# Electronic Supplementary Material (ESI) for ChemComm.
# 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_yuanbx_0424
_audit_block_doi                 10.5517/ccdc.csd.cc2gw1l0
_database_code_depnum_ccdc_archive 'CCDC 2290112'
loop_
_audit_author_name
_audit_author_address
yuanbx
;Lanzhou University
China
;
_audit_update_record             
;
2023-08-22 deposited with the CCDC.	2024-03-06 downloaded from the CCDC.
;
_audit_creation_date             2017-04-24
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5335)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C22 H17 F N2'
_chemical_formula_sum            'C22 H17 F N2'
_chemical_formula_weight         328.38
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   6.2418(3)
_cell_length_b                   18.1094(7)
_cell_length_c                   15.2988(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 96.701(4)
_cell_angle_gamma                90.00
_cell_volume                     1717.49(12)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1414
_cell_measurement_temperature    290.9(4)
_cell_measurement_theta_max      25.9550
_cell_measurement_theta_min      3.5780
_exptl_absorpt_coefficient_mu    0.083
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.64932
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_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    1.270
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             688
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.15
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0260
_diffrn_reflns_av_unetI/netI     0.0540
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            6256
_diffrn_reflns_theta_full        26.02
_diffrn_reflns_theta_max         26.02
_diffrn_reflns_theta_min         3.47
_diffrn_ambient_temperature      290.9(4)
_diffrn_detector_area_resol_mean 16.0733
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega   31.00   79.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       22.7867   77.0000   60.0000 48

#__ type_ start__ end____ width___ exp.time_
  2 omega    5.00   70.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       22.7867   77.0000  -90.0000 65

#__ type_ start__ end____ width___ exp.time_
  3 omega  -10.00   95.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       22.7867   77.0000 -180.0000 105
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0921668000
_diffrn_orient_matrix_UB_12      0.0072940000
_diffrn_orient_matrix_UB_13      0.0216908000
_diffrn_orient_matrix_UB_21      0.0531040000
_diffrn_orient_matrix_UB_22      -0.0153894000
_diffrn_orient_matrix_UB_23      0.0393419000
_diffrn_orient_matrix_UB_31      0.0422138000
_diffrn_orient_matrix_UB_32      0.0352690000
_diffrn_orient_matrix_UB_33      0.0126669000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                2104
_reflns_number_total             3383
_reflns_odcompleteness_completeness 99.75
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_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    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.134
_refine_diff_density_min         -0.225
_refine_diff_density_rms         0.044
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.019
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     226
_refine_ls_number_reflns         3383
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0901
_refine_ls_R_factor_gt           0.0524
_refine_ls_restrained_S_all      1.019
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0560P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1131
_refine_ls_wR_factor_ref         0.1337
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N2(H2), C3(H3), C4(H4), C6(H6), C7(H7), C8(H8), C9(H9), C10(H10), C12(H12),
 C13(H13), C14(H14), C15(H15), C16(H16), C19(H19), C20(H20), C21(H21), C22(H22)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_refinement_flags_posn
F0AA F 0.3818(2) 0.59557(8) 0.55346(9) 0.0760(4) Uani 1 d . . .
N1 N 0.2082(2) 0.74222(9) 0.63184(10) 0.0430(4) Uani 1 d . . .
N2 N -0.2252(3) 0.62867(10) 0.68929(11) 0.0552(5) Uani 1 d . . .
H2 H -0.3337 0.6307 0.6492 0.066 Uiso 1 calc . . R
C1 C 0.0590(3) 0.68553(10) 0.61206(12) 0.0390(5) Uani 1 d . . .
C2 C -0.0537(3) 0.67822(11) 0.68349(12) 0.0449(5) Uani 1 d . . .
C3 C 0.0265(3) 0.73060(12) 0.74735(13) 0.0544(6) Uani 1 d . . .
H3 H -0.0214 0.7376 0.8021 0.065 Uiso 1 calc . . R
C4 C 0.1851(3) 0.76860(12) 0.71481(12) 0.0536(6) Uani 1 d . . .
H4 H 0.2658 0.8064 0.7436 0.064 Uiso 1 calc . . R
C5 C -0.2296(3) 0.57700(11) 0.75548(12) 0.0420(5) Uani 1 d . . .
C6 C -0.0481(3) 0.55968(11) 0.81316(13) 0.0484(5) Uani 1 d . . .
H6 H 0.0817 0.5838 0.8087 0.058 Uiso 1 calc . . R
C7 C -0.0602(4) 0.50634(12) 0.87755(14) 0.0612(6) Uani 1 d . . .
H7 H 0.0620 0.4951 0.9161 0.073 Uiso 1 calc . . R
C8 C -0.2505(5) 0.46989(13) 0.88512(17) 0.0739(8) Uani 1 d . . .
H8 H -0.2579 0.4343 0.9285 0.089 Uiso 1 calc . . R
C9 C -0.4295(4) 0.48680(13) 0.82758(17) 0.0716(7) Uani 1 d . . .
H9 H -0.5583 0.4620 0.8320 0.086 Uiso 1 calc . . R
C10 C -0.4215(4) 0.53951(12) 0.76391(14) 0.0555(6) Uani 1 d . . .
H10 H -0.5449 0.5504 0.7260 0.067 Uiso 1 calc . . R
C11 C 0.3544(3) 0.77333(10) 0.57665(12) 0.0404(5) Uani 1 d . . .
C12 C 0.2945(3) 0.78509(11) 0.48806(13) 0.0496(5) Uani 1 d . . .
H12 H 0.1584 0.7709 0.4623 0.059 Uiso 1 calc . . R
C13 C 0.4382(4) 0.81805(11) 0.43784(15) 0.0591(6) Uani 1 d . . .
H13 H 0.3990 0.8253 0.3779 0.071 Uiso 1 calc . . R
C14 C 0.6389(4) 0.84022(12) 0.47571(17) 0.0630(7) Uani 1 d . . .
H14 H 0.7343 0.8627 0.4416 0.076 Uiso 1 calc . . R
C15 C 0.6977(3) 0.82892(11) 0.56413(15) 0.0556(6) Uani 1 d . . .
H15 H 0.8326 0.8443 0.5899 0.067 Uiso 1 calc . . R
C16 C 0.5568(3) 0.79475(10) 0.61498(14) 0.0461(5) Uani 1 d . . .
H16 H 0.5981 0.7863 0.6745 0.055 Uiso 1 calc . . R
C17 C 0.0312(3) 0.64432(10) 0.52876(12) 0.0392(5) Uani 1 d . . .
C18 C 0.1907(3) 0.59992(12) 0.50103(14) 0.0508(5) Uani 1 d . . .
C19 C 0.1664(4) 0.56011(14) 0.42457(16) 0.0686(7) Uani 1 d . . .
H19 H 0.2789 0.5314 0.4084 0.082 Uiso 1 calc . . R
C20 C -0.0275(4) 0.56338(15) 0.37228(16) 0.0750(7) Uani 1 d . . .
H20 H -0.0470 0.5369 0.3199 0.090 Uiso 1 calc . . R
C21 C -0.1929(4) 0.60567(13) 0.39719(15) 0.0687(7) Uani 1 d . . .
H21 H -0.3246 0.6074 0.3619 0.082 Uiso 1 calc . . R
C22 C -0.1636(3) 0.64546(12) 0.47443(13) 0.0501(5) Uani 1 d . . .
H22 H -0.2768 0.6738 0.4906 0.060 Uiso 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
F0AA C18 1.360(2) . ?
N1 C1 1.395(2) . ?
N1 C4 1.379(2) . ?
N1 C11 1.429(2) . ?
N2 H2 0.8600 . ?
N2 C2 1.407(2) . ?
N2 C5 1.381(2) . ?
C1 C2 1.373(2) . ?
C1 C17 1.469(2) . ?
C2 C3 1.411(3) . ?
C3 H3 0.9300 . ?
C3 C4 1.348(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.388(3) . ?
C5 C10 1.396(3) . ?
C6 H6 0.9300 . ?
C6 C7 1.388(3) . ?
C7 H7 0.9300 . ?
C7 C8 1.376(3) . ?
C8 H8 0.9300 . ?
C8 C9 1.374(4) . ?
C9 H9 0.9300 . ?
C9 C10 1.369(3) . ?
C10 H10 0.9300 . ?
C11 C12 1.380(3) . ?
C11 C16 1.385(3) . ?
C12 H12 0.9300 . ?
C12 C13 1.383(3) . ?
C13 H13 0.9300 . ?
C13 C14 1.377(3) . ?
C14 H14 0.9300 . ?
C14 C15 1.375(3) . ?
C15 H15 0.9300 . ?
C15 C16 1.386(3) . ?
C16 H16 0.9300 . ?
C17 C18 1.384(3) . ?
C17 C22 1.391(3) . ?
C18 C19 1.367(3) . ?
C19 H19 0.9300 . ?
C19 C20 1.372(3) . ?
C20 H20 0.9300 . ?
C20 C21 1.375(3) . ?
C21 H21 0.9300 . ?
C21 C22 1.378(3) . ?
C22 H22 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 N1 C11 128.15(15) . . ?
C4 N1 C1 108.42(16) . . ?
C4 N1 C11 123.32(16) . . ?
C2 N2 H2 118.0 . . ?
C5 N2 H2 118.0 . . ?
C5 N2 C2 123.94(17) . . ?
N1 C1 C17 124.76(16) . . ?
C2 C1 N1 106.80(16) . . ?
C2 C1 C17 128.42(17) . . ?
N2 C2 C3 126.58(17) . . ?
C1 C2 N2 125.14(18) . . ?
C1 C2 C3 108.24(17) . . ?
C2 C3 H3 126.2 . . ?
C4 C3 C2 107.69(17) . . ?
C4 C3 H3 126.2 . . ?
N1 C4 H4 125.6 . . ?
C3 C4 N1 108.85(18) . . ?
C3 C4 H4 125.6 . . ?
N2 C5 C6 122.31(18) . . ?
N2 C5 C10 119.20(19) . . ?
C6 C5 C10 118.48(18) . . ?
C5 C6 H6 120.0 . . ?
C7 C6 C5 120.0(2) . . ?
C7 C6 H6 120.0 . . ?
C6 C7 H7 119.6 . . ?
C8 C7 C6 120.8(2) . . ?
C8 C7 H7 119.6 . . ?
C7 C8 H8 120.5 . . ?
C9 C8 C7 119.0(2) . . ?
C9 C8 H8 120.5 . . ?
C8 C9 H9 119.4 . . ?
C10 C9 C8 121.1(2) . . ?
C10 C9 H9 119.4 . . ?
C5 C10 H10 119.7 . . ?
C9 C10 C5 120.5(2) . . ?
C9 C10 H10 119.7 . . ?
C12 C11 N1 121.52(18) . . ?
C12 C11 C16 120.10(18) . . ?
C16 C11 N1 118.31(17) . . ?
C11 C12 H12 120.2 . . ?
C11 C12 C13 119.6(2) . . ?
C13 C12 H12 120.2 . . ?
C12 C13 H13 119.7 . . ?
C14 C13 C12 120.6(2) . . ?
C14 C13 H13 119.7 . . ?
C13 C14 H14 120.1 . . ?
C15 C14 C13 119.7(2) . . ?
C15 C14 H14 120.1 . . ?
C14 C15 H15 119.8 . . ?
C14 C15 C16 120.3(2) . . ?
C16 C15 H15 119.8 . . ?
C11 C16 C15 119.6(2) . . ?
C11 C16 H16 120.2 . . ?
C15 C16 H16 120.2 . . ?
C18 C17 C1 122.98(18) . . ?
C18 C17 C22 115.80(18) . . ?
C22 C17 C1 121.17(18) . . ?
F0AA C18 C17 117.74(19) . . ?
F0AA C18 C19 118.4(2) . . ?
C19 C18 C17 123.8(2) . . ?
C18 C19 H19 120.7 . . ?
C18 C19 C20 118.6(2) . . ?
C20 C19 H19 120.7 . . ?
C19 C20 H20 119.9 . . ?
C19 C20 C21 120.2(2) . . ?
C21 C20 H20 119.9 . . ?
C20 C21 H21 120.0 . . ?
C20 C21 C22 120.0(2) . . ?
C22 C21 H21 120.0 . . ?
C17 C22 H22 119.2 . . ?
C21 C22 C17 121.6(2) . . ?
C21 C22 H22 119.2 . . ?

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
F0AA C18 C19 C20 178.9(2) . . . . ?
N1 C1 C2 N2 177.65(17) . . . . ?
N1 C1 C2 C3 0.0(2) . . . . ?
N1 C1 C17 C18 64.0(3) . . . . ?
N1 C1 C17 C22 -118.8(2) . . . . ?
N1 C11 C12 C13 177.41(18) . . . . ?
N1 C11 C16 C15 -176.35(16) . . . . ?
N2 C2 C3 C4 -177.74(19) . . . . ?
N2 C5 C6 C7 -178.82(17) . . . . ?
N2 C5 C10 C9 178.49(18) . . . . ?
C1 N1 C4 C3 -0.2(2) . . . . ?
C1 N1 C11 C12 39.2(3) . . . . ?
C1 N1 C11 C16 -143.66(19) . . . . ?
C1 C2 C3 C4 -0.1(2) . . . . ?
C1 C17 C18 F0AA -0.9(3) . . . . ?
C1 C17 C18 C19 178.7(2) . . . . ?
C1 C17 C22 C21 -178.49(19) . . . . ?
C2 N2 C5 C6 -12.5(3) . . . . ?
C2 N2 C5 C10 168.91(18) . . . . ?
C2 C1 C17 C18 -117.5(2) . . . . ?
C2 C1 C17 C22 59.7(3) . . . . ?
C2 C3 C4 N1 0.2(2) . . . . ?
C4 N1 C1 C2 0.1(2) . . . . ?
C4 N1 C1 C17 178.92(18) . . . . ?
C4 N1 C11 C12 -136.7(2) . . . . ?
C4 N1 C11 C16 40.5(3) . . . . ?
C5 N2 C2 C1 124.4(2) . . . . ?
C5 N2 C2 C3 -58.4(3) . . . . ?
C5 C6 C7 C8 0.2(3) . . . . ?
C6 C5 C10 C9 -0.2(3) . . . . ?
C6 C7 C8 C9 0.3(3) . . . . ?
C7 C8 C9 C10 -0.6(4) . . . . ?
C8 C9 C10 C5 0.6(3) . . . . ?
C10 C5 C6 C7 -0.2(3) . . . . ?
C11 N1 C1 C2 -176.18(18) . . . . ?
C11 N1 C1 C17 2.6(3) . . . . ?
C11 N1 C4 C3 176.31(18) . . . . ?
C11 C12 C13 C14 -1.0(3) . . . . ?
C12 C11 C16 C15 0.9(3) . . . . ?
C12 C13 C14 C15 0.5(4) . . . . ?
C13 C14 C15 C16 0.6(3) . . . . ?
C14 C15 C16 C11 -1.3(3) . . . . ?
C16 C11 C12 C13 0.3(3) . . . . ?
C17 C1 C2 N2 -1.1(3) . . . . ?
C17 C1 C2 C3 -178.72(19) . . . . ?
C17 C18 C19 C20 -0.7(4) . . . . ?
C18 C17 C22 C21 -1.1(3) . . . . ?
C18 C19 C20 C21 -0.3(4) . . . . ?
C19 C20 C21 C22 0.6(4) . . . . ?
C20 C21 C22 C17 0.1(4) . . . . ?
C22 C17 C18 F0AA -178.20(18) . . . . ?
C22 C17 C18 C19 1.4(3) . . . . ?

_olex2_date_sample_data_collection 2017-04-24
_olex2_submission_special_instructions 'No special instructions were received'
