# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2016

####################################################################### 
# 
# 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_0231_200
_database_code_depnum_ccdc_archive 'CCDC 968455'
_audit_update_record             
;
2013-10-24 deposited with the CCDC.
2016-09-14 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C14 H20 N2 O2 S'
_chemical_formula_sum            'C14 H20 N2 O2 S'
_chemical_formula_weight         280.38

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                   6.605
_cell_length_b                   13.973
_cell_length_c                   16.200
_cell_angle_alpha                90.00
_cell_angle_beta                 94.04
_cell_angle_gamma                90.00
_cell_volume                     1491.4
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    8231
_cell_measurement_theta_min      2.91
_cell_measurement_theta_max      30.47

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.15
_exptl_crystal_density_meas      1.247
_exptl_crystal_density_diffrn    1.249
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             600
_exptl_absorpt_coefficient_mu    0.217
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9579
_exptl_absorpt_correction_T_max  0.9682
_exptl_absorpt_process_details   SADABS

_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 APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            12478
_diffrn_reflns_av_R_equivalents  0.0183
_diffrn_reflns_av_sigmaI/netI    0.0142
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.52
_diffrn_reflns_theta_max         24.99
_reflns_number_total             2615
_reflns_number_gt                2293
_reflns_threshold_expression     >2σ(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_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 > 2σ(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)+(0.0699P)²+1.0101P] 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         2615
_refine_ls_number_parameters     184
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0536
_refine_ls_R_factor_gt           0.0474
_refine_ls_wR_factor_ref         0.1395
_refine_ls_wR_factor_gt          0.1303
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_restrained_S_all      1.041
_refine_ls_shift/su_max          0.000
_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
C1 C 0.4754(6) 0.4330(3) 1.0948(2) 0.1010(12) Uani 1 1 d . . .
H1A H 0.4795 0.5013 1.0887 0.151 Uiso 1 1 calc R . .
H1B H 0.5891 0.4050 1.0699 0.151 Uiso 1 1 calc R . .
H1C H 0.4813 0.4169 1.1525 0.151 Uiso 1 1 calc R . .
C2 C 0.2866(5) 0.3961(2) 1.0538(2) 0.0733(8) Uani 1 1 d . . .
H2A H 0.2794 0.4136 0.9958 0.088 Uiso 1 1 calc R . .
H2B H 0.1718 0.4249 1.0786 0.088 Uiso 1 1 calc R . .
C3 C -0.0628(5) 0.2581(3) 1.1113(2) 0.0877(10) Uani 1 1 d . . .
H3A H -0.1301 0.2336 1.1575 0.132 Uiso 1 1 calc R . .
H3B H -0.0987 0.2199 1.0632 0.132 Uiso 1 1 calc R . .
H3C H -0.1039 0.3231 1.1009 0.132 Uiso 1 1 calc R . .
C4 C 0.1618(4) 0.2544(2) 1.13037(15) 0.0620(7) Uani 1 1 d . . .
H4A H 0.1971 0.2922 1.1795 0.074 Uiso 1 1 calc R . .
H4B H 0.2022 0.1887 1.1421 0.074 Uiso 1 1 calc R . .
C5 C 0.3623(3) 0.23520(16) 1.00757(13) 0.0422(5) Uani 1 1 d . . .
C6 C 0.3559(4) 0.12938(18) 1.02026(17) 0.0585(6) Uani 1 1 d D . .
C7 C 0.2161(6) 0.0742(2) 0.9914(2) 0.0847(10) Uani 1 1 d D . .
C8 C 0.7067(3) 0.30528(16) 0.83476(13) 0.0416(5) Uani 1 1 d . . .
C9 C 0.6130(4) 0.36560(18) 0.77582(15) 0.0513(6) Uani 1 1 d . . .
H9 H 0.4760 0.3579 0.7597 0.062 Uiso 1 1 calc R . .
C10 C 0.7234(4) 0.43713(18) 0.74112(15) 0.0554(6) Uani 1 1 d . . .
H10 H 0.6591 0.4781 0.7023 0.067 Uiso 1 1 calc R . .
C11 C 0.9282(4) 0.44894(18) 0.76315(14) 0.0519(6) Uani 1 1 d . . .
C12 C 1.0191(4) 0.3873(2) 0.82117(16) 0.0611(7) Uani 1 1 d . . .
H12 H 1.1567 0.3940 0.8365 0.073 Uiso 1 1 calc R . .
C13 C 0.9099(4) 0.3157(2) 0.85696(15) 0.0555(6) Uani 1 1 d . . .
H13 H 0.9740 0.2749 0.8959 0.067 Uiso 1 1 calc R . .
C14 C 1.0486(5) 0.5265(2) 0.7241(2) 0.0783(9) Uani 1 1 d . . .
H14A H 0.9612 0.5619 0.6853 0.117 Uiso 1 1 calc R . .
H14B H 1.1565 0.4981 0.6959 0.117 Uiso 1 1 calc R . .
H14C H 1.1047 0.5690 0.7663 0.117 Uiso 1 1 calc R . .
N1 N 0.2747(3) 0.29086(14) 1.06135(12) 0.0527(5) Uani 1 1 d . . .
N2 N 0.4555(3) 0.27637(12) 0.94813(11) 0.0446(5) Uani 1 1 d . . .
O1 O 0.7096(3) 0.14690(12) 0.91779(12) 0.0646(5) Uani 1 1 d . . .
O2 O 0.4207(3) 0.17836(14) 0.81810(11) 0.0705(6) Uani 1 1 d . . .
S1 S 0.56602(8) 0.21422(4) 0.88033(3) 0.0442(2) Uani 1 1 d . . .
H7' H 0.224(6) -0.0021(15) 1.003(2) 0.125(13) Uiso 1 1 d D . .
H7'' H 0.099(6) 0.114(3) 0.957(3) 0.18(2) Uiso 1 1 d D . .
H6 H 0.466(4) 0.088(2) 1.0551(19) 0.097(11) Uiso 1 1 d D . .


_geom_special_details            
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s 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
C1 C2 1.464(5) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C2 N1 1.478(3) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 C4 1.495(4) . ?
C3 H3A 0.9600 . ?
C3 H3B 0.9600 . ?
C3 H3C 0.9600 . ?
C4 N1 1.478(3) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C5 N2 1.312(3) . ?
C5 N1 1.330(3) . ?
C5 C6 1.494(3) . ?
C6 C7 1.267(4) . ?
C6 H6 1.060(18) . ?
C7 H7' 1.082(19) . ?
C7 H7'' 1.076(19) . ?
C8 C13 1.373(3) . ?
C8 C9 1.386(3) . ?
C8 S1 1.768(2) . ?
C9 C10 1.380(3) . ?
C9 H9 0.9300 . ?
C10 C11 1.384(3) . ?
C10 H10 0.9300 . ?
C11 C12 1.381(4) . ?
C11 C14 1.510(3) . ?
C12 C13 1.384(4) . ?
C12 H12 0.9300 . ?
C13 H13 0.9300 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
N2 S1 1.6143(18) . ?
O1 S1 1.4391(18) . ?
O2 S1 1.4324(18) . ?

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
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 . . ?
C1 C2 N1 111.2(3) . . ?
C1 C2 H2A 109.4 . . ?
N1 C2 H2A 109.4 . . ?
C1 C2 H2B 109.4 . . ?
N1 C2 H2B 109.4 . . ?
H2A C2 H2B 108.0 . . ?
C4 C3 H3A 109.5 . . ?
C4 C3 H3B 109.5 . . ?
H3A C3 H3B 109.5 . . ?
C4 C3 H3C 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
N1 C4 C3 112.2(2) . . ?
N1 C4 H4A 109.2 . . ?
C3 C4 H4A 109.2 . . ?
N1 C4 H4B 109.2 . . ?
C3 C4 H4B 109.2 . . ?
H4A C4 H4B 107.9 . . ?
N2 C5 N1 118.2(2) . . ?
N2 C5 C6 123.7(2) . . ?
N1 C5 C6 118.1(2) . . ?
C7 C6 C5 125.4(3) . . ?
C7 C6 H6 108.6(19) . . ?
C5 C6 H6 126.0(19) . . ?
C6 C7 H7' 121(2) . . ?
C6 C7 H7'' 110(3) . . ?
H7' C7 H7'' 129(4) . . ?
C13 C8 C9 119.8(2) . . ?
C13 C8 S1 120.01(17) . . ?
C9 C8 S1 120.20(17) . . ?
C10 C9 C8 119.9(2) . . ?
C10 C9 H9 120.1 . . ?
C8 C9 H9 120.1 . . ?
C9 C10 C11 121.1(2) . . ?
C9 C10 H10 119.5 . . ?
C11 C10 H10 119.5 . . ?
C12 C11 C10 118.1(2) . . ?
C12 C11 C14 121.1(2) . . ?
C10 C11 C14 120.8(2) . . ?
C11 C12 C13 121.4(2) . . ?
C11 C12 H12 119.3 . . ?
C13 C12 H12 119.3 . . ?
C8 C13 C12 119.7(2) . . ?
C8 C13 H13 120.1 . . ?
C12 C13 H13 120.1 . . ?
C11 C14 H14A 109.5 . . ?
C11 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C11 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C5 N1 C2 120.0(2) . . ?
C5 N1 C4 124.0(2) . . ?
C2 N1 C4 116.0(2) . . ?
C5 N2 S1 121.44(16) . . ?
O2 S1 O1 117.19(13) . . ?
O2 S1 N2 110.76(11) . . ?
O1 S1 N2 112.38(10) . . ?
O2 S1 C8 107.67(11) . . ?
O1 S1 C8 107.25(10) . . ?
N2 S1 C8 99.97(10) . . ?

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
N2 C5 C6 C7 -93.6(4) . . . . ?
N1 C5 C6 C7 88.9(4) . . . . ?
C13 C8 C9 C10 -1.4(4) . . . . ?
S1 C8 C9 C10 179.36(18) . . . . ?
C8 C9 C10 C11 1.1(4) . . . . ?
C9 C10 C11 C12 -0.2(4) . . . . ?
C9 C10 C11 C14 179.2(2) . . . . ?
C10 C11 C12 C13 -0.3(4) . . . . ?
C14 C11 C12 C13 -179.7(3) . . . . ?
C9 C8 C13 C12 0.9(4) . . . . ?
S1 C8 C13 C12 -179.9(2) . . . . ?
C11 C12 C13 C8 -0.1(4) . . . . ?
N2 C5 N1 C2 -0.9(3) . . . . ?
C6 C5 N1 C2 176.8(3) . . . . ?
N2 C5 N1 C4 178.9(2) . . . . ?
C6 C5 N1 C4 -3.4(3) . . . . ?
C1 C2 N1 C5 -84.7(3) . . . . ?
C1 C2 N1 C4 95.4(3) . . . . ?
C3 C4 N1 C5 -100.8(3) . . . . ?
C3 C4 N1 C2 79.0(4) . . . . ?
N1 C5 N2 S1 179.91(17) . . . . ?
C6 C5 N2 S1 2.4(3) . . . . ?
C5 N2 S1 O2 79.3(2) . . . . ?
C5 N2 S1 O1 -53.8(2) . . . . ?
C5 N2 S1 C8 -167.31(18) . . . . ?
C13 C8 S1 O2 -143.6(2) . . . . ?
C9 C8 S1 O2 35.6(2) . . . . ?
C13 C8 S1 O1 -16.6(2) . . . . ?
C9 C8 S1 O1 162.59(18) . . . . ?
C13 C8 S1 N2 100.7(2) . . . . ?
C9 C8 S1 N2 -80.1(2) . . . . ?

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        24.99
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.574
_refine_diff_density_min         -0.303
_refine_diff_density_rms         0.049
