# Supplementary Information (SI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2025

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
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data_nmtw1_273k
_database_code_depnum_ccdc_archive 'CCDC 2362545'
loop_
_audit_author_name
_audit_author_address
'Dier Shi'
;Zhejiang University
China
;
_audit_update_record             
;
2024-06-13 deposited with the CCDC.	2025-08-07 downloaded from the CCDC.
;
_audit_creation_date             2023-08-30
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C23 H32 F3 N5 O4'
_chemical_formula_sum            'C23 H32 F3 N5 O4'
_chemical_formula_weight         499.53
_chemical_absolute_configuration unk
_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      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_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'

_cell_length_a                   9.6872(7)
_cell_length_b                   15.0069(8)
_cell_length_c                   18.0085(11)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2618.0(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1798
_cell_measurement_temperature    273.0
_cell_measurement_theta_max      32.59
_cell_measurement_theta_min      2.39
_shelx_estimated_absorpt_T_max   0.995
_shelx_estimated_absorpt_T_min   0.961
_exptl_absorpt_coefficient_mu    0.102
_exptl_absorpt_correction_T_max  0.7466
_exptl_absorpt_correction_T_min  0.6696
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1465 before and 0.0612 after correction.
The Ratio of minimum to maximum transmission is 0.8969.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.267
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             1056
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-1.00 0.00 1.00 0.1690
1.00 0.00 -1.00 0.1540
0.00 -1.00 1.00 0.0130
0.00 1.00 -1.00 0.0370
-1.00 1.00 0.00 0.1760
1.00 1.00 -1.00 0.1430
-1.00 0.00 -1.00 0.1740
1.00 0.00 1.00 0.1560
-1.00 -1.00 -1.00 0.1490
1.00 1.00 1.00 0.1450
0.00 -1.00 0.00 0.0180
0.00 1.00 0.00 0.0240
0.00 -1.00 -1.00 0.0350
0.00 1.00 1.00 0.0210
0.00 0.00 1.00 0.0130
0.00 0.00 -1.00 0.0420

_exptl_crystal_size_max          0.389
_exptl_crystal_size_mid          0.085
_exptl_crystal_size_min          0.048
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0906
_diffrn_reflns_av_unetI/netI     0.1498
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.827
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            18815
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.787
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         33.584
_diffrn_reflns_theta_min         2.262
_diffrn_ambient_temperature      273.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.827
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.723
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.739
_reflns_number_gt                3211
_reflns_number_total             8140
_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 (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.531
_refine_diff_density_min         -0.384
_refine_diff_density_rms         0.049
_refine_ls_abs_structure_details 
;
 Flack x determined using 888 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -1.5(9)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.998
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     321
_refine_ls_number_reflns         8140
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.2279
_refine_ls_R_factor_gt           0.0828
_refine_ls_restrained_S_all      0.998
_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)+(0.0998P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1812
_refine_ls_wR_factor_ref         0.2493
_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:
 C9(H9), C3(H3A), C17(H17), C6(H6), C10(H10), C11(H11)
2.b Secondary CH2 refined with riding coordinates:
 C5(H5A,H5B), C2(H2A,H2B), C12(H12A,H12B), C1(H1A,H1B)
2.c Aromatic/amide H refined with riding coordinates:
 N3(H3), N5(H5), N1(H1)
2.d Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C), C20(H20A,H20B,H20C), C21(H21A,H21B,H21C), C15(H15A,H15B,
 H15C), C19(H19A,H19B,H19C)
;
_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
O3 O 0.1832(5) 0.4250(3) 0.9133(2) 0.0659(12) Uani 1 1 d . . . . .
O2 O 0.2281(5) 0.4631(2) 0.7064(2) 0.0644(12) Uani 1 1 d . . . . .
N3 N 0.2690(5) 0.3543(3) 0.6213(2) 0.0433(10) Uani 1 1 d . . . . .
H3 H 0.280890 0.298002 0.615017 0.052 Uiso 1 1 calc R U . . .
N4 N 0.1260(5) 0.3474(3) 0.8112(2) 0.0453(11) Uani 1 1 d . . . . .
O1 O 0.6597(5) 0.2827(3) 0.4628(3) 0.0797(15) Uani 1 1 d . . . . .
N5 N 0.4507(5) 0.4396(3) 0.8480(2) 0.0539(12) Uani 1 1 d . . . . .
H5 H 0.439825 0.477244 0.883510 0.065 Uiso 1 1 calc R U . . .
O4 O 0.5692(5) 0.4104(3) 0.7422(2) 0.0780(14) Uani 1 1 d . . . . .
N1 N 0.7830(6) 0.3908(4) 0.5214(3) 0.0725(15) Uani 1 1 d . . . . .
H1 H 0.862080 0.377682 0.502706 0.087 Uiso 1 1 calc R U . . .
C8 C 0.2219(6) 0.3851(3) 0.6873(3) 0.0427(12) Uani 1 1 d . . . . .
C16 C 0.2180(6) 0.3797(3) 0.8594(3) 0.0462(12) Uani 1 1 d . . . . .
C9 C 0.1555(6) 0.3134(3) 0.7364(3) 0.0440(12) Uani 1 1 d . . . . .
H9 H 0.214340 0.260359 0.738957 0.053 Uiso 1 1 calc R U . . .
C3 C 0.5529(5) 0.3839(3) 0.5519(3) 0.0405(11) Uani 1 1 d . . . . .
H3A H 0.543935 0.349378 0.597792 0.049 Uiso 1 1 calc R U . . .
C4 C 0.6699(6) 0.3453(4) 0.5062(3) 0.0527(14) Uani 1 1 d . . . . .
C17 C 0.3708(6) 0.3572(3) 0.8484(3) 0.0450(13) Uani 1 1 d . . . . .
H17 H 0.381130 0.328692 0.799740 0.054 Uiso 1 1 calc R U . . .
C6 C 0.2996(6) 0.4156(3) 0.5609(3) 0.0441(12) Uani 1 1 d . . . . .
H6 H 0.325858 0.473295 0.582035 0.053 Uiso 1 1 calc R U . . .
C5 C 0.4164(6) 0.3827(4) 0.5115(3) 0.0447(12) Uani 1 1 d . . . . .
H5A H 0.396459 0.322407 0.495242 0.054 Uiso 1 1 calc R U . . .
H5B H 0.422383 0.420221 0.467767 0.054 Uiso 1 1 calc R U . . .
C10 C 0.0151(6) 0.2902(4) 0.7049(3) 0.0523(14) Uani 1 1 d . . . . .
H10 H 0.000056 0.299298 0.651671 0.063 Uiso 1 1 calc R U . . .
N2 N 0.0749(7) 0.4341(5) 0.4813(4) 0.095(2) Uani 1 1 d . . . . .
C18 C 0.4261(7) 0.2915(4) 0.9085(3) 0.0596(16) Uani 1 1 d . . . . .
C22 C 0.5400(7) 0.4579(4) 0.7940(3) 0.0559(15) Uani 1 1 d . . . . .
C13 C -0.0790(7) 0.2245(5) 0.7453(3) 0.0650(18) Uani 1 1 d . . . . .
C2 C 0.6097(7) 0.4762(4) 0.5709(3) 0.0627(17) Uani 1 1 d . . . . .
H2A H 0.582561 0.519582 0.533750 0.075 Uiso 1 1 calc R U . . .
H2B H 0.576512 0.495766 0.619057 0.075 Uiso 1 1 calc R U . . .
C7 C 0.1729(7) 0.4273(4) 0.5162(3) 0.0603(15) Uani 1 1 d . . . . .
C11 C -0.0947(7) 0.3241(4) 0.7582(3) 0.0645(17) Uani 1 1 d . . . . .
H11 H -0.175853 0.354068 0.737407 0.077 Uiso 1 1 calc R U . . .
C12 C -0.0203(6) 0.3681(5) 0.8217(3) 0.0620(16) Uani 1 1 d . . . . .
H12A H -0.035100 0.432025 0.820806 0.074 Uiso 1 1 calc R U . . .
H12B H -0.052763 0.344905 0.868797 0.074 Uiso 1 1 calc R U . . .
C1 C 0.7634(8) 0.4642(5) 0.5718(4) 0.076(2) Uani 1 1 d . . . . .
H1A H 0.810217 0.517361 0.554250 0.091 Uiso 1 1 calc R U . . .
H1B H 0.796335 0.449742 0.621162 0.091 Uiso 1 1 calc R U . . .
C14 C -0.0231(9) 0.1646(5) 0.8048(4) 0.079(2) Uani 1 1 d . . . . .
H14A H 0.024452 0.115379 0.782326 0.119 Uiso 1 1 calc R U . . .
H14B H -0.097877 0.142647 0.834590 0.119 Uiso 1 1 calc R U . . .
H14C H 0.039838 0.197498 0.835491 0.119 Uiso 1 1 calc R U . . .
C20 C 0.4353(10) 0.3330(5) 0.9855(3) 0.091(2) Uani 1 1 d . . . . .
H20A H 0.497825 0.382607 0.984280 0.136 Uiso 1 1 calc R U . . .
H20B H 0.468302 0.289374 1.020193 0.136 Uiso 1 1 calc R U . . .
H20C H 0.345511 0.353203 1.000548 0.136 Uiso 1 1 calc R U . . .
C21 C 0.3257(10) 0.2124(5) 0.9145(5) 0.095(3) Uani 1 1 d . . . . .
H21A H 0.234859 0.234057 0.925734 0.142 Uiso 1 1 calc R U . . .
H21B H 0.355880 0.173037 0.953199 0.142 Uiso 1 1 calc R U . . .
H21C H 0.323835 0.180826 0.868118 0.142 Uiso 1 1 calc R U . . .
C15 C -0.1885(8) 0.1825(6) 0.6970(4) 0.089(2) Uani 1 1 d . . . . .
H15A H -0.214781 0.223507 0.658592 0.134 Uiso 1 1 calc R U . . .
H15B H -0.267668 0.168144 0.726711 0.134 Uiso 1 1 calc R U . . .
H15C H -0.152658 0.129042 0.674857 0.134 Uiso 1 1 calc R U . . .
C19 C 0.5681(10) 0.2586(6) 0.8853(5) 0.103(3) Uani 1 1 d . . . . .
H19A H 0.605533 0.221260 0.923583 0.155 Uiso 1 1 calc R U . . .
H19B H 0.628056 0.308649 0.877452 0.155 Uiso 1 1 calc R U . . .
H19C H 0.560319 0.225060 0.840058 0.155 Uiso 1 1 calc R U . . .
F1 F 0.6775(12) 0.5690(6) 0.7462(3) 0.256(6) Uani 1 1 d . . . . .
F2 F 0.5482(7) 0.6088(4) 0.8314(6) 0.177(3) Uani 1 1 d . . . . .
F3 F 0.7115(8) 0.5407(5) 0.8536(4) 0.174(3) Uani 1 1 d . . . . .
C23 C 0.6152(10) 0.5438(6) 0.8013(4) 0.085(2) Uani 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
O3 C16 1.232(6) . ?
O2 C8 1.221(6) . ?
N3 H3 0.8600 . ?
N3 C8 1.354(6) . ?
N3 C6 1.454(6) . ?
N4 C16 1.334(7) . ?
N4 C9 1.468(6) . ?
N4 C12 1.463(7) . ?
O1 C4 1.227(6) . ?
N5 H5 0.8600 . ?
N5 C17 1.460(7) . ?
N5 C22 1.330(7) . ?
O4 C22 1.207(6) . ?
N1 H1 0.8600 . ?
N1 C4 1.320(8) . ?
N1 C1 1.439(8) . ?
C8 C9 1.535(7) . ?
C16 C17 1.531(8) . ?
C9 H9 0.9800 . ?
C9 C10 1.515(8) . ?
C3 H3A 0.9800 . ?
C3 C4 1.515(8) . ?
C3 C5 1.510(7) . ?
C3 C2 1.529(8) . ?
C17 H17 0.9800 . ?
C17 C18 1.559(8) . ?
C6 H6 0.9800 . ?
C6 C5 1.521(7) . ?
C6 C7 1.478(9) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C10 H10 0.9800 . ?
C10 C13 1.526(8) . ?
C10 C11 1.520(8) . ?
N2 C7 1.143(8) . ?
C18 C20 1.522(8) . ?
C18 C21 1.538(10) . ?
C18 C19 1.521(11) . ?
C22 C23 1.486(10) . ?
C13 C11 1.521(9) . ?
C13 C14 1.499(9) . ?
C13 C15 1.510(9) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C2 C1 1.500(10) . ?
C11 H11 0.9800 . ?
C11 C12 1.504(8) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
F1 C23 1.221(9) . ?
F2 C23 1.291(10) . ?
F3 C23 1.327(10) . ?

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 N3 H3 119.7 . . ?
C8 N3 C6 120.6(4) . . ?
C6 N3 H3 119.7 . . ?
C16 N4 C9 126.3(4) . . ?
C16 N4 C12 119.1(4) . . ?
C12 N4 C9 112.4(4) . . ?
C17 N5 H5 119.2 . . ?
C22 N5 H5 119.2 . . ?
C22 N5 C17 121.6(4) . . ?
C4 N1 H1 122.7 . . ?
C4 N1 C1 114.7(5) . . ?
C1 N1 H1 122.7 . . ?
O2 C8 N3 124.0(5) . . ?
O2 C8 C9 121.9(4) . . ?
N3 C8 C9 114.0(4) . . ?
O3 C16 N4 122.0(5) . . ?
O3 C16 C17 119.2(5) . . ?
N4 C16 C17 118.8(4) . . ?
N4 C9 C8 111.5(4) . . ?
N4 C9 H9 110.7 . . ?
N4 C9 C10 104.4(4) . . ?
C8 C9 H9 110.7 . . ?
C10 C9 C8 108.8(4) . . ?
C10 C9 H9 110.7 . . ?
C4 C3 H3A 108.8 . . ?
C4 C3 C2 101.5(5) . . ?
C5 C3 H3A 108.8 . . ?
C5 C3 C4 112.9(4) . . ?
C5 C3 C2 115.7(5) . . ?
C2 C3 H3A 108.8 . . ?
O1 C4 N1 126.6(6) . . ?
O1 C4 C3 125.4(6) . . ?
N1 C4 C3 108.0(5) . . ?
N5 C17 C16 109.0(4) . . ?
N5 C17 H17 108.1 . . ?
N5 C17 C18 110.9(4) . . ?
C16 C17 H17 108.1 . . ?
C16 C17 C18 112.5(5) . . ?
C18 C17 H17 108.1 . . ?
N3 C6 H6 108.7 . . ?
N3 C6 C5 112.6(4) . . ?
N3 C6 C7 108.2(4) . . ?
C5 C6 H6 108.7 . . ?
C7 C6 H6 108.7 . . ?
C7 C6 C5 109.7(4) . . ?
C3 C5 C6 111.5(4) . . ?
C3 C5 H5A 109.3 . . ?
C3 C5 H5B 109.3 . . ?
C6 C5 H5A 109.3 . . ?
C6 C5 H5B 109.3 . . ?
H5A C5 H5B 108.0 . . ?
C9 C10 H10 117.9 . . ?
C9 C10 C13 120.5(5) . . ?
C9 C10 C11 108.4(4) . . ?
C13 C10 H10 117.9 . . ?
C11 C10 H10 117.9 . . ?
C11 C10 C13 59.9(4) . . ?
C20 C18 C17 113.2(5) . . ?
C20 C18 C21 106.8(6) . . ?
C21 C18 C17 108.6(5) . . ?
C19 C18 C17 109.0(5) . . ?
C19 C18 C20 109.3(7) . . ?
C19 C18 C21 109.9(6) . . ?
N5 C22 C23 115.7(5) . . ?
O4 C22 N5 126.5(6) . . ?
O4 C22 C23 117.7(6) . . ?
C11 C13 C10 59.8(4) . . ?
C14 C13 C10 120.8(6) . . ?
C14 C13 C11 121.0(5) . . ?
C14 C13 C15 114.5(6) . . ?
C15 C13 C10 114.5(5) . . ?
C15 C13 C11 115.3(6) . . ?
C3 C2 H2A 110.8 . . ?
C3 C2 H2B 110.8 . . ?
H2A C2 H2B 108.9 . . ?
C1 C2 C3 104.5(5) . . ?
C1 C2 H2A 110.8 . . ?
C1 C2 H2B 110.8 . . ?
N2 C7 C6 178.3(8) . . ?
C10 C11 C13 60.3(4) . . ?
C10 C11 H11 118.3 . . ?
C13 C11 H11 118.3 . . ?
C12 C11 C10 106.9(5) . . ?
C12 C11 C13 120.0(6) . . ?
C12 C11 H11 118.3 . . ?
N4 C12 C11 105.9(5) . . ?
N4 C12 H12A 110.6 . . ?
N4 C12 H12B 110.6 . . ?
C11 C12 H12A 110.6 . . ?
C11 C12 H12B 110.6 . . ?
H12A C12 H12B 108.7 . . ?
N1 C1 C2 102.5(6) . . ?
N1 C1 H1A 111.3 . . ?
N1 C1 H1B 111.3 . . ?
C2 C1 H1A 111.3 . . ?
C2 C1 H1B 111.3 . . ?
H1A C1 H1B 109.2 . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C18 C20 H20A 109.5 . . ?
C18 C20 H20B 109.5 . . ?
C18 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C18 C21 H21A 109.5 . . ?
C18 C21 H21B 109.5 . . ?
C18 C21 H21C 109.5 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C13 C15 H15A 109.5 . . ?
C13 C15 H15B 109.5 . . ?
C13 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
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 . . ?
F1 C23 C22 116.0(7) . . ?
F1 C23 F2 110.9(9) . . ?
F1 C23 F3 103.9(9) . . ?
F2 C23 C22 116.5(7) . . ?
F2 C23 F3 94.7(7) . . ?
F3 C23 C22 112.1(7) . . ?

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
O3 C16 C17 N5 -54.7(6) . . . . ?
O3 C16 C17 C18 68.7(6) . . . . ?
O2 C8 C9 N4 -10.2(8) . . . . ?
O2 C8 C9 C10 104.4(6) . . . . ?
N3 C8 C9 N4 171.2(5) . . . . ?
N3 C8 C9 C10 -74.2(6) . . . . ?
N3 C6 C5 C3 -68.6(6) . . . . ?
N4 C16 C17 N5 127.3(5) . . . . ?
N4 C16 C17 C18 -109.3(5) . . . . ?
N4 C9 C10 C13 -57.1(6) . . . . ?
N4 C9 C10 C11 8.2(6) . . . . ?
N5 C17 C18 C20 53.2(7) . . . . ?
N5 C17 C18 C21 171.7(5) . . . . ?
N5 C17 C18 C19 -68.7(7) . . . . ?
N5 C22 C23 F1 -167.0(9) . . . . ?
N5 C22 C23 F2 -33.7(11) . . . . ?
N5 C22 C23 F3 73.9(9) . . . . ?
O4 C22 C23 F1 15.9(13) . . . . ?
O4 C22 C23 F2 149.2(8) . . . . ?
O4 C22 C23 F3 -103.3(8) . . . . ?
C8 N3 C6 C5 148.7(5) . . . . ?
C8 N3 C6 C7 -89.9(6) . . . . ?
C8 C9 C10 C13 -176.2(5) . . . . ?
C8 C9 C10 C11 -110.9(5) . . . . ?
C16 N4 C9 C8 -59.8(7) . . . . ?
C16 N4 C9 C10 -177.1(5) . . . . ?
C16 N4 C12 C11 178.9(5) . . . . ?
C16 C17 C18 C20 -69.2(7) . . . . ?
C16 C17 C18 C21 49.3(6) . . . . ?
C16 C17 C18 C19 168.9(6) . . . . ?
C9 N4 C16 O3 163.2(5) . . . . ?
C9 N4 C16 C17 -18.8(8) . . . . ?
C9 N4 C12 C11 14.7(7) . . . . ?
C9 C10 C13 C11 94.7(6) . . . . ?
C9 C10 C13 C14 -15.6(8) . . . . ?
C9 C10 C13 C15 -159.1(6) . . . . ?
C9 C10 C11 C13 -115.1(5) . . . . ?
C9 C10 C11 C12 0.2(7) . . . . ?
C3 C2 C1 N1 27.1(7) . . . . ?
C4 N1 C1 C2 -15.7(8) . . . . ?
C4 C3 C5 C6 175.8(4) . . . . ?
C4 C3 C2 C1 -28.6(6) . . . . ?
C17 N5 C22 O4 -2.5(9) . . . . ?
C17 N5 C22 C23 -179.4(6) . . . . ?
C6 N3 C8 O2 -15.4(8) . . . . ?
C6 N3 C8 C9 163.2(5) . . . . ?
C5 C3 C4 O1 -35.3(7) . . . . ?
C5 C3 C4 N1 144.5(5) . . . . ?
C5 C3 C2 C1 -151.2(5) . . . . ?
C10 C13 C11 C12 -93.2(6) . . . . ?
C10 C11 C12 N4 -8.7(7) . . . . ?
C22 N5 C17 C16 -129.0(5) . . . . ?
C22 N5 C17 C18 106.6(6) . . . . ?
C13 C10 C11 C12 115.4(6) . . . . ?
C13 C11 C12 N4 56.3(7) . . . . ?
C2 C3 C4 O1 -159.9(6) . . . . ?
C2 C3 C4 N1 19.9(6) . . . . ?
C2 C3 C5 C6 -67.8(6) . . . . ?
C7 C6 C5 C3 170.8(4) . . . . ?
C11 C10 C13 C14 -110.4(6) . . . . ?
C11 C10 C13 C15 106.2(7) . . . . ?
C12 N4 C16 O3 1.5(8) . . . . ?
C12 N4 C16 C17 179.5(5) . . . . ?
C12 N4 C9 C8 102.9(6) . . . . ?
C12 N4 C9 C10 -14.4(6) . . . . ?
C1 N1 C4 O1 176.8(6) . . . . ?
C1 N1 C4 C3 -3.0(7) . . . . ?
C14 C13 C11 C10 109.9(7) . . . . ?
C14 C13 C11 C12 16.7(9) . . . . ?
C15 C13 C11 C10 -104.8(6) . . . . ?
C15 C13 C11 C12 161.9(5) . . . . ?


_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_nmtw_1_268k_0m
_database_code_depnum_ccdc_archive 'CCDC 2362546'
loop_
_audit_author_name
_audit_author_address
'Dier Shi'
;Zhejiang University
China
;
_audit_update_record             
;
2024-06-13 deposited with the CCDC.	2025-08-07 downloaded from the CCDC.
;
_audit_creation_date             2023-05-17
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2019/2
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C23 H32 F3 N5 O4'
_chemical_formula_sum            'C23 H32 F3 N5 O4'
_chemical_formula_weight         499.53
_chemical_absolute_configuration unk
_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      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_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'

_cell_length_a                   9.2453(5)
_cell_length_b                   15.1879(8)
_cell_length_c                   18.1544(8)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2549.2(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4419
_cell_measurement_temperature    268.0
_cell_measurement_theta_max      27.31
_cell_measurement_theta_min      2.47
_shelx_estimated_absorpt_T_max   0.993
_shelx_estimated_absorpt_T_min   0.971
_exptl_absorpt_coefficient_mu    0.105
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6731
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1160 before and 0.0704 after correction.
The Ratio of minimum to maximum transmission is 0.9028.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.302
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             1056
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.113
_exptl_crystal_size_min          0.07
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0916
_diffrn_reflns_av_unetI/netI     0.0760
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            27731
_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         27.510
_diffrn_reflns_theta_min         2.244
_diffrn_ambient_temperature      268.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.773
_reflns_Friedel_fraction_full    0.997
_reflns_Friedel_fraction_max     0.996
_reflns_number_gt                3622
_reflns_number_total             5830
_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 (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/2 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.266
_refine_diff_density_min         -0.255
_refine_diff_density_rms         0.050
_refine_ls_abs_structure_details 
;
 Flack x determined using 1090 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.8(6)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.104
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     321
_refine_ls_number_reflns         5830
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1331
_refine_ls_R_factor_gt           0.0737
_refine_ls_restrained_S_all      1.104
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0369P)²+1.1552P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1255
_refine_ls_wR_factor_ref         0.1520
_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:
 C9(H9), C6(H6), C17(H17), C3(H3A), C10(H10), C11(H11)
2.b Secondary CH2 refined with riding coordinates:
 C5(H5A,H5B), C2(H2A,H2B), C12(H12A,H12B), C1(H1A,H1B)
2.c Aromatic/amide H refined with riding coordinates:
 N3(H3), N5(H5), N1(H1)
2.d Idealised Me refined as rotating group:
 C20(H20A,H20B,H20C), C14(H14A,H14B,H14C), C21(H21A,H21B,H21C), C19(H19A,H19B,
 H19C), C15(H15A,H15B,H15C)
;
_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
N4 N -0.8580(4) -0.6843(3) -0.1912(2) 0.0388(10) Uani 1 1 d . . . . .
O2 O -0.7600(4) -0.5563(2) -0.28528(19) 0.0548(10) Uani 1 1 d . . . . .
N3 N -0.6801(4) -0.6519(2) -0.3712(2) 0.0353(9) Uani 1 1 d . . . . .
H3 H -0.665082 -0.706161 -0.382397 0.042 Uiso 1 1 calc R U . . .
O3 O -0.8284(4) -0.6204(3) -0.0810(2) 0.0587(10) Uani 1 1 d . . . . .
O1 O -0.2777(4) -0.7319(2) -0.5177(2) 0.0605(11) Uani 1 1 d . . . . .
N5 N -0.5536(4) -0.5700(2) -0.1398(2) 0.0424(10) Uani 1 1 d . . . . .
H5 H -0.581627 -0.535866 -0.104767 0.051 Uiso 1 1 calc R U . . .
O4 O -0.4076(5) -0.5805(3) -0.2407(2) 0.0825(14) Uani 1 1 d . . . . .
C8 C -0.7492(5) -0.6314(3) -0.3079(3) 0.0355(10) Uani 1 1 d . . . . .
N1 N -0.1266(5) -0.6343(3) -0.4618(3) 0.0574(13) Uani 1 1 d . . . . .
H1 H -0.048198 -0.651905 -0.482633 0.069 Uiso 1 1 calc R U . . .
F2 F -0.4889(6) -0.3985(3) -0.1334(3) 0.1135(16) Uani 1 1 d . . . . .
C9 C -0.8104(5) -0.7104(3) -0.2653(2) 0.0334(10) Uani 1 1 d . . . . .
H9 H -0.737897 -0.757315 -0.262020 0.040 Uiso 1 1 calc R U . . .
C4 C -0.2544(6) -0.6713(3) -0.4748(3) 0.0434(12) Uani 1 1 d . . . . .
C16 C -0.7747(5) -0.6522(3) -0.1367(3) 0.0401(11) Uani 1 1 d . . . . .
C6 C -0.6312(5) -0.5826(3) -0.4204(3) 0.0395(11) Uani 1 1 d . . . . .
H6 H -0.598410 -0.532284 -0.391021 0.047 Uiso 1 1 calc R U . . .
C17 C -0.6101(5) -0.6593(3) -0.1440(3) 0.0396(11) Uani 1 1 d . . . . .
H17 H -0.588677 -0.682072 -0.193329 0.048 Uiso 1 1 calc R U . . .
C3 C -0.3663(5) -0.6254(3) -0.4281(3) 0.0384(11) Uani 1 1 d . . . . .
H3A H -0.384660 -0.660987 -0.384024 0.046 Uiso 1 1 calc R U . . .
C7 C -0.7522(6) -0.5543(4) -0.4681(3) 0.0509(13) Uani 1 1 d . . . . .
N2 N -0.8427(6) -0.5351(4) -0.5070(3) 0.0698(15) Uani 1 1 d . . . . .
C5 C -0.5068(5) -0.6139(3) -0.4696(3) 0.0395(11) Uani 1 1 d . . . . .
H5A H -0.533284 -0.669514 -0.492097 0.047 Uiso 1 1 calc R U . . .
H5B H -0.492349 -0.571396 -0.508863 0.047 Uiso 1 1 calc R U . . .
C2 C -0.2901(6) -0.5406(3) -0.4052(3) 0.0493(13) Uani 1 1 d . . . . .
H2A H -0.314792 -0.492825 -0.438329 0.059 Uiso 1 1 calc R U . . .
H2B H -0.316880 -0.524074 -0.355453 0.059 Uiso 1 1 calc R U . . .
C18 C -0.5378(6) -0.7215(3) -0.0873(3) 0.0487(13) Uani 1 1 d . . . . .
C10 C -0.9470(5) -0.7447(3) -0.3019(3) 0.0433(12) Uani 1 1 d . . . . .
H10 H -0.957152 -0.736352 -0.355176 0.052 Uiso 1 1 calc R U . . .
C12 C -1.0161(5) -0.6733(4) -0.1874(3) 0.0467(13) Uani 1 1 d . . . . .
H12A H -1.041982 -0.611475 -0.188724 0.056 Uiso 1 1 calc R U . . .
H12B H -1.054119 -0.699092 -0.142478 0.056 Uiso 1 1 calc R U . . .
C13 C -1.0367(6) -0.8155(3) -0.2658(3) 0.0503(13) Uani 1 1 d . . . . .
C1 C -0.1300(6) -0.5617(4) -0.4097(3) 0.0550(14) Uani 1 1 d . . . . .
H1A H -0.075237 -0.511685 -0.427789 0.066 Uiso 1 1 calc R U . . .
H1B H -0.092109 -0.579309 -0.362137 0.066 Uiso 1 1 calc R U . . .
C11 C -1.0738(6) -0.7203(4) -0.2535(3) 0.0525(14) Uani 1 1 d . . . . .
H11 H -1.160909 -0.696803 -0.277183 0.063 Uiso 1 1 calc R U . . .
C20 C -0.5359(8) -0.6818(4) -0.0099(3) 0.0662(17) Uani 1 1 d . . . . .
H20A H -0.632106 -0.664474 0.003611 0.099 Uiso 1 1 calc R U . . .
H20B H -0.473567 -0.631280 -0.009313 0.099 Uiso 1 1 calc R U . . .
H20C H -0.500776 -0.724822 0.024460 0.099 Uiso 1 1 calc R U . . .
C22 C -0.4592(7) -0.5401(4) -0.1894(3) 0.0561(15) Uani 1 1 d . . . . .
C14 C -0.9802(7) -0.8720(4) -0.2036(3) 0.0626(16) Uani 1 1 d . . . . .
H14A H -0.916776 -0.837690 -0.173114 0.094 Uiso 1 1 calc R U . . .
H14B H -0.928162 -0.921240 -0.223487 0.094 Uiso 1 1 calc R U . . .
H14C H -1.059927 -0.892987 -0.174545 0.094 Uiso 1 1 calc R U . . .
F1 F -0.2824(6) -0.4407(4) -0.1534(5) 0.193(4) Uani 1 1 d . . . . .
C21 C -0.6194(7) -0.8085(4) -0.0847(4) 0.0711(18) Uani 1 1 d . . . . .
H21A H -0.622512 -0.833722 -0.133148 0.107 Uiso 1 1 calc R U . . .
H21B H -0.716153 -0.798332 -0.067528 0.107 Uiso 1 1 calc R U . . .
H21C H -0.570928 -0.848181 -0.051783 0.107 Uiso 1 1 calc R U . . .
F3 F -0.4120(10) -0.4027(4) -0.2392(3) 0.209(4) Uani 1 1 d . . . . .
C19 C -0.3814(6) -0.7382(5) -0.1114(4) 0.078(2) Uani 1 1 d . . . . .
H19A H -0.329451 -0.683438 -0.111978 0.117 Uiso 1 1 calc R U . . .
H19B H -0.380770 -0.763510 -0.159794 0.117 Uiso 1 1 calc R U . . .
H19C H -0.336020 -0.777926 -0.077381 0.117 Uiso 1 1 calc R U . . .
C15 C -1.1352(7) -0.8648(4) -0.3183(3) 0.075(2) Uani 1 1 d . . . . .
H15A H -1.082261 -0.911816 -0.341158 0.112 Uiso 1 1 calc R U . . .
H15B H -1.169997 -0.825153 -0.355433 0.112 Uiso 1 1 calc R U . . .
H15C H -1.215619 -0.888679 -0.291461 0.112 Uiso 1 1 calc R U . . .
C23 C -0.4098(10) -0.4469(5) -0.1782(4) 0.089(2) Uani 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
N4 C9 1.469(6) . ?
N4 C16 1.345(6) . ?
N4 C12 1.473(6) . ?
O2 C8 1.217(5) . ?
N3 H3 0.8600 . ?
N3 C8 1.351(6) . ?
N3 C6 1.453(6) . ?
O3 C16 1.225(6) . ?
O1 C4 1.224(6) . ?
N5 H5 0.8600 . ?
N5 C17 1.456(6) . ?
N5 C22 1.334(6) . ?
O4 C22 1.214(7) . ?
C8 C9 1.536(6) . ?
N1 H1 0.8600 . ?
N1 C4 1.329(7) . ?
N1 C1 1.453(7) . ?
F2 C23 1.318(8) . ?
C9 H9 0.9800 . ?
C9 C10 1.519(6) . ?
C4 C3 1.509(7) . ?
C16 C17 1.531(7) . ?
C6 H6 0.9800 . ?
C6 C7 1.478(7) . ?
C6 C5 1.532(6) . ?
C17 H17 0.9800 . ?
C17 C18 1.549(7) . ?
C3 H3A 0.9800 . ?
C3 C5 1.512(6) . ?
C3 C2 1.526(7) . ?
C7 N2 1.133(7) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C2 C1 1.516(7) . ?
C18 C20 1.529(7) . ?
C18 C21 1.521(7) . ?
C18 C19 1.531(8) . ?
C10 H10 0.9800 . ?
C10 C13 1.509(7) . ?
C10 C11 1.511(7) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C12 C11 1.495(7) . ?
C13 C11 1.504(8) . ?
C13 C14 1.512(7) . ?
C13 C15 1.515(7) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C11 H11 0.9800 . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C22 C23 1.502(8) . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
F1 C23 1.265(10) . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
F3 C23 1.295(9) . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C9 N4 C12 111.7(4) . . ?
C16 N4 C9 126.8(4) . . ?
C16 N4 C12 119.5(4) . . ?
C8 N3 H3 119.9 . . ?
C8 N3 C6 120.2(4) . . ?
C6 N3 H3 119.9 . . ?
C17 N5 H5 119.5 . . ?
C22 N5 H5 119.5 . . ?
C22 N5 C17 121.1(4) . . ?
O2 C8 N3 122.8(4) . . ?
O2 C8 C9 122.1(4) . . ?
N3 C8 C9 115.0(4) . . ?
C4 N1 H1 122.7 . . ?
C4 N1 C1 114.7(4) . . ?
C1 N1 H1 122.7 . . ?
N4 C9 C8 111.2(4) . . ?
N4 C9 H9 110.2 . . ?
N4 C9 C10 104.1(4) . . ?
C8 C9 H9 110.2 . . ?
C10 C9 C8 110.7(4) . . ?
C10 C9 H9 110.2 . . ?
O1 C4 N1 125.9(5) . . ?
O1 C4 C3 125.7(5) . . ?
N1 C4 C3 108.3(4) . . ?
N4 C16 C17 118.7(4) . . ?
O3 C16 N4 121.2(4) . . ?
O3 C16 C17 120.1(4) . . ?
N3 C6 H6 109.1 . . ?
N3 C6 C7 109.6(4) . . ?
N3 C6 C5 111.6(4) . . ?
C7 C6 H6 109.1 . . ?
C7 C6 C5 108.4(4) . . ?
C5 C6 H6 109.1 . . ?
N5 C17 C16 106.6(4) . . ?
N5 C17 H17 107.7 . . ?
N5 C17 C18 112.3(4) . . ?
C16 C17 H17 107.7 . . ?
C16 C17 C18 114.5(4) . . ?
C18 C17 H17 107.7 . . ?
C4 C3 H3A 108.8 . . ?
C4 C3 C5 111.2(4) . . ?
C4 C3 C2 103.1(4) . . ?
C5 C3 H3A 108.8 . . ?
C5 C3 C2 115.8(4) . . ?
C2 C3 H3A 108.8 . . ?
N2 C7 C6 177.0(7) . . ?
C6 C5 H5A 109.0 . . ?
C6 C5 H5B 109.0 . . ?
C3 C5 C6 112.9(4) . . ?
C3 C5 H5A 109.0 . . ?
C3 C5 H5B 109.0 . . ?
H5A C5 H5B 107.8 . . ?
C3 C2 H2A 110.8 . . ?
C3 C2 H2B 110.8 . . ?
H2A C2 H2B 108.8 . . ?
C1 C2 C3 105.0(4) . . ?
C1 C2 H2A 110.8 . . ?
C1 C2 H2B 110.8 . . ?
C20 C18 C17 112.0(4) . . ?
C20 C18 C19 108.4(5) . . ?
C21 C18 C17 109.6(4) . . ?
C21 C18 C20 108.6(5) . . ?
C21 C18 C19 109.5(5) . . ?
C19 C18 C17 108.6(5) . . ?
C9 C10 H10 117.9 . . ?
C13 C10 C9 120.8(4) . . ?
C13 C10 H10 117.9 . . ?
C13 C10 C11 59.7(3) . . ?
C11 C10 C9 107.8(4) . . ?
C11 C10 H10 117.9 . . ?
N4 C12 H12A 110.7 . . ?
N4 C12 H12B 110.7 . . ?
N4 C12 C11 105.2(4) . . ?
H12A C12 H12B 108.8 . . ?
C11 C12 H12A 110.7 . . ?
C11 C12 H12B 110.7 . . ?
C10 C13 C14 122.6(5) . . ?
C10 C13 C15 114.2(4) . . ?
C11 C13 C10 60.2(3) . . ?
C11 C13 C14 120.9(5) . . ?
C11 C13 C15 115.6(5) . . ?
C14 C13 C15 113.4(5) . . ?
N1 C1 C2 102.5(4) . . ?
N1 C1 H1A 111.3 . . ?
N1 C1 H1B 111.3 . . ?
C2 C1 H1A 111.3 . . ?
C2 C1 H1B 111.3 . . ?
H1A C1 H1B 109.2 . . ?
C10 C11 H11 118.2 . . ?
C12 C11 C10 107.9(4) . . ?
C12 C11 C13 119.8(5) . . ?
C12 C11 H11 118.2 . . ?
C13 C11 C10 60.1(3) . . ?
C13 C11 H11 118.2 . . ?
C18 C20 H20A 109.5 . . ?
C18 C20 H20B 109.5 . . ?
C18 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
N5 C22 C23 115.4(5) . . ?
O4 C22 N5 127.1(5) . . ?
O4 C22 C23 117.5(6) . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C18 C21 H21A 109.5 . . ?
C18 C21 H21B 109.5 . . ?
C18 C21 H21C 109.5 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
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 . . ?
C13 C15 H15A 109.5 . . ?
C13 C15 H15B 109.5 . . ?
C13 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
F2 C23 C22 116.1(6) . . ?
F1 C23 F2 104.8(7) . . ?
F1 C23 C22 113.6(8) . . ?
F1 C23 F3 106.3(7) . . ?
F3 C23 F2 103.3(8) . . ?
F3 C23 C22 111.6(6) . . ?

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
N4 C9 C10 C13 -53.6(6) . . . . ?
N4 C9 C10 C11 11.3(5) . . . . ?
N4 C16 C17 N5 121.9(5) . . . . ?
N4 C16 C17 C18 -113.3(5) . . . . ?
N4 C12 C11 C10 -9.5(6) . . . . ?
N4 C12 C11 C13 55.7(6) . . . . ?
O2 C8 C9 N4 -9.7(6) . . . . ?
O2 C8 C9 C10 105.6(5) . . . . ?
N3 C8 C9 N4 169.0(4) . . . . ?
N3 C8 C9 C10 -75.8(5) . . . . ?
N3 C6 C5 C3 -71.8(5) . . . . ?
O3 C16 C17 N5 -60.4(6) . . . . ?
O3 C16 C17 C18 64.4(6) . . . . ?
O1 C4 C3 C5 -38.4(7) . . . . ?
O1 C4 C3 C2 -163.1(5) . . . . ?
N5 C17 C18 C20 49.1(6) . . . . ?
N5 C17 C18 C21 169.7(4) . . . . ?
N5 C17 C18 C19 -70.6(5) . . . . ?
N5 C22 C23 F2 -16.1(10) . . . . ?
N5 C22 C23 F1 105.6(8) . . . . ?
N5 C22 C23 F3 -134.2(8) . . . . ?
O4 C22 C23 F2 165.4(7) . . . . ?
O4 C22 C23 F1 -72.8(10) . . . . ?
O4 C22 C23 F3 47.4(11) . . . . ?
C8 N3 C6 C7 -83.3(5) . . . . ?
C8 N3 C6 C5 156.6(4) . . . . ?
C8 C9 C10 C13 -173.1(4) . . . . ?
C8 C9 C10 C11 -108.3(4) . . . . ?
N1 C4 C3 C5 141.1(4) . . . . ?
N1 C4 C3 C2 16.4(6) . . . . ?
C9 N4 C16 O3 168.9(4) . . . . ?
C9 N4 C16 C17 -13.4(7) . . . . ?
C9 N4 C12 C11 17.6(6) . . . . ?
C9 C10 C13 C11 93.8(5) . . . . ?
C9 C10 C13 C14 -15.9(8) . . . . ?
C9 C10 C13 C15 -159.5(5) . . . . ?
C9 C10 C11 C12 -1.1(6) . . . . ?
C9 C10 C11 C13 -115.7(4) . . . . ?
C4 N1 C1 C2 -14.6(7) . . . . ?
C4 C3 C5 C6 169.8(4) . . . . ?
C4 C3 C2 C1 -24.6(5) . . . . ?
C16 N4 C9 C8 -62.9(6) . . . . ?
C16 N4 C9 C10 177.9(4) . . . . ?
C16 N4 C12 C11 -177.1(4) . . . . ?
C16 C17 C18 C20 -72.7(6) . . . . ?
C16 C17 C18 C21 48.0(6) . . . . ?
C16 C17 C18 C19 167.6(5) . . . . ?
C6 N3 C8 O2 -8.0(7) . . . . ?
C6 N3 C8 C9 173.3(4) . . . . ?
C17 N5 C22 O4 -1.6(9) . . . . ?
C17 N5 C22 C23 -179.9(6) . . . . ?
C3 C2 C1 N1 23.7(6) . . . . ?
C7 C6 C5 C3 167.4(4) . . . . ?
C5 C3 C2 C1 -146.3(4) . . . . ?
C2 C3 C5 C6 -73.0(5) . . . . ?
C10 C13 C11 C12 -94.5(5) . . . . ?
C12 N4 C9 C8 101.1(5) . . . . ?
C12 N4 C9 C10 -18.1(5) . . . . ?
C12 N4 C16 O3 6.0(8) . . . . ?
C12 N4 C16 C17 -176.3(4) . . . . ?
C13 C10 C11 C12 114.6(5) . . . . ?
C1 N1 C4 O1 178.3(5) . . . . ?
C1 N1 C4 C3 -1.2(7) . . . . ?
C11 C10 C13 C14 -109.6(6) . . . . ?
C11 C10 C13 C15 106.8(6) . . . . ?
C22 N5 C17 C16 -130.9(5) . . . . ?
C22 N5 C17 C18 103.0(5) . . . . ?
C14 C13 C11 C10 112.4(6) . . . . ?
C14 C13 C11 C12 17.9(8) . . . . ?
C15 C13 C11 C10 -104.5(5) . . . . ?
C15 C13 C11 C12 161.0(5) . . . . ?

_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_nmtw_1_173k_0m
_database_code_depnum_ccdc_archive 'CCDC 2362548'
loop_
_audit_author_name
_audit_author_address
'Dier Shi'
;Zhejiang University
China
;
_audit_update_record             
;
2024-06-13 deposited with the CCDC.	2025-08-07 downloaded from the CCDC.
;
_audit_creation_date             2024-05-15
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C23 H32 F3 N5 O4'
_chemical_formula_sum            'C23 H32 F3 N5 O4'
_chemical_formula_weight         499.53
_chemical_absolute_configuration unk
_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      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_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'

_cell_length_a                   9.2125(4)
_cell_length_b                   15.0829(6)
_cell_length_c                   18.0498(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2508.04(16)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    6228
_cell_measurement_temperature    173.00
_cell_measurement_theta_max      27.14
_cell_measurement_theta_min      2.48
_shelx_estimated_absorpt_T_max   0.993
_shelx_estimated_absorpt_T_min   0.971
_exptl_absorpt_coefficient_mu    0.106
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6936
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.323
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             1056
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0.00 -1.00 -1.00 0.0350
0.00 1.00 1.00 0.0280
-1.00 1.00 1.00 0.0980
1.00 -1.00 -1.00 0.1260
1.00 0.00 0.00 0.1340
-1.00 0.00 0.00 0.1400
1.00 1.00 0.00 0.1170
0.00 1.00 -1.00 0.0490
0.00 -1.00 1.00 0.0120

_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.113
_exptl_crystal_size_min          0.07
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0787
_diffrn_reflns_av_unetI/netI     0.0582
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            28799
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.477
_diffrn_reflns_theta_min         2.257
_diffrn_ambient_temperature      173.00
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.773
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.999
_reflns_number_gt                4407
_reflns_number_total             5728
_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 (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.237
_refine_diff_density_min         -0.290
_refine_diff_density_rms         0.051
_refine_ls_abs_structure_details 
;
 Flack x determined using 1470 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.3(5)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.111
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     325
_refine_ls_number_reflns         5728
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0837
_refine_ls_R_factor_gt           0.0550
_refine_ls_restrained_S_all      1.111
_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)+(0.0297P)²+0.8346P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0981
_refine_ls_wR_factor_ref         0.1107
_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:
 C17(H17), C9(H9), C6(H6), C10(H10), C3(H3A), C11(H11)
2.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C5(H5A,H5B), C1(H1A,H1B), C12(H12A,H12B)
2.c Aromatic/amide H refined with riding coordinates:
 N3(H3), N1(H1)
2.d Idealised Me refined as rotating group:
 C20(H20A,H20B,H20C), C14(H14A,H14B,H14C), C15(H15A,H15B,H15C), C21(H21A,H21B,
 H21C), C19(H19A,H19B,H19C)
;
_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
O2 O 0.7568(3) 0.55558(14) 0.71582(13) 0.0336(6) Uani 1 1 d . . . . .
O3 O 0.8281(3) 0.62390(18) 0.92180(13) 0.0368(6) Uani 1 1 d . . . . .
N4 N 0.8559(3) 0.68585(18) 0.80954(14) 0.0245(6) Uani 1 1 d . . . . .
O1 O 0.2696(3) 0.73269(16) 0.48220(14) 0.0383(7) Uani 1 1 d . . . . .
N3 N 0.6729(3) 0.65216(17) 0.62973(14) 0.0228(6) Uani 1 1 d . . . . .
H3 H 0.656182 0.708034 0.618552 0.027 Uiso 1 1 calc R U . . .
F2 F 0.4960(4) 0.39521(16) 0.86759(15) 0.0656(8) Uani 1 1 d . . . . .
N5 N 0.5531(3) 0.56870(19) 0.86089(16) 0.0262(6) Uani 1 1 d . . . . .
O4 O 0.4067(3) 0.5792(2) 0.75939(15) 0.0516(8) Uani 1 1 d . . . . .
N1 N 0.1153(3) 0.6345(2) 0.53884(16) 0.0342(8) Uani 1 1 d . . . . .
H1 H 0.034882 0.652658 0.517374 0.041 Uiso 1 1 calc R U . . .
N2 N 0.8350(4) 0.5350(2) 0.49203(18) 0.0418(8) Uani 1 1 d . . . . .
C8 C 0.7447(4) 0.6312(2) 0.69313(17) 0.0224(7) Uani 1 1 d . . . . .
C4 C 0.2444(4) 0.6712(2) 0.52565(18) 0.0260(7) Uani 1 1 d . . . . .
C17 C 0.6079(4) 0.6599(2) 0.85776(18) 0.0254(7) Uani 1 1 d . . . . .
H17 H 0.585635 0.683885 0.807377 0.030 Uiso 1 1 calc R U . . .
C9 C 0.8061(4) 0.7114(2) 0.73522(17) 0.0226(7) Uani 1 1 d . . . . .
H9 H 0.731630 0.759455 0.738621 0.027 Uiso 1 1 calc R U . . .
C16 C 0.7730(4) 0.6546(2) 0.86536(18) 0.0252(7) Uani 1 1 d . . . . .
F1 F 0.2822(4) 0.4354(2) 0.8445(2) 0.1098(14) Uani 1 1 d . . . . .
C6 C 0.6236(4) 0.5820(2) 0.58035(18) 0.0240(7) Uani 1 1 d . . . . .
H6 H 0.590520 0.530363 0.610728 0.029 Uiso 1 1 calc R U . . .
C18 C 0.5326(4) 0.7206(2) 0.91525(19) 0.0299(8) Uani 1 1 d . . . . .
C7 C 0.7440(4) 0.5535(2) 0.53215(19) 0.0299(8) Uani 1 1 d . . . . .
C2 C 0.2797(4) 0.5388(2) 0.59532(19) 0.0282(8) Uani 1 1 d . . . . .
H2A H 0.303168 0.490206 0.560448 0.034 Uiso 1 1 calc R U . . .
H2B H 0.308087 0.520562 0.645971 0.034 Uiso 1 1 calc R U . . .
F3 F 0.4216(5) 0.3991(2) 0.75712(16) 0.1181(17) Uani 1 1 d . . . . .
C10 C 0.9422(4) 0.7456(2) 0.69730(19) 0.0273(8) Uani 1 1 d . . . . .
H10 H 0.951442 0.736576 0.642613 0.033 Uiso 1 1 calc R U . . .
C3 C 0.3572(4) 0.6248(2) 0.57285(18) 0.0250(7) Uani 1 1 d . . . . .
H3A H 0.375840 0.661039 0.618233 0.030 Uiso 1 1 calc R U . . .
C5 C 0.4978(4) 0.6130(2) 0.53111(18) 0.0266(7) Uani 1 1 d . . . . .
H5A H 0.524562 0.670041 0.507704 0.032 Uiso 1 1 calc R U . . .
H5B H 0.482910 0.569056 0.491061 0.032 Uiso 1 1 calc R U . . .
C1 C 0.1190(4) 0.5615(2) 0.5921(2) 0.0320(8) Uani 1 1 d . . . . .
H1A H 0.061012 0.510450 0.574495 0.038 Uiso 1 1 calc R U . . .
H1B H 0.082448 0.580510 0.641160 0.038 Uiso 1 1 calc R U . . .
C13 C 1.0323(4) 0.8179(2) 0.73273(19) 0.0322(8) Uani 1 1 d . . . . .
C11 C 1.0715(4) 0.7224(2) 0.74556(19) 0.0316(8) Uani 1 1 d . . . . .
H11 H 1.160748 0.698424 0.721158 0.038 Uiso 1 1 calc R U . . .
C20 C 0.5282(5) 0.6782(3) 0.99237(19) 0.0377(9) Uani 1 1 d . . . . .
H20A H 0.466578 0.625249 0.991064 0.057 Uiso 1 1 calc R U . . .
H20B H 0.488609 0.720730 1.028061 0.057 Uiso 1 1 calc R U . . .
H20C H 0.626767 0.661399 1.007310 0.057 Uiso 1 1 calc R U . . .
C22 C 0.4610(4) 0.5383(3) 0.8106(2) 0.0357(9) Uani 1 1 d . . . . .
C12 C 1.0147(4) 0.6759(2) 0.81336(19) 0.0293(8) Uani 1 1 d . . . . .
H12A H 1.042280 0.612430 0.812887 0.035 Uiso 1 1 calc R U . . .
H12B H 1.053401 0.703577 0.858978 0.035 Uiso 1 1 calc R U . . .
C14 C 0.9757(5) 0.8760(3) 0.7949(2) 0.0389(9) Uani 1 1 d . . . . .
H14A H 0.922500 0.926291 0.773884 0.058 Uiso 1 1 calc R U . . .
H14B H 1.057496 0.897912 0.824394 0.058 Uiso 1 1 calc R U . . .
H14C H 0.910679 0.841260 0.826570 0.058 Uiso 1 1 calc R U . . .
C15 C 1.1308(5) 0.8681(3) 0.6798(2) 0.0454(11) Uani 1 1 d . . . . .
H15A H 1.166211 0.827617 0.641399 0.068 Uiso 1 1 calc R U . . .
H15B H 1.213363 0.892519 0.707281 0.068 Uiso 1 1 calc R U . . .
H15C H 1.076230 0.916513 0.656684 0.068 Uiso 1 1 calc R U . . .
C21 C 0.6141(5) 0.8087(2) 0.9195(2) 0.0422(10) Uani 1 1 d . . . . .
H21A H 0.712434 0.798397 0.938277 0.063 Uiso 1 1 calc R U . . .
H21B H 0.562544 0.849059 0.952976 0.063 Uiso 1 1 calc R U . . .
H21C H 0.619408 0.835192 0.870004 0.063 Uiso 1 1 calc R U . . .
C19 C 0.3763(4) 0.7377(3) 0.8895(2) 0.0452(10) Uani 1 1 d . . . . .
H19A H 0.377697 0.766440 0.840828 0.068 Uiso 1 1 calc R U . . .
H19B H 0.327178 0.776267 0.925260 0.068 Uiso 1 1 calc R U . . .
H19C H 0.324187 0.681168 0.885970 0.068 Uiso 1 1 calc R U . . .
C23 C 0.4154(6) 0.4418(3) 0.8206(2) 0.0547(13) Uani 1 1 d . . . . .
H5 H 0.589(4) 0.535(2) 0.895(2) 0.027(10) 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
O2 C8 1.216(4) . ?
O3 C16 1.229(4) . ?
N4 C9 1.469(4) . ?
N4 C16 1.349(4) . ?
N4 C12 1.472(4) . ?
O1 C4 1.237(4) . ?
N3 H3 0.8800 . ?
N3 C8 1.360(4) . ?
N3 C6 1.456(4) . ?
F2 C23 1.328(5) . ?
N5 C17 1.466(4) . ?
N5 C22 1.324(4) . ?
N5 H5 0.86(4) . ?
O4 C22 1.219(4) . ?
N1 H1 0.8800 . ?
N1 C4 1.332(5) . ?
N1 C1 1.462(4) . ?
N2 C7 1.142(5) . ?
C8 C9 1.537(4) . ?
C4 C3 1.515(5) . ?
C17 H17 1.0000 . ?
C17 C16 1.530(5) . ?
C17 C18 1.548(5) . ?
C9 H9 1.0000 . ?
C9 C10 1.519(5) . ?
F1 C23 1.304(6) . ?
C6 H6 1.0000 . ?
C6 C7 1.474(5) . ?
C6 C5 1.533(5) . ?
C18 C20 1.533(5) . ?
C18 C21 1.528(5) . ?
C18 C19 1.535(5) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C2 C3 1.535(5) . ?
C2 C1 1.520(5) . ?
F3 C23 1.316(5) . ?
C10 H10 1.0000 . ?
C10 C13 1.512(5) . ?
C10 C11 1.517(5) . ?
C3 H3A 1.0000 . ?
C3 C5 1.509(5) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C13 C11 1.503(5) . ?
C13 C14 1.516(5) . ?
C13 C15 1.519(5) . ?
C11 H11 1.0000 . ?
C11 C12 1.505(5) . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C22 C23 1.526(6) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 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
C9 N4 C12 112.3(3) . . ?
C16 N4 C9 126.6(3) . . ?
C16 N4 C12 119.5(3) . . ?
C8 N3 H3 120.1 . . ?
C8 N3 C6 119.9(3) . . ?
C6 N3 H3 120.1 . . ?
C17 N5 H5 117(2) . . ?
C22 N5 C17 121.3(3) . . ?
C22 N5 H5 122(2) . . ?
C4 N1 H1 122.9 . . ?
C4 N1 C1 114.2(3) . . ?
C1 N1 H1 122.9 . . ?
O2 C8 N3 123.1(3) . . ?
O2 C8 C9 122.5(3) . . ?
N3 C8 C9 114.3(3) . . ?
O1 C4 N1 126.3(3) . . ?
O1 C4 C3 125.0(3) . . ?
N1 C4 C3 108.6(3) . . ?
N5 C17 H17 107.7 . . ?
N5 C17 C16 106.8(3) . . ?
N5 C17 C18 112.0(3) . . ?
C16 C17 H17 107.7 . . ?
C16 C17 C18 114.6(3) . . ?
C18 C17 H17 107.7 . . ?
N4 C9 C8 111.1(3) . . ?
N4 C9 H9 110.4 . . ?
N4 C9 C10 104.1(3) . . ?
C8 C9 H9 110.4 . . ?
C10 C9 C8 110.4(3) . . ?
C10 C9 H9 110.4 . . ?
O3 C16 N4 121.1(3) . . ?
O3 C16 C17 120.3(3) . . ?
N4 C16 C17 118.5(3) . . ?
N3 C6 H6 109.0 . . ?
N3 C6 C7 109.8(3) . . ?
N3 C6 C5 111.7(3) . . ?
C7 C6 H6 109.0 . . ?
C7 C6 C5 108.4(3) . . ?
C5 C6 H6 109.0 . . ?
C20 C18 C17 112.0(3) . . ?
C20 C18 C19 108.7(3) . . ?
C21 C18 C17 109.2(3) . . ?
C21 C18 C20 109.3(3) . . ?
C21 C18 C19 109.3(3) . . ?
C19 C18 C17 108.4(3) . . ?
N2 C7 C6 176.1(4) . . ?
H2A C2 H2B 108.9 . . ?
C3 C2 H2A 110.8 . . ?
C3 C2 H2B 110.8 . . ?
C1 C2 H2A 110.8 . . ?
C1 C2 H2B 110.8 . . ?
C1 C2 C3 104.6(3) . . ?
C9 C10 H10 118.0 . . ?
C13 C10 C9 120.5(3) . . ?
C13 C10 H10 118.0 . . ?
C13 C10 C11 59.5(2) . . ?
C11 C10 C9 108.1(3) . . ?
C11 C10 H10 118.0 . . ?
C4 C3 C2 102.7(3) . . ?
C4 C3 H3A 109.0 . . ?
C2 C3 H3A 109.0 . . ?
C5 C3 C4 111.3(3) . . ?
C5 C3 C2 115.6(3) . . ?
C5 C3 H3A 109.0 . . ?
C6 C5 H5A 108.9 . . ?
C6 C5 H5B 108.9 . . ?
C3 C5 C6 113.3(3) . . ?
C3 C5 H5A 108.9 . . ?
C3 C5 H5B 108.9 . . ?
H5A C5 H5B 107.7 . . ?
N1 C1 C2 102.6(3) . . ?
N1 C1 H1A 111.3 . . ?
N1 C1 H1B 111.3 . . ?
C2 C1 H1A 111.3 . . ?
C2 C1 H1B 111.3 . . ?
H1A C1 H1B 109.2 . . ?
C10 C13 C14 122.8(3) . . ?
C10 C13 C15 114.9(3) . . ?
C11 C13 C10 60.4(2) . . ?
C11 C13 C14 121.5(3) . . ?
C11 C13 C15 115.5(3) . . ?
C14 C13 C15 112.5(3) . . ?
C10 C11 H11 118.4 . . ?
C13 C11 C10 60.1(2) . . ?
C13 C11 H11 118.4 . . ?
C13 C11 C12 119.2(3) . . ?
C12 C11 C10 107.5(3) . . ?
C12 C11 H11 118.4 . . ?
C18 C20 H20A 109.5 . . ?
C18 C20 H20B 109.5 . . ?
C18 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
N5 C22 C23 115.2(3) . . ?
O4 C22 N5 127.4(4) . . ?
O4 C22 C23 117.3(4) . . ?
N4 C12 C11 105.1(3) . . ?
N4 C12 H12A 110.7 . . ?
N4 C12 H12B 110.7 . . ?
C11 C12 H12A 110.7 . . ?
C11 C12 H12B 110.7 . . ?
H12A C12 H12B 108.8 . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C13 C15 H15A 109.5 . . ?
C13 C15 H15B 109.5 . . ?
C13 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C18 C21 H21A 109.5 . . ?
C18 C21 H21B 109.5 . . ?
C18 C21 H21C 109.5 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
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 . . ?
F2 C23 C22 115.2(4) . . ?
F1 C23 F2 106.0(4) . . ?
F1 C23 F3 107.1(4) . . ?
F1 C23 C22 111.7(4) . . ?
F3 C23 F2 105.8(4) . . ?
F3 C23 C22 110.6(4) . . ?

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
_geom_hbond_publ_flag
N3 H3 O1 0.88 2.28 2.809(4) 118.6 4_566 yes
N1 H1 N2 0.88 2.60 3.104(5) 117.5 1_455 yes
C14 H14C N4 0.98 2.42 3.084(5) 124.9 . yes
N5 H5 N2 0.86(4) 2.16(4) 3.019(4) 171(3) 2_665 yes

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
O2 C8 C9 N4 -9.7(5) . . . . ?
O2 C8 C9 C10 105.2(4) . . . . ?
N4 C9 C10 C13 -54.0(4) . . . . ?
N4 C9 C10 C11 10.7(3) . . . . ?
O1 C4 C3 C2 -162.7(3) . . . . ?
O1 C4 C3 C5 -38.5(5) . . . . ?
N3 C8 C9 N4 168.6(3) . . . . ?
N3 C8 C9 C10 -76.5(3) . . . . ?
N3 C6 C5 C3 -71.6(4) . . . . ?
N5 C17 C16 O3 -61.9(4) . . . . ?
N5 C17 C16 N4 119.4(3) . . . . ?
N5 C17 C18 C20 48.0(4) . . . . ?
N5 C17 C18 C21 169.1(3) . . . . ?
N5 C17 C18 C19 -72.0(4) . . . . ?
N5 C22 C23 F2 -14.1(6) . . . . ?
N5 C22 C23 F1 106.9(5) . . . . ?
N5 C22 C23 F3 -134.0(4) . . . . ?
O4 C22 C23 F2 167.9(4) . . . . ?
O4 C22 C23 F1 -71.1(5) . . . . ?
O4 C22 C23 F3 48.0(6) . . . . ?
N1 C4 C3 C2 17.2(4) . . . . ?
N1 C4 C3 C5 141.4(3) . . . . ?
C8 N3 C6 C7 -82.5(4) . . . . ?
C8 N3 C6 C5 157.2(3) . . . . ?
C8 C9 C10 C13 -173.2(3) . . . . ?
C8 C9 C10 C11 -108.5(3) . . . . ?
C4 N1 C1 C2 -15.7(4) . . . . ?
C4 C3 C5 C6 169.5(3) . . . . ?
C17 N5 C22 O4 -3.0(6) . . . . ?
C17 N5 C22 C23 179.2(4) . . . . ?
C9 N4 C16 O3 170.0(3) . . . . ?
C9 N4 C16 C17 -11.3(5) . . . . ?
C9 N4 C12 C11 16.8(4) . . . . ?
C9 C10 C13 C11 94.2(3) . . . . ?
C9 C10 C13 C14 -16.3(5) . . . . ?
C9 C10 C13 C15 -159.4(3) . . . . ?
C9 C10 C11 C13 -115.2(3) . . . . ?
C9 C10 C11 C12 -1.1(4) . . . . ?
C16 N4 C9 C8 -63.9(4) . . . . ?
C16 N4 C9 C10 177.3(3) . . . . ?
C16 N4 C12 C11 -176.6(3) . . . . ?
C16 C17 C18 C20 -74.0(4) . . . . ?
C16 C17 C18 C21 47.2(4) . . . . ?
C16 C17 C18 C19 166.1(3) . . . . ?
C6 N3 C8 O2 -8.5(5) . . . . ?
C6 N3 C8 C9 173.1(3) . . . . ?
C18 C17 C16 O3 62.8(4) . . . . ?
C18 C17 C16 N4 -115.9(3) . . . . ?
C7 C6 C5 C3 167.3(3) . . . . ?
C2 C3 C5 C6 -73.9(4) . . . . ?
C10 C13 C11 C12 -94.4(3) . . . . ?
C10 C11 C12 N4 -9.0(4) . . . . ?
C3 C2 C1 N1 25.3(4) . . . . ?
C1 N1 C4 O1 178.8(3) . . . . ?
C1 N1 C4 C3 -1.0(4) . . . . ?
C1 C2 C3 C4 -25.9(4) . . . . ?
C1 C2 C3 C5 -147.3(3) . . . . ?
C13 C10 C11 C12 114.1(3) . . . . ?
C13 C11 C12 N4 56.0(4) . . . . ?
C11 C10 C13 C14 -110.4(4) . . . . ?
C11 C10 C13 C15 106.4(4) . . . . ?
C22 N5 C17 C16 -130.4(3) . . . . ?
C22 N5 C17 C18 103.3(4) . . . . ?
C12 N4 C9 C8 101.5(3) . . . . ?
C12 N4 C9 C10 -17.3(3) . . . . ?
C12 N4 C16 O3 5.5(5) . . . . ?
C12 N4 C16 C17 -175.8(3) . . . . ?
C14 C13 C11 C10 112.5(4) . . . . ?
C14 C13 C11 C12 18.1(5) . . . . ?
C15 C13 C11 C10 -105.4(3) . . . . ?
C15 C13 C11 C12 160.2(3) . . . . ?


_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_nmtw1_293k_0m
_database_code_depnum_ccdc_archive 'CCDC 2362549'
loop_
_audit_author_name
_audit_author_address
'Dier Shi'
;Zhejiang University
China
;
_audit_update_record             
;
2024-06-13 deposited with the CCDC.	2025-08-07 downloaded from the CCDC.
;
_audit_creation_date             2024-05-15
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C23 H32 F3 N5 O4'
_chemical_formula_sum            'C23 H32 F3 N5 O4'
_chemical_formula_weight         499.53
_chemical_absolute_configuration unk
_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      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_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'

_cell_length_a                   9.6828(5)
_cell_length_b                   15.0274(8)
_cell_length_c                   18.0229(7)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2622.5(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4173
_cell_measurement_temperature    293.0
_cell_measurement_theta_max      26.492
_cell_measurement_theta_min      2.388
_shelx_estimated_absorpt_T_max   0.993
_shelx_estimated_absorpt_T_min   0.972
_exptl_absorpt_coefficient_mu    0.102
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6714
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1306 before and 0.0770 after correction.
The Ratio of minimum to maximum transmission is 0.9005.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.265
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             1056
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.113
_exptl_crystal_size_min          0.07
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1038
_diffrn_reflns_av_unetI/netI     0.0735
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            33060
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.494
_diffrn_reflns_theta_min         2.260
_diffrn_ambient_temperature      293.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_reflns_Friedel_coverage         0.776
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.998
_reflns_number_gt                3643
_reflns_number_total             6026
_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 (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.566
_refine_diff_density_min         -0.297
_refine_diff_density_rms         0.050
_refine_ls_abs_structure_details 
;
 Flack x determined using 1016 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.9(7)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.110
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     321
_refine_ls_number_reflns         6026
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1649
_refine_ls_R_factor_gt           0.0983
_refine_ls_restrained_S_all      1.110
_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)+(0.0614P)²+2.5329P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1914
_refine_ls_wR_factor_ref         0.2243
_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:
 C3(H3A), C9(H9), C6(H6), C17(H17), C10(H10), C11(H11)
2.b Secondary CH2 refined with riding coordinates:
 C5(H5A,H5B), C2(H2A,H2B), C1(H1A,H1B), C12(H12A,H12B)
2.c Aromatic/amide H refined with riding coordinates:
 N3(H3), N5(H5), N1(H1)
2.d Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C), C20(H20A,H20B,H20C), C21(H21A,H21B,H21C), C15(H15A,H15B,
 H15C), C19(H19A,H19B,H19C)
;
_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
O3 O 0.8161(5) 0.5753(4) 0.9126(3) 0.0701(15) Uani 1 1 d . . . . .
N3 N 0.7309(5) 0.6459(3) 0.6215(3) 0.0425(12) Uani 1 1 d . . . . .
H3 H 0.718707 0.702168 0.615415 0.051 Uiso 1 1 calc R U . . .
O2 O 0.7724(6) 0.5377(3) 0.7058(3) 0.0689(15) Uani 1 1 d . . . . .
N4 N 0.8734(5) 0.6524(4) 0.8107(3) 0.0492(13) Uani 1 1 d . . . . .
O1 O 0.3400(6) 0.7172(4) 0.4630(3) 0.0823(18) Uani 1 1 d . . . . .
N5 N 0.5498(6) 0.5601(4) 0.8481(3) 0.0549(14) Uani 1 1 d . . . . .
H5 H 0.561146 0.522378 0.883476 0.066 Uiso 1 1 calc R U . . .
O4 O 0.4314(6) 0.5895(4) 0.7425(3) 0.0836(18) Uani 1 1 d . . . . .
C3 C 0.4469(6) 0.6166(4) 0.5521(3) 0.0416(14) Uani 1 1 d . . . . .
H3A H 0.455773 0.651001 0.598014 0.050 Uiso 1 1 calc R U . . .
C16 C 0.7820(7) 0.6195(4) 0.8591(3) 0.0481(15) Uani 1 1 d . . . . .
N1 N 0.2156(6) 0.6091(5) 0.5211(4) 0.078(2) Uani 1 1 d . . . . .
H1 H 0.136471 0.621795 0.502122 0.093 Uiso 1 1 calc R U . . .
C8 C 0.7776(6) 0.6150(4) 0.6866(3) 0.0430(14) Uani 1 1 d . . . . .
C4 C 0.3295(7) 0.6548(5) 0.5060(4) 0.0565(17) Uani 1 1 d . . . . .
C9 C 0.8431(7) 0.6861(4) 0.7360(3) 0.0458(15) Uani 1 1 d . . . . .
H9 H 0.783598 0.738775 0.738786 0.055 Uiso 1 1 calc R U . . .
C6 C 0.7008(6) 0.5847(4) 0.5609(3) 0.0463(15) Uani 1 1 d . . . . .
H6 H 0.674905 0.527029 0.582099 0.056 Uiso 1 1 calc R U . . .
C17 C 0.6284(6) 0.6427(5) 0.8484(4) 0.0481(16) Uani 1 1 d . . . . .
H17 H 0.617642 0.671098 0.799788 0.058 Uiso 1 1 calc R U . . .
C5 C 0.5829(6) 0.6173(5) 0.5117(3) 0.0457(15) Uani 1 1 d . . . . .
H5A H 0.602726 0.677302 0.494994 0.055 Uiso 1 1 calc R U . . .
H5B H 0.576395 0.579425 0.468217 0.055 Uiso 1 1 calc R U . . .
C10 C 0.9849(7) 0.7108(5) 0.7051(4) 0.0550(18) Uani 1 1 d . . . . .
H10 H 1.000330 0.702209 0.651814 0.066 Uiso 1 1 calc R U . . .
N2 N 0.9239(7) 0.5663(6) 0.4816(4) 0.097(3) Uani 1 1 d . . . . .
C22 C 0.4610(7) 0.5420(5) 0.7942(4) 0.0603(19) Uani 1 1 d . . . . .
C13 C 1.0780(8) 0.7754(6) 0.7452(4) 0.067(2) Uani 1 1 d . . . . .
C2 C 0.3907(7) 0.5235(5) 0.5706(4) 0.0628(19) Uani 1 1 d . . . . .
H2A H 0.417302 0.480597 0.533013 0.075 Uiso 1 1 calc R U . . .
H2B H 0.424305 0.503338 0.618484 0.075 Uiso 1 1 calc R U . . .
C18 C 0.5739(8) 0.7080(5) 0.9085(4) 0.0631(19) Uani 1 1 d . . . . .
C7 C 0.8265(7) 0.5728(5) 0.5161(4) 0.0623(19) Uani 1 1 d . . . . .
C1 C 0.2362(8) 0.5362(6) 0.5719(5) 0.079(2) Uani 1 1 d . . . . .
H1A H 0.188612 0.483092 0.555161 0.095 Uiso 1 1 calc R U . . .
H1B H 0.204118 0.551384 0.621330 0.095 Uiso 1 1 calc R U . . .
C12 C 1.0208(7) 0.6319(6) 0.8211(4) 0.064(2) Uani 1 1 d . . . . .
H12A H 1.036110 0.568160 0.820115 0.077 Uiso 1 1 calc R U . . .
H12B H 1.053455 0.655153 0.868164 0.077 Uiso 1 1 calc R U . . .
C11 C 1.0938(7) 0.6763(6) 0.7577(4) 0.066(2) Uani 1 1 d . . . . .
H11 H 1.174841 0.646565 0.736493 0.079 Uiso 1 1 calc R U . . .
C14 C 1.0223(10) 0.8353(6) 0.8045(5) 0.084(3) Uani 1 1 d . . . . .
H14A H 0.980562 0.886622 0.782102 0.127 Uiso 1 1 calc R U . . .
H14B H 1.096199 0.853796 0.836482 0.127 Uiso 1 1 calc R U . . .
H14C H 0.954259 0.803782 0.833047 0.127 Uiso 1 1 calc R U . . .
C20 C 0.5645(12) 0.6671(7) 0.9852(4) 0.095(3) Uani 1 1 d . . . . .
H20A H 0.499466 0.618904 0.984452 0.143 Uiso 1 1 calc R U . . .
H20B H 0.534396 0.711415 1.020004 0.143 Uiso 1 1 calc R U . . .
H20C H 0.653581 0.645163 0.999649 0.143 Uiso 1 1 calc R U . . .
C21 C 0.6739(11) 0.7871(6) 0.9137(6) 0.103(3) Uani 1 1 d . . . . .
H21A H 0.765713 0.765564 0.922738 0.155 Uiso 1 1 calc R U . . .
H21B H 0.646226 0.825443 0.953597 0.155 Uiso 1 1 calc R U . . .
H21C H 0.672323 0.819728 0.867884 0.155 Uiso 1 1 calc R U . . .
C15 C 1.1879(9) 0.8183(7) 0.6971(5) 0.101(3) Uani 1 1 d . . . . .
H15A H 1.212842 0.778341 0.657759 0.151 Uiso 1 1 calc R U . . .
H15B H 1.267882 0.831006 0.726776 0.151 Uiso 1 1 calc R U . . .
H15C H 1.152647 0.872554 0.676448 0.151 Uiso 1 1 calc R U . . .
C19 C 0.4312(10) 0.7408(8) 0.8849(6) 0.109(4) Uani 1 1 d . . . . .
H19A H 0.395016 0.780149 0.922062 0.164 Uiso 1 1 calc R U . . .
H19B H 0.370325 0.690887 0.879041 0.164 Uiso 1 1 calc R U . . .
H19C H 0.438588 0.772072 0.838560 0.164 Uiso 1 1 calc R U . . .
F1 F 0.3189(13) 0.4325(7) 0.7465(4) 0.254(7) Uani 1 1 d . . . . .
F2 F 0.2894(9) 0.4589(6) 0.8532(5) 0.186(4) Uani 1 1 d . . . . .
F3 F 0.4525(8) 0.3907(5) 0.8309(7) 0.194(5) Uani 1 1 d . . . . .
C23 C 0.3870(11) 0.4547(8) 0.8024(6) 0.091(3) Uani 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
O3 C16 1.218(7) . ?
N3 H3 0.8600 . ?
N3 C8 1.342(7) . ?
N3 C6 1.457(7) . ?
O2 C8 1.213(7) . ?
N4 C16 1.337(8) . ?
N4 C9 1.468(8) . ?
N4 C12 1.471(8) . ?
O1 C4 1.222(8) . ?
N5 H5 0.8600 . ?
N5 C17 1.456(8) . ?
N5 C22 1.325(8) . ?
O4 C22 1.208(8) . ?
C3 H3A 0.9800 . ?
C3 C4 1.520(9) . ?
C3 C5 1.505(8) . ?
C3 C2 1.538(9) . ?
C16 C17 1.540(9) . ?
N1 H1 0.8600 . ?
N1 C4 1.327(9) . ?
N1 C1 1.442(10) . ?
C8 C9 1.529(9) . ?
C9 H9 0.9800 . ?
C9 C10 1.528(9) . ?
C6 H6 0.9800 . ?
C6 C5 1.527(8) . ?
C6 C7 1.472(10) . ?
C17 H17 0.9800 . ?
C17 C18 1.555(10) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C10 H10 0.9800 . ?
C10 C13 1.509(10) . ?
C10 C11 1.510(9) . ?
N2 C7 1.134(9) . ?
C22 C23 1.502(12) . ?
C13 C11 1.514(11) . ?
C13 C14 1.499(12) . ?
C13 C15 1.515(11) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C2 C1 1.509(11) . ?
C18 C20 1.514(11) . ?
C18 C21 1.536(12) . ?
C18 C19 1.528(12) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C12 C11 1.501(10) . ?
C11 H11 0.9800 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
F1 C23 1.250(11) . ?
F2 C23 1.317(12) . ?
F3 C23 1.261(12) . ?

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 N3 H3 119.9 . . ?
C8 N3 C6 120.3(5) . . ?
C6 N3 H3 119.9 . . ?
C16 N4 C9 126.3(5) . . ?
C16 N4 C12 118.8(5) . . ?
C9 N4 C12 112.5(5) . . ?
C17 N5 H5 119.5 . . ?
C22 N5 H5 119.5 . . ?
C22 N5 C17 121.1(6) . . ?
C4 C3 H3A 109.1 . . ?
C4 C3 C2 101.4(5) . . ?
C5 C3 H3A 109.1 . . ?
C5 C3 C4 112.8(5) . . ?
C5 C3 C2 114.9(6) . . ?
C2 C3 H3A 109.1 . . ?
O3 C16 N4 122.6(6) . . ?
O3 C16 C17 119.0(6) . . ?
N4 C16 C17 118.3(5) . . ?
C4 N1 H1 123.0 . . ?
C4 N1 C1 114.1(6) . . ?
C1 N1 H1 123.0 . . ?
N3 C8 C9 114.0(5) . . ?
O2 C8 N3 124.6(6) . . ?
O2 C8 C9 121.4(5) . . ?
O1 C4 C3 125.0(6) . . ?
O1 C4 N1 126.6(7) . . ?
N1 C4 C3 108.3(6) . . ?
N4 C9 C8 112.1(5) . . ?
N4 C9 H9 110.5 . . ?
N4 C9 C10 103.8(5) . . ?
C8 C9 H9 110.5 . . ?
C10 C9 C8 109.2(5) . . ?
C10 C9 H9 110.5 . . ?
N3 C6 H6 108.6 . . ?
N3 C6 C5 112.5(5) . . ?
N3 C6 C7 108.8(5) . . ?
C5 C6 H6 108.6 . . ?
C7 C6 H6 108.6 . . ?
C7 C6 C5 109.7(5) . . ?
N5 C17 C16 108.2(5) . . ?
N5 C17 H17 108.2 . . ?
N5 C17 C18 111.3(5) . . ?
C16 C17 H17 108.2 . . ?
C16 C17 C18 112.6(6) . . ?
C18 C17 H17 108.2 . . ?
C3 C5 C6 111.8(5) . . ?
C3 C5 H5A 109.3 . . ?
C3 C5 H5B 109.3 . . ?
C6 C5 H5A 109.3 . . ?
C6 C5 H5B 109.3 . . ?
H5A C5 H5B 107.9 . . ?
C9 C10 H10 117.6 . . ?
C13 C10 C9 121.2(6) . . ?
C13 C10 H10 117.6 . . ?
C13 C10 C11 60.2(5) . . ?
C11 C10 C9 108.4(5) . . ?
C11 C10 H10 117.6 . . ?
N5 C22 C23 114.6(7) . . ?
O4 C22 N5 126.8(7) . . ?
O4 C22 C23 118.6(7) . . ?
C10 C13 C11 59.9(5) . . ?
C10 C13 C15 114.8(6) . . ?
C11 C13 C15 115.6(8) . . ?
C14 C13 C10 120.8(7) . . ?
C14 C13 C11 121.4(7) . . ?
C14 C13 C15 113.9(7) . . ?
C3 C2 H2A 111.0 . . ?
C3 C2 H2B 111.0 . . ?
H2A C2 H2B 109.0 . . ?
C1 C2 C3 103.8(6) . . ?
C1 C2 H2A 111.0 . . ?
C1 C2 H2B 111.0 . . ?
C20 C18 C17 113.6(7) . . ?
C20 C18 C21 107.3(7) . . ?
C20 C18 C19 109.4(8) . . ?
C21 C18 C17 108.4(6) . . ?
C19 C18 C17 108.4(7) . . ?
C19 C18 C21 109.7(8) . . ?
N2 C7 C6 177.9(9) . . ?
N1 C1 C2 102.9(6) . . ?
N1 C1 H1A 111.2 . . ?
N1 C1 H1B 111.2 . . ?
C2 C1 H1A 111.2 . . ?
C2 C1 H1B 111.2 . . ?
H1A C1 H1B 109.1 . . ?
N4 C12 H12A 110.6 . . ?
N4 C12 H12B 110.6 . . ?
N4 C12 C11 105.5(6) . . ?
H12A C12 H12B 108.8 . . ?
C11 C12 H12A 110.6 . . ?
C11 C12 H12B 110.6 . . ?
C10 C11 C13 59.9(5) . . ?
C10 C11 H11 118.1 . . ?
C13 C11 H11 118.1 . . ?
C12 C11 C10 107.6(6) . . ?
C12 C11 C13 120.2(7) . . ?
C12 C11 H11 118.1 . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C18 C20 H20A 109.5 . . ?
C18 C20 H20B 109.5 . . ?
C18 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C18 C21 H21A 109.5 . . ?
C18 C21 H21B 109.5 . . ?
C18 C21 H21C 109.5 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C13 C15 H15A 109.5 . . ?
C13 C15 H15B 109.5 . . ?
C13 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
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 . . ?
F1 C23 C22 113.9(9) . . ?
F1 C23 F2 101.1(10) . . ?
F1 C23 F3 112.9(12) . . ?
F2 C23 C22 111.7(10) . . ?
F3 C23 C22 117.8(8) . . ?
F3 C23 F2 96.6(10) . . ?

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
_geom_hbond_publ_flag
N3 H3 O1 0.86 2.20 2.768(7) 123.3 4_566 yes
N5 H5 N2 0.86 2.22 3.076(9) 174.2 2_665 yes
N1 H1 N2 0.86 2.25 2.982(9) 142.9 1_455 yes

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
O3 C16 C17 N5 -55.4(8) . . . . ?
O3 C16 C17 C18 68.0(8) . . . . ?
N3 C8 C9 N4 171.3(5) . . . . ?
N3 C8 C9 C10 -74.2(7) . . . . ?
N3 C6 C5 C3 -67.7(7) . . . . ?
O2 C8 C9 N4 -9.9(9) . . . . ?
O2 C8 C9 C10 104.6(7) . . . . ?
N4 C16 C17 N5 127.6(6) . . . . ?
N4 C16 C17 C18 -108.9(7) . . . . ?
N4 C9 C10 C13 -56.3(8) . . . . ?
N4 C9 C10 C11 9.4(7) . . . . ?
N4 C12 C11 C10 -8.1(9) . . . . ?
N4 C12 C11 C13 56.7(9) . . . . ?
N5 C17 C18 C20 52.5(8) . . . . ?
N5 C17 C18 C21 171.7(6) . . . . ?
N5 C17 C18 C19 -69.2(8) . . . . ?
N5 C22 C23 F1 -170.3(11) . . . . ?
N5 C22 C23 F2 75.8(11) . . . . ?
N5 C22 C23 F3 -34.6(14) . . . . ?
O4 C22 C23 F1 12.5(15) . . . . ?
O4 C22 C23 F2 -101.3(11) . . . . ?
O4 C22 C23 F3 148.3(10) . . . . ?
C3 C2 C1 N1 28.3(8) . . . . ?
C16 N4 C9 C8 -59.8(8) . . . . ?
C16 N4 C9 C10 -177.5(6) . . . . ?
C16 N4 C12 C11 178.7(6) . . . . ?
C16 C17 C18 C20 -69.1(8) . . . . ?
C16 C17 C18 C21 50.0(8) . . . . ?
C16 C17 C18 C19 169.1(7) . . . . ?
C8 N3 C6 C5 148.3(6) . . . . ?
C8 N3 C6 C7 -89.8(7) . . . . ?
C8 C9 C10 C13 -176.0(6) . . . . ?
C8 C9 C10 C11 -110.3(6) . . . . ?
C4 C3 C5 C6 176.0(5) . . . . ?
C4 C3 C2 C1 -29.5(8) . . . . ?
C4 N1 C1 C2 -16.6(10) . . . . ?
C9 N4 C16 O3 163.4(6) . . . . ?
C9 N4 C16 C17 -19.7(10) . . . . ?
C9 N4 C12 C11 15.0(8) . . . . ?
C9 C10 C13 C11 94.4(7) . . . . ?
C9 C10 C13 C14 -16.4(11) . . . . ?
C9 C10 C13 C15 -159.2(7) . . . . ?
C9 C10 C11 C13 -116.1(7) . . . . ?
C9 C10 C11 C12 -0.9(8) . . . . ?
C6 N3 C8 O2 -15.3(10) . . . . ?
C6 N3 C8 C9 163.3(5) . . . . ?
C17 N5 C22 O4 -2.4(11) . . . . ?
C17 N5 C22 C23 -179.3(7) . . . . ?
C5 C3 C4 O1 -36.4(10) . . . . ?
C5 C3 C4 N1 144.0(6) . . . . ?
C5 C3 C2 C1 -151.5(6) . . . . ?
C10 C13 C11 C12 -93.8(7) . . . . ?
C22 N5 C17 C16 -128.8(6) . . . . ?
C22 N5 C17 C18 107.0(7) . . . . ?
C13 C10 C11 C12 115.2(7) . . . . ?
C2 C3 C4 O1 -159.8(8) . . . . ?
C2 C3 C4 N1 20.6(8) . . . . ?
C2 C3 C5 C6 -68.4(7) . . . . ?
C7 C6 C5 C3 170.9(6) . . . . ?
C1 N1 C4 O1 177.5(8) . . . . ?
C1 N1 C4 C3 -2.9(9) . . . . ?
C12 N4 C16 O3 2.1(10) . . . . ?
C12 N4 C16 C17 178.9(6) . . . . ?
C12 N4 C9 C8 102.6(7) . . . . ?
C12 N4 C9 C10 -15.2(8) . . . . ?
C11 C10 C13 C14 -110.8(8) . . . . ?
C11 C10 C13 C15 106.4(9) . . . . ?
C14 C13 C11 C10 109.9(8) . . . . ?
C14 C13 C11 C12 16.1(10) . . . . ?
C15 C13 C11 C10 -105.1(7) . . . . ?
C15 C13 C11 C12 161.1(6) . . . . ?


_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_nmtw1_223k_0m
_database_code_depnum_ccdc_archive 'CCDC 2362547'
loop_
_audit_author_name
_audit_author_address
'Dier Shi'
;Zhejiang University
China
;
_audit_update_record             
;
2024-06-13 deposited with the CCDC.	2025-08-07 downloaded from the CCDC.
;
_audit_creation_date             2023-06-19
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C23 H32 F3 N5 O4'
_chemical_formula_sum            'C23 H32 F3 N5 O4'
_chemical_formula_weight         499.53
_chemical_absolute_configuration unk
_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      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_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'

_cell_length_a                   9.2308(5)
_cell_length_b                   15.1453(7)
_cell_length_c                   18.1170(8)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2532.8(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5290
_cell_measurement_temperature    223.0
_cell_measurement_theta_max      26.727
_cell_measurement_theta_min      2.477
_shelx_estimated_absorpt_T_max   0.993
_shelx_estimated_absorpt_T_min   0.971
_exptl_absorpt_coefficient_mu    0.105
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6888
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1304 before and 0.0768 after correction.
The Ratio of minimum to maximum transmission is 0.9238.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.310
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             1056
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.113
_exptl_crystal_size_min          0.07
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0956
_diffrn_reflns_av_unetI/netI     0.0656
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            34168
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.498
_diffrn_reflns_theta_min         2.248
_diffrn_ambient_temperature      223.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_reflns_Friedel_coverage         0.775
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.999
_reflns_number_gt                4190
_reflns_number_total             5802
_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 (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.267
_refine_diff_density_min         -0.280
_refine_diff_density_rms         0.050
_refine_ls_abs_structure_details 
;
 Flack x determined using 1289 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.3(6)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.128
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     321
_refine_ls_number_reflns         5802
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1116
_refine_ls_R_factor_gt           0.0731
_refine_ls_restrained_S_all      1.128
_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)+(0.0236P)²+1.7176P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1164
_refine_ls_wR_factor_ref         0.1317
_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:
 C17(H17), C9(H9), C6(H6), C3(H3A), C10(H10), C11(H11)
2.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C5(H5A,H5B), C1(H1A,H1B), C12(H12A,H12B)
2.c Aromatic/amide H refined with riding coordinates:
 N3(H3), N5(H5), N1(H1)
2.d Idealised Me refined as rotating group:
 C20(H20A,H20B,H20C), C14(H14A,H14B,H14C), C21(H21A,H21B,H21C), C19(H19A,H19B,
 H19C), C15(H15A,H15B,H15C)
;
_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
N4 N 0.8571(4) 0.3146(2) 0.19104(19) 0.0301(8) Uani 1 1 d . . . . .
O2 O 0.7586(4) 0.4440(2) 0.28469(17) 0.0435(8) Uani 1 1 d . . . . .
O3 O 0.8285(3) 0.3781(2) 0.07972(17) 0.0457(9) Uani 1 1 d . . . . .
N3 N 0.6764(4) 0.3481(2) 0.37078(18) 0.0285(8) Uani 1 1 d . . . . .
H3 H 0.660311 0.293085 0.382050 0.034 Uiso 1 1 calc R U . . .
O1 O 0.2737(4) 0.2673(2) 0.51794(19) 0.0482(9) Uani 1 1 d . . . . .
N5 N 0.5539(4) 0.4307(2) 0.13949(19) 0.0337(9) Uani 1 1 d . . . . .
H5 H 0.582658 0.465285 0.104041 0.040 Uiso 1 1 calc R U . . .
O4 O 0.4074(4) 0.4203(3) 0.2407(2) 0.0652(12) Uani 1 1 d . . . . .
F2 F 0.4924(5) 0.6034(2) 0.1324(2) 0.0885(12) Uani 1 1 d . . . . .
N1 N 0.1207(4) 0.3657(3) 0.4612(2) 0.0436(10) Uani 1 1 d . . . . .
H1 H 0.041096 0.347981 0.482263 0.052 Uiso 1 1 calc R U . . .
C8 C 0.7467(4) 0.3686(3) 0.3070(2) 0.0293(9) Uani 1 1 d . . . . .
C4 C 0.2494(5) 0.3285(3) 0.4747(2) 0.0344(10) Uani 1 1 d . . . . .
C17 C 0.6088(5) 0.3404(3) 0.1435(2) 0.0314(10) Uani 1 1 d . . . . .
H17 H 0.586816 0.317071 0.193274 0.038 Uiso 1 1 calc R U . . .
C9 C 0.8083(4) 0.2889(3) 0.2651(2) 0.0268(9) Uani 1 1 d . . . . .
H9 H 0.734868 0.241453 0.261858 0.032 Uiso 1 1 calc R U . . .
N2 N 0.8387(5) 0.4650(3) 0.5074(2) 0.0545(12) Uani 1 1 d . . . . .
C16 C 0.7740(5) 0.3464(3) 0.1358(2) 0.0321(10) Uani 1 1 d . . . . .
C7 C 0.7480(5) 0.4464(3) 0.4683(3) 0.0399(11) Uani 1 1 d . . . . .
C6 C 0.6281(5) 0.4175(3) 0.4199(2) 0.0302(10) Uani 1 1 d . . . . .
H6 H 0.595344 0.468438 0.389944 0.036 Uiso 1 1 calc R U . . .
C2 C 0.2847(5) 0.4604(3) 0.4050(3) 0.0381(11) Uani 1 1 d . . . . .
H2A H 0.308517 0.508400 0.439174 0.046 Uiso 1 1 calc R U . . .
H2B H 0.312467 0.478041 0.354920 0.046 Uiso 1 1 calc R U . . .
C3 C 0.3615(5) 0.3748(3) 0.4275(2) 0.0300(10) Uani 1 1 d . . . . .
H3A H 0.379971 0.339003 0.382757 0.036 Uiso 1 1 calc R U . . .
C18 C 0.5356(5) 0.2788(3) 0.0861(3) 0.0372(11) Uani 1 1 d . . . . .
C5 C 0.5024(5) 0.3867(3) 0.4692(2) 0.0335(10) Uani 1 1 d . . . . .
H5A H 0.528807 0.330567 0.492437 0.040 Uiso 1 1 calc R U . . .
H5B H 0.487654 0.430182 0.508620 0.040 Uiso 1 1 calc R U . . .
C10 C 0.9447(5) 0.2549(3) 0.3024(2) 0.0338(10) Uani 1 1 d . . . . .
H10 H 0.954193 0.263363 0.356380 0.041 Uiso 1 1 calc R U . . .
C1 C 0.1246(5) 0.4381(3) 0.4087(3) 0.0423(12) Uani 1 1 d . . . . .
H1A H 0.067787 0.488586 0.426269 0.051 Uiso 1 1 calc R U . . .
H1B H 0.087767 0.419684 0.360318 0.051 Uiso 1 1 calc R U . . .
C12 C 1.0158(4) 0.3254(3) 0.1871(2) 0.0368(11) Uani 1 1 d . . . . .
H12A H 1.042281 0.388095 0.188027 0.044 Uiso 1 1 calc R U . . .
H12B H 1.054325 0.298745 0.141907 0.044 Uiso 1 1 calc R U . . .
C13 C 1.0339(5) 0.1831(3) 0.2667(3) 0.0413(12) Uani 1 1 d . . . . .
C20 C 0.5317(6) 0.3196(4) 0.0087(3) 0.0499(14) Uani 1 1 d . . . . .
H20A H 0.471628 0.372153 0.009335 0.075 Uiso 1 1 calc R U . . .
H20B H 0.491870 0.277262 -0.025955 0.075 Uiso 1 1 calc R U . . .
H20C H 0.629280 0.335337 -0.006317 0.075 Uiso 1 1 calc R U . . .
C11 C 1.0727(5) 0.2786(3) 0.2543(3) 0.0402(12) Uani 1 1 d . . . . .
H11 H 1.160990 0.302106 0.278401 0.048 Uiso 1 1 calc R U . . .
F1 F 0.2818(5) 0.5619(3) 0.1547(4) 0.150(2) Uani 1 1 d . . . . .
C22 C 0.4607(5) 0.4606(4) 0.1894(3) 0.0451(13) Uani 1 1 d . . . . .
F3 F 0.4169(8) 0.5991(3) 0.2409(2) 0.163(3) Uani 1 1 d . . . . .
C14 C 0.9780(6) 0.1257(4) 0.2045(3) 0.0515(14) Uani 1 1 d . . . . .
H14A H 0.924558 0.076248 0.224873 0.077 Uiso 1 1 calc R U . . .
H14B H 1.058986 0.103894 0.175690 0.077 Uiso 1 1 calc R U . . .
H14C H 0.914540 0.160268 0.173058 0.077 Uiso 1 1 calc R U . . .
C21 C 0.6175(6) 0.1913(3) 0.0830(3) 0.0562(15) Uani 1 1 d . . . . .
H21A H 0.715191 0.201620 0.065234 0.084 Uiso 1 1 calc R U . . .
H21B H 0.567950 0.151177 0.049807 0.084 Uiso 1 1 calc R U . . .
H21C H 0.621415 0.165658 0.132000 0.084 Uiso 1 1 calc R U . . .
C19 C 0.3792(5) 0.2626(4) 0.1113(3) 0.0600(16) Uani 1 1 d . . . . .
H19A H 0.379731 0.233312 0.158941 0.090 Uiso 1 1 calc R U . . .
H19B H 0.330036 0.225521 0.075510 0.090 Uiso 1 1 calc R U . . .
H19C H 0.328897 0.318570 0.115426 0.090 Uiso 1 1 calc R U . . .
C15 C 1.1326(6) 0.1336(4) 0.3193(3) 0.0611(17) Uani 1 1 d . . . . .
H15A H 1.166776 0.173564 0.357361 0.092 Uiso 1 1 calc R U . . .
H15B H 1.214687 0.110061 0.292320 0.092 Uiso 1 1 calc R U . . .
H15C H 1.079379 0.085453 0.342002 0.092 Uiso 1 1 calc R U . . .
C23 C 0.4128(8) 0.5559(4) 0.1783(4) 0.0708(19) Uani 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
N4 C9 1.468(5) . ?
N4 C16 1.350(5) . ?
N4 C12 1.476(5) . ?
O2 C8 1.216(5) . ?
O3 C16 1.231(5) . ?
N3 H3 0.8700 . ?
N3 C8 1.361(5) . ?
N3 C6 1.448(5) . ?
O1 C4 1.234(5) . ?
N5 H5 0.8700 . ?
N5 C17 1.461(6) . ?
N5 C22 1.328(6) . ?
O4 C22 1.216(6) . ?
F2 C23 1.321(7) . ?
N1 H1 0.8700 . ?
N1 C4 1.337(6) . ?
N1 C1 1.453(6) . ?
C8 C9 1.535(6) . ?
C4 C3 1.515(6) . ?
C17 H17 0.9900 . ?
C17 C16 1.534(6) . ?
C17 C18 1.552(6) . ?
C9 H9 0.9900 . ?
C9 C10 1.519(6) . ?
N2 C7 1.132(6) . ?
C7 C6 1.478(6) . ?
C6 H6 0.9900 . ?
C6 C5 1.538(6) . ?
C2 H2A 0.9800 . ?
C2 H2B 0.9800 . ?
C2 C3 1.532(6) . ?
C2 C1 1.517(6) . ?
C3 H3A 0.9900 . ?
C3 C5 1.515(6) . ?
C18 C20 1.533(7) . ?
C18 C21 1.525(7) . ?
C18 C19 1.535(7) . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C10 H10 0.9900 . ?
C10 C13 1.510(6) . ?
C10 C11 1.512(6) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 C11 1.504(6) . ?
C13 C11 1.508(7) . ?
C13 C14 1.513(6) . ?
C13 C15 1.517(7) . ?
C20 H20A 0.9700 . ?
C20 H20B 0.9700 . ?
C20 H20C 0.9700 . ?
C11 H11 0.9900 . ?
F1 C23 1.287(8) . ?
C22 C23 1.522(8) . ?
F3 C23 1.311(7) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C14 H14C 0.9700 . ?
C21 H21A 0.9700 . ?
C21 H21B 0.9700 . ?
C21 H21C 0.9700 . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C19 H19C 0.9700 . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C15 H15C 0.9700 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C9 N4 C12 112.2(3) . . ?
C16 N4 C9 126.7(3) . . ?
C16 N4 C12 119.2(4) . . ?
C8 N3 H3 119.9 . . ?
C8 N3 C6 120.1(4) . . ?
C6 N3 H3 119.9 . . ?
C17 N5 H5 119.6 . . ?
C22 N5 H5 119.6 . . ?
C22 N5 C17 120.7(4) . . ?
C4 N1 H1 122.7 . . ?
C4 N1 C1 114.6(4) . . ?
C1 N1 H1 122.7 . . ?
O2 C8 N3 122.7(4) . . ?
O2 C8 C9 122.7(4) . . ?
N3 C8 C9 114.6(4) . . ?
O1 C4 N1 126.4(4) . . ?
O1 C4 C3 125.6(4) . . ?
N1 C4 C3 108.0(4) . . ?
N5 C17 H17 107.9 . . ?
N5 C17 C16 106.5(4) . . ?
N5 C17 C18 112.3(3) . . ?
C16 C17 H17 107.9 . . ?
C16 C17 C18 114.1(4) . . ?
C18 C17 H17 107.9 . . ?
N4 C9 C8 111.0(3) . . ?
N4 C9 H9 110.3 . . ?
N4 C9 C10 104.0(3) . . ?
C8 C9 H9 110.3 . . ?
C10 C9 C8 110.7(3) . . ?
C10 C9 H9 110.3 . . ?
N4 C16 C17 118.5(4) . . ?
O3 C16 N4 121.2(4) . . ?
O3 C16 C17 120.3(4) . . ?
N2 C7 C6 176.7(6) . . ?
N3 C6 C7 110.5(4) . . ?
N3 C6 H6 108.9 . . ?
N3 C6 C5 111.7(4) . . ?
C7 C6 H6 108.9 . . ?
C7 C6 C5 108.0(4) . . ?
C5 C6 H6 108.9 . . ?
H2A C2 H2B 108.9 . . ?
C3 C2 H2A 110.8 . . ?
C3 C2 H2B 110.8 . . ?
C1 C2 H2A 110.8 . . ?
C1 C2 H2B 110.8 . . ?
C1 C2 C3 104.5(4) . . ?
C4 C3 C2 103.1(4) . . ?
C4 C3 H3A 109.0 . . ?
C4 C3 C5 111.1(3) . . ?
C2 C3 H3A 109.0 . . ?
C5 C3 C2 115.4(4) . . ?
C5 C3 H3A 109.0 . . ?
C20 C18 C17 112.4(4) . . ?
C20 C18 C19 108.4(4) . . ?
C21 C18 C17 109.3(4) . . ?
C21 C18 C20 109.2(4) . . ?
C21 C18 C19 109.8(4) . . ?
C19 C18 C17 107.8(4) . . ?
C6 C5 H5A 108.9 . . ?
C6 C5 H5B 108.9 . . ?
C3 C5 C6 113.2(3) . . ?
C3 C5 H5A 108.9 . . ?
C3 C5 H5B 108.9 . . ?
H5A C5 H5B 107.8 . . ?
C9 C10 H10 117.9 . . ?
C13 C10 C9 120.4(4) . . ?
C13 C10 H10 117.9 . . ?
C13 C10 C11 59.9(3) . . ?
C11 C10 C9 108.1(3) . . ?
C11 C10 H10 117.9 . . ?
N1 C1 C2 102.7(4) . . ?
N1 C1 H1A 111.2 . . ?
N1 C1 H1B 111.2 . . ?
C2 C1 H1A 111.2 . . ?
C2 C1 H1B 111.2 . . ?
H1A C1 H1B 109.1 . . ?
N4 C12 H12A 110.8 . . ?
N4 C12 H12B 110.8 . . ?
N4 C12 C11 104.8(4) . . ?
H12A C12 H12B 108.9 . . ?
C11 C12 H12A 110.8 . . ?
C11 C12 H12B 110.8 . . ?
C10 C13 C14 123.1(4) . . ?
C10 C13 C15 114.4(4) . . ?
C11 C13 C10 60.1(3) . . ?
C11 C13 C14 121.4(4) . . ?
C11 C13 C15 115.1(4) . . ?
C14 C13 C15 112.9(4) . . ?
C18 C20 H20A 109.5 . . ?
C18 C20 H20B 109.5 . . ?
C18 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C10 C11 H11 118.4 . . ?
C12 C11 C10 107.8(4) . . ?
C12 C11 C13 119.3(4) . . ?
C12 C11 H11 118.4 . . ?
C13 C11 C10 60.0(3) . . ?
C13 C11 H11 118.4 . . ?
N5 C22 C23 114.9(5) . . ?
O4 C22 N5 127.7(5) . . ?
O4 C22 C23 117.4(5) . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C18 C21 H21A 109.5 . . ?
C18 C21 H21B 109.5 . . ?
C18 C21 H21C 109.5 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
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 . . ?
C13 C15 H15A 109.5 . . ?
C13 C15 H15B 109.5 . . ?
C13 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
F2 C23 C22 116.0(5) . . ?
F1 C23 F2 106.0(6) . . ?
F1 C23 C22 112.6(6) . . ?
F1 C23 F3 106.2(6) . . ?
F3 C23 F2 104.9(6) . . ?
F3 C23 C22 110.5(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
N4 C9 C10 C13 -54.0(5) . . . . ?
N4 C9 C10 C11 11.1(4) . . . . ?
N4 C12 C11 C10 -9.3(5) . . . . ?
N4 C12 C11 C13 55.7(5) . . . . ?
O2 C8 C9 N4 -10.2(6) . . . . ?
O2 C8 C9 C10 104.8(5) . . . . ?
N3 C8 C9 N4 169.1(3) . . . . ?
N3 C8 C9 C10 -75.9(4) . . . . ?
N3 C6 C5 C3 -71.2(5) . . . . ?
O1 C4 C3 C2 -162.7(4) . . . . ?
O1 C4 C3 C5 -38.6(6) . . . . ?
N5 C17 C16 N4 120.9(4) . . . . ?
N5 C17 C16 O3 -60.6(5) . . . . ?
N5 C17 C18 C20 47.7(5) . . . . ?
N5 C17 C18 C21 169.1(4) . . . . ?
N5 C17 C18 C19 -71.6(5) . . . . ?
N5 C22 C23 F2 -15.2(8) . . . . ?
N5 C22 C23 F1 107.1(6) . . . . ?
N5 C22 C23 F3 -134.3(6) . . . . ?
O4 C22 C23 F2 166.8(6) . . . . ?
O4 C22 C23 F1 -70.9(8) . . . . ?
O4 C22 C23 F3 47.6(9) . . . . ?
N1 C4 C3 C2 17.1(5) . . . . ?
N1 C4 C3 C5 141.3(4) . . . . ?
C8 N3 C6 C7 -83.2(5) . . . . ?
C8 N3 C6 C5 156.6(4) . . . . ?
C8 C9 C10 C13 -173.3(4) . . . . ?
C8 C9 C10 C11 -108.2(4) . . . . ?
C4 N1 C1 C2 -15.4(6) . . . . ?
C4 C3 C5 C6 169.3(4) . . . . ?
C17 N5 C22 O4 -2.2(8) . . . . ?
C17 N5 C22 C23 -180.0(5) . . . . ?
C9 N4 C16 O3 169.1(4) . . . . ?
C9 N4 C16 C17 -12.4(7) . . . . ?
C9 N4 C12 C11 17.3(5) . . . . ?
C9 C10 C13 C11 94.4(4) . . . . ?
C9 C10 C13 C14 -15.7(7) . . . . ?
C9 C10 C13 C15 -159.5(5) . . . . ?
C9 C10 C11 C12 -1.1(5) . . . . ?
C9 C10 C11 C13 -115.2(4) . . . . ?
C16 N4 C9 C8 -63.1(5) . . . . ?
C16 N4 C9 C10 177.8(4) . . . . ?
C16 N4 C12 C11 -177.0(4) . . . . ?
C16 C17 C18 C20 -73.6(5) . . . . ?
C16 C17 C18 C21 47.8(5) . . . . ?
C16 C17 C18 C19 167.1(4) . . . . ?
C7 C6 C5 C3 167.1(4) . . . . ?
C6 N3 C8 O2 -8.0(6) . . . . ?
C6 N3 C8 C9 172.7(4) . . . . ?
C2 C3 C5 C6 -73.9(5) . . . . ?
C3 C2 C1 N1 24.9(5) . . . . ?
C18 C17 C16 N4 -114.6(5) . . . . ?
C18 C17 C16 O3 63.8(6) . . . . ?
C10 C13 C11 C12 -94.6(4) . . . . ?
C1 N1 C4 O1 178.6(4) . . . . ?
C1 N1 C4 C3 -1.2(6) . . . . ?
C1 C2 C3 C4 -25.7(5) . . . . ?
C1 C2 C3 C5 -147.0(4) . . . . ?
C12 N4 C9 C8 101.2(4) . . . . ?
C12 N4 C9 C10 -17.9(5) . . . . ?
C12 N4 C16 O3 5.8(7) . . . . ?
C12 N4 C16 C17 -175.8(4) . . . . ?
C13 C10 C11 C12 114.1(4) . . . . ?
C11 C10 C13 C14 -110.1(5) . . . . ?
C11 C10 C13 C15 106.1(5) . . . . ?
C22 N5 C17 C16 -130.9(4) . . . . ?
C22 N5 C17 C18 103.5(5) . . . . ?
C14 C13 C11 C10 112.8(5) . . . . ?
C14 C13 C11 C12 18.2(7) . . . . ?
C15 C13 C11 C10 -104.9(5) . . . . ?
C15 C13 C11 C12 160.5(4) . . . . ?


_olex2_submission_special_instructions 'No special instructions were received'
