# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2019

####################################################################### 
# 
# 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_p
_database_code_depnum_ccdc_archive 'CCDC 1878328'
_audit_update_record             
;
2018-11-11 deposited with the CCDC.
2019-01-17 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C12 H12 N2 O2 S'
_chemical_formula_weight         248.30

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'
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'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P21/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                   8.9680(15)
_cell_length_b                   9.0840(16)
_cell_length_c                   14.804(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 105.357(4)
_cell_angle_gamma                90.00
_cell_volume                     1163.0(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    1679
_cell_measurement_theta_min      2.36
_cell_measurement_theta_max      22.39

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.17
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.418
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             520
_exptl_absorpt_coefficient_mu    0.269
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9432
_exptl_absorpt_correction_T_max  0.9557
_exptl_absorpt_process_details   'SADABS; Bruker, 2000'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(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         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            10174
_diffrn_reflns_av_R_equivalents  0.0525
_diffrn_reflns_av_sigmaI/netI    0.0504
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.36
_diffrn_reflns_theta_max         27.50
_reflns_number_total             2641
_reflns_number_gt                2032
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_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)+(0.0405P)²+0.2662P] 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     SHELXL
_refine_ls_extinction_coef       0.0130(17)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2641
_refine_ls_number_parameters     167
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0587
_refine_ls_R_factor_gt           0.0416
_refine_ls_wR_factor_ref         0.1012
_refine_ls_wR_factor_gt          0.0921
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_restrained_S_all      1.026
_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 0.45083(5) 0.77014(5) 0.20594(3) 0.02684(16) Uani 1 1 d . . .
O1 O 0.42207(15) 0.85066(15) 0.28340(9) 0.0343(3) Uani 1 1 d . . .
O2 O 0.60834(14) 0.73640(15) 0.20948(10) 0.0369(4) Uani 1 1 d . . .
N2 N 0.36637(17) 0.61065(18) 0.19866(12) 0.0296(4) Uani 1 1 d . . .
N1 N 0.4740(2) 0.6953(2) 0.01032(17) 0.0473(5) Uani 1 1 d . . .
C1 C 0.3637(2) 0.8656(2) 0.10340(13) 0.0269(4) Uani 1 1 d . . .
C2 C 0.20435(19) 0.5841(2) 0.17658(13) 0.0267(4) Uani 1 1 d . . .
C3 C 0.1035(2) 0.6789(2) 0.20396(15) 0.0358(5) Uani 1 1 d . . .
H3 H 0.1397 0.7662 0.2349 0.043 Uiso 1 1 calc R . .
C4 C 0.3870(2) 0.8178(2) 0.01760(14) 0.0324(4) Uani 1 1 d . . .
C5 C 0.2172(3) 1.0119(3) -0.05832(18) 0.0547(6) Uani 1 1 d . . .
H5 H 0.1671 1.0605 -0.1132 0.066 Uiso 1 1 calc R . .
C6 C -0.1067(2) 0.5144(3) 0.13918(17) 0.0506(6) Uani 1 1 d . . .
H6 H -0.2109 0.4904 0.1271 0.061 Uiso 1 1 calc R . .
C7 C 0.2697(2) 0.9861(2) 0.10727(15) 0.0368(5) Uani 1 1 d . . .
H7 H 0.2565 1.0172 0.1645 0.044 Uiso 1 1 calc R . .
C8 C 0.1494(2) 0.4558(2) 0.12995(16) 0.0405(5) Uani 1 1 d . . .
H8 H 0.2167 0.3923 0.1110 0.049 Uiso 1 1 calc R . .
C9 C -0.0516(2) 0.6427(3) 0.18498(17) 0.0449(6) Uani 1 1 d . . .
H9 H -0.1195 0.7061 0.2035 0.054 Uiso 1 1 calc R . .
C10 C 0.3105(3) 0.8948(3) -0.06226(16) 0.0464(6) Uani 1 1 d . . .
H10 H 0.3233 0.8658 -0.1200 0.056 Uiso 1 1 calc R . .
C11 C 0.1962(3) 1.0591(2) 0.02625(18) 0.0505(6) Uani 1 1 d . . .
H11 H 0.1329 1.1395 0.0284 0.061 Uiso 1 1 calc R . .
C12 C -0.0059(3) 0.4217(3) 0.11137(19) 0.0552(7) Uani 1 1 d . . .
H12 H -0.0427 0.3351 0.0797 0.066 Uiso 1 1 calc R . .
H40 H 0.425(3) 0.545(3) 0.1897(15) 0.048(7) Uiso 1 1 d . . .
H41 H 0.486(3) 0.683(3) -0.0467(19) 0.062(8) Uiso 1 1 d . . .
H42 H 0.558(3) 0.677(3) 0.0593(19) 0.062(8) Uiso 1 1 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 0.0223(2) 0.0277(3) 0.0308(3) -0.00058(19) 0.00766(17) -0.00267(17)
O1 0.0402(8) 0.0347(8) 0.0296(8) -0.0049(6) 0.0123(6) -0.0072(6)
O2 0.0211(6) 0.0439(9) 0.0453(9) 0.0030(6) 0.0080(6) -0.0011(6)
N2 0.0224(8) 0.0231(8) 0.0441(11) 0.0004(7) 0.0106(7) 0.0022(6)
N1 0.0504(12) 0.0530(13) 0.0423(13) -0.0128(10) 0.0189(10) 0.0062(9)
C1 0.0250(9) 0.0253(10) 0.0306(11) -0.0008(8) 0.0080(7) -0.0041(7)
C2 0.0236(9) 0.0260(10) 0.0317(11) 0.0068(8) 0.0092(7) -0.0013(7)
C3 0.0282(10) 0.0309(11) 0.0499(13) 0.0021(9) 0.0132(9) 0.0011(8)
C4 0.0314(10) 0.0323(11) 0.0343(12) -0.0022(8) 0.0104(8) -0.0074(8)
C5 0.0640(15) 0.0484(15) 0.0431(15) 0.0144(12) -0.0007(11) -0.0011(12)
C6 0.0249(10) 0.0499(14) 0.0742(18) 0.0162(12) 0.0079(10) -0.0080(9)
C7 0.0396(11) 0.0298(11) 0.0410(13) -0.0047(9) 0.0109(9) -0.0007(8)
C8 0.0341(10) 0.0344(11) 0.0536(14) -0.0064(10) 0.0128(9) -0.0022(8)
C9 0.0284(10) 0.0448(13) 0.0654(16) 0.0166(11) 0.0192(10) 0.0086(9)
C10 0.0579(14) 0.0484(14) 0.0320(13) 0.0000(10) 0.0105(10) -0.0069(11)
C11 0.0508(14) 0.0327(12) 0.0624(17) 0.0036(11) 0.0054(11) 0.0106(10)
C12 0.0405(12) 0.0417(13) 0.0783(19) -0.0079(12) 0.0067(12) -0.0146(10)

_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 1.4327(13) . ?
S1 O1 1.4399(14) . ?
S1 N2 1.6251(16) . ?
S1 C1 1.7431(19) . ?
N2 C2 1.423(2) . ?
N2 H40 0.83(2) . ?
N1 C4 1.380(3) . ?
N1 H41 0.88(3) . ?
N1 H42 0.91(3) . ?
C1 C7 1.392(3) . ?
C1 C4 1.409(3) . ?
C2 C8 1.378(3) . ?
C2 C3 1.385(3) . ?
C3 C9 1.384(3) . ?
C3 H3 0.9300 . ?
C4 C10 1.388(3) . ?
C5 C10 1.364(3) . ?
C5 C11 1.383(3) . ?
C5 H5 0.9300 . ?
C6 C9 1.373(3) . ?
C6 C12 1.376(3) . ?
C6 H6 0.9300 . ?
C7 C11 1.377(3) . ?
C7 H7 0.9300 . ?
C8 C12 1.381(3) . ?
C8 H8 0.9300 . ?
C9 H9 0.9300 . ?
C10 H10 0.9300 . ?
C11 H11 0.9300 . ?
C12 H12 0.9300 . ?

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 117.53(8) . . ?
O2 S1 N2 104.45(8) . . ?
O1 S1 N2 109.09(8) . . ?
O2 S1 C1 110.39(8) . . ?
O1 S1 C1 107.90(9) . . ?
N2 S1 C1 106.98(8) . . ?
C2 N2 S1 126.58(13) . . ?
C2 N2 H40 119.3(16) . . ?
S1 N2 H40 110.6(16) . . ?
C4 N1 H41 112.7(17) . . ?
C4 N1 H42 116.6(17) . . ?
H41 N1 H42 117(2) . . ?
C7 C1 C4 121.02(18) . . ?
C7 C1 S1 119.46(15) . . ?
C4 C1 S1 119.51(14) . . ?
C8 C2 C3 119.88(17) . . ?
C8 C2 N2 117.80(17) . . ?
C3 C2 N2 122.26(17) . . ?
C9 C3 C2 119.5(2) . . ?
C9 C3 H3 120.3 . . ?
C2 C3 H3 120.3 . . ?
N1 C4 C10 120.1(2) . . ?
N1 C4 C1 122.73(19) . . ?
C10 C4 C1 117.04(19) . . ?
C10 C5 C11 120.9(2) . . ?
C10 C5 H5 119.6 . . ?
C11 C5 H5 119.6 . . ?
C9 C6 C12 119.27(19) . . ?
C9 C6 H6 120.4 . . ?
C12 C6 H6 120.4 . . ?
C11 C7 C1 119.9(2) . . ?
C11 C7 H7 120.0 . . ?
C1 C7 H7 120.0 . . ?
C2 C8 C12 119.83(19) . . ?
C2 C8 H8 120.1 . . ?
C12 C8 H8 120.1 . . ?
C6 C9 C3 120.8(2) . . ?
C6 C9 H9 119.6 . . ?
C3 C9 H9 119.6 . . ?
C5 C10 C4 121.8(2) . . ?
C5 C10 H10 119.1 . . ?
C4 C10 H10 119.1 . . ?
C7 C11 C5 119.4(2) . . ?
C7 C11 H11 120.3 . . ?
C5 C11 H11 120.3 . . ?
C6 C12 C8 120.7(2) . . ?
C6 C12 H12 119.6 . . ?
C8 C12 H12 119.6 . . ?

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 N2 C2 -167.92(16) . . . . ?
O1 S1 N2 C2 65.62(18) . . . . ?
C1 S1 N2 C2 -50.86(18) . . . . ?
O2 S1 C1 C7 -137.05(15) . . . . ?
O1 S1 C1 C7 -7.38(17) . . . . ?
N2 S1 C1 C7 109.88(16) . . . . ?
O2 S1 C1 C4 44.24(17) . . . . ?
O1 S1 C1 C4 173.91(14) . . . . ?
N2 S1 C1 C4 -68.83(16) . . . . ?
S1 N2 C2 C8 148.89(16) . . . . ?
S1 N2 C2 C3 -34.0(3) . . . . ?
C8 C2 C3 C9 0.7(3) . . . . ?
N2 C2 C3 C9 -176.32(18) . . . . ?
C7 C1 C4 N1 -177.20(19) . . . . ?
S1 C1 C4 N1 1.5(3) . . . . ?
C7 C1 C4 C10 -0.9(3) . . . . ?
S1 C1 C4 C10 177.82(15) . . . . ?
C4 C1 C7 C11 0.9(3) . . . . ?
S1 C1 C7 C11 -177.80(16) . . . . ?
C3 C2 C8 C12 -0.5(3) . . . . ?
N2 C2 C8 C12 176.64(19) . . . . ?
C12 C6 C9 C3 -0.5(3) . . . . ?
C2 C3 C9 C6 -0.2(3) . . . . ?
C11 C5 C10 C4 0.5(4) . . . . ?
N1 C4 C10 C5 176.6(2) . . . . ?
C1 C4 C10 C5 0.2(3) . . . . ?
C1 C7 C11 C5 -0.2(3) . . . . ?
C10 C5 C11 C7 -0.5(4) . . . . ?
C9 C6 C12 C8 0.7(4) . . . . ?
C2 C8 C12 C6 -0.2(4) . . . . ?

_diffrn_measured_fraction_theta_max 0.990
_diffrn_reflns_theta_full        27.50
_diffrn_measured_fraction_theta_full 0.990
_refine_diff_density_max         0.350
_refine_diff_density_min         -0.301
_refine_diff_density_rms         0.050
