# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2022

####################################################################### 
# 
# 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_shelxl
_database_code_depnum_ccdc_archive 'CCDC 2111055'
loop_
_audit_author_name
_audit_author_address
'Pierre de Fremont'
;University of Strasbourg
France
;
_audit_update_record             
;
2021-09-21 deposited with the CCDC.	2022-09-13 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         'C16 H21 N2 O2, C2 F3 O2'
_chemical_formula_sum            'C18 H21 F3 N2 O4'
_exptl_crystal_recrystallization_method 'DCM - Octane'
_chemical_melting_point          ?

_exptl_crystal_description       Prism
_exptl_crystal_colour            Colorless
_diffrn_ambient_temperature      173(2)
_chemical_formula_weight         386.37

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

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

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

_cell_length_a                   8.790(5)
_cell_length_b                   9.963(5)
_cell_length_c                   10.845(5)
_cell_angle_alpha                88.953(5)
_cell_angle_beta                 89.952(5)
_cell_angle_gamma                73.603(5)
_cell_volume                     911.0(8)
_cell_formula_units_Z            2
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    5121
_cell_measurement_theta_min      0.998
_cell_measurement_theta_max      27.485
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.409
_exptl_crystal_F_000             404
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.20
_exptl_absorpt_coefficient_mu    0.119
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9362
_exptl_absorpt_correction_T_max  1.0225
_exptl_absorpt_process_details   
;
[c.f. r.h. blessing, acta cryst. (1995), a51, 33-38]
;
_exptl_absorpt_special_details   ?
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71069
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       'CCD rotation images, thick slices'
_diffrn_detector_area_resol_mean 9
_diffrn_reflns_number            8477
_diffrn_reflns_av_unetI/netI     0.0489
_diffrn_reflns_av_R_equivalents  0.0445
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         1.878
_diffrn_reflns_theta_max         25.999
_diffrn_reflns_theta_full        25.240
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             3574
_reflns_number_gt                2729
_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       'Collect (Bruker AXS BV, 1997-2004)'
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_reduction        
'HKL Denzo and Scalepack (Otwinowski & Minor 1997)'
_computing_structure_solution    'Sir 97'
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_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)+(0.1356P)²+0.5587P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3574
_refine_ls_number_parameters     257
_refine_ls_number_restraints     18
_refine_ls_R_factor_all          0.0961
_refine_ls_R_factor_gt           0.0704
_refine_ls_wR_factor_ref         0.2326
_refine_ls_wR_factor_gt          0.2019
_refine_ls_goodness_of_fit_ref   1.117
_refine_ls_restrained_S_all      1.125
_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 0.6178(4) 0.3957(3) 0.2815(3) 0.0399(8) Uani 1 1 d . . . . .
H1A H 0.6418 0.4833 0.2904 0.060 Uiso 1 1 calc R U . . .
H1B H 0.5595 0.3787 0.3521 0.060 Uiso 1 1 calc R U . . .
H1C H 0.5553 0.3993 0.2084 0.060 Uiso 1 1 calc R U . . .
C2 C 0.8731(4) 0.2671(4) 0.3887(3) 0.0390(7) Uani 1 1 d . . . . .
H2A H 0.9746 0.1999 0.3781 0.059 Uiso 1 1 calc R U . . .
H2B H 0.8192 0.2385 0.4570 0.059 Uiso 1 1 calc R U . . .
H2C H 0.8879 0.3571 0.4048 0.059 Uiso 1 1 calc R U . . .
C3 C 0.7741(3) 0.2763(3) 0.2714(3) 0.0277(6) Uani 1 1 d . . . . .
C4 C 0.8587(3) 0.3120(3) 0.1566(3) 0.0259(6) Uani 1 1 d . . . . .
C5 C 0.8387(3) 0.2221(3) 0.0592(2) 0.0250(6) Uani 1 1 d . . . . .
C6 C 0.7383(3) 0.1375(3) 0.2408(2) 0.0293(6) Uani 1 1 d . . . . .
H6A H 0.8077 0.0595 0.2866 0.035 Uiso 1 1 calc R U . . .
H6B H 0.6289 0.1420 0.2589 0.035 Uiso 1 1 calc R U . . .
C7 C 0.8699(3) 0.1983(3) -0.0650(2) 0.0240(6) Uani 1 1 d . . . . .
C8 C 0.9459(3) 0.2807(3) -0.1495(3) 0.0274(6) Uani 1 1 d . . . . .
H8A H 1.0222 0.2166 -0.2011 0.033 Uiso 1 1 calc R U . . .
H8B H 1.0033 0.3310 -0.1005 0.033 Uiso 1 1 calc R U . . .
C9 C 0.8275(3) 0.3847(3) -0.2317(3) 0.0285(6) Uani 1 1 d . . . . .
H9A H 0.7721 0.3353 -0.2834 0.034 Uiso 1 1 calc R U . . .
H9B H 0.7498 0.4488 -0.1811 0.034 Uiso 1 1 calc R U . . .
C10 C 0.8160(3) 0.0791(3) -0.0920(2) 0.0235(6) Uani 1 1 d . . . . .
C11 C 0.7560(3) 0.0346(3) 0.0187(2) 0.0241(6) Uani 1 1 d . . . . .
C12 C 0.6987(3) -0.0827(3) 0.0267(3) 0.0259(6) Uani 1 1 d . . . . .
H12 H 0.6604 -0.1099 0.1002 0.031 Uiso 1 1 calc R U . . .
C13 C 0.7022(3) -0.1557(3) -0.0802(3) 0.0279(6) Uani 1 1 d . . . . .
C14 C 0.7565(3) -0.1122(3) -0.1932(3) 0.0303(6) Uani 1 1 d . . . . .
H14 H 0.7536 -0.1625 -0.2641 0.036 Uiso 1 1 calc R U . . .
C15 C 0.8133(3) 0.0024(3) -0.1999(3) 0.0279(6) Uani 1 1 d . . . . .
H15 H 0.8495 0.0293 -0.2743 0.033 Uiso 1 1 calc R U . . .
C16 C 0.6077(4) -0.3289(3) 0.0236(3) 0.0396(7) Uani 1 1 d . . . . .
H16A H 0.6908 -0.3412 0.0838 0.059 Uiso 1 1 calc R U . . .
H16B H 0.5883 -0.4174 0.0088 0.059 Uiso 1 1 calc R U . . .
H16C H 0.5127 -0.2644 0.0538 0.059 Uiso 1 1 calc R U . . .
C17 C 0.4526(3) 0.1902(3) 0.5988(3) 0.0302(6) Uani 1 1 d D . . . .
C18 C 0.2938(4) 0.2808(3) 0.5446(3) 0.0343(7) Uani 1 1 d . . . . .
N1 N 0.7693(3) 0.1250(2) 0.1083(2) 0.0242(5) Uani 1 1 d . . . . .
N2 N 0.9114(3) 0.4644(3) -0.3102(2) 0.0305(6) Uani 1 1 d D . . . .
O1 O 0.9253(2) 0.4053(2) 0.14964(19) 0.0337(5) Uani 1 1 d . . . . .
O2 O 0.6540(3) -0.2752(2) -0.0883(2) 0.0365(5) Uani 1 1 d . . . . .
O3 O 0.3056(3) 0.3487(3) 0.4527(3) 0.0669(8) Uani 1 1 d . . . . .
O4 O 0.1764(3) 0.2720(3) 0.6006(3) 0.0683(9) Uani 1 1 d . . . . .
F1A F 0.5557(5) 0.1287(4) 0.5082(4) 0.0480(5) Uani 0.605(5) 1 d D . P A 1
F1B F 0.5775(7) 0.1697(6) 0.5295(6) 0.0480(5) Uani 0.395(5) 1 d D . P A 2
F2A F 0.5277(4) 0.2702(4) 0.6593(4) 0.0480(5) Uani 0.605(5) 1 d D . P A 1
F2B F 0.4863(7) 0.2486(6) 0.7049(6) 0.0480(5) Uani 0.395(5) 1 d D . P A 2
F3A F 0.4413(5) 0.0901(4) 0.6747(4) 0.0480(5) Uani 0.605(5) 1 d D . P A 1
F3B F 0.4459(8) 0.0595(6) 0.6331(6) 0.0480(5) Uani 0.395(5) 1 d D . P A 2
H91 H 0.844(4) 0.527(3) -0.359(3) 0.045(9) Uiso 1 1 d D . . . .
H90 H 0.990(4) 0.412(4) -0.354(3) 0.053(11) Uiso 1 1 d D . . . .
H92 H 0.966(4) 0.509(4) -0.264(3) 0.054(11) 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. The 
 trifluoroacetate anion is slightly disordered. Hydrogen atoms from the -NH3 
 group were localized on the Fourier difference density map.
;

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 C3 1.548(4) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C2 C3 1.529(4) . ?
C2 H2A 0.9600 . ?
C2 H2B 0.9600 . ?
C2 H2C 0.9600 . ?
C3 C4 1.536(4) . ?
C3 C6 1.544(4) . ?
C4 O1 1.232(3) . ?
C4 C5 1.440(4) . ?
C5 N1 1.381(3) . ?
C5 C7 1.385(4) . ?
C6 N1 1.463(3) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C7 C10 1.431(4) . ?
C7 C8 1.498(4) . ?
C8 C9 1.520(4) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 N2 1.484(3) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 C15 1.413(4) . ?
C10 C11 1.424(4) . ?
C11 N1 1.364(3) . ?
C11 C12 1.399(4) . ?
C12 C13 1.375(4) . ?
C12 H12 0.9300 . ?
C13 O2 1.376(3) . ?
C13 C14 1.420(4) . ?
C14 C15 1.369(4) . ?
C14 H14 0.9300 . ?
C15 H15 0.9300 . ?
C16 O2 1.423(4) . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C17 F1B 1.299(6) . ?
C17 F3A 1.307(5) . ?
C17 F2A 1.349(4) . ?
C17 F3B 1.365(6) . ?
C17 F1A 1.367(5) . ?
C17 F2B 1.369(6) . ?
C17 C18 1.543(4) . ?
C18 O3 1.215(4) . ?
C18 O4 1.220(4) . ?
N2 H91 0.90(2) . ?
N2 H90 0.89(2) . ?
N2 H92 0.90(2) . ?

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
C3 C1 H1A 109.5 . . ?
C3 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C3 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C3 C2 H2A 109.5 . . ?
C3 C2 H2B 109.5 . . ?
H2A C2 H2B 109.5 . . ?
C3 C2 H2C 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
C2 C3 C4 112.3(2) . . ?
C2 C3 C6 113.3(2) . . ?
C4 C3 C6 104.8(2) . . ?
C2 C3 C1 110.1(2) . . ?
C4 C3 C1 105.8(2) . . ?
C6 C3 C1 110.3(2) . . ?
O1 C4 C5 127.0(3) . . ?
O1 C4 C3 125.2(2) . . ?
C5 C4 C3 107.7(2) . . ?
N1 C5 C7 110.4(2) . . ?
N1 C5 C4 108.3(2) . . ?
C7 C5 C4 141.3(2) . . ?
N1 C6 C3 103.0(2) . . ?
N1 C6 H6A 111.2 . . ?
C3 C6 H6A 111.2 . . ?
N1 C6 H6B 111.2 . . ?
C3 C6 H6B 111.2 . . ?
H6A C6 H6B 109.1 . . ?
C5 C7 C10 105.1(2) . . ?
C5 C7 C8 126.2(2) . . ?
C10 C7 C8 128.7(2) . . ?
C7 C8 C9 113.2(2) . . ?
C7 C8 H8A 108.9 . . ?
C9 C8 H8A 108.9 . . ?
C7 C8 H8B 108.9 . . ?
C9 C8 H8B 108.9 . . ?
H8A C8 H8B 107.8 . . ?
N2 C9 C8 109.9(2) . . ?
N2 C9 H9A 109.7 . . ?
C8 C9 H9A 109.7 . . ?
N2 C9 H9B 109.7 . . ?
C8 C9 H9B 109.7 . . ?
H9A C9 H9B 108.2 . . ?
C15 C10 C11 117.9(2) . . ?
C15 C10 C7 133.9(2) . . ?
C11 C10 C7 108.2(2) . . ?
N1 C11 C12 129.5(2) . . ?
N1 C11 C10 107.1(2) . . ?
C12 C11 C10 123.5(2) . . ?
C13 C12 C11 116.3(2) . . ?
C13 C12 H12 121.9 . . ?
C11 C12 H12 121.9 . . ?
C12 C13 O2 124.0(3) . . ?
C12 C13 C14 121.9(2) . . ?
O2 C13 C14 114.1(2) . . ?
C15 C14 C13 121.3(3) . . ?
C15 C14 H14 119.3 . . ?
C13 C14 H14 119.3 . . ?
C14 C15 C10 119.1(3) . . ?
C14 C15 H15 120.5 . . ?
C10 C15 H15 120.5 . . ?
O2 C16 H16A 109.5 . . ?
O2 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
O2 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
F3A C17 F2A 107.4(3) . . ?
F1B C17 F3B 105.1(4) . . ?
F3A C17 F1A 106.8(3) . . ?
F2A C17 F1A 104.6(3) . . ?
F1B C17 F2B 106.5(4) . . ?
F3B C17 F2B 105.1(4) . . ?
F1B C17 C18 117.5(4) . . ?
F3A C17 C18 115.1(3) . . ?
F2A C17 C18 110.6(3) . . ?
F3B C17 C18 112.1(3) . . ?
F1A C17 C18 111.6(3) . . ?
F2B C17 C18 109.6(3) . . ?
O3 C18 O4 130.4(3) . . ?
O3 C18 C17 114.9(3) . . ?
O4 C18 C17 114.7(3) . . ?
C11 N1 C5 109.2(2) . . ?
C11 N1 C6 136.1(2) . . ?
C5 N1 C6 114.5(2) . . ?
C9 N2 H91 112(2) . . ?
C9 N2 H90 115(3) . . ?
H91 N2 H90 110(3) . . ?
C9 N2 H92 111(2) . . ?
H91 N2 H92 109(3) . . ?
H90 N2 H92 99(3) . . ?
C13 O2 C16 116.6(2) . . ?

_refine_diff_density_max         0.845
_refine_diff_density_min         -0.700
_refine_diff_density_rms         0.114

_shelxl_version_number           2014/6

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_h-m   'P -1'
_symmetry_int_tables_number      2
_chemical_absolute_configuration ?

