# Electronic Supplementary Material (ESI) for Chemical Communications.
# This journal is © The Royal Society of Chemistry 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_1_a
_database_code_depnum_ccdc_archive 'CCDC 1839767'
_audit_update_record             
;
2018-04-26 deposited with the CCDC.
2018-06-14 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C14 H16 N2 O2 S'
_chemical_formula_weight         276.35

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'
O O 0.0106 0.0060 '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'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

_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+1/2, -z'

_cell_length_a                   9.955(3)
_cell_length_b                   5.5629(19)
_cell_length_c                   12.732(4)
_cell_angle_alpha                90
_cell_angle_beta                 92.902(9)
_cell_angle_gamma                90
_cell_volume                     704.2(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    1421
_cell_measurement_theta_min      2.66
_cell_measurement_theta_max      28.35

_exptl_crystal_description       Block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.303
_exptl_crystal_F_000             292
_exptl_transmission_factor_min   0.864
_exptl_transmission_factor_max   0.864
_exptl_crystal_size_max          0.220
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.180
_exptl_absorpt_coefficient_mu    0.229
_shelx_estimated_absorpt_T_min   0.951
_shelx_estimated_absorpt_T_max   0.960
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  CCD
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            1887
_diffrn_reflns_av_unetI/netI     0.0424
_diffrn_reflns_av_R_equivalents  0.0909
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       1
_diffrn_reflns_theta_min         2.048
_diffrn_reflns_theta_max         24.994
_diffrn_reflns_theta_full        24.994
_diffrn_measured_fraction_theta_max 0.941
_diffrn_measured_fraction_theta_full 0.941
_diffrn_reflns_Laue_measured_fraction_max 0.941
_diffrn_reflns_Laue_measured_fraction_full 0.941
_diffrn_reflns_point_group_measured_fraction_max 0.955
_diffrn_reflns_point_group_measured_fraction_full 0.955
_reflns_number_total             1842
_reflns_number_gt                1580
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.824
_reflns_Friedel_fraction_max     0.973
_reflns_Friedel_fraction_full    0.973

_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.2000P)²] 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_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.4(4)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         1842
_refine_ls_number_parameters     151
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.1102
_refine_ls_R_factor_gt           0.0975
_refine_ls_wR_factor_ref         0.2910
_refine_ls_wR_factor_gt          0.2489
_refine_ls_goodness_of_fit_ref   1.243
_refine_ls_restrained_S_all      1.243
_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
C1 C 0.8566(13) 0.624(3) 0.4241(8) 0.077(4) Uani 1 1 d . . . . .
H1A H 0.8666 0.7958 0.4222 0.116 Uiso 1 1 calc R U . . .
H1B H 0.8216 0.5681 0.3569 0.116 Uiso 1 1 calc R U . . .
H1C H 0.9426 0.5513 0.4403 0.116 Uiso 1 1 calc R U . . .
C2 C 0.7584(6) 0.5556(10) 0.5097(4) 0.054(2) Uani 1 1 d G . . . .
C3 C 0.6832(7) 0.3453(9) 0.5022(4) 0.056(3) Uani 1 1 d G . . . .
H3 H 0.6945 0.2393 0.4468 0.067 Uiso 1 1 calc R U . . .
C4 C 0.5910(6) 0.2932(9) 0.5774(4) 0.053(2) Uani 1 1 d G . . . .
H4 H 0.5407 0.1525 0.5724 0.064 Uiso 1 1 calc R U . . .
C5 C 0.5742(5) 0.4515(11) 0.6602(4) 0.043(2) Uani 1 1 d G . . . .
C6 C 0.6494(5) 0.6618(10) 0.6677(3) 0.047(2) Uani 1 1 d G . . . .
H6 H 0.6382 0.7677 0.7231 0.056 Uiso 1 1 calc R U . . .
C7 C 0.7416(5) 0.7138(9) 0.5925(4) 0.049(2) Uani 1 1 d G . . . .
H7 H 0.7919 0.8545 0.5975 0.059 Uiso 1 1 calc R U . . .
C8 C 0.2266(5) 0.5191(10) 0.8581(4) 0.046(2) Uani 1 1 d G . . . .
C9 C 0.1229(6) 0.5974(10) 0.7893(4) 0.056(3) Uani 1 1 d G . . . .
H9 H 0.1344 0.7339 0.7484 0.068 Uiso 1 1 calc R U . . .
C10 C 0.0021(5) 0.4719(13) 0.7814(5) 0.067(3) Uani 1 1 d G . . . .
H10 H -0.0673 0.5243 0.7353 0.080 Uiso 1 1 calc R U . . .
C11 C -0.0150(5) 0.2680(12) 0.8424(5) 0.051(2) Uani 1 1 d G . . . .
C12 C 0.0887(6) 0.1896(10) 0.9112(4) 0.055(2) Uani 1 1 d G . . . .
H12 H 0.0772 0.0532 0.9521 0.066 Uiso 1 1 calc R U . . .
C13 C 0.2095(5) 0.3152(11) 0.9191(4) 0.052(2) Uani 1 1 d G . . . .
H13 H 0.2788 0.2628 0.9651 0.063 Uiso 1 1 calc R U . . .
C14 C -0.1475(12) 0.133(3) 0.8355(10) 0.086(4) Uani 1 1 d . . . . .
H14A H -0.2031 0.1876 0.8902 0.130 Uiso 1 1 calc R U . . .
H14B H -0.1308 -0.0359 0.8437 0.130 Uiso 1 1 calc R U . . .
H14C H -0.1925 0.1624 0.7682 0.130 Uiso 1 1 calc R U . . .
N1 N 0.4786(7) 0.3981(17) 0.7359(5) 0.053(2) Uani 1 1 d . . . . .
H1 H 0.4111 0.3062 0.7203 0.064 Uiso 1 1 calc R U . . .
N2 N 0.4967(8) 0.4969(15) 0.8353(5) 0.049(2) Uani 1 1 d . . . . .
H2 H 0.5657 0.4644 0.8761 0.059 Uiso 1 1 calc R U . . .
O1 O 0.4095(8) 0.7264(18) 0.9797(5) 0.074(3) Uani 1 1 d . . . . .
O2 O 0.3732(7) 0.8726(13) 0.7969(6) 0.0634(19) Uani 1 1 d . . . . .
S1 S 0.3791(2) 0.6782(5) 0.86984(14) 0.0487(8) Uani 1 1 d . . . . .


_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
C1 C2 1.548(11) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C2 C3 1.3900 . ?
C2 C7 1.3900 . ?
C3 C4 1.3900 . ?
C3 H3 0.9300 . ?
C4 C5 1.3900 . ?
C4 H4 0.9300 . ?
C5 C6 1.3900 . ?
C5 N1 1.419(8) . ?
C6 C7 1.3900 . ?
C6 H6 0.9300 . ?
C7 H7 0.9300 . ?
C8 C9 1.3900 . ?
C8 C13 1.3900 . ?
C8 S1 1.757(5) . ?
C9 C10 1.3900 . ?
C9 H9 0.9300 . ?
C10 C11 1.3900 . ?
C10 H10 0.9300 . ?
C11 C12 1.3900 . ?
C11 C14 1.516(13) . ?
C12 C13 1.3900 . ?
C12 H12 0.9300 . ?
C13 H13 0.9300 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
N1 N2 1.383(9) . ?
N1 H1 0.8600 . ?
N2 S1 1.623(8) . ?
N2 H2 0.8600 . ?
O1 S1 1.441(6) . ?
O2 S1 1.425(7) . ?

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 . . ?
C3 C2 C7 120.0 . . ?
C3 C2 C1 121.1(6) . . ?
C7 C2 C1 118.8(6) . . ?
C4 C3 C2 120.0 . . ?
C4 C3 H3 120.0 . . ?
C2 C3 H3 120.0 . . ?
C3 C4 C5 120.0 . . ?
C3 C4 H4 120.0 . . ?
C5 C4 H4 120.0 . . ?
C6 C5 C4 120.0 . . ?
C6 C5 N1 120.5(5) . . ?
C4 C5 N1 119.5(5) . . ?
C7 C6 C5 120.0 . . ?
C7 C6 H6 120.0 . . ?
C5 C6 H6 120.0 . . ?
C6 C7 C2 120.0 . . ?
C6 C7 H7 120.0 . . ?
C2 C7 H7 120.0 . . ?
C9 C8 C13 120.0 . . ?
C9 C8 S1 120.4(3) . . ?
C13 C8 S1 119.6(3) . . ?
C10 C9 C8 120.0 . . ?
C10 C9 H9 120.0 . . ?
C8 C9 H9 120.0 . . ?
C11 C10 C9 120.0 . . ?
C11 C10 H10 120.0 . . ?
C9 C10 H10 120.0 . . ?
C12 C11 C10 120.0 . . ?
C12 C11 C14 119.8(7) . . ?
C10 C11 C14 120.1(7) . . ?
C11 C12 C13 120.0 . . ?
C11 C12 H12 120.0 . . ?
C13 C12 H12 120.0 . . ?
C12 C13 C8 120.0 . . ?
C12 C13 H13 120.0 . . ?
C8 C13 H13 120.0 . . ?
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 . . ?
N2 N1 C5 118.5(6) . . ?
N2 N1 H1 120.7 . . ?
C5 N1 H1 120.7 . . ?
N1 N2 S1 115.7(6) . . ?
N1 N2 H2 122.2 . . ?
S1 N2 H2 122.2 . . ?
O2 S1 O1 119.4(5) . . ?
O2 S1 N2 107.5(4) . . ?
O1 S1 N2 105.0(4) . . ?
O2 S1 C8 108.7(4) . . ?
O1 S1 C8 108.3(4) . . ?
N2 S1 C8 107.2(4) . . ?

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
C7 C2 C3 C4 0.0 . . . . ?
C1 C2 C3 C4 -177.0(7) . . . . ?
C2 C3 C4 C5 0.0 . . . . ?
C3 C4 C5 C6 0.0 . . . . ?
C3 C4 C5 N1 179.2(6) . . . . ?
C4 C5 C6 C7 0.0 . . . . ?
N1 C5 C6 C7 -179.2(6) . . . . ?
C5 C6 C7 C2 0.0 . . . . ?
C3 C2 C7 C6 0.0 . . . . ?
C1 C2 C7 C6 177.0(7) . . . . ?
C13 C8 C9 C10 0.0 . . . . ?
S1 C8 C9 C10 -179.3(5) . . . . ?
C8 C9 C10 C11 0.0 . . . . ?
C9 C10 C11 C12 0.0 . . . . ?
C9 C10 C11 C14 178.9(8) . . . . ?
C10 C11 C12 C13 0.0 . . . . ?
C14 C11 C12 C13 -178.9(8) . . . . ?
C11 C12 C13 C8 0.0 . . . . ?
C9 C8 C13 C12 0.0 . . . . ?
S1 C8 C13 C12 179.3(5) . . . . ?
C6 C5 N1 N2 -25.4(9) . . . . ?
C4 C5 N1 N2 155.4(6) . . . . ?
C5 N1 N2 S1 117.4(7) . . . . ?
N1 N2 S1 O2 -60.4(7) . . . . ?
N1 N2 S1 O1 171.4(7) . . . . ?
N1 N2 S1 C8 56.3(7) . . . . ?
C9 C8 S1 O2 -2.8(5) . . . . ?
C13 C8 S1 O2 177.9(4) . . . . ?
C9 C8 S1 O1 128.3(5) . . . . ?
C13 C8 S1 O1 -51.0(6) . . . . ?
C9 C8 S1 N2 -118.8(4) . . . . ?
C13 C8 S1 N2 61.9(4) . . . . ?

_refine_diff_density_max         0.489
_refine_diff_density_min         -0.467
_refine_diff_density_rms         0.113

