# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2023

####################################################################### 
# 
# 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_230109lu_lgpz065018_8a_0m
_audit_block_doi                 10.5517/ccdc.csd.cc2f28wp
_database_code_depnum_ccdc_archive 'CCDC 2236522'
loop_
_audit_author_name
_audit_author_address
'Zhengshan Luo'
;Nankai University
China
;
_audit_update_record             
;
2023-01-16 deposited with the CCDC.	2023-05-12 downloaded from the CCDC.
;
_audit_creation_date             2023-01-14
_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         'C20 H24 F3 N5 O4 S, C4 H8 O2'
_chemical_formula_sum            'C24 H32 F3 N5 O6 S'
_chemical_formula_weight         575.60
_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'
S S 0.1246 0.1234 '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                   11.1319(6)
_cell_length_b                   12.1324(6)
_cell_length_c                   12.4463(6)
_cell_angle_alpha                68.619(2)
_cell_angle_beta                 81.912(2)
_cell_angle_gamma                65.651(2)
_cell_volume                     1425.95(13)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    3535
_cell_measurement_temperature    193.00
_cell_measurement_theta_max      27.11
_cell_measurement_theta_min      2.37
_shelx_estimated_absorpt_T_max   0.982
_shelx_estimated_absorpt_T_min   0.977
_exptl_absorpt_coefficient_mu    0.179
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6517
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1065 before and 0.0630 after correction.
The Ratio of minimum to maximum transmission is 0.8741.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.341
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             604
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0531
_diffrn_reflns_av_unetI/netI     0.0817
_diffrn_reflns_Laue_measured_fraction_full 0.985
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            13282
_diffrn_reflns_point_group_measured_fraction_full 0.985
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.520
_diffrn_reflns_theta_min         1.757
_diffrn_ambient_temperature      193.00
_diffrn_detector                 CPAD
_diffrn_detector_area_resol_mean 7.41
_diffrn_detector_type            'Bruker PHOTON 100'
_diffrn_measured_fraction_theta_full 0.985
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Bruker D8 VENTURE TXS PHOTON 100'
_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           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   TXS
_diffrn_source_current           40.0
_diffrn_source_power             2.0
_diffrn_source_type              'Rotaing Anode'
_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                3765
_reflns_number_total             6477
_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       'APEX4 V2022.1-1 (Bruker, 2022)'
_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         0.533
_refine_diff_density_min         -0.355
_refine_diff_density_rms         0.056
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     356
_refine_ls_number_reflns         6477
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1261
_refine_ls_R_factor_gt           0.0715
_refine_ls_restrained_S_all      1.040
_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)+(0.1022P)²+0.5457P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1884
_refine_ls_wR_factor_ref         0.2266
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C13(H13), C8(H8)
2.b Secondary CH2 refined with riding coordinates:
 C12(H12A,H12B), C9(H9A,H9B), C10(H10A,H10B), C11(H11A,H11B), C23(H23A,H23B)
2.c Aromatic/amide H refined with riding coordinates:
 N1(H1), N3(H3), N2(H2), C17(H17), C4(H4), C3(H3A), C6(H6), C7(H7)
2.d Idealised Me refined as rotating group:
 C19(H19A,H19B,H19C), C20(H20A,H20B,H20C), C21(H21A,H21B,H21C), C24(H24A,H24B,
 H24C)
;
_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
S1 S 0.68692(9) 0.72511(7) 0.09069(7) 0.0508(3) Uani 1 1 d . . . . .
O3 O 0.5192(2) 0.6258(2) 0.0173(2) 0.0560(6) Uani 1 1 d . . . . .
O1 O 0.8075(3) 0.7110(2) 0.1328(2) 0.0626(7) Uani 1 1 d . . . . .
N5 N 0.8071(3) 0.2150(2) 0.0868(2) 0.0446(6) Uani 1 1 d . . . . .
N4 N 0.8935(3) 0.3507(2) 0.1190(2) 0.0419(6) Uani 1 1 d . . . . .
N1 N 0.6762(3) 0.5151(2) 0.3300(2) 0.0459(7) Uani 1 1 d . . . . .
H1 H 0.632144 0.490454 0.296386 0.055 Uiso 1 1 calc R U . . .
N3 N 0.6794(3) 0.4273(2) 0.0487(2) 0.0457(6) Uani 1 1 d . . . . .
H3 H 0.624016 0.407390 0.023126 0.055 Uiso 1 1 calc R U . . .
O2 O 0.6308(3) 0.8259(2) -0.0141(2) 0.0720(8) Uani 1 1 d . . . . .
O4 O 0.9393(3) 0.0015(2) 0.1249(2) 0.0669(7) Uani 1 1 d . . . . .
N2 N 0.7227(3) 0.5862(2) 0.0747(2) 0.0476(7) Uani 1 1 d . . . . .
H2 H 0.805104 0.530286 0.085984 0.057 Uiso 1 1 calc R U . . .
F3 F 1.1999(3) 0.1556(3) 0.6295(3) 0.1170(11) Uani 1 1 d . . . . .
F2 F 1.1485(3) 0.0156(2) 0.6129(3) 0.1077(10) Uani 1 1 d . . . . .
O6 O 0.3122(3) 0.4282(3) 0.2467(2) 0.0770(8) Uani 1 1 d . . . . .
C15 C 0.8013(3) 0.3272(3) 0.0871(2) 0.0404(7) Uani 1 1 d . . . . .
F1 F 1.2485(3) 0.1053(3) 0.4803(3) 0.1489(16) Uani 1 1 d . . . . .
C13 C 0.5640(3) 0.7384(3) 0.2001(3) 0.0426(7) Uani 1 1 d . . . . .
H13 H 0.495227 0.713296 0.183778 0.051 Uiso 1 1 calc R U . . .
O5 O 0.5137(3) 0.3962(3) 0.2854(3) 0.0894(10) Uani 1 1 d . . . . .
C14 C 0.6335(3) 0.5519(3) 0.0451(3) 0.0454(7) Uani 1 1 d . . . . .
C5 C 0.7916(3) 0.4236(3) 0.3881(2) 0.0414(7) Uani 1 1 d . . . . .
C18 C 1.0101(3) 0.2492(3) 0.1559(3) 0.0461(7) Uani 1 1 d . . . . .
C8 C 0.6228(3) 0.6501(3) 0.3208(3) 0.0429(7) Uani 1 1 d . . . . .
H8 H 0.696437 0.670785 0.333930 0.051 Uiso 1 1 calc R U . . .
C16 C 0.9225(3) 0.1175(3) 0.1233(3) 0.0514(8) Uani 1 1 d . . . . .
C19 C 1.1127(3) 0.2795(4) 0.1915(3) 0.0599(9) Uani 1 1 d . . . . .
H19A H 1.118619 0.357022 0.132637 0.090 Uiso 1 1 calc R U . . .
H19B H 1.198248 0.207168 0.199750 0.090 Uiso 1 1 calc R U . . .
H19C H 1.088386 0.294199 0.265391 0.090 Uiso 1 1 calc R U . . .
C17 C 1.0272(3) 0.1312(3) 0.1586(3) 0.0574(9) Uani 1 1 d . . . . .
H17 H 1.108367 0.059702 0.183783 0.069 Uiso 1 1 calc R U . . .
C12 C 0.4997(4) 0.8792(3) 0.1925(3) 0.0597(10) Uani 1 1 d . . . . .
H12A H 0.568497 0.907619 0.200633 0.072 Uiso 1 1 calc R U . . .
H12B H 0.457242 0.932871 0.115693 0.072 Uiso 1 1 calc R U . . .
C2 C 1.0260(3) 0.2293(3) 0.5004(3) 0.0519(8) Uani 1 1 d . . . . .
C4 C 0.8146(3) 0.2947(3) 0.4181(3) 0.0557(9) Uani 1 1 d . . . . .
H4 H 0.749954 0.271264 0.400766 0.067 Uiso 1 1 calc R U . . .
C3 C 0.9308(4) 0.1998(3) 0.4731(3) 0.0600(10) Uani 1 1 d . . . . .
H3A H 0.944720 0.112042 0.492379 0.072 Uiso 1 1 calc R U . . .
C9 C 0.5192(4) 0.6738(3) 0.4131(3) 0.0616(10) Uani 1 1 d . . . . .
H9A H 0.560592 0.619959 0.490288 0.074 Uiso 1 1 calc R U . . .
H9B H 0.448906 0.647317 0.404825 0.074 Uiso 1 1 calc R U . . .
C20 C 0.8299(4) -0.0077(4) 0.0848(4) 0.0717(11) Uani 1 1 d . . . . .
H20A H 0.808272 0.050233 0.004793 0.108 Uiso 1 1 calc R U . . .
H20B H 0.753286 0.016808 0.133520 0.108 Uiso 1 1 calc R U . . .
H20C H 0.853530 -0.096321 0.088672 0.108 Uiso 1 1 calc R U . . .
C10 C 0.4575(4) 0.8152(3) 0.4050(3) 0.0674(11) Uani 1 1 d . . . . .
H10A H 0.388554 0.827155 0.464164 0.081 Uiso 1 1 calc R U . . .
H10B H 0.525916 0.840575 0.419546 0.081 Uiso 1 1 calc R U . . .
C1 C 1.1537(4) 0.1286(4) 0.5548(4) 0.0692(11) Uani 1 1 d . . . . .
C11 C 0.3973(4) 0.8989(3) 0.2855(4) 0.0697(11) Uani 1 1 d . . . . .
H11A H 0.324704 0.877331 0.273599 0.084 Uiso 1 1 calc R U . . .
H11B H 0.359791 0.990443 0.279624 0.084 Uiso 1 1 calc R U . . .
C6 C 0.8903(4) 0.4533(3) 0.4123(4) 0.0703(12) Uani 1 1 d . . . . .
H6 H 0.878438 0.540736 0.390923 0.084 Uiso 1 1 calc R U . . .
C7 C 1.0060(4) 0.3567(3) 0.4673(4) 0.0730(12) Uani 1 1 d . . . . .
H7 H 1.072657 0.379016 0.482479 0.088 Uiso 1 1 calc R U . . .
C22 C 0.4389(5) 0.3548(5) 0.2684(3) 0.0715(12) Uani 1 1 d . . . . .
C21 C 0.4749(5) 0.2225(4) 0.2680(4) 0.0828(13) Uani 1 1 d . . . . .
H21A H 0.417381 0.184279 0.320728 0.124 Uiso 1 1 calc R U . . .
H21B H 0.566912 0.169794 0.293237 0.124 Uiso 1 1 calc R U . . .
H21C H 0.464152 0.226215 0.189786 0.124 Uiso 1 1 calc R U . . .
C23 C 0.2679(5) 0.5609(5) 0.2433(4) 0.0852(13) Uani 1 1 d . . . . .
H23A H 0.314686 0.606753 0.182024 0.102 Uiso 1 1 calc R U . . .
H23B H 0.287061 0.562070 0.318119 0.102 Uiso 1 1 calc R U . . .
C24 C 0.1233(5) 0.6253(5) 0.2195(5) 0.1069(18) Uani 1 1 d . . . . .
H24A H 0.105347 0.624807 0.144824 0.160 Uiso 1 1 calc R U . . .
H24B H 0.091431 0.714340 0.217522 0.160 Uiso 1 1 calc R U . . .
H24C H 0.077819 0.579156 0.280401 0.160 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
S1 O1 1.431(3) . ?
S1 O2 1.422(2) . ?
S1 N2 1.646(2) . ?
S1 C13 1.791(3) . ?
O3 C14 1.224(4) . ?
N5 C15 1.338(4) . ?
N5 C16 1.332(4) . ?
N4 C15 1.316(4) . ?
N4 C18 1.360(4) . ?
N1 H1 0.8800 . ?
N1 C5 1.380(4) . ?
N1 C8 1.459(3) . ?
N3 H3 0.8800 . ?
N3 C15 1.395(4) . ?
N3 C14 1.366(4) . ?
O4 C16 1.334(4) . ?
O4 C20 1.439(4) . ?
N2 H2 0.8800 . ?
N2 C14 1.360(4) . ?
F3 C1 1.316(5) . ?
F2 C1 1.317(5) . ?
O6 C22 1.323(5) . ?
O6 C23 1.463(5) . ?
F1 C1 1.313(5) . ?
C13 H13 1.0000 . ?
C13 C8 1.536(4) . ?
C13 C12 1.528(4) . ?
O5 C22 1.209(5) . ?
C5 C4 1.387(4) . ?
C5 C6 1.388(5) . ?
C18 C19 1.497(5) . ?
C18 C17 1.353(4) . ?
C8 H8 1.0000 . ?
C8 C9 1.526(5) . ?
C16 C17 1.391(5) . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C17 H17 0.9500 . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C12 C11 1.518(5) . ?
C2 C3 1.368(5) . ?
C2 C1 1.486(5) . ?
C2 C7 1.373(5) . ?
C4 H4 0.9500 . ?
C4 C3 1.383(5) . ?
C3 H3A 0.9500 . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C9 C10 1.531(5) . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C10 C11 1.520(5) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C6 H6 0.9500 . ?
C6 C7 1.385(5) . ?
C7 H7 0.9500 . ?
C22 C21 1.488(6) . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C23 H23A 0.9900 . ?
C23 H23B 0.9900 . ?
C23 C24 1.490(7) . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 0.9800 . ?

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
O1 S1 N2 103.74(14) . . ?
O1 S1 C13 109.69(15) . . ?
O2 S1 O1 119.04(17) . . ?
O2 S1 N2 108.91(14) . . ?
O2 S1 C13 108.12(15) . . ?
N2 S1 C13 106.66(14) . . ?
C16 N5 C15 113.8(3) . . ?
C15 N4 C18 116.7(3) . . ?
C5 N1 H1 118.0 . . ?
C5 N1 C8 124.1(2) . . ?
C8 N1 H1 118.0 . . ?
C15 N3 H3 115.3 . . ?
C14 N3 H3 115.3 . . ?
C14 N3 C15 129.4(3) . . ?
C16 O4 C20 116.5(3) . . ?
S1 N2 H2 117.8 . . ?
C14 N2 S1 124.4(2) . . ?
C14 N2 H2 117.8 . . ?
C22 O6 C23 117.0(4) . . ?
N5 C15 N3 112.5(3) . . ?
N4 C15 N5 128.1(3) . . ?
N4 C15 N3 119.4(3) . . ?
S1 C13 H13 108.7 . . ?
C8 C13 S1 111.7(2) . . ?
C8 C13 H13 108.7 . . ?
C12 C13 S1 107.8(2) . . ?
C12 C13 H13 108.7 . . ?
C12 C13 C8 111.3(2) . . ?
O3 C14 N3 121.2(3) . . ?
O3 C14 N2 123.3(3) . . ?
N2 C14 N3 115.4(3) . . ?
N1 C5 C4 118.8(3) . . ?
N1 C5 C6 123.5(3) . . ?
C4 C5 C6 117.6(3) . . ?
N4 C18 C19 115.2(3) . . ?
C17 C18 N4 120.2(3) . . ?
C17 C18 C19 124.6(3) . . ?
N1 C8 C13 111.1(2) . . ?
N1 C8 H8 108.3 . . ?
N1 C8 C9 110.3(3) . . ?
C13 C8 H8 108.3 . . ?
C9 C8 C13 110.5(3) . . ?
C9 C8 H8 108.3 . . ?
N5 C16 O4 118.6(3) . . ?
N5 C16 C17 123.1(3) . . ?
O4 C16 C17 118.3(3) . . ?
C18 C19 H19A 109.5 . . ?
C18 C19 H19B 109.5 . . ?
C18 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C18 C17 C16 118.1(3) . . ?
C18 C17 H17 120.9 . . ?
C16 C17 H17 120.9 . . ?
C13 C12 H12A 109.3 . . ?
C13 C12 H12B 109.3 . . ?
H12A C12 H12B 108.0 . . ?
C11 C12 C13 111.6(3) . . ?
C11 C12 H12A 109.3 . . ?
C11 C12 H12B 109.3 . . ?
C3 C2 C1 122.1(3) . . ?
C3 C2 C7 118.1(3) . . ?
C7 C2 C1 119.5(4) . . ?
C5 C4 H4 119.7 . . ?
C3 C4 C5 120.7(3) . . ?
C3 C4 H4 119.7 . . ?
C2 C3 C4 121.5(3) . . ?
C2 C3 H3A 119.2 . . ?
C4 C3 H3A 119.2 . . ?
C8 C9 H9A 109.2 . . ?
C8 C9 H9B 109.2 . . ?
C8 C9 C10 112.3(3) . . ?
H9A C9 H9B 107.9 . . ?
C10 C9 H9A 109.2 . . ?
C10 C9 H9B 109.2 . . ?
O4 C20 H20A 109.5 . . ?
O4 C20 H20B 109.5 . . ?
O4 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C9 C10 H10A 109.8 . . ?
C9 C10 H10B 109.8 . . ?
H10A C10 H10B 108.2 . . ?
C11 C10 C9 109.5(3) . . ?
C11 C10 H10A 109.8 . . ?
C11 C10 H10B 109.8 . . ?
F3 C1 F2 104.7(3) . . ?
F3 C1 C2 114.0(3) . . ?
F2 C1 C2 113.7(4) . . ?
F1 C1 F3 105.6(4) . . ?
F1 C1 F2 104.4(4) . . ?
F1 C1 C2 113.5(3) . . ?
C12 C11 C10 111.1(3) . . ?
C12 C11 H11A 109.4 . . ?
C12 C11 H11B 109.4 . . ?
C10 C11 H11A 109.4 . . ?
C10 C11 H11B 109.4 . . ?
H11A C11 H11B 108.0 . . ?
C5 C6 H6 119.7 . . ?
C7 C6 C5 120.7(3) . . ?
C7 C6 H6 119.7 . . ?
C2 C7 C6 121.2(4) . . ?
C2 C7 H7 119.4 . . ?
C6 C7 H7 119.4 . . ?
O6 C22 C21 113.0(4) . . ?
O5 C22 O6 121.1(5) . . ?
O5 C22 C21 125.9(4) . . ?
C22 C21 H21A 109.5 . . ?
C22 C21 H21B 109.5 . . ?
C22 C21 H21C 109.5 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
O6 C23 H23A 110.1 . . ?
O6 C23 H23B 110.1 . . ?
O6 C23 C24 108.2(4) . . ?
H23A C23 H23B 108.4 . . ?
C24 C23 H23A 110.1 . . ?
C24 C23 H23B 110.1 . . ?
C23 C24 H24A 109.5 . . ?
C23 C24 H24B 109.5 . . ?
C23 C24 H24C 109.5 . . ?
H24A C24 H24B 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?

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
S1 N2 C14 O3 6.8(5) . . . . ?
S1 N2 C14 N3 -173.0(2) . . . . ?
S1 C13 C8 N1 -63.2(3) . . . . ?
S1 C13 C8 C9 174.0(2) . . . . ?
S1 C13 C12 C11 -177.8(3) . . . . ?
O1 S1 N2 C14 174.3(3) . . . . ?
O1 S1 C13 C8 -37.9(2) . . . . ?
O1 S1 C13 C12 84.7(2) . . . . ?
N5 C16 C17 C18 0.3(6) . . . . ?
N4 C18 C17 C16 -0.4(5) . . . . ?
N1 C5 C4 C3 177.9(3) . . . . ?
N1 C5 C6 C7 -177.7(4) . . . . ?
N1 C8 C9 C10 -178.5(3) . . . . ?
O2 S1 N2 C14 -58.0(3) . . . . ?
O2 S1 C13 C8 -169.1(2) . . . . ?
O2 S1 C13 C12 -46.6(3) . . . . ?
O4 C16 C17 C18 179.5(3) . . . . ?
N2 S1 C13 C8 73.9(2) . . . . ?
N2 S1 C13 C12 -163.6(2) . . . . ?
C15 N5 C16 O4 -179.1(3) . . . . ?
C15 N5 C16 C17 0.0(5) . . . . ?
C15 N4 C18 C19 180.0(3) . . . . ?
C15 N4 C18 C17 0.1(4) . . . . ?
C15 N3 C14 O3 -174.0(3) . . . . ?
C15 N3 C14 N2 5.7(5) . . . . ?
C13 S1 N2 C14 58.5(3) . . . . ?
C13 C8 C9 C10 -55.3(4) . . . . ?
C13 C12 C11 C10 57.3(4) . . . . ?
C14 N3 C15 N5 174.6(3) . . . . ?
C14 N3 C15 N4 -4.9(5) . . . . ?
C5 N1 C8 C13 140.8(3) . . . . ?
C5 N1 C8 C9 -96.2(4) . . . . ?
C5 C4 C3 C2 0.5(6) . . . . ?
C5 C6 C7 C2 -0.6(7) . . . . ?
C18 N4 C15 N5 0.3(5) . . . . ?
C18 N4 C15 N3 179.8(3) . . . . ?
C8 N1 C5 C4 162.7(3) . . . . ?
C8 N1 C5 C6 -21.3(5) . . . . ?
C8 C13 C12 C11 -54.9(4) . . . . ?
C8 C9 C10 C11 57.2(4) . . . . ?
C16 N5 C15 N4 -0.4(5) . . . . ?
C16 N5 C15 N3 -179.9(3) . . . . ?
C19 C18 C17 C16 179.7(3) . . . . ?
C12 C13 C8 N1 176.2(3) . . . . ?
C12 C13 C8 C9 53.4(4) . . . . ?
C4 C5 C6 C7 -1.6(6) . . . . ?
C3 C2 C1 F3 -144.5(4) . . . . ?
C3 C2 C1 F2 -24.6(6) . . . . ?
C3 C2 C1 F1 94.6(5) . . . . ?
C3 C2 C7 C6 2.7(7) . . . . ?
C9 C10 C11 C12 -57.5(5) . . . . ?
C20 O4 C16 N5 0.8(5) . . . . ?
C20 O4 C16 C17 -178.4(3) . . . . ?
C1 C2 C3 C4 -177.3(4) . . . . ?
C1 C2 C7 C6 177.5(4) . . . . ?
C6 C5 C4 C3 1.7(6) . . . . ?
C7 C2 C3 C4 -2.7(6) . . . . ?
C7 C2 C1 F3 40.9(6) . . . . ?
C7 C2 C1 F2 160.8(4) . . . . ?
C7 C2 C1 F1 -80.0(5) . . . . ?
C22 O6 C23 C24 -179.3(4) . . . . ?
C23 O6 C22 O5 0.6(6) . . . . ?
C23 O6 C22 C21 -179.0(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_site                            XU
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: ????'
####################################################################### 
# 
# 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_230109lu_lgpz065018_3f_0m
_audit_block_doi                 10.5517/ccdc.csd.cc2f233r
_database_code_depnum_ccdc_archive 'CCDC 2236343'
loop_
_audit_author_name
_audit_author_address
'Zhengshan Luo'
;Nankai University
China
;
_audit_update_record             
;
2023-01-15 deposited with the CCDC.	2023-05-12 downloaded from the CCDC.
;
_audit_creation_date             2023-01-14
_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         'C12 H15 N3'
_chemical_formula_sum            'C12 H15 N3'
_chemical_formula_weight         201.27
_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'

_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           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, z'

_cell_length_a                   8.2123(4)
_cell_length_b                   8.7897(3)
_cell_length_c                   30.3416(12)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2190.17(16)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    3972
_cell_measurement_temperature    193.00
_cell_measurement_theta_max      27.32
_cell_measurement_theta_min      2.69
_shelx_estimated_absorpt_T_max   0.993
_shelx_estimated_absorpt_T_min   0.990
_exptl_absorpt_coefficient_mu    0.075
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6757
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0928 before and 0.0638 after correction.
The Ratio of minimum to maximum transmission is 0.9062.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.221
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             864
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0629
_diffrn_reflns_av_unetI/netI     0.0390
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       39
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_number            18586
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.497
_diffrn_reflns_theta_min         2.685
_diffrn_ambient_temperature      193.00
_diffrn_detector                 CPAD
_diffrn_detector_area_resol_mean 7.41
_diffrn_detector_type            'Bruker PHOTON 100'
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Bruker D8 VENTURE TXS PHOTON 100'
_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           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   TXS
_diffrn_source_current           40.0
_diffrn_source_power             2.0
_diffrn_source_type              'Rotaing Anode'
_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                1867
_reflns_number_total             2511
_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       'APEX4 V2022.1-1 (Bruker, 2022)'
_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         0.220
_refine_diff_density_min         -0.191
_refine_diff_density_rms         0.050
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.154
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     136
_refine_ls_number_reflns         2511
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0975
_refine_ls_R_factor_gt           0.0684
_refine_ls_restrained_S_all      1.154
_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)+(0.0289P)²+2.5676P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1396
_refine_ls_wR_factor_ref         0.1531
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
2.a Ternary CH refined with riding coordinates:
 C6(H6), C11(H11)
2.b Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B), C7(H7A,H7B), C8(H8A,H8B), C9(H9A,H9B)
2.c Aromatic/amide H refined with riding coordinates:
 N2(H2), C4(H4), C1(H1), C3(H3), C2(H2A)
;
_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
N3 N 0.9084(2) 0.3665(2) 0.67148(6) 0.0270(4) Uani 1 1 d . . . . .
N2 N 0.7166(3) 0.1856(2) 0.64950(7) 0.0337(5) Uani 1 1 d . . . . .
H2 H 0.683816 0.090409 0.651163 0.040 Uiso 1 1 calc R U . . .
C5 C 0.8521(3) 0.2243(3) 0.67308(7) 0.0265(5) Uani 1 1 d . . . . .
C4 C 0.9286(3) 0.1113(3) 0.69904(8) 0.0307(5) Uani 1 1 d . . . . .
H4 H 0.884997 0.011318 0.700374 0.037 Uiso 1 1 calc R U . . .
C1 C 1.0448(3) 0.3972(3) 0.69463(8) 0.0326(6) Uani 1 1 d . . . . .
H1 H 1.086147 0.498036 0.693243 0.039 Uiso 1 1 calc R U . . .
C3 C 1.0660(3) 0.1477(3) 0.72222(8) 0.0314(5) Uani 1 1 d . . . . .
H3 H 1.118880 0.073130 0.739787 0.038 Uiso 1 1 calc R U . . .
C2 C 1.1280(3) 0.2950(3) 0.71985(8) 0.0339(6) Uani 1 1 d . . . . .
H2A H 1.224218 0.323150 0.735188 0.041 Uiso 1 1 calc R U . . .
C6 C 0.6218(3) 0.2876(3) 0.62194(8) 0.0287(5) Uani 1 1 d . . . . .
H6 H 0.651468 0.394667 0.629684 0.034 Uiso 1 1 calc R U . . .
C11 C 0.6565(3) 0.2630(3) 0.57252(8) 0.0324(6) Uani 1 1 d . . . . .
H11 H 0.632436 0.154469 0.565119 0.039 Uiso 1 1 calc R U . . .
N1 N 0.9604(3) 0.3211(4) 0.55547(9) 0.0699(10) Uani 1 1 d . . . . .
C10 C 0.5499(3) 0.3645(3) 0.54361(9) 0.0399(6) Uani 1 1 d . . . . .
H10A H 0.579330 0.472385 0.548614 0.048 Uiso 1 1 calc R U . . .
H10B H 0.570473 0.340679 0.512206 0.048 Uiso 1 1 calc R U . . .
C12 C 0.8288(3) 0.2926(4) 0.56314(9) 0.0426(7) Uani 1 1 d . . . . .
C7 C 0.4407(3) 0.2658(3) 0.63078(8) 0.0390(6) Uani 1 1 d . . . . .
H7A H 0.411099 0.158367 0.625087 0.047 Uiso 1 1 calc R U . . .
H7B H 0.417954 0.287684 0.662192 0.047 Uiso 1 1 calc R U . . .
C8 C 0.3362(3) 0.3687(4) 0.60210(9) 0.0457(7) Uani 1 1 d . . . . .
H8A H 0.219718 0.348781 0.608232 0.055 Uiso 1 1 calc R U . . .
H8B H 0.359049 0.476309 0.609445 0.055 Uiso 1 1 calc R U . . .
C9 C 0.3702(3) 0.3417(4) 0.55373(9) 0.0441(7) Uani 1 1 d . . . . .
H9A H 0.304574 0.413151 0.535796 0.053 Uiso 1 1 calc R U . . .
H9B H 0.337819 0.236805 0.545740 0.053 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
N3 C5 1.333(3) . ?
N3 C1 1.350(3) . ?
N2 H2 0.8800 . ?
N2 C5 1.366(3) . ?
N2 C6 1.453(3) . ?
C5 C4 1.415(3) . ?
C4 H4 0.9500 . ?
C4 C3 1.368(3) . ?
C1 H1 0.9500 . ?
C1 C2 1.363(3) . ?
C3 H3 0.9500 . ?
C3 C2 1.393(3) . ?
C2 H2A 0.9500 . ?
C6 H6 1.0000 . ?
C6 C11 1.542(3) . ?
C6 C7 1.523(3) . ?
C11 H11 1.0000 . ?
C11 C10 1.527(3) . ?
C11 C12 1.466(4) . ?
N1 C12 1.134(4) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C10 C9 1.521(4) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C7 C8 1.520(4) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C8 C9 1.513(4) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?

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 N3 C1 117.1(2) . . ?
C5 N2 H2 117.1 . . ?
C5 N2 C6 125.7(2) . . ?
C6 N2 H2 117.1 . . ?
N3 C5 N2 119.8(2) . . ?
N3 C5 C4 121.6(2) . . ?
N2 C5 C4 118.6(2) . . ?
C5 C4 H4 120.4 . . ?
C3 C4 C5 119.2(2) . . ?
C3 C4 H4 120.4 . . ?
N3 C1 H1 117.4 . . ?
N3 C1 C2 125.2(2) . . ?
C2 C1 H1 117.4 . . ?
C4 C3 H3 120.3 . . ?
C4 C3 C2 119.5(2) . . ?
C2 C3 H3 120.3 . . ?
C1 C2 C3 117.3(2) . . ?
C1 C2 H2A 121.4 . . ?
C3 C2 H2A 121.4 . . ?
N2 C6 H6 108.4 . . ?
N2 C6 C11 112.0(2) . . ?
N2 C6 C7 110.1(2) . . ?
C11 C6 H6 108.4 . . ?
C7 C6 H6 108.4 . . ?
C7 C6 C11 109.51(19) . . ?
C6 C11 H11 108.4 . . ?
C10 C11 C6 111.8(2) . . ?
C10 C11 H11 108.4 . . ?
C12 C11 C6 110.0(2) . . ?
C12 C11 H11 108.4 . . ?
C12 C11 C10 109.8(2) . . ?
C11 C10 H10A 109.4 . . ?
C11 C10 H10B 109.4 . . ?
H10A C10 H10B 108.0 . . ?
C9 C10 C11 111.3(2) . . ?
C9 C10 H10A 109.4 . . ?
C9 C10 H10B 109.4 . . ?
N1 C12 C11 177.3(4) . . ?
C6 C7 H7A 109.2 . . ?
C6 C7 H7B 109.2 . . ?
H7A C7 H7B 107.9 . . ?
C8 C7 C6 112.0(2) . . ?
C8 C7 H7A 109.2 . . ?
C8 C7 H7B 109.2 . . ?
C7 C8 H8A 109.4 . . ?
C7 C8 H8B 109.4 . . ?
H8A C8 H8B 108.0 . . ?
C9 C8 C7 111.0(2) . . ?
C9 C8 H8A 109.4 . . ?
C9 C8 H8B 109.4 . . ?
C10 C9 H9A 109.5 . . ?
C10 C9 H9B 109.5 . . ?
C8 C9 C10 110.7(2) . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
H9A C9 H9B 108.1 . . ?

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
N3 C5 C4 C3 -1.7(4) . . . . ?
N3 C1 C2 C3 -0.7(4) . . . . ?
N2 C5 C4 C3 178.9(2) . . . . ?
N2 C6 C11 C10 176.9(2) . . . . ?
N2 C6 C11 C12 -60.9(3) . . . . ?
N2 C6 C7 C8 -179.1(2) . . . . ?
C5 N3 C1 C2 -0.9(4) . . . . ?
C5 N2 C6 C11 103.4(3) . . . . ?
C5 N2 C6 C7 -134.5(2) . . . . ?
C5 C4 C3 C2 0.1(4) . . . . ?
C4 C3 C2 C1 1.1(4) . . . . ?
C1 N3 C5 N2 -178.5(2) . . . . ?
C1 N3 C5 C4 2.1(3) . . . . ?
C6 N2 C5 N3 -0.7(4) . . . . ?
C6 N2 C5 C4 178.8(2) . . . . ?
C6 C11 C10 C9 -55.3(3) . . . . ?
C6 C7 C8 C9 57.5(3) . . . . ?
C11 C6 C7 C8 -55.5(3) . . . . ?
C11 C10 C9 C8 55.8(3) . . . . ?
C12 C11 C10 C9 -177.7(2) . . . . ?
C7 C6 C11 C10 54.5(3) . . . . ?
C7 C6 C11 C12 176.7(2) . . . . ?
C7 C8 C9 C10 -56.6(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_site                            XU
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: ????/???'
####################################################################### 
# 
# 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_a
_audit_block_doi                 10.5517/ccdc.csd.cc2f234s
_database_code_depnum_ccdc_archive 'CCDC 2236344'
loop_
_audit_author_name
_audit_author_address
'Zhengshan Luo'
;Nankai University
China
;
_audit_update_record             
;
2023-01-15 deposited with the CCDC.	2023-05-12 downloaded from the CCDC.
;
_audit_creation_date             2023-01-14
_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         'C21 H23 F3 N2 O'
_chemical_formula_sum            'C21 H23 F3 N2 O'
_chemical_formula_weight         376.41
_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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   11.3145(15)
_cell_length_b                   4.9401(6)
_cell_length_c                   33.363(4)
_cell_angle_alpha                90
_cell_angle_beta                 92.022(4)
_cell_angle_gamma                90
_cell_volume                     1863.6(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2502
_cell_measurement_temperature    192.90
_cell_measurement_theta_max      26.59
_cell_measurement_theta_min      2.21
_shelx_estimated_absorpt_T_max   0.990
_shelx_estimated_absorpt_T_min   0.987
_exptl_absorpt_coefficient_mu    0.103
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6032
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1085 before and 0.0441 after correction.
The Ratio of minimum to maximum transmission is 0.8090.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.342
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             792
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0651
_diffrn_reflns_av_unetI/netI     0.0768
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       43
_diffrn_reflns_limit_l_min       -43
_diffrn_reflns_number            12894
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.679
_diffrn_reflns_theta_min         2.140
_diffrn_ambient_temperature      192.90
_diffrn_detector                 CPAD
_diffrn_detector_area_resol_mean 7.41
_diffrn_detector_type            'Bruker PHOTON 100'
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Bruker D8 VENTURE TXS PHOTON 100'
_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           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   TXS
_diffrn_source_current           40.0
_diffrn_source_power             2.0
_diffrn_source_type              'Rotaing Anode'
_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                2348
_reflns_number_total             4357
_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       'APEX4 V2022.1-1 (Bruker, 2022)'
_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         0.250
_refine_diff_density_min         -0.330
_refine_diff_density_rms         0.059
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     244
_refine_ls_number_reflns         4357
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1407
_refine_ls_R_factor_gt           0.0670
_refine_ls_restrained_S_all      1.028
_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)+(0.0514P)²+1.9239P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1408
_refine_ls_wR_factor_ref         0.1758
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
2.a Ternary CH refined with riding coordinates:
 C13(H13), C8(H8)
2.b Secondary CH2 refined with riding coordinates:
 C12(H12A,H12B), C15(H15A,H15B), C9(H9A,H9B), C10(H10A,H10B), C11(H11A,H11B)
2.c Aromatic/amide H refined with riding coordinates:
 N2(H2), N1(H1), C4(H4), C6(H6), C17(H17), C21(H21), C7(H7), C3(H3), C19(H19),
 C18(H18), C20(H20)
;
_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 0.77501(18) -0.1908(4) 0.37436(6) 0.0339(5) Uani 1 1 d . . . . .
F1 F 0.06566(17) 0.5609(6) 0.34211(7) 0.0754(8) Uani 1 1 d . . . . .
N2 N 0.8296(2) 0.2187(5) 0.35092(7) 0.0289(5) Uani 1 1 d . . . . .
H2 H 0.846205 0.387871 0.357136 0.035 Uiso 1 1 calc R U . . .
F2 F 0.04554(18) 0.5261(6) 0.40450(7) 0.0850(8) Uani 1 1 d . . . . .
N1 N 0.6011(2) 0.4012(5) 0.39935(7) 0.0351(6) Uani 1 1 d . . . . .
H1 H 0.649293 0.482474 0.383059 0.042 Uiso 1 1 calc R U . . .
F3 F 0.09118(18) 0.9036(5) 0.37876(10) 0.1004(11) Uani 1 1 d . . . . .
C14 C 0.7964(2) 0.0539(6) 0.37998(8) 0.0266(6) Uani 1 1 d . . . . .
C13 C 0.7841(2) 0.1825(6) 0.42108(8) 0.0280(6) Uani 1 1 d . . . . .
H13 H 0.822763 0.364517 0.420942 0.034 Uiso 1 1 calc R U . . .
C8 C 0.6528(2) 0.2203(6) 0.42980(8) 0.0300(6) Uani 1 1 d . . . . .
H8 H 0.612497 0.040538 0.427499 0.036 Uiso 1 1 calc R U . . .
C5 C 0.4817(2) 0.4532(6) 0.39443(9) 0.0321(7) Uani 1 1 d . . . . .
C4 C 0.4442(3) 0.6640(7) 0.36884(9) 0.0363(7) Uani 1 1 d . . . . .
H4 H 0.501097 0.768167 0.355327 0.044 Uiso 1 1 calc R U . . .
C16 C 0.7852(3) 0.3420(6) 0.28134(8) 0.0334(7) Uani 1 1 d . . . . .
C12 C 0.8467(3) 0.0085(7) 0.45324(8) 0.0378(7) Uani 1 1 d . . . . .
H12A H 0.814994 -0.178140 0.451646 0.045 Uiso 1 1 calc R U . . .
H12B H 0.932157 0.000305 0.447914 0.045 Uiso 1 1 calc R U . . .
C15 C 0.8399(3) 0.1340(6) 0.30928(8) 0.0343(7) Uani 1 1 d . . . . .
H15A H 0.799686 -0.042186 0.305065 0.041 Uiso 1 1 calc R U . . .
H15B H 0.924425 0.110453 0.303326 0.041 Uiso 1 1 calc R U . . .
C9 C 0.6390(3) 0.3283(6) 0.47241(9) 0.0381(7) Uani 1 1 d . . . . .
H9A H 0.672642 0.513035 0.474329 0.046 Uiso 1 1 calc R U . . .
H9B H 0.553834 0.340208 0.478062 0.046 Uiso 1 1 calc R U . . .
C6 C 0.3958(3) 0.3022(7) 0.41373(9) 0.0372(7) Uani 1 1 d . . . . .
H6 H 0.418987 0.157142 0.430975 0.045 Uiso 1 1 calc R U . . .
C2 C 0.2406(3) 0.5729(7) 0.38269(9) 0.0386(8) Uani 1 1 d . . . . .
C17 C 0.6703(3) 0.4314(7) 0.28636(10) 0.0426(8) Uani 1 1 d . . . . .
H17 H 0.626041 0.360104 0.307594 0.051 Uiso 1 1 calc R U . . .
C21 C 0.8469(3) 0.4466(7) 0.24989(9) 0.0460(8) Uani 1 1 d . . . . .
H21 H 0.925237 0.386266 0.245706 0.055 Uiso 1 1 calc R U . . .
C7 C 0.2770(3) 0.3639(7) 0.40774(10) 0.0401(8) Uani 1 1 d . . . . .
H7 H 0.219506 0.260553 0.421102 0.048 Uiso 1 1 calc R U . . .
C3 C 0.3257(3) 0.7211(7) 0.36314(10) 0.0417(8) Uani 1 1 d . . . . .
H3 H 0.301709 0.863878 0.345590 0.050 Uiso 1 1 calc R U . . .
C10 C 0.7008(3) 0.1475(7) 0.50378(9) 0.0460(9) Uani 1 1 d . . . . .
H10A H 0.691980 0.226683 0.530767 0.055 Uiso 1 1 calc R U . . .
H10B H 0.663117 -0.033439 0.503434 0.055 Uiso 1 1 calc R U . . .
C11 C 0.8308(3) 0.1188(8) 0.49541(9) 0.0478(9) Uani 1 1 d . . . . .
H11A H 0.868627 -0.005327 0.515308 0.057 Uiso 1 1 calc R U . . .
H11B H 0.869911 0.297500 0.498081 0.057 Uiso 1 1 calc R U . . .
C1 C 0.1135(3) 0.6414(8) 0.37702(11) 0.0486(9) Uani 1 1 d . . . . .
C19 C 0.6823(4) 0.7261(8) 0.22969(10) 0.0551(10) Uani 1 1 d . . . . .
H19 H 0.647175 0.856489 0.212056 0.066 Uiso 1 1 calc R U . . .
C18 C 0.6195(3) 0.6225(8) 0.26092(10) 0.0519(9) Uani 1 1 d . . . . .
H18 H 0.541111 0.682884 0.264936 0.062 Uiso 1 1 calc R U . . .
C20 C 0.7959(4) 0.6391(8) 0.22429(10) 0.0552(10) Uani 1 1 d . . . . .
H20 H 0.839826 0.710750 0.202981 0.066 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 C14 1.246(3) . ?
F1 C1 1.328(4) . ?
N2 H2 0.8800 . ?
N2 C14 1.330(3) . ?
N2 C15 1.460(3) . ?
F2 C1 1.344(4) . ?
N1 H1 0.8800 . ?
N1 C8 1.460(4) . ?
N1 C5 1.379(3) . ?
F3 C1 1.321(4) . ?
C14 C13 1.522(4) . ?
C13 H13 1.0000 . ?
C13 C8 1.535(4) . ?
C13 C12 1.529(4) . ?
C8 H8 1.0000 . ?
C8 C9 1.532(4) . ?
C5 C4 1.402(4) . ?
C5 C6 1.400(4) . ?
C4 H4 0.9500 . ?
C4 C3 1.377(4) . ?
C16 C15 1.506(4) . ?
C16 C17 1.388(4) . ?
C16 C21 1.381(4) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C12 C11 1.526(4) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C9 C10 1.526(4) . ?
C6 H6 0.9500 . ?
C6 C7 1.386(4) . ?
C2 C7 1.382(5) . ?
C2 C3 1.391(5) . ?
C2 C1 1.482(4) . ?
C17 H17 0.9500 . ?
C17 C18 1.381(5) . ?
C21 H21 0.9500 . ?
C21 C20 1.390(5) . ?
C7 H7 0.9500 . ?
C3 H3 0.9500 . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C10 C11 1.514(5) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C19 H19 0.9500 . ?
C19 C18 1.380(5) . ?
C19 C20 1.373(5) . ?
C18 H18 0.9500 . ?
C20 H20 0.9500 . ?

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
C14 N2 H2 118.2 . . ?
C14 N2 C15 123.6(2) . . ?
C15 N2 H2 118.2 . . ?
C8 N1 H1 117.8 . . ?
C5 N1 H1 117.8 . . ?
C5 N1 C8 124.3(2) . . ?
O1 C14 N2 122.8(3) . . ?
O1 C14 C13 121.1(3) . . ?
N2 C14 C13 116.0(3) . . ?
C14 C13 H13 108.5 . . ?
C14 C13 C8 109.9(2) . . ?
C14 C13 C12 110.1(2) . . ?
C8 C13 H13 108.5 . . ?
C12 C13 H13 108.5 . . ?
C12 C13 C8 111.3(2) . . ?
N1 C8 C13 108.0(2) . . ?
N1 C8 H8 108.6 . . ?
N1 C8 C9 112.4(2) . . ?
C13 C8 H8 108.6 . . ?
C9 C8 C13 110.5(2) . . ?
C9 C8 H8 108.6 . . ?
N1 C5 C4 119.0(3) . . ?
N1 C5 C6 122.6(3) . . ?
C6 C5 C4 118.4(3) . . ?
C5 C4 H4 119.7 . . ?
C3 C4 C5 120.6(3) . . ?
C3 C4 H4 119.7 . . ?
C17 C16 C15 120.6(3) . . ?
C21 C16 C15 121.2(3) . . ?
C21 C16 C17 118.2(3) . . ?
C13 C12 H12A 109.1 . . ?
C13 C12 H12B 109.1 . . ?
H12A C12 H12B 107.9 . . ?
C11 C12 C13 112.3(3) . . ?
C11 C12 H12A 109.1 . . ?
C11 C12 H12B 109.1 . . ?
N2 C15 C16 110.4(2) . . ?
N2 C15 H15A 109.6 . . ?
N2 C15 H15B 109.6 . . ?
C16 C15 H15A 109.6 . . ?
C16 C15 H15B 109.6 . . ?
H15A C15 H15B 108.1 . . ?
C8 C9 H9A 109.2 . . ?
C8 C9 H9B 109.2 . . ?
H9A C9 H9B 107.9 . . ?
C10 C9 C8 111.9(3) . . ?
C10 C9 H9A 109.2 . . ?
C10 C9 H9B 109.2 . . ?
C5 C6 H6 119.9 . . ?
C7 C6 C5 120.1(3) . . ?
C7 C6 H6 119.9 . . ?
C7 C2 C3 118.7(3) . . ?
C7 C2 C1 121.0(3) . . ?
C3 C2 C1 120.3(3) . . ?
C16 C17 H17 119.5 . . ?
C18 C17 C16 121.0(3) . . ?
C18 C17 H17 119.5 . . ?
C16 C21 H21 119.6 . . ?
C16 C21 C20 120.8(3) . . ?
C20 C21 H21 119.6 . . ?
C6 C7 H7 119.4 . . ?
C2 C7 C6 121.2(3) . . ?
C2 C7 H7 119.4 . . ?
C4 C3 C2 121.0(3) . . ?
C4 C3 H3 119.5 . . ?
C2 C3 H3 119.5 . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
H10A C10 H10B 108.1 . . ?
C11 C10 C9 110.7(3) . . ?
C11 C10 H10A 109.5 . . ?
C11 C10 H10B 109.5 . . ?
C12 C11 H11A 109.5 . . ?
C12 C11 H11B 109.5 . . ?
C10 C11 C12 110.5(3) . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
H11A C11 H11B 108.1 . . ?
F1 C1 F2 104.2(3) . . ?
F1 C1 C2 114.0(3) . . ?
F2 C1 C2 113.1(3) . . ?
F3 C1 F1 105.0(3) . . ?
F3 C1 F2 105.7(3) . . ?
F3 C1 C2 113.9(3) . . ?
C18 C19 H19 120.3 . . ?
C20 C19 H19 120.3 . . ?
C20 C19 C18 119.5(3) . . ?
C17 C18 H18 119.9 . . ?
C19 C18 C17 120.2(4) . . ?
C19 C18 H18 119.9 . . ?
C21 C20 H20 119.9 . . ?
C19 C20 C21 120.2(3) . . ?
C19 C20 H20 119.9 . . ?

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
O1 C14 C13 C8 -74.6(3) . . . . ?
O1 C14 C13 C12 48.3(3) . . . . ?
N2 C14 C13 C8 104.7(3) . . . . ?
N2 C14 C13 C12 -132.4(3) . . . . ?
N1 C8 C9 C10 -176.1(2) . . . . ?
N1 C5 C4 C3 179.8(3) . . . . ?
N1 C5 C6 C7 179.9(3) . . . . ?
C14 N2 C15 C16 135.3(3) . . . . ?
C14 C13 C8 N1 -61.2(3) . . . . ?
C14 C13 C8 C9 175.5(2) . . . . ?
C14 C13 C12 C11 -176.5(3) . . . . ?
C13 C8 C9 C10 -55.3(3) . . . . ?
C13 C12 C11 C10 55.9(4) . . . . ?
C8 N1 C5 C4 169.3(3) . . . . ?
C8 N1 C5 C6 -11.2(5) . . . . ?
C8 C13 C12 C11 -54.4(3) . . . . ?
C8 C9 C10 C11 57.4(4) . . . . ?
C5 N1 C8 C13 171.1(3) . . . . ?
C5 N1 C8 C9 -66.8(4) . . . . ?
C5 C4 C3 C2 0.3(5) . . . . ?
C5 C6 C7 C2 0.3(5) . . . . ?
C4 C5 C6 C7 -0.7(4) . . . . ?
C16 C17 C18 C19 0.6(5) . . . . ?
C16 C21 C20 C19 -0.7(5) . . . . ?
C12 C13 C8 N1 176.6(2) . . . . ?
C12 C13 C8 C9 53.3(3) . . . . ?
C15 N2 C14 O1 2.5(4) . . . . ?
C15 N2 C14 C13 -176.7(2) . . . . ?
C15 C16 C17 C18 179.9(3) . . . . ?
C15 C16 C21 C20 -179.8(3) . . . . ?
C9 C10 C11 C12 -56.7(4) . . . . ?
C6 C5 C4 C3 0.4(4) . . . . ?
C17 C16 C15 N2 -52.6(4) . . . . ?
C17 C16 C21 C20 0.9(5) . . . . ?
C21 C16 C15 N2 128.1(3) . . . . ?
C21 C16 C17 C18 -0.8(5) . . . . ?
C7 C2 C3 C4 -0.8(5) . . . . ?
C7 C2 C1 F1 -104.9(4) . . . . ?
C7 C2 C1 F2 14.0(5) . . . . ?
C7 C2 C1 F3 134.7(4) . . . . ?
C3 C2 C7 C6 0.4(5) . . . . ?
C3 C2 C1 F1 75.9(4) . . . . ?
C3 C2 C1 F2 -165.2(3) . . . . ?
C3 C2 C1 F3 -44.5(5) . . . . ?
C1 C2 C7 C6 -178.8(3) . . . . ?
C1 C2 C3 C4 178.5(3) . . . . ?
C18 C19 C20 C21 0.5(6) . . . . ?
C20 C19 C18 C17 -0.5(5) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_site                            XU
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: ????/???'
####################################################################### 
# 
# 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_r20221208b
_audit_block_doi                 10.5517/ccdc.csd.cc2f0d3z
_database_code_depnum_ccdc_archive 'CCDC 2234700'
loop_
_audit_author_name
_audit_author_address
'Zhengshan Luo'
;Nankai University
China
;
_audit_update_record             
;
2023-01-06 deposited with the CCDC.	2023-05-12 downloaded from the CCDC.
;
_audit_creation_date             2022-12-08
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.01.04 svn.r3372 for OlexSys, GUI svn.r5292)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        
(1S,2R,2'R,4R)-2'-((4-(trifluoromethyl)phenyl)amino)spiro[bicyclo[2.2.1]heptane-2,1'-cyclohexan]-3-one
_chemical_formula_moiety         'C19 H22 F3 N O'
_chemical_formula_sum            'C19 H22 F3 N O'
_chemical_formula_weight         337.37
_chemical_absolute_configuration unk
_chemical_melting_point          413-415
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      tetragonal
_space_group_IT_number           82
_space_group_name_Hall           'I -4'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z'
'y, -x, -z'
'-y, x, -z'
'x+1/2, y+1/2, z+1/2'
'-x+1/2, -y+1/2, z+1/2'
'y+1/2, -x+1/2, -z+1/2'
'-y+1/2, x+1/2, -z+1/2'

_cell_length_a                   13.5660(3)
_cell_length_b                   13.5660(3)
_cell_length_c                   18.1175(6)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3334.28(18)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    13864
_cell_measurement_temperature    113.15
_cell_measurement_theta_max      32.4920
_cell_measurement_theta_min      1.8560
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.105
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.67408
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'Light yellow solid'
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.344
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       flakes
_exptl_crystal_F_000             1424
_exptl_crystal_size_max          0.48
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.22
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0485
_diffrn_reflns_av_unetI/netI     0.0333
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            21324
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.691
_diffrn_reflns_theta_min         1.875
_diffrn_ambient_temperature      113.15
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -115.00  65.00   1.00    1.00    --  -25.00  45.00   0.00  180
  2  ω   -115.00  65.00   1.00    1.00    --  -25.00  45.00  90.00  180
  3  ω   -115.00  65.00   1.00    1.00    --  -25.00  45.00 180.00  180
;
_diffrn_measurement_device       'abstract diffractometer'
_diffrn_measurement_device_type  'Rigaku Saturn 70'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0507970000
_diffrn_orient_matrix_UB_12      0.0111191000
_diffrn_orient_matrix_UB_13      0.0040367000
_diffrn_orient_matrix_UB_21      0.0095126000
_diffrn_orient_matrix_UB_22      -0.0497310000
_diffrn_orient_matrix_UB_23      0.0097984000
_diffrn_orient_matrix_UB_31      0.0079212000
_diffrn_orient_matrix_UB_32      -0.0117140000
_diffrn_orient_matrix_UB_33      -0.0376868000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.937
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     1.000
_reflns_number_gt                3987
_reflns_number_total             4313
_reflns_odcompleteness_completeness 96.30
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     32.75
_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       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrystalClear(Rigaku, 2008)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_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         0.210
_refine_diff_density_min         -0.153
_refine_diff_density_rms         0.034
_refine_ls_abs_structure_details 
;
 Flack x determined using 1746 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.2(3)
_refine_ls_extinction_coef       0.0033(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2016/6 (Sheldrick 2016)'
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     222
_refine_ls_number_reflns         4313
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0405
_refine_ls_R_factor_gt           0.0368
_refine_ls_restrained_S_all      1.037
_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)+(0.0362P)²+1.3244P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0830
_refine_ls_wR_factor_ref         0.0859
_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:
 C3(H3), C6(H6), C8(H8)
2.b Secondary CH2 refined with riding coordinates:
 C4(H4A,H4B), C5(H5A,H5B), C7(H7A,H7B), C9(H9A,H9B), C10(H10A,H10B), C11(H11A,
 H11B), C12(H12A,H12B)
2.c Aromatic/amide H refined with riding coordinates:
 C14(H14), C15(H15), C17(H17), C18(H18)
;
_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 0.29164(12) 0.19797(15) 0.43043(9) 0.0509(5) Uani 1 1 d . . . . .
F2 F 0.38965(15) 0.30390(12) 0.38372(8) 0.0487(5) Uani 1 1 d . . . . .
F3 F 0.43681(13) 0.15423(13) 0.40090(9) 0.0471(4) Uani 1 1 d . . . . .
O1 O 0.63587(11) 0.50076(11) 0.75937(9) 0.0270(3) Uani 1 1 d . . . . .
N1 N 0.50692(13) 0.33055(14) 0.72112(10) 0.0236(4) Uani 1 1 d . . . . .
C1 C 0.63271(14) 0.33947(14) 0.82143(11) 0.0178(4) Uani 1 1 d . . . . .
C2 C 0.67998(15) 0.42878(15) 0.78242(11) 0.0201(4) Uani 1 1 d . . . . .
C3 C 0.79055(16) 0.41469(16) 0.78542(13) 0.0268(5) Uani 1 1 d . . . . .
H3 H 0.829710 0.451399 0.747585 0.032 Uiso 1 1 calc R . . . .
C4 C 0.81689(18) 0.43636(17) 0.86768(14) 0.0313(5) Uani 1 1 d . . . . .
H4A H 0.888845 0.445017 0.874053 0.038 Uiso 1 1 calc R . . . .
H4B H 0.782708 0.496261 0.885539 0.038 Uiso 1 1 calc R . . . .
C5 C 0.77986(17) 0.34318(16) 0.90893(13) 0.0274(5) Uani 1 1 d . . . . .
H5A H 0.835585 0.305322 0.929942 0.033 Uiso 1 1 calc R . . . .
H5B H 0.733673 0.360939 0.949092 0.033 Uiso 1 1 calc R . . . .
C6 C 0.72714(15) 0.28411(15) 0.84781(12) 0.0207(4) Uani 1 1 d . . . . .
H6 H 0.716239 0.213054 0.860026 0.025 Uiso 1 1 calc R . . . .
C7 C 0.79866(16) 0.30165(16) 0.78303(13) 0.0262(4) Uani 1 1 d . . . . .
H7A H 0.866203 0.277812 0.793487 0.031 Uiso 1 1 calc R . . . .
H7B H 0.774442 0.273396 0.736022 0.031 Uiso 1 1 calc R . . . .
C8 C 0.57367(15) 0.27256(14) 0.76707(12) 0.0202(4) Uani 1 1 d . . . . .
H8 H 0.622201 0.239580 0.733670 0.024 Uiso 1 1 calc R . . . .
C9 C 0.51771(17) 0.19096(17) 0.80961(13) 0.0286(5) Uani 1 1 d . . . . .
H9A H 0.476471 0.153259 0.774464 0.034 Uiso 1 1 calc R . . . .
H9B H 0.566103 0.144835 0.831514 0.034 Uiso 1 1 calc R . . . .
C10 C 0.4520(2) 0.2322(2) 0.87091(15) 0.0381(6) Uani 1 1 d . . . . .
H10A H 0.398824 0.272577 0.848889 0.046 Uiso 1 1 calc R . . . .
H10B H 0.421038 0.177062 0.898232 0.046 Uiso 1 1 calc R . . . .
C11 C 0.5123(2) 0.29522(19) 0.92414(14) 0.0344(5) Uani 1 1 d . . . . .
H11A H 0.468526 0.323339 0.962471 0.041 Uiso 1 1 calc R . . . .
H11B H 0.562514 0.253912 0.948913 0.041 Uiso 1 1 calc R . . . .
C12 C 0.56267(16) 0.37824(15) 0.88166(12) 0.0231(4) Uani 1 1 d . . . . .
H12A H 0.600523 0.419566 0.916666 0.028 Uiso 1 1 calc R . . . .
H12B H 0.511753 0.420380 0.858498 0.028 Uiso 1 1 calc R . . . .
C13 C 0.48049(14) 0.30469(15) 0.65095(12) 0.0200(4) Uani 1 1 d . . . . .
C14 C 0.50334(15) 0.21178(15) 0.62030(12) 0.0221(4) Uani 1 1 d . . . . .
H14 H 0.539169 0.165022 0.648653 0.027 Uiso 1 1 calc R . . . .
C15 C 0.47385(16) 0.18814(16) 0.54901(12) 0.0231(4) Uani 1 1 d . . . . .
H15 H 0.489676 0.125310 0.529126 0.028 Uiso 1 1 calc R . . . .
C16 C 0.42151(15) 0.25534(16) 0.50653(12) 0.0212(4) Uani 1 1 d . . . . .
C17 C 0.39908(15) 0.34794(15) 0.53610(12) 0.0215(4) Uani 1 1 d . . . . .
H17 H 0.363706 0.394424 0.507187 0.026 Uiso 1 1 calc R . . . .
C18 C 0.42779(14) 0.37243(15) 0.60678(12) 0.0204(4) Uani 1 1 d . . . . .
H18 H 0.411928 0.435622 0.625998 0.024 Uiso 1 1 calc R . . . .
C19 C 0.38581(17) 0.22859(16) 0.43150(12) 0.0256(4) Uani 1 1 d . . . . .
H1 H 0.491(2) 0.389(2) 0.7361(17) 0.040(8) Uiso 1 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
F1 C19 1.343(3) . ?
F2 C19 1.340(3) . ?
F3 C19 1.343(3) . ?
O1 C2 1.219(2) . ?
N1 C8 1.460(3) . ?
N1 C13 1.367(3) . ?
N1 H1 0.87(3) . ?
C1 C2 1.542(3) . ?
C1 C6 1.560(3) . ?
C1 C8 1.561(3) . ?
C1 C12 1.540(3) . ?
C2 C3 1.513(3) . ?
C3 H3 1.0000 . ?
C3 C4 1.560(3) . ?
C3 C7 1.538(3) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C4 C5 1.552(3) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C5 C6 1.543(3) . ?
C6 H6 1.0000 . ?
C6 C7 1.541(3) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 H8 1.0000 . ?
C8 C9 1.548(3) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C9 C10 1.530(3) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C10 C11 1.527(4) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C11 C12 1.526(3) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 C14 1.412(3) . ?
C13 C18 1.413(3) . ?
C14 H14 0.9500 . ?
C14 C15 1.390(3) . ?
C15 H15 0.9500 . ?
C15 C16 1.388(3) . ?
C16 C17 1.399(3) . ?
C16 C19 1.488(3) . ?
C17 H17 0.9500 . ?
C17 C18 1.379(3) . ?
C18 H18 0.9500 . ?

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
C8 N1 H1 118(2) . . ?
C13 N1 C8 123.70(18) . . ?
C13 N1 H1 118(2) . . ?
C2 C1 C6 100.20(15) . . ?
C2 C1 C8 112.40(16) . . ?
C6 C1 C8 109.56(16) . . ?
C12 C1 C2 108.24(16) . . ?
C12 C1 C6 117.01(17) . . ?
C12 C1 C8 109.22(16) . . ?
O1 C2 C1 125.60(19) . . ?
O1 C2 C3 126.9(2) . . ?
C3 C2 C1 107.25(16) . . ?
C2 C3 H3 116.1 . . ?
C2 C3 C4 103.73(18) . . ?
C2 C3 C7 101.29(16) . . ?
C4 C3 H3 116.1 . . ?
C7 C3 H3 116.1 . . ?
C7 C3 C4 101.44(18) . . ?
C3 C4 H4A 111.1 . . ?
C3 C4 H4B 111.1 . . ?
H4A C4 H4B 109.0 . . ?
C5 C4 C3 103.44(17) . . ?
C5 C4 H4A 111.1 . . ?
C5 C4 H4B 111.1 . . ?
C4 C5 H5A 111.1 . . ?
C4 C5 H5B 111.1 . . ?
H5A C5 H5B 109.1 . . ?
C6 C5 C4 103.15(18) . . ?
C6 C5 H5A 111.1 . . ?
C6 C5 H5B 111.1 . . ?
C1 C6 H6 114.2 . . ?
C5 C6 C1 110.52(17) . . ?
C5 C6 H6 114.2 . . ?
C7 C6 C1 102.08(16) . . ?
C7 C6 C5 100.06(17) . . ?
C7 C6 H6 114.2 . . ?
C3 C7 C6 95.02(17) . . ?
C3 C7 H7A 112.7 . . ?
C3 C7 H7B 112.7 . . ?
C6 C7 H7A 112.7 . . ?
C6 C7 H7B 112.7 . . ?
H7A C7 H7B 110.2 . . ?
N1 C8 C1 111.40(16) . . ?
N1 C8 H8 107.7 . . ?
N1 C8 C9 111.41(18) . . ?
C1 C8 H8 107.7 . . ?
C9 C8 C1 110.70(17) . . ?
C9 C8 H8 107.7 . . ?
C8 C9 H9A 109.1 . . ?
C8 C9 H9B 109.1 . . ?
H9A C9 H9B 107.8 . . ?
C10 C9 C8 112.71(19) . . ?
C10 C9 H9A 109.1 . . ?
C10 C9 H9B 109.1 . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
H10A C10 H10B 108.1 . . ?
C11 C10 C9 110.6(2) . . ?
C11 C10 H10A 109.5 . . ?
C11 C10 H10B 109.5 . . ?
C10 C11 H11A 109.8 . . ?
C10 C11 H11B 109.8 . . ?
H11A C11 H11B 108.2 . . ?
C12 C11 C10 109.6(2) . . ?
C12 C11 H11A 109.8 . . ?
C12 C11 H11B 109.8 . . ?
C1 C12 H12A 109.1 . . ?
C1 C12 H12B 109.1 . . ?
C11 C12 C1 112.45(18) . . ?
C11 C12 H12A 109.1 . . ?
C11 C12 H12B 109.1 . . ?
H12A C12 H12B 107.8 . . ?
N1 C13 C14 122.52(19) . . ?
N1 C13 C18 119.51(18) . . ?
C14 C13 C18 117.97(19) . . ?
C13 C14 H14 119.7 . . ?
C15 C14 C13 120.56(19) . . ?
C15 C14 H14 119.7 . . ?
C14 C15 H15 119.6 . . ?
C16 C15 C14 120.7(2) . . ?
C16 C15 H15 119.6 . . ?
C15 C16 C17 119.24(19) . . ?
C15 C16 C19 120.85(19) . . ?
C17 C16 C19 119.86(19) . . ?
C16 C17 H17 119.7 . . ?
C18 C17 C16 120.7(2) . . ?
C18 C17 H17 119.7 . . ?
C13 C18 H18 119.6 . . ?
C17 C18 C13 120.81(19) . . ?
C17 C18 H18 119.6 . . ?
F1 C19 C16 113.46(18) . . ?
F2 C19 F1 105.27(19) . . ?
F2 C19 F3 106.61(19) . . ?
F2 C19 C16 113.05(18) . . ?
F3 C19 F1 104.58(19) . . ?
F3 C19 C16 113.12(18) . . ?

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
O1 C2 C3 C4 100.9(3) . . . . ?
O1 C2 C3 C7 -154.3(2) . . . . ?
N1 C8 C9 C10 -70.6(2) . . . . ?
N1 C13 C14 C15 179.1(2) . . . . ?
N1 C13 C18 C17 -179.20(19) . . . . ?
C1 C2 C3 C4 -73.41(19) . . . . ?
C1 C2 C3 C7 31.5(2) . . . . ?
C1 C6 C7 C3 55.73(18) . . . . ?
C1 C8 C9 C10 53.9(2) . . . . ?
C2 C1 C6 C5 68.8(2) . . . . ?
C2 C1 C6 C7 -36.95(19) . . . . ?
C2 C1 C8 N1 -48.9(2) . . . . ?
C2 C1 C8 C9 -173.47(16) . . . . ?
C2 C1 C12 C11 -179.66(19) . . . . ?
C2 C3 C4 C5 74.3(2) . . . . ?
C2 C3 C7 C6 -52.52(19) . . . . ?
C3 C4 C5 C6 -5.7(2) . . . . ?
C4 C3 C7 C6 54.18(18) . . . . ?
C4 C5 C6 C1 -67.2(2) . . . . ?
C4 C5 C6 C7 39.9(2) . . . . ?
C5 C6 C7 C3 -57.97(18) . . . . ?
C6 C1 C2 O1 -171.1(2) . . . . ?
C6 C1 C2 C3 3.2(2) . . . . ?
C6 C1 C8 N1 -159.39(17) . . . . ?
C6 C1 C8 C9 76.1(2) . . . . ?
C6 C1 C12 C11 -67.5(2) . . . . ?
C7 C3 C4 C5 -30.5(2) . . . . ?
C8 N1 C13 C14 9.9(3) . . . . ?
C8 N1 C13 C18 -170.43(19) . . . . ?
C8 C1 C2 O1 72.6(3) . . . . ?
C8 C1 C2 C3 -113.00(19) . . . . ?
C8 C1 C6 C5 -172.89(18) . . . . ?
C8 C1 C6 C7 81.40(19) . . . . ?
C8 C1 C12 C11 57.7(2) . . . . ?
C8 C9 C10 C11 -55.9(3) . . . . ?
C9 C10 C11 C12 57.4(3) . . . . ?
C10 C11 C12 C1 -59.9(3) . . . . ?
C12 C1 C2 O1 -48.1(3) . . . . ?
C12 C1 C2 C3 126.28(19) . . . . ?
C12 C1 C6 C5 -47.9(2) . . . . ?
C12 C1 C6 C7 -153.62(17) . . . . ?
C12 C1 C8 N1 71.2(2) . . . . ?
C12 C1 C8 C9 -53.3(2) . . . . ?
C13 N1 C8 C1 149.67(19) . . . . ?
C13 N1 C8 C9 -86.2(2) . . . . ?
C13 C14 C15 C16 0.1(3) . . . . ?
C14 C13 C18 C17 0.5(3) . . . . ?
C14 C15 C16 C17 0.4(3) . . . . ?
C14 C15 C16 C19 -177.1(2) . . . . ?
C15 C16 C17 C18 -0.5(3) . . . . ?
C15 C16 C19 F1 96.4(2) . . . . ?
C15 C16 C19 F2 -143.9(2) . . . . ?
C15 C16 C19 F3 -22.6(3) . . . . ?
C16 C17 C18 C13 0.0(3) . . . . ?
C17 C16 C19 F1 -81.2(3) . . . . ?
C17 C16 C19 F2 38.6(3) . . . . ?
C17 C16 C19 F3 159.89(19) . . . . ?
C18 C13 C14 C15 -0.5(3) . . . . ?
C19 C16 C17 C18 177.12(19) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.188
_oxdiff_exptl_absorpt_empirical_full_min 0.690
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: n-hexane / dichloromethane'
