# Supplementary Information (SI) for Green Chemistry.
# This journal is © The Royal Society of Chemistry 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_ga_250123a_a
_database_code_depnum_ccdc_archive 'CCDC 2483414'
loop_
_audit_author_name
_audit_author_address
'Zhigang Liu'
;Fudan University
China
;
_audit_update_record             
;
2025-08-28 deposited with the CCDC.	2026-02-03 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2019/2
_shelx_SHELXL_version_number     2019/2
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C18 H17 F3 O2'
_chemical_formula_weight         322.32

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0137 0.0067 '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 0.0583 0.0400 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0389 0.0241 '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                   6.5279(14)
_cell_length_b                   11.063(2)
_cell_length_c                   22.438(5)
_cell_angle_alpha                90
_cell_angle_beta                 96.638(9)
_cell_angle_gamma                90
_cell_volume                     1609.5(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    5556
_cell_measurement_theta_min      3.88
_cell_measurement_theta_max      53.95

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.330
_exptl_crystal_F_000             672
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.030
_exptl_crystal_size_min          0.020
_exptl_absorpt_coefficient_mu    0.591
_shelx_estimated_absorpt_T_min   0.891
_shelx_estimated_absorpt_T_max   0.988
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.372
_exptl_absorpt_correction_T_max  0.970
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     1.34139
_diffrn_radiation_type           GaK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            8934
_diffrn_reflns_av_unetI/netI     0.0800
_diffrn_reflns_av_R_equivalents  0.0904
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_theta_min         3.881
_diffrn_reflns_theta_max         54.018
_diffrn_reflns_theta_full        53.594
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             2936
_reflns_number_gt                1878
_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 APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2019/2 (Sheldrick, 2019)'
_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)+(0.1830P)²+5.0000P] 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     'SHELXL-2019/2 (Sheldrick 2019)'
_refine_ls_extinction_coef       0.018(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2936
_refine_ls_number_parameters     213
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.1442
_refine_ls_R_factor_gt           0.1004
_refine_ls_wR_factor_ref         0.3013
_refine_ls_wR_factor_gt          0.2451
_refine_ls_goodness_of_fit_ref   0.869
_refine_ls_restrained_S_all      0.869
_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
F1 F 0.7424(4) 0.4948(2) 0.62026(12) 0.0524(8) Uani 1 1 d . . . . .
F2 F 1.0232(4) 0.3972(2) 0.64526(13) 0.0562(9) Uani 1 1 d . . . . .
F3 F 0.9434(5) 0.4521(2) 0.55388(13) 0.0593(9) Uani 1 1 d . . . . .
O1 O 0.8992(5) 0.2144(3) 0.56635(14) 0.0435(8) Uani 1 1 d D . . . .
H1 H 0.840(10) 0.145(4) 0.565(3) 0.09(2) Uiso 1 1 d D . . . .
O2 O 0.1996(5) 0.0256(3) 0.45834(16) 0.0527(10) Uani 1 1 d . . . . .
C1 C 0.6803(7) 0.2417(4) 0.6476(2) 0.0407(11) Uani 1 1 d . . . . .
C2 C 0.5015(8) 0.2810(5) 0.6689(2) 0.0523(13) Uani 1 1 d . . . . .
H2 H 0.415438 0.337713 0.646198 0.063 Uiso 1 1 calc R U . . .
C3 C 0.4460(9) 0.2387(5) 0.7231(2) 0.0620(15) Uani 1 1 d . . . . .
H3 H 0.322702 0.266478 0.737248 0.074 Uiso 1 1 calc R U . . .
C4 C 0.5689(9) 0.1569(5) 0.7562(2) 0.0604(14) Uani 1 1 d . . . . .
H4 H 0.530712 0.128167 0.793258 0.073 Uiso 1 1 calc R U . . .
C5 C 0.7489(8) 0.1158(5) 0.7358(2) 0.0552(13) Uani 1 1 d . . . . .
H5 H 0.833978 0.058653 0.758519 0.066 Uiso 1 1 calc R U . . .
C6 C 0.8032(7) 0.1589(4) 0.6819(2) 0.0483(12) Uani 1 1 d . . . . .
H6 H 0.927186 0.131401 0.668047 0.058 Uiso 1 1 calc R U . . .
C7 C 0.7470(7) 0.2896(4) 0.5881(2) 0.0401(10) Uani 1 1 d . . . . .
C8 C 0.5694(7) 0.3144(4) 0.5392(2) 0.0399(10) Uani 1 1 d . . . . .
H8A H 0.472934 0.372117 0.554960 0.048 Uiso 1 1 calc R U . . .
H8B H 0.625272 0.353494 0.504842 0.048 Uiso 1 1 calc R U . . .
C9 C 0.4496(7) 0.2016(4) 0.5169(2) 0.0438(11) Uani 1 1 d . . . . .
H9A H 0.539398 0.148664 0.495545 0.053 Uiso 1 1 calc R U . . .
H9B H 0.408100 0.156166 0.551521 0.053 Uiso 1 1 calc R U . . .
C10 C 0.2592(7) 0.2353(4) 0.47485(19) 0.0394(10) Uani 1 1 d . . . . .
H10A H 0.170673 0.287896 0.496762 0.047 Uiso 1 1 calc R U . . .
H10B H 0.302549 0.282851 0.441112 0.047 Uiso 1 1 calc R U . . .
C11 C 0.1319(7) 0.1286(4) 0.4494(2) 0.0406(11) Uani 1 1 d . . . . .
C12 C -0.0693(7) 0.1501(4) 0.4134(2) 0.0388(10) Uani 1 1 d . . . . .
C13 C -0.1925(7) 0.0515(4) 0.3932(2) 0.0457(11) Uani 1 1 d . . . . .
H13 H -0.145726 -0.028187 0.402990 0.055 Uiso 1 1 calc R U . . .
C14 C -0.3799(8) 0.0678(5) 0.3596(2) 0.0558(13) Uani 1 1 d . . . . .
H14 H -0.461177 -0.000252 0.346234 0.067 Uiso 1 1 calc R U . . .
C15 C -0.4514(8) 0.1844(5) 0.3451(2) 0.0542(13) Uani 1 1 d . . . . .
H15 H -0.581255 0.196061 0.322023 0.065 Uiso 1 1 calc R U . . .
C16 C -0.3311(8) 0.2822(5) 0.3647(2) 0.0534(13) Uani 1 1 d . . . . .
H16 H -0.377474 0.361688 0.354337 0.064 Uiso 1 1 calc R U . . .
C17 C -0.1440(7) 0.2659(4) 0.3994(2) 0.0470(12) Uani 1 1 d . . . . .
H17 H -0.065398 0.334322 0.413773 0.056 Uiso 1 1 calc R U . . .
C18 C 0.8637(7) 0.4085(4) 0.6021(2) 0.0434(11) 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
F1 C18 1.334(5) . ?
F2 C18 1.344(5) . ?
F3 C18 1.343(5) . ?
O1 C7 1.425(5) . ?
O1 H1 0.85(4) . ?
O2 C11 1.230(5) . ?
C1 C2 1.381(7) . ?
C1 C6 1.390(6) . ?
C1 C7 1.545(6) . ?
C2 C3 1.390(7) . ?
C2 H2 0.9500 . ?
C3 C4 1.370(8) . ?
C3 H3 0.9500 . ?
C4 C5 1.386(8) . ?
C4 H4 0.9500 . ?
C5 C6 1.383(7) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C7 C8 1.527(6) . ?
C7 C18 1.534(6) . ?
C8 C9 1.526(6) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 C10 1.517(6) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 C11 1.516(6) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 C12 1.480(6) . ?
C12 C17 1.394(6) . ?
C12 C13 1.399(6) . ?
C13 C14 1.373(7) . ?
C13 H13 0.9500 . ?
C14 C15 1.396(7) . ?
C14 H14 0.9500 . ?
C15 C16 1.379(7) . ?
C15 H15 0.9500 . ?
C16 C17 1.382(7) . ?
C16 H16 0.9500 . ?
C17 H17 0.9500 . ?

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
C7 O1 H1 102(5) . . ?
C2 C1 C6 118.3(4) . . ?
C2 C1 C7 121.7(4) . . ?
C6 C1 C7 120.1(4) . . ?
C1 C2 C3 120.8(5) . . ?
C1 C2 H2 119.6 . . ?
C3 C2 H2 119.6 . . ?
C4 C3 C2 120.1(5) . . ?
C4 C3 H3 120.0 . . ?
C2 C3 H3 120.0 . . ?
C3 C4 C5 120.2(5) . . ?
C3 C4 H4 119.9 . . ?
C5 C4 H4 119.9 . . ?
C6 C5 C4 119.2(5) . . ?
C6 C5 H5 120.4 . . ?
C4 C5 H5 120.4 . . ?
C5 C6 C1 121.4(5) . . ?
C5 C6 H6 119.3 . . ?
C1 C6 H6 119.3 . . ?
O1 C7 C8 111.1(4) . . ?
O1 C7 C18 102.8(3) . . ?
C8 C7 C18 108.0(3) . . ?
O1 C7 C1 112.0(3) . . ?
C8 C7 C1 114.6(4) . . ?
C18 C7 C1 107.5(4) . . ?
C9 C8 C7 114.0(3) . . ?
C9 C8 H8A 108.8 . . ?
C7 C8 H8A 108.8 . . ?
C9 C8 H8B 108.8 . . ?
C7 C8 H8B 108.8 . . ?
H8A C8 H8B 107.6 . . ?
C10 C9 C8 110.8(4) . . ?
C10 C9 H9A 109.5 . . ?
C8 C9 H9A 109.5 . . ?
C10 C9 H9B 109.5 . . ?
C8 C9 H9B 109.5 . . ?
H9A C9 H9B 108.1 . . ?
C11 C10 C9 114.6(4) . . ?
C11 C10 H10A 108.6 . . ?
C9 C10 H10A 108.6 . . ?
C11 C10 H10B 108.6 . . ?
C9 C10 H10B 108.6 . . ?
H10A C10 H10B 107.6 . . ?
O2 C11 C12 121.1(4) . . ?
O2 C11 C10 119.3(4) . . ?
C12 C11 C10 119.6(4) . . ?
C17 C12 C13 118.1(4) . . ?
C17 C12 C11 122.4(4) . . ?
C13 C12 C11 119.5(4) . . ?
C14 C13 C12 121.2(4) . . ?
C14 C13 H13 119.4 . . ?
C12 C13 H13 119.4 . . ?
C13 C14 C15 120.2(5) . . ?
C13 C14 H14 119.9 . . ?
C15 C14 H14 119.9 . . ?
C16 C15 C14 119.2(5) . . ?
C16 C15 H15 120.4 . . ?
C14 C15 H15 120.4 . . ?
C15 C16 C17 120.7(5) . . ?
C15 C16 H16 119.7 . . ?
C17 C16 H16 119.7 . . ?
C16 C17 C12 120.7(4) . . ?
C16 C17 H17 119.7 . . ?
C12 C17 H17 119.7 . . ?
F1 C18 F3 106.7(4) . . ?
F1 C18 F2 106.5(4) . . ?
F3 C18 F2 105.9(4) . . ?
F1 C18 C7 112.2(4) . . ?
F3 C18 C7 112.0(4) . . ?
F2 C18 C7 113.1(4) . . ?

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 C1 C2 C3 -0.1(7) . . . . ?
C7 C1 C2 C3 -178.8(5) . . . . ?
C1 C2 C3 C4 0.0(9) . . . . ?
C2 C3 C4 C5 -0.1(9) . . . . ?
C3 C4 C5 C6 0.4(8) . . . . ?
C4 C5 C6 C1 -0.6(8) . . . . ?
C2 C1 C6 C5 0.4(7) . . . . ?
C7 C1 C6 C5 179.1(4) . . . . ?
C2 C1 C7 O1 -163.4(4) . . . . ?
C6 C1 C7 O1 18.0(5) . . . . ?
C2 C1 C7 C8 -35.7(6) . . . . ?
C6 C1 C7 C8 145.7(4) . . . . ?
C2 C1 C7 C18 84.4(5) . . . . ?
C6 C1 C7 C18 -94.2(5) . . . . ?
O1 C7 C8 C9 63.1(5) . . . . ?
C18 C7 C8 C9 175.1(4) . . . . ?
C1 C7 C8 C9 -65.1(5) . . . . ?
C7 C8 C9 C10 172.2(4) . . . . ?
C8 C9 C10 C11 179.0(4) . . . . ?
C9 C10 C11 O2 -8.0(6) . . . . ?
C9 C10 C11 C12 173.2(4) . . . . ?
O2 C11 C12 C17 -175.9(4) . . . . ?
C10 C11 C12 C17 2.9(7) . . . . ?
O2 C11 C12 C13 5.4(7) . . . . ?
C10 C11 C12 C13 -175.9(4) . . . . ?
C17 C12 C13 C14 1.3(7) . . . . ?
C11 C12 C13 C14 -179.9(4) . . . . ?
C12 C13 C14 C15 -0.3(8) . . . . ?
C13 C14 C15 C16 0.3(8) . . . . ?
C14 C15 C16 C17 -1.3(8) . . . . ?
C15 C16 C17 C12 2.4(8) . . . . ?
C13 C12 C17 C16 -2.3(7) . . . . ?
C11 C12 C17 C16 178.9(4) . . . . ?
O1 C7 C18 F1 176.5(3) . . . . ?
C8 C7 C18 F1 58.9(5) . . . . ?
C1 C7 C18 F1 -65.2(5) . . . . ?
O1 C7 C18 F3 56.5(4) . . . . ?
C8 C7 C18 F3 -61.0(5) . . . . ?
C1 C7 C18 F3 174.8(4) . . . . ?
O1 C7 C18 F2 -63.1(5) . . . . ?
C8 C7 C18 F2 179.4(4) . . . . ?
C1 C7 C18 F2 55.2(5) . . . . ?

_refine_diff_density_max         0.537
_refine_diff_density_min         -0.616
_refine_diff_density_rms         0.131

