# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2020

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
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data_shelxl
_database_code_depnum_ccdc_archive 'CCDC 1975827'
loop_
_audit_author_name
_audit_author_address
'Fanfei Meng'
;Nankai University
China
;
_audit_update_record             
;
2020-01-07 deposited with the CCDC.	2020-04-07 downloaded from the CCDC.
;
_audit_creation_date             2019-12-27
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C17 H19 Cl N6 O5 S'
_chemical_formula_sum            'C17 H16 Cl N6 O5 S'
_chemical_formula_weight         451.87
_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 0.0033 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'
Cl Cl 0.1484 0.1585 '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'

_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                   7.8939(16)
_cell_length_b                   8.9985(18)
_cell_length_c                   14.466(3)
_cell_angle_alpha                85.32(3)
_cell_angle_beta                 81.63(3)
_cell_angle_gamma                72.73(3)
_cell_volume                     970.0(4)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    3013
_cell_measurement_temperature    113(2)
_cell_measurement_theta_max      27.8386
_cell_measurement_theta_min      1.4240
_shelx_estimated_absorpt_T_max   0.959
_shelx_estimated_absorpt_T_min   0.933
_exptl_absorpt_coefficient_mu    0.350
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_correction_T_min  0.8885
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   crystalclear
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.547
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             466
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.12
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0315
_diffrn_reflns_av_unetI/netI     0.0346
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            9370
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.026
_diffrn_reflns_theta_max         25.026
_diffrn_reflns_theta_min         2.372
_diffrn_ambient_temperature      113.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Rigaku Saturn 70 CCD'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  confocal
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2857
_reflns_number_total             3424
_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       crystalclear
_computing_data_collection       crystalclear
_computing_data_reduction        crystalclear
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         1.674
_refine_diff_density_min         -0.588
_refine_diff_density_rms         0.081
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     274
_refine_ls_number_reflns         3424
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0676
_refine_ls_R_factor_gt           0.0570
_refine_ls_restrained_S_all      1.060
_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)+(0.0863P)²+1.5493P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1506
_refine_ls_wR_factor_ref         0.1597
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Rigid bond restraints
 N5, N6, C15
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.002
3.a Riding coordinates:
 N2(H2)
3.b Ternary CH refined with riding coordinates:
 C3(H3A)
3.c Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C2(H2A,H2B)
3.d Aromatic/amide H refined with riding coordinates:
 N3(H3), C7(H7), C8(H8), C11(H11)
3.e Idealised Me refined as rotating group:
 C5(H5A,H5B,H5C), C16(H16A,H16B,H16C), C17(H17A,H17B,H17C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S -0.19144(11) 0.19752(9) 0.39516(5) 0.0214(2) Uani 1 1 d . . . . .
Cl1 Cl -0.54157(11) 0.07242(10) 0.38275(6) 0.0282(3) Uani 1 1 d . . . . .
O1 O 0.4658(3) -0.4478(3) 0.26174(16) 0.0243(5) Uani 1 1 d . . . . .
O2 O -0.3327(3) 0.2632(3) 0.46713(16) 0.0298(6) Uani 1 1 d . . . . .
O3 O -0.0144(3) 0.2051(3) 0.40020(18) 0.0293(6) Uani 1 1 d . . . . .
O4 O -0.0233(3) 0.1511(3) 0.19816(17) 0.0304(6) Uani 1 1 d . . . . .
O5 O 0.1353(4) 0.2045(3) -0.1323(2) 0.0408(7) Uani 1 1 d . . . . .
N1 N 0.1913(3) -0.3692(3) 0.34490(18) 0.0189(6) Uani 1 1 d . . . . .
N2 N -0.2607(4) 0.2893(3) 0.29801(19) 0.0227(6) Uani 1 1 d . . . . .
H2 H -0.370232 0.286729 0.294737 0.027 Uiso 1 1 d R . . . .
N3 N -0.2324(4) 0.3666(3) 0.14328(19) 0.0249(6) Uani 1 1 d . . . . .
H3 H -0.333017 0.436364 0.163097 0.030 Uiso 1 1 calc R . . . .
N4 N -0.2621(5) 0.5127(4) 0.0067(2) 0.0334(7) Uani 1 1 d . . . . .
N5 N -0.0733(4) 0.4361(4) -0.1304(2) 0.0373(8) Uani 1 1 d . U . . .
N6 N -0.0372(4) 0.2682(4) 0.0091(2) 0.0330(7) Uani 1 1 d . U . . .
C1 C 0.3732(5) -0.2145(4) 0.1124(2) 0.0287(8) Uani 1 1 d . . . . .
H1A H 0.469091 -0.310877 0.094788 0.034 Uiso 1 1 calc R . . . .
H1B H 0.308915 -0.157807 0.060280 0.034 Uiso 1 1 calc R . . . .
C2 C 0.4013(5) -0.1212(4) 0.1851(3) 0.0338(9) Uani 1 1 d . . . . .
H2A H 0.354495 -0.006420 0.178407 0.041 Uiso 1 1 calc R . . . .
H2B H 0.514701 -0.159519 0.212922 0.041 Uiso 1 1 calc R . . . .
C3 C 0.2672(4) -0.2130(4) 0.2080(2) 0.0222(7) Uani 1 1 d . . . . .
H3A H 0.138022 -0.151621 0.213253 0.027 Uiso 1 1 calc R . . . .
C4 C 0.3146(4) -0.3509(4) 0.2725(2) 0.0181(7) Uani 1 1 d . . . . .
C5 C 0.2334(5) -0.5106(4) 0.4060(2) 0.0260(8) Uani 1 1 d . . . . .
H5A H 0.229348 -0.599679 0.372560 0.039 Uiso 1 1 calc GR . . . .
H5B H 0.145560 -0.496816 0.462262 0.039 Uiso 1 1 calc GR . . . .
H5C H 0.353347 -0.529515 0.423812 0.039 Uiso 1 1 calc GR . . . .
C6 C 0.0157(4) -0.2625(4) 0.3600(2) 0.0182(7) Uani 1 1 d . . . . .
C7 C -0.1330(4) -0.3153(4) 0.3606(2) 0.0204(7) Uani 1 1 d . . . . .
H7 H -0.117904 -0.422612 0.353483 0.025 Uiso 1 1 calc R . . . .
C8 C -0.3035(4) -0.2113(4) 0.3717(2) 0.0222(7) Uani 1 1 d . . . . .
H8 H -0.405107 -0.248071 0.373775 0.027 Uiso 1 1 calc R . . . .
C9 C -0.3261(4) -0.0536(4) 0.3797(2) 0.0205(7) Uani 1 1 d . . . . .
C10 C -0.1771(4) -0.0006(4) 0.3818(2) 0.0193(7) Uani 1 1 d . . . . .
C11 C -0.0066(4) -0.1061(4) 0.3743(2) 0.0190(7) Uani 1 1 d . . . . .
H11 H 0.094311 -0.071538 0.378988 0.023 Uiso 1 1 calc R . . . .
C12 C -0.1575(4) 0.2585(4) 0.2104(2) 0.0216(7) Uani 1 1 d . . . . .
C13 C -0.1714(5) 0.3804(4) 0.0494(2) 0.0284(8) Uani 1 1 d . . . . .
C14 C -0.2082(5) 0.5347(5) -0.0833(3) 0.0359(9) Uani 1 1 d . . . . .
C15 C 0.0047(5) 0.3075(4) -0.0849(3) 0.0298(7) Uani 1 1 d . U . . .
C16 C -0.3096(5) 0.6835(4) -0.1311(3) 0.0321(8) Uani 1 1 d . . . . .
H16A H -0.435163 0.713013 -0.103214 0.048 Uiso 1 1 calc GR . . . .
H16B H -0.302467 0.667271 -0.197889 0.048 Uiso 1 1 calc GR . . . .
H16C H -0.256918 0.766818 -0.123213 0.048 Uiso 1 1 calc GR . . . .
C17 C 0.2136(5) 0.0605(4) -0.0870(3) 0.0324(8) Uani 1 1 d . . . . .
H17A H 0.274298 0.078020 -0.036195 0.049 Uiso 1 1 calc GR . . . .
H17B H 0.300542 -0.008044 -0.132025 0.049 Uiso 1 1 calc GR . . . .
H17C H 0.120267 0.011649 -0.061236 0.049 Uiso 1 1 calc GR . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 O2 1.431(3) . ?
S1 O3 1.431(3) . ?
S1 N2 1.650(3) . ?
S1 C10 1.777(3) . ?
Cl1 C9 1.738(3) . ?
O1 C4 1.249(4) . ?
O4 C12 1.206(4) . ?
O5 C15 1.313(5) . ?
O5 C17 1.412(5) . ?
N1 C4 1.357(4) . ?
N1 C5 1.470(4) . ?
N1 C6 1.431(4) . ?
N2 H2 0.8799 . ?
N2 C12 1.403(4) . ?
N3 H3 0.8800 . ?
N3 C12 1.382(4) . ?
N3 C13 1.381(4) . ?
N4 C13 1.347(5) . ?
N4 C14 1.327(5) . ?
N5 C14 1.309(5) . ?
N5 C15 1.312(5) . ?
N6 C13 1.328(5) . ?
N6 C15 1.394(5) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C1 C2 1.479(5) . ?
C1 C3 1.508(5) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C2 C3 1.512(5) . ?
C3 H3A 1.0000 . ?
C3 C4 1.479(4) . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C5 H5C 0.9800 . ?
C6 C7 1.389(5) . ?
C6 C11 1.395(5) . ?
C7 H7 0.9500 . ?
C7 C8 1.389(5) . ?
C8 H8 0.9500 . ?
C8 C9 1.389(5) . ?
C9 C10 1.399(5) . ?
C10 C11 1.393(5) . ?
C11 H11 0.9500 . ?
C14 C16 1.512(5) . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 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
O2 S1 O3 119.53(15) . . ?
O2 S1 N2 104.41(14) . . ?
O2 S1 C10 110.34(15) . . ?
O3 S1 N2 109.11(15) . . ?
O3 S1 C10 107.49(15) . . ?
N2 S1 C10 105.05(15) . . ?
C15 O5 C17 118.4(3) . . ?
C4 N1 C5 119.0(3) . . ?
C4 N1 C6 122.6(3) . . ?
C6 N1 C5 118.2(3) . . ?
S1 N2 H2 109.8 . . ?
C12 N2 S1 122.2(2) . . ?
C12 N2 H2 109.7 . . ?
C12 N3 H3 115.5 . . ?
C13 N3 H3 115.5 . . ?
C13 N3 C12 129.1(3) . . ?
C14 N4 C13 116.7(4) . . ?
C14 N5 C15 116.4(4) . . ?
C13 N6 C15 110.7(3) . . ?
H1A C1 H1B 114.8 . . ?
C2 C1 H1A 117.7 . . ?
C2 C1 H1B 117.7 . . ?
C2 C1 C3 60.8(2) . . ?
C3 C1 H1A 117.7 . . ?
C3 C1 H1B 117.7 . . ?
C1 C2 H2A 117.7 . . ?
C1 C2 H2B 117.7 . . ?
C1 C2 C3 60.5(2) . . ?
H2A C2 H2B 114.8 . . ?
C3 C2 H2A 117.7 . . ?
C3 C2 H2B 117.7 . . ?
C1 C3 C2 58.6(2) . . ?
C1 C3 H3A 116.5 . . ?
C2 C3 H3A 116.5 . . ?
C4 C3 C1 119.4(3) . . ?
C4 C3 C2 117.0(3) . . ?
C4 C3 H3A 116.5 . . ?
O1 C4 N1 120.4(3) . . ?
O1 C4 C3 120.9(3) . . ?
N1 C4 C3 118.7(3) . . ?
N1 C5 H5A 109.5 . . ?
N1 C5 H5B 109.5 . . ?
N1 C5 H5C 109.5 . . ?
H5A C5 H5B 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
C7 C6 N1 119.8(3) . . ?
C7 C6 C11 120.0(3) . . ?
C11 C6 N1 120.3(3) . . ?
C6 C7 H7 120.0 . . ?
C8 C7 C6 120.1(3) . . ?
C8 C7 H7 120.0 . . ?
C7 C8 H8 119.9 . . ?
C7 C8 C9 120.2(3) . . ?
C9 C8 H8 119.9 . . ?
C8 C9 Cl1 117.8(3) . . ?
C8 C9 C10 119.9(3) . . ?
C10 C9 Cl1 122.3(3) . . ?
C9 C10 S1 123.5(2) . . ?
C11 C10 S1 116.7(2) . . ?
C11 C10 C9 119.7(3) . . ?
C6 C11 H11 120.0 . . ?
C10 C11 C6 119.9(3) . . ?
C10 C11 H11 120.0 . . ?
O4 C12 N2 123.0(3) . . ?
O4 C12 N3 126.5(3) . . ?
N3 C12 N2 110.5(3) . . ?
N4 C13 N3 113.6(3) . . ?
N6 C13 N3 120.3(3) . . ?
N6 C13 N4 126.0(3) . . ?
N4 C14 C16 116.7(4) . . ?
N5 C14 N4 123.4(4) . . ?
N5 C14 C16 119.9(4) . . ?
O5 C15 N6 116.3(3) . . ?
N5 C15 O5 117.1(4) . . ?
N5 C15 N6 126.7(4) . . ?
C14 C16 H16A 109.5 . . ?
C14 C16 H16B 109.5 . . ?
C14 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
O5 C17 H17A 109.5 . . ?
O5 C17 H17B 109.5 . . ?
O5 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 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
_geom_hbond_publ_flag
C3 H3A O4 1.00 2.65 3.401(4) 132.2 . yes
C5 H5A Cl1 0.98 2.97 3.664(4) 128.5 1_645 yes

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
S1 N2 C12 O4 9.6(5) . . . . ?
S1 N2 C12 N3 -170.7(2) . . . . ?
S1 C10 C11 C6 -177.5(2) . . . . ?
Cl1 C9 C10 S1 4.2(4) . . . . ?
Cl1 C9 C10 C11 -176.7(2) . . . . ?
O2 S1 N2 C12 179.4(3) . . . . ?
O2 S1 C10 C9 44.4(3) . . . . ?
O2 S1 C10 C11 -134.8(2) . . . . ?
O3 S1 N2 C12 50.5(3) . . . . ?
O3 S1 C10 C9 176.3(3) . . . . ?
O3 S1 C10 C11 -2.9(3) . . . . ?
N1 C6 C7 C8 -177.6(3) . . . . ?
N1 C6 C11 C10 175.1(3) . . . . ?
N2 S1 C10 C9 -67.6(3) . . . . ?
N2 S1 C10 C11 113.2(3) . . . . ?
C1 C2 C3 C4 109.5(3) . . . . ?
C1 C3 C4 O1 20.4(5) . . . . ?
C1 C3 C4 N1 -160.6(3) . . . . ?
C2 C1 C3 C4 -105.4(3) . . . . ?
C2 C3 C4 O1 -47.0(4) . . . . ?
C2 C3 C4 N1 132.0(3) . . . . ?
C4 N1 C6 C7 120.5(3) . . . . ?
C4 N1 C6 C11 -59.7(4) . . . . ?
C5 N1 C4 O1 -4.6(4) . . . . ?
C5 N1 C4 C3 176.4(3) . . . . ?
C5 N1 C6 C7 -54.3(4) . . . . ?
C5 N1 C6 C11 125.4(3) . . . . ?
C6 N1 C4 O1 -179.4(3) . . . . ?
C6 N1 C4 C3 1.6(4) . . . . ?
C6 C7 C8 C9 1.7(5) . . . . ?
C7 C6 C11 C10 -5.1(5) . . . . ?
C7 C8 C9 Cl1 174.3(2) . . . . ?
C7 C8 C9 C10 -3.5(5) . . . . ?
C8 C9 C10 S1 -178.2(2) . . . . ?
C8 C9 C10 C11 1.0(5) . . . . ?
C9 C10 C11 C6 3.3(5) . . . . ?
C10 S1 N2 C12 -64.4(3) . . . . ?
C11 C6 C7 C8 2.7(5) . . . . ?
C12 N3 C13 N4 -170.6(3) . . . . ?
C12 N3 C13 N6 10.5(5) . . . . ?
C13 N3 C12 O4 -2.0(6) . . . . ?
C13 N3 C12 N2 178.3(3) . . . . ?
C13 N4 C14 N5 -0.6(5) . . . . ?
C13 N4 C14 C16 -179.7(3) . . . . ?
C13 N6 C15 O5 -179.6(3) . . . . ?
C13 N6 C15 N5 0.2(5) . . . . ?
C14 N4 C13 N3 178.8(3) . . . . ?
C14 N4 C13 N6 -2.3(5) . . . . ?
C14 N5 C15 O5 177.1(3) . . . . ?
C14 N5 C15 N6 -2.7(5) . . . . ?
C15 N5 C14 N4 2.8(5) . . . . ?
C15 N5 C14 C16 -178.0(3) . . . . ?
C15 N6 C13 N3 -178.8(3) . . . . ?
C15 N6 C13 N4 2.4(5) . . . . ?
C17 O5 C15 N5 -175.8(3) . . . . ?
C17 O5 C15 N6 4.1(5) . . . . ?

_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_r20191117b
_database_code_depnum_ccdc_archive 'CCDC 1975828'
_audit_update_record             
;
2020-01-07 deposited with the CCDC.	2020-04-07 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            'C16 H19 Cl N6 O4 S'
_chemical_formula_weight         426.88

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

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

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

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

_cell_length_a                   10.2847(5)
_cell_length_b                   17.1412(7)
_cell_length_c                   11.2410(5)
_cell_angle_alpha                90
_cell_angle_beta                 102.533(5)
_cell_angle_gamma                90
_cell_volume                     1934.48(15)
_cell_formula_units_Z            4
_cell_measurement_temperature    113(2)
_cell_measurement_reflns_used    12430
_cell_measurement_theta_min      2.0200
_cell_measurement_theta_max      32.4900

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.466
_exptl_crystal_F_000             888
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.120
_exptl_absorpt_coefficient_mu    0.342
_shelx_estimated_absorpt_T_min   0.935
_shelx_estimated_absorpt_T_max   0.960
_exptl_absorpt_correction_type   MULTI-SCAN
_exptl_absorpt_correction_T_min  0.51980
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_process_details   crystalclear
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      113(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'rigaku saturn'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0
_diffrn_reflns_number            20402
_diffrn_reflns_av_unetI/netI     0.0279
_diffrn_reflns_av_R_equivalents  0.0422
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.028
_diffrn_reflns_theta_max         26.372
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             3952
_reflns_number_gt                3383
_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       crystalclear
_computing_cell_refinement       crystalclear
_computing_data_reduction        crystalclear
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0639P)²+1.6125P] 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         3952
_refine_ls_number_parameters     262
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0589
_refine_ls_R_factor_gt           0.0496
_refine_ls_wR_factor_ref         0.1345
_refine_ls_wR_factor_gt          0.1274
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_restrained_S_all      1.039
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.32538(6) 0.13676(4) 0.78094(6) 0.03676(18) Uani 1 1 d . . . . .
Cl1 Cl 0.14602(7) 0.23134(4) 0.54591(6) 0.0473(2) Uani 1 1 d . . . . .
O1 O 0.38127(18) 0.07691(11) 0.86424(17) 0.0474(5) Uani 1 1 d . . . . .
O2 O 0.3159(2) 0.21458(11) 0.82384(18) 0.0485(5) Uani 1 1 d . . . . .
O3 O 0.40507(17) 0.02159(10) 0.60890(18) 0.0420(4) Uani 1 1 d . . . . .
O4 O 0.78328(19) 0.24640(11) 0.32951(17) 0.0465(5) Uani 1 1 d . . . . .
N1 N -0.0481(2) -0.06335(13) 0.7262(2) 0.0450(5) Uani 1 1 d . . . . .
N2 N 0.4166(2) 0.14726(12) 0.6784(2) 0.0371(5) Uani 1 1 d D . . . .
H2 H 0.442(3) 0.1946(9) 0.659(3) 0.045 Uiso 1 1 d D U . . .
N3 N 0.5279(2) 0.10882(11) 0.5291(2) 0.0364(5) Uani 1 1 d D . . . .
H3 H 0.548(3) 0.0696(12) 0.484(2) 0.044 Uiso 1 1 d D U . . .
N4 N 0.6545(2) 0.17936(12) 0.42584(19) 0.0353(5) Uani 1 1 d . . . . .
N5 N 0.55366(19) 0.24279(11) 0.57039(18) 0.0325(4) Uani 1 1 d . . . . .
N6 N 0.6870(2) 0.31573(12) 0.46407(19) 0.0371(5) Uani 1 1 d . . . . .
C1 C -0.2594(4) -0.0122(2) 0.8400(4) 0.0771(11) Uani 1 1 d . . . . .
H1A H -0.171345 0.005808 0.871470 0.093 Uiso 1 1 calc R U . . .
H1B H -0.330275 0.004776 0.875637 0.093 Uiso 1 1 calc R U . . .
C2 C -0.2831(3) -0.06042(19) 0.7480(3) 0.0539(7) Uani 1 1 d . . . . .
H2A H -0.372745 -0.076858 0.719697 0.065 Uiso 1 1 calc R U . . .
C3 C -0.1823(3) -0.09216(17) 0.6828(3) 0.0461(6) Uani 1 1 d . . . . .
H3A H -0.181022 -0.149707 0.690335 0.055 Uiso 1 1 calc R U . . .
H3B H -0.211047 -0.079391 0.595115 0.055 Uiso 1 1 calc R U . . .
C4 C 0.0363(3) -0.1054(2) 0.8263(4) 0.0697(10) Uani 1 1 d . . . . .
H4A H 0.124231 -0.113706 0.808095 0.105 Uiso 1 1 calc R U . . .
H4B H -0.004280 -0.155894 0.836948 0.105 Uiso 1 1 calc R U . . .
H4C H 0.045886 -0.074803 0.901411 0.105 Uiso 1 1 calc R U . . .
C5 C -0.0056(2) 0.00598(15) 0.6863(2) 0.0361(5) Uani 1 1 d . . . . .
C6 C -0.0815(2) 0.04888(15) 0.5891(2) 0.0385(6) Uani 1 1 d . . . . .
H6 H -0.168102 0.031130 0.551231 0.046 Uiso 1 1 calc R U . . .
C7 C -0.0330(3) 0.11615(16) 0.5478(2) 0.0388(6) Uani 1 1 d . . . . .
H7 H -0.086016 0.142995 0.480492 0.047 Uiso 1 1 calc R U . . .
C8 C 0.0912(3) 0.14573(14) 0.6017(2) 0.0357(5) Uani 1 1 d . . . . .
C9 C 0.1681(2) 0.10448(14) 0.6995(2) 0.0330(5) Uani 1 1 d . . . . .
C10 C 0.1212(2) 0.03575(14) 0.7401(2) 0.0354(5) Uani 1 1 d . . . . .
H10 H 0.175724 0.008165 0.805677 0.042 Uiso 1 1 calc R U . . .
C11 C 0.4467(2) 0.08813(14) 0.6070(2) 0.0344(5) Uani 1 1 d . . . . .
C12 C 0.5800(2) 0.18036(13) 0.5086(2) 0.0317(5) Uani 1 1 d . . . . .
C13 C 0.7057(2) 0.24872(15) 0.4090(2) 0.0357(5) Uani 1 1 d . . . . .
C14 C 0.6088(2) 0.30944(14) 0.5436(2) 0.0336(5) Uani 1 1 d . . . . .
C15 C 0.5803(3) 0.38077(14) 0.6094(2) 0.0423(6) Uani 1 1 d . . . . .
H15A H 0.627341 0.377619 0.695007 0.063 Uiso 1 1 calc R U . . .
H15B H 0.484263 0.384628 0.604760 0.063 Uiso 1 1 calc R U . . .
H15C H 0.610570 0.426970 0.571758 0.063 Uiso 1 1 calc R U . . .
C16 C 0.8445(3) 0.31804(18) 0.3039(3) 0.0586(8) Uani 1 1 d . . . . .
H16A H 0.775223 0.356244 0.270675 0.088 Uiso 1 1 calc R U . . .
H16B H 0.899450 0.308259 0.244313 0.088 Uiso 1 1 calc R U . . .
H16C H 0.900565 0.338472 0.379236 0.088 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 O1 1.4235(19) . ?
S1 O2 1.4288(19) . ?
S1 N2 1.647(2) . ?
S1 C9 1.766(2) . ?
Cl1 C8 1.737(3) . ?
O3 C11 1.220(3) . ?
O4 C13 1.321(3) . ?
O4 C16 1.437(3) . ?
N1 C5 1.375(3) . ?
N1 C3 1.447(3) . ?
N1 C4 1.454(4) . ?
N2 C11 1.369(3) . ?
N2 H2 0.893(10) . ?
N3 C12 1.377(3) . ?
N3 C11 1.382(3) . ?
N3 H3 0.893(10) . ?
N4 C12 1.328(3) . ?
N4 C13 1.330(3) . ?
N5 C12 1.335(3) . ?
N5 C14 1.338(3) . ?
N6 C14 1.330(3) . ?
N6 C13 1.339(3) . ?
C1 C2 1.305(5) . ?
C1 H1A 0.9500 . ?
C1 H1B 0.9500 . ?
C2 C3 1.496(4) . ?
C2 H2A 0.9500 . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 H4A 0.9800 . ?
C4 H4B 0.9800 . ?
C4 H4C 0.9800 . ?
C5 C6 1.405(4) . ?
C5 C10 1.408(3) . ?
C6 C7 1.377(4) . ?
C6 H6 0.9500 . ?
C7 C8 1.385(4) . ?
C7 H7 0.9500 . ?
C8 C9 1.399(3) . ?
C9 C10 1.388(3) . ?
C10 H10 0.9500 . ?
C14 C15 1.491(3) . ?
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
O1 S1 O2 119.88(12) . . ?
O1 S1 N2 109.22(12) . . ?
O2 S1 N2 103.02(11) . . ?
O1 S1 C9 108.00(11) . . ?
O2 S1 C9 110.24(12) . . ?
N2 S1 C9 105.54(11) . . ?
C13 O4 C16 117.7(2) . . ?
C5 N1 C3 122.2(2) . . ?
C5 N1 C4 120.1(2) . . ?
C3 N1 C4 117.2(2) . . ?
C11 N2 S1 124.39(17) . . ?
C11 N2 H2 114.4(19) . . ?
S1 N2 H2 120.8(19) . . ?
C12 N3 C11 130.1(2) . . ?
C12 N3 H3 115.4(19) . . ?
C11 N3 H3 114.4(19) . . ?
C12 N4 C13 113.2(2) . . ?
C12 N5 C14 115.1(2) . . ?
C14 N6 C13 114.2(2) . . ?
C2 C1 H1A 120.0 . . ?
C2 C1 H1B 120.0 . . ?
H1A C1 H1B 120.0 . . ?
C1 C2 C3 126.0(3) . . ?
C1 C2 H2A 117.0 . . ?
C3 C2 H2A 117.0 . . ?
N1 C3 C2 115.0(2) . . ?
N1 C3 H3A 108.5 . . ?
C2 C3 H3A 108.5 . . ?
N1 C3 H3B 108.5 . . ?
C2 C3 H3B 108.5 . . ?
H3A C3 H3B 107.5 . . ?
N1 C4 H4A 109.5 . . ?
N1 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
N1 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
N1 C5 C6 122.9(2) . . ?
N1 C5 C10 120.2(2) . . ?
C6 C5 C10 116.8(2) . . ?
C7 C6 C5 121.3(2) . . ?
C7 C6 H6 119.3 . . ?
C5 C6 H6 119.3 . . ?
C6 C7 C8 121.8(2) . . ?
C6 C7 H7 119.1 . . ?
C8 C7 H7 119.1 . . ?
C7 C8 C9 118.0(2) . . ?
C7 C8 Cl1 119.46(19) . . ?
C9 C8 Cl1 122.6(2) . . ?
C10 C9 C8 120.6(2) . . ?
C10 C9 S1 116.14(18) . . ?
C8 C9 S1 123.18(19) . . ?
C9 C10 C5 121.5(2) . . ?
C9 C10 H10 119.3 . . ?
C5 C10 H10 119.3 . . ?
O3 C11 N2 123.9(2) . . ?
O3 C11 N3 120.9(2) . . ?
N2 C11 N3 115.2(2) . . ?
N4 C12 N5 126.0(2) . . ?
N4 C12 N3 114.2(2) . . ?
N5 C12 N3 119.8(2) . . ?
O4 C13 N4 112.6(2) . . ?
O4 C13 N6 120.5(2) . . ?
N4 C13 N6 126.9(2) . . ?
N6 C14 N5 124.6(2) . . ?
N6 C14 C15 118.7(2) . . ?
N5 C14 C15 116.7(2) . . ?
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 . . ?
O4 C16 H16A 109.5 . . ?
O4 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
O4 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 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
O1 S1 N2 C11 55.2(2) . . . . ?
O2 S1 N2 C11 -176.3(2) . . . . ?
C9 S1 N2 C11 -60.7(2) . . . . ?
C5 N1 C3 C2 -84.3(3) . . . . ?
C4 N1 C3 C2 87.8(4) . . . . ?
C1 C2 C3 N1 -2.1(5) . . . . ?
C3 N1 C5 C6 -9.0(4) . . . . ?
C4 N1 C5 C6 179.2(3) . . . . ?
C3 N1 C5 C10 173.4(2) . . . . ?
C4 N1 C5 C10 1.5(4) . . . . ?
N1 C5 C6 C7 -176.8(2) . . . . ?
C10 C5 C6 C7 0.9(3) . . . . ?
C5 C6 C7 C8 -1.6(4) . . . . ?
C6 C7 C8 C9 0.9(3) . . . . ?
C6 C7 C8 Cl1 -179.44(18) . . . . ?
C7 C8 C9 C10 0.5(3) . . . . ?
Cl1 C8 C9 C10 -179.16(18) . . . . ?
C7 C8 C9 S1 -177.52(18) . . . . ?
Cl1 C8 C9 S1 2.8(3) . . . . ?
O1 S1 C9 C10 8.4(2) . . . . ?
O2 S1 C9 C10 -124.33(19) . . . . ?
N2 S1 C9 C10 125.08(18) . . . . ?
O1 S1 C9 C8 -173.55(19) . . . . ?
O2 S1 C9 C8 53.8(2) . . . . ?
N2 S1 C9 C8 -56.8(2) . . . . ?
C8 C9 C10 C5 -1.2(4) . . . . ?
S1 C9 C10 C5 176.98(18) . . . . ?
N1 C5 C10 C9 178.2(2) . . . . ?
C6 C5 C10 C9 0.4(3) . . . . ?
S1 N2 C11 O3 2.6(4) . . . . ?
S1 N2 C11 N3 -178.19(18) . . . . ?
C12 N3 C11 O3 176.7(2) . . . . ?
C12 N3 C11 N2 -2.6(4) . . . . ?
C13 N4 C12 N5 0.9(3) . . . . ?
C13 N4 C12 N3 -178.9(2) . . . . ?
C14 N5 C12 N4 0.3(3) . . . . ?
C14 N5 C12 N3 -179.9(2) . . . . ?
C11 N3 C12 N4 -179.6(2) . . . . ?
C11 N3 C12 N5 0.5(4) . . . . ?
C16 O4 C13 N4 -179.9(2) . . . . ?
C16 O4 C13 N6 -0.7(4) . . . . ?
C12 N4 C13 O4 177.9(2) . . . . ?
C12 N4 C13 N6 -1.3(3) . . . . ?
C14 N6 C13 O4 -178.7(2) . . . . ?
C14 N6 C13 N4 0.4(4) . . . . ?
C13 N6 C14 N5 1.1(3) . . . . ?
C13 N6 C14 C15 -179.5(2) . . . . ?
C12 N5 C14 N6 -1.4(3) . . . . ?
C12 N5 C14 C15 179.2(2) . . . . ?

_refine_diff_density_max         0.621
_refine_diff_density_min         -0.548
_refine_diff_density_rms         0.058

