# Supplementary Information (SI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2026

####################################################################### 
# 
# 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 2451045'
loop_
_audit_author_name
_audit_author_address
'Keyume Ablajan'
;Xinjiang University
China
;
_audit_update_record             
;
2025-05-14 deposited with the CCDC.	2025-12-08 downloaded from the CCDC.
;
_audit_creation_date             2025-05-14
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6403)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C20 H17 F N2 O2 S'
_chemical_formula_sum            'C20 H17 F N2 O2 S'
_chemical_formula_weight         368.41
_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'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      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                   14.458(3)
_cell_length_b                   7.3920(19)
_cell_length_c                   33.338(10)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3563.0(16)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    9968
_cell_measurement_temperature    296.15
_cell_measurement_theta_max      23.38
_cell_measurement_theta_min      3.10
_shelx_estimated_absorpt_T_max   0.984
_shelx_estimated_absorpt_T_min   0.975
_exptl_absorpt_coefficient_mu    0.208
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_correction_T_min  0.6424
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0992 before and 0.0815 after correction.
The Ratio of minimum to maximum transmission is 0.8621.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear whiteish colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   whiteish
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.374
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1536
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.08
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0788
_diffrn_reflns_av_unetI/netI     0.0592
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       38
_diffrn_reflns_limit_l_min       -39
_diffrn_reflns_number            45643
_diffrn_reflns_point_group_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_theta_full        25.052
_diffrn_reflns_theta_max         25.052
_diffrn_reflns_theta_min         2.818
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.995
_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         0.949
_reflns_Friedel_fraction_full    0.981
_reflns_Friedel_fraction_max     0.981
_reflns_number_gt                3928
_reflns_number_total             6259
_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  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.196
_refine_diff_density_min         -0.233
_refine_diff_density_rms         0.046
_refine_ls_abs_structure_details 
;
 Flack x determined using 1549 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.35(4)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     511
_refine_ls_number_reflns         6259
_refine_ls_number_restraints     119
_refine_ls_R_factor_all          0.0990
_refine_ls_R_factor_gt           0.0467
_refine_ls_restrained_S_all      1.053
_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)+(0.0624P)²+0.4075P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1026
_refine_ls_wR_factor_ref         0.1275
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 C7-C6 = C3-C2 = C5-C4 = C1-C0
 1.54 with sigma of 0.01
 O010-C7 \\sim O010-C3 \\sim O00O-C1 \\sim O00O-C5
 with sigma of 0.01
3. Rigid bond restraints
 O010, C2, C3, C6, C7
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.02
 O00O, C0, C1, C4, C5
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.02
4. Uiso/Uaniso restraints and constraints
O00O \\sim C0 \\sim C1 \\sim C4 \\sim C5: within 2A with sigma of 0.01 and
sigma for terminal atoms of 0.02 within 2A
O010 \\sim C2 \\sim C3 \\sim C6 \\sim C7: within 2A with sigma of 0.01 and
sigma for terminal atoms of 0.02 within 2A
5. Others
 Sof(C0)=Sof(H0A)=Sof(H0B)=Sof(H0C)=Sof(C1)=Sof(H1A)=Sof(H1B)=1-FVAR(1)
 Sof(C4)=Sof(H4A)=Sof(H4B)=Sof(H4C)=Sof(C5)=Sof(H5A)=Sof(H5B)=FVAR(1)
 Sof(C2)=Sof(H2A)=Sof(H2B)=Sof(H2C)=Sof(C3)=Sof(H3A)=Sof(H3B)=1-FVAR(2)
 Sof(C6)=Sof(H6A)=Sof(H6B)=Sof(H6C)=Sof(C7)=Sof(H7A)=Sof(H7B)=FVAR(2)
6.a Secondary CH2 refined with riding coordinates:
 C00I(H00D,H00F), C00P(H00A,H00B), C012(H01D,H01E), C016(H01A,H01B), C1(H1A,
 H1B), C3(H3A,H3B), C5(H5A,H5B), C7(H7A,H7B)
6.b Aromatic/amide H refined with riding coordinates:
 C00B(H00C), C00E(H00E), C00M(H00M), C00Q(H00Q), C00S(H00S), C00U(H00U),
 C00W(H00W), C00X(H00X), C00Y(H00Y), C00Z(H00Z), C011(H011), C013(H013),
 C017(H017), C019(H019), C01A(H01F), C01C(H01C)
6.c Idealised Me refined as rotating group:
 C0(H0A,H0B,H0C), C2(H2A,H2B,H2C), C4(H4A,H4B,H4C), C6(H6A,H6B,H6C)
;
_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
S001 S 0.10847(11) 1.3315(2) 0.34670(7) 0.0726(6) Uani 1 1 d . . . . .
S002 S 1.15010(11) 0.1594(2) 0.65260(7) 0.0768(6) Uani 1 1 d . . . . .
F003 F 0.0500(2) 0.7277(5) 0.37808(14) 0.0593(11) Uani 1 1 d . . . . .
F004 F 1.2128(2) 0.7642(4) 0.62352(15) 0.0613(11) Uani 1 1 d . . . . .
N005 N 1.2743(3) 0.5478(6) 0.66357(15) 0.0484(12) Uani 1 1 d . . . . .
N006 N -0.0134(3) 0.9400(6) 0.33742(15) 0.0485(12) Uani 1 1 d . . . . .
N007 N 1.3834(3) 0.3439(6) 0.68019(16) 0.0580(13) Uani 1 1 d . . . . .
N008 N -0.1252(3) 1.1386(6) 0.32195(16) 0.0590(13) Uani 1 1 d . . . . .
C009 C 1.4040(4) 0.5115(8) 0.6981(2) 0.0540(16) Uani 1 1 d . . . . .
C00A C -0.0768(4) 0.8453(8) 0.31359(19) 0.0487(16) Uani 1 1 d . . . . .
C00B C 1.4782(4) 0.5591(9) 0.72194(19) 0.0610(17) Uani 1 1 d . . . . .
H00C H 1.5225 0.4747 0.7296 0.073 Uiso 1 1 calc R U . . .
C00C C 1.3075(4) 0.3723(7) 0.65989(19) 0.0531(15) Uani 1 1 d . . . . .
C00D C 1.0372(4) 0.5862(8) 0.61761(17) 0.0494(14) Uani 1 1 d . . . . .
C00E C 0.2523(4) 0.7337(8) 0.3868(3) 0.0536(18) Uani 1 1 d . . . . .
H00E H 0.2205 0.6425 0.3734 0.064 Uiso 1 1 calc R U . . .
C00F C 0.0669(4) 0.8798(7) 0.35631(18) 0.0495(15) Uani 1 1 d . . . . .
C00G C 0.2249(3) 0.9107(8) 0.38244(17) 0.0499(15) Uani 1 1 d . . . . .
C00H C -0.0482(4) 1.1146(7) 0.3414(2) 0.0526(15) Uani 1 1 d . . . . .
C00I C 1.2599(4) 0.2411(8) 0.6341(3) 0.063(2) Uani 1 1 d . . . . .
H00D H 1.3004 0.1381 0.6301 0.076 Uiso 1 1 calc R U . . .
H00F H 1.2498 0.2965 0.6081 0.076 Uiso 1 1 calc R U . . .
C00J C 1.3366(4) 0.6397(8) 0.68820(19) 0.0479(16) Uani 1 1 d . . . . .
C00K C 0.1470(3) 0.9643(7) 0.35590(17) 0.0471(14) Uani 1 1 d . . . . .
O00L O 0.5024(4) 0.8987(11) 0.4727(2) 0.125(2) Uani 1 1 d . . . . .
C00M C -0.0805(4) 0.6671(8) 0.3016(2) 0.0542(16) Uani 1 1 d . . . . .
H00M H -0.0344 0.5843 0.3081 0.065 Uiso 1 1 calc R U . . .
C00N C 1.1956(3) 0.6134(7) 0.64425(18) 0.0469(14) Uani 1 1 d . . . . .
O00O O 0.7913(4) 0.9006(12) 0.5414(2) 0.125(3) Uani 1 1 d D U . . .
C00P C 0.1583(4) 1.1225(8) 0.3283(2) 0.0538(15) Uani 1 1 d . . . . .
H00A H 0.1299 1.0932 0.3028 0.065 Uiso 1 1 calc R U . . .
H00B H 0.2237 1.1415 0.3236 0.065 Uiso 1 1 calc R U . . .
C00Q C 1.4834(4) 0.7369(10) 0.7339(3) 0.066(2) Uani 1 1 d . . . . .
H00Q H 1.5340 0.7730 0.7492 0.079 Uiso 1 1 calc R U . . .
C00R C 1.1143(3) 0.5296(7) 0.64388(17) 0.0463(14) Uani 1 1 d . . . . .
C00S C 0.9901(4) 0.4573(9) 0.59542(19) 0.0660(18) Uani 1 1 d . . . . .
H00S H 1.0079 0.3367 0.5971 0.079 Uiso 1 1 calc R U . . .
O00T O 0.7607(4) 0.6103(12) 0.5273(2) 0.126(3) Uani 1 1 d . . . . .
C00U C 0.9353(4) 0.8116(10) 0.5908(2) 0.0660(17) Uani 1 1 d . . . . .
H00U H 0.9166 0.9317 0.5893 0.079 Uiso 1 1 calc R U . . .
C00V C -0.1451(4) 0.9714(8) 0.30469(19) 0.0519(15) Uani 1 1 d . . . . .
C00W C 0.3457(4) 0.9984(11) 0.4277(2) 0.072(2) Uani 1 1 d . . . . .
H00W H 0.3766 1.0886 0.4418 0.087 Uiso 1 1 calc R U . . .
C00X C -0.2250(5) 0.7437(10) 0.2687(3) 0.071(3) Uani 1 1 d . . . . .
H00X H -0.2739 0.7071 0.2526 0.085 Uiso 1 1 calc R U . . .
C00Y C 1.0087(4) 0.7647(9) 0.6146(3) 0.059(2) Uani 1 1 d . . . . .
H00Y H 1.0398 0.8538 0.6290 0.071 Uiso 1 1 calc R U . . .
C00Z C 1.3413(4) 0.8163(9) 0.7008(2) 0.0584(18) Uani 1 1 d . . . . .
H00Z H 1.2960 0.9000 0.6939 0.070 Uiso 1 1 calc R U . . .
O010 O 0.4719(4) 0.6093(12) 0.4605(2) 0.119(2) Uani 1 1 d D U . . .
C011 C 0.2724(4) 1.0447(10) 0.4034(2) 0.0678(19) Uani 1 1 d . . . . .
H011 H 0.2547 1.1652 0.4009 0.081 Uiso 1 1 calc R U . . .
C012 C 1.1020(4) 0.3699(8) 0.6709(2) 0.0588(17) Uani 1 1 d . . . . .
H01D H 1.0364 0.3526 0.6755 0.071 Uiso 1 1 calc R U . . .
H01E H 1.1303 0.3974 0.6966 0.071 Uiso 1 1 calc R U . . .
C013 C -0.1571(4) 0.6200(9) 0.2793(2) 0.0651(17) Uani 1 1 d . . . . .
H013 H -0.1635 0.5005 0.2710 0.078 Uiso 1 1 calc R U . . .
C014 C 0.8890(4) 0.6810(13) 0.5689(2) 0.071(2) Uani 1 1 d . . . . .
C015 C 0.4558(5) 0.7826(18) 0.4575(3) 0.089(3) Uani 1 1 d . . . . .
C016 C 0.0005(4) 1.2480(9) 0.3675(3) 0.068(2) Uani 1 1 d . . . . .
H01A H 0.0131 1.1918 0.3932 0.081 Uiso 1 1 calc R U . . .
H01B H -0.0404 1.3499 0.3722 0.081 Uiso 1 1 calc R U . . .
C017 C 0.9175(4) 0.5052(12) 0.5710(2) 0.080(2) Uani 1 1 d . . . . .
H017 H 0.8875 0.4173 0.5558 0.096 Uiso 1 1 calc R U . . .
C018 C 0.3740(4) 0.8220(13) 0.4317(2) 0.070(2) Uani 1 1 d . . . . .
C019 C 0.3272(4) 0.6900(10) 0.4111(2) 0.0663(19) Uani 1 1 d . . . . .
H019 H 0.3458 0.5700 0.4134 0.080 Uiso 1 1 calc R U . . .
C01A C 1.4171(4) 0.8646(10) 0.7243(2) 0.0650(18) Uani 1 1 d . . . . .
H01F H 1.4231 0.9827 0.7336 0.078 Uiso 1 1 calc R U . . .
C01B C 0.8065(6) 0.7283(19) 0.5434(3) 0.092(3) Uani 1 1 d . . . . .
C01C C -0.2207(4) 0.9183(11) 0.2818(2) 0.0696(19) Uani 1 1 d . . . . .
H01C H -0.2674 1.0001 0.2755 0.084 Uiso 1 1 calc R U . . .
C0 C 0.728(2) 1.113(4) 0.4938(10) 0.133(6) Uani 0.64(5) 1 d D U P A 2
H0A H 0.6804 1.1357 0.4741 0.199 Uiso 0.64(5) 1 calc R U P A 2
H0B H 0.7872 1.1181 0.4812 0.199 Uiso 0.64(5) 1 calc R U P A 2
H0C H 0.7242 1.2039 0.5144 0.199 Uiso 0.64(5) 1 calc R U P A 2
C2 C 0.523(3) 0.410(4) 0.5127(8) 0.111(7) Uani 0.48(3) 1 d D U P B 2
H2A H 0.4791 0.3200 0.5039 0.166 Uiso 0.48(3) 1 calc R U P B 2
H2B H 0.4927 0.4918 0.5308 0.166 Uiso 0.48(3) 1 calc R U P B 2
H2C H 0.5734 0.3518 0.5260 0.166 Uiso 0.48(3) 1 calc R U P B 2
C1 C 0.7132(13) 0.930(4) 0.5120(8) 0.123(5) Uani 0.64(5) 1 d D U P A 2
H1A H 0.7142 0.8371 0.4914 0.148 Uiso 0.64(5) 1 calc R U P A 2
H1B H 0.6541 0.9244 0.5258 0.148 Uiso 0.64(5) 1 calc R U P A 2
C3 C 0.5587(10) 0.515(5) 0.4763(9) 0.117(5) Uani 0.48(3) 1 d D U P B 2
H3A H 0.6055 0.6020 0.4842 0.140 Uiso 0.48(3) 1 calc R U P B 2
H3B H 0.5845 0.4338 0.4563 0.140 Uiso 0.48(3) 1 calc R U P B 2
C4 C 0.757(3) 1.112(8) 0.4917(15) 0.117(7) Uani 0.36(5) 1 d D U P A 1
H4A H 0.7118 1.1594 0.4735 0.175 Uiso 0.36(5) 1 calc R U P A 1
H4B H 0.7981 1.0323 0.4776 0.175 Uiso 0.36(5) 1 calc R U P A 1
H4C H 0.7919 1.2097 0.5032 0.175 Uiso 0.36(5) 1 calc R U P A 1
C5 C 0.7083(16) 1.007(7) 0.5253(15) 0.124(5) Uani 0.36(5) 1 d D U P A 1
H5A H 0.6822 1.0869 0.5454 0.149 Uiso 0.36(5) 1 calc R U P A 1
H5B H 0.6604 0.9278 0.5149 0.149 Uiso 0.36(5) 1 calc R U P A 1
C6 C 0.537(2) 0.385(3) 0.4981(11) 0.133(7) Uani 0.52(3) 1 d D U P B 1
H6A H 0.5372 0.3264 0.4725 0.200 Uiso 0.52(3) 1 calc R U P B 1
H6B H 0.4796 0.3597 0.5117 0.200 Uiso 0.52(3) 1 calc R U P B 1
H6C H 0.5876 0.3420 0.5140 0.200 Uiso 0.52(3) 1 calc R U P B 1
C7 C 0.5461(13) 0.589(3) 0.4923(7) 0.104(5) Uani 0.52(3) 1 d D U P B 1
H7A H 0.5319 0.6560 0.5165 0.125 Uiso 0.52(3) 1 calc R U P B 1
H7B H 0.6068 0.6228 0.4824 0.125 Uiso 0.52(3) 1 calc R U P B 1


_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
S001 C00P 1.811(6) . ?
S001 C016 1.817(7) . ?
S002 C00I 1.807(7) . ?
S002 C012 1.810(6) . ?
F003 C00F 1.360(6) . ?
F004 C00N 1.335(7) . ?
N005 C00C 1.389(7) . ?
N005 C00J 1.395(7) . ?
N005 C00N 1.395(7) . ?
N006 C00A 1.400(7) . ?
N006 C00F 1.394(7) . ?
N006 C00H 1.392(6) . ?
N007 C009 1.407(8) . ?
N007 C00C 1.306(7) . ?
N008 C00H 1.301(7) . ?
N008 C00V 1.394(7) . ?
C009 C00B 1.380(8) . ?
C009 C00J 1.398(8) . ?
C00A C00M 1.378(9) . ?
C00A C00V 1.390(8) . ?
C00B H00C 0.9300 . ?
C00B C00Q 1.376(9) . ?
C00C C00I 1.467(9) . ?
C00D C00R 1.478(7) . ?
C00D C00S 1.385(8) . ?
C00D C00Y 1.386(8) . ?
C00E H00E 0.9300 . ?
C00E C00G 1.375(8) . ?
C00E C019 1.391(10) . ?
C00F C00K 1.316(7) . ?
C00G C00K 1.486(8) . ?
C00G C011 1.393(8) . ?
C00H C016 1.491(9) . ?
C00I H00D 0.9700 . ?
C00I H00F 0.9700 . ?
C00J C00Z 1.372(8) . ?
C00K C00P 1.496(8) . ?
O00L C015 1.204(11) . ?
C00M H00M 0.9300 . ?
C00M C013 1.379(8) . ?
C00N C00R 1.328(7) . ?
O00O C01B 1.295(12) . ?
O00O C1 1.509(10) . ?
O00O C5 1.532(12) . ?
C00P H00A 0.9700 . ?
C00P H00B 0.9700 . ?
C00Q H00Q 0.9300 . ?
C00Q C01A 1.382(9) . ?
C00R C012 1.496(8) . ?
C00S H00S 0.9300 . ?
C00S C017 1.376(9) . ?
O00T C01B 1.219(12) . ?
C00U H00U 0.9300 . ?
C00U C00Y 1.371(9) . ?
C00U C014 1.383(10) . ?
C00V C01C 1.390(9) . ?
C00W H00W 0.9300 . ?
C00W C011 1.377(9) . ?
C00W C018 1.373(10) . ?
C00X H00X 0.9300 . ?
C00X C013 1.387(9) . ?
C00X C01C 1.363(10) . ?
C00Y H00Y 0.9300 . ?
C00Z H00Z 0.9300 . ?
C00Z C01A 1.395(9) . ?
O010 C015 1.306(12) . ?
O010 C3 1.530(11) . ?
O010 C7 1.514(10) . ?
C011 H011 0.9300 . ?
C012 H01D 0.9700 . ?
C012 H01E 0.9700 . ?
C013 H013 0.9300 . ?
C014 C017 1.365(10) . ?
C014 C01B 1.507(11) . ?
C015 C018 1.491(11) . ?
C016 H01A 0.9700 . ?
C016 H01B 0.9700 . ?
C017 H017 0.9300 . ?
C018 C019 1.371(10) . ?
C019 H019 0.9300 . ?
C01A H01F 0.9300 . ?
C01C H01C 0.9300 . ?
C0 H0A 0.9600 . ?
C0 H0B 0.9600 . ?
C0 H0C 0.9600 . ?
C0 C1 1.503(14) . ?
C2 H2A 0.9600 . ?
C2 H2B 0.9600 . ?
C2 H2C 0.9600 . ?
C2 C3 1.530(14) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C4 H4A 0.9600 . ?
C4 H4B 0.9600 . ?
C4 H4C 0.9600 . ?
C4 C5 1.533(15) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C6 H6A 0.9600 . ?
C6 H6B 0.9600 . ?
C6 H6C 0.9600 . ?
C6 C7 1.522(14) . ?
C7 H7A 0.9700 . ?
C7 H7B 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
C00P S001 C016 100.4(3) . . ?
C00I S002 C012 99.5(3) . . ?
C00C N005 C00J 106.5(4) . . ?
C00C N005 C00N 124.5(5) . . ?
C00N N005 C00J 129.0(5) . . ?
C00F N006 C00A 130.0(5) . . ?
C00H N006 C00A 106.3(4) . . ?
C00H N006 C00F 123.6(5) . . ?
C00C N007 C009 104.9(4) . . ?
C00H N008 C00V 105.2(4) . . ?
C00B C009 N007 129.3(5) . . ?
C00B C009 C00J 120.3(6) . . ?
C00J C009 N007 110.4(5) . . ?
C00M C00A N006 131.8(5) . . ?
C00M C00A C00V 123.5(6) . . ?
C00V C00A N006 104.6(5) . . ?
C009 C00B H00C 121.5 . . ?
C00Q C00B C009 116.9(6) . . ?
C00Q C00B H00C 121.5 . . ?
N005 C00C C00I 120.5(5) . . ?
N007 C00C N005 113.2(5) . . ?
N007 C00C C00I 126.3(5) . . ?
C00S C00D C00R 119.5(5) . . ?
C00S C00D C00Y 118.0(6) . . ?
C00Y C00D C00R 122.4(5) . . ?
C00G C00E H00E 119.8 . . ?
C00G C00E C019 120.4(6) . . ?
C019 C00E H00E 119.8 . . ?
F003 C00F N006 110.8(4) . . ?
C00K C00F F003 123.8(5) . . ?
C00K C00F N006 125.2(5) . . ?
C00E C00G C00K 122.3(5) . . ?
C00E C00G C011 118.8(6) . . ?
C011 C00G C00K 118.8(6) . . ?
N006 C00H C016 119.9(5) . . ?
N008 C00H N006 112.8(5) . . ?
N008 C00H C016 127.2(5) . . ?
S002 C00I H00D 108.4 . . ?
S002 C00I H00F 108.4 . . ?
C00C C00I S002 115.7(5) . . ?
C00C C00I H00D 108.4 . . ?
C00C C00I H00F 108.4 . . ?
H00D C00I H00F 107.4 . . ?
N005 C00J C009 105.0(5) . . ?
C00Z C00J N005 132.4(5) . . ?
C00Z C00J C009 122.5(6) . . ?
C00F C00K C00G 122.3(5) . . ?
C00F C00K C00P 118.2(5) . . ?
C00G C00K C00P 119.5(5) . . ?
C00A C00M H00M 122.3 . . ?
C00A C00M C013 115.4(6) . . ?
C013 C00M H00M 122.3 . . ?
F004 C00N N005 112.1(4) . . ?
C00R C00N F004 123.3(5) . . ?
C00R C00N N005 124.3(5) . . ?
C01B O00O C1 107.4(15) . . ?
C01B O00O C5 131(2) . . ?
S001 C00P H00A 108.6 . . ?
S001 C00P H00B 108.6 . . ?
C00K C00P S001 114.6(4) . . ?
C00K C00P H00A 108.6 . . ?
C00K C00P H00B 108.6 . . ?
H00A C00P H00B 107.6 . . ?
C00B C00Q H00Q 118.4 . . ?
C00B C00Q C01A 123.2(7) . . ?
C01A C00Q H00Q 118.4 . . ?
C00D C00R C012 119.4(5) . . ?
C00N C00R C00D 122.7(5) . . ?
C00N C00R C012 117.9(5) . . ?
C00D C00S H00S 119.5 . . ?
C017 C00S C00D 121.0(7) . . ?
C017 C00S H00S 119.5 . . ?
C00Y C00U H00U 119.9 . . ?
C00Y C00U C014 120.3(7) . . ?
C014 C00U H00U 119.9 . . ?
C00A C00V N008 111.1(5) . . ?
C00A C00V C01C 119.1(6) . . ?
C01C C00V N008 129.8(6) . . ?
C011 C00W H00W 119.3 . . ?
C018 C00W H00W 119.3 . . ?
C018 C00W C011 121.5(6) . . ?
C013 C00X H00X 119.6 . . ?
C01C C00X H00X 119.6 . . ?
C01C C00X C013 120.7(7) . . ?
C00D C00Y H00Y 119.6 . . ?
C00U C00Y C00D 120.8(6) . . ?
C00U C00Y H00Y 119.6 . . ?
C00J C00Z H00Z 121.5 . . ?
C00J C00Z C01A 117.0(6) . . ?
C01A C00Z H00Z 121.5 . . ?
C015 O010 C3 128.4(15) . . ?
C015 O010 C7 106.2(11) . . ?
C00G C011 H011 120.1 . . ?
C00W C011 C00G 119.8(7) . . ?
C00W C011 H011 120.1 . . ?
S002 C012 H01D 108.4 . . ?
S002 C012 H01E 108.4 . . ?
C00R C012 S002 115.5(5) . . ?
C00R C012 H01D 108.4 . . ?
C00R C012 H01E 108.4 . . ?
H01D C012 H01E 107.5 . . ?
C00M C013 C00X 122.6(7) . . ?
C00M C013 H013 118.7 . . ?
C00X C013 H013 118.7 . . ?
C00U C014 C01B 121.3(8) . . ?
C017 C014 C00U 119.5(6) . . ?
C017 C014 C01B 119.2(8) . . ?
O00L C015 O010 124.5(9) . . ?
O00L C015 C018 123.2(11) . . ?
O010 C015 C018 112.2(9) . . ?
S001 C016 H01A 108.7 . . ?
S001 C016 H01B 108.7 . . ?
C00H C016 S001 114.1(6) . . ?
C00H C016 H01A 108.7 . . ?
C00H C016 H01B 108.7 . . ?
H01A C016 H01B 107.6 . . ?
C00S C017 H017 119.8 . . ?
C014 C017 C00S 120.4(7) . . ?
C014 C017 H017 119.8 . . ?
C00W C018 C015 118.5(8) . . ?
C019 C018 C00W 118.7(6) . . ?
C019 C018 C015 122.7(9) . . ?
C00E C019 H019 119.7 . . ?
C018 C019 C00E 120.7(7) . . ?
C018 C019 H019 119.7 . . ?
C00Q C01A C00Z 120.0(7) . . ?
C00Q C01A H01F 120.0 . . ?
C00Z C01A H01F 120.0 . . ?
O00O C01B C014 113.0(9) . . ?
O00T C01B O00O 126.1(9) . . ?
O00T C01B C014 120.9(11) . . ?
C00V C01C H01C 120.7 . . ?
C00X C01C C00V 118.6(6) . . ?
C00X C01C H01C 120.7 . . ?
H0A C0 H0B 109.5 . . ?
H0A C0 H0C 109.5 . . ?
H0B C0 H0C 109.5 . . ?
C1 C0 H0A 109.5 . . ?
C1 C0 H0B 109.5 . . ?
C1 C0 H0C 109.5 . . ?
H2A C2 H2B 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
C3 C2 H2A 109.5 . . ?
C3 C2 H2B 109.5 . . ?
C3 C2 H2C 109.5 . . ?
O00O C1 H1A 110.4 . . ?
O00O C1 H1B 110.4 . . ?
C0 C1 O00O 106.7(16) . . ?
C0 C1 H1A 110.4 . . ?
C0 C1 H1B 110.4 . . ?
H1A C1 H1B 108.6 . . ?
O010 C3 C2 102.9(19) . . ?
O010 C3 H3A 111.2 . . ?
O010 C3 H3B 111.2 . . ?
C2 C3 H3A 111.2 . . ?
C2 C3 H3B 111.2 . . ?
H3A C3 H3B 109.1 . . ?
H4A C4 H4B 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
C5 C4 H4A 109.5 . . ?
C5 C4 H4B 109.5 . . ?
C5 C4 H4C 109.5 . . ?
O00O C5 C4 99(2) . . ?
O00O C5 H5A 112.0 . . ?
O00O C5 H5B 112.0 . . ?
C4 C5 H5A 112.0 . . ?
C4 C5 H5B 112.0 . . ?
H5A C5 H5B 109.7 . . ?
H6A C6 H6B 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
C7 C6 H6A 109.5 . . ?
C7 C6 H6B 109.5 . . ?
C7 C6 H6C 109.5 . . ?
O010 C7 C6 97.2(16) . . ?
O010 C7 H7A 112.3 . . ?
O010 C7 H7B 112.3 . . ?
C6 C7 H7A 112.3 . . ?
C6 C7 H7B 112.3 . . ?
H7A C7 H7B 109.9 . . ?

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
F003 C00F C00K C00G -5.9(9) . . . . ?
F003 C00F C00K C00P 175.7(5) . . . . ?
F004 C00N C00R C00D 5.5(9) . . . . ?
F004 C00N C00R C012 -175.4(5) . . . . ?
N005 C00C C00I S002 -71.9(7) . . . . ?
N005 C00J C00Z C01A -177.0(7) . . . . ?
N005 C00N C00R C00D -169.3(5) . . . . ?
N005 C00N C00R C012 9.8(9) . . . . ?
N006 C00A C00M C013 177.0(6) . . . . ?
N006 C00A C00V N008 0.4(7) . . . . ?
N006 C00A C00V C01C -178.6(5) . . . . ?
N006 C00F C00K C00G 168.8(5) . . . . ?
N006 C00F C00K C00P -9.7(9) . . . . ?
N006 C00H C016 S001 72.7(8) . . . . ?
N007 C009 C00B C00Q 176.9(6) . . . . ?
N007 C009 C00J N005 -0.4(7) . . . . ?
N007 C009 C00J C00Z -178.0(6) . . . . ?
N007 C00C C00I S002 110.2(6) . . . . ?
N008 C00H C016 S001 -110.2(6) . . . . ?
N008 C00V C01C C00X -178.9(7) . . . . ?
C009 N007 C00C N005 -1.2(6) . . . . ?
C009 N007 C00C C00I 176.7(6) . . . . ?
C009 C00B C00Q C01A 2.3(11) . . . . ?
C009 C00J C00Z C01A -0.2(9) . . . . ?
C00A N006 C00F F003 -50.5(8) . . . . ?
C00A N006 C00F C00K 134.2(6) . . . . ?
C00A N006 C00H N008 -1.4(7) . . . . ?
C00A N006 C00H C016 176.1(6) . . . . ?
C00A C00M C013 C00X 1.5(10) . . . . ?
C00A C00V C01C C00X -0.1(10) . . . . ?
C00B C009 C00J N005 178.8(5) . . . . ?
C00B C009 C00J C00Z 1.2(9) . . . . ?
C00B C00Q C01A C00Z -1.4(12) . . . . ?
C00C N005 C00J C009 -0.3(6) . . . . ?
C00C N005 C00J C00Z 177.0(7) . . . . ?
C00C N005 C00N F004 -126.7(5) . . . . ?
C00C N005 C00N C00R 48.6(9) . . . . ?
C00C N007 C009 C00B -178.1(6) . . . . ?
C00C N007 C009 C00J 1.0(7) . . . . ?
C00D C00R C012 S002 98.9(5) . . . . ?
C00D C00S C017 C014 -1.5(10) . . . . ?
C00E C00G C00K C00F 47.2(8) . . . . ?
C00E C00G C00K C00P -134.4(6) . . . . ?
C00E C00G C011 C00W 0.4(9) . . . . ?
C00F N006 C00A C00M 0.4(11) . . . . ?
C00F N006 C00A C00V 177.1(5) . . . . ?
C00F N006 C00H N008 -178.3(5) . . . . ?
C00F N006 C00H C016 -0.8(9) . . . . ?
C00F C00K C00P S001 79.5(6) . . . . ?
C00G C00E C019 C018 1.2(11) . . . . ?
C00G C00K C00P S001 -98.9(5) . . . . ?
C00H N006 C00A C00M -176.3(6) . . . . ?
C00H N006 C00A C00V 0.5(6) . . . . ?
C00H N006 C00F F003 125.6(5) . . . . ?
C00H N006 C00F C00K -49.6(9) . . . . ?
C00H N008 C00V C00A -1.2(7) . . . . ?
C00H N008 C00V C01C 177.6(6) . . . . ?
C00I S002 C012 C00R 43.6(5) . . . . ?
C00J N005 C00C N007 1.0(7) . . . . ?
C00J N005 C00C C00I -177.1(6) . . . . ?
C00J N005 C00N F004 50.3(8) . . . . ?
C00J N005 C00N C00R -134.3(6) . . . . ?
C00J C009 C00B C00Q -2.2(9) . . . . ?
C00J C00Z C01A C00Q 0.3(10) . . . . ?
C00K C00G C011 C00W -179.1(6) . . . . ?
O00L C015 C018 C00W -5.6(12) . . . . ?
O00L C015 C018 C019 173.0(8) . . . . ?
C00M C00A C00V N008 177.5(6) . . . . ?
C00M C00A C00V C01C -1.5(9) . . . . ?
C00N N005 C00C N007 178.6(5) . . . . ?
C00N N005 C00C C00I 0.5(9) . . . . ?
C00N N005 C00J C009 -177.8(5) . . . . ?
C00N N005 C00J C00Z -0.5(11) . . . . ?
C00N C00R C012 S002 -80.2(6) . . . . ?
C00P S001 C016 C00H -43.9(6) . . . . ?
C00R C00D C00S C017 179.3(6) . . . . ?
C00R C00D C00Y C00U -178.2(6) . . . . ?
C00S C00D C00R C00N 132.5(6) . . . . ?
C00S C00D C00R C012 -46.6(7) . . . . ?
C00S C00D C00Y C00U 0.8(10) . . . . ?
C00U C014 C017 C00S 1.6(11) . . . . ?
C00U C014 C01B O00O 6.4(11) . . . . ?
C00U C014 C01B O00T -172.8(8) . . . . ?
C00V N008 C00H N006 1.6(7) . . . . ?
C00V N008 C00H C016 -175.7(7) . . . . ?
C00V C00A C00M C013 0.8(9) . . . . ?
C00W C018 C019 C00E -0.2(11) . . . . ?
C00Y C00D C00R C00N -48.5(9) . . . . ?
C00Y C00D C00R C012 132.4(7) . . . . ?
C00Y C00D C00S C017 0.3(9) . . . . ?
C00Y C00U C014 C017 -0.6(11) . . . . ?
C00Y C00U C014 C01B 178.3(7) . . . . ?
O010 C015 C018 C00W 176.2(7) . . . . ?
O010 C015 C018 C019 -5.2(11) . . . . ?
C011 C00G C00K C00F -133.4(6) . . . . ?
C011 C00G C00K C00P 45.0(7) . . . . ?
C011 C00W C018 C015 178.0(6) . . . . ?
C011 C00W C018 C019 -0.6(11) . . . . ?
C012 S002 C00I C00C 42.4(6) . . . . ?
C013 C00X C01C C00V 2.3(12) . . . . ?
C014 C00U C00Y C00D -0.7(11) . . . . ?
C015 O010 C3 C2 118(2) . . . . ?
C015 O010 C7 C6 167(2) . . . . ?
C015 C018 C019 C00E -178.8(7) . . . . ?
C016 S001 C00P C00K -41.6(5) . . . . ?
C017 C014 C01B O00O -174.7(8) . . . . ?
C017 C014 C01B O00T 6.1(12) . . . . ?
C018 C00W C011 C00G 0.6(10) . . . . ?
C019 C00E C00G C00K 178.2(6) . . . . ?
C019 C00E C00G C011 -1.2(10) . . . . ?
C01B O00O C1 C0 -151(2) . . . . ?
C01B O00O C5 C4 -119(3) . . . . ?
C01B C014 C017 C00S -177.3(6) . . . . ?
C01C C00X C013 C00M -3.1(12) . . . . ?
C1 O00O C01B O00T -6.1(17) . . . . ?
C1 O00O C01B C014 174.8(13) . . . . ?
C3 O010 C015 O00L -12(2) . . . . ?
C3 O010 C015 C018 165.8(15) . . . . ?
C5 O00O C01B O00T 11(3) . . . . ?
C5 O00O C01B C014 -168(2) . . . . ?
C7 O010 C015 O00L 10.4(16) . . . . ?
C7 O010 C015 C018 -171.4(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 2470561'
loop_
_audit_author_name
_audit_author_address
'Keyume Ablajan'
;Xinjiang University
China
;
_audit_update_record             
;
2025-07-07 deposited with the CCDC.	2025-12-08 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C19 H13 F N2 O'
_chemical_formula_weight         304.31

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   11.149
_cell_length_b                   12.237
_cell_length_c                   11.005
_cell_angle_alpha                90
_cell_angle_beta                 97.90
_cell_angle_gamma                90
_cell_volume                     1487.1
_cell_formula_units_Z            4
_cell_measurement_temperature    273(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.359
_exptl_crystal_F_000             632
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.220
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.180
_exptl_absorpt_coefficient_mu    0.771
_shelx_estimated_absorpt_T_min   0.849
_shelx_estimated_absorpt_T_max   0.874
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      273(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            2595
_diffrn_reflns_av_unetI/netI     0.0394
_diffrn_reflns_av_R_equivalents  ?
_diffrn_reflns_limit_h_min       ?
_diffrn_reflns_limit_h_max       ?
_diffrn_reflns_limit_k_min       ?
_diffrn_reflns_limit_k_max       ?
_diffrn_reflns_limit_l_min       ?
_diffrn_reflns_limit_l_max       ?
_diffrn_reflns_theta_min         4.003
_diffrn_reflns_theta_max         66.674
_diffrn_reflns_theta_full        66.674
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measured_fraction_theta_full 0.986
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_Laue_measured_fraction_full 0.986
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_point_group_measured_fraction_full 0.986
_reflns_number_total             2595
_reflns_number_gt                2031
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0874P)²+0.4912P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2595
_refine_ls_number_parameters     208
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0726
_refine_ls_R_factor_gt           0.0593
_refine_ls_wR_factor_ref         0.1693
_refine_ls_wR_factor_gt          0.1615
_refine_ls_goodness_of_fit_ref   1.076
_refine_ls_restrained_S_all      1.076
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.4085(3) -0.1629(3) 0.3003(3) 0.0828(9) Uani 1 1 d . . . . .
H1 H 0.4063 -0.2386 0.3067 0.099 Uiso 1 1 calc R U . . .
C2 C 0.4564(3) -0.1149(3) 0.2067(3) 0.0887(10) Uani 1 1 d . . . . .
H2 H 0.4878 -0.1588 0.1496 0.106 Uiso 1 1 calc R U . . .
C3 C 0.4599(2) -0.0019(3) 0.1940(3) 0.0818(8) Uani 1 1 d . . . . .
H3 H 0.4929 0.0283 0.1285 0.098 Uiso 1 1 calc R U . . .
C4 C 0.4151(2) 0.0659(2) 0.2769(2) 0.0673(7) Uani 1 1 d . . . . .
H4 H 0.4170 0.1416 0.2690 0.081 Uiso 1 1 calc R U . . .
C5 C 0.36712(19) 0.0164(2) 0.3726(2) 0.0567(6) Uani 1 1 d . . . . .
C6 C 0.3622(2) -0.0970(2) 0.3872(2) 0.0651(7) Uani 1 1 d . . . . .
C7 C 0.3038(2) -0.1181(2) 0.4925(2) 0.0686(7) Uani 1 1 d . . . . .
H7 H 0.2881 -0.1868 0.5230 0.082 Uiso 1 1 calc R U . . .
C8 C 0.2753(2) -0.0218(2) 0.5402(2) 0.0588(6) Uani 1 1 d . . . . .
C9 C 0.2273(2) 0.0056(2) 0.6566(2) 0.0663(7) Uani 1 1 d . . . . .
H9A H 0.2227 -0.0613 0.7030 0.080 Uiso 1 1 calc R U . . .
H9B H 0.2850 0.0533 0.7047 0.080 Uiso 1 1 calc R U . . .
C10 C 0.0871(2) 0.12502(19) 0.5370(2) 0.0573(6) Uani 1 1 d . . . . .
H10A H 0.0115 0.1634 0.5403 0.069 Uiso 1 1 calc R U . . .
H10B H 0.0763 0.0788 0.4648 0.069 Uiso 1 1 calc R U . . .
C11 C 0.18477(19) 0.20847(18) 0.52269(19) 0.0517(5) Uani 1 1 d . . . . .
C12 C 0.28504(19) 0.17119(18) 0.4844(2) 0.0533(5) Uani 1 1 d . . . . .
C13 C 0.16609(19) 0.32366(18) 0.55339(19) 0.0508(5) Uani 1 1 d . . . . .
C14 C 0.2008(2) 0.40970(19) 0.4834(2) 0.0594(6) Uani 1 1 d . . . . .
H14 H 0.2372 0.3946 0.4141 0.071 Uiso 1 1 calc R U . . .
C15 C 0.1824(2) 0.5169(2) 0.5144(2) 0.0622(6) Uani 1 1 d . . . . .
H15 H 0.2068 0.5733 0.4668 0.075 Uiso 1 1 calc R U . . .
C16 C 0.1274(2) 0.54039(19) 0.6167(2) 0.0567(6) Uani 1 1 d . . . . .
C17 C 0.0888(2) 0.4564(2) 0.6860(2) 0.0587(6) Uani 1 1 d . . . . .
H17 H 0.0500 0.4718 0.7536 0.070 Uiso 1 1 calc R U . . .
C18 C 0.1082(2) 0.34944(19) 0.6539(2) 0.0562(6) Uani 1 1 d . . . . .
H18 H 0.0820 0.2932 0.7007 0.067 Uiso 1 1 calc R U . . .
C19 C 0.1102(2) 0.6521(2) 0.6514(2) 0.0647(6) Uani 1 1 d . . . . .
F1 F 0.37654(13) 0.23842(11) 0.46424(15) 0.0723(4) Uani 1 1 d . . . . .
N1 N 0.31365(17) 0.06297(15) 0.46846(17) 0.0561(5) Uani 1 1 d . . . . .
N2 N 0.0985(2) 0.7411(2) 0.6797(3) 0.0852(7) Uani 1 1 d . . . . .
O1 O 0.11119(15) 0.05717(14) 0.64290(15) 0.0648(5) 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
C1 C2 1.358(5) . ?
C1 C6 1.402(4) . ?
C1 H1 0.9300 . ?
C2 C3 1.391(5) . ?
C2 H2 0.9300 . ?
C3 C4 1.377(4) . ?
C3 H3 0.9300 . ?
C4 C5 1.385(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.399(4) . ?
C5 N1 1.402(3) . ?
C6 C7 1.429(4) . ?
C7 C8 1.346(3) . ?
C7 H7 0.9300 . ?
C8 N1 1.405(3) . ?
C8 C9 1.492(3) . ?
C9 O1 1.430(3) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 O1 1.426(3) . ?
C10 C11 1.517(3) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 C12 1.328(3) . ?
C11 C13 1.471(3) . ?
C12 F1 1.353(2) . ?
C12 N1 1.379(3) . ?
C13 C14 1.390(3) . ?
C13 C18 1.391(3) . ?
C14 C15 1.378(3) . ?
C14 H14 0.9300 . ?
C15 C16 1.384(3) . ?
C15 H15 0.9300 . ?
C16 C17 1.383(3) . ?
C16 C19 1.440(3) . ?
C17 C18 1.380(3) . ?
C17 H17 0.9300 . ?
C18 H18 0.9300 . ?
C19 N2 1.145(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 C6 119.3(3) . . ?
C2 C1 H1 120.4 . . ?
C6 C1 H1 120.4 . . ?
C1 C2 C3 121.7(3) . . ?
C1 C2 H2 119.2 . . ?
C3 C2 H2 119.2 . . ?
C4 C3 C2 121.0(3) . . ?
C4 C3 H3 119.5 . . ?
C2 C3 H3 119.5 . . ?
C3 C4 C5 116.9(3) . . ?
C3 C4 H4 121.5 . . ?
C5 C4 H4 121.5 . . ?
C4 C5 C6 123.1(2) . . ?
C4 C5 N1 130.0(2) . . ?
C6 C5 N1 106.9(2) . . ?
C5 C6 C1 117.9(3) . . ?
C5 C6 C7 107.5(2) . . ?
C1 C6 C7 134.5(3) . . ?
C8 C7 C6 108.4(2) . . ?
C8 C7 H7 125.8 . . ?
C6 C7 H7 125.8 . . ?
C7 C8 N1 108.7(2) . . ?
C7 C8 C9 131.5(2) . . ?
N1 C8 C9 119.3(2) . . ?
O1 C9 C8 115.8(2) . . ?
O1 C9 H9A 108.3 . . ?
C8 C9 H9A 108.3 . . ?
O1 C9 H9B 108.3 . . ?
C8 C9 H9B 108.3 . . ?
H9A C9 H9B 107.4 . . ?
O1 C10 C11 114.84(18) . . ?
O1 C10 H10A 108.6 . . ?
C11 C10 H10A 108.6 . . ?
O1 C10 H10B 108.6 . . ?
C11 C10 H10B 108.6 . . ?
H10A C10 H10B 107.5 . . ?
C12 C11 C13 123.6(2) . . ?
C12 C11 C10 116.7(2) . . ?
C13 C11 C10 119.67(19) . . ?
C11 C12 F1 122.0(2) . . ?
C11 C12 N1 126.1(2) . . ?
F1 C12 N1 111.73(18) . . ?
C14 C13 C18 117.6(2) . . ?
C14 C13 C11 122.6(2) . . ?
C18 C13 C11 119.7(2) . . ?
C15 C14 C13 121.4(2) . . ?
C15 C14 H14 119.3 . . ?
C13 C14 H14 119.3 . . ?
C14 C15 C16 119.8(2) . . ?
C14 C15 H15 120.1 . . ?
C16 C15 H15 120.1 . . ?
C17 C16 C15 120.0(2) . . ?
C17 C16 C19 119.8(2) . . ?
C15 C16 C19 120.2(2) . . ?
C18 C17 C16 119.5(2) . . ?
C18 C17 H17 120.3 . . ?
C16 C17 H17 120.3 . . ?
C17 C18 C13 121.6(2) . . ?
C17 C18 H18 119.2 . . ?
C13 C18 H18 119.2 . . ?
N2 C19 C16 178.9(3) . . ?
C12 N1 C5 128.0(2) . . ?
C12 N1 C8 122.91(19) . . ?
C5 N1 C8 108.46(19) . . ?
C10 O1 C9 114.15(17) . . ?

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
C6 C1 C2 C3 -0.7(4) . . . . ?
C1 C2 C3 C4 0.5(5) . . . . ?
C2 C3 C4 C5 0.0(4) . . . . ?
C3 C4 C5 C6 -0.3(4) . . . . ?
C3 C4 C5 N1 -178.7(2) . . . . ?
C4 C5 C6 C1 0.1(4) . . . . ?
N1 C5 C6 C1 178.8(2) . . . . ?
C4 C5 C6 C7 -178.1(2) . . . . ?
N1 C5 C6 C7 0.6(3) . . . . ?
C2 C1 C6 C5 0.4(4) . . . . ?
C2 C1 C6 C7 178.0(3) . . . . ?
C5 C6 C7 C8 -0.4(3) . . . . ?
C1 C6 C7 C8 -178.1(3) . . . . ?
C6 C7 C8 N1 0.0(3) . . . . ?
C6 C7 C8 C9 -171.7(3) . . . . ?
C7 C8 C9 O1 -118.0(3) . . . . ?
N1 C8 C9 O1 71.0(3) . . . . ?
O1 C10 C11 C12 75.6(3) . . . . ?
O1 C10 C11 C13 -103.1(2) . . . . ?
C13 C11 C12 F1 -3.6(4) . . . . ?
C10 C11 C12 F1 177.68(19) . . . . ?
C13 C11 C12 N1 171.7(2) . . . . ?
C10 C11 C12 N1 -6.9(3) . . . . ?
C12 C11 C13 C14 41.6(3) . . . . ?
C10 C11 C13 C14 -139.8(2) . . . . ?
C12 C11 C13 C18 -140.5(2) . . . . ?
C10 C11 C13 C18 38.2(3) . . . . ?
C18 C13 C14 C15 2.1(4) . . . . ?
C11 C13 C14 C15 -179.9(2) . . . . ?
C13 C14 C15 C16 -0.5(4) . . . . ?
C14 C15 C16 C17 -1.4(4) . . . . ?
C14 C15 C16 C19 178.6(2) . . . . ?
C15 C16 C17 C18 1.6(4) . . . . ?
C19 C16 C17 C18 -178.4(2) . . . . ?
C16 C17 C18 C13 0.1(4) . . . . ?
C14 C13 C18 C17 -1.9(3) . . . . ?
C11 C13 C18 C17 -180.0(2) . . . . ?
C11 C12 N1 C5 138.7(2) . . . . ?
F1 C12 N1 C5 -45.5(3) . . . . ?
C11 C12 N1 C8 -31.3(4) . . . . ?
F1 C12 N1 C8 144.5(2) . . . . ?
C4 C5 N1 C12 6.8(4) . . . . ?
C6 C5 N1 C12 -171.8(2) . . . . ?
C4 C5 N1 C8 178.0(2) . . . . ?
C6 C5 N1 C8 -0.6(3) . . . . ?
C7 C8 N1 C12 172.1(2) . . . . ?
C9 C8 N1 C12 -15.0(3) . . . . ?
C7 C8 N1 C5 0.4(3) . . . . ?
C9 C8 N1 C5 173.3(2) . . . . ?
C11 C10 O1 C9 -51.4(3) . . . . ?
C8 C9 O1 C10 -31.7(3) . . . . ?

_refine_diff_density_max         0.164
_refine_diff_density_min         -0.261
_refine_diff_density_rms         0.060



####################################################################### 
# 
# 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 2470562'
loop_
_audit_author_name
_audit_author_address
'Keyume Ablajan'
;Xinjiang University
China
;
_audit_update_record             
;
2025-07-07 deposited with the CCDC.	2025-12-08 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C22 H17 F N2 O2'
_chemical_formula_weight         360.37

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

_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.
;

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'
'-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                   14.974
_cell_length_b                   7.741
_cell_length_c                   29.954
_cell_angle_alpha                90
_cell_angle_beta                 91.40
_cell_angle_gamma                90
_cell_volume                     3471.1
_cell_formula_units_Z            8
_cell_measurement_temperature    273(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.379
_exptl_crystal_F_000             1504
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.120
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.080
_exptl_absorpt_coefficient_mu    0.793
_shelx_estimated_absorpt_T_min   0.911
_shelx_estimated_absorpt_T_max   0.939
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      273(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            5853
_diffrn_reflns_av_unetI/netI     0.0924
_diffrn_reflns_av_R_equivalents  0.1120
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_limit_l_max       35
_diffrn_reflns_theta_min         2.951
_diffrn_reflns_theta_max         67.205
_diffrn_reflns_theta_full        67.205
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_point_group_measured_fraction_full 0.993
_reflns_number_total             3085
_reflns_number_gt                1566
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1354P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3085
_refine_ls_number_parameters     245
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1104
_refine_ls_R_factor_gt           0.0724
_refine_ls_wR_factor_ref         0.2317
_refine_ls_wR_factor_gt          0.1988
_refine_ls_goodness_of_fit_ref   0.936
_refine_ls_restrained_S_all      0.936
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.4840(2) 0.5235(5) 0.87458(12) 0.0844(10) Uani 1 1 d . . . . .
H1 H 0.4943 0.6165 0.8937 0.101 Uiso 1 1 calc R U . . .
C2 C 0.5053(2) 0.3616(5) 0.88852(13) 0.0882(11) Uani 1 1 d . . . . .
H2 H 0.5299 0.3444 0.9170 0.106 Uiso 1 1 calc R U . . .
C3 C 0.4902(2) 0.2200(5) 0.86012(13) 0.0891(11) Uani 1 1 d . . . . .
H3 H 0.5061 0.1099 0.8699 0.107 Uiso 1 1 calc R U . . .
C4 C 0.4529(2) 0.2400(5) 0.81872(12) 0.0820(10) Uani 1 1 d . . . . .
H4 H 0.4430 0.1443 0.8005 0.098 Uiso 1 1 calc R U . . .
C5 C 0.4289(2) 0.4086(4) 0.80316(11) 0.0714(9) Uani 1 1 d . . . . .
C6 C 0.4464(2) 0.5538(5) 0.83112(11) 0.0746(9) Uani 1 1 d . . . . .
C7 C 0.4263(2) 0.7211(5) 0.81576(12) 0.0802(10) Uani 1 1 d . . . . .
H7 H 0.4372 0.8167 0.8339 0.096 Uiso 1 1 calc R U . . .
C8 C 0.3900(2) 0.7411(4) 0.77333(12) 0.0740(9) Uani 1 1 d . . . . .
C9 C 0.3697(2) 0.5956(4) 0.74674(11) 0.0700(9) Uani 1 1 d . . . . .
C10 C 0.3884(2) 0.4300(4) 0.76027(11) 0.0746(9) Uani 1 1 d . . . . .
H10 H 0.3750 0.3357 0.7421 0.089 Uiso 1 1 calc R U . . .
C11 C 0.3352(2) 0.8382(5) 0.71132(12) 0.0772(9) Uani 1 1 d . . . . .
C12 C 0.3051(3) 0.9523(5) 0.67458(13) 0.0875(11) Uani 1 1 d . . . . .
H12A H 0.2409 0.9423 0.6703 0.105 Uiso 1 1 calc R U . . .
H12B H 0.3189 1.0713 0.6821 0.105 Uiso 1 1 calc R U . . .
C13 C 0.3129(2) 0.7703(5) 0.61171(12) 0.0779(10) Uani 1 1 d . . . . .
C14 C 0.2810(2) 0.6212(5) 0.62624(11) 0.0744(9) Uani 1 1 d . . . . .
C15 C 0.2897(3) 0.5545(5) 0.67322(11) 0.0857(10) Uani 1 1 d . . . . .
H15A H 0.2300 0.5301 0.6834 0.103 Uiso 1 1 calc R U . . .
H15B H 0.3212 0.4451 0.6722 0.103 Uiso 1 1 calc R U . . .
C16 C 0.2342(2) 0.5010(4) 0.59492(11) 0.0734(9) Uani 1 1 d . . . . .
C17 C 0.1642(2) 0.5567(5) 0.56750(13) 0.0910(11) Uani 1 1 d . . . . .
H17 H 0.1461 0.6715 0.5689 0.109 Uiso 1 1 calc R U . . .
C18 C 0.1206(3) 0.4460(6) 0.53820(13) 0.0954(12) Uani 1 1 d . . . . .
H18 H 0.0750 0.4878 0.5195 0.115 Uiso 1 1 calc R U . . .
C19 C 0.1439(2) 0.2750(5) 0.53635(11) 0.0795(10) Uani 1 1 d . . . . .
C20 C 0.2127(2) 0.2139(5) 0.56369(12) 0.0809(10) Uani 1 1 d . . . . .
H20 H 0.2297 0.0984 0.5625 0.097 Uiso 1 1 calc R U . . .
C21 C 0.2559(2) 0.3271(4) 0.59278(11) 0.0806(10) Uani 1 1 d . . . . .
H21 H 0.3012 0.2849 0.6116 0.097 Uiso 1 1 calc R U . . .
C22 C 0.1218(3) -0.0024(6) 0.50313(13) 0.0972(12) Uani 1 1 d . . . . .
H22A H 0.0867 -0.0570 0.4799 0.146 Uiso 1 1 calc R U . . .
H22B H 0.1122 -0.0603 0.5309 0.146 Uiso 1 1 calc R U . . .
H22C H 0.1839 -0.0087 0.4961 0.146 Uiso 1 1 calc R U . . .
F1 F 0.31279(16) 0.8070(3) 0.56812(7) 0.1005(7) Uani 1 1 d . . . . .
N1 N 0.33425(18) 0.6614(4) 0.70713(9) 0.0740(8) Uani 1 1 d . . . . .
N2 N 0.3681(2) 0.8923(4) 0.74987(10) 0.0829(9) Uani 1 1 d . . . . .
O1 O 0.34897(17) 0.9055(3) 0.63370(9) 0.0865(7) Uani 1 1 d . . . . .
O2 O 0.09588(17) 0.1740(4) 0.50683(9) 0.0988(9) 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
C1 C2 1.357(5) . ?
C1 C6 1.425(4) . ?
C1 H1 0.9300 . ?
C2 C3 1.402(5) . ?
C2 H2 0.9300 . ?
C3 C4 1.356(5) . ?
C3 H3 0.9300 . ?
C4 C5 1.429(5) . ?
C4 H4 0.9300 . ?
C5 C10 1.417(4) . ?
C5 C6 1.422(4) . ?
C6 C7 1.405(5) . ?
C7 C8 1.379(5) . ?
C7 H7 0.9300 . ?
C8 N2 1.400(4) . ?
C8 C9 1.408(4) . ?
C9 C10 1.371(4) . ?
C9 N1 1.385(4) . ?
C10 H10 0.9300 . ?
C11 N2 1.313(4) . ?
C11 N1 1.375(4) . ?
C11 C12 1.473(5) . ?
C12 O1 1.450(5) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 C14 1.326(5) . ?
C13 F1 1.336(4) . ?
C13 O1 1.343(4) . ?
C14 C16 1.485(4) . ?
C14 C15 1.502(5) . ?
C15 N1 1.459(4) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C16 C17 1.385(4) . ?
C16 C21 1.387(5) . ?
C17 C18 1.380(5) . ?
C17 H17 0.9300 . ?
C18 C19 1.371(5) . ?
C18 H18 0.9300 . ?
C19 O2 1.371(4) . ?
C19 C20 1.383(4) . ?
C20 C21 1.385(4) . ?
C20 H20 0.9300 . ?
C21 H21 0.9300 . ?
C22 O2 1.424(5) . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 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
C2 C1 C6 121.1(4) . . ?
C2 C1 H1 119.4 . . ?
C6 C1 H1 119.4 . . ?
C1 C2 C3 120.2(3) . . ?
C1 C2 H2 119.9 . . ?
C3 C2 H2 119.9 . . ?
C4 C3 C2 121.4(4) . . ?
C4 C3 H3 119.3 . . ?
C2 C3 H3 119.3 . . ?
C3 C4 C5 119.8(3) . . ?
C3 C4 H4 120.1 . . ?
C5 C4 H4 120.1 . . ?
C10 C5 C6 120.7(3) . . ?
C10 C5 C4 120.1(3) . . ?
C6 C5 C4 119.2(3) . . ?
C7 C6 C5 120.1(3) . . ?
C7 C6 C1 121.8(3) . . ?
C5 C6 C1 118.1(3) . . ?
C8 C7 C6 118.8(3) . . ?
C8 C7 H7 120.6 . . ?
C6 C7 H7 120.6 . . ?
C7 C8 N2 129.7(3) . . ?
C7 C8 C9 120.4(3) . . ?
N2 C8 C9 109.9(3) . . ?
C10 C9 N1 131.9(3) . . ?
C10 C9 C8 122.7(3) . . ?
N1 C9 C8 105.3(3) . . ?
C9 C10 C5 117.2(3) . . ?
C9 C10 H10 121.4 . . ?
C5 C10 H10 121.4 . . ?
N2 C11 N1 113.6(3) . . ?
N2 C11 C12 124.6(3) . . ?
N1 C11 C12 121.8(3) . . ?
O1 C12 C11 110.2(3) . . ?
O1 C12 H12A 109.6 . . ?
C11 C12 H12A 109.6 . . ?
O1 C12 H12B 109.6 . . ?
C11 C12 H12B 109.6 . . ?
H12A C12 H12B 108.1 . . ?
C14 C13 F1 120.9(3) . . ?
C14 C13 O1 131.4(3) . . ?
F1 C13 O1 107.7(3) . . ?
C13 C14 C16 120.4(3) . . ?
C13 C14 C15 125.7(3) . . ?
C16 C14 C15 113.9(3) . . ?
N1 C15 C14 119.0(3) . . ?
N1 C15 H15A 107.6 . . ?
C14 C15 H15A 107.6 . . ?
N1 C15 H15B 107.6 . . ?
C14 C15 H15B 107.6 . . ?
H15A C15 H15B 107.0 . . ?
C17 C16 C21 116.7(3) . . ?
C17 C16 C14 121.2(3) . . ?
C21 C16 C14 122.0(3) . . ?
C18 C17 C16 121.6(3) . . ?
C18 C17 H17 119.2 . . ?
C16 C17 H17 119.2 . . ?
C19 C18 C17 120.6(3) . . ?
C19 C18 H18 119.7 . . ?
C17 C18 H18 119.7 . . ?
C18 C19 O2 116.5(3) . . ?
C18 C19 C20 119.6(3) . . ?
O2 C19 C20 123.9(3) . . ?
C19 C20 C21 119.1(3) . . ?
C19 C20 H20 120.5 . . ?
C21 C20 H20 120.5 . . ?
C20 C21 C16 122.5(3) . . ?
C20 C21 H21 118.8 . . ?
C16 C21 H21 118.8 . . ?
O2 C22 H22A 109.5 . . ?
O2 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
O2 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C11 N1 C9 106.6(2) . . ?
C11 N1 C15 129.2(3) . . ?
C9 N1 C15 123.2(3) . . ?
C11 N2 C8 104.6(3) . . ?
C13 O1 C12 115.0(3) . . ?
C19 O2 C22 117.2(3) . . ?

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
C6 C1 C2 C3 -0.1(6) . . . . ?
C1 C2 C3 C4 -1.2(6) . . . . ?
C2 C3 C4 C5 0.6(6) . . . . ?
C3 C4 C5 C10 -178.8(4) . . . . ?
C3 C4 C5 C6 1.3(5) . . . . ?
C10 C5 C6 C7 -2.2(5) . . . . ?
C4 C5 C6 C7 177.7(3) . . . . ?
C10 C5 C6 C1 177.6(3) . . . . ?
C4 C5 C6 C1 -2.6(5) . . . . ?
C2 C1 C6 C7 -178.3(4) . . . . ?
C2 C1 C6 C5 2.0(5) . . . . ?
C5 C6 C7 C8 -0.3(5) . . . . ?
C1 C6 C7 C8 179.9(3) . . . . ?
C6 C7 C8 N2 -176.8(3) . . . . ?
C6 C7 C8 C9 2.9(5) . . . . ?
C7 C8 C9 C10 -3.2(5) . . . . ?
N2 C8 C9 C10 176.6(3) . . . . ?
C7 C8 C9 N1 179.5(3) . . . . ?
N2 C8 C9 N1 -0.7(4) . . . . ?
N1 C9 C10 C5 177.1(3) . . . . ?
C8 C9 C10 C5 0.7(5) . . . . ?
C6 C5 C10 C9 1.9(5) . . . . ?
C4 C5 C10 C9 -177.9(3) . . . . ?
N2 C11 C12 O1 126.4(4) . . . . ?
N1 C11 C12 O1 -50.9(4) . . . . ?
F1 C13 C14 C16 -7.8(5) . . . . ?
O1 C13 C14 C16 172.5(3) . . . . ?
F1 C13 C14 C15 170.4(3) . . . . ?
O1 C13 C14 C15 -9.3(6) . . . . ?
C13 C14 C15 N1 1.9(6) . . . . ?
C16 C14 C15 N1 -179.8(3) . . . . ?
C13 C14 C16 C17 -51.9(5) . . . . ?
C15 C14 C16 C17 129.7(4) . . . . ?
C13 C14 C16 C21 130.5(4) . . . . ?
C15 C14 C16 C21 -47.9(5) . . . . ?
C21 C16 C17 C18 -2.5(6) . . . . ?
C14 C16 C17 C18 179.7(4) . . . . ?
C16 C17 C18 C19 2.0(7) . . . . ?
C17 C18 C19 O2 178.8(4) . . . . ?
C17 C18 C19 C20 -1.0(6) . . . . ?
C18 C19 C20 C21 0.7(6) . . . . ?
O2 C19 C20 C21 -179.1(3) . . . . ?
C19 C20 C21 C16 -1.5(6) . . . . ?
C17 C16 C21 C20 2.3(6) . . . . ?
C14 C16 C21 C20 -180.0(4) . . . . ?
N2 C11 N1 C9 0.2(4) . . . . ?
C12 C11 N1 C9 177.7(3) . . . . ?
N2 C11 N1 C15 168.3(3) . . . . ?
C12 C11 N1 C15 -14.1(6) . . . . ?
C10 C9 N1 C11 -176.6(4) . . . . ?
C8 C9 N1 C11 0.3(4) . . . . ?
C10 C9 N1 C15 14.4(6) . . . . ?
C8 C9 N1 C15 -168.7(3) . . . . ?
C14 C15 N1 C11 33.9(6) . . . . ?
C14 C15 N1 C9 -159.7(3) . . . . ?
N1 C11 N2 C8 -0.6(4) . . . . ?
C12 C11 N2 C8 -178.1(3) . . . . ?
C7 C8 N2 C11 -179.5(4) . . . . ?
C9 C8 N2 C11 0.8(4) . . . . ?
C14 C13 O1 C12 -41.0(5) . . . . ?
F1 C13 O1 C12 139.3(3) . . . . ?
C11 C12 O1 C13 80.9(3) . . . . ?
C18 C19 O2 C22 177.4(4) . . . . ?
C20 C19 O2 C22 -2.8(5) . . . . ?

_refine_diff_density_max         0.181
_refine_diff_density_min         -0.256
_refine_diff_density_rms         0.053



