# Supplementary Information (SI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 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. 
# 
#######################################################################

data_240114lu_lgpz115096_0m
_database_code_depnum_ccdc_archive 'CCDC 2326306'
loop_
_audit_author_name
_audit_author_address
'Hui Qin'
; Hangzhou Medical College
China
;
_audit_update_record             
;
2024-01-18 deposited with the CCDC.	2025-04-30 downloaded from the CCDC.
;
_audit_creation_date             2024-01-17
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2019/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C18 H14 F N3 O2, H2 O'
_chemical_formula_sum            'C18 H16 F N3 O3'
_chemical_formula_weight         341.34
_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'
F F 0.0583 0.0400 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0241 0.0134 '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'

_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           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   24.355(17)
_cell_length_b                   8.370(6)
_cell_length_c                   15.766(12)
_cell_angle_alpha                90
_cell_angle_beta                 100.14(2)
_cell_angle_gamma                90
_cell_volume                     3164(4)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    4216
_cell_measurement_temperature    193.00
_cell_measurement_theta_max      51.57
_cell_measurement_theta_min      4.87
_shelx_estimated_absorpt_T_max   0.950
_shelx_estimated_absorpt_T_min   0.934
_exptl_absorpt_coefficient_mu    0.573
_exptl_absorpt_correction_T_max  0.7518
_exptl_absorpt_correction_T_min  0.5486
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1528 before and 0.0902 after correction.
The Ratio of minimum to maximum transmission is 0.7297.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.433
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1424
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.09
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0814
_diffrn_reflns_av_unetI/netI     0.0722
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.968
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_h_min       -31
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            17700
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.968
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         60.748
_diffrn_reflns_theta_min         4.869
_diffrn_ambient_temperature      193.00
_diffrn_detector                 CPAD
_diffrn_detector_area_resol_mean 7.41
_diffrn_detector_type            'Bruker PHOTON II'
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.968
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Bruker D8 VENTURE Metaljet PHOTON II'
_diffrn_measurement_method       'ω and φ shutterless scans'
_diffrn_measurement_specimen_support 'nylon loop'
_diffrn_radiation_monochromator  'Helios Multi-layer Optic'
_diffrn_radiation_probe          X-ray
_diffrn_radiation_type           GaK\a
_diffrn_radiation_wavelength     1.34139
_diffrn_source                   MetalJet
_diffrn_source_current           2.85
_diffrn_source_power             0.1986735
_diffrn_source_type              'Liquid Metal source'
_diffrn_source_voltage           69.71
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1985
_reflns_number_total             3535
_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 (Bruker, 2019)'
_computing_data_collection       'APEX5 V2023.9-2 (Bruker, 2023)'
_computing_data_reduction        'SAINT V8.40B (Bruker, 2019)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.362
_refine_diff_density_min         -0.308
_refine_diff_density_rms         0.077
_refine_ls_extinction_coef       0.0040(8)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2019/2 (Sheldrick 2019)'
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     229
_refine_ls_number_reflns         3535
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1329
_refine_ls_R_factor_gt           0.0885
_refine_ls_restrained_S_all      1.038
_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)+(0.1842P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2547
_refine_ls_wR_factor_ref         0.2953
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H,H) groups
2.a Riding coordinates:
 O3(H3B,H3C)
2.b Aromatic/amide H refined with riding coordinates:
 N3(H3), C2(H2), C3(H3A), C4(H4), C5(H5), C14(H14), C15(H15), C16(H16)
2.c Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C), C18(H18A,H18B,H18C)
;
_atom_sites_solution_hydrogens   mixed
_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 0.53887(8) 0.4746(2) 0.59691(13) 0.0738(6) Uani 1 1 d . . . . .
O1 O 0.69448(11) 0.6834(3) 0.67707(16) 0.0744(8) Uani 1 1 d . . . . .
O2 O 0.58135(11) 0.7441(3) 0.51273(15) 0.0780(8) Uani 1 1 d . . . . .
N1 N 0.73717(12) 0.4471(3) 0.65403(17) 0.0659(8) Uani 1 1 d . . . . .
N2 N 0.63038(12) 0.3193(3) 0.59786(17) 0.0643(8) Uani 1 1 d . . . . .
N3 N 0.57164(13) 0.8382(3) 0.64581(18) 0.0677(8) Uani 1 1 d . . . . .
H3 H 0.565597 0.939735 0.633037 0.081 Uiso 1 1 calc R U . . .
C1 C 0.73147(16) 0.2903(4) 0.6211(2) 0.0666(9) Uani 1 1 d . . . . .
C2 C 0.77830(17) 0.1941(5) 0.6158(2) 0.0738(10) Uani 1 1 d . . . . .
H2 H 0.814970 0.233737 0.634719 0.089 Uiso 1 1 calc R U . . .
C3 C 0.77005(19) 0.0425(5) 0.5830(2) 0.0797(11) Uani 1 1 d . . . . .
H3A H 0.801536 -0.022533 0.579510 0.096 Uiso 1 1 calc R U . . .
C4 C 0.71671(17) -0.0189(4) 0.5547(2) 0.0734(10) Uani 1 1 d . . . . .
H4 H 0.712104 -0.124402 0.532386 0.088 Uiso 1 1 calc R U . . .
C5 C 0.67106(17) 0.0739(4) 0.5593(2) 0.0678(9) Uani 1 1 d . . . . .
H5 H 0.634666 0.032719 0.540004 0.081 Uiso 1 1 calc R U . . .
C6 C 0.67775(16) 0.2296(4) 0.5925(2) 0.0636(9) Uani 1 1 d . . . . .
C7 C 0.79250(16) 0.5136(5) 0.6879(3) 0.0789(10) Uani 1 1 d . . . . .
H7A H 0.814930 0.515749 0.642053 0.118 Uiso 1 1 calc R U . . .
H7B H 0.811095 0.446948 0.735534 0.118 Uiso 1 1 calc R U . . .
H7C H 0.788401 0.622519 0.708749 0.118 Uiso 1 1 calc R U . . .
C8 C 0.69130(15) 0.5420(4) 0.6541(2) 0.0661(9) Uani 1 1 d . . . . .
C9 C 0.63705(14) 0.4636(4) 0.6269(2) 0.0625(9) Uani 1 1 d . . . . .
C10 C 0.58608(15) 0.5606(4) 0.6364(2) 0.0644(9) Uani 1 1 d . . . . .
C11 C 0.58117(16) 0.7251(4) 0.5888(2) 0.0658(9) Uani 1 1 d . . . . .
C12 C 0.58101(15) 0.6066(4) 0.7271(2) 0.0643(9) Uani 1 1 d . . . . .
C13 C 0.57265(15) 0.7721(4) 0.7285(2) 0.0651(9) Uani 1 1 d . . . . .
C14 C 0.56597(16) 0.8529(5) 0.8022(2) 0.0715(10) Uani 1 1 d . . . . .
H14 H 0.560391 0.965168 0.802696 0.086 Uiso 1 1 calc R U . . .
C15 C 0.56791(16) 0.7594(5) 0.8762(2) 0.0752(10) Uani 1 1 d . . . . .
H15 H 0.564001 0.810301 0.928698 0.090 Uiso 1 1 calc R U . . .
C16 C 0.57529(16) 0.5958(5) 0.8758(2) 0.0716(10) Uani 1 1 d . . . . .
H16 H 0.575924 0.537000 0.927509 0.086 Uiso 1 1 calc R U . . .
C17 C 0.58189(15) 0.5148(4) 0.8000(2) 0.0697(9) Uani 1 1 d . . . . .
C18 C 0.5884(2) 0.3357(4) 0.7996(3) 0.0852(12) Uani 1 1 d . . . . .
H18A H 0.558123 0.288766 0.757894 0.128 Uiso 1 1 calc R U . . .
H18B H 0.587069 0.293542 0.857194 0.128 Uiso 1 1 calc R U . . .
H18C H 0.624340 0.308273 0.783487 0.128 Uiso 1 1 calc R U . . .
O3 O 0.52475(12) 0.1293(3) 0.58664(19) 0.0895(9) Uani 1 1 d . . . . .
H3B H 0.499105 0.174007 0.548637 0.134 Uiso 1 1 d R U . . .
H3C H 0.553135 0.193697 0.590907 0.134 Uiso 1 1 d 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 C10 1.405(4) . ?
O1 C8 1.237(4) . ?
O2 C11 1.210(4) . ?
N1 C1 1.409(4) . ?
N1 C7 1.469(5) . ?
N1 C8 1.371(5) . ?
N2 C6 1.391(5) . ?
N2 C9 1.292(4) . ?
N3 H3 0.8800 . ?
N3 C11 1.353(4) . ?
N3 C13 1.412(4) . ?
C1 C2 1.410(5) . ?
C1 C6 1.402(5) . ?
C2 H2 0.9500 . ?
C2 C3 1.372(5) . ?
C3 H3A 0.9500 . ?
C3 C4 1.395(6) . ?
C4 H4 0.9500 . ?
C4 C5 1.369(5) . ?
C5 H5 0.9500 . ?
C5 C6 1.403(5) . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C8 C9 1.470(5) . ?
C9 C10 1.513(5) . ?
C10 C11 1.563(5) . ?
C10 C12 1.507(5) . ?
C12 C13 1.401(5) . ?
C12 C17 1.379(5) . ?
C13 C14 1.379(5) . ?
C14 H14 0.9500 . ?
C14 C15 1.399(5) . ?
C15 H15 0.9500 . ?
C15 C16 1.381(6) . ?
C16 H16 0.9500 . ?
C16 C17 1.408(5) . ?
C17 C18 1.508(5) . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
O3 H3B 0.8702 . ?
O3 H3C 0.8700 . ?

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
C1 N1 C7 120.8(3) . . ?
C8 N1 C1 120.8(3) . . ?
C8 N1 C7 118.4(3) . . ?
C9 N2 C6 118.2(3) . . ?
C11 N3 H3 124.4 . . ?
C11 N3 C13 111.2(3) . . ?
C13 N3 H3 124.4 . . ?
N1 C1 C2 121.6(3) . . ?
C6 C1 N1 118.8(3) . . ?
C6 C1 C2 119.6(3) . . ?
C1 C2 H2 120.5 . . ?
C3 C2 C1 118.9(4) . . ?
C3 C2 H2 120.5 . . ?
C2 C3 H3A 119.1 . . ?
C2 C3 C4 121.8(4) . . ?
C4 C3 H3A 119.1 . . ?
C3 C4 H4 120.2 . . ?
C5 C4 C3 119.5(3) . . ?
C5 C4 H4 120.2 . . ?
C4 C5 H5 119.8 . . ?
C4 C5 C6 120.3(4) . . ?
C6 C5 H5 119.8 . . ?
N2 C6 C1 121.5(3) . . ?
N2 C6 C5 118.7(3) . . ?
C1 C6 C5 119.8(3) . . ?
N1 C7 H7A 109.5 . . ?
N1 C7 H7B 109.5 . . ?
N1 C7 H7C 109.5 . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
O1 C8 N1 123.1(3) . . ?
O1 C8 C9 121.3(3) . . ?
N1 C8 C9 115.6(3) . . ?
N2 C9 C8 124.8(3) . . ?
N2 C9 C10 118.9(3) . . ?
C8 C9 C10 116.3(3) . . ?
F1 C10 C9 107.6(3) . . ?
F1 C10 C11 104.5(3) . . ?
F1 C10 C12 110.7(3) . . ?
C9 C10 C11 114.9(3) . . ?
C12 C10 C9 115.9(3) . . ?
C12 C10 C11 102.6(3) . . ?
O2 C11 N3 126.7(3) . . ?
O2 C11 C10 125.3(3) . . ?
N3 C11 C10 107.7(3) . . ?
C13 C12 C10 107.7(3) . . ?
C17 C12 C10 131.0(3) . . ?
C17 C12 C13 121.3(3) . . ?
C12 C13 N3 110.6(3) . . ?
C14 C13 N3 126.9(3) . . ?
C14 C13 C12 122.5(3) . . ?
C13 C14 H14 122.0 . . ?
C13 C14 C15 115.9(4) . . ?
C15 C14 H14 122.0 . . ?
C14 C15 H15 118.8 . . ?
C16 C15 C14 122.4(3) . . ?
C16 C15 H15 118.8 . . ?
C15 C16 H16 119.5 . . ?
C15 C16 C17 121.1(3) . . ?
C17 C16 H16 119.5 . . ?
C12 C17 C16 116.9(3) . . ?
C12 C17 C18 122.5(3) . . ?
C16 C17 C18 120.7(3) . . ?
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 . . ?
H3B O3 H3C 104.5 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_site                            XU
