# Electronic Supplementary Material (ESI) for Chemical Communications.
# This journal is © The Royal Society of Chemistry 2016

####################################################################### 
# 
# 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_dlc1604
_database_code_depnum_ccdc_archive 'CCDC 1480572'
_audit_update_record             
;
2016-05-17 deposited with the CCDC.
2016-06-07 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         'C11 H16 N2 O5 S'
_chemical_formula_sum            'C11 H16 N2 O5 S'
_chemical_formula_weight         288.32

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_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+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   9.03667(17)
_cell_length_b                   6.90757(13)
_cell_length_c                   21.7122(4)
_cell_angle_alpha                90
_cell_angle_beta                 99.8233(9)
_cell_angle_gamma                90
_cell_volume                     1335.43(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    9265
_cell_measurement_theta_min      4.13
_cell_measurement_theta_max      73.93

_exptl_crystal_description       rod
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.434
_exptl_crystal_F_000             608
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.744
_exptl_crystal_size_mid          0.103
_exptl_crystal_size_min          0.065
_exptl_absorpt_coefficient_mu    2.347
_shelx_estimated_absorpt_T_min   0.274
_shelx_estimated_absorpt_T_max   0.862
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_correction_T_min  0.3361
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_process_details   'SADABS 2014/5'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            9189
_diffrn_reflns_av_unetI/netI     0.0324
_diffrn_reflns_av_R_equivalents  0.0428
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         4.133
_diffrn_reflns_theta_max         74.105
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.979
_diffrn_measured_fraction_theta_full 0.985
_diffrn_reflns_Laue_measured_fraction_max 0.979
_diffrn_reflns_Laue_measured_fraction_full 0.985
_diffrn_reflns_point_group_measured_fraction_max 0.979
_diffrn_reflns_point_group_measured_fraction_full 0.985
_reflns_number_total             2664
_reflns_number_gt                2517
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXD (Schneider & Sheldrick, 2002)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0731P)²+0.8643P] 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_number_reflns         2664
_refine_ls_number_parameters     174
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0508
_refine_ls_R_factor_gt           0.0493
_refine_ls_wR_factor_ref         0.1373
_refine_ls_wR_factor_gt          0.1361
_refine_ls_goodness_of_fit_ref   1.123
_refine_ls_restrained_S_all      1.123
_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_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
S S -0.02067(6) -0.13965(7) 0.39901(2) 0.02830(18) Uani 1 1 d . . . . .
O1 O -0.03494(18) 0.2686(2) 0.31281(7) 0.0333(4) Uani 1 1 d . . . . .
O2 O -0.0394(2) -0.2492(3) 0.18488(10) 0.0537(5) Uani 1 1 d . . . . .
O3 O 0.23359(19) -0.3515(2) 0.25189(8) 0.0387(4) Uani 1 1 d . . . . .
O4 O 0.17067(19) 0.2090(2) 0.44516(7) 0.0321(4) Uani 1 1 d . . . . .
O5 O 0.2946(2) 0.5039(2) 0.46774(8) 0.0432(4) Uani 1 1 d . . . . .
N1 N -0.05413(19) 0.0035(3) 0.25007(8) 0.0272(4) Uani 1 1 d . . . . .
N2 N 0.19336(18) -0.1541(2) 0.32991(8) 0.0238(4) Uani 1 1 d . . . . .
C1 C 0.0040(2) 0.1058(3) 0.30407(9) 0.0244(4) Uani 1 1 d . . . . .
C2 C 0.0101(2) -0.1645(3) 0.23268(11) 0.0323(5) Uani 1 1 d . . . . .
C3 C 0.1558(2) -0.2344(3) 0.27352(10) 0.0273(4) Uani 1 1 d . . . . .
C4 C 0.3485(2) -0.1665(3) 0.36438(10) 0.0296(5) Uani 1 1 d . . . . .
H4A H 0.4216 -0.1235 0.3381 0.036 Uiso 1 1 calc R U . . .
H4B H 0.3733 -0.3003 0.3789 0.036 Uiso 1 1 calc R U . . .
C5 C 0.3476(2) -0.0301(3) 0.41932(11) 0.0316(5) Uani 1 1 d . . . . .
H5A H 0.4464 0.0340 0.4312 0.038 Uiso 1 1 calc R U . . .
H5B H 0.3233 -0.1008 0.4560 0.038 Uiso 1 1 calc R U . . .
C6 C 0.2258(2) 0.1171(3) 0.39531(9) 0.0245(4) Uani 1 1 d . . . . .
H6 H 0.2663 0.2163 0.3690 0.029 Uiso 1 1 calc R U . . .
C7 C 0.1051(2) -0.0065(3) 0.35409(9) 0.0222(4) Uani 1 1 d . . . . .
C8 C -0.1776(2) 0.0919(4) 0.20620(11) 0.0376(5) Uani 1 1 d . . . . .
H8A H -0.2449 -0.0098 0.1863 0.045 Uiso 1 1 calc R U . . .
H8B H -0.1364 0.1641 0.1741 0.045 Uiso 1 1 calc R U . . .
H8C H -0.2338 0.1803 0.2290 0.045 Uiso 1 1 calc R U . . .
C9 C 0.1610(3) 0.4123(3) 0.44171(11) 0.0345(5) Uani 1 1 d . . . . .
H9A H 0.1337 0.4513 0.3973 0.041 Uiso 1 1 calc R U . . .
H9B H 0.0799 0.4565 0.4638 0.041 Uiso 1 1 calc R U . . .
C10 C 0.3295(4) 0.4827(4) 0.53454(13) 0.0530(7) Uani 1 1 d . . . . .
H10A H 0.4240 0.5494 0.5504 0.064 Uiso 1 1 calc R U . . .
H10B H 0.2486 0.5392 0.5536 0.064 Uiso 1 1 calc R U . . .
H10C H 0.3396 0.3449 0.5452 0.064 Uiso 1 1 calc R U . . .
C11 C -0.1518(3) 0.0386(4) 0.41864(12) 0.0373(5) Uani 1 1 d . . . . .
H11A H -0.2214 -0.0234 0.4426 0.045 Uiso 1 1 calc R U . . .
H11B H -0.2085 0.0940 0.3802 0.045 Uiso 1 1 calc R U . . .
H11C H -0.0966 0.1416 0.4438 0.045 Uiso 1 1 calc R U . . .


_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
S C11 1.810(2) . ?
S C7 1.8619(19) . ?
O1 C1 1.203(3) . ?
O2 C2 1.209(3) . ?
O3 C3 1.217(3) . ?
O4 C9 1.409(3) . ?
O4 C6 1.416(2) . ?
O5 C9 1.395(3) . ?
O5 C10 1.438(3) . ?
N1 C2 1.379(3) . ?
N1 C1 1.393(3) . ?
N1 C8 1.471(3) . ?
N2 C3 1.334(3) . ?
N2 C7 1.447(2) . ?
N2 C4 1.474(3) . ?
C1 C7 1.510(3) . ?
C2 C3 1.535(3) . ?
C4 C5 1.521(3) . ?
C5 C6 1.524(3) . ?
C6 C7 1.545(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
C11 S C7 105.69(10) . . ?
C9 O4 C6 115.66(17) . . ?
C9 O5 C10 112.8(2) . . ?
C2 N1 C1 122.80(18) . . ?
C2 N1 C8 118.73(19) . . ?
C1 N1 C8 118.03(18) . . ?
C3 N2 C7 123.81(17) . . ?
C3 N2 C4 120.83(17) . . ?
C7 N2 C4 113.06(16) . . ?
O1 C1 N1 121.93(18) . . ?
O1 C1 C7 121.62(18) . . ?
N1 C1 C7 116.10(17) . . ?
O2 C2 N1 122.1(2) . . ?
O2 C2 C3 120.0(2) . . ?
N1 C2 C3 117.81(18) . . ?
O3 C3 N2 123.9(2) . . ?
O3 C3 C2 118.8(2) . . ?
N2 C3 C2 117.26(17) . . ?
N2 C4 C5 103.34(16) . . ?
C4 C5 C6 104.17(17) . . ?
O4 C6 C5 111.44(17) . . ?
O4 C6 C7 112.62(16) . . ?
C5 C6 C7 103.10(16) . . ?
N2 C7 C1 113.86(16) . . ?
N2 C7 C6 102.79(15) . . ?
C1 C7 C6 114.43(16) . . ?
N2 C7 S 105.41(12) . . ?
C1 C7 S 106.37(13) . . ?
C6 C7 S 113.79(13) . . ?
O5 C9 O4 112.91(19) . . ?

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
C2 N1 C1 O1 165.8(2) . . . . ?
C8 N1 C1 O1 -6.4(3) . . . . ?
C2 N1 C1 C7 -20.8(3) . . . . ?
C8 N1 C1 C7 166.94(17) . . . . ?
C1 N1 C2 O2 -178.2(2) . . . . ?
C8 N1 C2 O2 -6.0(3) . . . . ?
C1 N1 C2 C3 -2.9(3) . . . . ?
C8 N1 C2 C3 169.30(19) . . . . ?
C7 N2 C3 O3 176.20(19) . . . . ?
C4 N2 C3 O3 14.6(3) . . . . ?
C7 N2 C3 C2 -0.1(3) . . . . ?
C4 N2 C3 C2 -161.64(18) . . . . ?
O2 C2 C3 O3 13.2(3) . . . . ?
N1 C2 C3 O3 -162.2(2) . . . . ?
O2 C2 C3 N2 -170.4(2) . . . . ?
N1 C2 C3 N2 14.3(3) . . . . ?
C3 N2 C4 C5 170.68(18) . . . . ?
C7 N2 C4 C5 7.3(2) . . . . ?
N2 C4 C5 C6 -27.4(2) . . . . ?
C9 O4 C6 C5 131.88(19) . . . . ?
C9 O4 C6 C7 -112.82(19) . . . . ?
C4 C5 C6 O4 157.98(17) . . . . ?
C4 C5 C6 C7 36.9(2) . . . . ?
C3 N2 C7 C1 -23.0(3) . . . . ?
C4 N2 C7 C1 139.85(17) . . . . ?
C3 N2 C7 C6 -147.33(18) . . . . ?
C4 N2 C7 C6 15.5(2) . . . . ?
C3 N2 C7 S 93.2(2) . . . . ?
C4 N2 C7 S -103.95(15) . . . . ?
O1 C1 C7 N2 -153.64(18) . . . . ?
N1 C1 C7 N2 33.0(2) . . . . ?
O1 C1 C7 C6 -35.8(3) . . . . ?
N1 C1 C7 C6 150.80(17) . . . . ?
O1 C1 C7 S 90.7(2) . . . . ?
N1 C1 C7 S -82.67(17) . . . . ?
O4 C6 C7 N2 -152.07(15) . . . . ?
C5 C6 C7 N2 -31.84(19) . . . . ?
O4 C6 C7 C1 84.0(2) . . . . ?
C5 C6 C7 C1 -155.81(17) . . . . ?
O4 C6 C7 S -38.63(19) . . . . ?
C5 C6 C7 S 81.60(17) . . . . ?
C11 S C7 N2 -170.96(14) . . . . ?
C11 S C7 C1 -49.74(16) . . . . ?
C11 S C7 C6 77.18(16) . . . . ?
C10 O5 C9 O4 -68.8(3) . . . . ?
C6 O4 C9 O5 -86.6(2) . . . . ?

_refine_diff_density_max         0.442
_refine_diff_density_min         -0.508
_refine_diff_density_rms         0.070


_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
_solvent_exptl_crystal_recrystallization_method 
'methanol, diethyl ether, hexanes'
####################################################################### 
# 
# 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_dlc1605
_database_code_depnum_ccdc_archive 'CCDC 1480573'
_audit_update_record             
;
2016-05-17 deposited with the CCDC.
2016-06-07 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         'C16 H15 N3 O7 S'
_chemical_formula_sum            'C16 H15 N3 O7 S'
_chemical_formula_weight         393.37

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'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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, -z'

_cell_length_a                   6.7169(3)
_cell_length_b                   7.9571(3)
_cell_length_c                   16.1794(6)
_cell_angle_alpha                91.3062(4)
_cell_angle_beta                 98.1391(4)
_cell_angle_gamma                92.2828(5)
_cell_volume                     855.00(6)
_cell_formula_units_Z            2
_cell_measurement_temperature    193(2)
_cell_measurement_reflns_used    8233
_cell_measurement_theta_min      2.54
_cell_measurement_theta_max      28.33

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.528
_exptl_crystal_F_000             408
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.375
_exptl_crystal_size_mid          0.212
_exptl_crystal_size_min          0.191
_exptl_absorpt_coefficient_mu    0.237
_shelx_estimated_absorpt_T_min   0.916
_shelx_estimated_absorpt_T_max   0.956
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_correction_T_min  0.9300
_exptl_absorpt_correction_T_max  0.9899
_exptl_absorpt_process_details   'SADABS 2014/5'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      193(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            8103
_diffrn_reflns_av_unetI/netI     0.0160
_diffrn_reflns_av_R_equivalents  0.0113
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         2.544
_diffrn_reflns_theta_max         28.335
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.978
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.978
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.978
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             4170
_reflns_number_gt                3842
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT-2014 (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0459P)²+0.2997P] 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_number_reflns         4170
_refine_ls_number_parameters     246
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0344
_refine_ls_R_factor_gt           0.0320
_refine_ls_wR_factor_ref         0.0877
_refine_ls_wR_factor_gt          0.0854
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_restrained_S_all      1.025
_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
S S 0.12702(4) 0.40398(3) 0.42307(2) 0.02272(8) Uani 1 1 d . . . . .
O1 O -0.05164(13) 0.24319(13) 0.24045(6) 0.0365(2) Uani 1 1 d . . . . .
O2 O 0.23680(18) -0.20069(12) 0.37358(7) 0.0463(3) Uani 1 1 d . . . . .
O3 O 0.59462(16) -0.01319(14) 0.40544(7) 0.0430(3) Uani 1 1 d . . . . .
O4 O 0.37572(13) 0.36071(11) 0.21349(5) 0.02681(18) Uani 1 1 d . . . . .
O5 O 0.15759(15) 0.50784(13) 0.12642(6) 0.0384(2) Uani 1 1 d . . . . .
O6 O 0.5853(2) 0.1419(2) -0.19648(7) 0.0638(4) Uani 1 1 d . . . . .
O7 O 0.8298(2) 0.06143(18) -0.10615(8) 0.0603(3) Uani 1 1 d . . . . .
N1 N 0.08633(15) 0.01701(12) 0.30588(6) 0.0274(2) Uani 1 1 d . . . . .
N2 N 0.42274(13) 0.21914(12) 0.37116(6) 0.02157(19) Uani 1 1 d . . . . .
N3 N 0.6698(2) 0.12875(17) -0.12464(8) 0.0432(3) Uani 1 1 d . . . . .
C1 C 0.08093(16) 0.18630(14) 0.28876(7) 0.0228(2) Uani 1 1 d . . . . .
C2 C 0.24497(19) -0.05495(15) 0.35486(8) 0.0287(2) Uani 1 1 d . . . . .
C3 C 0.43800(18) 0.05355(15) 0.38059(7) 0.0267(2) Uani 1 1 d . . . . .
C4 C 0.59932(17) 0.33767(17) 0.38301(8) 0.0312(3) Uani 1 1 d . . . . .
H4A H 0.7100 0.2938 0.3555 0.037 Uiso 1 1 calc R U . . .
H4B H 0.6485 0.3587 0.4431 0.037 Uiso 1 1 calc R U . . .
C5 C 0.52114(19) 0.49832(16) 0.34196(8) 0.0317(3) Uani 1 1 d . . . . .
H5A H 0.4982 0.5836 0.3847 0.038 Uiso 1 1 calc R U . . .
H5B H 0.6181 0.5466 0.3073 0.038 Uiso 1 1 calc R U . . .
C6 C 0.32344(17) 0.44245(14) 0.28797(7) 0.0235(2) Uani 1 1 d . . . . .
H6 H 0.2289 0.5356 0.2759 0.028 Uiso 1 1 calc R U . . .
C7 C 0.24129(15) 0.30151(13) 0.33903(6) 0.0183(2) Uani 1 1 d . . . . .
C8 C -0.0826(2) -0.09528(19) 0.26757(10) 0.0436(3) Uani 1 1 d . . . . .
H8A H -0.0307 -0.2009 0.2490 0.052 Uiso 1 1 calc R U . . .
H8B H -0.1563 -0.0408 0.2195 0.052 Uiso 1 1 calc R U . . .
H8C H -0.1734 -0.1188 0.3087 0.052 Uiso 1 1 calc R U . . .
C9 C 0.28935(18) 0.40975(15) 0.13781(7) 0.0267(2) Uani 1 1 d . . . . .
C10 C 0.38707(18) 0.32872(15) 0.07032(7) 0.0261(2) Uani 1 1 d . . . . .
C11 C 0.29406(19) 0.33674(17) -0.01216(8) 0.0312(3) Uani 1 1 d . . . . .
H11 H 0.1676 0.3868 -0.0244 0.037 Uiso 1 1 calc R U . . .
C12 C 0.3873(2) 0.27115(18) -0.07616(8) 0.0352(3) Uani 1 1 d . . . . .
H12 H 0.3258 0.2754 -0.1326 0.042 Uiso 1 1 calc R U . . .
C13 C 0.5712(2) 0.19949(17) -0.05635(8) 0.0326(3) Uani 1 1 d . . . . .
C14 C 0.6675(2) 0.18991(17) 0.02482(8) 0.0335(3) Uani 1 1 d . . . . .
H14 H 0.7943 0.1401 0.0365 0.040 Uiso 1 1 calc R U . . .
C15 C 0.57280(19) 0.25546(17) 0.08863(8) 0.0303(3) Uani 1 1 d . . . . .
H15 H 0.6349 0.2503 0.1450 0.036 Uiso 1 1 calc R U . . .
C16 C 0.0798(2) 0.22560(16) 0.48530(8) 0.0302(3) Uani 1 1 d . . . . .
H16A H 0.0336 0.2645 0.5370 0.036 Uiso 1 1 calc R U . . .
H16B H 0.2041 0.1654 0.4990 0.036 Uiso 1 1 calc R U . . .
H16C H -0.0240 0.1499 0.4538 0.036 Uiso 1 1 calc R U . . .


_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
S C16 1.8024(12) . ?
S C7 1.8433(11) . ?
O1 C1 1.2083(14) . ?
O2 C2 1.2063(15) . ?
O3 C3 1.2186(14) . ?
O4 C9 1.3515(14) . ?
O4 C6 1.4494(13) . ?
O5 C9 1.2008(15) . ?
O6 N3 1.2278(18) . ?
O7 N3 1.2221(19) . ?
N1 C1 1.3823(15) . ?
N1 C2 1.3862(16) . ?
N1 C8 1.4715(15) . ?
N2 C3 1.3362(15) . ?
N2 C7 1.4439(13) . ?
N2 C4 1.4736(15) . ?
N3 C13 1.4778(17) . ?
C1 C7 1.5170(14) . ?
C2 C3 1.5302(18) . ?
C4 C5 1.5311(19) . ?
C5 C6 1.5267(16) . ?
C6 C7 1.5385(15) . ?
C9 C10 1.4978(17) . ?
C10 C15 1.3947(17) . ?
C10 C11 1.3951(16) . ?
C11 C12 1.3865(19) . ?
C12 C13 1.381(2) . ?
C13 C14 1.3845(18) . ?
C14 C15 1.3893(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
C16 S C7 100.71(5) . . ?
C9 O4 C6 119.07(9) . . ?
C1 N1 C2 123.93(10) . . ?
C1 N1 C8 118.33(11) . . ?
C2 N1 C8 117.70(11) . . ?
C3 N2 C7 125.43(10) . . ?
C3 N2 C4 122.55(10) . . ?
C7 N2 C4 111.61(9) . . ?
O7 N3 O6 124.23(13) . . ?
O7 N3 C13 118.11(13) . . ?
O6 N3 C13 117.66(14) . . ?
O1 C1 N1 122.40(10) . . ?
O1 C1 C7 120.75(10) . . ?
N1 C1 C7 116.67(9) . . ?
O2 C2 N1 121.71(13) . . ?
O2 C2 C3 120.32(12) . . ?
N1 C2 C3 117.87(10) . . ?
O3 C3 N2 124.05(12) . . ?
O3 C3 C2 119.76(11) . . ?
N2 C3 C2 116.15(10) . . ?
N2 C4 C5 104.09(9) . . ?
C6 C5 C4 104.78(10) . . ?
O4 C6 C5 106.78(9) . . ?
O4 C6 C7 105.94(8) . . ?
C5 C6 C7 102.63(9) . . ?
N2 C7 C1 114.26(9) . . ?
N2 C7 C6 101.84(8) . . ?
C1 C7 C6 113.78(9) . . ?
N2 C7 S 111.84(7) . . ?
C1 C7 S 107.86(7) . . ?
C6 C7 S 107.05(7) . . ?
O5 C9 O4 124.98(11) . . ?
O5 C9 C10 124.90(11) . . ?
O4 C9 C10 110.09(10) . . ?
C15 C10 C11 120.44(11) . . ?
C15 C10 C9 120.93(10) . . ?
C11 C10 C9 118.52(11) . . ?
C12 C11 C10 119.58(12) . . ?
C13 C12 C11 118.82(12) . . ?
C12 C13 C14 122.96(12) . . ?
C12 C13 N3 118.71(12) . . ?
C14 C13 N3 118.32(13) . . ?
C13 C14 C15 117.88(12) . . ?
C14 C15 C10 120.31(11) . . ?

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
C2 N1 C1 O1 173.85(11) . . . . ?
C8 N1 C1 O1 -3.85(18) . . . . ?
C2 N1 C1 C7 -11.00(16) . . . . ?
C8 N1 C1 C7 171.29(10) . . . . ?
C1 N1 C2 O2 174.11(11) . . . . ?
C8 N1 C2 O2 -8.17(18) . . . . ?
C1 N1 C2 C3 -9.51(17) . . . . ?
C8 N1 C2 C3 168.20(11) . . . . ?
C7 N2 C3 O3 177.60(11) . . . . ?
C4 N2 C3 O3 5.57(18) . . . . ?
C7 N2 C3 C2 -0.10(16) . . . . ?
C4 N2 C3 C2 -172.12(10) . . . . ?
O2 C2 C3 O3 14.20(18) . . . . ?
N1 C2 C3 O3 -162.23(11) . . . . ?
O2 C2 C3 N2 -168.00(11) . . . . ?
N1 C2 C3 N2 15.57(15) . . . . ?
C3 N2 C4 C5 163.98(10) . . . . ?
C7 N2 C4 C5 -9.04(12) . . . . ?
N2 C4 C5 C6 -16.09(12) . . . . ?
C9 O4 C6 C5 -128.75(11) . . . . ?
C9 O4 C6 C7 122.36(10) . . . . ?
C4 C5 C6 O4 -77.58(11) . . . . ?
C4 C5 C6 C7 33.61(12) . . . . ?
C3 N2 C7 C1 -19.75(15) . . . . ?
C4 N2 C7 C1 153.03(10) . . . . ?
C3 N2 C7 C6 -142.86(11) . . . . ?
C4 N2 C7 C6 29.91(11) . . . . ?
C3 N2 C7 S 103.14(11) . . . . ?
C4 N2 C7 S -84.09(10) . . . . ?
O1 C1 C7 N2 -159.89(11) . . . . ?
N1 C1 C7 N2 24.88(14) . . . . ?
O1 C1 C7 C6 -43.50(15) . . . . ?
N1 C1 C7 C6 141.27(10) . . . . ?
O1 C1 C7 S 75.10(12) . . . . ?
N1 C1 C7 S -100.14(10) . . . . ?
O4 C6 C7 N2 73.54(10) . . . . ?
C5 C6 C7 N2 -38.29(10) . . . . ?
O4 C6 C7 C1 -49.91(11) . . . . ?
C5 C6 C7 C1 -161.73(9) . . . . ?
O4 C6 C7 S -168.96(7) . . . . ?
C5 C6 C7 S 79.21(9) . . . . ?
C16 S C7 N2 -59.93(9) . . . . ?
C16 S C7 C1 66.52(8) . . . . ?
C16 S C7 C6 -170.67(8) . . . . ?
C6 O4 C9 O5 -6.58(18) . . . . ?
C6 O4 C9 C10 171.36(9) . . . . ?
O5 C9 C10 C15 161.70(13) . . . . ?
O4 C9 C10 C15 -16.25(16) . . . . ?
O5 C9 C10 C11 -14.56(19) . . . . ?
O4 C9 C10 C11 167.50(11) . . . . ?
C15 C10 C11 C12 0.06(19) . . . . ?
C9 C10 C11 C12 176.33(11) . . . . ?
C10 C11 C12 C13 -0.13(19) . . . . ?
C11 C12 C13 C14 0.0(2) . . . . ?
C11 C12 C13 N3 179.63(12) . . . . ?
O7 N3 C13 C12 -177.97(13) . . . . ?
O6 N3 C13 C12 2.2(2) . . . . ?
O7 N3 C13 C14 1.7(2) . . . . ?
O6 N3 C13 C14 -178.19(13) . . . . ?
C12 C13 C14 C15 0.2(2) . . . . ?
N3 C13 C14 C15 -179.45(12) . . . . ?
C13 C14 C15 C10 -0.25(19) . . . . ?
C11 C10 C15 C14 0.14(19) . . . . ?
C9 C10 C15 C14 -176.05(11) . . . . ?

_refine_diff_density_max         0.385
_refine_diff_density_min         -0.220
_refine_diff_density_rms         0.045


_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
_solvent_exptl_crystal_recrystallization_method 'isopropyl alcohol, toluene'
