# 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
_audit_block_doi                 10.5517/cc1k2y1m
_database_code_depnum_ccdc_archive 'CCDC 1432790'
_audit_update_record             
;
2015-10-23 deposited with the CCDC.
2016-01-15 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C25 H20 N2 O2 S'
_chemical_formula_weight         412.49

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           Monoclinic
_symmetry_space_group_name_H-M   Cc

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

_cell_length_a                   19.897(4)
_cell_length_b                   12.667(3)
_cell_length_c                   8.4207(17)
_cell_angle_alpha                90.00
_cell_angle_beta                 108.18(3)
_cell_angle_gamma                90.00
_cell_volume                     2016.3(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    113(2)
_cell_measurement_reflns_used    3179
_cell_measurement_theta_min      1.9354
_cell_measurement_theta_max      27.8944

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.12
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.359
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             864
_exptl_absorpt_coefficient_mu    0.186
_exptl_absorpt_correction_type   MULTI-SCAN
_exptl_absorpt_correction_T_min  0.9638
_exptl_absorpt_correction_T_max  0.9781
_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            9734
_diffrn_reflns_av_R_equivalents  0.0392
_diffrn_reflns_av_sigmaI/netI    0.0570
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         1.94
_diffrn_reflns_theta_max         27.89
_reflns_number_total             4166
_reflns_number_gt                3359
_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)+(0.0398P)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     SHELXL
_refine_ls_extinction_coef       0.0133(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.03(5)
_refine_ls_number_reflns         4166
_refine_ls_number_parameters     277
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0405
_refine_ls_R_factor_gt           0.0317
_refine_ls_wR_factor_ref         0.0722
_refine_ls_wR_factor_gt          0.0692
_refine_ls_goodness_of_fit_ref   0.971
_refine_ls_restrained_S_all      0.970
_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
S1 S -0.06205(3) 0.71952(4) 0.86839(5) 0.02248(12) Uani 1 1 d . . .
O1 O 0.07033(7) 0.75613(10) 0.90827(17) 0.0224(3) Uani 1 1 d . . .
O2 O 0.07731(7) 0.45952(10) 0.5706(2) 0.0329(4) Uani 1 1 d . . .
N1 N -0.19081(7) 0.66704(12) 0.65151(18) 0.0180(3) Uani 1 1 d . . .
N2 N 0.09553(7) 0.62104(12) 0.6877(2) 0.0188(3) Uani 1 1 d D . .
C1 C -0.22579(10) 0.67896(17) 0.7780(2) 0.0254(4) Uani 1 1 d . . .
H1A H -0.2769 0.6697 0.7267 0.038 Uiso 1 1 calc R . .
H1B H -0.2163 0.7496 0.8274 0.038 Uiso 1 1 calc R . .
H1C H -0.2078 0.6257 0.8653 0.038 Uiso 1 1 calc R . .
C2 C -0.22282(9) 0.64085(13) 0.4857(2) 0.0156(4) Uani 1 1 d . . .
C3 C -0.29488(9) 0.62649(13) 0.3981(2) 0.0186(4) Uani 1 1 d . . .
H3 H -0.3300 0.6333 0.4523 0.022 Uiso 1 1 calc R . .
C4 C -0.31270(9) 0.60207(13) 0.2303(2) 0.0199(4) Uani 1 1 d . . .
H4 H -0.3610 0.5924 0.1675 0.024 Uiso 1 1 calc R . .
C5 C -0.26081(9) 0.59126(13) 0.1508(2) 0.0197(4) Uani 1 1 d . . .
H5 H -0.2747 0.5747 0.0350 0.024 Uiso 1 1 calc R . .
C6 C -0.18965(9) 0.60425(13) 0.2373(2) 0.0171(4) Uani 1 1 d . . .
H6 H -0.1550 0.5955 0.1823 0.021 Uiso 1 1 calc R . .
C7 C -0.16959(9) 0.63054(13) 0.4077(2) 0.0157(4) Uani 1 1 d . . .
C8 C -0.10333(9) 0.65194(13) 0.5335(2) 0.0167(4) Uani 1 1 d . . .
C9 C -0.11885(9) 0.67371(14) 0.6763(2) 0.0181(4) Uani 1 1 d . . .
C10 C -0.03024(9) 0.65267(14) 0.5175(2) 0.0163(4) Uani 1 1 d . . .
H10 H -0.0278 0.5937 0.4406 0.020 Uiso 1 1 calc R . .
C11 C -0.00975(9) 0.75404(14) 0.4452(2) 0.0186(4) Uani 1 1 d . . .
C12 C -0.02976(9) 0.85313(14) 0.4881(2) 0.0201(4) Uani 1 1 d . . .
H12 H -0.0590 0.8576 0.5580 0.024 Uiso 1 1 calc R . .
C13 C -0.00751(10) 0.94520(15) 0.4301(2) 0.0235(4) Uani 1 1 d . . .
H13 H -0.0218 1.0119 0.4598 0.028 Uiso 1 1 calc R . .
C14 C 0.03541(10) 0.93965(17) 0.3289(2) 0.0266(4) Uani 1 1 d . . .
H14 H 0.0514 1.0025 0.2906 0.032 Uiso 1 1 calc R . .
C15 C 0.05512(10) 0.84164(17) 0.2833(2) 0.0287(5) Uani 1 1 d . . .
H15 H 0.0842 0.8375 0.2129 0.034 Uiso 1 1 calc R . .
C16 C 0.03227(9) 0.74938(15) 0.3410(2) 0.0225(4) Uani 1 1 d . . .
H16 H 0.0456 0.6827 0.3088 0.027 Uiso 1 1 calc R . .
C17 C 0.02351(9) 0.62652(14) 0.6932(2) 0.0178(4) Uani 1 1 d . . .
H17 H 0.0110 0.5555 0.7276 0.021 Uiso 1 1 calc R . .
C18 C 0.02052(9) 0.70500(14) 0.8263(2) 0.0174(4) Uani 1 1 d . . .
C19 C 0.11760(9) 0.53440(14) 0.6228(2) 0.0204(4) Uani 1 1 d . . .
C20 C 0.19188(9) 0.53479(15) 0.6157(2) 0.0186(4) Uani 1 1 d . . .
C21 C 0.23413(10) 0.62424(15) 0.6410(3) 0.0230(4) Uani 1 1 d . . .
H21 H 0.2163 0.6896 0.6662 0.028 Uiso 1 1 calc R . .
C22 C 0.30185(10) 0.61917(15) 0.6298(3) 0.0246(4) Uani 1 1 d . . .
H22 H 0.3305 0.6807 0.6479 0.030 Uiso 1 1 calc R . .
C23 C 0.32796(10) 0.52376(15) 0.5920(3) 0.0254(4) Uani 1 1 d . . .
H23 H 0.3747 0.5201 0.5853 0.030 Uiso 1 1 calc R . .
C24 C 0.28622(10) 0.43422(16) 0.5643(3) 0.0273(4) Uani 1 1 d . . .
H24 H 0.3038 0.3695 0.5363 0.033 Uiso 1 1 calc R . .
C25 C 0.21822(10) 0.43925(14) 0.5777(2) 0.0231(4) Uani 1 1 d . . .
H25 H 0.1897 0.3775 0.5608 0.028 Uiso 1 1 calc R . .
H2 H 0.1263(8) 0.6721(11) 0.739(2) 0.017(5) 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 C9 1.7579(19) . ?
S1 C18 1.7950(18) . ?
O1 C18 1.205(2) . ?
O2 C19 1.231(2) . ?
N1 C2 1.382(2) . ?
N1 C9 1.384(2) . ?
N1 C1 1.451(2) . ?
N2 C19 1.359(2) . ?
N2 C17 1.450(2) . ?
N2 H2 0.902(9) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C2 C3 1.405(2) . ?
C2 C7 1.416(2) . ?
C3 C4 1.380(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.402(3) . ?
C4 H4 0.9500 . ?
C5 C6 1.385(2) . ?
C5 H5 0.9500 . ?
C6 C7 1.404(3) . ?
C6 H6 0.9500 . ?
C7 C8 1.436(2) . ?
C8 C9 1.360(3) . ?
C8 C10 1.502(2) . ?
C10 C11 1.530(3) . ?
C10 C17 1.567(3) . ?
C10 H10 1.0000 . ?
C11 C16 1.389(2) . ?
C11 C12 1.398(3) . ?
C12 C13 1.389(3) . ?
C12 H12 0.9500 . ?
C13 C14 1.383(3) . ?
C13 H13 0.9500 . ?
C14 C15 1.391(3) . ?
C14 H14 0.9500 . ?
C15 C16 1.395(3) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?
C17 C18 1.513(3) . ?
C17 H17 1.0000 . ?
C19 C20 1.498(2) . ?
C20 C21 1.387(3) . ?
C20 C25 1.395(3) . ?
C21 C22 1.381(3) . ?
C21 H21 0.9500 . ?
C22 C23 1.391(3) . ?
C22 H22 0.9500 . ?
C23 C24 1.382(3) . ?
C23 H23 0.9500 . ?
C24 C25 1.394(3) . ?
C24 H24 0.9500 . ?
C25 H25 0.9500 . ?

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
C9 S1 C18 98.61(9) . . ?
C2 N1 C9 107.21(14) . . ?
C2 N1 C1 126.25(15) . . ?
C9 N1 C1 126.44(15) . . ?
C19 N2 C17 119.89(14) . . ?
C19 N2 H2 120.9(12) . . ?
C17 N2 H2 118.8(12) . . ?
N1 C1 H1A 109.5 . . ?
N1 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
N1 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
N1 C2 C3 129.39(16) . . ?
N1 C2 C7 108.37(14) . . ?
C3 C2 C7 122.24(16) . . ?
C4 C3 C2 117.41(17) . . ?
C4 C3 H3 121.3 . . ?
C2 C3 H3 121.3 . . ?
C3 C4 C5 121.25(17) . . ?
C3 C4 H4 119.4 . . ?
C5 C4 H4 119.4 . . ?
C6 C5 C4 121.42(17) . . ?
C6 C5 H5 119.3 . . ?
C4 C5 H5 119.3 . . ?
C5 C6 C7 118.94(17) . . ?
C5 C6 H6 120.5 . . ?
C7 C6 H6 120.5 . . ?
C6 C7 C2 118.72(16) . . ?
C6 C7 C8 134.53(17) . . ?
C2 C7 C8 106.74(16) . . ?
C9 C8 C7 106.32(16) . . ?
C9 C8 C10 124.85(16) . . ?
C7 C8 C10 128.83(17) . . ?
C8 C9 N1 111.36(15) . . ?
C8 C9 S1 128.50(14) . . ?
N1 C9 S1 119.79(13) . . ?
C8 C10 C11 115.25(14) . . ?
C8 C10 C17 107.99(14) . . ?
C11 C10 C17 111.41(14) . . ?
C8 C10 H10 107.3 . . ?
C11 C10 H10 107.3 . . ?
C17 C10 H10 107.3 . . ?
C16 C11 C12 118.52(17) . . ?
C16 C11 C10 120.22(16) . . ?
C12 C11 C10 121.19(17) . . ?
C13 C12 C11 121.00(18) . . ?
C13 C12 H12 119.5 . . ?
C11 C12 H12 119.5 . . ?
C14 C13 C12 119.98(19) . . ?
C14 C13 H13 120.0 . . ?
C12 C13 H13 120.0 . . ?
C13 C14 C15 119.75(18) . . ?
C13 C14 H14 120.1 . . ?
C15 C14 H14 120.1 . . ?
C14 C15 C16 120.06(18) . . ?
C14 C15 H15 120.0 . . ?
C16 C15 H15 120.0 . . ?
C11 C16 C15 120.67(18) . . ?
C11 C16 H16 119.7 . . ?
C15 C16 H16 119.7 . . ?
N2 C17 C18 108.83(14) . . ?
N2 C17 C10 111.74(15) . . ?
C18 C17 C10 112.80(14) . . ?
N2 C17 H17 107.8 . . ?
C18 C17 H17 107.8 . . ?
C10 C17 H17 107.8 . . ?
O1 C18 C17 124.20(17) . . ?
O1 C18 S1 118.15(15) . . ?
C17 C18 S1 117.62(12) . . ?
O2 C19 N2 120.65(16) . . ?
O2 C19 C20 121.94(16) . . ?
N2 C19 C20 117.40(15) . . ?
C21 C20 C25 119.39(16) . . ?
C21 C20 C19 123.70(16) . . ?
C25 C20 C19 116.89(16) . . ?
C22 C21 C20 120.59(17) . . ?
C22 C21 H21 119.7 . . ?
C20 C21 H21 119.7 . . ?
C21 C22 C23 119.87(18) . . ?
C21 C22 H22 120.1 . . ?
C23 C22 H22 120.1 . . ?
C24 C23 C22 120.26(18) . . ?
C24 C23 H23 119.9 . . ?
C22 C23 H23 119.9 . . ?
C23 C24 C25 119.76(18) . . ?
C23 C24 H24 120.1 . . ?
C25 C24 H24 120.1 . . ?
C24 C25 C20 120.12(17) . . ?
C24 C25 H25 119.9 . . ?
C20 C25 H25 119.9 . . ?

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
C9 N1 C2 C3 -178.88(17) . . . . ?
C1 N1 C2 C3 4.5(3) . . . . ?
C9 N1 C2 C7 0.41(18) . . . . ?
C1 N1 C2 C7 -176.20(17) . . . . ?
N1 C2 C3 C4 178.88(18) . . . . ?
C7 C2 C3 C4 -0.3(2) . . . . ?
C2 C3 C4 C5 0.5(2) . . . . ?
C3 C4 C5 C6 0.2(3) . . . . ?
C4 C5 C6 C7 -1.1(3) . . . . ?
C5 C6 C7 C2 1.2(2) . . . . ?
C5 C6 C7 C8 -178.42(19) . . . . ?
N1 C2 C7 C6 -179.86(16) . . . . ?
C3 C2 C7 C6 -0.5(2) . . . . ?
N1 C2 C7 C8 -0.15(18) . . . . ?
C3 C2 C7 C8 179.20(16) . . . . ?
C6 C7 C8 C9 179.47(19) . . . . ?
C2 C7 C8 C9 -0.18(19) . . . . ?
C6 C7 C8 C10 0.2(3) . . . . ?
C2 C7 C8 C10 -179.46(16) . . . . ?
C7 C8 C9 N1 0.4(2) . . . . ?
C10 C8 C9 N1 179.77(15) . . . . ?
C7 C8 C9 S1 -172.63(14) . . . . ?
C10 C8 C9 S1 6.7(3) . . . . ?
C2 N1 C9 C8 -0.5(2) . . . . ?
C1 N1 C9 C8 176.06(17) . . . . ?
C2 N1 C9 S1 173.22(13) . . . . ?
C1 N1 C9 S1 -10.2(2) . . . . ?
C18 S1 C9 C8 -9.57(19) . . . . ?
C18 S1 C9 N1 177.86(14) . . . . ?
C9 C8 C10 C11 -97.8(2) . . . . ?
C7 C8 C10 C11 81.4(2) . . . . ?
C9 C8 C10 C17 27.5(2) . . . . ?
C7 C8 C10 C17 -153.32(17) . . . . ?
C8 C10 C11 C16 -143.98(17) . . . . ?
C17 C10 C11 C16 92.53(19) . . . . ?
C8 C10 C11 C12 39.1(2) . . . . ?
C17 C10 C11 C12 -84.39(19) . . . . ?
C16 C11 C12 C13 -0.8(3) . . . . ?
C10 C11 C12 C13 176.13(16) . . . . ?
C11 C12 C13 C14 -0.3(3) . . . . ?
C12 C13 C14 C15 1.1(3) . . . . ?
C13 C14 C15 C16 -0.7(3) . . . . ?
C12 C11 C16 C15 1.3(3) . . . . ?
C10 C11 C16 C15 -175.75(17) . . . . ?
C14 C15 C16 C11 -0.5(3) . . . . ?
C19 N2 C17 C18 157.90(16) . . . . ?
C19 N2 C17 C10 -76.9(2) . . . . ?
C8 C10 C17 N2 177.51(14) . . . . ?
C11 C10 C17 N2 -54.97(19) . . . . ?
C8 C10 C17 C18 -59.50(18) . . . . ?
C11 C10 C17 C18 68.02(19) . . . . ?
N2 C17 C18 O1 2.3(3) . . . . ?
C10 C17 C18 O1 -122.25(19) . . . . ?
N2 C17 C18 S1 -175.68(12) . . . . ?
C10 C17 C18 S1 59.72(18) . . . . ?
C9 S1 C18 O1 158.65(15) . . . . ?
C9 S1 C18 C17 -23.20(15) . . . . ?
C17 N2 C19 O2 -1.1(3) . . . . ?
C17 N2 C19 C20 178.15(16) . . . . ?
O2 C19 C20 C21 166.49(19) . . . . ?
N2 C19 C20 C21 -12.7(3) . . . . ?
O2 C19 C20 C25 -12.0(3) . . . . ?
N2 C19 C20 C25 168.75(17) . . . . ?
C25 C20 C21 C22 -0.4(3) . . . . ?
C19 C20 C21 C22 -178.91(18) . . . . ?
C20 C21 C22 C23 0.3(3) . . . . ?
C21 C22 C23 C24 0.5(3) . . . . ?
C22 C23 C24 C25 -1.3(3) . . . . ?
C23 C24 C25 C20 1.2(3) . . . . ?
C21 C20 C25 C24 -0.4(3) . . . . ?
C19 C20 C25 C24 178.23(18) . . . . ?

_diffrn_measured_fraction_theta_max 0.995
_diffrn_reflns_theta_full        27.89
_diffrn_measured_fraction_theta_full 0.995
_refine_diff_density_max         0.246
_refine_diff_density_min         -0.186
_refine_diff_density_rms         0.045
