# Electronic Supplementary Material (ESI) for Chemical Communications.
# 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_1
_database_code_depnum_ccdc_archive 'CCDC 2306402'
loop_
_audit_author_name
_audit_author_address
'Han Z.-G'
;P
China
;
_audit_update_record             
;
2023-11-08 deposited with the CCDC.	2024-04-16 downloaded from the CCDC.
;
_audit_creation_date             2023-11-07
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.06.28 svn.raecde09e for OlexSys, GUI svn.r6132)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C19 H19 F3 N2'
_chemical_formula_sum            'C19 H19 F3 N2'
_chemical_formula_weight         332.36
_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 0.0181 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'

_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                   10.340(3)
_cell_length_b                   15.240(5)
_cell_length_c                   11.008(3)
_cell_angle_alpha                90
_cell_angle_beta                 94.938(17)
_cell_angle_gamma                90
_cell_volume                     1728.2(9)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    6176
_cell_measurement_temperature    273.15
_cell_measurement_theta_max      63.71
_cell_measurement_theta_min      4.29
_shelx_estimated_absorpt_T_max   0.900
_shelx_estimated_absorpt_T_min   0.886
_exptl_absorpt_coefficient_mu    0.824
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.277
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             696
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.13
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0537
_diffrn_reflns_av_unetI/netI     0.0414
_diffrn_reflns_Laue_measured_fraction_full 0.986
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            14443
_diffrn_reflns_point_group_measured_fraction_full 0.986
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_theta_full        64.159
_diffrn_reflns_theta_max         64.159
_diffrn_reflns_theta_min         4.291
_diffrn_ambient_temperature      273.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   ?
_diffrn_source_current           1.0
_diffrn_source_power             0.05
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1996
_reflns_number_total             2887
_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 V8.38A (Bruker, 2018)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (Bruker, 2018)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_refine_diff_density_max         0.240
_refine_diff_density_min         -0.384
_refine_diff_density_rms         0.078
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.108
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     223
_refine_ls_number_reflns         2846
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1045
_refine_ls_R_factor_gt           0.0720
_refine_ls_restrained_S_all      1.108
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1223P)²+0.7770P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1845
_refine_ls_wR_factor_ref         0.2260
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C00B(H00A,H00B), C00G(H00E,H00G)
2.b Aromatic/amide H refined with riding coordinates:
 C009(H009), C00C(H00C), C00D(H00D), C00F(H00F), C00I(H00I), C00J(H00J),
 C00K(H00K), C00M(H00M)
2.c Idealised Me refined as rotating group:
 C00N(H00H,H00L,H00N), C00O(H00O,H00P,H00Q)
;
_atom_sites_solution_hydrogens   mixed
_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 0.2807(2) 0.52244(13) 0.3940(2) 0.0827(7) Uani 1 1 d . . . . .
F002 F 0.2498(2) 0.65766(15) 0.34706(19) 0.0887(7) Uani 1 1 d . . . . .
F003 F 0.1533(2) 0.60007(17) 0.4922(2) 0.0934(8) Uani 1 1 d . . . . .
N004 N 0.4940(2) 0.62328(15) 0.4597(2) 0.0522(7) Uani 1 1 d . . . . .
N005 N 0.4007(3) 0.56542(16) 0.6282(2) 0.0556(7) Uani 1 1 d . . . . .
C006 C 0.3409(3) 0.55982(17) 0.7365(3) 0.0478(7) Uani 1 1 d . . . . .
C007 C 0.3803(3) 0.62792(17) 0.5307(3) 0.0489(7) Uani 1 1 d . . . . .
C008 C 0.5368(3) 0.70055(18) 0.4434(3) 0.0510(8) Uani 1 1 d . . . . .
C009 C 0.3916(3) 0.50178(19) 0.8253(3) 0.0570(8) Uani 1 1 d . . . . .
H009 H 0.464684 0.468922 0.811319 0.068 Uiso 1 1 calc R U . . .
C00A C 0.6477(3) 0.71595(18) 0.3710(3) 0.0523(8) Uani 1 1 d . . . . .
C00B C 0.3690(3) 0.72435(18) 0.5727(3) 0.0575(8) Uani 1 1 d . . . . .
H00A H 0.281982 0.746726 0.552573 0.069 Uiso 1 1 calc R U . . .
H00B H 0.390381 0.729625 0.659957 0.069 Uiso 1 1 calc R U . . .
C00C C 0.7412(3) 0.6513(2) 0.3597(3) 0.0598(9) Uani 1 1 d . . . . .
H00C H 0.737848 0.599620 0.404211 0.072 Uiso 1 1 calc R U . . .
C00D C 0.3359(3) 0.4918(2) 0.9341(3) 0.0619(9) Uani 1 1 d . . . . .
H00D H 0.372292 0.452086 0.991358 0.074 Uiso 1 1 calc R U . . .
C00E C 0.2282(3) 0.5388(2) 0.9605(3) 0.0618(9) Uani 1 1 d . . . . .
C00F C 0.2330(3) 0.6080(2) 0.7626(3) 0.0575(8) Uani 1 1 d . . . . .
H00F H 0.196316 0.647786 0.705517 0.069 Uiso 1 1 calc R U . . .
C00G C 0.4672(3) 0.77323(19) 0.5024(3) 0.0614(9) Uani 1 1 d . . . . .
H00E H 0.424187 0.812004 0.441772 0.074 Uiso 1 1 calc R U . . .
H00G H 0.526537 0.807248 0.556792 0.074 Uiso 1 1 calc R U . . .
C00H C 0.2656(3) 0.6021(2) 0.4421(3) 0.0620(9) Uani 1 1 d . . . . .
C00I C 0.8382(3) 0.6631(2) 0.2835(3) 0.0675(9) Uani 1 1 d . . . . .
H00I H 0.899617 0.619076 0.277745 0.081 Uiso 1 1 calc R U . . .
C00J C 0.6586(3) 0.7932(2) 0.3051(3) 0.0625(9) Uani 1 1 d . . . . .
H00J H 0.599246 0.838307 0.312695 0.075 Uiso 1 1 calc R U . . .
C00K C 0.1788(3) 0.5977(2) 0.8734(3) 0.0623(9) Uani 1 1 d . . . . .
H00K H 0.107209 0.631587 0.889071 0.075 Uiso 1 1 calc R U . . .
C00L C 0.8469(3) 0.7389(2) 0.2148(3) 0.0664(9) Uani 1 1 d . . . . .
C00M C 0.7562(4) 0.8036(2) 0.2287(3) 0.0710(10) Uani 1 1 d . . . . .
H00M H 0.760986 0.855725 0.185304 0.085 Uiso 1 1 calc R U . . .
C00N C 0.1702(5) 0.5277(3) 1.0812(4) 0.0919(13) Uani 1 1 d . . . . .
H00H H 0.153188 0.466627 1.094411 0.138 Uiso 1 1 calc R U . . .
H00L H 0.090488 0.560103 1.079822 0.138 Uiso 1 1 calc R U . . .
H00N H 0.230045 0.549187 1.145832 0.138 Uiso 1 1 calc R U . . .
C00O C 0.9493(4) 0.7488(3) 0.1263(4) 0.0952(13) Uani 1 1 d . . . . .
H00O H 1.028474 0.721929 0.159637 0.143 Uiso 1 1 calc R U . . .
H00P H 0.964126 0.810014 0.112206 0.143 Uiso 1 1 calc R U . . .
H00Q H 0.920422 0.720844 0.050631 0.143 Uiso 1 1 calc R U . . .
H005 H 0.445(3) 0.522(2) 0.613(3) 0.047(8) 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
F001 C00H 1.339(4) . ?
F002 C00H 1.345(4) . ?
F003 C00H 1.328(4) . ?
N004 C007 1.469(4) . ?
N004 C008 1.276(4) . ?
N005 C006 1.393(4) . ?
N005 C007 1.436(4) . ?
N005 H005 0.83(3) . ?
C006 C009 1.387(4) . ?
C006 C00F 1.387(4) . ?
C007 C00B 1.548(4) . ?
C007 C00H 1.521(5) . ?
C008 C00A 1.471(4) . ?
C008 C00G 1.499(4) . ?
C009 H009 0.9300 . ?
C009 C00D 1.382(4) . ?
C00A C00C 1.393(4) . ?
C00A C00J 1.393(4) . ?
C00B H00A 0.9700 . ?
C00B H00B 0.9700 . ?
C00B C00G 1.524(4) . ?
C00C H00C 0.9300 . ?
C00C C00I 1.374(4) . ?
C00D H00D 0.9300 . ?
C00D C00E 1.375(5) . ?
C00E C00K 1.379(5) . ?
C00E C00N 1.514(5) . ?
C00F H00F 0.9300 . ?
C00F C00K 1.394(4) . ?
C00G H00E 0.9700 . ?
C00G H00G 0.9700 . ?
C00I H00I 0.9300 . ?
C00I C00L 1.387(5) . ?
C00J H00J 0.9300 . ?
C00J C00M 1.377(4) . ?
C00K H00K 0.9300 . ?
C00L C00M 1.380(5) . ?
C00L C00O 1.507(5) . ?
C00M H00M 0.9300 . ?
C00N H00H 0.9600 . ?
C00N H00L 0.9600 . ?
C00N H00N 0.9600 . ?
C00O H00O 0.9600 . ?
C00O H00P 0.9600 . ?
C00O H00Q 0.9600 . ?

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
C008 N004 C007 109.5(2) . . ?
C006 N005 C007 129.2(2) . . ?
C006 N005 H005 115(2) . . ?
C007 N005 H005 115(2) . . ?
C009 C006 N005 118.3(3) . . ?
C00F C006 N005 124.7(3) . . ?
C00F C006 C009 117.0(3) . . ?
N004 C007 C00B 106.8(2) . . ?
N004 C007 C00H 105.2(2) . . ?
N005 C007 N004 107.0(2) . . ?
N005 C007 C00B 114.6(3) . . ?
N005 C007 C00H 111.3(2) . . ?
C00H C007 C00B 111.3(3) . . ?
N004 C008 C00A 121.3(2) . . ?
N004 C008 C00G 115.8(3) . . ?
C00A C008 C00G 122.9(2) . . ?
C006 C009 H009 119.3 . . ?
C00D C009 C006 121.3(3) . . ?
C00D C009 H009 119.3 . . ?
C00C C00A C008 121.0(3) . . ?
C00C C00A C00J 117.6(3) . . ?
C00J C00A C008 121.3(3) . . ?
C007 C00B H00A 111.0 . . ?
C007 C00B H00B 111.0 . . ?
H00A C00B H00B 109.0 . . ?
C00G C00B C007 104.0(2) . . ?
C00G C00B H00A 111.0 . . ?
C00G C00B H00B 111.0 . . ?
C00A C00C H00C 119.6 . . ?
C00I C00C C00A 120.7(3) . . ?
C00I C00C H00C 119.6 . . ?
C009 C00D H00D 118.9 . . ?
C00E C00D C009 122.1(3) . . ?
C00E C00D H00D 118.9 . . ?
C00D C00E C00K 116.8(3) . . ?
C00D C00E C00N 121.1(3) . . ?
C00K C00E C00N 122.1(3) . . ?
C006 C00F H00F 119.6 . . ?
C006 C00F C00K 120.9(3) . . ?
C00K C00F H00F 119.6 . . ?
C008 C00G C00B 103.0(2) . . ?
C008 C00G H00E 111.2 . . ?
C008 C00G H00G 111.2 . . ?
C00B C00G H00E 111.2 . . ?
C00B C00G H00G 111.2 . . ?
H00E C00G H00G 109.1 . . ?
F001 C00H F002 105.9(3) . . ?
F001 C00H C007 112.1(3) . . ?
F002 C00H C007 111.8(3) . . ?
F003 C00H F001 106.2(3) . . ?
F003 C00H F002 106.6(3) . . ?
F003 C00H C007 113.6(3) . . ?
C00C C00I H00I 119.1 . . ?
C00C C00I C00L 121.8(3) . . ?
C00L C00I H00I 119.1 . . ?
C00A C00J H00J 119.6 . . ?
C00M C00J C00A 120.8(3) . . ?
C00M C00J H00J 119.6 . . ?
C00E C00K C00F 121.9(3) . . ?
C00E C00K H00K 119.1 . . ?
C00F C00K H00K 119.1 . . ?
C00I C00L C00O 121.2(3) . . ?
C00M C00L C00I 117.3(3) . . ?
C00M C00L C00O 121.5(3) . . ?
C00J C00M C00L 121.8(3) . . ?
C00J C00M H00M 119.1 . . ?
C00L C00M H00M 119.1 . . ?
C00E C00N H00H 109.5 . . ?
C00E C00N H00L 109.5 . . ?
C00E C00N H00N 109.5 . . ?
H00H C00N H00L 109.5 . . ?
H00H C00N H00N 109.5 . . ?
H00L C00N H00N 109.5 . . ?
C00L C00O H00O 109.5 . . ?
C00L C00O H00P 109.5 . . ?
C00L C00O H00Q 109.5 . . ?
H00O C00O H00P 109.5 . . ?
H00O C00O H00Q 109.5 . . ?
H00P C00O H00Q 109.5 . . ?

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
N004 C007 C00B C00G 9.5(3) . . . . ?
N004 C007 C00H F001 57.6(3) . . . . ?
N004 C007 C00H F002 -61.2(3) . . . . ?
N004 C007 C00H F003 178.1(2) . . . . ?
N004 C008 C00A C00C -26.4(5) . . . . ?
N004 C008 C00A C00J 149.4(3) . . . . ?
N004 C008 C00G C00B 3.9(4) . . . . ?
N005 C006 C009 C00D -178.9(3) . . . . ?
N005 C006 C00F C00K 179.5(3) . . . . ?
N005 C007 C00B C00G 127.9(3) . . . . ?
N005 C007 C00H F001 -57.9(3) . . . . ?
N005 C007 C00H F002 -176.7(2) . . . . ?
N005 C007 C00H F003 62.5(3) . . . . ?
C006 N005 C007 N004 161.6(3) . . . . ?
C006 N005 C007 C00B 43.4(4) . . . . ?
C006 N005 C007 C00H -84.0(4) . . . . ?
C006 C009 C00D C00E -0.3(5) . . . . ?
C006 C00F C00K C00E -1.0(5) . . . . ?
C007 N004 C008 C00A -177.7(3) . . . . ?
C007 N004 C008 C00G 2.4(4) . . . . ?
C007 N005 C006 C009 -169.9(3) . . . . ?
C007 N005 C006 C00F 10.3(5) . . . . ?
C007 C00B C00G C008 -7.9(3) . . . . ?
C008 N004 C007 N005 -130.8(3) . . . . ?
C008 N004 C007 C00B -7.6(3) . . . . ?
C008 N004 C007 C00H 110.7(3) . . . . ?
C008 C00A C00C C00I 174.2(3) . . . . ?
C008 C00A C00J C00M -173.9(3) . . . . ?
C009 C006 C00F C00K -0.2(5) . . . . ?
C009 C00D C00E C00K -0.8(5) . . . . ?
C009 C00D C00E C00N -179.1(3) . . . . ?
C00A C008 C00G C00B -176.0(3) . . . . ?
C00A C00C C00I C00L -0.3(5) . . . . ?
C00A C00J C00M C00L -0.4(6) . . . . ?
C00B C007 C00H F001 172.9(2) . . . . ?
C00B C007 C00H F002 54.1(3) . . . . ?
C00B C007 C00H F003 -66.7(3) . . . . ?
C00C C00A C00J C00M 2.0(5) . . . . ?
C00C C00I C00L C00M 1.9(5) . . . . ?
C00C C00I C00L C00O -176.5(3) . . . . ?
C00D C00E C00K C00F 1.5(5) . . . . ?
C00F C006 C009 C00D 0.8(4) . . . . ?
C00G C008 C00A C00C 153.5(3) . . . . ?
C00G C008 C00A C00J -30.8(5) . . . . ?
C00H C007 C00B C00G -104.7(3) . . . . ?
C00I C00L C00M C00J -1.6(6) . . . . ?
C00J C00A C00C C00I -1.7(5) . . . . ?
C00N C00E C00K C00F 179.7(3) . . . . ?
C00O C00L C00M C00J 176.8(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
