# Supplementary Information (SI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2025

####################################################################### 
# 
# 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_20241207_3f_0m_a
_database_code_depnum_ccdc_archive 'CCDC 2409040'
loop_
_audit_author_name
_audit_author_address
yx
;Zhejiang Normal University
China
;
_audit_update_record             
;
2024-12-10 deposited with the CCDC.	2025-05-27 downloaded from the CCDC.
;
_audit_creation_date             2024-12-08
_audit_creation_method           
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C18 H19 F3 O2'
_chemical_formula_sum            'C18 H19 F3 O2'
_chemical_formula_weight         324.33
_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'
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/n 1'
_space_group_name_Hall           '-P 2yn'
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                   13.5172(14)
_cell_length_b                   9.3987(10)
_cell_length_c                   13.5553(14)
_cell_angle_alpha                90
_cell_angle_beta                 106.810(5)
_cell_angle_gamma                90
_cell_volume                     1648.5(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5737
_cell_measurement_temperature    273.15
_cell_measurement_theta_max      68.03
_cell_measurement_theta_min      5.48
_shelx_estimated_absorpt_T_max   0.799
_shelx_estimated_absorpt_T_min   0.725
_exptl_absorpt_coefficient_mu    0.906
_exptl_absorpt_correction_T_max  0.7531
_exptl_absorpt_correction_T_min  0.6387
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1097 before and 0.0730 after correction.
The Ratio of minimum to maximum transmission is 0.8481.
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    1.307
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             680
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.34
_exptl_crystal_size_min          0.26
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0586
_diffrn_reflns_av_unetI/netI     0.0341
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            21741
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.323
_diffrn_reflns_theta_min         5.482
_diffrn_ambient_temperature      273.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   ?
_diffrn_source_current           1.1
_diffrn_source_power             0.05500000000000001
_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                2378
_reflns_number_total             3011
_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 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'olex2.solve 1.5 (Bourhis et al., 2015)'
_refine_diff_density_max         0.218
_refine_diff_density_min         -0.219
_refine_diff_density_rms         0.037
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     209
_refine_ls_number_reflns         3011
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0609
_refine_ls_R_factor_gt           0.0483
_refine_ls_restrained_S_all      1.031
_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)+(0.0543P)²+0.4276P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1177
_refine_ls_wR_factor_ref         0.1293
_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 Ternary CH refined with riding coordinates:
 C14(H14)
2.b Secondary CH2 refined with riding coordinates:
 C13(H13A,H13B), C15(H15A,H15B), C10(H10A,H10B), C12(H12A,H12B), C11(H11A,H11B)
2.c Aromatic/amide H refined with riding coordinates:
 C5(H5), C1(H1), C3(H3), C4(H4), C2(H2)
2.d Idealised Me refined as rotating group:
 C18(H18A,H18B,H18C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_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
F3 F 0.50976(12) 0.69861(17) 0.57932(10) 0.1038(5) Uani 1 1 d . . . . .
O2 O 0.31820(12) 1.04350(15) 0.37506(12) 0.0762(4) Uani 1 1 d . . . . .
F2 F 0.39556(13) 0.59001(16) 0.46452(11) 0.1091(6) Uani 1 1 d . . . . .
O1 O 0.41100(15) 1.08393(17) 0.06719(13) 0.0865(5) Uani 1 1 d . . . . .
F1 F 0.35696(14) 0.7802(2) 0.52786(12) 0.1251(7) Uani 1 1 d . . . . .
C6 C 0.59830(12) 0.55377(18) 0.17566(13) 0.0484(4) Uani 1 1 d . . . . .
C7 C 0.52892(13) 0.66286(19) 0.18942(13) 0.0521(4) Uani 1 1 d . . . . .
C8 C 0.47434(13) 0.75522(19) 0.20375(13) 0.0514(4) Uani 1 1 d . . . . .
C14 C 0.37040(13) 0.82441(17) 0.31689(13) 0.0476(4) Uani 1 1 d . . . . .
H14 H 0.335502 0.732653 0.298490 0.057 Uiso 1 1 calc R U . . .
C9 C 0.41033(13) 0.87187(17) 0.22439(13) 0.0486(4) Uani 1 1 d . . . . .
C17 C 0.29131(14) 0.92868(19) 0.33584(14) 0.0546(4) Uani 1 1 d . . . . .
C13 C 0.31851(14) 0.8982(2) 0.12761(14) 0.0589(5) Uani 1 1 d . . . . .
H13A H 0.281313 0.809754 0.106772 0.071 Uiso 1 1 calc R U . . .
H13B H 0.271364 0.965915 0.143827 0.071 Uiso 1 1 calc R U . . .
C15 C 0.45962(14) 0.8017(2) 0.41539(14) 0.0595(5) Uani 1 1 d . . . . .
H15A H 0.515316 0.752706 0.397702 0.071 Uiso 1 1 calc R U . . .
H15B H 0.485542 0.893879 0.443524 0.071 Uiso 1 1 calc R U . . .
C10 C 0.47574(15) 1.0090(2) 0.24672(16) 0.0614(5) Uani 1 1 d . . . . .
H10A H 0.437911 1.082549 0.270689 0.074 Uiso 1 1 calc R U . . .
H10B H 0.539316 0.990820 0.300811 0.074 Uiso 1 1 calc R U . . .
C5 C 0.62756(16) 0.5455(2) 0.08611(15) 0.0653(5) Uani 1 1 d . . . . .
H5 H 0.600894 0.609627 0.032811 0.078 Uiso 1 1 calc R U . . .
C18 C 0.18090(15) 0.8822(2) 0.30657(18) 0.0729(6) Uani 1 1 d . . . . .
H18A H 0.172575 0.808791 0.352737 0.109 Uiso 1 1 calc R U . . .
H18B H 0.161395 0.846278 0.237328 0.109 Uiso 1 1 calc R U . . .
H18C H 0.137802 0.961816 0.310838 0.109 Uiso 1 1 calc R U . . .
C1 C 0.63926(16) 0.4570(2) 0.25379(16) 0.0676(5) Uani 1 1 d . . . . .
H1 H 0.620166 0.461200 0.314364 0.081 Uiso 1 1 calc R U . . .
C16 C 0.43063(18) 0.7191(2) 0.49566(16) 0.0721(6) Uani 1 1 d . . . . .
C12 C 0.35500(19) 0.9550(3) 0.03947(16) 0.0761(6) Uani 1 1 d . . . . .
H12A H 0.398753 0.884754 0.020447 0.091 Uiso 1 1 calc R U . . .
H12B H 0.295743 0.971576 -0.019918 0.091 Uiso 1 1 calc R U . . .
C3 C 0.73628(16) 0.3474(2) 0.1538(2) 0.0765(6) Uani 1 1 d . . . . .
H3 H 0.782738 0.278136 0.146413 0.092 Uiso 1 1 calc R U . . .
C4 C 0.69640(17) 0.4419(3) 0.07588(19) 0.0770(6) Uani 1 1 d . . . . .
H4 H 0.715724 0.436379 0.015487 0.092 Uiso 1 1 calc R U . . .
C11 C 0.5012(2) 1.0602(3) 0.15052(19) 0.0808(7) Uani 1 1 d . . . . .
H11A H 0.540363 1.148014 0.166024 0.097 Uiso 1 1 calc R U . . .
H11B H 0.544109 0.989888 0.130320 0.097 Uiso 1 1 calc R U . . .
C2 C 0.70803(18) 0.3546(3) 0.24256(19) 0.0818(7) Uani 1 1 d . . . . .
H2 H 0.735296 0.290204 0.295537 0.098 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
F3 C16 1.329(2) . ?
O2 C17 1.211(2) . ?
F2 C16 1.326(3) . ?
O1 C12 1.420(3) . ?
O1 C11 1.419(3) . ?
F1 C16 1.328(3) . ?
C6 C7 1.438(2) . ?
C6 C5 1.383(2) . ?
C6 C1 1.384(3) . ?
C7 C8 1.191(2) . ?
C8 C9 1.473(2) . ?
C14 H14 0.9800 . ?
C14 C9 1.566(2) . ?
C14 C17 1.526(2) . ?
C14 C15 1.533(2) . ?
C9 C13 1.543(2) . ?
C9 C10 1.543(2) . ?
C17 C18 1.494(3) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C13 C12 1.516(3) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C15 C16 1.479(3) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C10 C11 1.520(3) . ?
C5 H5 0.9300 . ?
C5 C4 1.381(3) . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C1 H1 0.9300 . ?
C1 C2 1.377(3) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C3 H3 0.9300 . ?
C3 C4 1.366(3) . ?
C3 C2 1.365(3) . ?
C4 H4 0.9300 . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C2 H2 0.9300 . ?

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
C11 O1 C12 110.24(17) . . ?
C5 C6 C7 121.12(17) . . ?
C5 C6 C1 118.80(17) . . ?
C1 C6 C7 120.06(16) . . ?
C8 C7 C6 177.57(19) . . ?
C7 C8 C9 177.79(18) . . ?
C9 C14 H14 107.4 . . ?
C17 C14 H14 107.4 . . ?
C17 C14 C9 111.85(14) . . ?
C17 C14 C15 110.83(14) . . ?
C15 C14 H14 107.4 . . ?
C15 C14 C9 111.73(14) . . ?
C8 C9 C14 107.30(14) . . ?
C8 C9 C13 109.27(14) . . ?
C8 C9 C10 108.93(14) . . ?
C13 C9 C14 110.34(13) . . ?
C10 C9 C14 113.04(14) . . ?
C10 C9 C13 107.91(15) . . ?
O2 C17 C14 120.67(17) . . ?
O2 C17 C18 121.78(17) . . ?
C18 C17 C14 117.53(16) . . ?
C9 C13 H13A 109.4 . . ?
C9 C13 H13B 109.4 . . ?
H13A C13 H13B 108.0 . . ?
C12 C13 C9 111.20(16) . . ?
C12 C13 H13A 109.4 . . ?
C12 C13 H13B 109.4 . . ?
C14 C15 H15A 108.8 . . ?
C14 C15 H15B 108.8 . . ?
H15A C15 H15B 107.7 . . ?
C16 C15 C14 113.86(16) . . ?
C16 C15 H15A 108.8 . . ?
C16 C15 H15B 108.8 . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
H10A C10 H10B 108.1 . . ?
C11 C10 C9 110.82(16) . . ?
C11 C10 H10A 109.5 . . ?
C11 C10 H10B 109.5 . . ?
C6 C5 H5 120.0 . . ?
C4 C5 C6 119.98(19) . . ?
C4 C5 H5 120.0 . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C6 C1 H1 119.7 . . ?
C2 C1 C6 120.54(19) . . ?
C2 C1 H1 119.7 . . ?
F3 C16 C15 112.63(19) . . ?
F2 C16 F3 105.34(18) . . ?
F2 C16 F1 105.5(2) . . ?
F2 C16 C15 113.12(18) . . ?
F1 C16 F3 106.09(19) . . ?
F1 C16 C15 113.47(18) . . ?
O1 C12 C13 111.25(17) . . ?
O1 C12 H12A 109.4 . . ?
O1 C12 H12B 109.4 . . ?
C13 C12 H12A 109.4 . . ?
C13 C12 H12B 109.4 . . ?
H12A C12 H12B 108.0 . . ?
C4 C3 H3 120.0 . . ?
C2 C3 H3 120.0 . . ?
C2 C3 C4 120.07(19) . . ?
C5 C4 H4 119.8 . . ?
C3 C4 C5 120.5(2) . . ?
C3 C4 H4 119.8 . . ?
O1 C11 C10 112.16(18) . . ?
O1 C11 H11A 109.2 . . ?
O1 C11 H11B 109.2 . . ?
C10 C11 H11A 109.2 . . ?
C10 C11 H11B 109.2 . . ?
H11A C11 H11B 107.9 . . ?
C1 C2 H2 119.9 . . ?
C3 C2 C1 120.1(2) . . ?
C3 C2 H2 119.9 . . ?

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
C6 C5 C4 C3 -0.2(3) . . . . ?
C6 C1 C2 C3 -0.2(4) . . . . ?
C7 C6 C5 C4 178.34(18) . . . . ?
C7 C6 C1 C2 -178.16(19) . . . . ?
C8 C9 C13 C12 -66.6(2) . . . . ?
C8 C9 C10 C11 67.8(2) . . . . ?
C14 C9 C13 C12 175.65(15) . . . . ?
C14 C9 C10 C11 -172.98(16) . . . . ?
C14 C15 C16 F3 178.76(17) . . . . ?
C14 C15 C16 F2 59.4(2) . . . . ?
C14 C15 C16 F1 -60.7(2) . . . . ?
C9 C14 C17 O2 -73.9(2) . . . . ?
C9 C14 C17 C18 107.49(18) . . . . ?
C9 C14 C15 C16 -163.51(16) . . . . ?
C9 C13 C12 O1 -58.4(2) . . . . ?
C9 C10 C11 O1 57.1(2) . . . . ?
C17 C14 C9 C8 -172.30(14) . . . . ?
C17 C14 C9 C13 -53.34(18) . . . . ?
C17 C14 C9 C10 67.59(18) . . . . ?
C17 C14 C15 C16 71.0(2) . . . . ?
C13 C9 C10 C11 -50.7(2) . . . . ?
C15 C14 C9 C8 62.79(17) . . . . ?
C15 C14 C9 C13 -178.25(14) . . . . ?
C15 C14 C9 C10 -57.32(19) . . . . ?
C15 C14 C17 O2 51.5(2) . . . . ?
C15 C14 C17 C18 -127.10(18) . . . . ?
C10 C9 C13 C12 51.7(2) . . . . ?
C5 C6 C1 C2 0.1(3) . . . . ?
C1 C6 C5 C4 0.1(3) . . . . ?
C12 O1 C11 C10 -61.9(2) . . . . ?
C4 C3 C2 C1 0.0(4) . . . . ?
C11 O1 C12 C13 62.2(2) . . . . ?
C2 C3 C4 C5 0.2(4) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
