# Supplementary Information (SI) for Chemical Communications.
# This journal is © The Royal Society of Chemistry 2026

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
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# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
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# Please retain this information to preserve the provenance of 
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data_mj25463_0m
_database_code_depnum_ccdc_archive 'CCDC 2515239'
loop_
_audit_author_name
_audit_author_address
'Leng xuebing'
;University of Chinese Academy of Sciences
China
;
_audit_update_record             
;
2025-12-25 deposited with the CCDC.	2026-02-02 downloaded from the CCDC.
;
_audit_creation_date             2025-10-24
_audit_creation_method           
;
Olex2 1.5
(compiled 2025.05.31 svn.r86d253d1 for OlexSys, GUI svn.r7254)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C12 H12 F12 N6'
_chemical_formula_sum            'C12 H12 F12 N6'
_chemical_formula_weight         468.28
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0137 0.0067 '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 0.0241 0.0134 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0583 0.0400 '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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
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                   9.60800(10)
_cell_length_b                   9.00020(10)
_cell_length_c                   20.4814(3)
_cell_angle_alpha                90
_cell_angle_beta                 95.0680(10)
_cell_angle_gamma                90
_cell_volume                     1764.18(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9879
_cell_measurement_temperature    170.00
_cell_measurement_theta_max      63.48
_cell_measurement_theta_min      3.77
_shelx_estimated_absorpt_T_max   0.942
_shelx_estimated_absorpt_T_min   0.812
_exptl_absorpt_coefficient_mu    1.204
_exptl_absorpt_correction_T_max  0.7523
_exptl_absorpt_correction_T_min  0.6802
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1126 before and 0.0497 after correction.
The Ratio of minimum to maximum transmission is 0.9042.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.763
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             936
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0386
_diffrn_reflns_av_unetI/netI     0.0319
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            14636
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         63.449
_diffrn_reflns_theta_min         3.770
_diffrn_ambient_temperature      170.00
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           GaK\a
_diffrn_radiation_wavelength     1.34139
_diffrn_source                   ?
_diffrn_source_current           3.57
_diffrn_source_power             0.2491146
_diffrn_source_voltage           69.78
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3905
_reflns_number_total             4341
_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       'SAINT V8.41 (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.41 (?, 2016)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.804
_refine_diff_density_min         -0.288
_refine_diff_density_rms         0.058
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     274
_refine_ls_number_reflns         4341
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0460
_refine_ls_R_factor_gt           0.0401
_refine_ls_restrained_S_all      1.052
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0625P)²+0.7890P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1128
_refine_ls_wR_factor_ref         0.1165
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C4(H4), C6(H6)
2.b Idealised Me refined as rotating group:
 C8(H8A,H8B,H8C), C10(H10A,H10B,H10C), C12(H12A,H12B,H12C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_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
F1 F 0.28954(11) 0.19907(12) 0.43208(5) 0.0387(2) Uani 1 1 d . . . . .
F2 F 0.19945(10) 0.06950(11) 0.34984(5) 0.0374(2) Uani 1 1 d . . . . .
F3 F 0.48187(10) 0.11296(11) 0.27180(5) 0.0360(2) Uani 1 1 d . . . . .
F4 F 0.38420(12) 0.30329(12) 0.22220(5) 0.0376(2) Uani 1 1 d . . . . .
F5 F 0.70750(11) 0.62933(11) 0.23198(4) 0.0329(2) Uani 1 1 d . . . . .
F6 F 0.64371(10) 0.85966(9) 0.23694(4) 0.0292(2) Uani 1 1 d . . . . .
F7 F 0.43076(9) 0.79468(10) 0.34475(5) 0.0331(2) Uani 1 1 d . . . . .
F8 F 0.58860(12) 0.81726(12) 0.42658(5) 0.0398(2) Uani 1 1 d . . . . .
F9 F 0.68201(12) 0.40675(14) 0.55214(5) 0.0453(3) Uani 1 1 d . . . . .
F10 F 0.89032(14) 0.33165(14) 0.58372(5) 0.0498(3) Uani 1 1 d . . . . .
F11 F 1.03282(11) 0.21653(17) 0.49394(6) 0.0528(3) Uani 1 1 d . . . . .
F12 F 0.92487(12) 0.18702(16) 0.39787(5) 0.0511(3) Uani 1 1 d . . . . .
N1 N 0.32596(12) 0.13512(13) 0.37382(6) 0.0252(2) Uani 1 1 d . . . . .
N2 N 0.35396(12) 0.18914(13) 0.26514(6) 0.0251(2) Uani 1 1 d . . . . .
N3 N 0.60948(12) 0.71880(12) 0.25984(6) 0.0208(2) Uani 1 1 d . . . . .
N4 N 0.56992(13) 0.83874(13) 0.35825(6) 0.0258(2) Uani 1 1 d . . . . .
N5 N 0.81507(14) 0.39777(15) 0.52964(6) 0.0301(3) Uani 1 1 d . . . . .
N6 N 0.93787(13) 0.28975(19) 0.44928(7) 0.0346(3) Uani 1 1 d . . . . .
C1 C 0.47812(12) 0.34569(13) 0.35531(6) 0.0164(2) Uani 1 1 d . . . . .
C2 C 0.57490(12) 0.27564(13) 0.40018(6) 0.0179(2) Uani 1 1 d . . . . .
H2 H 0.558466 0.176999 0.414107 0.022 Uiso 1 1 calc R U . . .
C3 C 0.69496(12) 0.35029(14) 0.42435(6) 0.0170(2) Uani 1 1 d . . . . .
C4 C 0.72210(12) 0.49304(14) 0.40214(6) 0.0182(2) Uani 1 1 d . . . . .
H4 H 0.804973 0.543250 0.418424 0.022 Uiso 1 1 calc R U . . .
C5 C 0.62822(12) 0.56199(13) 0.35626(6) 0.0166(2) Uani 1 1 d . . . . .
C6 C 0.50503(12) 0.48845(13) 0.33344(6) 0.0172(2) Uani 1 1 d . . . . .
H6 H 0.439495 0.536156 0.302902 0.021 Uiso 1 1 calc R U . . .
C7 C 0.34356(12) 0.26761(13) 0.32973(6) 0.0178(2) Uani 1 1 d . . . . .
C8 C 0.21398(13) 0.36420(15) 0.32084(8) 0.0256(3) Uani 1 1 d . . . . .
H8A H 0.135203 0.304988 0.301532 0.038 Uiso 1 1 calc R U . . .
H8B H 0.230833 0.447443 0.291719 0.038 Uiso 1 1 calc R U . . .
H8C H 0.192138 0.402609 0.363533 0.038 Uiso 1 1 calc R U . . .
C9 C 0.65917(13) 0.71739(13) 0.33195(6) 0.0178(2) Uani 1 1 d . . . . .
C10 C 0.80891(14) 0.77134(16) 0.34601(8) 0.0273(3) Uani 1 1 d . . . . .
H10A H 0.872635 0.701062 0.327453 0.041 Uiso 1 1 calc R U . . .
H10B H 0.831757 0.778300 0.393497 0.041 Uiso 1 1 calc R U . . .
H10C H 0.818785 0.869388 0.326129 0.041 Uiso 1 1 calc R U . . .
C11 C 0.79681(13) 0.28021(14) 0.47671(6) 0.0195(2) Uani 1 1 d . . . . .
C12 C 0.76016(17) 0.12842(16) 0.50145(8) 0.0319(3) Uani 1 1 d . . . . .
H12A H 0.834522 0.094235 0.533796 0.048 Uiso 1 1 calc R U . . .
H12B H 0.750231 0.058442 0.464679 0.048 Uiso 1 1 calc R U . . .
H12C H 0.671920 0.134055 0.521950 0.048 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
F1 N1 1.3969(16) . ?
F2 N1 1.4007(13) . ?
F3 N2 1.4033(14) . ?
F4 N2 1.3995(16) . ?
F5 N3 1.3986(14) . ?
F6 N3 1.4009(13) . ?
F7 N4 1.3987(15) . ?
F8 N4 1.4084(15) . ?
F9 N5 1.3992(18) . ?
F10 N5 1.4008(15) . ?
F11 N6 1.3985(15) . ?
F12 N6 1.3987(19) . ?
N1 C7 1.5142(16) . ?
N2 C7 1.5107(17) . ?
N3 C9 1.5115(16) . ?
N4 C9 1.5165(17) . ?
N5 C11 1.5140(18) . ?
N6 C11 1.5147(18) . ?
C1 C2 1.3984(16) . ?
C1 C6 1.3923(16) . ?
C1 C7 1.5233(16) . ?
C2 H2 0.9500 . ?
C2 C3 1.3879(16) . ?
C3 C4 1.3951(17) . ?
C3 C11 1.5231(16) . ?
C4 H4 0.9500 . ?
C4 C5 1.3900(16) . ?
C5 C6 1.3999(15) . ?
C5 C9 1.5227(16) . ?
C6 H6 0.9500 . ?
C7 C8 1.5162(17) . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C9 C10 1.5216(17) . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 C12 1.5095(19) . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?

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 N1 F2 101.43(10) . . ?
F1 N1 C7 103.56(10) . . ?
F2 N1 C7 105.19(10) . . ?
F3 N2 C7 105.57(10) . . ?
F4 N2 F3 101.02(10) . . ?
F4 N2 C7 103.93(10) . . ?
F5 N3 F6 101.42(9) . . ?
F5 N3 C9 103.17(9) . . ?
F6 N3 C9 105.75(9) . . ?
F7 N4 F8 101.14(10) . . ?
F7 N4 C9 106.64(10) . . ?
F8 N4 C9 103.16(10) . . ?
F9 N5 F10 100.77(11) . . ?
F9 N5 C11 102.99(11) . . ?
F10 N5 C11 106.76(11) . . ?
F11 N6 F12 100.99(12) . . ?
F11 N6 C11 106.50(11) . . ?
F12 N6 C11 102.61(11) . . ?
C2 C1 C7 120.85(11) . . ?
C6 C1 C2 119.73(11) . . ?
C6 C1 C7 119.42(10) . . ?
C1 C2 H2 120.0 . . ?
C3 C2 C1 119.97(11) . . ?
C3 C2 H2 120.0 . . ?
C2 C3 C4 120.19(11) . . ?
C2 C3 C11 120.84(11) . . ?
C4 C3 C11 118.94(11) . . ?
C3 C4 H4 119.9 . . ?
C5 C4 C3 120.18(11) . . ?
C5 C4 H4 119.9 . . ?
C4 C5 C6 119.58(11) . . ?
C4 C5 C9 119.83(10) . . ?
C6 C5 C9 120.59(10) . . ?
C1 C6 C5 120.29(11) . . ?
C1 C6 H6 119.9 . . ?
C5 C6 H6 119.9 . . ?
N1 C7 C1 107.12(10) . . ?
N1 C7 C8 112.92(11) . . ?
N2 C7 N1 100.00(10) . . ?
N2 C7 C1 113.39(10) . . ?
N2 C7 C8 106.26(10) . . ?
C8 C7 C1 116.09(10) . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
C7 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
N3 C9 N4 101.61(9) . . ?
N3 C9 C5 105.86(9) . . ?
N3 C9 C10 113.20(11) . . ?
N4 C9 C5 114.36(10) . . ?
N4 C9 C10 104.94(11) . . ?
C10 C9 C5 116.10(10) . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
N5 C11 N6 100.08(11) . . ?
N5 C11 C3 103.97(10) . . ?
N6 C11 C3 104.81(10) . . ?
C12 C11 N5 114.06(12) . . ?
C12 C11 N6 114.76(12) . . ?
C12 C11 C3 117.18(11) . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?

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 N1 C7 N2 -169.36(9) . . . . ?
F1 N1 C7 C1 72.21(11) . . . . ?
F1 N1 C7 C8 -56.82(13) . . . . ?
F2 N1 C7 N2 -63.29(12) . . . . ?
F2 N1 C7 C1 178.28(10) . . . . ?
F2 N1 C7 C8 49.24(14) . . . . ?
F3 N2 C7 N1 -68.59(11) . . . . ?
F3 N2 C7 C1 45.11(13) . . . . ?
F3 N2 C7 C8 173.81(10) . . . . ?
F4 N2 C7 N1 -174.46(9) . . . . ?
F4 N2 C7 C1 -60.76(12) . . . . ?
F4 N2 C7 C8 67.94(12) . . . . ?
F5 N3 C9 N4 168.92(9) . . . . ?
F5 N3 C9 C5 -71.34(11) . . . . ?
F5 N3 C9 C10 56.93(13) . . . . ?
F6 N3 C9 N4 62.82(11) . . . . ?
F6 N3 C9 C5 -177.43(9) . . . . ?
F6 N3 C9 C10 -49.17(13) . . . . ?
F7 N4 C9 N3 60.49(11) . . . . ?
F7 N4 C9 C5 -53.04(13) . . . . ?
F7 N4 C9 C10 178.59(10) . . . . ?
F8 N4 C9 N3 166.56(10) . . . . ?
F8 N4 C9 C5 53.03(13) . . . . ?
F8 N4 C9 C10 -75.33(12) . . . . ?
F9 N5 C11 N6 173.47(10) . . . . ?
F9 N5 C11 C3 65.30(12) . . . . ?
F9 N5 C11 C12 -63.49(14) . . . . ?
F10 N5 C11 N6 -80.88(13) . . . . ?
F10 N5 C11 C3 170.95(11) . . . . ?
F10 N5 C11 C12 42.15(16) . . . . ?
F11 N6 C11 N5 76.75(14) . . . . ?
F11 N6 C11 C3 -175.76(12) . . . . ?
F11 N6 C11 C12 -45.80(16) . . . . ?
F12 N6 C11 N5 -177.58(10) . . . . ?
F12 N6 C11 C3 -70.09(13) . . . . ?
F12 N6 C11 C12 59.87(14) . . . . ?
C1 C2 C3 C4 -2.44(19) . . . . ?
C1 C2 C3 C11 175.79(11) . . . . ?
C2 C1 C6 C5 -0.11(18) . . . . ?
C2 C1 C7 N1 14.28(16) . . . . ?
C2 C1 C7 N2 -95.06(14) . . . . ?
C2 C1 C7 C8 141.47(13) . . . . ?
C2 C3 C4 C5 0.76(19) . . . . ?
C2 C3 C11 N5 -127.75(13) . . . . ?
C2 C3 C11 N6 127.64(13) . . . . ?
C2 C3 C11 C12 -0.88(19) . . . . ?
C3 C4 C5 C6 1.23(18) . . . . ?
C3 C4 C5 C9 -179.58(11) . . . . ?
C4 C3 C11 N5 50.50(15) . . . . ?
C4 C3 C11 N6 -54.11(15) . . . . ?
C4 C3 C11 C12 177.38(13) . . . . ?
C4 C5 C6 C1 -1.55(18) . . . . ?
C4 C5 C9 N3 142.10(11) . . . . ?
C4 C5 C9 N4 -106.90(13) . . . . ?
C4 C5 C9 C10 15.57(17) . . . . ?
C6 C1 C2 C3 2.11(19) . . . . ?
C6 C1 C7 N1 -165.96(11) . . . . ?
C6 C1 C7 N2 84.70(14) . . . . ?
C6 C1 C7 C8 -38.77(17) . . . . ?
C6 C5 C9 N3 -38.72(15) . . . . ?
C6 C5 C9 N4 72.27(15) . . . . ?
C6 C5 C9 C10 -165.25(12) . . . . ?
C7 C1 C2 C3 -178.13(11) . . . . ?
C7 C1 C6 C5 -179.88(11) . . . . ?
C9 C5 C6 C1 179.27(11) . . . . ?
C11 C3 C4 C5 -177.50(11) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'



data_mo_d8v25650_0m
_database_code_depnum_ccdc_archive 'CCDC 2518732'
loop_
_audit_author_name
_audit_author_address
'Leng xuebing'
;University of Chinese Academy of Sciences
China
;
_audit_update_record             
;
2025-12-25 deposited with the CCDC.	2026-02-05 downloaded from the CCDC.
;
_audit_creation_date             2025-10-20
_audit_creation_method           
;
Olex2 1.5
(compiled 2025.05.31 svn.r86d253d1 for OlexSys, GUI svn.r7254)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C10 H12 F8 N4'
_chemical_formula_sum            'C10 H12 F8 N4'
_chemical_formula_weight         340.24
_chemical_absolute_configuration rmad
_chemical_melting_point          ?
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'
F F 0.0171 0.0103 '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'

_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           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   7.4094(4)
_cell_length_b                   7.8335(4)
_cell_length_c                   21.8556(11)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1268.53(11)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    7948
_cell_measurement_temperature    296
_cell_measurement_theta_max      30.631
_cell_measurement_theta_min      2.762
_shelx_estimated_absorpt_T_max   0.990
_shelx_estimated_absorpt_T_min   0.966
_exptl_absorpt_coefficient_mu    0.193
_exptl_absorpt_correction_T_max  0.7465
_exptl_absorpt_correction_T_min  0.5972
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1406 before and 0.0729 after correction.
The Ratio of minimum to maximum transmission is 0.8000.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.782
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             688
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0605
_diffrn_reflns_av_unetI/netI     0.0408
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.869
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_number            18161
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.827
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         32.917
_diffrn_reflns_theta_min         1.864
_diffrn_ambient_temperature      296
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.869
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       ?
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_reflns_Friedel_coverage         0.662
_reflns_Friedel_fraction_full    0.996
_reflns_Friedel_fraction_max     0.770
_reflns_number_gt                2746
_reflns_number_total             3928
_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       'SAINT V8.40B (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_refine_diff_density_max         0.191
_refine_diff_density_min         -0.152
_refine_diff_density_rms         0.038
_refine_ls_abs_structure_details 
;
 Flack x determined using 862 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.1(3)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     199
_refine_ls_number_reflns         3928
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0725
_refine_ls_R_factor_gt           0.0466
_refine_ls_restrained_S_all      1.025
_refine_ls_shift/su_max          0.008
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0602P)²+0.1575P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1179
_refine_ls_wR_factor_ref         0.1344
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Ternary CH refined with riding coordinates:
 C2(H2), C4(H4), C6(H6), C8(H8)
2.b Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B), C7(H7A,H7B), C9(H9A,H9B), C10(H10A,H10B)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_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
F1 F 0.8027(5) 1.0151(3) 0.30211(12) 0.1130(10) Uani 1 1 d . . . . .
F2 F 0.8454(3) 0.8229(4) 0.23497(9) 0.0856(7) Uani 1 1 d . . . . .
F3 F 1.0545(3) 0.9152(3) 0.37086(15) 0.1133(10) Uani 1 1 d . . . . .
F4 F 1.1175(2) 0.7447(3) 0.29769(10) 0.0775(6) Uani 1 1 d . . . . .
F5 F 0.2536(3) 0.4675(4) 0.46142(12) 0.1085(9) Uani 1 1 d . . . . .
F6 F 0.4748(4) 0.3790(3) 0.51621(10) 0.0880(7) Uani 1 1 d . . . . .
F7 F 0.3251(3) 0.2381(3) 0.38394(15) 0.1074(9) Uani 1 1 d . . . . .
F8 F 0.5443(4) 0.1528(2) 0.43878(11) 0.0935(8) Uani 1 1 d . . . . .
N1 N 0.7505(3) 0.8507(4) 0.28827(12) 0.0601(6) Uani 1 1 d . . . . .
N2 N 1.0212(3) 0.7507(3) 0.35186(12) 0.0573(6) Uani 1 1 d . . . . .
N3 N 0.4365(4) 0.4959(3) 0.47059(12) 0.0607(6) Uani 1 1 d . . . . .
N4 N 0.5070(4) 0.2629(3) 0.39136(12) 0.0605(7) Uani 1 1 d . . . . .
C1 C 0.8252(3) 0.7360(3) 0.33693(12) 0.0420(5) Uani 1 1 d . . . . .
C2 C 0.7161(4) 0.7727(3) 0.39549(12) 0.0461(6) Uani 1 1 d . . . . .
H2 H 0.737785 0.890480 0.408676 0.055 Uiso 1 1 calc R U . . .
C3 C 0.5150(4) 0.7481(3) 0.38221(15) 0.0514(6) Uani 1 1 d . . . . .
H3A H 0.445395 0.773634 0.418668 0.062 Uiso 1 1 calc R U . . .
H3B H 0.477607 0.826188 0.350165 0.062 Uiso 1 1 calc R U . . .
C4 C 0.4787(3) 0.5644(3) 0.36214(12) 0.0463(6) Uani 1 1 d . . . . .
H4 H 0.349808 0.550061 0.353495 0.056 Uiso 1 1 calc R U . . .
C5 C 0.5353(4) 0.4416(3) 0.41362(13) 0.0439(5) Uani 1 1 d . . . . .
C6 C 0.7377(4) 0.4639(3) 0.42667(13) 0.0456(6) Uani 1 1 d . . . . .
H6 H 0.775372 0.385639 0.459232 0.055 Uiso 1 1 calc R U . . .
C7 C 0.8464(4) 0.4288(3) 0.36849(14) 0.0516(6) Uani 1 1 d . . . . .
H7A H 0.826849 0.311766 0.355588 0.062 Uiso 1 1 calc R U . . .
H7B H 0.974010 0.443008 0.376994 0.062 Uiso 1 1 calc R U . . .
C8 C 0.7904(4) 0.5504(3) 0.31692(13) 0.0466(6) Uani 1 1 d . . . . .
H8 H 0.859686 0.524903 0.279822 0.056 Uiso 1 1 calc R U . . .
C9 C 0.5878(4) 0.5265(4) 0.30447(13) 0.0533(7) Uani 1 1 d . . . . .
H9A H 0.550264 0.602685 0.271864 0.064 Uiso 1 1 calc R U . . .
H9B H 0.565191 0.410197 0.291344 0.064 Uiso 1 1 calc R U . . .
C10 C 0.7740(4) 0.6498(3) 0.44614(12) 0.0503(6) Uani 1 1 d . . . . .
H10A H 0.707577 0.675080 0.483301 0.060 Uiso 1 1 calc R U . . .
H10B H 0.901579 0.664668 0.454558 0.060 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
F1 N1 1.378(4) . ?
F2 N1 1.378(3) . ?
F3 N2 1.376(3) . ?
F4 N2 1.383(3) . ?
F5 N3 1.388(4) . ?
F6 N3 1.383(3) . ?
F7 N4 1.372(3) . ?
F8 N4 1.377(3) . ?
N1 C1 1.498(4) . ?
N2 C1 1.493(3) . ?
N3 C5 1.505(4) . ?
N4 C5 1.497(3) . ?
C1 C2 1.541(4) . ?
C1 C8 1.540(3) . ?
C2 H2 0.9800 . ?
C2 C3 1.530(4) . ?
C2 C10 1.528(4) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C3 C4 1.529(4) . ?
C4 H4 0.9800 . ?
C4 C5 1.538(4) . ?
C4 C9 1.526(4) . ?
C5 C6 1.537(4) . ?
C6 H6 0.9800 . ?
C6 C7 1.530(4) . ?
C6 C10 1.541(3) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C7 C8 1.533(4) . ?
C8 H8 0.9800 . ?
C8 C9 1.537(4) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?

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 N1 C1 107.5(2) . . ?
F2 N1 F1 101.0(2) . . ?
F2 N1 C1 108.5(2) . . ?
F3 N2 F4 101.4(2) . . ?
F3 N2 C1 108.2(2) . . ?
F4 N2 C1 108.2(2) . . ?
F5 N3 C5 108.1(2) . . ?
F6 N3 F5 101.4(2) . . ?
F6 N3 C5 108.0(2) . . ?
F7 N4 F8 101.4(2) . . ?
F7 N4 C5 108.0(2) . . ?
F8 N4 C5 108.3(2) . . ?
N1 C1 C2 106.5(2) . . ?
N1 C1 C8 107.6(2) . . ?
N2 C1 N1 117.9(2) . . ?
N2 C1 C2 108.3(2) . . ?
N2 C1 C8 107.3(2) . . ?
C2 C1 C8 108.9(2) . . ?
C1 C2 H2 109.5 . . ?
C3 C2 C1 109.2(2) . . ?
C3 C2 H2 109.5 . . ?
C10 C2 C1 109.7(2) . . ?
C10 C2 H2 109.5 . . ?
C10 C2 C3 109.4(2) . . ?
C2 C3 H3A 109.6 . . ?
C2 C3 H3B 109.6 . . ?
H3A C3 H3B 108.1 . . ?
C4 C3 C2 110.1(2) . . ?
C4 C3 H3A 109.6 . . ?
C4 C3 H3B 109.6 . . ?
C3 C4 H4 109.6 . . ?
C3 C4 C5 109.3(2) . . ?
C5 C4 H4 109.6 . . ?
C9 C4 C3 109.1(2) . . ?
C9 C4 H4 109.6 . . ?
C9 C4 C5 109.8(2) . . ?
N3 C5 C4 107.2(2) . . ?
N3 C5 C6 106.8(2) . . ?
N4 C5 N3 117.7(2) . . ?
N4 C5 C4 108.0(2) . . ?
N4 C5 C6 107.6(2) . . ?
C4 C5 C6 109.3(2) . . ?
C5 C6 H6 110.0 . . ?
C5 C6 C10 109.2(2) . . ?
C7 C6 C5 109.8(2) . . ?
C7 C6 H6 110.0 . . ?
C7 C6 C10 107.9(2) . . ?
C10 C6 H6 110.0 . . ?
C6 C7 H7A 109.5 . . ?
C6 C7 H7B 109.5 . . ?
C6 C7 C8 110.9(2) . . ?
H7A C7 H7B 108.0 . . ?
C8 C7 H7A 109.5 . . ?
C8 C7 H7B 109.5 . . ?
C1 C8 H8 109.9 . . ?
C7 C8 C1 109.4(2) . . ?
C7 C8 H8 109.9 . . ?
C7 C8 C9 108.6(2) . . ?
C9 C8 C1 109.2(2) . . ?
C9 C8 H8 109.9 . . ?
C4 C9 C8 110.3(2) . . ?
C4 C9 H9A 109.6 . . ?
C4 C9 H9B 109.6 . . ?
C8 C9 H9A 109.6 . . ?
C8 C9 H9B 109.6 . . ?
H9A C9 H9B 108.1 . . ?
C2 C10 C6 110.2(2) . . ?
C2 C10 H10A 109.6 . . ?
C2 C10 H10B 109.6 . . ?
C6 C10 H10A 109.6 . . ?
C6 C10 H10B 109.6 . . ?
H10A C10 H10B 108.1 . . ?

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 N1 C1 N2 -50.7(3) . . . . ?
F1 N1 C1 C2 71.2(3) . . . . ?
F1 N1 C1 C8 -172.1(2) . . . . ?
F2 N1 C1 N2 57.7(3) . . . . ?
F2 N1 C1 C2 179.6(2) . . . . ?
F2 N1 C1 C8 -63.7(3) . . . . ?
F3 N2 C1 N1 59.4(3) . . . . ?
F3 N2 C1 C2 -61.6(3) . . . . ?
F3 N2 C1 C8 -179.0(2) . . . . ?
F4 N2 C1 N1 -49.7(3) . . . . ?
F4 N2 C1 C2 -170.6(2) . . . . ?
F4 N2 C1 C8 71.9(3) . . . . ?
F5 N3 C5 N4 -55.4(3) . . . . ?
F5 N3 C5 C4 66.4(3) . . . . ?
F5 N3 C5 C6 -176.5(2) . . . . ?
F6 N3 C5 N4 53.6(3) . . . . ?
F6 N3 C5 C4 175.4(2) . . . . ?
F6 N3 C5 C6 -67.5(3) . . . . ?
F7 N4 C5 N3 55.0(3) . . . . ?
F7 N4 C5 C4 -66.5(3) . . . . ?
F7 N4 C5 C6 175.6(2) . . . . ?
F8 N4 C5 N3 -54.0(3) . . . . ?
F8 N4 C5 C4 -175.5(2) . . . . ?
F8 N4 C5 C6 66.6(3) . . . . ?
N1 C1 C2 C3 55.5(3) . . . . ?
N1 C1 C2 C10 175.4(2) . . . . ?
N1 C1 C8 C7 -174.0(2) . . . . ?
N1 C1 C8 C9 -55.3(3) . . . . ?
N2 C1 C2 C3 -176.7(2) . . . . ?
N2 C1 C2 C10 -56.9(3) . . . . ?
N2 C1 C8 C7 58.2(3) . . . . ?
N2 C1 C8 C9 176.9(2) . . . . ?
N3 C5 C6 C7 -174.17(19) . . . . ?
N3 C5 C6 C10 -56.0(3) . . . . ?
N4 C5 C6 C7 58.6(3) . . . . ?
N4 C5 C6 C10 176.7(2) . . . . ?
C1 C2 C3 C4 60.6(3) . . . . ?
C1 C2 C10 C6 -60.8(3) . . . . ?
C1 C8 C9 C4 -59.9(3) . . . . ?
C2 C1 C8 C7 -58.9(3) . . . . ?
C2 C1 C8 C9 59.8(3) . . . . ?
C2 C3 C4 C5 60.3(3) . . . . ?
C2 C3 C4 C9 -59.8(3) . . . . ?
C3 C2 C10 C6 59.0(3) . . . . ?
C3 C4 C5 N3 55.1(3) . . . . ?
C3 C4 C5 N4 -177.1(2) . . . . ?
C3 C4 C5 C6 -60.3(3) . . . . ?
C3 C4 C9 C8 59.4(3) . . . . ?
C4 C5 C6 C7 -58.5(3) . . . . ?
C4 C5 C6 C10 59.7(3) . . . . ?
C5 C4 C9 C8 -60.3(3) . . . . ?
C5 C6 C7 C8 59.1(3) . . . . ?
C5 C6 C10 C2 -59.4(3) . . . . ?
C6 C7 C8 C1 60.3(3) . . . . ?
C6 C7 C8 C9 -58.8(3) . . . . ?
C7 C6 C10 C2 59.9(3) . . . . ?
C7 C8 C9 C4 59.3(3) . . . . ?
C8 C1 C2 C3 -60.3(3) . . . . ?
C8 C1 C2 C10 59.6(3) . . . . ?
C9 C4 C5 N3 174.7(2) . . . . ?
C9 C4 C5 N4 -57.5(3) . . . . ?
C9 C4 C5 C6 59.3(3) . . . . ?
C10 C2 C3 C4 -59.5(3) . . . . ?
C10 C6 C7 C8 -59.8(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'

