# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2022

####################################################################### 
# 
# 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_20210120zxl0sb0z_0m
_database_code_depnum_ccdc_archive 'CCDC 2168952'
loop_
_audit_author_name
_audit_author_address
'xiaolei zhao'
;Changzhou Institute of Technology
China
;
_audit_update_record             
;
2022-04-27 deposited with the CCDC.	2022-08-22 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C18 H18 Cl3 N5 O4 S'
_chemical_formula_sum            'C18 H18 Cl3 N5 O4 S'
_chemical_formula_weight         506.78

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                   8.0328(6)
_cell_length_b                   10.5896(10)
_cell_length_c                   14.2584(10)
_cell_angle_alpha                79.176(3)
_cell_angle_beta                 77.012(3)
_cell_angle_gamma                75.686(3)
_cell_volume                     1133.87(16)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    3013
_cell_measurement_theta_min      2.654
_cell_measurement_theta_max      27.294

_exptl_crystal_description       needle
_exptl_crystal_colour            red
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.484
_exptl_crystal_F_000             520
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.100
_exptl_crystal_size_mid          0.090
_exptl_crystal_size_min          0.080
_exptl_absorpt_coefficient_mu    0.531
_shelx_estimated_absorpt_T_min   0.949
_shelx_estimated_absorpt_T_max   0.959
_exptl_absorpt_correction_type   'not measured'
_exptl_absorpt_correction_T_min  0.948
_exptl_absorpt_correction_T_max  0.958
_exptl_absorpt_process_details   'SADABS, Bruker(2000)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'BRUKER Smart Apex CCD area detector'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            8449
_diffrn_reflns_av_unetI/netI     0.0632
_diffrn_reflns_av_R_equivalents  0.0448
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.319
_diffrn_reflns_theta_max         24.998
_diffrn_reflns_theta_full        24.998
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measured_fraction_theta_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_point_group_measured_fraction_full 0.992
_reflns_number_total             3961
_reflns_number_gt                2995
_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       'SMART (BRUKER 2000)'
_computing_cell_refinement       SMART
_computing_data_reduction        'SAINT (BRUKER 2000)'
_computing_structure_solution    'SHELXTL (BRUKER 2000)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_publication_material  'SHELXL-2014/7 (Sheldrick, 2014)'
_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)+(0.0767P)²+1.8520P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3961
_refine_ls_number_parameters     288
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0904
_refine_ls_R_factor_gt           0.0688
_refine_ls_wR_factor_ref         0.1867
_refine_ls_wR_factor_gt          0.1726
_refine_ls_goodness_of_fit_ref   1.067
_refine_ls_restrained_S_all      1.067
_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
C1 C 0.1948(5) 0.4007(4) 0.7108(3) 0.0328(9) Uani 1 1 d . . . . .
C2 C 0.2566(5) 0.5189(4) 0.7121(3) 0.0317(9) Uani 1 1 d . . . . .
C3 C 0.3021(5) 0.6054(4) 0.6235(3) 0.0340(9) Uani 1 1 d . . . . .
C4 C 0.2825(5) 0.5719(4) 0.5394(3) 0.0334(9) Uani 1 1 d . . . . .
C5 C 0.2160(5) 0.4571(4) 0.5351(3) 0.0355(9) Uani 1 1 d . . . . .
C6 C 0.3733(7) 0.7210(5) 0.6270(3) 0.0467(11) Uani 1 1 d . . . . .
H6A H 0.3762 0.7768 0.5655 0.070 Uiso 1 1 calc R U . . .
H6B H 0.4896 0.6914 0.6405 0.070 Uiso 1 1 calc R U . . .
H6C H 0.3000 0.7694 0.6772 0.070 Uiso 1 1 calc R U . . .
C7 C 0.3338(6) 0.6475(4) 0.4470(3) 0.0378(10) Uani 1 1 d . . . . .
C8 C 0.1047(6) 0.2610(4) 0.6211(3) 0.0432(11) Uani 1 1 d . . . . .
H8A H 0.0485 0.2758 0.5653 0.052 Uiso 1 1 calc R U . . .
H8B H 0.0173 0.2482 0.6792 0.052 Uiso 1 1 calc R U . . .
C9 C 0.2473(8) 0.1391(5) 0.6159(4) 0.0657(15) Uani 1 1 d . . . . .
H9A H 0.3279 0.1479 0.5554 0.099 Uiso 1 1 calc R U . . .
H9B H 0.1972 0.0643 0.6203 0.099 Uiso 1 1 calc R U . . .
H9C H 0.3080 0.1271 0.6688 0.099 Uiso 1 1 calc R U . . .
C10 C 0.2541(5) 0.5214(4) 0.9596(3) 0.0310(9) Uani 1 1 d . . . . .
C11 C 0.2196(5) 0.4572(4) 1.0528(3) 0.0307(9) Uani 1 1 d . . . . .
C12 C 0.2495(5) 0.5292(4) 1.1209(3) 0.0313(9) Uani 1 1 d . . . . .
C13 C 0.3040(5) 0.6411(4) 1.0798(3) 0.0324(9) Uani 1 1 d . . . . .
C14 C 0.1635(5) 0.3362(4) 1.0757(3) 0.0364(10) Uani 1 1 d . . . . .
C15 C 0.3437(5) 0.7400(4) 1.1293(3) 0.0363(9) Uani 1 1 d . . . . .
H15 H 0.3994 0.6915 1.1837 0.044 Uiso 1 1 calc R U . . .
C16 C 0.5305(7) 0.8884(5) 1.1017(4) 0.0560(13) Uani 1 1 d . . . . .
H16A H 0.4458 0.9701 1.1037 0.084 Uiso 1 1 calc R U . . .
H16B H 0.6386 0.9037 1.0614 0.084 Uiso 1 1 calc R U . . .
H16C H 0.5494 0.8518 1.1663 0.084 Uiso 1 1 calc R U . . .
C17 C 0.0866(7) 0.9026(5) 1.0995(4) 0.0538(13) Uani 1 1 d . . . . .
H17A H 0.1577 0.9404 1.0429 0.081 Uiso 1 1 calc R U . . .
H17B H 0.0010 0.9715 1.1292 0.081 Uiso 1 1 calc R U . . .
H17C H 0.0286 0.8447 1.0809 0.081 Uiso 1 1 calc R U . . .
C18 C 0.7813(10) 0.9514(7) 0.6981(6) 0.099(2) Uani 1 1 d . . . . .
H18A H 0.7523 1.0464 0.6815 0.119 Uiso 1 1 calc R U . . .
H18B H 0.8305 0.9316 0.7567 0.119 Uiso 1 1 calc R U . . .
Cl1 Cl 0.22507(14) 0.47225(10) 1.24289(7) 0.0398(3) Uani 1 1 d . . . . .
Cl2 Cl 0.5922(3) 0.8920(2) 0.7210(3) 0.1574(13) Uani 1 1 d . . . . .
Cl3 Cl 0.9342(5) 0.8866(5) 0.6064(3) 0.236(2) Uani 1 1 d . . . . .
N1 N 0.1719(4) 0.3775(3) 0.6229(2) 0.0327(8) Uani 1 1 d . . . . .
N2 N 0.3800(5) 0.7064(4) 0.3743(3) 0.0497(10) Uani 1 1 d . . . . .
N3 N 0.2753(4) 0.5536(3) 0.7931(2) 0.0329(8) Uani 1 1 d . . . . .
N4 N 0.2393(5) 0.4798(4) 0.8766(2) 0.0333(8) Uani 1 1 d . . . . .
N5 N 0.1153(6) 0.2394(4) 1.0921(3) 0.0534(10) Uani 1 1 d . . . . .
O1 O 0.1609(4) 0.3229(3) 0.78544(19) 0.0398(7) Uani 1 1 d . . . . .
O2 O 0.2001(4) 0.4299(3) 0.45867(19) 0.0469(8) Uani 1 1 d . . . . .
O3 O 0.4674(4) 0.7985(3) 1.0626(2) 0.0468(8) Uani 1 1 d . . . . .
O4 O 0.1950(4) 0.8298(3) 1.1673(2) 0.0469(8) Uani 1 1 d . . . . .
S1 S 0.32249(14) 0.66404(11) 0.95410(7) 0.0353(3) Uani 1 1 d . . . . .
H4 H 0.209(7) 0.415(5) 0.875(4) 0.053(16) Uiso 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 O1 1.240(5) . ?
C1 N1 1.381(5) . ?
C1 C2 1.461(6) . ?
C2 N3 1.326(5) . ?
C2 C3 1.447(6) . ?
C3 C4 1.363(5) . ?
C3 C6 1.486(6) . ?
C4 C7 1.439(6) . ?
C4 C5 1.460(6) . ?
C5 O2 1.219(5) . ?
C5 N1 1.398(5) . ?
C6 H6A 0.9600 . ?
C6 H6B 0.9600 . ?
C6 H6C 0.9600 . ?
C7 N2 1.140(5) . ?
C8 N1 1.470(5) . ?
C8 C9 1.500(7) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C10 N4 1.376(5) . ?
C10 C11 1.376(5) . ?
C10 S1 1.714(4) . ?
C11 C14 1.418(6) . ?
C11 C12 1.434(5) . ?
C12 C13 1.349(6) . ?
C12 Cl1 1.715(4) . ?
C13 C15 1.496(6) . ?
C13 S1 1.740(4) . ?
C14 N5 1.150(6) . ?
C15 O3 1.390(5) . ?
C15 O4 1.402(5) . ?
C15 H15 0.9800 . ?
C16 O3 1.427(6) . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C17 O4 1.433(5) . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C18 Cl3 1.699(8) . ?
C18 Cl2 1.727(8) . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
N3 N4 1.311(5) . ?
N4 H4 0.78(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
O1 C1 N1 119.8(4) . . ?
O1 C1 C2 122.3(3) . . ?
N1 C1 C2 117.9(3) . . ?
N3 C2 C3 115.9(4) . . ?
N3 C2 C1 122.8(4) . . ?
C3 C2 C1 121.3(3) . . ?
C4 C3 C2 116.7(4) . . ?
C4 C3 C6 123.4(4) . . ?
C2 C3 C6 119.8(3) . . ?
C3 C4 C7 120.9(4) . . ?
C3 C4 C5 123.8(4) . . ?
C7 C4 C5 115.3(3) . . ?
O2 C5 N1 120.6(4) . . ?
O2 C5 C4 122.2(4) . . ?
N1 C5 C4 117.2(3) . . ?
C3 C6 H6A 109.5 . . ?
C3 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
C3 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
N2 C7 C4 177.7(4) . . ?
N1 C8 C9 112.0(4) . . ?
N1 C8 H8A 109.2 . . ?
C9 C8 H8A 109.2 . . ?
N1 C8 H8B 109.2 . . ?
C9 C8 H8B 109.2 . . ?
H8A C8 H8B 107.9 . . ?
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 . . ?
N4 C10 C11 125.9(4) . . ?
N4 C10 S1 121.1(3) . . ?
C11 C10 S1 113.0(3) . . ?
C10 C11 C14 123.5(4) . . ?
C10 C11 C12 110.5(4) . . ?
C14 C11 C12 126.0(4) . . ?
C13 C12 C11 114.1(3) . . ?
C13 C12 Cl1 124.0(3) . . ?
C11 C12 Cl1 121.9(3) . . ?
C12 C13 C15 128.0(3) . . ?
C12 C13 S1 111.3(3) . . ?
C15 C13 S1 120.7(3) . . ?
N5 C14 C11 178.0(4) . . ?
O3 C15 O4 114.0(4) . . ?
O3 C15 C13 106.4(3) . . ?
O4 C15 C13 113.8(3) . . ?
O3 C15 H15 107.5 . . ?
O4 C15 H15 107.5 . . ?
C13 C15 H15 107.5 . . ?
O3 C16 H16A 109.5 . . ?
O3 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
O3 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
O4 C17 H17A 109.5 . . ?
O4 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
O4 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
Cl3 C18 Cl2 113.0(4) . . ?
Cl3 C18 H18A 109.0 . . ?
Cl2 C18 H18A 109.0 . . ?
Cl3 C18 H18B 109.0 . . ?
Cl2 C18 H18B 109.0 . . ?
H18A C18 H18B 107.8 . . ?
C1 N1 C5 122.9(3) . . ?
C1 N1 C8 118.5(3) . . ?
C5 N1 C8 118.6(3) . . ?
N4 N3 C2 119.9(4) . . ?
N3 N4 C10 118.2(4) . . ?
N3 N4 H4 116(4) . . ?
C10 N4 H4 126(4) . . ?
C15 O3 C16 113.3(3) . . ?
C15 O4 C17 115.8(3) . . ?
C10 S1 C13 91.14(19) . . ?

_refine_diff_density_max         1.003
_refine_diff_density_min         -0.919
_refine_diff_density_rms         0.076



