# 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_shelxl
_database_code_depnum_ccdc_archive 'CCDC 1400823'
_audit_update_record             
;
2015-05-14 deposited with the CCDC.
2015-06-26 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 H27 N O3 S'
_chemical_formula_weight         421.54

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                   14.198(3)
_cell_length_b                   6.0639(12)
_cell_length_c                   25.178(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 100.14(3)
_cell_angle_gamma                90.00
_cell_volume                     2133.9(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    113(2)
_cell_measurement_reflns_used    5461
_cell_measurement_theta_min      1.4570
_cell_measurement_theta_max      27.9304

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_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    1.312
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             896
_exptl_absorpt_coefficient_mu    0.179
_exptl_absorpt_correction_type   MULTI-SCAN
_exptl_absorpt_correction_T_min  0.9651
_exptl_absorpt_correction_T_max  0.9789
_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            15871
_diffrn_reflns_av_R_equivalents  0.0444
_diffrn_reflns_av_sigmaI/netI    0.0463
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_theta_min         1.46
_diffrn_reflns_theta_max         27.94
_reflns_number_total             5063
_reflns_number_gt                4074
_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)+(0.0819P)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    CONSTR
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.014(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         5063
_refine_ls_number_parameters     275
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0551
_refine_ls_R_factor_gt           0.0443
_refine_ls_wR_factor_ref         0.1284
_refine_ls_wR_factor_gt          0.1187
_refine_ls_goodness_of_fit_ref   1.011
_refine_ls_restrained_S_all      1.011
_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 0.08564(3) 0.53921(6) 0.108695(15) 0.01557(13) Uani 1 1 d . . .
O1 O 0.08763(8) 0.77652(17) 0.10947(4) 0.0214(3) Uani 1 1 d . . .
O2 O 0.00256(8) 0.42444(18) 0.08065(4) 0.0206(3) Uani 1 1 d . . .
O3 O 0.16759(8) 0.35701(17) -0.02852(4) 0.0201(3) Uani 1 1 d . . .
H3 H 0.1225 0.4372 -0.0436 0.030 Uiso 1 1 calc R . .
N1 N 0.17485(9) 0.45946(19) 0.08159(5) 0.0150(3) Uani 1 1 d . . .
C1 C 0.10189(11) 0.4508(2) 0.17650(6) 0.0159(3) Uani 1 1 d . . .
C2 C 0.06814(11) 0.2441(2) 0.18899(6) 0.0195(3) Uani 1 1 d . . .
H2 H 0.0355 0.1513 0.1613 0.023 Uiso 1 1 calc R . .
C3 C 0.08319(12) 0.1762(3) 0.24280(7) 0.0223(3) Uani 1 1 d . . .
H3A H 0.0601 0.0364 0.2517 0.027 Uiso 1 1 calc R . .
C4 C 0.13162(12) 0.3103(3) 0.28377(7) 0.0244(4) Uani 1 1 d . . .
C5 C 0.16377(12) 0.5163(3) 0.26982(6) 0.0237(4) Uani 1 1 d . . .
H5 H 0.1964 0.6095 0.2974 0.028 Uiso 1 1 calc R . .
C6 C 0.14935(12) 0.5885(3) 0.21669(7) 0.0210(3) Uani 1 1 d . . .
H6 H 0.1715 0.7295 0.2079 0.025 Uiso 1 1 calc R . .
C7 C 0.14885(15) 0.2355(4) 0.34179(7) 0.0375(5) Uani 1 1 d . . .
H7A H 0.1002 0.2999 0.3603 0.056 Uiso 1 1 calc R . .
H7B H 0.2125 0.2837 0.3596 0.056 Uiso 1 1 calc R . .
H7C H 0.1451 0.0743 0.3431 0.056 Uiso 1 1 calc R . .
C8 C 0.26784(11) 0.5734(2) 0.08979(6) 0.0169(3) Uani 1 1 d . . .
H8A H 0.2718 0.6848 0.1188 0.020 Uiso 1 1 calc R . .
H8B H 0.2781 0.6473 0.0562 0.020 Uiso 1 1 calc R . .
C9 C 0.34180(11) 0.3884(2) 0.10580(6) 0.0153(3) Uani 1 1 d . . .
C10 C 0.29381(11) 0.2008(2) 0.06852(6) 0.0156(3) Uani 1 1 d . . .
H10A H 0.3128 0.2109 0.0326 0.019 Uiso 1 1 calc R . .
H10B H 0.3139 0.0551 0.0843 0.019 Uiso 1 1 calc R . .
C11 C 0.18451(11) 0.2282(2) 0.06324(6) 0.0148(3) Uani 1 1 d . . .
H11 H 0.1591 0.1230 0.0879 0.018 Uiso 1 1 calc R . .
C12 C 0.13159(11) 0.1974(2) 0.00496(6) 0.0174(3) Uani 1 1 d . . .
H12 H 0.0618 0.2243 0.0037 0.021 Uiso 1 1 calc R . .
C13 C 0.14518(13) -0.0339(2) -0.01605(7) 0.0235(4) Uani 1 1 d . . .
H13A H 0.1046 -0.0528 -0.0515 0.035 Uiso 1 1 calc R . .
H13B H 0.1273 -0.1430 0.0092 0.035 Uiso 1 1 calc R . .
H13C H 0.2124 -0.0549 -0.0193 0.035 Uiso 1 1 calc R . .
C14 C 0.44135(11) 0.4367(2) 0.09277(6) 0.0171(3) Uani 1 1 d . . .
C15 C 0.51111(12) 0.2706(3) 0.10241(7) 0.0238(4) Uani 1 1 d . . .
H15 H 0.4960 0.1340 0.1174 0.029 Uiso 1 1 calc R . .
C16 C 0.60203(13) 0.3028(3) 0.09039(7) 0.0296(4) Uani 1 1 d . . .
H16 H 0.6482 0.1882 0.0971 0.035 Uiso 1 1 calc R . .
C17 C 0.62602(12) 0.5015(3) 0.06856(7) 0.0286(4) Uani 1 1 d . . .
H17 H 0.6879 0.5225 0.0600 0.034 Uiso 1 1 calc R . .
C18 C 0.55849(13) 0.6677(3) 0.05952(7) 0.0272(4) Uani 1 1 d . . .
H18 H 0.5744 0.8048 0.0451 0.033 Uiso 1 1 calc R . .
C19 C 0.46677(12) 0.6355(3) 0.07148(6) 0.0224(3) Uani 1 1 d . . .
H19 H 0.4211 0.7512 0.0650 0.027 Uiso 1 1 calc R . .
C20 C 0.35194(11) 0.3397(2) 0.16660(6) 0.0163(3) Uani 1 1 d . . .
C21 C 0.32028(12) 0.1472(2) 0.18797(6) 0.0200(3) Uani 1 1 d . . .
H21 H 0.2879 0.0385 0.1643 0.024 Uiso 1 1 calc R . .
C22 C 0.33544(12) 0.1115(3) 0.24365(7) 0.0247(4) Uani 1 1 d . . .
H22 H 0.3139 -0.0215 0.2575 0.030 Uiso 1 1 calc R . .
C23 C 0.38161(12) 0.2685(3) 0.27874(6) 0.0259(4) Uani 1 1 d . . .
H23 H 0.3920 0.2437 0.3166 0.031 Uiso 1 1 calc R . .
C24 C 0.41273(12) 0.4633(3) 0.25820(7) 0.0256(4) Uani 1 1 d . . .
H24 H 0.4440 0.5726 0.2820 0.031 Uiso 1 1 calc R . .
C25 C 0.39788(12) 0.4975(3) 0.20274(6) 0.0211(3) Uani 1 1 d . . .
H25 H 0.4194 0.6309 0.1891 0.025 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 O1 1.4394(11) . ?
S1 O2 1.4426(12) . ?
S1 N1 1.6149(13) . ?
S1 C1 1.7653(15) . ?
O3 C12 1.4353(17) . ?
O3 H3 0.8400 . ?
N1 C8 1.4722(18) . ?
N1 C11 1.4906(17) . ?
C1 C6 1.391(2) . ?
C1 C2 1.397(2) . ?
C2 C3 1.396(2) . ?
C2 H2 0.9500 . ?
C3 C4 1.396(2) . ?
C3 H3A 0.9500 . ?
C4 C5 1.396(2) . ?
C4 C7 1.508(2) . ?
C5 C6 1.388(2) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C8 C9 1.541(2) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 C14 1.534(2) . ?
C9 C20 1.541(2) . ?
C9 C10 1.554(2) . ?
C10 C11 1.543(2) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 C12 1.538(2) . ?
C11 H11 1.0000 . ?
C12 C13 1.523(2) . ?
C12 H12 1.0000 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 C19 1.392(2) . ?
C14 C15 1.404(2) . ?
C15 C16 1.391(2) . ?
C15 H15 0.9500 . ?
C16 C17 1.391(3) . ?
C16 H16 0.9500 . ?
C17 C18 1.382(3) . ?
C17 H17 0.9500 . ?
C18 C19 1.401(2) . ?
C18 H18 0.9500 . ?
C19 H19 0.9500 . ?
C20 C21 1.392(2) . ?
C20 C25 1.400(2) . ?
C21 C22 1.397(2) . ?
C21 H21 0.9500 . ?
C22 C23 1.383(2) . ?
C22 H22 0.9500 . ?
C23 C24 1.392(2) . ?
C23 H23 0.9500 . ?
C24 C25 1.390(2) . ?
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
O1 S1 O2 120.08(7) . . ?
O1 S1 N1 106.87(6) . . ?
O2 S1 N1 106.46(7) . . ?
O1 S1 C1 106.96(7) . . ?
O2 S1 C1 106.45(7) . . ?
N1 S1 C1 109.81(7) . . ?
C12 O3 H3 109.5 . . ?
C8 N1 C11 110.85(11) . . ?
C8 N1 S1 123.43(10) . . ?
C11 N1 S1 122.32(10) . . ?
C6 C1 C2 121.08(14) . . ?
C6 C1 S1 119.02(11) . . ?
C2 C1 S1 119.90(11) . . ?
C3 C2 C1 118.87(14) . . ?
C3 C2 H2 120.6 . . ?
C1 C2 H2 120.6 . . ?
C2 C3 C4 121.13(15) . . ?
C2 C3 H3A 119.4 . . ?
C4 C3 H3A 119.4 . . ?
C5 C4 C3 118.40(14) . . ?
C5 C4 C7 120.57(16) . . ?
C3 C4 C7 121.03(16) . . ?
C6 C5 C4 121.71(15) . . ?
C6 C5 H5 119.1 . . ?
C4 C5 H5 119.1 . . ?
C5 C6 C1 118.81(15) . . ?
C5 C6 H6 120.6 . . ?
C1 C6 H6 120.6 . . ?
C4 C7 H7A 109.5 . . ?
C4 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C4 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
N1 C8 C9 104.37(11) . . ?
N1 C8 H8A 110.9 . . ?
C9 C8 H8A 110.9 . . ?
N1 C8 H8B 110.9 . . ?
C9 C8 H8B 110.9 . . ?
H8A C8 H8B 108.9 . . ?
C14 C9 C20 108.69(12) . . ?
C14 C9 C8 114.60(12) . . ?
C20 C9 C8 109.86(12) . . ?
C14 C9 C10 109.46(12) . . ?
C20 C9 C10 114.44(12) . . ?
C8 C9 C10 99.72(12) . . ?
C11 C10 C9 107.50(12) . . ?
C11 C10 H10A 110.2 . . ?
C9 C10 H10A 110.2 . . ?
C11 C10 H10B 110.2 . . ?
C9 C10 H10B 110.2 . . ?
H10A C10 H10B 108.5 . . ?
N1 C11 C12 110.72(12) . . ?
N1 C11 C10 102.75(11) . . ?
C12 C11 C10 112.60(12) . . ?
N1 C11 H11 110.2 . . ?
C12 C11 H11 110.2 . . ?
C10 C11 H11 110.2 . . ?
O3 C12 C13 109.70(12) . . ?
O3 C12 C11 108.29(12) . . ?
C13 C12 C11 111.88(12) . . ?
O3 C12 H12 109.0 . . ?
C13 C12 H12 109.0 . . ?
C11 C12 H12 109.0 . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C19 C14 C15 117.72(14) . . ?
C19 C14 C9 123.95(14) . . ?
C15 C14 C9 118.33(13) . . ?
C16 C15 C14 121.00(15) . . ?
C16 C15 H15 119.5 . . ?
C14 C15 H15 119.5 . . ?
C15 C16 C17 120.61(16) . . ?
C15 C16 H16 119.7 . . ?
C17 C16 H16 119.7 . . ?
C18 C17 C16 119.05(15) . . ?
C18 C17 H17 120.5 . . ?
C16 C17 H17 120.5 . . ?
C17 C18 C19 120.44(15) . . ?
C17 C18 H18 119.8 . . ?
C19 C18 H18 119.8 . . ?
C14 C19 C18 121.16(15) . . ?
C14 C19 H19 119.4 . . ?
C18 C19 H19 119.4 . . ?
C21 C20 C25 117.85(14) . . ?
C21 C20 C9 124.38(13) . . ?
C25 C20 C9 117.75(13) . . ?
C20 C21 C22 120.94(15) . . ?
C20 C21 H21 119.5 . . ?
C22 C21 H21 119.5 . . ?
C23 C22 C21 120.42(15) . . ?
C23 C22 H22 119.8 . . ?
C21 C22 H22 119.8 . . ?
C22 C23 C24 119.50(15) . . ?
C22 C23 H23 120.2 . . ?
C24 C23 H23 120.2 . . ?
C25 C24 C23 119.86(15) . . ?
C25 C24 H24 120.1 . . ?
C23 C24 H24 120.1 . . ?
C24 C25 C20 121.42(15) . . ?
C24 C25 H25 119.3 . . ?
C20 C25 H25 119.3 . . ?

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
O1 S1 N1 C8 36.02(13) . . . . ?
O2 S1 N1 C8 165.50(11) . . . . ?
C1 S1 N1 C8 -79.65(13) . . . . ?
O1 S1 N1 C11 -166.73(11) . . . . ?
O2 S1 N1 C11 -37.25(13) . . . . ?
C1 S1 N1 C11 77.60(12) . . . . ?
O1 S1 C1 C6 -25.10(14) . . . . ?
O2 S1 C1 C6 -154.63(12) . . . . ?
N1 S1 C1 C6 90.51(13) . . . . ?
O1 S1 C1 C2 155.57(12) . . . . ?
O2 S1 C1 C2 26.04(14) . . . . ?
N1 S1 C1 C2 -88.81(13) . . . . ?
C6 C1 C2 C3 -0.3(2) . . . . ?
S1 C1 C2 C3 178.97(12) . . . . ?
C1 C2 C3 C4 -0.5(2) . . . . ?
C2 C3 C4 C5 0.9(2) . . . . ?
C2 C3 C4 C7 -179.25(16) . . . . ?
C3 C4 C5 C6 -0.5(2) . . . . ?
C7 C4 C5 C6 179.60(16) . . . . ?
C4 C5 C6 C1 -0.3(2) . . . . ?
C2 C1 C6 C5 0.7(2) . . . . ?
S1 C1 C6 C5 -178.63(12) . . . . ?
C11 N1 C8 C9 -29.51(15) . . . . ?
S1 N1 C8 C9 130.02(11) . . . . ?
N1 C8 C9 C14 154.27(12) . . . . ?
N1 C8 C9 C20 -83.04(14) . . . . ?
N1 C8 C9 C10 37.51(13) . . . . ?
C14 C9 C10 C11 -154.44(12) . . . . ?
C20 C9 C10 C11 83.29(15) . . . . ?
C8 C9 C10 C11 -33.88(14) . . . . ?
C8 N1 C11 C12 -112.91(14) . . . . ?
S1 N1 C11 C12 87.29(14) . . . . ?
C8 N1 C11 C10 7.53(14) . . . . ?
S1 N1 C11 C10 -152.26(10) . . . . ?
C9 C10 C11 N1 17.32(14) . . . . ?
C9 C10 C11 C12 136.46(12) . . . . ?
N1 C11 C12 O3 55.59(15) . . . . ?
C10 C11 C12 O3 -58.80(15) . . . . ?
N1 C11 C12 C13 176.61(12) . . . . ?
C10 C11 C12 C13 62.23(16) . . . . ?
C20 C9 C14 C19 -119.30(15) . . . . ?
C8 C9 C14 C19 4.0(2) . . . . ?
C10 C9 C14 C19 115.05(15) . . . . ?
C20 C9 C14 C15 61.23(17) . . . . ?
C8 C9 C14 C15 -175.45(13) . . . . ?
C10 C9 C14 C15 -64.42(17) . . . . ?
C19 C14 C15 C16 -0.8(2) . . . . ?
C9 C14 C15 C16 178.66(14) . . . . ?
C14 C15 C16 C17 0.1(3) . . . . ?
C15 C16 C17 C18 0.7(3) . . . . ?
C16 C17 C18 C19 -0.9(3) . . . . ?
C15 C14 C19 C18 0.7(2) . . . . ?
C9 C14 C19 C18 -178.78(14) . . . . ?
C17 C18 C19 C14 0.2(3) . . . . ?
C14 C9 C20 C21 -123.70(15) . . . . ?
C8 C9 C20 C21 110.18(16) . . . . ?
C10 C9 C20 C21 -1.0(2) . . . . ?
C14 C9 C20 C25 54.90(17) . . . . ?
C8 C9 C20 C25 -71.22(17) . . . . ?
C10 C9 C20 C25 177.59(13) . . . . ?
C25 C20 C21 C22 -1.1(2) . . . . ?
C9 C20 C21 C22 177.50(14) . . . . ?
C20 C21 C22 C23 0.6(2) . . . . ?
C21 C22 C23 C24 0.2(2) . . . . ?
C22 C23 C24 C25 -0.5(2) . . . . ?
C23 C24 C25 C20 0.0(2) . . . . ?
C21 C20 C25 C24 0.8(2) . . . . ?
C9 C20 C25 C24 -177.90(14) . . . . ?

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
O3 H3 O2 0.84 2.04 2.8634(17) 168.6 3_565

_diffrn_measured_fraction_theta_max 0.994
_diffrn_reflns_theta_full        27.94
_diffrn_measured_fraction_theta_full 0.994
_refine_diff_density_max         0.317
_refine_diff_density_min         -0.511
_refine_diff_density_rms         0.061
####################################################################### 
# 
# 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 1400825'
_audit_update_record             
;
2015-05-14 deposited with the CCDC.
2015-06-26 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C13 H17 N O4 S'
_chemical_formula_weight         283.34

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   P2(1)2(1)2(1)

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'

_cell_length_a                   8.6906(17)
_cell_length_b                   11.953(2)
_cell_length_c                   13.546(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1407.1(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    113(2)
_cell_measurement_reflns_used    4233
_cell_measurement_theta_min      2.2724
_cell_measurement_theta_max      27.9825

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_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    1.337
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             600
_exptl_absorpt_coefficient_mu    0.239
_exptl_absorpt_correction_type   MULTI-SCAN
_exptl_absorpt_correction_T_min  0.9537
_exptl_absorpt_correction_T_max  0.9719
_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            16639
_diffrn_reflns_av_R_equivalents  0.0564
_diffrn_reflns_av_sigmaI/netI    0.0471
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.27
_diffrn_reflns_theta_max         27.99
_reflns_number_total             3374
_reflns_number_gt                3079
_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)+(0.0950P)²+1.1972P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.01(12)
_refine_ls_number_reflns         3374
_refine_ls_number_parameters     175
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0641
_refine_ls_R_factor_gt           0.0592
_refine_ls_wR_factor_ref         0.1598
_refine_ls_wR_factor_gt          0.1544
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_restrained_S_all      1.038
_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
S1 S 1.02816(8) 0.96261(6) 0.78655(5) 0.01741(19) Uani 1 1 d . . .
O1 O 1.0614(3) 0.8790(2) 0.86008(16) 0.0240(5) Uani 1 1 d . . .
O2 O 1.0860(3) 1.07318(18) 0.80330(18) 0.0246(5) Uani 1 1 d . . .
O3 O 0.8367(3) 1.0907(2) 0.6553(2) 0.0341(7) Uani 1 1 d . . .
O4 O 0.7036(4) 1.2412(2) 0.4391(2) 0.0509(9) Uani 1 1 d . . .
H4 H 0.6415 1.2020 0.4065 0.076 Uiso 1 1 calc R . .
N1 N 0.8388(3) 0.9608(2) 0.7783(2) 0.0223(5) Uani 1 1 d . . .
C1 C 1.0975(3) 0.9132(2) 0.6727(2) 0.0155(6) Uani 1 1 d . . .
C2 C 1.1536(4) 0.9886(3) 0.6033(2) 0.0197(6) Uani 1 1 d . . .
H2 H 1.1506 1.0668 0.6158 0.024 Uiso 1 1 calc R . .
C3 C 1.2140(4) 0.9479(3) 0.5154(2) 0.0254(7) Uani 1 1 d . . .
H3 H 1.2536 0.9986 0.4678 0.031 Uiso 1 1 calc R . .
C4 C 1.2169(4) 0.8328(3) 0.4966(3) 0.0283(7) Uani 1 1 d . . .
H4A H 1.2591 0.8049 0.4368 0.034 Uiso 1 1 calc R . .
C5 C 1.1568(5) 0.7597(3) 0.5671(3) 0.0280(7) Uani 1 1 d . . .
H5 H 1.1563 0.6816 0.5540 0.034 Uiso 1 1 calc R . .
C6 C 1.0981(4) 0.7985(3) 0.6553(2) 0.0217(6) Uani 1 1 d . . .
H6 H 1.0589 0.7479 0.7032 0.026 Uiso 1 1 calc R . .
C7 C 0.7685(3) 1.0213(2) 0.7143(2) 0.0171(6) Uani 1 1 d . . .
C8 C 0.5948(3) 1.0198(2) 0.7023(2) 0.0195(6) Uani 1 1 d . . .
C9 C 0.5788(4) 1.0805(3) 0.6026(3) 0.0254(7) Uani 1 1 d . . .
H9A H 0.5763 1.0263 0.5473 0.030 Uiso 1 1 calc R . .
H9B H 0.4840 1.1263 0.6008 0.030 Uiso 1 1 calc R . .
C10 C 0.7206(5) 1.1534(3) 0.5973(3) 0.0333(8) Uani 1 1 d . . .
H10 H 0.6994 1.2267 0.6301 0.040 Uiso 1 1 calc R . .
C11 C 0.7917(5) 1.1739(3) 0.4963(3) 0.0309(8) Uani 1 1 d . . .
H11A H 0.8943 1.2086 0.5049 0.037 Uiso 1 1 calc R . .
H11B H 0.8063 1.1013 0.4624 0.037 Uiso 1 1 calc R . .
C12 C 0.5360(4) 0.8991(3) 0.7011(3) 0.0306(8) Uani 1 1 d . . .
H12A H 0.5795 0.8596 0.6442 0.046 Uiso 1 1 calc R . .
H12B H 0.4234 0.8992 0.6963 0.046 Uiso 1 1 calc R . .
H12C H 0.5672 0.8613 0.7620 0.046 Uiso 1 1 calc R . .
C13 C 0.5232(4) 1.0858(3) 0.7877(3) 0.0311(7) Uani 1 1 d . . .
H13A H 0.5470 1.0486 0.8503 0.047 Uiso 1 1 calc R . .
H13B H 0.4113 1.0893 0.7789 0.047 Uiso 1 1 calc R . .
H13C H 0.5654 1.1619 0.7884 0.047 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 O2 1.432(2) . ?
S1 O1 1.441(2) . ?
S1 N1 1.650(3) . ?
S1 C1 1.758(3) . ?
O3 C7 1.297(4) . ?
O3 C10 1.481(4) . ?
O4 C11 1.354(5) . ?
O4 H4 0.8400 . ?
N1 C7 1.284(4) . ?
C1 C2 1.391(4) . ?
C1 C6 1.392(4) . ?
C2 C3 1.389(5) . ?
C2 H2 0.9500 . ?
C3 C4 1.400(5) . ?
C3 H3 0.9500 . ?
C4 C5 1.395(5) . ?
C4 H4A 0.9500 . ?
C5 C6 1.380(5) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C7 C8 1.518(4) . ?
C8 C12 1.531(4) . ?
C8 C13 1.532(5) . ?
C8 C9 1.539(4) . ?
C9 C10 1.512(5) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 C11 1.522(5) . ?
C10 H10 1.0000 . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?

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
O2 S1 O1 117.42(14) . . ?
O2 S1 N1 111.92(15) . . ?
O1 S1 N1 103.73(14) . . ?
O2 S1 C1 109.19(15) . . ?
O1 S1 C1 107.74(14) . . ?
N1 S1 C1 106.16(14) . . ?
C7 O3 C10 109.8(3) . . ?
C11 O4 H4 109.5 . . ?
C7 N1 S1 120.8(2) . . ?
C2 C1 C6 121.5(3) . . ?
C2 C1 S1 119.7(2) . . ?
C6 C1 S1 118.8(2) . . ?
C3 C2 C1 119.0(3) . . ?
C3 C2 H2 120.5 . . ?
C1 C2 H2 120.5 . . ?
C2 C3 C4 120.5(3) . . ?
C2 C3 H3 119.8 . . ?
C4 C3 H3 119.8 . . ?
C5 C4 C3 119.0(3) . . ?
C5 C4 H4A 120.5 . . ?
C3 C4 H4A 120.5 . . ?
C6 C5 C4 121.3(3) . . ?
C6 C5 H5 119.3 . . ?
C4 C5 H5 119.3 . . ?
C5 C6 C1 118.7(3) . . ?
C5 C6 H6 120.7 . . ?
C1 C6 H6 120.7 . . ?
N1 C7 O3 124.0(3) . . ?
N1 C7 C8 122.6(3) . . ?
O3 C7 C8 113.3(3) . . ?
C7 C8 C12 110.1(2) . . ?
C7 C8 C13 108.5(3) . . ?
C12 C8 C13 111.0(3) . . ?
C7 C8 C9 100.3(2) . . ?
C12 C8 C9 113.8(3) . . ?
C13 C8 C9 112.5(3) . . ?
C10 C9 C8 103.8(3) . . ?
C10 C9 H9A 111.0 . . ?
C8 C9 H9A 111.0 . . ?
C10 C9 H9B 111.0 . . ?
C8 C9 H9B 111.0 . . ?
H9A C9 H9B 109.0 . . ?
O3 C10 C9 103.8(3) . . ?
O3 C10 C11 106.3(3) . . ?
C9 C10 C11 117.8(3) . . ?
O3 C10 H10 109.5 . . ?
C9 C10 H10 109.5 . . ?
C11 C10 H10 109.5 . . ?
O4 C11 C10 112.4(4) . . ?
O4 C11 H11A 109.1 . . ?
C10 C11 H11A 109.1 . . ?
O4 C11 H11B 109.1 . . ?
C10 C11 H11B 109.1 . . ?
H11A C11 H11B 107.9 . . ?
C8 C12 H12A 109.5 . . ?
C8 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C8 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C8 C13 H13A 109.5 . . ?
C8 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C8 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?

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
O2 S1 N1 C7 56.7(3) . . . . ?
O1 S1 N1 C7 -175.8(3) . . . . ?
C1 S1 N1 C7 -62.3(3) . . . . ?
O2 S1 C1 C2 -18.7(3) . . . . ?
O1 S1 C1 C2 -147.3(2) . . . . ?
N1 S1 C1 C2 102.1(3) . . . . ?
O2 S1 C1 C6 159.8(3) . . . . ?
O1 S1 C1 C6 31.2(3) . . . . ?
N1 S1 C1 C6 -79.4(3) . . . . ?
C6 C1 C2 C3 -1.2(5) . . . . ?
S1 C1 C2 C3 177.3(2) . . . . ?
C1 C2 C3 C4 0.7(5) . . . . ?
C2 C3 C4 C5 0.6(5) . . . . ?
C3 C4 C5 C6 -1.4(6) . . . . ?
C4 C5 C6 C1 1.0(5) . . . . ?
C2 C1 C6 C5 0.3(5) . . . . ?
S1 C1 C6 C5 -178.1(3) . . . . ?
S1 N1 C7 O3 -3.1(5) . . . . ?
S1 N1 C7 C8 178.3(2) . . . . ?
C10 O3 C7 N1 -175.3(3) . . . . ?
C10 O3 C7 C8 3.4(4) . . . . ?
N1 C7 C8 C12 -45.9(4) . . . . ?
O3 C7 C8 C12 135.3(3) . . . . ?
N1 C7 C8 C13 75.7(4) . . . . ?
O3 C7 C8 C13 -103.0(3) . . . . ?
N1 C7 C8 C9 -166.2(3) . . . . ?
O3 C7 C8 C9 15.1(3) . . . . ?
C7 C8 C9 C10 -26.5(3) . . . . ?
C12 C8 C9 C10 -144.0(3) . . . . ?
C13 C8 C9 C10 88.7(3) . . . . ?
C7 O3 C10 C9 -21.1(4) . . . . ?
C7 O3 C10 C11 -146.0(3) . . . . ?
C8 C9 C10 O3 29.4(4) . . . . ?
C8 C9 C10 C11 146.6(3) . . . . ?
O3 C10 C11 O4 -173.4(3) . . . . ?
C9 C10 C11 O4 70.7(4) . . . . ?

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
O4 H4 O1 0.84 2.11 2.917(4) 161.8 2_674
O4 H4 N1 0.84 2.61 3.272(4) 136.3 2_674
O4 H4 S1 0.84 2.95 3.776(3) 169.6 2_674

_diffrn_measured_fraction_theta_max 0.995
_diffrn_reflns_theta_full        27.99
_diffrn_measured_fraction_theta_full 0.995
_refine_diff_density_max         1.113
_refine_diff_density_min         -0.448
_refine_diff_density_rms         0.091
