# Supplementary Information (SI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2025

####################################################################### 
# 
# 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_exp_9512
_database_code_depnum_ccdc_archive 'CCDC 2463469'
loop_
_audit_author_name
_audit_author_address
'Cong Li'
;Beijing Institute of Technology
China
;
_audit_update_record             
;
2025-06-11 deposited with the CCDC.	2025-07-15 downloaded from the CCDC.
;
_audit_creation_date             2024-11-14
_audit_creation_method           
;
  Olex2 1.1
  (compiled 2011.02.15 svn.r1672, GUI svn.r3494)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C3 H2 I N3 O2'
_chemical_formula_sum            'C3 H2 I N3 O2'
_chemical_formula_weight         238.98
_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'
I I -0.4742 1.8119 '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'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, -y, -z'

_cell_length_a                   8.9073(6)
_cell_length_b                   16.8666(11)
_cell_length_c                   20.2753(13)
_cell_angle_alpha                67.857(6)
_cell_angle_beta                 87.035(6)
_cell_angle_gamma                77.872(6)
_cell_volume                     2757.2(3)
_cell_formula_units_Z            18
_cell_measurement_reflns_used    3550
_cell_measurement_temperature    117.95(10)
_cell_measurement_theta_max      25.1800
_cell_measurement_theta_min      3.3040
_exptl_absorpt_coefficient_mu    5.151
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.80261
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    2.591
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             1980
_exptl_crystal_size_max          0.09
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.03
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0803
_diffrn_reflns_av_unetI/netI     0.1446
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            22312
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         2.92
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      117.95(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0971
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.9982
_diffrn_measured_fraction_theta_max 0.8153
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega   -1.00   82.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       15.9289   57.0000    0.0000 83

#__ type_ start__ end____ width___ exp.time_
  2 omega   26.00   65.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       15.9289   57.0000   60.0000 39

#__ type_ start__ end____ width___ exp.time_
  3 omega  -26.00   25.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       15.9289  -57.0000   90.0000 51

#__ type_ start__ end____ width___ exp.time_
  4 omega  -25.00   16.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      -10.8508  -99.0000  150.0000 41

#__ type_ start__ end____ width___ exp.time_
  5 omega  -25.00    0.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      -10.8508  -99.0000  -30.0000 25

#__ type_ start__ end____ width___ exp.time_
  6 omega    5.00   45.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       15.9289   57.0000 -120.0000 40

#__ type_ start__ end____ width___ exp.time_
  7 omega   35.00   75.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       15.9289  178.0000 -120.0000 40

#__ type_ start__ end____ width___ exp.time_
  8 omega  -44.00   35.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       15.9289  -37.0000 -150.0000 79
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0439668000
_diffrn_orient_matrix_UB_12      -0.0310253000
_diffrn_orient_matrix_UB_13      -0.0129633000
_diffrn_orient_matrix_UB_21      0.0044648000
_diffrn_orient_matrix_UB_22      -0.0328282000
_diffrn_orient_matrix_UB_23      0.0347461000
_diffrn_orient_matrix_UB_31      -0.0684917000
_diffrn_orient_matrix_UB_32      -0.0106624000
_diffrn_orient_matrix_UB_33      -0.0074489000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                6440
_reflns_number_total             10575
_reflns_odcompleteness_completeness 99.82
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     25.07
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_molecular_graphics    
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material  
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    
'A short history of SHELX (Sheldrick, 2007)/Bruker'
_refine_diff_density_max         2.106
_refine_diff_density_min         -1.432
_refine_diff_density_rms         0.292
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     730
_refine_ls_number_reflns         10575
_refine_ls_number_restraints     432
_refine_ls_R_factor_all          0.1125
_refine_ls_R_factor_gt           0.0632
_refine_ls_restrained_S_all      1.025
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0116P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0943
_refine_ls_wR_factor_ref         0.1249
_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. 
;
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
I1 I 0.01045(9) -0.55294(6) 1.85174(5) 0.0256(2) Uani 1 1 d . . .
O1 O 0.2761(9) -0.7350(6) 1.9258(5) 0.029(2) Uani 1 1 d U . .
O2 O 0.3122(10) -0.8148(6) 2.0382(5) 0.036(2) Uani 1 1 d U . .
N1 N -0.0727(11) -0.5830(7) 1.9991(6) 0.0231(18) Uani 1 1 d U . .
N2 N -0.0415(10) -0.6391(6) 2.0678(6) 0.0230(18) Uani 1 1 d U . .
H2 H -0.0923 -0.6312 2.1039 0.028 Uiso 1 1 calc R . .
N3 N 0.2444(11) -0.7506(7) 1.9886(6) 0.0254(19) Uani 1 1 d U . .
C1 C 0.0291(13) -0.6175(8) 1.9601(7) 0.0213(19) Uani 1 1 d U . .
C2 C 0.1175(13) -0.6934(8) 2.0064(7) 0.0235(18) Uani 1 1 d U . .
C3 C 0.0743(13) -0.7080(8) 2.0754(7) 0.026(2) Uani 1 1 d U . .
H3 H 0.1158 -0.7550 2.1179 0.031 Uiso 1 1 calc R . .
I2 I -0.07977(9) -0.74023(6) 2.28281(5) 0.0268(2) Uani 1 1 d . . .
O3 O -0.2970(10) -0.6467(6) 2.3836(5) 0.035(2) Uani 1 1 d U . .
O4 O -0.5009(11) -0.5445(6) 2.3503(5) 0.048(3) Uani 1 1 d U . .
N4 N -0.2596(11) -0.5971(6) 2.1648(5) 0.0209(17) Uani 1 1 d U . .
N5 N -0.3813(11) -0.5268(6) 2.1495(6) 0.0221(17) Uani 1 1 d U . .
H5 H -0.4137 -0.4920 2.1059 0.027 Uiso 1 1 calc R . .
N6 N -0.3903(13) -0.5904(7) 2.3374(6) 0.031(2) Uani 1 1 d U . .
C4 C -0.2501(14) -0.6303(8) 2.2355(7) 0.0233(19) Uani 1 1 d U . .
C5 C -0.3638(14) -0.5796(8) 2.2646(7) 0.0258(18) Uani 1 1 d U . .
C6 C -0.4441(14) -0.5171(8) 2.2070(7) 0.0248(19) Uani 1 1 d U . .
H6 H -0.5308 -0.4737 2.2078 0.030 Uiso 1 1 calc R . .
I3 I -0.66357(9) -0.29580(6) 2.02924(5) 0.0264(2) Uani 1 1 d . . .
O5 O -0.7067(10) -0.2080(6) 1.8530(5) 0.033(2) Uani 1 1 d U . .
O6 O -0.5339(10) -0.2247(6) 1.7770(5) 0.041(2) Uani 1 1 d U . .
N7 N -0.4063(11) -0.4156(7) 1.9991(6) 0.0270(18) Uani 1 1 d U . .
N8 N -0.3206(11) -0.4325(7) 1.9474(5) 0.0246(18) Uani 1 1 d U . .
H8 H -0.2424 -0.4770 1.9557 0.029 Uiso 1 1 calc R . .
N9 N -0.5852(12) -0.2444(7) 1.8369(6) 0.0288(19) Uani 1 1 d U . .
C7 C -0.5117(14) -0.3459(9) 1.9650(7) 0.027(2) Uani 1 1 d U . .
C8 C -0.4866(14) -0.3166(9) 1.8925(7) 0.0266(18) Uani 1 1 d U . .
C9 C -0.3675(14) -0.3735(8) 1.8811(7) 0.028(2) Uani 1 1 d U . .
H9 H -0.3258 -0.3725 1.8368 0.033 Uiso 1 1 calc R . .
I4 I -1.08189(10) 0.16068(6) 1.48882(5) 0.0308(2) Uani 1 1 d . . .
O7 O -0.7608(9) 0.0107(6) 1.5316(5) 0.035(2) Uani 1 1 d U . .
O8 O -0.6860(9) -0.0867(6) 1.6374(5) 0.035(2) Uani 1 1 d U . .
N10 N -1.1089(11) 0.1024(7) 1.6452(6) 0.0263(18) Uani 1 1 d U . .
N11 N -1.0466(11) 0.0460(7) 1.7077(6) 0.0243(18) Uani 1 1 d U . .
H11 H -1.0842 0.0442 1.7491 0.029 Uiso 1 1 calc R . .
N12 N -0.7754(12) -0.0226(8) 1.5967(6) 0.0301(19) Uani 1 1 d U . .
C10 C -1.0240(13) 0.0892(8) 1.5932(7) 0.0221(19) Uani 1 1 d U . .
C11 C -0.8979(14) 0.0185(8) 1.6266(7) 0.0247(18) Uani 1 1 d U . .
C12 C -0.9219(13) -0.0069(8) 1.6999(7) 0.0232(19) Uani 1 1 d U . .
H12 H -0.8598 -0.0534 1.7369 0.028 Uiso 1 1 calc R . .
I5 I -0.97916(9) -0.08524(6) 1.91933(5) 0.0300(2) Uani 1 1 d . . .
O9 O -1.2166(10) -0.0643(6) 2.0453(5) 0.037(2) Uani 1 1 d U . .
O10 O -1.4077(9) 0.0451(6) 2.0362(5) 0.030(2) Uani 1 1 d U . .
N13 N -1.1920(11) 0.0697(7) 1.8268(6) 0.0255(18) Uani 1 1 d U . .
N14 N -1.3210(11) 0.1316(7) 1.8259(6) 0.0257(18) Uani 1 1 d U . .
H14 H -1.3618 0.1756 1.7873 0.031 Uiso 1 1 calc R . .
N15 N -1.3020(12) 0.0043(7) 2.0112(6) 0.0290(19) Uani 1 1 d U . .
C13 C -1.1691(14) 0.0162(8) 1.8944(7) 0.025(2) Uani 1 1 d U . .
C14 C -1.2823(14) 0.0453(8) 1.9361(7) 0.0257(18) Uani 1 1 d U . .
C15 C -1.3771(14) 0.1162(8) 1.8918(7) 0.0235(19) Uani 1 1 d U . .
H15 H -1.4662 0.1491 1.9043 0.028 Uiso 1 1 calc R . .
I6 I -1.66513(9) 0.34559(6) 1.74736(5) 0.0285(2) Uani 1 1 d . . .
O11 O -1.7598(10) 0.4661(6) 1.5783(5) 0.043(2) Uani 1 1 d U . .
O12 O -1.6422(10) 0.4546(7) 1.4862(6) 0.049(3) Uani 1 1 d U . .
N16 N -1.4315(10) 0.2464(7) 1.6861(6) 0.0243(18) Uani 1 1 d U . .
N17 N -1.3714(11) 0.2399(7) 1.6244(6) 0.0237(18) Uani 1 1 d U . .
H17 H -1.2966 0.1974 1.6227 0.028 Uiso 1 1 calc R . .
N18 N -1.6585(12) 0.4307(7) 1.5511(6) 0.0300(19) Uani 1 1 d U . .
C16 C -1.5443(13) 0.3153(8) 1.6692(7) 0.0231(19) Uani 1 1 d U . .
C17 C -1.5515(13) 0.3530(9) 1.5934(7) 0.0257(18) Uani 1 1 d U . .
C18 C -1.4417(13) 0.3071(8) 1.5660(7) 0.026(2) Uani 1 1 d U . .
H18 H -1.4188 0.3190 1.5173 0.031 Uiso 1 1 calc R . .
I7 I -0.83058(9) -0.40484(5) 2.37471(5) 0.0262(2) Uani 1 1 d . . .
O13 O -0.9025(10) -0.2234(6) 2.1174(5) 0.033(2) Uani 1 1 d U . .
O14 O -0.7626(9) -0.3284(6) 2.2032(5) 0.030(2) Uani 1 1 d U . .
N19 N -1.0852(11) -0.2527(6) 2.3338(5) 0.0198(17) Uani 1 1 d U . .
N20 N -1.1586(11) -0.1828(6) 2.2785(5) 0.0205(17) Uani 1 1 d U . .
H20 H -1.2373 -0.1441 2.2833 0.025 Uiso 1 1 calc R . .
N21 N -0.8733(11) -0.2685(7) 2.1813(6) 0.0250(19) Uani 1 1 d U . .
C19 C -0.9730(13) -0.2933(8) 2.3061(7) 0.0213(19) Uani 1 1 d U . .
C20 C -0.9756(13) -0.2490(8) 2.2330(7) 0.0234(18) Uani 1 1 d U . .
C21 C -1.0996(13) -0.1789(8) 2.2168(7) 0.0222(19) Uani 1 1 d U . .
H21 H -1.1345 -0.1370 2.1710 0.027 Uiso 1 1 calc R . .
I8 I -1.44314(9) -0.20737(6) 2.60477(5) 0.0274(2) Uani 1 1 d . . .
O15 O -1.0063(10) -0.4577(6) 2.6923(5) 0.032(2) Uani 1 1 d U . .
O16 O -1.2244(11) -0.3883(6) 2.7164(5) 0.042(2) Uani 1 1 d U . .
N22 N -1.2602(11) -0.2512(7) 2.4958(6) 0.0233(18) Uani 1 1 d U . .
N23 N -1.1375(11) -0.3079(6) 2.4848(6) 0.0256(18) Uani 1 1 d U . .
H23 H -1.1071 -0.3054 2.4422 0.031 Uiso 1 1 calc R . .
N24 N -1.1286(12) -0.4024(7) 2.6740(6) 0.0267(19) Uani 1 1 d U . .
C22 C -1.2716(13) -0.2795(8) 2.5664(7) 0.0213(19) Uani 1 1 d U . .
C23 C -1.1540(14) -0.3539(8) 2.6003(7) 0.0228(17) Uani 1 1 d U . .
C24 C -1.0658(14) -0.3696(8) 2.5469(7) 0.0237(19) Uani 1 1 d U . .
H24 H -0.9756 -0.4132 2.5519 0.028 Uiso 1 1 calc R . .
I9 I -1.46883(9) 0.02423(6) 2.18114(5) 0.0260(2) Uani 1 1 d . . .
O17 O -1.8321(9) 0.0987(6) 2.3512(5) 0.030(2) Uani 1 1 d U . .
O18 O -1.7654(10) 0.1283(6) 2.2414(5) 0.040(2) Uani 1 1 d U . .
N25 N -1.4041(11) -0.0850(7) 2.3324(5) 0.0219(18) Uani 1 1 d U . .
N26 N -1.4507(11) -0.0974(7) 2.3994(6) 0.0240(18) Uani 1 1 d U . .
H26 H -1.4030 -0.1389 2.4377 0.029 Uiso 1 1 calc R . .
N27 N -1.7443(11) 0.0856(7) 2.3051(6) 0.0260(19) Uani 1 1 d U . .
C25 C -1.5030(13) -0.0157(8) 2.2883(7) 0.0215(19) Uani 1 1 d U . .
C26 C -1.6150(13) 0.0137(8) 2.3310(7) 0.0242(18) Uani 1 1 d U . .
C27 C -1.5763(13) -0.0401(8) 2.4009(7) 0.0226(19) Uani 1 1 d U . .
H27 H -1.6292 -0.0366 2.4419 0.027 Uiso 1 1 calc R . .


_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
I1 C1 2.049(13) . ?
O1 N3 1.229(12) . ?
O2 N3 1.231(13) . ?
N1 N2 1.359(13) . ?
N1 C1 1.355(14) . ?
N2 H2 0.8800 . ?
N2 C3 1.347(15) . ?
N3 C2 1.449(15) . ?
C1 C2 1.373(17) . ?
C2 C3 1.375(16) . ?
C3 H3 0.9500 . ?
I2 C4 2.071(13) . ?
O3 N6 1.244(13) . ?
O4 N6 1.202(12) . ?
N4 N5 1.376(13) . ?
N4 C4 1.327(15) . ?
N5 H5 0.8800 . ?
N5 C6 1.317(14) . ?
N6 C5 1.432(15) . ?
C4 C5 1.435(16) . ?
C5 C6 1.352(17) . ?
C6 H6 0.9500 . ?
I3 C7 2.100(13) . ?
O5 N9 1.221(12) . ?
O6 N9 1.224(12) . ?
N7 N8 1.347(13) . ?
N7 C7 1.315(16) . ?
N8 H8 0.8800 . ?
N8 C9 1.360(15) . ?
N9 C8 1.464(17) . ?
C7 C8 1.385(16) . ?
C8 C9 1.346(17) . ?
C9 H9 0.9500 . ?
I4 C10 2.031(13) . ?
O7 N12 1.236(13) . ?
O8 N12 1.232(13) . ?
N10 N11 1.327(14) . ?
N10 C10 1.326(14) . ?
N11 H11 0.8800 . ?
N11 C12 1.314(14) . ?
N12 C11 1.403(15) . ?
C10 C11 1.432(17) . ?
C11 C12 1.401(16) . ?
C12 H12 0.9500 . ?
I5 C13 2.066(13) . ?
O9 N15 1.216(13) . ?
O10 N15 1.248(12) . ?
N13 N14 1.375(13) . ?
N13 C13 1.324(15) . ?
N14 H14 0.8800 . ?
N14 C15 1.352(14) . ?
N15 C14 1.434(15) . ?
C13 C14 1.410(16) . ?
C14 C15 1.339(17) . ?
C15 H15 0.9500 . ?
I6 C16 2.034(12) . ?
O11 N18 1.203(12) . ?
O12 N18 1.233(13) . ?
N16 N17 1.369(13) . ?
N16 C16 1.313(15) . ?
N17 H17 0.8800 . ?
N17 C18 1.358(16) . ?
N18 C17 1.440(16) . ?
C16 C17 1.422(17) . ?
C17 C18 1.348(16) . ?
C18 H18 0.9500 . ?
I7 C19 2.071(13) . ?
O13 N21 1.240(12) . ?
O14 N21 1.216(12) . ?
N19 N20 1.353(13) . ?
N19 C19 1.314(14) . ?
N20 H20 0.8800 . ?
N20 C21 1.316(14) . ?
N21 C20 1.439(15) . ?
C19 C20 1.385(16) . ?
C20 C21 1.386(16) . ?
C21 H21 0.9500 . ?
I8 C22 2.056(11) . ?
O15 N24 1.244(13) . ?
O16 N24 1.232(12) . ?
N22 N23 1.362(12) . ?
N22 C22 1.333(15) . ?
N23 H23 0.8800 . ?
N23 C24 1.375(15) . ?
N24 C23 1.411(16) . ?
C22 C23 1.421(17) . ?
C23 C24 1.378(15) . ?
C24 H24 0.9500 . ?
I9 C25 2.045(12) . ?
O17 N27 1.242(12) . ?
O18 N27 1.220(13) . ?
N25 N26 1.352(13) . ?
N25 C25 1.343(15) . ?
N26 H26 0.8800 . ?
N26 C27 1.323(14) . ?
N27 C26 1.439(16) . ?
C25 C26 1.420(15) . ?
C26 C27 1.379(17) . ?
C27 H27 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
C1 N1 N2 105.2(10) . . ?
N1 N2 H2 123.1 . . ?
C3 N2 N1 113.9(10) . . ?
C3 N2 H2 123.1 . . ?
O1 N3 O2 123.4(11) . . ?
O1 N3 C2 119.5(11) . . ?
O2 N3 C2 117.1(10) . . ?
N1 C1 I1 116.6(9) . . ?
N1 C1 C2 107.7(11) . . ?
C2 C1 I1 135.7(10) . . ?
C1 C2 N3 126.9(12) . . ?
C1 C2 C3 110.6(12) . . ?
C3 C2 N3 122.4(12) . . ?
N2 C3 C2 102.8(12) . . ?
N2 C3 H3 128.6 . . ?
C2 C3 H3 128.6 . . ?
C4 N4 N5 103.6(10) . . ?
N4 N5 H5 123.5 . . ?
C6 N5 N4 113.0(11) . . ?
C6 N5 H5 123.5 . . ?
O3 N6 C5 118.0(11) . . ?
O4 N6 O3 123.9(11) . . ?
O4 N6 C5 118.1(12) . . ?
N4 C4 I2 116.9(9) . . ?
N4 C4 C5 110.9(11) . . ?
C5 C4 I2 132.2(10) . . ?
N6 C5 C4 129.3(12) . . ?
C6 C5 N6 126.4(12) . . ?
C6 C5 C4 104.4(12) . . ?
N5 C6 C5 108.1(12) . . ?
N5 C6 H6 125.9 . . ?
C5 C6 H6 125.9 . . ?
C7 N7 N8 104.7(11) . . ?
N7 N8 H8 123.6 . . ?
N7 N8 C9 112.9(11) . . ?
C9 N8 H8 123.6 . . ?
O5 N9 O6 125.5(12) . . ?
O5 N9 C8 119.4(11) . . ?
O6 N9 C8 115.1(11) . . ?
N7 C7 I3 115.8(9) . . ?
N7 C7 C8 110.2(12) . . ?
C8 C7 I3 133.6(10) . . ?
C7 C8 N9 126.2(12) . . ?
C9 C8 N9 125.3(12) . . ?
C9 C8 C7 107.9(13) . . ?
N8 C9 H9 127.9 . . ?
C8 C9 N8 104.2(11) . . ?
C8 C9 H9 127.9 . . ?
C10 N10 N11 109.6(11) . . ?
N10 N11 H11 124.3 . . ?
C12 N11 N10 111.5(10) . . ?
C12 N11 H11 124.3 . . ?
O7 N12 C11 117.5(12) . . ?
O8 N12 O7 124.5(11) . . ?
O8 N12 C11 117.9(11) . . ?
N10 C10 I4 122.1(10) . . ?
N10 C10 C11 106.6(12) . . ?
C11 C10 I4 131.3(9) . . ?
N12 C11 C10 130.5(12) . . ?
C12 C11 N12 124.2(12) . . ?
C12 C11 C10 105.4(11) . . ?
N11 C12 C11 107.0(12) . . ?
N11 C12 H12 126.5 . . ?
C11 C12 H12 126.5 . . ?
C13 N13 N14 105.1(10) . . ?
N13 N14 H14 124.3 . . ?
C15 N14 N13 111.4(11) . . ?
C15 N14 H14 124.3 . . ?
O9 N15 O10 125.4(11) . . ?
O9 N15 C14 119.6(11) . . ?
O10 N15 C14 115.1(11) . . ?
N13 C13 I5 117.4(9) . . ?
N13 C13 C14 109.6(12) . . ?
C14 C13 I5 133.0(10) . . ?
C13 C14 N15 127.4(12) . . ?
C15 C14 N15 125.1(12) . . ?
C15 C14 C13 107.4(12) . . ?
N14 C15 H15 126.8 . . ?
C14 C15 N14 106.4(11) . . ?
C14 C15 H15 126.8 . . ?
C16 N16 N17 108.2(11) . . ?
N16 N17 H17 124.2 . . ?
C18 N17 N16 111.7(10) . . ?
C18 N17 H17 124.2 . . ?
O11 N18 O12 123.6(12) . . ?
O11 N18 C17 121.1(12) . . ?
O12 N18 C17 115.2(11) . . ?
N16 C16 I6 119.8(10) . . ?
N16 C16 C17 105.8(11) . . ?
C17 C16 I6 134.5(9) . . ?
C16 C17 N18 125.2(11) . . ?
C18 C17 N18 124.0(13) . . ?
C18 C17 C16 110.7(12) . . ?
N17 C18 H18 128.2 . . ?
C17 C18 N17 103.6(12) . . ?
C17 C18 H18 128.2 . . ?
C19 N19 N20 106.0(10) . . ?
N19 N20 H20 123.7 . . ?
C21 N20 N19 112.6(10) . . ?
C21 N20 H20 123.7 . . ?
O13 N21 C20 118.4(10) . . ?
O14 N21 O13 123.7(11) . . ?
O14 N21 C20 117.8(11) . . ?
N19 C19 I7 117.9(9) . . ?
N19 C19 C20 109.5(11) . . ?
C20 C19 I7 132.7(9) . . ?
C19 C20 N21 128.9(12) . . ?
C19 C20 C21 106.6(11) . . ?
C21 C20 N21 124.5(12) . . ?
N20 C21 C20 105.3(12) . . ?
N20 C21 H21 127.4 . . ?
C20 C21 H21 127.4 . . ?
C22 N22 N23 104.6(10) . . ?
N22 N23 H23 123.3 . . ?
N22 N23 C24 113.3(10) . . ?
C24 N23 H23 123.3 . . ?
O15 N24 C23 116.4(10) . . ?
O16 N24 O15 123.6(12) . . ?
O16 N24 C23 120.0(11) . . ?
N22 C22 I8 116.3(9) . . ?
N22 C22 C23 110.7(10) . . ?
C23 C22 I8 132.9(10) . . ?
N24 C23 C22 127.6(11) . . ?
C24 C23 N24 125.9(12) . . ?
C24 C23 C22 106.6(12) . . ?
N23 C24 C23 104.7(11) . . ?
N23 C24 H24 127.7 . . ?
C23 C24 H24 127.7 . . ?
C25 N25 N26 106.9(10) . . ?
N25 N26 H26 123.8 . . ?
C27 N26 N25 112.4(11) . . ?
C27 N26 H26 123.8 . . ?
O17 N27 C26 115.6(11) . . ?
O18 N27 O17 123.7(11) . . ?
O18 N27 C26 120.7(11) . . ?
N25 C25 I9 118.5(8) . . ?
N25 C25 C26 107.4(11) . . ?
C26 C25 I9 134.1(10) . . ?
C25 C26 N27 125.8(12) . . ?
C27 C26 N27 127.3(11) . . ?
C27 C26 C25 106.9(11) . . ?
N26 C27 C26 106.3(11) . . ?
N26 C27 H27 126.9 . . ?
C26 C27 H27 126.9 . . ?

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
I1 C1 C2 N3 6(2) . . . . ?
I1 C1 C2 C3 -176.5(9) . . . . ?
O1 N3 C2 C1 -4.0(19) . . . . ?
O1 N3 C2 C3 178.9(11) . . . . ?
O2 N3 C2 C1 178.2(11) . . . . ?
O2 N3 C2 C3 1.0(17) . . . . ?
N1 N2 C3 C2 -0.1(13) . . . . ?
N1 C1 C2 N3 -177.8(11) . . . . ?
N1 C1 C2 C3 -0.4(14) . . . . ?
N2 N1 C1 I1 177.2(7) . . . . ?
N2 N1 C1 C2 0.3(12) . . . . ?
N3 C2 C3 N2 177.9(11) . . . . ?
C1 N1 N2 C3 -0.1(13) . . . . ?
C1 C2 C3 N2 0.3(14) . . . . ?
I2 C4 C5 N6 1(2) . . . . ?
I2 C4 C5 C6 -178.6(9) . . . . ?
O3 N6 C5 C4 6(2) . . . . ?
O3 N6 C5 C6 -173.7(12) . . . . ?
O4 N6 C5 C4 -173.8(13) . . . . ?
O4 N6 C5 C6 6(2) . . . . ?
N4 N5 C6 C5 1.9(14) . . . . ?
N4 C4 C5 N6 -177.7(11) . . . . ?
N4 C4 C5 C6 2.5(14) . . . . ?
N5 N4 C4 I2 179.5(7) . . . . ?
N5 N4 C4 C5 -1.4(13) . . . . ?
N6 C5 C6 N5 177.6(11) . . . . ?
C4 N4 N5 C6 -0.2(12) . . . . ?
C4 C5 C6 N5 -2.5(14) . . . . ?
I3 C7 C8 N9 -12(2) . . . . ?
I3 C7 C8 C9 176.6(10) . . . . ?
O5 N9 C8 C7 -4.6(19) . . . . ?
O5 N9 C8 C9 165.6(12) . . . . ?
O6 N9 C8 C7 173.7(12) . . . . ?
O6 N9 C8 C9 -16.1(18) . . . . ?
N7 N8 C9 C8 0.9(14) . . . . ?
N7 C7 C8 N9 175.7(11) . . . . ?
N7 C7 C8 C9 4.1(15) . . . . ?
N8 N7 C7 I3 -177.3(7) . . . . ?
N8 N7 C7 C8 -3.4(13) . . . . ?
N9 C8 C9 N8 -174.6(11) . . . . ?
C7 N7 N8 C9 1.5(13) . . . . ?
C7 C8 C9 N8 -2.9(14) . . . . ?
I4 C10 C11 N12 0(2) . . . . ?
I4 C10 C11 C12 -177.6(9) . . . . ?
O7 N12 C11 C10 8.2(19) . . . . ?
O7 N12 C11 C12 -174.4(11) . . . . ?
O8 N12 C11 C10 -175.2(12) . . . . ?
O8 N12 C11 C12 2.2(18) . . . . ?
N10 N11 C12 C11 1.8(13) . . . . ?
N10 C10 C11 N12 179.0(12) . . . . ?
N10 C10 C11 C12 1.3(13) . . . . ?
N11 N10 C10 I4 178.8(7) . . . . ?
N11 N10 C10 C11 -0.2(13) . . . . ?
N12 C11 C12 N11 -179.8(11) . . . . ?
C10 N10 N11 C12 -1.0(14) . . . . ?
C10 C11 C12 N11 -1.9(13) . . . . ?
I5 C13 C14 N15 -6(2) . . . . ?
I5 C13 C14 C15 178.4(10) . . . . ?
O9 N15 C14 C13 -1.6(19) . . . . ?
O9 N15 C14 C15 173.5(12) . . . . ?
O10 N15 C14 C13 177.2(12) . . . . ?
O10 N15 C14 C15 -7.6(18) . . . . ?
N13 N14 C15 C14 1.4(13) . . . . ?
N13 C13 C14 N15 177.7(11) . . . . ?
N13 C13 C14 C15 1.8(15) . . . . ?
N14 N13 C13 I5 -178.1(7) . . . . ?
N14 N13 C13 C14 -0.9(13) . . . . ?
N15 C14 C15 N14 -177.9(11) . . . . ?
C13 N13 N14 C15 -0.3(13) . . . . ?
C13 C14 C15 N14 -1.9(14) . . . . ?
I6 C16 C17 N18 0.6(19) . . . . ?
I6 C16 C17 C18 179.3(10) . . . . ?
O11 N18 C17 C16 -5.7(19) . . . . ?
O11 N18 C17 C18 175.7(12) . . . . ?
O12 N18 C17 C16 177.4(11) . . . . ?
O12 N18 C17 C18 -1.2(18) . . . . ?
N16 N17 C18 C17 -2.7(13) . . . . ?
N16 C16 C17 N18 -179.7(11) . . . . ?
N16 C16 C17 C18 -0.9(14) . . . . ?
N17 N16 C16 I6 179.0(7) . . . . ?
N17 N16 C16 C17 -0.8(13) . . . . ?
N18 C17 C18 N17 -179.0(10) . . . . ?
C16 N16 N17 C18 2.3(13) . . . . ?
C16 C17 C18 N17 2.2(14) . . . . ?
I7 C19 C20 N21 -1(2) . . . . ?
I7 C19 C20 C21 179.2(9) . . . . ?
O13 N21 C20 C19 175.1(11) . . . . ?
O13 N21 C20 C21 -4.8(18) . . . . ?
O14 N21 C20 C19 -5.1(19) . . . . ?
O14 N21 C20 C21 175.0(11) . . . . ?
N19 N20 C21 C20 -2.4(13) . . . . ?
N19 C19 C20 N21 178.7(12) . . . . ?
N19 C19 C20 C21 -1.4(14) . . . . ?
N20 N19 C19 I7 179.5(7) . . . . ?
N20 N19 C19 C20 -0.1(13) . . . . ?
N21 C20 C21 N20 -177.8(11) . . . . ?
C19 N19 N20 C21 1.6(13) . . . . ?
C19 C20 C21 N20 2.2(13) . . . . ?
I8 C22 C23 N24 3(2) . . . . ?
I8 C22 C23 C24 -175.7(9) . . . . ?
O15 N24 C23 C22 -170.3(12) . . . . ?
O15 N24 C23 C24 8.6(18) . . . . ?
O16 N24 C23 C22 8.9(19) . . . . ?
O16 N24 C23 C24 -172.1(12) . . . . ?
N22 N23 C24 C23 3.6(14) . . . . ?
N22 C22 C23 N24 -179.6(11) . . . . ?
N22 C22 C23 C24 1.3(14) . . . . ?
N23 N22 C22 I8 178.4(7) . . . . ?
N23 N22 C22 C23 0.8(13) . . . . ?
N24 C23 C24 N23 178.1(11) . . . . ?
C22 N22 N23 C24 -2.7(13) . . . . ?
C22 C23 C24 N23 -2.8(13) . . . . ?
I9 C25 C26 N27 1(2) . . . . ?
I9 C25 C26 C27 -179.8(9) . . . . ?
O17 N27 C26 C25 177.5(11) . . . . ?
O17 N27 C26 C27 -1.9(18) . . . . ?
O18 N27 C26 C25 -0.6(19) . . . . ?
O18 N27 C26 C27 180.0(12) . . . . ?
N25 N26 C27 C26 -0.3(14) . . . . ?
N25 C25 C26 N27 -178.7(11) . . . . ?
N25 C25 C26 C27 0.8(14) . . . . ?
N26 N25 C25 I9 179.5(7) . . . . ?
N26 N25 C25 C26 -1.0(13) . . . . ?
N27 C26 C27 N26 179.2(11) . . . . ?
C25 N25 N26 C27 0.8(13) . . . . ?
C25 C26 C27 N26 -0.3(14) . . . . ?

_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: ethyl acetate'
####################################################################### 
# 
# 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 2463470'
loop_
_audit_author_name
_audit_author_address
'Cong Li'
;Beijing Institute of Technology
China
;
_audit_update_record             
;
2025-06-11 deposited with the CCDC.	2025-07-15 downloaded from the CCDC.
;
_audit_creation_date             2025-02-23
_audit_creation_method           
;
Olex2 1.5-ac6-020
(compiled 2024.02.14 svn.r2f8d729c for Rigaku Oxford Diffraction, GUI svn.r6966)
;
_shelx_SHELXL_version_number     2018/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C8 H6 F2 N4 O2'
_chemical_formula_sum            'C8 H6 F2 N4 O2'
_chemical_formula_weight         228.17
_chemical_melting_point          ?
_chemical_oxdiff_formula         chonf
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'

_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/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   6.8400(3)
_cell_length_b                   18.3788(8)
_cell_length_c                   7.3602(4)
_cell_angle_alpha                90
_cell_angle_beta                 99.490(4)
_cell_angle_gamma                90
_cell_volume                     912.60(8)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3219
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      70.3770
_cell_measurement_theta_min      4.7660
_shelx_estimated_absorpt_T_max   0.868
_shelx_estimated_absorpt_T_min   0.778
_exptl_absorpt_coefficient_mu    1.323
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.70071
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.43.127a (Rigaku Oxford Diffraction, 2024)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.661
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             464
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.11
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0227
_diffrn_reflns_av_unetI/netI     0.0232
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.972
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_number            4179
_diffrn_reflns_point_group_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.972
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         70.513
_diffrn_reflns_theta_min         4.812
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.972
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -57.00 -17.00   0.50    0.05    --  -97.00  50.00  60.00   80
  2  ω    -45.00 -16.00   0.50    0.05    --  -97.00  38.00   0.00   58
  3  ω    -42.00 -16.00   0.50    0.05    --  -97.00  38.00 -30.00   52
  4  ω    -43.00 -18.00   0.50    0.05    --  -97.00  38.00 -60.00   50
  5  ω    -44.00 -14.00   0.50    0.05    --  -97.00  38.00-150.00   60
  6  ω    -46.00 -20.00   0.50    0.05    --  -97.00  38.00-180.00   52
  7  ω    -46.00 -21.00   0.50    0.05    --  -97.00  38.00-120.00   50
  8  ω    -15.00  22.00   0.50    0.05    --  -56.47  15.00-150.00   74
  9  ω    -26.00  25.00   0.50    0.05    --  -56.47  15.00 -30.00  102
 10  ω    -33.00  13.00   0.50    0.05    --  -56.47  30.00  90.00   92
 11  ω    -43.00 -18.00   0.50    0.05    --  -97.00  38.00 120.00   50
 12  ω    -45.00 -19.00   0.50    0.05    --  -97.00  38.00 150.00   52
 13  ω   -103.00 -50.00   0.50    0.05    --  -56.47 101.00 122.00  106
 14  ω   -121.00 -95.00   0.50    0.05    --  -56.47-101.00  18.00   52
 15  ω   -155.00-124.00   0.50    0.05    --  -56.47-101.00  18.00   62
 16  ω   -157.00-132.00   0.50    0.05    --  -97.00-101.00  18.00   50
 17  ω   -129.00-103.00   0.50    0.05    --  -97.00-104.00 150.00   52
 18  ω   -174.00-130.00   0.50    0.05    --  -97.00-104.00 150.00   88
 19  ω   -101.00 -51.00   0.50    0.05    --  -97.00 101.00 122.00  100
 20  ω    -45.00  20.00   0.50    0.05    --   56.47 -15.00  60.00  130
 21  ω     17.00  64.00   0.50    0.05    --  112.93 -64.00  60.00   94
 22  ω     45.00  70.00   0.50    0.05    --  112.93 -64.00  30.00   50
 23  ω     25.00  50.00   0.50    0.05    --  112.93 -50.00   0.00   50
 24  ω     16.00  72.00   0.50    0.05    --  112.93 -64.00 -30.00  112
 25  ω     29.00  70.00   0.50    0.05    --  112.93 -64.00-120.00   82
 26  ω     14.00  64.00   0.50    0.05    --  112.93 -64.00-150.00  100
 27  ω     15.00  40.00   0.50    0.05    --  112.93 -64.00-180.00   50
 28  ω     19.00  44.00   0.50    0.05    --  112.93 -50.00-180.00   50
 29  ω     20.00  46.00   0.50    0.05    --  112.93 -50.00-150.00   52
 30  ω     27.00  54.00   0.50    0.05    --  112.93 -50.00 -90.00   54
 31  ω     19.00  44.00   0.50    0.05    --  112.93 -50.00 -60.00   50
 32  ω     26.00  52.00   0.50    0.05    --  112.93 -50.00  60.00   52
 33  ω     21.00  47.00   0.50    0.05    --  112.93 -50.00  90.00   52
 34  ω     20.00  46.00   0.50    0.05    --  112.93 -92.00  60.00   52
 35  ω     17.00  42.00   0.50    0.05    --   56.47-101.00  18.00   50
 36  ω     52.00  89.00   0.50    0.05    --  112.93-101.00  18.00   74
 37  ω     53.00  99.00   0.50    0.05    --  112.93 -92.00  60.00   92
 38  ω     46.00  98.00   0.50    0.05    --  112.93-104.00 150.00  104
 39  ω      4.00  29.00   0.50    0.05    --    0.00-101.00  18.00   50
 40  ω     18.00  79.00   0.50    0.05    --    0.00  19.00   0.00  122
 41  ω     97.00 124.00   0.50    0.05    --   56.47 101.00 122.00   54
 42  ω     90.00 124.00   0.50    0.05    --  112.93 101.00 122.00   68
 43  ω     79.00 127.00   0.50    0.05    --   56.47 125.00  60.00   96
 44  ω    -29.00  -4.00   0.50    0.05    --    0.00  19.00   0.00   50
 45  ω    -55.00 -30.00   0.50    0.05    --    0.00 101.00 122.00   50
 46  ω   -105.00 -78.00   0.50    0.05    --    0.00 179.00  90.00   54
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'ROD, Synergy Custom system, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0594027000
_diffrn_orient_matrix_UB_12      0.0258513000
_diffrn_orient_matrix_UB_13      0.2007086000
_diffrn_orient_matrix_UB_21      -0.0891158000
_diffrn_orient_matrix_UB_22      0.0754344000
_diffrn_orient_matrix_UB_23      -0.0540357000
_diffrn_orient_matrix_UB_31      -0.2016563000
_diffrn_orient_matrix_UB_32      -0.0257199000
_diffrn_orient_matrix_UB_33      0.0433536000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1541
_reflns_number_total             1696
_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 1.171.43.127a (Rigaku OD, 2024)'
_computing_data_collection       
'CrysAlisPro system (CCD 43.127a 64-bit (release 16-06-2024))'
_computing_data_reduction        'CrysAlisPro 1.171.43.127a (Rigaku OD, 2024)'
_computing_molecular_graphics    'Olex2 1.5-ac6-020 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-ac6-020 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/1 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.224
_refine_diff_density_min         -0.255
_refine_diff_density_rms         0.048
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     146
_refine_ls_number_reflns         1696
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0386
_refine_ls_R_factor_gt           0.0351
_refine_ls_restrained_S_all      1.024
_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)+(0.0551P)²+0.4172P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0941
_refine_ls_wR_factor_ref         0.0964
_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 Ternary CH refined with riding coordinates:
 C00F(H00F)
2.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C2(H2)
2.c Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C)
;
_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 0.22285(14) 0.51076(5) 0.52761(14) 0.0338(3) Uani 1 1 d . . . . .
F2 F 0.34573(15) 0.51221(5) 0.27578(15) 0.0383(3) Uani 1 1 d . . . . .
O1 O -0.03613(15) 0.85023(6) 0.17041(15) 0.0258(3) Uani 1 1 d . . . . .
O2 O 0.11694(16) 0.90782(6) 0.40933(15) 0.0282(3) Uani 1 1 d . . . . .
N3 N -0.04304(17) 0.69820(6) 0.25563(17) 0.0202(3) Uani 1 1 d . . . . .
N1 N 0.14455(17) 0.60447(6) 0.32827(17) 0.0203(3) Uani 1 1 d . . . . .
N4 N 0.09410(17) 0.85467(6) 0.30662(16) 0.0197(3) Uani 1 1 d . . . . .
N2 N -0.04265(17) 0.62759(7) 0.25988(17) 0.0224(3) Uani 1 1 d . . . . .
C1 C 0.2700(2) 0.66235(7) 0.36885(19) 0.0184(3) Uani 1 1 d . . . . .
C6 C 0.14681(19) 0.72202(7) 0.32139(18) 0.0176(3) Uani 1 1 d . . . . .
C4 C 0.4264(2) 0.80199(8) 0.41872(19) 0.0201(3) Uani 1 1 d . . . . .
C3 C 0.5445(2) 0.73863(8) 0.46131(19) 0.0216(3) Uani 1 1 d . . . . .
H3 H 0.681551 0.744915 0.507461 0.026 Uiso 1 1 calc R U . . .
C5 C 0.2274(2) 0.79251(7) 0.35081(19) 0.0183(3) Uani 1 1 d . . . . .
C2 C 0.4723(2) 0.66900(8) 0.4397(2) 0.0210(3) Uani 1 1 d . . . . .
H2 H 0.554574 0.627717 0.471006 0.025 Uiso 1 1 calc R U . . .
C00F C 0.1812(2) 0.52829(8) 0.3459(2) 0.0263(3) Uani 1 1 d . . . . .
H00F H 0.065075 0.499859 0.282442 0.032 Uiso 1 1 calc R U . . .
C7 C 0.5279(2) 0.87480(8) 0.4427(2) 0.0269(3) Uani 1 1 d . . . . .
H7A H 0.530887 0.891868 0.569292 0.040 Uiso 1 1 calc R U . . .
H7B H 0.455153 0.909838 0.356582 0.040 Uiso 1 1 calc R U . . .
H7C H 0.663786 0.870109 0.417943 0.040 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 C00F 1.3598(19) . ?
F2 C00F 1.3455(19) . ?
O1 N4 1.2291(16) . ?
O2 N4 1.2293(16) . ?
N3 N2 1.2981(17) . ?
N3 C6 1.3802(18) . ?
N1 N2 1.3642(16) . ?
N1 C1 1.3684(18) . ?
N1 C00F 1.4245(18) . ?
N4 C5 1.4644(17) . ?
C1 C6 1.3919(19) . ?
C1 C2 1.402(2) . ?
C6 C5 1.4106(19) . ?
C4 C3 1.422(2) . ?
C4 C5 1.382(2) . ?
C4 C7 1.504(2) . ?
C3 C2 1.371(2) . ?

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
N2 N3 C6 108.09(11) . . ?
N2 N1 C1 110.78(11) . . ?
N2 N1 C00F 118.71(12) . . ?
C1 N1 C00F 130.51(12) . . ?
O1 N4 O2 123.78(12) . . ?
O1 N4 C5 118.05(11) . . ?
O2 N4 C5 118.16(12) . . ?
N3 N2 N1 108.57(11) . . ?
N1 C1 C6 103.07(12) . . ?
N1 C1 C2 133.95(13) . . ?
C6 C1 C2 122.98(13) . . ?
N3 C6 C1 109.49(12) . . ?
N3 C6 C5 131.79(12) . . ?
C1 C6 C5 118.69(12) . . ?
C3 C4 C7 117.91(13) . . ?
C5 C4 C3 117.80(13) . . ?
C5 C4 C7 124.23(13) . . ?
C2 C3 C4 123.91(13) . . ?
C6 C5 N4 117.98(12) . . ?
C4 C5 N4 121.49(12) . . ?
C4 C5 C6 120.53(12) . . ?
C3 C2 C1 116.04(12) . . ?
F1 C00F N1 109.11(12) . . ?
F2 C00F F1 105.81(12) . . ?
F2 C00F N1 109.09(13) . . ?

_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 2.728
_oxdiff_exptl_absorpt_empirical_full_min 0.680
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: ethyl acetate'
