# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2018

####################################################################### 
# 
# 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_2016-DECEMBER-14-JYPTHI-SK-27-2
_database_code_depnum_ccdc_archive 'CCDC 1544389'
_audit_update_record             
;
2018-07-25 deposited with the CCDC.
2018-11-19 downloaded from the CCDC.
;
_audit_creation_date             2018-07-25
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_chemical_formula_moiety         'C22 H15 Cl2 N3 O3 S2, C1.5 H3 O0.5'
_chemical_formula_sum            'C23.5 H18 Cl2 N3 O3.5 S2'
_chemical_formula_weight         533.46
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
C 0.00347 0.00161 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.215599998832
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
Cl 0.14873 0.16029 11.46040 7.19640 6.25560 1.64550 0.01040 1.16620 18.51940
47.77840 -9.55739974976
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.0030380000826
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
O 0.01158 0.00611 3.04850 2.28680 1.54630 0.86700 13.27710 5.70110 0.32390
32.90890 0.250800013542
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
N 0.00653 0.00323 12.21260 3.13220 2.01250 1.16630 0.00570 9.89330 28.99750
0.58260 -11.5290002823
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
S 0.12424 0.12443 6.90530 5.20340 1.43790 1.58630 1.46790 22.21510 0.25360
56.17200 0.866900026798
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x,y,-z+1/2
3 -x,-y,-z
4 x,-y,z-1/2
5 x+1/2,y+1/2,z
6 -x+1/2,y+1/2,-z+1/2
7 -x+1/2,-y+1/2,-z
8 x+1/2,-y+1/2,z-1/2

_symmetry_Int_Tables_number      15
_cell_length_a                   16.2075(8)
_cell_length_b                   11.8305(5)
_cell_length_c                   26.3964(12)
_cell_angle_alpha                90
_cell_angle_beta                 110.081(6)
_cell_angle_gamma                90
_cell_volume                     4753.7(4)
_cell_formula_units_Z            8
_exptl_absorpt_coefficient_mu    0.484
_exptl_crystal_density_diffrn    1.4907
_exptl_crystal_F_000             2197.2074
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.18
_diffrn_reflns_av_R_equivalents  0.0475
_diffrn_reflns_av_unetI/netI     0.0410
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       37
_diffrn_reflns_limit_l_min       -37
_diffrn_reflns_number            32621
_diffrn_reflns_theta_full        26.3721
_diffrn_reflns_theta_max         26.37
_diffrn_reflns_theta_min         2.16
_diffrn_measured_fraction_theta_full 0.9959
_diffrn_measured_fraction_theta_max 0.9959
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              18
_reflns_limit_h_min              -20
_reflns_limit_k_max              14
_reflns_limit_k_min              0
_reflns_limit_l_max              32
_reflns_limit_l_min              0
_reflns_number_gt                3922
_reflns_number_total             4863
_reflns_threshold_expression     I>=2u(I)
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine (Bourhis et al., 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.4444
_refine_diff_density_min         -0.4246
_refine_diff_density_rms         0.0637
_refine_ls_d_res_high            0.8000
_refine_ls_d_res_low             9.4206
_refine_ls_goodness_of_fit_ref   1.0471
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    34
_refine_ls_number_parameters     309
_refine_ls_number_reflns         4863
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0653
_refine_ls_R_factor_gt           0.0512
_refine_ls_restrained_S_all      1.0471
_refine_ls_shift/su_max          0.0000
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0485P)²+6.1708P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1174
_refine_ls_wR_factor_ref         0.1273
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Riding coordinates:
 N3(H3)
2.b Aromatic/amide H refined with riding coordinates:
 N1(H1), C22(H1A), C21(H2), C19(H4), C18(H5), C16(H7), C9(H12), C8(H13),
 C12(H15), C11(H16), C2(H18), C3(H19), C5(H21), C6(H22)
2.c Idealised Me refined as rotating group:
 C23(H23A,H23B,H23C)
;
_atom_sites_solution_primary     direct
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_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
Cl1 Cl 0.50720(8) 0.55733(10) 0.17483(6) 0.1115(4) Uani 1.000000 1 . . .
Cl2 Cl -0.17984(5) 0.79845(10) 0.45764(4) 0.0909(3) Uani 1.000000 1 . . .
S1 S 0.24846(4) 1.02251(6) 0.19687(2) 0.04745(19) Uani 1.000000 1 . . .
S2 S 0.25086(4) 0.93901(7) 0.45155(2) 0.0535(2) Uani 1.000000 1 . . .
O1 O 0.39396(12) 0.88736(19) 0.59957(7) 0.0631(5) Uani 1.000000 1 . . .
O2 O 0.18162(11) 0.93830(17) 0.17878(7) 0.0562(5) Uani 1.000000 1 . . .
O3 O 0.22968(14) 1.13849(17) 0.18181(7) 0.0663(6) Uani 1.000000 1 . . .
N1 N 0.40849(14) 0.9489(2) 0.52135(8) 0.0512(6) Uani 1.000000 1 . . .
H1 H 0.46391(14) 0.9619(2) 0.53544(8) 0.0615(7) Uiso 1.000000 1 R . .
N2 N 0.40417(14) 0.99767(19) 0.43589(8) 0.0482(5) Uani 1.000000 1 . . .
N3 N 0.32741(16) 0.99036(19) 0.17506(9) 0.0538(6) Uani 1.000000 1 . . .
H3 H 0.36761(16) 1.04102(19) 0.18644(9) 0.0646(7) Uiso 1.000000 1 R . .
C22 C 0.0694(2) 0.8215(3) 0.55262(11) 0.0586(7) Uani 1.000000 1 . . .
H1A H 0.1015(2) 0.8099(3) 0.58891(11) 0.0703(9) Uiso 1.000000 1 R . .
C21 C -0.0196(2) 0.8019(3) 0.53431(12) 0.0655(8) Uani 1.000000 1 . . .
H2 H -0.0470(2) 0.7753(3) 0.55770(12) 0.0787(10) Uiso 1.000000 1 R . .
C20 C -0.06763(19) 0.8221(2) 0.48109(12) 0.0565(7) Uani 1.000000 1 . . .
C19 C -0.02798(19) 0.8610(3) 0.44620(11) 0.0618(8) Uani 1.000000 1 . . .
H4 H -0.06111(19) 0.8752(3) 0.41030(11) 0.0741(9) Uiso 1.000000 1 R . .
C18 C 0.06140(19) 0.8789(3) 0.46486(11) 0.0580(7) Uani 1.000000 1 . . .
H5 H 0.08819(19) 0.9055(3) 0.44117(11) 0.0696(9) Uiso 1.000000 1 R . .
C17 C 0.11272(17) 0.8581(2) 0.51845(10) 0.0464(6) Uani 1.000000 1 . . .
C16 C 0.20732(17) 0.8730(2) 0.54112(10) 0.0487(6) Uani 1.000000 1 . . .
H7 H 0.23109(17) 0.8585(2) 0.57793(10) 0.0584(7) Uiso 1.000000 1 R . .
C15 C 0.26651(17) 0.9036(2) 0.51880(9) 0.0470(6) Uani 1.000000 1 . . .
C14 C 0.36127(18) 0.9109(2) 0.55205(10) 0.0497(6) Uani 1.000000 1 . . .
C13 C 0.36446(17) 0.9654(2) 0.46728(9) 0.0460(6) Uani 1.000000 1 . . .
C10 C 0.36112(15) 1.0036(2) 0.37933(9) 0.0416(5) Uani 1.000000 1 . . .
C9 C 0.31229(18) 0.9143(2) 0.34962(10) 0.0483(6) Uani 1.000000 1 . . .
H12 H 0.30301(18) 0.8501(2) 0.36728(10) 0.0580(7) Uiso 1.000000 1 R . .
C8 C 0.27744(17) 0.9203(2) 0.29407(10) 0.0472(6) Uani 1.000000 1 . . .
H13 H 0.24505(17) 0.8601(2) 0.27440(10) 0.0566(7) Uiso 1.000000 1 R . .
C7 C 0.29070(15) 1.0155(2) 0.26778(9) 0.0409(5) Uani 1.000000 1 . . .
C12 C 0.33915(17) 1.1050(2) 0.29702(10) 0.0476(6) Uani 1.000000 1 . . .
H15 H 0.34766(17) 1.1694(2) 0.27922(10) 0.0571(7) Uiso 1.000000 1 R . .
C11 C 0.37484(17) 1.0988(2) 0.35254(10) 0.0479(6) Uani 1.000000 1 . . .
H16 H 0.40815(17) 1.1585(2) 0.37203(10) 0.0574(7) Uiso 1.000000 1 R . .
C1 C 0.36909(16) 0.8840(2) 0.17785(9) 0.0450(6) Uani 1.000000 1 . . .
C2 C 0.32698(18) 0.7828(2) 0.17742(12) 0.0592(7) Uani 1.000000 1 . . .
H18 H 0.26948(18) 0.7827(2) 0.17721(12) 0.0711(9) Uiso 1.000000 1 R . .
C3 C 0.3691(2) 0.6819(3) 0.17731(14) 0.0695(9) Uani 1.000000 1 . . .
H19 H 0.3407(2) 0.6137(3) 0.17741(14) 0.0834(10) Uiso 1.000000 1 R . .
C4 C 0.4539(2) 0.6830(3) 0.17705(13) 0.0650(8) Uani 1.000000 1 . . .
C5 C 0.49655(19) 0.7823(3) 0.17791(13) 0.0669(8) Uani 1.000000 1 . . .
H21 H 0.55406(19) 0.7820(3) 0.17813(13) 0.0803(10) Uiso 1.000000 1 R . .
C6 C 0.45509(18) 0.8825(3) 0.17844(11) 0.0588(7) Uani 1.000000 1 . . .
H22 H 0.48462(18) 0.9503(3) 0.17920(11) 0.0706(9) Uiso 1.000000 1 R . .
O4 O 0.5 1.1394(6) 0.25 0.208(3) Uani 1.000000 2 S T P
C23 C 0.4400(6) 1.2967(7) 0.2033(4) 0.230(4) Uani 1.000000 1 . . .
H23A H 0.4711(13) 1.321(6) 0.1800(17) 0.345(6) Uiso 1.000000 1 GR . .
H23B H 0.394(3) 1.245(2) 0.184(2) 0.345(6) Uiso 1.000000 1 GR . .
H23C H 0.415(4) 1.361(4) 0.2144(4) 0.345(6) Uiso 1.000000 1 GR . .
C24 C 0.5 1.2415(8) 0.25 0.169(5) Uani 1.000000 2 S T P


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 C4 1.731(3) . ?
Cl2 C20 1.731(3) . ?
S1 O2 1.428(2) . ?
S1 O3 1.432(2) . ?
S1 N3 1.618(2) . ?
S1 C7 1.760(2) . ?
S2 C15 1.755(2) . ?
S2 C13 1.771(3) . ?
O1 C14 1.215(3) . ?
N1 C14 1.367(3) . ?
N1 C13 1.373(3) . ?
N2 C13 1.270(3) . ?
N2 C10 1.416(3) . ?
N3 C1 1.418(3) . ?
C22 C21 1.375(4) . ?
C22 C17 1.389(4) . ?
C21 C20 1.373(4) . ?
C20 C19 1.371(4) . ?
C19 C18 1.377(4) . ?
C18 C17 1.395(4) . ?
C17 C16 1.453(4) . ?
C16 C15 1.337(4) . ?
C15 C14 1.487(4) . ?
C10 C9 1.389(3) . ?
C10 C11 1.388(3) . ?
C9 C8 1.380(3) . ?
C8 C7 1.378(3) . ?
C7 C12 1.385(4) . ?
C12 C11 1.380(3) . ?
C1 C2 1.376(4) . ?
C1 C6 1.389(4) . ?
C2 C3 1.376(4) . ?
C3 C4 1.375(4) . ?
C4 C5 1.360(4) . ?
C5 C6 1.365(4) . ?
O4 C24 1.207(9) . ?
C23 C24 1.439(8) . ?

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
O3 S1 O2 120.75(12) . . ?
N3 S1 O2 108.59(12) . . ?
N3 S1 O3 104.18(12) . . ?
C7 S1 O2 107.22(12) . . ?
C7 S1 O3 107.97(12) . . ?
C7 S1 N3 107.50(11) . . ?
C13 S2 C15 91.56(12) . . ?
C13 N1 C14 117.8(2) . . ?
C10 N2 C13 121.7(2) . . ?
C1 N3 S1 127.64(18) . . ?
C17 C22 C21 121.9(3) . . ?
C20 C21 C22 119.2(3) . . ?
C21 C20 Cl2 119.6(2) . . ?
C19 C20 Cl2 119.4(2) . . ?
C19 C20 C21 121.0(3) . . ?
C18 C19 C20 119.3(3) . . ?
C17 C18 C19 121.6(3) . . ?
C18 C17 C22 117.1(2) . . ?
C16 C17 C22 117.9(2) . . ?
C16 C17 C18 125.0(2) . . ?
C15 C16 C17 131.8(2) . . ?
C16 C15 S2 129.3(2) . . ?
C14 C15 S2 110.15(18) . . ?
C14 C15 C16 120.5(2) . . ?
N1 C14 O1 123.6(2) . . ?
C15 C14 O1 126.3(2) . . ?
C15 C14 N1 110.1(2) . . ?
N1 C13 S2 110.25(18) . . ?
N2 C13 S2 128.25(19) . . ?
N2 C13 N1 121.5(2) . . ?
C9 C10 N2 122.4(2) . . ?
C11 C10 N2 118.0(2) . . ?
C11 C10 C9 119.3(2) . . ?
C8 C9 C10 120.4(2) . . ?
C7 C8 C9 119.9(2) . . ?
C8 C7 S1 120.21(19) . . ?
C12 C7 S1 119.71(19) . . ?
C12 C7 C8 120.1(2) . . ?
C11 C12 C7 120.1(2) . . ?
C12 C11 C10 120.1(2) . . ?
C2 C1 N3 123.0(2) . . ?
C6 C1 N3 118.0(2) . . ?
C6 C1 C2 118.9(3) . . ?
C3 C2 C1 120.6(3) . . ?
C4 C3 C2 119.3(3) . . ?
C3 C4 Cl1 120.2(3) . . ?
C5 C4 Cl1 119.0(2) . . ?
C5 C4 C3 120.7(3) . . ?
C6 C5 C4 120.1(3) . . ?
C5 C6 C1 120.4(3) . . ?
C23 C24 O4 117.0(5) . . ?
C23 C24 O4 117.0(5) 2_655 . ?
C23 C24 C23 125.9(10) 2_655 . ?

_olex2_submission_special_instructions 'No special instructions were received'
