# 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 2014

####################################################################### 
# 
# 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/. 
# 
# 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_collect_0m
_database_code_depnum_ccdc_archive 'CCDC 1033127'
_audit_update_record             
;
2014-11-06 deposited with the CCDC.
2014-12-11 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C16 H17 N O4 S'
_chemical_formula_weight         319.37

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                   15.7805(9)
_cell_length_b                   5.0908(3)
_cell_length_c                   21.0600(13)
_cell_angle_alpha                90.00
_cell_angle_beta                 110.8510(10)
_cell_angle_gamma                90.00
_cell_volume                     1581.06(16)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    4566
_cell_measurement_theta_min      2.76
_cell_measurement_theta_max      28.21

_exptl_crystal_description       Plate
_exptl_crystal_colour            Yellow
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.04
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.342
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             672
_exptl_absorpt_coefficient_mu    0.222
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9245
_exptl_absorpt_correction_T_max  0.9912
_exptl_absorpt_process_details   '(SADABS 2007/4 Bruker)'

_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 SMART APEX2 CCD diffractometer'
_diffrn_measurement_method       'omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            15173
_diffrn_reflns_av_R_equivalents  0.0255
_diffrn_reflns_av_sigmaI/netI    0.0248
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_theta_min         1.38
_diffrn_reflns_theta_max         28.00
_reflns_number_total             3809
_reflns_number_gt                2912
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'APEX2 v2.2-0 (Bruker, 2007)'
_computing_cell_refinement       'SAINT+  V7.46A (Bruker, 2007)'
_computing_data_reduction        'SAINT+  V7.46A (Bruker, 2007)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'XSHELL v4.02 (Bruker, 2000)'
_computing_publication_material  'XCIF v6.12 (Bruker, 2001)'

_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)+(0.0408P)²+0.4170P] 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         3809
_refine_ls_number_parameters     202
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0523
_refine_ls_R_factor_gt           0.0380
_refine_ls_wR_factor_ref         0.1034
_refine_ls_wR_factor_gt          0.0949
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_restrained_S_all      1.038
_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 0.39156(3) 0.31316(8) 0.43693(2) 0.05223(13) Uani 1 1 d . . .
C9 C 0.24822(10) 0.5458(3) 0.46000(7) 0.0411(3) Uani 1 1 d . . .
O1 O 0.06011(7) 0.8977(2) 0.33072(6) 0.0583(3) Uani 1 1 d . . .
C10 C 0.20149(10) 0.7264(3) 0.40961(7) 0.0420(3) Uani 1 1 d . . .
H10 H 0.2347 0.8475 0.3949 0.050 Uiso 1 1 calc R . .
C11 C 0.10823(10) 0.7318(3) 0.38085(7) 0.0449(3) Uani 1 1 d . . .
C1 C 0.38181(10) 0.4961(3) 0.36279(8) 0.0453(3) Uani 1 1 d . . .
C14 C 0.19497(11) 0.3739(3) 0.48098(7) 0.0456(3) Uani 1 1 d . . .
C8 C 0.34989(10) 0.5508(3) 0.48389(7) 0.0455(3) Uani 1 1 d . . .
H8A H 0.3748 0.5099 0.5320 0.055 Uiso 1 1 calc R . .
H8B H 0.3701 0.7255 0.4775 0.055 Uiso 1 1 calc R . .
N1 N 0.23532(12) 0.1757(3) 0.53345(7) 0.0578(4) Uani 1 1 d . . .
C13 C 0.10055(11) 0.3780(3) 0.45343(8) 0.0518(4) Uani 1 1 d . . .
H13 H 0.0673 0.2617 0.4694 0.062 Uiso 1 1 calc R . .
C12 C 0.05657(10) 0.5526(4) 0.40294(8) 0.0508(4) Uani 1 1 d . . .
O2 O -0.03482(8) 0.5695(3) 0.37077(7) 0.0713(4) Uani 1 1 d . . .
O3 O 0.31483(10) 0.1165(3) 0.54833(7) 0.0707(4) Uani 1 1 d . . .
C4 C 0.37208(12) 0.7595(3) 0.24344(9) 0.0541(4) Uani 1 1 d . . .
C6 C 0.32062(12) 0.4191(4) 0.30007(8) 0.0556(4) Uani 1 1 d . . .
H6 H 0.2822 0.2777 0.2974 0.067 Uiso 1 1 calc R . .
C2 C 0.43760(11) 0.7083(3) 0.36538(8) 0.0524(4) Uani 1 1 d . . .
H2 H 0.4788 0.7645 0.4069 0.063 Uiso 1 1 calc R . .
O4 O 0.18649(11) 0.0741(3) 0.56033(8) 0.0949(5) Uani 1 1 d . . .
C15 C 0.11027(13) 1.0622(4) 0.30161(9) 0.0645(5) Uani 1 1 d . . .
H15A H 0.1485 1.1780 0.3358 0.097 Uiso 1 1 calc R . .
H15B H 0.0689 1.1639 0.2654 0.097 Uiso 1 1 calc R . .
H15C H 0.1470 0.9550 0.2841 0.097 Uiso 1 1 calc R . .
C16 C -0.08863(14) 0.3642(5) 0.38334(12) 0.0831(7) Uani 1 1 d . . .
H16A H -0.0689 0.1979 0.3722 0.125 Uiso 1 1 calc R . .
H16B H -0.1512 0.3915 0.3558 0.125 Uiso 1 1 calc R . .
H16C H -0.0820 0.3655 0.4305 0.125 Uiso 1 1 calc R . .
C3 C 0.43230(12) 0.8370(4) 0.30643(10) 0.0599(4) Uani 1 1 d . . .
H3 H 0.4702 0.9796 0.3090 0.072 Uiso 1 1 calc R . .
C5 C 0.31602(12) 0.5497(4) 0.24155(8) 0.0583(4) Uani 1 1 d . . .
H5 H 0.2743 0.4952 0.2000 0.070 Uiso 1 1 calc R . .
C7 C 0.36810(16) 0.8980(4) 0.17885(10) 0.0779(6) Uani 1 1 d . . .
H7A H 0.3374 0.7883 0.1404 0.117 Uiso 1 1 calc R . .
H7B H 0.4286 0.9329 0.1804 0.117 Uiso 1 1 calc R . .
H7C H 0.3358 1.0606 0.1748 0.117 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 0.0621(3) 0.0446(2) 0.0524(2) 0.00349(18) 0.02331(19) 0.00959(19)
C9 0.0502(8) 0.0388(8) 0.0355(7) -0.0057(6) 0.0165(6) -0.0016(6)
O1 0.0494(6) 0.0612(7) 0.0556(7) 0.0089(6) 0.0079(5) -0.0007(6)
C10 0.0467(8) 0.0395(8) 0.0403(7) -0.0017(6) 0.0161(6) -0.0050(6)
C11 0.0480(8) 0.0443(8) 0.0404(7) -0.0031(6) 0.0134(6) -0.0019(7)
C1 0.0456(8) 0.0441(8) 0.0492(8) -0.0013(7) 0.0206(7) 0.0053(7)
C14 0.0601(9) 0.0432(8) 0.0359(7) -0.0011(6) 0.0200(7) -0.0035(7)
C8 0.0486(8) 0.0442(8) 0.0408(7) -0.0041(6) 0.0122(6) -0.0009(7)
N1 0.0804(11) 0.0516(8) 0.0432(7) 0.0032(6) 0.0243(7) -0.0048(8)
C13 0.0604(10) 0.0546(9) 0.0480(8) -0.0040(7) 0.0286(8) -0.0129(8)
C12 0.0438(8) 0.0602(10) 0.0496(8) -0.0081(8) 0.0180(7) -0.0082(7)
O2 0.0453(6) 0.0901(10) 0.0764(8) 0.0027(8) 0.0191(6) -0.0119(7)
O3 0.0827(10) 0.0628(8) 0.0622(8) 0.0148(6) 0.0203(7) 0.0108(7)
C4 0.0607(10) 0.0521(10) 0.0555(9) 0.0021(8) 0.0281(8) 0.0084(8)
C6 0.0566(10) 0.0546(10) 0.0551(9) -0.0060(8) 0.0193(8) -0.0098(8)
C2 0.0475(9) 0.0513(9) 0.0547(9) -0.0030(8) 0.0136(7) -0.0015(7)
O4 0.1063(12) 0.1045(12) 0.0857(10) 0.0431(9) 0.0485(9) -0.0049(10)
C15 0.0711(11) 0.0632(11) 0.0536(10) 0.0151(9) 0.0154(9) 0.0022(9)
C16 0.0571(11) 0.1070(18) 0.0923(15) -0.0144(13) 0.0352(11) -0.0295(12)
C3 0.0578(10) 0.0535(10) 0.0713(11) 0.0026(9) 0.0264(9) -0.0067(8)
C5 0.0643(10) 0.0612(11) 0.0460(9) -0.0054(8) 0.0154(8) -0.0020(9)
C7 0.1010(16) 0.0754(14) 0.0672(12) 0.0132(10) 0.0422(12) 0.0065(12)

_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 C1 1.7771(16) . ?
S1 C8 1.8267(15) . ?
C9 C14 1.390(2) . ?
C9 C10 1.399(2) . ?
C9 C8 1.501(2) . ?
O1 C11 1.3540(18) . ?
O1 C15 1.431(2) . ?
C10 C11 1.378(2) . ?
C11 C12 1.408(2) . ?
C1 C2 1.382(2) . ?
C1 C6 1.387(2) . ?
C14 C13 1.393(2) . ?
C14 N1 1.464(2) . ?
N1 O3 1.2179(19) . ?
N1 O4 1.2217(19) . ?
C13 C12 1.370(2) . ?
C12 O2 1.3603(19) . ?
O2 C16 1.429(2) . ?
C4 C5 1.378(3) . ?
C4 C3 1.386(2) . ?
C4 C7 1.513(2) . ?
C6 C5 1.379(2) . ?
C2 C3 1.380(2) . ?

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
C1 S1 C8 101.15(7) . . ?
C14 C9 C10 116.08(14) . . ?
C14 C9 C8 126.82(14) . . ?
C10 C9 C8 117.06(13) . . ?
C11 O1 C15 117.17(13) . . ?
C11 C10 C9 122.59(14) . . ?
O1 C11 C10 124.75(14) . . ?
O1 C11 C12 115.57(14) . . ?
C10 C11 C12 119.67(14) . . ?
C2 C1 C6 118.43(15) . . ?
C2 C1 S1 121.35(12) . . ?
C6 C1 S1 120.14(13) . . ?
C9 C14 C13 122.43(14) . . ?
C9 C14 N1 121.60(14) . . ?
C13 C14 N1 115.96(14) . . ?
C9 C8 S1 110.79(10) . . ?
O3 N1 O4 122.54(16) . . ?
O3 N1 C14 119.75(14) . . ?
O4 N1 C14 117.71(17) . . ?
C12 C13 C14 120.26(14) . . ?
O2 C12 C13 125.57(15) . . ?
O2 C12 C11 115.49(15) . . ?
C13 C12 C11 118.93(14) . . ?
C12 O2 C16 117.14(16) . . ?
C5 C4 C3 117.55(16) . . ?
C5 C4 C7 120.94(17) . . ?
C3 C4 C7 121.51(17) . . ?
C5 C6 C1 120.82(16) . . ?
C3 C2 C1 120.12(16) . . ?
C2 C3 C4 121.84(17) . . ?
C4 C5 C6 121.23(16) . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        28.00
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.227
_refine_diff_density_min         -0.161
_refine_diff_density_rms         0.033
