# 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_mj24097_0m
_audit_block_doi                 10.5517/ccdc.csd.cc2jghgz
_database_code_depnum_ccdc_archive 'CCDC 2337631'
loop_
_audit_author_name
_audit_author_address
FENFI-
;East China Normal University
China
;
_audit_update_record             
;
2024-03-05 deposited with the CCDC.	2025-04-22 downloaded from the CCDC.
;
_audit_creation_date             2024-01-29
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C17 H15 F O2'
_chemical_formula_sum            'C17 H15 F O2'
_chemical_formula_weight         270.29
_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 0.0137 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'
O O 0.0389 0.0241 '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'

_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      orthorhombic
_space_group_IT_number           56
_space_group_name_H-M_alt        'P c c n'
_space_group_name_Hall           '-P 2ab 2ac'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y+1/2, z'
'-x, y+1/2, -z+1/2'
'x+1/2, -y, -z+1/2'
'-x, -y, -z'
'x-1/2, y-1/2, -z'
'x, -y-1/2, z-1/2'
'-x-1/2, y, z-1/2'

_cell_length_a                   13.7828(3)
_cell_length_b                   27.4622(6)
_cell_length_c                   7.5425(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2854.88(12)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    9889
_cell_measurement_temperature    224.00
_cell_measurement_theta_max      55.016
_cell_measurement_theta_min      2.790
_shelx_estimated_absorpt_T_max   0.977
_shelx_estimated_absorpt_T_min   0.924
_exptl_absorpt_coefficient_mu    0.472
_exptl_absorpt_correction_T_max  0.7508
_exptl_absorpt_correction_T_min  0.6146
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1200 before and 0.0844 after correction.
The Ratio of minimum to maximum transmission is 0.8186.
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    1.258
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1136
_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0685
_diffrn_reflns_av_unetI/netI     0.0320
_diffrn_reflns_Laue_measured_fraction_full 0.996
_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       29
_diffrn_reflns_limit_k_min       -33
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            26007
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         55.020
_diffrn_reflns_theta_min         2.800
_diffrn_ambient_temperature      224.00
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           GaK\a
_diffrn_radiation_wavelength     1.34139
_diffrn_source                   ?
_diffrn_source_current           2.86
_diffrn_source_power             0.1995708
_diffrn_source_voltage           69.78
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2470
_reflns_number_total             2715
_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 V8.40B (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.256
_refine_diff_density_min         -0.303
_refine_diff_density_rms         0.053
_refine_ls_extinction_coef       0.0034(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.250
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     182
_refine_ls_number_reflns         2715
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0748
_refine_ls_R_factor_gt           0.0699
_refine_ls_restrained_S_all      1.250
_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)+5.8135P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1622
_refine_ls_wR_factor_ref         0.1641
_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 O(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B)
2.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2A), C7(H7), C8(H8), C9(H9), C10(H10), C11(H11), C13(H13),
 C14(H14), C15(H15), C16(H16), C17(H17)
2.c Tetrahedral OH refined with riding coordinates:
 O2(H2)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_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
F1 F 0.6441(2) 0.47738(9) -0.1897(3) 0.0739(8) Uani 1 1 d . . . . .
O1 O 0.43622(15) 0.44706(8) 0.4617(3) 0.0401(6) Uani 1 1 d . . . . .
O2 O 0.58804(16) 0.46717(8) 0.3896(3) 0.0410(6) Uani 1 1 d . . . . .
H2 H 0.568688 0.494550 0.419948 0.061 Uiso 1 1 calc R U . . .
C1 C 0.6583(3) 0.45281(13) -0.0349(5) 0.0504(9) Uani 1 1 d . . . . .
H1 H 0.710258 0.461660 0.039134 0.060 Uiso 1 1 calc R U . . .
C2 C 0.6013(2) 0.41732(12) 0.0122(5) 0.0369(8) Uani 1 1 d . . . . .
H2A H 0.547634 0.409672 -0.059361 0.044 Uiso 1 1 calc R U . . .
C3 C 0.6188(2) 0.38832(11) 0.1772(4) 0.0316(7) Uani 1 1 d . . . . .
H3A H 0.676337 0.401529 0.236577 0.038 Uiso 1 1 calc R U . . .
H3B H 0.633872 0.354759 0.142612 0.038 Uiso 1 1 calc R U . . .
C4 C 0.5344(2) 0.38704(10) 0.3130(4) 0.0265(6) Uani 1 1 d . . . . .
C5 C 0.5180(2) 0.43784(10) 0.3898(4) 0.0282(6) Uani 1 1 d . . . . .
C6 C 0.5607(2) 0.35552(10) 0.4760(4) 0.0279(6) Uani 1 1 d . . . . .
C7 C 0.6530(2) 0.33626(11) 0.5025(4) 0.0325(7) Uani 1 1 d . . . . .
H7 H 0.703041 0.343478 0.422101 0.039 Uiso 1 1 calc R U . . .
C8 C 0.6713(2) 0.30642(11) 0.6474(5) 0.0396(8) Uani 1 1 d . . . . .
H8 H 0.733799 0.293409 0.662980 0.047 Uiso 1 1 calc R U . . .
C9 C 0.5999(3) 0.29551(12) 0.7683(5) 0.0424(8) Uani 1 1 d . . . . .
H9 H 0.612950 0.274804 0.864693 0.051 Uiso 1 1 calc R U . . .
C10 C 0.5083(3) 0.31556(13) 0.7459(5) 0.0432(8) Uani 1 1 d . . . . .
H10 H 0.459148 0.309098 0.828991 0.052 Uiso 1 1 calc R U . . .
C11 C 0.4894(2) 0.34510(12) 0.6011(4) 0.0369(7) Uani 1 1 d . . . . .
H11 H 0.426979 0.358392 0.586952 0.044 Uiso 1 1 calc R U . . .
C12 C 0.4439(2) 0.36655(11) 0.2210(4) 0.0294(7) Uani 1 1 d . . . . .
C13 C 0.4308(2) 0.31637(11) 0.2116(4) 0.0348(7) Uani 1 1 d . . . . .
H13 H 0.475420 0.295619 0.267840 0.042 Uiso 1 1 calc R U . . .
C14 C 0.3527(3) 0.29645(13) 0.1205(5) 0.0435(9) Uani 1 1 d . . . . .
H14 H 0.344277 0.262489 0.117149 0.052 Uiso 1 1 calc R U . . .
C15 C 0.2878(3) 0.32626(15) 0.0354(5) 0.0482(9) Uani 1 1 d . . . . .
H15 H 0.235229 0.312713 -0.026903 0.058 Uiso 1 1 calc R U . . .
C16 C 0.2995(3) 0.37582(15) 0.0412(5) 0.0488(9) Uani 1 1 d . . . . .
H16 H 0.254924 0.396200 -0.016937 0.059 Uiso 1 1 calc R U . . .
C17 C 0.3779(2) 0.39620(12) 0.1337(5) 0.0383(8) Uani 1 1 d . . . . .
H17 H 0.385737 0.430195 0.136662 0.046 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
F1 C1 1.362(4) . ?
O1 C5 1.276(3) . ?
O2 H2 0.8300 . ?
O2 C5 1.257(3) . ?
C1 H1 0.9400 . ?
C1 C2 1.301(5) . ?
C2 H2A 0.9400 . ?
C2 C3 1.497(4) . ?
C3 H3A 0.9800 . ?
C3 H3B 0.9800 . ?
C3 C4 1.551(4) . ?
C4 C5 1.527(4) . ?
C4 C6 1.547(4) . ?
C4 C12 1.534(4) . ?
C6 C7 1.391(4) . ?
C6 C11 1.393(4) . ?
C7 H7 0.9400 . ?
C7 C8 1.389(4) . ?
C8 H8 0.9400 . ?
C8 C9 1.375(5) . ?
C9 H9 0.9400 . ?
C9 C10 1.388(5) . ?
C10 H10 0.9400 . ?
C10 C11 1.386(5) . ?
C11 H11 0.9400 . ?
C12 C13 1.392(4) . ?
C12 C17 1.387(4) . ?
C13 H13 0.9400 . ?
C13 C14 1.389(5) . ?
C14 H14 0.9400 . ?
C14 C15 1.372(5) . ?
C15 H15 0.9400 . ?
C15 C16 1.371(5) . ?
C16 H16 0.9400 . ?
C16 C17 1.402(5) . ?
C17 H17 0.9400 . ?

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
C5 O2 H2 109.5 . . ?
F1 C1 H1 119.4 . . ?
C2 C1 F1 121.2(4) . . ?
C2 C1 H1 119.4 . . ?
C1 C2 H2A 119.0 . . ?
C1 C2 C3 121.9(3) . . ?
C3 C2 H2A 119.0 . . ?
C2 C3 H3A 108.3 . . ?
C2 C3 H3B 108.3 . . ?
C2 C3 C4 116.1(2) . . ?
H3A C3 H3B 107.4 . . ?
C4 C3 H3A 108.3 . . ?
C4 C3 H3B 108.3 . . ?
C5 C4 C3 109.9(2) . . ?
C5 C4 C6 104.2(2) . . ?
C5 C4 C12 112.7(2) . . ?
C6 C4 C3 111.2(2) . . ?
C12 C4 C3 108.6(2) . . ?
C12 C4 C6 110.2(2) . . ?
O1 C5 C4 118.3(2) . . ?
O2 C5 O1 123.5(3) . . ?
O2 C5 C4 118.1(2) . . ?
C7 C6 C4 122.8(3) . . ?
C7 C6 C11 118.0(3) . . ?
C11 C6 C4 119.2(3) . . ?
C6 C7 H7 119.9 . . ?
C8 C7 C6 120.2(3) . . ?
C8 C7 H7 119.9 . . ?
C7 C8 H8 119.3 . . ?
C9 C8 C7 121.4(3) . . ?
C9 C8 H8 119.3 . . ?
C8 C9 H9 120.5 . . ?
C8 C9 C10 118.9(3) . . ?
C10 C9 H9 120.5 . . ?
C9 C10 H10 120.0 . . ?
C11 C10 C9 120.0(3) . . ?
C11 C10 H10 120.0 . . ?
C6 C11 H11 119.3 . . ?
C10 C11 C6 121.4(3) . . ?
C10 C11 H11 119.3 . . ?
C13 C12 C4 119.5(3) . . ?
C17 C12 C4 122.2(3) . . ?
C17 C12 C13 118.1(3) . . ?
C12 C13 H13 119.5 . . ?
C14 C13 C12 121.1(3) . . ?
C14 C13 H13 119.5 . . ?
C13 C14 H14 120.0 . . ?
C15 C14 C13 120.1(3) . . ?
C15 C14 H14 120.0 . . ?
C14 C15 H15 120.0 . . ?
C16 C15 C14 120.0(3) . . ?
C16 C15 H15 120.0 . . ?
C15 C16 H16 119.9 . . ?
C15 C16 C17 120.2(3) . . ?
C17 C16 H16 119.9 . . ?
C12 C17 C16 120.5(3) . . ?
C12 C17 H17 119.8 . . ?
C16 C17 H17 119.8 . . ?

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
F1 C1 C2 C3 176.9(3) . . . . ?
C1 C2 C3 C4 123.2(4) . . . . ?
C2 C3 C4 C5 -65.9(3) . . . . ?
C2 C3 C4 C6 179.3(2) . . . . ?
C2 C3 C4 C12 57.9(3) . . . . ?
C3 C4 C5 O1 159.9(3) . . . . ?
C3 C4 C5 O2 -24.9(4) . . . . ?
C3 C4 C6 C7 7.1(4) . . . . ?
C3 C4 C6 C11 -171.9(3) . . . . ?
C3 C4 C12 C13 85.1(3) . . . . ?
C3 C4 C12 C17 -89.7(3) . . . . ?
C4 C6 C7 C8 -177.1(3) . . . . ?
C4 C6 C11 C10 177.6(3) . . . . ?
C4 C12 C13 C14 -176.3(3) . . . . ?
C4 C12 C17 C16 175.8(3) . . . . ?
C5 C4 C6 C7 -111.3(3) . . . . ?
C5 C4 C6 C11 69.7(3) . . . . ?
C5 C4 C12 C13 -152.8(3) . . . . ?
C5 C4 C12 C17 32.4(4) . . . . ?
C6 C4 C5 O1 -80.9(3) . . . . ?
C6 C4 C5 O2 94.3(3) . . . . ?
C6 C4 C12 C13 -36.9(4) . . . . ?
C6 C4 C12 C17 148.3(3) . . . . ?
C6 C7 C8 C9 -0.6(5) . . . . ?
C7 C6 C11 C10 -1.5(5) . . . . ?
C7 C8 C9 C10 -1.1(5) . . . . ?
C8 C9 C10 C11 1.5(5) . . . . ?
C9 C10 C11 C6 -0.2(5) . . . . ?
C11 C6 C7 C8 1.9(4) . . . . ?
C12 C4 C5 O1 38.5(4) . . . . ?
C12 C4 C5 O2 -146.2(3) . . . . ?
C12 C4 C6 C7 127.6(3) . . . . ?
C12 C4 C6 C11 -51.4(3) . . . . ?
C12 C13 C14 C15 1.0(5) . . . . ?
C13 C12 C17 C16 0.9(5) . . . . ?
C13 C14 C15 C16 -0.5(5) . . . . ?
C14 C15 C16 C17 0.1(6) . . . . ?
C15 C16 C17 C12 -0.4(5) . . . . ?
C17 C12 C13 C14 -1.2(5) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
