# 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 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_d:\determination\solution\917\kh917
_database_code_depnum_ccdc_archive 'CCDC 1019143'
_audit_update_record             
;
2014-08-12 deposited with the CCDC.
2015-02-25 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C18 H16 N2 O2 S1'
_chemical_formula_weight         324.40

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           Orthorhombic
_symmetry_space_group_name_H-M   Pbna

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

_cell_length_a                   7.4296(5)
_cell_length_b                   19.375(2)
_cell_length_c                   22.6760(18)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     3264.3(5)
_cell_formula_units_Z            8
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    21994
_cell_measurement_theta_min      1.80
_cell_measurement_theta_max      29.22

_exptl_crystal_description       Needle
_exptl_crystal_colour            Colorless
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.45
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.320
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1360
_exptl_absorpt_coefficient_mu    0.209
_exptl_absorpt_correction_type   None
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      298(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  'STOE IPDS II'
_diffrn_measurement_method       'rotation method'
_diffrn_detector_area_resol_mean '0.15 mm'
_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            21994
_diffrn_reflns_av_R_equivalents  0.0998
_diffrn_reflns_av_sigmaI/netI    0.1330
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_theta_min         1.80
_diffrn_reflns_theta_max         29.22
_reflns_number_total             4421
_reflns_number_gt                3982
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'X-Area 1.31 (Stoe & Cie GmbH, 2005)'
_computing_cell_refinement       'X-Area 1.31 (Stoe & Cie GmbH, 2005)'
_computing_data_reduction        'X-Area 1.31 (Stoe & Cie GmbH, 2005)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX (Farrugia, 1999)'

_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)+(0.0331P)²+0.0000P] 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     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4421
_refine_ls_number_parameters     220
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.2351
_refine_ls_R_factor_gt           0.0882
_refine_ls_wR_factor_ref         0.1450
_refine_ls_wR_factor_gt          0.1063
_refine_ls_goodness_of_fit_ref   1.009
_refine_ls_restrained_S_all      1.009
_refine_ls_shift/su_max          0.003
_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
C1 C 0.1611(6) -0.2907(2) 0.6858(2) 0.0672(15) Uani 1 1 d . . .
H1 H 0.1949 -0.3116 0.7210 0.081 Uiso 1 1 calc R . .
C2 C 0.0122(8) -0.3129(2) 0.6565(3) 0.0873(19) Uani 1 1 d . . .
H2 H -0.0520 -0.3502 0.6716 0.105 Uiso 1 1 calc R . .
C3 C -0.0459(8) -0.2822(3) 0.6058(3) 0.0939(19) Uani 1 1 d . . .
H3 H -0.1493 -0.2976 0.5868 0.113 Uiso 1 1 calc R . .
C4 C 0.0532(7) -0.2273(3) 0.5831(2) 0.0783(15) Uani 1 1 d . . .
H4 H 0.0167 -0.2058 0.5484 0.094 Uiso 1 1 calc R . .
C5 C 0.2051(6) -0.2052(2) 0.6120(2) 0.0585(12) Uani 1 1 d . . .
H5 H 0.2701 -0.1683 0.5967 0.070 Uiso 1 1 calc R . .
C6 C 0.2631(6) -0.2364(2) 0.6629(2) 0.0523(11) Uani 1 1 d . . .
C7 C 0.5120(6) -0.1550(2) 0.68485(17) 0.0472(10) Uani 1 1 d . . .
C8 C 0.7005(6) -0.1533(2) 0.68242(19) 0.0544(12) Uani 1 1 d . . .
H8 H 0.7645 -0.1944 0.6844 0.065 Uiso 1 1 calc R . .
C9 C 0.7915(5) -0.0930(2) 0.6772(2) 0.0522(11) Uani 1 1 d . . .
H9 H 0.9166 -0.0937 0.6764 0.063 Uiso 1 1 calc R . .
C10 C 0.7018(5) -0.0297(2) 0.67310(18) 0.0428(10) Uani 1 1 d . . .
C11 C 0.5134(4) -0.03168(17) 0.67518(16) 0.0374(9) Uani 1 1 d . . .
C12 C 0.4213(5) -0.09290(19) 0.68194(16) 0.0424(10) Uani 1 1 d . . .
H12 H 0.2964 -0.0924 0.6846 0.051 Uiso 1 1 calc R . .
C13 C 0.3893(5) 0.06649(18) 0.59420(17) 0.0437(9) Uani 1 1 d . . .
C14 C 0.2810(6) 0.0328(2) 0.5547(2) 0.0662(13) Uani 1 1 d . . .
H14 H 0.2073 -0.0030 0.5674 0.079 Uiso 1 1 calc R . .
C15 C 0.2807(8) 0.0520(3) 0.4960(2) 0.0856(17) Uani 1 1 d . . .
H15 H 0.2100 0.0283 0.4688 0.103 Uiso 1 1 calc R . .
C16 C 0.3846(9) 0.1056(3) 0.4783(2) 0.0886(17) Uani 1 1 d . . .
H16 H 0.3818 0.1195 0.4391 0.106 Uiso 1 1 calc R . .
C17 C 0.4933(8) 0.1395(3) 0.5172(2) 0.0827(16) Uani 1 1 d . . .
H17 H 0.5653 0.1757 0.5043 0.099 Uiso 1 1 calc R . .
C18 C 0.4960(6) 0.1200(2) 0.5756(2) 0.0627(12) Uani 1 1 d . . .
H18 H 0.5699 0.1430 0.6022 0.075 Uiso 1 1 calc R . .
N1 N 0.4188(6) -0.2183(2) 0.6917(2) 0.0688(12) Uani 1 1 d . . .
H1B H 0.470(5) -0.240(2) 0.7156(18) 0.048(14) Uiso 1 1 d . . .
N2 N 0.7982(5) 0.0295(2) 0.6640(2) 0.0656(12) Uani 1 1 d . . .
H2B H 0.909(6) 0.028(2) 0.672(2) 0.074(15) Uiso 1 1 d . . .
H2C H 0.757(6) 0.068(2) 0.679(2) 0.064(15) Uiso 1 1 d . . .
O1 O 0.2013(3) 0.02549(14) 0.68348(13) 0.0555(8) Uani 1 1 d . . .
O2 O 0.4671(3) 0.09873(13) 0.70175(12) 0.0543(7) Uani 1 1 d . . .
S1 S 0.38385(13) 0.04380(5) 0.66918(4) 0.0410(2) Uani 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 C2 1.360(7) . ?
C1 C6 1.396(5) . ?
C1 H1 0.9300 . ?
C2 C3 1.366(8) . ?
C2 H2 0.9300 . ?
C3 C4 1.392(7) . ?
C3 H3 0.9300 . ?
C4 C5 1.374(6) . ?
C4 H4 0.9300 . ?
C5 C6 1.374(6) . ?
C5 H5 0.9300 . ?
C6 N1 1.373(6) . ?
C7 C12 1.380(5) . ?
C7 C8 1.402(5) . ?
C7 N1 1.417(5) . ?
C8 C9 1.355(6) . ?
C8 H8 0.9300 . ?
C9 C10 1.398(5) . ?
C9 H9 0.9300 . ?
C10 N2 1.369(5) . ?
C10 C11 1.401(4) . ?
C11 C12 1.378(5) . ?
C11 S1 1.756(3) . ?
C12 H12 0.9300 . ?
C13 C14 1.370(6) . ?
C13 C18 1.372(5) . ?
C13 S1 1.757(4) . ?
C14 C15 1.383(6) . ?
C14 H14 0.9300 . ?
C15 C16 1.354(7) . ?
C15 H15 0.9300 . ?
C16 C17 1.363(7) . ?
C16 H16 0.9300 . ?
C17 C18 1.377(6) . ?
C17 H17 0.9300 . ?
C18 H18 0.9300 . ?
N1 H1B 0.79(4) . ?
N2 H2B 0.84(4) . ?
N2 H2C 0.88(4) . ?
O1 S1 1.439(2) . ?
O2 S1 1.436(3) . ?

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
C2 C1 C6 119.9(5) . . ?
C2 C1 H1 120.0 . . ?
C6 C1 H1 120.0 . . ?
C1 C2 C3 122.0(5) . . ?
C1 C2 H2 119.0 . . ?
C3 C2 H2 119.0 . . ?
C2 C3 C4 118.5(5) . . ?
C2 C3 H3 120.7 . . ?
C4 C3 H3 120.7 . . ?
C5 C4 C3 119.8(5) . . ?
C5 C4 H4 120.1 . . ?
C3 C4 H4 120.1 . . ?
C4 C5 C6 121.4(5) . . ?
C4 C5 H5 119.3 . . ?
C6 C5 H5 119.3 . . ?
N1 C6 C5 123.4(4) . . ?
N1 C6 C1 118.3(5) . . ?
C5 C6 C1 118.3(5) . . ?
C12 C7 C8 117.7(4) . . ?
C12 C7 N1 121.4(4) . . ?
C8 C7 N1 120.9(4) . . ?
C9 C8 C7 121.5(4) . . ?
C9 C8 H8 119.2 . . ?
C7 C8 H8 119.2 . . ?
C8 C9 C10 121.6(4) . . ?
C8 C9 H9 119.2 . . ?
C10 C9 H9 119.2 . . ?
N2 C10 C9 119.7(4) . . ?
N2 C10 C11 123.4(4) . . ?
C9 C10 C11 116.8(4) . . ?
C12 C11 C10 121.5(3) . . ?
C12 C11 S1 116.9(2) . . ?
C10 C11 S1 121.5(3) . . ?
C11 C12 C7 120.9(3) . . ?
C11 C12 H12 119.6 . . ?
C7 C12 H12 119.6 . . ?
C14 C13 C18 119.9(4) . . ?
C14 C13 S1 120.0(3) . . ?
C18 C13 S1 120.0(3) . . ?
C13 C14 C15 120.2(5) . . ?
C13 C14 H14 119.9 . . ?
C15 C14 H14 119.9 . . ?
C16 C15 C14 119.3(5) . . ?
C16 C15 H15 120.3 . . ?
C14 C15 H15 120.3 . . ?
C15 C16 C17 121.1(5) . . ?
C15 C16 H16 119.4 . . ?
C17 C16 H16 119.4 . . ?
C16 C17 C18 119.8(5) . . ?
C16 C17 H17 120.1 . . ?
C18 C17 H17 120.1 . . ?
C13 C18 C17 119.6(5) . . ?
C13 C18 H18 120.2 . . ?
C17 C18 H18 120.2 . . ?
C6 N1 C7 125.6(4) . . ?
C6 N1 H1B 127(3) . . ?
C7 N1 H1B 108(3) . . ?
C10 N2 H2B 117(3) . . ?
C10 N2 H2C 118(3) . . ?
H2B N2 H2C 106(4) . . ?
O2 S1 O1 118.23(16) . . ?
O2 S1 C11 109.96(16) . . ?
O1 S1 C11 107.10(16) . . ?
O2 S1 C13 107.60(18) . . ?
O1 S1 C13 107.56(18) . . ?
C11 S1 C13 105.71(17) . . ?

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
C6 C1 C2 C3 -2.3(7) . . . . ?
C1 C2 C3 C4 1.2(8) . . . . ?
C2 C3 C4 C5 -0.3(8) . . . . ?
C3 C4 C5 C6 0.5(7) . . . . ?
C4 C5 C6 N1 176.6(4) . . . . ?
C4 C5 C6 C1 -1.5(6) . . . . ?
C2 C1 C6 N1 -175.9(4) . . . . ?
C2 C1 C6 C5 2.4(6) . . . . ?
C12 C7 C8 C9 -0.2(7) . . . . ?
N1 C7 C8 C9 -178.5(4) . . . . ?
C7 C8 C9 C10 -1.0(7) . . . . ?
C8 C9 C10 N2 -175.7(4) . . . . ?
C8 C9 C10 C11 0.6(6) . . . . ?
N2 C10 C11 C12 177.2(4) . . . . ?
C9 C10 C11 C12 1.0(6) . . . . ?
N2 C10 C11 S1 -2.7(6) . . . . ?
C9 C10 C11 S1 -178.9(3) . . . . ?
C10 C11 C12 C7 -2.3(6) . . . . ?
S1 C11 C12 C7 177.6(3) . . . . ?
C8 C7 C12 C11 1.8(6) . . . . ?
N1 C7 C12 C11 -179.8(4) . . . . ?
C18 C13 C14 C15 0.9(7) . . . . ?
S1 C13 C14 C15 178.0(4) . . . . ?
C13 C14 C15 C16 -1.9(8) . . . . ?
C14 C15 C16 C17 2.0(9) . . . . ?
C15 C16 C17 C18 -1.1(9) . . . . ?
C14 C13 C18 C17 0.0(6) . . . . ?
S1 C13 C18 C17 -177.0(4) . . . . ?
C16 C17 C18 C13 0.1(8) . . . . ?
C5 C6 N1 C7 19.6(7) . . . . ?
C1 C6 N1 C7 -162.2(4) . . . . ?
C12 C7 N1 C6 42.3(6) . . . . ?
C8 C7 N1 C6 -139.5(5) . . . . ?
C12 C11 S1 O2 139.8(3) . . . . ?
C10 C11 S1 O2 -40.3(4) . . . . ?
C12 C11 S1 O1 10.2(3) . . . . ?
C10 C11 S1 O1 -169.9(3) . . . . ?
C12 C11 S1 C13 -104.3(3) . . . . ?
C10 C11 S1 C13 75.6(4) . . . . ?
C14 C13 S1 O2 -163.5(3) . . . . ?
C18 C13 S1 O2 13.5(4) . . . . ?
C14 C13 S1 O1 -35.2(4) . . . . ?
C18 C13 S1 O1 141.9(3) . . . . ?
C14 C13 S1 C11 79.0(4) . . . . ?
C18 C13 S1 C11 -104.0(3) . . . . ?

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        29.22
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.279
_refine_diff_density_min         -0.245
_refine_diff_density_rms         0.045
