# 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 2023

####################################################################### 
# 
# 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_1_a
_database_code_depnum_ccdc_archive 'CCDC 2219240'
loop_
_audit_author_name
_audit_author_address
'wei wang'
;Wuhan Institute of Technology
China
;
_audit_update_record             
;
2022-11-12 deposited with the CCDC.	2023-05-09 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C17 H17 F2 N3 O2'
_chemical_formula_weight         333.33

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                   7.850(2)
_cell_length_b                   10.152(3)
_cell_length_c                   10.835(3)
_cell_angle_alpha                108.912(7)
_cell_angle_beta                 101.164(6)
_cell_angle_gamma                96.073(6)
_cell_volume                     788.1(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    3820
_cell_measurement_theta_min      2.39
_cell_measurement_theta_max      22.28

_exptl_crystal_description       Block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.405
_exptl_crystal_F_000             348
_exptl_transmission_factor_min   0.864
_exptl_transmission_factor_max   0.864
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    0.110
_shelx_estimated_absorpt_T_min   0.978
_shelx_estimated_absorpt_T_max   0.978
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  ccd
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            20998
_diffrn_reflns_av_unetI/netI     0.0695
_diffrn_reflns_av_R_equivalents  0.0880
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.393
_diffrn_reflns_theta_max         24.996
_diffrn_reflns_theta_full        24.996
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_point_group_measured_fraction_full 0.993
_reflns_number_total             2755
_reflns_number_gt                1531
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1323P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2755
_refine_ls_number_parameters     206
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1407
_refine_ls_R_factor_gt           0.0690
_refine_ls_wR_factor_ref         0.2173
_refine_ls_wR_factor_gt          0.1770
_refine_ls_goodness_of_fit_ref   1.002
_refine_ls_restrained_S_all      1.002
_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 -0.2282(5) 0.3259(4) 0.2984(4) 0.0666(11) Uani 1 1 d . . . . .
H1A H -0.1245 0.3236 0.3625 0.080 Uiso 1 1 calc R U . . .
H1B H -0.3272 0.3523 0.3364 0.080 Uiso 1 1 calc R U . . .
C2 C -0.2674(5) 0.2211(4) 0.1607(4) 0.0661(11) Uani 1 1 d . . . . .
H2A H -0.3904 0.1834 0.1143 0.079 Uiso 1 1 calc R U . . .
H2B H -0.1877 0.1547 0.1404 0.079 Uiso 1 1 calc R U . . .
C3 C -0.2005(4) 0.3718(4) 0.1864(4) 0.0548(10) Uani 1 1 d . . . . .
H3 H -0.2870 0.4246 0.1562 0.066 Uiso 1 1 calc R U . . .
C4 C 0.0473(4) 0.3662(4) 0.0775(4) 0.0485(9) Uani 1 1 d . . . . .
C5 C 0.2396(4) 0.4331(4) 0.1220(3) 0.0465(9) Uani 1 1 d . . . . .
C6 C 0.2603(4) 0.5617(3) 0.2456(3) 0.0442(9) Uani 1 1 d . . . . .
H6 H 0.2448 0.6429 0.2172 0.053 Uiso 1 1 calc R U . . .
C7 C 0.1005(4) 0.5259(4) 0.2987(3) 0.0512(9) Uani 1 1 d . . . . .
H7A H 0.1349 0.4915 0.3720 0.061 Uiso 1 1 calc R U . . .
H7B H 0.0467 0.6083 0.3302 0.061 Uiso 1 1 calc R U . . .
C8 C 0.4385(4) 0.5971(3) 0.3448(3) 0.0480(9) Uani 1 1 d . . . . .
H8A H 0.4507 0.5203 0.3787 0.058 Uiso 1 1 calc R U . . .
H8B H 0.5303 0.6028 0.2974 0.058 Uiso 1 1 calc R U . . .
C9 C 0.4672(4) 0.7319(3) 0.4612(3) 0.0428(8) Uani 1 1 d . . . . .
C10 C 0.6400(4) 0.7707(4) 0.5584(3) 0.0475(9) Uani 1 1 d . . . . .
C11 C 0.8373(5) 0.9372(4) 0.7639(4) 0.0778(13) Uani 1 1 d . . . . .
H11A H 0.9171 0.8770 0.7305 0.117 Uiso 1 1 calc R U . . .
H11B H 0.8225 0.9302 0.8476 0.117 Uiso 1 1 calc R U . . .
H11C H 0.8846 1.0335 0.7777 0.117 Uiso 1 1 calc R U . . .
C12 C 0.5326(2) 0.9721(2) 0.6838(2) 0.0434(9) Uani 1 1 d G . . . .
C13 C 0.3738(3) 0.92736(19) 0.58646(18) 0.0436(8) Uani 1 1 d G . . . .
C14 C 0.2372(2) 1.0031(2) 0.6024(2) 0.0607(10) Uani 1 1 d G . . . .
H14 H 0.1310 0.9732 0.5373 0.073 Uiso 1 1 calc R U . . .
C15 C 0.2594(3) 1.1237(2) 0.7157(3) 0.0697(12) Uani 1 1 d G . . . .
H15 H 0.1680 1.1744 0.7263 0.084 Uiso 1 1 calc R U . . .
C16 C 0.4181(3) 1.1684(2) 0.8130(2) 0.0691(11) Uani 1 1 d G . . . .
H16 H 0.4329 1.2490 0.8887 0.083 Uiso 1 1 calc R U . . .
C17 C 0.5548(3) 1.0926(2) 0.79703(19) 0.0573(10) Uani 1 1 d G . . . .
H17 H 0.6610 1.1225 0.8621 0.069 Uiso 1 1 calc R U . . .
F1 F 0.3351(2) 0.3348(2) 0.1469(2) 0.0629(7) Uani 1 1 d . . . . .
F2 F 0.2988(3) 0.4631(2) 0.0230(2) 0.0695(7) Uani 1 1 d . . . . .
N1 N -0.0211(3) 0.4151(3) 0.1828(3) 0.0456(7) Uani 1 1 d . . . . .
N2 N 0.3436(3) 0.8054(3) 0.4738(3) 0.0443(7) Uani 1 1 d . . . . .
N3 N 0.6649(3) 0.8926(3) 0.6655(3) 0.0475(8) Uani 1 1 d . . . . .
O1 O -0.0276(3) 0.2804(3) -0.0353(3) 0.0722(8) Uani 1 1 d . . . . .
O2 O 0.7531(3) 0.6965(3) 0.5417(3) 0.0685(8) 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 C2 1.476(5) . ?
C1 C3 1.478(5) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C2 C3 1.480(5) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 N1 1.442(4) . ?
C3 H3 0.9800 . ?
C4 O1 1.233(4) . ?
C4 N1 1.327(4) . ?
C4 C5 1.504(5) . ?
C5 F2 1.355(4) . ?
C5 F1 1.373(4) . ?
C5 C6 1.503(5) . ?
C6 C8 1.517(4) . ?
C6 C7 1.535(4) . ?
C6 H6 0.9800 . ?
C7 N1 1.465(4) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 C9 1.490(5) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 N2 1.286(4) . ?
C9 C10 1.473(4) . ?
C10 O2 1.226(4) . ?
C10 N3 1.359(4) . ?
C11 N3 1.474(4) . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C12 N3 1.386(3) . ?
C12 C13 1.3900 . ?
C12 C17 1.3900 . ?
C13 N2 1.388(3) . ?
C13 C14 1.3900 . ?
C14 C15 1.3900 . ?
C14 H14 0.9300 . ?
C15 C16 1.3900 . ?
C15 H15 0.9300 . ?
C16 C17 1.3900 . ?
C16 H16 0.9300 . ?
C17 H17 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
C2 C1 C3 60.1(3) . . ?
C2 C1 H1A 117.8 . . ?
C3 C1 H1A 117.8 . . ?
C2 C1 H1B 117.8 . . ?
C3 C1 H1B 117.8 . . ?
H1A C1 H1B 114.9 . . ?
C1 C2 C3 60.0(2) . . ?
C1 C2 H2A 117.8 . . ?
C3 C2 H2A 117.8 . . ?
C1 C2 H2B 117.8 . . ?
C3 C2 H2B 117.8 . . ?
H2A C2 H2B 114.9 . . ?
N1 C3 C1 117.7(3) . . ?
N1 C3 C2 119.7(3) . . ?
C1 C3 C2 59.8(3) . . ?
N1 C3 H3 116.0 . . ?
C1 C3 H3 116.0 . . ?
C2 C3 H3 116.0 . . ?
O1 C4 N1 128.0(3) . . ?
O1 C4 C5 125.2(3) . . ?
N1 C4 C5 106.7(3) . . ?
F2 C5 F1 104.4(3) . . ?
F2 C5 C6 113.1(3) . . ?
F1 C5 C6 112.5(3) . . ?
F2 C5 C4 112.1(3) . . ?
F1 C5 C4 108.0(3) . . ?
C6 C5 C4 106.8(3) . . ?
C5 C6 C8 114.1(3) . . ?
C5 C6 C7 102.3(3) . . ?
C8 C6 C7 115.4(3) . . ?
C5 C6 H6 108.2 . . ?
C8 C6 H6 108.2 . . ?
C7 C6 H6 108.2 . . ?
N1 C7 C6 104.4(2) . . ?
N1 C7 H7A 110.9 . . ?
C6 C7 H7A 110.9 . . ?
N1 C7 H7B 110.9 . . ?
C6 C7 H7B 110.9 . . ?
H7A C7 H7B 108.9 . . ?
C9 C8 C6 114.6(3) . . ?
C9 C8 H8A 108.6 . . ?
C6 C8 H8A 108.6 . . ?
C9 C8 H8B 108.6 . . ?
C6 C8 H8B 108.6 . . ?
H8A C8 H8B 107.6 . . ?
N2 C9 C10 123.9(3) . . ?
N2 C9 C8 120.1(3) . . ?
C10 C9 C8 116.0(3) . . ?
O2 C10 N3 123.0(3) . . ?
O2 C10 C9 121.2(3) . . ?
N3 C10 C9 115.9(3) . . ?
N3 C11 H11A 109.5 . . ?
N3 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
N3 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
N3 C12 C13 118.38(17) . . ?
N3 C12 C17 121.61(17) . . ?
C13 C12 C17 120.0 . . ?
N2 C13 C14 117.88(16) . . ?
N2 C13 C12 122.09(16) . . ?
C14 C13 C12 120.0 . . ?
C13 C14 C15 120.0 . . ?
C13 C14 H14 120.0 . . ?
C15 C14 H14 120.0 . . ?
C14 C15 C16 120.0 . . ?
C14 C15 H15 120.0 . . ?
C16 C15 H15 120.0 . . ?
C17 C16 C15 120.0 . . ?
C17 C16 H16 120.0 . . ?
C15 C16 H16 120.0 . . ?
C16 C17 C12 120.0 . . ?
C16 C17 H17 120.0 . . ?
C12 C17 H17 120.0 . . ?
C4 N1 C3 125.2(3) . . ?
C4 N1 C7 114.1(3) . . ?
C3 N1 C7 120.7(3) . . ?
C9 N2 C13 118.1(2) . . ?
C10 N3 C12 121.6(2) . . ?
C10 N3 C11 117.8(3) . . ?
C12 N3 C11 120.6(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
C2 C1 C3 N1 -110.0(4) . . . . ?
C1 C2 C3 N1 106.7(4) . . . . ?
O1 C4 C5 F2 37.4(5) . . . . ?
N1 C4 C5 F2 -143.8(3) . . . . ?
O1 C4 C5 F1 -77.0(4) . . . . ?
N1 C4 C5 F1 101.7(3) . . . . ?
O1 C4 C5 C6 161.8(3) . . . . ?
N1 C4 C5 C6 -19.5(4) . . . . ?
F2 C5 C6 C8 -87.2(4) . . . . ?
F1 C5 C6 C8 30.7(4) . . . . ?
C4 C5 C6 C8 149.0(3) . . . . ?
F2 C5 C6 C7 147.4(3) . . . . ?
F1 C5 C6 C7 -94.6(3) . . . . ?
C4 C5 C6 C7 23.6(3) . . . . ?
C5 C6 C7 N1 -19.6(3) . . . . ?
C8 C6 C7 N1 -144.0(3) . . . . ?
C5 C6 C8 C9 174.4(3) . . . . ?
C7 C6 C8 C9 -67.5(4) . . . . ?
C6 C8 C9 N2 2.3(5) . . . . ?
C6 C8 C9 C10 -179.1(3) . . . . ?
N2 C9 C10 O2 179.8(3) . . . . ?
C8 C9 C10 O2 1.2(5) . . . . ?
N2 C9 C10 N3 -0.6(5) . . . . ?
C8 C9 C10 N3 -179.1(3) . . . . ?
N3 C12 C13 N2 1.0(3) . . . . ?
C17 C12 C13 N2 -178.0(2) . . . . ?
N3 C12 C13 C14 179.0(2) . . . . ?
C17 C12 C13 C14 0.0 . . . . ?
N2 C13 C14 C15 178.1(2) . . . . ?
C12 C13 C14 C15 0.0 . . . . ?
C13 C14 C15 C16 0.0 . . . . ?
C14 C15 C16 C17 0.0 . . . . ?
C15 C16 C17 C12 0.0 . . . . ?
N3 C12 C17 C16 -179.0(2) . . . . ?
C13 C12 C17 C16 0.0 . . . . ?
O1 C4 N1 C3 2.5(6) . . . . ?
C5 C4 N1 C3 -176.2(3) . . . . ?
O1 C4 N1 C7 -174.8(3) . . . . ?
C5 C4 N1 C7 6.4(4) . . . . ?
C1 C3 N1 C4 128.3(4) . . . . ?
C2 C3 N1 C4 59.0(5) . . . . ?
C1 C3 N1 C7 -54.6(4) . . . . ?
C2 C3 N1 C7 -123.8(4) . . . . ?
C6 C7 N1 C4 8.7(4) . . . . ?
C6 C7 N1 C3 -168.7(3) . . . . ?
C10 C9 N2 C13 -0.9(5) . . . . ?
C8 C9 N2 C13 177.6(3) . . . . ?
C14 C13 N2 C9 -177.4(2) . . . . ?
C12 C13 N2 C9 0.7(3) . . . . ?
O2 C10 N3 C12 -178.0(3) . . . . ?
C9 C10 N3 C12 2.3(5) . . . . ?
O2 C10 N3 C11 0.9(5) . . . . ?
C9 C10 N3 C11 -178.7(3) . . . . ?
C13 C12 N3 C10 -2.6(4) . . . . ?
C17 C12 N3 C10 176.4(2) . . . . ?
C13 C12 N3 C11 178.5(3) . . . . ?
C17 C12 N3 C11 -2.5(4) . . . . ?

_refine_diff_density_max         0.237
_refine_diff_density_min         -0.246
_refine_diff_density_rms         0.065



_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: n-Hexane/EtOAc'
