3 121.4(3) . . ?
C32 C31 C30 111.7(4) . . ?
C23 C24 C25 119.2(4) . . ?
F1 C21 F3 105.1(5) . . ?
F1 C21 F2 105.6(4) . . ?
F3 C21 F2 102.7(4) . . ?
F1 C21 C17 114.7(4) . . ?
F3 C21 C17 115.2(3) . . ?
F2 C21 C17 112.4(4) . . ?
C26 C27 C28 108.0(4) . . ?
F2A C21A F3A 103.3(8) . . ?
F2A C21A F1A 106.9(6) . . ?
F3A C21A F1A 97.3(6) . . ?
F2A C21A C17A 116.1(4) . . ?
F3A C21A C17A 114.5(5) . . ?
F1A C21A C17A 116.5(6) . . ?
C31 C32 C33 113.2(5) . . ?
C29 C28 C27 117.0(7) . . ?

_refine_diff_density_max         0.547
_refine_diff_density_min         -0.388
_refine_diff_density_rms         0.043


# start Validation Reply Form
_vrf_PLAT230_Benz_m_CF3_dep_Benz_m_CF3_TBA 
;
PROBLEM: Hirshfeld Test Diff for    C28      --C29      .        9.4 s.u.  
RESPONSE: This alert is due to significant disorder present in the long 
chain of the tetrabutylammonium cation (TBA). RIGU restraints were 
applied to atoms in the disordered chain. The atoms were still not 
ideally shaped, however, this does not indicate an incorrect 
atom-type assignment. However, for our study, the TBA part does 
not carry that much importance.
;
# end Validation Reply Form



####################################################################### 
# 
# 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_Dep_Benz_d_CF3
_audit_block_doi                 10.5517/ccdc.csd.cc2j82rn
_database_code_depnum_ccdc_archive 'CCDC 2331471'
loop_
_citation_id
_citation_doi
_citation_year
1 10.1039/D4TC00643G 2024
loop_
_audit_author_name
_audit_author_address
'Oiyao Appun Pegu'
;Indian Institute of Technology Guwahati
India
;
_audit_update_record             
;
2024-02-07 deposited with the CCDC.	2024-04-17 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C38 H47 F7 N5'
_chemical_formula_weight         706.80

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 '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                   15.182(3)
_cell_length_b                   16.695(4)
_cell_length_c                   15.637(4)
_cell_angle_alpha                90
_cell_angle_beta                 108.957(7)
_cell_angle_gamma                90
_cell_volume                     3748.2(15)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    9986
_cell_measurement_theta_min      2.80
_cell_measurement_theta_max      25.88

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.253
_exptl_crystal_F_000             1492
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.15
_exptl_absorpt_coefficient_mu    0.099
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            71667
_diffrn_reflns_av_unetI/netI     0.0341
_diffrn_reflns_av_R_equivalents  0.0554
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         1.624
_diffrn_reflns_theta_max         24.998
_diffrn_reflns_theta_full        24.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             6581
_reflns_number_gt                3273
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1000P)²+0.6096P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         6581
_refine_ls_number_parameters     455
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.2538
_refine_ls_R_factor_gt           0.1653
_refine_ls_wR_factor_ref         0.4555
_refine_ls_wR_factor_gt          0.4011
_refine_ls_goodness_of_fit_ref   2.201
_refine_ls_restrained_S_all      2.226
_refine_ls_shift/su_max          0.000
_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
N001 N 0.2077(3) 0.7918(3) 0.5234(3) 0.0986(15) Uani 1 1 d . . . . .
C14 C 0.6074(4) 0.2707(4) 0.1464(4) 0.0835(16) Uani 1 1 d . . . . .
N4 N 0.5985(5) 0.3108(4) 0.2129(4) 0.146(3) Uani 1 1 d . . . . .
C25 C 0.2198(4) 0.8054(4) 0.6210(4) 0.0944(18) Uani 1 1 d . . . . .
H25A H 0.233521 0.861631 0.634194 0.113 Uiso 1 1 calc R U . . .
H25B H 0.273778 0.775177 0.656745 0.113 Uiso 1 1 calc R U . . .
N2 N 0.6681(4) 0.3022(5) 0.1022(5) 0.137(3) Uani 1 1 d . . . . .
C5 C 0.7316(5) 0.3754(4) 0.1388(8) 0.116(3) Uani 1 1 d . . . . .
C9 C 0.6482(5) 0.1815(6) -0.0992(7) 0.121(2) Uani 1 1 d . . . . .
H9 H 0.687986 0.205009 -0.126358 0.146 Uiso 1 1 calc R U . . .
C8 C 0.6403(5) 0.2120(4) -0.0191(6) 0.107(2) Uani 1 1 d . . . . .
N3 N 0.5629(4) 0.2052(4) 0.1066(6) 0.155(3) Uani 1 1 d . . . . .
C13 C 0.5811(7) 0.1754(6) 0.0186(4) 0.113(3) Uani 1 1 d . . . . .
C12 C 0.5348(5) 0.1121(5) -0.0174(7) 0.111(2) Uani 1 1 d . . . . .
H12 H 0.497413 0.086725 0.011146 0.134 Uiso 1 1 calc R U . . .
C4 C 0.7414(5) 0.4284(6) 0.2138(6) 0.120(2) Uani 1 1 d . . . . .
H4 H 0.706241 0.424048 0.252434 0.144 Uiso 1 1 calc R U . . .
C00D C 0.2546(4) 0.6442(4) 0.5450(4) 0.1003(18) Uani 1 1 d . . . . .
H00A H 0.271426 0.651636 0.609836 0.120 Uiso 1 1 calc R U . . .
H00B H 0.310104 0.652487 0.528185 0.120 Uiso 1 1 calc R U . . .
C19 C 0.4214(5) 0.1877(5) 0.2945(5) 0.109(2) Uani 1 1 d . . . . .
C15 C 0.5235(4) 0.2807(6) 0.2577(5) 0.108(2) Uani 1 1 d . . . . .
C7 C 0.6937(5) 0.2848(4) 0.0361(5) 0.100(2) Uani 1 1 d . . . . .
C2 C 0.8588(6) 0.4895(6) 0.1629(8) 0.127(3) Uani 1 1 d . . . . .
H2 H 0.904420 0.528503 0.170400 0.152 Uiso 1 1 calc R U . . .
C18 C 0.4017(5) 0.2435(5) 0.3467(5) 0.109(2) Uani 1 1 d . . . . .
H18 H 0.360453 0.234055 0.378389 0.130 Uiso 1 1 calc R U . . .
C00J C 0.1277(5) 0.8431(4) 0.4633(5) 0.122(2) Uani 1 1 d . . . . .
H00C H 0.122938 0.833734 0.400694 0.146 Uiso 1 1 calc R U . . .
H00D H 0.070119 0.824612 0.470910 0.146 Uiso 1 1 calc R U . . .
C00K C 0.3000(4) 0.8129(4) 0.5092(5) 0.116(2) Uani 1 1 d . . . . .
H00E H 0.314111 0.868569 0.525581 0.140 Uiso 1 1 calc R U . . .
H00F H 0.348831 0.780699 0.550270 0.140 Uiso 1 1 calc R U . . .
N1 N 0.7492(6) 0.3148(5) 0.0092(5) 0.153(3) Uani 1 1 d . . . . .
C00M C 0.2198(5) 0.5600(4) 0.5210(5) 0.128(2) Uani 1 1 d . . . . .
H00G H 0.167893 0.551041 0.543170 0.154 Uiso 1 1 calc R U . . .
H00H H 0.196246 0.555398 0.455665 0.154 Uiso 1 1 calc R U . . .
C20 C 0.4859(5) 0.2038(5) 0.2433(4) 0.108(2) Uani 1 1 d . . . . .
H20 H 0.499910 0.166513 0.205472 0.129 Uiso 1 1 calc R U . . .
C11 C 0.5399(5) 0.0831(5) -0.0947(6) 0.116(2) Uani 1 1 d . . . . .
H11 H 0.503903 0.038793 -0.120574 0.140 Uiso 1 1 calc R U . . .
C00P C 0.1828(4) 0.7046(4) 0.4980(4) 0.1024(19) Uani 1 1 d . . . . .
H00I H 0.125780 0.692166 0.510478 0.123 Uiso 1 1 calc R U . . .
H00J H 0.170027 0.698897 0.433355 0.123 Uiso 1 1 calc R U . . .
C10 C 0.5960(7) 0.1159(6) -0.1368(5) 0.127(3) Uani 1 1 d . . . . .
H10 H 0.599009 0.094321 -0.190635 0.152 Uiso 1 1 calc R U . . .
F7 F 0.3989(7) 0.0586(4) 0.2420(6) 0.266(4) Uani 1 1 d . . . . .
C3 C 0.8105(6) 0.4883(5) 0.2227(6) 0.119(2) Uani 1 1 d . . . . .
H3 H 0.822659 0.526105 0.268796 0.143 Uiso 1 1 calc R U . . .
C1 C 0.8448(7) 0.4388(7) 0.0948(8) 0.140(3) Uani 1 1 d . . . . .
H1 H 0.879753 0.442745 0.055958 0.168 Uiso 1 1 calc R U . . .
C6 C 0.7827(8) 0.3844(7) 0.0829(7) 0.127(3) Uani 1 1 d . . . . .
F5 F 0.3812(12) 0.0766(5) 0.3611(6) 0.336(8) Uani 1 1 d . . . . .
F4 F 0.3941(11) 0.3568(5) 0.4680(8) 0.265(4) Uani 1 1 d . . . . .
C22 C 0.3809(9) 0.1170(9) 0.2890(7) 0.160(4) Uani 1 1 d . . . . .
F1 F 0.3447(9) 0.4143(8) 0.3622(10) 0.296(5) Uani 1 1 d . . . . .
C00Z C 0.1390(5) 0.7832(4) 0.6523(5) 0.112(2) Uani 1 1 d . . . . .
H00K H 0.081641 0.803317 0.609418 0.134 Uiso 1 1 calc R U . . .
H00L H 0.134296 0.725349 0.654526 0.134 Uiso 1 1 calc R U . . .
C010 C 0.2886(6) 0.4962(5) 0.5565(6) 0.145(3) Uani 1 1 d . . . . .
H01A H 0.339420 0.502908 0.533274 0.217 Uiso 1 1 calc R U . . .
H01B H 0.259822 0.445052 0.538060 0.217 Uiso 1 1 calc R U . . .
H01C H 0.311521 0.498988 0.621312 0.217 Uiso 1 1 calc R U . . .
C16 C 0.5064(6) 0.3345(6) 0.3094(6) 0.135(3) Uani 1 1 d . . . . .
H16 H 0.534990 0.384439 0.317510 0.163 Uiso 1 1 calc R U . . .
C012 C 0.1353(5) 0.9305(4) 0.4800(6) 0.153(3) Uani 1 1 d . . . . .
H01D H 0.197374 0.948317 0.484227 0.183 Uiso 1 1 calc R U . . .
H01E H 0.125717 0.942046 0.537161 0.183 Uiso 1 1 calc R U . . .
F2 F 0.4478(19) 0.4488(17) 0.3758(12) 0.428(12) Uani 1 1 d . . . . .
C014 C 0.1511(6) 0.8175(5) 0.7443(6) 0.129(2) Uani 1 1 d . . . . .
H01F H 0.211585 0.801811 0.785268 0.155 Uiso 1 1 calc R U . . .
H01G H 0.150011 0.875513 0.740273 0.155 Uiso 1 1 calc R U . . .
C17 C 0.4450(5) 0.3139(7) 0.3506(6) 0.128(3) Uani 1 1 d . . . . .
C21 C 0.4366(15) 0.3724(10) 0.414(3) 0.269(12) Uani 1 1 d . . . . .
F6 F 0.2917(7) 0.1108(5) 0.2575(12) 0.344(8) Uani 1 1 d . . . . .
F3 F 0.4964(11) 0.4153(17) 0.4617(16) 0.432(15) Uani 1 1 d . . . . .
C019 C 0.0787(7) 0.7912(6) 0.7819(7) 0.166(3) Uani 1 1 d . . . . .
H01H H 0.019260 0.811191 0.744934 0.249 Uiso 1 1 calc R U . . .
H01I H 0.092659 0.811549 0.842305 0.249 Uiso 1 1 calc R U . . .
H01J H 0.077075 0.733752 0.783098 0.249 Uiso 1 1 calc R U . . .
C01A C 0.3027(7) 0.8008(7) 0.4165(7) 0.184(4) Uani 1 1 d D . . . .
H01K H 0.266058 0.842543 0.377849 0.220 Uiso 1 1 calc R U . . .
H01L H 0.273498 0.749882 0.393987 0.220 Uiso 1 1 calc R U . . .
C01B C 0.4047(11) 0.8016(12) 0.4085(13) 0.271(9) Uani 1 1 d D . . . .
H01M H 0.452492 0.786206 0.464219 0.325 Uiso 1 1 calc R U . . .
H01N H 0.409624 0.769869 0.358352 0.325 Uiso 1 1 calc R U . . .
C01C C 0.0639(7) 0.9757(7) 0.4047(8) 0.199(5) Uani 1 1 d . . . . .
H01O H 0.046430 0.941167 0.351919 0.239 Uiso 1 1 calc R U . . .
H01P H 0.008912 0.982054 0.422716 0.239 Uiso 1 1 calc R U . . .
C24 C 0.0819(10) 1.0414(10) 0.3802(12) 0.340(13) Uani 1 1 d . . . . .
H24A H 0.083140 1.080569 0.425510 0.510 Uiso 1 1 calc R U . . .
H24B H 0.035153 1.055664 0.324336 0.510 Uiso 1 1 calc R U . . .
H24C H 0.141683 1.039534 0.371572 0.510 Uiso 1 1 calc R U . . .
C188 C 0.4029(15) 0.8783(13) 0.3932(19) 0.356(14) Uani 1 1 d D . . . .
H18A H 0.427286 0.888730 0.344845 0.533 Uiso 1 1 calc R U . . .
H18B H 0.440176 0.905496 0.446844 0.533 Uiso 1 1 calc R U . . .
H18C H 0.339856 0.897255 0.376626 0.533 Uiso 1 1 calc R U . . .


_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
N001 C25 1.495(8) . ?
N001 C00P 1.524(8) . ?
N001 C00K 1.530(8) . ?
N001 C00J 1.533(8) . ?
C14 N4 1.280(8) . ?
C14 N3 1.329(8) . ?
C14 N2 1.421(9) . ?
N4 C15 1.599(10) . ?
C25 C00Z 1.507(9) . ?
N2 C7 1.250(9) . ?
N2 C5 1.547(9) . ?
C5 C6 1.353(11) . ?
C5 C4 1.438(11) . ?
C9 C10 1.367(11) . ?
C9 C8 1.394(11) . ?
C8 C13 1.368(11) . ?
C8 C7 1.556(10) . ?
N3 C13 1.571(10) . ?
C13 C12 1.292(11) . ?
C12 C11 1.329(10) . ?
C4 C3 1.423(11) . ?
C00D C00P 1.491(8) . ?
C00D C00M 1.507(9) . ?
C19 C22 1.321(13) . ?
C19 C18 1.334(9) . ?
C19 C20 1.476(10) . ?
C15 C16 1.288(10) . ?
C15 C20 1.394(10) . ?
C7 N1 1.170(8) . ?
C2 C1 1.322(12) . ?
C2 C3 1.363(11) . ?
C18 C17 1.338(10) . ?
C00J C012 1.480(10) . ?
C00K C01A 1.477(12) . ?
N1 C6 1.597(13) . ?
C00M C010 1.468(10) . ?
C11 C10 1.350(10) . ?
F7 C22 1.303(11) . ?
C1 C6 1.279(12) . ?
F5 C22 1.314(13) . ?
F4 C21 1.24(2) . ?
C22 F6 1.285(12) . ?
F1 C21 1.54(3) . ?
F1 F2 1.62(3) . ?
C00Z C014 1.503(10) . ?
C16 C17 1.339(11) . ?
C012 C01C 1.517(10) . ?
F2 F3 1.42(4) . ?
F2 C21 1.44(3) . ?
C014 C019 1.472(11) . ?
C17 C21 1.43(2) . ?
C21 F3 1.21(2) . ?
C01A C01B 1.593(12) . ?
C01B C188 1.301(15) . ?
C01C C24 1.222(13) . ?

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
C25 N001 C00P 110.4(5) . . ?
C25 N001 C00K 107.4(5) . . ?
C00P N001 C00K 110.1(5) . . ?
C25 N001 C00J 110.6(5) . . ?
C00P N001 C00J 107.1(4) . . ?
C00K N001 C00J 111.3(5) . . ?
N4 C14 N3 129.7(8) . . ?
N4 C14 N2 117.3(7) . . ?
N3 C14 N2 112.8(7) . . ?
C14 N4 C15 118.0(7) . . ?
N001 C25 C00Z 116.9(5) . . ?
C7 N2 C14 137.8(8) . . ?
C7 N2 C5 99.6(7) . . ?
C14 N2 C5 122.5(8) . . ?
C6 C5 C4 122.0(7) . . ?
C6 C5 N2 105.5(10) . . ?
C4 C5 N2 132.5(10) . . ?
C10 C9 C8 118.2(7) . . ?
C13 C8 C9 118.9(7) . . ?
C13 C8 C7 114.0(9) . . ?
C9 C8 C7 127.1(9) . . ?
C14 N3 C13 117.7(7) . . ?
C12 C13 C8 121.3(7) . . ?
C12 C13 N3 114.5(10) . . ?
C8 C13 N3 124.2(10) . . ?
C13 C12 C11 120.6(8) . . ?
C3 C4 C5 113.0(7) . . ?
C00P C00D C00M 111.6(5) . . ?
C22 C19 C18 118.1(9) . . ?
C22 C19 C20 120.2(9) . . ?
C18 C19 C20 121.6(8) . . ?
C16 C15 C20 126.0(8) . . ?
C16 C15 N4 111.9(9) . . ?
C20 C15 N4 122.1(8) . . ?
N1 C7 N2 130.6(10) . . ?
N1 C7 C8 116.2(9) . . ?
N2 C7 C8 113.2(8) . . ?
C1 C2 C3 124.2(9) . . ?
C19 C18 C17 115.9(8) . . ?
C012 C00J N001 116.2(5) . . ?
C01A C00K N001 115.4(6) . . ?
C7 N1 C6 98.6(8) . . ?
C010 C00M C00D 115.7(6) . . ?
C15 C20 C19 112.9(6) . . ?
C12 C11 C10 121.9(7) . . ?
C00D C00P N001 116.0(5) . . ?
C11 C10 C9 119.0(7) . . ?
C2 C3 C4 119.1(8) . . ?
C6 C1 C2 119.4(10) . . ?
C1 C6 C5 122.3(10) . . ?
C1 C6 N1 132.0(11) . . ?
C5 C6 N1 105.7(10) . . ?
F6 C22 F7 96.4(10) . . ?
F6 C22 F5 89.8(12) . . ?
F7 C22 F5 99.0(13) . . ?
F6 C22 C19 120.5(12) . . ?
F7 C22 C19 121.8(11) . . ?
F5 C22 C19 122.1(9) . . ?
C21 F1 F2 54.4(11) . . ?
C014 C00Z C25 111.0(6) . . ?
C15 C16 C17 115.9(9) . . ?
C00J C012 C01C 111.0(7) . . ?
F3 F2 C21 49.9(14) . . ?
F3 F2 F1 100(2) . . ?
C21 F2 F1 60.0(19) . . ?
C019 C014 C00Z 113.2(8) . . ?
C18 C17 C16 127.7(9) . . ?
C18 C17 C21 118.6(9) . . ?
C16 C17 C21 113.1(11) . . ?
F3 C21 F4 99(3) . . ?
F3 C21 C17 128.0(14) . . ?
F4 C21 C17 120.7(12) . . ?
F3 C21 F2 64.1(14) . . ?
F4 C21 F2 128.6(19) . . ?
C17 C21 F2 106(2) . . ?
F3 C21 F1 115.4(19) . . ?
F4 C21 F1 82.6(10) . . ?
C17 C21 F1 102(2) . . ?
F2 C21 F1 65.6(17) . . ?
C21 F3 F2 66.0(17) . . ?
C00K C01A C01B 114.3(10) . . ?
C188 C01B C01A 93.5(15) . . ?
C24 C01C C012 120.9(10) . . ?

_refine_diff_density_max         0.744
_refine_diff_density_min         -0.314
_refine_diff_density_rms         0.068

