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

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# 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_fassr02
_database_code_depnum_ccdc_archive 'CCDC 2495142'
loop_
_audit_author_name
_audit_author_address
'William Brennessel'
;University of Rochester
United States of America
;
_audit_update_record             
;
2026-02-18 deposited with the CCDC.	2026-03-09 downloaded from the CCDC.
;
_audit_creation_date             2022-04-27
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C11 H10 F N O'
_chemical_formula_sum            'C11 H10 F N O'
_chemical_formula_weight         191.20
_chemical_absolute_configuration ad
_chemical_melting_point          ?
_chemical_oxdiff_formula         ?
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      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   7.18760(5)
_cell_length_b                   7.88139(5)
_cell_length_c                   33.6858(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1908.24(2)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    24541
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      79.7280
_cell_measurement_theta_min      3.8350
_shelx_estimated_absorpt_T_max   0.934
_shelx_estimated_absorpt_T_min   0.822
_exptl_absorpt_coefficient_mu    0.826
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.76894
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.120a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.331
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             800
_exptl_crystal_size_max          0.247
_exptl_crystal_size_mid          0.227
_exptl_crystal_size_min          0.084
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0382
_diffrn_reflns_av_unetI/netI     0.0191
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       42
_diffrn_reflns_limit_l_min       -42
_diffrn_reflns_number            32458
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         80.393
_diffrn_reflns_theta_min         5.252
_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 1.000
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    101.00 178.00   0.50    0.31    --  113.25  45.00   0.00  154
  2  ω    101.00 178.00   0.50    0.31    --  113.25  40.00  82.00  154
  3  ω     97.00 178.00   0.50    0.31    --  113.25  61.00-180.00  162
  4  ω    101.00 178.00   0.50    0.31    --  113.25  30.00-120.00  154
  5  ω    101.00 178.00   0.50    0.31    --  113.25  30.00 -30.00  154
  6  ω    101.00 178.00   0.50    0.31    --  113.25  30.00 150.00  154
  7  ω   -119.00 -25.00   0.50    0.08    --  -47.32 -77.00   0.00  188
  8  ω   -119.00 -32.00   0.50    0.08    --  -47.32 -57.00  90.00  174
  9  ω   -119.00 -32.00   0.50    0.08    --  -47.32 -57.00 -90.00  174
 10  ω   -119.00 -25.00   0.50    0.08    --  -47.32 -77.00-150.00  188
 11  ω     42.00 106.00   0.50    0.31    --  113.25 -93.00  84.00  128
 12  ω     42.00 106.00   0.50    0.31    --  113.25 -94.00  60.00  128
 13  ω     42.00 111.00   0.50    0.31    --  113.25-125.00  60.00  138
 14  ω     42.00 106.00   0.50    0.31    --  113.25 -94.00 -30.00  128
 15  ω     42.00 111.00   0.50    0.31    --  113.25-125.00-120.00  138
 16  ω    -27.00  30.00   0.50    0.08    --   47.32 -19.00-180.00  114
 17  ω     42.00 136.00   0.50    0.31    --  113.25 -77.00-180.00  188
 18  ω     42.00  79.00   0.50    0.31    --  113.25 -61.00 -90.00   74
 19  ω     42.00  79.00   0.50    0.31    --  113.25 -61.00-120.00   74
 20  ω     42.00  79.00   0.50    0.31    --  113.25 -61.00 -30.00   74
 21  ω     42.00  79.00   0.50    0.31    --  113.25 -61.00   0.00   74
 22  ω     42.00  79.00   0.50    0.31    --  113.25 -61.00  60.00   74
 23  ω    106.00 178.00   0.50    0.31    --  113.25  98.00 -67.00  144
 24  ω    -65.00 -19.00   0.50    0.31    --  -91.75  61.00 150.00   92
 25  ω    -80.00  25.00   0.50    0.08    --  -47.32  98.00 -67.00  210
 26  ω    -65.00 -19.00   0.50    0.31    --  -91.75  61.00 -90.00   92
 27  ω   -163.00 -79.00   0.50    0.31    --  -91.75 -45.00  30.00  168
 28  ω   -163.00 -69.00   0.50    0.31    --  -91.75 -77.00  90.00  188
 29  ω   -164.00 -78.00   0.50    0.31    --  -91.75 -40.00 -71.00  172
 30  ω   -163.00 -75.00   0.50    0.31    --  -91.75 -61.00-180.00  176
 31  ω   -163.00 -75.00   0.50    0.31    --  -91.75 -61.00 -90.00  176
 32  ω   -163.00 -69.00   0.50    0.31    --  -91.75 -77.00 150.00  188
 33  ω   -119.00 -73.00   0.50    0.08    --  -47.32-125.00 120.00   92
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1086187000
_diffrn_orient_matrix_UB_12      0.0963005000
_diffrn_orient_matrix_UB_13      -0.0323666000
_diffrn_orient_matrix_UB_21      -0.0097095000
_diffrn_orient_matrix_UB_22      0.1572275000
_diffrn_orient_matrix_UB_23      0.0270820000
_diffrn_orient_matrix_UB_31      0.1844970000
_diffrn_orient_matrix_UB_32      0.0649703000
_diffrn_orient_matrix_UB_33      -0.0176201000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_reflns_Friedel_coverage         0.702
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.978
_reflns_number_gt                4012
_reflns_number_total             4116
_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 1.171.41.120a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.120a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.120a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015b)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2015a)'
_refine_diff_density_max         0.133
_refine_diff_density_min         -0.188
_refine_diff_density_rms         0.036
_refine_ls_abs_structure_details 
;
 Flack x determined using 1637 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.03(4)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     261
_refine_ls_number_reflns         4116
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0299
_refine_ls_R_factor_gt           0.0290
_refine_ls_restrained_S_all      1.057
_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)+(0.0316P)²+0.4071P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0719
_refine_ls_wR_factor_ref         0.0727
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Ternary CH refined with riding coordinates:
 C3(H3), C14(H14)
2.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C13(H13A,H13B)
2.c Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5), C7(H7), C8(H8), C10(H10), C11(H11), C15(H15), C16(H16),
 C18(H18), C19(H19), C21(H21), C22(H22)
;
_atom_sites_solution_hydrogens   mixed
_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_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 0.93797(17) 0.41748(18) 0.53173(3) 0.0476(3) Uani 1 1 d . . . . .
O1 O -0.05331(17) 0.49102(15) 0.76755(3) 0.0274(2) Uani 1 1 d . . . . .
N1 N 0.0714(2) 0.34502(17) 0.71301(4) 0.0247(3) Uani 1 1 d . . . . .
C1 C -0.0097(2) 0.47357(19) 0.73271(5) 0.0240(3) Uani 1 1 d . . . . .
C2 C -0.0311(2) 0.5807(2) 0.69517(5) 0.0268(3) Uani 1 1 d . . . . .
H2A H 0.048193 0.683317 0.694434 0.032 Uiso 1 1 calc R U . . .
H2B H -0.161523 0.607045 0.687977 0.032 Uiso 1 1 calc R U . . .
C3 C 0.0524(2) 0.4236(2) 0.67314(4) 0.0248(3) Uani 1 1 d . . . . .
H3 H -0.042144 0.364187 0.656386 0.030 Uiso 1 1 calc R U . . .
C4 C 0.2315(2) 0.4480(2) 0.65186(5) 0.0251(3) Uani 1 1 d . . . . .
H4 H 0.323121 0.518362 0.663809 0.030 Uiso 1 1 calc R U . . .
C5 C 0.2710(2) 0.3768(2) 0.61696(5) 0.0253(3) Uani 1 1 d . . . . .
H5 H 0.175966 0.310435 0.605026 0.030 Uiso 1 1 calc R U . . .
C6 C 0.4474(2) 0.3913(2) 0.59520(4) 0.0256(3) Uani 1 1 d . . . . .
C7 C 0.5973(2) 0.4884(2) 0.60880(5) 0.0277(3) Uani 1 1 d . . . . .
H7 H 0.585804 0.548638 0.633108 0.033 Uiso 1 1 calc R U . . .
C8 C 0.7624(2) 0.4989(2) 0.58757(5) 0.0304(3) Uani 1 1 d . . . . .
H8 H 0.863052 0.566246 0.596799 0.036 Uiso 1 1 calc R U . . .
C9 C 0.7757(3) 0.4081(3) 0.55254(5) 0.0334(4) Uani 1 1 d . . . . .
C10 C 0.6332(3) 0.3100(3) 0.53806(5) 0.0357(4) Uani 1 1 d . . . . .
H10 H 0.646988 0.248653 0.513962 0.043 Uiso 1 1 calc R U . . .
C11 C 0.4687(3) 0.3028(2) 0.55946(5) 0.0308(4) Uani 1 1 d . . . . .
H11 H 0.368368 0.236504 0.549663 0.037 Uiso 1 1 calc R U . . .
F2 F -0.43426(19) 0.28513(18) 0.95741(4) 0.0502(3) Uani 1 1 d . . . . .
O2 O 0.49354(18) 0.61688(14) 0.72757(3) 0.0309(3) Uani 1 1 d . . . . .
N2 N 0.4837(2) 0.47391(18) 0.78889(4) 0.0271(3) Uani 1 1 d . . . . .
C12 C 0.4672(2) 0.6044(2) 0.76336(5) 0.0243(3) Uani 1 1 d . . . . .
C13 C 0.4040(2) 0.7258(2) 0.79570(5) 0.0271(3) Uani 1 1 d . . . . .
H13A H 0.275252 0.768171 0.792466 0.033 Uiso 1 1 calc R U . . .
H13B H 0.492083 0.819466 0.801219 0.033 Uiso 1 1 calc R U . . .
C14 C 0.4228(2) 0.5710(2) 0.82420(5) 0.0253(3) Uani 1 1 d . . . . .
H14 H 0.524767 0.586051 0.844085 0.030 Uiso 1 1 calc R U . . .
C15 C 0.2469(2) 0.5093(2) 0.84256(5) 0.0253(3) Uani 1 1 d . . . . .
H15 H 0.149055 0.475328 0.825332 0.030 Uiso 1 1 calc R U . . .
C16 C 0.2175(2) 0.4985(2) 0.88140(5) 0.0266(3) Uani 1 1 d . . . . .
H16 H 0.318141 0.528592 0.898284 0.032 Uiso 1 1 calc R U . . .
C17 C 0.0438(2) 0.4445(2) 0.90072(5) 0.0260(3) Uani 1 1 d . . . . .
C18 C -0.1200(2) 0.4131(2) 0.87942(5) 0.0258(3) Uani 1 1 d . . . . .
H18 H -0.121389 0.429800 0.851486 0.031 Uiso 1 1 calc R U . . .
C19 C -0.2801(3) 0.3583(2) 0.89839(5) 0.0303(4) Uani 1 1 d . . . . .
H19 H -0.390293 0.336026 0.883716 0.036 Uiso 1 1 calc R U . . .
C20 C -0.2762(3) 0.3366(2) 0.93900(6) 0.0349(4) Uani 1 1 d . . . . .
C21 C -0.1198(3) 0.3666(3) 0.96123(5) 0.0372(4) Uani 1 1 d . . . . .
H21 H -0.120867 0.350857 0.989191 0.045 Uiso 1 1 calc R U . . .
C22 C 0.0400(3) 0.4203(2) 0.94190(5) 0.0331(4) Uani 1 1 d . . . . .
H22 H 0.149475 0.441302 0.956943 0.040 Uiso 1 1 calc R U . . .
H2 H 0.500(3) 0.365(3) 0.7851(6) 0.034(5) Uiso 1 1 d . . . . .
H1 H 0.085(3) 0.239(3) 0.7184(6) 0.035(6) Uiso 1 1 d . . . . .


_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 C9 1.363(2) . ?
O1 C1 1.2226(19) . ?
N1 C1 1.344(2) . ?
N1 C3 1.485(2) . ?
N1 H1 0.86(2) . ?
C1 C2 1.528(2) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C2 C3 1.563(2) . ?
C3 H3 1.0000 . ?
C3 C4 1.486(2) . ?
C4 H4 0.9500 . ?
C4 C5 1.333(2) . ?
C5 H5 0.9500 . ?
C5 C6 1.469(2) . ?
C6 C7 1.399(2) . ?
C6 C11 1.400(2) . ?
C7 H7 0.9500 . ?
C7 C8 1.388(2) . ?
C8 H8 0.9500 . ?
C8 C9 1.383(3) . ?
C9 C10 1.373(3) . ?
C10 H10 0.9500 . ?
C10 C11 1.386(3) . ?
C11 H11 0.9500 . ?
F2 C20 1.356(2) . ?
O2 C12 1.2244(19) . ?
N2 C12 1.346(2) . ?
N2 C14 1.480(2) . ?
N2 H2 0.88(2) . ?
C12 C13 1.520(2) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C13 C14 1.558(2) . ?
C14 H14 1.0000 . ?
C14 C15 1.489(2) . ?
C15 H15 0.9500 . ?
C15 C16 1.328(2) . ?
C16 H16 0.9500 . ?
C16 C17 1.471(2) . ?
C17 C18 1.401(2) . ?
C17 C22 1.400(2) . ?
C18 H18 0.9500 . ?
C18 C19 1.385(2) . ?
C19 H19 0.9500 . ?
C19 C20 1.379(2) . ?
C20 C21 1.372(3) . ?
C21 H21 0.9500 . ?
C21 C22 1.387(3) . ?
C22 H22 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 C3 95.29(12) . . ?
C1 N1 H1 132.8(15) . . ?
C3 N1 H1 127.2(14) . . ?
O1 C1 N1 132.06(15) . . ?
O1 C1 C2 134.94(15) . . ?
N1 C1 C2 92.95(12) . . ?
C1 C2 H2A 114.4 . . ?
C1 C2 H2B 114.4 . . ?
C1 C2 C3 85.22(11) . . ?
H2A C2 H2B 111.6 . . ?
C3 C2 H2A 114.4 . . ?
C3 C2 H2B 114.4 . . ?
N1 C3 C2 86.35(11) . . ?
N1 C3 H3 112.2 . . ?
N1 C3 C4 114.24(13) . . ?
C2 C3 H3 112.2 . . ?
C4 C3 C2 117.34(13) . . ?
C4 C3 H3 112.2 . . ?
C3 C4 H4 118.1 . . ?
C5 C4 C3 123.73(15) . . ?
C5 C4 H4 118.1 . . ?
C4 C5 H5 116.9 . . ?
C4 C5 C6 126.26(16) . . ?
C6 C5 H5 116.9 . . ?
C7 C6 C5 122.92(14) . . ?
C7 C6 C11 118.03(16) . . ?
C11 C6 C5 119.05(16) . . ?
C6 C7 H7 119.3 . . ?
C8 C7 C6 121.47(15) . . ?
C8 C7 H7 119.3 . . ?
C7 C8 H8 121.0 . . ?
C9 C8 C7 117.92(17) . . ?
C9 C8 H8 121.0 . . ?
F1 C9 C8 118.04(17) . . ?
F1 C9 C10 119.10(16) . . ?
C10 C9 C8 122.86(17) . . ?
C9 C10 H10 120.8 . . ?
C9 C10 C11 118.34(16) . . ?
C11 C10 H10 120.8 . . ?
C6 C11 H11 119.3 . . ?
C10 C11 C6 121.37(17) . . ?
C10 C11 H11 119.3 . . ?
C12 N2 C14 95.32(12) . . ?
C12 N2 H2 132.0(13) . . ?
C14 N2 H2 131.4(13) . . ?
O2 C12 N2 132.63(15) . . ?
O2 C12 C13 134.55(15) . . ?
N2 C12 C13 92.83(13) . . ?
C12 C13 H13A 114.4 . . ?
C12 C13 H13B 114.4 . . ?
C12 C13 C14 85.56(11) . . ?
H13A C13 H13B 111.5 . . ?
C14 C13 H13A 114.4 . . ?
C14 C13 H13B 114.4 . . ?
N2 C14 C13 86.29(11) . . ?
N2 C14 H14 112.5 . . ?
N2 C14 C15 114.58(14) . . ?
C13 C14 H14 112.5 . . ?
C15 C14 C13 115.97(14) . . ?
C15 C14 H14 112.5 . . ?
C14 C15 H15 117.8 . . ?
C16 C15 C14 124.38(15) . . ?
C16 C15 H15 117.8 . . ?
C15 C16 H16 117.0 . . ?
C15 C16 C17 126.09(15) . . ?
C17 C16 H16 117.0 . . ?
C18 C17 C16 122.53(14) . . ?
C22 C17 C16 119.60(15) . . ?
C22 C17 C18 117.86(16) . . ?
C17 C18 H18 119.4 . . ?
C19 C18 C17 121.11(15) . . ?
C19 C18 H18 119.4 . . ?
C18 C19 H19 120.7 . . ?
C20 C19 C18 118.67(17) . . ?
C20 C19 H19 120.7 . . ?
F2 C20 C19 118.29(18) . . ?
F2 C20 C21 119.24(16) . . ?
C21 C20 C19 122.47(17) . . ?
C20 C21 H21 120.8 . . ?
C20 C21 C22 118.39(16) . . ?
C22 C21 H21 120.8 . . ?
C17 C22 H22 119.3 . . ?
C21 C22 C17 121.50(17) . . ?
C21 C22 H22 119.2 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N2 H2 O2 0.88(2) 2.00(2) 2.8727(18) 172(2) 3_646 yes
N1 H1 O1 0.86(2) 2.02(2) 2.8687(18) 167(2) 3_546 yes

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
F1 C9 C10 C11 -179.55(16) . . . . ?
O1 C1 C2 C3 -174.55(19) . . . . ?
N1 C1 C2 C3 3.28(12) . . . . ?
N1 C3 C4 C5 119.59(17) . . . . ?
C1 N1 C3 C2 3.38(13) . . . . ?
C1 N1 C3 C4 121.80(14) . . . . ?
C1 C2 C3 N1 -2.97(11) . . . . ?
C1 C2 C3 C4 -118.44(14) . . . . ?
C2 C3 C4 C5 -141.55(16) . . . . ?
C3 N1 C1 O1 174.48(18) . . . . ?
C3 N1 C1 C2 -3.45(13) . . . . ?
C3 C4 C5 C6 -177.70(14) . . . . ?
C4 C5 C6 C7 -1.7(3) . . . . ?
C4 C5 C6 C11 177.56(16) . . . . ?
C5 C6 C7 C8 179.76(15) . . . . ?
C5 C6 C11 C10 -179.03(16) . . . . ?
C6 C7 C8 C9 -0.8(3) . . . . ?
C7 C6 C11 C10 0.3(2) . . . . ?
C7 C8 C9 F1 -179.71(15) . . . . ?
C7 C8 C9 C10 0.4(3) . . . . ?
C8 C9 C10 C11 0.3(3) . . . . ?
C9 C10 C11 C6 -0.7(3) . . . . ?
C11 C6 C7 C8 0.5(2) . . . . ?
F2 C20 C21 C22 -179.50(17) . . . . ?
O2 C12 C13 C14 179.2(2) . . . . ?
N2 C12 C13 C14 -0.57(13) . . . . ?
N2 C14 C15 C16 139.51(17) . . . . ?
C12 N2 C14 C13 -0.59(13) . . . . ?
C12 N2 C14 C15 116.34(14) . . . . ?
C12 C13 C14 N2 0.52(12) . . . . ?
C12 C13 C14 C15 -115.08(14) . . . . ?
C13 C14 C15 C16 -122.23(18) . . . . ?
C14 N2 C12 O2 -179.13(19) . . . . ?
C14 N2 C12 C13 0.60(13) . . . . ?
C14 C15 C16 C17 177.57(15) . . . . ?
C15 C16 C17 C18 -6.5(3) . . . . ?
C15 C16 C17 C22 172.56(17) . . . . ?
C16 C17 C18 C19 178.37(15) . . . . ?
C16 C17 C22 C21 -178.84(17) . . . . ?
C17 C18 C19 C20 0.7(3) . . . . ?
C18 C17 C22 C21 0.3(3) . . . . ?
C18 C19 C20 F2 179.07(16) . . . . ?
C18 C19 C20 C21 -0.3(3) . . . . ?
C19 C20 C21 C22 -0.1(3) . . . . ?
C20 C21 C22 C17 0.2(3) . . . . ?
C22 C17 C18 C19 -0.7(2) . . . . ?

_olex2_submission_original_sample_id fassr02
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.336
_oxdiff_exptl_absorpt_empirical_full_min 0.814
