# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2022

####################################################################### 
# 
# 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_11
_database_code_depnum_ccdc_archive 'CCDC 2088601'
loop_
_audit_author_name
_audit_author_address
'Bo Lin'
;Fuzhou university
China
;
_audit_update_record             
;
2021-06-08 deposited with the CCDC.	2022-10-05 downloaded from the CCDC.
;
_audit_creation_date             2021-02-25
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C9 H5 F3 N2 O'
_chemical_formula_sum            'C9 H5 F3 N2 O'
_chemical_formula_weight         214.15
_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 0.0181 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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, y, -z+1/2'
3 'x+1/2, y+1/2, z'
4 '-x+1/2, y+1/2, -z+1/2'
5 '-x, -y, -z'
6 'x, -y, z-1/2'
7 '-x+1/2, -y+1/2, -z'
8 'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   17.5653(19)
_cell_length_b                   4.4815(5)
_cell_length_c                   24.060(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 93.245(11)
_cell_angle_gamma                90.00
_cell_volume                     1890.9(3)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    3620
_cell_measurement_temperature    296.15
_cell_measurement_theta_max      66.81
_cell_measurement_theta_min      3.68
_exptl_absorpt_coefficient_mu    1.251
_exptl_absorpt_correction_T_max  0.9401
_exptl_absorpt_correction_T_min  0.8851
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   ?
_exptl_crystal_colour            'clear light white'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    white
_exptl_crystal_density_diffrn    1.504
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             864
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.05
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0833
_diffrn_reflns_av_unetI/netI     0.0641
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            6581
_diffrn_reflns_theta_full        66.51
_diffrn_reflns_theta_max         66.51
_diffrn_reflns_theta_min         3.68
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.963
_diffrn_measured_fraction_theta_max 0.963
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   'fine-focus sealed tube'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         0
_reflns_number_gt                1206
_reflns_number_total             1610
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       lb20201022
_computing_data_collection       ?
_computing_data_reduction        lb20201022
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.301
_refine_diff_density_min         -0.272
_refine_diff_density_rms         0.075
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.096
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     136
_refine_ls_number_reflns         1610
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0998
_refine_ls_R_factor_gt           0.0778
_refine_ls_restrained_S_all      1.096
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1027P)²+3.8934P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2165
_refine_ls_wR_factor_ref         0.2352
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C00A(H00A), C00B(H00B), C00C(H00C), C00D(H00D), C00E(H00E)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
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_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_refinement_flags_posn
O001 O 0.76854(14) 0.5746(7) 0.65461(10) 0.0566(8) Uani 1 d . . .
F002 F 0.84354(15) 0.7226(8) 0.50328(10) 0.0867(10) Uani 1 d . . .
F003 F 0.95193(14) 0.7353(8) 0.54494(13) 0.0966(11) Uani 1 d . . .
N004 N 0.79290(17) 0.6087(8) 0.60053(12) 0.0541(9) Uani 1 d . . .
F005 F 0.8863(3) 1.1273(7) 0.53654(14) 0.1300(16) Uani 1 d . . .
N006 N 0.45948(19) -0.2877(10) 0.67943(15) 0.0716(11) Uani 1 d . . .
C007 C 0.70573(19) 0.3878(9) 0.65630(15) 0.0497(9) Uani 1 d . . .
C008 C 0.5134(2) -0.1480(10) 0.67532(16) 0.0562(10) Uani 1 d . . .
C009 C 0.58037(19) 0.0339(9) 0.66911(15) 0.0503(10) Uani 1 d . . .
C00A C 0.8489(2) 0.7809(9) 0.60030(17) 0.0558(10) Uani 1 d . . .
H00A H 0.8688 0.8684 0.6330 0.067 Uiso 1 calc . . R
C00B C 0.6716(2) 0.2472(10) 0.61029(15) 0.0541(10) Uani 1 d . . .
H00B H 0.6906 0.2717 0.5753 0.065 Uiso 1 calc . . R
C00C C 0.6086(2) 0.0690(10) 0.61745(16) 0.0544(10) Uani 1 d . . .
H00C H 0.5851 -0.0282 0.5869 0.065 Uiso 1 calc . . R
C00D C 0.6777(2) 0.3537(10) 0.70852(16) 0.0560(10) Uani 1 d . . .
H00D H 0.7010 0.4516 0.7390 0.067 Uiso 1 calc . . R
C00E C 0.6155(2) 0.1750(10) 0.71510(16) 0.0572(11) Uani 1 d . . .
H00E H 0.5970 0.1485 0.7502 0.069 Uiso 1 calc . . R
C00F C 0.8828(2) 0.8416(10) 0.54623(19) 0.0625(11) Uani 1 d . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
O001 0.0425(15) 0.0726(19) 0.0548(14) 0.0009(12) 0.0040(11) -0.0079(13)
F002 0.0681(17) 0.129(3) 0.0640(15) -0.0006(15) 0.0129(12) -0.0112(17)
F003 0.0406(14) 0.138(3) 0.113(2) 0.0179(19) 0.0222(13) 0.0003(16)
N004 0.0379(18) 0.068(2) 0.0567(18) 0.0006(15) 0.0074(13) 0.0059(16)
F005 0.223(4) 0.0616(19) 0.114(2) 0.0097(16) 0.085(3) 0.005(2)
N006 0.041(2) 0.093(3) 0.082(2) -0.013(2) 0.0059(17) -0.015(2)
C007 0.0294(18) 0.060(2) 0.059(2) 0.0022(17) 0.0020(15) 0.0061(17)
C008 0.036(2) 0.067(3) 0.066(2) -0.0079(19) 0.0024(17) 0.0028(19)
C009 0.0299(19) 0.058(2) 0.063(2) -0.0023(17) 0.0031(15) 0.0060(17)
C00A 0.046(2) 0.058(2) 0.063(2) -0.0006(18) 0.0039(18) -0.003(2)
C00B 0.038(2) 0.070(3) 0.054(2) -0.0022(18) 0.0056(16) 0.0047(19)
C00C 0.0327(19) 0.068(3) 0.062(2) -0.0105(18) 0.0014(16) 0.0039(18)
C00D 0.044(2) 0.068(3) 0.056(2) -0.0026(18) 0.0020(17) -0.005(2)
C00E 0.043(2) 0.072(3) 0.058(2) -0.0002(19) 0.0079(17) -0.001(2)
C00F 0.055(3) 0.059(3) 0.074(3) -0.003(2) 0.013(2) 0.005(2)

_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
O001 N004 1.401(4) . ?
O001 C007 1.387(4) . ?
F002 C00F 1.322(5) . ?
F003 C00F 1.307(5) . ?
N004 C00A 1.250(5) . ?
F005 C00F 1.304(5) . ?
N006 C008 1.144(5) . ?
C007 C00B 1.381(5) . ?
C007 C00D 1.384(5) . ?
C008 C009 1.446(5) . ?
C009 C00C 1.373(5) . ?
C009 C00E 1.389(6) . ?
C00A H00A 0.9300 . ?
C00A C00F 1.486(6) . ?
C00B H00B 0.9300 . ?
C00B C00C 1.383(5) . ?
C00C H00C 0.9300 . ?
C00D H00D 0.9300 . ?
C00D C00E 1.370(5) . ?
C00E H00E 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
C007 O001 N004 112.2(3) . . ?
C00A N004 O001 110.7(3) . . ?
C00B C007 O001 124.2(3) . . ?
C00B C007 C00D 121.1(4) . . ?
C00D C007 O001 114.7(3) . . ?
N006 C008 C009 178.5(5) . . ?
C00C C009 C008 119.7(3) . . ?
C00C C009 C00E 120.1(4) . . ?
C00E C009 C008 120.2(3) . . ?
N004 C00A H00A 120.9 . . ?
N004 C00A C00F 118.1(4) . . ?
C00F C00A H00A 120.9 . . ?
C007 C00B H00B 120.7 . . ?
C007 C00B C00C 118.5(3) . . ?
C00C C00B H00B 120.7 . . ?
C009 C00C C00B 120.8(4) . . ?
C009 C00C H00C 119.6 . . ?
C00B C00C H00C 119.6 . . ?
C007 C00D H00D 120.1 . . ?
C00E C00D C007 119.8(4) . . ?
C00E C00D H00D 120.1 . . ?
C009 C00E H00E 120.2 . . ?
C00D C00E C009 119.7(3) . . ?
C00D C00E H00E 120.2 . . ?
F002 C00F C00A 113.2(4) . . ?
F003 C00F F002 106.2(4) . . ?
F003 C00F C00A 111.9(4) . . ?
F005 C00F F002 106.5(4) . . ?
F005 C00F F003 107.5(4) . . ?
F005 C00F C00A 111.2(4) . . ?

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
O001 N004 C00A C00F 179.6(3) . . . . ?
O001 C007 C00B C00C -179.3(3) . . . . ?
O001 C007 C00D C00E 179.7(4) . . . . ?
N004 O001 C007 C00B 1.0(5) . . . . ?
N004 O001 C007 C00D -178.0(3) . . . . ?
N004 C00A C00F F002 6.0(6) . . . . ?
N004 C00A C00F F003 -113.9(5) . . . . ?
N004 C00A C00F F005 125.8(5) . . . . ?
N006 C008 C009 C00C -60(18) . . . . ?
N006 C008 C009 C00E 119(18) . . . . ?
C007 O001 N004 C00A 179.2(3) . . . . ?
C007 C00B C00C C009 0.3(6) . . . . ?
C007 C00D C00E C009 -1.1(6) . . . . ?
C008 C009 C00C C00B 178.5(4) . . . . ?
C008 C009 C00E C00D -178.2(4) . . . . ?
C00B C007 C00D C00E 0.7(6) . . . . ?
C00C C009 C00E C00D 1.2(6) . . . . ?
C00D C007 C00B C00C -0.3(6) . . . . ?
C00E C009 C00C C00B -0.8(6) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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 2156038'
loop_
_audit_author_name
_audit_author_address
'Bo Lin'
;Fuzhou University
China
;
_audit_update_record             
;
2022-03-03 deposited with the CCDC.	2022-10-05 downloaded from the CCDC.
;
_audit_creation_date             2021-06-06
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C15 H10 F3 N3'
_chemical_formula_sum            'C15 H10 F3 N3'
_chemical_formula_weight         289.26
_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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, y+1/2, -z+1/2'
3 '-x, -y, -z'
4 'x, -y-1/2, z-1/2'

_cell_length_a                   7.3715(7)
_cell_length_b                   15.6061(16)
_cell_length_c                   11.7583(14)
_cell_angle_alpha                90.00
_cell_angle_beta                 106.836(4)
_cell_angle_gamma                90.00
_cell_volume                     1294.7(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4244
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      29.587
_cell_measurement_theta_min      2.231
_exptl_absorpt_coefficient_mu    0.121
_exptl_absorpt_correction_T_max  0.9880
_exptl_absorpt_correction_T_min  0.9762
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   ?
_exptl_crystal_colour            'clear light orange'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.484
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             592
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0813
_diffrn_reflns_av_unetI/netI     0.0757
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            22392
_diffrn_reflns_theta_full        29.68
_diffrn_reflns_theta_max         29.68
_diffrn_reflns_theta_min         2.23
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed tube'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                2198
_reflns_number_total             3637
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       lb20201022
_computing_data_collection       ?
_computing_data_reduction        lb20201022
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.331
_refine_diff_density_min         -0.318
_refine_diff_density_rms         0.051
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.014
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     190
_refine_ls_number_reflns         3637
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1073
_refine_ls_R_factor_gt           0.0541
_refine_ls_restrained_S_all      1.014
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0495P)²+0.4523P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1185
_refine_ls_wR_factor_ref         0.1393
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C7(H7), C8(H8), C10(H10), C11(H11), C13(H13), C14(H14), C15(H15),
 C16(H16), C17(H17)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
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_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_refinement_flags_posn
C2 C 0.6079(3) 0.28208(13) 0.29041(16) 0.0374(4) Uani 1 d . . .
H2 H 0.5665 0.3177 0.2245 0.045 Uiso 1 calc . . R
C5 C 0.6739(2) 0.17733(11) 0.40165(15) 0.0322(4) Uani 1 d . . .
C6 C 0.7140(2) 0.39583(11) 0.44599(15) 0.0282(4) Uani 1 d . . .
C7 C 0.7398(2) 0.46096(11) 0.37282(15) 0.0319(4) Uani 1 d . . .
H7 H 0.7397 0.4491 0.2953 0.038 Uiso 1 calc . . R
C8 C 0.7659(2) 0.54374(12) 0.41527(15) 0.0318(4) Uani 1 d . . .
H8 H 0.7819 0.5875 0.3653 0.038 Uiso 1 calc . . R
C9 C 0.7687(2) 0.56336(11) 0.53169(14) 0.0286(4) Uani 1 d . . .
C10 C 0.7420(2) 0.49592(12) 0.60319(15) 0.0322(4) Uani 1 d . . .
H10 H 0.7427 0.5073 0.6809 0.039 Uiso 1 calc . . R
C11 C 0.7146(2) 0.41292(12) 0.56181(15) 0.0314(4) Uani 1 d . . .
H11 H 0.6968 0.3690 0.6109 0.038 Uiso 1 calc . . R
C12 C 0.8006(2) 0.65247(11) 0.57667(15) 0.0299(4) Uani 1 d . . .
C13 C 0.7426(3) 0.72224(12) 0.50079(16) 0.0356(4) Uani 1 d . . .
H13 H 0.6789 0.7128 0.4211 0.043 Uiso 1 calc . . R
C14 C 0.7783(3) 0.80512(13) 0.54204(18) 0.0418(5) Uani 1 d . . .
H14 H 0.7388 0.8509 0.4901 0.050 Uiso 1 calc . . R
C15 C 0.8724(3) 0.82054(13) 0.66020(18) 0.0427(5) Uani 1 d . . .
H15 H 0.8971 0.8765 0.6875 0.051 Uiso 1 calc . . R
C16 C 0.9292(3) 0.75303(13) 0.73702(17) 0.0417(5) Uani 1 d . . .
H16 H 0.9917 0.7633 0.8167 0.050 Uiso 1 calc . . R
C17 C 0.8937(2) 0.66940(13) 0.69620(16) 0.0363(4) Uani 1 d . . .
H17 H 0.9322 0.6241 0.7490 0.044 Uiso 1 calc . . R
C18 C 0.6968(3) 0.08675(13) 0.44248(17) 0.0425(5) Uani 1 d . . .
F19 F 0.5424(2) 0.04079(8) 0.39430(12) 0.0666(4) Uani 1 d . . .
F20 F 0.8356(2) 0.04654(8) 0.41280(14) 0.0703(4) Uani 1 d . . .
F21 F 0.7342(2) 0.08031(8) 0.55938(10) 0.0696(5) Uani 1 d . . .
N1 N 0.5999(2) 0.19788(10) 0.28604(13) 0.0379(4) Uani 1 d . . .
N3 N 0.6836(2) 0.31008(9) 0.40205(12) 0.0298(3) Uani 1 d . . .
N4 N 0.7273(2) 0.24163(9) 0.47607(12) 0.0327(4) Uani 1 d . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
C2 0.0379(11) 0.0453(11) 0.0255(9) 0.0001(8) 0.0036(8) 0.0006(8)
C5 0.0283(9) 0.0404(10) 0.0286(9) -0.0021(8) 0.0090(7) -0.0049(7)
C6 0.0201(8) 0.0371(10) 0.0266(9) -0.0020(7) 0.0054(7) 0.0021(7)
C7 0.0304(9) 0.0434(10) 0.0235(9) -0.0004(7) 0.0102(7) 0.0024(7)
C8 0.0308(9) 0.0376(10) 0.0277(9) 0.0032(7) 0.0098(7) 0.0035(7)
C9 0.0195(8) 0.0408(10) 0.0244(8) 0.0000(7) 0.0046(6) 0.0039(7)
C10 0.0292(10) 0.0456(11) 0.0212(8) -0.0013(7) 0.0063(7) 0.0023(8)
C11 0.0286(9) 0.0415(10) 0.0242(9) 0.0030(7) 0.0077(7) 0.0009(7)
C12 0.0216(8) 0.0413(10) 0.0268(9) -0.0032(7) 0.0071(7) 0.0010(7)
C13 0.0328(10) 0.0410(11) 0.0313(9) -0.0023(8) 0.0069(8) 0.0008(8)
C14 0.0435(11) 0.0417(11) 0.0411(11) -0.0027(9) 0.0140(9) 0.0008(9)
C15 0.0415(11) 0.0446(12) 0.0464(12) -0.0150(9) 0.0199(10) -0.0088(9)
C16 0.0342(11) 0.0583(13) 0.0319(10) -0.0122(9) 0.0081(8) -0.0033(9)
C17 0.0289(10) 0.0491(11) 0.0295(9) -0.0033(8) 0.0061(7) 0.0023(8)
C18 0.0498(13) 0.0455(12) 0.0317(10) -0.0040(9) 0.0109(9) -0.0107(9)
F19 0.0742(10) 0.0533(8) 0.0619(9) -0.0006(6) 0.0030(7) -0.0298(7)
F20 0.0798(11) 0.0489(8) 0.0911(11) 0.0148(7) 0.0385(9) 0.0151(7)
F21 0.1204(13) 0.0503(8) 0.0313(7) 0.0045(6) 0.0116(7) -0.0182(7)
N1 0.0405(9) 0.0442(10) 0.0276(8) -0.0022(7) 0.0075(7) -0.0036(7)
N3 0.0259(8) 0.0386(8) 0.0241(7) 0.0011(6) 0.0059(6) 0.0003(6)
N4 0.0320(8) 0.0387(9) 0.0264(8) 0.0015(6) 0.0068(6) -0.0021(6)

_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
C2 H2 0.9300 . ?
C2 N1 1.316(2) . ?
C2 N3 1.342(2) . ?
C5 C18 1.487(3) . ?
C5 N1 1.349(2) . ?
C5 N4 1.315(2) . ?
C6 C7 1.380(2) . ?
C6 C11 1.386(2) . ?
C6 N3 1.429(2) . ?
C7 H7 0.9300 . ?
C7 C8 1.378(2) . ?
C8 H8 0.9300 . ?
C8 C9 1.397(2) . ?
C9 C10 1.396(2) . ?
C9 C12 1.482(2) . ?
C10 H10 0.9300 . ?
C10 C11 1.378(3) . ?
C11 H11 0.9300 . ?
C12 C13 1.394(2) . ?
C12 C17 1.399(2) . ?
C13 H13 0.9300 . ?
C13 C14 1.380(3) . ?
C14 H14 0.9300 . ?
C14 C15 1.383(3) . ?
C15 H15 0.9300 . ?
C15 C16 1.372(3) . ?
C16 H16 0.9300 . ?
C16 C17 1.389(3) . ?
C17 H17 0.9300 . ?
C18 F19 1.325(2) . ?
C18 F20 1.331(2) . ?
C18 F21 1.325(2) . ?
N3 N4 1.3566(19) . ?

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
N1 C2 H2 124.3 . . ?
N1 C2 N3 111.39(16) . . ?
N3 C2 H2 124.3 . . ?
N1 C5 C18 121.77(16) . . ?
N4 C5 C18 121.79(16) . . ?
N4 C5 N1 116.44(16) . . ?
C7 C6 C11 120.59(16) . . ?
C7 C6 N3 120.00(15) . . ?
C11 C6 N3 119.40(15) . . ?
C6 C7 H7 120.2 . . ?
C8 C7 C6 119.64(15) . . ?
C8 C7 H7 120.2 . . ?
C7 C8 H8 119.3 . . ?
C7 C8 C9 121.42(16) . . ?
C9 C8 H8 119.3 . . ?
C8 C9 C12 120.73(15) . . ?
C10 C9 C8 117.40(16) . . ?
C10 C9 C12 121.87(15) . . ?
C9 C10 H10 119.1 . . ?
C11 C10 C9 121.86(16) . . ?
C11 C10 H10 119.1 . . ?
C6 C11 H11 120.5 . . ?
C10 C11 C6 119.09(16) . . ?
C10 C11 H11 120.5 . . ?
C13 C12 C9 121.12(15) . . ?
C13 C12 C17 117.76(17) . . ?
C17 C12 C9 121.11(16) . . ?
C12 C13 H13 119.5 . . ?
C14 C13 C12 121.02(18) . . ?
C14 C13 H13 119.5 . . ?
C13 C14 H14 119.8 . . ?
C13 C14 C15 120.37(19) . . ?
C15 C14 H14 119.8 . . ?
C14 C15 H15 120.1 . . ?
C16 C15 C14 119.78(18) . . ?
C16 C15 H15 120.1 . . ?
C15 C16 H16 119.9 . . ?
C15 C16 C17 120.20(18) . . ?
C17 C16 H16 119.9 . . ?
C12 C17 H17 119.6 . . ?
C16 C17 C12 120.87(18) . . ?
C16 C17 H17 119.6 . . ?
F19 C18 C5 111.94(18) . . ?
F19 C18 F20 105.25(17) . . ?
F20 C18 C5 112.79(16) . . ?
F21 C18 C5 112.16(16) . . ?
F21 C18 F19 107.32(16) . . ?
F21 C18 F20 106.93(18) . . ?
C2 N1 C5 101.39(15) . . ?
C2 N3 C6 129.50(15) . . ?
C2 N3 N4 108.99(14) . . ?
N4 N3 C6 121.49(14) . . ?
C5 N4 N3 101.79(14) . . ?

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 N3 N4 C5 0.16(18) . . . . ?
C6 C7 C8 C9 0.7(3) . . . . ?
C6 N3 N4 C5 178.48(14) . . . . ?
C7 C6 C11 C10 -0.2(3) . . . . ?
C7 C6 N3 C2 -27.1(3) . . . . ?
C7 C6 N3 N4 154.93(15) . . . . ?
C7 C8 C9 C10 -0.7(3) . . . . ?
C7 C8 C9 C12 178.77(16) . . . . ?
C8 C9 C10 C11 0.3(2) . . . . ?
C8 C9 C12 C13 30.4(2) . . . . ?
C8 C9 C12 C17 -148.24(17) . . . . ?
C9 C10 C11 C6 0.2(3) . . . . ?
C9 C12 C13 C14 -177.75(16) . . . . ?
C9 C12 C17 C16 177.69(16) . . . . ?
C10 C9 C12 C13 -150.16(17) . . . . ?
C10 C9 C12 C17 31.2(2) . . . . ?
C11 C6 C7 C8 -0.2(3) . . . . ?
C11 C6 N3 C2 151.96(18) . . . . ?
C11 C6 N3 N4 -26.0(2) . . . . ?
C12 C9 C10 C11 -179.19(16) . . . . ?
C12 C13 C14 C15 -0.2(3) . . . . ?
C13 C12 C17 C16 -1.0(2) . . . . ?
C13 C14 C15 C16 -0.5(3) . . . . ?
C14 C15 C16 C17 0.5(3) . . . . ?
C15 C16 C17 C12 0.3(3) . . . . ?
C17 C12 C13 C14 0.9(3) . . . . ?
C18 C5 N1 C2 -179.40(17) . . . . ?
C18 C5 N4 N3 179.19(16) . . . . ?
N1 C2 N3 C6 -178.52(15) . . . . ?
N1 C2 N3 N4 -0.4(2) . . . . ?
N1 C5 C18 F19 -46.2(2) . . . . ?
N1 C5 C18 F20 72.3(2) . . . . ?
N1 C5 C18 F21 -166.92(17) . . . . ?
N1 C5 N4 N3 0.10(19) . . . . ?
N3 C2 N1 C5 0.4(2) . . . . ?
N3 C6 C7 C8 178.87(15) . . . . ?
N3 C6 C11 C10 -179.29(15) . . . . ?
N4 C5 C18 F19 134.75(18) . . . . ?
N4 C5 C18 F20 -106.8(2) . . . . ?
N4 C5 C18 F21 14.0(3) . . . . ?
N4 C5 N1 C2 -0.3(2) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
