# Supplementary Information (SI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 2213074'
loop_
_audit_author_name
_audit_author_address
'Oscar Enrique Piro'
;Universidad Nacional de La Plata
Argentina
;
_audit_update_record             
;
2022-10-14 deposited with the CCDC.	2025-12-15 downloaded from the CCDC.
;
_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        
(Z)-3-(butylamino)-4,4,4-trifluoro-1-(2-hydroxy-5-nitrophenyl)but-2-en-1-one
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C14 H15 F3 N2 O4'
_chemical_formula_weight         332.28

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      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                   5.3850(6)
_cell_length_b                   10.5397(9)
_cell_length_c                   14.0749(14)
_cell_angle_alpha                87.615(7)
_cell_angle_beta                 82.484(9)
_cell_angle_gamma                78.659(8)
_cell_volume                     776.41(14)
_cell_formula_units_Z            2
_cell_measurement_temperature    295(2)
_cell_measurement_reflns_used    944
_cell_measurement_theta_min      3.5000
_cell_measurement_theta_max      22.0970
_exptl_crystal_description       plate
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.421
_exptl_crystal_F_000             344
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.779
_exptl_crystal_size_mid          0.430
_exptl_crystal_size_min          0.037
_exptl_absorpt_coefficient_mu    0.127
_shelx_estimated_absorpt_T_min   0.907
_shelx_estimated_absorpt_T_max   0.995
_exptl_absorpt_correction_T_min  0.76421
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_oxdiff_exptl_absorpt_empirical_full_min 0.767
_oxdiff_exptl_absorpt_empirical_full_max 1.199
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      295(2)
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            Eos
_diffrn_detector_area_resol_mean 16.0604
_diffrn_reflns_number            5974
_diffrn_reflns_av_unetI/netI     0.0610
_diffrn_reflns_av_R_equivalents  0.0314
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         3.497
_diffrn_reflns_theta_max         28.987
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.804
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.804
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.804
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             3328
_reflns_number_gt                1489
_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       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'ORTEP for Windows (Farrugia, 2012)'
_computing_publication_material  'SHELXL-2014/7 (Sheldrick, 2014)'
_refine_special_details          
;The butyl group showed librational disorder and was refined with anisotropic 
displacement parameters and restraining the C-C distances to be equal to one 
another
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1364P)²+0.0945P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3328
_refine_ls_number_parameters     210
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.1587
_refine_ls_R_factor_gt           0.0780
_refine_ls_wR_factor_ref         0.2887
_refine_ls_wR_factor_gt          0.2149
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_restrained_S_all      1.048
_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
C1 C 0.1899(6) 0.2897(3) 0.4082(2) 0.0477(8) Uani 1 1 d . . . . .
C2 C 0.0949(6) 0.3125(3) 0.5053(3) 0.0525(9) Uani 1 1 d . . . . .
C3 C -0.0939(7) 0.2490(4) 0.5507(3) 0.0600(10) Uani 1 1 d . . . . .
H3 H -0.1561 0.2654 0.6147 0.072 Uiso 1 1 calc R U . . .
C4 C -0.1878(7) 0.1634(4) 0.5025(3) 0.0612(10) Uani 1 1 d . . . . .
H4 H -0.3139 0.1214 0.5327 0.073 Uiso 1 1 calc R U . . .
C5 C -0.0910(7) 0.1402(3) 0.4068(3) 0.0577(10) Uani 1 1 d . . . . .
C6 C 0.0927(6) 0.2012(3) 0.3600(3) 0.0539(9) Uani 1 1 d . . . . .
H6 H 0.1527 0.1836 0.2960 0.065 Uiso 1 1 calc R U . . .
C7 C 0.3848(6) 0.3616(3) 0.3590(3) 0.0506(9) Uani 1 1 d . . . . .
C8 C 0.4950(6) 0.3315(4) 0.2638(3) 0.0565(9) Uani 1 1 d . . . . .
H8 H 0.4477 0.2642 0.2342 0.068 Uiso 1 1 calc R U . . .
C9 C 0.6688(7) 0.3965(4) 0.2126(3) 0.0601(10) Uani 1 1 d . . . . .
C10 C 0.7809(9) 0.3516(5) 0.1130(3) 0.0845(14) Uani 1 1 d . . . . .
C11 C 0.9214(9) 0.5774(5) 0.1996(4) 0.0841(13) Uani 1 1 d D . . . .
H11A H 1.0677 0.5702 0.2344 0.101 Uiso 1 1 calc R U . . .
H11B H 0.9837 0.5466 0.1352 0.101 Uiso 1 1 calc R U . . .
C12 C 0.7977(13) 0.7130(7) 0.1942(7) 0.156(3) Uani 1 1 d D . . . .
H12A H 0.7616 0.7430 0.2597 0.188 Uiso 1 1 calc R U . . .
H12B H 0.9266 0.7583 0.1624 0.188 Uiso 1 1 calc R U . . .
C13 C 0.5862(15) 0.7577(8) 0.1536(8) 0.188(4) Uani 1 1 d D . . . .
H13A H 0.4494 0.7244 0.1921 0.226 Uiso 1 1 calc R U . . .
H13B H 0.6106 0.7167 0.0917 0.226 Uiso 1 1 calc R U . . .
C14 C 0.4874(16) 0.8974(8) 0.1367(6) 0.176(3) Uani 1 1 d D . . . .
H14A H 0.4423 0.9405 0.1970 0.264 Uiso 1 1 calc R U . . .
H14B H 0.3393 0.9074 0.1038 0.264 Uiso 1 1 calc R U . . .
H14C H 0.6168 0.9346 0.0984 0.264 Uiso 1 1 calc R U . . .
N1 N 0.7527(6) 0.4946(3) 0.2464(2) 0.0679(9) Uani 1 1 d . . . . .
H1 H 0.6983 0.5119 0.3055 0.081 Uiso 1 1 calc R U . . .
N2 N -0.1918(7) 0.0495(3) 0.3533(3) 0.0738(10) Uani 1 1 d . . . . .
O1 O 0.1798(5) 0.3946(3) 0.55736(18) 0.0660(8) Uani 1 1 d . . . . .
H1A H 0.2913 0.4252 0.5242 0.099 Uiso 1 1 calc R U . . .
O2 O 0.4479(5) 0.4474(2) 0.40452(18) 0.0621(8) Uani 1 1 d . . . . .
O3 O -0.0949(7) 0.0258(4) 0.2714(3) 0.1175(15) Uani 1 1 d . . . . .
O4 O -0.3659(6) 0.0013(3) 0.3917(3) 0.0960(11) Uani 1 1 d . . . . .
F1 F 0.7352(6) 0.4433(4) 0.04650(19) 0.1175(11) Uani 1 1 d . . . . .
F2 F 1.0339(5) 0.3140(3) 0.1055(2) 0.1143(12) Uani 1 1 d . . . . .
F3 F 0.6899(6) 0.2526(3) 0.08695(19) 0.1195(12) 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
C1 C6 1.393(4) . ?
C1 C2 1.409(5) . ?
C1 C7 1.495(5) . ?
C2 O1 1.338(4) . ?
C2 C3 1.398(5) . ?
C3 C4 1.360(5) . ?
C4 C5 1.392(5) . ?
C5 C6 1.367(5) . ?
C5 N2 1.466(5) . ?
C7 O2 1.252(4) . ?
C7 C8 1.415(5) . ?
C8 C9 1.378(5) . ?
C9 N1 1.334(5) . ?
C9 C10 1.508(6) . ?
C10 F2 1.334(5) . ?
C10 F3 1.320(5) . ?
C10 F1 1.328(6) . ?
C11 C12 1.457(8) . ?
C11 N1 1.459(5) . ?
C12 C13 1.335(8) . ?
C13 C14 1.484(9) . ?
N2 O4 1.208(4) . ?
N2 O3 1.216(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
C6 C1 C2 118.0(3) . . ?
C6 C1 C7 121.9(3) . . ?
C2 C1 C7 120.1(3) . . ?
O1 C2 C1 122.0(3) . . ?
O1 C2 C3 117.5(3) . . ?
C1 C2 C3 120.4(3) . . ?
C4 C3 C2 120.8(4) . . ?
C3 C4 C5 118.5(3) . . ?
C4 C5 C6 122.3(3) . . ?
C4 C5 N2 119.3(3) . . ?
C6 C5 N2 118.4(4) . . ?
C1 C6 C5 120.0(3) . . ?
O2 C7 C8 121.6(3) . . ?
O2 C7 C1 118.3(3) . . ?
C8 C7 C1 120.1(3) . . ?
C9 C8 C7 123.5(3) . . ?
N1 C9 C8 124.3(3) . . ?
N1 C9 C10 117.2(3) . . ?
C8 C9 C10 118.5(4) . . ?
F2 C10 F3 106.7(4) . . ?
F2 C10 F1 106.2(4) . . ?
F3 C10 F1 106.2(4) . . ?
F2 C10 C9 111.9(4) . . ?
F3 C10 C9 112.6(4) . . ?
F1 C10 C9 112.8(4) . . ?
C12 C11 N1 113.3(4) . . ?
C13 C12 C11 125.1(8) . . ?
C12 C13 C14 123.4(8) . . ?
C9 N1 C11 130.6(4) . . ?
O4 N2 O3 122.7(4) . . ?
O4 N2 C5 119.3(4) . . ?
O3 N2 C5 118.0(3) . . ?

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
C6 C1 C2 O1 179.1(3) . . . . ?
C7 C1 C2 O1 -2.3(5) . . . . ?
C6 C1 C2 C3 -0.9(5) . . . . ?
C7 C1 C2 C3 177.7(3) . . . . ?
O1 C2 C3 C4 -179.5(3) . . . . ?
C1 C2 C3 C4 0.5(5) . . . . ?
C2 C3 C4 C5 0.2(6) . . . . ?
C3 C4 C5 C6 -0.6(6) . . . . ?
C3 C4 C5 N2 -179.3(3) . . . . ?
C2 C1 C6 C5 0.5(5) . . . . ?
C7 C1 C6 C5 -178.1(3) . . . . ?
C4 C5 C6 C1 0.2(5) . . . . ?
N2 C5 C6 C1 178.9(3) . . . . ?
C6 C1 C7 O2 174.2(3) . . . . ?
C2 C1 C7 O2 -4.4(5) . . . . ?
C6 C1 C7 C8 -6.4(5) . . . . ?
C2 C1 C7 C8 175.0(3) . . . . ?
O2 C7 C8 C9 -3.0(6) . . . . ?
C1 C7 C8 C9 177.6(3) . . . . ?
C7 C8 C9 N1 0.0(6) . . . . ?
C7 C8 C9 C10 177.5(4) . . . . ?
N1 C9 C10 F2 58.5(6) . . . . ?
C8 C9 C10 F2 -119.2(4) . . . . ?
N1 C9 C10 F3 178.7(4) . . . . ?
C8 C9 C10 F3 1.0(6) . . . . ?
N1 C9 C10 F1 -61.2(5) . . . . ?
C8 C9 C10 F1 121.2(4) . . . . ?
N1 C11 C12 C13 -56.7(11) . . . . ?
C11 C12 C13 C14 -170.6(8) . . . . ?
C8 C9 N1 C11 -175.6(4) . . . . ?
C10 C9 N1 C11 6.9(6) . . . . ?
C12 C11 N1 C9 116.9(6) . . . . ?
C4 C5 N2 O4 3.7(5) . . . . ?
C6 C5 N2 O4 -175.1(3) . . . . ?
C4 C5 N2 O3 -176.3(4) . . . . ?
C6 C5 N2 O3 4.9(6) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O1 H1A O2 0.82 1.81 2.535(3) 146.5 .
O1 H1A O2 0.82 2.45 2.959(3) 121.1 2_666
N1 H1 O2 0.86 2.00 2.678(4) 134.5 .
N1 H1 O1 0.86 2.42 3.135(4) 140.5 2_666
C4 H4 O4 0.93 2.46 3.391(5) 176.7 2_456
C11 H11B F2 0.97 2.46 3.043(6) 118.3 .
C11 H11B F1 0.97 2.38 3.003(6) 121.6 .

_refine_diff_density_max         0.390
_refine_diff_density_min         -0.250
_refine_diff_density_rms         0.050


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Petroleum ether'
####################################################################### 
# 
# 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_shelx_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 2424049'
loop_
_audit_author_name
_audit_author_address
'Oscar Enrique Piro'
;Universidad Nacional de La Plata
Argentina
;
_audit_update_record             
;
2025-02-14 deposited with the CCDC.	2025-12-15 downloaded from the CCDC.
;
_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        
(2Z)-3-amino-4,4,4-trifluoro-1-(2-hidroxy-5-nitrophenyl)but-2-en-1-one
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C10 H7 F3 N2 O4'
_chemical_formula_weight         276.18

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/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                   5.0511(3)
_cell_length_b                   15.3395(7)
_cell_length_c                   14.7473(11)
_cell_angle_alpha                90
_cell_angle_beta                 94.606(7)
_cell_angle_gamma                90
_cell_volume                     1138.95(12)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    1168
_cell_measurement_theta_min      3.8330
_cell_measurement_theta_max      27.507<0
_exptl_crystal_description       fragment
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.611
_exptl_crystal_F_000             560
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.758
_exptl_crystal_size_mid          0.465
_exptl_crystal_size_min          0.138
_exptl_absorpt_coefficient_mu    0.156
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_T_min  0.86242
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_oxdiff_exptl_absorpt_empirical_full_min 0.845
_oxdiff_exptl_absorpt_empirical_full_max 1.191
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      295(2)
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            Eos
_diffrn_detector_area_resol_mean 16.0604
_diffrn_reflns_number            5157
_diffrn_reflns_av_unetI/netI     0.0373
_diffrn_reflns_av_R_equivalents  0.0262
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         3.073
_diffrn_reflns_theta_max         28.652
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.845
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.845
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.845
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             2475
_reflns_number_gt                1600
_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       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'ORTEP for Windows (Farrugia, 2012)'
_computing_publication_material  'SHELXL-2014/7 (Sheldrick, 2014)'
_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)+(0.0900P)²+0.3884P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2475
_refine_ls_number_parameters     200
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0938
_refine_ls_R_factor_gt           0.0607
_refine_ls_wR_factor_ref         0.1884
_refine_ls_wR_factor_gt          0.1612
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_restrained_S_all      1.035
_refine_ls_shift/su_max          0.019
_refine_ls_shift/su_mean         0.004

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 1.2747(5) 0.88687(13) 0.5637(2) 0.1246(11) Uani 1 1 d . . . . .
F2 F 1.0024(6) 0.90873(12) 0.45231(16) 0.1112(9) Uani 1 1 d . . . . .
F3 F 0.8758(5) 0.90624(11) 0.58427(18) 0.1004(8) Uani 1 1 d . . . . .
O1 O 0.6838(4) 0.45665(11) 0.58751(14) 0.0546(6) Uani 1 1 d . . . . .
O2 O 0.8975(4) 0.59058(11) 0.52437(13) 0.0504(5) Uani 1 1 d . . . . .
O3 O 0.1340(5) 0.75116(14) 0.79395(18) 0.0860(8) Uani 1 1 d . . . . .
O4 O -0.0478(5) 0.63894(17) 0.84727(17) 0.0851(8) Uani 1 1 d . . . . .
N1 N 1.1466(5) 0.73428(17) 0.46327(18) 0.0545(7) Uani 1 1 d . . . . .
N2 N 0.1058(5) 0.67301(17) 0.79832(16) 0.0551(6) Uani 1 1 d . . . . .
C1 C 0.5815(5) 0.60269(15) 0.63315(16) 0.0371(5) Uani 1 1 d . . . . .
C2 C 0.5467(5) 0.51128(15) 0.63659(17) 0.0415(6) Uani 1 1 d . . . . .
C3 C 0.3663(6) 0.47524(18) 0.69320(19) 0.0512(7) Uani 1 1 d . . . . .
C4 C 0.2228(6) 0.52708(18) 0.74632(19) 0.0511(7) Uani 1 1 d . . . . .
C5 C 0.2580(5) 0.61647(17) 0.74260(17) 0.0436(6) Uani 1 1 d . . . . .
C6 C 0.4323(5) 0.65421(16) 0.68755(17) 0.0416(6) Uani 1 1 d . . . . .
C7 C 0.7730(5) 0.64082(15) 0.57293(16) 0.0404(6) Uani 1 1 d . . . . .
C8 C 0.8182(5) 0.73212(16) 0.57304(18) 0.0439(6) Uani 1 1 d . . . . .
C9 C 0.9945(5) 0.77158(15) 0.52084(17) 0.0429(6) Uani 1 1 d . . . . .
C10 C 1.0345(6) 0.86872(18) 0.5310(2) 0.0559(7) Uani 1 1 d . . . . .
H1O H 0.796(7) 0.490(2) 0.555(2) 0.078(11) Uiso 1 1 d . . . . .
H1N H 1.130(6) 0.675(2) 0.456(2) 0.068(9) Uiso 1 1 d . . . . .
H2N H 1.247(6) 0.765(2) 0.434(2) 0.066(10) Uiso 1 1 d . . . . .
H3 H 0.350(6) 0.413(2) 0.696(2) 0.063(9) Uiso 1 1 d . . . . .
H4 H 0.108(6) 0.505(2) 0.791(2) 0.068(9) Uiso 1 1 d . . . . .
H6 H 0.453(5) 0.7146(19) 0.6879(18) 0.049(7) Uiso 1 1 d . . . . .
H8 H 0.730(5) 0.7696(18) 0.6109(19) 0.051(8) Uiso 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F1 C10 1.299(4) . ?
F2 C10 1.311(3) . ?
F3 C10 1.301(3) . ?
O1 C2 1.337(3) . ?
O2 C7 1.255(3) . ?
O3 N2 1.210(3) . ?
O4 N2 1.219(3) . ?
N1 C9 1.320(3) . ?
N2 C5 1.456(3) . ?
C1 C6 1.390(3) . ?
C1 C2 1.415(3) . ?
C1 C7 1.485(3) . ?
C2 C3 1.398(3) . ?
C3 C4 1.365(4) . ?
C4 C5 1.384(4) . ?
C5 C6 1.373(4) . ?
C7 C8 1.419(3) . ?
C8 C9 1.365(3) . ?
C9 C10 1.510(3) . ?

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
O4 N2 O3 122.7(2) . . ?
O4 N2 C5 118.0(2) . . ?
O3 N2 C5 119.4(2) . . ?
C6 C1 C2 117.9(2) . . ?
C6 C1 C7 122.0(2) . . ?
C2 C1 C7 120.0(2) . . ?
O1 C2 C3 117.8(2) . . ?
O1 C2 C1 122.1(2) . . ?
C3 C2 C1 120.1(2) . . ?
C4 C3 C2 120.9(3) . . ?
C3 C4 C5 118.6(2) . . ?
C6 C5 C4 122.1(2) . . ?
C6 C5 N2 118.4(2) . . ?
C4 C5 N2 119.5(2) . . ?
C5 C6 C1 120.3(2) . . ?
O2 C7 C8 121.2(2) . . ?
O2 C7 C1 118.7(2) . . ?
C8 C7 C1 120.0(2) . . ?
C9 C8 C7 123.3(2) . . ?
N1 C9 C8 127.6(2) . . ?
N1 C9 C10 114.3(2) . . ?
C8 C9 C10 118.0(2) . . ?
F1 C10 F3 106.5(3) . . ?
F1 C10 F2 105.9(3) . . ?
F3 C10 F2 106.8(3) . . ?
F1 C10 C9 111.2(2) . . ?
F3 C10 C9 114.4(2) . . ?
F2 C10 C9 111.6(2) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 C1 C2 O1 -179.2(2) . . . . ?
C7 C1 C2 O1 0.7(4) . . . . ?
C6 C1 C2 C3 0.2(4) . . . . ?
C7 C1 C2 C3 -179.9(2) . . . . ?
O1 C2 C3 C4 178.9(3) . . . . ?
C1 C2 C3 C4 -0.5(4) . . . . ?
C2 C3 C4 C5 0.5(4) . . . . ?
C3 C4 C5 C6 -0.2(4) . . . . ?
C3 C4 C5 N2 179.6(2) . . . . ?
O4 N2 C5 C6 -179.7(3) . . . . ?
O3 N2 C5 C6 0.9(4) . . . . ?
O4 N2 C5 C4 0.5(4) . . . . ?
O3 N2 C5 C4 -178.9(3) . . . . ?
C4 C5 C6 C1 -0.1(4) . . . . ?
N2 C5 C6 C1 -179.9(2) . . . . ?
C2 C1 C6 C5 0.1(4) . . . . ?
C7 C1 C6 C5 -179.8(2) . . . . ?
C6 C1 C7 O2 -178.7(2) . . . . ?
C2 C1 C7 O2 1.4(3) . . . . ?
C6 C1 C7 C8 3.2(4) . . . . ?
C2 C1 C7 C8 -176.7(2) . . . . ?
O2 C7 C8 C9 0.7(4) . . . . ?
C1 C7 C8 C9 178.8(2) . . . . ?
C7 C8 C9 N1 0.4(4) . . . . ?
C7 C8 C9 C10 -176.8(2) . . . . ?
N1 C9 C10 F1 -62.5(4) . . . . ?
C8 C9 C10 F1 115.0(3) . . . . ?
N1 C9 C10 F3 176.8(3) . . . . ?
C8 C9 C10 F3 -5.7(4) . . . . ?
N1 C9 C10 F2 55.5(3) . . . . ?
C8 C9 C10 F2 -127.0(3) . . . . ?

_refine_diff_density_max         0.392
_refine_diff_density_min         -0.311
_refine_diff_density_rms         0.051


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: petroleum ether:ethyl acetate (9:1)'
