# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2023

####################################################################### 
# 
# 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_I596
_database_code_depnum_ccdc_archive 'CCDC 2236983'
loop_
_audit_author_name
_audit_author_address
'Mikhail Grigoriev'
;IPCE RAS
Russia
;
_audit_update_record             
;
2023-01-18 deposited with the CCDC.	2023-02-28 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            'C15 H16 Cl2 N2 O3 S'
_chemical_formula_weight         375.26

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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

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

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.3058(11)
_cell_length_b                   10.1615(14)
_cell_length_c                   12.4124(18)
_cell_angle_alpha                105.388(6)
_cell_angle_beta                 106.574(6)
_cell_angle_gamma                100.321(6)
_cell_volume                     818.5(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    1398
_cell_measurement_theta_min      2.93
_cell_measurement_theta_max      23.44

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.523
_exptl_crystal_F_000             388
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.050
_exptl_crystal_size_min          0.040
_exptl_absorpt_coefficient_mu    0.539
_shelx_estimated_absorpt_T_min   0.813
_shelx_estimated_absorpt_T_max   0.979
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8653
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_process_details   
;
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;
_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            18356
_diffrn_reflns_av_unetI/netI     0.1363
_diffrn_reflns_av_R_equivalents  0.1086
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         4.093
_diffrn_reflns_theta_max         29.999
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.973
_diffrn_measured_fraction_theta_full 0.978
_diffrn_reflns_Laue_measured_fraction_max 0.973
_diffrn_reflns_Laue_measured_fraction_full 0.978
_diffrn_reflns_point_group_measured_fraction_max 0.973
_diffrn_reflns_point_group_measured_fraction_full 0.978
_reflns_number_total             4650
_reflns_number_gt                2573
_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)+(0.0663P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4650
_refine_ls_number_parameters     215
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1396
_refine_ls_R_factor_gt           0.0633
_refine_ls_wR_factor_ref         0.1520
_refine_ls_wR_factor_gt          0.1243
_refine_ls_goodness_of_fit_ref   0.965
_refine_ls_restrained_S_all      0.965
_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 0.80847(12) 0.72093(10) 1.02254(9) 0.0300(2) Uani 1 1 d . . . . .
Cl2 Cl 0.80462(11) 0.42469(10) 0.82136(9) 0.0258(2) Uani 1 1 d . . . . .
S1 S 0.36863(12) 0.61433(10) 0.89171(9) 0.0232(2) Uani 1 1 d . . . . .
O1 O 0.5796(3) 0.3213(3) 0.5215(2) 0.0238(6) Uani 1 1 d . . . . .
O2 O 0.0983(3) -0.0126(3) 0.7464(2) 0.0231(6) Uani 1 1 d . . . . .
O3 O 0.4125(3) 0.0916(3) 0.7686(2) 0.0236(6) Uani 1 1 d . . . . .
N1 N -0.0651(4) 0.2455(3) 0.5296(3) 0.0177(6) Uani 1 1 d . . . . .
H1 H -0.170(5) 0.262(4) 0.512(3) 0.021 Uiso 1 1 d . U . . .
N2 N 0.2625(4) 0.4672(3) 0.7752(3) 0.0202(6) Uani 1 1 d . . . . .
C2 C 0.0661(4) 0.2995(3) 0.4820(3) 0.0153(7) Uani 1 1 d . . . . .
C3 C 0.2596(4) 0.2973(3) 0.5268(3) 0.0139(7) Uani 1 1 d . . . . .
C4 C 0.3290(4) 0.2684(4) 0.6445(3) 0.0161(7) Uani 1 1 d . . . . .
H4A H 0.443952 0.227219 0.646764 0.019 Uiso 1 1 calc R U . . .
C5 C 0.1626(4) 0.1608(4) 0.6517(3) 0.0154(7) Uani 1 1 d . . . . .
C6 C -0.0284(4) 0.1619(4) 0.6000(3) 0.0162(7) Uani 1 1 d . . . . .
C7 C -0.0274(4) 0.3527(4) 0.3837(3) 0.0188(7) Uani 1 1 d . . . . .
H7A H -0.146298 0.378273 0.393474 0.028 Uiso 1 1 calc R U . . .
H7B H -0.064607 0.278097 0.306451 0.028 Uiso 1 1 calc R U . . .
H7C H 0.067573 0.436457 0.387129 0.028 Uiso 1 1 calc R U . . .
C8 C 0.4039(4) 0.3140(3) 0.4677(3) 0.0155(7) Uani 1 1 d . . . . .
C9 C 0.3482(5) 0.3152(4) 0.3417(3) 0.0226(8) Uani 1 1 d . . . . .
H9A H 0.229068 0.237091 0.290611 0.034 Uiso 1 1 calc R U . . .
H9B H 0.457897 0.303623 0.312823 0.034 Uiso 1 1 calc R U . . .
H9C H 0.321301 0.405773 0.339593 0.034 Uiso 1 1 calc R U . . .
C10 C 0.2128(4) 0.0708(4) 0.7243(3) 0.0183(7) Uani 1 1 d . . . . .
C11 C 0.4780(5) 0.0117(5) 0.8469(4) 0.0327(10) Uani 1 1 d . . . . .
H11A H 0.428216 -0.091455 0.801802 0.039 Uiso 1 1 calc R U . . .
H11B H 0.425915 0.031721 0.913176 0.039 Uiso 1 1 calc R U . . .
C12 C 0.7022(5) 0.0565(4) 0.8955(4) 0.0308(9) Uani 1 1 d . . . . .
H12A H 0.749990 0.009698 0.953235 0.046 Uiso 1 1 calc R U . . .
H12B H 0.749955 0.159760 0.934913 0.046 Uiso 1 1 calc R U . . .
H12C H 0.752161 0.029300 0.829824 0.046 Uiso 1 1 calc R U . . .
C13 C -0.2126(4) 0.0773(4) 0.6067(3) 0.0213(8) Uani 1 1 d . . . . .
H13A H -0.318032 0.041758 0.528102 0.032 Uiso 1 1 calc R U . . .
H13B H -0.255608 0.137833 0.664835 0.032 Uiso 1 1 calc R U . . .
H13C H -0.184736 -0.003026 0.631598 0.032 Uiso 1 1 calc R U . . .
C14 C 0.3967(4) 0.4040(4) 0.7501(3) 0.0159(7) Uani 1 1 d . . . . .
C15 C 0.5973(4) 0.4783(4) 0.8301(3) 0.0176(7) Uani 1 1 d . . . . .
C16 C 0.6042(4) 0.5984(4) 0.9133(3) 0.0202(7) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl1 C16 1.703(4) . ?
Cl2 C15 1.720(3) . ?
S1 N2 1.651(3) . ?
S1 C16 1.709(3) . ?
O1 C8 1.245(3) . ?
O2 C10 1.222(4) . ?
O3 C10 1.359(4) . ?
O3 C11 1.458(4) . ?
N1 C2 1.370(4) . ?
N1 C6 1.379(4) . ?
N1 H1 0.80(3) . ?
N2 C14 1.329(4) . ?
C2 C3 1.371(4) . ?
C2 C7 1.501(4) . ?
C3 C8 1.456(4) . ?
C3 C4 1.528(4) . ?
C4 C14 1.512(5) . ?
C4 C5 1.523(4) . ?
C4 H4A 1.0000 . ?
C5 C6 1.363(4) . ?
C5 C10 1.467(4) . ?
C6 C13 1.498(4) . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C8 C9 1.504(5) . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C11 C12 1.509(5) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 C15 1.442(4) . ?
C15 C16 1.357(5) . ?

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
N2 S1 C16 94.65(15) . . ?
C10 O3 C11 115.1(2) . . ?
C2 N1 C6 124.2(2) . . ?
C2 N1 H1 116(3) . . ?
C6 N1 H1 120(3) . . ?
C14 N2 S1 111.1(2) . . ?
N1 C2 C3 118.0(3) . . ?
N1 C2 C7 113.4(2) . . ?
C3 C2 C7 128.6(3) . . ?
C2 C3 C8 124.8(3) . . ?
C2 C3 C4 118.4(2) . . ?
C8 C3 C4 116.8(2) . . ?
C14 C4 C5 110.5(3) . . ?
C14 C4 C3 111.1(3) . . ?
C5 C4 C3 110.0(3) . . ?
C14 C4 H4A 108.4 . . ?
C5 C4 H4A 108.4 . . ?
C3 C4 H4A 108.4 . . ?
C6 C5 C10 122.1(3) . . ?
C6 C5 C4 118.2(3) . . ?
C10 C5 C4 119.3(3) . . ?
C5 C6 N1 118.9(3) . . ?
C5 C6 C13 127.5(3) . . ?
N1 C6 C13 113.5(2) . . ?
C2 C7 H7A 109.5 . . ?
C2 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C2 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
O1 C8 C3 118.9(3) . . ?
O1 C8 C9 118.2(3) . . ?
C3 C8 C9 122.9(3) . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C8 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
O2 C10 O3 121.6(3) . . ?
O2 C10 C5 127.4(3) . . ?
O3 C10 C5 110.9(3) . . ?
O3 C11 C12 107.9(3) . . ?
O3 C11 H11A 110.1 . . ?
C12 C11 H11A 110.1 . . ?
O3 C11 H11B 110.1 . . ?
C12 C11 H11B 110.1 . . ?
H11A C11 H11B 108.4 . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C6 C13 H13A 109.5 . . ?
C6 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C6 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
N2 C14 C15 113.5(3) . . ?
N2 C14 C4 119.2(3) . . ?
C15 C14 C4 127.4(3) . . ?
C16 C15 C14 111.6(3) . . ?
C16 C15 Cl2 123.5(3) . . ?
C14 C15 Cl2 124.9(3) . . ?
C15 C16 Cl1 127.9(2) . . ?
C15 C16 S1 109.2(2) . . ?
Cl1 C16 S1 122.9(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
C16 S1 N2 C14 0.0(3) . . . . ?
C6 N1 C2 C3 -14.9(5) . . . . ?
C6 N1 C2 C7 164.4(3) . . . . ?
N1 C2 C3 C8 162.8(3) . . . . ?
C7 C2 C3 C8 -16.3(6) . . . . ?
N1 C2 C3 C4 -14.2(5) . . . . ?
C7 C2 C3 C4 166.7(3) . . . . ?
C2 C3 C4 C14 -86.4(3) . . . . ?
C8 C3 C4 C14 96.4(3) . . . . ?
C2 C3 C4 C5 36.2(4) . . . . ?
C8 C3 C4 C5 -141.0(3) . . . . ?
C14 C4 C5 C6 89.6(4) . . . . ?
C3 C4 C5 C6 -33.4(4) . . . . ?
C14 C4 C5 C10 -83.7(3) . . . . ?
C3 C4 C5 C10 153.2(3) . . . . ?
C10 C5 C6 N1 -177.9(3) . . . . ?
C4 C5 C6 N1 9.0(5) . . . . ?
C10 C5 C6 C13 0.0(6) . . . . ?
C4 C5 C6 C13 -173.1(3) . . . . ?
C2 N1 C6 C5 17.7(5) . . . . ?
C2 N1 C6 C13 -160.5(3) . . . . ?
C2 C3 C8 O1 174.4(3) . . . . ?
C4 C3 C8 O1 -8.6(5) . . . . ?
C2 C3 C8 C9 -8.9(5) . . . . ?
C4 C3 C8 C9 168.1(3) . . . . ?
C11 O3 C10 O2 -2.2(5) . . . . ?
C11 O3 C10 C5 177.2(3) . . . . ?
C6 C5 C10 O2 1.1(6) . . . . ?
C4 C5 C10 O2 174.2(3) . . . . ?
C6 C5 C10 O3 -178.2(3) . . . . ?
C4 C5 C10 O3 -5.2(4) . . . . ?
C10 O3 C11 C12 -175.4(3) . . . . ?
S1 N2 C14 C15 0.4(3) . . . . ?
S1 N2 C14 C4 -178.9(2) . . . . ?
C5 C4 C14 N2 -52.1(4) . . . . ?
C3 C4 C14 N2 70.3(3) . . . . ?
C5 C4 C14 C15 128.7(3) . . . . ?
C3 C4 C14 C15 -108.9(3) . . . . ?
N2 C14 C15 C16 -0.7(4) . . . . ?
C4 C14 C15 C16 178.5(3) . . . . ?
N2 C14 C15 Cl2 -179.8(2) . . . . ?
C4 C14 C15 Cl2 -0.5(5) . . . . ?
C14 C15 C16 Cl1 -178.0(2) . . . . ?
Cl2 C15 C16 Cl1 1.0(5) . . . . ?
C14 C15 C16 S1 0.7(3) . . . . ?
Cl2 C15 C16 S1 179.71(18) . . . . ?
N2 S1 C16 C15 -0.4(3) . . . . ?
N2 S1 C16 Cl1 178.4(2) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N1 H1 O1 0.80(3) 2.05(3) 2.819(3) 162(4) 1_455 yes

_refine_diff_density_max         0.472
_refine_diff_density_min         -0.681
_refine_diff_density_rms         0.106



# start Validation Reply Form
_vrf_PLAT910_I596                
;
PROBLEM: Missing # of FCF Reflection(s) Below Theta(Min).         14 Note  
RESPONSE: Closed by beamstop.
;
# end Validation Reply Form
####################################################################### 
# 
# 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_I631
_database_code_depnum_ccdc_archive 'CCDC 2243955'
loop_
_audit_author_name
_audit_author_address
'Mikhail Grigoriev'
;IPCE RAS
Russia
;
_audit_update_record             
;
2023-02-22 deposited with the CCDC.	2023-02-28 downloaded from the CCDC.
;
_audit_creation_date             2023-02-21
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelxl_version_number           2013-4
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C16 H18 Cl2 N2 O4 S'
_chemical_formula_sum            'C16 H18 Cl2 N2 O4 S'
_chemical_formula_weight         405.28
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.7279(3)
_cell_length_b                   9.6603(3)
_cell_length_c                   11.4482(4)
_cell_angle_alpha                86.524(3)
_cell_angle_beta                 77.743(3)
_cell_angle_gamma                71.031(3)
_cell_volume                     891.98(6)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    15374
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      79.0
_cell_measurement_theta_min      3.9
_shelx_estimated_absorpt_T_max   0.492
_shelx_estimated_absorpt_T_min   0.393
_exptl_absorpt_coefficient_mu    4.588
_exptl_absorpt_correction_T_max  0.432
_exptl_absorpt_correction_T_min  0.333
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.117a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.509
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             420
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.18
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0591
_diffrn_reflns_av_unetI/netI     0.0317
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            19809
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         79.456
_diffrn_reflns_theta_min         3.952
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'φ and ω'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3755
_reflns_number_total             3836
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.41.117a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.117a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.117a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_refine_diff_density_max         0.541
_refine_diff_density_min         -0.608
_refine_diff_density_rms         0.092
_refine_ls_extinction_coef       0.0105(9)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     234
_refine_ls_number_reflns         3836
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0421
_refine_ls_R_factor_gt           0.0415
_refine_ls_restrained_S_all      1.061
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0781P)²+0.4496P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1139
_refine_ls_wR_factor_ref         0.1147
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1.a Ternary CH refined with riding coordinates:
 C4(H4)
1.b Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B), C14(H14A,H14B)
1.c Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C9(H9A,H9B,H9C), C15(H15A,H15B,H15C), C16(H16A,H16B,H16C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     difmap
_atom_sites_solution_secondary   difmap
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 0.59376(5) 0.54580(4) 0.09473(3) 0.01511(14) Uani 1 1 d . . . . .
Cl2 Cl 0.82253(5) 0.72975(4) -0.07384(3) 0.01741(14) Uani 1 1 d . . . . .
S1 S 0.99131(5) 0.67750(4) 0.13423(3) 0.01292(14) Uani 1 1 d . . . . .
O1 O 0.45108(16) 0.79892(13) 0.52683(12) 0.0191(3) Uani 1 1 d . . . . .
O2 O 0.46959(14) 0.70179(12) 0.34825(10) 0.0128(3) Uani 1 1 d . . . . .
O3 O 1.00206(16) 0.08045(13) 0.29906(11) 0.0173(3) Uani 1 1 d . . . . .
O4 O 0.79972(15) 0.22834(12) 0.21409(10) 0.0128(3) Uani 1 1 d . . . . .
N1 N 0.87079(17) 0.42174(15) 0.55654(12) 0.0106(3) Uani 1 1 d . . . . .
H1 H 0.927(3) 0.418(2) 0.615(2) 0.013 Uiso 1 1 d . U . . .
N2 N 0.93236(17) 0.59017(15) 0.25566(12) 0.0108(3) Uani 1 1 d . . . . .
C1 C 0.6806(2) 0.63265(19) 0.66890(15) 0.0146(3) Uani 1 1 d . . . . .
H1A H 0.6166 0.5871 0.7308 0.022 Uiso 1 1 calc R U . . .
H1B H 0.6118 0.7321 0.6542 0.022 Uiso 1 1 calc R U . . .
H1C H 0.7785 0.6367 0.6957 0.022 Uiso 1 1 calc R U . . .
C2 C 0.73401(19) 0.54362(17) 0.55535(14) 0.0099(3) Uani 1 1 d . . . . .
C3 C 0.66044(19) 0.56954(16) 0.45948(14) 0.0087(3) Uani 1 1 d . . . . .
C4 C 0.73093(19) 0.46820(16) 0.34991(14) 0.0082(3) Uani 1 1 d . . . . .
H4 H 0.6377 0.4448 0.3270 0.010 Uiso 1 1 calc R U . . .
C5 C 0.85832(19) 0.32448(16) 0.37577(14) 0.0091(3) Uani 1 1 d . . . . .
C6 C 0.92865(19) 0.31114(17) 0.47239(14) 0.0096(3) Uani 1 1 d . . . . .
C7 C 0.5179(2) 0.70114(17) 0.45349(15) 0.0112(3) Uani 1 1 d . . . . .
C8 C 0.3450(2) 0.83368(18) 0.32063(17) 0.0166(3) Uani 1 1 d . . . . .
H8A H 0.2671 0.8775 0.3952 0.020 Uiso 1 1 calc R U . . .
H8B H 0.2812 0.8091 0.2676 0.020 Uiso 1 1 calc R U . . .
C9 C 0.4267(2) 0.9424(2) 0.25957(19) 0.0246(4) Uani 1 1 d . . . . .
H9A H 0.5063 0.8975 0.1872 0.037 Uiso 1 1 calc R U . . .
H9B H 0.4844 0.9707 0.3140 0.037 Uiso 1 1 calc R U . . .
H9C H 0.3422 1.0294 0.2379 0.037 Uiso 1 1 calc R U . . .
C10 C 0.80683(19) 0.54657(16) 0.24600(14) 0.0082(3) Uani 1 1 d . . . . .
C11 C 0.75385(19) 0.58374(16) 0.13486(14) 0.0100(3) Uani 1 1 d . . . . .
C12 C 0.8457(2) 0.65893(17) 0.06341(14) 0.0120(3) Uani 1 1 d . . . . .
C13 C 0.8975(2) 0.19862(17) 0.29586(14) 0.0107(3) Uani 1 1 d . . . . .
C14 C 0.8189(2) 0.10251(19) 0.14228(17) 0.0194(4) Uani 1 1 d . . . . .
H14A H 0.7997 0.0219 0.1947 0.023 Uiso 1 1 calc R U . . .
H14B H 0.9325 0.0673 0.0934 0.023 Uiso 1 1 calc R U . . .
C15 C 0.6945(2) 0.1488(2) 0.06233(17) 0.0207(4) Uani 1 1 d . . . . .
H15A H 0.7062 0.0656 0.0124 0.031 Uiso 1 1 calc R U . . .
H15B H 0.7140 0.2289 0.0111 0.031 Uiso 1 1 calc R U . . .
H15C H 0.5824 0.1819 0.1115 0.031 Uiso 1 1 calc R U . . .
C16 C 1.0656(2) 0.18290(18) 0.50420(15) 0.0136(3) Uani 1 1 d . . . . .
H16A H 1.1248 0.2166 0.5543 0.020 Uiso 1 1 calc R U . . .
H16B H 1.1426 0.1376 0.4309 0.020 Uiso 1 1 calc R U . . .
H16C H 1.0185 0.1109 0.5481 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
Cl1 C11 1.7098(16) . ?
Cl2 C12 1.7007(16) . ?
S1 N2 1.6569(14) . ?
S1 C12 1.7051(17) . ?
O1 C7 1.211(2) . ?
O2 C7 1.357(2) . ?
O2 C8 1.4501(19) . ?
O3 C13 1.212(2) . ?
O4 C13 1.3545(19) . ?
O4 C14 1.4533(19) . ?
N1 H1 0.90(2) . ?
N1 C2 1.379(2) . ?
N1 C6 1.376(2) . ?
N2 C10 1.322(2) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C1 C2 1.505(2) . ?
C2 C3 1.357(2) . ?
C3 C4 1.530(2) . ?
C3 C7 1.472(2) . ?
C4 H4 1.0000 . ?
C4 C5 1.529(2) . ?
C4 C10 1.520(2) . ?
C5 C6 1.355(2) . ?
C5 C13 1.471(2) . ?
C6 C16 1.504(2) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C8 C9 1.512(3) . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 C11 1.431(2) . ?
C11 C12 1.367(2) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C14 C15 1.508(2) . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N2 S1 C12 94.13(7) . . ?
C7 O2 C8 116.69(13) . . ?
C13 O4 C14 114.02(13) . . ?
C2 N1 H1 116.8(14) . . ?
C6 N1 H1 119.0(14) . . ?
C6 N1 C2 124.15(14) . . ?
C10 N2 S1 111.29(11) . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
N1 C2 C1 112.78(14) . . ?
C3 C2 N1 119.96(14) . . ?
C3 C2 C1 127.23(15) . . ?
C2 C3 C4 120.86(14) . . ?
C2 C3 C7 121.37(14) . . ?
C7 C3 C4 117.63(13) . . ?
C3 C4 H4 108.2 . . ?
C5 C4 C3 111.86(13) . . ?
C5 C4 H4 108.2 . . ?
C10 C4 C3 109.62(12) . . ?
C10 C4 H4 108.2 . . ?
C10 C4 C5 110.60(12) . . ?
C6 C5 C4 121.07(14) . . ?
C6 C5 C13 120.62(14) . . ?
C13 C5 C4 118.25(13) . . ?
N1 C6 C16 112.78(14) . . ?
C5 C6 N1 119.69(14) . . ?
C5 C6 C16 127.50(14) . . ?
O1 C7 O2 122.56(15) . . ?
O1 C7 C3 127.83(15) . . ?
O2 C7 C3 109.60(13) . . ?
O2 C8 H8A 109.7 . . ?
O2 C8 H8B 109.7 . . ?
O2 C8 C9 109.91(14) . . ?
H8A C8 H8B 108.2 . . ?
C9 C8 H8A 109.7 . . ?
C9 C8 H8B 109.7 . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
C8 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
N2 C10 C4 119.43(13) . . ?
N2 C10 C11 113.97(14) . . ?
C11 C10 C4 126.59(14) . . ?
C10 C11 Cl1 125.81(12) . . ?
C12 C11 Cl1 123.04(13) . . ?
C12 C11 C10 111.13(14) . . ?
Cl2 C12 S1 123.01(10) . . ?
C11 C12 Cl2 127.50(13) . . ?
C11 C12 S1 109.48(12) . . ?
O3 C13 O4 121.65(14) . . ?
O3 C13 C5 126.68(15) . . ?
O4 C13 C5 111.67(13) . . ?
O4 C14 H14A 110.1 . . ?
O4 C14 H14B 110.1 . . ?
O4 C14 C15 108.16(14) . . ?
H14A C14 H14B 108.4 . . ?
C15 C14 H14A 110.1 . . ?
C15 C14 H14B 110.1 . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C6 C16 H16A 109.5 . . ?
C6 C16 H16B 109.5 . . ?
C6 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1 N2 0.90(2) 2.10(2) 3.000(2) 178(2) 2_766
C1 H1B O1 0.98 2.16 2.866(2) 127 .
C16 H16B O3 0.98 2.33 2.827(2) 111 .

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
Cl1 C11 C12 Cl2 0.6(2) . . . . ?
Cl1 C11 C12 S1 179.14(9) . . . . ?
S1 N2 C10 C4 -178.14(11) . . . . ?
S1 N2 C10 C11 0.38(17) . . . . ?
N1 C2 C3 C4 -2.3(2) . . . . ?
N1 C2 C3 C7 -177.85(13) . . . . ?
N2 S1 C12 Cl2 178.10(11) . . . . ?
N2 S1 C12 C11 -0.53(13) . . . . ?
N2 C10 C11 Cl1 -179.07(11) . . . . ?
N2 C10 C11 C12 -0.79(19) . . . . ?
C1 C2 C3 C4 179.78(14) . . . . ?
C1 C2 C3 C7 4.2(2) . . . . ?
C2 N1 C6 C5 5.7(2) . . . . ?
C2 N1 C6 C16 -172.48(14) . . . . ?
C2 C3 C4 C5 13.8(2) . . . . ?
C2 C3 C4 C10 -109.26(16) . . . . ?
C2 C3 C7 O1 0.7(3) . . . . ?
C2 C3 C7 O2 179.14(14) . . . . ?
C3 C4 C5 C6 -16.7(2) . . . . ?
C3 C4 C5 C13 160.66(13) . . . . ?
C3 C4 C10 N2 61.53(18) . . . . ?
C3 C4 C10 C11 -116.79(16) . . . . ?
C4 C3 C7 O1 -175.04(16) . . . . ?
C4 C3 C7 O2 3.45(19) . . . . ?
C4 C5 C6 N1 8.0(2) . . . . ?
C4 C5 C6 C16 -174.16(15) . . . . ?
C4 C5 C13 O3 175.07(15) . . . . ?
C4 C5 C13 O4 -5.3(2) . . . . ?
C4 C10 C11 Cl1 -0.7(2) . . . . ?
C4 C10 C11 C12 177.60(14) . . . . ?
C5 C4 C10 N2 -62.28(17) . . . . ?
C5 C4 C10 C11 119.41(16) . . . . ?
C6 N1 C2 C1 169.59(14) . . . . ?
C6 N1 C2 C3 -8.6(2) . . . . ?
C6 C5 C13 O3 -7.5(3) . . . . ?
C6 C5 C13 O4 172.10(14) . . . . ?
C7 O2 C8 C9 86.51(18) . . . . ?
C7 C3 C4 C5 -170.48(13) . . . . ?
C7 C3 C4 C10 66.46(17) . . . . ?
C8 O2 C7 O1 6.7(2) . . . . ?
C8 O2 C7 C3 -171.85(13) . . . . ?
C10 C4 C5 C6 105.77(16) . . . . ?
C10 C4 C5 C13 -76.84(17) . . . . ?
C10 C11 C12 Cl2 -177.75(12) . . . . ?
C10 C11 C12 S1 0.81(17) . . . . ?
C12 S1 N2 C10 0.08(12) . . . . ?
C13 O4 C14 C15 175.84(14) . . . . ?
C13 C5 C6 N1 -169.32(14) . . . . ?
C13 C5 C6 C16 8.5(2) . . . . ?
C14 O4 C13 O3 6.8(2) . . . . ?
C14 O4 C13 C5 -172.84(14) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_I681
_database_code_depnum_ccdc_archive 'CCDC 2236984'
loop_
_audit_author_name
_audit_author_address
'Mikhail Grigoriev'
;IPCE RAS
Russia
;
_audit_update_record             
;
2023-01-18 deposited with the CCDC.	2023-02-28 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            'C14 H14 Cl2 N2 O2 S'
_chemical_formula_weight         345.23

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

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

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

_cell_length_a                   7.2276(5)
_cell_length_b                   26.5464(19)
_cell_length_c                   8.5613(6)
_cell_angle_alpha                90
_cell_angle_beta                 112.990(3)
_cell_angle_gamma                90
_cell_volume                     1512.16(19)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    3912
_cell_measurement_theta_min      3.14
_cell_measurement_theta_max      24.93

_exptl_crystal_description       fragment
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.516
_exptl_crystal_F_000             712
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.320
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.160
_exptl_absorpt_coefficient_mu    0.572
_shelx_estimated_absorpt_T_min   0.838
_shelx_estimated_absorpt_T_max   0.914
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9229
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_process_details   
;
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;
_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            25913
_diffrn_reflns_av_unetI/netI     0.0936
_diffrn_reflns_av_R_equivalents  0.0655
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -37
_diffrn_reflns_limit_k_max       37
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         4.337
_diffrn_reflns_theta_max         29.999
_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 0.973
_diffrn_reflns_point_group_measured_fraction_full 0.982
_reflns_number_total             8579
_reflns_number_gt                6270
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.915
_reflns_Friedel_fraction_max     0.950
_reflns_Friedel_fraction_full    0.969

_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)+(0.0353P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 2247 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.04(4)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         8579
_refine_ls_number_parameters     393
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0840
_refine_ls_R_factor_gt           0.0507
_refine_ls_wR_factor_ref         0.0982
_refine_ls_wR_factor_gt          0.0867
_refine_ls_goodness_of_fit_ref   1.016
_refine_ls_restrained_S_all      1.016
_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 0.70922(16) 0.59150(4) 0.45439(14) 0.0150(2) Uani 1 1 d . . . . .
Cl2 Cl 0.67179(19) 0.48511(5) 0.64165(15) 0.0241(3) Uani 1 1 d . . . . .
S1 S 0.2376(2) 0.51665(5) 0.52255(16) 0.0198(3) Uani 1 1 d . . . . .
O1 O 0.4278(5) 0.63844(15) 0.0658(4) 0.0258(9) Uani 1 1 d . . . . .
O2 O 0.4720(5) 0.69944(14) 0.5707(5) 0.0274(9) Uani 1 1 d . . . . .
N1 N -0.1553(5) 0.65402(16) 0.1639(5) 0.0142(9) Uani 1 1 d D . . . .
H1 H -0.274(5) 0.654(2) 0.139(6) 0.017 Uiso 1 1 d D U . . .
N2 N 0.1528(6) 0.56982(16) 0.4179(5) 0.0172(9) Uani 1 1 d . . . . .
C2 C -0.0731(7) 0.63421(19) 0.0577(6) 0.0130(11) Uani 1 1 d . . . . .
C3 C 0.1319(7) 0.63451(17) 0.1117(5) 0.0099(9) Uani 1 1 d . . . . .
C4 C 0.2553(7) 0.64386(17) 0.2985(5) 0.0114(9) Uani 1 1 d . . . . .
H4A H 0.386165 0.659184 0.309261 0.014 Uiso 1 1 calc R U . . .
C5 C 0.1516(7) 0.68029(17) 0.3755(6) 0.0111(9) Uani 1 1 d . . . . .
C6 C -0.0512(7) 0.68224(19) 0.3086(6) 0.0128(10) Uani 1 1 d . . . . .
C7 C -0.2273(7) 0.6155(2) -0.1066(6) 0.0169(10) Uani 1 1 d . . . . .
H7A H -0.346089 0.603823 -0.088568 0.025 Uiso 1 1 calc R U . . .
H7B H -0.171098 0.587565 -0.148788 0.025 Uiso 1 1 calc R U . . .
H7C H -0.265716 0.642895 -0.189980 0.025 Uiso 1 1 calc R U . . .
C8 C 0.2455(7) 0.63017(18) 0.0038(6) 0.0122(10) Uani 1 1 d . . . . .
C9 C 0.1496(7) 0.6179(2) -0.1824(6) 0.0180(11) Uani 1 1 d . . . . .
H9A H 0.033339 0.639896 -0.237422 0.027 Uiso 1 1 calc R U . . .
H9B H 0.105640 0.582651 -0.196925 0.027 Uiso 1 1 calc R U . . .
H9C H 0.247479 0.623105 -0.234155 0.027 Uiso 1 1 calc R U . . .
C10 C 0.2910(8) 0.70719(19) 0.5254(6) 0.0137(10) Uani 1 1 d . . . . .
C11 C 0.2232(7) 0.74221(19) 0.6295(6) 0.0194(11) Uani 1 1 d . . . . .
H11A H 0.136531 0.723961 0.674227 0.029 Uiso 1 1 calc R U . . .
H11B H 0.147985 0.770238 0.558539 0.029 Uiso 1 1 calc R U . . .
H11C H 0.340612 0.755364 0.724050 0.029 Uiso 1 1 calc R U . . .
C12 C -0.1887(7) 0.71349(19) 0.3643(6) 0.0175(11) Uani 1 1 d . . . . .
H12A H -0.328779 0.706856 0.289255 0.026 Uiso 1 1 calc R U . . .
H12B H -0.158847 0.749295 0.358844 0.026 Uiso 1 1 calc R U . . .
H12C H -0.167979 0.704612 0.481113 0.026 Uiso 1 1 calc R U . . .
C13 C 0.3001(7) 0.59416(19) 0.3948(5) 0.0118(9) Uani 1 1 d . . . . .
C14 C 0.4903(7) 0.56963(18) 0.4645(6) 0.0115(9) Uani 1 1 d . . . . .
C15 C 0.4786(7) 0.52539(18) 0.5393(6) 0.0158(11) Uani 1 1 d . . . . .
Cl21 Cl 0.60100(16) 0.40731(5) 0.93553(14) 0.0177(3) Uani 1 1 d . . . . .
Cl22 Cl 0.5683(2) 0.51400(5) 1.12360(16) 0.0291(3) Uani 1 1 d . . . . .
S21 S 0.1363(2) 0.48261(5) 1.01216(16) 0.0220(3) Uani 1 1 d . . . . .
O21 O 0.3170(5) 0.37323(16) 0.5532(4) 0.0266(10) Uani 1 1 d . . . . .
O22 O 0.3589(5) 0.30230(16) 1.0534(4) 0.0249(9) Uani 1 1 d . . . . .
N21 N -0.2702(6) 0.34561(16) 0.6426(5) 0.0143(9) Uani 1 1 d D . . . .
H21 H -0.387(5) 0.350(2) 0.614(6) 0.017 Uiso 1 1 d D U . . .
N22 N 0.0479(6) 0.43000(15) 0.9046(5) 0.0166(9) Uani 1 1 d . . . . .
C22 C -0.1874(7) 0.36581(19) 0.5379(5) 0.0120(10) Uani 1 1 d . . . . .
C23 C 0.0176(7) 0.36632(18) 0.5923(6) 0.0115(10) Uani 1 1 d . . . . .
C24 C 0.1416(6) 0.35643(17) 0.7784(5) 0.0106(9) Uani 1 1 d . . . . .
H24A H 0.271117 0.340752 0.787200 0.013 Uiso 1 1 calc R U . . .
C25 C 0.0396(7) 0.32008(18) 0.8556(6) 0.0117(10) Uani 1 1 d . . . . .
C26 C -0.1660(7) 0.31766(17) 0.7865(5) 0.0108(9) Uani 1 1 d . . . . .
C27 C -0.3425(7) 0.38318(19) 0.3706(6) 0.0159(10) Uani 1 1 d . . . . .
H27A H -0.291975 0.412784 0.331290 0.024 Uiso 1 1 calc R U . . .
H27B H -0.466755 0.391990 0.384718 0.024 Uiso 1 1 calc R U . . .
H27C H -0.369806 0.356066 0.286853 0.024 Uiso 1 1 calc R U . . .
C28 C 0.1318(7) 0.37472(18) 0.4861(6) 0.0133(10) Uani 1 1 d . . . . .
C29 C 0.0367(7) 0.3840(2) 0.2987(6) 0.0209(11) Uani 1 1 d . . . . .
H29A H -0.073757 0.360152 0.246391 0.031 Uiso 1 1 calc R U . . .
H29B H 0.137268 0.379533 0.249383 0.031 Uiso 1 1 calc R U . . .
H29C H -0.015686 0.418522 0.277662 0.031 Uiso 1 1 calc R U . . .
C30 C 0.1787(7) 0.29376(18) 1.0073(6) 0.0152(10) Uani 1 1 d . . . . .
C31 C 0.1097(7) 0.25788(19) 1.1094(6) 0.0200(11) Uani 1 1 d . . . . .
H31A H 0.024485 0.231826 1.034542 0.030 Uiso 1 1 calc R U . . .
H31B H 0.032866 0.276361 1.163123 0.030 Uiso 1 1 calc R U . . .
H31C H 0.226898 0.242072 1.197129 0.030 Uiso 1 1 calc R U . . .
C32 C -0.3012(7) 0.28672(19) 0.8445(6) 0.0183(11) Uani 1 1 d . . . . .
H32A H -0.441813 0.294340 0.773635 0.027 Uiso 1 1 calc R U . . .
H32B H -0.274537 0.294770 0.963101 0.027 Uiso 1 1 calc R U . . .
H32C H -0.275445 0.250850 0.834757 0.027 Uiso 1 1 calc R U . . .
C33 C 0.1917(6) 0.40562(19) 0.8773(5) 0.0109(9) Uani 1 1 d . . . . .
C34 C 0.3834(7) 0.42926(18) 0.9446(6) 0.0131(10) Uani 1 1 d . . . . .
C35 C 0.3770(8) 0.4733(2) 1.0253(6) 0.0176(12) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl1 C14 1.719(5) . ?
Cl2 C15 1.705(5) . ?
S1 N2 1.656(4) . ?
S1 C15 1.707(5) . ?
O1 C8 1.233(5) . ?
O2 C10 1.228(6) . ?
N1 C2 1.370(6) . ?
N1 C6 1.391(6) . ?
N1 H1 0.80(3) . ?
N2 C13 1.325(6) . ?
C2 C3 1.369(6) . ?
C2 C7 1.498(6) . ?
C3 C8 1.460(6) . ?
C3 C4 1.517(6) . ?
C4 C13 1.522(6) . ?
C4 C5 1.523(6) . ?
C4 H4A 1.0000 . ?
C5 C6 1.350(6) . ?
C5 C10 1.470(6) . ?
C6 C12 1.508(6) . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C8 C9 1.505(6) . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 C11 1.497(7) . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 C14 1.424(6) . ?
C14 C15 1.356(6) . ?
Cl21 C34 1.707(5) . ?
Cl22 C35 1.697(5) . ?
S21 N22 1.657(4) . ?
S21 C35 1.717(5) . ?
O21 C28 1.234(5) . ?
O22 C30 1.225(5) . ?
N21 C22 1.366(6) . ?
N21 C26 1.382(6) . ?
N21 H21 0.79(3) . ?
N22 C33 1.320(5) . ?
C22 C23 1.369(6) . ?
C22 C27 1.505(6) . ?
C23 C28 1.464(6) . ?
C23 C24 1.515(6) . ?
C24 C25 1.514(6) . ?
C24 C33 1.521(6) . ?
C24 H24A 1.0000 . ?
C25 C26 1.370(6) . ?
C25 C30 1.471(7) . ?
C26 C32 1.502(6) . ?
C27 H27A 0.9800 . ?
C27 H27B 0.9800 . ?
C27 H27C 0.9800 . ?
C28 C29 1.499(6) . ?
C29 H29A 0.9800 . ?
C29 H29B 0.9800 . ?
C29 H29C 0.9800 . ?
C30 C31 1.504(6) . ?
C31 H31A 0.9800 . ?
C31 H31B 0.9800 . ?
C31 H31C 0.9800 . ?
C32 H32A 0.9800 . ?
C32 H32B 0.9800 . ?
C32 H32C 0.9800 . ?
C33 C34 1.422(6) . ?
C34 C35 1.368(7) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N2 S1 C15 94.5(2) . . ?
C2 N1 C6 125.0(4) . . ?
C2 N1 H1 121(4) . . ?
C6 N1 H1 113(4) . . ?
C13 N2 S1 110.3(3) . . ?
C3 C2 N1 117.8(4) . . ?
C3 C2 C7 129.0(4) . . ?
N1 C2 C7 113.2(4) . . ?
C2 C3 C8 126.0(4) . . ?
C2 C3 C4 118.1(4) . . ?
C8 C3 C4 115.8(4) . . ?
C3 C4 C13 110.0(4) . . ?
C3 C4 C5 112.0(4) . . ?
C13 C4 C5 110.6(3) . . ?
C3 C4 H4A 108.0 . . ?
C13 C4 H4A 108.0 . . ?
C5 C4 H4A 108.0 . . ?
C6 C5 C10 127.7(4) . . ?
C6 C5 C4 118.5(4) . . ?
C10 C5 C4 113.6(4) . . ?
C5 C6 N1 118.5(4) . . ?
C5 C6 C12 128.8(4) . . ?
N1 C6 C12 112.6(4) . . ?
C2 C7 H7A 109.5 . . ?
C2 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C2 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
O1 C8 C3 118.9(4) . . ?
O1 C8 C9 117.8(4) . . ?
C3 C8 C9 123.2(4) . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C8 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
O2 C10 C5 118.5(4) . . ?
O2 C10 C11 118.2(4) . . ?
C5 C10 C11 123.3(4) . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C6 C12 H12A 109.5 . . ?
C6 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C6 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
N2 C13 C14 114.5(5) . . ?
N2 C13 C4 119.4(4) . . ?
C14 C13 C4 126.1(4) . . ?
C15 C14 C13 111.5(4) . . ?
C15 C14 Cl1 123.0(4) . . ?
C13 C14 Cl1 125.5(4) . . ?
C14 C15 Cl2 126.6(4) . . ?
C14 C15 S1 109.1(3) . . ?
Cl2 C15 S1 124.2(3) . . ?
N22 S21 C35 94.3(2) . . ?
C22 N21 C26 124.7(4) . . ?
C22 N21 H21 115(4) . . ?
C26 N21 H21 120(4) . . ?
C33 N22 S21 110.6(4) . . ?
N21 C22 C23 118.3(4) . . ?
N21 C22 C27 113.0(4) . . ?
C23 C22 C27 128.7(4) . . ?
C22 C23 C28 126.0(4) . . ?
C22 C23 C24 118.2(4) . . ?
C28 C23 C24 115.7(4) . . ?
C25 C24 C23 112.4(4) . . ?
C25 C24 C33 110.8(3) . . ?
C23 C24 C33 110.5(4) . . ?
C25 C24 H24A 107.6 . . ?
C23 C24 H24A 107.6 . . ?
C33 C24 H24A 107.6 . . ?
C26 C25 C30 127.7(4) . . ?
C26 C25 C24 118.2(4) . . ?
C30 C25 C24 114.0(4) . . ?
C25 C26 N21 118.8(4) . . ?
C25 C26 C32 128.2(4) . . ?
N21 C26 C32 113.0(4) . . ?
C22 C27 H27A 109.5 . . ?
C22 C27 H27B 109.5 . . ?
H27A C27 H27B 109.5 . . ?
C22 C27 H27C 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
O21 C28 C23 118.5(4) . . ?
O21 C28 C29 117.7(4) . . ?
C23 C28 C29 123.7(4) . . ?
C28 C29 H29A 109.5 . . ?
C28 C29 H29B 109.5 . . ?
H29A C29 H29B 109.5 . . ?
C28 C29 H29C 109.5 . . ?
H29A C29 H29C 109.5 . . ?
H29B C29 H29C 109.5 . . ?
O22 C30 C25 118.1(4) . . ?
O22 C30 C31 118.8(4) . . ?
C25 C30 C31 123.1(4) . . ?
C30 C31 H31A 109.5 . . ?
C30 C31 H31B 109.5 . . ?
H31A C31 H31B 109.5 . . ?
C30 C31 H31C 109.5 . . ?
H31A C31 H31C 109.5 . . ?
H31B C31 H31C 109.5 . . ?
C26 C32 H32A 109.5 . . ?
C26 C32 H32B 109.5 . . ?
H32A C32 H32B 109.5 . . ?
C26 C32 H32C 109.5 . . ?
H32A C32 H32C 109.5 . . ?
H32B C32 H32C 109.5 . . ?
N22 C33 C34 114.9(5) . . ?
N22 C33 C24 119.1(4) . . ?
C34 C33 C24 125.9(4) . . ?
C35 C34 C33 111.2(4) . . ?
C35 C34 Cl21 121.9(4) . . ?
C33 C34 Cl21 126.9(4) . . ?
C34 C35 Cl22 127.8(4) . . ?
C34 C35 S21 108.9(4) . . ?
Cl22 C35 S21 123.3(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
C15 S1 N2 C13 0.0(3) . . . . ?
C6 N1 C2 C3 11.8(7) . . . . ?
C6 N1 C2 C7 -167.4(4) . . . . ?
N1 C2 C3 C8 -159.9(5) . . . . ?
C7 C2 C3 C8 19.1(8) . . . . ?
N1 C2 C3 C4 15.4(6) . . . . ?
C7 C2 C3 C4 -165.5(5) . . . . ?
C2 C3 C4 C13 89.3(5) . . . . ?
C8 C3 C4 C13 -94.9(5) . . . . ?
C2 C3 C4 C5 -34.2(5) . . . . ?
C8 C3 C4 C5 141.6(4) . . . . ?
C3 C4 C5 C6 28.9(6) . . . . ?
C13 C4 C5 C6 -94.3(5) . . . . ?
C3 C4 C5 C10 -155.0(4) . . . . ?
C13 C4 C5 C10 81.9(5) . . . . ?
C10 C5 C6 N1 179.3(4) . . . . ?
C4 C5 C6 N1 -5.3(6) . . . . ?
C10 C5 C6 C12 2.4(8) . . . . ?
C4 C5 C6 C12 177.9(4) . . . . ?
C2 N1 C6 C5 -17.3(7) . . . . ?
C2 N1 C6 C12 160.0(4) . . . . ?
C2 C3 C8 O1 169.4(5) . . . . ?
C4 C3 C8 O1 -6.1(7) . . . . ?
C2 C3 C8 C9 -8.3(7) . . . . ?
C4 C3 C8 C9 176.3(4) . . . . ?
C6 C5 C10 O2 177.8(5) . . . . ?
C4 C5 C10 O2 2.1(6) . . . . ?
C6 C5 C10 C11 0.0(7) . . . . ?
C4 C5 C10 C11 -175.6(4) . . . . ?
S1 N2 C13 C14 -0.4(5) . . . . ?
S1 N2 C13 C4 179.0(3) . . . . ?
C3 C4 C13 N2 -71.0(5) . . . . ?
C5 C4 C13 N2 53.2(5) . . . . ?
C3 C4 C13 C14 108.4(5) . . . . ?
C5 C4 C13 C14 -127.4(5) . . . . ?
N2 C13 C14 C15 0.8(6) . . . . ?
C4 C13 C14 C15 -178.6(4) . . . . ?
N2 C13 C14 Cl1 179.7(3) . . . . ?
C4 C13 C14 Cl1 0.2(7) . . . . ?
C13 C14 C15 Cl2 -178.5(4) . . . . ?
Cl1 C14 C15 Cl2 2.6(6) . . . . ?
C13 C14 C15 S1 -0.7(5) . . . . ?
Cl1 C14 C15 S1 -179.6(3) . . . . ?
N2 S1 C15 C14 0.4(3) . . . . ?
N2 S1 C15 Cl2 178.2(3) . . . . ?
C35 S21 N22 C33 -0.2(3) . . . . ?
C26 N21 C22 C23 -11.9(7) . . . . ?
C26 N21 C22 C27 165.9(4) . . . . ?
N21 C22 C23 C28 164.3(5) . . . . ?
C27 C22 C23 C28 -13.2(8) . . . . ?
N21 C22 C23 C24 -14.5(6) . . . . ?
C27 C22 C23 C24 168.0(5) . . . . ?
C22 C23 C24 C25 32.8(6) . . . . ?
C28 C23 C24 C25 -146.1(4) . . . . ?
C22 C23 C24 C33 -91.6(5) . . . . ?
C28 C23 C24 C33 89.5(5) . . . . ?
C23 C24 C25 C26 -27.5(6) . . . . ?
C33 C24 C25 C26 96.7(5) . . . . ?
C23 C24 C25 C30 156.6(4) . . . . ?
C33 C24 C25 C30 -79.2(5) . . . . ?
C30 C25 C26 N21 179.9(4) . . . . ?
C24 C25 C26 N21 4.6(6) . . . . ?
C30 C25 C26 C32 -1.7(8) . . . . ?
C24 C25 C26 C32 -177.0(4) . . . . ?
C22 N21 C26 C25 17.2(7) . . . . ?
C22 N21 C26 C32 -161.4(4) . . . . ?
C22 C23 C28 O21 -178.8(5) . . . . ?
C24 C23 C28 O21 0.0(7) . . . . ?
C22 C23 C28 C29 -0.1(8) . . . . ?
C24 C23 C28 C29 178.7(4) . . . . ?
C26 C25 C30 O22 -177.2(5) . . . . ?
C24 C25 C30 O22 -1.8(6) . . . . ?
C26 C25 C30 C31 1.5(8) . . . . ?
C24 C25 C30 C31 176.9(4) . . . . ?
S21 N22 C33 C34 0.1(5) . . . . ?
S21 N22 C33 C24 -179.3(3) . . . . ?
C25 C24 C33 N22 -53.3(5) . . . . ?
C23 C24 C33 N22 72.0(5) . . . . ?
C25 C24 C33 C34 127.4(4) . . . . ?
C23 C24 C33 C34 -107.3(5) . . . . ?
N22 C33 C34 C35 0.1(6) . . . . ?
C24 C33 C34 C35 179.5(4) . . . . ?
N22 C33 C34 Cl21 178.6(3) . . . . ?
C24 C33 C34 Cl21 -2.0(7) . . . . ?
C33 C34 C35 Cl22 -179.8(4) . . . . ?
Cl21 C34 C35 Cl22 1.6(6) . . . . ?
C33 C34 C35 S21 -0.2(5) . . . . ?
Cl21 C34 C35 S21 -178.8(3) . . . . ?
N22 S21 C35 C34 0.3(4) . . . . ?
N22 S21 C35 Cl22 179.9(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
N1 H1 O1 0.80(3) 2.04(4) 2.825(5) 169(5) 1_455 yes
C4 H4A Cl1 1.00 2.82 3.325(4) 111.8 . yes
C11 H11C O22 0.98 2.58 3.554(6) 171.4 2_657 yes
N21 H21 O21 0.79(3) 2.09(4) 2.871(5) 170(5) 1_455 yes
C27 H27B O21 0.98 2.56 3.403(5) 144.6 1_455 yes
C31 H31C O2 0.98 2.57 3.546(6) 178.6 2_647 yes

_refine_diff_density_max         0.449
_refine_diff_density_min         -0.423
_refine_diff_density_rms         0.084



# start Validation Reply Form
_vrf_PLAT910_I681                
;
PROBLEM: Missing # of FCF Reflection(s) Below Theta(Min). 15 Note
RESPONSE: Closed by beamstop.
;
# end Validation Reply Form
####################################################################### 
# 
# 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_I607
_database_code_depnum_ccdc_archive 'CCDC 2243956'
loop_
_audit_author_name
_audit_author_address
'Mikhail Grigoriev'
;IPCE RAS
Russia
;
_audit_update_record             
;
2023-02-22 deposited with the CCDC.	2023-02-28 downloaded from the CCDC.
;
_audit_creation_date             2023-02-21
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelxl_version_number           2013-4
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C12 H9 Cl2 N3 O2 S'
_chemical_formula_sum            'C12 H9 Cl2 N3 O2 S'
_chemical_formula_weight         330.18
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.1335(2)
_cell_length_b                   9.2637(2)
_cell_length_c                   10.0924(3)
_cell_angle_alpha                72.817(2)
_cell_angle_beta                 72.328(3)
_cell_angle_gamma                76.935(2)
_cell_volume                     684.39(3)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    11855
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      79.0
_cell_measurement_theta_min      4.7
_shelx_estimated_absorpt_T_max   0.479
_shelx_estimated_absorpt_T_min   0.339
_exptl_absorpt_coefficient_mu    5.746
_exptl_absorpt_correction_T_max  0.408
_exptl_absorpt_correction_T_min  0.264
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.117a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.602
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             336
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.15
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0511
_diffrn_reflns_av_unetI/netI     0.0293
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            14966
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         79.561
_diffrn_reflns_theta_min         4.742
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'φ and ω'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2876
_reflns_number_total             2945
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.41.117a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.117a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.117a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_refine_diff_density_max         0.637
_refine_diff_density_min         -0.502
_refine_diff_density_rms         0.083
_refine_ls_extinction_coef       0.0070(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     190
_refine_ls_number_reflns         2945
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0363
_refine_ls_R_factor_gt           0.0358
_refine_ls_restrained_S_all      1.031
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0682P)²+0.3244P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0985
_refine_ls_wR_factor_ref         0.0992
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1.a Ternary CH refined with riding coordinates:
 C4(H4)
1.b Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C), C12(H12A,H12B,H12C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     difmap
_atom_sites_solution_secondary   difmap
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 -0.00588(5) 0.51834(4) 0.81004(4) 0.01651(14) Uani 1 1 d . . . . .
Cl2 Cl 0.05875(5) 0.73080(4) 0.46838(4) 0.01901(14) Uani 1 1 d . . . . .
S1 S 0.33805(5) 0.46459(4) 0.41858(4) 0.01653(14) Uani 1 1 d . . . . .
O1 O 0.64919(14) 0.06246(13) 0.80858(13) 0.0156(2) Uani 1 1 d . . . . .
O2 O 0.07793(16) 0.05726(14) 0.79342(15) 0.0236(3) Uani 1 1 d . . . . .
N1 N 0.72418(19) 0.22759(17) 0.89299(16) 0.0178(3) Uani 1 1 d . . . . .
H1A H 0.828(3) 0.173(3) 0.872(2) 0.021 Uiso 1 1 d . U . . .
H1B H 0.702(3) 0.304(3) 0.924(3) 0.021 Uiso 1 1 d . U . . .
N2 N 0.34057(18) 0.51824(16) 0.94841(16) 0.0180(3) Uani 1 1 d . . . . .
N3 N 0.38050(17) 0.31696(15) 0.54892(14) 0.0150(3) Uani 1 1 d . . . . .
C1 C 0.38151(19) 0.40496(18) 0.91317(16) 0.0137(3) Uani 1 1 d . . . . .
C2 C 0.5952(2) 0.19188(17) 0.85791(16) 0.0131(3) Uani 1 1 d . . . . .
C3 C 0.4290(2) 0.26722(17) 0.86756(16) 0.0125(3) Uani 1 1 d . . . . .
C4 C 0.30069(19) 0.22021(17) 0.81216(16) 0.0124(3) Uani 1 1 d . . . . .
H4 H 0.1859 0.2188 0.8855 0.015 Uiso 1 1 calc R U . . .
C5 C 0.3656(2) 0.06231(17) 0.78505(16) 0.0127(3) Uani 1 1 d . . . . .
C6 C 0.5312(2) -0.00480(17) 0.78080(17) 0.0140(3) Uani 1 1 d . . . . .
C7 C 0.27604(19) 0.33507(17) 0.67424(16) 0.0126(3) Uani 1 1 d . . . . .
C8 C 0.15432(19) 0.47260(17) 0.66650(16) 0.0134(3) Uani 1 1 d . . . . .
C9 C 0.1750(2) 0.55870(18) 0.52869(17) 0.0148(3) Uani 1 1 d . . . . .
C10 C 0.2294(2) -0.00382(18) 0.76138(17) 0.0153(3) Uani 1 1 d . . . . .
C11 C 0.2703(2) -0.1369(2) 0.6947(2) 0.0249(4) Uani 1 1 d . . . . .
H11A H 0.2985 -0.2314 0.7648 0.037 Uiso 1 1 calc R U . . .
H11B H 0.3704 -0.1226 0.6108 0.037 Uiso 1 1 calc R U . . .
H11C H 0.1689 -0.1437 0.6649 0.037 Uiso 1 1 calc R U . . .
C12 C 0.6249(2) -0.15408(18) 0.74751(19) 0.0189(3) Uani 1 1 d . . . . .
H12A H 0.6494 -0.1447 0.6443 0.028 Uiso 1 1 calc R U . . .
H12B H 0.5516 -0.2340 0.8002 0.028 Uiso 1 1 calc R U . . .
H12C H 0.7348 -0.1811 0.7762 0.028 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 C8 1.7155(15) . ?
Cl2 C9 1.7031(16) . ?
S1 N3 1.6490(14) . ?
S1 C9 1.7056(16) . ?
O1 C2 1.3638(19) . ?
O1 C6 1.3873(18) . ?
O2 C10 1.222(2) . ?
N1 H1A 0.88(3) . ?
N1 H1B 0.82(3) . ?
N1 C2 1.336(2) . ?
N2 C1 1.153(2) . ?
N3 C7 1.326(2) . ?
C1 C3 1.416(2) . ?
C2 C3 1.363(2) . ?
C3 C4 1.515(2) . ?
C4 H4 1.0000 . ?
C4 C5 1.514(2) . ?
C4 C7 1.519(2) . ?
C5 C6 1.344(2) . ?
C5 C10 1.488(2) . ?
C6 C12 1.499(2) . ?
C7 C8 1.424(2) . ?
C8 C9 1.365(2) . ?
C10 C11 1.501(2) . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N3 S1 C9 94.76(7) . . ?
C2 O1 C6 120.58(12) . . ?
H1A N1 H1B 126(2) . . ?
C2 N1 H1A 117.3(15) . . ?
C2 N1 H1B 116.7(16) . . ?
C7 N3 S1 110.46(11) . . ?
N2 C1 C3 178.58(17) . . ?
N1 C2 O1 110.87(13) . . ?
N1 C2 C3 127.94(15) . . ?
C3 C2 O1 121.19(14) . . ?
C1 C3 C4 118.47(13) . . ?
C2 C3 C1 119.09(14) . . ?
C2 C3 C4 121.92(14) . . ?
C3 C4 H4 109.0 . . ?
C3 C4 C7 109.58(12) . . ?
C5 C4 C3 110.57(12) . . ?
C5 C4 H4 109.0 . . ?
C5 C4 C7 109.79(12) . . ?
C7 C4 H4 109.0 . . ?
C6 C5 C4 121.48(14) . . ?
C6 C5 C10 125.60(14) . . ?
C10 C5 C4 112.90(13) . . ?
O1 C6 C12 107.54(13) . . ?
C5 C6 O1 122.12(14) . . ?
C5 C6 C12 130.34(14) . . ?
N3 C7 C4 120.19(13) . . ?
N3 C7 C8 114.60(14) . . ?
C8 C7 C4 125.03(14) . . ?
C7 C8 Cl1 124.33(12) . . ?
C9 C8 Cl1 124.42(13) . . ?
C9 C8 C7 111.13(14) . . ?
Cl2 C9 S1 123.32(10) . . ?
C8 C9 Cl2 127.63(13) . . ?
C8 C9 S1 109.03(12) . . ?
O2 C10 C5 117.94(14) . . ?
O2 C10 C11 118.86(14) . . ?
C5 C10 C11 123.15(14) . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C6 C12 H12A 109.5 . . ?
C6 C12 H12B 109.5 . . ?
C6 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1A O2 0.88(3) 2.11(3) 2.984(2) 172(2) 1_655
N1 H1B N2 0.82(3) 2.28(3) 3.088(2) 168(2) 2_667

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
Cl1 C8 C9 Cl2 3.5(2) . . . . ?
Cl1 C8 C9 S1 -175.24(9) . . . . ?
S1 N3 C7 C4 -174.74(11) . . . . ?
S1 N3 C7 C8 0.72(17) . . . . ?
O1 C2 C3 C1 -177.12(13) . . . . ?
O1 C2 C3 C4 -5.5(2) . . . . ?
N1 C2 C3 C1 3.3(3) . . . . ?
N1 C2 C3 C4 174.91(15) . . . . ?
N3 S1 C9 Cl2 -179.38(10) . . . . ?
N3 S1 C9 C8 -0.59(12) . . . . ?
N3 C7 C8 Cl1 175.11(11) . . . . ?
N3 C7 C8 C9 -1.2(2) . . . . ?
C1 C3 C4 C5 -173.48(13) . . . . ?
C1 C3 C4 C7 65.37(17) . . . . ?
C2 O1 C6 C5 7.7(2) . . . . ?
C2 O1 C6 C12 -172.61(13) . . . . ?
C2 C3 C4 C5 14.9(2) . . . . ?
C2 C3 C4 C7 -106.25(16) . . . . ?
C3 C4 C5 C6 -13.9(2) . . . . ?
C3 C4 C5 C10 167.46(12) . . . . ?
C3 C4 C7 N3 88.52(16) . . . . ?
C3 C4 C7 C8 -86.44(17) . . . . ?
C4 C5 C6 O1 3.6(2) . . . . ?
C4 C5 C6 C12 -175.96(15) . . . . ?
C4 C5 C10 O2 -14.2(2) . . . . ?
C4 C5 C10 C11 163.16(15) . . . . ?
C4 C7 C8 Cl1 -9.7(2) . . . . ?
C4 C7 C8 C9 174.03(14) . . . . ?
C5 C4 C7 N3 -33.11(18) . . . . ?
C5 C4 C7 C8 151.94(14) . . . . ?
C6 O1 C2 N1 172.93(13) . . . . ?
C6 O1 C2 C3 -6.7(2) . . . . ?
C6 C5 C10 O2 167.22(16) . . . . ?
C6 C5 C10 C11 -15.4(3) . . . . ?
C7 C4 C5 C6 107.16(16) . . . . ?
C7 C4 C5 C10 -71.51(16) . . . . ?
C7 C8 C9 Cl2 179.77(11) . . . . ?
C7 C8 C9 S1 1.05(17) . . . . ?
C9 S1 N3 C7 -0.08(12) . . . . ?
C10 C5 C6 O1 -177.92(14) . . . . ?
C10 C5 C6 C12 2.5(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_I677
_database_code_depnum_ccdc_archive 'CCDC 2236986'
loop_
_audit_author_name
_audit_author_address
'Mikhail Grigoriev'
;IPCE RAS
Russia
;
_audit_update_record             
;
2023-01-18 deposited with the CCDC.	2023-02-28 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            'C14 H14 Cl2 N2 O4 S'
_chemical_formula_weight         377.23

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

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

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

_cell_length_a                   12.2812(6)
_cell_length_b                   7.3500(4)
_cell_length_c                   17.4340(9)
_cell_angle_alpha                90
_cell_angle_beta                 97.212(2)
_cell_angle_gamma                90
_cell_volume                     1561.26(14)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    8644
_cell_measurement_theta_min      2.71
_cell_measurement_theta_max      29.98

_exptl_crystal_description       fragment
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.605
_exptl_crystal_F_000             776
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.500
_exptl_crystal_size_mid          0.400
_exptl_crystal_size_min          0.320
_exptl_absorpt_coefficient_mu    0.571
_shelx_estimated_absorpt_T_min   0.763
_shelx_estimated_absorpt_T_max   0.838
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9412
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_process_details   
;
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;
_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            26683
_diffrn_reflns_av_unetI/netI     0.0527
_diffrn_reflns_av_R_equivalents  0.0379
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         4.096
_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 0.914
_diffrn_reflns_point_group_measured_fraction_full 0.924
_reflns_number_total             8322
_reflns_number_gt                7453
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.712
_reflns_Friedel_fraction_max     0.820
_reflns_Friedel_fraction_full    0.843

_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)+(0.0343P)²+0.0188P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.30(5)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         8322
_refine_ls_number_parameters     434
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0446
_refine_ls_R_factor_gt           0.0362
_refine_ls_wR_factor_ref         0.0727
_refine_ls_wR_factor_gt          0.0697
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_restrained_S_all      1.037
_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 0.88734(5) 0.70700(9) 0.80023(4) 0.01423(14) Uani 1 1 d . . . . .
Cl2 Cl 0.87747(6) 1.16581(10) 0.79271(4) 0.02020(16) Uani 1 1 d . . . . .
S1 S 0.69241(6) 1.10640(9) 0.88611(4) 0.01443(15) Uani 1 1 d . . . . .
O1 O 0.51120(15) 0.5639(3) 0.98752(11) 0.0138(4) Uani 1 1 d . . . . .
O2 O 0.63811(16) 0.5175(3) 0.74570(11) 0.0188(5) Uani 1 1 d . . . . .
O3 O 0.83459(16) 0.4890(3) 1.09547(11) 0.0169(4) Uani 1 1 d . . . . .
O4 O 0.89047(15) 0.5071(3) 0.97704(10) 0.0121(4) Uani 1 1 d . . . . .
N1 N 0.6132(2) 0.5190(4) 1.10087(14) 0.0165(5) Uani 1 1 d . . . . .
H1A H 0.677(3) 0.496(5) 1.1299(19) 0.020 Uiso 1 1 d . U . . .
H1B H 0.555(3) 0.481(5) 1.1153(19) 0.020 Uiso 1 1 d . U . . .
N2 N 0.64961(19) 0.9022(3) 0.90848(13) 0.0125(5) Uani 1 1 d . . . . .
C2 C 0.4895(2) 0.5364(4) 0.90853(16) 0.0115(5) Uani 1 1 d . . . . .
C3 C 0.5714(2) 0.5300(4) 0.86424(15) 0.0100(5) Uani 1 1 d . . . . .
C4 C 0.6874(2) 0.5766(3) 0.89878(15) 0.0076(5) Uani 1 1 d . . . . .
H4A H 0.739581 0.499175 0.873517 0.009 Uiso 1 1 calc R U . . .
C5 C 0.7036(2) 0.5388(4) 0.98449(15) 0.0103(5) Uani 1 1 d . . . . .
C6 C 0.6150(2) 0.5384(4) 1.02429(15) 0.0107(5) Uani 1 1 d . . . . .
C7 C 0.3682(2) 0.5248(4) 0.88819(18) 0.0189(6) Uani 1 1 d . . . . .
H7A H 0.347730 0.571369 0.835691 0.028 Uiso 1 1 calc R U . . .
H7B H 0.332161 0.597696 0.924783 0.028 Uiso 1 1 calc R U . . .
H7C H 0.344814 0.397665 0.890742 0.028 Uiso 1 1 calc R U . . .
C8 C 0.5594(2) 0.4876(4) 0.78076(16) 0.0121(5) Uani 1 1 d . . . . .
C9 C 0.4579(2) 0.4025(4) 0.73861(18) 0.0188(6) Uani 1 1 d . . . . .
H9A H 0.475022 0.349907 0.689876 0.028 Uiso 1 1 calc R U . . .
H9B H 0.400850 0.495474 0.727733 0.028 Uiso 1 1 calc R U . . .
H9C H 0.431583 0.306551 0.770712 0.028 Uiso 1 1 calc R U . . .
C10 C 0.7103(2) 0.7752(3) 0.88229(14) 0.0070(5) Uani 1 1 d . . . . .
C11 C 0.7955(2) 0.8406(4) 0.84036(14) 0.0097(5) Uani 1 1 d . . . . .
C12 C 0.7947(2) 1.0262(4) 0.83765(15) 0.0119(5) Uani 1 1 d . . . . .
C13 C 0.8125(2) 0.5093(4) 1.02572(16) 0.0112(5) Uani 1 1 d . . . . .
C14 C 1.0017(2) 0.4788(4) 1.01440(16) 0.0135(6) Uani 1 1 d . . . . .
H14A H 1.005760 0.365439 1.045305 0.016 Uiso 1 1 calc R U . . .
H14B H 1.024519 0.581706 1.049410 0.016 Uiso 1 1 calc R U . . .
C15 C 1.0761(2) 0.4655(4) 0.95191(16) 0.0150(6) Uani 1 1 d . . . . .
H15A H 1.151009 0.437806 0.975377 0.023 Uiso 1 1 calc R U . . .
H15B H 1.075662 0.581458 0.924155 0.023 Uiso 1 1 calc R U . . .
H15C H 1.049916 0.368463 0.915643 0.023 Uiso 1 1 calc R U . . .
Cl21 Cl 0.84617(6) 0.28719(9) 0.24483(4) 0.01435(14) Uani 1 1 d . . . . .
Cl22 Cl 0.88571(6) -0.16602(11) 0.24393(4) 0.02324(17) Uani 1 1 d . . . . .
S21 S 0.78667(6) -0.14205(9) 0.39168(4) 0.01192(13) Uani 1 1 d . . . . .
O21 O 0.62480(15) 0.3591(3) 0.53927(11) 0.0134(4) Uani 1 1 d . . . . .
O22 O 0.58225(16) 0.3712(3) 0.26742(11) 0.0183(4) Uani 1 1 d . . . . .
O23 O 0.95342(17) 0.5290(3) 0.54975(11) 0.0171(4) Uani 1 1 d . . . . .
O24 O 0.93625(15) 0.5021(3) 0.41940(11) 0.0130(4) Uani 1 1 d . . . . .
N21 N 0.7731(2) 0.4456(4) 0.61769(14) 0.0192(5) Uani 1 1 d . . . . .
H21A H 0.835(3) 0.497(5) 0.6217(19) 0.023 Uiso 1 1 d . U . . .
H21B H 0.729(3) 0.446(5) 0.647(2) 0.023 Uiso 1 1 d . U . . .
N22 N 0.74227(18) 0.0504(3) 0.42530(13) 0.0102(5) Uani 1 1 d . . . . .
C22 C 0.5594(2) 0.3608(4) 0.46864(16) 0.0114(5) Uani 1 1 d . . . . .
C23 C 0.6030(2) 0.3803(3) 0.40226(15) 0.0092(5) Uani 1 1 d . . . . .
C24 C 0.7268(2) 0.3770(4) 0.40143(15) 0.0090(5) Uani 1 1 d . . . . .
H24A H 0.746605 0.465119 0.361728 0.011 Uiso 1 1 calc R U . . .
C25 C 0.7841(2) 0.4324(4) 0.48016(15) 0.0097(5) Uani 1 1 d . . . . .
C26 C 0.7322(2) 0.4152(4) 0.54375(16) 0.0117(5) Uani 1 1 d . . . . .
C27 C 0.4432(2) 0.3317(4) 0.48322(17) 0.0161(6) Uani 1 1 d . . . . .
H27A H 0.401896 0.273953 0.437914 0.024 Uiso 1 1 calc R U . . .
H27B H 0.409659 0.449091 0.492867 0.024 Uiso 1 1 calc R U . . .
H27C H 0.441915 0.252802 0.528427 0.024 Uiso 1 1 calc R U . . .
C28 C 0.5373(2) 0.3990(4) 0.32487(16) 0.0123(6) Uani 1 1 d . . . . .
C29 C 0.4191(2) 0.4598(4) 0.31554(17) 0.0181(6) Uani 1 1 d . . . . .
H29A H 0.401409 0.520195 0.265420 0.027 Uiso 1 1 calc R U . . .
H29B H 0.407794 0.544877 0.357077 0.027 Uiso 1 1 calc R U . . .
H29C H 0.371352 0.353699 0.318059 0.027 Uiso 1 1 calc R U . . .
C30 C 0.7610(2) 0.1873(4) 0.38007(15) 0.0090(5) Uani 1 1 d . . . . .
C31 C 0.8133(2) 0.1394(4) 0.31438(15) 0.0105(5) Uani 1 1 d . . . . .
C32 C 0.8319(2) -0.0431(4) 0.31319(15) 0.0123(5) Uani 1 1 d . . . . .
C33 C 0.8976(2) 0.4912(3) 0.48847(16) 0.0117(5) Uani 1 1 d . . . . .
C34 C 1.0459(2) 0.5775(4) 0.41783(18) 0.0166(6) Uani 1 1 d . . . . .
H34A H 1.074193 0.624569 0.469728 0.020 Uiso 1 1 calc R U . . .
H34B H 1.042156 0.680242 0.380871 0.020 Uiso 1 1 calc R U . . .
C35 C 1.1220(2) 0.4357(5) 0.39440(17) 0.0193(6) Uani 1 1 d . . . . .
H35A H 1.193376 0.490849 0.389424 0.029 Uiso 1 1 calc R U . . .
H35B H 1.091306 0.383152 0.344674 0.029 Uiso 1 1 calc R U . . .
H35C H 1.131223 0.339703 0.433716 0.029 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 1.710(3) . ?
Cl2 C12 1.703(3) . ?
S1 N2 1.653(2) . ?
S1 C12 1.704(3) . ?
O1 C6 1.366(3) . ?
O1 C2 1.384(3) . ?
O2 C8 1.227(3) . ?
O3 C13 1.221(3) . ?
O4 C13 1.358(3) . ?
O4 C14 1.453(3) . ?
N1 C6 1.346(3) . ?
N1 H1A 0.89(3) . ?
N1 H1B 0.83(3) . ?
N2 C10 1.312(3) . ?
C2 C3 1.343(4) . ?
C2 C7 1.491(4) . ?
C3 C8 1.478(4) . ?
C3 C4 1.515(4) . ?
C4 C5 1.508(4) . ?
C4 C10 1.521(3) . ?
C4 H4A 1.0000 . ?
C5 C6 1.362(4) . ?
C5 C13 1.452(4) . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C8 C9 1.502(4) . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 C11 1.433(3) . ?
C11 C12 1.365(4) . ?
C14 C15 1.510(4) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
Cl21 C31 1.714(3) . ?
Cl22 C32 1.706(3) . ?
S21 N22 1.650(2) . ?
S21 C32 1.703(3) . ?
O21 C26 1.375(3) . ?
O21 C22 1.383(3) . ?
O22 C28 1.220(3) . ?
O23 C33 1.227(3) . ?
O24 C33 1.351(3) . ?
O24 C34 1.460(3) . ?
N21 C26 1.342(4) . ?
N21 H21A 0.84(4) . ?
N21 H21B 0.79(3) . ?
N22 C30 1.316(3) . ?
C22 C23 1.342(4) . ?
C22 C27 1.497(4) . ?
C23 C28 1.489(4) . ?
C23 C24 1.522(4) . ?
C24 C30 1.516(4) . ?
C24 C25 1.518(4) . ?
C24 H24A 1.0000 . ?
C25 C26 1.353(4) . ?
C25 C33 1.449(4) . ?
C27 H27A 0.9800 . ?
C27 H27B 0.9800 . ?
C27 H27C 0.9800 . ?
C28 C29 1.508(4) . ?
C29 H29A 0.9800 . ?
C29 H29B 0.9800 . ?
C29 H29C 0.9800 . ?
C30 C31 1.426(4) . ?
C31 C32 1.361(4) . ?
C34 C35 1.491(4) . ?
C34 H34A 0.9900 . ?
C34 H34B 0.9900 . ?
C35 H35A 0.9800 . ?
C35 H35B 0.9800 . ?
C35 H35C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N2 S1 C12 94.53(13) . . ?
C6 O1 C2 119.9(2) . . ?
C13 O4 C14 114.8(2) . . ?
C6 N1 H1A 117(2) . . ?
C6 N1 H1B 117(2) . . ?
H1A N1 H1B 119(3) . . ?
C10 N2 S1 110.64(18) . . ?
C3 C2 O1 120.9(2) . . ?
C3 C2 C7 131.3(3) . . ?
O1 C2 C7 107.8(2) . . ?
C2 C3 C8 125.8(3) . . ?
C2 C3 C4 119.9(2) . . ?
C8 C3 C4 114.3(2) . . ?
C5 C4 C3 110.7(2) . . ?
C5 C4 C10 111.1(2) . . ?
C3 C4 C10 109.2(2) . . ?
C5 C4 H4A 108.6 . . ?
C3 C4 H4A 108.6 . . ?
C10 C4 H4A 108.6 . . ?
C6 C5 C13 119.5(2) . . ?
C6 C5 C4 119.4(2) . . ?
C13 C5 C4 121.1(2) . . ?
N1 C6 C5 128.3(3) . . ?
N1 C6 O1 110.4(2) . . ?
C5 C6 O1 121.3(2) . . ?
C2 C7 H7A 109.5 . . ?
C2 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C2 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
O2 C8 C3 117.7(2) . . ?
O2 C8 C9 119.2(3) . . ?
C3 C8 C9 123.0(2) . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C8 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
N2 C10 C11 115.0(2) . . ?
N2 C10 C4 119.4(2) . . ?
C11 C10 C4 125.7(2) . . ?
C12 C11 C10 110.5(2) . . ?
C12 C11 Cl1 124.2(2) . . ?
C10 C11 Cl1 125.3(2) . . ?
C11 C12 Cl2 128.0(2) . . ?
C11 C12 S1 109.4(2) . . ?
Cl2 C12 S1 122.64(17) . . ?
O3 C13 O4 122.3(2) . . ?
O3 C13 C5 126.0(2) . . ?
O4 C13 C5 111.7(2) . . ?
O4 C14 C15 107.8(2) . . ?
O4 C14 H14A 110.1 . . ?
C15 C14 H14A 110.1 . . ?
O4 C14 H14B 110.1 . . ?
C15 C14 H14B 110.1 . . ?
H14A C14 H14B 108.5 . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
N22 S21 C32 94.30(13) . . ?
C26 O21 C22 119.6(2) . . ?
C33 O24 C34 117.9(2) . . ?
C26 N21 H21A 112(2) . . ?
C26 N21 H21B 115(3) . . ?
H21A N21 H21B 128(4) . . ?
C30 N22 S21 110.63(18) . . ?
C23 C22 O21 121.3(2) . . ?
C23 C22 C27 130.8(3) . . ?
O21 C22 C27 107.9(2) . . ?
C22 C23 C28 124.2(2) . . ?
C22 C23 C24 120.9(2) . . ?
C28 C23 C24 114.9(2) . . ?
C30 C24 C25 110.9(2) . . ?
C30 C24 C23 109.0(2) . . ?
C25 C24 C23 109.7(2) . . ?
C30 C24 H24A 109.1 . . ?
C25 C24 H24A 109.1 . . ?
C23 C24 H24A 109.1 . . ?
C26 C25 C33 119.5(2) . . ?
C26 C25 C24 120.2(2) . . ?
C33 C25 C24 120.1(2) . . ?
N21 C26 C25 127.9(3) . . ?
N21 C26 O21 110.2(2) . . ?
C25 C26 O21 121.9(2) . . ?
C22 C27 H27A 109.5 . . ?
C22 C27 H27B 109.5 . . ?
H27A C27 H27B 109.5 . . ?
C22 C27 H27C 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
O22 C28 C23 118.6(2) . . ?
O22 C28 C29 119.3(3) . . ?
C23 C28 C29 122.0(2) . . ?
C28 C29 H29A 109.5 . . ?
C28 C29 H29B 109.5 . . ?
H29A C29 H29B 109.5 . . ?
C28 C29 H29C 109.5 . . ?
H29A C29 H29C 109.5 . . ?
H29B C29 H29C 109.5 . . ?
N22 C30 C31 115.0(2) . . ?
N22 C30 C24 118.8(2) . . ?
C31 C30 C24 126.3(2) . . ?
C32 C31 C30 110.5(2) . . ?
C32 C31 Cl21 124.0(2) . . ?
C30 C31 Cl21 125.6(2) . . ?
C31 C32 S21 109.6(2) . . ?
C31 C32 Cl22 127.9(2) . . ?
S21 C32 Cl22 122.46(17) . . ?
O23 C33 O24 122.9(3) . . ?
O23 C33 C25 125.5(3) . . ?
O24 C33 C25 111.7(2) . . ?
O24 C34 C35 110.5(2) . . ?
O24 C34 H34A 109.5 . . ?
C35 C34 H34A 109.5 . . ?
O24 C34 H34B 109.5 . . ?
C35 C34 H34B 109.5 . . ?
H34A C34 H34B 108.1 . . ?
C34 C35 H35A 109.5 . . ?
C34 C35 H35B 109.5 . . ?
H35A C35 H35B 109.5 . . ?
C34 C35 H35C 109.5 . . ?
H35A C35 H35C 109.5 . . ?
H35B C35 H35C 109.5 . . ?

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
C12 S1 N2 C10 1.2(2) . . . . ?
C6 O1 C2 C3 -16.8(4) . . . . ?
C6 O1 C2 C7 165.1(2) . . . . ?
O1 C2 C3 C8 175.0(2) . . . . ?
C7 C2 C3 C8 -7.4(5) . . . . ?
O1 C2 C3 C4 -7.8(4) . . . . ?
C7 C2 C3 C4 169.8(3) . . . . ?
C2 C3 C4 C5 26.9(3) . . . . ?
C8 C3 C4 C5 -155.5(2) . . . . ?
C2 C3 C4 C10 -95.7(3) . . . . ?
C8 C3 C4 C10 81.9(3) . . . . ?
C3 C4 C5 C6 -24.4(3) . . . . ?
C10 C4 C5 C6 97.1(3) . . . . ?
C3 C4 C5 C13 157.8(2) . . . . ?
C10 C4 C5 C13 -80.6(3) . . . . ?
C13 C5 C6 N1 2.3(4) . . . . ?
C4 C5 C6 N1 -175.5(3) . . . . ?
C13 C5 C6 O1 -179.4(2) . . . . ?
C4 C5 C6 O1 2.8(4) . . . . ?
C2 O1 C6 N1 -162.0(2) . . . . ?
C2 O1 C6 C5 19.4(4) . . . . ?
C2 C3 C8 O2 167.7(3) . . . . ?
C4 C3 C8 O2 -9.6(4) . . . . ?
C2 C3 C8 C9 -15.2(4) . . . . ?
C4 C3 C8 C9 167.4(2) . . . . ?
S1 N2 C10 C11 -1.2(3) . . . . ?
S1 N2 C10 C4 178.03(18) . . . . ?
C5 C4 C10 N2 -62.2(3) . . . . ?
C3 C4 C10 N2 60.2(3) . . . . ?
C5 C4 C10 C11 116.9(3) . . . . ?
C3 C4 C10 C11 -120.7(3) . . . . ?
N2 C10 C11 C12 0.5(3) . . . . ?
C4 C10 C11 C12 -178.6(2) . . . . ?
N2 C10 C11 Cl1 179.59(19) . . . . ?
C4 C10 C11 Cl1 0.4(4) . . . . ?
C10 C11 C12 Cl2 -178.3(2) . . . . ?
Cl1 C11 C12 Cl2 2.6(4) . . . . ?
C10 C11 C12 S1 0.4(3) . . . . ?
Cl1 C11 C12 S1 -178.71(14) . . . . ?
N2 S1 C12 C11 -0.9(2) . . . . ?
N2 S1 C12 Cl2 177.90(17) . . . . ?
C14 O4 C13 O3 0.0(4) . . . . ?
C14 O4 C13 C5 179.8(2) . . . . ?
C6 C5 C13 O3 -2.6(4) . . . . ?
C4 C5 C13 O3 175.2(3) . . . . ?
C6 C5 C13 O4 177.6(2) . . . . ?
C4 C5 C13 O4 -4.6(4) . . . . ?
C13 O4 C14 C15 175.7(2) . . . . ?
C32 S21 N22 C30 -0.5(2) . . . . ?
C26 O21 C22 C23 13.6(4) . . . . ?
C26 O21 C22 C27 -168.3(2) . . . . ?
O21 C22 C23 C28 -174.6(2) . . . . ?
C27 C22 C23 C28 7.9(5) . . . . ?
O21 C22 C23 C24 7.9(4) . . . . ?
C27 C22 C23 C24 -169.6(3) . . . . ?
C22 C23 C24 C30 97.0(3) . . . . ?
C28 C23 C24 C30 -80.7(3) . . . . ?
C22 C23 C24 C25 -24.6(3) . . . . ?
C28 C23 C24 C25 157.7(2) . . . . ?
C30 C24 C25 C26 -97.8(3) . . . . ?
C23 C24 C25 C26 22.7(3) . . . . ?
C30 C24 C25 C33 77.6(3) . . . . ?
C23 C24 C25 C33 -161.9(2) . . . . ?
C33 C25 C26 N21 -0.4(4) . . . . ?
C24 C25 C26 N21 175.1(3) . . . . ?
C33 C25 C26 O21 -179.7(2) . . . . ?
C24 C25 C26 O21 -4.3(4) . . . . ?
C22 O21 C26 N21 165.0(2) . . . . ?
C22 O21 C26 C25 -15.5(4) . . . . ?
C22 C23 C28 O22 -162.2(3) . . . . ?
C24 C23 C28 O22 15.5(4) . . . . ?
C22 C23 C28 C29 20.8(4) . . . . ?
C24 C23 C28 C29 -161.5(2) . . . . ?
S21 N22 C30 C31 0.2(3) . . . . ?
S21 N22 C30 C24 -179.56(19) . . . . ?
C25 C24 C30 N22 59.7(3) . . . . ?
C23 C24 C30 N22 -61.2(3) . . . . ?
C25 C24 C30 C31 -120.0(3) . . . . ?
C23 C24 C30 C31 119.1(3) . . . . ?
N22 C30 C31 C32 0.3(3) . . . . ?
C24 C30 C31 C32 -179.9(2) . . . . ?
N22 C30 C31 Cl21 179.1(2) . . . . ?
C24 C30 C31 Cl21 -1.2(4) . . . . ?
C30 C31 C32 S21 -0.7(3) . . . . ?
Cl21 C31 C32 S21 -179.46(15) . . . . ?
C30 C31 C32 Cl22 176.3(2) . . . . ?
Cl21 C31 C32 Cl22 -2.4(4) . . . . ?
N22 S21 C32 C31 0.7(2) . . . . ?
N22 S21 C32 Cl22 -176.50(18) . . . . ?
C34 O24 C33 O23 -5.6(4) . . . . ?
C34 O24 C33 C25 173.8(2) . . . . ?
C26 C25 C33 O23 -0.2(4) . . . . ?
C24 C25 C33 O23 -175.7(2) . . . . ?
C26 C25 C33 O24 -179.6(2) . . . . ?
C24 C25 C33 O24 4.9(3) . . . . ?
C33 O24 C34 C35 114.3(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
N1 H1A O3 0.89(3) 2.10(3) 2.741(3) 128(3) . yes
N1 H1B N2 0.83(3) 2.57(3) 3.324(4) 152(3) 2_647 yes
C4 H4A Cl1 1.00 2.80 3.311(3) 112.2 . yes
N21 H21A O23 0.84(4) 2.05(3) 2.710(4) 135(3) . yes
N21 H21B O2 0.79(3) 2.22(3) 2.989(3) 162(4) . yes
C24 H24A Cl21 1.00 2.83 3.323(3) 111.4 . yes
C27 H27B N22 0.98 2.60 3.351(3) 133.9 2_656 yes
C29 H29A S1 0.98 2.82 3.767(3) 163.0 2_646 yes
C35 H35C O23 0.98 2.54 3.311(4) 135.5 2_746 yes

_refine_diff_density_max         0.378
_refine_diff_density_min         -0.282
_refine_diff_density_rms         0.065



# start Validation Reply Form
_vrf_PLAT035_I677                
;
PROBLEM: _chemical_absolute_configuration Info Not Given Please Do !
RESPONSE: ...
;
_vrf_PLAT910_I677                
;
PROBLEM: Missing # of FCF Reflection(s) Below Theta(Min). 19 Note
RESPONSE: Closed by beamstop.
;
# end Validation Reply Form
####################################################################### 
# 
# 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_I625
_database_code_depnum_ccdc_archive 'CCDC 2236985'
loop_
_audit_author_name
_audit_author_address
'Mikhail Grigoriev'
;IPCE RAS
Russia
;
_audit_update_record             
;
2023-01-18 deposited with the CCDC.	2023-02-28 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            'C13 H11 Cl2 N3 O3 S'
_chemical_formula_weight         360.21

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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

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

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.5420(14)
_cell_length_b                   8.8365(16)
_cell_length_c                   11.384(2)
_cell_angle_alpha                83.566(6)
_cell_angle_beta                 83.963(6)
_cell_angle_gamma                88.682(6)
_cell_volume                     749.7(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    1717
_cell_measurement_theta_min      2.32
_cell_measurement_theta_max      27.12

_exptl_crystal_description       fragment
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.596
_exptl_crystal_F_000             368
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.260
_exptl_crystal_size_mid          0.140
_exptl_crystal_size_min          0.060
_exptl_absorpt_coefficient_mu    0.587
_shelx_estimated_absorpt_T_min   0.862
_shelx_estimated_absorpt_T_max   0.966
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8524
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_process_details   
;
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;
_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            13476
_diffrn_reflns_av_unetI/netI     0.1054
_diffrn_reflns_av_R_equivalents  0.0823
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         4.081
_diffrn_reflns_theta_max         29.993
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.972
_diffrn_measured_fraction_theta_full 0.977
_diffrn_reflns_Laue_measured_fraction_max 0.972
_diffrn_reflns_Laue_measured_fraction_full 0.977
_diffrn_reflns_point_group_measured_fraction_max 0.972
_diffrn_reflns_point_group_measured_fraction_full 0.977
_reflns_number_total             4251
_reflns_number_gt                2571
_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)+(0.0448P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4251
_refine_ls_number_parameters     207
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1077
_refine_ls_R_factor_gt           0.0527
_refine_ls_wR_factor_ref         0.1207
_refine_ls_wR_factor_gt          0.1013
_refine_ls_goodness_of_fit_ref   0.993
_refine_ls_restrained_S_all      0.993
_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 0.20356(10) 0.86381(9) 0.55508(6) 0.02148(18) Uani 1 1 d . . . . .
Cl2 Cl 0.56383(10) 0.81026(9) 0.36799(5) 0.02074(18) Uani 1 1 d . . . . .
S1 S 0.66826(10) 0.59797(9) 0.57638(6) 0.01878(18) Uani 1 1 d . . . . .
O1 O 0.2866(2) 0.4984(2) 1.03854(15) 0.0151(4) Uani 1 1 d . . . . .
O2 O 0.0763(3) 0.4864(2) 0.66254(16) 0.0225(5) Uani 1 1 d . . . . .
O3 O 0.0381(3) 0.2801(2) 0.79650(15) 0.0178(4) Uani 1 1 d . . . . .
N1 N 0.5359(3) 0.5696(3) 0.70252(19) 0.0165(5) Uani 1 1 d . . . . .
N2 N 0.4047(3) 0.6941(3) 1.1056(2) 0.0159(5) Uani 1 1 d . . . . .
H2A H 0.449(4) 0.781(4) 1.103(3) 0.019 Uiso 1 1 d . U . . .
H2B H 0.416(4) 0.625(4) 1.167(3) 0.019 Uiso 1 1 d . U . . .
N3 N 0.4285(3) 1.0008(3) 0.86925(19) 0.0193(5) Uani 1 1 d . . . . .
C2 C 0.3399(3) 0.6454(3) 1.0119(2) 0.0135(6) Uani 1 1 d . . . . .
C3 C 0.3214(4) 0.7243(3) 0.9044(2) 0.0137(6) Uani 1 1 d . . . . .
C4 C 0.2500(4) 0.6513(3) 0.8043(2) 0.0132(6) Uani 1 1 d . . . . .
H4A H 0.145261 0.713343 0.779011 0.016 Uiso 1 1 calc R U . . .
C5 C 0.1858(3) 0.4923(3) 0.8485(2) 0.0131(6) Uani 1 1 d . . . . .
C6 C 0.2074(3) 0.4246(3) 0.9572(2) 0.0136(6) Uani 1 1 d . . . . .
C7 C 0.0958(4) 0.4216(3) 0.7594(2) 0.0160(6) Uani 1 1 d . . . . .
C8 C -0.0479(4) 0.2054(3) 0.7107(2) 0.0189(6) Uani 1 1 d . . . . .
H8A H 0.033452 0.200177 0.637065 0.023 Uiso 1 1 calc R U . . .
H8B H -0.157371 0.261778 0.690171 0.023 Uiso 1 1 calc R U . . .
C9 C -0.0931(4) 0.0476(3) 0.7692(3) 0.0231(7) Uani 1 1 d . . . . .
H9A H -0.152170 -0.007937 0.714678 0.035 Uiso 1 1 calc R U . . .
H9B H -0.173104 0.054711 0.842034 0.035 Uiso 1 1 calc R U . . .
H9C H 0.016505 -0.006670 0.788890 0.035 Uiso 1 1 calc R U . . .
C10 C 0.1586(4) 0.2696(3) 1.0147(2) 0.0172(6) Uani 1 1 d . . . . .
H10A H 0.198781 0.255113 1.094359 0.026 Uiso 1 1 calc R U . . .
H10B H 0.216077 0.193144 0.966788 0.026 Uiso 1 1 calc R U . . .
H10C H 0.028935 0.258267 1.020827 0.026 Uiso 1 1 calc R U . . .
C11 C 0.3804(4) 0.8764(3) 0.8843(2) 0.0153(6) Uani 1 1 d . . . . .
C12 C 0.3901(4) 0.6531(3) 0.6975(2) 0.0145(6) Uani 1 1 d . . . . .
C13 C 0.3788(4) 0.7451(3) 0.5877(2) 0.0147(6) Uani 1 1 d . . . . .
C14 C 0.5269(4) 0.7258(3) 0.5102(2) 0.0165(6) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl1 C13 1.713(3) . ?
Cl2 C14 1.703(3) . ?
S1 N1 1.659(2) . ?
S1 C14 1.704(3) . ?
O1 C2 1.360(3) . ?
O1 C6 1.382(3) . ?
O2 C7 1.206(3) . ?
O3 C7 1.342(3) . ?
O3 C8 1.452(3) . ?
N1 C12 1.313(3) . ?
N2 C2 1.336(3) . ?
N2 H2A 0.84(3) . ?
N2 H2B 0.89(3) . ?
N3 C11 1.154(4) . ?
C2 C3 1.358(4) . ?
C3 C11 1.412(4) . ?
C3 C4 1.521(4) . ?
C4 C5 1.511(4) . ?
C4 C12 1.524(3) . ?
C4 H4A 1.0000 . ?
C5 C6 1.337(3) . ?
C5 C7 1.479(4) . ?
C6 C10 1.487(4) . ?
C8 C9 1.507(4) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C12 C13 1.423(4) . ?
C13 C14 1.368(4) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 S1 C14 94.03(12) . . ?
C2 O1 C6 120.8(2) . . ?
C7 O3 C8 115.6(2) . . ?
C12 N1 S1 111.02(19) . . ?
C2 N2 H2A 122(2) . . ?
C2 N2 H2B 117(2) . . ?
H2A N2 H2B 121(3) . . ?
N2 C2 C3 128.2(3) . . ?
N2 C2 O1 110.0(2) . . ?
C3 C2 O1 121.8(2) . . ?
C2 C3 C11 118.0(2) . . ?
C2 C3 C4 122.1(3) . . ?
C11 C3 C4 119.7(2) . . ?
C5 C4 C3 110.1(2) . . ?
C5 C4 C12 112.2(2) . . ?
C3 C4 C12 110.7(2) . . ?
C5 C4 H4A 107.9 . . ?
C3 C4 H4A 107.9 . . ?
C12 C4 H4A 107.9 . . ?
C6 C5 C7 124.1(3) . . ?
C6 C5 C4 123.1(2) . . ?
C7 C5 C4 112.8(2) . . ?
C5 C6 O1 121.6(3) . . ?
C5 C6 C10 130.8(2) . . ?
O1 C6 C10 107.6(2) . . ?
O2 C7 O3 123.5(3) . . ?
O2 C7 C5 122.6(3) . . ?
O3 C7 C5 113.9(2) . . ?
O3 C8 C9 106.2(2) . . ?
O3 C8 H8A 110.5 . . ?
C9 C8 H8A 110.5 . . ?
O3 C8 H8B 110.5 . . ?
C9 C8 H8B 110.5 . . ?
H8A C8 H8B 108.7 . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C8 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C6 C10 H10A 109.5 . . ?
C6 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C6 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
N3 C11 C3 179.3(3) . . ?
N1 C12 C13 114.7(2) . . ?
N1 C12 C4 121.0(2) . . ?
C13 C12 C4 124.3(2) . . ?
C14 C13 C12 110.9(2) . . ?
C14 C13 Cl1 124.1(2) . . ?
C12 C13 Cl1 125.0(2) . . ?
C13 C14 Cl2 126.0(2) . . ?
C13 C14 S1 109.4(2) . . ?
Cl2 C14 S1 124.54(16) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C14 S1 N1 C12 -0.5(2) . . . . ?
C6 O1 C2 N2 177.2(2) . . . . ?
C6 O1 C2 C3 -1.5(4) . . . . ?
N2 C2 C3 C11 1.6(4) . . . . ?
O1 C2 C3 C11 -180.0(2) . . . . ?
N2 C2 C3 C4 178.1(3) . . . . ?
O1 C2 C3 C4 -3.5(4) . . . . ?
C2 C3 C4 C5 6.7(4) . . . . ?
C11 C3 C4 C5 -176.8(2) . . . . ?
C2 C3 C4 C12 -117.9(3) . . . . ?
C11 C3 C4 C12 58.6(3) . . . . ?
C3 C4 C5 C6 -6.0(4) . . . . ?
C12 C4 C5 C6 117.8(3) . . . . ?
C3 C4 C5 C7 173.4(2) . . . . ?
C12 C4 C5 C7 -62.8(3) . . . . ?
C7 C5 C6 O1 -177.5(2) . . . . ?
C4 C5 C6 O1 1.9(4) . . . . ?
C7 C5 C6 C10 2.6(5) . . . . ?
C4 C5 C6 C10 -178.1(3) . . . . ?
C2 O1 C6 C5 2.4(4) . . . . ?
C2 O1 C6 C10 -177.7(2) . . . . ?
C8 O3 C7 O2 1.4(4) . . . . ?
C8 O3 C7 C5 -178.8(2) . . . . ?
C6 C5 C7 O2 179.0(3) . . . . ?
C4 C5 C7 O2 -0.4(4) . . . . ?
C6 C5 C7 O3 -0.8(4) . . . . ?
C4 C5 C7 O3 179.8(2) . . . . ?
C7 O3 C8 C9 177.5(2) . . . . ?
S1 N1 C12 C13 0.5(3) . . . . ?
S1 N1 C12 C4 -177.8(2) . . . . ?
C5 C4 C12 N1 -55.3(3) . . . . ?
C3 C4 C12 N1 68.1(3) . . . . ?
C5 C4 C12 C13 126.5(3) . . . . ?
C3 C4 C12 C13 -110.1(3) . . . . ?
N1 C12 C13 C14 -0.3(4) . . . . ?
C4 C12 C13 C14 178.0(3) . . . . ?
N1 C12 C13 Cl1 179.3(2) . . . . ?
C4 C12 C13 Cl1 -2.4(4) . . . . ?
C12 C13 C14 Cl2 178.0(2) . . . . ?
Cl1 C13 C14 Cl2 -1.6(4) . . . . ?
C12 C13 C14 S1 0.0(3) . . . . ?
Cl1 C13 C14 S1 -179.65(17) . . . . ?
N1 S1 C14 C13 0.3(2) . . . . ?
N1 S1 C14 Cl2 -177.75(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
N2 H2A N3 0.84(3) 2.22(3) 3.056(4) 169(3) 2_677 yes
N2 H2B N1 0.89(3) 2.19(3) 3.069(3) 170(3) 2_667 yes
C4 H4A Cl1 1.00 2.74 3.269(3) 113.6 . yes
C10 H10B N3 0.98 2.57 3.532(4) 166.5 1_545 yes

_refine_diff_density_max         0.583
_refine_diff_density_min         -0.644
_refine_diff_density_rms         0.107



# start Validation Reply Form
_vrf_PLAT910_I625                
;
PROBLEM: Missing # of FCF Reflection(s) Below Theta(Min). 13 Note
RESPONSE: Closed by beamstop.
;
# end Validation Reply Form
