# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2016

####################################################################### 
# 
# 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_shelxl
_database_code_depnum_ccdc_archive 'CCDC 1426721'
_audit_update_record             
;
2015-09-23 deposited with the CCDC.
2016-02-22 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C15 H18 Cl N5 O4 S'
_chemical_formula_weight         399.85

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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/n

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

_cell_length_a                   9.4336(19)
_cell_length_b                   11.524(2)
_cell_length_c                   16.608(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 100.88(3)
_cell_angle_gamma                90.00
_cell_volume                     1773.1(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    113(2)
_cell_measurement_reflns_used    5506
_cell_measurement_theta_min      2.1639
_cell_measurement_theta_max      27.9143

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.12
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.498
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             832
_exptl_absorpt_coefficient_mu    0.366
_exptl_absorpt_correction_type   MULTI-SCAN
_exptl_absorpt_correction_T_min  0.9304
_exptl_absorpt_correction_T_max  0.9574
_exptl_absorpt_process_details   crystalclear

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      113(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'rotating anode'
_diffrn_radiation_monochromator  confocal
_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            17832
_diffrn_reflns_av_R_equivalents  0.0549
_diffrn_reflns_av_sigmaI/netI    0.0506
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.16
_diffrn_reflns_theta_max         27.92
_reflns_number_total             4240
_reflns_number_gt                3495
_reflns_threshold_expression     >2sigma(I)

_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          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0567P)²+0.3384P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0155(15)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         4240
_refine_ls_number_parameters     248
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0540
_refine_ls_R_factor_gt           0.0439
_refine_ls_wR_factor_ref         0.1156
_refine_ls_wR_factor_gt          0.1090
_refine_ls_goodness_of_fit_ref   1.070
_refine_ls_restrained_S_all      1.070
_refine_ls_shift/su_max          0.002
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.42706(5) 0.82026(4) 0.23246(3) 0.01864(14) Uani 1 1 d . . .
Cl1 Cl 0.38797(5) 1.10153(4) 0.26992(3) 0.02516(15) Uani 1 1 d . . .
O1 O 0.48840(14) 0.71696(11) 0.20663(9) 0.0264(3) Uani 1 1 d . . .
O2 O 0.32635(14) 0.81189(12) 0.28642(8) 0.0244(3) Uani 1 1 d . . .
O3 O 0.52443(13) 0.91457(12) 0.08473(8) 0.0231(3) Uani 1 1 d . . .
O4 O 0.00332(15) 1.31321(12) -0.02371(9) 0.0294(3) Uani 1 1 d . . .
N1 N 0.33642(16) 0.88827(14) 0.15149(9) 0.0186(3) Uani 1 1 d D . .
N2 N 0.31988(16) 1.01957(14) 0.04308(9) 0.0182(3) Uani 1 1 d D . .
N3 N 0.15817(16) 1.16784(14) 0.00770(9) 0.0204(3) Uani 1 1 d . . .
N4 N -0.05885(16) 1.17280(13) 0.06210(9) 0.0191(3) Uani 1 1 d . . .
N5 N 0.11068(15) 1.02116(13) 0.10018(9) 0.0175(3) Uani 1 1 d . . .
C1 C 0.57050(18) 0.91313(15) 0.27632(11) 0.0169(4) Uani 1 1 d . . .
C2 C 0.55189(19) 1.02956(16) 0.29639(11) 0.0186(4) Uani 1 1 d . . .
C3 C 0.6692(2) 1.09216(16) 0.33779(11) 0.0205(4) Uani 1 1 d . . .
H3 H 0.6577 1.1713 0.3512 0.025 Uiso 1 1 calc R . .
C4 C 0.80323(19) 1.03908(16) 0.35964(11) 0.0196(4) Uani 1 1 d . . .
H4 H 0.8822 1.0827 0.3886 0.024 Uiso 1 1 calc R . .
C5 C 0.82472(19) 0.92396(16) 0.34027(11) 0.0192(4) Uani 1 1 d . . .
C6 C 0.70602(19) 0.86243(16) 0.29743(11) 0.0195(4) Uani 1 1 d . . .
H6 H 0.7185 0.7841 0.2824 0.023 Uiso 1 1 calc R . .
C7 C 0.96837(19) 0.86180(17) 0.36431(13) 0.0253(4) Uani 1 1 d . . .
H7 H 0.9859 0.8169 0.3156 0.030 Uiso 1 1 calc R . .
C8 C 0.9609(2) 0.7751(2) 0.43354(17) 0.0429(6) Uani 1 1 d . . .
H8A H 0.9441 0.8172 0.4822 0.064 Uiso 1 1 calc R . .
H8B H 1.0521 0.7324 0.4469 0.064 Uiso 1 1 calc R . .
H8C H 0.8816 0.7205 0.4158 0.064 Uiso 1 1 calc R . .
C9 C 1.0965(2) 0.94274(18) 0.39075(13) 0.0280(5) Uani 1 1 d . . .
H9A H 1.0986 1.0009 0.3479 0.042 Uiso 1 1 calc R . .
H9B H 1.1861 0.8977 0.3994 0.042 Uiso 1 1 calc R . .
H9C H 1.0870 0.9817 0.4419 0.042 Uiso 1 1 calc R . .
C10 C 0.40199(19) 0.93802(16) 0.09299(11) 0.0181(4) Uani 1 1 d . . .
C11 C 0.19078(18) 1.07168(16) 0.05129(10) 0.0173(4) Uani 1 1 d . . .
C12 C 0.03324(19) 1.21472(17) 0.01765(11) 0.0200(4) Uani 1 1 d . . .
C13 C -0.01408(19) 1.07524(16) 0.10263(10) 0.0178(4) Uani 1 1 d . . .
C14 C -0.1083(2) 1.02191(17) 0.15417(11) 0.0213(4) Uani 1 1 d . . .
H14A H -0.0954 0.9375 0.1549 0.032 Uiso 1 1 calc R . .
H14B H -0.2093 1.0407 0.1315 0.032 Uiso 1 1 calc R . .
H14C H -0.0827 1.0522 0.2102 0.032 Uiso 1 1 calc R . .
C15 C -0.1295(2) 1.3710(2) -0.01750(14) 0.0344(5) Uani 1 1 d . . .
H15A H -0.2114 1.3220 -0.0416 0.052 Uiso 1 1 calc R . .
H15B H -0.1352 1.4451 -0.0470 0.052 Uiso 1 1 calc R . .
H15C H -0.1323 1.3854 0.0403 0.052 Uiso 1 1 calc R . .
H1 H 0.2481(15) 0.912(2) 0.1564(16) 0.050(8) Uiso 1 1 d D . .
H2 H 0.366(2) 1.0508(19) 0.0061(11) 0.033(6) Uiso 1 1 d 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
S1 O1 1.4247(14) . ?
S1 O2 1.4271(15) . ?
S1 N1 1.6492(16) . ?
S1 C1 1.7706(18) . ?
Cl1 C2 1.7367(18) . ?
O3 C10 1.219(2) . ?
O4 C12 1.329(2) . ?
O4 C15 1.440(2) . ?
N1 C10 1.372(2) . ?
N1 H1 0.895(10) . ?
N2 C11 1.387(2) . ?
N2 C10 1.389(2) . ?
N2 H2 0.890(10) . ?
N3 C11 1.328(2) . ?
N3 C12 1.335(2) . ?
N4 C12 1.332(2) . ?
N4 C13 1.337(2) . ?
N5 C13 1.339(2) . ?
N5 C11 1.342(2) . ?
C1 C6 1.389(2) . ?
C1 C2 1.402(3) . ?
C2 C3 1.389(3) . ?
C3 C4 1.390(2) . ?
C3 H3 0.9500 . ?
C4 C5 1.389(3) . ?
C4 H4 0.9500 . ?
C5 C6 1.401(2) . ?
C5 C7 1.518(2) . ?
C6 H6 0.9500 . ?
C7 C9 1.524(3) . ?
C7 C8 1.535(3) . ?
C7 H7 1.0000 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C13 C14 1.479(3) . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 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 119.27(9) . . ?
O1 S1 N1 109.22(8) . . ?
O2 S1 N1 103.89(8) . . ?
O1 S1 C1 107.86(8) . . ?
O2 S1 C1 109.27(8) . . ?
N1 S1 C1 106.65(8) . . ?
C12 O4 C15 117.44(16) . . ?
C10 N1 S1 122.85(13) . . ?
C10 N1 H1 119.2(17) . . ?
S1 N1 H1 114.9(17) . . ?
C11 N2 C10 129.45(16) . . ?
C11 N2 H2 116.2(15) . . ?
C10 N2 H2 113.4(15) . . ?
C11 N3 C12 112.93(16) . . ?
C12 N4 C13 114.00(16) . . ?
C13 N5 C11 114.51(16) . . ?
C6 C1 C2 119.55(16) . . ?
C6 C1 S1 116.43(14) . . ?
C2 C1 S1 123.79(13) . . ?
C3 C2 C1 119.41(16) . . ?
C3 C2 Cl1 117.72(14) . . ?
C1 C2 Cl1 122.86(14) . . ?
C2 C3 C4 120.07(17) . . ?
C2 C3 H3 120.0 . . ?
C4 C3 H3 120.0 . . ?
C5 C4 C3 121.68(17) . . ?
C5 C4 H4 119.2 . . ?
C3 C4 H4 119.2 . . ?
C4 C5 C6 117.61(16) . . ?
C4 C5 C7 123.49(16) . . ?
C6 C5 C7 118.89(17) . . ?
C1 C6 C5 121.65(17) . . ?
C1 C6 H6 119.2 . . ?
C5 C6 H6 119.2 . . ?
C5 C7 C9 114.00(16) . . ?
C5 C7 C8 109.82(17) . . ?
C9 C7 C8 109.19(17) . . ?
C5 C7 H7 107.9 . . ?
C9 C7 H7 107.9 . . ?
C8 C7 H7 107.9 . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C7 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C7 C9 H9A 109.5 . . ?
C7 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C7 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
O3 C10 N1 123.40(17) . . ?
O3 C10 N2 121.10(17) . . ?
N1 C10 N2 115.49(16) . . ?
N3 C11 N5 126.37(17) . . ?
N3 C11 N2 115.16(16) . . ?
N5 C11 N2 118.46(16) . . ?
O4 C12 N4 119.93(17) . . ?
O4 C12 N3 112.83(17) . . ?
N4 C12 N3 127.23(18) . . ?
N4 C13 N5 124.89(17) . . ?
N4 C13 C14 118.25(16) . . ?
N5 C13 C14 116.86(16) . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
O4 C15 H15A 109.5 . . ?
O4 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
O4 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 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 N1 C10 -67.34(16) . . . . ?
O2 S1 N1 C10 164.37(14) . . . . ?
C1 S1 N1 C10 48.97(17) . . . . ?
O1 S1 C1 C6 -16.14(17) . . . . ?
O2 S1 C1 C6 114.92(14) . . . . ?
N1 S1 C1 C6 -133.36(14) . . . . ?
O1 S1 C1 C2 169.29(15) . . . . ?
O2 S1 C1 C2 -59.65(17) . . . . ?
N1 S1 C1 C2 52.07(18) . . . . ?
C6 C1 C2 C3 -0.6(3) . . . . ?
S1 C1 C2 C3 173.82(14) . . . . ?
C6 C1 C2 Cl1 178.07(14) . . . . ?
S1 C1 C2 Cl1 -7.5(2) . . . . ?
C1 C2 C3 C4 -0.6(3) . . . . ?
Cl1 C2 C3 C4 -179.30(14) . . . . ?
C2 C3 C4 C5 0.8(3) . . . . ?
C3 C4 C5 C6 0.1(3) . . . . ?
C3 C4 C5 C7 -178.76(17) . . . . ?
C2 C1 C6 C5 1.6(3) . . . . ?
S1 C1 C6 C5 -173.24(14) . . . . ?
C4 C5 C6 C1 -1.3(3) . . . . ?
C7 C5 C6 C1 177.61(17) . . . . ?
C4 C5 C7 C9 -15.7(3) . . . . ?
C6 C5 C7 C9 165.39(17) . . . . ?
C4 C5 C7 C8 107.2(2) . . . . ?
C6 C5 C7 C8 -71.7(2) . . . . ?
S1 N1 C10 O3 17.6(3) . . . . ?
S1 N1 C10 N2 -161.71(13) . . . . ?
C11 N2 C10 O3 -168.02(17) . . . . ?
C11 N2 C10 N1 11.3(3) . . . . ?
C12 N3 C11 N5 1.1(3) . . . . ?
C12 N3 C11 N2 -179.97(15) . . . . ?
C13 N5 C11 N3 0.8(3) . . . . ?
C13 N5 C11 N2 -178.08(15) . . . . ?
C10 N2 C11 N3 162.37(17) . . . . ?
C10 N2 C11 N5 -18.6(3) . . . . ?
C15 O4 C12 N4 0.5(3) . . . . ?
C15 O4 C12 N3 179.81(16) . . . . ?
C13 N4 C12 O4 -178.08(16) . . . . ?
C13 N4 C12 N3 2.8(3) . . . . ?
C11 N3 C12 O4 177.72(15) . . . . ?
C11 N3 C12 N4 -3.1(3) . . . . ?
C12 N4 C13 N5 -0.4(2) . . . . ?
C12 N4 C13 C14 179.71(15) . . . . ?
C11 N5 C13 N4 -1.2(2) . . . . ?
C11 N5 C13 C14 178.70(14) . . . . ?

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        27.92
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.527
_refine_diff_density_min         -0.525
_refine_diff_density_rms         0.076
