# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2021

####################################################################### 
# 
# 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_e9218
_database_code_depnum_ccdc_archive 'CCDC 1998062'
loop_
_audit_author_name
_audit_author_address
'Nigam Rath'
;University of Missouri, Saint Louis
United States of America
;
_audit_update_record             
;
2020-11-19 deposited with the CCDC.	2021-02-08 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C16 H17 N4 O2, C2 F3 O2'
_chemical_formula_sum            'C18 H17 F3 N4 O4'
_chemical_formula_weight         410.35

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                   16.983(3)
_cell_length_b                   5.7953(9)
_cell_length_c                   19.334(3)
_cell_angle_alpha                90
_cell_angle_beta                 111.694(11)
_cell_angle_gamma                90
_cell_volume                     1768.1(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    815
_cell_measurement_theta_min      2.73
_cell_measurement_theta_max      21.11

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.542
_exptl_crystal_F_000             848
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.576
_exptl_crystal_size_mid          0.084
_exptl_crystal_size_min          0.043
_exptl_absorpt_coefficient_mu    0.131
_shelx_estimated_absorpt_T_min   0.928
_shelx_estimated_absorpt_T_max   0.994
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7637
_exptl_absorpt_correction_T_max  0.9281
_exptl_absorpt_process_details   'SADABS V2016/2 (Bruker AXS Inc.)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed tube'
_diffrn_measurement_device_type  'Bruker SMART APEX CCD area detector'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_detector_area_resol_mean 8
_diffrn_reflns_number            12882
_diffrn_reflns_av_unetI/netI     0.1315
_diffrn_reflns_av_R_equivalents  0.1399
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         2.008
_diffrn_reflns_theta_max         25.427
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             3252
_reflns_number_gt                1647
_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 APEX2'
_computing_cell_refinement       'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_structure_solution    'SHELXT-2014 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          
; 
  
All  H atoms were positioned geometrically and refined using a 
riding model with C---H = 0.95--0.99 Å and with Uiso(H) 
= 1.2 (1.5 for methyl groups) times Ueq(C). 
  
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0762P)²] 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         3252
_refine_ls_number_parameters     263
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1562
_refine_ls_R_factor_gt           0.0655
_refine_ls_wR_factor_ref         0.1787
_refine_ls_wR_factor_gt          0.1408
_refine_ls_goodness_of_fit_ref   1.008
_refine_ls_restrained_S_all      1.008
_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
F1 F 0.84808(18) 0.4689(5) 0.50971(15) 0.0401(8) Uani 1 1 d . . . . .
F2 F 0.94257(15) 0.2970(4) 0.47990(15) 0.0328(7) Uani 1 1 d . . . . .
F3 F 0.87648(16) 0.5893(4) 0.41705(16) 0.0391(8) Uani 1 1 d . . . . .
O3 O 0.7967(2) 0.0421(5) 0.42772(16) 0.0270(8) Uani 1 1 d . . . . .
O4 O 0.75519(18) 0.3101(5) 0.33833(16) 0.0235(8) Uani 1 1 d . . . . .
C17 C 0.8669(3) 0.3983(8) 0.4523(3) 0.0265(12) Uani 1 1 d . . . . .
C18 C 0.7989(3) 0.2345(7) 0.4016(2) 0.0177(10) Uani 1 1 d . . . . .
O1 O 0.62063(18) 0.4682(5) 0.20259(16) 0.0236(8) Uani 1 1 d . . . . .
O2 O 0.50759(18) 0.7051(5) 0.16163(16) 0.0246(8) Uani 1 1 d . . . . .
N1 N 0.7177(2) 0.7760(6) 0.29978(19) 0.0187(9) Uani 1 1 d . . . . .
H1A H 0.747392 0.794587 0.269430 0.022 Uiso 1 1 calc R U . . .
H1B H 0.720378 0.625795 0.314153 0.022 Uiso 1 1 calc R U . . .
H1C H 0.740487 0.867251 0.340682 0.022 Uiso 1 1 calc R U . . .
N2 N 0.4100(2) 0.3967(7) 0.1359(2) 0.0286(10) Uani 1 1 d . . . . .
N3 N 0.4404(3) 0.1977(7) 0.1735(2) 0.0380(12) Uani 1 1 d . . . . .
N4 N 0.3815(3) 0.1029(7) 0.1937(2) 0.0413(12) Uani 1 1 d . . . . .
C1 C 0.5729(3) 0.6916(8) 0.3570(3) 0.0234(11) Uani 1 1 d . . . . .
C2 C 0.4999(3) 0.5573(8) 0.3311(3) 0.0289(12) Uani 1 1 d . . . . .
H2 H 0.455969 0.596130 0.285259 0.035 Uiso 1 1 calc R U . . .
C3 C 0.4901(3) 0.3691(9) 0.3705(3) 0.0371(14) Uani 1 1 d . . . . .
H3 H 0.439594 0.280015 0.352066 0.045 Uiso 1 1 calc R U . . .
C4 C 0.5531(3) 0.3101(9) 0.4366(3) 0.0397(14) Uani 1 1 d . . . . .
H4 H 0.546392 0.180498 0.464023 0.048 Uiso 1 1 calc R U . . .
C5 C 0.6269(3) 0.4411(9) 0.4633(3) 0.0365(14) Uani 1 1 d . . . . .
H5 H 0.670884 0.400247 0.508777 0.044 Uiso 1 1 calc R U . . .
C6 C 0.6364(3) 0.6303(8) 0.4236(3) 0.0294(12) Uani 1 1 d . . . . .
H6 H 0.686858 0.719377 0.442225 0.035 Uiso 1 1 calc R U . . .
C7 C 0.5826(3) 0.8950(7) 0.3126(2) 0.0223(11) Uani 1 1 d . . . . .
H7A H 0.614780 1.016707 0.347560 0.027 Uiso 1 1 calc R U . . .
H7B H 0.525609 0.957586 0.283764 0.027 Uiso 1 1 calc R U . . .
C8 C 0.6273(3) 0.8425(7) 0.2589(2) 0.0192(11) Uani 1 1 d . . . . .
H8 H 0.626040 0.984630 0.229129 0.023 Uiso 1 1 calc R U . . .
C9 C 0.5872(3) 0.6470(8) 0.2056(2) 0.0191(11) Uani 1 1 d . . . . .
C10 C 0.4612(3) 0.5336(8) 0.1074(2) 0.0272(12) Uani 1 1 d . . . . .
H10A H 0.424645 0.611165 0.061040 0.033 Uiso 1 1 calc R U . . .
H10B H 0.501494 0.433030 0.095430 0.033 Uiso 1 1 calc R U . . .
C11 C 0.3288(3) 0.4335(8) 0.1316(3) 0.0303(12) Uani 1 1 d . . . . .
C12 C 0.2687(3) 0.6053(9) 0.0994(3) 0.0357(14) Uani 1 1 d . . . . .
H12 H 0.280651 0.735328 0.075025 0.043 Uiso 1 1 calc R U . . .
C13 C 0.1920(3) 0.5749(7) 0.1052(3) 0.0230(11) Uani 1 1 d . . . . .
H13 H 0.149008 0.686606 0.083259 0.028 Uiso 1 1 calc R U . . .
C14 C 0.1732(3) 0.3879(8) 0.1419(3) 0.0318(13) Uani 1 1 d . . . . .
H14 H 0.118146 0.378304 0.143657 0.038 Uiso 1 1 calc R U . . .
C15 C 0.2320(3) 0.2127(9) 0.1763(3) 0.0348(13) Uani 1 1 d . . . . .
H15 H 0.219494 0.085395 0.201434 0.042 Uiso 1 1 calc R U . . .
C16 C 0.3116(3) 0.2451(8) 0.1696(3) 0.0314(13) 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
F1 C17 1.329(5) . ?
F2 C17 1.331(5) . ?
F3 C17 1.341(5) . ?
O3 C18 1.231(5) . ?
O4 C18 1.252(5) . ?
C17 C18 1.537(6) . ?
O1 C9 1.193(5) . ?
O2 C9 1.347(5) . ?
O2 C10 1.448(5) . ?
N1 C8 1.495(5) . ?
N1 H1A 0.9100 . ?
N1 H1B 0.9100 . ?
N1 H1C 0.9100 . ?
N2 N3 1.359(5) . ?
N2 C11 1.368(6) . ?
N2 C10 1.428(6) . ?
N3 N4 1.321(6) . ?
N4 C16 1.377(6) . ?
C1 C6 1.386(6) . ?
C1 C2 1.392(6) . ?
C1 C7 1.502(6) . ?
C2 C3 1.376(7) . ?
C2 H2 0.9500 . ?
C3 C4 1.373(7) . ?
C3 H3 0.9500 . ?
C4 C5 1.391(7) . ?
C4 H4 0.9500 . ?
C5 C6 1.381(7) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C7 C8 1.527(6) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 C9 1.514(6) . ?
C8 H8 1.0000 . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 C12 1.397(6) . ?
C11 C16 1.406(7) . ?
C12 C13 1.360(7) . ?
C12 H12 0.9500 . ?
C13 C14 1.394(6) . ?
C13 H13 0.9500 . ?
C14 C15 1.406(7) . ?
C14 H14 0.9500 . ?
C15 C16 1.418(7) . ?
C15 H15 0.9500 . ?

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
F1 C17 F2 107.2(4) . . ?
F1 C17 F3 106.4(4) . . ?
F2 C17 F3 106.7(4) . . ?
F1 C17 C18 111.5(4) . . ?
F2 C17 C18 111.7(4) . . ?
F3 C17 C18 112.9(4) . . ?
O3 C18 O4 128.4(4) . . ?
O3 C18 C17 115.3(4) . . ?
O4 C18 C17 116.2(4) . . ?
C9 O2 C10 115.8(3) . . ?
C8 N1 H1A 109.5 . . ?
C8 N1 H1B 109.5 . . ?
H1A N1 H1B 109.5 . . ?
C8 N1 H1C 109.5 . . ?
H1A N1 H1C 109.5 . . ?
H1B N1 H1C 109.5 . . ?
N3 N2 C11 109.9(4) . . ?
N3 N2 C10 120.8(4) . . ?
C11 N2 C10 129.3(4) . . ?
N4 N3 N2 109.4(4) . . ?
N3 N4 C16 107.7(4) . . ?
C6 C1 C2 118.3(5) . . ?
C6 C1 C7 121.3(4) . . ?
C2 C1 C7 120.3(4) . . ?
C3 C2 C1 121.2(5) . . ?
C3 C2 H2 119.4 . . ?
C1 C2 H2 119.4 . . ?
C4 C3 C2 120.1(5) . . ?
C4 C3 H3 120.0 . . ?
C2 C3 H3 120.0 . . ?
C3 C4 C5 119.6(5) . . ?
C3 C4 H4 120.2 . . ?
C5 C4 H4 120.2 . . ?
C6 C5 C4 120.1(5) . . ?
C6 C5 H5 119.9 . . ?
C4 C5 H5 119.9 . . ?
C5 C6 C1 120.6(5) . . ?
C5 C6 H6 119.7 . . ?
C1 C6 H6 119.7 . . ?
C1 C7 C8 114.8(4) . . ?
C1 C7 H7A 108.6 . . ?
C8 C7 H7A 108.6 . . ?
C1 C7 H7B 108.6 . . ?
C8 C7 H7B 108.6 . . ?
H7A C7 H7B 107.5 . . ?
N1 C8 C9 106.5(3) . . ?
N1 C8 C7 111.3(3) . . ?
C9 C8 C7 113.6(4) . . ?
N1 C8 H8 108.5 . . ?
C9 C8 H8 108.5 . . ?
C7 C8 H8 108.5 . . ?
O1 C9 O2 124.9(4) . . ?
O1 C9 C8 125.5(4) . . ?
O2 C9 C8 109.7(4) . . ?
N2 C10 O2 110.4(4) . . ?
N2 C10 H10A 109.6 . . ?
O2 C10 H10A 109.6 . . ?
N2 C10 H10B 109.6 . . ?
O2 C10 H10B 109.6 . . ?
H10A C10 H10B 108.1 . . ?
N2 C11 C12 133.9(5) . . ?
N2 C11 C16 104.3(4) . . ?
C12 C11 C16 121.8(5) . . ?
C13 C12 C11 115.8(5) . . ?
C13 C12 H12 122.1 . . ?
C11 C12 H12 122.1 . . ?
C12 C13 C14 123.2(5) . . ?
C12 C13 H13 118.4 . . ?
C14 C13 H13 118.4 . . ?
C13 C14 C15 123.1(5) . . ?
C13 C14 H14 118.5 . . ?
C15 C14 H14 118.5 . . ?
C14 C15 C16 113.3(5) . . ?
C14 C15 H15 123.3 . . ?
C16 C15 H15 123.3 . . ?
N4 C16 C11 108.8(5) . . ?
N4 C16 C15 128.5(5) . . ?
C11 C16 C15 122.6(5) . . ?

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
F1 C17 C18 O3 -70.9(5) . . . . ?
F2 C17 C18 O3 49.0(6) . . . . ?
F3 C17 C18 O3 169.3(4) . . . . ?
F1 C17 C18 O4 111.6(5) . . . . ?
F2 C17 C18 O4 -128.5(4) . . . . ?
F3 C17 C18 O4 -8.1(6) . . . . ?
C11 N2 N3 N4 0.2(5) . . . . ?
C10 N2 N3 N4 -179.8(4) . . . . ?
N2 N3 N4 C16 -0.9(5) . . . . ?
C6 C1 C2 C3 0.6(7) . . . . ?
C7 C1 C2 C3 179.4(4) . . . . ?
C1 C2 C3 C4 -0.3(8) . . . . ?
C2 C3 C4 C5 -0.2(8) . . . . ?
C3 C4 C5 C6 0.4(8) . . . . ?
C4 C5 C6 C1 -0.2(8) . . . . ?
C2 C1 C6 C5 -0.3(7) . . . . ?
C7 C1 C6 C5 -179.1(5) . . . . ?
C6 C1 C7 C8 86.4(5) . . . . ?
C2 C1 C7 C8 -92.4(5) . . . . ?
C1 C7 C8 N1 -65.6(5) . . . . ?
C1 C7 C8 C9 54.5(5) . . . . ?
C10 O2 C9 O1 0.0(6) . . . . ?
C10 O2 C9 C8 179.9(4) . . . . ?
N1 C8 C9 O1 5.8(6) . . . . ?
C7 C8 C9 O1 -117.0(5) . . . . ?
N1 C8 C9 O2 -174.1(4) . . . . ?
C7 C8 C9 O2 63.1(5) . . . . ?
N3 N2 C10 O2 -91.4(5) . . . . ?
C11 N2 C10 O2 88.7(5) . . . . ?
C9 O2 C10 N2 95.3(4) . . . . ?
N3 N2 C11 C12 -179.3(5) . . . . ?
C10 N2 C11 C12 0.7(9) . . . . ?
N3 N2 C11 C16 0.6(5) . . . . ?
C10 N2 C11 C16 -179.5(4) . . . . ?
N2 C11 C12 C13 177.8(5) . . . . ?
C16 C11 C12 C13 -2.0(7) . . . . ?
C11 C12 C13 C14 1.2(7) . . . . ?
C12 C13 C14 C15 0.0(8) . . . . ?
C13 C14 C15 C16 -0.3(7) . . . . ?
N3 N4 C16 C11 1.2(5) . . . . ?
N3 N4 C16 C15 177.9(5) . . . . ?
N2 C11 C16 N4 -1.1(5) . . . . ?
C12 C11 C16 N4 178.8(4) . . . . ?
N2 C11 C16 C15 -178.0(5) . . . . ?
C12 C11 C16 C15 1.9(7) . . . . ?
C14 C15 C16 N4 -176.9(5) . . . . ?
C14 C15 C16 C11 -0.6(7) . . . . ?

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
N1 H1A O4 0.91 2.07 2.879(5) 147.5 2_655
N1 H1A O1 0.91 2.33 2.978(5) 128.0 2_655
N1 H1B O4 0.91 1.93 2.811(4) 163.5 .
N1 H1C O3 0.91 1.89 2.800(4) 175.0 1_565
N1 H1C O4 0.91 2.58 3.192(4) 125.1 1_565
C7 H7B N3 0.99 2.51 3.368(6) 144.9 1_565
C7 H7B N4 0.99 2.57 3.549(6) 172.4 1_565
C10 H10B F2 0.99 2.47 3.045(5) 116.4 4_565
#C12 H12 F1  0.95 2.63 3.556(6) 165.2 4_575 

_refine_diff_density_max         0.343
_refine_diff_density_min         -0.388
_refine_diff_density_rms         0.073

