# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2024

####################################################################### 
# 
# 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_wch2
_database_code_depnum_ccdc_archive 'CCDC 2368143'
loop_
_audit_author_name
_audit_author_address
'chuanhu Wang'
;Northwest University
China
;
_audit_update_record             
;
2024-07-04 deposited with the CCDC.	2024-07-17 downloaded from the CCDC.
;
_audit_creation_date             2024-07-04
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.02.04 svn.rd84adfe8 for OlexSys, GUI svn.r6032)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C22 H18 F N O'
_chemical_formula_sum            'C22 H18 F N O'
_chemical_formula_weight         331.37
_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 0.0148 0.0070 '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 0.0599 0.0411 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0253 0.0136 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0412 0.0250 '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           61
_space_group_name_H-M_alt        'P b c a'
_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'
'-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                   15.9994(8)
_cell_length_b                   11.0230(6)
_cell_length_c                   19.3105(9)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3405.6(3)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    9838
_cell_measurement_temperature    200.0
_cell_measurement_theta_max      57.27
_cell_measurement_theta_min      4.68
_shelx_estimated_absorpt_T_max   0.948
_shelx_estimated_absorpt_T_min   0.932
_exptl_absorpt_coefficient_mu    0.447
_exptl_absorpt_correction_T_max  0.7512
_exptl_absorpt_correction_T_min  0.5682
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1317 before and 0.0659 after correction.
The Ratio of minimum to maximum transmission is 0.7564.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.293
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1392
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.12
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0504
_diffrn_reflns_av_unetI/netI     0.0247
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            37620
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         57.285
_diffrn_reflns_theta_min         3.983
_diffrn_ambient_temperature      200.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           GaK\a
_diffrn_radiation_wavelength     1.34139
_diffrn_source                   ?
_diffrn_source_current           2.86
_diffrn_source_power             0.1997996
_diffrn_source_voltage           69.86
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3112
_reflns_number_total             3512
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2014/7 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.170
_refine_diff_density_min         -0.262
_refine_diff_density_rms         0.067
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.072
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     227
_refine_ls_number_reflns         3512
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0441
_refine_ls_R_factor_gt           0.0394
_refine_ls_restrained_S_all      1.072
_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)+(0.0500P)²+0.8700P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0968
_refine_ls_wR_factor_ref         0.1004
_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:
 C006(H006), C009(H009)
2.b Aromatic/amide H refined with riding coordinates:
 C00A(H00A), C00C(H00C), C00D(H00D), C00F(H00F), C00G(H00G), C00H(H00H),
 C00I(H00I), C00J(H00J), C00K(H00K), C00M(H00M), C00N(H00N), C00O(H00O),
 C00P(H00P)
2.c Idealised Me refined as rotating group:
 C00L(H00B,H00E,H00L)
;
_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
F001 F 0.44717(5) 0.18054(7) 0.68342(4) 0.0497(2) Uani 1 1 d . . . . .
O002 O 0.34621(6) 0.33241(8) 0.50799(4) 0.0375(2) Uani 1 1 d . . . . .
N003 N 0.23575(6) 0.16395(9) 0.55383(5) 0.0277(2) Uani 1 1 d . . . . .
C004 C 0.22681(7) 0.19645(10) 0.72036(5) 0.0245(2) Uani 1 1 d . . . . .
C005 C 0.17024(7) 0.24598(10) 0.55631(5) 0.0262(2) Uani 1 1 d . . . . .
C006 C 0.25072(7) 0.27504(10) 0.65864(5) 0.0239(2) Uani 1 1 d . . . . .
H006 H 0.2832 0.3474 0.6746 0.029 Uiso 1 1 calc R U . . .
C007 C 0.43381(7) 0.34543(10) 0.60522(5) 0.0260(2) Uani 1 1 d . . . . .
C008 C 0.17509(7) 0.31527(9) 0.61713(5) 0.0243(2) Uani 1 1 d . . . . .
C009 C 0.30046(7) 0.20575(10) 0.60118(5) 0.0248(2) Uani 1 1 d . . . . .
H009 H 0.3319 0.1357 0.6213 0.030 Uiso 1 1 calc R U . . .
C00A C 0.11399(7) 0.39853(10) 0.63304(6) 0.0309(3) Uani 1 1 d . . . . .
H00A H 0.1172 0.4448 0.6745 0.037 Uiso 1 1 calc R U . . .
C00B C 0.36006(7) 0.29577(10) 0.56617(5) 0.0262(2) Uani 1 1 d . . . . .
C00C C 0.46558(7) 0.45747(11) 0.58393(6) 0.0323(3) Uani 1 1 d . . . . .
H00C H 0.4393 0.4991 0.5468 0.039 Uiso 1 1 calc R U . . .
C00D C 0.16579(7) 0.10725(11) 0.71412(6) 0.0306(3) Uani 1 1 d . . . . .
H00D H 0.1408 0.0924 0.6703 0.037 Uiso 1 1 calc R U . . .
C00E C 0.47480(7) 0.28908(10) 0.65966(6) 0.0308(3) Uani 1 1 d . . . . .
C00F C 0.26328(7) 0.21494(11) 0.78489(6) 0.0316(3) Uani 1 1 d . . . . .
H00F H 0.3057 0.2746 0.7900 0.038 Uiso 1 1 calc R U . . .
C00G C 0.10446(8) 0.26119(12) 0.51012(6) 0.0350(3) Uani 1 1 d . . . . .
H00G H 0.1013 0.2155 0.4685 0.042 Uiso 1 1 calc R U . . .
C00H C 0.54444(8) 0.33721(12) 0.69145(7) 0.0385(3) Uani 1 1 d . . . . .
H00H H 0.5715 0.2948 0.7279 0.046 Uiso 1 1 calc R U . . .
C00I C 0.14103(8) 0.03979(11) 0.77111(6) 0.0361(3) Uani 1 1 d . . . . .
H00I H 0.0992 -0.0207 0.7661 0.043 Uiso 1 1 calc R U . . .
C00J C 0.23841(8) 0.14713(13) 0.84207(6) 0.0384(3) Uani 1 1 d . . . . .
H00J H 0.2638 0.1607 0.8859 0.046 Uiso 1 1 calc R U . . .
C00K C 0.17691(8) 0.06012(12) 0.83520(6) 0.0377(3) Uani 1 1 d . . . . .
H00K H 0.1593 0.0145 0.8743 0.045 Uiso 1 1 calc R U . . .
C00L C 0.25706(9) 0.09442(11) 0.49269(6) 0.0368(3) Uani 1 1 d . . . . .
H00B H 0.2068 0.0547 0.4746 0.055 Uiso 1 1 calc R U . . .
H00E H 0.2988 0.0328 0.5047 0.055 Uiso 1 1 calc R U . . .
H00L H 0.2800 0.1487 0.4573 0.055 Uiso 1 1 calc R U . . .
C00M C 0.53436(8) 0.50912(12) 0.61561(7) 0.0400(3) Uani 1 1 d . . . . .
H00M H 0.5544 0.5860 0.6008 0.048 Uiso 1 1 calc R U . . .
C00N C 0.04706(8) 0.41396(12) 0.58729(7) 0.0395(3) Uani 1 1 d . . . . .
H00N H 0.0043 0.4710 0.5975 0.047 Uiso 1 1 calc R U . . .
C00O C 0.57398(8) 0.44808(13) 0.66925(7) 0.0417(3) Uani 1 1 d . . . . .
H00O H 0.6217 0.4829 0.6908 0.050 Uiso 1 1 calc R U . . .
C00P C 0.04325(8) 0.34596(13) 0.52720(7) 0.0414(3) Uani 1 1 d . . . . .
H00P H -0.0026 0.3574 0.4966 0.050 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
F001 C00E 1.3556(14) . ?
O002 C00B 1.2143(13) . ?
N003 C005 1.3851(14) . ?
N003 C009 1.4561(13) . ?
N003 C00L 1.4484(14) . ?
C004 C006 1.5223(14) . ?
C004 C00D 1.3908(16) . ?
C004 C00F 1.3909(15) . ?
C005 C008 1.4030(15) . ?
C005 C00G 1.3898(15) . ?
C006 H006 1.0000 . ?
C006 C008 1.5176(15) . ?
C006 C009 1.5647(14) . ?
C007 C00B 1.5035(15) . ?
C007 C00C 1.3974(16) . ?
C007 C00E 1.3859(16) . ?
C008 C00A 1.3757(15) . ?
C009 H009 1.0000 . ?
C009 C00B 1.5332(15) . ?
C00A H00A 0.9500 . ?
C00A C00N 1.3985(17) . ?
C00C H00C 0.9500 . ?
C00C C00M 1.3818(17) . ?
C00D H00D 0.9500 . ?
C00D C00I 1.3860(16) . ?
C00E C00H 1.3783(17) . ?
C00F H00F 0.9500 . ?
C00F C00J 1.3916(17) . ?
C00G H00G 0.9500 . ?
C00G C00P 1.3931(19) . ?
C00H H00H 0.9500 . ?
C00H C00O 1.3787(19) . ?
C00I H00I 0.9500 . ?
C00I C00K 1.3826(18) . ?
C00J H00J 0.9500 . ?
C00J C00K 1.3805(19) . ?
C00K H00K 0.9500 . ?
C00L H00B 0.9800 . ?
C00L H00E 0.9800 . ?
C00L H00L 0.9800 . ?
C00M H00M 0.9500 . ?
C00M C00O 1.3884(19) . ?
C00N H00N 0.9500 . ?
C00N C00P 1.383(2) . ?
C00O H00O 0.9500 . ?
C00P H00P 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
C005 N003 C009 108.04(9) . . ?
C005 N003 C00L 123.49(9) . . ?
C00L N003 C009 120.79(10) . . ?
C00D C004 C006 120.72(9) . . ?
C00D C004 C00F 118.41(10) . . ?
C00F C004 C006 120.83(10) . . ?
N003 C005 C008 110.03(9) . . ?
N003 C005 C00G 129.02(10) . . ?
C00G C005 C008 120.90(11) . . ?
C004 C006 H006 110.1 . . ?
C004 C006 C009 113.91(9) . . ?
C008 C006 C004 112.30(9) . . ?
C008 C006 H006 110.1 . . ?
C008 C006 C009 100.00(8) . . ?
C009 C006 H006 110.1 . . ?
C00C C007 C00B 117.37(10) . . ?
C00E C007 C00B 126.06(10) . . ?
C00E C007 C00C 116.56(11) . . ?
C005 C008 C006 109.10(9) . . ?
C00A C008 C005 120.71(10) . . ?
C00A C008 C006 130.06(10) . . ?
N003 C009 C006 103.77(8) . . ?
N003 C009 H009 111.0 . . ?
N003 C009 C00B 111.73(9) . . ?
C006 C009 H009 111.0 . . ?
C00B C009 C006 108.24(9) . . ?
C00B C009 H009 111.0 . . ?
C008 C00A H00A 120.5 . . ?
C008 C00A C00N 118.96(11) . . ?
C00N C00A H00A 120.5 . . ?
O002 C00B C007 119.09(10) . . ?
O002 C00B C009 120.64(10) . . ?
C007 C00B C009 120.17(9) . . ?
C007 C00C H00C 119.2 . . ?
C00M C00C C007 121.57(11) . . ?
C00M C00C H00C 119.2 . . ?
C004 C00D H00D 119.6 . . ?
C00I C00D C004 120.74(11) . . ?
C00I C00D H00D 119.6 . . ?
F001 C00E C007 119.87(10) . . ?
F001 C00E C00H 116.91(11) . . ?
C00H C00E C007 123.22(11) . . ?
C004 C00F H00F 119.6 . . ?
C004 C00F C00J 120.81(11) . . ?
C00J C00F H00F 119.6 . . ?
C005 C00G H00G 121.3 . . ?
C005 C00G C00P 117.47(12) . . ?
C00P C00G H00G 121.3 . . ?
C00E C00H H00H 120.7 . . ?
C00E C00H C00O 118.68(12) . . ?
C00O C00H H00H 120.7 . . ?
C00D C00I H00I 119.8 . . ?
C00K C00I C00D 120.34(12) . . ?
C00K C00I H00I 119.8 . . ?
C00F C00J H00J 120.0 . . ?
C00K C00J C00F 120.04(11) . . ?
C00K C00J H00J 120.0 . . ?
C00I C00K H00K 120.2 . . ?
C00J C00K C00I 119.65(11) . . ?
C00J C00K H00K 120.2 . . ?
N003 C00L H00B 109.5 . . ?
N003 C00L H00E 109.5 . . ?
N003 C00L H00L 109.5 . . ?
H00B C00L H00E 109.5 . . ?
H00B C00L H00L 109.5 . . ?
H00E C00L H00L 109.5 . . ?
C00C C00M H00M 120.2 . . ?
C00C C00M C00O 119.62(12) . . ?
C00O C00M H00M 120.2 . . ?
C00A C00N H00N 120.1 . . ?
C00P C00N C00A 119.86(12) . . ?
C00P C00N H00N 120.1 . . ?
C00H C00O C00M 120.33(12) . . ?
C00H C00O H00O 119.8 . . ?
C00M C00O H00O 119.8 . . ?
C00G C00P H00P 119.0 . . ?
C00N C00P C00G 122.09(11) . . ?
C00N C00P H00P 119.0 . . ?

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
F001 C00E C00H C00O -179.34(12) . . . . ?
N003 C005 C008 C006 -0.11(12) . . . . ?
N003 C005 C008 C00A -176.36(10) . . . . ?
N003 C005 C00G C00P 175.88(12) . . . . ?
N003 C009 C00B O002 6.47(15) . . . . ?
N003 C009 C00B C007 -177.14(9) . . . . ?
C004 C006 C008 C005 -103.73(10) . . . . ?
C004 C006 C008 C00A 72.07(14) . . . . ?
C004 C006 C009 N003 92.34(10) . . . . ?
C004 C006 C009 C00B -148.83(9) . . . . ?
C004 C00D C00I C00K -0.14(19) . . . . ?
C004 C00F C00J C00K 0.09(19) . . . . ?
C005 N003 C009 C006 29.74(11) . . . . ?
C005 N003 C009 C00B -86.67(10) . . . . ?
C005 C008 C00A C00N -0.54(16) . . . . ?
C005 C00G C00P C00N 0.52(19) . . . . ?
C006 C004 C00D C00I -176.75(11) . . . . ?
C006 C004 C00F C00J 176.78(11) . . . . ?
C006 C008 C00A C00N -175.92(11) . . . . ?
C006 C009 C00B O002 -107.18(11) . . . . ?
C006 C009 C00B C007 69.20(12) . . . . ?
C007 C00C C00M C00O 0.95(19) . . . . ?
C007 C00E C00H C00O 1.5(2) . . . . ?
C008 C005 C00G C00P -1.09(17) . . . . ?
C008 C006 C009 N003 -27.63(10) . . . . ?
C008 C006 C009 C00B 91.19(9) . . . . ?
C008 C00A C00N C00P -0.03(18) . . . . ?
C009 N003 C005 C008 -19.28(12) . . . . ?
C009 N003 C005 C00G 163.50(11) . . . . ?
C009 C006 C008 C005 17.41(11) . . . . ?
C009 C006 C008 C00A -166.79(11) . . . . ?
C00A C00N C00P C00G 0.0(2) . . . . ?
C00B C007 C00C C00M -178.52(11) . . . . ?
C00B C007 C00E F001 -2.02(18) . . . . ?
C00B C007 C00E C00H 177.14(11) . . . . ?
C00C C007 C00B O002 21.25(15) . . . . ?
C00C C007 C00B C009 -155.19(10) . . . . ?
C00C C007 C00E F001 179.57(10) . . . . ?
C00C C007 C00E C00H -1.28(17) . . . . ?
C00C C00M C00O C00H -0.8(2) . . . . ?
C00D C004 C006 C008 41.83(14) . . . . ?
C00D C004 C006 C009 -70.95(13) . . . . ?
C00D C004 C00F C00J -0.99(18) . . . . ?
C00D C00I C00K C00J -0.8(2) . . . . ?
C00E C007 C00B O002 -157.15(11) . . . . ?
C00E C007 C00B C009 26.41(16) . . . . ?
C00E C007 C00C C00M 0.04(17) . . . . ?
C00E C00H C00O C00M -0.4(2) . . . . ?
C00F C004 C006 C008 -135.89(11) . . . . ?
C00F C004 C006 C009 111.34(11) . . . . ?
C00F C004 C00D C00I 1.01(17) . . . . ?
C00F C00J C00K C00I 0.8(2) . . . . ?
C00G C005 C008 C006 177.38(10) . . . . ?
C00G C005 C008 C00A 1.12(16) . . . . ?
C00L N003 C005 C008 -168.72(10) . . . . ?
C00L N003 C005 C00G 14.06(18) . . . . ?
C00L N003 C009 C006 -179.84(9) . . . . ?
C00L N003 C009 C00B 63.76(13) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
