# 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_2019jrh0011-hjs2
_database_code_depnum_ccdc_archive 'CCDC 1999018'
loop_
_audit_author_name
_audit_author_address
'Jennifer Hiscock'
;University of Kent
United Kingdom
;
_audit_update_record             
;
2020-05-01 deposited with the CCDC.	2021-02-26 downloaded from the CCDC.
;
_audit_creation_date             2020-05-01
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.02.04 svn.rd84adfe8 for OlexSys, GUI svn.r6032)
;
_shelxl_version_number           2013-4
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C9 H8 F3 N2 O4 S, C9 H12 N3 O'
_chemical_formula_sum            'C18 H20 F3 N5 O5 S'
_chemical_formula_weight         475.45
_chemical_absolute_configuration ?
_chemical_melting_point          ?
_chemical_oxdiff_formula         C20H20N5O5F3
_chemical_oxdiff_usercomment     '100 K repete of 2019jrh0008'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_H-M_alt        'P n a 21'
_space_group_name_Hall           'P 2c -2n'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'-x+1/2, y+1/2, z+1/2'
'x+1/2, -y+1/2, z'

_cell_length_a                   8.3209(5)
_cell_length_b                   46.084(5)
_cell_length_c                   5.1719(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1983.2(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    951
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      65.3310
_cell_measurement_theta_min      5.3990
_shelx_estimated_absorpt_T_max   0.977
_shelx_estimated_absorpt_T_min   0.786
_exptl_absorpt_coefficient_mu    2.114
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.53377
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.67a (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.592
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plank
_exptl_crystal_F_000             984
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
1 -5 -3 0.0504
-1 -5 0 0.0195
-1 5 3 0.0504
0 1 0 0.0055
0 -1 0 0.0055
1 5 0 0.0195

_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.062
_exptl_crystal_size_min          0.011
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
0.9934 -4.9999 -3.0037 0.1141 -0.0579 -0.9198
-0.9998 -4.9960 -0.0004 0.1913 -0.1546 0.0401
-0.9934 4.9999 3.0037 -0.1141 0.0579 0.9198
0.0002 0.9997 0.0003 -0.0331 -0.0042 0.0023
-0.0002 -0.9997 -0.0003 0.0331 0.0042 -0.0023
0.9998 4.9960 0.0004 -0.1913 0.1546 -0.0401

_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1296
_diffrn_reflns_av_unetI/netI     0.1161
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       57
_diffrn_reflns_limit_k_min       -49
_diffrn_reflns_limit_l_max       6
_diffrn_reflns_limit_l_min       -4
_diffrn_reflns_number            12545
_diffrn_reflns_point_group_measured_fraction_full 0.873
_diffrn_reflns_point_group_measured_fraction_max 0.849
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.178
_diffrn_reflns_theta_min         3.837
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2887
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -107.00 -19.00   1.00   12.50    --  -41.91 -38.00 -90.00   88
  2  ω    -98.00 -19.00   1.00   12.50    --  -41.91 -57.00 150.00   79
  3  ω    -66.00  32.00   1.00   12.50    --  -41.91  38.00  90.00   98
  4  ω    -66.00 -27.00   1.00   12.50    --  -41.91  57.00 -60.00   39
  5  ω     47.00  80.00   1.00   12.50    --   41.91 -99.00  60.00   33
  6  ω     72.00 132.00   1.00   20.00    --  105.91 -45.00  90.00   60
  7  ω     71.00 121.00   1.00   20.00    --  105.91-125.00-120.00   50
  8  ω     34.00 135.00   1.00   20.00    --  105.91 -61.00-150.00  101
  9  ω     33.00  59.00   1.00   20.00    --  105.91-125.00-120.00   26
 10  ω     85.00 121.00   1.00   20.00    --  105.91-125.00  30.00   36
 11  ω     40.00 134.00   1.00   20.00    --  105.91 -61.00 -30.00   94
 12  ω     99.00 145.00   1.00   20.00    --  105.91  30.00 120.00   46
 13  ω    153.00 178.00   1.00   20.00    --  105.91 125.00-150.00   25
 14  ω     83.00 173.00   1.00   20.00    --  105.91  61.00 -60.00   90
 15  ω     48.00 111.00   1.00   20.00    --  105.91-125.00-180.00   63
 16  ω     53.00 178.00   1.00   20.00    --  105.91  15.00  60.00  125
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0260788000
_diffrn_orient_matrix_UB_12      -0.0330751000
_diffrn_orient_matrix_UB_13      0.0084411000
_diffrn_orient_matrix_UB_21      0.1759569000
_diffrn_orient_matrix_UB_22      -0.0042692000
_diffrn_orient_matrix_UB_23      0.0845643000
_diffrn_orient_matrix_UB_31      -0.0514333000
_diffrn_orient_matrix_UB_32      0.0022410000
_diffrn_orient_matrix_UB_33      0.2854864000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.534
_reflns_Friedel_fraction_full    0.713
_reflns_Friedel_fraction_max     0.669
_reflns_number_gt                2324
_reflns_number_total             3395
_reflns_odcompleteness_completeness 99.86
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2013/4 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS  (Sheldrick, 2008)'
_refine_diff_density_max         0.815
_refine_diff_density_min         -0.683
_refine_diff_density_rms         0.093
_refine_ls_abs_structure_details 
;
 Flack x determined using 532 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   -0.01(5)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     291
_refine_ls_number_reflns         3395
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.1158
_refine_ls_R_factor_gt           0.0787
_refine_ls_restrained_S_all      1.037
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0275P)²+6.0310P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1516
_refine_ls_wR_factor_ref         0.1732
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B)
2.b Aromatic/amide H refined with riding coordinates:
 N2(H2), C6(H6), N1(H1), C4(H4), C3(H3), C7(H7), N4(H4A), N3(H3A), C13(H13),
 C10(H10), C14(H14), C11(H11)
2.c Idealised Me refined as rotating group:
 C17(H17A,H17B,H17C), C16(H16A,H16B,H16C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
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
S1 S 0.3785(3) 0.22152(5) 0.9500(4) 0.0276(5) Uani 1 1 d . . . . .
F1 F 0.7384(8) 0.01714(13) 0.4725(13) 0.0491(16) Uani 1 1 d . . . . .
F3 F 0.8080(8) 0.02916(13) 0.0838(12) 0.0456(16) Uani 1 1 d . . . . .
O1 O 0.3336(9) 0.14450(14) 0.7995(13) 0.0370(17) Uani 1 1 d . . . . .
C8 C 0.3627(11) 0.1570(2) 0.5942(16) 0.030(2) Uani 1 1 d . . . . .
O3 O 0.2733(7) 0.23247(14) 1.1584(12) 0.0292(15) Uani 1 1 d . . . . .
N2 N 0.3284(9) 0.18539(17) 0.5509(15) 0.0287(18) Uani 1 1 d . . . . .
H2 H 0.3576 0.1935 0.4088 0.034 Uiso 1 1 calc R U . . .
O2 O 0.4979(7) 0.20044(14) 1.0474(13) 0.0317(16) Uani 1 1 d . . . . .
O4 O 0.4493(8) 0.24493(14) 0.7946(12) 0.0328(16) Uani 1 1 d . . . . .
C5 C 0.5023(11) 0.1158(2) 0.3719(18) 0.029(2) Uani 1 1 d . . . . .
C6 C 0.6046(12) 0.1099(2) 0.1654(19) 0.036(2) Uani 1 1 d . . . . .
H6 H 0.6319 0.1248 0.0516 0.043 Uiso 1 1 calc R U . . .
N1 N 0.4393(10) 0.14425(17) 0.3887(14) 0.0304(19) Uani 1 1 d . . . . .
H1 H 0.4504 0.1549 0.2531 0.036 Uiso 1 1 calc R U . . .
C9 C 0.2431(10) 0.2017(2) 0.7432(17) 0.029(2) Uani 1 1 d . . . . .
H9A H 0.1788 0.1886 0.8473 0.035 Uiso 1 1 calc R U . . .
H9B H 0.1709 0.2153 0.6586 0.035 Uiso 1 1 calc R U . . .
F2 F 0.5704(8) 0.01312(14) 0.1587(14) 0.0552(19) Uani 1 1 d . . . . .
C4 C 0.4670(12) 0.0938(2) 0.5522(18) 0.032(2) Uani 1 1 d . . . . .
H4 H 0.4014 0.0976 0.6938 0.038 Uiso 1 1 calc R U . . .
C1 C 0.6872(12) 0.0308(2) 0.256(2) 0.038(3) Uani 1 1 d . . . . .
C3 C 0.5321(12) 0.0664(2) 0.5146(18) 0.033(2) Uani 1 1 d . . . . .
H3 H 0.5118 0.0518 0.6343 0.040 Uiso 1 1 calc R U . . .
C7 C 0.6664(12) 0.0823(2) 0.1268(19) 0.037(2) Uani 1 1 d . . . . .
H7 H 0.7330 0.0785 -0.0136 0.044 Uiso 1 1 calc R U . . .
C2 C 0.6279(12) 0.0605(2) 0.299(2) 0.032(2) Uani 1 1 d . . . . .
C12 C 0.3930(10) 0.3405(2) 1.4976(18) 0.028(2) Uani 1 1 d . . . . .
C0AA C 0.4363(11) 0.3700(2) 1.604(2) 0.031(2) Uani 1 1 d . . . . .
C15 C 0.6018(11) 0.4337(2) 1.3536(18) 0.031(2) Uani 1 1 d . . . . .
N4 N 0.4893(9) 0.38912(17) 1.4272(16) 0.0325(19) Uani 1 1 d . . . . .
H4A H 0.5053 0.3841 1.2692 0.039 Uiso 1 1 calc R U . . .
O5 O 0.4217(8) 0.37505(15) 1.8367(12) 0.0338(16) Uani 1 1 d . . . . .
N5 N 0.5176(10) 0.41785(17) 1.5112(16) 0.034(2) Uani 1 1 d . . . . .
C17 C 0.6715(12) 0.4242(2) 1.1021(19) 0.038(2) Uani 1 1 d . . . . .
H17A H 0.7049 0.4043 1.1148 0.057 Uiso 1 1 calc R U . . .
H17B H 0.7626 0.4361 1.0610 0.057 Uiso 1 1 calc R U . . .
H17C H 0.5920 0.4261 0.9686 0.057 Uiso 1 1 calc R U . . .
N3 N 0.3178(9) 0.28540(17) 1.3497(15) 0.0278(18) Uani 1 1 d . . . . .
H3A H 0.2935 0.2681 1.3021 0.033 Uiso 1 1 calc R U . . .
C13 C 0.4687(11) 0.3283(2) 1.2862(19) 0.030(2) Uani 1 1 d . . . . .
H13 H 0.5453 0.3387 1.1941 0.037 Uiso 1 1 calc R U . . .
C10 C 0.2443(11) 0.2967(2) 1.5562(18) 0.029(2) Uani 1 1 d . . . . .
H10 H 0.1696 0.2857 1.6474 0.035 Uiso 1 1 calc R U . . .
C14 C 0.4289(11) 0.3002(2) 1.2134(18) 0.034(2) Uani 1 1 d . . . . .
H14 H 0.4786 0.2917 1.0714 0.041 Uiso 1 1 calc R U . . .
C16 C 0.6272(13) 0.4643(2) 1.437(2) 0.040(2) Uani 1 1 d . . . . .
H16A H 0.7403 0.4681 1.4498 0.060 Uiso 1 1 calc R U . . .
H16B H 0.5774 0.4673 1.6019 0.060 Uiso 1 1 calc R U . . .
H16C H 0.5802 0.4771 1.3118 0.060 Uiso 1 1 calc R U . . .
C11 C 0.2786(11) 0.3246(2) 1.6343(19) 0.032(2) Uani 1 1 d . . . . .
H11 H 0.2264 0.3327 1.7759 0.039 Uiso 1 1 calc R U . . .


_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
S1 O3 1.477(6) . ?
S1 O2 1.478(6) . ?
S1 O4 1.468(7) . ?
S1 C9 1.801(9) . ?
F1 C1 1.355(12) . ?
F3 C1 1.344(12) . ?
O1 C8 1.232(11) . ?
C8 N2 1.358(12) . ?
C8 N1 1.371(11) . ?
N2 H2 0.8600 . ?
N2 C9 1.436(11) . ?
C5 C6 1.392(14) . ?
C5 N1 1.414(12) . ?
C5 C4 1.408(13) . ?
C6 H6 0.9300 . ?
C6 C7 1.387(15) . ?
N1 H1 0.8600 . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
F2 C1 1.363(12) . ?
C4 H4 0.9300 . ?
C4 C3 1.390(13) . ?
C1 C2 1.472(14) . ?
C3 H3 0.9300 . ?
C3 C2 1.399(14) . ?
C7 H7 0.9300 . ?
C7 C2 1.380(14) . ?
C12 C0AA 1.510(13) . ?
C12 C13 1.381(13) . ?
C12 C11 1.393(13) . ?
C0AA N4 1.345(12) . ?
C0AA O5 1.232(12) . ?
C15 N5 1.299(12) . ?
C15 C17 1.490(13) . ?
C15 C16 1.487(13) . ?
N4 H4A 0.8600 . ?
N4 N5 1.413(11) . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
N3 H3A 0.8600 . ?
N3 C10 1.337(11) . ?
N3 C14 1.349(12) . ?
C13 H13 0.9300 . ?
C13 C14 1.385(13) . ?
C10 H10 0.9300 . ?
C10 C11 1.376(13) . ?
C14 H14 0.9300 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C11 H11 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
O3 S1 O2 112.0(4) . . ?
O3 S1 C9 103.6(4) . . ?
O2 S1 C9 106.9(4) . . ?
O4 S1 O3 112.7(4) . . ?
O4 S1 O2 113.6(4) . . ?
O4 S1 C9 107.3(4) . . ?
O1 C8 N2 123.4(8) . . ?
O1 C8 N1 124.0(9) . . ?
N2 C8 N1 112.5(8) . . ?
C8 N2 H2 120.1 . . ?
C8 N2 C9 119.7(8) . . ?
C9 N2 H2 120.1 . . ?
C6 C5 N1 117.0(9) . . ?
C6 C5 C4 119.7(9) . . ?
C4 C5 N1 123.3(9) . . ?
C5 C6 H6 119.5 . . ?
C7 C6 C5 121.0(10) . . ?
C7 C6 H6 119.5 . . ?
C8 N1 C5 128.1(8) . . ?
C8 N1 H1 116.0 . . ?
C5 N1 H1 116.0 . . ?
S1 C9 H9A 109.3 . . ?
S1 C9 H9B 109.3 . . ?
N2 C9 S1 111.6(6) . . ?
N2 C9 H9A 109.3 . . ?
N2 C9 H9B 109.3 . . ?
H9A C9 H9B 108.0 . . ?
C5 C4 H4 120.6 . . ?
C3 C4 C5 118.7(9) . . ?
C3 C4 H4 120.6 . . ?
F1 C1 F2 104.6(9) . . ?
F1 C1 C2 114.3(9) . . ?
F3 C1 F1 106.6(8) . . ?
F3 C1 F2 104.8(8) . . ?
F3 C1 C2 113.7(9) . . ?
F2 C1 C2 111.9(9) . . ?
C4 C3 H3 119.7 . . ?
C4 C3 C2 120.7(10) . . ?
C2 C3 H3 119.7 . . ?
C6 C7 H7 120.3 . . ?
C2 C7 C6 119.3(10) . . ?
C2 C7 H7 120.3 . . ?
C3 C2 C1 119.5(10) . . ?
C7 C2 C1 120.2(10) . . ?
C7 C2 C3 120.4(9) . . ?
C13 C12 C0AA 123.1(9) . . ?
C13 C12 C11 119.9(9) . . ?
C11 C12 C0AA 116.8(8) . . ?
N4 C0AA C12 114.9(9) . . ?
O5 C0AA C12 120.2(9) . . ?
O5 C0AA N4 124.8(10) . . ?
N5 C15 C17 126.3(9) . . ?
N5 C15 C16 115.3(9) . . ?
C16 C15 C17 118.3(9) . . ?
C0AA N4 H4A 121.3 . . ?
C0AA N4 N5 117.5(8) . . ?
N5 N4 H4A 121.3 . . ?
C15 N5 N4 115.1(8) . . ?
C15 C17 H17A 109.5 . . ?
C15 C17 H17B 109.5 . . ?
C15 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C10 N3 H3A 118.9 . . ?
C10 N3 C14 122.2(9) . . ?
C14 N3 H3A 118.9 . . ?
C12 C13 H13 120.4 . . ?
C12 C13 C14 119.1(9) . . ?
C14 C13 H13 120.4 . . ?
N3 C10 H10 119.9 . . ?
N3 C10 C11 120.2(9) . . ?
C11 C10 H10 119.9 . . ?
N3 C14 C13 119.6(9) . . ?
N3 C14 H14 120.2 . . ?
C13 C14 H14 120.2 . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C12 C11 H11 120.6 . . ?
C10 C11 C12 118.9(9) . . ?
C10 C11 H11 120.6 . . ?

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 C1 C2 C3 -41.4(13) . . . . ?
F1 C1 C2 C7 138.7(9) . . . . ?
F3 C1 C2 C3 -164.3(8) . . . . ?
F3 C1 C2 C7 15.9(13) . . . . ?
O1 C8 N2 C9 -4.8(14) . . . . ?
O1 C8 N1 C5 -2.0(16) . . . . ?
C8 N2 C9 S1 95.4(9) . . . . ?
O3 S1 C9 N2 -170.4(6) . . . . ?
N2 C8 N1 C5 175.4(9) . . . . ?
O2 S1 C9 N2 -52.0(8) . . . . ?
O4 S1 C9 N2 70.1(8) . . . . ?
C5 C6 C7 C2 -1.2(15) . . . . ?
C5 C4 C3 C2 -1.4(14) . . . . ?
C6 C5 N1 C8 -166.5(9) . . . . ?
C6 C5 C4 C3 -1.9(14) . . . . ?
C6 C7 C2 C1 177.7(9) . . . . ?
C6 C7 C2 C3 -2.2(14) . . . . ?
N1 C8 N2 C9 177.8(8) . . . . ?
N1 C5 C6 C7 -177.1(9) . . . . ?
N1 C5 C4 C3 178.5(9) . . . . ?
F2 C1 C2 C3 77.2(12) . . . . ?
F2 C1 C2 C7 -102.7(11) . . . . ?
C4 C5 C6 C7 3.2(14) . . . . ?
C4 C5 N1 C8 13.2(15) . . . . ?
C4 C3 C2 C1 -176.3(9) . . . . ?
C4 C3 C2 C7 3.5(14) . . . . ?
C12 C0AA N4 N5 174.3(7) . . . . ?
C12 C13 C14 N3 -0.1(14) . . . . ?
C0AA C12 C13 C14 175.5(9) . . . . ?
C0AA C12 C11 C10 -175.1(8) . . . . ?
C0AA N4 N5 C15 165.0(9) . . . . ?
O5 C0AA N4 N5 -5.5(14) . . . . ?
C17 C15 N5 N4 -1.3(14) . . . . ?
N3 C10 C11 C12 -1.2(14) . . . . ?
C13 C12 C0AA N4 31.2(13) . . . . ?
C13 C12 C0AA O5 -149.0(9) . . . . ?
C13 C12 C11 C10 0.5(14) . . . . ?
C10 N3 C14 C13 -0.5(14) . . . . ?
C14 N3 C10 C11 1.1(14) . . . . ?
C16 C15 N5 N4 178.0(8) . . . . ?
C11 C12 C0AA N4 -153.3(8) . . . . ?
C11 C12 C0AA O5 26.5(13) . . . . ?
C11 C12 C13 C14 0.1(14) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.668
_oxdiff_exptl_absorpt_empirical_full_min 0.631
