# Electronic Supplementary Material (ESI) for Catalysis Science & Technology.
# This journal is © The Royal Society of Chemistry 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_1
_database_code_depnum_ccdc_archive 'CCDC 1514749'
_audit_update_record             
;
2016-11-03 deposited with the CCDC.	2019-02-22 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C15 H18 N2 O S'
_chemical_formula_weight         274.37

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           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                   5.9659(3)
_cell_length_b                   16.3145(7)
_cell_length_c                   14.5127(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 99.253(3)
_cell_angle_gamma                90.00
_cell_volume                     1394.15(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    273(2)
_cell_measurement_reflns_used    1428
_cell_measurement_theta_min      2.497
_cell_measurement_theta_max      23.071

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.307
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             584
_exptl_absorpt_coefficient_mu    0.226
_exptl_absorpt_correction_type   'multi scan'
_exptl_absorpt_correction_T_min  0.2000
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      273(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            8769
_diffrn_reflns_av_R_equivalents  0.0418
_diffrn_reflns_av_sigmaI/netI    0.0547
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         1.89
_diffrn_reflns_theta_max         27.49
_reflns_number_total             3159
_reflns_number_gt                2097
_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)+(0.0429P)²+0.1776P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    contr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3159
_refine_ls_number_parameters     172
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0792
_refine_ls_R_factor_gt           0.0455
_refine_ls_wR_factor_ref         0.1086
_refine_ls_wR_factor_gt          0.0951
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_restrained_S_all      1.040
_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 0.18418(9) 0.83627(4) 0.85197(4) 0.03900(18) Uani 1 1 d . . .
N1 N 0.8520(3) 0.83044(9) 1.09827(11) 0.0251(4) Uani 1 1 d . . .
C2 C 0.6193(3) 0.83814(11) 0.95360(13) 0.0252(4) Uani 1 1 d . . .
H2A H 0.6470 0.8169 0.8933 0.030 Uiso 1 1 calc R . .
N2 N 0.7254(3) 0.70508(9) 1.03629(11) 0.0262(4) Uani 1 1 d . . .
C1 C 0.3609(3) 0.84430(12) 0.95604(14) 0.0292(5) Uani 1 1 d . . .
O1 O 0.3075(2) 0.85659(11) 1.03342(10) 0.0522(5) Uani 1 1 d . . .
C5 C 0.7362(3) 0.78622(12) 1.03204(13) 0.0229(4) Uani 1 1 d . . .
C9 C 0.5740(3) 0.65697(12) 0.96776(13) 0.0286(4) Uani 1 1 d . . .
H9A H 0.4690 0.6939 0.9303 0.034 Uiso 1 1 calc R . .
H9B H 0.4856 0.6204 1.0006 0.034 Uiso 1 1 calc R . .
C11 C 0.5963(3) 0.53497(12) 0.86445(14) 0.0306(5) Uani 1 1 d . . .
H11A H 0.4631 0.5158 0.8825 0.037 Uiso 1 1 calc R . .
C10 C 0.6954(3) 0.60661(11) 0.90346(13) 0.0244(4) Uani 1 1 d . . .
C4 C 0.8370(3) 0.91865(11) 1.07857(14) 0.0310(5) Uani 1 1 d . . .
H4A H 0.9856 0.9442 1.0908 0.037 Uiso 1 1 calc R . .
H4B H 0.7372 0.9457 1.1156 0.037 Uiso 1 1 calc R . .
C6 C 0.9902(3) 0.79563(13) 1.18075(14) 0.0336(5) Uani 1 1 d . . .
H6A H 0.9031 0.7930 1.2317 0.040 Uiso 1 1 calc R . .
H6B H 1.1226 0.8297 1.2001 0.040 Uiso 1 1 calc R . .
C15 C 0.8963(3) 0.63343(12) 0.87689(14) 0.0298(5) Uani 1 1 d . . .
H15A H 0.9653 0.6811 0.9028 0.036 Uiso 1 1 calc R . .
C3 C 0.7396(3) 0.92140(12) 0.97542(14) 0.0312(5) Uani 1 1 d . . .
H3A H 0.8595 0.9286 0.9383 0.037 Uiso 1 1 calc R . .
H3B H 0.6323 0.9662 0.9623 0.037 Uiso 1 1 calc R . .
C14 C 0.9954(4) 0.58947(13) 0.81157(14) 0.0359(5) Uani 1 1 d . . .
H14A H 1.1297 0.6079 0.7939 0.043 Uiso 1 1 calc R . .
C8 C 0.8591(4) 0.66012(13) 1.11432(14) 0.0345(5) Uani 1 1 d . . .
H8A H 0.9093 0.6083 1.0920 0.041 Uiso 1 1 calc R . .
H8B H 0.7650 0.6486 1.1614 0.041 Uiso 1 1 calc R . .
C12 C 0.6940(4) 0.49165(13) 0.79878(15) 0.0378(5) Uani 1 1 d . . .
H12A H 0.6243 0.4444 0.7721 0.045 Uiso 1 1 calc R . .
C7 C 1.0634(4) 0.71019(13) 1.15703(15) 0.0365(5) Uani 1 1 d . . .
H7A H 1.1702 0.7138 1.1134 0.044 Uiso 1 1 calc R . .
H7B H 1.1390 0.6834 1.2132 0.044 Uiso 1 1 calc R . .
C13 C 0.8942(4) 0.51843(14) 0.77308(15) 0.0389(5) Uani 1 1 d . . .
H13A H 0.9610 0.4888 0.7299 0.047 Uiso 1 1 calc R . .

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 0.0306(3) 0.0463(4) 0.0394(3) -0.0030(3) 0.0036(2) 0.0086(2)
N1 0.0269(8) 0.0198(9) 0.0291(9) -0.0030(7) 0.0058(7) 0.0016(7)
C2 0.0280(10) 0.0233(10) 0.0263(10) 0.0028(8) 0.0107(8) 0.0039(8)
N2 0.0344(9) 0.0173(9) 0.0260(9) -0.0012(7) 0.0023(7) 0.0009(7)
C1 0.0288(10) 0.0270(11) 0.0341(11) 0.0065(9) 0.0120(9) 0.0046(8)
O1 0.0362(9) 0.0896(14) 0.0345(9) 0.0055(8) 0.0167(7) 0.0130(8)
C5 0.0233(9) 0.0214(10) 0.0261(10) -0.0014(8) 0.0103(8) 0.0028(8)
C9 0.0284(10) 0.0235(11) 0.0333(11) -0.0016(9) 0.0038(9) -0.0029(8)
C11 0.0318(11) 0.0198(11) 0.0386(12) 0.0017(9) 0.0002(9) -0.0001(8)
C10 0.0271(10) 0.0177(10) 0.0267(10) 0.0021(8) -0.0010(8) 0.0039(8)
C4 0.0359(11) 0.0176(11) 0.0419(13) -0.0036(9) 0.0134(9) -0.0010(8)
C6 0.0390(12) 0.0310(12) 0.0290(11) -0.0031(9) 0.0001(9) -0.0016(9)
C15 0.0282(10) 0.0249(11) 0.0349(12) -0.0010(9) 0.0006(9) -0.0010(8)
C3 0.0348(11) 0.0227(11) 0.0401(12) 0.0045(9) 0.0184(9) 0.0035(9)
C14 0.0321(11) 0.0417(14) 0.0344(12) 0.0028(10) 0.0062(9) 0.0057(10)
C8 0.0503(13) 0.0226(11) 0.0285(11) 0.0031(9) -0.0002(10) 0.0045(10)
C12 0.0489(13) 0.0211(12) 0.0395(13) -0.0070(10) -0.0045(10) 0.0053(10)
C7 0.0433(12) 0.0314(13) 0.0326(12) 0.0019(10) -0.0009(10) 0.0102(10)
C13 0.0448(13) 0.0376(14) 0.0339(12) -0.0052(10) 0.0048(10) 0.0140(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 C1 1.702(2) . ?
N1 C5 1.307(2) . ?
N1 C6 1.455(2) . ?
N1 C4 1.467(2) . ?
C2 C5 1.498(3) . ?
C2 C3 1.545(3) . ?
C2 C1 1.551(2) . ?
N2 C5 1.327(2) . ?
N2 C9 1.460(2) . ?
N2 C8 1.472(2) . ?
C1 O1 1.232(2) . ?
C9 C10 1.512(3) . ?
C11 C12 1.388(3) . ?
C11 C10 1.389(3) . ?
C10 C15 1.388(3) . ?
C4 C3 1.517(3) . ?
C6 C7 1.517(3) . ?
C15 C14 1.394(3) . ?
C14 C13 1.383(3) . ?
C8 C7 1.515(3) . ?
C12 C13 1.378(3) . ?

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 C6 123.51(16) . . ?
C5 N1 C4 112.93(16) . . ?
C6 N1 C4 123.49(16) . . ?
C5 C2 C3 101.39(16) . . ?
C5 C2 C1 111.23(15) . . ?
C3 C2 C1 111.65(15) . . ?
C5 N2 C9 122.26(16) . . ?
C5 N2 C8 120.56(16) . . ?
C9 N2 C8 117.10(15) . . ?
O1 C1 C2 115.78(18) . . ?
O1 C1 S1 127.41(16) . . ?
C2 C1 S1 116.79(14) . . ?
N1 C5 N2 122.70(17) . . ?
N1 C5 C2 111.91(16) . . ?
N2 C5 C2 125.39(17) . . ?
N2 C9 C10 114.03(15) . . ?
C12 C11 C10 120.68(19) . . ?
C15 C10 C11 118.83(18) . . ?
C15 C10 C9 121.38(17) . . ?
C11 C10 C9 119.61(17) . . ?
N1 C4 C3 102.89(15) . . ?
N1 C6 C7 108.53(16) . . ?
C10 C15 C14 120.43(19) . . ?
C4 C3 C2 105.53(15) . . ?
C13 C14 C15 120.0(2) . . ?
N2 C8 C7 110.31(16) . . ?
C13 C12 C11 120.2(2) . . ?
C8 C7 C6 110.25(17) . . ?
C12 C13 C14 119.85(19) . . ?

_diffrn_measured_fraction_theta_max 0.984
_diffrn_reflns_theta_full        27.49
_diffrn_measured_fraction_theta_full 0.984
_refine_diff_density_max         0.271
_refine_diff_density_min         -0.232
_refine_diff_density_rms         0.051
####################################################################### 
# 
# 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_16sep26a
_database_code_depnum_ccdc_archive 'CCDC 1514750'
_audit_update_record             
;
2016-11-03 deposited with the CCDC.	2019-02-22 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 O2 S'
_chemical_formula_weight         220.28

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'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Orthorhombic
_symmetry_space_group_name_H-M   Pbca

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

_cell_length_a                   16.151(15)
_cell_length_b                   7.314(7)
_cell_length_c                   19.036(19)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     2249(4)
_cell_formula_units_Z            8
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    1278
_cell_measurement_theta_min      2.48
_cell_measurement_theta_max      21.07

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.18
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.301
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             928
_exptl_absorpt_coefficient_mu    0.264
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9369
_exptl_absorpt_correction_T_max  0.9540
_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         0
_diffrn_standards_interval_count ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            13307
_diffrn_reflns_av_R_equivalents  0.0790
_diffrn_reflns_av_sigmaI/netI    0.0535
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         2.52
_diffrn_reflns_theta_max         28.02
_reflns_number_total             2645
_reflns_number_gt                1139
_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 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_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)+(0.1775P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2645
_refine_ls_number_parameters     138
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1591
_refine_ls_R_factor_gt           0.0847
_refine_ls_wR_factor_ref         0.3243
_refine_ls_wR_factor_gt          0.2319
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_restrained_S_all      1.048
_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
S1 S 0.60260(9) 0.14691(18) 0.24059(7) 0.0752(6) Uani 1 1 d . . .
O1 O 0.61580(19) 0.1661(4) 0.10772(17) 0.0699(9) Uani 1 1 d . . .
O2 O 0.6071(2) -0.1135(5) 0.1480(2) 0.0835(11) Uani 1 1 d . . .
C1 C 0.5970(2) 0.4370(7) 0.3649(2) 0.0643(12) Uani 1 1 d . . .
H1 H 0.5657 0.3382 0.3493 0.077 Uiso 1 1 calc R . .
C2 C 0.6007(3) 0.4739(8) 0.4351(3) 0.0811(15) Uani 1 1 d . . .
H2 H 0.5719 0.4014 0.4669 0.097 Uiso 1 1 calc R . .
C3 C 0.6464(3) 0.6162(8) 0.4582(3) 0.0879(17) Uani 1 1 d . . .
H3 H 0.6496 0.6398 0.5061 0.105 Uiso 1 1 calc R . .
C4 C 0.6877(3) 0.7249(8) 0.4127(3) 0.0850(16) Uani 1 1 d . . .
H4 H 0.7192 0.8224 0.4292 0.102 Uiso 1 1 calc R . .
C5 C 0.6827(3) 0.6898(7) 0.3420(3) 0.0736(13) Uani 1 1 d . . .
H5 H 0.7097 0.7667 0.3106 0.088 Uiso 1 1 calc R . .
C6 C 0.6385(2) 0.5432(6) 0.3168(2) 0.0564(10) Uani 1 1 d . . .
C7 C 0.6347(2) 0.5128(7) 0.2422(2) 0.0585(11) Uani 1 1 d . . .
H7 H 0.6450 0.6156 0.2148 0.070 Uiso 1 1 calc R . .
C8 C 0.6189(2) 0.3620(5) 0.2065(2) 0.0497(9) Uani 1 1 d . . .
C9 C 0.6111(2) 0.3581(5) 0.1281(2) 0.0523(10) Uani 1 1 d . . .
C10 C 0.6811(3) 0.4473(7) 0.0907(3) 0.0785(14) Uani 1 1 d . . .
H10A H 0.7323 0.3941 0.1060 0.118 Uiso 1 1 calc R . .
H10B H 0.6812 0.5757 0.1011 0.118 Uiso 1 1 calc R . .
H10C H 0.6749 0.4296 0.0411 0.118 Uiso 1 1 calc R . .
C11 C 0.5288(3) 0.4245(7) 0.1041(2) 0.0764(14) Uani 1 1 d . . .
H11A H 0.5246 0.4105 0.0541 0.115 Uiso 1 1 calc R . .
H11B H 0.5228 0.5513 0.1161 0.115 Uiso 1 1 calc R . .
H11C H 0.4860 0.3548 0.1266 0.115 Uiso 1 1 calc R . .
C12 C 0.6083(2) 0.0506(7) 0.1585(3) 0.0632(11) Uani 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 0.1026(11) 0.0682(10) 0.0547(8) 0.0090(5) 0.0019(6) -0.0116(6)
O1 0.095(2) 0.062(2) 0.0520(17) 0.0014(14) 0.0062(14) 0.0035(15)
O2 0.101(3) 0.064(2) 0.086(3) 0.0005(19) 0.0034(18) 0.0034(17)
C1 0.070(3) 0.071(3) 0.051(2) -0.001(2) -0.0004(19) -0.003(2)
C2 0.082(3) 0.108(5) 0.053(3) 0.003(3) 0.000(2) 0.006(3)
C3 0.080(3) 0.123(5) 0.061(3) -0.018(3) -0.015(2) 0.011(3)
C4 0.068(3) 0.104(4) 0.083(4) -0.032(3) -0.011(2) -0.007(3)
C5 0.069(3) 0.082(3) 0.070(3) -0.015(2) 0.005(2) -0.004(2)
C6 0.053(2) 0.062(3) 0.054(2) -0.0066(19) -0.0018(16) 0.0021(19)
C7 0.064(2) 0.062(3) 0.050(2) 0.0045(19) 0.0030(17) -0.002(2)
C8 0.0486(18) 0.055(2) 0.046(2) 0.0005(18) 0.0023(15) -0.0007(16)
C9 0.061(2) 0.048(2) 0.047(2) -0.0019(17) 0.0046(16) 0.0014(17)
C10 0.085(3) 0.088(4) 0.062(3) 0.003(3) 0.020(2) -0.007(3)
C11 0.079(3) 0.090(4) 0.060(3) -0.004(2) -0.012(2) 0.014(3)
C12 0.065(2) 0.056(3) 0.069(3) -0.003(2) 0.000(2) 0.002(2)

_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 C12 1.717(5) . ?
S1 C8 1.722(4) . ?
O1 C12 1.289(6) . ?
O1 C9 1.458(5) . ?
O2 C12 1.217(5) . ?
C1 C2 1.364(7) . ?
C1 C6 1.376(6) . ?
C1 H1 0.9300 . ?
C2 C3 1.350(7) . ?
C2 H2 0.9300 . ?
C3 C4 1.351(8) . ?
C3 H3 0.9300 . ?
C4 C5 1.373(7) . ?
C4 H4 0.9300 . ?
C5 C6 1.374(6) . ?
C5 H5 0.9300 . ?
C6 C7 1.439(6) . ?
C7 C8 1.321(6) . ?
C7 H7 0.9300 . ?
C8 C9 1.499(6) . ?
C9 C10 1.485(6) . ?
C9 C11 1.487(6) . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 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
C12 S1 C8 91.3(2) . . ?
C12 O1 C9 115.3(4) . . ?
C2 C1 C6 121.3(5) . . ?
C2 C1 H1 119.4 . . ?
C6 C1 H1 119.4 . . ?
C3 C2 C1 119.7(5) . . ?
C3 C2 H2 120.2 . . ?
C1 C2 H2 120.2 . . ?
C2 C3 C4 121.1(5) . . ?
C2 C3 H3 119.5 . . ?
C4 C3 H3 119.5 . . ?
C3 C4 C5 119.2(5) . . ?
C3 C4 H4 120.4 . . ?
C5 C4 H4 120.4 . . ?
C4 C5 C6 121.3(5) . . ?
C4 C5 H5 119.4 . . ?
C6 C5 H5 119.4 . . ?
C5 C6 C1 117.5(4) . . ?
C5 C6 C7 119.2(4) . . ?
C1 C6 C7 123.3(4) . . ?
C8 C7 C6 130.2(4) . . ?
C8 C7 H7 114.9 . . ?
C6 C7 H7 114.9 . . ?
C7 C8 C9 123.0(4) . . ?
C7 C8 S1 126.8(3) . . ?
C9 C8 S1 110.2(3) . . ?
O1 C9 C10 104.9(3) . . ?
O1 C9 C11 106.2(3) . . ?
C10 C9 C11 112.9(4) . . ?
O1 C9 C8 106.2(3) . . ?
C10 C9 C8 113.9(3) . . ?
C11 C9 C8 112.0(3) . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C9 C11 H11A 109.5 . . ?
C9 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C9 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
O2 C12 O1 121.7(5) . . ?
O2 C12 S1 123.5(4) . . ?
O1 C12 S1 114.8(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
C6 C1 C2 C3 -0.5(7) . . . . ?
C1 C2 C3 C4 1.0(8) . . . . ?
C2 C3 C4 C5 0.2(8) . . . . ?
C3 C4 C5 C6 -2.0(8) . . . . ?
C4 C5 C6 C1 2.4(7) . . . . ?
C4 C5 C6 C7 179.6(4) . . . . ?
C2 C1 C6 C5 -1.2(7) . . . . ?
C2 C1 C6 C7 -178.2(4) . . . . ?
C5 C6 C7 C8 157.7(5) . . . . ?
C1 C6 C7 C8 -25.2(7) . . . . ?
C6 C7 C8 C9 175.2(4) . . . . ?
C6 C7 C8 S1 -3.6(7) . . . . ?
C12 S1 C8 C7 -169.3(4) . . . . ?
C12 S1 C8 C9 11.7(3) . . . . ?
C12 O1 C9 C10 134.1(4) . . . . ?
C12 O1 C9 C11 -106.1(4) . . . . ?
C12 O1 C9 C8 13.3(4) . . . . ?
C7 C8 C9 O1 165.3(3) . . . . ?
S1 C8 C9 O1 -15.7(4) . . . . ?
C7 C8 C9 C10 50.4(5) . . . . ?
S1 C8 C9 C10 -130.6(3) . . . . ?
C7 C8 C9 C11 -79.2(5) . . . . ?
S1 C8 C9 C11 99.8(4) . . . . ?
C9 O1 C12 O2 176.4(4) . . . . ?
C9 O1 C12 S1 -5.0(4) . . . . ?
C8 S1 C12 O2 174.2(4) . . . . ?
C8 S1 C12 O1 -4.3(3) . . . . ?

_diffrn_measured_fraction_theta_max 0.972
_diffrn_reflns_theta_full        26.00
_diffrn_measured_fraction_theta_full 0.975
_refine_diff_density_max         0.352
_refine_diff_density_min         -1.050
_refine_diff_density_rms         0.101
####################################################################### 
# 
# 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_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 1525402'
_audit_update_record             
;
2017-01-03 deposited with the CCDC.	2019-02-22 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C9 H14 N2 O S'
_chemical_formula_weight         198.28

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           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                   7.5382(2)
_cell_length_b                   12.2061(3)
_cell_length_c                   10.8739(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 95.949(2)
_cell_angle_gamma                90.00
_cell_volume                     995.14(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    273(2)
_cell_measurement_reflns_used    1357
_cell_measurement_theta_min      2.52
_cell_measurement_theta_max      24.32

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.21
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.323
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             424
_exptl_absorpt_coefficient_mu    0.288
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9383
_exptl_absorpt_correction_T_max  0.9532
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      273(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            5993
_diffrn_reflns_av_R_equivalents  0.0357
_diffrn_reflns_av_sigmaI/netI    0.0480
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.52
_diffrn_reflns_theta_max         27.51
_reflns_number_total             2251
_reflns_number_gt                1712
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SMART'
_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)+(0.0633P)²+0.7904P] 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         2251
_refine_ls_number_parameters     118
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0736
_refine_ls_R_factor_gt           0.0529
_refine_ls_wR_factor_ref         0.1401
_refine_ls_wR_factor_gt          0.1292
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_restrained_S_all      1.063
_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 0.06350(9) 0.78548(5) 0.34210(6) 0.0253(2) Uani 1 1 d . . .
O1 O -0.0597(2) 0.65974(15) 0.51200(18) 0.0308(5) Uani 1 1 d . . .
N2 N 0.4659(3) 0.65164(17) 0.36715(19) 0.0200(5) Uani 1 1 d . . .
N1 N 0.2669(3) 0.55981(17) 0.2267(2) 0.0243(5) Uani 1 1 d . . .
C9 C 0.0541(3) 0.6763(2) 0.4394(2) 0.0210(5) Uani 1 1 d . . .
C5 C 0.3136(3) 0.60021(18) 0.3371(2) 0.0178(5) Uani 1 1 d . . .
C4 C 0.5807(3) 0.6863(2) 0.2744(3) 0.0270(6) Uani 1 1 d . . .
H4A H 0.7033 0.6913 0.3111 0.032 Uiso 1 1 calc R . .
H4B H 0.5440 0.7578 0.2423 0.032 Uiso 1 1 calc R . .
C2 C 0.3715(4) 0.5833(2) 0.1237(2) 0.0284(6) Uani 1 1 d . . .
H2A H 0.3239 0.6479 0.0799 0.034 Uiso 1 1 calc R . .
H2B H 0.3623 0.5223 0.0663 0.034 Uiso 1 1 calc R . .
C8 C 0.2082(4) 0.5935(2) 0.4483(3) 0.0304(6) Uani 1 1 d . . .
H8A H 0.1649 0.5189 0.4597 0.037 Uiso 1 1 calc R . .
C3 C 0.5660(4) 0.6024(2) 0.1703(3) 0.0277(6) Uani 1 1 d . . .
H3A H 0.6297 0.6286 0.1030 0.033 Uiso 1 1 calc R . .
H3B H 0.6199 0.5340 0.2000 0.033 Uiso 1 1 calc R . .
C6 C 0.4871(3) 0.6934(2) 0.4942(2) 0.0260(6) Uani 1 1 d . . .
H6A H 0.4596 0.7710 0.4966 0.031 Uiso 1 1 calc R . .
H6B H 0.6073 0.6814 0.5330 0.031 Uiso 1 1 calc R . .
C1 C 0.0907(4) 0.5102(2) 0.1976(3) 0.0354(7) Uani 1 1 d . . .
H1A H 0.0359 0.4995 0.2726 0.053 Uiso 1 1 calc R . .
H1B H 0.1032 0.4408 0.1579 0.053 Uiso 1 1 calc R . .
H1C H 0.0175 0.5578 0.1434 0.053 Uiso 1 1 calc R . .
C7 C 0.3533(4) 0.6264(2) 0.5559(3) 0.0334(7) Uani 1 1 d . . .
H7A H 0.4091 0.5619 0.5949 0.040 Uiso 1 1 calc R . .
H7B H 0.3010 0.6694 0.6180 0.040 Uiso 1 1 calc R . .

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 0.0265(4) 0.0230(3) 0.0259(4) 0.0012(3) 0.0007(3) 0.0055(3)
O1 0.0254(10) 0.0294(11) 0.0399(12) -0.0061(9) 0.0148(9) -0.0026(8)
N2 0.0160(10) 0.0239(11) 0.0200(10) -0.0002(9) 0.0018(8) -0.0003(8)
N1 0.0226(11) 0.0209(11) 0.0292(13) -0.0080(9) 0.0016(9) -0.0006(8)
C9 0.0180(12) 0.0213(12) 0.0235(13) -0.0040(10) 0.0013(10) -0.0028(9)
C5 0.0174(11) 0.0122(11) 0.0243(13) 0.0012(9) 0.0042(9) 0.0031(9)
C4 0.0202(12) 0.0314(14) 0.0304(15) 0.0049(11) 0.0071(11) -0.0045(11)
C2 0.0393(16) 0.0255(14) 0.0205(13) -0.0025(11) 0.0036(12) 0.0056(12)
C8 0.0324(15) 0.0245(14) 0.0368(16) 0.0065(12) 0.0152(12) 0.0044(11)
C3 0.0297(14) 0.0284(14) 0.0275(14) 0.0056(11) 0.0147(11) 0.0075(11)
C6 0.0213(12) 0.0343(15) 0.0216(13) -0.0062(11) -0.0022(10) 0.0020(11)
C1 0.0258(14) 0.0331(16) 0.0462(18) -0.0183(14) -0.0014(13) -0.0024(12)
C7 0.0338(15) 0.0363(16) 0.0299(15) 0.0004(12) 0.0024(12) 0.0080(13)

_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 C9 1.707(3) . ?
O1 C9 1.241(3) . ?
N2 C5 1.320(3) . ?
N2 C4 1.458(3) . ?
N2 C6 1.466(3) . ?
N1 C5 1.312(3) . ?
N1 C2 1.463(3) . ?
N1 C1 1.464(3) . ?
C9 C8 1.536(4) . ?
C5 C8 1.516(4) . ?
C4 C3 1.521(4) . ?
C2 C3 1.519(4) . ?
C8 C7 1.568(4) . ?
C6 C7 1.508(4) . ?

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 N2 C4 122.0(2) . . ?
C5 N2 C6 113.9(2) . . ?
C4 N2 C6 122.5(2) . . ?
C5 N1 C2 120.8(2) . . ?
C5 N1 C1 120.3(2) . . ?
C2 N1 C1 117.7(2) . . ?
O1 C9 C8 114.9(2) . . ?
O1 C9 S1 126.7(2) . . ?
C8 C9 S1 118.24(18) . . ?
N1 C5 N2 123.3(2) . . ?
N1 C5 C8 126.7(2) . . ?
N2 C5 C8 110.0(2) . . ?
N2 C4 C3 108.5(2) . . ?
N1 C2 C3 110.7(2) . . ?
C5 C8 C9 111.7(2) . . ?
C5 C8 C7 101.5(2) . . ?
C9 C8 C7 110.1(2) . . ?
C2 C3 C4 110.2(2) . . ?
N2 C6 C7 102.6(2) . . ?
C8 C7 C6 104.7(2) . . ?

_diffrn_measured_fraction_theta_max 0.984
_diffrn_reflns_theta_full        27.51
_diffrn_measured_fraction_theta_full 0.984
_refine_diff_density_max         1.132
_refine_diff_density_min         -0.458
_refine_diff_density_rms         0.072
####################################################################### 
# 
# 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_16nov14a_a_pl
_database_code_depnum_ccdc_archive 'CCDC 1525403'
_audit_update_record             
;
2017-01-03 deposited with the CCDC.	2019-02-22 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C15 H16 O2 S'
_chemical_formula_weight         260.34

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'
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   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                   11.978(6)
_cell_length_b                   7.388(4)
_cell_length_c                   16.198(8)
_cell_angle_alpha                90.00
_cell_angle_beta                 109.288(9)
_cell_angle_gamma                90.00
_cell_volume                     1353.0(12)
_cell_formula_units_Z            4
_cell_measurement_temperature    273(2)
_cell_measurement_reflns_used    1683
_cell_measurement_theta_min      2.66
_cell_measurement_theta_max      23.25

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.21
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.278
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             552
_exptl_absorpt_coefficient_mu    0.230
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9383
_exptl_absorpt_correction_T_max  0.9532
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      273(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         0
_diffrn_standards_interval_count ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            8228
_diffrn_reflns_av_R_equivalents  0.0509
_diffrn_reflns_av_sigmaI/netI    0.0697
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         1.80
_diffrn_reflns_theta_max         26.57
_reflns_number_total             2782
_reflns_number_gt                1847
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_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)+(0.1116P)²+1.7598P] 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         2782
_refine_ls_number_parameters     163
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1123
_refine_ls_R_factor_gt           0.0834
_refine_ls_wR_factor_ref         0.2561
_refine_ls_wR_factor_gt          0.2367
_refine_ls_goodness_of_fit_ref   1.086
_refine_ls_restrained_S_all      1.086
_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
S1 S 0.49452(11) -0.18558(16) 0.85983(10) 0.0627(5) Uani 1 1 d . . .
O1 O 0.2691(2) -0.1559(4) 0.8201(2) 0.0515(8) Uani 1 1 d . . .
O2 O 0.3319(3) -0.4403(4) 0.8299(2) 0.0684(10) Uani 1 1 d . . .
C1 C 0.6340(3) 0.2086(6) 0.9097(3) 0.0439(10) Uani 1 1 d . . .
C2 C 0.6841(4) 0.3501(7) 0.9651(3) 0.0609(12) Uani 1 1 d . . .
H2 H 0.6356 0.4308 0.9814 0.073 Uiso 1 1 calc R . .
C3 C 0.8062(5) 0.3739(9) 0.9969(4) 0.0751(16) Uani 1 1 d . . .
H3 H 0.8389 0.4677 1.0356 0.090 Uiso 1 1 calc R . .
C4 C 0.8773(4) 0.2601(9) 0.9714(4) 0.0752(17) Uani 1 1 d . . .
H4 H 0.9589 0.2763 0.9924 0.090 Uiso 1 1 calc R . .
C5 C 0.8298(4) 0.1229(9) 0.9153(4) 0.0730(15) Uani 1 1 d . . .
H5 H 0.8790 0.0454 0.8978 0.088 Uiso 1 1 calc R . .
C6 C 0.7081(4) 0.0974(7) 0.8837(3) 0.0576(12) Uani 1 1 d . . .
H6 H 0.6764 0.0039 0.8445 0.069 Uiso 1 1 calc R . .
C7 C 0.5055(4) 0.1861(6) 0.8804(3) 0.0465(10) Uani 1 1 d . . .
H7 H 0.4625 0.2922 0.8772 0.056 Uiso 1 1 calc R . .
C8 C 0.4407(3) 0.0352(5) 0.8574(3) 0.0382(9) Uani 1 1 d . . .
C9 C 0.3074(3) 0.0336(5) 0.8254(2) 0.0366(8) Uani 1 1 d . . .
C10 C 0.2563(4) 0.1123(6) 0.7344(3) 0.0511(11) Uani 1 1 d . . .
H10A H 0.2843 0.0425 0.6944 0.061 Uiso 1 1 calc R . .
H10B H 0.2842 0.2356 0.7346 0.061 Uiso 1 1 calc R . .
C11 C 0.1212(4) 0.1117(8) 0.7019(4) 0.0676(15) Uani 1 1 d . . .
H11A H 0.0923 0.1710 0.6454 0.081 Uiso 1 1 calc R . .
H11B H 0.0931 -0.0123 0.6944 0.081 Uiso 1 1 calc R . .
C12 C 0.0724(4) 0.2067(8) 0.7646(4) 0.0772(18) Uani 1 1 d . . .
H12A H -0.0131 0.1975 0.7436 0.093 Uiso 1 1 calc R . .
H12B H 0.0932 0.3340 0.7673 0.093 Uiso 1 1 calc R . .
C13 C 0.1207(4) 0.1249(7) 0.8552(4) 0.0673(14) Uani 1 1 d . . .
H13A H 0.0924 0.0016 0.8536 0.081 Uiso 1 1 calc R . .
H13B H 0.0916 0.1934 0.8950 0.081 Uiso 1 1 calc R . .
C14 C 0.2547(4) 0.1252(6) 0.8889(3) 0.0477(10) Uani 1 1 d . . .
H14A H 0.2822 0.0628 0.9447 0.057 Uiso 1 1 calc R . .
H14B H 0.2827 0.2492 0.8985 0.057 Uiso 1 1 calc R . .
C15 C 0.3518(4) -0.2798(6) 0.8341(3) 0.0504(11) Uani 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 0.0518(7) 0.0367(7) 0.0938(10) -0.0047(6) 0.0163(6) 0.0135(5)
O1 0.0490(16) 0.0240(14) 0.079(2) 0.0036(13) 0.0181(15) -0.0011(11)
O2 0.092(3) 0.0279(17) 0.086(3) -0.0002(15) 0.031(2) 0.0009(16)
C1 0.040(2) 0.049(2) 0.042(2) 0.0033(18) 0.0120(17) -0.0028(17)
C2 0.064(3) 0.059(3) 0.063(3) 0.001(2) 0.025(2) -0.001(2)
C3 0.061(3) 0.091(4) 0.069(3) -0.021(3) 0.015(3) -0.023(3)
C4 0.039(2) 0.115(5) 0.066(3) -0.007(3) 0.009(2) -0.013(3)
C5 0.045(3) 0.095(4) 0.082(4) 0.002(3) 0.025(3) 0.008(3)
C6 0.045(2) 0.070(3) 0.061(3) -0.010(2) 0.022(2) -0.005(2)
C7 0.041(2) 0.039(2) 0.059(3) 0.0023(18) 0.0157(18) 0.0057(17)
C8 0.038(2) 0.0295(19) 0.046(2) 0.0022(16) 0.0130(16) 0.0073(15)
C9 0.038(2) 0.0241(18) 0.047(2) 0.0007(15) 0.0134(16) -0.0028(14)
C10 0.050(2) 0.045(2) 0.052(2) 0.0065(19) 0.0079(19) 0.0001(19)
C11 0.045(3) 0.065(3) 0.072(3) 0.017(3) -0.008(2) 0.001(2)
C12 0.037(2) 0.061(3) 0.115(5) 0.003(3) 0.000(3) 0.010(2)
C13 0.050(3) 0.056(3) 0.105(4) -0.017(3) 0.036(3) -0.003(2)
C14 0.045(2) 0.045(2) 0.058(3) -0.0059(19) 0.0232(19) -0.0009(18)
C15 0.064(3) 0.033(2) 0.055(3) 0.0021(18) 0.020(2) 0.0080(18)

_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 C8 1.750(4) . ?
S1 C15 1.764(5) . ?
O1 C15 1.313(5) . ?
O1 C9 1.467(4) . ?
O2 C15 1.207(5) . ?
C1 C6 1.373(6) . ?
C1 C2 1.379(7) . ?
C1 C7 1.463(6) . ?
C2 C3 1.392(7) . ?
C2 H2 0.9300 . ?
C3 C4 1.355(9) . ?
C3 H3 0.9300 . ?
C4 C5 1.355(8) . ?
C4 H4 0.9300 . ?
C5 C6 1.390(6) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C7 C8 1.339(6) . ?
C7 H7 0.9300 . ?
C8 C9 1.507(5) . ?
C9 C10 1.514(6) . ?
C9 C14 1.530(5) . ?
C10 C11 1.528(6) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 C12 1.501(9) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 C13 1.514(8) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 C14 1.515(6) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?

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
C8 S1 C15 92.37(19) . . ?
C15 O1 C9 116.9(3) . . ?
C6 C1 C2 117.8(4) . . ?
C6 C1 C7 123.3(4) . . ?
C2 C1 C7 118.9(4) . . ?
C1 C2 C3 121.0(5) . . ?
C1 C2 H2 119.5 . . ?
C3 C2 H2 119.5 . . ?
C4 C3 C2 119.9(5) . . ?
C4 C3 H3 120.0 . . ?
C2 C3 H3 120.0 . . ?
C5 C4 C3 120.1(5) . . ?
C5 C4 H4 120.0 . . ?
C3 C4 H4 120.0 . . ?
C4 C5 C6 120.4(5) . . ?
C4 C5 H5 119.8 . . ?
C6 C5 H5 119.8 . . ?
C1 C6 C5 120.8(5) . . ?
C1 C6 H6 119.6 . . ?
C5 C6 H6 119.6 . . ?
C8 C7 C1 129.5(4) . . ?
C8 C7 H7 115.2 . . ?
C1 C7 H7 115.2 . . ?
C7 C8 C9 123.6(3) . . ?
C7 C8 S1 126.5(3) . . ?
C9 C8 S1 110.0(3) . . ?
O1 C9 C8 107.6(3) . . ?
O1 C9 C10 107.0(3) . . ?
C8 C9 C10 111.9(3) . . ?
O1 C9 C14 105.7(3) . . ?
C8 C9 C14 113.0(3) . . ?
C10 C9 C14 111.2(3) . . ?
C9 C10 C11 112.0(4) . . ?
C9 C10 H10A 109.2 . . ?
C11 C10 H10A 109.2 . . ?
C9 C10 H10B 109.2 . . ?
C11 C10 H10B 109.2 . . ?
H10A C10 H10B 107.9 . . ?
C12 C11 C10 111.7(4) . . ?
C12 C11 H11A 109.3 . . ?
C10 C11 H11A 109.3 . . ?
C12 C11 H11B 109.3 . . ?
C10 C11 H11B 109.3 . . ?
H11A C11 H11B 107.9 . . ?
C11 C12 C13 111.1(4) . . ?
C11 C12 H12A 109.4 . . ?
C13 C12 H12A 109.4 . . ?
C11 C12 H12B 109.4 . . ?
C13 C12 H12B 109.4 . . ?
H12A C12 H12B 108.0 . . ?
C12 C13 C14 111.6(4) . . ?
C12 C13 H13A 109.3 . . ?
C14 C13 H13A 109.3 . . ?
C12 C13 H13B 109.3 . . ?
C14 C13 H13B 109.3 . . ?
H13A C13 H13B 108.0 . . ?
C13 C14 C9 112.4(4) . . ?
C13 C14 H14A 109.1 . . ?
C9 C14 H14A 109.1 . . ?
C13 C14 H14B 109.1 . . ?
C9 C14 H14B 109.1 . . ?
H14A C14 H14B 107.9 . . ?
O2 C15 O1 123.5(5) . . ?
O2 C15 S1 124.0(4) . . ?
O1 C15 S1 112.5(3) . . ?

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 -3.1(7) . . . . ?
C7 C1 C2 C3 178.0(5) . . . . ?
C1 C2 C3 C4 2.0(9) . . . . ?
C2 C3 C4 C5 -0.3(10) . . . . ?
C3 C4 C5 C6 -0.2(10) . . . . ?
C2 C1 C6 C5 2.6(7) . . . . ?
C7 C1 C6 C5 -178.6(5) . . . . ?
C4 C5 C6 C1 -1.0(8) . . . . ?
C6 C1 C7 C8 29.9(7) . . . . ?
C2 C1 C7 C8 -151.3(5) . . . . ?
C1 C7 C8 C9 -177.9(4) . . . . ?
C1 C7 C8 S1 2.4(7) . . . . ?
C15 S1 C8 C7 172.9(4) . . . . ?
C15 S1 C8 C9 -6.7(3) . . . . ?
C15 O1 C9 C8 -6.7(5) . . . . ?
C15 O1 C9 C10 113.7(4) . . . . ?
C15 O1 C9 C14 -127.7(4) . . . . ?
C7 C8 C9 O1 -171.2(4) . . . . ?
S1 C8 C9 O1 8.5(4) . . . . ?
C7 C8 C9 C10 71.6(5) . . . . ?
S1 C8 C9 C10 -108.7(3) . . . . ?
C7 C8 C9 C14 -54.8(5) . . . . ?
S1 C8 C9 C14 124.9(3) . . . . ?
O1 C9 C10 C11 62.6(5) . . . . ?
C8 C9 C10 C11 -179.7(4) . . . . ?
C14 C9 C10 C11 -52.3(5) . . . . ?
C9 C10 C11 C12 54.8(6) . . . . ?
C10 C11 C12 C13 -55.8(6) . . . . ?
C11 C12 C13 C14 55.6(6) . . . . ?
C12 C13 C14 C9 -54.0(5) . . . . ?
O1 C9 C14 C13 -63.4(5) . . . . ?
C8 C9 C14 C13 179.1(4) . . . . ?
C10 C9 C14 C13 52.3(5) . . . . ?
C9 O1 C15 O2 -178.4(4) . . . . ?
C9 O1 C15 S1 1.7(5) . . . . ?
C8 S1 C15 O2 -176.7(4) . . . . ?
C8 S1 C15 O1 3.1(4) . . . . ?

_diffrn_measured_fraction_theta_max 0.984
_diffrn_reflns_theta_full        26.57
_diffrn_measured_fraction_theta_full 0.984
_refine_diff_density_max         0.847
_refine_diff_density_min         -0.565
_refine_diff_density_rms         0.084
