#------------------------------------------------------------------------------
#$Date: 2020-09-09 04:02:55 +0300 (Wed, 09 Sep 2020) $
#$Revision: 256236 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/55/90/1559016.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_1559016
loop_
_publ_author_name
'Lai, Zengwei'
'Zhang, Renwei'
'Feng, Qiang'
'Sun, Jianwei'
_publ_section_title
;
 3-Aminooxetanes: versatile 1,3-amphoteric molecules for intermolecular
 annulation reactions
;
_journal_name_full               'Chemical Science'
_journal_paper_doi               10.1039/D0SC04254D
_journal_year                    2020
_chemical_formula_moiety         'C17 H17 F N2 O S'
_chemical_formula_sum            'C17 H17 F N2 O S'
_chemical_formula_weight         316.38
_chemical_name_systematic
(Z)-(3-Benzyl-2-((2-fluorophenyl)imino)thiazolidin-4-yl)methanol
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2020-03-01
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2020-03-01 deposited with the CCDC.	2020-08-31 downloaded from the CCDC.
;
_cell_angle_alpha                110.620(4)
_cell_angle_beta                 90.804(3)
_cell_angle_gamma                101.885(3)
_cell_formula_units_Z            4
_cell_length_a                   9.7070(3)
_cell_length_b                   12.3991(6)
_cell_length_c                   13.7578(6)
_cell_measurement_reflns_used    6199
_cell_measurement_temperature    102(3)
_cell_measurement_theta_max      75.4600
_cell_measurement_theta_min      4.6520
_cell_volume                     1509.77(12)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      100.15
_diffrn_detector_area_resol_mean 10.3587
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.983
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measurement_details
;
#__ type_ start__ end____ width___ exp.time_
  1 omega   57.00  141.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      110.5703  -61.0000   30.0000 84

#__ type_ start__ end____ width___ exp.time_
  2 omega  -49.00   35.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.9453   37.0000    0.0000 84

#__ type_ start__ end____ width___ exp.time_
  3 omega  -96.00   -2.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.9453  125.0000   60.0000 94

#__ type_ start__ end____ width___ exp.time_
  4 omega -115.00  -11.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.9453  -57.0000 -150.0000 104

#__ type_ start__ end____ width___ exp.time_
  5 omega   31.00  108.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      110.5703  -94.0000  -30.0000 77

#__ type_ start__ end____ width___ exp.time_
  6 omega   81.00  178.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      110.5703   30.0000  120.0000 97

#__ type_ start__ end____ width___ exp.time_
  7 omega   73.00  112.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      110.5703 -111.0000   90.0000 39

#__ type_ start__ end____ width___ exp.time_
  8 omega   42.00   90.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      110.5703  -30.0000  150.0000 48

#__ type_ start__ end____ width___ exp.time_
  9 omega   38.00   67.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      110.5703 -111.0000   90.0000 29

#__ type_ start__ end____ width___ exp.time_
 10 omega   33.00   87.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      110.5703  -30.0000  -60.0000 54

#__ type_ start__ end____ width___ exp.time_
 11 omega  127.00  178.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      110.5703   30.0000 -150.0000 51

#__ type_ start__ end____ width___ exp.time_
 12 omega   80.00  124.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      110.5703   30.0000 -150.0000 44

#__ type_ start__ end____ width___ exp.time_
 13 omega   33.00   83.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      110.5703  -30.0000 -150.0000 50

#__ type_ start__ end____ width___ exp.time_
 14 omega   51.00  103.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      110.5703  -94.0000 -120.0000 52

#__ type_ start__ end____ width___ exp.time_
 15 omega   39.00  101.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      110.5703 -111.0000 -150.0000 62
;
_diffrn_measurement_device       'kappa diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0147
_diffrn_reflns_av_unetI/netI     0.0198
_diffrn_reflns_Laue_measured_fraction_full 0.983
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            8240
_diffrn_reflns_point_group_measured_fraction_full 0.983
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_theta_full        67.497
_diffrn_reflns_theta_max         67.497
_diffrn_reflns_theta_min         4.171
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_current           0.80
_diffrn_source_power             0.040
_diffrn_source_target            Cu
_diffrn_source_voltage           50
_exptl_absorpt_coefficient_mu    2.029
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.88879
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.392
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             664
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: diethyl ether'
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.343
_refine_diff_density_min         -0.213
_refine_diff_density_rms         0.040
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     399
_refine_ls_number_reflns         5347
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.023
_refine_ls_R_factor_all          0.0287
_refine_ls_R_factor_gt           0.0276
_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)+(0.0360P)²+0.5130P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0695
_refine_ls_wR_factor_ref         0.0705
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5108
_reflns_number_total             5347
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d0sc04254d2.cif
_cod_data_source_block           lai1cult
_cod_database_code               1559016
_shelx_shelxl_version_number     2014/7
_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.
;
_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 O(H) groups
2.a Ternary CH refined with riding coordinates:
 C3(H3), C3A(H3A)
2.b Secondary CH2 refined with riding coordinates:
 C4(H4a,H4b), C5(H5a,H5b), C10(H10a,H10b), C4A(H4Aa,H4Ab), C5A(H5Aa,H5Ab),
 C10A(H10c,H10d)
2.c Aromatic/amide H refined with riding coordinates:
 C12(H12), C13(H13), C14(H14), C15(H15), C16(H16), C23(H23), C24(H24),
 C25(H25), C26(H26), C12A(H12A), C13A(H13A), C14A(H14A), C15A(H15A), C16A(H16A),
  C23A(H23A), C24A(H24A), C25A(H25A), C26A(H26A)
2.d Idealised tetrahedral OH refined as rotating group:
 O1(H1), O1A(H1A)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.79193(3) 0.71421(3) 0.42458(2) 0.01777(8) Uani 1 1 d . . . . .
F1 F 0.41098(8) 0.57360(6) 0.24960(6) 0.02428(17) Uani 1 1 d . . . . .
O1 O 0.76740(9) 0.41469(7) 0.52866(7) 0.01963(18) Uani 1 1 d . . . . .
H1 H 0.6826 0.3876 0.5348 0.029 Uiso 1 1 calc GR . . . .
N1 N 0.51347(10) 0.69729(9) 0.45607(8) 0.0166(2) Uani 1 1 d . . . . .
N2 N 0.65265(10) 0.62829(9) 0.55103(8) 0.0152(2) Uani 1 1 d . . . . .
C1 C 0.63319(12) 0.67868(10) 0.48010(9) 0.0147(2) Uani 1 1 d . . . . .
C3 C 0.80060(12) 0.63022(10) 0.57812(9) 0.0167(2) Uani 1 1 d . . . . .
H3 H 0.8422 0.7058 0.6372 0.020 Uiso 1 1 calc R . . . .
C4 C 0.87575(13) 0.62930(11) 0.48147(10) 0.0192(2) Uani 1 1 d . . . . .
H4A H 0.8652 0.5473 0.4315 0.023 Uiso 1 1 calc R . . . .
H4B H 0.9778 0.6660 0.5007 0.023 Uiso 1 1 calc R . . . .
C5 C 0.81667(13) 0.52662(11) 0.60912(10) 0.0186(2) Uani 1 1 d . . . . .
H5A H 0.9178 0.5360 0.6299 0.022 Uiso 1 1 calc R . . . .
H5B H 0.7639 0.5290 0.6706 0.022 Uiso 1 1 calc R . . . .
C10 C 0.54787(12) 0.62141(10) 0.62492(9) 0.0155(2) Uani 1 1 d . . . . .
H10A H 0.5495 0.5516 0.6438 0.019 Uiso 1 1 calc R . . . .
H10B H 0.4529 0.6088 0.5900 0.019 Uiso 1 1 calc R . . . .
C11 C 0.57000(12) 0.72986(10) 0.72422(9) 0.0152(2) Uani 1 1 d . . . . .
C12 C 0.65290(13) 0.83881(11) 0.73230(10) 0.0185(2) Uani 1 1 d . . . . .
H12 H 0.6975 0.8477 0.6737 0.022 Uiso 1 1 calc R . . . .
C13 C 0.67089(13) 0.93493(11) 0.82578(10) 0.0217(3) Uani 1 1 d . . . . .
H13 H 0.7299 1.0086 0.8313 0.026 Uiso 1 1 calc R . . . .
C14 C 0.60326(14) 0.92397(11) 0.91106(10) 0.0228(3) Uani 1 1 d . . . . .
H14 H 0.6158 0.9898 0.9749 0.027 Uiso 1 1 calc R . . . .
C15 C 0.51710(13) 0.81623(12) 0.90255(10) 0.0209(3) Uani 1 1 d . . . . .
H15 H 0.4684 0.8087 0.9600 0.025 Uiso 1 1 calc R . . . .
C16 C 0.50203(12) 0.71946(11) 0.81014(10) 0.0175(2) Uani 1 1 d . . . . .
H16 H 0.4448 0.6454 0.8054 0.021 Uiso 1 1 calc R . . . .
C21 C 0.51243(12) 0.75507(11) 0.38382(9) 0.0167(2) Uani 1 1 d . . . . .
C22 C 0.45868(13) 0.69298(11) 0.28058(10) 0.0182(2) Uani 1 1 d . . . . .
C23 C 0.45061(13) 0.74509(12) 0.20777(10) 0.0228(3) Uani 1 1 d . . . . .
H23 H 0.4136 0.6989 0.1377 0.027 Uiso 1 1 calc R . . . .
C24 C 0.49810(15) 0.86687(13) 0.23972(11) 0.0268(3) Uani 1 1 d . . . . .
H24 H 0.4954 0.9051 0.1911 0.032 Uiso 1 1 calc R . . . .
C25 C 0.54967(15) 0.93277(12) 0.34301(11) 0.0265(3) Uani 1 1 d . . . . .
H25 H 0.5802 1.0163 0.3651 0.032 Uiso 1 1 calc R . . . .
C26 C 0.55688(13) 0.87737(11) 0.41428(10) 0.0220(3) Uani 1 1 d . . . . .
H26 H 0.5926 0.9235 0.4846 0.026 Uiso 1 1 calc R . . . .
S1A S 0.18959(3) 0.28531(3) 0.06976(2) 0.01876(8) Uani 1 1 d . . . . .
F1A F -0.13785(9) 0.41075(7) 0.24464(6) 0.02595(17) Uani 1 1 d . . . . .
O1A O 0.30469(9) 0.58351(7) -0.03646(7) 0.02001(18) Uani 1 1 d . . . . .
H1A H 0.2328 0.6095 -0.0420 0.030 Uiso 1 1 calc GR . . . .
N1A N -0.08339(11) 0.29840(9) 0.04209(8) 0.0176(2) Uani 1 1 d . . . . .
N2A N 0.08258(10) 0.36797(9) -0.05634(8) 0.0161(2) Uani 1 1 d . . . . .
C1A C 0.04378(13) 0.31803(10) 0.01575(9) 0.0155(2) Uani 1 1 d . . . . .
C3A C 0.22810(13) 0.36789(11) -0.08507(9) 0.0174(2) Uani 1 1 d . . . . .
H3A H 0.2279 0.2925 -0.1442 0.021 Uiso 1 1 calc R . . . .
C4A C 0.31137(13) 0.37027(11) 0.01054(10) 0.0198(3) Uani 1 1 d . . . . .
H4AA H 0.3459 0.4526 0.0599 0.024 Uiso 1 1 calc R . . . .
H4AB H 0.3936 0.3343 -0.0099 0.024 Uiso 1 1 calc R . . . .
C5A C 0.29291(13) 0.47173(11) -0.11705(9) 0.0190(2) Uani 1 1 d . . . . .
H5AA H 0.3882 0.4639 -0.1390 0.023 Uiso 1 1 calc R . . . .
H5AB H 0.2341 0.4682 -0.1779 0.023 Uiso 1 1 calc R . . . .
C10A C -0.02472(13) 0.37145(10) -0.13018(9) 0.0168(2) Uani 1 1 d . . . . .
H10C H 0.0078 0.4429 -0.1477 0.020 Uiso 1 1 calc R . . . .
H10D H -0.1130 0.3790 -0.0957 0.020 Uiso 1 1 calc R . . . .
C11A C -0.05780(12) 0.26382(10) -0.23082(9) 0.0159(2) Uani 1 1 d . . . . .
C12A C -0.03391(13) 0.15457(11) -0.23767(10) 0.0200(3) Uani 1 1 d . . . . .
H12A H 0.0054 0.1458 -0.1780 0.024 Uiso 1 1 calc R . . . .
C13A C -0.06715(14) 0.05837(11) -0.33104(11) 0.0237(3) Uani 1 1 d . . . . .
H13A H -0.0489 -0.0154 -0.3351 0.028 Uiso 1 1 calc R . . . .
C14A C -0.12677(14) 0.06904(12) -0.41845(10) 0.0243(3) Uani 1 1 d . . . . .
H14A H -0.1491 0.0031 -0.4823 0.029 Uiso 1 1 calc R . . . .
C15A C -0.15355(13) 0.17723(12) -0.41168(10) 0.0228(3) Uani 1 1 d . . . . .
H15A H -0.1963 0.1850 -0.4707 0.027 Uiso 1 1 calc R . . . .
C16A C -0.11790(12) 0.27395(11) -0.31879(10) 0.0186(2) Uani 1 1 d . . . . .
H16A H -0.1347 0.3480 -0.3152 0.022 Uiso 1 1 calc R . . . .
C21A C -0.10777(12) 0.23751(11) 0.11222(9) 0.0177(2) Uani 1 1 d . . . . .
C22A C -0.13914(13) 0.29379(11) 0.21339(10) 0.0190(2) Uani 1 1 d . . . . .
C23A C -0.17059(13) 0.23797(12) 0.28362(10) 0.0234(3) Uani 1 1 d . . . . .
H23A H -0.1914 0.2801 0.3521 0.028 Uiso 1 1 calc R . . . .
C24A C -0.17096(14) 0.11845(13) 0.25156(11) 0.0273(3) Uani 1 1 d . . . . .
H24A H -0.1914 0.0778 0.2985 0.033 Uiso 1 1 calc R . . . .
C25A C -0.14144(15) 0.05832(12) 0.15098(12) 0.0281(3) Uani 1 1 d . . . . .
H25A H -0.1428 -0.0237 0.1291 0.034 Uiso 1 1 calc R . . . .
C26A C -0.10988(14) 0.11728(12) 0.08218(10) 0.0229(3) Uani 1 1 d . . . . .
H26A H -0.0894 0.0751 0.0136 0.028 Uiso 1 1 calc R . . . .
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
C1 S1 C4 90.70(6) . . ?
C5 O1 H1 109.5 . . ?
C1 N1 C21 116.85(10) . . ?
C1 N2 C3 115.34(10) . . ?
C1 N2 C10 119.91(10) . . ?
C10 N2 C3 119.75(9) . . ?
N1 C1 S1 124.50(9) . . ?
N1 C1 N2 123.92(11) . . ?
N2 C1 S1 111.58(8) . . ?
N2 C3 H3 108.9 . . ?
N2 C3 C4 105.19(9) . . ?
N2 C3 C5 113.29(10) . . ?
C4 C3 H3 108.9 . . ?
C4 C3 C5 111.39(10) . . ?
C5 C3 H3 108.9 . . ?
S1 C4 H4A 110.6 . . ?
S1 C4 H4B 110.6 . . ?
C3 C4 S1 105.90(8) . . ?
C3 C4 H4A 110.6 . . ?
C3 C4 H4B 110.6 . . ?
H4A C4 H4B 108.7 . . ?
O1 C5 C3 113.66(10) . . ?
O1 C5 H5A 108.8 . . ?
O1 C5 H5B 108.8 . . ?
C3 C5 H5A 108.8 . . ?
C3 C5 H5B 108.8 . . ?
H5A C5 H5B 107.7 . . ?
N2 C10 H10A 108.6 . . ?
N2 C10 H10B 108.6 . . ?
N2 C10 C11 114.48(10) . . ?
H10A C10 H10B 107.6 . . ?
C11 C10 H10A 108.6 . . ?
C11 C10 H10B 108.6 . . ?
C12 C11 C10 122.79(11) . . ?
C12 C11 C16 118.99(11) . . ?
C16 C11 C10 118.21(11) . . ?
C11 C12 H12 119.9 . . ?
C11 C12 C13 120.30(12) . . ?
C13 C12 H12 119.9 . . ?
C12 C13 H13 119.8 . . ?
C14 C13 C12 120.42(12) . . ?
C14 C13 H13 119.8 . . ?
C13 C14 H14 120.2 . . ?
C13 C14 C15 119.53(12) . . ?
C15 C14 H14 120.2 . . ?
C14 C15 H15 120.0 . . ?
C14 C15 C16 120.07(12) . . ?
C16 C15 H15 120.0 . . ?
C11 C16 H16 119.7 . . ?
C15 C16 C11 120.65(11) . . ?
C15 C16 H16 119.7 . . ?
C22 C21 N1 121.34(11) . . ?
C22 C21 C26 116.85(11) . . ?
C26 C21 N1 121.69(11) . . ?
F1 C22 C21 117.95(11) . . ?
F1 C22 C23 118.20(11) . . ?
C23 C22 C21 123.85(12) . . ?
C22 C23 H23 120.9 . . ?
C22 C23 C24 118.12(12) . . ?
C24 C23 H23 120.9 . . ?
C23 C24 H24 120.0 . . ?
C23 C24 C25 119.90(12) . . ?
C25 C24 H24 120.0 . . ?
C24 C25 H25 119.8 . . ?
C26 C25 C24 120.48(12) . . ?
C26 C25 H25 119.8 . . ?
C21 C26 H26 119.6 . . ?
C25 C26 C21 120.77(12) . . ?
C25 C26 H26 119.6 . . ?
C1A S1A C4A 90.78(6) . . ?
C5A O1A H1A 109.5 . . ?
C1A N1A C21A 116.63(10) . . ?
C1A N2A C3A 115.10(10) . . ?
C1A N2A C10A 120.09(10) . . ?
C10A N2A C3A 119.58(10) . . ?
N1A C1A S1A 124.36(9) . . ?
N1A C1A N2A 123.95(11) . . ?
N2A C1A S1A 111.69(9) . . ?
N2A C3A H3A 108.9 . . ?
N2A C3A C4A 105.44(9) . . ?
N2A C3A C5A 113.05(10) . . ?
C4A C3A H3A 108.9 . . ?
C4A C3A C5A 111.47(10) . . ?
C5A C3A H3A 108.9 . . ?
S1A C4A H4AA 110.5 . . ?
S1A C4A H4AB 110.5 . . ?
C3A C4A S1A 105.97(8) . . ?
C3A C4A H4AA 110.5 . . ?
C3A C4A H4AB 110.5 . . ?
H4AA C4A H4AB 108.7 . . ?
O1A C5A C3A 113.50(10) . . ?
O1A C5A H5AA 108.9 . . ?
O1A C5A H5AB 108.9 . . ?
C3A C5A H5AA 108.9 . . ?
C3A C5A H5AB 108.9 . . ?
H5AA C5A H5AB 107.7 . . ?
N2A C10A H10C 108.7 . . ?
N2A C10A H10D 108.7 . . ?
N2A C10A C11A 114.41(10) . . ?
H10C C10A H10D 107.6 . . ?
C11A C10A H10C 108.7 . . ?
C11A C10A H10D 108.7 . . ?
C12A C11A C10A 122.50(11) . . ?
C12A C11A C16A 118.68(11) . . ?
C16A C11A C10A 118.79(11) . . ?
C11A C12A H12A 119.8 . . ?
C13A C12A C11A 120.48(12) . . ?
C13A C12A H12A 119.8 . . ?
C12A C13A H13A 119.7 . . ?
C14A C13A C12A 120.57(12) . . ?
C14A C13A H13A 119.7 . . ?
C13A C14A H14A 120.4 . . ?
C13A C14A C15A 119.29(12) . . ?
C15A C14A H14A 120.4 . . ?
C14A C15A H15A 120.0 . . ?
C16A C15A C14A 120.08(12) . . ?
C16A C15A H15A 120.0 . . ?
C11A C16A H16A 119.6 . . ?
C15A C16A C11A 120.87(12) . . ?
C15A C16A H16A 119.6 . . ?
C22A C21A N1A 121.11(11) . . ?
C22A C21A C26A 116.62(11) . . ?
C26A C21A N1A 122.17(11) . . ?
F1A C22A C21A 117.84(11) . . ?
F1A C22A C23A 118.30(11) . . ?
C23A C22A C21A 123.86(12) . . ?
C22A C23A H23A 120.9 . . ?
C22A C23A C24A 118.13(12) . . ?
C24A C23A H23A 120.9 . . ?
C23A C24A H24A 120.0 . . ?
C25A C24A C23A 120.05(12) . . ?
C25A C24A H24A 120.0 . . ?
C24A C25A H25A 119.8 . . ?
C24A C25A C26A 120.37(13) . . ?
C26A C25A H25A 119.8 . . ?
C21A C26A H26A 119.5 . . ?
C25A C26A C21A 120.97(12) . . ?
C25A C26A H26A 119.5 . . ?
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 C1 1.7727(12) . ?
S1 C4 1.8163(12) . ?
F1 C22 1.3619(14) . ?
O1 H1 0.8400 . ?
O1 C5 1.4177(15) . ?
N1 C1 1.2910(16) . ?
N1 C21 1.4162(15) . ?
N2 C1 1.3604(15) . ?
N2 C3 1.4719(15) . ?
N2 C10 1.4594(15) . ?
C3 H3 1.0000 . ?
C3 C4 1.5232(16) . ?
C3 C5 1.5240(16) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C10 C11 1.5164(16) . ?
C11 C12 1.3888(17) . ?
C11 C16 1.3941(17) . ?
C12 H12 0.9500 . ?
C12 C13 1.3905(18) . ?
C13 H13 0.9500 . ?
C13 C14 1.3869(19) . ?
C14 H14 0.9500 . ?
C14 C15 1.3873(19) . ?
C15 H15 0.9500 . ?
C15 C16 1.3876(18) . ?
C16 H16 0.9500 . ?
C21 C22 1.3878(18) . ?
C21 C26 1.3925(18) . ?
C22 C23 1.3789(18) . ?
C23 H23 0.9500 . ?
C23 C24 1.388(2) . ?
C24 H24 0.9500 . ?
C24 C25 1.390(2) . ?
C25 H25 0.9500 . ?
C25 C26 1.3895(19) . ?
C26 H26 0.9500 . ?
S1A C1A 1.7718(12) . ?
S1A C4A 1.8137(12) . ?
F1A C22A 1.3569(15) . ?
O1A H1A 0.8400 . ?
O1A C5A 1.4184(15) . ?
N1A C1A 1.2904(16) . ?
N1A C21A 1.4153(16) . ?
N2A C1A 1.3624(16) . ?
N2A C3A 1.4722(15) . ?
N2A C10A 1.4624(15) . ?
C3A H3A 1.0000 . ?
C3A C4A 1.5223(17) . ?
C3A C5A 1.5233(17) . ?
C4A H4AA 0.9900 . ?
C4A H4AB 0.9900 . ?
C5A H5AA 0.9900 . ?
C5A H5AB 0.9900 . ?
C10A H10C 0.9900 . ?
C10A H10D 0.9900 . ?
C10A C11A 1.5201(16) . ?
C11A C12A 1.3921(17) . ?
C11A C16A 1.3921(17) . ?
C12A H12A 0.9500 . ?
C12A C13A 1.3884(19) . ?
C13A H13A 0.9500 . ?
C13A C14A 1.387(2) . ?
C14A H14A 0.9500 . ?
C14A C15A 1.390(2) . ?
C15A H15A 0.9500 . ?
C15A C16A 1.3887(18) . ?
C16A H16A 0.9500 . ?
C21A C22A 1.3900(18) . ?
C21A C26A 1.3953(18) . ?
C22A C23A 1.3777(18) . ?
C23A H23A 0.9500 . ?
C23A C24A 1.389(2) . ?
C24A H24A 0.9500 . ?
C24A C25A 1.388(2) . ?
C25A H25A 0.9500 . ?
C25A C26A 1.3883(19) . ?
C26A H26A 0.9500 . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O1 H1 N1 0.84 2.01 2.8403(13) 172.7 2_666
O1A H1A N1A 0.84 2.02 2.8522(13) 169.5 2_565
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 C22 C23 C24 179.43(11) . . . . ?
N1 C21 C22 F1 -2.16(17) . . . . ?
N1 C21 C22 C23 177.74(11) . . . . ?
N1 C21 C26 C25 -177.39(11) . . . . ?
N2 C3 C4 S1 34.46(11) . . . . ?
N2 C3 C5 O1 61.62(13) . . . . ?
N2 C10 C11 C12 18.72(16) . . . . ?
N2 C10 C11 C16 -162.33(10) . . . . ?
C1 S1 C4 C3 -26.64(8) . . . . ?
C1 N1 C21 C22 103.47(13) . . . . ?
C1 N1 C21 C26 -80.61(14) . . . . ?
C1 N2 C3 C4 -28.69(13) . . . . ?
C1 N2 C3 C5 -150.58(10) . . . . ?
C1 N2 C10 C11 -86.98(13) . . . . ?
C3 N2 C1 S1 8.74(12) . . . . ?
C3 N2 C1 N1 -171.70(11) . . . . ?
C3 N2 C10 C11 66.85(13) . . . . ?
C4 S1 C1 N1 -168.22(11) . . . . ?
C4 S1 C1 N2 11.33(9) . . . . ?
C4 C3 C5 O1 -56.74(13) . . . . ?
C5 C3 C4 S1 157.57(8) . . . . ?
C10 N2 C1 S1 163.68(8) . . . . ?
C10 N2 C1 N1 -16.77(17) . . . . ?
C10 N2 C3 C4 176.33(10) . . . . ?
C10 N2 C3 C5 54.44(14) . . . . ?
C10 C11 C12 C13 -179.19(11) . . . . ?
C10 C11 C16 C15 -179.18(11) . . . . ?
C11 C12 C13 C14 -1.75(19) . . . . ?
C12 C11 C16 C15 -0.19(18) . . . . ?
C12 C13 C14 C15 -0.08(19) . . . . ?
C13 C14 C15 C16 1.76(19) . . . . ?
C14 C15 C16 C11 -1.63(18) . . . . ?
C16 C11 C12 C13 1.87(18) . . . . ?
C21 N1 C1 S1 -3.03(15) . . . . ?
C21 N1 C1 N2 177.47(10) . . . . ?
C21 C22 C23 C24 -0.47(19) . . . . ?
C22 C21 C26 C25 -1.30(18) . . . . ?
C22 C23 C24 C25 -1.05(19) . . . . ?
C23 C24 C25 C26 1.4(2) . . . . ?
C24 C25 C26 C21 -0.1(2) . . . . ?
C26 C21 C22 F1 -178.27(10) . . . . ?
C26 C21 C22 C23 1.63(18) . . . . ?
F1A C22A C23A C24A -179.61(11) . . . . ?
N1A C21A C22A F1A -3.62(17) . . . . ?
N1A C21A C22A C23A 176.74(11) . . . . ?
N1A C21A C26A C25A -176.56(12) . . . . ?
N2A C3A C4A S1A 34.10(11) . . . . ?
N2A C3A C5A O1A 61.70(13) . . . . ?
N2A C10A C11A C12A 23.80(16) . . . . ?
N2A C10A C11A C16A -158.03(10) . . . . ?
C1A S1A C4A C3A -26.32(9) . . . . ?
C1A N1A C21A C22A 111.94(13) . . . . ?
C1A N1A C21A C26A -71.89(15) . . . . ?
C1A N2A C3A C4A -28.32(13) . . . . ?
C1A N2A C3A C5A -150.34(10) . . . . ?
C1A N2A C10A C11A -89.30(13) . . . . ?
C3A N2A C1A S1A 8.59(12) . . . . ?
C3A N2A C1A N1A -172.15(11) . . . . ?
C3A N2A C10A C11A 63.91(14) . . . . ?
C4A S1A C1A N1A -168.05(11) . . . . ?
C4A S1A C1A N2A 11.21(9) . . . . ?
C4A C3A C5A O1A -56.87(13) . . . . ?
C5A C3A C4A S1A 157.13(8) . . . . ?
C10A N2A C1A S1A 162.95(8) . . . . ?
C10A N2A C1A N1A -17.80(17) . . . . ?
C10A N2A C3A C4A 177.19(10) . . . . ?
C10A N2A C3A C5A 55.17(14) . . . . ?
C10A C11A C12A C13A 179.33(11) . . . . ?
C10A C11A C16A C15A -178.22(11) . . . . ?
C11A C12A C13A C14A -1.07(19) . . . . ?
C12A C11A C16A C15A 0.02(18) . . . . ?
C12A C13A C14A C15A -0.22(19) . . . . ?
C13A C14A C15A C16A 1.39(19) . . . . ?
C14A C15A C16A C11A -1.30(19) . . . . ?
C16A C11A C12A C13A 1.16(18) . . . . ?
C21A N1A C1A S1A -5.61(15) . . . . ?
C21A N1A C1A N2A 175.23(11) . . . . ?
C21A C22A C23A C24A 0.02(19) . . . . ?
C22A C21A C26A C25A -0.22(19) . . . . ?
C22A C23A C24A C25A -0.6(2) . . . . ?
C23A C24A C25A C26A 0.7(2) . . . . ?
C24A C25A C26A C21A -0.3(2) . . . . ?
C26A C21A C22A F1A 180.00(10) . . . . ?
C26A C21A C22A C23A 0.37(18) . . . . ?
