# 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_Compound2
_database_code_depnum_ccdc_archive 'CCDC 917624'
_audit_update_record             
;
2012-12-30 deposited with the CCDC.
2015-02-10 downloaded from the CCDC.
;
#TrackingRef 'Compound 2.cif'


_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C15 H17 N O2 S'
_chemical_formula_sum            'C15 H17 N O2 S'
_chemical_formula_weight         275.36

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                   7.298(5)
_cell_length_b                   9.090(5)
_cell_length_c                   10.762(5)
_cell_angle_alpha                75.500(5)
_cell_angle_beta                 78.979(5)
_cell_angle_gamma                89.218(5)
_cell_volume                     678.0(7)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    999
_cell_measurement_theta_min      1.99
_cell_measurement_theta_max      25.50

_exptl_crystal_description       Block
_exptl_crystal_colour            Colorless
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.14
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.349
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             292
_exptl_absorpt_coefficient_mu    0.236
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.953
_exptl_absorpt_correction_T_max  0.967
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      100(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  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            3515
_diffrn_reflns_av_R_equivalents  0.0212
_diffrn_reflns_av_sigmaI/netI    0.0362
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         1.99
_diffrn_reflns_theta_max         25.50
_reflns_number_total             2443
_reflns_number_gt                2240
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+(0.1128P)²+0.8522P] 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         2443
_refine_ls_number_parameters     176
_refine_ls_number_restraints     5
_refine_ls_R_factor_all          0.0626
_refine_ls_R_factor_gt           0.0543
_refine_ls_wR_factor_ref         0.1974
_refine_ls_wR_factor_gt          0.1554
_refine_ls_goodness_of_fit_ref   1.166
_refine_ls_restrained_S_all      1.201
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.001

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 0.49125(10) 0.31284(8) 0.18404(7) 0.0241(3) Uani 1 1 d . . .
O1 O 0.2775(3) 0.2591(2) 0.0080(2) 0.0234(5) Uani 1 1 d D . .
O2 O 0.9122(3) 0.1482(2) -0.1249(2) 0.0245(5) Uani 1 1 d . . .
N1 N 0.8289(3) 0.2457(3) 0.0850(2) 0.0195(5) Uani 1 1 d D . .
C1 C 0.6509(4) 0.2559(3) 0.0701(3) 0.0205(6) Uani 1 1 d D . .
C2 C 0.6034(4) 0.2133(3) -0.0430(3) 0.0182(6) Uani 1 1 d D . .
H2 H 0.5787 0.1079 0.0089 0.022 Uiso 1 1 calc R . .
C3 C 0.7468(4) 0.1627(3) -0.1377(3) 0.0189(6) Uani 1 1 d . . .
C4 C 0.6945(4) 0.1226(3) -0.2549(3) 0.0211(6) Uani 1 1 d . . .
H4A H 0.6682 0.0138 -0.2332 0.025 Uiso 1 1 calc R . .
H4B H 0.8014 0.1457 -0.3265 0.025 Uiso 1 1 calc R . .
C5 C 0.5268(4) 0.2040(3) -0.3021(3) 0.0210(6) Uani 1 1 d . . .
C6 C 0.3691(4) 0.1772(3) -0.1825(3) 0.0202(6) Uani 1 1 d . . .
H6A H 0.2634 0.2358 -0.2064 0.024 Uiso 1 1 calc R . .
H6B H 0.3298 0.0706 -0.1570 0.024 Uiso 1 1 calc R . .
C7 C 0.4207(4) 0.2194(3) -0.0668(3) 0.0190(6) Uani 1 1 d D . .
C8 C 0.5735(4) 0.3741(3) -0.3569(3) 0.0252(7) Uani 1 1 d . . .
H8A H 0.6088 0.4151 -0.2905 0.038 Uiso 1 1 calc R . .
H8B H 0.4660 0.4247 -0.3839 0.038 Uiso 1 1 calc R . .
H8C H 0.6751 0.3895 -0.4306 0.038 Uiso 1 1 calc R . .
C9 C 0.4703(4) 0.1373(4) -0.4067(3) 0.0281(7) Uani 1 1 d . . .
H9A H 0.3648 0.1894 -0.4356 0.042 Uiso 1 1 calc R . .
H9B H 0.4378 0.0312 -0.3708 0.042 Uiso 1 1 calc R . .
H9C H 0.5729 0.1495 -0.4796 0.042 Uiso 1 1 calc R . .
C10 C 0.8991(4) 0.2816(3) 0.1893(3) 0.0204(6) Uani 1 1 d . . .
C11 C 0.9105(4) 0.4316(3) 0.1977(3) 0.0230(6) Uani 1 1 d . . .
H11 H 0.8681 0.5094 0.1368 0.028 Uiso 1 1 calc R . .
C12 C 0.9854(4) 0.4643(3) 0.2972(3) 0.0256(7) Uani 1 1 d . . .
H12 H 0.9941 0.5644 0.3024 0.031 Uiso 1 1 calc R . .
C13 C 1.0474(4) 0.3483(3) 0.3891(3) 0.0244(7) Uani 1 1 d . . .
H13 H 1.0955 0.3703 0.4567 0.029 Uiso 1 1 calc R . .
C14 C 0.9616(4) 0.1650(3) 0.2803(3) 0.0206(6) Uani 1 1 d . . .
H14 H 0.9529 0.0649 0.2749 0.025 Uiso 1 1 calc R . .
C15 C 1.0370(4) 0.1988(3) 0.3793(3) 0.0222(6) Uani 1 1 d . . .
H15 H 1.0809 0.1212 0.4395 0.027 Uiso 1 1 calc R . .
H1N1 H 0.904(4) 0.213(4) 0.024(3) 0.025(8) Uiso 1 1 d D . .

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 0.0184(4) 0.0326(5) 0.0246(5) -0.0131(3) -0.0040(3) 0.0032(3)
O1 0.0147(10) 0.0314(11) 0.0253(11) -0.0093(9) -0.0040(8) 0.0058(8)
O2 0.0145(11) 0.0363(12) 0.0277(11) -0.0159(9) -0.0068(8) 0.0081(9)
N1 0.0168(12) 0.0241(13) 0.0200(12) -0.0097(10) -0.0040(10) 0.0036(10)
C1 0.0194(14) 0.0161(13) 0.0258(15) -0.0032(11) -0.0070(11) 0.0021(11)
C2 0.0159(14) 0.0154(13) 0.0222(15) -0.0009(11) -0.0060(11) 0.0003(11)
C3 0.0177(14) 0.0150(13) 0.0222(14) -0.0026(10) -0.0024(11) -0.0001(10)
C4 0.0182(14) 0.0233(14) 0.0236(15) -0.0080(11) -0.0063(11) 0.0046(11)
C5 0.0201(14) 0.0243(15) 0.0214(14) -0.0083(11) -0.0074(11) 0.0035(11)
C6 0.0179(14) 0.0216(14) 0.0227(15) -0.0053(11) -0.0082(11) -0.0005(11)
C7 0.0201(14) 0.0164(13) 0.0192(14) -0.0016(10) -0.0039(11) 0.0006(11)
C8 0.0279(16) 0.0236(15) 0.0223(15) -0.0019(12) -0.0056(12) 0.0031(12)
C9 0.0263(16) 0.0355(17) 0.0266(16) -0.0121(13) -0.0098(13) 0.0054(13)
C10 0.0133(13) 0.0269(15) 0.0234(15) -0.0102(12) -0.0044(11) 0.0043(11)
C11 0.0223(15) 0.0220(15) 0.0263(15) -0.0053(12) -0.0098(12) 0.0042(11)
C12 0.0249(15) 0.0234(15) 0.0302(16) -0.0095(12) -0.0062(12) 0.0009(12)
C13 0.0213(15) 0.0291(16) 0.0240(15) -0.0081(12) -0.0054(12) -0.0032(12)
C14 0.0176(14) 0.0196(14) 0.0246(15) -0.0056(11) -0.0038(11) 0.0011(11)
C15 0.0189(14) 0.0249(15) 0.0216(14) -0.0011(11) -0.0076(11) 0.0004(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 C1 1.698(3) . ?
O1 C7 1.297(3) . ?
O2 C3 1.242(4) . ?
N1 C1 1.338(4) . ?
N1 C10 1.428(4) . ?
C1 C2 1.466(4) . ?
C2 C7 1.403(4) . ?
C2 C3 1.470(4) . ?
C3 C4 1.513(4) . ?
C4 C5 1.526(4) . ?
C5 C6 1.525(4) . ?
C5 C9 1.526(4) . ?
C5 C8 1.528(4) . ?
C6 C7 1.504(4) . ?
C10 C14 1.388(4) . ?
C10 C11 1.393(4) . ?
C11 C12 1.386(4) . ?
C12 C13 1.390(4) . ?
C13 C15 1.393(4) . ?
C14 C15 1.388(4) . ?

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 N1 C10 125.2(2) . . ?
N1 C1 C2 117.8(3) . . ?
N1 C1 S1 118.7(2) . . ?
C2 C1 S1 123.4(2) . . ?
C7 C2 C1 122.1(3) . . ?
C7 C2 C3 116.7(3) . . ?
C1 C2 C3 121.2(2) . . ?
O2 C3 C2 122.6(3) . . ?
O2 C3 C4 117.4(2) . . ?
C2 C3 C4 120.0(2) . . ?
C3 C4 C5 115.3(2) . . ?
C6 C5 C4 106.1(2) . . ?
C6 C5 C9 110.0(2) . . ?
C4 C5 C9 110.2(2) . . ?
C6 C5 C8 110.2(2) . . ?
C4 C5 C8 110.1(2) . . ?
C9 C5 C8 110.0(2) . . ?
C7 C6 C5 114.1(2) . . ?
O1 C7 C2 124.6(3) . . ?
O1 C7 C6 112.3(2) . . ?
C2 C7 C6 123.0(3) . . ?
C14 C10 C11 120.4(3) . . ?
C14 C10 N1 118.9(3) . . ?
C11 C10 N1 120.7(3) . . ?
C12 C11 C10 119.7(3) . . ?
C11 C12 C13 120.4(3) . . ?
C12 C13 C15 119.5(3) . . ?
C15 C14 C10 119.6(3) . . ?
C14 C15 C13 120.4(3) . . ?

_diffrn_measured_fraction_theta_max 0.974
_diffrn_reflns_theta_full        25.50
_diffrn_measured_fraction_theta_full 0.974
_refine_diff_density_max         0.590
_refine_diff_density_min         -0.882
_refine_diff_density_rms         0.109


