# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2021

####################################################################### 
# 
# 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. 
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data_201009_jmx_1_0m
_database_code_depnum_ccdc_archive 'CCDC 2058180'
loop_
_audit_author_name
_audit_author_address
skybasket
;Zhejiang University
China
;
_audit_update_record             
;
2021-01-23 deposited with the CCDC.	2021-03-25 downloaded from the CCDC.
;
_audit_creation_date             2020-10-10
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C20 H21 F3 N2 O2'
_chemical_formula_sum            'C20 H21 F3 N2 O2'
_chemical_formula_weight         378.39
_chemical_absolute_configuration ad
_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'
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      tetragonal
_space_group_IT_number           78
_space_group_name_H-M_alt        'P 43'
_space_group_name_Hall           'P 4cw'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'-y, x, z+3/4'
'y, -x, z+1/4'

_cell_length_a                   10.1440(7)
_cell_length_b                   10.1440(7)
_cell_length_c                   19.1105(14)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1966.5(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9853
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      68.25
_cell_measurement_theta_min      4.36
_shelx_estimated_absorpt_T_max   0.974
_shelx_estimated_absorpt_T_min   0.746
_exptl_absorpt_coefficient_mu    0.866
_exptl_absorpt_correction_T_max  0.7531
_exptl_absorpt_correction_T_min  0.6280
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1481 before and 0.0664 after correction.
The Ratio of minimum to maximum transmission is 0.8339.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.278
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             792
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.03
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0453
_diffrn_reflns_av_unetI/netI     0.0264
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            27618
_diffrn_reflns_point_group_measured_fraction_full 0.984
_diffrn_reflns_point_group_measured_fraction_max 0.981
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.313
_diffrn_reflns_theta_min         4.358
_diffrn_ambient_temperature      301.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'zju Bruker D8 Venture Ims3.0'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.901
_reflns_Friedel_fraction_full    0.967
_reflns_Friedel_fraction_max     0.962
_reflns_number_gt                3206
_reflns_number_total             3546
_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 AXS Inc., 2017)'
_computing_data_collection       'Bruker Instrument Service vV6.2.10'
_computing_data_reduction        'SAINT V8.38A (Bruker AXS Inc., 2017)'
_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         0.127
_refine_diff_density_min         -0.175
_refine_diff_density_rms         0.048
_refine_ls_abs_structure_details 
;
 Flack x determined using 1304 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.05(5)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     274
_refine_ls_number_reflns         3546
_refine_ls_number_restraints     76
_refine_ls_R_factor_all          0.0415
_refine_ls_R_factor_gt           0.0340
_refine_ls_restrained_S_all      1.068
_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)+(0.0529P)²+0.1121P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0889
_refine_ls_wR_factor_ref         0.0923
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 F3-C20 \\sim F3A-C20
 with sigma of 0.02
 F2-C20 \\sim F2A-C20
 with sigma of 0.02
 F1-C20 \\sim F1A-C20
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
C20 \\sim F1 \\sim F2 \\sim F3 \\sim F1A \\sim F2A \\sim F3A: within 1.7A with
sigma of 0.02 and sigma for terminal atoms of 0.04
4. Others
 Sof(F1A)=Sof(F2A)=Sof(F3A)=1-FVAR(1)
 Sof(F1)=Sof(F2)=Sof(F3)=FVAR(1)
5.a Ternary CH refined with riding coordinates:
 C11(H11)
5.b Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B), C12(H12A,H12B), C13(H13A,H13B)
5.c Aromatic/amide H refined with riding coordinates:
 N2(H2), C1(H1), C2(H2A), C3(H3), C4(H4), C16(H16), C18(H18), C19(H19)
5.d Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C), C8(H8A,H8B,H8C)
;
_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
O1 O 0.51560(18) 0.50888(17) 0.44483(9) 0.0612(4) Uani 1 1 d . . . . .
O2 O 0.9613(2) 0.5740(2) 0.61968(15) 0.0981(8) Uani 1 1 d . . . . .
N1 N 0.1963(3) 0.3466(3) 0.42362(13) 0.0814(7) Uani 1 1 d . . . . .
N2 N 0.42890(19) 0.46446(19) 0.55110(8) 0.0540(5) Uani 1 1 d . . . . .
H2 H 0.430920 0.484156 0.594861 0.065 Uiso 1 1 calc R . . . .
C1 C 0.1089(4) 0.3965(4) 0.3778(2) 0.1037(13) Uani 1 1 d . . . . .
H1 H 0.077068 0.341011 0.342957 0.124 Uiso 1 1 calc R . . . .
C2 C 0.0640(3) 0.5226(5) 0.3791(2) 0.0983(12) Uani 1 1 d . . . . .
H2A H 0.002871 0.551691 0.346318 0.118 Uiso 1 1 calc R . . . .
C3 C 0.1100(3) 0.6049(4) 0.4291(2) 0.0896(10) Uani 1 1 d . . . . .
H3 H 0.082168 0.692187 0.430897 0.108 Uiso 1 1 calc R . . . .
C4 C 0.1994(3) 0.5569(3) 0.47752(16) 0.0723(7) Uani 1 1 d . . . . .
H4 H 0.231807 0.611470 0.512640 0.087 Uiso 1 1 calc R . . . .
C5 C 0.2402(2) 0.4271(3) 0.47323(13) 0.0580(5) Uani 1 1 d . . . . .
C6 C 0.3324(3) 0.3660(2) 0.52771(12) 0.0593(6) Uani 1 1 d . . . . .
C7 C 0.4026(4) 0.2450(3) 0.5011(2) 0.0873(9) Uani 1 1 d . . . . .
H7A H 0.447606 0.265685 0.458326 0.131 Uiso 1 1 calc GR . . . .
H7B H 0.339524 0.176208 0.492707 0.131 Uiso 1 1 calc GR . . . .
H7C H 0.465357 0.215910 0.535413 0.131 Uiso 1 1 calc GR . . . .
C8 C 0.2470(4) 0.3325(4) 0.59185(15) 0.0893(10) Uani 1 1 d . . . . .
H8A H 0.302150 0.298892 0.628586 0.134 Uiso 1 1 calc GR . . . .
H8B H 0.182931 0.267056 0.579198 0.134 Uiso 1 1 calc GR . . . .
H8C H 0.202754 0.410550 0.607782 0.134 Uiso 1 1 calc GR . . . .
C9 C 0.5134(2) 0.5250(2) 0.50871(11) 0.0465(4) Uani 1 1 d . . . . .
C10 C 0.6069(2) 0.6213(2) 0.54315(11) 0.0506(5) Uani 1 1 d . . . . .
H10A H 0.604665 0.608266 0.593415 0.061 Uiso 1 1 calc R . . . .
H10B H 0.577505 0.710524 0.533588 0.061 Uiso 1 1 calc R . . . .
C11 C 0.7485(2) 0.6052(2) 0.51726(12) 0.0520(5) Uani 1 1 d . . . . .
H11 H 0.747368 0.610789 0.466069 0.062 Uiso 1 1 calc R . . . .
C12 C 0.8102(3) 0.4739(3) 0.5371(2) 0.0784(8) Uani 1 1 d . . . . .
H12A H 0.745140 0.404442 0.532314 0.094 Uiso 1 1 calc R . . . .
H12B H 0.882638 0.454671 0.505643 0.094 Uiso 1 1 calc R . . . .
C13 C 0.8590(4) 0.4768(3) 0.6096(2) 0.0973(11) Uani 1 1 d . . . . .
H13A H 0.786234 0.496072 0.640917 0.117 Uiso 1 1 calc R . . . .
H13B H 0.893228 0.390488 0.621779 0.117 Uiso 1 1 calc R . . . .
C14 C 0.9350(3) 0.6948(2) 0.59200(16) 0.0691(7) Uani 1 1 d . . . . .
C15 C 0.8343(2) 0.7164(2) 0.54440(12) 0.0494(4) Uani 1 1 d . . . . .
C16 C 0.8161(2) 0.8444(2) 0.52069(12) 0.0529(5) Uani 1 1 d . . . . .
H16 H 0.750313 0.861368 0.488034 0.064 Uiso 1 1 calc R . . . .
C17 C 0.8934(3) 0.9472(2) 0.54441(15) 0.0626(6) Uani 1 1 d . . . . .
C18 C 0.9956(3) 0.9228(3) 0.5895(2) 0.0859(10) Uani 1 1 d . . . . .
H18 H 1.050280 0.991148 0.604001 0.103 Uiso 1 1 calc R . . . .
C19 C 1.0166(3) 0.7971(3) 0.6132(2) 0.0938(11) Uani 1 1 d . . . . .
H19 H 1.086065 0.780169 0.643660 0.113 Uiso 1 1 calc R . . . .
C20 C 0.8651(4) 1.0853(3) 0.5226(2) 0.0864(9) Uani 1 1 d D U . . .
F1 F 0.7566(17) 1.1019(10) 0.4854(14) 0.131(5) Uani 0.45(3) 1 d D U P A 1
F2 F 0.844(3) 1.1592(13) 0.5781(7) 0.151(6) Uani 0.45(3) 1 d D U P A 1
F3 F 0.9615(15) 1.1387(14) 0.4921(11) 0.156(5) Uani 0.45(3) 1 d D U P A 1
F1A F 0.8185(19) 1.0876(9) 0.4573(6) 0.126(3) Uani 0.55(3) 1 d D U P A 2
F2A F 0.7798(13) 1.1439(11) 0.5637(10) 0.142(5) Uani 0.55(3) 1 d D U P A 2
F3A F 0.9670(8) 1.1642(9) 0.5187(10) 0.140(4) Uani 0.55(3) 1 d D U P A 2


_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
O1 C9 1.232(2) . ?
O2 C13 1.444(4) . ?
O2 C14 1.361(3) . ?
N1 C1 1.345(4) . ?
N1 C5 1.329(3) . ?
N2 H2 0.8600 . ?
N2 C6 1.468(3) . ?
N2 C9 1.330(3) . ?
C1 H1 0.9300 . ?
C1 C2 1.358(6) . ?
C2 H2A 0.9300 . ?
C2 C3 1.352(6) . ?
C3 H3 0.9300 . ?
C3 C4 1.384(5) . ?
C4 H4 0.9300 . ?
C4 C5 1.382(4) . ?
C5 C6 1.530(3) . ?
C6 C7 1.508(4) . ?
C6 C8 1.539(4) . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C9 C10 1.513(3) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C10 C11 1.528(3) . ?
C11 H11 0.9800 . ?
C11 C12 1.519(3) . ?
C11 C15 1.516(3) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C12 C13 1.472(5) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C14 C15 1.385(3) . ?
C14 C19 1.388(4) . ?
C15 C16 1.388(3) . ?
C16 H16 0.9300 . ?
C16 C17 1.381(3) . ?
C17 C18 1.371(4) . ?
C17 C20 1.489(4) . ?
C18 H18 0.9300 . ?
C18 C19 1.370(5) . ?
C19 H19 0.9300 . ?
C20 F1 1.321(10) . ?
C20 F2 1.316(11) . ?
C20 F3 1.260(10) . ?
C20 F1A 1.334(9) . ?
C20 F2A 1.311(10) . ?
C20 F3A 1.310(7) . ?

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
C14 O2 C13 115.0(2) . . ?
C5 N1 C1 117.0(3) . . ?
C6 N2 H2 118.0 . . ?
C9 N2 H2 118.0 . . ?
C9 N2 C6 123.93(17) . . ?
N1 C1 H1 117.8 . . ?
N1 C1 C2 124.3(3) . . ?
C2 C1 H1 117.8 . . ?
C1 C2 H2A 120.7 . . ?
C3 C2 C1 118.6(3) . . ?
C3 C2 H2A 120.7 . . ?
C2 C3 H3 120.6 . . ?
C2 C3 C4 118.8(4) . . ?
C4 C3 H3 120.6 . . ?
C3 C4 H4 120.3 . . ?
C5 C4 C3 119.4(3) . . ?
C5 C4 H4 120.3 . . ?
N1 C5 C4 121.9(3) . . ?
N1 C5 C6 116.2(2) . . ?
C4 C5 C6 121.9(2) . . ?
N2 C6 C5 109.83(19) . . ?
N2 C6 C7 110.0(2) . . ?
N2 C6 C8 106.44(19) . . ?
C5 C6 C8 106.7(2) . . ?
C7 C6 C5 112.9(2) . . ?
C7 C6 C8 110.7(3) . . ?
C6 C7 H7A 109.5 . . ?
C6 C7 H7B 109.5 . . ?
C6 C7 H7C 109.5 . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C6 C8 H8A 109.5 . . ?
C6 C8 H8B 109.5 . . ?
C6 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
O1 C9 N2 123.7(2) . . ?
O1 C9 C10 120.4(2) . . ?
N2 C9 C10 115.93(17) . . ?
C9 C10 H10A 109.1 . . ?
C9 C10 H10B 109.1 . . ?
C9 C10 C11 112.30(18) . . ?
H10A C10 H10B 107.9 . . ?
C11 C10 H10A 109.1 . . ?
C11 C10 H10B 109.1 . . ?
C10 C11 H11 107.8 . . ?
C12 C11 C10 113.6(2) . . ?
C12 C11 H11 107.8 . . ?
C15 C11 C10 110.44(18) . . ?
C15 C11 H11 107.8 . . ?
C15 C11 C12 109.3(2) . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 108.0 . . ?
C13 C12 C11 110.9(3) . . ?
C13 C12 H12A 109.5 . . ?
C13 C12 H12B 109.5 . . ?
O2 C13 C12 112.4(3) . . ?
O2 C13 H13A 109.1 . . ?
O2 C13 H13B 109.1 . . ?
C12 C13 H13A 109.1 . . ?
C12 C13 H13B 109.1 . . ?
H13A C13 H13B 107.9 . . ?
O2 C14 C15 122.8(2) . . ?
O2 C14 C19 116.3(2) . . ?
C15 C14 C19 120.9(2) . . ?
C14 C15 C11 122.0(2) . . ?
C14 C15 C16 117.4(2) . . ?
C16 C15 C11 120.5(2) . . ?
C15 C16 H16 119.2 . . ?
C17 C16 C15 121.6(2) . . ?
C17 C16 H16 119.2 . . ?
C16 C17 C20 120.6(2) . . ?
C18 C17 C16 120.0(2) . . ?
C18 C17 C20 119.5(3) . . ?
C17 C18 H18 120.2 . . ?
C19 C18 C17 119.6(2) . . ?
C19 C18 H18 120.2 . . ?
C14 C19 H19 119.8 . . ?
C18 C19 C14 120.5(2) . . ?
C18 C19 H19 119.8 . . ?
F1 C20 C17 115.5(5) . . ?
F2 C20 C17 110.0(7) . . ?
F2 C20 F1 103.0(8) . . ?
F3 C20 C17 112.6(7) . . ?
F3 C20 F1 110.1(10) . . ?
F3 C20 F2 104.7(9) . . ?
F1A C20 C17 110.3(5) . . ?
F2A C20 C17 112.7(6) . . ?
F2A C20 F1A 108.6(7) . . ?
F3A C20 C17 116.0(5) . . ?
F3A C20 F1A 102.5(7) . . ?
F3A C20 F2A 106.1(7) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
