# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2023

####################################################################### 
# 
# 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_dot150
_database_code_depnum_ccdc_archive 'CCDC 2245446'
loop_
_audit_author_name
_audit_author_address
'GAVIN CHIT TSUI'
;Chinese University of Hong Kong
Hong Kong
;
_audit_update_record             
;
2023-03-01 deposited with the CCDC.	2023-08-16 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C22 H24 F5 N O3'
_chemical_formula_weight         445.42

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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 '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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   15.81(2)
_cell_length_b                   8.079(11)
_cell_length_c                   16.97(2)
_cell_angle_alpha                90
_cell_angle_beta                 94.93(4)
_cell_angle_gamma                90
_cell_volume                     2160(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    1505
_cell_measurement_theta_min      15
_cell_measurement_theta_max      15

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.370
_exptl_crystal_F_000             928
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.500
_exptl_crystal_size_mid          0.400
_exptl_crystal_size_min          0.300
_exptl_absorpt_coefficient_mu    0.119
_shelx_estimated_absorpt_T_min   0.943
_shelx_estimated_absorpt_T_max   0.965
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5261
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'BRUKER D8VENTURE DIFFRACTOMETER'
_diffrn_measurement_method       'PHI & OMEGA SCAN'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            20663
_diffrn_reflns_av_unetI/netI     0.0865
_diffrn_reflns_av_R_equivalents  0.1331
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.410
_diffrn_reflns_theta_max         25.248
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measured_fraction_theta_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_point_group_measured_fraction_full 0.991
_reflns_number_total             3887
_reflns_number_gt                1987
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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.
;

_computing_data_collection       'BRUKER D8VENTURE DIFFRACTOMETER'
_computing_cell_refinement       'BRUKER D8VENTURE DIFFRACTOMETER'
_computing_data_reduction        'BRUKER D8VENTURE DIFFRACTOMETER'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'BRUKER SHELXTL'
_computing_publication_material  'BRUKER SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1584P)²+0.6885P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3887
_refine_ls_number_parameters     350
_refine_ls_number_restraints     70
_refine_ls_R_factor_all          0.1708
_refine_ls_R_factor_gt           0.0860
_refine_ls_wR_factor_ref         0.2933
_refine_ls_wR_factor_gt          0.2305
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_restrained_S_all      1.108
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.000

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
N1 N 0.6404(2) 0.8602(4) 0.46684(15) 0.0522(9) Uani 1 1 d . . . . .
O1 O 0.6853(3) 0.4199(5) 0.7016(2) 0.1020(14) Uani 1 1 d . . . . .
O2 O 0.5990(2) 0.6328(4) 0.67606(15) 0.0703(10) Uani 1 1 d . . . . .
O3 O 0.68652(17) 0.9265(4) 0.40122(13) 0.0570(8) Uani 1 1 d . . . . .
C1 C 0.5642(3) 0.4546(6) 0.77616(19) 0.0521(11) Uani 1 1 d . . . . .
C2 C 0.5115(3) 0.5736(7) 0.8000(2) 0.0702(14) Uani 1 1 d . . . . .
H2A H 0.511538 0.677665 0.776579 0.084 Uiso 1 1 calc R U . . .
C3 C 0.4568(4) 0.5432(8) 0.8594(3) 0.0861(17) Uani 1 1 d . . . . .
H3A H 0.421927 0.627185 0.875492 0.103 Uiso 1 1 calc R U . . .
C4 C 0.4549(3) 0.3945(7) 0.8926(3) 0.0808(16) Uani 1 1 d . . . . .
H4A H 0.418163 0.375483 0.931567 0.097 Uiso 1 1 calc R U . . .
C5 C 0.5066(3) 0.2668(6) 0.8702(2) 0.0604(12) Uani 1 1 d . . . . .
C6 C 0.5033(3) 0.1092(7) 0.9039(2) 0.0730(14) Uani 1 1 d . . . . .
H6A H 0.465139 0.089134 0.941586 0.088 Uiso 1 1 calc R U . . .
C7 C 0.5542(4) -0.0140(7) 0.8832(3) 0.0776(15) Uani 1 1 d . . . . .
H7A H 0.551801 -0.117072 0.907273 0.093 Uiso 1 1 calc R U . . .
C8 C 0.6107(3) 0.0127(7) 0.8255(2) 0.0733(14) Uani 1 1 d . . . . .
H8A H 0.645754 -0.072909 0.811379 0.088 Uiso 1 1 calc R U . . .
C9 C 0.6147(3) 0.1609(6) 0.7903(2) 0.0604(12) Uani 1 1 d . . . . .
H9A H 0.652153 0.175617 0.751462 0.073 Uiso 1 1 calc R U . . .
C10 C 0.5638(2) 0.2947(5) 0.81056(19) 0.0496(11) Uani 1 1 d . . . . .
C11 C 0.6232(3) 0.4956(6) 0.7148(2) 0.0583(11) Uani 1 1 d . . . . .
C12 C 0.6483(3) 0.6879(6) 0.6120(2) 0.0612(12) Uani 1 1 d . . . . .
H12A H 0.708313 0.658221 0.622713 0.073 Uiso 1 1 calc R U . . .
C13 C 0.6117(3) 0.6125(6) 0.5366(2) 0.0683(13) Uani 1 1 d . . . . .
H13A H 0.551204 0.634180 0.530562 0.082 Uiso 1 1 calc R U . . .
H13B H 0.619571 0.493501 0.539443 0.082 Uiso 1 1 calc R U . . .
C14 C 0.6518(3) 0.6785(6) 0.4635(2) 0.0667(13) Uani 1 1 d . . . . .
C15 C 0.5966(5) 0.6148(7) 0.3911(3) 0.102(2) Uani 1 1 d . . . . .
H15A H 0.602629 0.496927 0.387290 0.153 Uiso 1 1 calc R U . . .
H15B H 0.538233 0.641731 0.396530 0.153 Uiso 1 1 calc R U . . .
H15C H 0.614278 0.665980 0.344170 0.153 Uiso 1 1 calc R U . . .
C16 C 0.7420(5) 0.6144(11) 0.4609(4) 0.098(2) Uani 1 1 d . . . . .
C17 C 0.6770(3) 0.9494(6) 0.5389(2) 0.0672(14) Uani 1 1 d . . . . .
C18 C 0.6374(4) 0.8694(6) 0.6083(2) 0.0754(15) Uani 1 1 d . . . . .
H18A H 0.662751 0.917449 0.657127 0.090 Uiso 1 1 calc R U . . .
H18B H 0.577260 0.894745 0.604392 0.090 Uiso 1 1 calc R U . . .
C19 C 0.7750(5) 0.9495(13) 0.5504(4) 0.113(3) Uani 1 1 d . . . . .
C20 C 0.6459(6) 1.1243(7) 0.5339(3) 0.122(3) Uani 1 1 d . . . . .
H20A H 0.668630 1.184379 0.579755 0.183 Uiso 1 1 calc R U . . .
H20B H 0.664140 1.175431 0.487193 0.183 Uiso 1 1 calc R U . . .
H20C H 0.585047 1.125272 0.531571 0.183 Uiso 1 1 calc R U . . .
C21 C 0.6382(3) 1.0037(6) 0.3443(2) 0.0745(15) Uani 1 1 d D . . . .
C22 C 0.6922(5) 1.0845(9) 0.2919(3) 0.119(3) Uani 1 1 d D . . . .
F1 F 0.5625(5) 0.9465(14) 0.3211(6) 0.138(4) Uani 0.630(8) 1 d D U P A 1
F2 F 0.6103(8) 1.1545(13) 0.3727(7) 0.144(5) Uani 0.630(8) 1 d D U P A 1
F3 F 0.7397(5) 1.2018(8) 0.3366(4) 0.131(3) Uani 0.630(8) 1 d D U P A 1
F4 F 0.6530(12) 1.1754(17) 0.2331(9) 0.114(4) Uani 0.630(8) 1 d D U P A 1
F5 F 0.6982(12) 0.9326(14) 0.2501(5) 0.239(6) Uani 0.630(8) 1 d D U P A 1
F1' F 0.6098(8) 0.8764(13) 0.2900(5) 0.099(4) Uani 0.370(8) 1 d D U P A 2
F2' F 0.5748(8) 1.094(2) 0.3655(10) 0.110(6) Uani 0.370(8) 1 d D U P A 2
F3' F 0.7725(6) 1.067(2) 0.2835(9) 0.110(6) Uani 0.370(8) 1 d D U P A 2
F4' F 0.6407(19) 1.116(3) 0.2245(12) 0.102(6) Uani 0.370(8) 1 d D U P A 2
F5' F 0.7545(6) 0.9924(14) 0.2673(7) 0.074(3) Uani 0.370(8) 1 d D U P A 2
H16A H 0.769(4) 0.680(7) 0.424(3) 0.098(18) Uiso 1 1 d . . . . .
H16B H 0.788(4) 0.659(7) 0.508(3) 0.096(18) Uiso 1 1 d . . . . .
H16C H 0.744(5) 0.497(11) 0.452(5) 0.16(3) Uiso 1 1 d . . . . .
H19A H 0.798(4) 1.006(9) 0.508(4) 0.13(2) Uiso 1 1 d . . . . .
H19B H 0.808(4) 0.855(8) 0.568(4) 0.11(2) Uiso 1 1 d . . . . .
H19C H 0.794(4) 1.030(8) 0.590(4) 0.12(2) 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
N1 C14 1.481(6) . ?
N1 O3 1.483(4) . ?
N1 C17 1.493(5) . ?
O1 C11 1.195(6) . ?
O2 C11 1.328(6) . ?
O2 C12 1.461(5) . ?
O3 C21 1.334(5) . ?
C1 C2 1.357(6) . ?
C1 C10 1.418(6) . ?
C1 C11 1.493(6) . ?
C2 C3 1.404(7) . ?
C2 H2A 0.9300 . ?
C3 C4 1.328(7) . ?
C3 H3A 0.9300 . ?
C4 C5 1.390(7) . ?
C4 H4A 0.9300 . ?
C5 C6 1.399(7) . ?
C5 C10 1.432(6) . ?
C6 C7 1.346(7) . ?
C6 H6A 0.9300 . ?
C7 C8 1.398(7) . ?
C7 H7A 0.9300 . ?
C8 C9 1.342(7) . ?
C8 H8A 0.9300 . ?
C9 C10 1.408(6) . ?
C9 H9A 0.9300 . ?
C12 C18 1.477(7) . ?
C12 C13 1.488(6) . ?
C12 H12A 0.9800 . ?
C13 C14 1.536(6) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C14 C16 1.522(9) . ?
C14 C15 1.534(6) . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C16 H16A 0.95(6) . ?
C16 H16B 1.10(6) . ?
C16 H16C 0.96(9) . ?
C17 C20 1.496(8) . ?
C17 C18 1.523(6) . ?
C17 C19 1.545(9) . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C19 H19A 0.94(7) . ?
C19 H19B 0.96(6) . ?
C19 H19C 0.97(6) . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C21 F1 1.311(7) . ?
C21 F2' 1.314(9) . ?
C21 F2 1.395(8) . ?
C21 F1' 1.427(8) . ?
C21 C22 1.440(8) . ?
C22 F3' 1.299(9) . ?
C22 F5' 1.331(9) . ?
C22 F4 1.346(8) . ?
C22 F4' 1.370(10) . ?
C22 F3 1.393(8) . ?
C22 F5 1.425(9) . ?
F3' F5' 0.708(15) . ?

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 N1 O3 105.1(3) . . ?
C14 N1 C17 118.0(3) . . ?
O3 N1 C17 105.1(3) . . ?
C11 O2 C12 118.2(4) . . ?
C21 O3 N1 115.1(3) . . ?
C2 C1 C10 119.9(4) . . ?
C2 C1 C11 119.2(4) . . ?
C10 C1 C11 120.9(4) . . ?
C1 C2 C3 121.5(5) . . ?
C1 C2 H2A 119.3 . . ?
C3 C2 H2A 119.3 . . ?
C4 C3 C2 120.0(5) . . ?
C4 C3 H3A 120.0 . . ?
C2 C3 H3A 120.0 . . ?
C3 C4 C5 121.4(5) . . ?
C3 C4 H4A 119.3 . . ?
C5 C4 H4A 119.3 . . ?
C4 C5 C6 121.4(4) . . ?
C4 C5 C10 119.9(4) . . ?
C6 C5 C10 118.7(4) . . ?
C7 C6 C5 121.4(4) . . ?
C7 C6 H6A 119.3 . . ?
C5 C6 H6A 119.3 . . ?
C6 C7 C8 120.2(5) . . ?
C6 C7 H7A 119.9 . . ?
C8 C7 H7A 119.9 . . ?
C9 C8 C7 120.4(5) . . ?
C9 C8 H8A 119.8 . . ?
C7 C8 H8A 119.8 . . ?
C8 C9 C10 121.8(4) . . ?
C8 C9 H9A 119.1 . . ?
C10 C9 H9A 119.1 . . ?
C9 C10 C1 125.2(4) . . ?
C9 C10 C5 117.4(4) . . ?
C1 C10 C5 117.4(4) . . ?
O1 C11 O2 122.7(4) . . ?
O1 C11 C1 126.2(4) . . ?
O2 C11 C1 111.1(4) . . ?
O2 C12 C18 105.4(4) . . ?
O2 C12 C13 108.8(4) . . ?
C18 C12 C13 109.5(4) . . ?
O2 C12 H12A 111.0 . . ?
C18 C12 H12A 111.0 . . ?
C13 C12 H12A 111.0 . . ?
C12 C13 C14 113.3(4) . . ?
C12 C13 H13A 108.9 . . ?
C14 C13 H13A 108.9 . . ?
C12 C13 H13B 108.9 . . ?
C14 C13 H13B 108.9 . . ?
H13A C13 H13B 107.7 . . ?
N1 C14 C16 117.2(5) . . ?
N1 C14 C15 107.5(4) . . ?
C16 C14 C15 109.5(5) . . ?
N1 C14 C13 104.6(4) . . ?
C16 C14 C13 111.0(4) . . ?
C15 C14 C13 106.5(4) . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C14 C16 H16A 108(3) . . ?
C14 C16 H16B 116(3) . . ?
H16A C16 H16B 89(4) . . ?
C14 C16 H16C 113(5) . . ?
H16A C16 H16C 115(6) . . ?
H16B C16 H16C 114(6) . . ?
N1 C17 C20 107.9(4) . . ?
N1 C17 C18 105.8(4) . . ?
C20 C17 C18 106.9(5) . . ?
N1 C17 C19 114.6(5) . . ?
C20 C17 C19 109.1(6) . . ?
C18 C17 C19 112.2(4) . . ?
C12 C18 C17 113.6(4) . . ?
C12 C18 H18A 108.8 . . ?
C17 C18 H18A 108.8 . . ?
C12 C18 H18B 108.8 . . ?
C17 C18 H18B 108.8 . . ?
H18A C18 H18B 107.7 . . ?
C17 C19 H19A 110(4) . . ?
C17 C19 H19B 124(4) . . ?
H19A C19 H19B 113(6) . . ?
C17 C19 H19C 110(4) . . ?
H19A C19 H19C 95(5) . . ?
H19B C19 H19C 101(5) . . ?
C17 C20 H20A 109.5 . . ?
C17 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C17 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
F1 C21 O3 120.2(5) . . ?
F2' C21 O3 117.6(8) . . ?
F1 C21 F2 96.0(8) . . ?
O3 C21 F2 109.7(6) . . ?
F2' C21 F1' 111.8(10) . . ?
O3 C21 F1' 105.0(6) . . ?
F1 C21 C22 123.2(6) . . ?
F2' C21 C22 115.2(9) . . ?
O3 C21 C22 109.0(4) . . ?
F2 C21 C22 92.2(7) . . ?
F1' C21 C22 95.6(6) . . ?
F3' C22 F5' 31.2(7) . . ?
F3' C22 F4' 116.4(17) . . ?
F5' C22 F4' 104.1(16) . . ?
F4 C22 F3 103.0(8) . . ?
F4 C22 F5 98.5(10) . . ?
F3 C22 F5 143.2(10) . . ?
F3' C22 C21 130.9(8) . . ?
F5' C22 C21 115.8(7) . . ?
F4 C22 C21 116.4(11) . . ?
F4' C22 C21 105.0(14) . . ?
F3 C22 C21 107.1(5) . . ?
F5 C22 C21 89.2(8) . . ?
F5' F3' C22 76.9(10) . . ?
F3' F5' C22 71.9(11) . . ?

_refine_diff_density_max         0.278
_refine_diff_density_min         -0.432
_refine_diff_density_rms         0.068

