# Supplementary Information (SI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2026

####################################################################### 
# 
# 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_mg222
_audit_block_doi                 10.5517/ccdc.csd.cc2pvy7r
_database_code_depnum_ccdc_archive 'CCDC 2498545'
loop_
_audit_author_name
_audit_author_address
'Shaoyu Mai'
;Southern Medical University
China
;
_audit_update_record             
;
2025-10-28 deposited with the CCDC.	2025-10-30 downloaded from the CCDC.
;
_audit_creation_date             2025-10-28
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r1)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C15 H10 F3 N O3'
_chemical_formula_sum            'C15 H10 F3 N O3'
_chemical_formula_weight         309.24
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C64 H44 F12 O12 '
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      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                   17.7622(4)
_cell_length_b                   9.9265(3)
_cell_length_c                   7.4546(2)
_cell_angle_alpha                90
_cell_angle_beta                 97.718(2)
_cell_angle_gamma                90
_cell_volume                     1302.46(6)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2843
_cell_measurement_temperature    156(11)
_cell_measurement_theta_max      73.2590
_cell_measurement_theta_min      5.0710
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    1.208
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.72488
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.33c (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_density_diffrn    1.577
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             632
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0211
_diffrn_reflns_av_unetI/netI     0.0255
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.959
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            6977
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.959
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.584
_diffrn_reflns_theta_min         2.510
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      156(11)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.959
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -10.00  15.00   0.50    1.00    --    0.00 -82.00 -60.00   50
  2  ω    -32.00  30.00   0.50    1.00    --    0.00 -82.00 120.00  124
  3  ω    -26.00  11.00   0.50    1.00    --    0.00 -82.00 -30.00   74
  4  ω    -46.00 -12.00   0.50    1.00    --    0.00 -77.00-120.00   68
  5  ω     71.00 104.00   0.50    5.00    --   94.60 -82.00 120.00   66
  6  ω      5.00 111.00   0.50    5.00    --   94.60 -61.00-150.00  212
  7  ω     41.00 123.00   0.50    5.00    --   94.60 -82.00-150.00  164
  8  ω     89.00 126.00   0.50    5.00    --   94.60 -82.00 -90.00   74
  9  ω     89.00 114.00   0.50    5.00    --   94.60 -45.00 -30.00   50
 10  ω     71.00 168.00   0.50    5.00    --   94.60  15.00-180.00  194
 11  ω      5.00  39.00   0.50    5.00    --   94.60 -45.00 -30.00   68
 12  ω    102.00 131.00   0.50    5.00    --   94.60  15.00 120.00   58
 13  ω     20.00  46.00   0.50    5.00    --   94.60 -30.00 -30.00   52
 14  ω     53.00 106.00   0.50    5.00    --   94.60 -30.00 -30.00  106
 15  ω     84.00 110.00   0.50    5.00    --   94.60 -82.00 -60.00   52
 16  ω     73.00  99.00   0.50    5.00    --   94.60  15.00 120.00   52
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RINC): Kappa single'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0479948000
_diffrn_orient_matrix_UB_12      -0.0456715000
_diffrn_orient_matrix_UB_13      -0.1771673000
_diffrn_orient_matrix_UB_21      -0.0160127000
_diffrn_orient_matrix_UB_22      0.1483643000
_diffrn_orient_matrix_UB_23      -0.0526710000
_diffrn_orient_matrix_UB_31      0.0713860000
_diffrn_orient_matrix_UB_32      0.0028358000
_diffrn_orient_matrix_UB_33      -0.0965593000
_diffrn_oxdiff_ac3_digest_frames 
;
01a9b80c77a6c4f4b429c645ac2383e18f000273914
;
_diffrn_oxdiff_ac3_digest_hkl    
;
01d82d4f67fee07ee199a0d2d817119c6abdef
;
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2228
_reflns_number_total             2526
_reflns_odcompleteness_completeness 99.03
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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       'CrysAlisPro 1.171.39.33c (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.33c (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.33c (Rigaku OD, 2017)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.246
_refine_diff_density_min         -0.253
_refine_diff_density_rms         0.042
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     201
_refine_ls_number_reflns         2526
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0437
_refine_ls_R_factor_gt           0.0376
_refine_ls_restrained_S_all      1.053
_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)+(0.0527P)²+0.4317P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1056
_refine_ls_wR_factor_ref         0.1091
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C00C(H00C), C00F(H00F), C00J(H00J), C00K(H00K)
2.b Idealised Me refined as rotating group:
 C00H(H00A,H00B,H00D), C00L(H00E,H00G,H00H)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_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
O001 O 0.45076(5) 0.62227(9) 0.61754(12) 0.0293(2) Uani 1 1 d . . . . .
O002 O 0.35210(6) 0.49784(10) 0.51347(14) 0.0357(3) Uani 1 1 d . . . . .
O003 O 0.11588(6) 0.51389(11) 0.13331(13) 0.0405(3) Uani 1 1 d . . . . .
F004 F 0.04149(7) 0.34442(12) 0.14294(16) 0.0672(4) Uani 1 1 d . . . . .
F005 F 0.11316(8) 0.39689(12) 0.38558(15) 0.0753(4) Uani 1 1 d . . . . .
N006 N 0.34092(6) 0.98096(12) 0.47139(15) 0.0305(3) Uani 1 1 d . . . . .
F007 F 0.01969(7) 0.52082(14) 0.2919(2) 0.0842(5) Uani 1 1 d . . . . .
C008 C 0.37393(8) 0.85767(14) 0.51548(17) 0.0272(3) Uani 1 1 d . . . . .
C009 C 0.37745(8) 0.61068(14) 0.52978(17) 0.0277(3) Uani 1 1 d . . . . .
C00A C 0.33859(7) 0.73547(14) 0.46904(17) 0.0266(3) Uani 1 1 d . . . . .
C00B C 0.48600(8) 0.74442(13) 0.65628(17) 0.0277(3) Uani 1 1 d . . . . .
C00C C 0.44908(8) 0.85954(14) 0.61260(18) 0.0285(3) Uani 1 1 d . . . . .
H00C H 0.4724 0.9414 0.6455 0.034 Uiso 1 1 calc R . . . .
C00D C 0.26419(7) 0.73614(14) 0.36654(17) 0.0275(3) Uani 1 1 d . . . . .
C00E C 0.23036(8) 0.86389(14) 0.32335(17) 0.0291(3) Uani 1 1 d . . . . .
C00F C 0.22383(8) 0.61821(15) 0.30424(17) 0.0303(3) Uani 1 1 d . . . . .
H00F H 0.2449 0.5334 0.3290 0.036 Uiso 1 1 calc R . . . .
C00G C 0.15335(8) 0.63172(15) 0.20716(18) 0.0331(3) Uani 1 1 d . . . . .
C00H C 0.56563(8) 0.72875(15) 0.74274(19) 0.0317(3) Uani 1 1 d . . . . .
H00A H 0.5666 0.6789 0.8533 0.048 Uiso 1 1 calc GR . . . .
H00B H 0.5877 0.8160 0.7686 0.048 Uiso 1 1 calc GR . . . .
H00D H 0.5942 0.6812 0.6622 0.048 Uiso 1 1 calc GR . . . .
C00I C 0.27241(8) 0.98379(14) 0.38086(18) 0.0310(3) Uani 1 1 d . . . . .
C00J C 0.15687(8) 0.87024(16) 0.22404(19) 0.0342(3) Uani 1 1 d . . . . .
H00J H 0.1343 0.9537 0.1975 0.041 Uiso 1 1 calc R . . . .
C00K C 0.11827(8) 0.75525(16) 0.16622(19) 0.0366(3) Uani 1 1 d . . . . .
H00K H 0.0698 0.7597 0.1012 0.044 Uiso 1 1 calc R . . . .
C00L C 0.23950(9) 1.12118(16) 0.3371(2) 0.0405(4) Uani 1 1 d . . . . .
H00E H 0.2738 1.1886 0.3922 0.061 Uiso 1 1 calc GR . . . .
H00G H 0.1917 1.1290 0.3828 0.061 Uiso 1 1 calc GR . . . .
H00H H 0.2320 1.1338 0.2082 0.061 Uiso 1 1 calc GR . . . .
C00M C 0.07366(9) 0.44623(18) 0.2368(2) 0.0456(4) Uani 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
O001 C009 1.3813(16) . ?
O001 C00B 1.3772(16) . ?
O002 C009 1.2072(17) . ?
O003 C00G 1.4198(17) . ?
O003 C00M 1.328(2) . ?
F004 C00M 1.3152(19) . ?
F005 C00M 1.324(2) . ?
N006 C008 1.3776(17) . ?
N006 C00I 1.3101(18) . ?
F007 C00M 1.320(2) . ?
C008 C00A 1.3881(19) . ?
C008 C00C 1.4307(19) . ?
C009 C00A 1.4600(19) . ?
C00A C00D 1.4350(18) . ?
C00B C00C 1.3359(19) . ?
C00B C00H 1.4816(18) . ?
C00C H00C 0.9300 . ?
C00D C00E 1.4215(19) . ?
C00D C00F 1.4180(19) . ?
C00E C00I 1.439(2) . ?
C00E C00J 1.4130(19) . ?
C00F H00F 0.9300 . ?
C00F C00G 1.3658(19) . ?
C00G C00K 1.391(2) . ?
C00H H00A 0.9600 . ?
C00H H00B 0.9600 . ?
C00H H00D 0.9600 . ?
C00I C00L 1.502(2) . ?
C00J H00J 0.9300 . ?
C00J C00K 1.371(2) . ?
C00K H00K 0.9300 . ?
C00L H00E 0.9600 . ?
C00L H00G 0.9600 . ?
C00L H00H 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
C00B O001 C009 123.07(10) . . ?
C00M O003 C00G 117.60(11) . . ?
C00I N006 C008 118.55(12) . . ?
N006 C008 C00A 123.58(12) . . ?
N006 C008 C00C 116.58(12) . . ?
C00A C008 C00C 119.83(12) . . ?
O001 C009 C00A 116.90(11) . . ?
O002 C009 O001 116.11(12) . . ?
O002 C009 C00A 126.99(12) . . ?
C008 C00A C009 119.01(12) . . ?
C008 C00A C00D 118.81(12) . . ?
C00D C00A C009 122.16(12) . . ?
O001 C00B C00H 112.29(11) . . ?
C00C C00B O001 120.50(12) . . ?
C00C C00B C00H 127.19(12) . . ?
C008 C00C H00C 119.8 . . ?
C00B C00C C008 120.42(12) . . ?
C00B C00C H00C 119.8 . . ?
C00E C00D C00A 117.12(12) . . ?
C00F C00D C00A 124.02(12) . . ?
C00F C00D C00E 118.85(12) . . ?
C00D C00E C00I 118.91(12) . . ?
C00J C00E C00D 119.41(13) . . ?
C00J C00E C00I 121.67(13) . . ?
C00D C00F H00F 120.7 . . ?
C00G C00F C00D 118.66(13) . . ?
C00G C00F H00F 120.7 . . ?
C00F C00G O003 118.24(13) . . ?
C00F C00G C00K 123.69(13) . . ?
C00K C00G O003 117.93(12) . . ?
C00B C00H H00A 109.5 . . ?
C00B C00H H00B 109.5 . . ?
C00B C00H H00D 109.5 . . ?
H00A C00H H00B 109.5 . . ?
H00A C00H H00D 109.5 . . ?
H00B C00H H00D 109.5 . . ?
N006 C00I C00E 123.00(13) . . ?
N006 C00I C00L 116.02(13) . . ?
C00E C00I C00L 120.98(12) . . ?
C00E C00J H00J 119.5 . . ?
C00K C00J C00E 121.03(14) . . ?
C00K C00J H00J 119.5 . . ?
C00G C00K H00K 120.8 . . ?
C00J C00K C00G 118.34(13) . . ?
C00J C00K H00K 120.8 . . ?
C00I C00L H00E 109.5 . . ?
C00I C00L H00G 109.5 . . ?
C00I C00L H00H 109.5 . . ?
H00E C00L H00G 109.5 . . ?
H00E C00L H00H 109.5 . . ?
H00G C00L H00H 109.5 . . ?
F004 C00M O003 108.57(14) . . ?
F004 C00M F005 107.75(15) . . ?
F004 C00M F007 108.36(14) . . ?
F005 C00M O003 113.37(13) . . ?
F007 C00M O003 112.80(15) . . ?
F007 C00M F005 105.77(15) . . ?

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
O001 C009 C00A C008 -5.53(18) . . . . ?
O001 C009 C00A C00D 176.04(10) . . . . ?
O001 C00B C00C C008 -3.66(19) . . . . ?
O002 C009 C00A C008 173.56(13) . . . . ?
O002 C009 C00A C00D -4.9(2) . . . . ?
O003 C00G C00K C00J -174.56(12) . . . . ?
N006 C008 C00A C009 -177.26(12) . . . . ?
N006 C008 C00A C00D 1.22(19) . . . . ?
N006 C008 C00C C00B -178.16(11) . . . . ?
C008 N006 C00I C00E -0.80(19) . . . . ?
C008 N006 C00I C00L 179.93(12) . . . . ?
C008 C00A C00D C00E -1.76(18) . . . . ?
C008 C00A C00D C00F 177.06(12) . . . . ?
C009 O001 C00B C00C 1.42(19) . . . . ?
C009 O001 C00B C00H -177.17(11) . . . . ?
C009 C00A C00D C00E 176.68(11) . . . . ?
C009 C00A C00D C00F -4.5(2) . . . . ?
C00A C008 C00C C00B 1.1(2) . . . . ?
C00A C00D C00E C00I 1.12(18) . . . . ?
C00A C00D C00E C00J -179.44(11) . . . . ?
C00A C00D C00F C00G -179.76(11) . . . . ?
C00B O001 C009 O002 -176.01(11) . . . . ?
C00B O001 C009 C00A 3.19(18) . . . . ?
C00C C008 C00A C009 3.51(19) . . . . ?
C00C C008 C00A C00D -178.00(11) . . . . ?
C00D C00E C00I N006 0.2(2) . . . . ?
C00D C00E C00I C00L 179.41(12) . . . . ?
C00D C00E C00J C00K -1.1(2) . . . . ?
C00D C00F C00G O003 175.16(11) . . . . ?
C00D C00F C00G C00K -0.4(2) . . . . ?
C00E C00D C00F C00G -0.96(19) . . . . ?
C00E C00J C00K C00G -0.2(2) . . . . ?
C00F C00D C00E C00I -177.77(11) . . . . ?
C00F C00D C00E C00J 1.68(19) . . . . ?
C00F C00G C00K C00J 1.0(2) . . . . ?
C00G O003 C00M F004 177.50(13) . . . . ?
C00G O003 C00M F005 -62.80(19) . . . . ?
C00G O003 C00M F007 57.39(19) . . . . ?
C00H C00B C00C C008 174.69(12) . . . . ?
C00I N006 C008 C00A 0.09(19) . . . . ?
C00I N006 C008 C00C 179.33(11) . . . . ?
C00I C00E C00J C00K 178.34(12) . . . . ?
C00J C00E C00I N006 -179.26(12) . . . . ?
C00J C00E C00I C00L 0.0(2) . . . . ?
C00M O003 C00G C00F 87.96(17) . . . . ?
C00M O003 C00G C00K -96.23(16) . . . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.459
_oxdiff_exptl_absorpt_empirical_full_min 0.552
