# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2021

####################################################################### 
# 
# 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_z
_database_code_depnum_ccdc_archive 'CCDC 2113410'
loop_
_audit_author_name
_audit_author_address
'Andrei Churakov'
;Institute of General and Inorganic Chemistry RAS
Russia
;
_audit_update_record             
;
2021-10-01 deposited with the CCDC.	2021-11-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         
;
C22 H18 F2 N5 O S, C7 H7 O3 S, 0.212(C2 H3 N)
;
_chemical_formula_sum            'C29.42 H25.64 F2 N5.21 O4 S2'
_chemical_formula_weight         618.35

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'
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'
F F 0.0171 0.0103 '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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           5
_space_group_name_H-M_alt        'C 2'
_space_group_name_Hall           'C 2y'

_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'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z'

_cell_length_a                   29.078(4)
_cell_length_b                   8.7230(12)
_cell_length_c                   12.0174(16)
_cell_angle_alpha                90
_cell_angle_beta                 93.915(6)
_cell_angle_gamma                90
_cell_volume                     3041.1(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    3424
_cell_measurement_theta_min      2.438
_cell_measurement_theta_max      26.249

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.351
_exptl_crystal_F_000             1283
_exptl_transmission_factor_min   0.5291
_exptl_transmission_factor_max   0.9281
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.030
_exptl_absorpt_coefficient_mu    0.231
_shelx_estimated_absorpt_T_min   0.913
_shelx_estimated_absorpt_T_max   0.993
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   'SADABS (Bruker, 2016)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            8833
_diffrn_reflns_av_unetI/netI     0.0782
_diffrn_reflns_av_R_equivalents  0.0415
_diffrn_reflns_limit_h_min       -35
_diffrn_reflns_limit_h_max       35
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.277
_diffrn_reflns_theta_max         25.997
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measured_fraction_theta_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.837
_diffrn_reflns_point_group_measured_fraction_full 0.838
_reflns_number_total             5000
_reflns_number_gt                4268
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.579
_reflns_Friedel_fraction_max     0.660
_reflns_Friedel_fraction_full    0.660

_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       'APEX3 (Bruker, 2018)'
_computing_cell_refinement       'SAINT (Bruker, 2018)'
_computing_data_reduction        'SAINT (Bruker, 2018)'
_computing_structure_solution    'SHELXT (Sheldrick, 2016)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_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)+(0.0789P)²+0.7051P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 1213 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.08(11)
_chemical_absolute_configuration rmad
_refine_ls_number_reflns         5000
_refine_ls_number_parameters     416
_refine_ls_number_restraints     13
_refine_ls_R_factor_all          0.0745
_refine_ls_R_factor_gt           0.0623
_refine_ls_wR_factor_ref         0.1454
_refine_ls_wR_factor_gt          0.1397
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_restrained_S_all      1.049
_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
S1 S 0.22249(5) -0.12982(16) 0.23249(13) 0.0230(4) Uani 1 1 d . . . . .
F1 F 0.09653(12) 0.2014(4) 0.1222(4) 0.0361(10) Uani 1 1 d . . . . .
F2 F 0.14148(15) 0.7856(4) 0.0223(4) 0.0478(12) Uani 1 1 d . . . . .
O1 O 0.23258(13) 0.3761(5) 0.1807(3) 0.0200(9) Uani 1 1 d . . . . .
H11 H 0.255(2) 0.317(8) 0.195(6) 0.030 Uiso 1 1 d . U . . .
N1 N 0.17006(15) 0.3892(6) 0.3539(4) 0.0176(10) Uani 1 1 d . . . . .
N2 N 0.12708(15) 0.4530(6) 0.3484(4) 0.0248(12) Uani 1 1 d . . . . .
N3 N 0.17825(17) 0.5980(6) 0.4432(4) 0.0212(11) Uani 1 1 d . . . . .
H3 H 0.191(2) 0.663(8) 0.494(6) 0.025 Uiso 1 1 d . U . . .
N4 N 0.27684(17) 0.0867(6) 0.1871(4) 0.0194(11) Uani 1 1 d . . . . .
N5 N 0.5291(2) 0.1672(11) 0.3765(8) 0.078(3) Uani 1 1 d . . . . .
C1 C 0.1341(2) 0.5822(8) 0.4035(5) 0.0260(14) Uani 1 1 d . . . . .
H1 H 0.110751 0.655783 0.414023 0.031 Uiso 1 1 calc R U . . .
C2 C 0.20043(18) 0.4735(7) 0.4099(5) 0.0173(11) Uani 1 1 d . . . . .
H2 H 0.232239 0.450983 0.424422 0.021 Uiso 1 1 calc R U . . .
C3 C 0.1783(2) 0.2491(7) 0.2921(5) 0.0190(12) Uani 1 1 d . . . . .
H3A H 0.150214 0.184606 0.288243 0.023 Uiso 1 1 calc R U . . .
H3B H 0.203642 0.190239 0.331045 0.023 Uiso 1 1 calc R U . . .
C4 C 0.19116(19) 0.2893(6) 0.1727(5) 0.0186(13) Uani 1 1 d . . . . .
C5 C 0.19845(19) 0.1377(7) 0.1074(5) 0.0185(12) Uani 1 1 d . . . . .
H5 H 0.168806 0.079130 0.102560 0.022 Uiso 1 1 calc R U . . .
C6 C 0.2119(2) 0.1703(8) -0.0112(5) 0.0254(14) Uani 1 1 d . . . . .
H6A H 0.215871 0.073196 -0.050484 0.038 Uiso 1 1 calc R U . . .
H6B H 0.240902 0.227941 -0.008062 0.038 Uiso 1 1 calc R U . . .
H6C H 0.187599 0.230633 -0.051115 0.038 Uiso 1 1 calc R U . . .
C7 C 0.2343(2) 0.0423(7) 0.1684(5) 0.0184(13) Uani 1 1 d . . . . .
C8 C 0.2782(2) -0.1391(8) 0.2861(5) 0.0276(14) Uani 1 1 d . . . . .
H8 H 0.290605 -0.219253 0.332457 0.033 Uiso 1 1 calc R U . . .
C9 C 0.30263(19) -0.0141(7) 0.2529(5) 0.0202(12) Uani 1 1 d . . . . .
C10 C 0.4922(3) 0.1296(11) 0.3571(8) 0.056(2) Uani 1 1 d . . . . .
C11 C 0.3516(2) 0.0179(7) 0.2805(5) 0.0222(13) Uani 1 1 d . . . . .
C12 C 0.3717(2) 0.1457(9) 0.2354(6) 0.0338(17) Uani 1 1 d . . . . .
H12 H 0.353606 0.210485 0.186311 0.041 Uiso 1 1 calc R U . . .
C13 C 0.4175(2) 0.1809(10) 0.2602(6) 0.0390(18) Uani 1 1 d . . . . .
H13 H 0.430691 0.268743 0.228267 0.047 Uiso 1 1 calc R U . . .
C14 C 0.4439(2) 0.0878(10) 0.3317(7) 0.0408(19) Uani 1 1 d . . . . .
C15 C 0.4240(3) -0.0395(10) 0.3783(7) 0.049(2) Uani 1 1 d . . . . .
H15 H 0.442191 -0.103484 0.427943 0.059 Uiso 1 1 calc R U . . .
C16 C 0.3782(3) -0.0741(9) 0.3534(6) 0.0416(19) Uani 1 1 d . . . . .
H16 H 0.364857 -0.161031 0.386241 0.050 Uiso 1 1 calc R U . . .
C21 C 0.1546(2) 0.3912(7) 0.1153(5) 0.0221(13) Uani 1 1 d . . . . .
C22 C 0.1647(2) 0.5423(8) 0.0877(5) 0.0244(14) Uani 1 1 d . . . . .
H22 H 0.195358 0.579828 0.098018 0.029 Uiso 1 1 calc R U . . .
C23 C 0.1298(3) 0.6363(8) 0.0454(6) 0.0347(17) Uani 1 1 d . . . . .
C24 C 0.0850(3) 0.5927(9) 0.0313(7) 0.046(2) Uani 1 1 d . . . . .
H24 H 0.061717 0.663610 0.006338 0.055 Uiso 1 1 calc R U . . .
C25 C 0.0742(2) 0.4424(9) 0.0544(7) 0.043(2) Uani 1 1 d . . . . .
H25 H 0.043504 0.405684 0.041437 0.051 Uiso 1 1 calc R U . . .
C26 C 0.1088(2) 0.3470(8) 0.0967(5) 0.0289(15) Uani 1 1 d . . . . .
S2 S 0.16951(4) 0.97287(16) 0.52941(11) 0.0163(3) Uani 1 1 d . . . . .
O11 O 0.14584(13) 0.9366(5) 0.4236(3) 0.0231(10) Uani 1 1 d . . . . .
O12 O 0.19636(13) 0.8416(4) 0.5773(3) 0.0189(9) Uani 1 1 d . . . . .
O13 O 0.19804(13) 1.1102(5) 0.5303(4) 0.0221(10) Uani 1 1 d . . . . .
C31 C 0.1258(2) 1.0114(7) 0.6221(5) 0.0229(14) Uani 1 1 d . . . . .
C32 C 0.1377(2) 1.0414(8) 0.7330(5) 0.0282(15) Uani 1 1 d . . . . .
H32 H 0.168965 1.035403 0.761089 0.034 Uiso 1 1 calc R U . . .
C33 C 0.1038(3) 1.0804(10) 0.8031(7) 0.045(2) Uani 1 1 d . . . . .
H33 H 0.111885 1.097882 0.879947 0.054 Uiso 1 1 calc R U . . .
C34 C 0.0579(3) 1.0943(11) 0.7628(7) 0.055(2) Uani 1 1 d . . . . .
C35 C 0.0470(3) 1.0620(11) 0.6522(7) 0.053(2) Uani 1 1 d . . . . .
H35 H 0.015813 1.068626 0.623779 0.063 Uiso 1 1 calc R U . . .
C36 C 0.0805(2) 1.0199(8) 0.5811(6) 0.0330(17) Uani 1 1 d . . . . .
H36 H 0.072198 0.997184 0.505053 0.040 Uiso 1 1 calc R U . . .
C37 C 0.0208(3) 1.1439(17) 0.8389(9) 0.107(5) Uani 1 1 d . . . . .
H37D H 0.022984 1.081501 0.906863 0.160 Uiso 1 1 calc R U . . .
H37A H -0.009675 1.129854 0.800046 0.160 Uiso 1 1 calc R U . . .
H37B H 0.025131 1.252167 0.858633 0.160 Uiso 1 1 calc R U . . .
N6 N 0.0034(11) 0.826(4) 0.089(3) 0.057(9) Uani 0.212(12) 1 d . U P A -1
C41 C 0.0353(12) 0.860(6) 0.143(3) 0.054(9) Uani 0.212(12) 1 d . U P A -1
C42 C 0.0771(10) 0.878(6) 0.217(3) 0.055(9) Uani 0.212(12) 1 d . U P A -1
H42A H 0.103447 0.897409 0.171978 0.083 Uiso 0.212(12) 1 calc R U P A -1
H42B H 0.082606 0.783926 0.260280 0.083 Uiso 0.212(12) 1 calc R U P A -1
H42C H 0.073278 0.964357 0.267334 0.083 Uiso 0.212(12) 1 calc R U P A -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
S1 C8 1.703(7) . ?
S1 C7 1.732(6) . ?
F1 C26 1.359(7) . ?
F2 C23 1.379(8) . ?
O1 C4 1.421(7) . ?
O1 H11 0.84(7) . ?
N1 C2 1.301(7) . ?
N1 N2 1.366(6) . ?
N1 C3 1.458(7) . ?
N2 C1 1.315(8) . ?
N3 C2 1.338(8) . ?
N3 C1 1.345(7) . ?
N3 H3 0.89(7) . ?
N4 C7 1.300(8) . ?
N4 C9 1.371(7) . ?
N5 C10 1.129(10) . ?
C1 H1 0.9500 . ?
C2 H2 0.9500 . ?
C3 C4 1.547(8) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 C21 1.516(8) . ?
C4 C5 1.560(8) . ?
C5 C7 1.488(8) . ?
C5 C6 1.530(8) . ?
C5 H5 1.0000 . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?
C8 C9 1.376(9) . ?
C8 H8 0.9500 . ?
C9 C11 1.466(8) . ?
C10 C14 1.464(10) . ?
C11 C16 1.385(9) . ?
C11 C12 1.387(9) . ?
C12 C13 1.377(9) . ?
C12 H12 0.9500 . ?
C13 C14 1.378(10) . ?
C13 H13 0.9500 . ?
C14 C15 1.388(12) . ?
C15 C16 1.380(10) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?
C21 C26 1.389(8) . ?
C21 C22 1.396(9) . ?
C22 C23 1.374(9) . ?
C22 H22 0.9500 . ?
C23 C24 1.357(10) . ?
C24 C25 1.381(11) . ?
C24 H24 0.9500 . ?
C25 C26 1.377(9) . ?
C25 H25 0.9500 . ?
S2 O11 1.440(4) . ?
S2 O13 1.457(4) . ?
S2 O12 1.480(4) . ?
S2 C31 1.778(6) . ?
C31 C36 1.377(9) . ?
C31 C32 1.380(8) . ?
C32 C33 1.382(9) . ?
C32 H32 0.9500 . ?
C33 C34 1.392(11) . ?
C33 H33 0.9500 . ?
C34 C35 1.374(11) . ?
C34 C37 1.525(10) . ?
C35 C36 1.387(9) . ?
C35 H35 0.9500 . ?
C36 H36 0.9500 . ?
C37 H37D 0.9800 . ?
C37 H37A 0.9800 . ?
C37 H37B 0.9800 . ?
N6 C41 1.13(4) . ?
C41 C42 1.46(4) . ?
C42 H42A 0.9800 . ?
C42 H42B 0.9800 . ?
C42 H42C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C8 S1 C7 89.8(3) . . ?
C4 O1 H11 109(5) . . ?
C2 N1 N2 112.4(5) . . ?
C2 N1 C3 127.4(5) . . ?
N2 N1 C3 119.9(5) . . ?
C1 N2 N1 102.4(5) . . ?
C2 N3 C1 106.1(5) . . ?
C2 N3 H3 121(4) . . ?
C1 N3 H3 131(4) . . ?
C7 N4 C9 112.6(5) . . ?
N2 C1 N3 112.3(5) . . ?
N2 C1 H1 123.9 . . ?
N3 C1 H1 123.9 . . ?
N1 C2 N3 106.8(5) . . ?
N1 C2 H2 126.6 . . ?
N3 C2 H2 126.6 . . ?
N1 C3 C4 109.9(5) . . ?
N1 C3 H3A 109.7 . . ?
C4 C3 H3A 109.7 . . ?
N1 C3 H3B 109.7 . . ?
C4 C3 H3B 109.7 . . ?
H3A C3 H3B 108.2 . . ?
O1 C4 C21 106.5(5) . . ?
O1 C4 C3 108.4(5) . . ?
C21 C4 C3 110.4(4) . . ?
O1 C4 C5 110.0(4) . . ?
C21 C4 C5 112.5(5) . . ?
C3 C4 C5 108.9(4) . . ?
C7 C5 C6 110.3(5) . . ?
C7 C5 C4 109.9(5) . . ?
C6 C5 C4 111.3(5) . . ?
C7 C5 H5 108.4 . . ?
C6 C5 H5 108.4 . . ?
C4 C5 H5 108.4 . . ?
C5 C6 H6A 109.5 . . ?
C5 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
C5 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
N4 C7 C5 123.0(5) . . ?
N4 C7 S1 113.4(4) . . ?
C5 C7 S1 123.3(4) . . ?
C9 C8 S1 110.5(5) . . ?
C9 C8 H8 124.8 . . ?
S1 C8 H8 124.8 . . ?
N4 C9 C8 113.7(5) . . ?
N4 C9 C11 119.5(5) . . ?
C8 C9 C11 126.8(5) . . ?
N5 C10 C14 177.5(11) . . ?
C16 C11 C12 118.7(6) . . ?
C16 C11 C9 121.6(6) . . ?
C12 C11 C9 119.7(6) . . ?
C13 C12 C11 121.5(7) . . ?
C13 C12 H12 119.3 . . ?
C11 C12 H12 119.3 . . ?
C12 C13 C14 119.5(7) . . ?
C12 C13 H13 120.2 . . ?
C14 C13 H13 120.2 . . ?
C13 C14 C15 119.6(7) . . ?
C13 C14 C10 118.1(8) . . ?
C15 C14 C10 122.4(8) . . ?
C16 C15 C14 120.6(7) . . ?
C16 C15 H15 119.7 . . ?
C14 C15 H15 119.7 . . ?
C15 C16 C11 120.0(7) . . ?
C15 C16 H16 120.0 . . ?
C11 C16 H16 120.0 . . ?
C26 C21 C22 116.0(6) . . ?
C26 C21 C4 123.0(6) . . ?
C22 C21 C4 120.6(6) . . ?
C23 C22 C21 119.3(6) . . ?
C23 C22 H22 120.4 . . ?
C21 C22 H22 120.4 . . ?
C24 C23 C22 123.9(7) . . ?
C24 C23 F2 119.1(6) . . ?
C22 C23 F2 116.9(6) . . ?
C23 C24 C25 118.1(7) . . ?
C23 C24 H24 121.0 . . ?
C25 C24 H24 121.0 . . ?
C26 C25 C24 118.5(6) . . ?
C26 C25 H25 120.8 . . ?
C24 C25 H25 120.8 . . ?
F1 C26 C25 116.8(6) . . ?
F1 C26 C21 119.1(6) . . ?
C25 C26 C21 124.1(6) . . ?
O11 S2 O13 115.2(3) . . ?
O11 S2 O12 112.4(2) . . ?
O13 S2 O12 110.4(2) . . ?
O11 S2 C31 106.0(3) . . ?
O13 S2 C31 105.7(2) . . ?
O12 S2 C31 106.4(3) . . ?
C36 C31 C32 120.3(6) . . ?
C36 C31 S2 119.6(5) . . ?
C32 C31 S2 119.9(5) . . ?
C31 C32 C33 119.6(6) . . ?
C31 C32 H32 120.2 . . ?
C33 C32 H32 120.2 . . ?
C32 C33 C34 121.0(7) . . ?
C32 C33 H33 119.5 . . ?
C34 C33 H33 119.5 . . ?
C35 C34 C33 118.1(7) . . ?
C35 C34 C37 120.8(8) . . ?
C33 C34 C37 121.2(8) . . ?
C34 C35 C36 121.7(7) . . ?
C34 C35 H35 119.2 . . ?
C36 C35 H35 119.2 . . ?
C31 C36 C35 119.2(6) . . ?
C31 C36 H36 120.4 . . ?
C35 C36 H36 120.4 . . ?
C34 C37 H37D 109.5 . . ?
C34 C37 H37A 109.5 . . ?
H37D C37 H37A 109.5 . . ?
C34 C37 H37B 109.5 . . ?
H37D C37 H37B 109.5 . . ?
H37A C37 H37B 109.5 . . ?
N6 C41 C42 171(5) . . ?
C41 C42 H42A 109.5 . . ?
C41 C42 H42B 109.5 . . ?
H42A C42 H42B 109.5 . . ?
C41 C42 H42C 109.5 . . ?
H42A C42 H42C 109.5 . . ?
H42B C42 H42C 109.5 . . ?

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
N3 H3 O12 0.89(7) 1.86(7) 2.697(6) 156(6) .
O1 H11 N4 0.84(7) 2.11(7) 2.832(7) 144(6) .

_refine_diff_density_max         0.306
_refine_diff_density_min         -0.337
_refine_diff_density_rms         0.065



####################################################################### 
# 
# 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_a
_database_code_depnum_ccdc_archive 'CCDC 2113411'
loop_
_audit_author_name
_audit_author_address
'Andrei Churakov'
;Institute of General and Inorganic Chemistry RAS
Russia
;
_audit_update_record             
;
2021-10-01 deposited with the CCDC.	2021-11-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C22 H17 F2 N5 O S, H2 O'
_chemical_formula_sum            'C22 H19 F2 N5 O2 S'
_chemical_formula_weight         455.48

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'
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'
F F 0.0171 0.0103 '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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

_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+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   7.8920(2)
_cell_length_b                   11.2256(3)
_cell_length_c                   24.2967(6)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2152.50(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    9981
_cell_measurement_theta_min      2.470
_cell_measurement_theta_max      30.432

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.406
_exptl_crystal_F_000             944
_exptl_transmission_factor_min   0.8042
_exptl_transmission_factor_max   0.8622
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.198
_shelx_estimated_absorpt_T_min   0.943
_shelx_estimated_absorpt_T_max   0.981
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   'SADABS (Bruker, 2016)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            18824
_diffrn_reflns_av_unetI/netI     0.0207
_diffrn_reflns_av_R_equivalents  0.0238
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_theta_min         1.998
_diffrn_reflns_theta_max         26.989
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             4693
_reflns_number_gt                4447
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.747
_reflns_Friedel_fraction_max     0.999
_reflns_Friedel_fraction_full    0.999

_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       'APEX3 (Bruker, 2018)'
_computing_cell_refinement       'SAINT (Bruker, 2018)'
_computing_data_reduction        'SAINT (Bruker, 2018)'
_computing_structure_solution    'SHELXT (Sheldrick, 2016)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_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)+(0.0378P)²+0.3191P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 1794 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.04(3)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         4693
_refine_ls_number_parameters     365
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0310
_refine_ls_R_factor_gt           0.0285
_refine_ls_wR_factor_ref         0.0711
_refine_ls_wR_factor_gt          0.0697
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_restrained_S_all      1.035
_refine_ls_shift/su_max          0.001
_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
S1 S 0.26349(7) 0.47592(4) 0.31285(2) 0.03123(13) Uani 1 1 d . . . . .
F1 F 0.0750(2) 0.68204(16) 0.01169(5) 0.0610(5) Uani 1 1 d . . . . .
F2 F 0.2528(2) 0.90630(11) 0.20036(5) 0.0519(4) Uani 1 1 d . . . . .
O1 O 0.25881(18) 0.52668(12) 0.19323(5) 0.0254(3) Uani 1 1 d . . . . .
H10 H 0.170(4) 0.499(3) 0.1827(11) 0.046(8) Uiso 1 1 d . . . . .
N1 N 0.7103(2) 0.53914(16) 0.11903(8) 0.0362(4) Uani 1 1 d . . . . .
N2 N 0.6020(2) 0.72175(16) 0.13457(7) 0.0319(4) Uani 1 1 d . . . . .
N3 N 0.5535(2) 0.64443(15) 0.17478(7) 0.0247(3) Uani 1 1 d . . . . .
N4 N 0.1642(2) 0.67428(14) 0.35363(6) 0.0250(3) Uani 1 1 d . . . . .
N5 N 0.1135(3) 0.8105(2) 0.66032(8) 0.0551(6) Uani 1 1 d . . . . .
C1 C 0.6957(3) 0.6539(2) 0.10280(9) 0.0343(5) Uani 1 1 d . . . . .
C2 C 0.6178(3) 0.5378(2) 0.16422(10) 0.0328(5) Uani 1 1 d . . . . .
C3 C 0.4399(3) 0.6793(2) 0.21898(9) 0.0290(4) Uani 1 1 d . . . . .
C4 C 0.2547(3) 0.65051(16) 0.20420(7) 0.0240(4) Uani 1 1 d . . . . .
C5 C 0.2038(3) 0.72371(18) 0.15378(8) 0.0266(4) Uani 1 1 d . . . . .
C6 C 0.1576(3) 0.6692(2) 0.10443(8) 0.0293(4) Uani 1 1 d . . . . .
C7 C 0.1213(3) 0.7390(2) 0.05901(9) 0.0398(5) Uani 1 1 d . . . . .
C8 C 0.1277(4) 0.8606(3) 0.05955(11) 0.0489(7) Uani 1 1 d . . . . .
C9 C 0.1714(4) 0.9160(2) 0.10803(11) 0.0487(7) Uani 1 1 d . . . . .
C10 C 0.2079(3) 0.84756(19) 0.15351(9) 0.0364(5) Uani 1 1 d . . . . .
C11 C -0.0500(3) 0.6484(2) 0.23981(10) 0.0329(5) Uani 1 1 d . . . . .
C12 C 0.1352(3) 0.67889(19) 0.25331(8) 0.0258(4) Uani 1 1 d . . . . .
C13 C 0.1857(3) 0.61956(16) 0.30673(8) 0.0247(4) Uani 1 1 d . . . . .
C14 C 0.2687(3) 0.49285(18) 0.38279(8) 0.0309(4) Uani 1 1 d . . . . .
C15 C 0.2111(3) 0.60246(17) 0.39745(8) 0.0259(4) Uani 1 1 d . . . . .
C16 C 0.1935(3) 0.64803(18) 0.45442(8) 0.0265(4) Uani 1 1 d . . . . .
C17 C 0.1805(3) 0.5692(2) 0.49857(9) 0.0331(5) Uani 1 1 d . . . . .
C18 C 0.1590(3) 0.6115(2) 0.55137(9) 0.0355(5) Uani 1 1 d . . . . .
C19 C 0.1523(3) 0.7325(2) 0.56086(8) 0.0323(5) Uani 1 1 d . . . . .
C20 C 0.1673(3) 0.8125(2) 0.51735(9) 0.0384(5) Uani 1 1 d . . . . .
C21 C 0.1878(3) 0.76964(19) 0.46432(8) 0.0346(5) Uani 1 1 d . . . . .
C22 C 0.1295(3) 0.7762(2) 0.61644(9) 0.0393(5) Uani 1 1 d . . . . .
H1 H 0.747(3) 0.683(2) 0.0709(10) 0.036(6) Uiso 1 1 d . . . . .
H2 H 0.596(3) 0.472(3) 0.1871(11) 0.049(7) Uiso 1 1 d . . . . .
H6 H 0.151(3) 0.586(2) 0.1014(9) 0.029(6) Uiso 1 1 d . . . . .
H8 H 0.095(4) 0.905(3) 0.0266(13) 0.070(10) Uiso 1 1 d . . . . .
H9 H 0.167(4) 1.008(3) 0.1141(12) 0.062(9) Uiso 1 1 d . . . . .
H12 H 0.142(3) 0.762(2) 0.2604(8) 0.020(5) Uiso 1 1 d . . . . .
H14 H 0.309(3) 0.429(2) 0.4027(11) 0.045(7) Uiso 1 1 d . . . . .
H17 H 0.179(3) 0.481(3) 0.4912(10) 0.049(7) Uiso 1 1 d . . . . .
H18 H 0.150(3) 0.556(2) 0.5798(9) 0.026(6) Uiso 1 1 d . . . . .
H20 H 0.160(3) 0.897(2) 0.5240(10) 0.038(7) Uiso 1 1 d . . . . .
H21 H 0.200(3) 0.825(2) 0.4340(10) 0.037(6) Uiso 1 1 d . . . . .
H31 H 0.453(3) 0.764(2) 0.2246(10) 0.037(7) Uiso 1 1 d . . . . .
H32 H 0.474(3) 0.639(2) 0.2504(11) 0.032(6) Uiso 1 1 d . . . . .
H111 H -0.120(3) 0.671(2) 0.2699(10) 0.034(6) Uiso 1 1 d . . . . .
H112 H -0.085(4) 0.688(3) 0.2067(12) 0.052(8) Uiso 1 1 d . . . . .
H113 H -0.063(3) 0.564(2) 0.2339(9) 0.032(6) Uiso 1 1 d . . . . .
O2 O 0.0018(2) 0.40572(15) 0.14831(7) 0.0361(4) Uani 1 1 d . . . . .
H3 H -0.030(5) 0.334(4) 0.1469(14) 0.076(11) Uiso 1 1 d . . . . .
H4 H -0.086(4) 0.449(3) 0.1364(12) 0.054(8) Uiso 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 C14 1.710(2) . ?
S1 C13 1.7317(19) . ?
F1 C7 1.366(3) . ?
F2 C10 1.362(3) . ?
O1 C4 1.416(2) . ?
O1 H10 0.81(3) . ?
N1 C2 1.319(3) . ?
N1 C1 1.352(3) . ?
N2 C1 1.313(3) . ?
N2 N3 1.362(2) . ?
N3 C2 1.325(3) . ?
N3 C3 1.453(3) . ?
N4 C13 1.306(2) . ?
N4 C15 1.386(2) . ?
N5 C22 1.141(3) . ?
C1 H1 0.93(2) . ?
C2 H2 0.94(3) . ?
C3 C4 1.539(3) . ?
C3 H31 0.97(3) . ?
C3 H32 0.93(3) . ?
C4 C5 1.529(3) . ?
C4 C12 1.554(3) . ?
C5 C10 1.391(3) . ?
C5 C6 1.395(3) . ?
C6 C7 1.384(3) . ?
C6 H6 0.94(2) . ?
C7 C8 1.366(4) . ?
C8 C9 1.376(4) . ?
C8 H8 0.98(3) . ?
C9 C10 1.376(3) . ?
C9 H9 1.05(3) . ?
C11 C12 1.537(3) . ?
C11 H111 0.95(3) . ?
C11 H112 0.96(3) . ?
C11 H113 0.96(3) . ?
C12 C13 1.512(3) . ?
C12 H12 0.95(2) . ?
C14 C15 1.359(3) . ?
C14 H14 0.92(3) . ?
C15 C16 1.482(3) . ?
C16 C21 1.387(3) . ?
C16 C17 1.395(3) . ?
C17 C18 1.379(3) . ?
C17 H17 1.00(3) . ?
C18 C19 1.379(3) . ?
C18 H18 0.94(2) . ?
C19 C20 1.392(3) . ?
C19 C22 1.448(3) . ?
C20 C21 1.385(3) . ?
C20 H20 0.96(3) . ?
C21 H21 0.97(2) . ?
O2 H3 0.85(4) . ?
O2 H4 0.89(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
C14 S1 C13 89.45(10) . . ?
C4 O1 H10 114(2) . . ?
C2 N1 C1 101.92(18) . . ?
C1 N2 N3 102.15(17) . . ?
C2 N3 N2 109.21(17) . . ?
C2 N3 C3 128.53(18) . . ?
N2 N3 C3 122.15(17) . . ?
C13 N4 C15 111.23(16) . . ?
N2 C1 N1 115.4(2) . . ?
N2 C1 H1 121.7(15) . . ?
N1 C1 H1 122.9(15) . . ?
N1 C2 N3 111.27(19) . . ?
N1 C2 H2 127.1(17) . . ?
N3 C2 H2 121.6(17) . . ?
N3 C3 C4 110.91(15) . . ?
N3 C3 H31 107.7(15) . . ?
C4 C3 H31 109.9(16) . . ?
N3 C3 H32 107.3(16) . . ?
C4 C3 H32 111.5(16) . . ?
H31 C3 H32 109(2) . . ?
O1 C4 C5 112.52(15) . . ?
O1 C4 C3 103.21(16) . . ?
C5 C4 C3 108.87(16) . . ?
O1 C4 C12 111.07(15) . . ?
C5 C4 C12 110.22(16) . . ?
C3 C4 C12 110.74(15) . . ?
C10 C5 C6 116.16(19) . . ?
C10 C5 C4 122.35(18) . . ?
C6 C5 C4 121.43(18) . . ?
C7 C6 C5 119.4(2) . . ?
C7 C6 H6 119.3(14) . . ?
C5 C6 H6 121.3(14) . . ?
F1 C7 C8 119.1(2) . . ?
F1 C7 C6 117.5(2) . . ?
C8 C7 C6 123.4(2) . . ?
C7 C8 C9 117.9(2) . . ?
C7 C8 H8 119.5(19) . . ?
C9 C8 H8 122.5(19) . . ?
C8 C9 C10 119.2(2) . . ?
C8 C9 H9 124.0(16) . . ?
C10 C9 H9 116.5(16) . . ?
F2 C10 C9 117.1(2) . . ?
F2 C10 C5 119.07(19) . . ?
C9 C10 C5 123.8(2) . . ?
C12 C11 H111 109.3(15) . . ?
C12 C11 H112 110.4(18) . . ?
H111 C11 H112 111(2) . . ?
C12 C11 H113 110.8(15) . . ?
H111 C11 H113 108(2) . . ?
H112 C11 H113 108(2) . . ?
C13 C12 C11 109.63(18) . . ?
C13 C12 C4 114.11(17) . . ?
C11 C12 C4 111.59(17) . . ?
C13 C12 H12 105.1(12) . . ?
C11 C12 H12 108.1(13) . . ?
C4 C12 H12 107.9(13) . . ?
N4 C13 C12 120.51(17) . . ?
N4 C13 S1 114.15(14) . . ?
C12 C13 S1 125.26(14) . . ?
C15 C14 S1 110.66(15) . . ?
C15 C14 H14 132.9(16) . . ?
S1 C14 H14 116.4(16) . . ?
C14 C15 N4 114.50(17) . . ?
C14 C15 C16 126.05(18) . . ?
N4 C15 C16 119.45(17) . . ?
C21 C16 C17 119.30(19) . . ?
C21 C16 C15 120.30(18) . . ?
C17 C16 C15 120.40(18) . . ?
C18 C17 C16 120.4(2) . . ?
C18 C17 H17 120.2(15) . . ?
C16 C17 H17 119.3(15) . . ?
C19 C18 C17 120.0(2) . . ?
C19 C18 H18 122.3(14) . . ?
C17 C18 H18 117.7(14) . . ?
C18 C19 C20 120.33(19) . . ?
C18 C19 C22 119.6(2) . . ?
C20 C19 C22 120.0(2) . . ?
C21 C20 C19 119.5(2) . . ?
C21 C20 H20 120.3(14) . . ?
C19 C20 H20 120.2(14) . . ?
C20 C21 C16 120.5(2) . . ?
C20 C21 H21 119.7(14) . . ?
C16 C21 H21 119.8(14) . . ?
N5 C22 C19 179.2(3) . . ?
H3 O2 H4 106(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
C1 N2 N3 C2 -0.9(2) . . . . ?
C1 N2 N3 C3 -177.38(18) . . . . ?
N3 N2 C1 N1 0.5(2) . . . . ?
C2 N1 C1 N2 0.0(3) . . . . ?
C1 N1 C2 N3 -0.6(2) . . . . ?
N2 N3 C2 N1 1.0(2) . . . . ?
C3 N3 C2 N1 177.20(18) . . . . ?
C2 N3 C3 C4 -82.6(3) . . . . ?
N2 N3 C3 C4 93.2(2) . . . . ?
N3 C3 C4 O1 56.7(2) . . . . ?
N3 C3 C4 C5 -63.0(2) . . . . ?
N3 C3 C4 C12 175.62(16) . . . . ?
O1 C4 C5 C10 -173.43(19) . . . . ?
C3 C4 C5 C10 -59.7(2) . . . . ?
C12 C4 C5 C10 62.0(2) . . . . ?
O1 C4 C5 C6 3.7(3) . . . . ?
C3 C4 C5 C6 117.5(2) . . . . ?
C12 C4 C5 C6 -120.9(2) . . . . ?
C10 C5 C6 C7 0.8(3) . . . . ?
C4 C5 C6 C7 -176.54(19) . . . . ?
C5 C6 C7 F1 -179.4(2) . . . . ?
C5 C6 C7 C8 -0.2(4) . . . . ?
F1 C7 C8 C9 178.7(2) . . . . ?
C6 C7 C8 C9 -0.5(4) . . . . ?
C7 C8 C9 C10 0.5(4) . . . . ?
C8 C9 C10 F2 179.1(2) . . . . ?
C8 C9 C10 C5 0.2(4) . . . . ?
C6 C5 C10 F2 -179.73(19) . . . . ?
C4 C5 C10 F2 -2.4(3) . . . . ?
C6 C5 C10 C9 -0.8(4) . . . . ?
C4 C5 C10 C9 176.5(2) . . . . ?
O1 C4 C12 C13 60.2(2) . . . . ?
C5 C4 C12 C13 -174.44(17) . . . . ?
C3 C4 C12 C13 -53.9(2) . . . . ?
O1 C4 C12 C11 -64.8(2) . . . . ?
C5 C4 C12 C11 60.6(2) . . . . ?
C3 C4 C12 C11 -178.87(18) . . . . ?
C15 N4 C13 C12 177.15(18) . . . . ?
C15 N4 C13 S1 0.4(2) . . . . ?
C11 C12 C13 N4 -89.8(2) . . . . ?
C4 C12 C13 N4 144.22(19) . . . . ?
C11 C12 C13 S1 86.6(2) . . . . ?
C4 C12 C13 S1 -39.4(2) . . . . ?
C14 S1 C13 N4 -0.66(17) . . . . ?
C14 S1 C13 C12 -177.24(19) . . . . ?
C13 S1 C14 C15 0.73(18) . . . . ?
S1 C14 C15 N4 -0.7(3) . . . . ?
S1 C14 C15 C16 178.50(17) . . . . ?
C13 N4 C15 C14 0.2(3) . . . . ?
C13 N4 C15 C16 -179.05(18) . . . . ?
C14 C15 C16 C21 158.7(2) . . . . ?
N4 C15 C16 C21 -22.2(3) . . . . ?
C14 C15 C16 C17 -22.0(3) . . . . ?
N4 C15 C16 C17 157.1(2) . . . . ?
C21 C16 C17 C18 1.2(3) . . . . ?
C15 C16 C17 C18 -178.1(2) . . . . ?
C16 C17 C18 C19 -0.7(4) . . . . ?
C17 C18 C19 C20 -0.1(4) . . . . ?
C17 C18 C19 C22 179.9(2) . . . . ?
C18 C19 C20 C21 0.5(4) . . . . ?
C22 C19 C20 C21 -179.5(2) . . . . ?
C19 C20 C21 C16 0.0(4) . . . . ?
C17 C16 C21 C20 -0.8(4) . . . . ?
C15 C16 C21 C20 178.4(2) . . . . ?

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 H10 O2 0.81(3) 1.89(3) 2.674(2) 164(3) .
O2 H3 N4 0.85(4) 2.08(4) 2.910(2) 166(3) 3_545
O2 H4 N1 0.89(3) 1.95(3) 2.835(3) 173(3) 1_455

_refine_diff_density_max         0.196
_refine_diff_density_min         -0.157
_refine_diff_density_rms         0.031



####################################################################### 
# 
# 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_a_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 2113413'
loop_
_audit_author_name
_audit_author_address
'Andrei Churakov'
;Institute of General and Inorganic Chemistry RAS
Russia
;
_audit_update_record             
;
2021-10-01 deposited with the CCDC.	2021-11-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C22 H17 F2 N5 O S'
_chemical_formula_sum            'C22 H17 F2 N5 O S'
_chemical_formula_weight         437.46

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'
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'
F F 0.0171 0.0103 '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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

_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'

_cell_length_a                   5.8250(3)
_cell_length_b                   17.3293(8)
_cell_length_c                   9.7547(4)
_cell_angle_alpha                90
_cell_angle_beta                 97.072(2)
_cell_angle_gamma                90
_cell_volume                     977.18(8)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9908
_cell_measurement_theta_min      2.410
_cell_measurement_theta_max      30.525

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.487
_exptl_crystal_F_000             452
_exptl_transmission_factor_min   0.6734
_exptl_transmission_factor_max   0.7461
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.211
_shelx_estimated_absorpt_T_min   0.949
_shelx_estimated_absorpt_T_max   0.979
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   'SADABS (Bruker, 2016)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            42105
_diffrn_reflns_av_unetI/netI     0.0202
_diffrn_reflns_av_R_equivalents  0.0317
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.104
_diffrn_reflns_theta_max         29.997
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             5667
_reflns_number_gt                5522
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.928
_reflns_Friedel_fraction_max     0.986
_reflns_Friedel_fraction_full    0.992

_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       'APEX3 (Bruker, 2018)'
_computing_cell_refinement       'SAINT (Bruker, 2018)'
_computing_data_reduction        'SAINT (Bruker, 2018)'
_computing_structure_solution    'SHELXT (Sheldrick, 2016)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_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)+(0.0389P)²+0.1631P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 2556 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.014(19)
_chemical_absolute_configuration rmad
_refine_ls_number_reflns         5667
_refine_ls_number_parameters     348
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0269
_refine_ls_R_factor_gt           0.0258
_refine_ls_wR_factor_ref         0.0663
_refine_ls_wR_factor_gt          0.0655
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_restrained_S_all      1.053
_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
S1 S -0.30597(6) 0.49247(2) 0.71659(4) 0.01504(8) Uani 1 1 d . . . . .
F1 F -0.24333(19) 0.62941(7) 0.28992(11) 0.0230(2) Uani 1 1 d . . . . .
F2 F 0.4285(2) 0.52550(8) -0.00163(12) 0.0306(3) Uani 1 1 d . . . . .
O1 O 0.29916(18) 0.48172(7) 0.46514(12) 0.0145(2) Uani 1 1 d . . . . .
N1 N 0.2819(2) 0.65939(8) 0.50282(14) 0.0142(3) Uani 1 1 d . . . . .
N2 N 0.5073(2) 0.65797(9) 0.55998(16) 0.0194(3) Uani 1 1 d . . . . .
N3 N 0.4254(3) 0.77011(9) 0.44484(17) 0.0226(3) Uani 1 1 d . . . . .
N4 N 0.0531(2) 0.41588(8) 0.67100(13) 0.0136(2) Uani 1 1 d . . . . .
N5 N 0.8805(3) 0.22980(9) 1.24248(15) 0.0191(3) Uani 1 1 d . . . . .
C1 C 0.5835(3) 0.72542(11) 0.5215(2) 0.0215(4) Uani 1 1 d . . . . .
C2 C 0.2373(3) 0.72647(10) 0.43619(18) 0.0188(3) Uani 1 1 d . . . . .
C3 C 0.1187(3) 0.60018(9) 0.53331(16) 0.0138(3) Uani 1 1 d . . . . .
C4 C 0.1015(3) 0.52950(9) 0.43567(15) 0.0118(3) Uani 1 1 d . . . . .
C5 C -0.1234(2) 0.48435(9) 0.46011(14) 0.0119(3) Uani 1 1 d . . . . .
C6 C -0.1620(3) 0.41372(10) 0.36638(17) 0.0169(3) Uani 1 1 d . . . . .
C7 C -0.1096(3) 0.46056(9) 0.61007(16) 0.0127(3) Uani 1 1 d . . . . .
C8 C -0.1612(3) 0.44216(10) 0.85000(16) 0.0150(3) Uani 1 1 d . . . . .
C9 C 0.0260(3) 0.40481(9) 0.80920(15) 0.0132(3) Uani 1 1 d . . . . .
C10 C 0.7267(3) 0.25222(9) 1.16889(17) 0.0162(3) Uani 1 1 d . . . . .
C11 C 0.1954(3) 0.35894(10) 0.89899(16) 0.0135(3) Uani 1 1 d . . . . .
C12 C 0.1799(3) 0.35393(11) 1.04088(17) 0.0173(3) Uani 1 1 d . . . . .
C13 C 0.3504(3) 0.31716(11) 1.12915(17) 0.0179(3) Uani 1 1 d . . . . .
C14 C 0.5386(3) 0.28393(10) 1.07540(17) 0.0152(3) Uani 1 1 d . . . . .
C15 C 0.5506(3) 0.28503(10) 0.93317(17) 0.0163(3) Uani 1 1 d . . . . .
C16 C 0.3795(3) 0.32233(10) 0.84576(16) 0.0154(3) Uani 1 1 d . . . . .
C21 C 0.0947(3) 0.55387(9) 0.28499(16) 0.0129(3) Uani 1 1 d . . . . .
C22 C 0.2671(3) 0.52862(10) 0.20751(17) 0.0163(3) Uani 1 1 d . . . . .
C23 C 0.2583(3) 0.55125(11) 0.07103(18) 0.0202(3) Uani 1 1 d . . . . .
C24 C 0.0881(3) 0.59758(11) 0.00495(18) 0.0220(4) Uani 1 1 d . . . . .
C25 C -0.0819(3) 0.62399(11) 0.08148(18) 0.0204(3) Uani 1 1 d . . . . .
C26 C -0.0746(3) 0.60185(10) 0.21827(17) 0.0162(3) Uani 1 1 d . . . . .
H1 H 0.733(5) 0.7395(18) 0.546(3) 0.040(8) Uiso 1 1 d . . . . .
H2 H 0.099(5) 0.7374(16) 0.394(3) 0.027(6) Uiso 1 1 d . . . . .
H4 H 0.282(4) 0.4566(15) 0.526(3) 0.021(6) Uiso 1 1 d . . . . .
H5 H -0.243(4) 0.5176(12) 0.443(2) 0.008(5) Uiso 1 1 d . . . . .
H8 H -0.210(4) 0.4432(14) 0.941(3) 0.021(6) Uiso 1 1 d . . . . .
H12 H 0.055(5) 0.3772(17) 1.076(3) 0.032(7) Uiso 1 1 d . . . . .
H13 H 0.341(5) 0.3169(17) 1.223(3) 0.031(7) Uiso 1 1 d . . . . .
H15 H 0.672(4) 0.2625(14) 0.897(2) 0.018(5) Uiso 1 1 d . . . . .
H16 H 0.392(4) 0.3226(15) 0.752(2) 0.019(5) Uiso 1 1 d . . . . .
H22 H 0.391(4) 0.4940(15) 0.248(2) 0.018(5) Uiso 1 1 d . . . . .
H24 H 0.079(5) 0.6112(16) -0.094(3) 0.034(7) Uiso 1 1 d . . . . .
H25 H -0.196(5) 0.6542(16) 0.050(3) 0.025(6) Uiso 1 1 d . . . . .
H31 H -0.022(4) 0.6241(14) 0.530(2) 0.014(5) Uiso 1 1 d . . . . .
H32 H 0.162(4) 0.5835(14) 0.625(3) 0.017(5) Uiso 1 1 d . . . . .
H61 H -0.031(5) 0.3774(16) 0.381(3) 0.028(6) Uiso 1 1 d . . . . .
H62 H -0.300(4) 0.3834(15) 0.388(3) 0.025(6) Uiso 1 1 d . . . . .
H63 H -0.175(4) 0.4279(14) 0.274(2) 0.017(5) Uiso 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 C8 1.7013(16) . ?
S1 C7 1.7280(16) . ?
F1 C26 1.3606(19) . ?
F2 C23 1.363(2) . ?
O1 C4 1.4186(18) . ?
O1 H4 0.75(3) . ?
N1 C2 1.341(2) . ?
N1 N2 1.362(2) . ?
N1 C3 1.454(2) . ?
N2 C1 1.321(2) . ?
N3 C2 1.325(2) . ?
N3 C1 1.356(3) . ?
N4 C7 1.309(2) . ?
N4 C9 1.3898(19) . ?
N5 C10 1.145(2) . ?
C1 H1 0.91(3) . ?
C2 H2 0.88(3) . ?
C3 C4 1.547(2) . ?
C3 H31 0.91(2) . ?
C3 H32 0.95(2) . ?
C4 C21 1.525(2) . ?
C4 C5 1.569(2) . ?
C5 C7 1.512(2) . ?
C5 C6 1.528(2) . ?
C5 H5 0.90(2) . ?
C6 H61 0.98(3) . ?
C6 H62 1.00(3) . ?
C6 H63 0.93(2) . ?
C8 C9 1.369(2) . ?
C8 H8 0.96(3) . ?
C9 C11 1.469(2) . ?
C10 C14 1.445(2) . ?
C11 C16 1.400(2) . ?
C11 C12 1.401(2) . ?
C12 C13 1.387(2) . ?
C12 H12 0.93(3) . ?
C13 C14 1.397(2) . ?
C13 H13 0.93(3) . ?
C14 C15 1.398(2) . ?
C15 C16 1.389(2) . ?
C15 H15 0.91(2) . ?
C16 H16 0.93(2) . ?
C21 C26 1.389(2) . ?
C21 C22 1.399(2) . ?
C22 C23 1.383(2) . ?
C22 H22 0.98(2) . ?
C23 C24 1.373(3) . ?
C24 C25 1.389(3) . ?
C24 H24 0.99(3) . ?
C25 C26 1.384(2) . ?
C25 H25 0.87(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
C8 S1 C7 89.64(8) . . ?
C4 O1 H4 108(2) . . ?
C2 N1 N2 109.47(14) . . ?
C2 N1 C3 128.19(14) . . ?
N2 N1 C3 121.67(14) . . ?
C1 N2 N1 102.03(15) . . ?
C2 N3 C1 102.09(15) . . ?
C7 N4 C9 111.10(13) . . ?
N2 C1 N3 115.65(16) . . ?
N2 C1 H1 121(2) . . ?
N3 C1 H1 124(2) . . ?
N3 C2 N1 110.76(16) . . ?
N3 C2 H2 127.6(17) . . ?
N1 C2 H2 121.7(18) . . ?
N1 C3 C4 115.29(13) . . ?
N1 C3 H31 106.1(15) . . ?
C4 C3 H31 110.2(15) . . ?
N1 C3 H32 107.8(14) . . ?
C4 C3 H32 109.3(15) . . ?
H31 C3 H32 108(2) . . ?
O1 C4 C21 106.31(12) . . ?
O1 C4 C3 110.35(12) . . ?
C21 C4 C3 111.47(13) . . ?
O1 C4 C5 110.50(12) . . ?
C21 C4 C5 111.19(12) . . ?
C3 C4 C5 107.06(12) . . ?
C7 C5 C6 110.29(13) . . ?
C7 C5 C4 109.70(12) . . ?
C6 C5 C4 111.88(12) . . ?
C7 C5 H5 107.5(13) . . ?
C6 C5 H5 110.4(13) . . ?
C4 C5 H5 106.9(13) . . ?
C5 C6 H61 111.7(16) . . ?
C5 C6 H62 111.0(15) . . ?
H61 C6 H62 105(2) . . ?
C5 C6 H63 111.0(15) . . ?
H61 C6 H63 106(2) . . ?
H62 C6 H63 111(2) . . ?
N4 C7 C5 123.35(13) . . ?
N4 C7 S1 114.34(11) . . ?
C5 C7 S1 122.29(11) . . ?
C9 C8 S1 110.95(12) . . ?
C9 C8 H8 127.6(15) . . ?
S1 C8 H8 121.4(15) . . ?
C8 C9 N4 113.98(14) . . ?
C8 C9 C11 125.66(14) . . ?
N4 C9 C11 120.32(14) . . ?
N5 C10 C14 177.26(18) . . ?
C16 C11 C12 118.94(15) . . ?
C16 C11 C9 120.86(14) . . ?
C12 C11 C9 120.14(14) . . ?
C13 C12 C11 120.90(15) . . ?
C13 C12 H12 120.4(17) . . ?
C11 C12 H12 118.7(17) . . ?
C12 C13 C14 119.46(15) . . ?
C12 C13 H13 119.5(17) . . ?
C14 C13 H13 121.0(17) . . ?
C13 C14 C15 120.29(15) . . ?
C13 C14 C10 119.29(15) . . ?
C15 C14 C10 120.33(15) . . ?
C16 C15 C14 119.74(15) . . ?
C16 C15 H15 119.7(15) . . ?
C14 C15 H15 120.6(15) . . ?
C15 C16 C11 120.53(15) . . ?
C15 C16 H16 118.0(15) . . ?
C11 C16 H16 121.5(15) . . ?
C26 C21 C22 116.71(14) . . ?
C26 C21 C4 123.35(14) . . ?
C22 C21 C4 119.93(14) . . ?
C23 C22 C21 119.18(16) . . ?
C23 C22 H22 120.1(13) . . ?
C21 C22 H22 120.7(13) . . ?
F2 C23 C24 118.47(16) . . ?
F2 C23 C22 117.71(17) . . ?
C24 C23 C22 123.82(16) . . ?
C23 C24 C25 117.49(16) . . ?
C23 C24 H24 123.1(17) . . ?
C25 C24 H24 119.4(17) . . ?
C26 C25 C24 119.19(17) . . ?
C26 C25 H25 116.2(16) . . ?
C24 C25 H25 124.6(16) . . ?
F1 C26 C25 117.37(15) . . ?
F1 C26 C21 119.05(14) . . ?
C25 C26 C21 123.58(16) . . ?

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
C2 N1 N2 C1 -0.58(18) . . . . ?
C3 N1 N2 C1 -171.86(14) . . . . ?
N1 N2 C1 N3 0.2(2) . . . . ?
C2 N3 C1 N2 0.2(2) . . . . ?
C1 N3 C2 N1 -0.56(19) . . . . ?
N2 N1 C2 N3 0.75(19) . . . . ?
C3 N1 C2 N3 171.31(15) . . . . ?
C2 N1 C3 C4 100.51(19) . . . . ?
N2 N1 C3 C4 -89.97(18) . . . . ?
N1 C3 C4 O1 74.25(17) . . . . ?
N1 C3 C4 C21 -43.64(18) . . . . ?
N1 C3 C4 C5 -165.44(13) . . . . ?
O1 C4 C5 C7 61.70(16) . . . . ?
C21 C4 C5 C7 179.51(13) . . . . ?
C3 C4 C5 C7 -58.51(16) . . . . ?
O1 C4 C5 C6 -61.04(16) . . . . ?
C21 C4 C5 C6 56.78(17) . . . . ?
C3 C4 C5 C6 178.75(13) . . . . ?
C9 N4 C7 C5 178.77(14) . . . . ?
C9 N4 C7 S1 0.24(17) . . . . ?
C6 C5 C7 N4 63.64(19) . . . . ?
C4 C5 C7 N4 -60.03(19) . . . . ?
C6 C5 C7 S1 -117.94(14) . . . . ?
C4 C5 C7 S1 118.39(13) . . . . ?
C8 S1 C7 N4 -0.42(13) . . . . ?
C8 S1 C7 C5 -178.97(14) . . . . ?
C7 S1 C8 C9 0.48(13) . . . . ?
S1 C8 C9 N4 -0.46(18) . . . . ?
S1 C8 C9 C11 177.07(13) . . . . ?
C7 N4 C9 C8 0.14(19) . . . . ?
C7 N4 C9 C11 -177.53(14) . . . . ?
C8 C9 C11 C16 179.24(16) . . . . ?
N4 C9 C11 C16 -3.4(2) . . . . ?
C8 C9 C11 C12 -3.4(3) . . . . ?
N4 C9 C11 C12 173.96(15) . . . . ?
C16 C11 C12 C13 3.6(3) . . . . ?
C9 C11 C12 C13 -173.76(16) . . . . ?
C11 C12 C13 C14 -0.7(3) . . . . ?
C12 C13 C14 C15 -2.5(3) . . . . ?
C12 C13 C14 C10 174.11(17) . . . . ?
C13 C14 C15 C16 2.8(3) . . . . ?
C10 C14 C15 C16 -173.74(16) . . . . ?
C14 C15 C16 C11 0.1(3) . . . . ?
C12 C11 C16 C15 -3.3(2) . . . . ?
C9 C11 C16 C15 174.07(16) . . . . ?
O1 C4 C21 C26 -179.48(15) . . . . ?
C3 C4 C21 C26 -59.18(19) . . . . ?
C5 C4 C21 C26 60.2(2) . . . . ?
O1 C4 C21 C22 -0.48(19) . . . . ?
C3 C4 C21 C22 119.82(16) . . . . ?
C5 C4 C21 C22 -120.80(15) . . . . ?
C26 C21 C22 C23 -0.9(2) . . . . ?
C4 C21 C22 C23 179.99(15) . . . . ?
C21 C22 C23 F2 -179.85(15) . . . . ?
C21 C22 C23 C24 -0.2(3) . . . . ?
F2 C23 C24 C25 -179.16(15) . . . . ?
C22 C23 C24 C25 1.2(3) . . . . ?
C23 C24 C25 C26 -1.0(3) . . . . ?
C24 C25 C26 F1 179.54(16) . . . . ?
C24 C25 C26 C21 -0.2(3) . . . . ?
C22 C21 C26 F1 -178.56(15) . . . . ?
C4 C21 C26 F1 0.5(2) . . . . ?
C22 C21 C26 C25 1.1(2) . . . . ?
C4 C21 C26 C25 -179.83(16) . . . . ?

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 H4 N4 0.75(3) 2.18(3) 2.8457(18) 148(3) .

_refine_diff_density_max         0.312
_refine_diff_density_min         -0.186
_refine_diff_density_rms         0.041



####################################################################### 
# 
# 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_a_CCDC2
_database_code_depnum_ccdc_archive 'CCDC 2113412'
loop_
_audit_author_name
_audit_author_address
'Andrei Churakov'
;Institute of General and Inorganic Chemistry RAS
Russia
;
_audit_update_record             
;
2021-10-01 deposited with the CCDC.	2021-11-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C22 H17.52 F2 N5 O S, H2.48 O4 P'
_chemical_formula_sum            'C22 H20 F2 N5 O5 P S'
_chemical_formula_weight         535.46

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'
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'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.1023 0.0942 '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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

_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+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   6.1215(3)
_cell_length_b                   11.1722(5)
_cell_length_c                   34.3989(17)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2352.56(19)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9940
_cell_measurement_theta_min      2.174
_cell_measurement_theta_max      30.491

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.512
_exptl_crystal_F_000             1104
_exptl_transmission_factor_min   0.8588
_exptl_transmission_factor_max   0.9281
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.050
_exptl_absorpt_coefficient_mu    0.267
_shelx_estimated_absorpt_T_min   0.924
_shelx_estimated_absorpt_T_max   0.987
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   'SADABS (Bruker, 2016)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            26066
_diffrn_reflns_av_unetI/netI     0.0281
_diffrn_reflns_av_R_equivalents  0.0297
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -48
_diffrn_reflns_limit_l_max       48
_diffrn_reflns_theta_min         1.917
_diffrn_reflns_theta_max         29.998
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             6870
_reflns_number_gt                6622
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.747
_reflns_Friedel_fraction_max     0.999
_reflns_Friedel_fraction_full    0.999

_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       'APEX3 (Bruker, 2018)'
_computing_cell_refinement       'SAINT (Bruker, 2018)'
_computing_data_reduction        'SAINT (Bruker, 2018)'
_computing_structure_solution    'SHELXT (Sheldrick, 2016)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_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)+(0.0339P)²+0.3870P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refxyz
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 2717 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.00(2)
_chemical_absolute_configuration rmad
_refine_ls_number_reflns         6870
_refine_ls_number_parameters     408
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0292
_refine_ls_R_factor_gt           0.0276
_refine_ls_wR_factor_ref         0.0670
_refine_ls_wR_factor_gt          0.0660
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_restrained_S_all      1.062
_refine_ls_shift/su_max          0.002
_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
S1 S 1.52875(7) 0.32657(4) 0.62543(2) 0.01682(9) Uani 1 1 d . . . . .
F1 F 1.4081(2) 0.73575(10) 0.58136(3) 0.0234(2) Uani 1 1 d . . . . .
F2 F 0.6594(2) 0.94000(11) 0.63338(4) 0.0343(3) Uani 1 1 d . . . . .
O1 O 0.9065(2) 0.53410(11) 0.63646(4) 0.0153(2) Uani 1 1 d . . . . .
N1 N 0.9269(2) 0.55249(12) 0.55158(4) 0.0125(3) Uani 1 1 d . . . . .
N2 N 0.9249(2) 0.65887(13) 0.53205(4) 0.0154(3) Uani 1 1 d . . . . .
N3 N 0.6283(2) 0.55143(13) 0.51836(4) 0.0149(3) Uani 1 1 d . . . . .
H3A H 0.510(9) 0.533(4) 0.5075(14) 0.018 Uiso 0.52(5) 1 d . U P A 1
N4 N 1.1759(2) 0.34853(12) 0.66449(4) 0.0132(3) Uani 1 1 d . . . . .
N5 N 0.5506(3) -0.17641(17) 0.75268(5) 0.0301(4) Uani 1 1 d . . . . .
C1 C 0.7420(3) 0.65469(16) 0.51238(5) 0.0158(3) Uani 1 1 d . . . . .
C2 C 0.7498(3) 0.48954(15) 0.54337(5) 0.0142(3) Uani 1 1 d . . . . .
C3 C 1.1102(3) 0.52109(16) 0.57668(5) 0.0135(3) Uani 1 1 d . . . . .
C4 C 1.0960(3) 0.57826(14) 0.61740(5) 0.0115(3) Uani 1 1 d . . . . .
C5 C 1.3081(3) 0.54477(14) 0.64014(5) 0.0122(3) Uani 1 1 d . . . . .
C6 C 1.3224(4) 0.60801(16) 0.67967(5) 0.0180(3) Uani 1 1 d . . . . .
C7 C 1.3207(3) 0.41057(14) 0.64536(5) 0.0126(3) Uani 1 1 d . . . . .
C8 C 1.4136(3) 0.20000(15) 0.64423(5) 0.0166(3) Uani 1 1 d . . . . .
C9 C 1.2299(3) 0.22753(14) 0.66486(5) 0.0130(3) Uani 1 1 d . . . . .
C10 C 0.6744(3) -0.10930(16) 0.74038(5) 0.0202(4) Uani 1 1 d . . . . .
C11 C 1.0934(3) 0.14239(15) 0.68658(5) 0.0136(3) Uani 1 1 d . . . . .
C12 C 1.1644(3) 0.02480(16) 0.69308(5) 0.0170(3) Uani 1 1 d . . . . .
C13 C 1.0312(3) -0.05731(16) 0.71174(5) 0.0180(3) Uani 1 1 d . . . . .
C14 C 0.8231(3) -0.02303(15) 0.72381(5) 0.0161(3) Uani 1 1 d . . . . .
C15 C 0.7533(3) 0.09502(16) 0.71896(5) 0.0167(3) Uani 1 1 d . . . . .
C16 C 0.8888(3) 0.17699(16) 0.70074(5) 0.0158(3) Uani 1 1 d . . . . .
C21 C 1.0686(3) 0.71369(14) 0.61377(5) 0.0132(3) Uani 1 1 d . . . . .
C22 C 0.8776(3) 0.76872(16) 0.62685(5) 0.0173(3) Uani 1 1 d . . . . .
C23 C 0.8491(3) 0.88971(17) 0.62035(6) 0.0228(4) Uani 1 1 d . . . . .
C24 C 1.0002(4) 0.96060(17) 0.60213(6) 0.0266(5) Uani 1 1 d . . . . .
C25 C 1.1919(4) 0.90761(16) 0.58936(5) 0.0228(4) Uani 1 1 d . . . . .
C26 C 1.2205(3) 0.78613(16) 0.59540(5) 0.0177(3) Uani 1 1 d . . . . .
H1 H 0.698(4) 0.720(2) 0.4944(7) 0.019(6) Uiso 1 1 d . . . . .
H2 H 0.722(4) 0.415(2) 0.5525(6) 0.015(5) Uiso 1 1 d . . . . .
H4 H 0.947(4) 0.468(2) 0.6479(7) 0.025(6) Uiso 1 1 d . . . . .
H5 H 1.423(3) 0.5692(18) 0.6241(6) 0.008(5) Uiso 1 1 d . . . . .
H8 H 1.476(4) 0.124(2) 0.6408(7) 0.021(6) Uiso 1 1 d . . . . .
H12 H 1.305(4) 0.0012(18) 0.6843(6) 0.011(5) Uiso 1 1 d . . . . .
H13 H 1.082(4) -0.138(2) 0.7157(6) 0.020(6) Uiso 1 1 d . . . . .
H15 H 0.619(4) 0.119(2) 0.7284(6) 0.015(5) Uiso 1 1 d . . . . .
H16 H 0.844(4) 0.2562(19) 0.6996(6) 0.013(5) Uiso 1 1 d . . . . .
H22 H 0.763(4) 0.722(2) 0.6396(7) 0.031(7) Uiso 1 1 d . . . . .
H24 H 0.972(5) 1.039(2) 0.5997(7) 0.034(7) Uiso 1 1 d . . . . .
H25 H 1.299(4) 0.953(2) 0.5773(7) 0.030(7) Uiso 1 1 d . . . . .
H31 H 1.238(4) 0.5464(19) 0.5630(6) 0.011(5) Uiso 1 1 d . . . . .
H32 H 1.108(4) 0.439(2) 0.5798(6) 0.013(5) Uiso 1 1 d . . . . .
H61 H 1.328(4) 0.693(2) 0.6762(6) 0.019(6) Uiso 1 1 d . . . . .
H62 H 1.184(5) 0.590(2) 0.6942(7) 0.028(6) Uiso 1 1 d . . . . .
H63 H 1.449(4) 0.578(2) 0.6938(6) 0.017(6) Uiso 1 1 d . . . . .
P1 P 0.19756(7) 0.36329(4) 0.48102(2) 0.01155(9) Uani 1 1 d . . . . .
O10 O -0.0329(2) 0.37322(12) 0.46207(4) 0.0169(3) Uani 1 1 d . . . . .
O11 O 0.3388(2) 0.29379(11) 0.45011(4) 0.0152(2) Uani 1 1 d . . . . .
O12 O 0.2793(2) 0.48951(11) 0.48587(4) 0.0175(3) Uani 1 1 d . . . . .
H3B H 0.408(11) 0.493(5) 0.4943(17) 0.026 Uiso 0.48(5) 1 d . U P A 2
O13 O 0.1905(2) 0.29087(11) 0.51831(3) 0.0154(2) Uani 1 1 d . . . . .
H10 H -0.100(5) 0.318(3) 0.4666(9) 0.043(9) Uiso 1 1 d . . . . .
H11 H 0.453(5) 0.268(2) 0.4587(8) 0.033(7) Uiso 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 C8 1.7073(18) . ?
S1 C7 1.7242(17) . ?
F1 C26 1.367(2) . ?
F2 C23 1.366(2) . ?
O1 C4 1.421(2) . ?
O1 H4 0.87(2) . ?
N1 C2 1.322(2) . ?
N1 N2 1.3653(19) . ?
N1 C3 1.459(2) . ?
N2 C1 1.309(2) . ?
N3 C2 1.331(2) . ?
N3 C1 1.363(2) . ?
N3 H3A 0.84(6) . ?
N4 C7 1.303(2) . ?
N4 C9 1.392(2) . ?
N5 C10 1.147(3) . ?
C1 H1 0.99(2) . ?
C2 H2 0.91(2) . ?
C3 C4 1.542(2) . ?
C3 H31 0.96(2) . ?
C3 H32 0.92(2) . ?
C4 C21 1.527(2) . ?
C4 C5 1.561(2) . ?
C5 C7 1.512(2) . ?
C5 C6 1.535(2) . ?
C5 H5 0.93(2) . ?
C6 H61 0.96(2) . ?
C6 H62 1.00(3) . ?
C6 H63 0.97(2) . ?
C8 C9 1.365(2) . ?
C8 H8 0.94(2) . ?
C9 C11 1.470(2) . ?
C10 C14 1.443(3) . ?
C11 C16 1.398(2) . ?
C11 C12 1.402(2) . ?
C12 C13 1.385(3) . ?
C12 H12 0.95(2) . ?
C13 C14 1.394(3) . ?
C13 H13 0.97(2) . ?
C14 C15 1.396(2) . ?
C15 C16 1.385(3) . ?
C15 H15 0.92(2) . ?
C16 H16 0.93(2) . ?
C21 C26 1.385(2) . ?
C21 C22 1.395(2) . ?
C22 C23 1.381(2) . ?
C22 H22 0.98(3) . ?
C23 C24 1.370(3) . ?
C24 C25 1.386(3) . ?
C24 H24 0.90(3) . ?
C25 C26 1.384(2) . ?
C25 H25 0.93(3) . ?
P1 O12 1.5055(13) . ?
P1 O13 1.5174(12) . ?
P1 O10 1.5579(13) . ?
P1 O11 1.5749(13) . ?
O10 H10 0.76(3) . ?
O11 H11 0.81(3) . ?
O12 H3B 0.84(7) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C8 S1 C7 89.73(9) . . ?
C4 O1 H4 105.7(17) . . ?
C2 N1 N2 110.53(14) . . ?
C2 N1 C3 128.97(14) . . ?
N2 N1 C3 120.49(14) . . ?
C1 N2 N1 103.34(14) . . ?
C2 N3 C1 104.59(15) . . ?
C2 N3 H3A 130(3) . . ?
C1 N3 H3A 125(3) . . ?
C7 N4 C9 111.10(14) . . ?
N2 C1 N3 112.89(15) . . ?
N2 C1 H1 121.7(14) . . ?
N3 C1 H1 125.4(14) . . ?
N1 C2 N3 108.66(15) . . ?
N1 C2 H2 124.8(14) . . ?
N3 C2 H2 126.4(14) . . ?
N1 C3 C4 113.25(14) . . ?
N1 C3 H31 105.4(12) . . ?
C4 C3 H31 111.8(12) . . ?
N1 C3 H32 107.2(14) . . ?
C4 C3 H32 107.7(13) . . ?
H31 C3 H32 111.4(19) . . ?
O1 C4 C21 106.98(14) . . ?
O1 C4 C3 108.74(13) . . ?
C21 C4 C3 110.02(13) . . ?
O1 C4 C5 111.38(13) . . ?
C21 C4 C5 111.69(14) . . ?
C3 C4 C5 108.01(13) . . ?
C7 C5 C6 110.38(13) . . ?
C7 C5 C4 109.86(14) . . ?
C6 C5 C4 112.40(14) . . ?
C7 C5 H5 108.8(12) . . ?
C6 C5 H5 110.2(13) . . ?
C4 C5 H5 105.0(12) . . ?
C5 C6 H61 110.3(13) . . ?
C5 C6 H62 107.5(15) . . ?
H61 C6 H62 107(2) . . ?
C5 C6 H63 109.3(13) . . ?
H61 C6 H63 112(2) . . ?
H62 C6 H63 110.5(18) . . ?
N4 C7 C5 123.54(15) . . ?
N4 C7 S1 114.42(12) . . ?
C5 C7 S1 122.03(13) . . ?
C9 C8 S1 110.52(13) . . ?
C9 C8 H8 127.1(15) . . ?
S1 C8 H8 122.4(15) . . ?
C8 C9 N4 114.17(15) . . ?
C8 C9 C11 125.93(16) . . ?
N4 C9 C11 119.90(15) . . ?
N5 C10 C14 177.6(2) . . ?
C16 C11 C12 118.78(16) . . ?
C16 C11 C9 120.48(15) . . ?
C12 C11 C9 120.74(16) . . ?
C13 C12 C11 120.81(17) . . ?
C13 C12 H12 119.8(13) . . ?
C11 C12 H12 119.3(13) . . ?
C12 C13 C14 119.61(16) . . ?
C12 C13 H13 119.8(15) . . ?
C14 C13 H13 120.6(15) . . ?
C13 C14 C15 120.23(16) . . ?
C13 C14 C10 120.71(17) . . ?
C15 C14 C10 119.03(18) . . ?
C16 C15 C14 119.70(17) . . ?
C16 C15 H15 120.2(14) . . ?
C14 C15 H15 120.0(14) . . ?
C15 C16 C11 120.73(17) . . ?
C15 C16 H16 118.3(14) . . ?
C11 C16 H16 120.9(14) . . ?
C26 C21 C22 116.87(16) . . ?
C26 C21 C4 122.84(16) . . ?
C22 C21 C4 120.14(16) . . ?
C23 C22 C21 119.02(18) . . ?
C23 C22 H22 120.0(15) . . ?
C21 C22 H22 120.9(15) . . ?
F2 C23 C24 119.12(18) . . ?
F2 C23 C22 117.20(19) . . ?
C24 C23 C22 123.68(19) . . ?
C23 C24 C25 118.03(17) . . ?
C23 C24 H24 118.6(18) . . ?
C25 C24 H24 123.4(18) . . ?
C26 C25 C24 118.6(2) . . ?
C26 C25 H25 120.9(16) . . ?
C24 C25 H25 120.6(16) . . ?
F1 C26 C25 117.19(18) . . ?
F1 C26 C21 118.98(15) . . ?
C25 C26 C21 123.81(19) . . ?
O12 P1 O13 114.52(7) . . ?
O12 P1 O10 106.29(8) . . ?
O13 P1 O10 111.46(7) . . ?
O12 P1 O11 110.75(7) . . ?
O13 P1 O11 108.88(7) . . ?
O10 P1 O11 104.46(7) . . ?
P1 O10 H10 110(2) . . ?
P1 O11 H11 113.5(19) . . ?
P1 O12 H3B 113(4) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C2 N1 N2 C1 -0.14(18) . . . . ?
C3 N1 N2 C1 178.72(15) . . . . ?
N1 N2 C1 N3 -0.11(19) . . . . ?
C2 N3 C1 N2 0.3(2) . . . . ?
N2 N1 C2 N3 0.34(19) . . . . ?
C3 N1 C2 N3 -178.39(16) . . . . ?
C1 N3 C2 N1 -0.38(19) . . . . ?
C2 N1 C3 C4 -99.7(2) . . . . ?
N2 N1 C3 C4 81.70(18) . . . . ?
N1 C3 C4 O1 62.75(18) . . . . ?
N1 C3 C4 C21 -54.11(19) . . . . ?
N1 C3 C4 C5 -176.25(13) . . . . ?
O1 C4 C5 C7 56.68(17) . . . . ?
C21 C4 C5 C7 176.23(14) . . . . ?
C3 C4 C5 C7 -62.66(17) . . . . ?
O1 C4 C5 C6 -66.66(17) . . . . ?
C21 C4 C5 C6 52.89(19) . . . . ?
C3 C4 C5 C6 174.00(14) . . . . ?
C9 N4 C7 C5 -179.50(15) . . . . ?
C9 N4 C7 S1 1.55(18) . . . . ?
C6 C5 C7 N4 62.9(2) . . . . ?
C4 C5 C7 N4 -61.6(2) . . . . ?
C6 C5 C7 S1 -118.23(15) . . . . ?
C4 C5 C7 S1 117.26(14) . . . . ?
C8 S1 C7 N4 -0.22(14) . . . . ?
C8 S1 C7 C5 -179.18(15) . . . . ?
C7 S1 C8 C9 -1.21(14) . . . . ?
S1 C8 C9 N4 2.4(2) . . . . ?
S1 C8 C9 C11 -177.14(14) . . . . ?
C7 N4 C9 C8 -2.5(2) . . . . ?
C7 N4 C9 C11 176.99(15) . . . . ?
C8 C9 C11 C16 -168.46(17) . . . . ?
N4 C9 C11 C16 12.1(2) . . . . ?
C8 C9 C11 C12 10.7(3) . . . . ?
N4 C9 C11 C12 -168.72(16) . . . . ?
C16 C11 C12 C13 2.7(3) . . . . ?
C9 C11 C12 C13 -176.57(16) . . . . ?
C11 C12 C13 C14 0.7(3) . . . . ?
C12 C13 C14 C15 -3.3(3) . . . . ?
C12 C13 C14 C10 174.80(17) . . . . ?
C13 C14 C15 C16 2.4(3) . . . . ?
C10 C14 C15 C16 -175.71(17) . . . . ?
C14 C15 C16 C11 1.0(3) . . . . ?
C12 C11 C16 C15 -3.5(3) . . . . ?
C9 C11 C16 C15 175.69(16) . . . . ?
O1 C4 C21 C26 -177.84(15) . . . . ?
C3 C4 C21 C26 -59.9(2) . . . . ?
C5 C4 C21 C26 60.0(2) . . . . ?
O1 C4 C21 C22 -2.4(2) . . . . ?
C3 C4 C21 C22 115.56(17) . . . . ?
C5 C4 C21 C22 -124.50(16) . . . . ?
C26 C21 C22 C23 1.0(2) . . . . ?
C4 C21 C22 C23 -174.69(16) . . . . ?
C21 C22 C23 F2 179.60(15) . . . . ?
C21 C22 C23 C24 -1.1(3) . . . . ?
F2 C23 C24 C25 179.64(16) . . . . ?
C22 C23 C24 C25 0.3(3) . . . . ?
C23 C24 C25 C26 0.4(3) . . . . ?
C24 C25 C26 F1 177.93(16) . . . . ?
C24 C25 C26 C21 -0.4(3) . . . . ?
C22 C21 C26 F1 -178.63(15) . . . . ?
C4 C21 C26 F1 -3.0(3) . . . . ?
C22 C21 C26 C25 -0.3(3) . . . . ?
C4 C21 C26 C25 175.27(17) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N3 H3A^a O12 0.84(6) 1.67(6) 2.508(2) 177(5) . yes
O12 H3B^b N3 0.84(7) 1.71(7) 2.508(2) 158(6) . yes
O1 H4 N4 0.87(2) 2.02(3) 2.8193(19) 152(2) . yes
O10 H10 O13 0.76(3) 1.84(3) 2.5853(18) 167(3) 4_456 yes
O11 H11 O13 0.81(3) 1.78(3) 2.5903(18) 175(3) 4_556 yes

_refine_diff_density_max         0.298
_refine_diff_density_min         -0.279
_refine_diff_density_rms         0.044



