# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2019

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

data_compound_3b
_database_code_depnum_ccdc_archive 'CCDC 1895628'
loop_
_audit_author_name
_audit_author_address
'Manfredo Horner'
;UFSM
Brazil
;
_audit_update_record             
;
2019-06-21 deposited with the CCDC.	2019-07-16 downloaded from the CCDC.
;


_audit_creation_method           SHELXL-2018/3
_chemical_name_systematic        
(Z)-4-((4-aminophenyl)amino)-1,1,1-trifluoro-4-phenylbut-3-en-2-one
_chemical_name_common            'enamino ketone trifluoromethyl'
_chemical_melting_point          .
_chemical_formula_moiety         'C16  H13  F3  N2  O'
_chemical_formula_sum            'C16 H13 F3 N2 O'
_chemical_formula_weight         306.28

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                   12.0703(9)
_cell_length_b                   5.8282(4)
_cell_length_c                   20.5755(14)
_cell_angle_alpha                90
_cell_angle_beta                 100.792(2)
_cell_angle_gamma                90
_cell_volume                     1421.85(17)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9925
_cell_measurement_theta_min      2.39
_cell_measurement_theta_max      26.64

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.431
_exptl_crystal_F_000             632
_exptl_transmission_factor_min   0.5601
_exptl_transmission_factor_max   0.7455
_exptl_crystal_size_max          0.397
_exptl_crystal_size_mid          0.091
_exptl_crystal_size_min          0.055
_exptl_absorpt_coefficient_mu    0.118
_shelx_estimated_absorpt_T_min   0.955
_shelx_estimated_absorpt_T_max   0.994
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.56
_exptl_absorpt_correction_T_max  0.746
_exptl_absorpt_process_details   
;
   SADABS-2016/2 - Bruker AXS area detector scaling and absorption correction.
Reference: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.
J. Appl. Cryst. 48 (2015) 3-10.
;
_exptl_absorpt_special_details   none
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean 10.4167
_diffrn_reflns_number            38690
_diffrn_reflns_av_unetI/netI     0.0389
_diffrn_reflns_av_R_equivalents  0.0919
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_theta_min         2.391
_diffrn_reflns_theta_max         27.152
_diffrn_reflns_theta_full        25.242
_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             3156
_reflns_number_gt                2384
_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 APEX-III'
_computing_cell_refinement       'BRUKER SAINT'
_computing_data_reduction        'BRUKER SOFTWARE'
_computing_structure_solution    'SHELXT-2014 (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 2012)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'
_refine_special_details          
;
Fixed Uiso - At -1.2 times:
All C(H) groups, N(H,H) group
Restrained distances
(H41 N41), (H41A N414), (N414 H41B)
Rotating group:
N414(H41A,H41B)
Aromatic/amide H refined with riding coordinates:
C413(H413), C412(H412), C42(H42), C43(H43), C44(H44), C415(H415),
C416(H416), C45(H45), C46(H46), C3(H3)
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0749P)²+1.0510P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3156
_refine_ls_number_parameters     204
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0830
_refine_ls_R_factor_gt           0.0585
_refine_ls_wR_factor_ref         0.1505
_refine_ls_wR_factor_gt          0.1377
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_restrained_S_all      1.055
_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
C1 C 0.12818(19) 0.7652(4) 0.50820(10) 0.0255(5) Uani 1 1 d . . . . .
C2 C 0.19370(17) 0.5724(4) 0.48289(9) 0.0199(4) Uani 1 1 d . . . . .
C3 C 0.17013(17) 0.5242(4) 0.41472(9) 0.0188(4) Uani 1 1 d . . . . .
H3 H 0.112305 0.608382 0.387104 0.023 Uiso 1 1 calc R U . . .
C4 C 0.22838(16) 0.3579(3) 0.38634(9) 0.0165(4) Uani 1 1 d . . . . .
C41 C 0.19743(17) 0.3237(3) 0.31349(9) 0.0177(4) Uani 1 1 d . . . . .
C42 C 0.14510(18) 0.1215(4) 0.28857(10) 0.0236(5) Uani 1 1 d . . . . .
H42 H 0.132246 0.002558 0.317844 0.028 Uiso 1 1 calc R U . . .
C43 C 0.11149(19) 0.0938(4) 0.22035(11) 0.0300(5) Uani 1 1 d . . . . .
H43 H 0.074775 -0.043330 0.203046 0.036 Uiso 1 1 calc R U . . .
C44 C 0.1317(2) 0.2659(4) 0.17820(10) 0.0310(6) Uani 1 1 d . . . . .
H44 H 0.110185 0.245348 0.131742 0.037 Uiso 1 1 calc R U . . .
C45 C 0.1830(2) 0.4679(4) 0.20269(10) 0.0295(5) Uani 1 1 d . . . . .
H45 H 0.196039 0.585946 0.173168 0.035 Uiso 1 1 calc R U . . .
C46 C 0.21557(18) 0.4985(4) 0.27073(10) 0.0230(5) Uani 1 1 d . . . . .
H46 H 0.249992 0.637993 0.287809 0.028 Uiso 1 1 calc R U . . .
C411 C 0.38315(16) 0.0716(3) 0.40042(9) 0.0165(4) Uani 1 1 d . . . . .
C412 C 0.41181(17) -0.1285(3) 0.43634(9) 0.0176(4) Uani 1 1 d . . . . .
H412 H 0.380663 -0.158088 0.474624 0.021 Uiso 1 1 calc R U . . .
C413 C 0.48515(16) -0.2845(4) 0.41688(9) 0.0178(4) Uani 1 1 d . . . . .
H413 H 0.503797 -0.420834 0.441857 0.021 Uiso 1 1 calc R U . . .
C414 C 0.53254(16) -0.2442(4) 0.36061(9) 0.0174(4) Uani 1 1 d . . . . .
C415 C 0.50542(17) -0.0403(4) 0.32615(10) 0.0221(5) Uani 1 1 d . . . . .
H415 H 0.537685 -0.008321 0.288414 0.026 Uiso 1 1 calc R U . . .
C416 C 0.43248(17) 0.1167(4) 0.34579(9) 0.0215(5) Uani 1 1 d . . . . .
H416 H 0.415928 0.255890 0.321922 0.026 Uiso 1 1 calc R U . . .
N41 N 0.30788(14) 0.2292(3) 0.42273(8) 0.0187(4) Uani 1 1 d D . . . .
N414 N 0.60175(15) -0.4075(3) 0.33947(8) 0.0226(4) Uani 1 1 d D . . . .
H41A H 0.644523 -0.490560 0.371652 0.027 Uiso 1 1 d DR U . . .
H41B H 0.645004 -0.350917 0.313847 0.027 Uiso 1 1 d DR U . . .
O21 O 0.26527(12) 0.4754(3) 0.52543(6) 0.0253(4) Uani 1 1 d . . . . .
F11 F 0.19694(13) 0.9264(2) 0.53840(7) 0.0417(4) Uani 1 1 d . . . . .
F12 F 0.07069(13) 0.6896(3) 0.55294(8) 0.0478(4) Uani 1 1 d . . . . .
F13 F 0.05702(16) 0.8716(3) 0.46093(7) 0.0677(6) Uani 1 1 d . . . . .
H41 H 0.316(2) 0.259(5) 0.4661(9) 0.048(8) Uiso 1 1 d D . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 F13 1.325(3) . ?
C1 F12 1.328(3) . ?
C1 F11 1.328(3) . ?
C1 C2 1.521(3) . ?
C2 O21 1.244(2) . ?
C2 C3 1.406(3) . ?
C3 C4 1.389(3) . ?
C3 H3 0.9500 . ?
C4 N41 1.332(3) . ?
C4 C41 1.489(3) . ?
C41 C42 1.389(3) . ?
C41 C46 1.390(3) . ?
C42 C43 1.395(3) . ?
C42 H42 0.9500 . ?
C43 C44 1.378(4) . ?
C43 H43 0.9500 . ?
C44 C45 1.381(3) . ?
C44 H44 0.9500 . ?
C45 C46 1.393(3) . ?
C45 H45 0.9500 . ?
C46 H46 0.9500 . ?
C411 C412 1.389(3) . ?
C411 C416 1.392(3) . ?
C411 N41 1.427(2) . ?
C412 C413 1.380(3) . ?
C412 H412 0.9500 . ?
C413 C414 1.404(3) . ?
C413 H413 0.9500 . ?
C414 N414 1.388(3) . ?
C414 C415 1.391(3) . ?
C415 C416 1.381(3) . ?
C415 H415 0.9500 . ?
C416 H416 0.9500 . ?
N41 H41 0.896(17) . ?
N414 H41A 0.9008 . ?
N414 H41B 0.8731 . ?

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
F13 C1 F12 108.25(19) . . ?
F13 C1 F11 106.0(2) . . ?
F12 C1 F11 105.80(17) . . ?
F13 C1 C2 113.68(16) . . ?
F12 C1 C2 111.41(19) . . ?
F11 C1 C2 111.30(18) . . ?
O21 C2 C3 126.51(19) . . ?
O21 C2 C1 115.58(17) . . ?
C3 C2 C1 117.90(17) . . ?
C4 C3 C2 122.35(18) . . ?
C4 C3 H3 118.8 . . ?
C2 C3 H3 118.8 . . ?
N41 C4 C3 121.64(17) . . ?
N41 C4 C41 120.62(17) . . ?
C3 C4 C41 117.73(17) . . ?
C42 C41 C46 120.18(18) . . ?
C42 C41 C4 119.73(18) . . ?
C46 C41 C4 120.00(18) . . ?
C41 C42 C43 119.7(2) . . ?
C41 C42 H42 120.1 . . ?
C43 C42 H42 120.1 . . ?
C44 C43 C42 119.8(2) . . ?
C44 C43 H43 120.1 . . ?
C42 C43 H43 120.1 . . ?
C43 C44 C45 120.76(19) . . ?
C43 C44 H44 119.6 . . ?
C45 C44 H44 119.6 . . ?
C44 C45 C46 119.9(2) . . ?
C44 C45 H45 120.0 . . ?
C46 C45 H45 120.0 . . ?
C41 C46 C45 119.6(2) . . ?
C41 C46 H46 120.2 . . ?
C45 C46 H46 120.2 . . ?
C412 C411 C416 119.11(18) . . ?
C412 C411 N41 118.64(17) . . ?
C416 C411 N41 122.18(18) . . ?
C413 C412 C411 120.55(18) . . ?
C413 C412 H412 119.7 . . ?
C411 C412 H412 119.7 . . ?
C412 C413 C414 120.77(18) . . ?
C412 C413 H413 119.6 . . ?
C414 C413 H413 119.6 . . ?
N414 C414 C415 121.58(17) . . ?
N414 C414 C413 120.37(18) . . ?
C415 C414 C413 118.02(18) . . ?
C416 C415 C414 121.25(18) . . ?
C416 C415 H415 119.4 . . ?
C414 C415 H415 119.4 . . ?
C415 C416 C411 120.23(19) . . ?
C415 C416 H416 119.9 . . ?
C411 C416 H416 119.9 . . ?
C4 N41 C411 128.07(16) . . ?
C4 N41 H41 112.8(18) . . ?
C411 N41 H41 118.9(18) . . ?
C414 N414 H41A 115.7 . . ?
C414 N414 H41B 113.2 . . ?
H41A N414 H41B 108.8 . . ?

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
F13 C1 C2 O21 176.7(2) . . . . ?
F12 C1 C2 O21 -60.6(3) . . . . ?
F11 C1 C2 O21 57.2(2) . . . . ?
F13 C1 C2 C3 -1.9(3) . . . . ?
F12 C1 C2 C3 120.7(2) . . . . ?
F11 C1 C2 C3 -121.5(2) . . . . ?
O21 C2 C3 C4 -1.1(3) . . . . ?
C1 C2 C3 C4 177.39(19) . . . . ?
C2 C3 C4 N41 2.1(3) . . . . ?
C2 C3 C4 C41 -179.13(19) . . . . ?
N41 C4 C41 C42 66.9(3) . . . . ?
C3 C4 C41 C42 -111.8(2) . . . . ?
N41 C4 C41 C46 -116.4(2) . . . . ?
C3 C4 C41 C46 64.9(3) . . . . ?
C46 C41 C42 C43 0.4(3) . . . . ?
C4 C41 C42 C43 177.11(19) . . . . ?
C41 C42 C43 C44 0.8(3) . . . . ?
C42 C43 C44 C45 -1.3(3) . . . . ?
C43 C44 C45 C46 0.5(4) . . . . ?
C42 C41 C46 C45 -1.3(3) . . . . ?
C4 C41 C46 C45 -177.92(19) . . . . ?
C44 C45 C46 C41 0.8(3) . . . . ?
C416 C411 C412 C413 -2.2(3) . . . . ?
N41 C411 C412 C413 -179.38(17) . . . . ?
C411 C412 C413 C414 0.2(3) . . . . ?
C412 C413 C414 N414 -176.74(18) . . . . ?
C412 C413 C414 C415 1.5(3) . . . . ?
N414 C414 C415 C416 177.06(18) . . . . ?
C413 C414 C415 C416 -1.2(3) . . . . ?
C414 C415 C416 C411 -0.9(3) . . . . ?
C412 C411 C416 C415 2.6(3) . . . . ?
N41 C411 C416 C415 179.62(18) . . . . ?
C3 C4 N41 C411 -172.22(19) . . . . ?
C41 C4 N41 C411 9.1(3) . . . . ?
C412 C411 N41 C4 -143.8(2) . . . . ?
C416 C411 N41 C4 39.2(3) . . . . ?

_refine_diff_density_max         0.572
_refine_diff_density_min         -0.457
_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_Compound_4d
_database_code_depnum_ccdc_archive 'CCDC 1895629'
loop_
_audit_author_name
_audit_author_address
'Manfredo Horner'
;UFSM
Brazil
;
_audit_update_record             
;
2019-06-21 deposited with the CCDC.	2019-07-16 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_chemical_name_systematic        
;
2-(4-fluorophenyl)-4-(trifluoromethyl)quinolin-6-amine
;
_chemical_name_common            'amino quinoline'
_chemical_melting_point          .
_chemical_formula_moiety         'C16 H10 F4 N2'
_chemical_formula_sum            'C16 H10 F4 N2'
_chemical_formula_weight         306.26

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 '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                   14.122(3)
_cell_length_b                   4.6032(10)
_cell_length_c                   21.574(5)
_cell_angle_alpha                90
_cell_angle_beta                 106.541(11)
_cell_angle_gamma                90
_cell_volume                     1344.4(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    4470
_cell_measurement_theta_min      3.26
_cell_measurement_theta_max      69.22

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.513
_exptl_crystal_F_000             624
_exptl_transmission_factor_min   0.6708
_exptl_transmission_factor_max   0.7531
_exptl_crystal_size_max          0.318
_exptl_crystal_size_mid          0.248
_exptl_crystal_size_min          0.094
_exptl_absorpt_coefficient_mu    1.126
_shelx_estimated_absorpt_T_min   0.716
_shelx_estimated_absorpt_T_max   0.902
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.671
_exptl_absorpt_correction_T_max  0.753
_exptl_absorpt_process_details   
;
SADABS-2016/2 - Bruker AXS area detector scaling and absorption correction.
Reference: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.
J. Appl. Cryst. 48 (2015) 3-10.
;
_exptl_absorpt_special_details   none
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker D8 Quest'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean 10.4167
_diffrn_reflns_number            8521
_diffrn_reflns_av_unetI/netI     0.0189
_diffrn_reflns_av_R_equivalents  0.0199
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         3.264
_diffrn_reflns_theta_max         68.481
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.948
_diffrn_measured_fraction_theta_full 0.914
_diffrn_reflns_Laue_measured_fraction_max 0.948
_diffrn_reflns_Laue_measured_fraction_full 0.914
_diffrn_reflns_point_group_measured_fraction_max 0.948
_diffrn_reflns_point_group_measured_fraction_full 0.914
_reflns_number_total             2353
_reflns_number_gt                1879
_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 APEX-III'
_computing_cell_refinement       'BRUKER SAINT'
_computing_data_reduction        'BRUKER SOFTWARE'
_computing_structure_solution    'SHELXS-2013 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 2012)'
_computing_publication_material  
;
'WinGX publication routines (Farrugia, 2012)'
;
_refine_special_details          
;
Fixed Uiso - At -1.2 times:
All C(H) groups, N(H,H) group
Restrained distances
(H61B N61), (H61A N61)
Rotating group:
N61(H61A,H61B)
Aromatic/amide H refined with riding coordinates:
C5(H5), C7(H7), C8(H8), C3(H3), C22(H22), C23(H23),
C25(H25), C26(H26)
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0586P)²+0.2157P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2353
_refine_ls_number_parameters     200
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0485
_refine_ls_R_factor_gt           0.0359
_refine_ls_wR_factor_ref         0.1026
_refine_ls_wR_factor_gt          0.0931
_refine_ls_goodness_of_fit_ref   1.019
_refine_ls_restrained_S_all      1.019
_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
F43 F 0.63093(8) 0.3559(3) 0.65162(5) 0.0724(3) Uani 1 1 d . . . . .
F42 F 0.57925(7) 0.7306(2) 0.59305(5) 0.0658(3) Uani 1 1 d . . . . .
F44 F 0.52337(7) 0.3106(2) 0.55957(5) 0.0626(3) Uani 1 1 d . . . . .
N61 N 0.91708(11) 1.0494(3) 0.71674(6) 0.0625(4) Uani 1 1 d D . . . .
H61A H 0.864726 1.124821 0.726137 0.075 Uiso 1 1 d DR U . . .
H61B H 0.962679 1.179188 0.717484 0.075 Uiso 1 1 d DR U . . .
N1 N 0.83854(9) 0.3262(3) 0.50157(6) 0.0468(3) Uani 1 1 d . . . . .
F241 F 0.69547(10) -0.4899(3) 0.25809(6) 0.1032(5) Uani 1 1 d . . . . .
C6 C 0.89318(12) 0.8729(3) 0.66211(7) 0.0488(4) Uani 1 1 d . . . . .
C5 C 0.80211(12) 0.7453(3) 0.64010(7) 0.0478(4) Uani 1 1 d . . . . .
H5 H 0.754190 0.783294 0.660971 0.057 Uiso 1 1 calc R U . . .
C4A C 0.77996(10) 0.5575(3) 0.58638(7) 0.0423(3) Uani 1 1 d . . . . .
C8A C 0.85340(11) 0.4997(3) 0.55454(7) 0.0448(4) Uani 1 1 d . . . . .
C2 C 0.75078(11) 0.2065(3) 0.47759(7) 0.0454(4) Uani 1 1 d . . . . .
C21 C 0.73528(12) 0.0242(3) 0.41887(7) 0.0485(4) Uani 1 1 d . . . . .
C26 C 0.81474(13) -0.1113(4) 0.40532(8) 0.0569(4) Uani 1 1 d . . . . .
H26 H 0.877893 -0.085290 0.433121 0.068 Uiso 1 1 calc R U . . .
C24 C 0.70867(17) -0.3172(4) 0.31115(9) 0.0711(6) Uani 1 1 d . . . . .
C7 C 0.96608(12) 0.8123(4) 0.63078(8) 0.0540(4) Uani 1 1 d . . . . .
H7 H 1.028190 0.896920 0.646003 0.065 Uiso 1 1 calc R U . . .
C8 C 0.94710(12) 0.6325(4) 0.57879(8) 0.0523(4) Uani 1 1 d . . . . .
H8 H 0.996261 0.596104 0.558855 0.063 Uiso 1 1 calc R U . . .
C4 C 0.68757(10) 0.4167(3) 0.55990(7) 0.0426(3) Uani 1 1 d . . . . .
C3 C 0.67324(11) 0.2461(3) 0.50662(7) 0.0452(4) Uani 1 1 d . . . . .
H3 H 0.612645 0.155451 0.489166 0.054 Uiso 1 1 calc R U . . .
C23 C 0.62776(16) -0.1866(5) 0.32190(10) 0.0782(6) Uani 1 1 d . . . . .
H23 H 0.565127 -0.212621 0.293420 0.094 Uiso 1 1 calc R U . . .
C22 C 0.64178(14) -0.0148(5) 0.37630(9) 0.0659(5) Uani 1 1 d . . . . .
H22 H 0.587795 0.076108 0.384525 0.079 Uiso 1 1 calc R U . . .
C41 C 0.60583(11) 0.4524(3) 0.59101(8) 0.0497(4) Uani 1 1 d . . . . .
C25 C 0.80173(16) -0.2839(4) 0.35132(10) 0.0682(5) Uani 1 1 d . . . . .
H25 H 0.855213 -0.375432 0.342549 0.082 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
F43 C41 1.3300(18) . ?
F42 C41 1.3386(19) . ?
F44 C41 1.3389(19) . ?
N61 C6 1.392(2) . ?
N61 H61A 0.8908 . ?
N61 H61B 0.8752 . ?
N1 C2 1.320(2) . ?
N1 C8A 1.3606(19) . ?
F241 C24 1.362(2) . ?
C6 C5 1.370(2) . ?
C6 C7 1.411(2) . ?
C5 C4A 1.408(2) . ?
C5 H5 0.9300 . ?
C4A C8A 1.423(2) . ?
C4A C4 1.423(2) . ?
C8A C8 1.416(2) . ?
C2 C3 1.420(2) . ?
C2 C21 1.483(2) . ?
C21 C26 1.386(2) . ?
C21 C22 1.389(2) . ?
C26 C25 1.379(2) . ?
C26 H26 0.9300 . ?
C24 C25 1.361(3) . ?
C24 C23 1.368(3) . ?
C7 C8 1.358(2) . ?
C7 H7 0.9300 . ?
C8 H8 0.9300 . ?
C4 C3 1.359(2) . ?
C4 C41 1.500(2) . ?
C3 H3 0.9300 . ?
C23 C22 1.382(3) . ?
C23 H23 0.9300 . ?
C22 H22 0.9300 . ?
C25 H25 0.9300 . ?

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
C6 N61 H61A 113.8 . . ?
C6 N61 H61B 114.4 . . ?
H61A N61 H61B 112.6 . . ?
C2 N1 C8A 118.52(13) . . ?
C5 C6 N61 121.41(15) . . ?
C5 C6 C7 119.36(15) . . ?
N61 C6 C7 119.14(15) . . ?
C6 C5 C4A 121.02(14) . . ?
C6 C5 H5 119.5 . . ?
C4A C5 H5 119.5 . . ?
C5 C4A C8A 119.38(14) . . ?
C5 C4A C4 125.01(14) . . ?
C8A C4A C4 115.61(13) . . ?
N1 C8A C8 117.92(14) . . ?
N1 C8A C4A 123.77(14) . . ?
C8 C8A C4A 118.30(14) . . ?
N1 C2 C3 121.97(14) . . ?
N1 C2 C21 117.70(13) . . ?
C3 C2 C21 120.33(14) . . ?
C26 C21 C22 118.48(16) . . ?
C26 C21 C2 120.22(15) . . ?
C22 C21 C2 121.29(15) . . ?
C25 C26 C21 121.10(17) . . ?
C25 C26 H26 119.4 . . ?
C21 C26 H26 119.4 . . ?
C25 C24 F241 118.48(19) . . ?
C25 C24 C23 122.97(18) . . ?
F241 C24 C23 118.5(2) . . ?
C8 C7 C6 121.12(15) . . ?
C8 C7 H7 119.4 . . ?
C6 C7 H7 119.4 . . ?
C7 C8 C8A 120.82(15) . . ?
C7 C8 H8 119.6 . . ?
C8A C8 H8 119.6 . . ?
C3 C4 C4A 120.10(13) . . ?
C3 C4 C41 119.58(14) . . ?
C4A C4 C41 120.31(14) . . ?
C4 C3 C2 119.99(14) . . ?
C4 C3 H3 120.0 . . ?
C2 C3 H3 120.0 . . ?
C24 C23 C22 118.09(19) . . ?
C24 C23 H23 121.0 . . ?
C22 C23 H23 121.0 . . ?
C23 C22 C21 121.00(18) . . ?
C23 C22 H22 119.5 . . ?
C21 C22 H22 119.5 . . ?
F43 C41 F42 106.62(14) . . ?
F43 C41 F44 106.55(13) . . ?
F42 C41 F44 105.75(12) . . ?
F43 C41 C4 112.30(13) . . ?
F42 C41 C4 112.23(13) . . ?
F44 C41 C4 112.89(13) . . ?
C24 C25 C26 118.35(18) . . ?
C24 C25 H25 120.8 . . ?
C26 C25 H25 120.8 . . ?

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
N61 C6 C5 C4A -177.36(14) . . . . ?
C7 C6 C5 C4A -0.7(2) . . . . ?
C6 C5 C4A C8A 0.0(2) . . . . ?
C6 C5 C4A C4 -179.63(14) . . . . ?
C2 N1 C8A C8 -178.45(14) . . . . ?
C2 N1 C8A C4A 0.8(2) . . . . ?
C5 C4A C8A N1 -178.66(13) . . . . ?
C4 C4A C8A N1 1.0(2) . . . . ?
C5 C4A C8A C8 0.6(2) . . . . ?
C4 C4A C8A C8 -179.73(13) . . . . ?
C8A N1 C2 C3 -2.1(2) . . . . ?
C8A N1 C2 C21 178.47(13) . . . . ?
N1 C2 C21 C26 25.6(2) . . . . ?
C3 C2 C21 C26 -153.85(15) . . . . ?
N1 C2 C21 C22 -154.27(16) . . . . ?
C3 C2 C21 C22 26.3(2) . . . . ?
C22 C21 C26 C25 -0.8(3) . . . . ?
C2 C21 C26 C25 179.35(16) . . . . ?
C5 C6 C7 C8 0.8(2) . . . . ?
N61 C6 C7 C8 177.52(15) . . . . ?
C6 C7 C8 C8A -0.2(3) . . . . ?
N1 C8A C8 C7 178.78(15) . . . . ?
C4A C8A C8 C7 -0.5(2) . . . . ?
C5 C4A C4 C3 178.04(14) . . . . ?
C8A C4A C4 C3 -1.6(2) . . . . ?
C5 C4A C4 C41 -2.7(2) . . . . ?
C8A C4A C4 C41 177.66(13) . . . . ?
C4A C4 C3 C2 0.5(2) . . . . ?
C41 C4 C3 C2 -178.77(13) . . . . ?
N1 C2 C3 C4 1.5(2) . . . . ?
C21 C2 C3 C4 -179.10(13) . . . . ?
C25 C24 C23 C22 -0.4(3) . . . . ?
F241 C24 C23 C22 179.19(18) . . . . ?
C24 C23 C22 C21 0.0(3) . . . . ?
C26 C21 C22 C23 0.6(3) . . . . ?
C2 C21 C22 C23 -179.54(17) . . . . ?
C3 C4 C41 F43 118.60(16) . . . . ?
C4A C4 C41 F43 -60.66(19) . . . . ?
C3 C4 C41 F42 -121.29(16) . . . . ?
C4A C4 C41 F42 59.44(19) . . . . ?
C3 C4 C41 F44 -1.9(2) . . . . ?
C4A C4 C41 F44 178.85(12) . . . . ?
F241 C24 C25 C26 -179.38(17) . . . . ?
C23 C24 C25 C26 0.2(3) . . . . ?
C21 C26 C25 C24 0.4(3) . . . . ?

_refine_diff_density_max         0.134
_refine_diff_density_min         -0.130
_refine_diff_density_rms         0.029

