#------------------------------------------------------------------------------
#$Date: 2020-06-14 01:41:01 +0300 (Sun, 14 Jun 2020) $
#$Revision: 253154 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/55/83/1558317.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_1558317
loop_
_publ_author_name
'Zhang, Chen'
'Ye, Fei'
'Wang, Jianmin'
'He, Ping'
'Lei, Ming'
'Huang, Longbin'
'Huang, Anbang'
'Tang, Pingming'
'Lin, Hongjun'
'Liao, Yuting'
'Liang, Yong'
'Ni, Jia'
'Yan, Pangke'
_publ_section_title
;
 Design, Synthesis, and Evaluation of a Series of Novel Super Long-Acting
 DPP-4 Inhibitors for the Treatment of Type 2 Diabetes.
;
_journal_name_full               'Journal of medicinal chemistry'
_journal_paper_doi               10.1021/acs.jmedchem.0c00374
_journal_year                    2020
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C18 H20 F5 N4 O3 S, C2 F3 O2'
_chemical_formula_sum            'C20 H20 F8 N4 O5 S'
_chemical_formula_weight         580.46
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2016-03-31
_audit_creation_method
;
  Olex2 1.1
  (compiled 2011.02.15 svn.r1672, GUI svn.r3494)
;
_cell_angle_alpha                90.00
_cell_angle_beta                 94.623(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   6.12766(15)
_cell_length_b                   20.2470(5)
_cell_length_c                   10.0261(2)
_cell_measurement_reflns_used    4587
_cell_measurement_temperature    103.1
_cell_measurement_theta_max      70.8954
_cell_measurement_theta_min      4.3635
_cell_volume                     1239.86(5)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_molecular_graphics
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution
'A short history of SHELX (Sheldrick, 2007)/Bruker'
_diffrn_ambient_temperature      103.1
_diffrn_detector_area_resol_mean 16.0971
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_details
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -36.00   -9.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       -8.5000  111.0000  -30.0000 27

#__ type_ start__ end____ width___ exp.time_
  2 omega  -23.00   15.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       -8.5000  111.0000 -120.0000 38

#__ type_ start__ end____ width___ exp.time_
  3 omega   65.00   94.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       36.7852   37.0000   90.0000 29

#__ type_ start__ end____ width___ exp.time_
  4 omega  -26.00   43.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       36.7852  -77.0000 -180.0000 69

#__ type_ start__ end____ width___ exp.time_
  5 omega   18.00  101.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       36.7852   77.0000  -60.0000 83

#__ type_ start__ end____ width___ exp.time_
  6 omega   18.00  105.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       36.7852   37.0000 -120.0000 87

#__ type_ start__ end____ width___ exp.time_
  7 omega  -31.00   61.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       36.7852  -77.0000   90.0000 92

#__ type_ start__ end____ width___ exp.time_
  8 omega   54.00   79.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       36.7852   37.0000    0.0000 25

#__ type_ start__ end____ width___ exp.time_
  9 omega  -27.00   39.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       36.7852  -37.0000  -60.0000 66

#__ type_ start__ end____ width___ exp.time_
 10 omega  145.00  174.00   1.0000    1.9000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000  -60.0000 29

#__ type_ start__ end____ width___ exp.time_
 11 omega   82.00  111.00   1.0000    1.9000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000  -60.0000 29

#__ type_ start__ end____ width___ exp.time_
 12 omega  127.00  169.00   1.0000    1.9000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000  120.0000 42

#__ type_ start__ end____ width___ exp.time_
 13 omega   42.00  130.00   1.0000    1.9000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -77.0000  120.0000 88

#__ type_ start__ end____ width___ exp.time_
 14 omega   82.00  175.00   1.0000    1.9000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   76.0000 -129.0000 93

#__ type_ start__ end____ width___ exp.time_
 15 omega   83.00  151.00   1.0000    1.9000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000 -180.0000 68

#__ type_ start__ end____ width___ exp.time_
 16 omega   70.00  117.00   1.0000    1.9000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   15.0000  -30.0000 47

#__ type_ start__ end____ width___ exp.time_
 17 omega   54.00   96.00   1.0000    1.9000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -77.0000   60.0000 42

#__ type_ start__ end____ width___ exp.time_
 18 omega   75.00  101.00   1.0000    1.9000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   15.0000 -150.0000 26

#__ type_ start__ end____ width___ exp.time_
 19 omega  142.00  173.00   1.0000    1.9000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000  -30.0000 31

#__ type_ start__ end____ width___ exp.time_
 20 omega   70.00  147.00   1.0000    1.9000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   15.0000   30.0000 77

#__ type_ start__ end____ width___ exp.time_
 21 omega   81.00  107.00   1.0000    1.9000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000  -30.0000 26

#__ type_ start__ end____ width___ exp.time_
 22 omega   85.00  164.00   1.0000    1.9000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000    0.0000 79

#__ type_ start__ end____ width___ exp.time_
 23 omega   81.00  176.00   1.0000    1.9000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000  150.0000 95

#__ type_ start__ end____ width___ exp.time_
 24 omega   62.00  115.00   1.0000    1.9000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -15.0000   30.0000 53

#__ type_ start__ end____ width___ exp.time_
 25 omega  102.00  178.00   1.0000    1.9000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  111.0000 -180.0000 76
;
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.1198403000
_diffrn_orient_matrix_UB_12      -0.0615519000
_diffrn_orient_matrix_UB_13      -0.0592388000
_diffrn_orient_matrix_UB_21      0.0850871000
_diffrn_orient_matrix_UB_22      0.0149524000
_diffrn_orient_matrix_UB_23      -0.1373181000
_diffrn_orient_matrix_UB_31      0.2049376000
_diffrn_orient_matrix_UB_32      -0.0421393000
_diffrn_orient_matrix_UB_33      0.0376325000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.5418
_diffrn_reflns_av_R_equivalents  0.0313
_diffrn_reflns_av_unetI/netI     0.0451
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            8355
_diffrn_reflns_theta_full        71.03
_diffrn_reflns_theta_max         71.03
_diffrn_reflns_theta_min         4.37
_diffrn_source                   'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.093
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.65432
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.555
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       'not measured'
_exptl_crystal_F_000             592
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.371
_refine_diff_density_min         -0.249
_refine_diff_density_rms         0.052
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.010(15)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     345
_refine_ls_number_reflns         4695
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.036
_refine_ls_R_factor_all          0.0377
_refine_ls_R_factor_gt           0.0364
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0578P)²+0.1823P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0942
_refine_ls_wR_factor_ref         0.0959
_reflns_number_gt                4557
_reflns_number_total             4695
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jm0c00374_si_001.cif
_cod_data_source_block           exp_3941
_cod_database_code               1558317
_reflns_odcompleteness_completeness 99.91
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, y+1/2, -z'
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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S -0.21367(10) -0.47968(2) -0.51188(5) 0.02068(14) Uani 1 1 d . . .
F4 F 0.0109(2) -0.59583(7) -1.14700(15) 0.0230(3) Uani 1 1 d . . .
F5 F 0.0086(2) -0.64556(7) -1.33695(15) 0.0264(3) Uani 1 1 d . . .
F3 F 0.0010(2) -0.70218(7) -1.15595(15) 0.0221(3) Uani 1 1 d . . .
F2 F -0.9551(3) -0.75254(12) -1.72722(18) 0.0492(5) Uani 1 1 d . . .
O1 O -0.4094(2) -0.67429(7) -1.35478(16) 0.0145(3) Uani 1 1 d . . .
F1 F -0.1578(3) -0.82985(8) -1.51112(17) 0.0345(4) Uani 1 1 d . . .
O3 O -0.2876(3) -0.41327(8) -0.53209(17) 0.0251(4) Uani 1 1 d . . .
N1 N -0.3527(3) -0.63582(8) -0.99127(18) 0.0126(4) Uani 1 1 d . . .
N3 N -0.3332(4) -0.52412(9) -0.63898(19) 0.0199(4) Uani 1 1 d . . .
N2 N -0.3306(3) -0.49762(9) -0.76658(19) 0.0176(4) Uani 1 1 d . . .
C17 C -0.3594(4) -0.59256(11) -0.6392(2) 0.0227(5) Uani 1 1 d . . .
H17 H -0.3589 -0.6205 -0.5656 0.027 Uiso 1 1 calc R . .
C10 C -0.4474(3) -0.66690(10) -1.1143(2) 0.0113(4) Uani 1 1 d . . .
H10 H -0.5999 -0.6522 -1.1284 0.014 Uiso 1 1 calc R . .
C6 C -0.4782(4) -0.76823(10) -1.4910(2) 0.0166(4) Uani 1 1 d . . .
C11 C -0.3270(4) -0.64255(10) -1.2345(2) 0.0122(4) Uani 1 1 d . . .
H11 H -0.3630 -0.5956 -1.2456 0.015 Uiso 1 1 calc R . .
C9 C -0.4492(4) -0.74231(10) -1.1065(2) 0.0136(4) Uani 1 1 d . . .
H9A H -0.5441 -0.7565 -1.0391 0.016 Uiso 1 1 calc R . .
H9B H -0.3026 -0.7584 -1.0811 0.016 Uiso 1 1 calc R . .
O2 O -0.2589(4) -0.51401(9) -0.39372(18) 0.0354(5) Uani 1 1 d . . .
N4 N -0.5215(3) -0.84433(8) -1.23582(18) 0.0138(4) Uani 1 1 d . . .
H4A H -0.6042 -0.8586 -1.1727 0.017 Uiso 1 1 calc R . .
H4B H -0.3836 -0.8571 -1.2162 0.017 Uiso 1 1 calc R . .
H4C H -0.5709 -0.8612 -1.3145 0.017 Uiso 1 1 calc R . .
C13 C -0.3921(4) -0.56307(10) -0.9892(2) 0.0143(4) Uani 1 1 d . . .
H13A H -0.5381 -0.5519 -1.0271 0.017 Uiso 1 1 calc R . .
H13B H -0.2847 -0.5391 -1.0363 0.017 Uiso 1 1 calc R . .
C14 C -0.3655(4) -0.55018(11) -0.8417(2) 0.0149(4) Uani 1 1 d . . .
C15 C -0.3857(4) -0.60929(11) -0.7699(2) 0.0192(5) Uani 1 1 d . . .
C8 C -0.5312(3) -0.77091(10) -1.2427(2) 0.0130(4) Uani 1 1 d . . .
H8 H -0.6837 -0.7574 -1.2634 0.016 Uiso 1 1 calc R . .
C3 C -0.6350(6) -0.81569(14) -1.7436(3) 0.0341(7) Uani 1 1 d . . .
H3 H -0.6901 -0.8318 -1.8264 0.041 Uiso 1 1 calc R . .
C2 C -0.4318(6) -0.83416(13) -1.6890(3) 0.0336(6) Uani 1 1 d . . .
H2 H -0.3454 -0.8624 -1.7356 0.040 Uiso 1 1 calc R . .
C4 C -0.7550(5) -0.77271(15) -1.6727(3) 0.0307(6) Uani 1 1 d . . .
C7 C -0.3945(3) -0.74549(10) -1.3530(2) 0.0131(4) Uani 1 1 d . . .
H7 H -0.2415 -0.7590 -1.3343 0.016 Uiso 1 1 calc R . .
C1 C -0.3562(5) -0.81068(11) -1.5647(3) 0.0231(5) Uani 1 1 d . . .
C5 C -0.6832(4) -0.74863(13) -1.5480(3) 0.0237(5) Uani 1 1 d . . .
H5 H -0.7698 -0.7199 -1.5028 0.028 Uiso 1 1 calc R . .
C12 C -0.0762(4) -0.64684(11) -1.2175(2) 0.0175(4) Uani 1 1 d . . .
C16 C -0.4299(4) -0.66488(10) -0.8667(2) 0.0185(5) Uani 1 1 d . . .
H16A H -0.3471 -0.7041 -0.8391 0.022 Uiso 1 1 calc R . .
H16B H -0.5845 -0.6757 -0.8776 0.022 Uiso 1 1 calc R . .
C18 C 0.0669(5) -0.48421(14) -0.5372(3) 0.0362(6) Uani 1 1 d . . .
H18A H 0.1123 -0.5296 -0.5360 0.054 Uiso 1 1 calc R . .
H18B H 0.1497 -0.4605 -0.4672 0.054 Uiso 1 1 calc R . .
H18C H 0.0918 -0.4650 -0.6221 0.054 Uiso 1 1 calc R . .
F6 F -0.3106(2) -0.91021(9) -0.98625(16) 0.0305(4) Uani 1 1 d . . .
O5 O -0.0755(3) -0.86877(8) -1.19099(17) 0.0208(3) Uani 1 1 d . . .
O4 O 0.2142(3) -0.87347(8) -1.03954(17) 0.0219(4) Uani 1 1 d . . .
F7 F -0.1238(3) -0.99216(7) -1.0513(2) 0.0407(4) Uani 1 1 d . . .
F8 F -0.0151(3) -0.94000(11) -0.87336(17) 0.0445(5) Uani 1 1 d . . .
C19 C -0.1066(4) -0.93191(13) -0.9963(3) 0.0230(5) Uani 1 1 d . . .
C20 C 0.0240(4) -0.88571(10) -1.0852(2) 0.0160(4) Uani 1 1 d . . .
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'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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
O3 S1 N3 106.43(10) . . ?
O3 S1 C18 109.32(13) . . ?
N3 S1 C18 103.54(13) . . ?
O2 S1 O3 119.89(12) . . ?
O2 S1 N3 105.56(11) . . ?
O2 S1 C18 110.69(14) . . ?
C11 O1 C7 115.01(16) . . ?
C10 N1 C13 112.51(16) . . ?
C10 N1 C16 113.92(16) . . ?
C16 N1 C13 108.35(16) . . ?
N2 N3 S1 117.09(15) . . ?
N2 N3 C17 113.08(19) . . ?
C17 N3 S1 125.23(17) . . ?
C14 N2 N3 101.66(17) . . ?
N3 C17 H17 127.6 . . ?
C15 C17 N3 104.8(2) . . ?
C15 C17 H17 127.6 . . ?
N1 C10 H10 107.5 . . ?
N1 C10 C11 109.81(16) . . ?
N1 C10 C9 113.01(17) . . ?
C11 C10 H10 107.5 . . ?
C9 C10 H10 107.5 . . ?
C9 C10 C11 111.38(17) . . ?
C1 C6 C7 121.3(2) . . ?
C1 C6 C5 117.6(2) . . ?
C5 C6 C7 121.1(2) . . ?
O1 C11 C10 111.00(16) . . ?
O1 C11 H11 106.3 . . ?
O1 C11 C12 110.60(17) . . ?
C10 C11 H11 106.3 . . ?
C12 C11 C10 115.62(18) . . ?
C12 C11 H11 106.3 . . ?
C10 C9 H9A 109.7 . . ?
C10 C9 H9B 109.7 . . ?
C10 C9 C8 109.62(18) . . ?
H9A C9 H9B 108.2 . . ?
C8 C9 H9A 109.7 . . ?
C8 C9 H9B 109.7 . . ?
H4A N4 H4B 109.5 . . ?
H4A N4 H4C 109.5 . . ?
H4B N4 H4C 109.5 . . ?
C8 N4 H4A 109.5 . . ?
C8 N4 H4B 109.5 . . ?
C8 N4 H4C 109.5 . . ?
N1 C13 H13A 111.7 . . ?
N1 C13 H13B 111.7 . . ?
N1 C13 C14 100.43(17) . . ?
H13A C13 H13B 109.5 . . ?
C14 C13 H13A 111.7 . . ?
C14 C13 H13B 111.7 . . ?
N2 C14 C13 135.1(2) . . ?
N2 C14 C15 114.4(2) . . ?
C15 C14 C13 110.50(19) . . ?
C17 C15 C14 105.9(2) . . ?
C17 C15 C16 145.0(2) . . ?
C14 C15 C16 109.0(2) . . ?
C9 C8 H8 108.8 . . ?
N4 C8 C9 109.12(17) . . ?
N4 C8 H8 108.8 . . ?
N4 C8 C7 110.33(17) . . ?
C7 C8 C9 111.00(17) . . ?
C7 C8 H8 108.8 . . ?
C2 C3 H3 120.9 . . ?
C2 C3 C4 118.2(3) . . ?
C4 C3 H3 120.9 . . ?
C3 C2 H2 120.2 . . ?
C3 C2 C1 119.6(3) . . ?
C1 C2 H2 120.2 . . ?
F2 C4 C3 118.9(3) . . ?
F2 C4 C5 117.9(3) . . ?
C3 C4 C5 123.2(3) . . ?
O1 C7 C6 106.07(17) . . ?
O1 C7 C8 107.87(17) . . ?
O1 C7 H7 109.8 . . ?
C6 C7 C8 113.27(17) . . ?
C6 C7 H7 109.8 . . ?
C8 C7 H7 109.8 . . ?
F1 C1 C6 118.2(2) . . ?
F1 C1 C2 119.2(2) . . ?
C2 C1 C6 122.6(3) . . ?
C6 C5 H5 120.6 . . ?
C4 C5 C6 118.8(3) . . ?
C4 C5 H5 120.6 . . ?
F4 C12 F5 106.83(18) . . ?
F4 C12 F3 106.82(19) . . ?
F4 C12 C11 111.59(17) . . ?
F5 C12 F3 106.12(18) . . ?
F5 C12 C11 110.87(19) . . ?
F3 C12 C11 114.18(18) . . ?
N1 C16 C15 101.15(17) . . ?
N1 C16 H16A 111.5 . . ?
N1 C16 H16B 111.5 . . ?
C15 C16 H16A 111.5 . . ?
C15 C16 H16B 111.5 . . ?
H16A C16 H16B 109.4 . . ?
S1 C18 H18A 109.5 . . ?
S1 C18 H18B 109.5 . . ?
S1 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
F6 C19 F7 106.7(2) . . ?
F6 C19 C20 111.89(19) . . ?
F7 C19 C20 109.8(2) . . ?
F8 C19 F6 107.4(2) . . ?
F8 C19 F7 106.5(2) . . ?
F8 C19 C20 114.1(2) . . ?
O5 C20 O4 130.4(2) . . ?
O5 C20 C19 114.8(2) . . ?
O4 C20 C19 114.8(2) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 O3 1.4280(17) . ?
S1 N3 1.679(2) . ?
S1 O2 1.420(2) . ?
S1 C18 1.760(3) . ?
F4 C12 1.338(3) . ?
F5 C12 1.343(3) . ?
F3 C12 1.347(3) . ?
F2 C4 1.364(4) . ?
O1 C11 1.423(3) . ?
O1 C7 1.444(2) . ?
F1 C1 1.346(3) . ?
N1 C10 1.462(3) . ?
N1 C13 1.493(2) . ?
N1 C16 1.492(3) . ?
N3 N2 1.389(3) . ?
N3 C17 1.395(3) . ?
N2 C14 1.311(3) . ?
C17 H17 0.9300 . ?
C17 C15 1.350(3) . ?
C10 H10 0.9800 . ?
C10 C11 1.544(3) . ?
C10 C9 1.529(3) . ?
C6 C7 1.508(3) . ?
C6 C1 1.390(3) . ?
C6 C5 1.395(4) . ?
C11 H11 0.9800 . ?
C11 C12 1.535(3) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C9 C8 1.530(3) . ?
N4 H4A 0.8900 . ?
N4 H4B 0.8900 . ?
N4 H4C 0.8900 . ?
N4 C8 1.489(3) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C13 C14 1.497(3) . ?
C14 C15 1.407(3) . ?
C15 C16 1.497(3) . ?
C8 H8 0.9800 . ?
C8 C7 1.529(3) . ?
C3 H3 0.9300 . ?
C3 C2 1.371(5) . ?
C3 C4 1.374(5) . ?
C2 H2 0.9300 . ?
C2 C1 1.379(4) . ?
C4 C5 1.381(4) . ?
C7 H7 0.9800 . ?
C5 H5 0.9300 . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
F6 C19 1.336(3) . ?
O5 C20 1.229(3) . ?
O4 C20 1.242(3) . ?
F7 C19 1.340(3) . ?
F8 C19 1.323(3) . ?
C19 C20 1.557(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
S1 N3 N2 C14 160.05(16) . . . . ?
S1 N3 C17 C15 -158.32(19) . . . . ?
F2 C4 C5 C6 -179.4(2) . . . . ?
O1 C11 C12 F4 151.69(18) . . . . ?
O1 C11 C12 F5 32.7(2) . . . . ?
O1 C11 C12 F3 -87.1(2) . . . . ?
O3 S1 N3 N2 45.7(2) . . . . ?
O3 S1 N3 C17 -160.1(2) . . . . ?
N1 C10 C11 O1 177.37(16) . . . . ?
N1 C10 C11 C12 50.3(2) . . . . ?
N1 C10 C9 C8 -174.92(17) . . . . ?
N1 C13 C14 N2 162.3(3) . . . . ?
N1 C13 C14 C15 -18.4(2) . . . . ?
N3 N2 C14 C13 177.9(2) . . . . ?
N3 N2 C14 C15 -1.3(3) . . . . ?
N3 C17 C15 C14 2.2(3) . . . . ?
N3 C17 C15 C16 -176.7(3) . . . . ?
N2 N3 C17 C15 -3.3(3) . . . . ?
N2 C14 C15 C17 -0.6(3) . . . . ?
N2 C14 C15 C16 178.7(2) . . . . ?
C17 N3 N2 C14 2.8(3) . . . . ?
C17 C15 C16 N1 -161.6(4) . . . . ?
C10 N1 C13 C14 158.06(17) . . . . ?
C10 N1 C16 C15 -157.90(18) . . . . ?
C10 C11 C12 F4 -81.1(2) . . . . ?
C10 C11 C12 F5 159.96(17) . . . . ?
C10 C11 C12 F3 40.2(3) . . . . ?
C10 C9 C8 N4 177.16(17) . . . . ?
C10 C9 C8 C7 55.4(2) . . . . ?
C11 O1 C7 C6 -176.96(16) . . . . ?
C11 O1 C7 C8 61.4(2) . . . . ?
C11 C10 C9 C8 -50.7(2) . . . . ?
C9 C10 C11 O1 51.4(2) . . . . ?
C9 C10 C11 C12 -75.6(2) . . . . ?
C9 C8 C7 O1 -58.8(2) . . . . ?
C9 C8 C7 C6 -175.84(17) . . . . ?
O2 S1 N3 N2 174.13(18) . . . . ?
O2 S1 N3 C17 -31.7(3) . . . . ?
N4 C8 C7 O1 -179.84(17) . . . . ?
N4 C8 C7 C6 63.1(2) . . . . ?
C13 N1 C10 C11 66.5(2) . . . . ?
C13 N1 C10 C9 -168.43(18) . . . . ?
C13 N1 C16 C15 -31.9(2) . . . . ?
C13 C14 C15 C17 180.0(2) . . . . ?
C13 C14 C15 C16 -0.7(3) . . . . ?
C14 C15 C16 N1 19.5(3) . . . . ?
C3 C2 C1 F1 179.0(2) . . . . ?
C3 C2 C1 C6 -0.2(4) . . . . ?
C3 C4 C5 C6 0.5(4) . . . . ?
C2 C3 C4 F2 178.3(2) . . . . ?
C2 C3 C4 C5 -1.7(4) . . . . ?
C4 C3 C2 C1 1.5(4) . . . . ?
C7 O1 C11 C10 -58.2(2) . . . . ?
C7 O1 C11 C12 71.6(2) . . . . ?
C7 C6 C1 F1 -1.7(3) . . . . ?
C7 C6 C1 C2 177.6(2) . . . . ?
C7 C6 C5 C4 -177.8(2) . . . . ?
C1 C6 C7 O1 127.8(2) . . . . ?
C1 C6 C7 C8 -114.1(2) . . . . ?
C1 C6 C5 C4 0.7(3) . . . . ?
C5 C6 C7 O1 -53.8(3) . . . . ?
C5 C6 C7 C8 64.4(3) . . . . ?
C5 C6 C1 F1 179.8(2) . . . . ?
C5 C6 C1 C2 -0.9(4) . . . . ?
C16 N1 C10 C11 -169.64(17) . . . . ?
C16 N1 C10 C9 -44.6(2) . . . . ?
C16 N1 C13 C14 31.2(2) . . . . ?
C18 S1 N3 N2 -69.5(2) . . . . ?
C18 S1 N3 C17 84.7(2) . . . . ?
F6 C19 C20 O5 -46.0(3) . . . . ?
F6 C19 C20 O4 136.0(2) . . . . ?
F7 C19 C20 O5 72.3(3) . . . . ?
F7 C19 C20 O4 -105.7(2) . . . . ?
F8 C19 C20 O5 -168.2(2) . . . . ?
F8 C19 C20 O4 13.8(3) . . . . ?
