# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2020

####################################################################### 
# 
# 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_AK119
_database_code_depnum_ccdc_archive 'CCDC 1969751'
loop_
_audit_author_name
_audit_author_address
'Anna Sinelshchikova'
;Frumkin Institute of Physical Chemistry and Electrochemistry, Russian Academy of Sciences (IPCE RAS)
Russia
;
_audit_update_record             
;
2019-12-03 deposited with the CCDC.	2020-08-12 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         'C19 H23 Cl2 N3 O4 S2'
_chemical_formula_sum            'C19 H23 Cl2 N3 O4 S2'
_chemical_formula_weight         492.42

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'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           62
_space_group_name_H-M_alt        'P n m a'
_space_group_name_Hall           '-P 2ac 2n'

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

_cell_length_a                   15.0501(4)
_cell_length_b                   23.9887(8)
_cell_length_c                   6.1915(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2235.33(12)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    5592
_cell_measurement_theta_min      2.84
_cell_measurement_theta_max      27.79

_exptl_crystal_description       fragment
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.463
_exptl_crystal_F_000             1024
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.060
_exptl_absorpt_coefficient_mu    0.508
_shelx_estimated_absorpt_T_min   0.822
_shelx_estimated_absorpt_T_max   0.970
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.873
_exptl_absorpt_correction_T_max  0.970
_exptl_absorpt_process_details   'SADABS (Bruker, 2008)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  
'Bruker KAPPA APEX II area-detector diffractometer'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            23321
_diffrn_reflns_av_unetI/netI     0.0202
_diffrn_reflns_av_R_equivalents  0.0298
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_k_min       -33
_diffrn_reflns_limit_k_max       33
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_theta_min         3.943
_diffrn_reflns_theta_max         30.000
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.994
_reflns_number_total             3322
_reflns_number_gt                2344
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-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)+(0.0514P)²+1.5273P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3322
_refine_ls_number_parameters     142
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0771
_refine_ls_R_factor_gt           0.0508
_refine_ls_wR_factor_ref         0.1375
_refine_ls_wR_factor_gt          0.1212
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_restrained_S_all      1.029
_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
Cl1 Cl 0.65756(5) 0.47550(3) 0.80188(16) 0.0867(3) Uani 1 1 d . . . . .
S1 S 0.35220(4) 0.35607(3) 0.30119(9) 0.05291(18) Uani 1 1 d . . . . .
O1 O 0.27328(12) 0.38833(8) 0.3231(4) 0.0771(6) Uani 1 1 d . . . . .
O2 O 0.38531(14) 0.34111(8) 0.0931(3) 0.0722(6) Uani 1 1 d . . . . .
N1 N 0.23557(16) 0.250000 0.6729(4) 0.0447(6) Uani 1 2 d S T P . .
N3 N 0.33405(12) 0.29858(8) 0.4291(3) 0.0506(4) Uani 1 1 d . . . . .
C2 C 0.28932(17) 0.29873(11) 0.6440(4) 0.0581(6) Uani 1 1 d . . . . .
H2A H 0.333900 0.300258 0.757005 0.070 Uiso 1 1 calc R U . . .
H2B H 0.252356 0.331697 0.656396 0.070 Uiso 1 1 calc R U . . .
C4 C 0.3907(2) 0.250000 0.3973(6) 0.0524(7) Uani 1 2 d S T P . .
H4A H 0.439110 0.250000 0.500809 0.063 Uiso 1 2 calc R U P . .
H4B H 0.415551 0.250000 0.252766 0.063 Uiso 1 2 calc R U P . .
C5 C 0.14363(19) 0.250000 0.5793(5) 0.0427(6) Uani 1 2 d S T P . .
C6 C 0.1410(2) 0.250000 0.3332(5) 0.0555(8) Uani 1 2 d S T P . .
H6A H 0.080311 0.250000 0.285350 0.083 Uiso 1 2 calc R U P . .
H6B H 0.170488 0.282675 0.279628 0.083 Uiso 0.5 1 calc R U P . .
H6C H 0.170488 0.217325 0.279627 0.083 Uiso 0.5 1 calc R U P . .
C7 C 0.09532(19) 0.30102(12) 0.6646(5) 0.0706(7) Uani 1 1 d . . . . .
H7A H 0.036146 0.301956 0.606799 0.106 Uiso 1 1 calc R U . . .
H7B H 0.092594 0.299314 0.819347 0.106 Uiso 1 1 calc R U . . .
H7C H 0.126677 0.334053 0.621533 0.106 Uiso 1 1 calc R U . . .
C8 C 0.43799(13) 0.39190(8) 0.4372(3) 0.0412(4) Uani 1 1 d . . . . .
C9 C 0.42026(15) 0.41747(9) 0.6328(4) 0.0507(5) Uani 1 1 d . . . . .
H9A H 0.363019 0.417168 0.689392 0.061 Uiso 1 1 calc R U . . .
C10 C 0.48826(17) 0.44338(10) 0.7431(4) 0.0555(6) Uani 1 1 d . . . . .
H10A H 0.477321 0.460324 0.875515 0.067 Uiso 1 1 calc R U . . .
C11 C 0.57192(15) 0.44407(9) 0.6567(4) 0.0520(5) Uani 1 1 d . . . . .
C12 C 0.59017(15) 0.41996(10) 0.4615(4) 0.0585(6) Uani 1 1 d . . . . .
H12A H 0.647164 0.421537 0.403837 0.070 Uiso 1 1 calc R U . . .
C13 C 0.52228(15) 0.39305(9) 0.3506(4) 0.0504(5) Uani 1 1 d . . . . .
H13A H 0.533704 0.375926 0.218776 0.060 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl1 C11 1.743(2) . ?
S1 O1 1.4241(19) . ?
S1 O2 1.4275(19) . ?
S1 N3 1.614(2) . ?
S1 C8 1.765(2) . ?
N1 C2 1.433(3) 7_565 ?
N1 C2 1.433(3) . ?
N1 C5 1.500(4) . ?
N3 C4 1.458(3) . ?
N3 C2 1.491(3) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C5 C7 1.518(3) . ?
C5 C7 1.519(3) 7_565 ?
C5 C6 1.524(4) . ?
C6 H6A 0.9600 . ?
C6 H6B 0.9600 . ?
C6 H6C 0.9600 . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C8 C13 1.377(3) . ?
C8 C9 1.384(3) . ?
C9 C10 1.378(3) . ?
C9 H9A 0.9300 . ?
C10 C11 1.368(3) . ?
C10 H10A 0.9300 . ?
C11 C12 1.368(4) . ?
C12 C13 1.390(3) . ?
C12 H12A 0.9300 . ?
C13 H13A 0.9300 . ?

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
O1 S1 O2 120.92(13) . . ?
O1 S1 N3 106.05(11) . . ?
O2 S1 N3 106.71(11) . . ?
O1 S1 C8 107.46(10) . . ?
O2 S1 C8 107.31(11) . . ?
N3 S1 C8 107.81(10) . . ?
C2 N1 C2 109.3(3) 7_565 . ?
C2 N1 C5 118.21(15) 7_565 . ?
C2 N1 C5 118.21(15) . . ?
C4 N3 C2 112.7(2) . . ?
C4 N3 S1 121.19(16) . . ?
C2 N3 S1 120.83(16) . . ?
N1 C2 N3 111.36(18) . . ?
N1 C2 H2A 109.4 . . ?
N3 C2 H2A 109.4 . . ?
N1 C2 H2B 109.4 . . ?
N3 C2 H2B 109.4 . . ?
H2A C2 H2B 108.0 . . ?
N3 C4 N3 106.2(2) . 7_565 ?
N3 C4 H4A 110.5 . . ?
N3 C4 H4A 110.5 7_565 . ?
N3 C4 H4B 110.5 . . ?
N3 C4 H4B 110.5 7_565 . ?
H4A C4 H4B 108.7 . . ?
N1 C5 C7 107.89(18) . . ?
N1 C5 C7 107.89(18) . 7_565 ?
C7 C5 C7 107.4(3) . 7_565 ?
N1 C5 C6 114.2(2) . . ?
C7 C5 C6 109.59(19) . . ?
C7 C5 C6 109.59(19) 7_565 . ?
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 . . ?
C5 C7 H7A 109.5 . . ?
C5 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C5 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C13 C8 C9 120.61(19) . . ?
C13 C8 S1 119.87(17) . . ?
C9 C8 S1 119.50(16) . . ?
C10 C9 C8 119.4(2) . . ?
C10 C9 H9A 120.3 . . ?
C8 C9 H9A 120.3 . . ?
C11 C10 C9 119.7(2) . . ?
C11 C10 H10A 120.2 . . ?
C9 C10 H10A 120.2 . . ?
C12 C11 C10 121.7(2) . . ?
C12 C11 Cl1 119.36(19) . . ?
C10 C11 Cl1 119.0(2) . . ?
C11 C12 C13 119.0(2) . . ?
C11 C12 H12A 120.5 . . ?
C13 C12 H12A 120.5 . . ?
C8 C13 C12 119.6(2) . . ?
C8 C13 H13A 120.2 . . ?
C12 C13 H13A 120.2 . . ?

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
O1 S1 N3 C4 164.5(2) . . . . ?
O2 S1 N3 C4 34.4(2) . . . . ?
C8 S1 N3 C4 -80.6(2) . . . . ?
O1 S1 N3 C2 -42.9(2) . . . . ?
O2 S1 N3 C2 -173.03(17) . . . . ?
C8 S1 N3 C2 71.96(19) . . . . ?
C2 N1 C2 N3 56.2(3) 7_565 . . . ?
C5 N1 C2 N3 -83.0(3) . . . . ?
C4 N3 C2 N1 -58.7(3) . . . . ?
S1 N3 C2 N1 146.56(18) . . . . ?
C2 N3 C4 N3 56.4(3) . . . 7_565 ?
S1 N3 C4 N3 -149.02(13) . . . 7_565 ?
C2 N1 C5 C7 170.1(2) 7_565 . . . ?
C2 N1 C5 C7 -54.3(3) . . . . ?
C2 N1 C5 C7 54.3(3) 7_565 . . 7_565 ?
C2 N1 C5 C7 -170.1(2) . . . 7_565 ?
C2 N1 C5 C6 -67.79(18) 7_565 . . . ?
C2 N1 C5 C6 67.79(18) . . . . ?
O1 S1 C8 C13 -141.23(19) . . . . ?
O2 S1 C8 C13 -9.8(2) . . . . ?
N3 S1 C8 C13 104.85(19) . . . . ?
O1 S1 C8 C9 40.3(2) . . . . ?
O2 S1 C8 C9 171.81(18) . . . . ?
N3 S1 C8 C9 -73.58(19) . . . . ?
C13 C8 C9 C10 -1.2(3) . . . . ?
S1 C8 C9 C10 177.26(18) . . . . ?
C8 C9 C10 C11 0.8(4) . . . . ?
C9 C10 C11 C12 0.5(4) . . . . ?
C9 C10 C11 Cl1 -178.38(18) . . . . ?
C10 C11 C12 C13 -1.4(4) . . . . ?
Cl1 C11 C12 C13 177.49(18) . . . . ?
C9 C8 C13 C12 0.3(3) . . . . ?
S1 C8 C13 C12 -178.14(17) . . . . ?
C11 C12 C13 C8 1.0(4) . . . . ?

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
C2 H2A O2 0.97 2.43 3.294(3) 148.7 1_556 yes
C12 H12A O1 0.93 2.49 3.358(3) 155.0 8_656 yes

_refine_diff_density_max         0.545
_refine_diff_density_min         -0.419
_refine_diff_density_rms         0.048


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: CH2Cl2'
####################################################################### 
# 
# 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_ftr
_database_code_depnum_ccdc_archive 'CCDC 1969754'
loop_
_audit_author_name
_audit_author_address
'Anna Sinelshchikova'
;Frumkin Institute of Physical Chemistry and Electrochemistry, Russian Academy of Sciences (IPCE RAS)
Russia
;
_audit_update_record             
;
2019-12-03 deposited with the CCDC.	2020-08-12 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         'C19 H23 F2 N3 O4 S2'
_chemical_formula_sum            'C19 H23 F2 N3 O4 S2'
_chemical_formula_weight         459.52

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

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   15.0587(11)
_cell_length_b                   11.9394(9)
_cell_length_c                   11.6556(8)
_cell_angle_alpha                90
_cell_angle_beta                 90.844(4)
_cell_angle_gamma                90
_cell_volume                     2095.4(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    7718
_cell_measurement_theta_min      2.78
_cell_measurement_theta_max      30.12

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.457
_exptl_crystal_F_000             960
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.360
_exptl_crystal_size_mid          0.320
_exptl_crystal_size_min          0.060
_exptl_absorpt_coefficient_mu    0.303
_shelx_estimated_absorpt_T_min   0.899
_shelx_estimated_absorpt_T_max   0.982
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.794
_exptl_absorpt_correction_T_max  0.982
_exptl_absorpt_process_details   'SADABS (Bruker, 2008)'
_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 KAPPA APEX II area-detector diffractometer'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            22747
_diffrn_reflns_av_unetI/netI     0.0506
_diffrn_reflns_av_R_equivalents  0.0557
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         4.076
_diffrn_reflns_theta_max         29.999
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.993
_reflns_number_total             6088
_reflns_number_gt                5033
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-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)+(0.0427P)²+0.7757P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         6088
_refine_ls_number_parameters     271
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0475
_refine_ls_R_factor_gt           0.0368
_refine_ls_wR_factor_ref         0.1008
_refine_ls_wR_factor_gt          0.0936
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_restrained_S_all      1.026
_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 0.59964(2) 0.72027(3) 0.54180(3) 0.01419(8) Uani 1 1 d . . . . .
S2 S 0.92184(2) 0.84991(3) 0.64110(3) 0.01238(8) Uani 1 1 d . . . . .
F1 F 0.60499(7) 0.31685(8) 0.25844(9) 0.0315(2) Uani 1 1 d . . . . .
F2 F 1.16212(7) 0.51681(8) 0.45015(9) 0.0304(2) Uani 1 1 d . . . . .
O1 O 0.60642(7) 0.68696(9) 0.65963(8) 0.0205(2) Uani 1 1 d . . . . .
O2 O 0.52757(7) 0.78927(9) 0.50292(9) 0.0202(2) Uani 1 1 d . . . . .
O3 O 0.89387(7) 0.81332(9) 0.75210(8) 0.0172(2) Uani 1 1 d . . . . .
O4 O 0.96244(6) 0.95818(8) 0.62892(8) 0.0163(2) Uani 1 1 d . . . . .
N1 N 0.76007(7) 0.92275(9) 0.38685(9) 0.0134(2) Uani 1 1 d . . . . .
N3 N 0.69025(7) 0.79033(9) 0.51350(10) 0.0138(2) Uani 1 1 d . . . . .
N5 N 0.83448(7) 0.84992(9) 0.55693(9) 0.0131(2) Uani 1 1 d . . . . .
C2 C 0.70114(9) 0.82840(11) 0.39256(11) 0.0147(2) Uani 1 1 d . . . . .
H2A H 0.725150 0.766162 0.346244 0.018 Uiso 1 1 calc R U . . .
H2B H 0.642462 0.849335 0.359685 0.018 Uiso 1 1 calc R U . . .
C4 C 0.77524(9) 0.75183(11) 0.56189(12) 0.0144(2) Uani 1 1 d . . . . .
H4A H 0.799227 0.689150 0.516185 0.017 Uiso 1 1 calc R U . . .
H4B H 0.768144 0.726491 0.642107 0.017 Uiso 1 1 calc R U . . .
C6 C 0.84482(9) 0.89311(11) 0.43656(11) 0.0139(2) Uani 1 1 d . . . . .
H6A H 0.884034 0.959664 0.437635 0.017 Uiso 1 1 calc R U . . .
H6B H 0.873075 0.834845 0.388936 0.017 Uiso 1 1 calc R U . . .
C7 C 0.72569(9) 1.03770(11) 0.41248(12) 0.0155(3) Uani 1 1 d . . . . .
C8 C 0.73535(10) 1.07077(12) 0.53917(12) 0.0202(3) Uani 1 1 d . . . . .
H8A H 0.711746 1.146453 0.550110 0.030 Uiso 1 1 calc R U . . .
H8B H 0.702234 1.017799 0.586438 0.030 Uiso 1 1 calc R U . . .
H8C H 0.798249 1.069209 0.561927 0.030 Uiso 1 1 calc R U . . .
C9 C 0.62812(9) 1.04532(13) 0.37684(14) 0.0219(3) Uani 1 1 d . . . . .
H9A H 0.605736 1.120535 0.393653 0.033 Uiso 1 1 calc R U . . .
H9B H 0.621976 1.030541 0.294395 0.033 Uiso 1 1 calc R U . . .
H9C H 0.593896 0.989792 0.419533 0.033 Uiso 1 1 calc R U . . .
C10 C 0.77863(10) 1.11852(12) 0.33734(13) 0.0203(3) Uani 1 1 d . . . . .
H10A H 0.758601 1.195421 0.350908 0.030 Uiso 1 1 calc R U . . .
H10B H 0.841984 1.112411 0.356788 0.030 Uiso 1 1 calc R U . . .
H10C H 0.769129 1.099352 0.256332 0.030 Uiso 1 1 calc R U . . .
C11 C 0.59973(8) 0.59810(11) 0.45702(11) 0.0143(2) Uani 1 1 d . . . . .
C12 C 0.57014(9) 0.60372(12) 0.34309(12) 0.0167(3) Uani 1 1 d . . . . .
H12 H 0.548375 0.672208 0.312169 0.020 Uiso 1 1 calc R U . . .
C13 C 0.57287(9) 0.50805(13) 0.27548(12) 0.0190(3) Uani 1 1 d . . . . .
H13 H 0.554028 0.510199 0.197365 0.023 Uiso 1 1 calc R U . . .
C14 C 0.60340(10) 0.41026(12) 0.32395(13) 0.0207(3) Uani 1 1 d . . . . .
C15 C 0.63205(10) 0.40239(12) 0.43679(14) 0.0228(3) Uani 1 1 d . . . . .
H15 H 0.652265 0.333100 0.467549 0.027 Uiso 1 1 calc R U . . .
C16 C 0.63056(10) 0.49829(12) 0.50414(12) 0.0185(3) Uani 1 1 d . . . . .
H16 H 0.650474 0.495668 0.581812 0.022 Uiso 1 1 calc R U . . .
C21 C 0.99650(8) 0.74981(11) 0.58716(11) 0.0134(2) Uani 1 1 d . . . . .
C22 C 1.04064(9) 0.77395(11) 0.48592(12) 0.0162(3) Uani 1 1 d . . . . .
H22 H 1.032204 0.844267 0.449190 0.019 Uiso 1 1 calc R U . . .
C23 C 1.09693(9) 0.69490(12) 0.43899(12) 0.0187(3) Uani 1 1 d . . . . .
H23 H 1.126971 0.709204 0.369404 0.022 Uiso 1 1 calc R U . . .
C24 C 1.10795(10) 0.59456(12) 0.49671(14) 0.0207(3) Uani 1 1 d . . . . .
C25 C 1.06649(10) 0.56931(13) 0.59798(14) 0.0227(3) Uani 1 1 d . . . . .
H25 H 1.076994 0.499879 0.635610 0.027 Uiso 1 1 calc R U . . .
C26 C 1.00904(10) 0.64773(12) 0.64367(12) 0.0183(3) Uani 1 1 d . . . . .
H26 H 0.978542 0.632212 0.712649 0.022 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 O2 1.4309(11) . ?
S1 O1 1.4319(10) . ?
S1 N3 1.6381(12) . ?
S1 C11 1.7619(14) . ?
S2 O3 1.4346(10) . ?
S2 O4 1.4379(10) . ?
S2 N5 1.6295(11) . ?
S2 C21 1.7630(14) . ?
F1 C14 1.3520(16) . ?
F2 C24 1.3545(16) . ?
N1 C2 1.4362(17) . ?
N1 C6 1.4381(17) . ?
N1 C7 1.4984(17) . ?
N3 C4 1.4650(17) . ?
N3 C2 1.4924(17) . ?
N5 C4 1.4738(16) . ?
N5 C6 1.5050(16) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 C9 1.5238(19) . ?
C7 C8 1.533(2) . ?
C7 C10 1.5344(19) . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 C16 1.3891(19) . ?
C11 C12 1.3961(19) . ?
C12 C13 1.389(2) . ?
C12 H12 0.9500 . ?
C13 C14 1.373(2) . ?
C13 H13 0.9500 . ?
C14 C15 1.381(2) . ?
C15 C16 1.389(2) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?
C21 C22 1.3930(19) . ?
C21 C26 1.3969(18) . ?
C22 C23 1.3865(19) . ?
C22 H22 0.9500 . ?
C23 C24 1.383(2) . ?
C23 H23 0.9500 . ?
C24 C25 1.377(2) . ?
C25 C26 1.387(2) . ?
C25 H25 0.9500 . ?
C26 H26 0.9500 . ?

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
O2 S1 O1 120.44(7) . . ?
O2 S1 N3 105.80(6) . . ?
O1 S1 N3 106.69(6) . . ?
O2 S1 C11 107.81(6) . . ?
O1 S1 C11 107.90(7) . . ?
N3 S1 C11 107.60(6) . . ?
O3 S2 O4 119.59(6) . . ?
O3 S2 N5 107.32(6) . . ?
O4 S2 N5 106.33(6) . . ?
O3 S2 C21 108.21(6) . . ?
O4 S2 C21 107.46(6) . . ?
N5 S2 C21 107.38(6) . . ?
C2 N1 C6 109.48(10) . . ?
C2 N1 C7 119.58(11) . . ?
C6 N1 C7 116.89(11) . . ?
C4 N3 C2 110.59(10) . . ?
C4 N3 S1 119.19(9) . . ?
C2 N3 S1 116.69(9) . . ?
C4 N5 C6 112.32(10) . . ?
C4 N5 S2 117.40(9) . . ?
C6 N5 S2 117.88(9) . . ?
N1 C2 N3 111.05(10) . . ?
N1 C2 H2A 109.4 . . ?
N3 C2 H2A 109.4 . . ?
N1 C2 H2B 109.4 . . ?
N3 C2 H2B 109.4 . . ?
H2A C2 H2B 108.0 . . ?
N3 C4 N5 105.16(10) . . ?
N3 C4 H4A 110.7 . . ?
N5 C4 H4A 110.7 . . ?
N3 C4 H4B 110.7 . . ?
N5 C4 H4B 110.7 . . ?
H4A C4 H4B 108.8 . . ?
N1 C6 N5 110.89(10) . . ?
N1 C6 H6A 109.5 . . ?
N5 C6 H6A 109.5 . . ?
N1 C6 H6B 109.5 . . ?
N5 C6 H6B 109.5 . . ?
H6A C6 H6B 108.0 . . ?
N1 C7 C9 109.57(11) . . ?
N1 C7 C8 113.56(11) . . ?
C9 C7 C8 108.94(12) . . ?
N1 C7 C10 106.16(11) . . ?
C9 C7 C10 108.29(12) . . ?
C8 C7 C10 110.18(12) . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C7 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C7 C9 H9A 109.5 . . ?
C7 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C7 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C7 C10 H10A 109.5 . . ?
C7 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C7 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C16 C11 C12 121.16(13) . . ?
C16 C11 S1 119.43(10) . . ?
C12 C11 S1 119.40(11) . . ?
C13 C12 C11 119.24(13) . . ?
C13 C12 H12 120.4 . . ?
C11 C12 H12 120.4 . . ?
C14 C13 C12 118.58(13) . . ?
C14 C13 H13 120.7 . . ?
C12 C13 H13 120.7 . . ?
F1 C14 C13 118.53(14) . . ?
F1 C14 C15 118.28(14) . . ?
C13 C14 C15 123.20(13) . . ?
C14 C15 C16 118.35(14) . . ?
C14 C15 H15 120.8 . . ?
C16 C15 H15 120.8 . . ?
C15 C16 C11 119.46(13) . . ?
C15 C16 H16 120.3 . . ?
C11 C16 H16 120.3 . . ?
C22 C21 C26 121.14(13) . . ?
C22 C21 S2 118.46(10) . . ?
C26 C21 S2 120.38(11) . . ?
C23 C22 C21 119.70(13) . . ?
C23 C22 H22 120.2 . . ?
C21 C22 H22 120.2 . . ?
C24 C23 C22 117.88(13) . . ?
C24 C23 H23 121.1 . . ?
C22 C23 H23 121.1 . . ?
F2 C24 C25 118.48(13) . . ?
F2 C24 C23 117.87(14) . . ?
C25 C24 C23 123.66(14) . . ?
C24 C25 C26 118.35(13) . . ?
C24 C25 H25 120.8 . . ?
C26 C25 H25 120.8 . . ?
C25 C26 C21 119.27(13) . . ?
C25 C26 H26 120.4 . . ?
C21 C26 H26 120.4 . . ?

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
O2 S1 N3 C4 168.81(10) . . . . ?
O1 S1 N3 C4 39.43(12) . . . . ?
C11 S1 N3 C4 -76.15(11) . . . . ?
O2 S1 N3 C2 -54.16(11) . . . . ?
O1 S1 N3 C2 176.46(10) . . . . ?
C11 S1 N3 C2 60.88(11) . . . . ?
O3 S2 N5 C4 -44.91(11) . . . . ?
O4 S2 N5 C4 -173.98(9) . . . . ?
C21 S2 N5 C4 71.23(11) . . . . ?
O3 S2 N5 C6 175.79(9) . . . . ?
O4 S2 N5 C6 46.72(11) . . . . ?
C21 S2 N5 C6 -68.06(11) . . . . ?
C6 N1 C2 N3 58.01(14) . . . . ?
C7 N1 C2 N3 -80.79(14) . . . . ?
C4 N3 C2 N1 -62.81(14) . . . . ?
S1 N3 C2 N1 156.66(9) . . . . ?
C2 N3 C4 N5 60.42(13) . . . . ?
S1 N3 C4 N5 -160.16(9) . . . . ?
C6 N5 C4 N3 -58.70(13) . . . . ?
S2 N5 C4 N3 159.85(9) . . . . ?
C2 N1 C6 N5 -55.14(14) . . . . ?
C7 N1 C6 N5 84.90(13) . . . . ?
C4 N5 C6 N1 57.98(14) . . . . ?
S2 N5 C6 N1 -160.76(9) . . . . ?
C2 N1 C7 C9 -31.35(16) . . . . ?
C6 N1 C7 C9 -167.22(11) . . . . ?
C2 N1 C7 C8 90.71(14) . . . . ?
C6 N1 C7 C8 -45.16(16) . . . . ?
C2 N1 C7 C10 -148.07(11) . . . . ?
C6 N1 C7 C10 76.05(14) . . . . ?
O2 S1 C11 C16 -149.76(11) . . . . ?
O1 S1 C11 C16 -18.23(13) . . . . ?
N3 S1 C11 C16 96.54(12) . . . . ?
O2 S1 C11 C12 31.26(13) . . . . ?
O1 S1 C11 C12 162.79(11) . . . . ?
N3 S1 C11 C12 -82.44(12) . . . . ?
C16 C11 C12 C13 -0.9(2) . . . . ?
S1 C11 C12 C13 178.02(10) . . . . ?
C11 C12 C13 C14 1.1(2) . . . . ?
C12 C13 C14 F1 179.19(13) . . . . ?
C12 C13 C14 C15 -0.3(2) . . . . ?
F1 C14 C15 C16 179.92(13) . . . . ?
C13 C14 C15 C16 -0.5(2) . . . . ?
C14 C15 C16 C11 0.7(2) . . . . ?
C12 C11 C16 C15 0.0(2) . . . . ?
S1 C11 C16 C15 -178.92(11) . . . . ?
O3 S2 C21 C22 -172.59(10) . . . . ?
O4 S2 C21 C22 -42.18(12) . . . . ?
N5 S2 C21 C22 71.85(12) . . . . ?
O3 S2 C21 C26 8.96(13) . . . . ?
O4 S2 C21 C26 139.37(11) . . . . ?
N5 S2 C21 C26 -106.60(12) . . . . ?
C26 C21 C22 C23 1.1(2) . . . . ?
S2 C21 C22 C23 -177.35(10) . . . . ?
C21 C22 C23 C24 -1.0(2) . . . . ?
C22 C23 C24 F2 179.23(13) . . . . ?
C22 C23 C24 C25 -0.3(2) . . . . ?
F2 C24 C25 C26 -178.12(13) . . . . ?
C23 C24 C25 C26 1.4(2) . . . . ?
C24 C25 C26 C21 -1.2(2) . . . . ?
C22 C21 C26 C25 0.0(2) . . . . ?
S2 C21 C26 C25 178.44(11) . . . . ?

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
C2 H2B O1 0.99 2.43 3.0538(17) 120.9 4_575 yes
C6 H6B O3 0.99 2.41 3.3600(17) 161.8 4_575 yes
C22 H22 O4 0.95 2.53 3.4670(17) 168.9 3_776 yes

_refine_diff_density_max         0.420
_refine_diff_density_min         -0.431
_refine_diff_density_rms         0.064


# start Validation Reply Form
_vrf_PLAT910_ftr                 
;
PROBLEM: Missing # of FCF Reflection(s) Below Theta(Min). 18 Note
RESPONSE: Closed by beamstop.
;
# end Validation Reply Form
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: hexane/ethylacetate or hexane/CH2Cl2'
####################################################################### 
# 
# 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_AK50
_database_code_depnum_ccdc_archive 'CCDC 1969757'
loop_
_audit_author_name
_audit_author_address
'Anna Sinelshchikova'
;Frumkin Institute of Physical Chemistry and Electrochemistry, Russian Academy of Sciences (IPCE RAS)
Russia
;
_audit_update_record             
;
2019-12-03 deposited with the CCDC.	2020-08-12 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         'C19 H23 Cl2 N3 O4 S2, C D Cl3'
_chemical_formula_sum            'C20 H23 Cl5 D N3 O4 S2'
_chemical_formula_weight         612.80

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'
D D 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'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 '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+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x+1/2, -y, z+1/2'

_cell_length_a                   10.5857(3)
_cell_length_b                   14.0014(4)
_cell_length_c                   17.5197(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2596.68(13)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9851
_cell_measurement_theta_min      2.91
_cell_measurement_theta_max      29.86

_exptl_crystal_description       fragment
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.568
_exptl_crystal_F_000             1256
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.500
_exptl_crystal_size_mid          0.420
_exptl_crystal_size_min          0.320
_exptl_absorpt_coefficient_mu    0.753
_shelx_estimated_absorpt_T_min   0.705
_shelx_estimated_absorpt_T_max   0.795
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.741
_exptl_absorpt_correction_T_max  0.795
_exptl_absorpt_process_details   'SADABS (Bruker, 2008)'
_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 KAPPA APEX II area-detector diffractometer'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            44030
_diffrn_reflns_av_unetI/netI     0.0252
_diffrn_reflns_av_R_equivalents  0.0354
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         3.489
_diffrn_reflns_theta_max         29.996
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             7555
_reflns_number_gt                7256
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.796
_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. Completness statistics refer to single and
 composite reflections containing twin component 1 only.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0305P)²+1.0591P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.48(5)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         7555
_refine_ls_number_parameters     308
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0286
_refine_ls_R_factor_gt           0.0267
_refine_ls_wR_factor_ref         0.0658
_refine_ls_wR_factor_gt          0.0648
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_restrained_S_all      1.056
_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
Cl1 Cl 0.62060(5) 0.35571(4) 0.70556(3) 0.01929(11) Uani 1 1 d . . . . .
Cl2 Cl 0.63573(5) 0.41324(4) 0.25989(3) 0.01621(10) Uani 1 1 d . . . . .
Cl3 Cl 0.55396(9) 0.13814(7) 0.54808(7) 0.0614(3) Uani 1 1 d . . . . .
Cl4 Cl 0.80351(7) 0.21962(6) 0.54339(4) 0.03461(16) Uani 1 1 d . . . . .
Cl5 Cl 0.62602(7) 0.26401(6) 0.42395(4) 0.03643(17) Uani 1 1 d . . . . .
S1 S 0.19122(5) 0.65209(4) 0.64179(3) 0.01096(9) Uani 1 1 d . . . . .
S2 S 0.18797(5) 0.68272(4) 0.34607(3) 0.01064(9) Uani 1 1 d . . . . .
O1 O 0.07904(14) 0.59921(12) 0.62462(9) 0.0153(3) Uani 1 1 d . . . . .
O2 O 0.19240(16) 0.72113(12) 0.70233(8) 0.0156(3) Uani 1 1 d . . . . .
O3 O 0.07832(14) 0.62446(12) 0.35641(9) 0.0154(3) Uani 1 1 d . . . . .
O4 O 0.18490(15) 0.76276(11) 0.29486(8) 0.0149(3) Uani 1 1 d . . . . .
N1 N 0.34198(16) 0.84146(13) 0.50518(9) 0.0105(3) Uani 1 1 d . . . . .
N3 N 0.22910(17) 0.71061(13) 0.56407(9) 0.0109(3) Uani 1 1 d . . . . .
N5 N 0.22462(16) 0.72572(13) 0.43034(9) 0.0107(3) Uani 1 1 d . . . . .
C1 C 0.6438(3) 0.2376(2) 0.52156(15) 0.0250(5) Uani 1 1 d . . . . .
D1A D 0.613263 0.293793 0.551563 0.030 Uiso 1 1 calc R U . . .
C2 C 0.34273(19) 0.77442(15) 0.56753(11) 0.0119(4) Uani 1 1 d . . . . .
H2A H 0.343027 0.809588 0.616558 0.014 Uiso 1 1 calc R U . . .
H2B H 0.420425 0.735181 0.565131 0.014 Uiso 1 1 calc R U . . .
C4 C 0.2241(2) 0.65579(16) 0.49290(11) 0.0128(4) Uani 1 1 d . . . . .
H4A H 0.146437 0.616505 0.491058 0.015 Uiso 1 1 calc R U . . .
H4B H 0.298236 0.612940 0.488942 0.015 Uiso 1 1 calc R U . . .
C6 C 0.33834(19) 0.78998(15) 0.43416(11) 0.0120(4) Uani 1 1 d . . . . .
H6A H 0.416040 0.751180 0.428949 0.014 Uiso 1 1 calc R U . . .
H6B H 0.335743 0.835913 0.391228 0.014 Uiso 1 1 calc R U . . .
C7 C 0.2659(2) 0.93057(16) 0.51282(12) 0.0122(4) Uani 1 1 d . . . . .
C8 C 0.3045(3) 0.97877(16) 0.58751(12) 0.0189(4) Uani 1 1 d . . . . .
H8A H 0.255921 1.037770 0.594135 0.028 Uiso 1 1 calc R U . . .
H8B H 0.287506 0.935566 0.630302 0.028 Uiso 1 1 calc R U . . .
H8C H 0.394870 0.993899 0.586004 0.028 Uiso 1 1 calc R U . . .
C9 C 0.3006(3) 0.99640(17) 0.44646(13) 0.0209(5) Uani 1 1 d . . . . .
H9A H 0.251711 1.055668 0.450180 0.031 Uiso 1 1 calc R U . . .
H9B H 0.390981 1.011249 0.448593 0.031 Uiso 1 1 calc R U . . .
H9C H 0.281269 0.964505 0.398056 0.031 Uiso 1 1 calc R U . . .
C10 C 0.1217(2) 0.91473(19) 0.51274(16) 0.0232(5) Uani 1 1 d . . . . .
H10A H 0.078642 0.976352 0.517945 0.035 Uiso 1 1 calc R U . . .
H10B H 0.096385 0.884492 0.464658 0.035 Uiso 1 1 calc R U . . .
H10C H 0.098395 0.873267 0.555553 0.035 Uiso 1 1 calc R U . . .
C11 C 0.3132(2) 0.56885(15) 0.65977(11) 0.0125(4) Uani 1 1 d . . . . .
C12 C 0.2977(2) 0.47448(16) 0.63588(12) 0.0153(4) Uani 1 1 d . . . . .
H12A H 0.222653 0.455411 0.610382 0.018 Uiso 1 1 calc R U . . .
C13 C 0.3936(2) 0.40846(17) 0.64984(13) 0.0172(4) Uani 1 1 d . . . . .
H13A H 0.384780 0.343876 0.634119 0.021 Uiso 1 1 calc R U . . .
C14 C 0.5019(2) 0.43856(17) 0.68695(12) 0.0154(4) Uani 1 1 d . . . . .
C15 C 0.5184(2) 0.53261(17) 0.71071(13) 0.0165(4) Uani 1 1 d . . . . .
H15A H 0.593943 0.551639 0.735750 0.020 Uiso 1 1 calc R U . . .
C16 C 0.4226(2) 0.59799(16) 0.69717(12) 0.0147(4) Uani 1 1 d . . . . .
H16A H 0.431641 0.662396 0.713336 0.018 Uiso 1 1 calc R U . . .
C21 C 0.3136(2) 0.60747(15) 0.31902(11) 0.0115(4) Uani 1 1 d . . . . .
C22 C 0.3062(2) 0.51024(15) 0.33646(11) 0.0141(4) Uani 1 1 d . . . . .
H22A H 0.233065 0.485049 0.360645 0.017 Uiso 1 1 calc R U . . .
C23 C 0.4066(2) 0.45089(16) 0.31811(12) 0.0151(4) Uani 1 1 d . . . . .
H23A H 0.402856 0.384605 0.329492 0.018 Uiso 1 1 calc R U . . .
C24 C 0.5123(2) 0.48922(16) 0.28303(12) 0.0135(4) Uani 1 1 d . . . . .
C25 C 0.5215(2) 0.58565(17) 0.26565(13) 0.0163(4) Uani 1 1 d . . . . .
H25A H 0.595088 0.610405 0.241739 0.020 Uiso 1 1 calc R U . . .
C26 C 0.4210(2) 0.64538(17) 0.28388(12) 0.0150(4) Uani 1 1 d . . . . .
H26A H 0.425315 0.711643 0.272515 0.018 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl1 C14 1.741(2) . ?
Cl2 C24 1.733(2) . ?
Cl3 C1 1.749(3) . ?
Cl4 C1 1.751(3) . ?
Cl5 C1 1.760(3) . ?
S1 O1 1.4313(16) . ?
S1 O2 1.4352(16) . ?
S1 N3 1.6389(17) . ?
S1 C11 1.768(2) . ?
S2 O3 1.4303(16) . ?
S2 O4 1.4359(16) . ?
S2 N5 1.6409(18) . ?
S2 C21 1.762(2) . ?
N1 C6 1.438(3) . ?
N1 C2 1.440(3) . ?
N1 C7 1.491(3) . ?
N3 C4 1.465(3) . ?
N3 C2 1.500(3) . ?
N5 C4 1.470(3) . ?
N5 C6 1.504(3) . ?
C1 D1A 1.0000 . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 C8 1.528(3) . ?
C7 C9 1.528(3) . ?
C7 C10 1.543(3) . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 C16 1.392(3) . ?
C11 C12 1.396(3) . ?
C12 C13 1.395(3) . ?
C12 H12A 0.9500 . ?
C13 C14 1.383(3) . ?
C13 H13A 0.9500 . ?
C14 C15 1.392(3) . ?
C15 C16 1.387(3) . ?
C15 H15A 0.9500 . ?
C16 H16A 0.9500 . ?
C21 C26 1.398(3) . ?
C21 C22 1.398(3) . ?
C22 C23 1.387(3) . ?
C22 H22A 0.9500 . ?
C23 C24 1.385(3) . ?
C23 H23A 0.9500 . ?
C24 C25 1.388(3) . ?
C25 C26 1.390(3) . ?
C25 H25A 0.9500 . ?
C26 H26A 0.9500 . ?

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
O1 S1 O2 120.72(10) . . ?
O1 S1 N3 106.68(9) . . ?
O2 S1 N3 105.97(9) . . ?
O1 S1 C11 107.61(10) . . ?
O2 S1 C11 107.82(10) . . ?
N3 S1 C11 107.40(9) . . ?
O3 S2 O4 120.39(10) . . ?
O3 S2 N5 106.69(9) . . ?
O4 S2 N5 106.33(9) . . ?
O3 S2 C21 107.79(10) . . ?
O4 S2 C21 108.40(10) . . ?
N5 S2 C21 106.44(9) . . ?
C6 N1 C2 109.25(17) . . ?
C6 N1 C7 118.85(16) . . ?
C2 N1 C7 118.70(16) . . ?
C4 N3 C2 112.05(16) . . ?
C4 N3 S1 115.87(14) . . ?
C2 N3 S1 117.42(13) . . ?
C4 N5 C6 111.59(16) . . ?
C4 N5 S2 115.20(14) . . ?
C6 N5 S2 116.66(13) . . ?
Cl3 C1 Cl4 110.64(15) . . ?
Cl3 C1 Cl5 111.53(15) . . ?
Cl4 C1 Cl5 110.24(15) . . ?
Cl3 C1 D1A 108.1 . . ?
Cl4 C1 D1A 108.1 . . ?
Cl5 C1 D1A 108.1 . . ?
N1 C2 N3 110.68(16) . . ?
N1 C2 H2A 109.5 . . ?
N3 C2 H2A 109.5 . . ?
N1 C2 H2B 109.5 . . ?
N3 C2 H2B 109.5 . . ?
H2A C2 H2B 108.1 . . ?
N3 C4 N5 106.59(17) . . ?
N3 C4 H4A 110.4 . . ?
N5 C4 H4A 110.4 . . ?
N3 C4 H4B 110.4 . . ?
N5 C4 H4B 110.4 . . ?
H4A C4 H4B 108.6 . . ?
N1 C6 N5 111.08(16) . . ?
N1 C6 H6A 109.4 . . ?
N5 C6 H6A 109.4 . . ?
N1 C6 H6B 109.4 . . ?
N5 C6 H6B 109.4 . . ?
H6A C6 H6B 108.0 . . ?
N1 C7 C8 107.58(17) . . ?
N1 C7 C9 107.86(17) . . ?
C8 C7 C9 108.72(19) . . ?
N1 C7 C10 114.46(19) . . ?
C8 C7 C10 109.21(19) . . ?
C9 C7 C10 108.9(2) . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C7 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C7 C9 H9A 109.5 . . ?
C7 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C7 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C7 C10 H10A 109.5 . . ?
C7 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C7 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C16 C11 C12 121.1(2) . . ?
C16 C11 S1 119.90(17) . . ?
C12 C11 S1 119.01(16) . . ?
C13 C12 C11 119.3(2) . . ?
C13 C12 H12A 120.3 . . ?
C11 C12 H12A 120.4 . . ?
C14 C13 C12 118.9(2) . . ?
C14 C13 H13A 120.5 . . ?
C12 C13 H13A 120.5 . . ?
C13 C14 C15 122.2(2) . . ?
C13 C14 Cl1 118.88(18) . . ?
C15 C14 Cl1 118.91(17) . . ?
C16 C15 C14 118.8(2) . . ?
C16 C15 H15A 120.6 . . ?
C14 C15 H15A 120.6 . . ?
C15 C16 C11 119.7(2) . . ?
C15 C16 H16A 120.1 . . ?
C11 C16 H16A 120.1 . . ?
C26 C21 C22 120.8(2) . . ?
C26 C21 S2 120.36(16) . . ?
C22 C21 S2 118.77(17) . . ?
C23 C22 C21 119.3(2) . . ?
C23 C22 H22A 120.3 . . ?
C21 C22 H22A 120.3 . . ?
C24 C23 C22 119.3(2) . . ?
C24 C23 H23A 120.3 . . ?
C22 C23 H23A 120.3 . . ?
C23 C24 C25 122.1(2) . . ?
C23 C24 Cl2 118.37(17) . . ?
C25 C24 Cl2 119.54(17) . . ?
C24 C25 C26 118.8(2) . . ?
C24 C25 H25A 120.6 . . ?
C26 C25 H25A 120.6 . . ?
C25 C26 C21 119.7(2) . . ?
C25 C26 H26A 120.2 . . ?
C21 C26 H26A 120.2 . . ?

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
O1 S1 N3 C4 -45.44(17) . . . . ?
O2 S1 N3 C4 -175.27(15) . . . . ?
C11 S1 N3 C4 69.70(17) . . . . ?
O1 S1 N3 C2 178.38(15) . . . . ?
O2 S1 N3 C2 48.55(17) . . . . ?
C11 S1 N3 C2 -66.48(17) . . . . ?
O3 S2 N5 C4 46.23(17) . . . . ?
O4 S2 N5 C4 175.89(14) . . . . ?
C21 S2 N5 C4 -68.67(16) . . . . ?
O3 S2 N5 C6 179.97(14) . . . . ?
O4 S2 N5 C6 -50.37(17) . . . . ?
C21 S2 N5 C6 65.06(17) . . . . ?
C6 N1 C2 N3 -57.7(2) . . . . ?
C7 N1 C2 N3 83.0(2) . . . . ?
C4 N3 C2 N1 59.7(2) . . . . ?
S1 N3 C2 N1 -162.49(14) . . . . ?
C2 N3 C4 N5 -57.5(2) . . . . ?
S1 N3 C4 N5 163.99(13) . . . . ?
C6 N5 C4 N3 57.0(2) . . . . ?
S2 N5 C4 N3 -166.96(13) . . . . ?
C2 N1 C6 N5 57.7(2) . . . . ?
C7 N1 C6 N5 -82.9(2) . . . . ?
C4 N5 C6 N1 -59.3(2) . . . . ?
S2 N5 C6 N1 165.43(14) . . . . ?
C6 N1 C7 C8 -170.49(18) . . . . ?
C2 N1 C7 C8 52.6(2) . . . . ?
C6 N1 C7 C9 -53.4(2) . . . . ?
C2 N1 C7 C9 169.68(18) . . . . ?
C6 N1 C7 C10 68.0(2) . . . . ?
C2 N1 C7 C10 -69.0(2) . . . . ?
O1 S1 C11 C16 -162.99(16) . . . . ?
O2 S1 C11 C16 -31.3(2) . . . . ?
N3 S1 C11 C16 82.48(18) . . . . ?
O1 S1 C11 C12 17.09(19) . . . . ?
O2 S1 C11 C12 148.77(17) . . . . ?
N3 S1 C11 C12 -97.43(18) . . . . ?
C16 C11 C12 C13 0.0(3) . . . . ?
S1 C11 C12 C13 179.95(17) . . . . ?
C11 C12 C13 C14 -0.1(3) . . . . ?
C12 C13 C14 C15 -0.1(3) . . . . ?
C12 C13 C14 Cl1 179.09(17) . . . . ?
C13 C14 C15 C16 0.5(3) . . . . ?
Cl1 C14 C15 C16 -178.73(17) . . . . ?
C14 C15 C16 C11 -0.6(3) . . . . ?
C12 C11 C16 C15 0.3(3) . . . . ?
S1 C11 C16 C15 -179.58(17) . . . . ?
O3 S2 C21 C26 161.29(16) . . . . ?
O4 S2 C21 C26 29.47(19) . . . . ?
N5 S2 C21 C26 -84.56(18) . . . . ?
O3 S2 C21 C22 -21.58(19) . . . . ?
O4 S2 C21 C22 -153.40(16) . . . . ?
N5 S2 C21 C22 92.57(18) . . . . ?
C26 C21 C22 C23 -0.4(3) . . . . ?
S2 C21 C22 C23 -177.53(16) . . . . ?
C21 C22 C23 C24 0.1(3) . . . . ?
C22 C23 C24 C25 0.2(3) . . . . ?
C22 C23 C24 Cl2 -179.39(16) . . . . ?
C23 C24 C25 C26 -0.2(3) . . . . ?
Cl2 C24 C25 C26 179.32(16) . . . . ?
C24 C25 C26 C21 0.0(3) . . . . ?
C22 C21 C26 C25 0.3(3) . . . . ?
S2 C21 C26 C25 177.42(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
_geom_hbond_publ_flag
C1 D1A Cl1 1.00 2.83 3.631(3) 137.0 . yes
C6 H6B Cl2 0.99 2.88 3.823(2) 160.2 3_655 yes
C8 H8A Cl2 0.98 2.94 3.553(2) 121.8 2_466 yes
C8 H8C Cl3 0.98 2.71 3.525(3) 140.7 1_565 yes
C10 H10B N5 0.98 2.67 3.205(3) 114.4 . yes
C10 H10C N3 0.98 2.67 3.205(3) 114.7 . yes
C15 H15A Cl2 0.95 2.93 3.837(2) 159.1 4_665 yes
C23 H23A Cl4 0.95 2.86 3.574(2) 132.6 2_456 yes
C26 H26A Cl2 0.95 2.95 3.875(2) 164.6 3_655 yes

_refine_diff_density_max         0.395
_refine_diff_density_min         -0.539
_refine_diff_density_rms         0.057

####################################################################### 
# 
# 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_AK119_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 1969753'
loop_
_audit_author_name
_audit_author_address
'Anna Sinelshchikova'
;Frumkin Institute of Physical Chemistry and Electrochemistry, Russian Academy of Sciences (IPCE RAS)
Russia
;
_audit_update_record             
;
2019-12-03 deposited with the CCDC.	2020-08-12 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         'C19 H23 Cl2 N3 O4 S2'
_chemical_formula_sum            'C19 H23 Cl2 N3 O4 S2'
_chemical_formula_weight         492.42

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'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           62
_space_group_name_H-M_alt        'P n m a'
_space_group_name_Hall           '-P 2ac 2n'

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

_cell_length_a                   15.0515(5)
_cell_length_b                   23.4696(8)
_cell_length_c                   6.1833(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2184.27(13)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    5390
_cell_measurement_theta_min      2.84
_cell_measurement_theta_max      29.86

_exptl_crystal_description       fragment
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.497
_exptl_crystal_F_000             1024
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.060
_exptl_absorpt_coefficient_mu    0.520
_shelx_estimated_absorpt_T_min   0.819
_shelx_estimated_absorpt_T_max   0.969
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.836
_exptl_absorpt_correction_T_max  0.969
_exptl_absorpt_process_details   'SADABS (Bruker, 2008)'
_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 KAPPA APEX II area-detector diffractometer'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            22380
_diffrn_reflns_av_unetI/netI     0.0309
_diffrn_reflns_av_R_equivalents  0.0481
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_k_min       -33
_diffrn_reflns_limit_k_max       33
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_theta_min         4.201
_diffrn_reflns_theta_max         29.997
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.994
_reflns_number_total             3242
_reflns_number_gt                2474
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-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)+(0.0458P)²+1.6773P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3242
_refine_ls_number_parameters     142
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0600
_refine_ls_R_factor_gt           0.0395
_refine_ls_wR_factor_ref         0.1106
_refine_ls_wR_factor_gt          0.0953
_refine_ls_goodness_of_fit_ref   1.087
_refine_ls_restrained_S_all      1.087
_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
Cl1 Cl 0.65265(3) 0.47342(2) 0.80793(8) 0.03114(14) Uani 1 1 d . . . . .
S1 S 0.34202(3) 0.35888(2) 0.29829(7) 0.02094(12) Uani 1 1 d . . . . .
O1 O 0.26377(9) 0.39275(6) 0.3227(2) 0.0307(3) Uani 1 1 d . . . . .
O2 O 0.37468(10) 0.34417(6) 0.0875(2) 0.0285(3) Uani 1 1 d . . . . .
N1 N 0.22311(14) 0.250000 0.6679(3) 0.0190(4) Uani 1 2 d S T P . .
N3 N 0.32192(10) 0.29954(7) 0.4235(2) 0.0217(3) Uani 1 1 d . . . . .
C2 C 0.27727(13) 0.29989(9) 0.6397(3) 0.0252(4) Uani 1 1 d . . . . .
H2A H 0.322841 0.301295 0.755032 0.030 Uiso 1 1 calc R U . . .
H2B H 0.239766 0.334371 0.652639 0.030 Uiso 1 1 calc R U . . .
C4 C 0.37898(16) 0.250000 0.3926(4) 0.0214(5) Uani 1 2 d S T P . .
H4A H 0.404794 0.250000 0.245338 0.026 Uiso 1 2 calc R U P . .
H4B H 0.427980 0.250000 0.499397 0.026 Uiso 1 2 calc R U P . .
C5 C 0.13202(16) 0.250000 0.5724(4) 0.0172(4) Uani 1 2 d S T P . .
C6 C 0.13009(17) 0.250000 0.3232(4) 0.0227(5) Uani 1 2 d S T P . .
H6A H 0.068308 0.250000 0.273177 0.034 Uiso 1 2 calc R U P . .
H6B H 0.160371 0.284094 0.268962 0.034 Uiso 0.5 1 calc R U P . .
H6C H 0.160371 0.215906 0.268962 0.034 Uiso 0.5 1 calc R U P . .
C7 C 0.08340(13) 0.30249(9) 0.6568(3) 0.0282(4) Uani 1 1 d . . . . .
H7A H 0.023227 0.303537 0.596440 0.042 Uiso 1 1 calc R U . . .
H7B H 0.080032 0.300782 0.814972 0.042 Uiso 1 1 calc R U . . .
H7C H 0.115711 0.336882 0.613313 0.042 Uiso 1 1 calc R U . . .
C8 C 0.42906(11) 0.39378(7) 0.4365(3) 0.0177(3) Uani 1 1 d . . . . .
C9 C 0.41212(12) 0.41865(8) 0.6366(3) 0.0208(3) Uani 1 1 d . . . . .
H9A H 0.353667 0.418604 0.694574 0.025 Uiso 1 1 calc R U . . .
C10 C 0.48109(13) 0.44342(7) 0.7501(3) 0.0218(3) Uani 1 1 d . . . . .
H10A H 0.470724 0.460019 0.887964 0.026 Uiso 1 1 calc R U . . .
C11 C 0.56542(12) 0.44380(7) 0.6610(3) 0.0204(3) Uani 1 1 d . . . . .
C12 C 0.58290(12) 0.42031(8) 0.4593(3) 0.0225(4) Uani 1 1 d . . . . .
H12A H 0.640951 0.421765 0.399216 0.027 Uiso 1 1 calc R U . . .
C13 C 0.51368(12) 0.39467(8) 0.3474(3) 0.0206(3) Uani 1 1 d . . . . .
H13A H 0.524196 0.377771 0.210191 0.025 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl1 C11 1.7411(18) . ?
S1 O1 1.4291(15) . ?
S1 O2 1.4349(14) . ?
S1 N3 1.6218(16) . ?
S1 C8 1.7655(17) . ?
N1 C2 1.437(2) . ?
N1 C2 1.437(2) 7_565 ?
N1 C5 1.493(3) . ?
N3 C4 1.458(2) . ?
N3 C2 1.496(2) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 C7 1.525(2) . ?
C5 C7 1.525(2) 7_565 ?
C5 C6 1.541(3) . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C8 C13 1.388(2) . ?
C8 C9 1.392(2) . ?
C9 C10 1.381(2) . ?
C9 H9A 0.9500 . ?
C10 C11 1.384(3) . ?
C10 H10A 0.9500 . ?
C11 C12 1.389(3) . ?
C12 C13 1.388(2) . ?
C12 H12A 0.9500 . ?
C13 H13A 0.9500 . ?

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
O1 S1 O2 120.82(9) . . ?
O1 S1 N3 105.87(9) . . ?
O2 S1 N3 106.90(8) . . ?
O1 S1 C8 107.60(8) . . ?
O2 S1 C8 107.27(8) . . ?
N3 S1 C8 107.81(8) . . ?
C2 N1 C2 109.1(2) . 7_565 ?
C2 N1 C5 118.22(12) . . ?
C2 N1 C5 118.22(12) 7_565 . ?
C4 N3 C2 112.69(16) . . ?
C4 N3 S1 120.83(13) . . ?
C2 N3 S1 120.36(13) . . ?
N1 C2 N3 111.02(15) . . ?
N1 C2 H2A 109.4 . . ?
N3 C2 H2A 109.4 . . ?
N1 C2 H2B 109.4 . . ?
N3 C2 H2B 109.4 . . ?
H2A C2 H2B 108.0 . . ?
N3 C4 N3 105.77(19) 7_565 . ?
N3 C4 H4A 110.6 7_565 . ?
N3 C4 H4A 110.6 . . ?
N3 C4 H4B 110.6 7_565 . ?
N3 C4 H4B 110.6 . . ?
H4A C4 H4B 108.7 . . ?
N1 C5 C7 107.78(14) . . ?
N1 C5 C7 107.78(14) . 7_565 ?
C7 C5 C7 107.8(2) . 7_565 ?
N1 C5 C6 114.38(19) . . ?
C7 C5 C6 109.46(14) . . ?
C7 C5 C6 109.46(14) 7_565 . ?
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 . . ?
C5 C7 H7A 109.5 . . ?
C5 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C5 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C13 C8 C9 120.97(16) . . ?
C13 C8 S1 119.73(13) . . ?
C9 C8 S1 119.27(13) . . ?
C10 C9 C8 119.38(17) . . ?
C10 C9 H9A 120.3 . . ?
C8 C9 H9A 120.3 . . ?
C9 C10 C11 119.33(16) . . ?
C9 C10 H10A 120.3 . . ?
C11 C10 H10A 120.3 . . ?
C10 C11 C12 121.91(16) . . ?
C10 C11 Cl1 119.12(14) . . ?
C12 C11 Cl1 118.95(14) . . ?
C13 C12 C11 118.52(16) . . ?
C13 C12 H12A 120.7 . . ?
C11 C12 H12A 120.7 . . ?
C8 C13 C12 119.86(16) . . ?
C8 C13 H13A 120.1 . . ?
C12 C13 H13A 120.1 . . ?

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
O1 S1 N3 C4 166.40(15) . . . . ?
O2 S1 N3 C4 36.38(17) . . . . ?
C8 S1 N3 C4 -78.68(16) . . . . ?
O1 S1 N3 C2 -43.11(16) . . . . ?
O2 S1 N3 C2 -173.13(13) . . . . ?
C8 S1 N3 C2 71.81(15) . . . . ?
C2 N1 C2 N3 56.7(2) 7_565 . . . ?
C5 N1 C2 N3 -82.3(2) . . . . ?
C4 N3 C2 N1 -59.4(2) . . . . ?
S1 N3 C2 N1 147.86(14) . . . . ?
C2 N3 C4 N3 57.1(2) . . . 7_565 ?
S1 N3 C4 N3 -150.31(10) . . . 7_565 ?
C2 N1 C5 C7 -54.4(2) . . . . ?
C2 N1 C5 C7 170.44(16) 7_565 . . . ?
C2 N1 C5 C7 -170.44(16) . . . 7_565 ?
C2 N1 C5 C7 54.4(2) 7_565 . . 7_565 ?
C2 N1 C5 C6 67.59(15) . . . . ?
C2 N1 C5 C6 -67.60(15) 7_565 . . . ?
O1 S1 C8 C13 -140.65(15) . . . . ?
O2 S1 C8 C13 -9.24(17) . . . . ?
N3 S1 C8 C13 105.57(15) . . . . ?
O1 S1 C8 C9 41.13(16) . . . . ?
O2 S1 C8 C9 172.54(14) . . . . ?
N3 S1 C8 C9 -72.64(15) . . . . ?
C13 C8 C9 C10 -1.5(3) . . . . ?
S1 C8 C9 C10 176.69(14) . . . . ?
C8 C9 C10 C11 1.0(3) . . . . ?
C9 C10 C11 C12 0.5(3) . . . . ?
C9 C10 C11 Cl1 -178.34(14) . . . . ?
C10 C11 C12 C13 -1.5(3) . . . . ?
Cl1 C11 C12 C13 177.32(14) . . . . ?
C9 C8 C13 C12 0.5(3) . . . . ?
S1 C8 C13 C12 -177.71(14) . . . . ?
C11 C12 C13 C8 1.0(3) . . . . ?

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
C2 H2A O2 0.99 2.42 3.301(2) 148.2 1_556 yes
C12 H12A O1 0.95 2.40 3.297(2) 157.1 8_656 yes

_refine_diff_density_max         0.463
_refine_diff_density_min         -0.438
_refine_diff_density_rms         0.071


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: CH2Cl2'
####################################################################### 
# 
# 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_ak117
_database_code_depnum_ccdc_archive 'CCDC 1969752'
loop_
_audit_author_name
_audit_author_address
'Anna Sinelshchikova'
;Frumkin Institute of Physical Chemistry and Electrochemistry, Russian Academy of Sciences (IPCE RAS)
Russia
;
_audit_update_record             
;
2019-12-03 deposited with the CCDC.	2020-08-12 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         ?
_chemical_formula_sum            'C19 H23 Br2 N3 O4 S2'
_chemical_formula_weight         581.34

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'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           62
_space_group_name_H-M_alt        'P n m a'
_space_group_name_Hall           '-P 2ac 2n'

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

_cell_length_a                   15.1555(7)
_cell_length_b                   24.3132(12)
_cell_length_c                   6.1544(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2267.77(19)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    3071
_cell_measurement_theta_min      3.17
_cell_measurement_theta_max      23.08

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.703
_exptl_crystal_F_000             1168
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.500
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.040
_exptl_absorpt_coefficient_mu    3.790
_shelx_estimated_absorpt_T_min   0.253
_shelx_estimated_absorpt_T_max   0.863
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.587
_exptl_absorpt_correction_T_max  0.863
_exptl_absorpt_process_details   'SADABS (Bruker, 2008)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  
'Bruker KAPPA APEX II area-detector diffractometer'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            18873
_diffrn_reflns_av_unetI/netI     0.0380
_diffrn_reflns_av_R_equivalents  0.0587
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -31
_diffrn_reflns_limit_k_max       31
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_theta_min         3.947
_diffrn_reflns_theta_max         27.616
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             2670
_reflns_number_gt                1712
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-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)+(0.0260P)²+2.6827P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2670
_refine_ls_number_parameters     142
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0816
_refine_ls_R_factor_gt           0.0417
_refine_ls_wR_factor_ref         0.0931
_refine_ls_wR_factor_gt          0.0793
_refine_ls_goodness_of_fit_ref   1.011
_refine_ls_restrained_S_all      1.011
_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
Br1 Br 0.66453(3) 0.47635(2) 0.80928(8) 0.07585(18) Uani 1 1 d . . . . .
S1 S 0.35515(6) 0.35430(4) 0.29434(16) 0.0524(2) Uani 1 1 d . . . . .
O1 O 0.27641(16) 0.38584(11) 0.3154(5) 0.0753(8) Uani 1 1 d . . . . .
O2 O 0.38886(19) 0.33920(11) 0.0857(4) 0.0704(8) Uani 1 1 d . . . . .
N1 N 0.2389(2) 0.250000 0.6695(5) 0.0447(9) Uani 1 2 d S T P . .
N3 N 0.33754(17) 0.29800(11) 0.4242(5) 0.0495(7) Uani 1 1 d . . . . .
C2 C 0.2926(2) 0.29803(16) 0.6403(6) 0.0606(10) Uani 1 1 d . . . . .
H2A H 0.336652 0.299532 0.754412 0.073 Uiso 1 1 calc R U . . .
H2B H 0.255901 0.330586 0.652452 0.073 Uiso 1 1 calc R U . . .
C4 C 0.3938(3) 0.250000 0.3943(9) 0.0533(13) Uani 1 2 d S T P . .
H4A H 0.419351 0.250000 0.249708 0.064 Uiso 1 2 calc R U P . .
H4B H 0.441301 0.250000 0.499991 0.064 Uiso 1 2 calc R U P . .
C5 C 0.1479(3) 0.250000 0.5786(7) 0.0412(10) Uani 1 2 d S T P . .
C6 C 0.1447(3) 0.250000 0.3304(7) 0.0556(13) Uani 1 2 d S T P . .
H6A H 0.084319 0.250000 0.283069 0.083 Uiso 1 2 calc R U P . .
H6B H 0.173856 0.282239 0.276118 0.083 Uiso 0.5 1 calc R U P . .
H6C H 0.173856 0.217761 0.276118 0.083 Uiso 0.5 1 calc R U P . .
C7 C 0.1006(3) 0.30023(16) 0.6661(7) 0.0697(11) Uani 1 1 d . . . . .
H7A H 0.041497 0.301224 0.609827 0.104 Uiso 1 1 calc R U . . .
H7B H 0.098659 0.298481 0.821847 0.104 Uiso 1 1 calc R U . . .
H7C H 0.131539 0.332810 0.622007 0.104 Uiso 1 1 calc R U . . .
C8 C 0.4400(2) 0.39033(12) 0.4316(5) 0.0391(7) Uani 1 1 d . . . . .
C9 C 0.4220(2) 0.41595(14) 0.6260(6) 0.0496(9) Uani 1 1 d . . . . .
H9A H 0.364934 0.415699 0.681874 0.059 Uiso 1 1 calc R U . . .
C10 C 0.4888(2) 0.44196(14) 0.7374(6) 0.0495(8) Uani 1 1 d . . . . .
H10A H 0.477555 0.459026 0.869731 0.059 Uiso 1 1 calc R U . . .
C11 C 0.5724(2) 0.44240(12) 0.6508(6) 0.0444(8) Uani 1 1 d . . . . .
C12 C 0.5910(2) 0.41798(13) 0.4549(6) 0.0515(9) Uani 1 1 d . . . . .
H12A H 0.647664 0.419218 0.396944 0.062 Uiso 1 1 calc R U . . .
C13 C 0.5236(2) 0.39158(13) 0.3462(5) 0.0483(8) Uani 1 1 d . . . . .
H13A H 0.534929 0.374470 0.213986 0.058 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br1 C11 1.893(3) . ?
S1 O1 1.424(3) . ?
S1 O2 1.430(3) . ?
S1 N3 1.607(3) . ?
S1 C8 1.770(3) . ?
N1 C2 1.434(4) . ?
N1 C2 1.434(4) 7_565 ?
N1 C5 1.490(5) . ?
N3 C4 1.457(4) . ?
N3 C2 1.494(4) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C5 C7 1.515(4) 7_565 ?
C5 C7 1.515(4) . ?
C5 C6 1.528(6) . ?
C6 H6A 0.9600 . ?
C6 H6B 0.9600 . ?
C6 H6C 0.9600 . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C8 C13 1.372(4) . ?
C8 C9 1.377(4) . ?
C9 C10 1.377(4) . ?
C9 H9A 0.9300 . ?
C10 C11 1.373(5) . ?
C10 H10A 0.9300 . ?
C11 C12 1.373(5) . ?
C12 C13 1.380(4) . ?
C12 H12A 0.9300 . ?
C13 H13A 0.9300 . ?

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
O1 S1 O2 121.27(18) . . ?
O1 S1 N3 105.91(16) . . ?
O2 S1 N3 106.69(16) . . ?
O1 S1 C8 107.38(15) . . ?
O2 S1 C8 107.22(16) . . ?
N3 S1 C8 107.74(15) . . ?
C2 N1 C2 109.0(4) . 7_565 ?
C2 N1 C5 118.6(2) . . ?
C2 N1 C5 118.6(2) 7_565 . ?
C4 N3 C2 112.3(3) . . ?
C4 N3 S1 121.5(2) . . ?
C2 N3 S1 121.2(2) . . ?
N1 C2 N3 111.7(3) . . ?
N1 C2 H2A 109.3 . . ?
N3 C2 H2A 109.3 . . ?
N1 C2 H2B 109.3 . . ?
N3 C2 H2B 109.3 . . ?
H2A C2 H2B 107.9 . . ?
N3 C4 N3 106.4(4) 7_565 . ?
N3 C4 H4A 110.4 7_565 . ?
N3 C4 H4A 110.4 . . ?
N3 C4 H4B 110.4 7_565 . ?
N3 C4 H4B 110.4 . . ?
H4A C4 H4B 108.6 . . ?
N1 C5 C7 107.8(3) . 7_565 ?
N1 C5 C7 107.8(3) . . ?
C7 C5 C7 107.4(4) 7_565 . ?
N1 C5 C6 113.9(4) . . ?
C7 C5 C6 109.9(3) 7_565 . ?
C7 C5 C6 109.9(3) . . ?
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 . . ?
C5 C7 H7A 109.5 . . ?
C5 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C5 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C13 C8 C9 120.4(3) . . ?
C13 C8 S1 119.9(2) . . ?
C9 C8 S1 119.6(2) . . ?
C8 C9 C10 119.6(3) . . ?
C8 C9 H9A 120.2 . . ?
C10 C9 H9A 120.2 . . ?
C11 C10 C9 119.3(3) . . ?
C11 C10 H10A 120.4 . . ?
C9 C10 H10A 120.4 . . ?
C10 C11 C12 121.8(3) . . ?
C10 C11 Br1 118.9(3) . . ?
C12 C11 Br1 119.3(3) . . ?
C11 C12 C13 118.3(3) . . ?
C11 C12 H12A 120.9 . . ?
C13 C12 H12A 120.9 . . ?
C8 C13 C12 120.6(3) . . ?
C8 C13 H13A 119.7 . . ?
C12 C13 H13A 119.7 . . ?

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
O1 S1 N3 C4 164.4(3) . . . . ?
O2 S1 N3 C4 33.9(3) . . . . ?
C8 S1 N3 C4 -81.0(3) . . . . ?
O1 S1 N3 C2 -42.6(3) . . . . ?
O2 S1 N3 C2 -173.1(2) . . . . ?
C8 S1 N3 C2 72.0(3) . . . . ?
C2 N1 C2 N3 56.0(5) 7_565 . . . ?
C5 N1 C2 N3 -83.8(4) . . . . ?
C4 N3 C2 N1 -58.8(4) . . . . ?
S1 N3 C2 N1 145.9(3) . . . . ?
C2 N3 C4 N3 56.8(4) . . . 7_565 ?
S1 N3 C4 N3 -148.1(2) . . . 7_565 ?
C2 N1 C5 C7 -169.8(3) . . . 7_565 ?
C2 N1 C5 C7 54.2(4) 7_565 . . 7_565 ?
C2 N1 C5 C7 -54.2(4) . . . . ?
C2 N1 C5 C7 169.8(3) 7_565 . . . ?
C2 N1 C5 C6 68.0(3) . . . . ?
C2 N1 C5 C6 -68.0(3) 7_565 . . . ?
O1 S1 C8 C13 -141.5(3) . . . . ?
O2 S1 C8 C13 -9.7(3) . . . . ?
N3 S1 C8 C13 104.8(3) . . . . ?
O1 S1 C8 C9 39.9(3) . . . . ?
O2 S1 C8 C9 171.7(3) . . . . ?
N3 S1 C8 C9 -73.8(3) . . . . ?
C13 C8 C9 C10 -1.4(5) . . . . ?
S1 C8 C9 C10 177.2(3) . . . . ?
C8 C9 C10 C11 0.8(5) . . . . ?
C9 C10 C11 C12 0.6(5) . . . . ?
C9 C10 C11 Br1 -178.1(2) . . . . ?
C10 C11 C12 C13 -1.2(5) . . . . ?
Br1 C11 C12 C13 177.5(2) . . . . ?
C9 C8 C13 C12 0.7(5) . . . . ?
S1 C8 C13 C12 -177.9(3) . . . . ?
C11 C12 C13 C8 0.6(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
_geom_hbond_publ_flag
C2 H2A O2 0.97 2.39 3.263(4) 149.4 1_556 yes
C12 H12A O1 0.93 2.48 3.357(4) 156.3 6_656 yes

_refine_diff_density_max         0.578
_refine_diff_density_min         -0.614
_refine_diff_density_rms         0.062

####################################################################### 
# 
# 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_FT
_database_code_depnum_ccdc_archive 'CCDC 1969756'
loop_
_audit_author_name
_audit_author_address
'Anna Sinelshchikova'
;Frumkin Institute of Physical Chemistry and Electrochemistry, Russian Academy of Sciences (IPCE RAS)
Russia
;
_audit_update_record             
;
2019-12-03 deposited with the CCDC.	2020-08-12 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         'C19 H23 F2 N3 O4 S2, C D Cl3'
_chemical_formula_sum            'C20 H23 Cl3 D F2 N3 O4 S2'
_chemical_formula_weight         579.90

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'
D D 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 '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+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x+1/2, -y, z+1/2'

_cell_length_a                   10.4481(2)
_cell_length_b                   14.3121(3)
_cell_length_c                   16.4591(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2461.20(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    8174
_cell_measurement_theta_min      3.45
_cell_measurement_theta_max      28.43

_exptl_crystal_description       fragment
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.565
_exptl_crystal_F_000             1192
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.180
_exptl_absorpt_coefficient_mu    0.591
_shelx_estimated_absorpt_T_min   0.798
_shelx_estimated_absorpt_T_max   0.901
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.821
_exptl_absorpt_correction_T_max  0.901
_exptl_absorpt_process_details   'SADABS (Bruker, 2008)'
_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 KAPPA APEX II area-detector diffractometer'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            38251
_diffrn_reflns_av_unetI/netI     0.0375
_diffrn_reflns_av_R_equivalents  0.0499
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         3.451
_diffrn_reflns_theta_max         29.995
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             7167
_reflns_number_gt                6426
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.794
_reflns_Friedel_fraction_max     1.000
_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. Completness statistics refer to single and
 composite reflections containing twin component 1 only.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0392P)²+0.8280P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.48(6)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         7167
_refine_ls_number_parameters     308
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0417
_refine_ls_R_factor_gt           0.0347
_refine_ls_wR_factor_ref         0.0830
_refine_ls_wR_factor_gt          0.0796
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_restrained_S_all      1.028
_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
F1 F 0.61959(16) 0.38223(13) 0.69091(11) 0.0269(4) Uani 1 1 d . . . . .
F2 F 0.63384(16) 0.44717(13) 0.25333(11) 0.0258(4) Uani 1 1 d . . . . .
Cl3 Cl 0.57808(11) 0.14490(8) 0.55863(8) 0.0594(3) Uani 1 1 d . . . . .
Cl4 Cl 0.83022(8) 0.22712(7) 0.56127(5) 0.0395(2) Uani 1 1 d . . . . .
Cl5 Cl 0.66341(9) 0.26219(7) 0.42584(5) 0.0381(2) Uani 1 1 d . . . . .
S1 S 0.20640(6) 0.65263(4) 0.64619(3) 0.01345(12) Uani 1 1 d . . . . .
S2 S 0.20571(6) 0.69342(4) 0.33173(3) 0.01364(12) Uani 1 1 d . . . . .
O1 O 0.09256(18) 0.60131(14) 0.62779(11) 0.0184(4) Uani 1 1 d . . . . .
O2 O 0.20966(19) 0.71603(13) 0.71346(10) 0.0183(4) Uani 1 1 d . . . . .
O3 O 0.09314(18) 0.63735(14) 0.33925(11) 0.0192(4) Uani 1 1 d . . . . .
O4 O 0.20788(19) 0.77169(14) 0.27759(10) 0.0192(4) Uani 1 1 d . . . . .
N1 N 0.3576(2) 0.84376(16) 0.50600(12) 0.0120(4) Uani 1 1 d . . . . .
N3 N 0.2408(2) 0.71494(15) 0.56514(12) 0.0127(4) Uani 1 1 d . . . . .
N5 N 0.2367(2) 0.73485(15) 0.42300(12) 0.0125(4) Uani 1 1 d . . . . .
C1 C 0.6706(3) 0.2416(2) 0.53099(19) 0.0277(6) Uani 1 1 d . . . . .
D1A D 0.635492 0.297694 0.559466 0.033 Uiso 1 1 calc R U . . .
C2 C 0.3571(2) 0.77576(18) 0.57022(15) 0.0138(5) Uani 1 1 d . . . . .
H2A H 0.358541 0.808106 0.623386 0.017 Uiso 1 1 calc R U . . .
H2B H 0.434926 0.736546 0.566326 0.017 Uiso 1 1 calc R U . . .
C4 C 0.2347(2) 0.66375(18) 0.48805(14) 0.0140(5) Uani 1 1 d . . . . .
H4A H 0.155238 0.626260 0.485094 0.017 Uiso 1 1 calc R U . . .
H4B H 0.308977 0.621195 0.482792 0.017 Uiso 1 1 calc R U . . .
C6 C 0.3527(2) 0.79671(18) 0.42911(14) 0.0132(5) Uani 1 1 d . . . . .
H6A H 0.430850 0.758454 0.422191 0.016 Uiso 1 1 calc R U . . .
H6B H 0.350516 0.843572 0.384886 0.016 Uiso 1 1 calc R U . . .
C7 C 0.2820(2) 0.93129(18) 0.51748(15) 0.0135(5) Uani 1 1 d . . . . .
C8 C 0.3222(3) 0.97476(19) 0.59840(16) 0.0188(5) Uani 1 1 d . . . . .
H8A H 0.273775 1.032500 0.607394 0.028 Uiso 1 1 calc R U . . .
H8B H 0.304509 0.930712 0.642595 0.028 Uiso 1 1 calc R U . . .
H8C H 0.413900 0.988924 0.597101 0.028 Uiso 1 1 calc R U . . .
C9 C 0.3190(3) 0.99837(19) 0.44898(17) 0.0210(6) Uani 1 1 d . . . . .
H9A H 0.270869 1.056752 0.454802 0.032 Uiso 1 1 calc R U . . .
H9B H 0.410924 1.011610 0.451835 0.032 Uiso 1 1 calc R U . . .
H9C H 0.298903 0.969690 0.396441 0.032 Uiso 1 1 calc R U . . .
C10 C 0.1358(2) 0.9173(2) 0.51668(17) 0.0189(5) Uani 1 1 d . . . . .
H10A H 0.093328 0.977696 0.524537 0.028 Uiso 1 1 calc R U . . .
H10B H 0.109756 0.890672 0.464380 0.028 Uiso 1 1 calc R U . . .
H10C H 0.111306 0.874691 0.560607 0.028 Uiso 1 1 calc R U . . .
C11 C 0.3317(2) 0.57101(18) 0.65971(15) 0.0143(5) Uani 1 1 d . . . . .
C12 C 0.3172(3) 0.48071(19) 0.62962(16) 0.0175(5) Uani 1 1 d . . . . .
H12A H 0.240822 0.463332 0.602145 0.021 Uiso 1 1 calc R U . . .
C13 C 0.4148(3) 0.41652(19) 0.64005(17) 0.0195(5) Uani 1 1 d . . . . .
H13A H 0.406743 0.354411 0.620333 0.023 Uiso 1 1 calc R U . . .
C14 C 0.5245(3) 0.4454(2) 0.68004(17) 0.0190(6) Uani 1 1 d . . . . .
C15 C 0.5413(3) 0.5350(2) 0.70949(16) 0.0176(5) Uani 1 1 d . . . . .
H15A H 0.618612 0.552449 0.735872 0.021 Uiso 1 1 calc R U . . .
C16 C 0.4429(3) 0.59874(19) 0.69957(15) 0.0161(5) Uani 1 1 d . . . . .
H16A H 0.451062 0.660645 0.719743 0.019 Uiso 1 1 calc R U . . .
C21 C 0.3342(2) 0.61958(18) 0.30655(15) 0.0142(5) Uani 1 1 d . . . . .
C22 C 0.3281(3) 0.52520(19) 0.32780(16) 0.0174(5) Uani 1 1 d . . . . .
H22A H 0.254320 0.500982 0.354137 0.021 Uiso 1 1 calc R U . . .
C23 C 0.4301(3) 0.4674(2) 0.31024(16) 0.0190(5) Uani 1 1 d . . . . .
H23A H 0.427973 0.403161 0.324573 0.023 Uiso 1 1 calc R U . . .
C24 C 0.5353(3) 0.5049(2) 0.27144(16) 0.0180(5) Uani 1 1 d . . . . .
C25 C 0.5446(3) 0.5976(2) 0.25027(16) 0.0192(5) Uani 1 1 d . . . . .
H25A H 0.618845 0.620914 0.223854 0.023 Uiso 1 1 calc R U . . .
C26 C 0.4425(3) 0.6562(2) 0.26850(15) 0.0163(5) Uani 1 1 d . . . . .
H26A H 0.446489 0.720728 0.255175 0.020 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F1 C14 1.355(3) . ?
F2 C24 1.354(3) . ?
Cl3 C1 1.748(3) . ?
Cl4 C1 1.752(3) . ?
Cl5 C1 1.757(3) . ?
S1 O1 1.430(2) . ?
S1 O2 1.4321(19) . ?
S1 N3 1.644(2) . ?
S1 C11 1.769(3) . ?
S2 O3 1.429(2) . ?
S2 O4 1.431(2) . ?
S2 N5 1.647(2) . ?
S2 C21 1.758(3) . ?
N1 C6 1.435(3) . ?
N1 C2 1.437(3) . ?
N1 C7 1.493(3) . ?
N3 C4 1.466(3) . ?
N3 C2 1.497(3) . ?
N5 C4 1.477(3) . ?
N5 C6 1.504(3) . ?
C1 D1A 1.0000 . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 C9 1.530(3) . ?
C7 C8 1.529(4) . ?
C7 C10 1.541(4) . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 C12 1.392(4) . ?
C11 C16 1.391(4) . ?
C12 C13 1.383(4) . ?
C12 H12A 0.9500 . ?
C13 C14 1.385(4) . ?
C13 H13A 0.9500 . ?
C14 C15 1.383(4) . ?
C15 C16 1.385(4) . ?
C15 H15A 0.9500 . ?
C16 H16A 0.9500 . ?
C21 C26 1.396(4) . ?
C21 C22 1.397(4) . ?
C22 C23 1.379(4) . ?
C22 H22A 0.9500 . ?
C23 C24 1.380(4) . ?
C23 H23A 0.9500 . ?
C24 C25 1.374(4) . ?
C25 C26 1.390(4) . ?
C25 H25A 0.9500 . ?
C26 H26A 0.9500 . ?

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
O1 S1 O2 120.59(12) . . ?
O1 S1 N3 106.76(11) . . ?
O2 S1 N3 106.17(11) . . ?
O1 S1 C11 107.64(12) . . ?
O2 S1 C11 107.67(12) . . ?
N3 S1 C11 107.38(11) . . ?
O3 S2 O4 120.42(12) . . ?
O3 S2 N5 106.55(11) . . ?
O4 S2 N5 106.44(11) . . ?
O3 S2 C21 108.14(12) . . ?
O4 S2 C21 108.16(12) . . ?
N5 S2 C21 106.33(11) . . ?
C6 N1 C2 109.3(2) . . ?
C6 N1 C7 119.12(19) . . ?
C2 N1 C7 118.26(19) . . ?
C4 N3 C2 111.94(19) . . ?
C4 N3 S1 114.93(16) . . ?
C2 N3 S1 116.56(16) . . ?
C4 N5 C6 111.61(19) . . ?
C4 N5 S2 114.23(17) . . ?
C6 N5 S2 115.55(15) . . ?
Cl3 C1 Cl4 111.04(18) . . ?
Cl3 C1 Cl5 111.44(18) . . ?
Cl4 C1 Cl5 109.92(17) . . ?
Cl3 C1 D1A 108.1 . . ?
Cl4 C1 D1A 108.1 . . ?
Cl5 C1 D1A 108.1 . . ?
N1 C2 N3 110.82(19) . . ?
N1 C2 H2A 109.5 . . ?
N3 C2 H2A 109.5 . . ?
N1 C2 H2B 109.5 . . ?
N3 C2 H2B 109.5 . . ?
H2A C2 H2B 108.1 . . ?
N3 C4 N5 106.4(2) . . ?
N3 C4 H4A 110.4 . . ?
N5 C4 H4A 110.4 . . ?
N3 C4 H4B 110.4 . . ?
N5 C4 H4B 110.4 . . ?
H4A C4 H4B 108.6 . . ?
N1 C6 N5 111.36(19) . . ?
N1 C6 H6A 109.4 . . ?
N5 C6 H6A 109.4 . . ?
N1 C6 H6B 109.4 . . ?
N5 C6 H6B 109.4 . . ?
H6A C6 H6B 108.0 . . ?
N1 C7 C9 107.4(2) . . ?
N1 C7 C8 107.9(2) . . ?
C9 C7 C8 108.5(2) . . ?
N1 C7 C10 114.5(2) . . ?
C9 C7 C10 109.0(2) . . ?
C8 C7 C10 109.4(2) . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C7 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C7 C9 H9A 109.5 . . ?
C7 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C7 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C7 C10 H10A 109.5 . . ?
C7 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C7 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C12 C11 C16 121.6(2) . . ?
C12 C11 S1 119.2(2) . . ?
C16 C11 S1 119.3(2) . . ?
C13 C12 C11 119.5(2) . . ?
C13 C12 H12A 120.3 . . ?
C11 C12 H12A 120.3 . . ?
C12 C13 C14 118.1(3) . . ?
C12 C13 H13A 120.9 . . ?
C14 C13 H13A 120.9 . . ?
F1 C14 C15 118.6(3) . . ?
F1 C14 C13 118.1(3) . . ?
C15 C14 C13 123.3(3) . . ?
C14 C15 C16 118.4(3) . . ?
C14 C15 H15A 120.8 . . ?
C16 C15 H15A 120.8 . . ?
C15 C16 C11 119.2(3) . . ?
C15 C16 H16A 120.4 . . ?
C11 C16 H16A 120.4 . . ?
C26 C21 C22 120.8(2) . . ?
C26 C21 S2 120.0(2) . . ?
C22 C21 S2 119.2(2) . . ?
C23 C22 C21 119.5(3) . . ?
C23 C22 H22A 120.3 . . ?
C21 C22 H22A 120.3 . . ?
C22 C23 C24 118.6(3) . . ?
C22 C23 H23A 120.7 . . ?
C24 C23 H23A 120.7 . . ?
F2 C24 C25 118.6(3) . . ?
F2 C24 C23 118.1(3) . . ?
C25 C24 C23 123.3(3) . . ?
C24 C25 C26 118.3(3) . . ?
C24 C25 H25A 120.9 . . ?
C26 C25 H25A 120.9 . . ?
C25 C26 C21 119.5(3) . . ?
C25 C26 H26A 120.3 . . ?
C21 C26 H26A 120.3 . . ?

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
O1 S1 N3 C4 -46.6(2) . . . . ?
O2 S1 N3 C4 -176.41(18) . . . . ?
C11 S1 N3 C4 68.6(2) . . . . ?
O1 S1 N3 C2 179.56(18) . . . . ?
O2 S1 N3 C2 49.7(2) . . . . ?
C11 S1 N3 C2 -65.2(2) . . . . ?
O3 S2 N5 C4 48.6(2) . . . . ?
O4 S2 N5 C4 178.28(17) . . . . ?
C21 S2 N5 C4 -66.57(19) . . . . ?
O3 S2 N5 C6 -179.88(17) . . . . ?
O4 S2 N5 C6 -50.2(2) . . . . ?
C21 S2 N5 C6 64.9(2) . . . . ?
C6 N1 C2 N3 -57.9(3) . . . . ?
C7 N1 C2 N3 82.8(3) . . . . ?
C4 N3 C2 N1 60.2(3) . . . . ?
S1 N3 C2 N1 -164.60(17) . . . . ?
C2 N3 C4 N5 -57.6(2) . . . . ?
S1 N3 C4 N5 166.43(16) . . . . ?
C6 N5 C4 N3 56.6(2) . . . . ?
S2 N5 C4 N3 -169.98(16) . . . . ?
C2 N1 C6 N5 57.4(3) . . . . ?
C7 N1 C6 N5 -82.9(3) . . . . ?
C4 N5 C6 N1 -58.7(3) . . . . ?
S2 N5 C6 N1 168.56(16) . . . . ?
C6 N1 C7 C9 -53.8(3) . . . . ?
C2 N1 C7 C9 169.4(2) . . . . ?
C6 N1 C7 C8 -170.6(2) . . . . ?
C2 N1 C7 C8 52.6(3) . . . . ?
C6 N1 C7 C10 67.4(3) . . . . ?
C2 N1 C7 C10 -69.5(3) . . . . ?
O1 S1 C11 C12 18.2(2) . . . . ?
O2 S1 C11 C12 149.6(2) . . . . ?
N3 S1 C11 C12 -96.4(2) . . . . ?
O1 S1 C11 C16 -162.30(19) . . . . ?
O2 S1 C11 C16 -30.9(2) . . . . ?
N3 S1 C11 C16 83.1(2) . . . . ?
C16 C11 C12 C13 0.6(4) . . . . ?
S1 C11 C12 C13 -179.9(2) . . . . ?
C11 C12 C13 C14 -0.4(4) . . . . ?
C12 C13 C14 F1 179.4(2) . . . . ?
C12 C13 C14 C15 -0.4(4) . . . . ?
F1 C14 C15 C16 -178.8(2) . . . . ?
C13 C14 C15 C16 1.0(4) . . . . ?
C14 C15 C16 C11 -0.8(4) . . . . ?
C12 C11 C16 C15 0.0(4) . . . . ?
S1 C11 C16 C15 -179.44(19) . . . . ?
O3 S2 C21 C26 157.7(2) . . . . ?
O4 S2 C21 C26 25.8(2) . . . . ?
N5 S2 C21 C26 -88.2(2) . . . . ?
O3 S2 C21 C22 -24.7(2) . . . . ?
O4 S2 C21 C22 -156.6(2) . . . . ?
N5 S2 C21 C22 89.4(2) . . . . ?
C26 C21 C22 C23 -0.6(4) . . . . ?
S2 C21 C22 C23 -178.2(2) . . . . ?
C21 C22 C23 C24 -0.5(4) . . . . ?
C22 C23 C24 F2 -178.9(2) . . . . ?
C22 C23 C24 C25 1.0(4) . . . . ?
F2 C24 C25 C26 179.5(2) . . . . ?
C23 C24 C25 C26 -0.4(4) . . . . ?
C24 C25 C26 C21 -0.7(4) . . . . ?
C22 C21 C26 C25 1.2(4) . . . . ?
S2 C21 C26 C25 178.77(19) . . . . ?

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
C1 D1A F1 1.00 2.48 3.356(4) 145.5 . yes
C2 H2A O3 0.99 2.64 3.138(3) 110.9 2_566 yes
C8 H8C Cl3 0.98 2.89 3.675(3) 138.3 1_565 yes
C9 H9C F2 0.98 2.58 3.445(3) 146.7 3_655 yes
C10 H10B N5 0.98 2.68 3.211(4) 114.2 . yes
C10 H10C N3 0.98 2.66 3.198(4) 115.0 . yes
C15 H15A F2 0.95 2.60 3.479(3) 153.6 4_665 yes
C23 H23A Cl4 0.95 2.84 3.649(3) 144.0 2_456 yes

_refine_diff_density_max         0.427
_refine_diff_density_min         -0.536
_refine_diff_density_rms         0.060


_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: CDCl3'
####################################################################### 
# 
# 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_AK118
_database_code_depnum_ccdc_archive 'CCDC 1969755'
loop_
_audit_author_name
_audit_author_address
'Anna Sinelshchikova'
;Frumkin Institute of Physical Chemistry and Electrochemistry, Russian Academy of Sciences (IPCE RAS)
Russia
;
_audit_update_record             
;
2019-12-03 deposited with the CCDC.	2020-08-12 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         'C19 H23 I2 N3 O4 S2'
_chemical_formula_sum            'C19 H23 I2 N3 O4 S2'
_chemical_formula_weight         675.32

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'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           62
_space_group_name_H-M_alt        'P n m a'
_space_group_name_Hall           '-P 2ac 2n'

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

_cell_length_a                   15.4374(4)
_cell_length_b                   24.9622(6)
_cell_length_c                   6.1336(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2363.59(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    9915
_cell_measurement_theta_min      2.64
_cell_measurement_theta_max      29.74

_exptl_crystal_description       fragment
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.898
_exptl_crystal_F_000             1312
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.500
_exptl_crystal_size_mid          0.420
_exptl_crystal_size_min          0.180
_exptl_absorpt_coefficient_mu    2.868
_shelx_estimated_absorpt_T_min   0.328
_shelx_estimated_absorpt_T_max   0.626
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.451
_exptl_absorpt_correction_T_max  0.626
_exptl_absorpt_process_details   'SADABS (Bruker, 2008)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  
'Bruker KAPPA APEX II area-detector diffractometer'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            28130
_diffrn_reflns_av_unetI/netI     0.0154
_diffrn_reflns_av_R_equivalents  0.0268
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_k_min       -35
_diffrn_reflns_limit_k_max       35
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_theta_min         3.930
_diffrn_reflns_theta_max         29.995
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             3510
_reflns_number_gt                2929
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-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)+(0.0258P)²+3.9448P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3510
_refine_ls_number_parameters     142
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0474
_refine_ls_R_factor_gt           0.0383
_refine_ls_wR_factor_ref         0.0854
_refine_ls_wR_factor_gt          0.0815
_refine_ls_goodness_of_fit_ref   1.110
_refine_ls_restrained_S_all      1.110
_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
I1 I 0.66688(2) 0.47570(2) 0.81041(5) 0.05925(10) Uani 1 1 d . . . . .
S1 S 0.35303(6) 0.35147(4) 0.28140(15) 0.0501(2) Uani 1 1 d . . . . .
O1 O 0.27583(18) 0.38275(12) 0.3004(6) 0.0760(9) Uani 1 1 d . . . . .
O2 O 0.3866(2) 0.33656(11) 0.0727(4) 0.0679(8) Uani 1 1 d . . . . .
N1 N 0.2389(3) 0.250000 0.6608(6) 0.0452(8) Uani 1 2 d S T P . .
N3 N 0.33457(17) 0.29650(11) 0.4120(5) 0.0493(6) Uani 1 1 d . . . . .
C2 C 0.2912(2) 0.29700(17) 0.6294(6) 0.0596(10) Uani 1 1 d . . . . .
H2A H 0.334800 0.298797 0.743096 0.072 Uiso 1 1 calc R U . . .
H2B H 0.255020 0.328643 0.641153 0.072 Uiso 1 1 calc R U . . .
C4 C 0.3905(3) 0.250000 0.3832(9) 0.0522(11) Uani 1 2 d S T P . .
H4A H 0.416159 0.249999 0.238846 0.063 Uiso 1 2 calc R U P . .
H4B H 0.436594 0.250000 0.490753 0.063 Uiso 1 2 calc R U P . .
C5 C 0.1484(3) 0.250000 0.5746(7) 0.0414(9) Uani 1 2 d S T P . .
C6 C 0.1427(3) 0.250000 0.3259(8) 0.0558(13) Uani 1 2 d S T P . .
H6A H 0.083019 0.250000 0.282261 0.084 Uiso 1 2 calc R U P . .
H6B H 0.170821 0.281401 0.269634 0.084 Uiso 0.5 1 calc R U P . .
H6C H 0.170821 0.218599 0.269634 0.084 Uiso 0.5 1 calc R U P . .
C7 C 0.1020(3) 0.29915(17) 0.6646(7) 0.0676(11) Uani 1 1 d . . . . .
H7A H 0.043573 0.299906 0.611122 0.101 Uiso 1 1 calc R U . . .
H7B H 0.101394 0.297570 0.821019 0.101 Uiso 1 1 calc R U . . .
H7C H 0.131810 0.330940 0.618482 0.101 Uiso 1 1 calc R U . . .
C8 C 0.43635(18) 0.38637(11) 0.4195(5) 0.0371(6) Uani 1 1 d . . . . .
C9 C 0.41892(19) 0.41189(14) 0.6141(6) 0.0463(7) Uani 1 1 d . . . . .
H9A H 0.363129 0.411405 0.671277 0.056 Uiso 1 1 calc R U . . .
C10 C 0.4843(2) 0.43809(13) 0.7236(5) 0.0447(7) Uani 1 1 d . . . . .
H10A H 0.472886 0.455566 0.854416 0.054 Uiso 1 1 calc R U . . .
C11 C 0.56701(18) 0.43817(11) 0.6373(5) 0.0371(6) Uani 1 1 d . . . . .
C12 C 0.58446(19) 0.41357(13) 0.4412(6) 0.0468(7) Uani 1 1 d . . . . .
H12A H 0.639932 0.414659 0.382249 0.056 Uiso 1 1 calc R U . . .
C13 C 0.5184(2) 0.38723(14) 0.3332(5) 0.0480(7) Uani 1 1 d . . . . .
H13A H 0.529569 0.370037 0.201649 0.058 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
I1 C11 2.093(3) . ?
S1 O1 1.430(3) . ?
S1 O2 1.430(3) . ?
S1 N3 1.614(3) . ?
S1 C8 1.769(3) . ?
N1 C2 1.437(4) . ?
N1 C2 1.437(4) 7_565 ?
N1 C5 1.494(6) . ?
N3 C4 1.457(4) . ?
N3 C2 1.493(5) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C5 C7 1.524(4) . ?
C5 C7 1.524(4) 7_565 ?
C5 C6 1.528(6) . ?
C6 H6A 0.9600 . ?
C6 H6B 0.9600 . ?
C6 H6C 0.9600 . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C8 C13 1.373(4) . ?
C8 C9 1.380(4) . ?
C9 C10 1.377(4) . ?
C9 H9A 0.9300 . ?
C10 C11 1.382(4) . ?
C10 H10A 0.9300 . ?
C11 C12 1.377(4) . ?
C12 C13 1.383(4) . ?
C12 H12A 0.9300 . ?
C13 H13A 0.9300 . ?

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
O1 S1 O2 121.13(19) . . ?
O1 S1 N3 106.06(18) . . ?
O2 S1 N3 106.67(16) . . ?
O1 S1 C8 107.34(15) . . ?
O2 S1 C8 107.06(16) . . ?
N3 S1 C8 108.02(15) . . ?
C2 N1 C2 109.5(4) . 7_565 ?
C2 N1 C5 118.6(2) . . ?
C2 N1 C5 118.6(2) 7_565 . ?
C4 N3 C2 112.4(3) . . ?
C4 N3 S1 120.8(3) . . ?
C2 N3 S1 121.0(2) . . ?
N1 C2 N3 111.4(3) . . ?
N1 C2 H2A 109.4 . . ?
N3 C2 H2A 109.4 . . ?
N1 C2 H2B 109.4 . . ?
N3 C2 H2B 109.4 . . ?
H2A C2 H2B 108.0 . . ?
N3 C4 N3 105.6(4) 7_565 . ?
N3 C4 H4A 110.6 7_565 . ?
N3 C4 H4A 110.6 . . ?
N3 C4 H4B 110.6 7_565 . ?
N3 C4 H4B 110.6 . . ?
H4A C4 H4B 108.8 . . ?
N1 C5 C7 108.1(3) . . ?
N1 C5 C7 108.1(3) . 7_565 ?
C7 C5 C7 107.2(4) . 7_565 ?
N1 C5 C6 114.0(4) . . ?
C7 C5 C6 109.6(3) . . ?
C7 C5 C6 109.6(3) 7_565 . ?
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 . . ?
C5 C7 H7A 109.5 . . ?
C5 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C5 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C13 C8 C9 120.4(3) . . ?
C13 C8 S1 119.6(2) . . ?
C9 C8 S1 120.0(2) . . ?
C10 C9 C8 119.9(3) . . ?
C10 C9 H9A 120.1 . . ?
C8 C9 H9A 120.1 . . ?
C9 C10 C11 119.4(3) . . ?
C9 C10 H10A 120.3 . . ?
C11 C10 H10A 120.3 . . ?
C12 C11 C10 121.0(3) . . ?
C12 C11 I1 119.9(2) . . ?
C10 C11 I1 119.1(2) . . ?
C11 C12 C13 119.1(3) . . ?
C11 C12 H12A 120.4 . . ?
C13 C12 H12A 120.4 . . ?
C8 C13 C12 120.2(3) . . ?
C8 C13 H13A 119.9 . . ?
C12 C13 H13A 119.9 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 S1 N3 C4 165.0(3) . . . . ?
O2 S1 N3 C4 34.6(3) . . . . ?
C8 S1 N3 C4 -80.2(3) . . . . ?
O1 S1 N3 C2 -43.8(3) . . . . ?
O2 S1 N3 C2 -174.2(3) . . . . ?
C8 S1 N3 C2 71.0(3) . . . . ?
C2 N1 C2 N3 55.3(5) 7_565 . . . ?
C5 N1 C2 N3 -85.0(4) . . . . ?
C4 N3 C2 N1 -59.3(4) . . . . ?
S1 N3 C2 N1 147.3(3) . . . . ?
C2 N3 C4 N3 58.2(5) . . . 7_565 ?
S1 N3 C4 N3 -148.3(2) . . . 7_565 ?
C2 N1 C5 C7 -53.7(5) . . . . ?
C2 N1 C5 C7 169.5(3) 7_565 . . . ?
C2 N1 C5 C7 -169.5(3) . . . 7_565 ?
C2 N1 C5 C7 53.7(5) 7_565 . . 7_565 ?
C2 N1 C5 C6 68.4(3) . . . . ?
C2 N1 C5 C6 -68.4(3) 7_565 . . . ?
O1 S1 C8 C13 -141.0(3) . . . . ?
O2 S1 C8 C13 -9.5(3) . . . . ?
N3 S1 C8 C13 105.0(3) . . . . ?
O1 S1 C8 C9 39.9(3) . . . . ?
O2 S1 C8 C9 171.4(3) . . . . ?
N3 S1 C8 C9 -74.1(3) . . . . ?
C13 C8 C9 C10 -0.5(5) . . . . ?
S1 C8 C9 C10 178.7(3) . . . . ?
C8 C9 C10 C11 -0.4(5) . . . . ?
C9 C10 C11 C12 1.6(5) . . . . ?
C9 C10 C11 I1 -177.8(3) . . . . ?
C10 C11 C12 C13 -1.8(5) . . . . ?
I1 C11 C12 C13 177.5(3) . . . . ?
C9 C8 C13 C12 0.2(5) . . . . ?
S1 C8 C13 C12 -178.9(3) . . . . ?
C11 C12 C13 C8 0.9(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
_geom_hbond_publ_flag
C2 H2A O2 0.97 2.37 3.246(4) 149.9 1_556 yes
C12 H12A O1 0.93 2.51 3.394(4) 159.2 6_656 yes

_refine_diff_density_max         1.132
_refine_diff_density_min         -0.783
_refine_diff_density_rms         0.082


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: DMSO-d6'
####################################################################### 
# 
# 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_ak118_lt
_database_code_depnum_ccdc_archive 'CCDC 1969758'
loop_
_audit_author_name
_audit_author_address
'Anna Sinelshchikova'
;Frumkin Institute of Physical Chemistry and Electrochemistry, Russian Academy of Sciences (IPCE RAS)
Russia
;
_audit_update_record             
;
2019-12-03 deposited with the CCDC.	2020-08-12 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         'C19 H23 I2 N3 O4 S2'
_chemical_formula_sum            'C19 H23 I2 N3 O4 S2'
_chemical_formula_weight         675.32

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'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           62
_space_group_name_H-M_alt        'P n m a'
_space_group_name_Hall           '-P 2ac 2n'

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

_cell_length_a                   15.4193(4)
_cell_length_b                   24.5788(7)
_cell_length_c                   6.1039(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2313.30(12)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9837
_cell_measurement_theta_min      3.44
_cell_measurement_theta_max      34.94

_exptl_crystal_description       fragment
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.939
_exptl_crystal_F_000             1312
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.320
_exptl_crystal_size_min          0.160
_exptl_absorpt_coefficient_mu    2.930
_shelx_estimated_absorpt_T_min   0.387
_shelx_estimated_absorpt_T_max   0.651
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.484
_exptl_absorpt_correction_T_max  0.651
_exptl_absorpt_process_details   'SADABS (Bruker, 2008)'
_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 KAPPA APEX II area-detector diffractometer'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            57033
_diffrn_reflns_av_unetI/netI     0.0157
_diffrn_reflns_av_R_equivalents  0.0325
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_k_min       -39
_diffrn_reflns_limit_k_max       39
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_theta_min         3.955
_diffrn_reflns_theta_max         34.996
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             5176
_reflns_number_gt                4646
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-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)+(0.0145P)²+2.2020P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5176
_refine_ls_number_parameters     142
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0303
_refine_ls_R_factor_gt           0.0253
_refine_ls_wR_factor_ref         0.0543
_refine_ls_wR_factor_gt          0.0523
_refine_ls_goodness_of_fit_ref   1.198
_refine_ls_restrained_S_all      1.198
_refine_ls_shift/su_max          0.003
_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
I1 I 0.66785(2) 0.47517(2) 0.81732(2) 0.02315(3) Uani 1 1 d . . . . .
S1 S 0.35100(3) 0.35333(2) 0.27679(7) 0.02246(8) Uani 1 1 d . . . . .
O1 O 0.27354(9) 0.38525(6) 0.2962(3) 0.0367(4) Uani 1 1 d . . . . .
O2 O 0.38452(9) 0.33861(6) 0.0659(2) 0.0299(3) Uani 1 1 d . . . . .
N1 N 0.23614(12) 0.250000 0.6579(3) 0.0204(3) Uani 1 2 d S T P . .
N3 N 0.33171(9) 0.29723(6) 0.4065(3) 0.0228(3) Uani 1 1 d . . . . .
C2 C 0.28841(12) 0.29780(9) 0.6258(3) 0.0296(4) Uani 1 1 d . . . . .
H2A H 0.333065 0.299739 0.742072 0.036 Uiso 1 1 calc R U . . .
H2B H 0.251382 0.330571 0.637822 0.036 Uiso 1 1 calc R U . . .
C4 C 0.38811(14) 0.250000 0.3780(4) 0.0219(4) Uani 1 2 d S T P . .
H4A H 0.414492 0.250000 0.230099 0.026 Uiso 1 2 calc R U P . .
H4B H 0.435026 0.250000 0.488705 0.026 Uiso 1 2 calc R U P . .
C5 C 0.14547(13) 0.250000 0.5700(4) 0.0166(3) Uani 1 2 d S T P . .
C6 C 0.13995(15) 0.250000 0.3196(4) 0.0242(4) Uani 1 2 d S T P . .
H6A H 0.078940 0.250000 0.274558 0.036 Uiso 1 2 calc R U P . .
H6B H 0.168684 0.282555 0.261924 0.036 Uiso 0.5 1 calc R U P . .
H6C H 0.168683 0.217445 0.261924 0.036 Uiso 0.5 1 calc R U P . .
C7 C 0.09929(13) 0.30007(7) 0.6614(3) 0.0284(4) Uani 1 1 d . . . . .
H7A H 0.039609 0.301095 0.606330 0.043 Uiso 1 1 calc R U . . .
H7B H 0.098590 0.298266 0.821762 0.043 Uiso 1 1 calc R U . . .
H7C H 0.130039 0.332982 0.614671 0.043 Uiso 1 1 calc R U . . .
C8 C 0.43478(9) 0.38810(6) 0.4172(3) 0.0173(2) Uani 1 1 d . . . . .
C9 C 0.41714(9) 0.41326(7) 0.6159(3) 0.0203(3) Uani 1 1 d . . . . .
H9A H 0.359974 0.413022 0.673942 0.024 Uiso 1 1 calc R U . . .
C10 C 0.48382(9) 0.43876(6) 0.7290(3) 0.0188(3) Uani 1 1 d . . . . .
H10A H 0.472830 0.455909 0.865676 0.023 Uiso 1 1 calc R U . . .
C11 C 0.56687(9) 0.43897(6) 0.6403(3) 0.0159(2) Uani 1 1 d . . . . .
C12 C 0.58458(9) 0.41479(7) 0.4399(3) 0.0201(3) Uani 1 1 d . . . . .
H12A H 0.641400 0.415923 0.379936 0.024 Uiso 1 1 calc R U . . .
C13 C 0.51757(10) 0.38880(7) 0.3283(3) 0.0201(3) Uani 1 1 d . . . . .
H13A H 0.528515 0.371607 0.191646 0.024 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
I1 C11 2.0939(14) . ?
S1 O2 1.4338(15) . ?
S1 O1 1.4338(14) . ?
S1 N3 1.6178(15) . ?
S1 C8 1.7704(15) . ?
N1 C2 1.438(2) 7_565 ?
N1 C2 1.438(2) . ?
N1 C5 1.497(3) . ?
N3 C4 1.4609(19) . ?
N3 C2 1.496(2) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 C7 1.527(2) . ?
C5 C7 1.527(2) 7_565 ?
C5 C6 1.531(3) . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C8 C13 1.387(2) . ?
C8 C9 1.388(2) . ?
C9 C10 1.388(2) . ?
C9 H9A 0.9500 . ?
C10 C11 1.390(2) . ?
C10 H10A 0.9500 . ?
C11 C12 1.387(2) . ?
C12 C13 1.393(2) . ?
C12 H12A 0.9500 . ?
C13 H13A 0.9500 . ?

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
O2 S1 O1 120.85(9) . . ?
O2 S1 N3 106.90(8) . . ?
O1 S1 N3 105.83(9) . . ?
O2 S1 C8 107.07(8) . . ?
O1 S1 C8 107.67(8) . . ?
N3 S1 C8 107.97(8) . . ?
C2 N1 C2 109.6(2) 7_565 . ?
C2 N1 C5 118.32(12) 7_565 . ?
C2 N1 C5 118.32(12) . . ?
C4 N3 C2 112.34(17) . . ?
C4 N3 S1 120.62(12) . . ?
C2 N3 S1 120.81(12) . . ?
N1 C2 N3 111.37(14) . . ?
N1 C2 H2A 109.4 . . ?
N3 C2 H2A 109.4 . . ?
N1 C2 H2B 109.4 . . ?
N3 C2 H2B 109.4 . . ?
H2A C2 H2B 108.0 . . ?
N3 C4 N3 105.23(17) 7_565 . ?
N3 C4 H4A 110.7 7_565 . ?
N3 C4 H4A 110.7 . . ?
N3 C4 H4B 110.7 7_565 . ?
N3 C4 H4B 110.7 . . ?
H4A C4 H4B 108.8 . . ?
N1 C5 C7 107.73(13) . . ?
N1 C5 C7 107.73(13) . 7_565 ?
C7 C5 C7 107.4(2) . 7_565 ?
N1 C5 C6 114.18(18) . . ?
C7 C5 C6 109.79(13) . . ?
C7 C5 C6 109.79(13) 7_565 . ?
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 . . ?
C5 C7 H7A 109.5 . . ?
C5 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C5 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C13 C8 C9 121.11(14) . . ?
C13 C8 S1 119.20(12) . . ?
C9 C8 S1 119.67(11) . . ?
C10 C9 C8 119.37(14) . . ?
C10 C9 H9A 120.3 . . ?
C8 C9 H9A 120.3 . . ?
C9 C10 C11 119.35(14) . . ?
C9 C10 H10A 120.3 . . ?
C11 C10 H10A 120.3 . . ?
C12 C11 C10 121.56(13) . . ?
C12 C11 I1 119.40(10) . . ?
C10 C11 I1 119.03(11) . . ?
C11 C12 C13 118.81(14) . . ?
C11 C12 H12A 120.6 . . ?
C13 C12 H12A 120.6 . . ?
C8 C13 C12 119.78(14) . . ?
C8 C13 H13A 120.1 . . ?
C12 C13 H13A 120.1 . . ?

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
O2 S1 N3 C4 35.47(17) . . . . ?
O1 S1 N3 C4 165.51(15) . . . . ?
C8 S1 N3 C4 -79.43(16) . . . . ?
O2 S1 N3 C2 -174.40(13) . . . . ?
O1 S1 N3 C2 -44.37(15) . . . . ?
C8 S1 N3 C2 70.70(14) . . . . ?
C2 N1 C2 N3 55.1(3) 7_565 . . . ?
C5 N1 C2 N3 -84.6(2) . . . . ?
C4 N3 C2 N1 -59.5(2) . . . . ?
S1 N3 C2 N1 148.15(14) . . . . ?
C2 N3 C4 N3 58.6(2) . . . 7_565 ?
S1 N3 C4 N3 -148.95(10) . . . 7_565 ?
C2 N1 C5 C7 169.65(16) 7_565 . . . ?
C2 N1 C5 C7 -54.1(2) . . . . ?
C2 N1 C5 C7 54.1(2) 7_565 . . 7_565 ?
C2 N1 C5 C7 -169.65(16) . . . 7_565 ?
C2 N1 C5 C6 -68.13(15) 7_565 . . . ?
C2 N1 C5 C6 68.13(15) . . . . ?
O2 S1 C8 C13 -9.38(15) . . . . ?
O1 S1 C8 C13 -140.74(14) . . . . ?
N3 S1 C8 C13 105.42(14) . . . . ?
O2 S1 C8 C9 171.86(13) . . . . ?
O1 S1 C8 C9 40.50(16) . . . . ?
N3 S1 C8 C9 -73.35(14) . . . . ?
C13 C8 C9 C10 -1.1(2) . . . . ?
S1 C8 C9 C10 177.69(13) . . . . ?
C8 C9 C10 C11 0.5(2) . . . . ?
C9 C10 C11 C12 0.7(2) . . . . ?
C9 C10 C11 I1 -177.88(12) . . . . ?
C10 C11 C12 C13 -1.3(2) . . . . ?
I1 C11 C12 C13 177.26(12) . . . . ?
C9 C8 C13 C12 0.4(2) . . . . ?
S1 C8 C13 C12 -178.31(12) . . . . ?
C11 C12 C13 C8 0.8(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
_geom_hbond_publ_flag
C2 H2A O2 0.99 2.33 3.228(2) 149.7 1_556 yes
C12 H12A O1 0.95 2.42 3.331(2) 159.6 6_656 yes

_refine_diff_density_max         0.551
_refine_diff_density_min         -0.938
_refine_diff_density_rms         0.088


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: DMSO-d6'
