# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2015

####################################################################### 
# 
# 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_2h
_database_code_depnum_ccdc_archive 'CCDC 1413437'
_audit_update_record             
;
2015-07-17 deposited with the CCDC.
2015-09-15 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C9 H8.50 N O2.50 S'
_chemical_formula_weight         202.73

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'

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   'P-1   '

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.6539(17)
_cell_length_b                   8.7824(18)
_cell_length_c                   12.894(3)
_cell_angle_alpha                100.90(3)
_cell_angle_beta                 90.99(3)
_cell_angle_gamma                107.77(3)
_cell_volume                     913.4(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    2702
_cell_measurement_theta_min      2.4794
_cell_measurement_theta_max      27.3679

_exptl_crystal_description       Prism
_exptl_crystal_colour            Colorless
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.16
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.474
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             422
_exptl_absorpt_coefficient_mu    0.325
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.7869
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  Saturn724
_diffrn_measurement_method       dtprofit.ref
_diffrn_detector_area_resol_mean 28.5714
_diffrn_standards_number         4062
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            9503
_diffrn_reflns_av_R_equivalents  0.0461
_diffrn_reflns_av_sigmaI/netI    0.0572
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         1.61
_diffrn_reflns_theta_max         27.47
_reflns_number_total             4062
_reflns_number_gt                3092
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrystalClear (Rigaku/MSC Inc., 2006)'
_computing_cell_refinement       'CrystalClear (Rigaku/MSC Inc., 2006)'
_computing_data_reduction        'CrystalClear (Rigaku/MSC Inc., 2006)'
_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)+(0.1000P)²+0.1557P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4062
_refine_ls_number_parameters     229
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1873
_refine_ls_R_factor_gt           0.1601
_refine_ls_wR_factor_ref         0.3724
_refine_ls_wR_factor_gt          0.3531
_refine_ls_goodness_of_fit_ref   1.831
_refine_ls_restrained_S_all      1.831
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.27689(19) 0.20988(18) 0.36261(13) 0.0752(6) Uani 1 1 d . . .
O1 O 0.1759(6) 0.0581(5) 0.3866(3) 0.0896(14) Uani 1 1 d . . .
O2 O 0.4295(6) 0.3013(6) 0.4248(4) 0.1103(17) Uani 1 1 d . . .
O3 O 0.6705(5) 0.4374(5) 0.0679(4) 0.0832(13) Uani 1 1 d . . .
O4 O 0.4783(7) 0.1568(7) -0.2746(5) 0.1149(17) Uani 1 1 d . . .
O5 O 0.3118(8) 0.0439(8) -0.1662(4) 0.121(2) Uani 1 1 d . . .
N1 N 0.3246(6) 0.1611(6) 0.2389(4) 0.0778(14) Uani 1 1 d . . .
C1 C -0.1311(8) 0.6636(8) 0.3399(5) 0.0904(19) Uani 1 1 d . . .
H1A H -0.1665 0.6561 0.2675 0.136 Uiso 1 1 calc R . .
H1B H -0.0678 0.7743 0.3702 0.136 Uiso 1 1 calc R . .
H1C H -0.2243 0.6308 0.3794 0.136 Uiso 1 1 calc R . .
C2 C -0.0286(7) 0.5532(7) 0.3438(4) 0.0694(15) Uani 1 1 d . . .
C3 C 0.1264(8) 0.6109(7) 0.3988(5) 0.0780(16) Uani 1 1 d . . .
H3 H 0.1664 0.7201 0.4328 0.094 Uiso 1 1 calc R . .
C4 C 0.2230(7) 0.5098(7) 0.4045(5) 0.0757(16) Uani 1 1 d . . .
H4 H 0.3256 0.5516 0.4409 0.091 Uiso 1 1 calc R . .
C5 C 0.1618(6) 0.3429(6) 0.3538(4) 0.0617(13) Uani 1 1 d . . .
C6 C 0.0067(7) 0.2823(7) 0.2983(5) 0.0723(15) Uani 1 1 d . . .
H6 H -0.0341 0.1730 0.2646 0.087 Uiso 1 1 calc R . .
C7 C -0.0847(7) 0.3856(7) 0.2943(5) 0.0765(16) Uani 1 1 d . . .
H7 H -0.1871 0.3436 0.2577 0.092 Uiso 1 1 calc R . .
C8 C 0.2351(8) 0.0247(7) 0.1608(5) 0.0777(17) Uani 1 1 d . . .
H8 H 0.1507 -0.0639 0.1726 0.093 Uiso 1 1 calc R . .
C9 C 0.2943(9) 0.0456(8) 0.0640(6) 0.093(2) Uani 1 1 d . . .
H9 H 0.2595 -0.0256 -0.0011 0.112 Uiso 1 1 calc R . .
C10 C 0.4222(7) 0.2020(8) 0.0852(6) 0.081(2) Uani 1 1 d . . .
C11 C 0.4391(7) 0.2704(8) 0.1903(6) 0.0831(18) Uani 1 1 d . . .
H11 H 0.5124 0.3703 0.2235 0.100 Uiso 1 1 calc R . .
C12 C 0.5281(9) 0.2838(9) 0.0083(7) 0.097(2) Uani 1 1 d . . .
C13 C 0.5467(8) 0.2773(8) -0.0947(4) 0.0743(17) Uani 1 1 d . . .
C14 C 0.6842(10) 0.4032(11) -0.1117(8) 0.118(3) Uani 1 1 d . . .
H14 H 0.7231 0.4180 -0.1770 0.142 Uiso 1 1 calc R . .
C15 C 0.7482(10) 0.4966(10) -0.0188(6) 0.109(3) Uani 1 1 d . . .
C16 C 0.8964(9) 0.6552(9) 0.0165(6) 0.105(2) Uani 1 1 d . . .
H16A H 0.9457 0.6889 -0.0450 0.157 Uiso 1 1 calc R . .
H16B H 0.9748 0.6338 0.0605 0.157 Uiso 1 1 calc R . .
H16C H 0.8597 0.7403 0.0557 0.157 Uiso 1 1 calc R . .
C17 C 0.4271(10) 0.1407(10) -0.1787(7) 0.093(2) Uani 1 1 d . . .
C18 C 0.3823(9) 0.0423(9) -0.3650(5) 0.102(2) Uani 1 1 d . . .
H18A H 0.3834 -0.0657 -0.3618 0.152 Uiso 1 1 calc R . .
H18B H 0.4271 0.0710 -0.4288 0.152 Uiso 1 1 calc R . .
H18C H 0.2723 0.0452 -0.3645 0.152 Uiso 1 1 calc R . .


_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 1.446(4) . ?
S1 O2 1.450(4) . ?
S1 N1 1.665(6) . ?
S1 C5 1.769(5) . ?
O3 C15 1.416(10) . ?
O3 C12 1.577(9) . ?
O4 C17 1.339(10) . ?
O4 C18 1.440(8) . ?
O5 C17 1.132(9) . ?
N1 C11 1.401(7) . ?
N1 C8 1.414(8) . ?
C1 C2 1.507(8) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C2 C3 1.406(8) . ?
C2 C7 1.416(8) . ?
C3 C4 1.403(8) . ?
C3 H3 0.9300 . ?
C4 C5 1.417(7) . ?
C4 H4 0.9300 . ?
C5 C6 1.408(7) . ?
C6 C7 1.381(8) . ?
C6 H6 0.9300 . ?
C7 H7 0.9300 . ?
C8 C9 1.379(9) . ?
C8 H8 0.9300 . ?
C9 C10 1.451(9) . ?
C9 H9 0.9300 . ?
C10 C11 1.359(9) . ?
C10 C12 1.497(9) . ?
C11 H11 0.9300 . ?
C12 C13 1.332(9) . ?
C13 C14 1.409(9) . ?
C13 C17 1.548(9) . ?
C14 C15 1.320(10) . ?
C14 H14 0.9300 . ?
C15 C16 1.562(10) . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?

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 120.5(3) . . ?
O1 S1 N1 105.3(3) . . ?
O2 S1 N1 106.1(3) . . ?
O1 S1 C5 110.8(3) . . ?
O2 S1 C5 109.1(3) . . ?
N1 S1 C5 103.6(2) . . ?
C15 O3 C12 100.9(5) . . ?
C17 O4 C18 117.5(6) . . ?
C11 N1 C8 109.1(6) . . ?
C11 N1 S1 123.2(5) . . ?
C8 N1 S1 126.3(4) . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C3 C2 C7 116.6(5) . . ?
C3 C2 C1 121.5(6) . . ?
C7 C2 C1 121.9(5) . . ?
C4 C3 C2 122.4(5) . . ?
C4 C3 H3 118.8 . . ?
C2 C3 H3 118.8 . . ?
C3 C4 C5 118.9(5) . . ?
C3 C4 H4 120.5 . . ?
C5 C4 H4 120.5 . . ?
C6 C5 C4 119.7(5) . . ?
C6 C5 S1 120.0(4) . . ?
C4 C5 S1 120.3(4) . . ?
C7 C6 C5 119.7(5) . . ?
C7 C6 H6 120.1 . . ?
C5 C6 H6 120.1 . . ?
C6 C7 C2 122.6(5) . . ?
C6 C7 H7 118.7 . . ?
C2 C7 H7 118.7 . . ?
C9 C8 N1 108.4(6) . . ?
C9 C8 H8 125.8 . . ?
N1 C8 H8 125.8 . . ?
C8 C9 C10 105.6(6) . . ?
C8 C9 H9 127.2 . . ?
C10 C9 H9 127.2 . . ?
C11 C10 C9 110.3(6) . . ?
C11 C10 C12 121.7(7) . . ?
C9 C10 C12 128.0(7) . . ?
C10 C11 N1 106.7(6) . . ?
C10 C11 H11 126.6 . . ?
N1 C11 H11 126.6 . . ?
C13 C12 C10 143.2(8) . . ?
C13 C12 O3 105.8(6) . . ?
C10 C12 O3 111.0(6) . . ?
C12 C13 C14 111.5(7) . . ?
C12 C13 C17 120.6(7) . . ?
C14 C13 C17 127.9(7) . . ?
C15 C14 C13 108.1(8) . . ?
C15 C14 H14 125.9 . . ?
C13 C14 H14 125.9 . . ?
C14 C15 O3 113.5(8) . . ?
C14 C15 C16 133.6(10) . . ?
O3 C15 C16 112.9(6) . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
O5 C17 O4 123.2(8) . . ?
O5 C17 C13 128.4(9) . . ?
O4 C17 C13 108.4(7) . . ?
O4 C18 H18A 109.5 . . ?
O4 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
O4 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 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 C11 -171.2(4) . . . . ?
O2 S1 N1 C11 -42.5(5) . . . . ?
C5 S1 N1 C11 72.3(5) . . . . ?
O1 S1 N1 C8 24.2(6) . . . . ?
O2 S1 N1 C8 153.0(5) . . . . ?
C5 S1 N1 C8 -92.3(5) . . . . ?
C7 C2 C3 C4 0.6(9) . . . . ?
C1 C2 C3 C4 179.3(5) . . . . ?
C2 C3 C4 C5 -0.7(9) . . . . ?
C3 C4 C5 C6 0.5(9) . . . . ?
C3 C4 C5 S1 -177.9(4) . . . . ?
O1 S1 C5 C6 -44.1(5) . . . . ?
O2 S1 C5 C6 -179.1(4) . . . . ?
N1 S1 C5 C6 68.3(5) . . . . ?
O1 S1 C5 C4 134.3(5) . . . . ?
O2 S1 C5 C4 -0.7(6) . . . . ?
N1 S1 C5 C4 -113.3(5) . . . . ?
C4 C5 C6 C7 -0.3(9) . . . . ?
S1 C5 C6 C7 178.1(4) . . . . ?
C5 C6 C7 C2 0.3(9) . . . . ?
C3 C2 C7 C6 -0.5(9) . . . . ?
C1 C2 C7 C6 -179.1(6) . . . . ?
C11 N1 C8 C9 1.2(7) . . . . ?
S1 N1 C8 C9 167.6(4) . . . . ?
N1 C8 C9 C10 -1.0(7) . . . . ?
C8 C9 C10 C11 0.5(7) . . . . ?
C8 C9 C10 C12 179.3(5) . . . . ?
C9 C10 C11 N1 0.2(6) . . . . ?
C12 C10 C11 N1 -178.7(4) . . . . ?
C8 N1 C11 C10 -0.8(6) . . . . ?
S1 N1 C11 C10 -167.7(4) . . . . ?
C11 C10 C12 C13 -169.9(7) . . . . ?
C9 C10 C12 C13 11.4(12) . . . . ?
C11 C10 C12 O3 8.5(7) . . . . ?
C9 C10 C12 O3 -170.2(5) . . . . ?
C15 O3 C12 C13 1.2(5) . . . . ?
C15 O3 C12 C10 -177.8(4) . . . . ?
C10 C12 C13 C14 179.9(7) . . . . ?
O3 C12 C13 C14 1.4(6) . . . . ?
C10 C12 C13 C17 -1.3(11) . . . . ?
O3 C12 C13 C17 -179.8(4) . . . . ?
C12 C13 C14 C15 -3.7(7) . . . . ?
C17 C13 C14 C15 177.6(5) . . . . ?
C13 C14 C15 O3 4.6(7) . . . . ?
C13 C14 C15 C16 -178.4(6) . . . . ?
C12 O3 C15 C14 -3.6(6) . . . . ?
C12 O3 C15 C16 178.8(4) . . . . ?
C18 O4 C17 O5 -1.3(11) . . . . ?
C18 O4 C17 C13 -179.2(5) . . . . ?
C12 C13 C17 O5 5.7(11) . . . . ?
C14 C13 C17 O5 -175.7(8) . . . . ?
C12 C13 C17 O4 -176.5(5) . . . . ?
C14 C13 C17 O4 2.1(8) . . . . ?

_diffrn_measured_fraction_theta_max 0.970
_diffrn_reflns_theta_full        27.47
_diffrn_measured_fraction_theta_full 0.970
_refine_diff_density_max         0.871
_refine_diff_density_min         -0.381
_refine_diff_density_rms         0.077
