# Electronic Supplementary Material (ESI) for Green Chemistry.
# 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_shelxl
_database_code_depnum_ccdc_archive 'CCDC 1039273'
_audit_update_record             
;
2014-12-14 deposited with the CCDC.
2015-12-09 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C28 H24 N2 O3 S'
_chemical_formula_sum            'C28 H24 N2 O3 S'
_chemical_formula_weight         468.55

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           triclinic
_symmetry_space_group_name_H-M   P-1

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

_cell_length_a                   9.0258(9)
_cell_length_b                   11.0099(10)
_cell_length_c                   12.4506(12)
_cell_angle_alpha                79.449(4)
_cell_angle_beta                 76.110(4)
_cell_angle_gamma                80.803(3)
_cell_volume                     1172.03(19)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    2977
_cell_measurement_theta_min      4.700
_cell_measurement_theta_max      55.373

_exptl_crystal_description       block
_exptl_crystal_colour            gold
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.30
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.328
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             492
_exptl_absorpt_coefficient_mu    0.172
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9424
_exptl_absorpt_correction_T_max  0.9503
_exptl_absorpt_process_details   'SADABS (Bruker, 1999)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(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 axs kappa apex2 CCD Diffractometer'
_diffrn_measurement_method       'ω and φ scan'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            9142
_diffrn_reflns_av_R_equivalents  0.0193
_diffrn_reflns_av_sigmaI/netI    0.0405
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         1.70
_diffrn_reflns_theta_max         28.26
_reflns_number_total             5609
_reflns_number_gt                3956
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'APEX2 (Bruker, 2004)'
_computing_cell_refinement       'APEX2/SAINT (Bruker, 2004)'
_computing_data_reduction        'SAINT/XPREP (Bruker, 2004)'
_computing_structure_solution    'SIR92 (Altornare et al., 1993)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    
'ORTEP3 (Farrugia, 1997) and Mercury (Bruno et al., 2002)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'

_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)+(0.0931P)²+0.0294P] 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         5609
_refine_ls_number_parameters     309
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0756
_refine_ls_R_factor_gt           0.0496
_refine_ls_wR_factor_ref         0.1625
_refine_ls_wR_factor_gt          0.1400
_refine_ls_goodness_of_fit_ref   1.068
_refine_ls_restrained_S_all      1.068
_refine_ls_shift/su_max          0.022
_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 0.64301(6) 0.51264(5) 0.33024(5) 0.05035(18) Uani 1 1 d . . .
O1 O 1.07847(19) 0.92023(12) 0.21429(13) 0.0542(4) Uani 1 1 d . . .
O2 O 1.0502(2) 0.81486(15) 0.08411(13) 0.0686(5) Uani 1 1 d . . .
O3 O 0.96242(19) 0.76817(14) 0.52434(12) 0.0574(4) Uani 1 1 d . . .
N1 N 0.83231(17) 0.61546(13) 0.41018(13) 0.0378(4) Uani 1 1 d . . .
N2 N 1.2731(2) 0.67673(18) 0.36070(17) 0.0551(5) Uani 1 1 d . . .
C1 C 1.5220(3) 0.2982(2) -0.0204(2) 0.0648(7) Uani 1 1 d . . .
H1A H 1.4927 0.2173 -0.0171 0.097 Uiso 1 1 calc R . .
H1B H 1.6115 0.2899 0.0104 0.097 Uiso 1 1 calc R . .
H1C H 1.5445 0.3378 -0.0969 0.097 Uiso 1 1 calc R . .
C2 C 1.3917(2) 0.37639(18) 0.04619(18) 0.0466(5) Uani 1 1 d . . .
C3 C 1.3826(2) 0.37862(18) 0.15882(18) 0.0480(5) Uani 1 1 d . . .
H3 H 1.4595 0.3330 0.1929 0.058 Uiso 1 1 calc R . .
C4 C 1.2615(2) 0.44735(18) 0.22136(17) 0.0433(5) Uani 1 1 d . . .
H4 H 1.2569 0.4456 0.2971 0.052 Uiso 1 1 calc R . .
C5 C 1.1476(2) 0.51845(16) 0.17279(15) 0.0352(4) Uani 1 1 d . . .
C6 C 1.0095(2) 0.59108(15) 0.23803(15) 0.0333(4) Uani 1 1 d . . .
H6 H 0.9338 0.6133 0.1907 0.040 Uiso 1 1 calc R . .
C7 C 1.0302(2) 0.71286(15) 0.27491(14) 0.0338(4) Uani 1 1 d . . .
C8 C 0.8721(2) 0.74074(16) 0.35969(15) 0.0347(4) Uani 1 1 d . . .
C9 C 0.7547(2) 0.83079(16) 0.30507(16) 0.0376(4) Uani 1 1 d . . .
C10 C 0.7180(2) 0.93782(16) 0.35794(16) 0.0361(4) Uani 1 1 d . . .
C11 C 0.6134(2) 1.03990(17) 0.32907(18) 0.0435(5) Uani 1 1 d . . .
C12 C 0.5907(2) 1.13912(18) 0.3915(2) 0.0509(5) Uani 1 1 d . . .
H12 H 0.5228 1.2093 0.3753 0.061 Uiso 1 1 calc R . .
C13 C 0.6661(2) 1.13369(19) 0.4747(2) 0.0510(5) Uani 1 1 d . . .
H13 H 0.6488 1.2009 0.5136 0.061 Uiso 1 1 calc R . .
C14 C 0.6852(3) 0.82668(19) 0.22045(19) 0.0516(5) Uani 1 1 d . . .
H14 H 0.7079 0.7581 0.1829 0.062 Uiso 1 1 calc R . .
C15 C 0.5775(3) 0.9282(2) 0.1903(2) 0.0620(6) Uani 1 1 d . . .
H15 H 0.5288 0.9241 0.1334 0.074 Uiso 1 1 calc R . .
C16 C 0.5426(3) 1.03173(19) 0.2414(2) 0.0572(6) Uani 1 1 d . . .
H16 H 0.4723 1.0969 0.2186 0.069 Uiso 1 1 calc R . .
C17 C 0.9300(2) 0.51909(16) 0.34825(15) 0.0353(4) Uani 1 1 d . . .
H17 H 1.0070 0.4752 0.3899 0.042 Uiso 1 1 calc R . .
C18 C 0.8296(2) 0.42682(17) 0.33295(19) 0.0451(5) Uani 1 1 d . . .
H18A H 0.8226 0.3582 0.3944 0.054 Uiso 1 1 calc R . .
H18B H 0.8724 0.3937 0.2635 0.054 Uiso 1 1 calc R . .
C19 C 0.6718(2) 0.59411(19) 0.43732(18) 0.0478(5) Uani 1 1 d . . .
H19A H 0.6057 0.6728 0.4383 0.057 Uiso 1 1 calc R . .
H19B H 0.6471 0.5442 0.5105 0.057 Uiso 1 1 calc R . .
C20 C 1.1641(2) 0.69364(17) 0.32742(16) 0.0384(4) Uani 1 1 d . . .
C21 C 1.0544(2) 0.82080(17) 0.17760(17) 0.0430(5) Uani 1 1 d . . .
C22 C 1.0895(4) 1.0349(2) 0.1342(2) 0.0884(10) Uani 1 1 d . . .
H22A H 1.1885 1.0296 0.0821 0.106 Uiso 1 1 calc R . .
H22B H 1.0100 1.0452 0.0917 0.106 Uiso 1 1 calc R . .
C23 C 1.0728(5) 1.1386(3) 0.1897(3) 0.1215(15) Uani 1 1 d . . .
H23A H 0.9666 1.1579 0.2247 0.182 Uiso 1 1 calc R . .
H23B H 1.1070 1.2088 0.1366 0.182 Uiso 1 1 calc R . .
H23C H 1.1334 1.1197 0.2457 0.182 Uiso 1 1 calc R . .
C24 C 1.2781(2) 0.4469(2) -0.00176(18) 0.0510(5) Uani 1 1 d . . .
H24 H 1.2815 0.4471 -0.0770 0.061 Uiso 1 1 calc R . .
C25 C 1.1579(2) 0.51813(19) 0.05996(16) 0.0432(5) Uani 1 1 d . . .
H25 H 1.0833 0.5663 0.0251 0.052 Uiso 1 1 calc R . .
C26 C 0.8884(2) 0.81125(17) 0.45489(16) 0.0387(4) Uani 1 1 d . . .
C27 C 0.7937(2) 0.93244(17) 0.44483(16) 0.0367(4) Uani 1 1 d . . .
C28 C 0.7690(2) 1.03053(18) 0.50405(18) 0.0442(5) Uani 1 1 d . . .
H28 H 0.8190 1.0283 0.5617 0.053 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 C18 1.799(2) . ?
S1 C19 1.824(2) . ?
O1 C21 1.327(2) . ?
O1 C22 1.459(3) . ?
O2 C21 1.188(2) . ?
O3 C26 1.202(2) . ?
N1 C19 1.454(2) . ?
N1 C8 1.469(2) . ?
N1 C17 1.474(2) . ?
N2 C20 1.133(3) . ?
C1 C2 1.510(3) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C2 C24 1.371(3) . ?
C2 C3 1.390(3) . ?
C3 C4 1.384(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.380(3) . ?
C4 H4 0.9300 . ?
C5 C25 1.386(3) . ?
C5 C6 1.512(2) . ?
C6 C17 1.529(2) . ?
C6 C7 1.546(2) . ?
C6 H6 0.9800 . ?
C7 C20 1.476(3) . ?
C7 C21 1.535(3) . ?
C7 C8 1.582(2) . ?
C8 C9 1.526(3) . ?
C8 C26 1.577(3) . ?
C9 C14 1.360(3) . ?
C9 C10 1.409(2) . ?
C10 C27 1.400(3) . ?
C10 C11 1.400(3) . ?
C11 C16 1.413(3) . ?
C11 C12 1.415(3) . ?
C12 C13 1.357(3) . ?
C12 H12 0.9300 . ?
C13 C28 1.400(3) . ?
C13 H13 0.9300 . ?
C14 C15 1.417(3) . ?
C14 H14 0.9300 . ?
C15 C16 1.363(3) . ?
C15 H15 0.9300 . ?
C16 H16 0.9300 . ?
C17 C18 1.529(3) . ?
C17 H17 0.9800 . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C22 C23 1.411(4) . ?
C22 H22A 0.9700 . ?
C22 H22B 0.9700 . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 0.9600 . ?
C24 C25 1.389(3) . ?
C24 H24 0.9300 . ?
C25 H25 0.9300 . ?
C26 C27 1.467(3) . ?
C27 C28 1.377(2) . ?
C28 H28 0.9300 . ?

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
C18 S1 C19 87.34(10) . . ?
C21 O1 C22 116.80(19) . . ?
C19 N1 C8 118.80(15) . . ?
C19 N1 C17 111.02(14) . . ?
C8 N1 C17 111.72(13) . . ?
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 . . ?
C24 C2 C3 117.68(17) . . ?
C24 C2 C1 121.4(2) . . ?
C3 C2 C1 120.9(2) . . ?
C4 C3 C2 121.3(2) . . ?
C4 C3 H3 119.3 . . ?
C2 C3 H3 119.3 . . ?
C5 C4 C3 120.83(19) . . ?
C5 C4 H4 119.6 . . ?
C3 C4 H4 119.6 . . ?
C4 C5 C25 117.91(16) . . ?
C4 C5 C6 123.04(16) . . ?
C25 C5 C6 118.98(17) . . ?
C5 C6 C17 114.92(14) . . ?
C5 C6 C7 119.02(14) . . ?
C17 C6 C7 102.00(14) . . ?
C5 C6 H6 106.7 . . ?
C17 C6 H6 106.7 . . ?
C7 C6 H6 106.7 . . ?
C20 C7 C21 107.61(15) . . ?
C20 C7 C6 110.54(14) . . ?
C21 C7 C6 113.13(15) . . ?
C20 C7 C8 113.05(15) . . ?
C21 C7 C8 110.60(14) . . ?
C6 C7 C8 101.96(13) . . ?
N1 C8 C9 118.03(15) . . ?
N1 C8 C26 108.77(14) . . ?
C9 C8 C26 102.17(13) . . ?
N1 C8 C7 102.72(13) . . ?
C9 C8 C7 112.87(14) . . ?
C26 C8 C7 112.56(14) . . ?
C14 C9 C10 118.09(18) . . ?
C14 C9 C8 133.50(16) . . ?
C10 C9 C8 108.41(16) . . ?
C27 C10 C11 122.29(17) . . ?
C27 C10 C9 113.79(17) . . ?
C11 C10 C9 123.90(18) . . ?
C10 C11 C16 116.32(17) . . ?
C10 C11 C12 116.0(2) . . ?
C16 C11 C12 127.7(2) . . ?
C13 C12 C11 121.2(2) . . ?
C13 C12 H12 119.4 . . ?
C11 C12 H12 119.4 . . ?
C12 C13 C28 122.36(19) . . ?
C12 C13 H13 118.8 . . ?
C28 C13 H13 118.8 . . ?
C9 C14 C15 119.15(19) . . ?
C9 C14 H14 120.4 . . ?
C15 C14 H14 120.4 . . ?
C16 C15 C14 122.6(2) . . ?
C16 C15 H15 118.7 . . ?
C14 C15 H15 118.7 . . ?
C15 C16 C11 119.9(2) . . ?
C15 C16 H16 120.0 . . ?
C11 C16 H16 120.0 . . ?
N1 C17 C18 109.30(14) . . ?
N1 C17 C6 104.69(13) . . ?
C18 C17 C6 113.50(16) . . ?
N1 C17 H17 109.7 . . ?
C18 C17 H17 109.7 . . ?
C6 C17 H17 109.7 . . ?
C17 C18 S1 106.18(12) . . ?
C17 C18 H18A 110.5 . . ?
S1 C18 H18A 110.5 . . ?
C17 C18 H18B 110.5 . . ?
S1 C18 H18B 110.5 . . ?
H18A C18 H18B 108.7 . . ?
N1 C19 S1 107.52(12) . . ?
N1 C19 H19A 110.2 . . ?
S1 C19 H19A 110.2 . . ?
N1 C19 H19B 110.2 . . ?
S1 C19 H19B 110.2 . . ?
H19A C19 H19B 108.5 . . ?
N2 C20 C7 175.1(2) . . ?
O2 C21 O1 125.90(19) . . ?
O2 C21 C7 124.24(18) . . ?
O1 C21 C7 109.85(17) . . ?
C23 C22 O1 110.7(3) . . ?
C23 C22 H22A 109.5 . . ?
O1 C22 H22A 109.5 . . ?
C23 C22 H22B 109.5 . . ?
O1 C22 H22B 109.5 . . ?
H22A C22 H22B 108.1 . . ?
C22 C23 H23A 109.5 . . ?
C22 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
C22 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C2 C24 C25 121.27(19) . . ?
C2 C24 H24 119.4 . . ?
C25 C24 H24 119.4 . . ?
C5 C25 C24 121.0(2) . . ?
C5 C25 H25 119.5 . . ?
C24 C25 H25 119.5 . . ?
O3 C26 C27 127.77(18) . . ?
O3 C26 C8 124.28(16) . . ?
C27 C26 C8 107.90(16) . . ?
C28 C27 C10 120.21(18) . . ?
C28 C27 C26 132.17(19) . . ?
C10 C27 C26 107.61(15) . . ?
C27 C28 C13 117.9(2) . . ?
C27 C28 H28 121.1 . . ?
C13 C28 H28 121.1 . . ?

_diffrn_measured_fraction_theta_max 0.968
_diffrn_reflns_theta_full        28.26
_diffrn_measured_fraction_theta_full 0.968
_refine_diff_density_max         0.331
_refine_diff_density_min         -0.302
_refine_diff_density_rms         0.088
