# Electronic Supplementary Material (ESI) 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. 
# 
#######################################################################

data_y
_database_code_depnum_ccdc_archive 'CCDC 2342462'
loop_
_audit_author_name
_audit_author_address
'Xianggao Meng'
;Central China Normal University
China
;
_audit_update_record             
;
2024-03-22 deposited with the CCDC.	2024-06-18 downloaded from the CCDC.
;
_audit_creation_date             2023-05-08
_audit_creation_method           
; 
Olex2 1.2 
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506) 
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C22 H18 Cl N2, C2 H F3 O2, C2 F3 O2'
_chemical_formula_sum            'C26 H19 Cl F6 N2 O4'
_chemical_formula_weight         572.88
_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'
Cl Cl 0.1484 0.1585 '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      orthorhombic
_space_group_IT_number           60
_space_group_name_H-M_alt        'P b c n'
_space_group_name_Hall           '-P 2n 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'x+1/2, -y+1/2, -z'
'-x, y, -z+1/2'
'-x+1/2, -y+1/2, z+1/2'
'-x, -y, -z'
'-x-1/2, y-1/2, z'
'x, -y, z-1/2'
'x-1/2, y-1/2, -z-1/2'

_cell_length_a                   16.652(3)
_cell_length_b                   14.997(2)
_cell_length_c                   21.130(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     5277.0(14)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    9980
_cell_measurement_temperature    296(1)
_cell_measurement_theta_max      26.16
_cell_measurement_theta_min      2.28
_shelx_estimated_absorpt_T_max   0.978
_shelx_estimated_absorpt_T_min   0.974
_exptl_absorpt_coefficient_mu    0.222
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.6050
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS-2008/1 (Bruker,2008)'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.442
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             2336
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0374
_diffrn_reflns_av_unetI/netI     0.0245
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            34374
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        24.997
_diffrn_reflns_theta_max         24.997
_diffrn_reflns_theta_min         2.066
_diffrn_ambient_temperature      296(1)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_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                3441
_reflns_number_total             4625
_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 v7.68A (Bruker, 2009)'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'SAINT v7.68A (Bruker, 2009)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XM (Sheldrick, 2008)'
_refine_diff_density_max         0.410
_refine_diff_density_min         -0.484
_refine_diff_density_rms         0.065
_refine_ls_extinction_coef       0.0043(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     405
_refine_ls_number_reflns         4625
_refine_ls_number_restraints     78
_refine_ls_R_factor_all          0.0825
_refine_ls_R_factor_gt           0.0611
_refine_ls_restrained_S_all      1.097
_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)+(0.0898P)²+4.1136P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1581
_refine_ls_wR_factor_ref         0.1894
_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) groups 
2. Restrained distances 
 F3-C23 \\sim F3A-C23 
 with sigma of 0.02 
 F1-C23 \\sim F1A-C23 
 with sigma of 0.02 
 C23-F2 \\sim C23-F2A 
 with sigma of 0.02 
 F6-C25 \\sim F6A-C25 
 with sigma of 0.02 
 F4-C25 \\sim F4A-C25 
 with sigma of 0.02 
 F5-C25 \\sim F5A-C25 
 with sigma of 0.02 
3. Uiso/Uaniso restraints and constraints 
Uanis(F6) \\sim Ueq, Uanis(F4) \\sim Ueq, Uanis(F5) \\sim Ueq, Uanis(F6A) \\sim 
Ueq, Uanis(F4A) \\sim Ueq, Uanis(F5A) \\sim Ueq, Uanis(F3) \\sim Ueq, Uanis(F1) 
\\sim Ueq, Uanis(F2) \\sim Ueq, Uanis(F1A) \\sim Ueq, Uanis(F2A) \\sim Ueq, 
Uanis(F3A) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02 
Uanis(F3) = Uanis(F2A) 
4. Others 
 Sof(F1A)=Sof(F2A)=Sof(F3A)=1-FVAR(1) 
 Sof(F1)=Sof(F2)=Sof(F3)=FVAR(1) 
 Sof(F4A)=Sof(F5A)=Sof(F6A)=1-FVAR(2) 
 Sof(F4)=Sof(F5)=Sof(F6)=FVAR(2) 
5.a Aromatic/amide H refined with riding coordinates: 
 C2(H2), C3(H3), C5(H5), C6(H6), C8(H8), C11(H11), C12(H12), C14(H14), 
 C15(H15), C18(H18), C19(H19), C20(H20), C21(H21), C22(H22), N2(H2A) 
5.b Idealised Me refined as rotating group: 
 C16(H16A,H16B,H16C) 
5.c Idealised tetrahedral OH refined as rotating group: 
 O1(H1) 
;
_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
C1 C 0.15772(17) 0.61428(18) 0.08839(13) 0.0513(7) Uani 1 1 d . . . . .
C2 C 0.19707(19) 0.5680(2) 0.13514(13) 0.0580(7) Uani 1 1 d . . . . .
H2 H 0.2270 0.5981 0.1655 0.070 Uiso 1 1 calc R . . . .
C3 C 0.19171(19) 0.47624(19) 0.13646(13) 0.0568(7) Uani 1 1 d . . . . .
H3 H 0.2196 0.4445 0.1672 0.068 Uiso 1 1 calc R . . . .
C4 C 0.14514(17) 0.43052(18) 0.09233(12) 0.0473(6) Uani 1 1 d . . . . .
C5 C 0.10713(18) 0.47926(18) 0.04497(13) 0.0535(7) Uani 1 1 d . . . . .
H5 H 0.0769 0.4498 0.0145 0.064 Uiso 1 1 calc R . . . .
C6 C 0.11389(18) 0.57112(19) 0.04278(14) 0.0556(7) Uani 1 1 d . . . . .
H6 H 0.0890 0.6033 0.0107 0.067 Uiso 1 1 calc R . . . .
C7 C 0.13549(18) 0.33417(18) 0.10135(12) 0.0491(6) Uani 1 1 d . . . . .
C8 C 0.1300(2) 0.28984(19) 0.15669(13) 0.0596(8) Uani 1 1 d . . . . .
H8 H 0.1317 0.3152 0.1968 0.072 Uiso 1 1 calc R . . . .
C9 C 0.12167(17) 0.18851(18) 0.08148(13) 0.0485(6) Uani 1 1 d . . . . .
C10 C 0.12902(16) 0.28558(16) -0.01337(11) 0.0421(6) Uani 1 1 d . . . . .
C11 C 0.19857(18) 0.3122(2) -0.04273(13) 0.0588(7) Uani 1 1 d . . . . .
H11 H 0.2455 0.3200 -0.0195 0.071 Uiso 1 1 calc R . . . .
C12 C 0.1977(2) 0.3271(2) -0.10725(15) 0.0687(9) Uani 1 1 d . . . . .
H12 H 0.2447 0.3450 -0.1274 0.082 Uiso 1 1 calc R . . . .
C13 C 0.1283(2) 0.3159(2) -0.14239(14) 0.0641(8) Uani 1 1 d . . . . .
C14 C 0.0599(2) 0.2891(2) -0.11154(14) 0.0619(8) Uani 1 1 d . . . . .
H14 H 0.0129 0.2811 -0.1346 0.074 Uiso 1 1 calc R . . . .
C15 C 0.05932(17) 0.27365(18) -0.04696(13) 0.0495(6) Uani 1 1 d . . . . .
H15 H 0.0125 0.2555 -0.0267 0.059 Uiso 1 1 calc R . . . .
C16 C 0.1289(3) 0.3329(3) -0.21321(17) 0.1061(15) Uani 1 1 d . . . . .
H16A H 0.1309 0.3960 -0.2209 0.159 Uiso 1 1 calc GR . . . .
H16B H 0.0810 0.3087 -0.2317 0.159 Uiso 1 1 calc GR . . . .
H16C H 0.1750 0.3049 -0.2317 0.159 Uiso 1 1 calc GR . . . .
C17 C 0.11660(16) 0.10064(17) 0.05130(12) 0.0483(6) Uani 1 1 d . . . . .
C18 C 0.16049(18) 0.08003(19) -0.00266(14) 0.0557(7) Uani 1 1 d . . . . .
H18 H 0.1924 0.1231 -0.0218 0.067 Uiso 1 1 calc R . . . .
C19 C 0.1563(2) -0.0051(2) -0.02763(15) 0.0649(8) Uani 1 1 d . . . . .
H19 H 0.1855 -0.0192 -0.0638 0.078 Uiso 1 1 calc R . . . .
C20 C 0.1092(2) -0.0690(2) 0.00061(17) 0.0674(9) Uani 1 1 d . . . . .
H20 H 0.1059 -0.1258 -0.0169 0.081 Uiso 1 1 calc R . . . .
C21 C 0.0671(2) -0.0495(2) 0.05438(17) 0.0672(9) Uani 1 1 d . . . . .
H21 H 0.0363 -0.0934 0.0738 0.081 Uiso 1 1 calc R . . . .
C22 C 0.07009(19) 0.03504(19) 0.07991(15) 0.0588(7) Uani 1 1 d . . . . .
H22 H 0.0410 0.0482 0.1163 0.071 Uiso 1 1 calc R . . . .
C23 C 0.4046(4) 0.8968(4) 0.3470(2) 0.1094(17) Uani 1 1 d D . . . .
C24 C 0.4146(2) 0.7998(3) 0.35900(17) 0.0801(10) Uani 1 1 d . . . . .
C25 C 0.3799(3) 0.4441(3) 0.2884(2) 0.0913(12) Uani 1 1 d D . . . .
C26 C 0.3838(2) 0.5437(2) 0.27790(15) 0.0672(9) Uani 1 1 d . . . . .
Cl09 Cl 0.16410(6) 0.73008(5) 0.08772(5) 0.0762(3) Uani 1 1 d . . . . .
N1 N 0.12918(13) 0.26920(14) 0.05399(10) 0.0437(5) Uani 1 1 d . . . . .
N2 N 0.12161(16) 0.20115(16) 0.14349(10) 0.0583(7) Uani 1 1 d . . . . .
H2A H 0.1170 0.1597 0.1713 0.070 Uiso 1 1 calc R . . . .
O1 O 0.4029(2) 0.75298(19) 0.30938(12) 0.1015(10) Uani 1 1 d . . . . .
H1 H 0.4076 0.7000 0.3182 0.152 Uiso 1 1 calc GR . . . .
O2 O 0.4333(2) 0.7741(2) 0.41040(13) 0.1069(10) Uani 1 1 d . . . . .
O3 O 0.4095(3) 0.5878(2) 0.32238(15) 0.1215(13) Uani 1 1 d . . . . .
O4 O 0.3574(2) 0.5699(2) 0.22859(13) 0.1158(12) Uani 1 1 d . . . . .
F1 F 0.4551(8) 0.9427(10) 0.3698(9) 0.200(8) Uani 0.532(11) 1 d D U P A 1
F2 F 0.3310(7) 0.9175(7) 0.3801(5) 0.192(5) Uani 0.532(11) 1 d D U P A 1
F3 F 0.3829(10) 0.9216(14) 0.2902(7) 0.164(5) Uani 0.532(11) 1 d D U P A 1
F4 F 0.4421(7) 0.4134(5) 0.3184(7) 0.166(4) Uani 0.732(18) 1 d D U P B 1
F5 F 0.3166(7) 0.4253(5) 0.3234(6) 0.184(4) Uani 0.732(18) 1 d D U P B 1
F6 F 0.3721(9) 0.3989(3) 0.2366(3) 0.157(4) Uani 0.732(18) 1 d D U P B 1
F1A F 0.4151(12) 0.9465(8) 0.3883(5) 0.157(6) Uani 0.468(11) 1 d D U P A 2
F2A F 0.3458(10) 0.9139(17) 0.3062(9) 0.164(5) Uani 0.468(11) 1 d D U P A 2
F3A F 0.4679(7) 0.9204(6) 0.3018(6) 0.177(5) Uani 0.468(11) 1 d D U P A 2
F4A F 0.3995(18) 0.4188(13) 0.3409(6) 0.122(7) Uani 0.268(18) 1 d D U P B 2
F5A F 0.3088(11) 0.4109(13) 0.2782(17) 0.155(9) Uani 0.268(18) 1 d D U P B 2
F6A F 0.434(2) 0.4079(15) 0.2485(16) 0.190(11) Uani 0.268(18) 1 d D U P B 2


_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
C1 C2 1.374(4) . ?
C1 C6 1.371(4) . ?
C1 Cl09 1.740(3) . ?
C2 H2 0.9300 . ?
C2 C3 1.379(4) . ?
C3 H3 0.9300 . ?
C3 C4 1.393(4) . ?
C4 C5 1.391(4) . ?
C4 C7 1.466(4) . ?
C5 H5 0.9300 . ?
C5 C6 1.383(4) . ?
C6 H6 0.9300 . ?
C7 C8 1.348(4) . ?
C7 N1 1.401(3) . ?
C8 H8 0.9300 . ?
C8 N2 1.366(4) . ?
C9 C17 1.466(4) . ?
C9 N1 1.348(3) . ?
C9 N2 1.324(3) . ?
C10 C11 1.373(4) . ?
C10 C15 1.372(4) . ?
C10 N1 1.444(3) . ?
C11 H11 0.9300 . ?
C11 C12 1.382(4) . ?
C12 H12 0.9300 . ?
C12 C13 1.384(5) . ?
C13 C14 1.373(5) . ?
C13 C16 1.518(4) . ?
C14 H14 0.9300 . ?
C14 C15 1.384(4) . ?
C15 H15 0.9300 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C17 C18 1.389(4) . ?
C17 C22 1.390(4) . ?
C18 H18 0.9300 . ?
C18 C19 1.383(4) . ?
C19 H19 0.9300 . ?
C19 C20 1.375(5) . ?
C20 H20 0.9300 . ?
C20 C21 1.367(5) . ?
C21 H21 0.9300 . ?
C21 C22 1.378(4) . ?
C22 H22 0.9300 . ?
C23 C24 1.485(6) . ?
C23 F1 1.187(10) . ?
C23 F2 1.445(10) . ?
C23 F3 1.308(14) . ?
C23 F1A 1.160(10) . ?
C23 F2A 1.330(15) . ?
C23 F3A 1.465(11) . ?
C24 O1 1.277(4) . ?
C24 O2 1.194(4) . ?
C25 C26 1.512(5) . ?
C25 F4 1.298(8) . ?
C25 F5 1.317(8) . ?
C25 F6 1.294(6) . ?
C25 F4A 1.216(13) . ?
C25 F5A 1.303(14) . ?
C25 F6A 1.354(14) . ?
C26 O3 1.226(4) . ?
C26 O4 1.198(4) . ?
N2 H2A 0.8600 . ?
O1 H1 0.8200 . ?

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
C2 C1 Cl09 118.8(2) . . ?
C6 C1 C2 121.4(3) . . ?
C6 C1 Cl09 119.9(2) . . ?
C1 C2 H2 120.4 . . ?
C1 C2 C3 119.2(3) . . ?
C3 C2 H2 120.4 . . ?
C2 C3 H3 119.6 . . ?
C2 C3 C4 120.9(3) . . ?
C4 C3 H3 119.6 . . ?
C3 C4 C7 117.3(2) . . ?
C5 C4 C3 118.4(3) . . ?
C5 C4 C7 124.1(2) . . ?
C4 C5 H5 119.7 . . ?
C6 C5 C4 120.7(3) . . ?
C6 C5 H5 119.7 . . ?
C1 C6 C5 119.3(3) . . ?
C1 C6 H6 120.3 . . ?
C5 C6 H6 120.3 . . ?
C8 C7 C4 127.3(2) . . ?
C8 C7 N1 105.8(2) . . ?
N1 C7 C4 126.9(2) . . ?
C7 C8 H8 126.0 . . ?
C7 C8 N2 108.1(2) . . ?
N2 C8 H8 126.0 . . ?
N1 C9 C17 128.6(2) . . ?
N2 C9 C17 124.0(2) . . ?
N2 C9 N1 107.3(2) . . ?
C11 C10 N1 119.6(2) . . ?
C15 C10 C11 121.2(2) . . ?
C15 C10 N1 119.3(2) . . ?
C10 C11 H11 120.5 . . ?
C10 C11 C12 119.0(3) . . ?
C12 C11 H11 120.5 . . ?
C11 C12 H12 119.4 . . ?
C11 C12 C13 121.2(3) . . ?
C13 C12 H12 119.4 . . ?
C12 C13 C16 120.2(3) . . ?
C14 C13 C12 118.3(3) . . ?
C14 C13 C16 121.5(3) . . ?
C13 C14 H14 119.2 . . ?
C13 C14 C15 121.5(3) . . ?
C15 C14 H14 119.2 . . ?
C10 C15 C14 118.8(3) . . ?
C10 C15 H15 120.6 . . ?
C14 C15 H15 120.6 . . ?
C13 C16 H16A 109.5 . . ?
C13 C16 H16B 109.5 . . ?
C13 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C18 C17 C9 121.8(3) . . ?
C18 C17 C22 119.5(3) . . ?
C22 C17 C9 118.6(2) . . ?
C17 C18 H18 120.3 . . ?
C19 C18 C17 119.5(3) . . ?
C19 C18 H18 120.3 . . ?
C18 C19 H19 119.8 . . ?
C20 C19 C18 120.5(3) . . ?
C20 C19 H19 119.8 . . ?
C19 C20 H20 119.9 . . ?
C21 C20 C19 120.2(3) . . ?
C21 C20 H20 119.9 . . ?
C20 C21 H21 119.9 . . ?
C20 C21 C22 120.3(3) . . ?
C22 C21 H21 119.9 . . ?
C17 C22 H22 120.0 . . ?
C21 C22 C17 120.0(3) . . ?
C21 C22 H22 120.0 . . ?
F1 C23 C24 114.8(9) . . ?
F1 C23 F2 106.2(10) . . ?
F1 C23 F3 113.7(14) . . ?
F2 C23 C24 102.9(6) . . ?
F3 C23 C24 117.7(10) . . ?
F3 C23 F2 98.6(9) . . ?
F1A C23 C24 118.9(8) . . ?
F1A C23 F2A 118.3(15) . . ?
F1A C23 F3A 103.1(11) . . ?
F2A C23 C24 112.4(12) . . ?
F2A C23 F3A 93.5(10) . . ?
F3A C23 C24 105.5(5) . . ?
O1 C24 C23 112.5(3) . . ?
O2 C24 C23 120.0(4) . . ?
O2 C24 O1 127.5(4) . . ?
F4 C25 C26 112.8(6) . . ?
F4 C25 F5 106.8(7) . . ?
F5 C25 C26 109.2(5) . . ?
F6 C25 C26 113.4(4) . . ?
F6 C25 F4 107.9(7) . . ?
F6 C25 F5 106.5(7) . . ?
F4A C25 C26 115.5(10) . . ?
F4A C25 F5A 106.0(15) . . ?
F4A C25 F6A 105.2(15) . . ?
F5A C25 C26 113.1(9) . . ?
F5A C25 F6A 110.7(16) . . ?
F6A C25 C26 106.0(11) . . ?
O3 C26 C25 115.8(3) . . ?
O4 C26 C25 115.8(3) . . ?
O4 C26 O3 128.2(4) . . ?
C7 N1 C10 125.9(2) . . ?
C9 N1 C7 108.9(2) . . ?
C9 N1 C10 125.2(2) . . ?
C8 N2 H2A 125.0 . . ?
C9 N2 C8 110.0(2) . . ?
C9 N2 H2A 125.0 . . ?
C24 O1 H1 109.5 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N2 H2A O4 0.86 1.86 2.689(3) 161.5 6_655
O1 H1 O3 0.82 1.69 2.495(4) 169.0 .

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
C1 C2 C3 C4 -2.0(5) . . . . ?
C2 C1 C6 C5 2.0(4) . . . . ?
C2 C3 C4 C5 3.0(4) . . . . ?
C2 C3 C4 C7 -173.3(3) . . . . ?
C3 C4 C5 C6 -1.6(4) . . . . ?
C3 C4 C7 C8 35.1(5) . . . . ?
C3 C4 C7 N1 -145.7(3) . . . . ?
C4 C5 C6 C1 -0.9(4) . . . . ?
C4 C7 C8 N2 -180.0(3) . . . . ?
C4 C7 N1 C9 179.5(3) . . . . ?
C4 C7 N1 C10 -1.6(4) . . . . ?
C5 C4 C7 C8 -141.0(3) . . . . ?
C5 C4 C7 N1 38.2(4) . . . . ?
C6 C1 C2 C3 -0.6(4) . . . . ?
C7 C4 C5 C6 174.5(3) . . . . ?
C7 C8 N2 C9 0.0(4) . . . . ?
C8 C7 N1 C9 -1.1(3) . . . . ?
C8 C7 N1 C10 177.7(3) . . . . ?
C9 C17 C18 C19 177.1(3) . . . . ?
C9 C17 C22 C21 -176.9(3) . . . . ?
C10 C11 C12 C13 0.2(5) . . . . ?
C11 C10 C15 C14 -0.1(4) . . . . ?
C11 C10 N1 C7 70.8(4) . . . . ?
C11 C10 N1 C9 -110.5(3) . . . . ?
C11 C12 C13 C14 -0.3(5) . . . . ?
C11 C12 C13 C16 179.8(4) . . . . ?
C12 C13 C14 C15 0.2(5) . . . . ?
C13 C14 C15 C10 0.0(4) . . . . ?
C15 C10 C11 C12 0.0(4) . . . . ?
C15 C10 N1 C7 -109.6(3) . . . . ?
C15 C10 N1 C9 69.1(3) . . . . ?
C16 C13 C14 C15 -179.9(3) . . . . ?
C17 C9 N1 C7 -177.2(3) . . . . ?
C17 C9 N1 C10 3.9(4) . . . . ?
C17 C9 N2 C8 177.7(3) . . . . ?
C17 C18 C19 C20 -0.1(5) . . . . ?
C18 C17 C22 C21 -0.7(5) . . . . ?
C18 C19 C20 C21 -1.2(5) . . . . ?
C19 C20 C21 C22 1.5(5) . . . . ?
C20 C21 C22 C17 -0.6(5) . . . . ?
C22 C17 C18 C19 1.0(4) . . . . ?
Cl09 C1 C2 C3 179.3(2) . . . . ?
Cl09 C1 C6 C5 -177.9(2) . . . . ?
N1 C7 C8 N2 0.6(3) . . . . ?
N1 C9 C17 C18 36.8(4) . . . . ?
N1 C9 C17 C22 -147.0(3) . . . . ?
N1 C9 N2 C8 -0.7(3) . . . . ?
N1 C10 C11 C12 179.6(3) . . . . ?
N1 C10 C15 C14 -179.7(2) . . . . ?
N2 C9 C17 C18 -141.3(3) . . . . ?
N2 C9 C17 C22 34.9(4) . . . . ?
N2 C9 N1 C7 1.1(3) . . . . ?
N2 C9 N1 C10 -177.7(2) . . . . ?
F1 C23 C24 O1 -135.5(12) . . . . ?
F1 C23 C24 O2 43.0(14) . . . . ?
F2 C23 C24 O1 109.5(7) . . . . ?
F2 C23 C24 O2 -72.0(8) . . . . ?
F3 C23 C24 O1 2.5(11) . . . . ?
F3 C23 C24 O2 -179.0(10) . . . . ?
F4 C25 C26 O3 -40.7(10) . . . . ?
F4 C25 C26 O4 143.3(9) . . . . ?
F5 C25 C26 O3 77.8(9) . . . . ?
F5 C25 C26 O4 -98.2(8) . . . . ?
F6 C25 C26 O3 -163.7(9) . . . . ?
F6 C25 C26 O4 20.3(10) . . . . ?
F1A C23 C24 O1 -178.7(13) . . . . ?
F1A C23 C24 O2 -0.2(15) . . . . ?
F2A C23 C24 O1 36.8(12) . . . . ?
F2A C23 C24 O2 -144.7(11) . . . . ?
F3A C23 C24 O1 -63.7(8) . . . . ?
F3A C23 C24 O2 114.8(8) . . . . ?
F4A C25 C26 O3 2.9(18) . . . . ?
F4A C25 C26 O4 -173.1(17) . . . . ?
F5A C25 C26 O3 125.3(19) . . . . ?
F5A C25 C26 O4 -50.7(19) . . . . ?
F6A C25 C26 O3 -113(2) . . . . ?
F6A C25 C26 O4 71(2) . . . . ?


_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_y_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 2359610'
loop_
_audit_author_name
_audit_author_address
'Yongxing Tang'
;Central China Normal University
China
;
_audit_update_record             
;
2024-05-31 deposited with the CCDC.	2024-06-18 downloaded from the CCDC.
;
_audit_creation_date             2024-05-30
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C15 H13 N O2'
_chemical_formula_sum            'C15 H13 N O2'
_chemical_formula_weight         239.26
_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'
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'

_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_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, y, -z+1/2'
3 'x+1/2, y+1/2, z'
4 '-x+1/2, y+1/2, -z+1/2'
5 '-x, -y, -z'
6 'x, -y, z-1/2'
7 '-x+1/2, -y+1/2, -z'
8 'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   12.719(3)
_cell_length_b                   13.852(3)
_cell_length_c                   14.156(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 97.096(4)
_cell_angle_gamma                90.00
_cell_volume                     2474.9(11)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    2672
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      25.99
_cell_measurement_theta_min      2.18
_exptl_absorpt_coefficient_mu    0.086
_exptl_absorpt_correction_T_max  0.7458
_exptl_absorpt_correction_T_min  0.6917
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS-2008/1 (Bruker,2008)'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.284
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1008
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.1
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0416
_diffrn_reflns_av_unetI/netI     0.0404
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            11520
_diffrn_reflns_theta_full        29.02
_diffrn_reflns_theta_max         29.02
_diffrn_reflns_theta_min         2.18
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed tube'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         0
_reflns_number_gt                2212
_reflns_number_total             3298
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       'SAINT v7.68A (Bruker, 2009)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v7.68A (Bruker, 2009)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XH (Sheldrick, 2008)'
_computing_structure_solution    'XM (Sheldrick, 2008)'
_refine_diff_density_max         0.204
_refine_diff_density_min         -0.145
_refine_diff_density_rms         0.034
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     163
_refine_ls_number_reflns         3298
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0757
_refine_ls_R_factor_gt           0.0490
_refine_ls_restrained_S_all      1.024
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0659P)²+0.6606P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1294
_refine_ls_wR_factor_ref         0.1470
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C8(H8B,H8A)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C6(H6), C9(H9), C11(H11), C12(H12), C13(H13),
 C14(H14), C15(H15)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_special_details      
;
The structure was solved using Direct Methods (ShelXS). RE = 0.2, Nqual =  -1, Ralpha = 0.024
;
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_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_refinement_flags_posn
C1 C 0.86333(11) 0.77080(10) 0.68199(10) 0.0429(3) Uani 1 d . . .
C2 C 0.86267(13) 0.71209(11) 0.60240(11) 0.0521(4) Uani 1 d . . .
H2 H 0.8764 0.7386 0.5449 0.063 Uiso 1 calc . . R
C3 C 0.84160(15) 0.61398(12) 0.60805(14) 0.0656(5) Uani 1 d . . .
H3 H 0.8397 0.5754 0.5541 0.079 Uiso 1 calc . . R
C4 C 0.82349(15) 0.57389(13) 0.69351(15) 0.0712(5) Uani 1 d . . .
H4 H 0.8096 0.5082 0.6973 0.085 Uiso 1 calc . . R
C5 C 0.82594(14) 0.63086(14) 0.77332(14) 0.0695(5) Uani 1 d . . .
H5 H 0.8150 0.6032 0.8312 0.083 Uiso 1 calc . . R
C6 C 0.84458(13) 0.72911(12) 0.76817(12) 0.0578(4) Uani 1 d . . .
H6 H 0.8446 0.7674 0.8222 0.069 Uiso 1 calc . . R
C7 C 0.87966(11) 0.87703(10) 0.67804(10) 0.0450(3) Uani 1 d . . .
C8 C 0.92129(14) 0.91776(10) 0.59021(10) 0.0511(4) Uani 1 d . . .
H8B H 0.9961 0.9029 0.5930 0.061 Uiso 1 calc . . R
H8A H 0.8848 0.8868 0.5340 0.061 Uiso 1 calc . . R
C9 C 0.98073(11) 1.08160(10) 0.61798(9) 0.0429(3) Uani 1 d . . .
H9 H 1.0405 1.0534 0.6512 0.051 Uiso 1 calc . . R
C10 C 0.98037(11) 1.18635(10) 0.61239(9) 0.0404(3) Uani 1 d . . .
C11 C 0.89779(13) 1.24264(11) 0.56765(11) 0.0526(4) Uani 1 d . . .
H11 H 0.8361 1.2132 0.5394 0.063 Uiso 1 calc . . R
C12 C 0.90755(14) 1.34207(12) 0.56526(13) 0.0637(5) Uani 1 d . . .
H12 H 0.8521 1.3790 0.5353 0.076 Uiso 1 calc . . R
C13 C 0.99839(14) 1.38699(12) 0.60678(13) 0.0630(4) Uani 1 d . . .
H13 H 1.0043 1.4539 0.6047 0.076 Uiso 1 calc . . R
C14 C 1.08005(13) 1.33246(12) 0.65116(13) 0.0577(4) Uani 1 d . . .
H14 H 1.1414 1.3625 0.6794 0.069 Uiso 1 calc . . R
C15 C 1.07161(12) 1.23309(11) 0.65408(11) 0.0489(4) Uani 1 d . . .
H15 H 1.1275 1.1969 0.6843 0.059 Uiso 1 calc . . R
N1 N 0.90665(10) 1.02286(8) 0.58160(8) 0.0483(3) Uani 1 d . . .
O1 O 0.86457(10) 0.92993(9) 0.74335(8) 0.0666(4) Uani 1 d . . .
O2 O 0.81657(11) 1.04862(9) 0.53671(11) 0.0826(5) Uani 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
C1 C2 1.389(2) . ?
C1 C6 1.397(2) . ?
C1 C7 1.488(2) . ?
C2 H2 0.9300 . ?
C2 C3 1.389(2) . ?
C3 H3 0.9300 . ?
C3 C4 1.376(3) . ?
C4 H4 0.9300 . ?
C4 C5 1.375(3) . ?
C5 H5 0.9300 . ?
C5 C6 1.385(2) . ?
C6 H6 0.9300 . ?
C7 C8 1.519(2) . ?
C7 O1 1.2134(17) . ?
C8 H8B 0.9700 . ?
C8 H8A 0.9700 . ?
C8 N1 1.4709(18) . ?
C9 H9 0.9300 . ?
C9 C10 1.4531(19) . ?
C9 N1 1.3020(18) . ?
C10 C11 1.3957(19) . ?
C10 C15 1.395(2) . ?
C11 H11 0.9300 . ?
C11 C12 1.384(2) . ?
C12 H12 0.9300 . ?
C12 C13 1.378(2) . ?
C13 H13 0.9300 . ?
C13 C14 1.372(2) . ?
C14 H14 0.9300 . ?
C14 C15 1.382(2) . ?
C15 H15 0.9300 . ?
N1 O2 1.2900(16) . ?

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
C2 C1 C6 118.81(14) . . ?
C2 C1 C7 122.38(13) . . ?
C6 C1 C7 118.77(13) . . ?
C1 C2 H2 119.7 . . ?
C1 C2 C3 120.53(15) . . ?
C3 C2 H2 119.7 . . ?
C2 C3 H3 120.0 . . ?
C4 C3 C2 119.98(17) . . ?
C4 C3 H3 120.0 . . ?
C3 C4 H4 120.0 . . ?
C5 C4 C3 120.09(17) . . ?
C5 C4 H4 120.0 . . ?
C4 C5 H5 119.8 . . ?
C4 C5 C6 120.48(16) . . ?
C6 C5 H5 119.8 . . ?
C1 C6 H6 120.0 . . ?
C5 C6 C1 120.08(16) . . ?
C5 C6 H6 120.0 . . ?
C1 C7 C8 117.54(12) . . ?
O1 C7 C1 122.18(13) . . ?
O1 C7 C8 120.22(13) . . ?
C7 C8 H8B 109.1 . . ?
C7 C8 H8A 109.1 . . ?
H8B C8 H8A 107.8 . . ?
N1 C8 C7 112.46(12) . . ?
N1 C8 H8B 109.1 . . ?
N1 C8 H8A 109.1 . . ?
C10 C9 H9 116.4 . . ?
N1 C9 H9 116.4 . . ?
N1 C9 C10 127.25(13) . . ?
C11 C10 C9 125.43(13) . . ?
C15 C10 C9 116.34(12) . . ?
C15 C10 C11 118.22(13) . . ?
C10 C11 H11 119.9 . . ?
C12 C11 C10 120.16(14) . . ?
C12 C11 H11 119.9 . . ?
C11 C12 H12 119.6 . . ?
C13 C12 C11 120.80(15) . . ?
C13 C12 H12 119.6 . . ?
C12 C13 H13 120.2 . . ?
C14 C13 C12 119.60(15) . . ?
C14 C13 H13 120.2 . . ?
C13 C14 H14 119.8 . . ?
C13 C14 C15 120.33(15) . . ?
C15 C14 H14 119.8 . . ?
C10 C15 H15 119.6 . . ?
C14 C15 C10 120.89(14) . . ?
C14 C15 H15 119.6 . . ?
C9 N1 C8 120.52(13) . . ?
O2 N1 C8 114.22(12) . . ?
O2 N1 C9 125.26(12) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
