# Electronic Supplementary Material (ESI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2023

####################################################################### 
# 
# 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_2110b0035
_database_code_depnum_ccdc_archive 'CCDC 2236596'
loop_
_audit_author_name
_audit_author_address
'Huang Shiwen'
;South China University of Technology
China
;
_audit_update_record             
;
2023-01-17 deposited with the CCDC.	2023-08-17 downloaded from the CCDC.
;
_audit_creation_date             2021-10-29
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C10 H8 F4 I N O, I, C15 H24 N3'
_chemical_formula_sum            'C25 H32 F4 I2 N4 O'
_chemical_formula_weight         734.34
_chemical_melting_point          ?
_chemical_oxdiff_formula         C25H32F4I2N4O
_chemical_oxdiff_usercomment     PYCPI-4FPHI
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'
I I -0.3257 6.8362 '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/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                   10.9182(2)
_cell_length_b                   22.7514(5)
_cell_length_c                   11.4864(3)
_cell_angle_alpha                90
_cell_angle_beta                 101.588(2)
_cell_angle_gamma                90
_cell_volume                     2795.11(11)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4623
_cell_measurement_temperature    150.0(2)
_cell_measurement_theta_max      72.7280
_cell_measurement_theta_min      3.8540
_shelx_estimated_absorpt_T_max   0.713
_shelx_estimated_absorpt_T_min   0.103
_exptl_absorpt_coefficient_mu    18.125
_exptl_absorpt_correction_T_max  0.665
_exptl_absorpt_correction_T_min  0.067
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.84a (Rigaku Oxford Diffraction, 2020)
Analytical numeric absorption correction using a multifaceted crystal
model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.745
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             1440
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 -1 2 0.2783
0 1 -2 0.2783
0 -1 0 0.0416
0 1 0 0.0416
-2 0 1 0.6739
2 0 -1 0.6739

_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.02
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
0.0037 -1.0034 1.9997 0.0578 0.2713 0.0519
-0.0037 1.0034 -1.9997 -0.0578 -0.2713 -0.0519
0.0009 -0.9990 -0.0000 0.0673 0.0037 -0.0056
-0.0009 0.9990 0.0000 -0.0673 -0.0037 0.0056
-1.9993 -0.0149 1.0025 0.0236 0.0191 0.2913
1.9993 0.0149 -1.0025 -0.0236 -0.0191 -0.2913

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0486
_diffrn_reflns_av_unetI/netI     0.0577
_diffrn_reflns_Laue_measured_fraction_full 0.960
_diffrn_reflns_Laue_measured_fraction_max 0.935
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            10904
_diffrn_reflns_point_group_measured_fraction_full 0.960
_diffrn_reflns_point_group_measured_fraction_max 0.935
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.843
_diffrn_reflns_theta_min         3.886
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150.0(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2913
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.960
_diffrn_measured_fraction_theta_max 0.935
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -114.00 -20.00   1.00    1.00    --  -41.14 -38.00-150.00   94
  2  ω    -46.00 -20.00   1.00    1.00    --  -41.14 -38.00 -60.00   26
  3  ω   -106.00 -77.00   1.00    1.00    --  -41.14 -38.00 -60.00   29
  4  ω    -66.00  -8.00   1.00    1.00    --  -41.14 125.00   0.00   58
  5  ω     58.00  92.00   1.00    1.00    --   41.14-125.00-120.00   34
  6  ω    107.00 161.00   1.00    1.50    --  104.98  77.00-180.00   54
  7  ω    110.00 178.00   1.00    1.50    --  104.98  77.00  30.00   68
  8  ω     71.00 112.00   1.00    1.50    --  104.98-125.00 120.00   41
  9  ω    106.00 133.00   1.00    1.50    --  104.98  77.00-120.00   27
 10  ω     46.00 107.00   1.00    1.50    --  104.98 -94.00 -60.00   61
 11  ω     46.00 101.00   1.00    1.50    --  104.98 -94.00-180.00   55
 12  ω    109.00 175.00   1.00    1.50    --  104.98 125.00-120.00   66
 13  ω     58.00 130.00   1.00    1.50    --  104.98 -30.00-120.00   72
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0137705000
_diffrn_orient_matrix_UB_12      -0.0674254000
_diffrn_orient_matrix_UB_13      -0.0048964000
_diffrn_orient_matrix_UB_21      0.0575257000
_diffrn_orient_matrix_UB_22      -0.0036231000
_diffrn_orient_matrix_UB_23      0.1337665000
_diffrn_orient_matrix_UB_31      -0.1312380000
_diffrn_orient_matrix_UB_32      0.0054614000
_diffrn_orient_matrix_UB_33      0.0289198000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4370
_reflns_number_total             5213
_reflns_odcompleteness_completeness 99.90
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         1.758
_refine_diff_density_min         -2.101
_refine_diff_density_rms         0.182
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     326
_refine_ls_number_reflns         5213
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0745
_refine_ls_R_factor_gt           0.0642
_refine_ls_restrained_S_all      1.050
_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)+(0.1080P)²+3.1070P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1662
_refine_ls_wR_factor_ref         0.1788
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B), C9(H9A,H9B), C14(H14A,H14B), C15(H15A,H15B), C16(H16A,H16B),
 C17(H17A,H17B), C18(H18A,H18B), C19(H19A,H19B), C20(H20A,H20B), C21(H21A,H21B),
  C22(H22A,H22B), C23(H23A,H23B), C24(H24A,H24B), C25(H25A,H25B)
2.b Aromatic/amide H refined with riding coordinates:
 N1(H1)
2.c Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C)
;
_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
I1 I 0.40301(4) 0.23207(2) 0.91452(4) 0.03437(17) Uani 1 1 d . . . . .
F1 F 0.3329(4) 0.20837(19) 0.6304(4) 0.0426(10) Uani 1 1 d . . . . .
F2 F 0.2669(5) 0.2806(2) 0.4442(4) 0.0484(11) Uani 1 1 d . . . . .
F3 F 0.3122(5) 0.4437(2) 0.7001(5) 0.0542(12) Uani 1 1 d . . . . .
F4 F 0.3763(5) 0.3732(2) 0.8879(4) 0.0492(12) Uani 1 1 d . . . . .
O1 O 0.3192(6) 0.4220(4) 0.4029(7) 0.072(2) Uani 1 1 d . . . . .
N1 N 0.1257(6) 0.4208(3) 0.4478(6) 0.0398(14) Uani 1 1 d . . . . .
H1 H 0.0800 0.4072 0.4945 0.048 Uiso 1 1 calc R . . . .
C1 C 0.3561(6) 0.2885(3) 0.7644(7) 0.0318(14) Uani 1 1 d . . . . .
C2 C 0.3276(6) 0.2673(3) 0.6506(7) 0.0315(14) Uani 1 1 d . . . . .
C3 C 0.2939(6) 0.3036(3) 0.5543(7) 0.0331(14) Uani 1 1 d . . . . .
C4 C 0.2849(6) 0.3643(3) 0.5668(7) 0.0352(16) Uani 1 1 d . . . . .
C5 C 0.3173(7) 0.3851(3) 0.6811(7) 0.0338(15) Uani 1 1 d . . . . .
C6 C 0.3498(7) 0.3488(3) 0.7794(8) 0.0376(16) Uani 1 1 d . . . . .
C7 C 0.2449(7) 0.4041(3) 0.4626(8) 0.0400(17) Uani 1 1 d . . . . .
C8 C 0.0712(7) 0.4618(3) 0.3538(8) 0.0437(18) Uani 1 1 d . . . . .
H8A H 0.1268 0.4656 0.2981 0.052 Uiso 1 1 calc R . . . .
H8B H 0.0634 0.5002 0.3884 0.052 Uiso 1 1 calc R . . . .
C9 C -0.0556(7) 0.4419(4) 0.2879(9) 0.049(2) Uani 1 1 d . . . . .
H9A H -0.1129 0.4406 0.3424 0.058 Uiso 1 1 calc R . . . .
H9B H -0.0490 0.4025 0.2574 0.058 Uiso 1 1 calc R . . . .
C10 C -0.1078(9) 0.4832(4) 0.1847(8) 0.051(2) Uani 1 1 d . . . . .
H10A H -0.0646 0.4766 0.1209 0.076 Uiso 1 1 calc GR . . . .
H10B H -0.0961 0.5232 0.2110 0.076 Uiso 1 1 calc GR . . . .
H10C H -0.1953 0.4756 0.1575 0.076 Uiso 1 1 calc GR . . . .
I2 I 0.46245(5) 0.14595(3) 1.14501(5) 0.0484(2) Uani 1 1 d . . . . .
N2 N 0.5787(6) 0.3619(3) 0.3756(5) 0.0328(12) Uani 1 1 d . . . . .
N3 N 0.6454(5) 0.3751(2) 0.7023(6) 0.0309(12) Uani 1 1 d . . . . .
N4 N 0.6025(6) 0.2300(3) 0.5591(6) 0.0328(13) Uani 1 1 d . . . . .
C11 C 0.5968(6) 0.3385(3) 0.4822(7) 0.0322(14) Uani 1 1 d . . . . .
C12 C 0.6062(6) 0.2874(3) 0.5522(7) 0.0302(14) Uani 1 1 d . . . . .
C13 C 0.6231(6) 0.3426(3) 0.6045(6) 0.0294(14) Uani 1 1 d . . . . .
C14 C 0.5530(7) 0.3272(3) 0.2671(7) 0.0388(16) Uani 1 1 d . . . . .
H14A H 0.4676 0.3129 0.2504 0.047 Uiso 1 1 calc R . . . .
H14B H 0.6098 0.2941 0.2716 0.047 Uiso 1 1 calc R . . . .
C15 C 0.5747(9) 0.3713(4) 0.1742(7) 0.0464(19) Uani 1 1 d . . . . .
H15A H 0.5231 0.3624 0.0971 0.056 Uiso 1 1 calc R . . . .
H15B H 0.6618 0.3718 0.1672 0.056 Uiso 1 1 calc R . . . .
C16 C 0.5373(9) 0.4297(4) 0.2211(8) 0.048(2) Uani 1 1 d . . . . .
H16A H 0.4472 0.4344 0.2038 0.057 Uiso 1 1 calc R . . . .
H16B H 0.5748 0.4623 0.1867 0.057 Uiso 1 1 calc R . . . .
C17 C 0.5883(7) 0.4258(3) 0.3566(7) 0.0377(16) Uani 1 1 d . . . . .
H17A H 0.6741 0.4394 0.3778 0.045 Uiso 1 1 calc R . . . .
H17B H 0.5371 0.4480 0.4009 0.045 Uiso 1 1 calc R . . . .
C18 C 0.6676(8) 0.4390(3) 0.6997(8) 0.0422(17) Uani 1 1 d . . . . .
H18A H 0.5896 0.4607 0.6870 0.051 Uiso 1 1 calc R . . . .
H18B H 0.7130 0.4493 0.6382 0.051 Uiso 1 1 calc R . . . .
C19 C 0.7469(11) 0.4507(4) 0.8247(9) 0.059(2) Uani 1 1 d . . . . .
H19A H 0.8354 0.4483 0.8239 0.071 Uiso 1 1 calc R . . . .
H19B H 0.7290 0.4894 0.8528 0.071 Uiso 1 1 calc R . . . .
C20 C 0.7090(11) 0.4030(4) 0.9029(9) 0.059(2) Uani 1 1 d . . . . .
H20A H 0.6329 0.4135 0.9293 0.071 Uiso 1 1 calc R . . . .
H20B H 0.7747 0.3958 0.9719 0.071 Uiso 1 1 calc R . . . .
C21 C 0.6884(8) 0.3490(3) 0.8208(8) 0.0400(17) Uani 1 1 d . . . . .
H21A H 0.7654 0.3273 0.8247 0.048 Uiso 1 1 calc R . . . .
H21B H 0.6255 0.3231 0.8414 0.048 Uiso 1 1 calc R . . . .
C22 C 0.6587(8) 0.1983(3) 0.6708(7) 0.0404(17) Uani 1 1 d . . . . .
H22A H 0.5996 0.1938 0.7230 0.048 Uiso 1 1 calc R . . . .
H22B H 0.7336 0.2176 0.7133 0.048 Uiso 1 1 calc R . . . .
C23 C 0.6879(10) 0.1402(4) 0.6186(9) 0.054(2) Uani 1 1 d . . . . .
H23A H 0.7703 0.1411 0.5992 0.065 Uiso 1 1 calc R . . . .
H23B H 0.6853 0.1085 0.6746 0.065 Uiso 1 1 calc R . . . .
C24 C 0.5921(10) 0.1318(4) 0.5117(10) 0.058(2) Uani 1 1 d . . . . .
H24A H 0.5146 0.1182 0.5314 0.069 Uiso 1 1 calc R . . . .
H24B H 0.6193 0.1037 0.4588 0.069 Uiso 1 1 calc R . . . .
C25 C 0.5758(7) 0.1925(3) 0.4553(8) 0.0406(17) Uani 1 1 d . . . . .
H25A H 0.6345 0.1990 0.4034 0.049 Uiso 1 1 calc R . . . .
H25B H 0.4913 0.1983 0.4107 0.049 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 2.128(8) . ?
F1 C2 1.363(8) . ?
F2 C3 1.346(9) . ?
F3 C5 1.354(8) . ?
F4 C6 1.342(9) . ?
O1 C7 1.232(10) . ?
N1 H1 0.8600 . ?
N1 C7 1.334(10) . ?
N1 C8 1.460(10) . ?
C1 C2 1.370(11) . ?
C1 C6 1.386(10) . ?
C2 C3 1.371(11) . ?
C3 C4 1.393(10) . ?
C4 C5 1.374(11) . ?
C4 C7 1.493(12) . ?
C5 C6 1.387(11) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C8 C9 1.508(11) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C9 C10 1.529(12) . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
N2 C11 1.312(10) . ?
N2 C14 1.455(10) . ?
N2 C17 1.478(9) . ?
N3 C13 1.326(10) . ?
N3 C18 1.473(9) . ?
N3 C21 1.473(10) . ?
N4 C12 1.308(9) . ?
N4 C22 1.493(9) . ?
N4 C25 1.448(10) . ?
C11 C12 1.406(10) . ?
C11 C13 1.379(11) . ?
C12 C13 1.390(10) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C14 C15 1.518(11) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C15 C16 1.519(13) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C16 C17 1.547(12) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C18 C19 1.543(13) . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C19 C20 1.518(14) . ?
C20 H20A 0.9700 . ?
C20 H20B 0.9700 . ?
C20 C21 1.537(12) . ?
C21 H21A 0.9700 . ?
C21 H21B 0.9700 . ?
C22 H22A 0.9700 . ?
C22 H22B 0.9700 . ?
C22 C23 1.511(12) . ?
C23 H23A 0.9700 . ?
C23 H23B 0.9700 . ?
C23 C24 1.456(15) . ?
C24 H24A 0.9700 . ?
C24 H24B 0.9700 . ?
C24 C25 1.519(12) . ?
C25 H25A 0.9700 . ?
C25 H25B 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
C7 N1 H1 119.4 . . ?
C7 N1 C8 121.3(7) . . ?
C8 N1 H1 119.4 . . ?
C2 C1 I1 122.1(5) . . ?
C2 C1 C6 117.4(7) . . ?
C6 C1 I1 120.5(6) . . ?
F1 C2 C1 120.0(7) . . ?
F1 C2 C3 118.0(6) . . ?
C1 C2 C3 122.0(6) . . ?
F2 C3 C2 119.8(6) . . ?
F2 C3 C4 118.4(7) . . ?
C2 C3 C4 121.8(7) . . ?
C3 C4 C7 122.2(7) . . ?
C5 C4 C3 115.5(7) . . ?
C5 C4 C7 122.3(7) . . ?
F3 C5 C4 118.9(7) . . ?
F3 C5 C6 117.9(7) . . ?
C4 C5 C6 123.1(7) . . ?
F4 C6 C1 121.1(8) . . ?
F4 C6 C5 118.8(6) . . ?
C1 C6 C5 120.0(7) . . ?
O1 C7 N1 124.6(8) . . ?
O1 C7 C4 121.9(7) . . ?
N1 C7 C4 113.3(7) . . ?
N1 C8 H8A 109.2 . . ?
N1 C8 H8B 109.2 . . ?
N1 C8 C9 112.1(6) . . ?
H8A C8 H8B 107.9 . . ?
C9 C8 H8A 109.2 . . ?
C9 C8 H8B 109.2 . . ?
C8 C9 H9A 109.3 . . ?
C8 C9 H9B 109.3 . . ?
C8 C9 C10 111.5(7) . . ?
H9A C9 H9B 108.0 . . ?
C10 C9 H9A 109.3 . . ?
C10 C9 H9B 109.3 . . ?
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 . . ?
C11 N2 C14 123.1(6) . . ?
C11 N2 C17 122.4(7) . . ?
C14 N2 C17 114.5(6) . . ?
C13 N3 C18 122.4(6) . . ?
C13 N3 C21 121.9(6) . . ?
C21 N3 C18 113.1(6) . . ?
C12 N4 C22 121.5(6) . . ?
C12 N4 C25 122.8(6) . . ?
C25 N4 C22 113.7(6) . . ?
N2 C11 C12 148.1(7) . . ?
N2 C11 C13 152.0(7) . . ?
C13 C11 C12 59.9(5) . . ?
N4 C12 C11 149.3(8) . . ?
N4 C12 C13 151.6(7) . . ?
C13 C12 C11 59.1(5) . . ?
N3 C13 C11 150.0(7) . . ?
N3 C13 C12 148.9(7) . . ?
C11 C13 C12 61.0(5) . . ?
N2 C14 H14A 111.3 . . ?
N2 C14 H14B 111.3 . . ?
N2 C14 C15 102.3(6) . . ?
H14A C14 H14B 109.2 . . ?
C15 C14 H14A 111.3 . . ?
C15 C14 H14B 111.3 . . ?
C14 C15 H15A 111.0 . . ?
C14 C15 H15B 111.0 . . ?
C14 C15 C16 103.7(7) . . ?
H15A C15 H15B 109.0 . . ?
C16 C15 H15A 111.0 . . ?
C16 C15 H15B 111.0 . . ?
C15 C16 H16A 111.0 . . ?
C15 C16 H16B 111.0 . . ?
C15 C16 C17 103.8(6) . . ?
H16A C16 H16B 109.0 . . ?
C17 C16 H16A 111.0 . . ?
C17 C16 H16B 111.0 . . ?
N2 C17 C16 100.5(6) . . ?
N2 C17 H17A 111.7 . . ?
N2 C17 H17B 111.7 . . ?
C16 C17 H17A 111.7 . . ?
C16 C17 H17B 111.7 . . ?
H17A C17 H17B 109.4 . . ?
N3 C18 H18A 111.3 . . ?
N3 C18 H18B 111.3 . . ?
N3 C18 C19 102.5(6) . . ?
H18A C18 H18B 109.2 . . ?
C19 C18 H18A 111.3 . . ?
C19 C18 H18B 111.3 . . ?
C18 C19 H19A 110.8 . . ?
C18 C19 H19B 110.8 . . ?
H19A C19 H19B 108.8 . . ?
C20 C19 C18 105.0(8) . . ?
C20 C19 H19A 110.8 . . ?
C20 C19 H19B 110.8 . . ?
C19 C20 H20A 111.1 . . ?
C19 C20 H20B 111.1 . . ?
C19 C20 C21 103.4(8) . . ?
H20A C20 H20B 109.0 . . ?
C21 C20 H20A 111.1 . . ?
C21 C20 H20B 111.1 . . ?
N3 C21 C20 103.0(6) . . ?
N3 C21 H21A 111.2 . . ?
N3 C21 H21B 111.2 . . ?
C20 C21 H21A 111.2 . . ?
C20 C21 H21B 111.2 . . ?
H21A C21 H21B 109.1 . . ?
N4 C22 H22A 111.9 . . ?
N4 C22 H22B 111.9 . . ?
N4 C22 C23 99.5(7) . . ?
H22A C22 H22B 109.6 . . ?
C23 C22 H22A 111.9 . . ?
C23 C22 H22B 111.9 . . ?
C22 C23 H23A 110.5 . . ?
C22 C23 H23B 110.5 . . ?
H23A C23 H23B 108.7 . . ?
C24 C23 C22 106.0(8) . . ?
C24 C23 H23A 110.5 . . ?
C24 C23 H23B 110.5 . . ?
C23 C24 H24A 110.9 . . ?
C23 C24 H24B 110.9 . . ?
C23 C24 C25 104.2(7) . . ?
H24A C24 H24B 108.9 . . ?
C25 C24 H24A 110.9 . . ?
C25 C24 H24B 110.9 . . ?
N4 C25 C24 101.4(7) . . ?
N4 C25 H25A 111.5 . . ?
N4 C25 H25B 111.5 . . ?
C24 C25 H25A 111.5 . . ?
C24 C25 H25B 111.5 . . ?
H25A C25 H25B 109.3 . . ?

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 F1 -2.2(9) . . . . ?
I1 C1 C2 C3 178.1(5) . . . . ?
I1 C1 C6 F4 1.8(10) . . . . ?
I1 C1 C6 C5 -179.1(5) . . . . ?
F1 C2 C3 F2 0.2(10) . . . . ?
F1 C2 C3 C4 179.3(6) . . . . ?
F2 C3 C4 C5 -178.1(6) . . . . ?
F2 C3 C4 C7 0.8(10) . . . . ?
F3 C5 C6 F4 -0.9(10) . . . . ?
F3 C5 C6 C1 179.9(6) . . . . ?
N1 C8 C9 C10 -176.3(8) . . . . ?
C1 C2 C3 F2 180.0(6) . . . . ?
C1 C2 C3 C4 -0.9(11) . . . . ?
C2 C1 C6 F4 -179.9(6) . . . . ?
C2 C1 C6 C5 -0.8(10) . . . . ?
C2 C3 C4 C5 2.8(10) . . . . ?
C2 C3 C4 C7 -178.3(6) . . . . ?
C3 C4 C5 F3 179.2(6) . . . . ?
C3 C4 C5 C6 -3.8(10) . . . . ?
C3 C4 C7 O1 -83.7(11) . . . . ?
C3 C4 C7 N1 100.9(8) . . . . ?
C4 C5 C6 F4 -177.9(7) . . . . ?
C4 C5 C6 C1 2.9(11) . . . . ?
C5 C4 C7 O1 95.1(10) . . . . ?
C5 C4 C7 N1 -80.3(9) . . . . ?
C6 C1 C2 F1 179.6(6) . . . . ?
C6 C1 C2 C3 -0.1(10) . . . . ?
C7 N1 C8 C9 134.7(9) . . . . ?
C7 C4 C5 F3 0.4(10) . . . . ?
C7 C4 C5 C6 177.3(7) . . . . ?
C8 N1 C7 O1 2.0(13) . . . . ?
C8 N1 C7 C4 177.2(7) . . . . ?
N2 C11 C12 N4 -1(2) . . . . ?
N2 C11 C12 C13 178.2(13) . . . . ?
N2 C11 C13 N3 4(2) . . . . ?
N2 C11 C13 C12 -178.0(15) . . . . ?
N2 C14 C15 C16 -31.5(8) . . . . ?
N3 C18 C19 C20 -27.4(10) . . . . ?
N4 C12 C13 N3 -3(2) . . . . ?
N4 C12 C13 C11 179.1(14) . . . . ?
N4 C22 C23 C24 -31.4(9) . . . . ?
C11 N2 C14 C15 -165.3(7) . . . . ?
C11 N2 C17 C16 -170.7(7) . . . . ?
C11 C12 C13 N3 178.4(13) . . . . ?
C12 N4 C22 C23 -153.1(7) . . . . ?
C12 N4 C25 C24 176.1(7) . . . . ?
C12 C11 C13 N3 -178.3(13) . . . . ?
C13 N3 C18 C19 -154.2(7) . . . . ?
C13 N3 C21 C20 176.5(7) . . . . ?
C13 C11 C12 N4 -179.1(13) . . . . ?
C14 N2 C11 C12 1.7(16) . . . . ?
C14 N2 C11 C13 178.4(11) . . . . ?
C14 N2 C17 C16 11.7(8) . . . . ?
C14 C15 C16 C17 39.7(8) . . . . ?
C15 C16 C17 N2 -30.9(8) . . . . ?
C17 N2 C11 C12 -175.7(10) . . . . ?
C17 N2 C11 C13 1.0(18) . . . . ?
C17 N2 C14 C15 12.2(8) . . . . ?
C18 N3 C13 C11 -10.1(16) . . . . ?
C18 N3 C13 C12 172.8(10) . . . . ?
C18 N3 C21 C20 14.4(9) . . . . ?
C18 C19 C20 C21 36.6(11) . . . . ?
C19 C20 C21 N3 -30.9(10) . . . . ?
C21 N3 C13 C11 -170.5(11) . . . . ?
C21 N3 C13 C12 12.3(15) . . . . ?
C21 N3 C18 C19 7.8(9) . . . . ?
C22 N4 C12 C11 161.6(10) . . . . ?
C22 N4 C12 C13 -16.8(17) . . . . ?
C22 N4 C25 C24 11.9(9) . . . . ?
C22 C23 C24 C25 40.6(10) . . . . ?
C23 C24 C25 N4 -31.5(10) . . . . ?
C25 N4 C12 C11 -1.4(16) . . . . ?
C25 N4 C12 C13 -179.8(11) . . . . ?
C25 N4 C22 C23 11.3(9) . . . . ?

_olex2_date_sample_data_collection 2021-10-20
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Frame scaling
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.386
_oxdiff_exptl_absorpt_empirical_full_min 0.664
