# Supplementary Information (SI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2024

####################################################################### 
# 
# 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_zj1018_0m
_database_code_depnum_ccdc_archive 'CCDC 2336722'
loop_
_audit_author_name
_audit_author_address
'Zhang Jinhui'
;South China University of Technology
China
;
_audit_update_record             
;
2024-03-01 deposited with the CCDC.	2024-07-29 downloaded from the CCDC.
;
_audit_creation_date             2022-10-22
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C18 H14 F N O2'
_chemical_formula_sum            'C18 H14 F N O2'
_chemical_formula_weight         295.30
_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                   9.2770(6)
_cell_length_b                   9.5602(6)
_cell_length_c                   9.7665(6)
_cell_angle_alpha                104.289(2)
_cell_angle_beta                 110.312(2)
_cell_angle_gamma                107.388(2)
_cell_volume                     713.26(8)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2054
_cell_measurement_temperature    170
_cell_measurement_theta_max      25.185
_cell_measurement_theta_min      2.584
_shelx_estimated_absorpt_T_max   0.995
_shelx_estimated_absorpt_T_min   0.988
_exptl_absorpt_coefficient_mu    0.099
_exptl_absorpt_correction_T_max  0.9281
_exptl_absorpt_correction_T_min  0.7302
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1628 before and 0.0604 after correction. The Ratio of minimum to maximum transmission is 0.7868. 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    1.375
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             308
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0626
_diffrn_reflns_av_unetI/netI     0.0806
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            8815
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.509
_diffrn_reflns_theta_min         2.584
_diffrn_ambient_temperature      170.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_device_type  'Bruker D8 VENTURE'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1888
_reflns_number_total             3229
_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 (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.179
_refine_diff_density_min         -0.240
_refine_diff_density_rms         0.048
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     199
_refine_ls_number_reflns         3229
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1178
_refine_ls_R_factor_gt           0.0529
_refine_ls_restrained_S_all      1.050
_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)+(0.0358P)²+0.1896P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1009
_refine_ls_wR_factor_ref         0.1309
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Ternary CH refined with riding coordinates:
 C4(H4)
2.b Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B), C2(H2A,H2B)
2.c Aromatic/amide H refined with riding coordinates:
 C9(H9), C5(H5), C18(H18), C8(H8), C12(H12), C6(H6), C14(H14), C16(H16),
 C15(H15)
;
_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 0.63346(18) 0.58846(16) 0.23119(16) 0.0371(4) Uani 1 1 d . . . . .
F1 F 0.22074(17) -0.23241(16) 0.18325(17) 0.0620(4) Uani 1 1 d . . . . .
O2 O 0.6319(2) 0.71645(18) 0.06985(18) 0.0573(5) Uani 1 1 d . . . . .
N1 N 0.7491(2) 0.5042(2) 0.43343(19) 0.0340(4) Uani 1 1 d . . . . .
C4 C 0.6896(3) 0.4681(2) 0.2669(2) 0.0340(5) Uani 1 1 d . . . . .
H4 H 0.591093 0.361021 0.206145 0.041 Uiso 1 1 calc R . . . .
C17 C 0.8653(3) 0.6548(2) 0.5531(2) 0.0343(5) Uani 1 1 d . . . . .
C9 C 0.4189(3) 0.1817(3) 0.4470(3) 0.0415(6) Uani 1 1 d . . . . .
H9 H 0.404155 0.250464 0.524421 0.050 Uiso 1 1 calc R . . . .
C10 C 0.5511(3) 0.2433(2) 0.4118(2) 0.0344(5) Uani 1 1 d . . . . .
C5 C 0.5706(3) 0.1393(3) 0.2991(3) 0.0393(5) Uani 1 1 d . . . . .
H5 H 0.661295 0.178939 0.274571 0.047 Uiso 1 1 calc R . . . .
C1 C 0.6785(3) 0.6285(3) 0.1238(2) 0.0415(6) Uani 1 1 d . . . . .
C11 C 0.6702(3) 0.4120(2) 0.5001(2) 0.0352(5) Uani 1 1 d . . . . .
C13 C 0.8575(3) 0.6553(3) 0.6938(2) 0.0407(6) Uani 1 1 d . . . . .
C18 C 0.9709(3) 0.7881(3) 0.5463(3) 0.0417(6) Uani 1 1 d . . . . .
H18 H 0.971968 0.787445 0.449207 0.050 Uiso 1 1 calc R . . . .
C3 C 0.8213(3) 0.4717(3) 0.2069(3) 0.0452(6) Uani 1 1 d . . . . .
H3A H 0.937683 0.537147 0.294497 0.054 Uiso 1 1 calc R . . . .
H3B H 0.809703 0.362778 0.156858 0.054 Uiso 1 1 calc R . . . .
C8 C 0.3080(3) 0.0213(3) 0.3708(3) 0.0468(6) Uani 1 1 d . . . . .
H8 H 0.218376 -0.020661 0.395828 0.056 Uiso 1 1 calc R . . . .
C7 C 0.3310(3) -0.0748(3) 0.2590(3) 0.0444(6) Uani 1 1 d . . . . .
C12 C 0.7353(3) 0.5018(3) 0.6576(2) 0.0435(6) Uani 1 1 d . . . . .
H12 H 0.704440 0.467690 0.730901 0.052 Uiso 1 1 calc R . . . .
C6 C 0.4599(3) -0.0212(3) 0.2217(3) 0.0440(6) Uani 1 1 d . . . . .
H6 H 0.473833 -0.091742 0.144984 0.053 Uiso 1 1 calc R . . . .
C14 C 0.9646(3) 0.7927(3) 0.8335(3) 0.0524(7) Uani 1 1 d . . . . .
H14 H 0.962638 0.795068 0.930667 0.063 Uiso 1 1 calc R . . . .
C2 C 0.7817(3) 0.5458(3) 0.0863(3) 0.0545(7) Uani 1 1 d . . . . .
H2A H 0.887459 0.622700 0.096168 0.065 Uiso 1 1 calc R . . . .
H2B H 0.716765 0.462919 -0.022925 0.065 Uiso 1 1 calc R . . . .
C16 C 1.0747(3) 0.9220(3) 0.6863(3) 0.0479(6) Uani 1 1 d . . . . .
H16 H 1.149006 1.014491 0.685206 0.058 Uiso 1 1 calc R . . . .
C15 C 1.0724(3) 0.9238(3) 0.8284(3) 0.0529(7) Uani 1 1 d . . . . .
H15 H 1.146214 1.016633 0.922896 0.063 Uiso 1 1 calc R . . . .


_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 C4 1.465(2) . ?
O1 C1 1.352(3) . ?
F1 C7 1.366(2) . ?
O2 C1 1.204(3) . ?
N1 C4 1.434(2) . ?
N1 C17 1.403(3) . ?
N1 C11 1.401(3) . ?
C4 C3 1.523(3) . ?
C17 C13 1.399(3) . ?
C17 C18 1.389(3) . ?
C9 C10 1.390(3) . ?
C9 C8 1.388(3) . ?
C10 C5 1.392(3) . ?
C10 C11 1.467(3) . ?
C5 C6 1.388(3) . ?
C1 C2 1.493(3) . ?
C11 C12 1.364(3) . ?
C13 C12 1.427(3) . ?
C13 C14 1.403(3) . ?
C18 C16 1.386(3) . ?
C3 C2 1.514(3) . ?
C8 C7 1.366(3) . ?
C7 C6 1.361(3) . ?
C14 C15 1.375(3) . ?
C16 C15 1.391(3) . ?

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 O1 C4 110.60(16) . . ?
C17 N1 C4 124.35(17) . . ?
C11 N1 C4 125.20(17) . . ?
C11 N1 C17 108.42(16) . . ?
O1 C4 C3 105.51(16) . . ?
N1 C4 O1 108.48(15) . . ?
N1 C4 C3 115.48(17) . . ?
C13 C17 N1 107.54(19) . . ?
C18 C17 N1 130.41(19) . . ?
C18 C17 C13 122.03(19) . . ?
C8 C9 C10 121.0(2) . . ?
C9 C10 C5 118.2(2) . . ?
C9 C10 C11 119.3(2) . . ?
C5 C10 C11 122.4(2) . . ?
C6 C5 C10 121.2(2) . . ?
O1 C1 C2 110.36(19) . . ?
O2 C1 O1 120.5(2) . . ?
O2 C1 C2 129.2(2) . . ?
N1 C11 C10 123.27(18) . . ?
C12 C11 N1 108.33(19) . . ?
C12 C11 C10 128.2(2) . . ?
C17 C13 C12 107.13(18) . . ?
C17 C13 C14 119.0(2) . . ?
C14 C13 C12 133.9(2) . . ?
C16 C18 C17 117.5(2) . . ?
C2 C3 C4 103.75(18) . . ?
C7 C8 C9 118.4(2) . . ?
C8 C7 F1 118.2(2) . . ?
C6 C7 F1 118.7(2) . . ?
C6 C7 C8 123.0(2) . . ?
C11 C12 C13 108.6(2) . . ?
C7 C6 C5 118.2(2) . . ?
C15 C14 C13 119.3(2) . . ?
C1 C2 C3 105.14(18) . . ?
C18 C16 C15 121.4(2) . . ?
C14 C15 C16 120.8(2) . . ?


_olex2_submission_special_instructions 'No special instructions were received'
