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

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

data_09127z
_database_code_depnum_ccdc_archive 'CCDC 2482768'
loop_
_audit_author_name
_audit_author_address
'William Ojala'
;University of St Thomas
United States of America
;
_audit_update_record             
;
2025-08-25 deposited with the CCDC.	2025-12-16 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2019/3
_shelx_SHELXL_version_number     2019/3
_chemical_name_systematic        
N,N^'^-(1,4-phenylenedimethylidyne)bis(2-trifluoromethyl)benzenamine
_chemical_name_common            ?
_chemical_melting_point          '409-411 K'
_chemical_formula_moiety         ?
_chemical_formula_sum            'C22 H14 F6 N2'
_chemical_formula_weight         420.35

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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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                   8.3139(15)
_cell_length_b                   12.128(2)
_cell_length_c                   19.032(3)
_cell_angle_alpha                90
_cell_angle_beta                 94.887(2)
_cell_angle_gamma                90
_cell_volume                     1912.0(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    4024
_cell_measurement_theta_min      2.60
_cell_measurement_theta_max      27.32

_exptl_crystal_description       prism
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.460
_exptl_crystal_F_000             856
_exptl_transmission_factor_min   0.6877
_exptl_transmission_factor_max   0.7456
_exptl_crystal_size_max          0.530
_exptl_crystal_size_mid          0.250
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    0.128
_shelx_estimated_absorpt_T_min   0.935
_shelx_estimated_absorpt_T_max   0.975
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6877
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   
'Sheldrick, G. M. (2008) SADABS, Version 2008/1, Bruker AXS Inc., Madison'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed tube'
_diffrn_measurement_device_type  'Siemens SMART platform CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            21004
_diffrn_reflns_av_unetI/netI     0.0210
_diffrn_reflns_av_R_equivalents  0.0272
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         1.993
_diffrn_reflns_theta_max         27.530
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             4363
_reflns_number_gt                3335
_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2019/2 (Sheldrick, 2019)'
_computing_molecular_graphics    
'Mercury (Macrae et al., J. Appl. Cryst., 53, 226-235, 2020) and ORTEP-3 for Windows (L. J. Farrugia, J. Appl. Cryst. (2012),45, 849-854)'
_computing_publication_material  
'enCIFer (Allen et al., J. Appl. Cryst., 37, 335-338, 2004)'
_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)+(0.0414P)²+0.4804P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_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         4363
_refine_ls_number_parameters     271
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0587
_refine_ls_R_factor_gt           0.0398
_refine_ls_wR_factor_ref         0.0974
_refine_ls_wR_factor_gt          0.0900
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_restrained_S_all      1.034
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
F1 F 0.43943(12) -0.22626(9) 0.29187(6) 0.0640(3) Uani 1 1 d . . . . .
F2 F 0.46990(11) -0.12993(8) 0.38637(5) 0.0563(3) Uani 1 1 d . . . . .
F3 F 0.51995(12) -0.05876(8) 0.28764(5) 0.0585(3) Uani 1 1 d . . . . .
F4 F 0.75071(11) 0.47427(7) 0.68280(5) 0.0529(2) Uani 1 1 d . . . . .
F5 F 0.49800(12) 0.48418(9) 0.65220(6) 0.0700(3) Uani 1 1 d . . . . .
F6 F 0.60012(17) 0.57025(9) 0.74412(5) 0.0817(4) Uani 1 1 d . . . . .
N1 N 0.78177(14) -0.01743(9) 0.39756(6) 0.0377(3) Uani 1 1 d . . . . .
N2 N 0.69601(14) 0.52232(9) 0.53707(6) 0.0359(3) Uani 1 1 d . . . . .
C1 C 0.82491(17) -0.12195(11) 0.37176(7) 0.0351(3) Uani 1 1 d . . . . .
C2 C 0.70682(17) -0.18982(11) 0.33695(7) 0.0354(3) Uani 1 1 d . . . . .
C3 C 0.74958(19) -0.29259(12) 0.31215(7) 0.0416(3) Uani 1 1 d . . . . .
H3 H 0.670162 -0.337676 0.287480 0.050 Uiso 1 1 calc R U . . .
C4 C 0.9073(2) -0.32968(12) 0.32317(8) 0.0454(4) Uani 1 1 d . . . . .
H4 H 0.936044 -0.399683 0.305660 0.054 Uiso 1 1 calc R U . . .
C5 C 1.0223(2) -0.26508(13) 0.35949(8) 0.0451(4) Uani 1 1 d . . . . .
H5 H 1.129798 -0.291386 0.368152 0.054 Uiso 1 1 calc R U . . .
C6 C 0.98159(18) -0.16167(12) 0.38348(8) 0.0420(3) Uani 1 1 d . . . . .
H6 H 1.061893 -0.117414 0.408254 0.050 Uiso 1 1 calc R U . . .
C7 C 0.86014(17) 0.06611(11) 0.37903(7) 0.0363(3) Uani 1 1 d . . . . .
H7 H 0.939450 0.056046 0.346498 0.044 Uiso 1 1 calc R U . . .
C8 C 0.83327(16) 0.17735(11) 0.40574(7) 0.0338(3) Uani 1 1 d . . . . .
C9 C 0.91546(18) 0.26570(11) 0.37892(7) 0.0381(3) Uani 1 1 d . . . . .
H9 H 0.985532 0.253489 0.342782 0.046 Uiso 1 1 calc R U . . .
C10 C 0.89590(17) 0.37118(12) 0.40445(8) 0.0382(3) Uani 1 1 d . . . . .
H10 H 0.951800 0.431025 0.385424 0.046 Uiso 1 1 calc R U . . .
C11 C 0.68785(16) 0.63107(11) 0.56336(7) 0.0344(3) Uani 1 1 d . . . . .
C12 C 0.65234(17) 0.64356(12) 0.63360(7) 0.0372(3) Uani 1 1 d . . . . .
C13 C 0.64171(19) 0.74837(13) 0.66272(8) 0.0451(4) Uani 1 1 d . . . . .
H13 H 0.619111 0.756361 0.710548 0.054 Uiso 1 1 calc R U . . .
C14 C 0.6639(2) 0.84082(13) 0.62219(9) 0.0486(4) Uani 1 1 d . . . . .
H14 H 0.657185 0.912229 0.642248 0.058 Uiso 1 1 calc R U . . .
C15 C 0.69599(19) 0.82941(12) 0.55254(8) 0.0461(4) Uani 1 1 d . . . . .
H15 H 0.710108 0.892999 0.524572 0.055 Uiso 1 1 calc R U . . .
C16 C 0.70757(18) 0.72534(12) 0.52344(8) 0.0406(3) Uani 1 1 d . . . . .
H16 H 0.729318 0.718266 0.475443 0.049 Uiso 1 1 calc R U . . .
C17 C 0.78204(16) 0.50176(11) 0.48657(7) 0.0356(3) Uani 1 1 d . . . . .
H17 H 0.839605 0.560215 0.466888 0.043 Uiso 1 1 calc R U . . .
C18 C 0.79483(16) 0.39025(11) 0.45787(7) 0.0334(3) Uani 1 1 d . . . . .
C19 C 0.71112(16) 0.30141(12) 0.48453(7) 0.0356(3) Uani 1 1 d . . . . .
H19 H 0.641404 0.313560 0.520803 0.043 Uiso 1 1 calc R U . . .
C20 C 0.72919(17) 0.19671(11) 0.45853(7) 0.0360(3) Uani 1 1 d . . . . .
H20 H 0.670728 0.137189 0.476494 0.043 Uiso 1 1 calc R U . . .
C21 C 0.53585(19) -0.15148(12) 0.32601(8) 0.0433(3) Uani 1 1 d . . . . .
C22 C 0.6253(2) 0.54389(13) 0.67739(8) 0.0468(4) 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
F1 C21 1.3411(18) . ?
F2 C21 1.3402(17) . ?
F3 C21 1.3412(17) . ?
F4 C22 1.3387(18) . ?
F5 C22 1.3373(19) . ?
F6 C22 1.3431(18) . ?
N1 C7 1.2707(18) . ?
N1 C1 1.4165(17) . ?
N2 C17 1.2708(17) . ?
N2 C11 1.4143(17) . ?
C1 C6 1.389(2) . ?
C1 C2 1.403(2) . ?
C2 C3 1.390(2) . ?
C2 C21 1.493(2) . ?
C3 C4 1.385(2) . ?
C3 H3 0.9500 . ?
C4 C5 1.376(2) . ?
C4 H4 0.9500 . ?
C5 C6 1.386(2) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C7 C8 1.4655(19) . ?
C7 H7 0.9500 . ?
C8 C9 1.391(2) . ?
C8 C20 1.4005(19) . ?
C9 C10 1.3830(19) . ?
C9 H9 0.9500 . ?
C10 C18 1.3924(19) . ?
C10 H10 0.9500 . ?
C11 C16 1.390(2) . ?
C11 C12 1.4015(19) . ?
C12 C13 1.393(2) . ?
C12 C22 1.496(2) . ?
C13 C14 1.382(2) . ?
C13 H13 0.9500 . ?
C14 C15 1.381(2) . ?
C14 H14 0.9500 . ?
C15 C16 1.385(2) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?
C17 C18 1.4656(19) . ?
C17 H17 0.9500 . ?
C18 C19 1.4010(19) . ?
C19 C20 1.376(2) . ?
C19 H19 0.9500 . ?
C20 H20 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
C7 N1 C1 117.79(12) . . ?
C17 N2 C11 119.85(12) . . ?
C6 C1 C2 118.76(13) . . ?
C6 C1 N1 121.09(13) . . ?
C2 C1 N1 120.05(12) . . ?
C3 C2 C1 119.83(13) . . ?
C3 C2 C21 119.99(13) . . ?
C1 C2 C21 120.17(13) . . ?
C4 C3 C2 120.40(14) . . ?
C4 C3 H3 119.8 . . ?
C2 C3 H3 119.8 . . ?
C5 C4 C3 119.97(14) . . ?
C5 C4 H4 120.0 . . ?
C3 C4 H4 120.0 . . ?
C4 C5 C6 120.12(15) . . ?
C4 C5 H5 119.9 . . ?
C6 C5 H5 119.9 . . ?
C5 C6 C1 120.85(14) . . ?
C5 C6 H6 119.6 . . ?
C1 C6 H6 119.6 . . ?
N1 C7 C8 122.73(13) . . ?
N1 C7 H7 118.6 . . ?
C8 C7 H7 118.6 . . ?
C9 C8 C20 119.14(13) . . ?
C9 C8 C7 119.18(12) . . ?
C20 C8 C7 121.67(13) . . ?
C10 C9 C8 120.49(13) . . ?
C10 C9 H9 119.8 . . ?
C8 C9 H9 119.8 . . ?
C9 C10 C18 120.44(13) . . ?
C9 C10 H10 119.8 . . ?
C18 C10 H10 119.8 . . ?
C16 C11 C12 118.47(13) . . ?
C16 C11 N2 124.20(12) . . ?
C12 C11 N2 117.29(12) . . ?
C13 C12 C11 120.25(13) . . ?
C13 C12 C22 119.89(13) . . ?
C11 C12 C22 119.86(13) . . ?
C14 C13 C12 120.16(14) . . ?
C14 C13 H13 119.9 . . ?
C12 C13 H13 119.9 . . ?
C15 C14 C13 120.01(14) . . ?
C15 C14 H14 120.0 . . ?
C13 C14 H14 120.0 . . ?
C14 C15 C16 120.06(14) . . ?
C14 C15 H15 120.0 . . ?
C16 C15 H15 120.0 . . ?
C15 C16 C11 121.02(14) . . ?
C15 C16 H16 119.5 . . ?
C11 C16 H16 119.5 . . ?
N2 C17 C18 121.76(13) . . ?
N2 C17 H17 119.1 . . ?
C18 C17 H17 119.1 . . ?
C10 C18 C19 119.07(12) . . ?
C10 C18 C17 119.52(13) . . ?
C19 C18 C17 121.37(12) . . ?
C20 C19 C18 120.45(13) . . ?
C20 C19 H19 119.8 . . ?
C18 C19 H19 119.8 . . ?
C19 C20 C8 120.39(13) . . ?
C19 C20 H20 119.8 . . ?
C8 C20 H20 119.8 . . ?
F2 C21 F1 106.01(12) . . ?
F2 C21 F3 105.94(12) . . ?
F1 C21 F3 106.03(12) . . ?
F2 C21 C2 113.28(12) . . ?
F1 C21 C2 112.31(12) . . ?
F3 C21 C2 112.68(12) . . ?
F5 C22 F4 105.87(13) . . ?
F5 C22 F6 106.58(13) . . ?
F4 C22 F6 105.10(13) . . ?
F5 C22 C12 112.94(13) . . ?
F4 C22 C12 113.55(12) . . ?
F6 C22 C12 112.17(13) . . ?

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
C7 N1 C1 C6 56.72(18) . . . . ?
C7 N1 C1 C2 -126.72(14) . . . . ?
N1 C1 C2 C3 -179.58(12) . . . . ?
C6 C1 C2 C21 177.58(12) . . . . ?
N1 C1 C2 C21 0.94(19) . . . . ?
C21 C2 C3 C4 -178.83(13) . . . . ?
N1 C1 C6 C5 178.52(13) . . . . ?
C1 N1 C7 C8 -176.13(12) . . . . ?
N1 C7 C8 C9 -175.26(14) . . . . ?
N1 C7 C8 C20 5.9(2) . . . . ?
C7 C8 C9 C10 -178.24(13) . . . . ?
C17 N2 C11 C16 28.2(2) . . . . ?
C17 N2 C11 C12 -153.92(13) . . . . ?
N2 C11 C12 C13 -179.69(13) . . . . ?
C16 C11 C12 C22 178.11(14) . . . . ?
N2 C11 C12 C22 0.1(2) . . . . ?
C22 C12 C13 C14 -178.94(15) . . . . ?
N2 C11 C16 C15 179.19(14) . . . . ?
C11 N2 C17 C18 179.67(12) . . . . ?
C9 C10 C18 C17 177.00(13) . . . . ?
N2 C17 C18 C10 -177.38(13) . . . . ?
N2 C17 C18 C19 0.7(2) . . . . ?
C17 C18 C19 C20 -177.71(13) . . . . ?
C7 C8 C20 C19 177.46(13) . . . . ?
C3 C2 C21 F2 120.49(14) . . . . ?
C1 C2 C21 F2 -60.02(17) . . . . ?
C3 C2 C21 F1 0.41(19) . . . . ?
C1 C2 C21 F1 179.90(12) . . . . ?
C3 C2 C21 F3 -119.25(14) . . . . ?
C1 C2 C21 F3 60.23(17) . . . . ?
C13 C12 C22 F5 117.42(16) . . . . ?
C11 C12 C22 F5 -62.42(18) . . . . ?
C13 C12 C22 F4 -122.03(15) . . . . ?
C11 C12 C22 F4 58.14(19) . . . . ?
C13 C12 C22 F6 -3.0(2) . . . . ?
C11 C12 C22 F6 177.12(13) . . . . ?

_refine_diff_density_max         0.159
_refine_diff_density_min         -0.206
_refine_diff_density_rms         0.039


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: ethanol'
####################################################################### 
# 
# 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_13287z
_database_code_depnum_ccdc_archive 'CCDC 2482772'
loop_
_audit_author_name
_audit_author_address
'William Ojala'
;University of St Thomas
United States of America
;
_audit_update_record             
;
2025-08-25 deposited with the CCDC.	2025-12-16 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2019/3
_shelx_SHELXL_version_number     2019/3
_chemical_name_systematic        
N,N^'^-(1,4-phenylenedimethylidyne)bis(4-trifluoromethyl)benzenamine
_chemical_name_common            ?
_chemical_melting_point          '462-466 K'
_chemical_formula_moiety         ?
_chemical_formula_sum            'C22 H14 F6 N2'
_chemical_formula_weight         420.35

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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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                   14.9937(12)
_cell_length_b                   7.5042(6)
_cell_length_c                   16.9077(13)
_cell_angle_alpha                90
_cell_angle_beta                 100.8584(10)
_cell_angle_gamma                90
_cell_volume                     1868.3(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    2975
_cell_measurement_theta_min      2.45
_cell_measurement_theta_max      27.44

_exptl_crystal_description       needle
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.494
_exptl_crystal_F_000             856
_exptl_transmission_factor_min   0.6867
_exptl_transmission_factor_max   0.7456
_exptl_crystal_size_max          0.500
_exptl_crystal_size_mid          0.250
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.131
_shelx_estimated_absorpt_T_min   0.6867
_shelx_estimated_absorpt_T_max   0.7456
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.938
_exptl_absorpt_correction_T_max  0.987
_exptl_absorpt_process_details   'SADABS 2012/1 (Bruker, 2012)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed tube'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            17834
_diffrn_reflns_av_unetI/netI     0.0221
_diffrn_reflns_av_R_equivalents  0.0326
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         1.667
_diffrn_reflns_theta_max         25.245
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             3364
_reflns_number_gt                2665
_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2019/2 (Sheldrick, 2019)'
_computing_molecular_graphics    
'Mercury (Macrae et al., J. Appl. Cryst., 53, 226-235, 2020)and ORTEP-3 for Windows (L. J. Farrugia, J. Appl. Cryst. (2012),45, 849-854)'
_computing_publication_material  
'enCIFer (Allen et al., J. Appl. Cryst., 37, 335-338, 2004)'
_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)+(0.0551P)²+1.1640P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2019/2 (Sheldrick 2019)'
_refine_ls_extinction_coef       0.0029(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3364
_refine_ls_number_parameters     285
_refine_ls_number_restraints     111
_refine_ls_R_factor_all          0.0584
_refine_ls_R_factor_gt           0.0455
_refine_ls_wR_factor_ref         0.1272
_refine_ls_wR_factor_gt          0.1156
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_restrained_S_all      1.039
_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
N1 N 0.50070(10) 0.7704(2) 0.04937(9) 0.0324(4) Uani 1 1 d . . . . .
N2 N 0.97241(11) 0.7471(2) 0.27907(9) 0.0353(4) Uani 1 1 d . . . . .
C1 C 0.40528(12) 0.7481(2) 0.03112(11) 0.0293(4) Uani 1 1 d . . . . .
C3 C 0.27607(12) 0.6356(3) -0.06264(11) 0.0323(4) Uani 1 1 d . . . . .
H3 H 0.251902 0.574502 -0.111161 0.039 Uiso 1 1 calc R U . . .
C2 C 0.36844(12) 0.6625(3) -0.04086(11) 0.0333(4) Uani 1 1 d . . . . .
H2 H 0.407491 0.622146 -0.075324 0.040 Uiso 1 1 calc R U . . .
C4 C 0.21831(12) 0.6983(2) -0.01320(11) 0.0313(4) Uani 1 1 d D . . . .
C21 C 0.11820(12) 0.6771(2) -0.03962(11) 0.0368(5) Uani 1 1 d D . . . .
F1 F 0.07176(8) 0.7081(2) 0.01843(8) 0.0625(4) Uani 1 1 d D . . . .
F2 F 0.09464(9) 0.51456(19) -0.06646(10) 0.0704(5) Uani 1 1 d D . . . .
F3 F 0.08450(9) 0.7885(2) -0.09916(9) 0.0775(5) Uani 1 1 d D . . . .
C5 C 0.25415(13) 0.7874(3) 0.05759(11) 0.0344(4) Uani 1 1 d . . . . .
H5 H 0.214749 0.831897 0.090883 0.041 Uiso 1 1 calc R U . . .
C6 C 0.34696(13) 0.8119(3) 0.07995(11) 0.0337(4) Uani 1 1 d . . . . .
H6 H 0.371044 0.872205 0.128694 0.040 Uiso 1 1 calc R U . . .
C7 C 0.54178(13) 0.7519(2) 0.12185(11) 0.0321(4) Uani 1 1 d . . . . .
H7 H 0.507497 0.724865 0.162177 0.039 Uiso 1 1 calc R U . . .
C8 C 0.64075(12) 0.7714(2) 0.14501(11) 0.0301(4) Uani 1 1 d . . . . .
C9 C 0.68498(13) 0.7101(3) 0.22048(11) 0.0323(4) Uani 1 1 d . . . . .
H9 H 0.650231 0.665042 0.257573 0.039 Uiso 1 1 calc R U . . .
C10 C 0.77829(12) 0.7145(2) 0.24159(11) 0.0319(4) Uani 1 1 d . . . . .
H10 H 0.807477 0.670492 0.292602 0.038 Uiso 1 1 calc R U . . .
C11 C 1.06853(13) 0.7429(2) 0.29389(11) 0.0317(4) Uani 1 1 d . . . . .
C12 C 1.11509(13) 0.7990(3) 0.36924(11) 0.0359(5) Uani 1 1 d . . . . .
H12 H 1.082173 0.842197 0.408093 0.043 Uiso 1 1 calc R U . . .
C13 C 1.20872(13) 0.7919(3) 0.38746(11) 0.0358(5) Uani 1 1 d . . . . .
H13 H 1.240722 0.839366 0.440279 0.054 Uiso 1 1 d R U . A .
C15 C 1.21154(13) 0.6643(3) 0.25741(12) 0.0368(5) Uani 1 1 d . . . . .
H15 H 1.245571 0.615187 0.216582 0.055 Uiso 1 1 d R U . A .
C16 C 1.11778(13) 0.6744(3) 0.23868(12) 0.0368(5) Uani 1 1 d . . . . .
H16 H 1.086661 0.634277 0.187600 0.044 Uiso 1 1 calc R U . . .
C17 C 0.92951(13) 0.7893(2) 0.20909(11) 0.0328(4) Uani 1 1 d . . . . .
H17 H 0.962981 0.825557 0.169412 0.039 Uiso 1 1 calc R U . . .
C18 C 0.83027(12) 0.7837(2) 0.18806(11) 0.0301(4) Uani 1 1 d . . . . .
C19 C 0.78588(12) 0.8466(2) 0.11303(11) 0.0320(4) Uani 1 1 d . . . . .
H19 H 0.820553 0.893948 0.076358 0.038 Uiso 1 1 calc R U . . .
C20 C 0.69245(12) 0.8408(2) 0.09149(11) 0.0323(4) Uani 1 1 d . . . . .
H20 H 0.663263 0.884020 0.040317 0.039 Uiso 1 1 calc R U . . .
C14 C 1.25726(12) 0.7241(2) 0.33174(11) 0.0341(4) Uani 0.887(3) 1 d D . P A 1
C22 C 1.35874(14) 0.7149(3) 0.35172(13) 0.0403(5) Uani 0.887(3) 1 d D . P A 1
F4 F 1.38904(10) 0.5695(2) 0.39277(17) 0.0892(9) Uani 0.887(3) 1 d D . P A 1
F5 F 1.39456(10) 0.8519(2) 0.39623(11) 0.0577(5) Uani 0.887(3) 1 d D . P A 1
F6 F 1.39788(10) 0.7162(3) 0.28740(10) 0.0754(7) Uani 0.887(3) 1 d D . P A 1
C14' C 1.25726(12) 0.7241(2) 0.33174(11) 0.0341(4) Uani 0.113(3) 1 d D . P A 2
C22' C 1.3566(3) 0.6998(11) 0.3613(5) 0.0403(5) Uani 0.113(3) 1 d D . P A 2
F4' F 1.4034(6) 0.8481(14) 0.3568(11) 0.0892(9) Uani 0.113(3) 1 d D . P A 2
F5' F 1.3916(5) 0.5796(17) 0.3185(8) 0.0577(5) Uani 0.113(3) 1 d D . P A 2
F6' F 1.3770(6) 0.647(2) 0.4372(5) 0.0754(7) Uani 0.113(3) 1 d D . P A 2


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C7 1.271(2) . ?
N1 C1 1.415(2) . ?
N2 C17 1.276(2) . ?
N2 C11 1.416(2) . ?
C1 C2 1.395(3) . ?
C1 C6 1.395(3) . ?
C3 C2 1.379(3) . ?
C3 C4 1.394(3) . ?
C3 H3 0.9500 . ?
C2 H2 0.9500 . ?
C4 C5 1.388(3) . ?
C4 C21 1.492(2) . ?
C21 F2 1.326(2) . ?
C21 F1 1.3264(19) . ?
C21 F3 1.332(2) . ?
C5 C6 1.384(3) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C7 C8 1.469(3) . ?
C7 H7 0.9500 . ?
C8 C20 1.399(3) . ?
C8 C9 1.400(3) . ?
C9 C10 1.378(3) . ?
C9 H9 0.9500 . ?
C10 C18 1.400(3) . ?
C10 H10 0.9500 . ?
C11 C16 1.393(3) . ?
C11 C12 1.397(3) . ?
C12 C13 1.380(3) . ?
C12 H12 0.9500 . ?
C13 C14' 1.391(3) . ?
C13 C14 1.391(3) . ?
C13 H13 0.9966 . ?
C15 C16 1.384(3) . ?
C15 C14' 1.388(3) . ?
C15 C14 1.388(3) . ?
C15 H15 1.0027 . ?
C16 H16 0.9500 . ?
C17 C18 1.464(3) . ?
C17 H17 0.9500 . ?
C18 C19 1.399(3) . ?
C19 C20 1.380(3) . ?
C19 H19 0.9500 . ?
C20 H20 0.9500 . ?
C14 C22 1.497(3) . ?
C22 F4 1.326(2) . ?
C22 F5 1.327(2) . ?
C22 F6 1.329(2) . ?
C14' C22' 1.491(4) . ?
C22' F6' 1.324(4) . ?
C22' F4' 1.325(4) . ?
C22' F5' 1.325(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 N1 C1 118.92(16) . . ?
C17 N2 C11 119.23(17) . . ?
C2 C1 C6 119.00(17) . . ?
C2 C1 N1 117.53(16) . . ?
C6 C1 N1 123.44(17) . . ?
C2 C3 C4 119.77(17) . . ?
C2 C3 H3 120.1 . . ?
C4 C3 H3 120.1 . . ?
C3 C2 C1 120.86(17) . . ?
C3 C2 H2 119.6 . . ?
C1 C2 H2 119.6 . . ?
C5 C4 C3 119.76(17) . . ?
C5 C4 C21 120.93(16) . . ?
C3 C4 C21 119.22(16) . . ?
F2 C21 F1 105.74(15) . . ?
F2 C21 F3 106.25(16) . . ?
F1 C21 F3 105.78(16) . . ?
F2 C21 C4 112.88(15) . . ?
F1 C21 C4 113.48(15) . . ?
F3 C21 C4 112.10(15) . . ?
C6 C5 C4 120.37(17) . . ?
C6 C5 H5 119.8 . . ?
C4 C5 H5 119.8 . . ?
C5 C6 C1 120.20(17) . . ?
C5 C6 H6 119.9 . . ?
C1 C6 H6 119.9 . . ?
N1 C7 C8 121.87(17) . . ?
N1 C7 H7 119.1 . . ?
C8 C7 H7 119.1 . . ?
C20 C8 C9 119.14(17) . . ?
C20 C8 C7 121.31(16) . . ?
C9 C8 C7 119.46(17) . . ?
C10 C9 C8 120.79(17) . . ?
C10 C9 H9 119.6 . . ?
C8 C9 H9 119.6 . . ?
C9 C10 C18 120.20(17) . . ?
C9 C10 H10 119.9 . . ?
C18 C10 H10 119.9 . . ?
C16 C11 C12 119.03(17) . . ?
C16 C11 N2 122.69(16) . . ?
C12 C11 N2 118.14(17) . . ?
C13 C12 C11 120.28(18) . . ?
C13 C12 H12 119.9 . . ?
C11 C12 H12 119.9 . . ?
C12 C13 C14' 120.19(17) . . ?
C12 C13 C14 120.19(17) . . ?
C12 C13 H13 118.9 . . ?
C14' C13 H13 120.8 . . ?
C14 C13 H13 120.8 . . ?
C16 C15 C14' 119.78(18) . . ?
C16 C15 C14 119.78(18) . . ?
C16 C15 H15 119.3 . . ?
C14' C15 H15 120.9 . . ?
C14 C15 H15 120.9 . . ?
C15 C16 C11 120.72(17) . . ?
C15 C16 H16 119.6 . . ?
C11 C16 H16 119.6 . . ?
N2 C17 C18 122.00(18) . . ?
N2 C17 H17 119.0 . . ?
C18 C17 H17 119.0 . . ?
C19 C18 C10 118.91(17) . . ?
C19 C18 C17 119.91(17) . . ?
C10 C18 C17 121.17(17) . . ?
C20 C19 C18 120.97(17) . . ?
C20 C19 H19 119.5 . . ?
C18 C19 H19 119.5 . . ?
C19 C20 C8 119.98(17) . . ?
C19 C20 H20 120.0 . . ?
C8 C20 H20 120.0 . . ?
C15 C14 C13 119.96(17) . . ?
C15 C14 C22 119.80(17) . . ?
C13 C14 C22 120.24(17) . . ?
F4 C22 F5 106.17(19) . . ?
F4 C22 F6 105.9(2) . . ?
F5 C22 F6 105.33(18) . . ?
F4 C22 C14 112.93(17) . . ?
F5 C22 C14 112.19(17) . . ?
F6 C22 C14 113.68(17) . . ?
C15 C14' C13 119.96(17) . . ?
C15 C14' C22' 123.7(3) . . ?
C13 C14' C22' 115.8(3) . . ?
F6' C22' F4' 106.2(5) . . ?
F6' C22' F5' 106.4(5) . . ?
F4' C22' F5' 105.8(5) . . ?
F6' C22' C14' 113.3(5) . . ?
F4' C22' C14' 112.6(5) . . ?
F5' C22' C14' 112.0(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
C7 N1 C1 C2 -141.54(19) . . . . ?
C7 N1 C1 C6 40.5(3) . . . . ?
N1 C1 C2 C3 179.84(17) . . . . ?
C2 C3 C4 C21 176.71(17) . . . . ?
C5 C4 C21 F2 -136.51(19) . . . . ?
C3 C4 C21 F2 46.8(2) . . . . ?
C5 C4 C21 F1 -16.2(2) . . . . ?
C3 C4 C21 F1 167.11(17) . . . . ?
C5 C4 C21 F3 103.5(2) . . . . ?
C3 C4 C21 F3 -73.1(2) . . . . ?
C21 C4 C5 C6 -177.65(17) . . . . ?
N1 C1 C6 C5 179.02(17) . . . . ?
C1 N1 C7 C8 179.39(16) . . . . ?
N1 C7 C8 C20 11.2(3) . . . . ?
N1 C7 C8 C9 -165.20(18) . . . . ?
C7 C8 C9 C10 175.21(17) . . . . ?
C17 N2 C11 C16 -40.9(3) . . . . ?
C17 N2 C11 C12 143.48(19) . . . . ?
N2 C11 C12 C13 177.92(18) . . . . ?
C11 C12 C13 C14' -1.8(3) . . . . ?
C11 C12 C13 C14 -1.8(3) . . . . ?
C14' C15 C16 C11 -0.5(3) . . . . ?
C14 C15 C16 C11 -0.5(3) . . . . ?
N2 C11 C16 C15 -176.56(18) . . . . ?
C11 N2 C17 C18 175.44(16) . . . . ?
C9 C10 C18 C17 -179.85(17) . . . . ?
N2 C17 C18 C19 174.19(18) . . . . ?
N2 C17 C18 C10 -6.5(3) . . . . ?
C17 C18 C19 C20 179.27(17) . . . . ?
C7 C8 C20 C19 -175.74(17) . . . . ?
C16 C15 C14 C13 0.8(3) . . . . ?
C16 C15 C14 C22 -179.39(18) . . . . ?
C12 C13 C14 C15 0.3(3) . . . . ?
C12 C13 C14 C22 -179.45(18) . . . . ?
C15 C14 C22 F4 -95.5(3) . . . . ?
C13 C14 C22 F4 84.3(3) . . . . ?
C15 C14 C22 F5 144.6(2) . . . . ?
C13 C14 C22 F5 -35.6(3) . . . . ?
C15 C14 C22 F6 25.2(3) . . . . ?
C13 C14 C22 F6 -155.0(2) . . . . ?
C16 C15 C14' C13 0.8(3) . . . . ?
C16 C15 C14' C22' 172.6(4) . . . . ?
C12 C13 C14' C15 0.3(3) . . . . ?
C12 C13 C14' C22' -172.1(4) . . . . ?
C15 C14' C22' F6' -135.7(8) . . . . ?
C13 C14' C22' F6' 36.5(8) . . . . ?
C15 C14' C22' F4' 103.8(8) . . . . ?
C13 C14' C22' F4' -84.1(8) . . . . ?
C15 C14' C22' F5' -15.3(9) . . . . ?
C13 C14' C22' F5' 156.8(7) . . . . ?

_refine_diff_density_max         0.419
_refine_diff_density_min         -0.262
_refine_diff_density_rms         0.044


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: 1:1 diethyl ether/hexane'
####################################################################### 
# 
# 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_15018z
_database_code_depnum_ccdc_archive 'CCDC 2482771'
loop_
_audit_author_name
_audit_author_address
'William Ojala'
;University of St Thomas
United States of America
;
_audit_update_record             
;
2025-08-25 deposited with the CCDC.	2025-12-16 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2019/3
_shelx_SHELXL_version_number     2019/3
_chemical_name_systematic        
N,N^'^-(1,4-phenylenedimethylidyne)bis(3-trifluoromethyl)benzenamine
_chemical_name_common            ?
_chemical_melting_point          '403-405 K'
_chemical_formula_moiety         ?
_chemical_formula_sum            'C22 H14 F6 N2'
_chemical_formula_weight         420.35

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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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                   12.786(3)
_cell_length_b                   4.7478(10)
_cell_length_c                   14.494(3)
_cell_angle_alpha                90
_cell_angle_beta                 96.023(2)
_cell_angle_gamma                90
_cell_volume                     875.0(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    2990
_cell_measurement_theta_min      2.83
_cell_measurement_theta_max      27.35

_exptl_crystal_description       needle
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.595
_exptl_crystal_F_000             428
_exptl_transmission_factor_min   0.6972
_exptl_transmission_factor_max   0.7456
_exptl_crystal_size_max          0.350
_exptl_crystal_size_mid          0.220
_exptl_crystal_size_min          0.110
_exptl_absorpt_coefficient_mu    0.139
_shelx_estimated_absorpt_T_min   0.953
_shelx_estimated_absorpt_T_max   0.985
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6972
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   'SADABS 2012/1 (Sheldrick, 2012)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed tube'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            9477
_diffrn_reflns_av_unetI/netI     0.0204
_diffrn_reflns_av_R_equivalents  0.0270
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.022
_diffrn_reflns_theta_max         27.556
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             2010
_reflns_number_gt                1699
_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT-2014/4 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2019/2 (Sheldrick, 2019)'
_computing_molecular_graphics    
'Mercury (Macrae et al., J. Appl. Cryst., 53, 226-235, 2020)and ORTEP-3 for Windows (L. J. Farrugia, J. Appl. Cryst. (2012),45, 849-854)'
_computing_publication_material  
'enCIFer (Allen et al., J. Appl. Cryst., 37, 335-338, 2004)'
_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)+(0.0452P)²+0.3384P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_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         2010
_refine_ls_number_parameters     136
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0425
_refine_ls_R_factor_gt           0.0356
_refine_ls_wR_factor_ref         0.0954
_refine_ls_wR_factor_gt          0.0900
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_restrained_S_all      1.063
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
F1 F 0.29889(6) -0.44336(19) 0.89736(6) 0.0356(2) Uani 1 1 d . . . . .
F2 F 0.36831(7) -0.8376(2) 0.94245(6) 0.0378(2) Uani 1 1 d . . . . .
F3 F 0.30358(6) -0.7829(2) 0.80091(6) 0.0353(2) Uani 1 1 d . . . . .
N1 N 0.57101(8) -0.0476(2) 0.68035(7) 0.0210(2) Uani 1 1 d . . . . .
C1 C 0.56005(9) -0.2514(3) 0.75084(8) 0.0185(3) Uani 1 1 d . . . . .
C2 C 0.46444(9) -0.3493(3) 0.77739(8) 0.0196(3) Uani 1 1 d . . . . .
H2 H 0.399917 -0.277934 0.748074 0.024 Uiso 1 1 calc R U . . .
C3 C 0.46411(9) -0.5518(3) 0.84689(8) 0.0187(3) Uani 1 1 d . . . . .
C4 C 0.55726(10) -0.6619(3) 0.89034(9) 0.0223(3) Uani 1 1 d . . . . .
H4 H 0.556165 -0.800074 0.937620 0.027 Uiso 1 1 calc R U . . .
C5 C 0.65213(10) -0.5657(3) 0.86325(9) 0.0245(3) Uani 1 1 d . . . . .
H5 H 0.716526 -0.639517 0.892013 0.029 Uiso 1 1 calc R U . . .
C6 C 0.65339(10) -0.3631(3) 0.79460(9) 0.0213(3) Uani 1 1 d . . . . .
H6 H 0.718847 -0.299078 0.777014 0.026 Uiso 1 1 calc R U . . .
C7 C 0.49104(10) 0.0841(3) 0.64284(8) 0.0202(3) Uani 1 1 d . . . . .
H7 H 0.424262 0.043595 0.662899 0.024 Uiso 1 1 calc R U . . .
C8 C 0.49736(10) 0.2961(3) 0.56981(8) 0.0188(3) Uani 1 1 d . . . . .
C9 C 0.59240(10) 0.3642(3) 0.53556(9) 0.0217(3) Uani 1 1 d . . . . .
H9 H 0.655470 0.272097 0.559443 0.026 Uiso 1 1 calc R U . . .
C10 C 0.40548(10) 0.4340(3) 0.53325(9) 0.0219(3) Uani 1 1 d . . . . .
H10 H 0.340552 0.388420 0.556012 0.026 Uiso 1 1 calc R U . . .
C11 C 0.36026(10) -0.6540(3) 0.87226(9) 0.0224(3) 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
F1 C11 1.3447(15) . ?
F2 C11 1.3357(15) . ?
F3 C11 1.3461(15) . ?
N1 C7 1.2710(17) . ?
N1 C1 1.4244(15) . ?
C1 C6 1.3961(17) . ?
C1 C2 1.3991(17) . ?
C2 C3 1.3928(17) . ?
C2 H2 0.9500 . ?
C3 C4 1.3896(17) . ?
C3 C11 1.4954(17) . ?
C4 C5 1.3906(18) . ?
C4 H4 0.9500 . ?
C5 C6 1.3853(18) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C7 C8 1.4693(17) . ?
C7 H7 0.9500 . ?
C8 C9 1.3978(18) . ?
C8 C10 1.3996(17) . ?
C9 C10 1.3853(17) 3_666 ?
C9 H9 0.9500 . ?
C10 H10 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
C7 N1 C1 120.37(11) . . ?
C6 C1 C2 118.60(11) . . ?
C6 C1 N1 116.11(11) . . ?
C2 C1 N1 125.28(11) . . ?
C3 C2 C1 119.83(11) . . ?
C3 C2 H2 120.1 . . ?
C1 C2 H2 120.1 . . ?
C4 C3 C2 121.32(11) . . ?
C4 C3 C11 120.50(11) . . ?
C2 C3 C11 118.16(11) . . ?
C3 C4 C5 118.70(11) . . ?
C3 C4 H4 120.7 . . ?
C5 C4 H4 120.7 . . ?
C6 C5 C4 120.46(11) . . ?
C6 C5 H5 119.8 . . ?
C4 C5 H5 119.8 . . ?
C5 C6 C1 121.09(11) . . ?
C5 C6 H6 119.5 . . ?
C1 C6 H6 119.5 . . ?
N1 C7 C8 122.86(11) . . ?
N1 C7 H7 118.6 . . ?
C8 C7 H7 118.6 . . ?
C9 C8 C10 118.95(11) . . ?
C9 C8 C7 121.99(11) . . ?
C10 C8 C7 119.07(11) . . ?
C10 C9 C8 119.92(11) 3_666 . ?
C10 C9 H9 120.0 3_666 . ?
C8 C9 H9 120.0 . . ?
C9 C10 C8 121.14(11) 3_666 . ?
C9 C10 H10 119.4 3_666 . ?
C8 C10 H10 119.4 . . ?
F2 C11 F1 106.25(10) . . ?
F2 C11 F3 106.29(11) . . ?
F1 C11 F3 105.28(10) . . ?
F2 C11 C3 113.56(10) . . ?
F1 C11 C3 112.56(11) . . ?
F3 C11 C3 112.28(10) . . ?

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
C7 N1 C1 C6 -173.50(12) . . . . ?
C7 N1 C1 C2 7.85(19) . . . . ?
N1 C1 C2 C3 179.34(11) . . . . ?
C1 C2 C3 C11 -179.12(11) . . . . ?
C11 C3 C4 C5 178.55(12) . . . . ?
N1 C1 C6 C5 -179.06(11) . . . . ?
C1 N1 C7 C8 -179.94(10) . . . . ?
N1 C7 C8 C9 1.02(19) . . . . ?
N1 C7 C8 C10 -179.09(12) . . . . ?
C7 C8 C9 C10 -179.89(11) . . . 3_666 ?
C7 C8 C10 C9 179.88(11) . . . 3_666 ?
C4 C3 C11 F2 4.46(17) . . . . ?
C2 C3 C11 F2 -177.02(11) . . . . ?
C4 C3 C11 F1 125.24(13) . . . . ?
C2 C3 C11 F1 -56.24(15) . . . . ?
C4 C3 C11 F3 -116.16(13) . . . . ?
C2 C3 C11 F3 62.36(15) . . . . ?

_refine_diff_density_max         0.281
_refine_diff_density_min         -0.307
_refine_diff_density_rms         0.051


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: ethanol'
####################################################################### 
# 
# 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_25094z
_database_code_depnum_ccdc_archive 'CCDC 2482769'
loop_
_audit_author_name
_audit_author_address
'William Ojala'
;University of St Thomas
United States of America
;
_audit_update_record             
;
2025-10-30 deposited with the CCDC.	2025-12-16 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2019/3
_shelx_SHELXL_version_number     2019/3
_chemical_name_systematic        
N¹,N⁴-bis[[3-(trifluoromethyl)phenyl]methylene]-1,4-benzenediamine
_chemical_name_common            ?
_chemical_melting_point          '380-381 K'
_chemical_formula_moiety         ?
_chemical_formula_sum            'C22 H14 F6 N2'
_chemical_formula_weight         420.35

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/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                   12.5991(11)
_cell_length_b                   4.8277(4)
_cell_length_c                   14.9975(13)
_cell_angle_alpha                90
_cell_angle_beta                 98.831(3)
_cell_angle_gamma                90
_cell_volume                     901.40(13)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    2718
_cell_measurement_theta_min      2.29
_cell_measurement_theta_max      28.22

_exptl_crystal_description       needle
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.549
_exptl_crystal_F_000             428
_exptl_transmission_factor_min   0.6258
_exptl_transmission_factor_max   0.7457
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.110
_exptl_crystal_size_min          0.045
_exptl_absorpt_coefficient_mu    0.135
_shelx_estimated_absorpt_T_min   0.967
_shelx_estimated_absorpt_T_max   0.994
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6258
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_process_details   'SADABS 2016/2 (Krause et al., 2015)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed tube'
_diffrn_measurement_device_type  'Bruker Photon-III CPAD diffractometer'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            14081
_diffrn_reflns_av_unetI/netI     0.0248
_diffrn_reflns_av_R_equivalents  0.0336
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         1.968
_diffrn_reflns_theta_max         28.324
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             2242
_reflns_number_gt                1801
_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT-2018/2 (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2019/2 (Sheldrick, 2019)'
_computing_molecular_graphics    
'Mercury (Macrae et al., J. Appl. Cryst., (2020), 53, 226-235) and ORTEP-3 for Windows (L. J. Farrugia, J. Appl. Cryst., (2012), 45, 849-854)'
_computing_publication_material  
'encifer (Allen et al., J. Appl Cryst. (2004), 37, 335-338'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0456P)²+0.4159P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_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         2242
_refine_ls_number_parameters     136
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0507
_refine_ls_R_factor_gt           0.0394
_refine_ls_wR_factor_ref         0.1051
_refine_ls_wR_factor_gt          0.0976
_refine_ls_goodness_of_fit_ref   1.046
_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
N1 N 0.56568(9) 0.1129(2) 0.63935(7) 0.0229(3) Uani 1 1 d . . . . .
C1 C 0.52797(10) -0.2378(3) 0.74505(8) 0.0204(3) Uani 1 1 d . . . . .
C2 C 0.44526(11) -0.3770(3) 0.77749(9) 0.0217(3) Uani 1 1 d . . . . .
H2 H 0.372922 -0.341252 0.751616 0.026 Uiso 1 1 calc R U . . .
C3 C 0.46688(10) -0.5676(3) 0.84719(9) 0.0204(3) Uani 1 1 d . . . . .
C4 C 0.57241(11) -0.6266(3) 0.88440(9) 0.0219(3) Uani 1 1 d . . . . .
H4 H 0.587540 -0.758254 0.931723 0.026 Uiso 1 1 calc R U . . .
C5 C 0.65558(11) -0.4901(3) 0.85140(9) 0.0225(3) Uani 1 1 d . . . . .
H5 H 0.727904 -0.530912 0.876052 0.027 Uiso 1 1 calc R U . . .
C6 C 0.63439(11) -0.2957(3) 0.78314(9) 0.0216(3) Uani 1 1 d . . . . .
H6 H 0.691937 -0.201429 0.762097 0.026 Uiso 1 1 calc R U . . .
C7 C 0.49848(11) -0.0365(3) 0.67192(9) 0.0240(3) Uani 1 1 d . . . . .
H7 H 0.424633 -0.017315 0.647663 0.029 Uiso 1 1 calc R U . . .
C8 C 0.52838(11) 0.3048(3) 0.56946(9) 0.0210(3) Uani 1 1 d . . . . .
C9 C 0.60595(12) 0.4327(3) 0.52755(10) 0.0285(3) Uani 1 1 d . . . . .
H9 H 0.679483 0.389055 0.546482 0.034 Uiso 1 1 calc R U . . .
C10 C 0.42133(12) 0.3773(3) 0.54131(11) 0.0324(4) Uani 1 1 d . . . . .
H10 H 0.366583 0.295437 0.569657 0.039 Uiso 1 1 calc R U . . .
C11 C 0.37411(11) -0.7051(3) 0.87988(9) 0.0245(3) Uani 1 1 d . . . . .
F1 F 0.30624(7) -0.52108(19) 0.90857(6) 0.0344(2) Uani 1 1 d . . . . .
F2 F 0.40255(7) -0.8810(2) 0.94795(6) 0.0392(3) Uani 1 1 d . . . . .
F3 F 0.31340(7) -0.85084(19) 0.81406(6) 0.0337(2) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C7 1.2659(18) . ?
N1 C8 1.4237(16) . ?
C1 C2 1.3892(19) . ?
C1 C6 1.4024(18) . ?
C1 C7 1.4700(18) . ?
C2 C3 1.3879(18) . ?
C2 H2 0.9500 . ?
C3 C4 1.3901(18) . ?
C3 C11 1.4910(19) . ?
C4 C5 1.3916(19) . ?
C4 H4 0.9500 . ?
C5 C6 1.3843(18) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C7 H7 0.9500 . ?
C8 C9 1.386(2) . ?
C8 C10 1.395(2) . ?
C9 C10 1.385(2) 3_666 ?
C9 H9 0.9500 . ?
C10 H10 0.9500 . ?
C11 F2 1.3338(15) . ?
C11 F1 1.3485(17) . ?
C11 F3 1.3501(16) . ?

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 N1 C8 119.34(12) . . ?
C2 C1 C6 118.86(12) . . ?
C2 C1 C7 117.64(12) . . ?
C6 C1 C7 123.50(12) . . ?
C3 C2 C1 120.90(12) . . ?
C3 C2 H2 119.6 . . ?
C1 C2 H2 119.6 . . ?
C2 C3 C4 120.20(12) . . ?
C2 C3 C11 118.02(12) . . ?
C4 C3 C11 121.78(12) . . ?
C3 C4 C5 119.10(12) . . ?
C3 C4 H4 120.5 . . ?
C5 C4 H4 120.5 . . ?
C6 C5 C4 120.92(12) . . ?
C6 C5 H5 119.5 . . ?
C4 C5 H5 119.5 . . ?
C5 C6 C1 120.00(12) . . ?
C5 C6 H6 120.0 . . ?
C1 C6 H6 120.0 . . ?
N1 C7 C1 123.85(12) . . ?
N1 C7 H7 118.1 . . ?
C1 C7 H7 118.1 . . ?
C9 C8 C10 117.88(12) . . ?
C9 C8 N1 116.61(12) . . ?
C10 C8 N1 125.50(12) . . ?
C10 C9 C8 121.46(13) 3_666 . ?
C10 C9 H9 119.3 3_666 . ?
C8 C9 H9 119.3 . . ?
C9 C10 C8 120.65(13) 3_666 . ?
C9 C10 H10 119.7 3_666 . ?
C8 C10 H10 119.7 . . ?
F2 C11 F1 106.51(11) . . ?
F2 C11 F3 106.47(11) . . ?
F1 C11 F3 105.12(11) . . ?
F2 C11 C3 113.76(11) . . ?
F1 C11 C3 112.28(11) . . ?
F3 C11 C3 112.10(11) . . ?

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

C7 C1 C2 C3 -179.22(12) . . . . ?
C1 C2 C3 C11 178.78(12) . . . . ?
C11 C3 C4 C5 -179.58(12) . . . . ?
C7 C1 C6 C5 -179.46(13) . . . . ?
C8 N1 C7 C1 -179.00(12) . . . . ?
C2 C1 C7 N1 176.60(13) . . . . ?
C6 C1 C7 N1 -3.5(2) . . . . ?
C7 N1 C8 C9 -170.86(13) . . . . ?
C7 N1 C8 C10 10.4(2) . . . . ?
N1 C8 C9 C10 179.95(14) . . . 3_666 ?
N1 C8 C10 C9 179.93(14) . . . 3_666 ?
C2 C3 C11 F2 -178.85(12) . . . . ?
C4 C3 C11 F2 1.33(19) . . . . ?
C2 C3 C11 F1 -57.79(16) . . . . ?
C4 C3 C11 F1 122.39(13) . . . . ?
C2 C3 C11 F3 60.27(16) . . . . ?
C4 C3 C11 F3 -119.54(14) . . . . ?

_refine_diff_density_max         0.251
_refine_diff_density_min         -0.253
_refine_diff_density_rms         0.049


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: ethanol'
####################################################################### 
# 
# 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_09016z
_database_code_depnum_ccdc_archive 'CCDC 2482770'
loop_
_audit_author_name
_audit_author_address
'William Ojala'
;University of St Thomas
United States of America
;
_audit_update_record             
;
2025-08-25 deposited with the CCDC.	2025-12-16 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2019/3
_shelx_SHELXL_version_number     2019/3
_chemical_name_systematic        
N¹,N⁴-bis[[2-(trifluoromethyl)phenyl]methylene]-1,4-benzenediamine
_chemical_name_common            ?
_chemical_melting_point          423-425K
_chemical_formula_moiety         ?
_chemical_formula_sum            'C22 H14 F6 N2'
_chemical_formula_weight         420.35

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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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                   4.9998(10)
_cell_length_b                   12.277(2)
_cell_length_c                   14.928(3)
_cell_angle_alpha                90
_cell_angle_beta                 92.252(3)
_cell_angle_gamma                90
_cell_volume                     915.6(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    2322
_cell_measurement_theta_min      2.15
_cell_measurement_theta_max      27.26

_exptl_crystal_description       needle
_exptl_crystal_colour            green
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.525
_exptl_crystal_F_000             428
_exptl_transmission_factor_min   0.6634
_exptl_transmission_factor_max   0.7456
_exptl_crystal_size_max          0.500
_exptl_crystal_size_mid          0.250
_exptl_crystal_size_min          0.250
_exptl_absorpt_coefficient_mu    0.133
_shelx_estimated_absorpt_T_min   0.936
_shelx_estimated_absorpt_T_max   0.967
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6634
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   
'SADABS 2016/2 Krause et al., J. Appl. Cryst. 48 (2015) 3-10'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed tube'
_diffrn_measurement_device_type  'Siemens SMART platform CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            10454
_diffrn_reflns_av_unetI/netI     0.0221
_diffrn_reflns_av_R_equivalents  0.0287
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.148
_diffrn_reflns_theta_max         27.512
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             2109
_reflns_number_gt                1612
_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2019/2 (Sheldrick, 2019)'
_computing_molecular_graphics    
'Mercury (Macrae et al., J. Appl. Cryst., 53, 226-235, 2020)and ORTEP-3 for Windows (L. J. Farrugia, J. Appl. Cryst. (2012),45, 849-854)'
_computing_publication_material  
'enCIFer (Allen et al., J. Appl. Cryst., 37, 335-338, 2004)'
_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)+(0.0500P)²+0.1281P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_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         2109
_refine_ls_number_parameters     136
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0543
_refine_ls_R_factor_gt           0.0369
_refine_ls_wR_factor_ref         0.1012
_refine_ls_wR_factor_gt          0.0939
_refine_ls_goodness_of_fit_ref   1.095
_refine_ls_restrained_S_all      1.095
_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
F1 F -0.07664(18) 0.09095(7) 0.42081(7) 0.0551(3) Uani 1 1 d . . . . .
F2 F -0.3678(2) 0.19372(8) 0.47946(6) 0.0585(3) Uani 1 1 d . . . . .
F3 F -0.49176(19) 0.05025(8) 0.40718(6) 0.0554(3) Uani 1 1 d . . . . .
N1 N 0.1497(2) 0.41586(9) 0.36464(7) 0.0344(3) Uani 1 1 d . . . . .
C1 C -0.1805(3) 0.28991(11) 0.30828(9) 0.0339(3) Uani 1 1 d . . . . .
C2 C -0.3449(3) 0.19931(11) 0.32179(9) 0.0328(3) Uani 1 1 d . . . . .
C3 C -0.5404(3) 0.17012(11) 0.25732(9) 0.0369(3) Uani 1 1 d . . . . .
H3 H -0.650414 0.108388 0.266720 0.044 Uiso 1 1 calc R U . . .
C4 C -0.5752(3) 0.23069(12) 0.17956(9) 0.0400(3) Uani 1 1 d . . . . .
H4 H -0.710392 0.211102 0.136036 0.048 Uiso 1 1 calc R U . . .
C5 C -0.4135(3) 0.31947(13) 0.16528(10) 0.0443(4) Uani 1 1 d . . . . .
H5 H -0.436846 0.360844 0.111758 0.053 Uiso 1 1 calc R U . . .
C6 C -0.2173(3) 0.34840(12) 0.22886(10) 0.0413(3) Uani 1 1 d . . . . .
H6 H -0.105688 0.409268 0.218094 0.050 Uiso 1 1 calc R U . . .
C7 C 0.0245(3) 0.32735(11) 0.37541(9) 0.0365(3) Uani 1 1 d . . . . .
H7 H 0.062989 0.284496 0.427319 0.044 Uiso 1 1 calc R U . . .
C8 C 0.3255(2) 0.45478(10) 0.43422(9) 0.0309(3) Uani 1 1 d . . . . .
C9 C 0.5354(2) 0.52180(11) 0.41027(9) 0.0333(3) Uani 1 1 d . . . . .
H9 H 0.560080 0.537488 0.348825 0.040 Uiso 1 1 calc R U . . .
C10 C 0.2914(3) 0.43424(11) 0.52484(9) 0.0335(3) Uani 1 1 d . . . . .
H10 H 0.147466 0.389479 0.542289 0.040 Uiso 1 1 calc R U . . .
C11 C -0.3208(3) 0.13392(12) 0.40641(9) 0.0402(3) 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
F1 C11 1.3393(17) . ?
F2 C11 1.3428(17) . ?
F3 C11 1.3368(17) . ?
N1 C7 1.2673(18) . ?
N1 C8 1.4170(16) . ?
C1 C6 1.392(2) . ?
C1 C2 1.4024(19) . ?
C1 C7 1.4785(17) . ?
C2 C3 1.3915(17) . ?
C2 C11 1.4975(19) . ?
C3 C4 1.384(2) . ?
C3 H3 0.9500 . ?
C4 C5 1.378(2) . ?
C4 H4 0.9500 . ?
C5 C6 1.3844(19) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C7 H7 0.9500 . ?
C8 C9 1.3915(19) . ?
C8 C10 1.3931(19) . ?
C9 C10 1.3831(17) 3_666 ?
C9 H9 0.9500 . ?
C10 H10 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
C7 N1 C8 119.42(12) . . ?
C6 C1 C2 118.24(12) . . ?
C6 C1 C7 118.80(13) . . ?
C2 C1 C7 122.94(12) . . ?
C3 C2 C1 120.30(12) . . ?
C3 C2 C11 118.46(12) . . ?
C1 C2 C11 121.22(11) . . ?
C4 C3 C2 120.23(13) . . ?
C4 C3 H3 119.9 . . ?
C2 C3 H3 119.9 . . ?
C5 C4 C3 119.98(13) . . ?
C5 C4 H4 120.0 . . ?
C3 C4 H4 120.0 . . ?
C4 C5 C6 120.06(14) . . ?
C4 C5 H5 120.0 . . ?
C6 C5 H5 120.0 . . ?
C5 C6 C1 121.19(14) . . ?
C5 C6 H6 119.4 . . ?
C1 C6 H6 119.4 . . ?
N1 C7 C1 120.88(13) . . ?
N1 C7 H7 119.6 . . ?
C1 C7 H7 119.6 . . ?
C9 C8 C10 118.61(11) . . ?
C9 C8 N1 117.61(12) . . ?
C10 C8 N1 123.69(12) . . ?
C10 C9 C8 120.57(12) 3_666 . ?
C10 C9 H9 119.7 3_666 . ?
C8 C9 H9 119.7 . . ?
C9 C10 C8 120.82(12) 3_666 . ?
C9 C10 H10 119.6 3_666 . ?
C8 C10 H10 119.6 . . ?
F3 C11 F1 105.97(11) . . ?
F3 C11 F2 106.30(12) . . ?
F1 C11 F2 105.81(11) . . ?
F3 C11 C2 112.88(11) . . ?
F1 C11 C2 112.91(12) . . ?
F2 C11 C2 112.40(12) . . ?

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
C7 C1 C2 C3 177.88(12) . . . . ?
C6 C1 C2 C11 -178.69(13) . . . . ?
C7 C1 C2 C11 -0.3(2) . . . . ?
C11 C2 C3 C4 177.81(13) . . . . ?
C7 C1 C6 C5 -177.43(13) . . . . ?
C8 N1 C7 C1 173.80(12) . . . . ?
C6 C1 C7 N1 5.8(2) . . . . ?
C2 C1 C7 N1 -172.67(13) . . . . ?
C7 N1 C8 C9 153.90(13) . . . . ?
C7 N1 C8 C10 -29.50(19) . . . . ?
N1 C8 C9 C10 177.66(12) . . . 3_666 ?
N1 C8 C10 C9 -177.45(12) . . . 3_666 ?
C3 C2 C11 F3 2.34(18) . . . . ?
C1 C2 C11 F3 -179.49(12) . . . . ?
C3 C2 C11 F1 122.50(13) . . . . ?
C1 C2 C11 F1 -59.33(17) . . . . ?
C3 C2 C11 F2 -117.89(14) . . . . ?
C1 C2 C11 F2 60.28(17) . . . . ?

_refine_diff_density_max         0.183
_refine_diff_density_min         -0.242
_refine_diff_density_rms         0.040


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: toluene'
