# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# 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_mo_150128j_0m
_database_code_depnum_ccdc_archive 'CCDC 1431979'
_audit_update_record             
;
2015-10-17 deposited with the CCDC.
2015-11-30 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 H14 N2 O3 S'
_chemical_formula_weight         266.31

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                   8.3507(13)
_cell_length_b                   8.6494(14)
_cell_length_c                   9.0014(15)
_cell_angle_alpha                79.307(3)
_cell_angle_beta                 84.564(3)
_cell_angle_gamma                79.146(3)
_cell_volume                     626.23(18)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    3429
_cell_measurement_theta_min      2.31
_cell_measurement_theta_max      30.28

_exptl_crystal_description       block
_exptl_crystal_colour            'pale yellow'
_exptl_crystal_size_max          0.27
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.19
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.412
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             280
_exptl_absorpt_coefficient_mu    0.260
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9330
_exptl_absorpt_correction_T_max  0.9522
_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         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            3408
_diffrn_reflns_av_R_equivalents  0.0212
_diffrn_reflns_av_sigmaI/netI    0.0342
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         2.31
_diffrn_reflns_theta_max         25.00
_reflns_number_total             2165
_reflns_number_gt                2018
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_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 > 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)+(0.0891P)²+0.2763P] 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       0.124(17)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2165
_refine_ls_number_parameters     165
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0457
_refine_ls_R_factor_gt           0.0422
_refine_ls_wR_factor_ref         0.1468
_refine_ls_wR_factor_gt          0.1353
_refine_ls_goodness_of_fit_ref   1.113
_refine_ls_restrained_S_all      1.113
_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 0.3430(2) -0.0612(3) 0.3847(2) 0.0327(5) Uani 1 1 d . . .
C2 C 0.4091(3) -0.2203(3) 0.4254(3) 0.0409(5) Uani 1 1 d . . .
H2 H 0.4610 -0.2809 0.3538 0.049 Uiso 1 1 calc R . .
C3 C 0.3950(3) -0.2862(3) 0.5777(3) 0.0462(6) Uani 1 1 d . . .
H3 H 0.4371 -0.3936 0.6090 0.055 Uiso 1 1 calc R . .
C4 C 0.3196(3) -0.1950(3) 0.6836(3) 0.0477(6) Uani 1 1 d . . .
H4 H 0.3139 -0.2416 0.7854 0.057 Uiso 1 1 calc R . .
C5 C 0.2521(3) -0.0354(3) 0.6412(3) 0.0454(6) Uani 1 1 d . . .
H5 H 0.2011 0.0254 0.7130 0.055 Uiso 1 1 calc R . .
C6 C 0.2626(3) 0.0316(3) 0.4886(2) 0.0349(5) Uani 1 1 d . . .
C7 C 0.2067(3) 0.1929(3) 0.4033(2) 0.0345(5) Uani 1 1 d . . .
C8 C 0.1837(3) 0.3477(3) 0.4650(3) 0.0477(6) Uani 1 1 d . . .
H8A H 0.2037 0.3406 0.5707 0.057 Uiso 1 1 calc R . .
H8B H 0.2152 0.4401 0.3982 0.057 Uiso 1 1 calc R . .
C9 C 0.0377(3) 0.2925(3) 0.4315(3) 0.0468(6) Uani 1 1 d . . .
H9A H -0.0200 0.3505 0.3438 0.056 Uiso 1 1 calc R . .
H9B H -0.0315 0.2510 0.5165 0.056 Uiso 1 1 calc R . .
C10 C 0.2685(2) 0.1848(2) 0.2447(2) 0.0312(5) Uani 1 1 d . . .
C11 C -0.0189(4) 0.3044(4) -0.0656(5) 0.0706(9) Uani 1 1 d . . .
H11A H -0.0463 0.3211 0.0381 0.085 Uiso 1 1 calc R . .
H11B H -0.0239 0.4081 -0.1301 0.085 Uiso 1 1 calc R . .
C12 C -0.1356(4) 0.2192(5) -0.1109(4) 0.0786(10) Uani 1 1 d . . .
H12A H -0.1166 0.2146 -0.2169 0.118 Uiso 1 1 calc R . .
H12B H -0.2446 0.2742 -0.0918 0.118 Uiso 1 1 calc R . .
H12C H -0.1226 0.1127 -0.0538 0.118 Uiso 1 1 calc R . .
N1 N 0.3437(2) 0.0350(2) 0.2400(2) 0.0334(4) Uani 1 1 d . . .
H1 H 0.3877 -0.0045 0.1557 0.040 Uiso 1 1 d R . .
N2 N 0.2450(2) 0.3110(2) 0.1362(2) 0.0372(5) Uani 1 1 d . . .
O1 O 0.1459(2) 0.2122(2) -0.07775(19) 0.0485(5) Uani 1 1 d . . .
O2 O 0.2811(3) 0.4443(2) -0.1258(2) 0.0599(6) Uani 1 1 d . . .
O3 O 0.4309(2) 0.1726(2) -0.0579(2) 0.0589(6) Uani 1 1 d . . .
S1 S 0.28880(7) 0.29019(6) -0.03649(6) 0.0393(3) 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 1.378(3) . ?
C1 C6 1.388(3) . ?
C1 N1 1.410(3) . ?
C2 C3 1.387(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.380(4) . ?
C3 H3 0.9300 . ?
C4 C5 1.386(4) . ?
C4 H4 0.9300 . ?
C5 C6 1.389(3) . ?
C5 H5 0.9300 . ?
C6 C7 1.476(3) . ?
C7 C10 1.481(3) . ?
C7 C8 1.515(3) . ?
C7 C9 1.534(3) . ?
C8 C9 1.465(4) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 N2 1.320(3) . ?
C10 N1 1.336(3) . ?
C11 C12 1.454(4) . ?
C11 O1 1.461(3) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
N1 H1 0.9073 . ?
N2 S1 1.5979(19) . ?
O1 S1 1.5800(19) . ?
O2 S1 1.4164(18) . ?
O3 S1 1.4331(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 C6 122.7(2) . . ?
C2 C1 N1 128.6(2) . . ?
C6 C1 N1 108.64(18) . . ?
C1 C2 C3 117.1(2) . . ?
C1 C2 H2 121.4 . . ?
C3 C2 H2 121.4 . . ?
C4 C3 C2 121.1(2) . . ?
C4 C3 H3 119.4 . . ?
C2 C3 H3 119.4 . . ?
C3 C4 C5 121.2(2) . . ?
C3 C4 H4 119.4 . . ?
C5 C4 H4 119.4 . . ?
C4 C5 C6 118.3(2) . . ?
C4 C5 H5 120.8 . . ?
C6 C5 H5 120.8 . . ?
C1 C6 C5 119.4(2) . . ?
C1 C6 C7 107.11(18) . . ?
C5 C6 C7 133.4(2) . . ?
C6 C7 C10 105.00(17) . . ?
C6 C7 C8 125.7(2) . . ?
C10 C7 C8 121.2(2) . . ?
C6 C7 C9 123.63(19) . . ?
C10 C7 C9 118.31(18) . . ?
C8 C7 C9 57.42(16) . . ?
C9 C8 C7 61.91(15) . . ?
C9 C8 H8A 117.6 . . ?
C7 C8 H8A 117.6 . . ?
C9 C8 H8B 117.6 . . ?
C7 C8 H8B 117.6 . . ?
H8A C8 H8B 114.7 . . ?
C8 C9 C7 60.67(15) . . ?
C8 C9 H9A 117.7 . . ?
C7 C9 H9A 117.7 . . ?
C8 C9 H9B 117.7 . . ?
C7 C9 H9B 117.7 . . ?
H9A C9 H9B 114.8 . . ?
N2 C10 N1 130.65(19) . . ?
N2 C10 C7 121.74(18) . . ?
N1 C10 C7 107.61(17) . . ?
C12 C11 O1 109.9(3) . . ?
C12 C11 H11A 109.7 . . ?
O1 C11 H11A 109.7 . . ?
C12 C11 H11B 109.7 . . ?
O1 C11 H11B 109.7 . . ?
H11A C11 H11B 108.2 . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C10 N1 C1 111.57(17) . . ?
C10 N1 H1 126.1 . . ?
C1 N1 H1 122.3 . . ?
C10 N2 S1 119.71(15) . . ?
C11 O1 S1 116.42(16) . . ?
O2 S1 O3 117.95(12) . . ?
O2 S1 O1 108.60(11) . . ?
O3 S1 O1 102.90(11) . . ?
O2 S1 N2 108.12(11) . . ?
O3 S1 N2 113.81(10) . . ?
O1 S1 N2 104.37(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
C6 C1 C2 C3 -1.1(3) . . . . ?
N1 C1 C2 C3 178.4(2) . . . . ?
C1 C2 C3 C4 -0.8(4) . . . . ?
C2 C3 C4 C5 1.4(4) . . . . ?
C3 C4 C5 C6 -0.2(4) . . . . ?
C2 C1 C6 C5 2.2(3) . . . . ?
N1 C1 C6 C5 -177.31(19) . . . . ?
C2 C1 C6 C7 -178.93(19) . . . . ?
N1 C1 C6 C7 1.5(2) . . . . ?
C4 C5 C6 C1 -1.5(3) . . . . ?
C4 C5 C6 C7 180.0(2) . . . . ?
C1 C6 C7 C10 -2.5(2) . . . . ?
C5 C6 C7 C10 176.1(2) . . . . ?
C1 C6 C7 C8 -150.9(2) . . . . ?
C5 C6 C7 C8 27.7(4) . . . . ?
C1 C6 C7 C9 137.7(2) . . . . ?
C5 C6 C7 C9 -43.7(4) . . . . ?
C6 C7 C8 C9 -110.5(2) . . . . ?
C10 C7 C8 C9 105.7(2) . . . . ?
C6 C7 C9 C8 114.0(2) . . . . ?
C10 C7 C9 C8 -110.7(2) . . . . ?
C6 C7 C10 N2 -177.95(18) . . . . ?
C8 C7 C10 N2 -27.8(3) . . . . ?
C9 C7 C10 N2 39.3(3) . . . . ?
C6 C7 C10 N1 2.6(2) . . . . ?
C8 C7 C10 N1 152.8(2) . . . . ?
C9 C7 C10 N1 -140.1(2) . . . . ?
N2 C10 N1 C1 178.8(2) . . . . ?
C7 C10 N1 C1 -1.7(2) . . . . ?
C2 C1 N1 C10 -179.4(2) . . . . ?
C6 C1 N1 C10 0.1(2) . . . . ?
N1 C10 N2 S1 9.0(3) . . . . ?
C7 C10 N2 S1 -170.35(15) . . . . ?
C12 C11 O1 S1 178.5(2) . . . . ?
C11 O1 S1 O2 -54.7(2) . . . . ?
C11 O1 S1 O3 179.5(2) . . . . ?
C11 O1 S1 N2 60.4(2) . . . . ?
C10 N2 S1 O2 -169.44(17) . . . . ?
C10 N2 S1 O3 -36.3(2) . . . . ?
C10 N2 S1 O1 75.08(18) . . . . ?

_diffrn_measured_fraction_theta_max 0.981
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.981
_refine_diff_density_max         0.382
_refine_diff_density_min         -0.331
_refine_diff_density_rms         0.071
