# 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_131026h
_database_code_depnum_ccdc_archive 'CCDC 969639'
_audit_update_record             
;
2013-10-31 deposited with the CCDC.
2015-04-07 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C16 H17 N3 O2 S'
_chemical_formula_weight         315.39

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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/n

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   7.9805(7)
_cell_length_b                   23.492(2)
_cell_length_c                   9.3323(8)
_cell_angle_alpha                90.00
_cell_angle_beta                 112.494(2)
_cell_angle_gamma                90.00
_cell_volume                     1616.5(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    1447
_cell_measurement_theta_min      2.867
_cell_measurement_theta_max      22.696

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.43
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.21
_exptl_crystal_density_meas      0
_exptl_crystal_density_diffrn    1.296
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             664
_exptl_absorpt_coefficient_mu    0.210
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9150
_exptl_absorpt_correction_T_max  0.9571
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      298(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  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            8057
_diffrn_reflns_av_R_equivalents  0.0532
_diffrn_reflns_av_sigmaI/netI    0.0681
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         2.87
_diffrn_reflns_theta_max         25.01
_reflns_number_total             2843
_reflns_number_gt                1482
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_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)+(0.0778P)²+0.7236P] 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         2843
_refine_ls_number_parameters     222
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1192
_refine_ls_R_factor_gt           0.0582
_refine_ls_wR_factor_ref         0.1831
_refine_ls_wR_factor_gt          0.1427
_refine_ls_goodness_of_fit_ref   1.014
_refine_ls_restrained_S_all      1.014
_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
N1 N 1.2038(4) 0.07888(12) 0.5292(3) 0.0434(8) Uani 1 1 d . . .
H1 H 1.2724 0.0501 0.5341 0.052 Uiso 1 1 calc R . .
N2 N 1.2668(4) 0.19971(12) 0.5140(3) 0.0442(8) Uani 1 1 d . . .
H2 H 1.3358 0.2292 0.5322 0.053 Uiso 1 1 calc R . .
N3 N 0.7749(5) 0.05132(14) 0.4129(5) 0.0683(11) Uani 1 1 d . A .
O1 O 0.9042(4) 0.08962(11) 0.0765(3) 0.0619(8) Uani 1 1 d . C .
O2 O 0.9098(4) 0.18312(12) 0.0458(3) 0.0661(8) Uani 1 1 d . . .
S1 S 0.807(3) 0.1569(3) 0.481(4) 0.068(4) Uani 0.72(8) 1 d P A 1
S1' S 0.756(7) 0.1523(8) 0.404(11) 0.068(9) Uani 0.28(8) 1 d P A 2
C1 C 1.0479(4) 0.09166(14) 0.3867(4) 0.0395(9) Uani 1 1 d . A .
H1A H 1.0349 0.0588 0.3186 0.047 Uiso 1 1 calc R . .
C2 C 1.0708(5) 0.14268(14) 0.2969(4) 0.0396(9) Uani 1 1 d . . .
C3 C 1.1766(5) 0.18858(15) 0.3597(4) 0.0416(9) Uani 1 1 d . . .
C4 C 1.2690(5) 0.17258(16) 0.6485(4) 0.0442(9) Uani 1 1 d . . .
C5 C 1.2386(5) 0.11471(16) 0.6573(4) 0.0437(9) Uani 1 1 d . . .
C6 C 1.2538(6) 0.09163(19) 0.7996(5) 0.0619(12) Uani 1 1 d . . .
H6 H 1.2288 0.0532 0.8055 0.074 Uiso 1 1 calc R . .
C7 C 1.3049(7) 0.1246(2) 0.9314(6) 0.0812(15) Uani 1 1 d . . .
H7 H 1.3188 0.1083 1.0261 0.097 Uiso 1 1 calc R . .
C8 C 1.3357(7) 0.1824(2) 0.9215(6) 0.0822(15) Uani 1 1 d . . .
H8 H 1.3698 0.2051 1.0097 0.099 Uiso 1 1 calc R . .
C9 C 1.3155(6) 0.20588(18) 0.7812(5) 0.0599(11) Uani 1 1 d . . .
H9 H 1.3334 0.2448 0.7748 0.072 Uiso 1 1 calc R . .
C10 C 0.8737(5) 0.09425(15) 0.4152(4) 0.0436(9) Uani 1 1 d . . .
C11 C 0.6295(6) 0.0675(2) 0.4479(6) 0.0781(15) Uani 1 1 d . . .
H11 H 0.5424 0.0413 0.4485 0.094 Uiso 1 1 calc R A .
C12 C 0.6187(6) 0.1208(2) 0.4799(6) 0.0744(14) Uani 1 1 d . A .
H12 H 0.5232 0.1371 0.4994 0.089 Uiso 1 1 calc R B 1
C13 C 0.9578(5) 0.14204(16) 0.1313(5) 0.0464(10) Uani 1 1 d . . .
C14 C 0.7832(7) 0.0857(2) -0.0855(5) 0.0828(15) Uani 1 1 d . . .
H14A H 0.8507 0.0917 -0.1513 0.099 Uiso 0.63(7) 1 calc PR C 1
H14B H 0.6901 0.1148 -0.1095 0.099 Uiso 0.63(7) 1 calc PR C 1
H14C H 0.8303 0.1074 -0.1503 0.099 Uiso 0.37(7) 1 d PR C 2
H14D H 0.6641 0.1005 -0.1004 0.099 Uiso 0.37(7) 1 d PR C 2
C15 C 0.698(6) 0.0280(17) -0.115(5) 0.096(7) Uani 0.63(7) 1 d P C 1
H15A H 0.7878 -0.0001 -0.1078 0.145 Uiso 0.63(7) 1 calc PR C 1
H15B H 0.6034 0.0270 -0.2167 0.145 Uiso 0.63(7) 1 calc PR C 1
H15C H 0.6467 0.0201 -0.0390 0.145 Uiso 0.63(7) 1 calc PR C 1
C15' C 0.770(9) 0.024(3) -0.123(8) 0.096(12) Uani 0.37(7) 1 d P C 2
H15D H 0.8831 0.0106 -0.1251 0.145 Uiso 0.37(7) 1 calc PR C 2
H15E H 0.6749 0.0175 -0.2226 0.145 Uiso 0.37(7) 1 calc PR C 2
H15F H 0.7436 0.0030 -0.0454 0.145 Uiso 0.37(7) 1 calc PR C 2
C16 C 1.2208(6) 0.23437(16) 0.2649(5) 0.0537(11) Uani 1 1 d . . .
H16A H 1.1600 0.2690 0.2706 0.081 Uiso 1 1 calc R . .
H16B H 1.1811 0.2223 0.1587 0.081 Uiso 1 1 calc R . .
H16C H 1.3494 0.2407 0.3053 0.081 Uiso 1 1 calc R . .


_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
N1 C5 1.400(5) . ?
N1 C1 1.463(4) . ?
N1 H1 0.8600 . ?
N2 C3 1.367(4) . ?
N2 C4 1.402(4) . ?
N2 H2 0.8600 . ?
N3 C10 1.275(4) . ?
N3 C11 1.374(5) . ?
O1 C13 1.339(4) . ?
O1 C14 1.453(5) . ?
O2 C13 1.216(4) . ?
S1 C12 1.720(10) . ?
S1 C10 1.757(14) . ?
S1' C10 1.637(12) . ?
S1' C12 1.688(19) . ?
C1 C10 1.512(5) . ?
C1 C2 1.513(5) . ?
C1 H1A 0.9800 . ?
C2 C3 1.356(5) . ?
C2 C13 1.462(5) . ?
C3 C16 1.518(5) . ?
C4 C5 1.389(5) . ?
C4 C9 1.389(5) . ?
C5 C6 1.396(5) . ?
C6 C7 1.376(6) . ?
C6 H6 0.9300 . ?
C7 C8 1.389(6) . ?
C7 H7 0.9300 . ?
C8 C9 1.373(6) . ?
C8 H8 0.9300 . ?
C9 H9 0.9300 . ?
C11 C12 1.298(6) . ?
C11 H11 0.9300 . ?
C12 H12 0.9300 . ?
C14 C15' 1.49(7) . ?
C14 C15 1.49(4) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C14 H14C 0.9700 . ?
C14 H14D 0.9700 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C15' H15D 0.9600 . ?
C15' H15E 0.9600 . ?
C15' H15F 0.9600 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?

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
C5 N1 C1 118.3(3) . . ?
C5 N1 H1 120.8 . . ?
C1 N1 H1 120.8 . . ?
C3 N2 C4 132.7(3) . . ?
C3 N2 H2 113.7 . . ?
C4 N2 H2 113.7 . . ?
C10 N3 C11 110.5(4) . . ?
C13 O1 C14 116.3(3) . . ?
C12 S1 C10 88.0(7) . . ?
C10 S1' C12 93.2(9) . . ?
N1 C1 C10 111.6(3) . . ?
N1 C1 C2 115.1(3) . . ?
C10 C1 C2 112.3(3) . . ?
N1 C1 H1A 105.6 . . ?
C10 C1 H1A 105.6 . . ?
C2 C1 H1A 105.6 . . ?
C3 C2 C13 119.7(3) . . ?
C3 C2 C1 125.3(3) . . ?
C13 C2 C1 114.9(3) . . ?
C2 C3 N2 126.7(3) . . ?
C2 C3 C16 123.8(3) . . ?
N2 C3 C16 109.4(3) . . ?
C5 C4 C9 119.5(4) . . ?
C5 C4 N2 123.7(3) . . ?
C9 C4 N2 116.7(3) . . ?
C4 C5 C6 118.9(4) . . ?
C4 C5 N1 121.3(3) . . ?
C6 C5 N1 119.7(4) . . ?
C7 C6 C5 121.3(4) . . ?
C7 C6 H6 119.3 . . ?
C5 C6 H6 119.3 . . ?
C6 C7 C8 119.3(4) . . ?
C6 C7 H7 120.3 . . ?
C8 C7 H7 120.3 . . ?
C9 C8 C7 119.8(4) . . ?
C9 C8 H8 120.1 . . ?
C7 C8 H8 120.1 . . ?
C8 C9 C4 121.1(4) . . ?
C8 C9 H9 119.4 . . ?
C4 C9 H9 119.4 . . ?
N3 C10 C1 124.7(3) . . ?
N3 C10 S1' 108.7(10) . . ?
C1 C10 S1' 124.4(5) . . ?
N3 C10 S1 113.5(3) . . ?
C1 C10 S1 121.2(4) . . ?
S1' C10 S1 23(2) . . ?
C12 C11 N3 117.3(4) . . ?
C12 C11 H11 121.4 . . ?
N3 C11 H11 121.4 . . ?
C11 C12 S1' 102.4(13) . . ?
C11 C12 S1 110.0(5) . . ?
S1' C12 S1 23(2) . . ?
C11 C12 H12 125.0 . . ?
S1' C12 H12 127.8 . . ?
S1 C12 H12 125.0 . . ?
O2 C13 O1 120.3(4) . . ?
O2 C13 C2 126.7(4) . . ?
O1 C13 C2 113.0(3) . . ?
O1 C14 C15' 105(2) . . ?
O1 C14 C15 108.8(15) . . ?
C15' C14 C15 24(2) . . ?
O1 C14 H14A 109.9 . . ?
C15' C14 H14A 89.9 . . ?
C15 C14 H14A 109.9 . . ?
O1 C14 H14B 109.9 . . ?
C15' C14 H14B 130.9 . . ?
C15 C14 H14B 109.9 . . ?
H14A C14 H14B 108.3 . . ?
O1 C14 H14C 110.7 . . ?
C15' C14 H14C 112.1 . . ?
C15 C14 H14C 128.4 . . ?
H14A C14 H14C 24.1 . . ?
H14B C14 H14C 86.1 . . ?
O1 C14 H14D 110.5 . . ?
C15' C14 H14D 109.8 . . ?
C15 C14 H14D 86.8 . . ?
H14A C14 H14D 127.5 . . ?
H14B C14 H14D 25.0 . . ?
H14C C14 H14D 108.4 . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
C14 C15' H15D 109.5 . . ?
C14 C15' H15E 109.5 . . ?
H15D C15' H15E 109.5 . . ?
C14 C15' H15F 109.5 . . ?
H15D C15' H15F 109.5 . . ?
H15E C15' H15F 109.5 . . ?
C3 C16 H16A 109.5 . . ?
C3 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C3 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?

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
C5 N1 C1 C10 -56.4(4) . . . . ?
C5 N1 C1 C2 73.1(4) . . . . ?
N1 C1 C2 C3 -28.9(5) . . . . ?
C10 C1 C2 C3 100.3(4) . . . . ?
N1 C1 C2 C13 155.3(3) . . . . ?
C10 C1 C2 C13 -75.5(4) . . . . ?
C13 C2 C3 N2 169.0(3) . . . . ?
C1 C2 C3 N2 -6.7(6) . . . . ?
C13 C2 C3 C16 -14.7(5) . . . . ?
C1 C2 C3 C16 169.6(3) . . . . ?
C4 N2 C3 C2 -5.7(6) . . . . ?
C4 N2 C3 C16 177.5(3) . . . . ?
C3 N2 C4 C5 29.0(6) . . . . ?
C3 N2 C4 C9 -155.1(4) . . . . ?
C9 C4 C5 C6 0.7(5) . . . . ?
N2 C4 C5 C6 176.5(3) . . . . ?
C9 C4 C5 N1 -175.5(3) . . . . ?
N2 C4 C5 N1 0.3(5) . . . . ?
C1 N1 C5 C4 -58.4(4) . . . . ?
C1 N1 C5 C6 125.4(4) . . . . ?
C4 C5 C6 C7 -2.6(6) . . . . ?
N1 C5 C6 C7 173.7(4) . . . . ?
C5 C6 C7 C8 2.4(8) . . . . ?
C6 C7 C8 C9 -0.3(8) . . . . ?
C7 C8 C9 C4 -1.6(7) . . . . ?
C5 C4 C9 C8 1.3(6) . . . . ?
N2 C4 C9 C8 -174.8(4) . . . . ?
C11 N3 C10 C1 178.1(4) . . . . ?
C11 N3 C10 S1' -18(3) . . . . ?
C11 N3 C10 S1 6.4(13) . . . . ?
N1 C1 C10 N3 -86.2(5) . . . . ?
C2 C1 C10 N3 142.8(4) . . . . ?
N1 C1 C10 S1' 112(4) . . . . ?
C2 C1 C10 S1' -19(4) . . . . ?
N1 C1 C10 S1 85.0(13) . . . . ?
C2 C1 C10 S1 -46.0(13) . . . . ?
C12 S1' C10 N3 25(4) . . . . ?
C12 S1' C10 C1 -170.6(12) . . . . ?
C12 S1' C10 S1 -81(4) . . . . ?
C12 S1 C10 N3 -7.3(16) . . . . ?
C12 S1 C10 C1 -179.3(5) . . . . ?
C12 S1 C10 S1' 75.4(16) . . . . ?
C10 N3 C11 C12 -1.7(7) . . . . ?
N3 C11 C12 S1' 19(3) . . . . ?
N3 C11 C12 S1 -3.9(13) . . . . ?
C10 S1' C12 C11 -24(4) . . . . ?
C10 S1' C12 S1 88(4) . . . . ?
C10 S1 C12 C11 5.9(15) . . . . ?
C10 S1 C12 S1' -68.5(15) . . . . ?
C14 O1 C13 O2 -2.1(5) . . . . ?
C14 O1 C13 C2 176.7(3) . . . . ?
C3 C2 C13 O2 -20.0(6) . . . . ?
C1 C2 C13 O2 156.1(4) . . . . ?
C3 C2 C13 O1 161.3(3) . . . . ?
C1 C2 C13 O1 -22.6(4) . . . . ?
C13 O1 C14 C15' 171(3) . . . . ?
C13 O1 C14 C15 -164(2) . . . . ?

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        25.01
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         0.531
_refine_diff_density_min         -0.380
_refine_diff_density_rms         0.061
