# 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_250113_z2_0m
_database_code_depnum_ccdc_archive 'CCDC 2480505'
loop_
_audit_author_name
_audit_author_address
'Yulei Zhao'
;Qufu Normal University
China
;
_audit_update_record             
;
2025-08-14 deposited with the CCDC.	2025-10-13 downloaded from the CCDC.
;
_audit_creation_date             2025-03-02
_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         '0.143(C14 H13 F3 N2 O)'
_chemical_formula_sum            'C2 H1.86 F0.43 N0.29 O0.14'
_chemical_formula_weight         40.32
_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 0.0033 0.0016 '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 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 '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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.3506(11)
_cell_length_b                   9.0318(12)
_cell_length_c                   11.0779(17)
_cell_angle_alpha                77.137(4)
_cell_angle_beta                 72.363(4)
_cell_angle_gamma                83.642(4)
_cell_volume                     682.55(17)
_cell_formula_units_Z            14
_cell_measurement_reflns_used    3933
_cell_measurement_temperature    273.15
_cell_measurement_theta_max      25.66
_cell_measurement_theta_min      2.32
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.116
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.5423
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0957 before and 0.0722 after correction.
The Ratio of minimum to maximum transmission is 0.7272.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.373
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             292
_exptl_crystal_preparation       ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0460
_diffrn_reflns_av_unetI/netI     0.0445
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            12622
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.267
_diffrn_reflns_theta_min         2.316
_diffrn_ambient_temperature      273.15
_diffrn_detector_area_resol_mean 8
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker SMART APEX CCD area detector'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'sealed tube'
_diffrn_source_current           30.0
_diffrn_source_power             1.5
_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                2049
_reflns_number_total             3362
_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 V8.40A (Bruker, 2019)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40A (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 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.277
_refine_diff_density_min         -0.220
_refine_diff_density_rms         0.041
_refine_ls_extinction_coef       0.039(10)
_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   1.008
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     184
_refine_ls_number_reflns         3362
_refine_ls_number_restraints     4
_refine_ls_R_factor_all          0.0981
_refine_ls_R_factor_gt           0.0559
_refine_ls_restrained_S_all      1.013
_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)+(0.0846P)²+0.1316P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1468
_refine_ls_wR_factor_ref         0.1747
_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. Rigid bond restraints
 F3, C14
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
 F2, C14
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.002
 F1, C14
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.002
 C2, C3
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.002
3.a Aromatic/amide H refined with riding coordinates:
 C10(H10), C11(H11), C5(H5), C1(H1), C4(H4), C3(H3), C2(H2)
3.b Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C), C13(H13A,H13B,H13C)
;
_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
O1 O 0.3085(2) 0.14822(19) 0.67516(15) 0.0632(5) Uani 1 1 d . . . . .
F1 F 0.5343(3) 0.1368(2) 1.09736(14) 0.1006(6) Uani 1 1 d . U . . .
N2 N 0.5416(2) 0.21947(19) 0.82039(15) 0.0469(4) Uani 1 1 d . . . . .
F2 F 0.6405(3) 0.3548(2) 1.01823(16) 0.1086(7) Uani 1 1 d . U . . .
N1 N 0.5403(2) 0.2222(2) 0.49088(16) 0.0482(4) Uani 1 1 d . . . . .
F3 F 0.8335(3) 0.1647(3) 1.03633(17) 0.1161(7) Uani 1 1 d . U . . .
C9 C 0.6072(3) 0.1865(2) 0.69828(18) 0.0433(4) Uani 1 1 d . . . . .
C8 C 0.4734(3) 0.1864(2) 0.62193(19) 0.0451(5) Uani 1 1 d . . . . .
C6 C 0.7200(3) 0.2883(2) 0.41890(18) 0.0453(5) Uani 1 1 d . . . . .
C10 C 0.7942(3) 0.1348(2) 0.67883(19) 0.0498(5) Uani 1 1 d . . . . .
H10 H 0.872775 0.104521 0.604416 0.060 Uiso 1 1 calc R U . . .
C11 C 0.8465(3) 0.1353(3) 0.7897(2) 0.0535(5) Uani 1 1 d . . . . .
H11 H 0.965110 0.105374 0.803240 0.064 Uiso 1 1 calc R U . . .
C12 C 0.6899(3) 0.1883(2) 0.87434(19) 0.0502(5) Uani 1 1 d . . . . .
C5 C 0.7625(3) 0.4268(2) 0.4341(2) 0.0559(5) Uani 1 1 d . . . . .
H5 H 0.677035 0.476335 0.494963 0.067 Uiso 1 1 calc R U . . .
C14 C 0.6738(4) 0.2118(3) 1.0076(2) 0.0675(5) Uani 1 1 d . U . . .
C1 C 0.8479(3) 0.2143(3) 0.3280(2) 0.0622(6) Uani 1 1 d . . . . .
H1 H 0.819265 0.121346 0.317062 0.075 Uiso 1 1 calc R U . . .
C4 C 0.9321(4) 0.4917(3) 0.3590(3) 0.0678(7) Uani 1 1 d . . . . .
H4 H 0.960910 0.585176 0.369018 0.081 Uiso 1 1 calc R U . . .
C7 C 0.4119(3) 0.2055(3) 0.4163(2) 0.0679(7) Uani 1 1 d . . . . .
H7A H 0.329588 0.123378 0.462658 0.102 Uiso 1 1 calc R U . . .
H7B H 0.486168 0.184157 0.333874 0.102 Uiso 1 1 calc R U . . .
H7C H 0.336056 0.298050 0.403560 0.102 Uiso 1 1 calc R U . . .
C13 C 0.3515(3) 0.2814(3) 0.8799(2) 0.0756(8) Uani 1 1 d . . . . .
H13A H 0.300831 0.343182 0.813878 0.113 Uiso 1 1 calc R U . . .
H13B H 0.359889 0.342225 0.938684 0.113 Uiso 1 1 calc R U . . .
H13C H 0.268763 0.199489 0.926121 0.113 Uiso 1 1 calc R U . . .
C3 C 1.0587(4) 0.4177(3) 0.2690(3) 0.0748(7) Uani 1 1 d . U . . .
H3 H 1.172692 0.461606 0.218067 0.090 Uiso 1 1 calc R U . . .
C2 C 1.0169(4) 0.2792(3) 0.2546(2) 0.0761(7) Uani 1 1 d . U . . .
H2 H 1.103516 0.229125 0.194609 0.091 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
O1 C8 1.226(2) . ?
F1 C14 1.317(3) . ?
N2 C9 1.380(2) . ?
N2 C12 1.370(3) . ?
N2 C13 1.460(3) . ?
F2 C14 1.312(3) . ?
N1 C8 1.359(3) . ?
N1 C6 1.436(2) . ?
N1 C7 1.468(3) . ?
F3 C14 1.309(3) . ?
C9 C8 1.479(3) . ?
C9 C10 1.370(3) . ?
C6 C5 1.379(3) . ?
C6 C1 1.389(3) . ?
C10 H10 0.9300 . ?
C10 C11 1.395(3) . ?
C11 H11 0.9300 . ?
C11 C12 1.363(3) . ?
C12 C14 1.506(3) . ?
C5 H5 0.9300 . ?
C5 C4 1.381(3) . ?
C1 H1 0.9300 . ?
C1 C2 1.372(3) . ?
C4 H4 0.9300 . ?
C4 C3 1.380(4) . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C3 H3 0.9300 . ?
C3 C2 1.375(4) . ?
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
C9 N2 C13 126.52(18) . . ?
C12 N2 C9 107.36(16) . . ?
C12 N2 C13 126.09(18) . . ?
C8 N1 C6 125.40(16) . . ?
C8 N1 C7 117.63(17) . . ?
C6 N1 C7 116.71(17) . . ?
N2 C9 C8 120.59(16) . . ?
C10 C9 N2 107.98(17) . . ?
C10 C9 C8 130.59(18) . . ?
O1 C8 N1 120.72(18) . . ?
O1 C8 C9 120.87(18) . . ?
N1 C8 C9 118.33(16) . . ?
C5 C6 N1 121.05(18) . . ?
C5 C6 C1 119.9(2) . . ?
C1 C6 N1 118.93(18) . . ?
C9 C10 H10 125.8 . . ?
C9 C10 C11 108.33(18) . . ?
C11 C10 H10 125.8 . . ?
C10 C11 H11 126.7 . . ?
C12 C11 C10 106.61(18) . . ?
C12 C11 H11 126.7 . . ?
N2 C12 C14 123.06(19) . . ?
C11 C12 N2 109.72(18) . . ?
C11 C12 C14 127.2(2) . . ?
C6 C5 H5 120.0 . . ?
C6 C5 C4 120.0(2) . . ?
C4 C5 H5 120.0 . . ?
F1 C14 C12 112.5(2) . . ?
F2 C14 F1 106.0(2) . . ?
F2 C14 C12 112.9(2) . . ?
F3 C14 F1 107.8(2) . . ?
F3 C14 F2 107.7(2) . . ?
F3 C14 C12 109.6(2) . . ?
C6 C1 H1 120.2 . . ?
C2 C1 C6 119.7(2) . . ?
C2 C1 H1 120.2 . . ?
C5 C4 H4 120.1 . . ?
C3 C4 C5 119.8(2) . . ?
C3 C4 H4 120.1 . . ?
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 . . ?
N2 C13 H13A 109.5 . . ?
N2 C13 H13B 109.5 . . ?
N2 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C4 C3 H3 119.9 . . ?
C2 C3 C4 120.2(2) . . ?
C2 C3 H3 119.9 . . ?
C1 C2 C3 120.4(2) . . ?
C1 C2 H2 119.8 . . ?
C3 C2 H2 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
N2 C9 C8 O1 -32.7(3) . . . . ?
N2 C9 C8 N1 150.61(18) . . . . ?
N2 C9 C10 C11 0.0(2) . . . . ?
N2 C12 C14 F1 56.6(3) . . . . ?
N2 C12 C14 F2 -63.4(3) . . . . ?
N2 C12 C14 F3 176.5(2) . . . . ?
N1 C6 C5 C4 -176.66(19) . . . . ?
N1 C6 C1 C2 177.3(2) . . . . ?
C9 N2 C12 C11 -0.5(2) . . . . ?
C9 N2 C12 C14 179.29(19) . . . . ?
C9 C10 C11 C12 -0.3(2) . . . . ?
C8 N1 C6 C5 -59.1(3) . . . . ?
C8 N1 C6 C1 124.1(2) . . . . ?
C8 C9 C10 C11 -169.3(2) . . . . ?
C6 N1 C8 O1 170.71(19) . . . . ?
C6 N1 C8 C9 -12.6(3) . . . . ?
C6 C5 C4 C3 -0.1(3) . . . . ?
C6 C1 C2 C3 -1.0(4) . . . . ?
C10 C9 C8 O1 135.5(2) . . . . ?
C10 C9 C8 N1 -41.2(3) . . . . ?
C10 C11 C12 N2 0.5(2) . . . . ?
C10 C11 C12 C14 -179.3(2) . . . . ?
C11 C12 C14 F1 -123.7(3) . . . . ?
C11 C12 C14 F2 116.3(3) . . . . ?
C11 C12 C14 F3 -3.8(3) . . . . ?
C12 N2 C9 C8 170.87(17) . . . . ?
C12 N2 C9 C10 0.3(2) . . . . ?
C5 C6 C1 C2 0.5(3) . . . . ?
C5 C4 C3 C2 -0.3(4) . . . . ?
C1 C6 C5 C4 0.1(3) . . . . ?
C4 C3 C2 C1 0.9(4) . . . . ?
C7 N1 C8 O1 -3.2(3) . . . . ?
C7 N1 C8 C9 173.52(18) . . . . ?
C7 N1 C6 C5 114.9(2) . . . . ?
C7 N1 C6 C1 -61.9(3) . . . . ?
C13 N2 C9 C8 -11.1(3) . . . . ?
C13 N2 C9 C10 178.3(2) . . . . ?
C13 N2 C12 C11 -178.5(2) . . . . ?
C13 N2 C12 C14 1.3(3) . . . . ?


_olex2_submission_special_instructions 'No special instructions were received'
