# Electronic Supplementary Material (ESI) for Catalysis Science & Technology.
# 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_3b
_database_code_depnum_ccdc_archive 'CCDC 2271746'
loop_
_audit_author_name
_audit_author_address
'Dejan-Kresimir Bucar'
;University College London
United Kingdom
;
_audit_update_record             
;
2023-06-22 deposited with the CCDC.	2024-03-12 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_chemical_formula_moiety         'C16 H16 N O3, C2 F3 O2'
_chemical_formula_sum            'C18 H16 F3 N O5'
_chemical_formula_weight         383.37

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'
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'
F F 0.0727 0.0534 '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                   4.38440(10)
_cell_length_b                   16.8800(3)
_cell_length_c                   23.4788(4)
_cell_angle_alpha                90
_cell_angle_beta                 91.0715(19)
_cell_angle_gamma                90
_cell_volume                     1737.34(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    150.0(1)
_cell_measurement_reflns_used    11656
_cell_measurement_theta_min      4.5370
_cell_measurement_theta_max      72.2030

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.04
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-1 -6 -12 0.0383
-3 2 5 0.1401
0 7 -11 0.0167
-1 8 -9 0.0512
0 11 1 0.0299
0 -9 -9 0.0052
0 -10 5 0.0115
0 5 14 0.0338
2 -2 -7 0.0710
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.465
_exptl_crystal_F_000             792.1
_exptl_absorpt_coefficient_mu    1.109
_exptl_absorpt_correction_T_min  0.867
_exptl_absorpt_correction_T_max  0.967
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.53 (Rigaku Oxford Diffraction, 2019)
Analytical numeric absorption correction using a multifaceted crystal
			model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_diffrn_ambient_temperature      150.0(1)
_diffrn_ambient_environment      N~2~
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            Atlas
_diffrn_detector_area_resol_mean 5.2031
_diffrn_reflns_number            26141
_diffrn_reflns_av_unetI/netI     0.0161
_diffrn_reflns_av_R_equivalents  0.0348
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_theta_min         3.225
_diffrn_reflns_theta_max         66.591
_diffrn_reflns_theta_full        66.591
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             3070
_reflns_number_gt                2748
_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       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_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)+(0.0487P)²+0.9981P] 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         3070
_refine_ls_number_parameters     283
_refine_ls_number_restraints     46
_refine_ls_R_factor_all          0.0501
_refine_ls_R_factor_gt           0.0450
_refine_ls_wR_factor_ref         0.1134
_refine_ls_wR_factor_gt          0.1100
_refine_ls_goodness_of_fit_ref   1.073
_refine_ls_restrained_S_all      1.094
_refine_ls_shift/su_max          0.000
_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
F1A F 0.8150(6) 0.7049(3) 0.58671(16) 0.0655(10) Uani 0.4575(18) 1 d DG . P A 1
F2A F 0.3416(5) 0.72863(17) 0.60033(14) 0.0635(8) Uani 0.4575(18) 1 d DG . P A
1
F3A F 0.6032(10) 0.66573(19) 0.66333(14) 0.0933(17) Uani 0.4575(18) 1 d DG . P
A 1
C18A C 0.6160(5) 0.72510(15) 0.62668(10) 0.0428(8) Uani 0.4575(18) 1 d DG . P A
1
C17A C 0.7091(10) 0.80488(18) 0.65402(19) 0.0332(8) Uani 0.4575(18) 1 d DG . P
A 1
O4A O 0.6522(15) 0.86446(16) 0.6231(3) 0.0379(12) Uani 0.4575(18) 1 d DG . P A
1
O5A O 0.8352(13) 0.8025(3) 0.7011(2) 0.0488(12) Uani 0.4575(18) 1 d DG . P A 1
F1B F 0.788(2) 0.6686(5) 0.6745(4) 0.0933(17) Uani 0.306(3) 1 d D . P B 2
F2B F 0.7009(19) 0.7002(6) 0.5867(3) 0.0655(10) Uani 0.306(3) 1 d D . P B 2
F3B F 0.3565(11) 0.7112(4) 0.6450(3) 0.0635(8) Uani 0.306(3) 1 d D . P B 2
C18B C 0.656(2) 0.7208(5) 0.6411(4) 0.0428(8) Uani 0.306(3) 1 d D . P B 2
C17B C 0.754(2) 0.8056(4) 0.6559(4) 0.0332(8) Uani 0.306(3) 1 d D . P B 2
O4B O 0.692(5) 0.8548(6) 0.6173(7) 0.0379(12) Uani 0.306(3) 1 d D . P B 2
O5B O 0.898(2) 0.8182(6) 0.7003(4) 0.0488(12) Uani 0.306(3) 1 d D . P B 2
F1C F 0.630(3) 0.7074(6) 0.5866(3) 0.0933(17) Uani 0.237(3) 1 d D . P C 3
F2C F 0.3836(15) 0.7132(5) 0.6655(3) 0.0655(10) Uani 0.237(3) 1 d D . P C 3
F3C F 0.8172(16) 0.6634(5) 0.6644(4) 0.0635(8) Uani 0.237(3) 1 d D . P C 3
C18C C 0.658(2) 0.7213(5) 0.6415(5) 0.0428(8) Uani 0.237(3) 1 d D . P C 3
C17C C 0.796(3) 0.8039(5) 0.6530(6) 0.0332(8) Uani 0.237(3) 1 d D . P C 3
O4C O 0.662(6) 0.8580(6) 0.6255(8) 0.0379(12) Uani 0.237(3) 1 d D . P C 3
O5C O 0.979(2) 0.8107(7) 0.6924(4) 0.0488(12) Uani 0.237(3) 1 d D . P C 3
O1 O 1.3707(3) 0.90033(8) 0.52519(6) 0.0411(3) Uani 1 1 d . . . . .
H1O H 1.437(5) 0.8778(10) 0.5548(12) 0.062 Uiso 1 1 calc R U . . .
O2 O 0.5183(3) 0.85903(7) 0.32277(5) 0.0326(3) Uani 1 1 d . . . . .
O3 O 0.7314(3) 0.74425(8) 0.28688(5) 0.0376(3) Uani 1 1 d . . . . .
H3O H 0.654(6) 0.7345(15) 0.2552(11) 0.056 Uiso 1 1 d . U . . .
N1 N 1.0487(3) 0.99834(9) 0.38018(6) 0.0312(3) Uani 1 1 d . . . . .
H1N H 1.120602 1.044209 0.371822 0.037 Uiso 1 1 calc R U . . .
C1 C 0.8465(4) 0.96498(11) 0.34354(7) 0.0309(4) Uani 1 1 d . . . . .
C2 C 0.7374(4) 0.89087(11) 0.35766(7) 0.0286(4) Uani 1 1 d . . . . .
C3 C 0.8341(4) 0.85178(10) 0.40717(7) 0.0276(4) Uani 1 1 d . . . . .
C4 C 1.0432(4) 0.89045(10) 0.44401(7) 0.0284(4) Uani 1 1 d . . . . .
C5 C 1.1450(4) 0.96411(11) 0.42917(7) 0.0301(4) Uani 1 1 d . . . . .
H5 H 1.281877 0.990763 0.453079 0.036 Uiso 1 1 calc R U . . .
C6 C 0.7566(5) 1.00794(12) 0.29018(8) 0.0405(5) Uani 1 1 d . . . . .
H6A H 0.814670 0.977191 0.257740 0.061 Uiso 1 1 calc R U . . .
H6B H 0.857697 1.058362 0.289323 0.061 Uiso 1 1 calc R U . . .
H6C H 0.539779 1.015854 0.289205 0.061 Uiso 1 1 calc R U . . .
C7 C 1.1444(4) 0.85268(11) 0.49905(7) 0.0305(4) Uani 1 1 d . . . . .
H7A H 0.971997 0.847325 0.524066 0.037 Uiso 1 1 calc R U . . .
H7B H 1.225477 0.800250 0.491793 0.037 Uiso 1 1 calc R U . . .
C8 C 0.7096(4) 0.77472(11) 0.41854(7) 0.0294(4) Uani 1 1 d . . . . .
H8 H 0.748193 0.750890 0.453652 0.035 Uiso 1 1 calc R U . . .
C9 C 0.5379(4) 0.73648(11) 0.37906(7) 0.0298(4) Uani 1 1 d . . . . .
C10 C 0.5015(4) 0.77311(11) 0.32062(7) 0.0310(4) Uani 1 1 d . . . . .
H10 H 0.299(5) 0.7659(12) 0.3040(9) 0.037 Uiso 1 1 d . U . . .
C11 C 0.4003(4) 0.65808(11) 0.38855(8) 0.0334(4) Uani 1 1 d . . . . .
C12 C 0.3729(5) 0.62819(12) 0.44338(8) 0.0431(5) Uani 1 1 d . . . . .
H12 H 0.440822 0.658354 0.474243 0.052 Uiso 1 1 calc R U . . .
C13 C 0.2473(6) 0.55488(14) 0.45284(9) 0.0535(6) Uani 1 1 d . . . . .
H13 H 0.232183 0.535825 0.489841 0.064 Uiso 1 1 calc R U . . .
C14 C 0.1428(6) 0.50918(14) 0.40739(10) 0.0554(6) Uani 1 1 d . . . . .
H14 H 0.057684 0.459541 0.413624 0.066 Uiso 1 1 calc R U . . .
C15 C 0.1669(6) 0.53825(14) 0.35326(10) 0.0590(7) Uani 1 1 d . . . . .
H15 H 0.097317 0.507972 0.322583 0.071 Uiso 1 1 calc R U . . .
C16 C 0.2929(5) 0.61184(13) 0.34351(9) 0.0476(5) Uani 1 1 d . . . . .
H16 H 0.306008 0.630668 0.306410 0.057 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
F1A C18A 1.3375 . ?
F2A C18A 1.3438 . ?
F3A C18A 1.3228 . ?
C18A C17A 1.5435 . ?
C17A O5A 1.2273 . ?
C17A O4A 1.2621 . ?
F1B C18B 1.308(8) . ?
F2B C18B 1.343(8) . ?
F3B C18B 1.327(8) . ?
C18B C17B 1.532(6) . ?
C17B O5B 1.226(6) . ?
C17B O4B 1.257(6) . ?
F1C C18C 1.315(8) . ?
F2C C18C 1.344(9) . ?
F3C C18C 1.311(8) . ?
C18C C17C 1.542(6) . ?
C17C O5C 1.220(6) . ?
C17C O4C 1.256(7) . ?
O1 C7 1.409(2) . ?
O2 C2 1.361(2) . ?
O2 C10 1.453(2) . ?
O3 C10 1.382(2) . ?
N1 C1 1.347(2) . ?
N1 C5 1.348(2) . ?
C1 C2 1.382(3) . ?
C1 C6 1.494(2) . ?
C2 C3 1.395(2) . ?
C3 C4 1.409(2) . ?
C3 C8 1.438(3) . ?
C4 C5 1.368(3) . ?
C4 C7 1.501(2) . ?
C8 C9 1.348(2) . ?
C9 C11 1.473(3) . ?
C9 C10 1.511(2) . ?
C11 C16 1.389(3) . ?
C11 C12 1.390(3) . ?
C12 C13 1.374(3) . ?
C13 C14 1.387(3) . ?
C14 C15 1.368(3) . ?
C15 C16 1.380(3) . ?

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
F3A C18A F1A 107.4 . . ?
F3A C18A F2A 106.5 . . ?
F1A C18A F2A 106.2 . . ?
F3A C18A C17A 113.9 . . ?
F1A C18A C17A 110.1 . . ?
F2A C18A C17A 112.4 . . ?
O5A C17A O4A 128.7 . . ?
O5A C17A C18A 117.2 . . ?
O4A C17A C18A 114.1 . . ?
F1B C18B F3B 107.6(7) . . ?
F1B C18B F2B 108.9(6) . . ?
F3B C18B F2B 101.4(6) . . ?
F1B C18B C17B 111.9(6) . . ?
F3B C18B C17B 112.0(6) . . ?
F2B C18B C17B 114.3(6) . . ?
O5B C17B O4B 126.9(5) . . ?
O5B C17B C18B 119.6(5) . . ?
O4B C17B C18B 113.4(5) . . ?
F3C C18C F1C 108.0(7) . . ?
F3C C18C F2C 103.1(7) . . ?
F1C C18C F2C 109.0(7) . . ?
F3C C18C C17C 113.4(7) . . ?
F1C C18C C17C 111.2(7) . . ?
F2C C18C C17C 111.7(7) . . ?
O5C C17C O4C 128.0(7) . . ?
O5C C17C C18C 117.9(6) . . ?
O4C C17C C18C 113.0(6) . . ?
C2 O2 C10 116.72(13) . . ?
C1 N1 C5 123.89(16) . . ?
N1 C1 C2 116.87(15) . . ?
N1 C1 C6 119.52(16) . . ?
C2 C1 C6 123.60(16) . . ?
O2 C2 C1 117.16(15) . . ?
O2 C2 C3 120.96(16) . . ?
C1 C2 C3 121.78(16) . . ?
C2 C3 C4 118.44(16) . . ?
C2 C3 C8 118.17(15) . . ?
C4 C3 C8 123.37(15) . . ?
C5 C4 C3 118.45(15) . . ?
C5 C4 C7 120.83(15) . . ?
C3 C4 C7 120.69(16) . . ?
N1 C5 C4 120.54(16) . . ?
O1 C7 C4 109.09(15) . . ?
C9 C8 C3 120.98(16) . . ?
C8 C9 C11 123.46(16) . . ?
C8 C9 C10 118.47(16) . . ?
C11 C9 C10 117.94(15) . . ?
O3 C10 O2 109.55(15) . . ?
O3 C10 C9 108.10(15) . . ?
O2 C10 C9 111.88(14) . . ?
C16 C11 C12 117.84(18) . . ?
C16 C11 C9 121.57(17) . . ?
C12 C11 C9 120.59(16) . . ?
C13 C12 C11 121.22(18) . . ?
C12 C13 C14 120.3(2) . . ?
C15 C14 C13 119.0(2) . . ?
C14 C15 C16 121.0(2) . . ?
C15 C16 C11 120.7(2) . . ?

_refine_diff_density_max         0.232
_refine_diff_density_min         -0.313
_refine_diff_density_rms         0.039





_chemical_properties_physical    Photo-sensitive
