# Supplementary Information (SI) for Chemical Science.
# 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_1
_database_code_depnum_ccdc_archive 'CCDC 2380818'
loop_
_audit_author_name
_audit_author_address
THEAT
;jilin university
China
;
_audit_update_record             
;
2024-08-30 deposited with the CCDC.	2025-03-27 downloaded from the CCDC.
;
_audit_creation_date             2024-05-16
_audit_creation_method           
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C12 H10 F3 N3 O2'
_chemical_formula_sum            'C12 H10 F3 N3 O2'
_chemical_formula_weight         285.23
_chemical_absolute_configuration ?
_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           33
_space_group_name_H-M_alt        'P n a 21'
_space_group_name_Hall           'P 2c -2n'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'x+1/2, -y+1/2, z'
'-x+1/2, y+1/2, z+1/2'

_cell_length_a                   13.4921(4)
_cell_length_b                   17.9826(6)
_cell_length_c                   5.17080(10)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1254.56(6)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    8234
_cell_measurement_temperature    298
_cell_measurement_theta_max      29.541
_cell_measurement_theta_min      2.723
_shelx_estimated_absorpt_T_max   0.987
_shelx_estimated_absorpt_T_min   0.987
_exptl_absorpt_coefficient_mu    0.135
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.510
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             584
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0280
_diffrn_reflns_av_unetI/netI     0.0247
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_number            17868
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.619
_diffrn_reflns_theta_min         2.722
_diffrn_ambient_temperature      298
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           30.0
_diffrn_source_power             1.5
_diffrn_source_voltage           50.0
_reflns_Friedel_coverage         0.798
_reflns_Friedel_fraction_full    0.992
_reflns_Friedel_fraction_max     0.976
_reflns_number_gt                2483
_reflns_number_total             3479
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.40A (Bruker, 2019)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40A (Bruker, 2019)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.205
_refine_diff_density_min         -0.156
_refine_diff_density_rms         0.031
_refine_ls_abs_structure_details 
;
 Flack x determined using 828 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.0(2)
_refine_ls_extinction_coef       0.012(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     199
_refine_ls_number_reflns         3479
_refine_ls_number_restraints     8
_refine_ls_R_factor_all          0.0733
_refine_ls_R_factor_gt           0.0455
_refine_ls_restrained_S_all      1.075
_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)+(0.0317P)²+0.2770P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0882
_refine_ls_wR_factor_ref         0.1000
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H,H) groups, All C(H,H,H,H) groups, All N(H) groups
 At 1.5 times of:
  All O(H) groups
2. Restrained distances
 C9-C11 \\sim C9-C10
 with sigma of 0.02
 C14-C12 \\sim C14-C13
 with sigma of 0.02
 O2-C11 \\sim O1-C10
 with sigma of 0.02
 O2-C12 \\sim O1-C13
 with sigma of 0.02
 C9-O2 \\sim C9-O1
 with sigma of 0.04
 C14-O2 \\sim C14-O1
 with sigma of 0.04
 C11-C12 \\sim C10-C13
 with sigma of 0.04
3. Uiso/Uaniso restraints and constraints
Uanis(C11) = Uanis(C10) = Uanis(C9)
4. Others
 Sof(H9BC)=Sof(H9BD)=Sof(H14C)=Sof(H14D)=Sof(O1)=Sof(C10)=Sof(H10A)=Sof(H10B)=
 Sof(C13)=Sof(H13A)=Sof(H13B)=1-FVAR(1)
 Sof(H9AA)=Sof(H9AB)=Sof(H14A)=Sof(H14B)=Sof(O2)=Sof(C11)=Sof(H11A)=Sof(H11B)=
 Sof(C12)=Sof(H12A)=Sof(H12B)=FVAR(1)
5.a Secondary CH2 refined with riding coordinates:
 C9(H9AA,H9AB), C9(H9BC,H9BD), C14(H14A,H14B), C14(H14C,H14D), C11(H11A,H11B),
 C12(H12A,H12B), C10(H10A,H10B), C13(H13A,H13B)
5.b Aromatic/amide H refined with riding coordinates:
 N005(H005)
5.c Idealised tetrahedral OH refined as rotating group:
 O3(H3)
;
_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
F1 F 0.41929(15) 0.75106(11) -0.5074(5) 0.0811(6) Uani 1 1 d . . . . .
F2 F 0.53370(12) 0.68489(11) -0.1480(5) 0.0783(6) Uani 1 1 d . . . . .
F3 F 0.14774(10) 0.60975(10) -0.2269(4) 0.0675(5) Uani 1 1 d . . . . .
O3 O -0.02583(15) 0.46540(11) 0.6545(5) 0.0602(5) Uani 1 1 d . . . . .
H3 H -0.021431 0.494505 0.776085 0.090 Uiso 1 1 calc R U . . .
N1 N 0.1750(2) 0.74490(18) -0.7158(8) 0.0857(9) Uani 1 1 d . . . . .
N2 N 0.5283(2) 0.56632(17) 0.3313(7) 0.0783(8) Uani 1 1 d . . . . .
N005 N 0.25437(16) 0.53868(13) 0.1351(5) 0.0556(6) Uani 1 1 d . . . . .
H005 H 0.190632 0.538847 0.136396 0.067 Uiso 1 1 calc R U . . .
C1 C 0.2198(2) 0.71688(16) -0.5569(6) 0.0581(7) Uani 1 1 d . . . . .
C2 C 0.2803(2) 0.68164(14) -0.3645(6) 0.0469(6) Uani 1 1 d . . . . .
C3 C 0.3804(2) 0.70074(15) -0.3452(7) 0.0534(7) Uani 1 1 d . . . . .
C4 C 0.43780(19) 0.66636(15) -0.1655(7) 0.0521(6) Uani 1 1 d . . . . .
C5 C 0.40032(19) 0.61251(14) 0.0021(6) 0.0448(6) Uani 1 1 d . . . . .
C6 C 0.29960(18) 0.59043(14) -0.0143(6) 0.0435(6) Uani 1 1 d . . . . .
C7 C 0.24342(17) 0.62798(14) -0.2024(6) 0.0463(6) Uani 1 1 d . . . . .
C8 C 0.4692(2) 0.58462(16) 0.1885(6) 0.0535(7) Uani 1 1 d . . . . .
C9 C 0.3035(2) 0.48279(16) 0.2936(7) 0.0617(7) Uani 1 1 d D . . . .
H9AA H 0.362041 0.466252 0.201312 0.074 Uiso 0.498(9) 1 calc R U P A 1
H9AB H 0.325928 0.506906 0.450798 0.074 Uiso 0.498(9) 1 calc R U P A 1
H9BC H 0.304969 0.498567 0.472926 0.074 Uiso 0.502(9) 1 calc R U P A 2
H9BD H 0.371077 0.475491 0.235168 0.074 Uiso 0.502(9) 1 calc R U P A 2
C14 C 0.0257(2) 0.39866(17) 0.7155(7) 0.0639(9) Uani 1 1 d D . . . .
H14A H 0.061385 0.405489 0.876652 0.077 Uiso 0.498(9) 1 calc R U P A 1
H14B H -0.021974 0.358980 0.740901 0.077 Uiso 0.498(9) 1 calc R U P A 1
H14C H -0.007616 0.356987 0.634185 0.077 Uiso 0.502(9) 1 calc R U P A 2
H14D H 0.024091 0.390928 0.901086 0.077 Uiso 0.502(9) 1 calc R U P A 2
O2 O 0.1645(3) 0.4376(3) 0.5000(15) 0.0589(18) Uani 0.498(9) 1 d D . P A 1
C11 C 0.2479(6) 0.4178(5) 0.3669(17) 0.0617(7) Uani 0.498(9) 1 d D . P A 1
H11A H 0.229395 0.390163 0.213187 0.074 Uiso 0.498(9) 1 calc R U P A 1
H11B H 0.288764 0.385895 0.474011 0.074 Uiso 0.498(9) 1 calc R U P A 1
C12 C 0.0934(5) 0.3773(4) 0.5208(16) 0.0523(18) Uani 0.498(9) 1 d D . P A 1
H12A H 0.059349 0.369998 0.357629 0.063 Uiso 0.498(9) 1 calc R U P A 1
H12B H 0.126534 0.331405 0.567818 0.063 Uiso 0.498(9) 1 calc R U P A 1
O1 O 0.1448(3) 0.4113(3) 0.3504(11) 0.0507(15) Uani 0.502(9) 1 d D . P A 2
C10 C 0.2451(6) 0.4112(5) 0.2671(18) 0.0617(7) Uani 0.502(9) 1 d D . P A 2
H10A H 0.246184 0.396810 0.086402 0.074 Uiso 0.502(9) 1 calc R U P A 2
H10B H 0.279890 0.372893 0.362980 0.074 Uiso 0.502(9) 1 calc R U P A 2
C13 C 0.1330(6) 0.4009(5) 0.6253(17) 0.064(2) Uani 0.502(9) 1 d D . P A 2
H13A H 0.166714 0.441021 0.714530 0.076 Uiso 0.502(9) 1 calc R U P A 2
H13B H 0.164977 0.354723 0.674685 0.076 Uiso 0.502(9) 1 calc R U P A 2


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F1 C3 1.341(3) . ?
F2 C4 1.339(3) . ?
F3 C7 1.338(3) . ?
O3 H3 0.8200 . ?
O3 C14 1.423(3) . ?
N1 C1 1.138(4) . ?
N2 C8 1.135(4) . ?
N005 H005 0.8600 . ?
N005 C6 1.355(3) . ?
N005 C9 1.456(3) . ?
C1 C2 1.434(4) . ?
C2 C3 1.397(4) . ?
C2 C7 1.372(4) . ?
C3 C4 1.358(4) . ?
C4 C5 1.394(4) . ?
C5 C6 1.418(4) . ?
C5 C8 1.430(4) . ?
C6 C7 1.406(4) . ?
C9 H9AA 0.9700 . ?
C9 H9AB 0.9700 . ?
C9 H9BC 0.9700 . ?
C9 H9BD 0.9700 . ?
C9 C11 1.439(8) . ?
C9 C10 1.515(9) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C14 H14C 0.9700 . ?
C14 H14D 0.9700 . ?
C14 C12 1.412(7) . ?
C14 C13 1.520(8) . ?
O2 C11 1.366(8) . ?
O2 C12 1.451(9) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
O1 C10 1.420(8) . ?
O1 C13 1.443(10) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C13 H13A 0.9700 . ?
C13 H13B 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
C14 O3 H3 109.5 . . ?
C6 N005 H005 116.9 . . ?
C6 N005 C9 126.2(2) . . ?
C9 N005 H005 116.9 . . ?
N1 C1 C2 177.3(4) . . ?
C3 C2 C1 119.4(3) . . ?
C7 C2 C1 121.9(3) . . ?
C7 C2 C3 118.7(2) . . ?
F1 C3 C2 120.0(3) . . ?
F1 C3 C4 120.8(3) . . ?
C4 C3 C2 119.2(3) . . ?
F2 C4 C3 118.9(3) . . ?
F2 C4 C5 118.8(3) . . ?
C3 C4 C5 122.3(2) . . ?
C4 C5 C6 120.3(3) . . ?
C4 C5 C8 115.3(2) . . ?
C6 C5 C8 124.4(3) . . ?
N005 C6 C5 126.2(2) . . ?
N005 C6 C7 118.8(2) . . ?
C7 C6 C5 115.1(2) . . ?
F3 C7 C2 117.7(2) . . ?
F3 C7 C6 117.9(2) . . ?
C2 C7 C6 124.4(2) . . ?
N2 C8 C5 175.3(3) . . ?
N005 C9 H9AA 107.8 . . ?
N005 C9 H9AB 107.8 . . ?
N005 C9 H9BC 110.2 . . ?
N005 C9 H9BD 110.2 . . ?
N005 C9 C10 107.4(4) . . ?
H9AA C9 H9AB 107.1 . . ?
H9BC C9 H9BD 108.5 . . ?
C11 C9 N005 118.1(4) . . ?
C11 C9 H9AA 107.8 . . ?
C11 C9 H9AB 107.8 . . ?
C10 C9 H9BC 110.2 . . ?
C10 C9 H9BD 110.2 . . ?
O3 C14 H14A 109.0 . . ?
O3 C14 H14B 109.0 . . ?
O3 C14 H14C 109.2 . . ?
O3 C14 H14D 109.2 . . ?
O3 C14 C13 112.0(4) . . ?
H14A C14 H14B 107.8 . . ?
H14C C14 H14D 107.9 . . ?
C12 C14 O3 112.8(4) . . ?
C12 C14 H14A 109.0 . . ?
C12 C14 H14B 109.0 . . ?
C13 C14 H14C 109.2 . . ?
C13 C14 H14D 109.2 . . ?
C11 O2 C12 112.8(5) . . ?
C9 C11 H11A 109.5 . . ?
C9 C11 H11B 109.5 . . ?
O2 C11 C9 110.5(6) . . ?
O2 C11 H11A 109.5 . . ?
O2 C11 H11B 109.5 . . ?
H11A C11 H11B 108.1 . . ?
C14 C12 O2 106.1(6) . . ?
C14 C12 H12A 110.5 . . ?
C14 C12 H12B 110.5 . . ?
O2 C12 H12A 110.5 . . ?
O2 C12 H12B 110.5 . . ?
H12A C12 H12B 108.7 . . ?
C10 O1 C13 113.8(6) . . ?
C9 C10 H10A 107.8 . . ?
C9 C10 H10B 107.8 . . ?
O1 C10 C9 117.9(6) . . ?
O1 C10 H10A 107.8 . . ?
O1 C10 H10B 107.8 . . ?
H10A C10 H10B 107.2 . . ?
C14 C13 H13A 108.7 . . ?
C14 C13 H13B 108.7 . . ?
O1 C13 C14 114.3(6) . . ?
O1 C13 H13A 108.7 . . ?
O1 C13 H13B 108.7 . . ?
H13A C13 H13B 107.6 . . ?

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
F1 C3 C4 F2 1.7(5) . . . . ?
F1 C3 C4 C5 -178.5(3) . . . . ?
F2 C4 C5 C6 -178.7(3) . . . . ?
F2 C4 C5 C8 3.0(4) . . . . ?
O3 C14 C12 O2 60.9(7) . . . . ?
O3 C14 C13 O1 -59.6(9) . . . . ?
N005 C6 C7 F3 -1.0(4) . . . . ?
N005 C6 C7 C2 179.7(3) . . . . ?
N005 C9 C11 O2 -58.2(7) . . . . ?
N005 C9 C10 O1 -61.5(7) . . . . ?
C1 C2 C3 F1 -0.7(4) . . . . ?
C1 C2 C3 C4 -179.0(3) . . . . ?
C1 C2 C7 F3 -0.8(4) . . . . ?
C1 C2 C7 C6 178.6(3) . . . . ?
C2 C3 C4 F2 180.0(3) . . . . ?
C2 C3 C4 C5 -0.2(5) . . . . ?
C3 C2 C7 F3 -179.0(3) . . . . ?
C3 C2 C7 C6 0.3(4) . . . . ?
C3 C4 C5 C6 1.4(4) . . . . ?
C3 C4 C5 C8 -176.9(3) . . . . ?
C4 C5 C6 N005 179.6(3) . . . . ?
C4 C5 C6 C7 -1.6(4) . . . . ?
C5 C6 C7 F3 -179.8(2) . . . . ?
C5 C6 C7 C2 0.8(4) . . . . ?
C6 N005 C9 C11 -158.9(5) . . . . ?
C6 N005 C9 C10 -140.0(4) . . . . ?
C7 C2 C3 F1 177.6(3) . . . . ?
C7 C2 C3 C4 -0.7(4) . . . . ?
C8 C5 C6 N005 -2.3(4) . . . . ?
C8 C5 C6 C7 176.5(2) . . . . ?
C9 N005 C6 C5 -16.7(5) . . . . ?
C9 N005 C6 C7 164.5(3) . . . . ?
C11 O2 C12 C14 164.9(6) . . . . ?
C12 O2 C11 C9 165.1(8) . . . . ?
C10 O1 C13 C14 -178.4(6) . . . . ?
C13 O1 C10 C9 -82.1(10) . . . . ?


_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_0830
_database_code_depnum_ccdc_archive 'CCDC 2380828'
loop_
_audit_author_name
_audit_author_address
'Tingting Ji'
;Jilin University
China
;
_audit_update_record             
;
2024-08-30 deposited with the CCDC.	2025-03-27 downloaded from the CCDC.
;
_audit_creation_date             2024-08-30
_audit_creation_method           
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C11 H8 F3 N3 O'
_chemical_formula_sum            'C11 H8 F3 N3 O'
_chemical_formula_weight         255.20
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   9.6318(4)
_cell_length_b                   6.3855(2)
_cell_length_c                   17.9069(7)
_cell_angle_alpha                90
_cell_angle_beta                 93.530(2)
_cell_angle_gamma                90
_cell_volume                     1099.25(7)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9939
_cell_measurement_temperature    100.00
_cell_measurement_theta_max      27.465
_cell_measurement_theta_min      3.388
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.137
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear bluish blue'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   bluish
_exptl_crystal_colour_primary    blue
_exptl_crystal_density_diffrn    1.542
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             520
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0256
_diffrn_reflns_av_unetI/netI     0.0137
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            21630
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.492
_diffrn_reflns_theta_min         3.388
_diffrn_ambient_temperature      100.00
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           30.0
_diffrn_source_power             1.5
_diffrn_source_voltage           50.0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2208
_reflns_number_total             2513
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.40A (Bruker, 2019)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40A (Bruker, 2019)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.292
_refine_diff_density_min         -0.346
_refine_diff_density_rms         0.041
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     164
_refine_ls_number_reflns         2513
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0366
_refine_ls_R_factor_gt           0.0311
_refine_ls_restrained_S_all      1.033
_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)+(0.0365P)²+0.5333P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0788
_refine_ls_wR_factor_ref         0.0829
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All O(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C00G(H00A,H00B), C00H(H00C,H00D), C00I(H00E,H00F)
2.b Aromatic/amide H refined with riding coordinates:
 N005(H005)
2.c Idealised tetrahedral OH refined as rotating group:
 O004(H004)
;
_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
F001 F 0.59371(7) 0.71272(11) 0.53204(4) 0.02157(16) Uani 1 1 d . . . . .
F002 F 0.32209(7) 0.57448(12) 0.73653(4) 0.02651(18) Uani 1 1 d . . . . .
F003 F 0.46761(7) 0.21520(12) 0.76284(4) 0.02861(18) Uani 1 1 d . . . . .
O004 O 1.14285(9) 0.33483(14) 0.54499(5) 0.0250(2) Uani 1 1 d . . . . .
H004 H 1.193789 0.231950 0.557011 0.038 Uiso 1 1 calc R U . . .
N005 N 0.74369(10) 0.36474(16) 0.55229(5) 0.0194(2) Uani 1 1 d . . . . .
H005 H 0.749523 0.451401 0.514401 0.023 Uiso 1 1 calc R U . . .
N006 N 0.31775(10) 0.98517(17) 0.60334(6) 0.0255(2) Uani 1 1 d . . . . .
N007 N 0.71035(11) -0.08354(17) 0.69803(6) 0.0274(2) Uani 1 1 d . . . . .
C008 C 0.64230(11) 0.40205(17) 0.59980(6) 0.0170(2) Uani 1 1 d . . . . .
C009 C 0.56182(11) 0.58591(17) 0.58874(6) 0.0172(2) Uani 1 1 d . . . . .
C00A C 0.45467(11) 0.64389(17) 0.63165(6) 0.0180(2) Uani 1 1 d . . . . .
C00B C 0.60405(11) 0.27505(18) 0.66006(6) 0.0186(2) Uani 1 1 d . . . . .
C00C C 0.37844(11) 0.83383(19) 0.61571(6) 0.0202(2) Uani 1 1 d . . . . .
C00D C 0.49700(12) 0.33749(19) 0.70518(6) 0.0206(2) Uani 1 1 d . . . . .
C00E C 0.42315(11) 0.51689(19) 0.69213(6) 0.0200(2) Uani 1 1 d . . . . .
C00F C 0.66729(12) 0.07783(19) 0.67999(7) 0.0214(2) Uani 1 1 d . . . . .
C00G C 0.95578(11) 0.22174(19) 0.62234(6) 0.0207(2) Uani 1 1 d . . . . .
H00A H 0.910017 0.258728 0.668565 0.025 Uiso 1 1 calc R U . . .
H00B H 1.005034 0.087145 0.631311 0.025 Uiso 1 1 calc R U . . .
C00H C 0.84421(11) 0.19315(18) 0.55846(6) 0.0202(2) Uani 1 1 d . . . . .
H00C H 0.890228 0.180924 0.510714 0.024 Uiso 1 1 calc R U . . .
H00D H 0.793835 0.060575 0.566290 0.024 Uiso 1 1 calc R U . . .
C00I C 1.06133(12) 0.38995(19) 0.60655(7) 0.0222(2) Uani 1 1 d . . . . .
H00E H 1.012058 0.523258 0.595071 0.027 Uiso 1 1 calc R U . . .
H00F H 1.123916 0.412003 0.651812 0.027 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F001 C009 1.3487(12) . ?
F002 C00E 1.3455(13) . ?
F003 C00D 1.3387(13) . ?
O004 H004 0.8400 . ?
O004 C00I 1.4359(14) . ?
N005 H005 0.8800 . ?
N005 C008 1.3552(14) . ?
N005 C00H 1.4618(14) . ?
N006 C00C 1.1440(16) . ?
N007 C00F 1.1496(16) . ?
C008 C009 1.4141(15) . ?
C008 C00B 1.4166(15) . ?
C009 C00A 1.3748(16) . ?
C00A C00C 1.4373(16) . ?
C00A C00E 1.4011(16) . ?
C00B C00D 1.4062(16) . ?
C00B C00F 1.4344(16) . ?
C00D C00E 1.3610(17) . ?
C00G H00A 0.9900 . ?
C00G H00B 0.9900 . ?
C00G C00H 1.5315(15) . ?
C00G C00I 1.5174(17) . ?
C00H H00C 0.9900 . ?
C00H H00D 0.9900 . ?
C00I H00E 0.9900 . ?
C00I H00F 0.9900 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C00I O004 H004 109.5 . . ?
C008 N005 H005 117.1 . . ?
C008 N005 C00H 125.72(10) . . ?
C00H N005 H005 117.1 . . ?
N005 C008 C009 117.91(10) . . ?
N005 C008 C00B 127.50(10) . . ?
C009 C008 C00B 114.58(10) . . ?
F001 C009 C008 117.10(9) . . ?
F001 C009 C00A 118.20(10) . . ?
C00A C009 C008 124.69(10) . . ?
C009 C00A C00C 120.54(10) . . ?
C009 C00A C00E 118.81(10) . . ?
C00E C00A C00C 120.63(10) . . ?
C008 C00B C00F 124.46(10) . . ?
C00D C00B C008 120.64(10) . . ?
C00D C00B C00F 114.90(10) . . ?
N006 C00C C00A 179.72(13) . . ?
F003 C00D C00B 118.37(10) . . ?
F003 C00D C00E 119.36(10) . . ?
C00E C00D C00B 122.27(10) . . ?
F002 C00E C00A 119.84(10) . . ?
F002 C00E C00D 121.20(10) . . ?
C00D C00E C00A 118.95(10) . . ?
N007 C00F C00B 175.68(13) . . ?
H00A C00G H00B 107.8 . . ?
C00H C00G H00A 109.0 . . ?
C00H C00G H00B 109.0 . . ?
C00I C00G H00A 109.0 . . ?
C00I C00G H00B 109.0 . . ?
C00I C00G C00H 113.11(10) . . ?
N005 C00H C00G 113.46(9) . . ?
N005 C00H H00C 108.9 . . ?
N005 C00H H00D 108.9 . . ?
C00G C00H H00C 108.9 . . ?
C00G C00H H00D 108.9 . . ?
H00C C00H H00D 107.7 . . ?
O004 C00I C00G 111.95(10) . . ?
O004 C00I H00E 109.2 . . ?
O004 C00I H00F 109.2 . . ?
C00G C00I H00E 109.2 . . ?
C00G C00I H00F 109.2 . . ?
H00E C00I H00F 107.9 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
F001 C009 C00A C00C 0.54(15) . . . . ?
F001 C009 C00A C00E -178.09(9) . . . . ?
F003 C00D C00E F002 0.63(16) . . . . ?
F003 C00D C00E C00A 179.99(10) . . . . ?
N005 C008 C009 F001 -1.00(14) . . . . ?
N005 C008 C009 C00A 179.26(10) . . . . ?
N005 C008 C00B C00D 179.09(11) . . . . ?
N005 C008 C00B C00F -1.31(18) . . . . ?
C008 N005 C00H C00G -72.60(14) . . . . ?
C008 C009 C00A C00C -179.72(10) . . . . ?
C008 C009 C00A C00E 1.65(16) . . . . ?
C008 C00B C00D F003 -177.98(10) . . . . ?
C008 C00B C00D C00E 1.98(17) . . . . ?
C009 C008 C00B C00D -2.06(15) . . . . ?
C009 C008 C00B C00F 177.54(10) . . . . ?
C009 C00A C00E F002 177.59(10) . . . . ?
C009 C00A C00E C00D -1.79(16) . . . . ?
C00B C008 C009 F001 -179.97(9) . . . . ?
C00B C008 C009 C00A 0.29(16) . . . . ?
C00B C00D C00E F002 -179.33(10) . . . . ?
C00B C00D C00E C00A 0.04(17) . . . . ?
C00C C00A C00E F002 -1.05(16) . . . . ?
C00C C00A C00E C00D 179.58(10) . . . . ?
C00F C00B C00D F003 2.39(15) . . . . ?
C00F C00B C00D C00E -177.66(10) . . . . ?
C00H N005 C008 C009 174.74(10) . . . . ?
C00H N005 C008 C00B -6.44(18) . . . . ?
C00H C00G C00I O004 -65.21(12) . . . . ?
C00I C00G C00H N005 -72.58(12) . . . . ?

_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_1_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 2380823'
loop_
_audit_author_name
_audit_author_address
'Tingting Ji'
;Jilin University
China
;
_audit_update_record             
;
2024-08-30 deposited with the CCDC.	2025-03-27 downloaded from the CCDC.
;
_audit_creation_date             2024-07-12
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C12 H10 F3 N3 O2'
_chemical_formula_sum            'C12 H10 F3 N3 O2'
_chemical_formula_weight         285.23
_chemical_absolute_configuration ?
_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           33
_space_group_name_H-M_alt        'P n a 21'
_space_group_name_Hall           'P 2c -2n'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'-x+1/2, y+1/2, z+1/2'
'x+1/2, -y+1/2, z'

_cell_length_a                   13.3841(8)
_cell_length_b                   17.8129(10)
_cell_length_c                   5.0896(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1213.41(11)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9838
_cell_measurement_temperature    100
_cell_measurement_theta_max      29.559
_cell_measurement_theta_min      2.747
_shelx_estimated_absorpt_T_max   0.986
_shelx_estimated_absorpt_T_min   0.986
_exptl_absorpt_coefficient_mu    0.139
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.561
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             584
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0303
_diffrn_reflns_av_unetI/netI     0.0160
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       6
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_number            31168
_diffrn_reflns_point_group_measured_fraction_full 0.971
_diffrn_reflns_point_group_measured_fraction_max 0.938
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.608
_diffrn_reflns_theta_min         2.747
_diffrn_ambient_temperature      100
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           30.0
_diffrn_source_power             1.5
_diffrn_source_voltage           50.0
_reflns_Friedel_coverage         0.699
_reflns_Friedel_fraction_full    0.937
_reflns_Friedel_fraction_max     0.863
_reflns_number_gt                2981
_reflns_number_total             3193
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.40A (Bruker, 2019)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40A (Bruker, 2019)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve 1.5 (Bourhis et al., 2015)'
_refine_diff_density_max         0.220
_refine_diff_density_min         -0.194
_refine_diff_density_rms         0.040
_refine_ls_abs_structure_details 
;
 Flack x determined using 1175 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.10(16)
_refine_ls_extinction_coef       0.014(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     182
_refine_ls_number_reflns         3193
_refine_ls_number_restraints     5
_refine_ls_R_factor_all          0.0349
_refine_ls_R_factor_gt           0.0310
_refine_ls_restrained_S_all      1.076
_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)+(0.0397P)²+0.3917P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0790
_refine_ls_wR_factor_ref         0.0823
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H,H) groups, All C(H,H,H,H) groups, All N(H) groups
 At 1.5 times of:
  All O(H) groups
2. Restrained distances
 O1-C10 \\sim O4A-C10
 with sigma of 0.02
 O1-C11 \\sim O4A-C6A
 with sigma of 0.02
 C11-C12 \\sim C6A-C12
 with sigma of 0.02
 O1-C12 \\sim O4A-C12
 with sigma of 0.04
 C10-C11 \\sim C10-C6A
 with sigma of 0.04
 C9-C10 \\sim C9-CA
 with sigma of 0.02
 O1-C10 \\sim O1-CA
 with sigma of 0.02
 C10-O4A \\sim CA-O4A
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(C10) = Uanis(CA) = Uanis(O1) = Uanis(O4A) = Uanis(C11) = Uanis(C6A)
4. Others
 Sof(H12c)=Sof(H12d)=Sof(O4A)=Sof(C6A)=Sof(H6Aa)=Sof(H6Ab)=1-FVAR(1)
 Sof(H12a)=Sof(H12b)=Sof(O1)=Sof(C11)=Sof(H11a)=Sof(H11b)=FVAR(1)
 Sof(H9bc)=Sof(H9bd)=Sof(CA)=Sof(HAa)=Sof(HAb)=1-FVAR(2)
 Sof(H9aa)=Sof(H9ab)=Sof(C10)=Sof(H10a)=Sof(H10b)=FVAR(2)
5.a Secondary CH2 refined with riding coordinates:
 C9(H9aa,H9ab), C9(H9bc,H9bd), C12(H12a,H12b), C12(H12c,H12d), C10(H10a,H10b),
 C11(H11a,H11b), CA(HAa,HAb), C6A(H6Aa,H6Ab)
5.b Aromatic/amide H refined with riding coordinates:
 N3(H3)
5.c Idealised tetrahedral OH refined as rotating group:
 O2(H2)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
F1 F 0.91956(9) 0.24902(6) 0.3908(3) 0.0295(3) Uani 1 1 d . . . . .
F2 F 1.03595(8) 0.31550(6) 0.0250(3) 0.0290(3) Uani 1 1 d . . . . .
F3 F 0.64522(7) 0.39114(6) 0.0941(3) 0.0264(3) Uani 1 1 d . . . . .
O2 O 0.47290(9) 0.53359(7) -0.7886(3) 0.0233(3) Uani 1 1 d . . . . .
H2 H 0.482111 0.502820 -0.911331 0.035 Uiso 1 1 calc R U . . .
N1 N 0.67153(13) 0.25545(10) 0.5983(4) 0.0315(4) Uani 1 1 d . . . . .
N2 N 1.03258(13) 0.43377(10) -0.4675(4) 0.0305(4) Uani 1 1 d . . . . .
N3 N 0.75338(11) 0.46183(8) -0.2741(4) 0.0227(3) Uani 1 1 d . . . . .
H3 H 0.687631 0.461739 -0.275693 0.027 Uiso 1 1 calc R U . . .
C1 C 0.71756(14) 0.28387(10) 0.4359(4) 0.0226(4) Uani 1 1 d . . . . .
C2 C 0.77935(13) 0.31865(9) 0.2400(4) 0.0185(3) Uani 1 1 d . . . . .
C3 C 0.74179(12) 0.37226(9) 0.0717(4) 0.0181(3) Uani 1 1 d . . . . .
C4 C 0.79934(12) 0.41006(9) -0.1211(4) 0.0181(3) Uani 1 1 d . . . . .
C5 C 0.90110(12) 0.38784(9) -0.1336(4) 0.0181(3) Uani 1 1 d . . . . .
C6 C 0.97171(13) 0.41566(10) -0.3223(4) 0.0217(3) Uani 1 1 d . . . . .
C7 C 0.93924(12) 0.33368(9) 0.0400(4) 0.0200(3) Uani 1 1 d . . . . .
C8 C 0.88061(13) 0.29934(9) 0.2234(4) 0.0205(3) Uani 1 1 d . . . . .
C9 C 0.80377(14) 0.51778(10) -0.4368(4) 0.0259(4) Uani 1 1 d D . . . .
H9AA H 0.802651 0.502512 -0.623837 0.031 Uiso 0.565(7) 1 calc R U P A 1
H9AB H 0.874162 0.523811 -0.380933 0.031 Uiso 0.565(7) 1 calc R U P A 1
H9BC H 0.867326 0.531203 -0.349112 0.031 Uiso 0.435(7) 1 calc R U P A 2
H9BD H 0.821168 0.493683 -0.606036 0.031 Uiso 0.435(7) 1 calc R U P A 2
C12 C 0.52276(13) 0.60294(10) -0.8491(4) 0.0240(4) Uani 1 1 d D . . . .
H12A H 0.489373 0.644758 -0.755836 0.029 Uiso 0.611(2) 1 calc R U P B 1
H12B H 0.518257 0.612776 -1.040214 0.029 Uiso 0.611(2) 1 calc R U P B 1
H12C H 0.554529 0.598547 -1.024126 0.029 Uiso 0.389(2) 1 calc R U P B 2
H12D H 0.472493 0.643615 -0.858867 0.029 Uiso 0.389(2) 1 calc R U P B 2
O1 O 0.64305(15) 0.59272(11) -0.4878(4) 0.0214(3) Uani 0.611(2) 1 d D . P A 1
C10 C 0.7432(3) 0.5948(2) -0.3962(10) 0.0214(3) Uani 0.565(7) 1 d D . P A 1
H10A H 0.742730 0.607242 -0.206620 0.026 Uiso 0.565(7) 1 calc R U P A 1
H10B H 0.779039 0.635538 -0.488813 0.026 Uiso 0.565(7) 1 calc R U P A 1
C11 C 0.6345(2) 0.59927(16) -0.7656(7) 0.0214(3) Uani 0.611(2) 1 d D . P A 1
H11A H 0.666849 0.555593 -0.850585 0.026 Uiso 0.611(2) 1 calc R U P B 1
H11B H 0.669313 0.645256 -0.825191 0.026 Uiso 0.611(2) 1 calc R U P B 1
O4A O 0.6669(2) 0.56358(18) -0.6526(7) 0.0214(3) Uani 0.389(2) 1 d D . P A 2
CA C 0.7524(3) 0.5849(3) -0.4931(13) 0.0214(3) Uani 0.435(7) 1 d D . P A 2
HAA H 0.796106 0.620062 -0.590388 0.026 Uiso 0.435(7) 1 calc R U P A 2
HAB H 0.730152 0.609467 -0.328725 0.026 Uiso 0.435(7) 1 calc R U P A 2
C6A C 0.5960(3) 0.6227(3) -0.6638(10) 0.0214(3) Uani 0.389(2) 1 d D . P A 2
H6AA H 0.564981 0.630153 -0.489118 0.026 Uiso 0.389(2) 1 calc R U P B 2
H6AB H 0.629089 0.670079 -0.716411 0.026 Uiso 0.389(2) 1 calc R U P B 2


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F1 C8 1.342(2) . ?
F2 C7 1.3365(19) . ?
F3 C3 1.3403(18) . ?
O2 H2 0.8400 . ?
O2 C12 1.437(2) . ?
N1 C1 1.148(3) . ?
N2 C6 1.146(3) . ?
N3 H3 0.8800 . ?
N3 C4 1.355(2) . ?
N3 C9 1.461(2) . ?
C1 C2 1.436(2) . ?
C2 C3 1.378(2) . ?
C2 C8 1.401(2) . ?
C3 C4 1.417(2) . ?
C4 C5 1.420(2) . ?
C5 C6 1.435(2) . ?
C5 C7 1.404(2) . ?
C7 C8 1.364(3) . ?
C9 H9AA 0.9900 . ?
C9 H9AB 0.9900 . ?
C9 H9BC 0.9900 . ?
C9 H9BD 0.9900 . ?
C9 C10 1.607(4) . ?
C9 CA 1.408(5) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C12 H12C 0.9900 . ?
C12 H12D 0.9900 . ?
C12 C11 1.556(3) . ?
C12 C6A 1.405(5) . ?
O1 C10 1.419(4) . ?
O1 C11 1.424(4) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
O4A CA 1.453(6) . ?
O4A C6A 1.419(5) . ?
CA HAA 0.9900 . ?
CA HAB 0.9900 . ?
C6A H6AA 0.9900 . ?
C6A H6AB 0.9900 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C12 O2 H2 109.5 . . ?
C4 N3 H3 117.2 . . ?
C4 N3 C9 125.50(15) . . ?
C9 N3 H3 117.2 . . ?
N1 C1 C2 177.3(2) . . ?
C3 C2 C1 121.38(16) . . ?
C3 C2 C8 119.04(16) . . ?
C8 C2 C1 119.56(16) . . ?
F3 C3 C2 118.21(15) . . ?
F3 C3 C4 117.63(14) . . ?
C2 C3 C4 124.15(15) . . ?
N3 C4 C3 118.33(15) . . ?
N3 C4 C5 126.81(16) . . ?
C3 C4 C5 114.85(15) . . ?
C4 C5 C6 124.45(16) . . ?
C7 C5 C4 120.78(16) . . ?
C7 C5 C6 114.75(15) . . ?
N2 C6 C5 175.1(2) . . ?
F2 C7 C5 118.86(16) . . ?
F2 C7 C8 119.17(16) . . ?
C8 C7 C5 121.97(15) . . ?
F1 C8 C2 120.09(16) . . ?
F1 C8 C7 120.70(15) . . ?
C7 C8 C2 119.19(16) . . ?
N3 C9 H9AA 110.5 . . ?
N3 C9 H9AB 110.5 . . ?
N3 C9 H9BC 107.8 . . ?
N3 C9 H9BD 107.8 . . ?
N3 C9 C10 106.0(2) . . ?
H9AA C9 H9AB 108.7 . . ?
H9BC C9 H9BD 107.2 . . ?
C10 C9 H9AA 110.5 . . ?
C10 C9 H9AB 110.5 . . ?
CA C9 N3 118.0(3) . . ?
CA C9 H9BC 107.8 . . ?
CA C9 H9BD 107.8 . . ?
O2 C12 H12A 109.5 . . ?
O2 C12 H12B 109.5 . . ?
O2 C12 H12C 108.9 . . ?
O2 C12 H12D 108.9 . . ?
O2 C12 C11 110.58(17) . . ?
H12A C12 H12B 108.1 . . ?
H12C C12 H12D 107.7 . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
C6A C12 O2 113.3(2) . . ?
C6A C12 H12C 108.9 . . ?
C6A C12 H12D 108.9 . . ?
C10 O1 C11 113.6(3) . . ?
C9 C10 H10A 108.7 . . ?
C9 C10 H10B 108.7 . . ?
O1 C10 C9 114.3(3) . . ?
O1 C10 H10A 108.7 . . ?
O1 C10 H10B 108.7 . . ?
H10A C10 H10B 107.6 . . ?
C12 C11 H11A 109.5 . . ?
C12 C11 H11B 109.5 . . ?
O1 C11 C12 110.6(2) . . ?
O1 C11 H11A 109.5 . . ?
O1 C11 H11B 109.5 . . ?
H11A C11 H11B 108.1 . . ?
C6A O4A CA 110.8(4) . . ?
C9 CA O4A 106.0(4) . . ?
C9 CA HAA 110.5 . . ?
C9 CA HAB 110.5 . . ?
O4A CA HAA 110.5 . . ?
O4A CA HAB 110.5 . . ?
HAA CA HAB 108.7 . . ?
C12 C6A O4A 107.9(4) . . ?
C12 C6A H6AA 110.1 . . ?
C12 C6A H6AB 110.1 . . ?
O4A C6A H6AA 110.1 . . ?
O4A C6A H6AB 110.1 . . ?
H6AA C6A H6AB 108.4 . . ?

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
F2 C7 C8 F1 1.4(3) . . . . ?
F2 C7 C8 C2 179.69(16) . . . . ?
F3 C3 C4 N3 -1.2(2) . . . . ?
F3 C3 C4 C5 179.61(15) . . . . ?
O2 C12 C11 O1 -65.0(3) . . . . ?
O2 C12 C6A O4A 58.4(4) . . . . ?
N3 C4 C5 C6 -2.5(3) . . . . ?
N3 C4 C5 C7 179.37(17) . . . . ?
N3 C9 C10 O1 -64.2(4) . . . . ?
N3 C9 CA O4A -65.3(5) . . . . ?
C1 C2 C3 F3 -0.3(3) . . . . ?
C1 C2 C3 C4 178.30(16) . . . . ?
C1 C2 C8 F1 -0.5(3) . . . . ?
C1 C2 C8 C7 -178.77(17) . . . . ?
C2 C3 C4 N3 -179.84(17) . . . . ?
C2 C3 C4 C5 1.0(2) . . . . ?
C3 C2 C8 F1 177.88(16) . . . . ?
C3 C2 C8 C7 -0.4(3) . . . . ?
C3 C4 C5 C6 176.61(16) . . . . ?
C3 C4 C5 C7 -1.5(2) . . . . ?
C4 N3 C9 C10 -137.4(2) . . . . ?
C4 N3 C9 CA -153.6(3) . . . . ?
C4 C5 C7 F2 -178.65(16) . . . . ?
C4 C5 C7 C8 1.2(3) . . . . ?
C5 C7 C8 F1 -178.46(16) . . . . ?
C5 C7 C8 C2 -0.1(3) . . . . ?
C6 C5 C7 F2 3.0(2) . . . . ?
C6 C5 C7 C8 -177.11(17) . . . . ?
C8 C2 C3 F3 -178.64(16) . . . . ?
C8 C2 C3 C4 0.0(3) . . . . ?
C9 N3 C4 C3 164.87(18) . . . . ?
C9 N3 C4 C5 -16.0(3) . . . . ?
C10 O1 C11 C12 -175.5(2) . . . . ?
C11 O1 C10 C9 -77.4(4) . . . . ?
CA O4A C6A C12 171.8(4) . . . . ?
C6A O4A CA C9 164.7(4) . . . . ?

_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_1_CCDC2
_database_code_depnum_ccdc_archive 'CCDC 2380824'
loop_
_audit_author_name
_audit_author_address
'Tingting Ji'
;Jilin University
China
;
_audit_update_record             
;
2024-08-30 deposited with the CCDC.	2025-03-27 downloaded from the CCDC.
;
_audit_creation_date             2024-07-25
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C11 H8 F3 N3 O'
_chemical_formula_sum            'C11 H8 F3 N3 O'
_chemical_formula_weight         255.20
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   9.7492(8)
_cell_length_b                   6.1659(5)
_cell_length_c                   18.7972(16)
_cell_angle_alpha                90
_cell_angle_beta                 91.957(3)
_cell_angle_gamma                90
_cell_volume                     1129.29(16)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9903
_cell_measurement_temperature    298
_cell_measurement_theta_max      29.450
_cell_measurement_theta_min      3.253
_shelx_estimated_absorpt_T_max   0.985
_shelx_estimated_absorpt_T_min   0.979
_exptl_absorpt_coefficient_mu    0.134
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear yellowish colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   yellowish
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.501
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             520
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.11
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0273
_diffrn_reflns_av_unetI/netI     0.0146
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            26783
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.574
_diffrn_reflns_theta_min         3.478
_diffrn_ambient_temperature      298
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           30.0
_diffrn_source_power             1.5
_diffrn_source_voltage           50.0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2083
_reflns_number_total             3157
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.40A (Bruker, 2019)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40A (Bruker, 2019)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.177
_refine_diff_density_min         -0.182
_refine_diff_density_rms         0.041
_refine_ls_extinction_coef       0.052(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     172
_refine_ls_number_reflns         3157
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0828
_refine_ls_R_factor_gt           0.0534
_refine_ls_restrained_S_all      1.060
_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)+(0.0555P)²+0.5212P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1292
_refine_ls_wR_factor_ref         0.1598
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C9(H9a,H9b), C10(H10a,H10b), C11(H11a,H11b)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
F1 F 0.47187(14) 0.7957(3) 0.75874(8) 0.0925(5) Uani 1 1 d . . . . .
F2 F 0.32299(12) 0.4330(3) 0.73178(7) 0.0874(5) Uani 1 1 d . . . . .
F3 F 0.59157(12) 0.2978(2) 0.53354(6) 0.0676(4) Uani 1 1 d . . . . .
O1 O 1.14462(17) 0.6531(3) 0.54621(9) 0.0778(5) Uani 1 1 d . . . . .
H1 H 1.192(3) 0.763(6) 0.5603(18) 0.113(11) Uiso 1 1 d . . . . .
N1 N 0.3131(2) 0.0225(4) 0.59998(12) 0.0830(6) Uani 1 1 d . . . . .
N2 N 0.7182(2) 1.0988(4) 0.69803(13) 0.0866(6) Uani 1 1 d . . . . .
N3 N 0.74852(17) 0.6447(3) 0.55658(10) 0.0602(4) Uani 1 1 d . . . . .
C1 C 0.50064(19) 0.6718(4) 0.70293(11) 0.0628(5) Uani 1 1 d . . . . .
C2 C 0.42507(18) 0.4919(4) 0.68936(11) 0.0618(5) Uani 1 1 d . . . . .
C3 C 0.45441(17) 0.3649(3) 0.63033(10) 0.0532(4) Uani 1 1 d . . . . .
C4 C 0.56230(18) 0.4238(3) 0.58923(9) 0.0516(4) Uani 1 1 d . . . . .
C5 C 0.64546(17) 0.6073(3) 0.60163(9) 0.0508(4) Uani 1 1 d . . . . .
C6 C 0.60896(18) 0.7351(3) 0.66016(10) 0.0554(5) Uani 1 1 d . . . . .
C7 C 0.3754(2) 0.1746(4) 0.61321(11) 0.0626(5) Uani 1 1 d . . . . .
C8 C 0.6740(2) 0.9350(4) 0.67995(12) 0.0656(5) Uani 1 1 d . . . . .
C9 C 0.8524(2) 0.8138(4) 0.56288(11) 0.0627(5) Uani 1 1 d . . . . .
H9A H 0.807480 0.950947 0.571938 0.075 Uiso 1 1 calc R U . . .
H9B H 0.897497 0.826524 0.517864 0.075 Uiso 1 1 calc R U . . .
C10 C 0.9606(2) 0.7733(4) 0.62154(11) 0.0676(6) Uani 1 1 d . . . . .
H10A H 1.010581 0.906880 0.630806 0.081 Uiso 1 1 calc R U . . .
H10B H 0.915037 0.733871 0.664763 0.081 Uiso 1 1 calc R U . . .
C11 C 1.0611(2) 0.5978(4) 0.60410(12) 0.0701(6) Uani 1 1 d . . . . .
H11A H 1.119663 0.568921 0.645787 0.084 Uiso 1 1 calc R U . . .
H11B H 1.011053 0.465812 0.592482 0.084 Uiso 1 1 calc R U . . .
H3 H 0.764(2) 0.548(4) 0.5254(13) 0.067(7) Uiso 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F1 C1 1.335(2) . ?
F2 C2 1.346(2) . ?
F3 C4 1.342(2) . ?
O1 H1 0.85(4) . ?
O1 C11 1.422(3) . ?
N1 C7 1.140(3) . ?
N2 C8 1.145(3) . ?
N3 C5 1.356(2) . ?
N3 C9 1.456(3) . ?
N3 H3 0.85(2) . ?
C1 C2 1.351(3) . ?
C1 C6 1.404(3) . ?
C2 C3 1.395(3) . ?
C3 C4 1.375(2) . ?
C3 C7 1.434(3) . ?
C4 C5 1.407(3) . ?
C5 C6 1.409(3) . ?
C6 C8 1.430(3) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C9 C10 1.520(3) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C10 C11 1.504(3) . ?
C11 H11A 0.9700 . ?
C11 H11B 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
C11 O1 H1 106(2) . . ?
C5 N3 C9 126.82(18) . . ?
C5 N3 H3 117.8(16) . . ?
C9 N3 H3 114.5(16) . . ?
F1 C1 C2 119.36(19) . . ?
F1 C1 C6 118.2(2) . . ?
C2 C1 C6 122.41(18) . . ?
F2 C2 C1 121.25(19) . . ?
F2 C2 C3 119.7(2) . . ?
C1 C2 C3 119.05(18) . . ?
C2 C3 C7 120.96(18) . . ?
C4 C3 C2 118.69(18) . . ?
C4 C3 C7 120.35(18) . . ?
F3 C4 C3 118.19(17) . . ?
F3 C4 C5 117.27(16) . . ?
C3 C4 C5 124.54(17) . . ?
N3 C5 C4 117.93(17) . . ?
N3 C5 C6 127.24(18) . . ?
C4 C5 C6 114.82(16) . . ?
C1 C6 C5 120.43(18) . . ?
C1 C6 C8 115.24(18) . . ?
C5 C6 C8 124.32(19) . . ?
N1 C7 C3 179.5(3) . . ?
N2 C8 C6 175.4(2) . . ?
N3 C9 H9A 108.8 . . ?
N3 C9 H9B 108.8 . . ?
N3 C9 C10 113.87(18) . . ?
H9A C9 H9B 107.7 . . ?
C10 C9 H9A 108.8 . . ?
C10 C9 H9B 108.8 . . ?
C9 C10 H10A 108.8 . . ?
C9 C10 H10B 108.8 . . ?
H10A C10 H10B 107.7 . . ?
C11 C10 C9 113.67(19) . . ?
C11 C10 H10A 108.8 . . ?
C11 C10 H10B 108.8 . . ?
O1 C11 C10 112.9(2) . . ?
O1 C11 H11A 109.0 . . ?
O1 C11 H11B 109.0 . . ?
C10 C11 H11A 109.0 . . ?
C10 C11 H11B 109.0 . . ?
H11A C11 H11B 107.8 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
F1 C1 C2 F2 -1.2(3) . . . . ?
F1 C1 C2 C3 179.06(18) . . . . ?
F1 C1 C6 C5 178.53(17) . . . . ?
F1 C1 C6 C8 -2.6(3) . . . . ?
F2 C2 C3 C4 -177.68(17) . . . . ?
F2 C2 C3 C7 1.3(3) . . . . ?
F3 C4 C5 N3 0.3(2) . . . . ?
F3 C4 C5 C6 179.20(15) . . . . ?
N3 C5 C6 C1 -178.62(18) . . . . ?
N3 C5 C6 C8 2.6(3) . . . . ?
N3 C9 C10 C11 73.4(2) . . . . ?
C1 C2 C3 C4 2.0(3) . . . . ?
C1 C2 C3 C7 -178.96(19) . . . . ?
C2 C1 C6 C5 -1.8(3) . . . . ?
C2 C1 C6 C8 177.11(19) . . . . ?
C2 C3 C4 F3 178.51(16) . . . . ?
C2 C3 C4 C5 -1.1(3) . . . . ?
C3 C4 C5 N3 179.87(17) . . . . ?
C3 C4 C5 C6 -1.2(3) . . . . ?
C4 C5 C6 C1 2.6(2) . . . . ?
C4 C5 C6 C8 -176.20(17) . . . . ?
C5 N3 C9 C10 73.1(3) . . . . ?
C6 C1 C2 F2 179.05(18) . . . . ?
C6 C1 C2 C3 -0.6(3) . . . . ?
C7 C3 C4 F3 -0.5(3) . . . . ?
C7 C3 C4 C5 179.89(17) . . . . ?
C9 N3 C5 C4 -174.83(18) . . . . ?
C9 N3 C5 C6 6.4(3) . . . . ?
C9 C10 C11 O1 65.6(2) . . . . ?


_olex2_submission_special_instructions 'No special instructions were received'
