# 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_1
_database_code_depnum_ccdc_archive 'CCDC 1885335'
loop_
_audit_author_name
_audit_author_address
'Shu-Lin Jiao'
;Southeast University
China
;
_audit_update_record             
;
2018-12-16 deposited with the CCDC.	2019-11-04 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            'C23 H16 F3 N3 O4'
_chemical_formula_weight         455.39

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                   7.9040(14)
_cell_length_b                   29.488(5)
_cell_length_c                   9.471(2)
_cell_angle_alpha                90
_cell_angle_beta                 103.898(19)
_cell_angle_gamma                90
_cell_volume                     2142.9(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    1081
_cell_measurement_theta_min      2.6100
_cell_measurement_theta_max      21.2150

_exptl_crystal_description       Needlelike
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.412
_exptl_crystal_F_000             936
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_absorpt_coefficient_mu    0.115
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            15944
_diffrn_reflns_av_unetI/netI     0.1483
_diffrn_reflns_av_R_equivalents  0.1030
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -38
_diffrn_reflns_limit_k_max       38
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.320
_diffrn_reflns_theta_max         27.499
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measured_fraction_theta_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_point_group_measured_fraction_full 0.990
_reflns_number_total             4866
_reflns_number_gt                2335
_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)+(0.1477P)²+1.8917P] 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         4866
_refine_ls_number_parameters     301
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.2346
_refine_ls_R_factor_gt           0.1234
_refine_ls_wR_factor_ref         0.3407
_refine_ls_wR_factor_gt          0.2943
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_restrained_S_all      1.050
_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
N3 N 0.9259(5) 0.24091(13) 1.0255(5) 0.0443(10) Uani 1 1 d . . . . .
N2 N 0.7619(5) 0.27427(14) 0.8249(5) 0.0433(10) Uani 1 1 d . . . . .
N1 N 0.8228(5) 0.20931(13) 0.9372(5) 0.0435(10) Uani 1 1 d . . . . .
C7 C 0.7281(6) 0.23025(16) 0.8171(5) 0.0400(11) Uani 1 1 d . . . . .
C16 C 0.8305(6) 0.16311(16) 0.9846(6) 0.0433(12) Uani 1 1 d . . . . .
O1 O 0.4630(6) 0.28064(14) 0.6191(5) 0.0736(13) Uani 1 1 d . . . . .
H1 H 0.5489 0.2906 0.6774 0.110 Uiso 1 1 calc R U . . .
C10 C 0.9329(7) 0.36166(18) 0.9253(6) 0.0544(14) Uani 1 1 d . . . . .
H10 H 0.8595 0.3602 0.8325 0.065 Uiso 1 1 calc R U . . .
C20 C 1.0037(7) 0.09794(18) 1.0732(6) 0.0477(13) Uani 1 1 d . . . . .
C15 C 1.0736(6) 0.32550(17) 1.1477(6) 0.0443(12) Uani 1 1 d . . . . .
C14 C 1.1465(7) 0.36672(19) 1.1991(6) 0.0529(14) Uani 1 1 d . . . . .
H14 H 1.2193 0.3685 1.2920 0.064 Uiso 1 1 calc R U . . .
C9 C 0.9644(6) 0.32230(16) 1.0076(5) 0.0403(12) Uani 1 1 d . . . . .
C8 C 0.8840(6) 0.27933(16) 0.9519(5) 0.0407(12) Uani 1 1 d . . . . .
C17 C 0.6824(7) 0.14003(18) 0.9921(6) 0.0500(13) Uani 1 1 d . . . . .
H17 H 0.5748 0.1545 0.9679 0.060 Uiso 1 1 calc R U . . .
C1 C 0.6105(6) 0.20877(18) 0.6892(5) 0.0443(12) Uani 1 1 d . . . . .
C21 C 0.9936(7) 0.14252(17) 1.0270(6) 0.0456(13) Uani 1 1 d . . . . .
H21 H 1.0941 0.1585 1.0242 0.055 Uiso 1 1 calc R U . . .
C6 C 0.4858(7) 0.2362(2) 0.5973(6) 0.0539(14) Uani 1 1 d . . . . .
C12 C 1.1125(8) 0.40501(19) 1.1145(7) 0.0577(15) Uani 1 1 d . . . . .
C2 C 0.6234(7) 0.16388(19) 0.6515(6) 0.0508(14) Uani 1 1 d . . . . .
H2 H 0.7066 0.1455 0.7108 0.061 Uiso 1 1 calc R U . . .
C18 C 0.6933(7) 0.09507(19) 1.0358(7) 0.0574(16) Uani 1 1 d . . . . .
H18 H 0.5928 0.0790 1.0380 0.069 Uiso 1 1 calc R U . . .
C19 C 0.8547(8) 0.07413(18) 1.0761(7) 0.0561(15) Uani 1 1 d . . . . .
H19 H 0.8623 0.0439 1.1051 0.067 Uiso 1 1 calc R U . . .
C11 C 1.0047(8) 0.40232(18) 0.9744(7) 0.0640(17) Uani 1 1 d . . . . .
H11 H 0.9824 0.4279 0.9156 0.077 Uiso 1 1 calc R U . . .
C4 C 0.3950(8) 0.1731(3) 0.4395(7) 0.0700(19) Uani 1 1 d . . . . .
H4 H 0.3232 0.1611 0.3553 0.084 Uiso 1 1 calc R U . . .
C3 C 0.5160(8) 0.1457(2) 0.5283(7) 0.0639(17) Uani 1 1 d . . . . .
H3 H 0.5252 0.1153 0.5054 0.077 Uiso 1 1 calc R U . . .
C5 C 0.3788(8) 0.2177(2) 0.4734(7) 0.0664(17) Uani 1 1 d . . . . .
H5 H 0.2953 0.2357 0.4127 0.080 Uiso 1 1 calc R U . . .
O2 O 1.1129(6) 0.28936(13) 1.2380(4) 0.0628(11) Uani 1 1 d . . . . .
H2A H 1.0783 0.2661 1.1931 0.094 Uiso 1 1 calc R U . . .
O3 O 1.1757(6) 0.03567(17) 1.1725(7) 0.1053(19) Uani 1 1 d . . . . .
C22 C 1.1775(10) 0.0776(2) 1.1191(8) 0.0740(19) Uani 1 1 d . . . . .
O4 O 1.3134(7) 0.09614(18) 1.1116(8) 0.111(2) Uani 1 1 d . . . . .
C13 C 1.1928(13) 0.4476(2) 1.1710(11) 0.095(3) Uani 1 1 d . . . . .
C23 C 1.3436(12) 0.0138(3) 1.2257(13) 0.140(4) Uani 1 1 d . . . . .
H23A H 1.4013 0.0110 1.1477 0.210 Uiso 1 1 calc R U . . .
H23B H 1.3265 -0.0158 1.2621 0.210 Uiso 1 1 calc R U . . .
H23C H 1.4139 0.0317 1.3025 0.210 Uiso 1 1 calc R U . . .
F1 F 1.3157(12) 0.44737(19) 1.2779(9) 0.233(5) Uani 1 1 d . . . . .
F2 F 1.2429(15) 0.4728(3) 1.0818(9) 0.240(6) Uani 1 1 d . . . . .
F3 F 1.0888(11) 0.4754(3) 1.2033(14) 0.261(7) 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
N3 C8 1.330(6) . ?
N3 N1 1.380(6) . ?
N2 C7 1.324(6) . ?
N2 C8 1.358(6) . ?
N1 C7 1.351(6) . ?
N1 C16 1.431(6) . ?
C7 C1 1.481(7) . ?
C16 C17 1.371(7) . ?
C16 C21 1.394(7) . ?
O1 C6 1.345(7) . ?
C10 C11 1.360(8) . ?
C10 C9 1.387(7) . ?
C20 C19 1.377(7) . ?
C20 C21 1.382(7) . ?
C20 C22 1.466(8) . ?
C15 O2 1.356(6) . ?
C15 C14 1.382(8) . ?
C15 C9 1.402(7) . ?
C14 C12 1.373(8) . ?
C9 C8 1.458(7) . ?
C17 C18 1.385(7) . ?
C1 C2 1.381(7) . ?
C1 C6 1.404(7) . ?
C6 C5 1.384(8) . ?
C12 C11 1.396(8) . ?
C12 C13 1.451(9) . ?
C2 C3 1.376(8) . ?
C18 C19 1.385(8) . ?
C4 C5 1.367(9) . ?
C4 C3 1.374(9) . ?
O3 C22 1.337(8) . ?
O3 C23 1.453(8) . ?
C22 O4 1.222(8) . ?
C13 F1 1.224(9) . ?
C13 F3 1.249(10) . ?
C13 F2 1.258(11) . ?

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
C8 N3 N1 102.8(4) . . ?
C7 N2 C8 104.4(4) . . ?
C7 N1 N3 109.2(4) . . ?
C7 N1 C16 132.2(4) . . ?
N3 N1 C16 118.5(4) . . ?
N2 C7 N1 109.7(4) . . ?
N2 C7 C1 122.9(4) . . ?
N1 C7 C1 127.3(4) . . ?
C17 C16 C21 120.7(5) . . ?
C17 C16 N1 121.1(4) . . ?
C21 C16 N1 118.2(4) . . ?
C11 C10 C9 122.8(5) . . ?
C19 C20 C21 120.4(5) . . ?
C19 C20 C22 122.1(5) . . ?
C21 C20 C22 117.5(5) . . ?
O2 C15 C14 117.1(5) . . ?
O2 C15 C9 122.7(5) . . ?
C14 C15 C9 120.2(5) . . ?
C12 C14 C15 120.7(5) . . ?
C10 C9 C15 117.5(5) . . ?
C10 C9 C8 121.3(5) . . ?
C15 C9 C8 121.1(4) . . ?
N3 C8 N2 113.9(4) . . ?
N3 C8 C9 121.3(5) . . ?
N2 C8 C9 124.8(4) . . ?
C16 C17 C18 119.9(5) . . ?
C2 C1 C6 118.5(5) . . ?
C2 C1 C7 123.4(5) . . ?
C6 C1 C7 118.0(5) . . ?
C20 C21 C16 119.0(5) . . ?
O1 C6 C5 115.9(5) . . ?
O1 C6 C1 124.5(5) . . ?
C5 C6 C1 119.6(6) . . ?
C14 C12 C11 119.8(5) . . ?
C14 C12 C13 119.3(6) . . ?
C11 C12 C13 120.9(6) . . ?
C3 C2 C1 121.6(5) . . ?
C19 C18 C17 119.7(5) . . ?
C20 C19 C18 120.2(5) . . ?
C10 C11 C12 119.0(5) . . ?
C5 C4 C3 120.9(6) . . ?
C4 C3 C2 119.1(6) . . ?
C4 C5 C6 120.4(6) . . ?
C22 O3 C23 116.7(7) . . ?
O4 C22 O3 121.7(6) . . ?
O4 C22 C20 125.0(6) . . ?
O3 C22 C20 113.3(6) . . ?
F1 C13 F3 103.9(10) . . ?
F1 C13 F2 104.1(9) . . ?
F3 C13 F2 96.3(9) . . ?
F1 C13 C12 119.4(7) . . ?
F3 C13 C12 113.8(8) . . ?
F2 C13 C12 116.3(8) . . ?

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
O2 H2A N3 0.82 1.90 2.617(6) 145.9 .
C5 H5 O2 0.93 2.48 3.406(8) 170.7 1_454
O1 H1 N2 0.82 1.97 2.684(6) 144.8 .
O1 H1 N2 0.82 1.97 2.684(6) 144.8 .
C5 H5 O2 0.93 2.48 3.406(8) 170.7 1_454
O2 H2A N3 0.82 1.90 2.617(6) 145.9 .
O1 H1 N2 0.82 1.97 2.684(6) 144.8 .
C5 H5 O2 0.93 2.48 3.406(8) 170.7 1_454
O2 H2A N3 0.82 1.90 2.617(6) 145.9 .

_refine_diff_density_max         0.444
_refine_diff_density_min         -0.413
_refine_diff_density_rms         0.067

