# Electronic Supplementary Material (ESI) for RSC Advances
# This journal is © The Royal Society of Chemistry 2013


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#                                CCDC 
# 
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# 
#  This CIF contains data from an original supplementary publication 
#  deposited with the CCDC, and may include chemical, crystal,   
#  experimental, refinement, atomic coordinates, 
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted. 
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data_a20423a
_database_code_depnum_ccdc_archive 'CCDC 902005'
#TrackingRef 'a20423a.cif'
_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C30 H23 N O2 S'
_chemical_formula_weight         461.55
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   P2(1)/c
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
_cell_length_a                   12.023(8)
_cell_length_b                   12.412(8)
_cell_length_c                   16.806(11)
_cell_angle_alpha                90.00
_cell_angle_beta                 109.855(7)
_cell_angle_gamma                90.00
_cell_volume                     2359(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    Monoclinic
_cell_measurement_theta_min      P2(1)/c
_cell_measurement_theta_max      882
_exptl_crystal_description       polyhedral
_exptl_crystal_colour            orange
_exptl_crystal_size_max          0.55
_exptl_crystal_size_mid          0.54
_exptl_crystal_size_min          0.25
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.300
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             968
_exptl_absorpt_coefficient_mu    0.165
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9145
_exptl_absorpt_correction_T_max  0.9598
_exptl_absorpt_process_details   sadabs
_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  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            9941
_diffrn_reflns_av_R_equivalents  0.0513
_diffrn_reflns_av_sigmaI/netI    0.0472
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         1.80
_diffrn_reflns_theta_max         25.51
_reflns_number_total             4400
_reflns_number_gt                3458
_reflns_threshold_expression     >2sigma(I)
_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_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 F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ 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/[\s^2^(Fo^2^)+(0.0800P)^2^+0.0967P] where P=(Fo^2^+2Fc^2^)/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     SHELXL
_refine_ls_extinction_coef       0.043(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_number_reflns         4400
_refine_ls_number_parameters     310
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0623
_refine_ls_R_factor_gt           0.0498
_refine_ls_wR_factor_ref         0.1336
_refine_ls_wR_factor_gt          0.1251
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_restrained_S_all      1.065
_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 0.93731(4) 0.51248(4) 0.24849(3) 0.04216(19) Uani 1 1 d . . .
N1 N 0.98617(12) 0.62135(12) 0.30518(10) 0.0403(4) Uani 1 1 d . . .
O1 O 0.91614(12) 0.43278(10) 0.30230(9) 0.0486(4) Uani 1 1 d . . .
O2 O 1.01779(12) 0.49028(12) 0.20496(10) 0.0576(4) Uani 1 1 d . . .
C1 C 0.80323(16) 0.55488(15) 0.17498(12) 0.0412(4) Uani 1 1 d . . .
C2 C 0.78688(19) 0.55402(19) 0.08951(13) 0.0544(5) Uani 1 1 d . . .
H2 H 0.8468 0.5297 0.0707 0.065 Uiso 1 1 calc R . .
C3 C 0.6812(2) 0.5894(2) 0.03234(14) 0.0598(6) Uani 1 1 d . . .
H3 H 0.6695 0.5876 -0.0253 0.072 Uiso 1 1 calc R . .
C4 C 0.59204(17) 0.62753(17) 0.05987(13) 0.0506(5) Uani 1 1 d . . .
C5 C 0.61111(16) 0.62876(15) 0.14566(12) 0.0417(4) Uani 1 1 d . . .
H5 H 0.5517 0.6553 0.1641 0.050 Uiso 1 1 calc R . .
C6 C 0.71561(15) 0.59195(14) 0.20589(11) 0.0362(4) Uani 1 1 d . . .
C7 C 0.4772(2) 0.6676(2) -0.00266(14) 0.0681(7) Uani 1 1 d . . .
H7A H 0.4781 0.7448 -0.0044 0.102 Uiso 1 1 calc R . .
H7B H 0.4126 0.6439 0.0144 0.102 Uiso 1 1 calc R . .
H7C H 0.4677 0.6394 -0.0578 0.102 Uiso 1 1 calc R . .
C8 C 0.72904(14) 0.59254(14) 0.29656(11) 0.0343(4) Uani 1 1 d . . .
C9 C 0.63937(14) 0.56734(14) 0.32559(11) 0.0357(4) Uani 1 1 d . . .
C10 C 0.67602(15) 0.59027(14) 0.41594(11) 0.0367(4) Uani 1 1 d . . .
C11 C 0.79290(15) 0.63012(13) 0.44303(11) 0.0359(4) Uani 1 1 d . . .
C12 C 0.83194(14) 0.63042(13) 0.36843(11) 0.0343(4) Uani 1 1 d . . .
C13 C 0.52582(15) 0.51294(15) 0.27970(11) 0.0389(4) Uani 1 1 d . . .
C14 C 0.52688(19) 0.41460(17) 0.24109(12) 0.0508(5) Uani 1 1 d . . .
H14 H 0.5979 0.3866 0.2396 0.061 Uiso 1 1 calc R . .
C15 C 0.4229(2) 0.3579(2) 0.20478(15) 0.0692(7) Uani 1 1 d . . .
H15 H 0.4247 0.2915 0.1796 0.083 Uiso 1 1 calc R . .
C16 C 0.3181(2) 0.3983(2) 0.20556(15) 0.0739(8) Uani 1 1 d . . .
H16 H 0.2485 0.3597 0.1812 0.089 Uiso 1 1 calc R . .
C17 C 0.31547(18) 0.4958(2) 0.24227(15) 0.0641(7) Uani 1 1 d . . .
H17 H 0.2437 0.5238 0.2422 0.077 Uiso 1 1 calc R . .
C18 C 0.41854(16) 0.55339(18) 0.27958(13) 0.0509(5) Uani 1 1 d . . .
H18 H 0.4157 0.6196 0.3047 0.061 Uiso 1 1 calc R . .
C19 C 0.61672(17) 0.57488(17) 0.47235(12) 0.0474(5) Uani 1 1 d . . .
H19 H 0.5396 0.5489 0.4538 0.057 Uiso 1 1 calc R . .
C20 C 0.67343(19) 0.59853(18) 0.55672(13) 0.0527(5) Uani 1 1 d . . .
H20 H 0.6335 0.5907 0.5951 0.063 Uiso 1 1 calc R . .
C21 C 0.78936(19) 0.63380(17) 0.58441(13) 0.0510(5) Uani 1 1 d . . .
H21 H 0.8272 0.6474 0.6417 0.061 Uiso 1 1 calc R . .
C22 C 0.84989(16) 0.64914(16) 0.52898(11) 0.0426(4) Uani 1 1 d . . .
H22 H 0.9282 0.6720 0.5488 0.051 Uiso 1 1 calc R . .
C23 C 0.94348(15) 0.65240(14) 0.37006(11) 0.0362(4) Uani 1 1 d . . .
C24 C 1.03401(15) 0.70494(14) 0.44223(12) 0.0387(4) Uani 1 1 d . . .
C25 C 1.01760(18) 0.80686(16) 0.47017(13) 0.0502(5) Uani 1 1 d . . .
H25 H 0.9488 0.8450 0.4421 0.060 Uiso 1 1 calc R . .
C26 C 1.1021(2) 0.85175(18) 0.53884(14) 0.0593(6) Uani 1 1 d . . .
H26 H 1.0901 0.9201 0.5571 0.071 Uiso 1 1 calc R . .
C27 C 1.2038(2) 0.7968(2) 0.58075(15) 0.0685(7) Uani 1 1 d . . .
H27 H 1.2605 0.8277 0.6275 0.082 Uiso 1 1 calc R . .
C28 C 1.2222(2) 0.6966(2) 0.55378(15) 0.0689(7) Uani 1 1 d . . .
H28 H 1.2911 0.6591 0.5826 0.083 Uiso 1 1 calc R . .
C29 C 1.13910(17) 0.65110(17) 0.48420(14) 0.0521(5) Uani 1 1 d . . .
H29 H 1.1532 0.5839 0.4651 0.062 Uiso 1 1 calc R . .
C30 C 1.0510(2) 0.70140(19) 0.27255(16) 0.0637(6) Uani 1 1 d . . .
H30A H 1.0398 0.7719 0.2921 0.096 Uiso 1 1 calc R . .
H30B H 1.0215 0.7002 0.2118 0.096 Uiso 1 1 calc R . .
H30C H 1.1337 0.6841 0.2926 0.096 Uiso 1 1 calc R . .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
S1 0.0341(3) 0.0409(3) 0.0511(3) -0.0066(2) 0.0140(2) 0.00110(18)
N1 0.0327(7) 0.0395(9) 0.0511(9) -0.0027(7) 0.0172(7) -0.0041(6)
O1 0.0474(7) 0.0340(7) 0.0614(9) -0.0006(6) 0.0145(7) 0.0000(6)
O2 0.0429(8) 0.0670(10) 0.0670(10) -0.0136(7) 0.0239(7) 0.0042(7)
C1 0.0375(9) 0.0413(11) 0.0446(10) -0.0063(8) 0.0136(8) -0.0051(8)
C2 0.0493(11) 0.0709(14) 0.0471(11) -0.0080(10) 0.0217(10) -0.0033(10)
C3 0.0590(13) 0.0823(16) 0.0371(10) -0.0022(10) 0.0149(10) -0.0068(12)
C4 0.0460(11) 0.0572(13) 0.0436(11) 0.0031(9) 0.0085(9) -0.0087(9)
C5 0.0360(9) 0.0439(11) 0.0438(10) 0.0019(8) 0.0119(8) -0.0024(8)
C6 0.0325(9) 0.0337(9) 0.0407(10) -0.0023(7) 0.0103(8) -0.0060(7)
C7 0.0558(13) 0.0871(18) 0.0505(13) 0.0113(12) 0.0040(11) -0.0021(12)
C8 0.0300(8) 0.0323(9) 0.0391(9) -0.0002(7) 0.0096(7) 0.0009(7)
C9 0.0313(8) 0.0332(9) 0.0403(10) 0.0018(7) 0.0094(7) 0.0000(7)
C10 0.0328(9) 0.0352(9) 0.0398(10) 0.0020(7) 0.0095(7) -0.0002(7)
C11 0.0333(8) 0.0312(9) 0.0409(10) 0.0014(7) 0.0095(8) 0.0000(7)
C12 0.0302(8) 0.0312(9) 0.0389(9) 0.0015(7) 0.0084(7) 0.0013(7)
C13 0.0335(9) 0.0436(11) 0.0359(9) 0.0054(8) 0.0072(8) -0.0059(7)
C14 0.0508(11) 0.0469(12) 0.0488(11) 0.0009(9) 0.0091(9) -0.0089(9)
C15 0.0803(18) 0.0577(15) 0.0565(14) -0.0044(11) 0.0059(12) -0.0293(13)
C16 0.0585(15) 0.088(2) 0.0553(14) 0.0165(13) -0.0066(12) -0.0381(14)
C17 0.0319(10) 0.091(2) 0.0604(14) 0.0272(13) 0.0043(10) -0.0095(11)
C18 0.0363(10) 0.0621(13) 0.0519(12) 0.0115(10) 0.0118(9) -0.0016(9)
C19 0.0400(10) 0.0548(12) 0.0482(11) 0.0030(9) 0.0162(9) -0.0066(9)
C20 0.0549(12) 0.0625(13) 0.0446(11) 0.0030(10) 0.0219(10) -0.0059(10)
C21 0.0546(12) 0.0559(13) 0.0388(10) -0.0033(9) 0.0109(9) -0.0049(10)
C22 0.0379(9) 0.0434(11) 0.0421(10) -0.0021(8) 0.0077(8) -0.0035(8)
C23 0.0328(8) 0.0294(9) 0.0445(10) 0.0030(7) 0.0107(8) 0.0010(7)
C24 0.0333(9) 0.0343(10) 0.0474(10) -0.0003(8) 0.0121(8) -0.0056(7)
C25 0.0461(10) 0.0387(11) 0.0605(13) -0.0040(9) 0.0111(10) 0.0006(9)
C26 0.0664(14) 0.0445(12) 0.0643(14) -0.0153(10) 0.0185(12) -0.0129(10)
C27 0.0602(14) 0.0727(17) 0.0587(14) -0.0155(12) 0.0023(12) -0.0212(13)
C28 0.0489(12) 0.0688(17) 0.0683(15) -0.0032(12) -0.0070(11) 0.0025(11)
C29 0.0430(11) 0.0415(11) 0.0625(13) -0.0028(9) 0.0060(10) 0.0010(9)
C30 0.0725(15) 0.0543(13) 0.0765(15) -0.0041(11) 0.0410(13) -0.0184(11)
_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 1.4204(16) . ?
S1 O2 1.4242(16) . ?
S1 N1 1.6426(17) . ?
S1 C1 1.746(2) . ?
N1 C23 1.408(2) . ?
N1 C30 1.478(3) . ?
C1 C2 1.382(3) . ?
C1 C6 1.401(3) . ?
C2 C3 1.379(3) . ?
C3 C4 1.387(3) . ?
C4 C5 1.381(3) . ?
C4 C7 1.507(3) . ?
C5 C6 1.396(3) . ?
C6 C8 1.477(3) . ?
C8 C9 1.362(2) . ?
C8 C12 1.482(2) . ?
C9 C10 1.458(3) . ?
C9 C13 1.483(2) . ?
C10 C19 1.379(3) . ?
C10 C11 1.411(3) . ?
C11 C22 1.393(3) . ?
C11 C12 1.481(3) . ?
C12 C23 1.360(2) . ?
C13 C18 1.384(3) . ?
C13 C14 1.384(3) . ?
C14 C15 1.383(3) . ?
C15 C16 1.362(4) . ?
C16 C17 1.363(4) . ?
C17 C18 1.383(3) . ?
C19 C20 1.380(3) . ?
C20 C21 1.382(3) . ?
C21 C22 1.376(3) . ?
C23 C24 1.478(2) . ?
C24 C25 1.387(3) . ?
C24 C29 1.391(3) . ?
C25 C26 1.370(3) . ?
C26 C27 1.368(3) . ?
C27 C28 1.368(4) . ?
C28 C29 1.375(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
O1 S1 O2 119.49(9) . . ?
O1 S1 N1 108.05(9) . . ?
O2 S1 N1 106.59(9) . . ?
O1 S1 C1 109.78(9) . . ?
O2 S1 C1 108.65(10) . . ?
N1 S1 C1 102.99(9) . . ?
C23 N1 C30 118.70(16) . . ?
C23 N1 S1 121.46(12) . . ?
C30 N1 S1 117.87(14) . . ?
C2 C1 C6 121.90(18) . . ?
C2 C1 S1 120.29(15) . . ?
C6 C1 S1 117.79(14) . . ?
C3 C2 C1 119.6(2) . . ?
C2 C3 C4 120.7(2) . . ?
C5 C4 C3 118.62(19) . . ?
C5 C4 C7 120.8(2) . . ?
C3 C4 C7 120.6(2) . . ?
C4 C5 C6 122.89(18) . . ?
C5 C6 C1 116.33(17) . . ?
C5 C6 C8 120.18(16) . . ?
C1 C6 C8 123.49(16) . . ?
C9 C8 C6 123.09(15) . . ?
C9 C8 C12 108.91(16) . . ?
C6 C8 C12 127.67(15) . . ?
C8 C9 C10 109.40(15) . . ?
C8 C9 C13 128.25(16) . . ?
C10 C9 C13 121.98(15) . . ?
C19 C10 C11 121.14(17) . . ?
C19 C10 C9 130.15(16) . . ?
C11 C10 C9 108.66(15) . . ?
C22 C11 C10 118.63(17) . . ?
C22 C11 C12 133.80(16) . . ?
C10 C11 C12 107.16(15) . . ?
C23 C12 C11 125.28(16) . . ?
C23 C12 C8 128.67(17) . . ?
C11 C12 C8 105.81(14) . . ?
C18 C13 C14 118.44(18) . . ?
C18 C13 C9 121.92(18) . . ?
C14 C13 C9 119.46(17) . . ?
C15 C14 C13 120.3(2) . . ?
C16 C15 C14 120.6(2) . . ?
C15 C16 C17 119.7(2) . . ?
C16 C17 C18 120.6(2) . . ?
C17 C18 C13 120.3(2) . . ?
C10 C19 C20 119.10(18) . . ?
C19 C20 C21 120.20(19) . . ?
C22 C21 C20 121.37(19) . . ?
C21 C22 C11 119.45(18) . . ?
C12 C23 N1 123.10(16) . . ?
C12 C23 C24 123.47(17) . . ?
N1 C23 C24 113.32(15) . . ?
C25 C24 C29 118.41(17) . . ?
C25 C24 C23 122.05(16) . . ?
C29 C24 C23 119.54(17) . . ?
C26 C25 C24 120.41(19) . . ?
C27 C26 C25 120.6(2) . . ?
C28 C27 C26 120.0(2) . . ?
C27 C28 C29 120.2(2) . . ?
C28 C29 C24 120.4(2) . . ?
_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        25.51
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.308
_refine_diff_density_min         -0.421
_refine_diff_density_rms         0.089