# 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_g:\141218a\work\mo_141218a_0m
_database_code_depnum_ccdc_archive 'CCDC 1057970'
_audit_update_record             
;
2015-04-05 deposited with the CCDC.
2015-08-24 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C24 H18 N2 O3 S'
_chemical_formula_weight         414.46

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   Pbca

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

_cell_length_a                   11.3834(14)
_cell_length_b                   12.9542(16)
_cell_length_c                   26.397(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     3892.5(8)
_cell_formula_units_Z            8
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    9954
_cell_measurement_theta_min      2.36
_cell_measurement_theta_max      30.12

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      0
_exptl_crystal_density_diffrn    1.414
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1728
_exptl_absorpt_coefficient_mu    0.196
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  0.9618
_exptl_absorpt_correction_T_max  0.9618
_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  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            39995
_diffrn_reflns_av_R_equivalents  0.0298
_diffrn_reflns_av_sigmaI/netI    0.0190
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -37
_diffrn_reflns_limit_l_max       36
_diffrn_reflns_theta_min         2.36
_diffrn_reflns_theta_max         30.00
_reflns_number_total             5669
_reflns_number_gt                4552
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_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)+(0.0722P)²+1.1203P] 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         5669
_refine_ls_number_parameters     271
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0549
_refine_ls_R_factor_gt           0.0423
_refine_ls_wR_factor_ref         0.1341
_refine_ls_wR_factor_gt          0.1213
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_restrained_S_all      1.035
_refine_ls_shift/su_max          0.001
_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 0.35376(12) -0.04556(10) 0.69373(5) 0.0345(3) Uani 1 1 d . . .
C2 C 0.39500(14) -0.03891(12) 0.64461(6) 0.0415(3) Uani 1 1 d . . .
H2 H 0.4724 -0.0201 0.6382 0.050 Uiso 1 1 calc R . .
C3 C 0.31927(16) -0.06071(13) 0.60517(6) 0.0488(4) Uani 1 1 d . . .
H3 H 0.3451 -0.0568 0.5718 0.059 Uiso 1 1 calc R . .
C4 C 0.20523(16) -0.08830(13) 0.61575(7) 0.0539(4) Uani 1 1 d . . .
H4 H 0.1523 -0.1025 0.5898 0.065 Uiso 1 1 calc R . .
C5 C 0.17191(15) -0.09422(14) 0.66529(8) 0.0545(4) Uani 1 1 d . . .
H5 H 0.0953 -0.1145 0.6723 0.065 Uiso 1 1 calc R . .
C6 C 0.42977(13) -0.02493(13) 0.73938(6) 0.0422(3) Uani 1 1 d . . .
H6A H 0.3886 0.0223 0.7617 0.051 Uiso 1 1 calc R . .
H6B H 0.4409 -0.0892 0.7576 0.051 Uiso 1 1 calc R . .
C7 C 0.54908(11) 0.17936(11) 0.79320(5) 0.0338(3) Uani 1 1 d . . .
C8 C 0.44142(12) 0.21280(12) 0.81135(6) 0.0391(3) Uani 1 1 d . . .
H8 H 0.3789 0.2235 0.7893 0.047 Uiso 1 1 calc R . .
C9 C 0.42811(12) 0.23009(12) 0.86288(6) 0.0402(3) Uani 1 1 d . . .
H9 H 0.3563 0.2534 0.8752 0.048 Uiso 1 1 calc R . .
C10 C 0.52053(12) 0.21314(11) 0.89643(5) 0.0355(3) Uani 1 1 d . . .
C11 C 0.62932(12) 0.18196(11) 0.87687(5) 0.0373(3) Uani 1 1 d . . .
H11 H 0.6923 0.1719 0.8988 0.045 Uiso 1 1 calc R . .
C12 C 0.64450(12) 0.16596(11) 0.82559(5) 0.0369(3) Uani 1 1 d . . .
H12 H 0.7174 0.1465 0.8128 0.044 Uiso 1 1 calc R . .
C13 C 0.50640(13) 0.23492(11) 0.95103(5) 0.0393(3) Uani 1 1 d . . .
C14 C 0.44021(15) 0.31956(14) 0.96781(7) 0.0501(4) Uani 1 1 d . . .
H14 H 0.4021 0.3605 0.9440 0.060 Uiso 1 1 calc R . .
C15 C 0.42963(17) 0.34451(15) 1.01894(7) 0.0571(5) Uani 1 1 d . . .
H15 H 0.3840 0.4009 1.0283 0.069 Uiso 1 1 calc R . .
C16 C 0.48517(16) 0.28750(14) 1.05598(6) 0.0507(4) Uani 1 1 d . . .
H16 H 0.4789 0.3054 1.0900 0.061 Uiso 1 1 calc R . .
C17 C 0.55064(13) 0.20267(12) 1.04097(6) 0.0408(3) Uani 1 1 d . . .
C18 C 0.61775(13) 0.12442(13) 1.06731(6) 0.0426(3) Uani 1 1 d . . .
C19 C 0.65044(15) 0.10759(16) 1.11777(6) 0.0530(4) Uani 1 1 d . . .
H19 H 0.6265 0.1523 1.1433 0.064 Uiso 1 1 calc R . .
C20 C 0.71914(16) 0.02288(18) 1.12836(7) 0.0617(5) Uani 1 1 d . . .
H20 H 0.7422 0.0107 1.1616 0.074 Uiso 1 1 calc R . .
C21 C 0.75475(17) -0.04461(17) 1.09069(8) 0.0610(5) Uani 1 1 d . . .
H21 H 0.8007 -0.1012 1.0994 0.073 Uiso 1 1 calc R . .
C22 C 0.72387(16) -0.03036(14) 1.04009(7) 0.0528(4) Uani 1 1 d . . .
H22 H 0.7470 -0.0759 1.0147 0.063 Uiso 1 1 calc R . .
C23 C 0.65651(14) 0.05617(12) 1.03015(6) 0.0427(3) Uani 1 1 d . . .
C24 C 0.55802(12) 0.17719(11) 0.98950(5) 0.0382(3) Uani 1 1 d . . .
N1 N 0.54533(11) 0.01870(10) 0.72744(5) 0.0390(3) Uani 1 1 d . . .
H1 H 0.6032 -0.0210 0.7197 0.047 Uiso 1 1 calc R . .
N3 N 0.24280(11) -0.07254(11) 0.70452(5) 0.0455(3) Uani 1 1 d . . .
O1 O 0.46664(12) 0.18743(10) 0.70161(4) 0.0527(3) Uani 1 1 d . . .
O2 O 0.68051(11) 0.16152(11) 0.71310(5) 0.0594(3) Uani 1 1 d . . .
O3 O 0.62103(10) 0.08714(8) 0.98217(4) 0.0426(2) Uani 1 1 d . . .
S1 S 0.56234(3) 0.14307(3) 0.729104(13) 0.03736(11) 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 N3 1.3412(18) . ?
C1 C2 1.382(2) . ?
C1 C6 1.507(2) . ?
C2 C3 1.381(2) . ?
C2 H2 0.9300 . ?
C3 C4 1.375(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.364(3) . ?
C4 H4 0.9300 . ?
C5 N3 1.343(2) . ?
C5 H5 0.9300 . ?
C6 N1 1.4660(18) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C7 C8 1.3854(19) . ?
C7 C12 1.3933(19) . ?
C7 S1 1.7624(14) . ?
C8 C9 1.387(2) . ?
C8 H8 0.9300 . ?
C9 C10 1.393(2) . ?
C9 H9 0.9300 . ?
C10 C11 1.4011(19) . ?
C10 C13 1.4775(19) . ?
C11 C12 1.380(2) . ?
C11 H11 0.9300 . ?
C12 H12 0.9300 . ?
C13 C24 1.391(2) . ?
C13 C14 1.402(2) . ?
C14 C15 1.393(2) . ?
C14 H14 0.9300 . ?
C15 C16 1.379(3) . ?
C15 H15 0.9300 . ?
C16 C17 1.386(2) . ?
C16 H16 0.9300 . ?
C17 C24 1.401(2) . ?
C17 C18 1.447(2) . ?
C18 C23 1.392(2) . ?
C18 C19 1.400(2) . ?
C19 C20 1.376(3) . ?
C19 H19 0.9300 . ?
C20 C21 1.385(3) . ?
C20 H20 0.9300 . ?
C21 C22 1.393(3) . ?
C21 H21 0.9300 . ?
C22 C23 1.383(2) . ?
C22 H22 0.9300 . ?
C23 O3 1.3884(18) . ?
C24 O3 1.3830(18) . ?
N1 S1 1.6234(14) . ?
N1 H1 0.8600 . ?
O1 S1 1.4296(12) . ?
O2 S1 1.4300(12) . ?

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
N3 C1 C2 122.37(14) . . ?
N3 C1 C6 114.66(13) . . ?
C2 C1 C6 122.96(13) . . ?
C3 C2 C1 118.86(15) . . ?
C3 C2 H2 120.6 . . ?
C1 C2 H2 120.6 . . ?
C4 C3 C2 119.30(16) . . ?
C4 C3 H3 120.3 . . ?
C2 C3 H3 120.3 . . ?
C5 C4 C3 118.16(16) . . ?
C5 C4 H4 120.9 . . ?
C3 C4 H4 120.9 . . ?
N3 C5 C4 124.10(16) . . ?
N3 C5 H5 118.0 . . ?
C4 C5 H5 118.0 . . ?
N1 C6 C1 114.31(12) . . ?
N1 C6 H6A 108.7 . . ?
C1 C6 H6A 108.7 . . ?
N1 C6 H6B 108.7 . . ?
C1 C6 H6B 108.7 . . ?
H6A C6 H6B 107.6 . . ?
C8 C7 C12 121.09(13) . . ?
C8 C7 S1 119.42(10) . . ?
C12 C7 S1 119.29(10) . . ?
C7 C8 C9 119.10(13) . . ?
C7 C8 H8 120.4 . . ?
C9 C8 H8 120.4 . . ?
C8 C9 C10 121.04(13) . . ?
C8 C9 H9 119.5 . . ?
C10 C9 H9 119.5 . . ?
C9 C10 C11 118.62(13) . . ?
C9 C10 C13 120.53(13) . . ?
C11 C10 C13 120.71(13) . . ?
C12 C11 C10 121.01(13) . . ?
C12 C11 H11 119.5 . . ?
C10 C11 H11 119.5 . . ?
C11 C12 C7 119.05(13) . . ?
C11 C12 H12 120.5 . . ?
C7 C12 H12 120.5 . . ?
C24 C13 C14 114.63(14) . . ?
C24 C13 C10 124.29(13) . . ?
C14 C13 C10 121.07(14) . . ?
C15 C14 C13 122.27(16) . . ?
C15 C14 H14 118.9 . . ?
C13 C14 H14 118.9 . . ?
C16 C15 C14 121.54(16) . . ?
C16 C15 H15 119.2 . . ?
C14 C15 H15 119.2 . . ?
C15 C16 C17 117.94(15) . . ?
C15 C16 H16 121.0 . . ?
C17 C16 H16 121.0 . . ?
C16 C17 C24 119.77(15) . . ?
C16 C17 C18 134.59(15) . . ?
C24 C17 C18 105.62(13) . . ?
C23 C18 C19 119.15(16) . . ?
C23 C18 C17 105.88(13) . . ?
C19 C18 C17 134.94(16) . . ?
C20 C19 C18 117.94(18) . . ?
C20 C19 H19 121.0 . . ?
C18 C19 H19 121.0 . . ?
C19 C20 C21 121.59(17) . . ?
C19 C20 H20 119.2 . . ?
C21 C20 H20 119.2 . . ?
C20 C21 C22 122.06(18) . . ?
C20 C21 H21 119.0 . . ?
C22 C21 H21 119.0 . . ?
C23 C22 C21 115.41(18) . . ?
C23 C22 H22 122.3 . . ?
C21 C22 H22 122.3 . . ?
C22 C23 O3 124.65(15) . . ?
C22 C23 C18 123.82(15) . . ?
O3 C23 C18 111.52(13) . . ?
O3 C24 C13 124.78(13) . . ?
O3 C24 C17 111.44(13) . . ?
C13 C24 C17 123.78(14) . . ?
C6 N1 S1 118.94(10) . . ?
C6 N1 H1 120.5 . . ?
S1 N1 H1 120.5 . . ?
C1 N3 C5 117.19(15) . . ?
C24 O3 C23 105.49(11) . . ?
O1 S1 O2 119.98(8) . . ?
O1 S1 N1 107.11(7) . . ?
O2 S1 N1 105.67(8) . . ?
O1 S1 C7 108.35(7) . . ?
O2 S1 C7 108.64(7) . . ?
N1 S1 C7 106.29(7) . . ?

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
N3 C1 C2 C3 0.1(2) . . . . ?
C6 C1 C2 C3 179.04(15) . . . . ?
C1 C2 C3 C4 0.0(2) . . . . ?
C2 C3 C4 C5 -0.8(3) . . . . ?
C3 C4 C5 N3 1.5(3) . . . . ?
N3 C1 C6 N1 -171.65(13) . . . . ?
C2 C1 C6 N1 9.3(2) . . . . ?
C12 C7 C8 C9 -1.9(2) . . . . ?
S1 C7 C8 C9 172.80(12) . . . . ?
C7 C8 C9 C10 -0.8(2) . . . . ?
C8 C9 C10 C11 2.5(2) . . . . ?
C8 C9 C10 C13 178.10(14) . . . . ?
C9 C10 C11 C12 -1.5(2) . . . . ?
C13 C10 C11 C12 -177.07(14) . . . . ?
C10 C11 C12 C7 -1.2(2) . . . . ?
C8 C7 C12 C11 2.9(2) . . . . ?
S1 C7 C12 C11 -171.81(11) . . . . ?
C9 C10 C13 C24 144.84(15) . . . . ?
C11 C10 C13 C24 -39.6(2) . . . . ?
C9 C10 C13 C14 -36.8(2) . . . . ?
C11 C10 C13 C14 138.69(16) . . . . ?
C24 C13 C14 C15 1.3(3) . . . . ?
C10 C13 C14 C15 -177.15(17) . . . . ?
C13 C14 C15 C16 0.7(3) . . . . ?
C14 C15 C16 C17 -1.2(3) . . . . ?
C15 C16 C17 C24 -0.3(3) . . . . ?
C15 C16 C17 C18 -178.40(18) . . . . ?
C16 C17 C18 C23 176.13(18) . . . . ?
C24 C17 C18 C23 -2.13(16) . . . . ?
C16 C17 C18 C19 -5.8(3) . . . . ?
C24 C17 C18 C19 175.96(17) . . . . ?
C23 C18 C19 C20 -0.6(2) . . . . ?
C17 C18 C19 C20 -178.50(17) . . . . ?
C18 C19 C20 C21 -0.4(3) . . . . ?
C19 C20 C21 C22 0.4(3) . . . . ?
C20 C21 C22 C23 0.7(3) . . . . ?
C21 C22 C23 O3 176.87(15) . . . . ?
C21 C22 C23 C18 -1.8(3) . . . . ?
C19 C18 C23 C22 1.8(2) . . . . ?
C17 C18 C23 C22 -179.74(15) . . . . ?
C19 C18 C23 O3 -177.00(14) . . . . ?
C17 C18 C23 O3 1.44(17) . . . . ?
C14 C13 C24 O3 175.89(14) . . . . ?
C10 C13 C24 O3 -5.7(2) . . . . ?
C14 C13 C24 C17 -3.0(2) . . . . ?
C10 C13 C24 C17 175.45(14) . . . . ?
C16 C17 C24 O3 -176.41(14) . . . . ?
C18 C17 C24 O3 2.16(17) . . . . ?
C16 C17 C24 C13 2.6(2) . . . . ?
C18 C17 C24 C13 -178.85(14) . . . . ?
C1 C6 N1 S1 94.81(14) . . . . ?
C2 C1 N3 C5 0.6(2) . . . . ?
C6 C1 N3 C5 -178.46(14) . . . . ?
C4 C5 N3 C1 -1.4(3) . . . . ?
C13 C24 O3 C23 179.73(14) . . . . ?
C17 C24 O3 C23 -1.29(16) . . . . ?
C22 C23 O3 C24 -178.95(16) . . . . ?
C18 C23 O3 C24 -0.15(17) . . . . ?
C6 N1 S1 O1 -47.77(12) . . . . ?
C6 N1 S1 O2 -176.78(11) . . . . ?
C6 N1 S1 C7 67.89(12) . . . . ?
C8 C7 S1 O1 19.59(14) . . . . ?
C12 C7 S1 O1 -165.57(12) . . . . ?
C8 C7 S1 O2 151.46(13) . . . . ?
C12 C7 S1 O2 -33.70(14) . . . . ?
C8 C7 S1 N1 -95.24(13) . . . . ?
C12 C7 S1 N1 79.60(12) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1 N3 0.86 2.64 3.1107(19) 115.6 6_657

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        30.00
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.455
_refine_diff_density_min         -0.487
_refine_diff_density_rms         0.049
