# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2018

####################################################################### 
# 
# 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_SOUMYA_a
_database_code_depnum_ccdc_archive 'CCDC 1856683'
_audit_update_record             
;
2018-07-19 deposited with the CCDC.
2018-11-16 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C14 H18 N2 O S'
_chemical_formula_weight         262.36
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'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   5.5091(7)
_cell_length_b                   7.2665(8)
_cell_length_c                   16.992(2)
_cell_angle_alpha                80.823(5)
_cell_angle_beta                 83.934(4)
_cell_angle_gamma                78.863(4)
_cell_volume                     656.90(14)
_cell_formula_units_Z            2
_cell_measurement_temperature    99(2)
_cell_measurement_reflns_used    3535
_cell_measurement_theta_min      2.89
_cell_measurement_theta_max      27.08

_exptl_crystal_description       Niddle
_exptl_crystal_colour            White
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.326
_exptl_crystal_F_000             280.0
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_absorpt_coefficient_mu    0.236
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      99(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            6348
_diffrn_reflns_av_unetI/netI     0.0675
_diffrn_reflns_av_R_equivalents  0.0640
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.436
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_full        24.999
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             2310
_reflns_number_gt                1873
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1231P)²+2.4644P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2310
_refine_ls_number_parameters     164
_refine_ls_number_restraints     42
_refine_ls_R_factor_all          0.1205
_refine_ls_R_factor_gt           0.1014
_refine_ls_wR_factor_ref         0.2926
_refine_ls_wR_factor_gt          0.2704
_refine_ls_goodness_of_fit_ref   1.091
_refine_ls_restrained_S_all      1.178
_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.7406(3) 0.2674(2) 0.18428(10) 0.0529(6) Uani 1 1 d . . . . .
O1 O 0.7044(6) 0.3055(5) 0.5895(2) 0.0394(9) Uani 1 1 d . . . . .
N1 N 0.6750(8) 0.5065(6) 0.2927(3) 0.0386(10) Uani 1 1 d . . . . .
H1 H 0.582658 0.605710 0.311242 0.046 Uiso 1 1 calc R U . . .
C12 C 0.8013(8) 0.3702(6) 0.4235(3) 0.0312(11) Uani 1 1 d . . . . .
H12 H 0.639861 0.419279 0.445013 0.037 Uiso 1 1 calc R U . . .
C11 C 0.9811(8) 0.2714(6) 0.4753(3) 0.0335(11) Uani 1 1 d . . . . .
C13 C 0.9162(8) 0.2485(6) 0.5627(3) 0.0341(11) Uani 1 1 d . . . . .
C7 C 0.8565(9) 0.3968(6) 0.3416(3) 0.0353(11) Uani 1 1 d . . . . .
C14 C 1.1118(9) 0.1509(7) 0.6177(4) 0.0439(13) Uani 1 1 d . . . . .
H14A H 1.061176 0.182191 0.671738 0.066 Uiso 1 1 calc R U . . .
H14B H 1.268967 0.193104 0.598682 0.066 Uiso 1 1 calc R U . . .
H14C H 1.133122 0.013495 0.618702 0.066 Uiso 1 1 calc R U . . .
C10 C 1.2157(8) 0.1958(6) 0.4421(4) 0.0420(13) Uani 1 1 d . . . . .
H10 H 1.338770 0.126648 0.476012 0.050 Uiso 1 1 calc R U . . .
C8 C 1.0940(9) 0.3242(7) 0.3099(4) 0.0439(13) Uani 1 1 d . . . . .
H8 H 1.135309 0.345206 0.253842 0.053 Uiso 1 1 calc R U . . .
C9 C 1.2683(9) 0.2217(7) 0.3605(4) 0.0454(14) Uani 1 1 d . . . . .
H9 H 1.427198 0.168035 0.338646 0.054 Uiso 1 1 calc R U . . .
C1 C 0.6281(11) 0.4731(8) 0.2187(4) 0.0494(14) Uani 1 1 d . . . . .
N2 N 0.4795(14) 0.6171(7) 0.1780(4) 0.084(2) Uani 1 1 d . . . . .
C4 C 0.2147(14) 0.9268(9) 0.0755(3) 0.0577(17) Uani 1 1 d . . . . .
H4A H 0.036343 0.984124 0.076133 0.069 Uiso 1 1 calc R U . . .
H4B H 0.301932 0.995989 0.029648 0.069 Uiso 1 1 calc R U . . .
C5 C 0.313(2) 0.9526(9) 0.1511(5) 0.100(3) Uani 1 1 d D U . . .
H5A H 0.402966 1.060245 0.138156 0.120 Uiso 1 1 calc R U . . .
H5B H 0.167718 0.992138 0.188252 0.120 Uiso 1 1 calc R U . . .
C3 C 0.243(3) 0.7290(11) 0.0633(6) 0.151(6) Uani 1 1 d D U . . .
H3A H 0.075057 0.696760 0.071782 0.182 Uiso 1 1 calc R U . . .
H3B H 0.296590 0.725025 0.006030 0.182 Uiso 1 1 calc R U . . .
C2 C 0.394(3) 0.5840(13) 0.1048(8) 0.182(7) Uani 1 1 d D U . . .
H2A H 0.542274 0.545043 0.068743 0.219 Uiso 1 1 calc R U . . .
H2B H 0.305841 0.475387 0.117807 0.219 Uiso 1 1 calc R U . . .
C6 C 0.462(3) 0.8094(11) 0.1914(7) 0.186(7) Uani 1 1 d D U . . .
H15A H 0.412398 0.812763 0.248979 0.223 Uiso 1 1 calc R U . . .
H15B H 0.631492 0.838641 0.181805 0.223 Uiso 1 1 calc R U . . .


_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 1.674(6) . ?
O1 C13 1.226(6) . ?
N1 C1 1.378(7) . ?
N1 C7 1.407(6) . ?
N1 H1 0.8800 . ?
C12 C7 1.383(7) . ?
C12 C11 1.407(6) . ?
C12 H12 0.9500 . ?
C11 C10 1.400(7) . ?
C11 C13 1.481(8) . ?
C13 C14 1.498(6) . ?
C7 C8 1.398(7) . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C10 C9 1.376(8) . ?
C10 H10 0.9500 . ?
C8 C9 1.383(8) . ?
C8 H8 0.9500 . ?
C9 H9 0.9500 . ?
C1 N2 1.342(8) . ?
N2 C6 1.435(9) . ?
N2 C2 1.445(9) . ?
C4 C3 1.461(9) . ?
C4 C5 1.497(8) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 C6 1.337(9) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C3 C2 1.358(10) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C6 H15A 0.9900 . ?
C6 H15B 0.9900 . ?

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 C7 126.1(4) . . ?
C1 N1 H1 116.9 . . ?
C7 N1 H1 116.9 . . ?
C7 C12 C11 120.9(4) . . ?
C7 C12 H12 119.6 . . ?
C11 C12 H12 119.6 . . ?
C10 C11 C12 118.6(5) . . ?
C10 C11 C13 122.1(4) . . ?
C12 C11 C13 119.3(4) . . ?
O1 C13 C11 120.5(4) . . ?
O1 C13 C14 120.5(5) . . ?
C11 C13 C14 119.0(4) . . ?
C12 C7 C8 119.6(5) . . ?
C12 C7 N1 118.6(4) . . ?
C8 C7 N1 121.7(5) . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C9 C10 C11 120.1(5) . . ?
C9 C10 H10 120.0 . . ?
C11 C10 H10 120.0 . . ?
C9 C8 C7 119.6(6) . . ?
C9 C8 H8 120.2 . . ?
C7 C8 H8 120.2 . . ?
C10 C9 C8 121.2(5) . . ?
C10 C9 H9 119.4 . . ?
C8 C9 H9 119.4 . . ?
N2 C1 N1 114.2(5) . . ?
N2 C1 S1 123.3(4) . . ?
N1 C1 S1 122.5(4) . . ?
C1 N2 C6 121.8(5) . . ?
C1 N2 C2 117.6(6) . . ?
C6 N2 C2 118.2(6) . . ?
C3 C4 C5 113.9(5) . . ?
C3 C4 H4A 108.8 . . ?
C5 C4 H4A 108.8 . . ?
C3 C4 H4B 108.8 . . ?
C5 C4 H4B 108.8 . . ?
H4A C4 H4B 107.7 . . ?
C6 C5 C4 120.2(6) . . ?
C6 C5 H5A 107.3 . . ?
C4 C5 H5A 107.3 . . ?
C6 C5 H5B 107.3 . . ?
C4 C5 H5B 107.3 . . ?
H5A C5 H5B 106.9 . . ?
C2 C3 C4 123.8(7) . . ?
C2 C3 H3A 106.4 . . ?
C4 C3 H3A 106.4 . . ?
C2 C3 H3B 106.4 . . ?
C4 C3 H3B 106.4 . . ?
H3A C3 H3B 106.5 . . ?
C3 C2 N2 117.9(7) . . ?
C3 C2 H2A 107.8 . . ?
N2 C2 H2A 107.8 . . ?
C3 C2 H2B 107.8 . . ?
N2 C2 H2B 107.8 . . ?
H2A C2 H2B 107.2 . . ?
C5 C6 N2 121.8(7) . . ?
C5 C6 H15A 106.9 . . ?
N2 C6 H15A 106.9 . . ?
C5 C6 H15B 106.9 . . ?
N2 C6 H15B 106.9 . . ?
H15A C6 H15B 106.7 . . ?

_refine_diff_density_max         1.099
_refine_diff_density_min         -1.166
_refine_diff_density_rms         0.102



