# Electronic Supplementary Material (ESI) for ChemComm.
# 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 1498572'
_audit_update_record             
;
2016-08-10 deposited with the CCDC.
2016-09-02 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         ?
_chemical_formula_sum            'C4 H4 N2 O2.50 S0.50'
_chemical_formula_weight         136.12

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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

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

_cell_length_a                   8.5330(10)
_cell_length_b                   13.0141(10)
_cell_length_c                   9.6918(12)
_cell_angle_alpha                90
_cell_angle_beta                 92.1310(10)
_cell_angle_gamma                90
_cell_volume                     1075.5(2)
_cell_formula_units_Z            8
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    820
_cell_measurement_theta_min      2.9713
_cell_measurement_theta_max      28.4520

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.08
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.681
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             560
_exptl_absorpt_coefficient_mu    0.324
_exptl_transmission_factor_min   0.84176
_exptl_transmission_factor_max   1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35h (release 09-02-2015 CrysAlis171 .NET)
(compiled Feb  9 2015,16:26:32)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_absorpt_special_details   
;
 ?   
;

_diffrn_ambient_temperature      295(2)
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            Sapphire3
_diffrn_detector_area_resol_mean 16.1340
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            4693
_diffrn_reflns_av_unetI/netI     0.0959
_diffrn_reflns_av_R_equivalents  0.0464
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         2.856
_diffrn_reflns_theta_max         29.356
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.829
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.830
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.829
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             2458
_reflns_number_gt                1359
_reflns_threshold_expression     'I > 2σ(I)'
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35h (release 09-02-2015 CrysAlis171 .NET)
(compiled Feb  9 2015,16:26:32)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35h (release 09-02-2015 CrysAlis171 .NET)
(compiled Feb  9 2015,16:26:32)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35h (release 09-02-2015 CrysAlis171 .NET)
(compiled Feb  9 2015,16:26:32)
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2005)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_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 > 2σ(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     
'w=1/[σ²(Fo²)+(0.0349P)²] 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     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.0020(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2458
_refine_ls_number_parameters     182
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1644
_refine_ls_R_factor_gt           0.0856
_refine_ls_wR_factor_ref         0.1552
_refine_ls_wR_factor_gt          0.1302
_refine_ls_goodness_of_fit_ref   1.167
_refine_ls_restrained_S_all      1.167
_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
O1A O 0.6975(17) 0.2149(9) 0.1344(11) 0.088(5) Uani 0.5 1 d . . P A 1
S1A S 0.7102(5) 0.1908(3) 0.0916(4) 0.0401(8) Uani 0.5 1 d . . P A 2
C1 C 0.6132(5) 0.2785(3) 0.1714(4) 0.0330(10) Uani 1 1 d . . . . .
N2 N 0.6216(4) 0.3782(2) 0.1317(3) 0.0382(9) Uani 1 1 d . . . . .
H2 H 0.6827 0.3922 0.0657 0.046 Uiso 1 1 calc R U . . .
C4 C 0.4220(5) 0.3243(3) 0.3434(4) 0.0371(10) Uani 1 1 d . . . . .
O2 O 0.5661(4) 0.54638(19) 0.1512(3) 0.0528(9) Uani 1 1 d . . . . .
C3 C 0.4258(5) 0.4311(3) 0.2915(5) 0.0494(12) Uani 1 1 d . . . . .
H3A H 0.4440 0.4760 0.3704 0.059 Uiso 1 1 calc R U . . .
H3B H 0.3224 0.4472 0.2525 0.059 Uiso 1 1 calc R U . . .
C2 C 0.5424(5) 0.4582(3) 0.1867(4) 0.0366(10) Uani 1 1 d . . . . .
O3 O 0.3440(4) 0.2960(2) 0.4385(3) 0.0530(9) Uani 1 1 d . . . . .
N1 N 0.5129(4) 0.2549(2) 0.2724(3) 0.0381(9) Uani 1 1 d . . . . .
H1 H 0.5051 0.1911 0.2945 0.046 Uiso 1 1 calc R U . . .
S1B S 0.8140(5) 0.0542(3) -0.0706(4) 0.0414(8) Uani 0.5 1 d . . P B 1
O1B O 0.8355(17) 0.0251(9) -0.0981(15) 0.089(5) Uani 0.5 1 d . . P B 2
C5 C 0.8904(5) -0.0338(3) -0.1645(4) 0.0313(10) Uani 1 1 d . . . . .
N4 N 0.8611(4) -0.1367(2) -0.1458(3) 0.0325(8) Uani 1 1 d . . . . .
H4 H 0.8002 -0.1530 -0.0805 0.039 Uiso 1 1 calc R U . . .
C6 C 1.0611(5) -0.0782(3) -0.3518(4) 0.0327(10) Uani 1 1 d . . . . .
O4 O 0.8997(3) -0.30403(18) -0.1868(3) 0.0427(8) Uani 1 1 d . . . . .
C7 C 0.9997(5) -0.1856(3) -0.3493(4) 0.0339(10) Uani 1 1 d . . . . .
H7A H 0.9263 -0.1945 -0.4272 0.041 Uiso 1 1 calc R U . . .
H7B H 1.0865 -0.2324 -0.3620 0.041 Uiso 1 1 calc R U . . .
O5 O 1.1596(3) -0.0497(2) -0.4301(3) 0.0468(8) Uani 1 1 d . . . . .
C8 C 0.9202(5) -0.2156(3) -0.2217(4) 0.0306(9) Uani 1 1 d . . . . .
N3 N 0.9922(4) -0.0096(2) -0.2654(3) 0.0344(9) Uani 1 1 d . . . . .
H3 H 1.0149 0.0542 -0.2755 0.041 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
O1A C1 1.163(11) . ?
S1A C1 1.623(5) . ?
C1 N2 1.356(5) . ?
C1 N1 1.359(4) . ?
N2 C2 1.360(5) . ?
N2 H2 0.8600 . ?
C4 O3 1.214(5) . ?
C4 N1 1.390(5) . ?
C4 C3 1.479(5) . ?
O2 C2 1.217(4) . ?
C3 C2 1.491(6) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
N1 H1 0.8600 . ?
S1B C5 1.616(5) . ?
O1B C5 1.115(10) . ?
C5 N3 1.368(5) . ?
C5 N4 1.375(4) . ?
N4 C8 1.370(4) . ?
N4 H4 0.8600 . ?
C6 O5 1.211(4) . ?
C6 N3 1.371(5) . ?
C6 C7 1.494(5) . ?
O4 C8 1.214(4) . ?
C7 C8 1.485(5) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
N3 H3 0.8600 . ?

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
O1A C1 N2 123.7(8) . . ?
O1A C1 N1 118.3(7) . . ?
N2 C1 N1 117.5(3) . . ?
N2 C1 S1A 120.3(3) . . ?
N1 C1 S1A 122.0(3) . . ?
C1 N2 C2 126.1(4) . . ?
C1 N2 H2 116.9 . . ?
C2 N2 H2 116.9 . . ?
O3 C4 N1 120.7(4) . . ?
O3 C4 C3 124.2(4) . . ?
N1 C4 C3 115.0(4) . . ?
C4 C3 C2 118.6(4) . . ?
C4 C3 H3A 107.7 . . ?
C2 C3 H3A 107.7 . . ?
C4 C3 H3B 107.7 . . ?
C2 C3 H3B 107.7 . . ?
H3A C3 H3B 107.1 . . ?
O2 C2 N2 121.4(4) . . ?
O2 C2 C3 122.6(4) . . ?
N2 C2 C3 116.1(3) . . ?
C1 N1 C4 126.0(3) . . ?
C1 N1 H1 117.0 . . ?
C4 N1 H1 117.0 . . ?
O1B C5 N3 123.1(8) . . ?
O1B C5 N4 120.7(8) . . ?
N3 C5 N4 116.2(3) . . ?
N3 C5 S1B 121.3(3) . . ?
N4 C5 S1B 122.5(3) . . ?
C5 N4 C8 125.9(3) . . ?
C5 N4 H4 117.0 . . ?
C8 N4 H4 117.0 . . ?
O5 C6 N3 120.5(3) . . ?
O5 C6 C7 123.3(4) . . ?
N3 C6 C7 116.1(3) . . ?
C8 C7 C6 115.6(3) . . ?
C8 C7 H7A 108.4 . . ?
C6 C7 H7A 108.4 . . ?
C8 C7 H7B 108.4 . . ?
C6 C7 H7B 108.4 . . ?
H7A C7 H7B 107.5 . . ?
O4 C8 N4 120.1(4) . . ?
O4 C8 C7 123.8(3) . . ?
N4 C8 C7 116.0(3) . . ?
C5 N3 C6 125.8(3) . . ?
C5 N3 H3 117.1 . . ?
C6 N3 H3 117.1 . . ?

_refine_diff_density_max         0.245
_refine_diff_density_min         -0.234
_refine_diff_density_rms         0.057


####################################################################### 
# 
# 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 1498573'
_audit_update_record             
;
2016-08-10 deposited with the CCDC.
2016-09-02 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         ?
_chemical_formula_sum            'C8 H8 N4 O5.40 S0.60'
_chemical_formula_weight         265.82

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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

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

_cell_length_a                   8.4569(9)
_cell_length_b                   12.9400(10)
_cell_length_c                   9.5593(9)
_cell_angle_alpha                90
_cell_angle_beta                 92.626(10)
_cell_angle_gamma                90
_cell_volume                     1045.00(17)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    737
_cell_measurement_theta_min      3.5010
_cell_measurement_theta_max      22.9940

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.08
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.690
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             547
_exptl_absorpt_coefficient_mu    0.256
_exptl_absorpt_correction_T_min  0.95550
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35h (release 09-02-2015 CrysAlis171 .NET)
(compiled Feb  9 2015,16:26:32)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_special_details           
;
 ?   
;

_diffrn_ambient_temperature      295(2)
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            Sapphire3
_diffrn_detector_area_resol_mean 16.1340
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            4818
_diffrn_reflns_av_unetI/netI     0.1280
_diffrn_reflns_av_R_equivalents  0.0704
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -6
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         3.518
_diffrn_reflns_theta_max         29.473
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.830
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.830
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.830
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             2417
_reflns_number_gt                956
_reflns_threshold_expression     'I > 2σ(I)'
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35h (release 09-02-2015 CrysAlis171 .NET)
(compiled Feb  9 2015,16:26:32)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35h (release 09-02-2015 CrysAlis171 .NET)
(compiled Feb  9 2015,16:26:32)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35h (release 09-02-2015 CrysAlis171 .NET)
(compiled Feb  9 2015,16:26:32)
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2005)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_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 > 2σ(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     
'w=1/[σ²(Fo²)+(0.0399P)²] 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         2417
_refine_ls_number_parameters     181
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.2080
_refine_ls_R_factor_gt           0.0743
_refine_ls_wR_factor_ref         0.1604
_refine_ls_wR_factor_gt          0.1139
_refine_ls_goodness_of_fit_ref   0.985
_refine_ls_restrained_S_all      0.985
_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
O1A O 0.6660(14) -0.0338(9) -0.4070(12) 0.066(4) Uani 0.7 1 d . . P A 1
S1A S 0.6877(12) -0.0567(8) -0.4326(11) 0.0359(15) Uani 0.3 1 d . . P A 1
O1B O 0.1996(15) 0.2899(8) 0.1238(11) 0.069(4) Uani 0.7 1 d . . P B 2
S1B S 0.2115(13) 0.3125(7) 0.0915(10) 0.0367(15) Uani 0.3 1 d . . P B 2
C4 C 0.5803(5) 0.2162(3) -0.2804(4) 0.0392(11) Uani 1 1 d . . . . .
O4 O -0.1531(4) 0.2031(2) 0.4388(3) 0.0608(10) Uani 1 1 d . . . . .
O3 O 0.6012(3) 0.3047(2) -0.3149(3) 0.0516(9) Uani 1 1 d . . . . .
N1 N 0.6381(4) 0.1358(3) -0.3553(3) 0.0413(10) Uani 1 1 d . . . . .
H1 H 0.6998 0.1517 -0.4210 0.050 Uiso 1 1 calc R U . . .
O5 O 0.0680(3) -0.0465(2) 0.1508(3) 0.0574(10) Uani 1 1 d . . . . .
N3 N 0.1244(4) 0.1223(3) 0.1322(3) 0.0466(10) Uani 1 1 d . . . . .
H3 H 0.1865 0.1082 0.0659 0.056 Uiso 1 1 calc R U . . .
N4 N 0.0140(4) 0.2451(3) 0.2749(3) 0.0468(10) Uani 1 1 d . . . . .
H4 H 0.0049 0.3090 0.2980 0.056 Uiso 1 1 calc R U . . .
O2 O 0.3382(3) 0.0505(2) -0.0709(3) 0.0546(9) Uani 1 1 d . . . . .
C2 C 0.4378(5) 0.0781(3) -0.1490(4) 0.0406(11) Uani 1 1 d . . . . .
C6 C 0.0454(5) 0.0420(4) 0.1873(5) 0.0427(12) Uani 1 1 d . . . . .
N2 N 0.5056(4) 0.0098(3) -0.2362(3) 0.0408(10) Uani 1 1 d . . . . .
H2 H 0.4811 -0.0542 -0.2268 0.049 Uiso 1 1 calc R U . . .
C8 C -0.0729(5) 0.1758(4) 0.3440(4) 0.0454(13) Uani 1 1 d . . . . .
C1 C 0.6085(5) 0.0330(3) -0.3371(4) 0.0372(11) Uani 1 1 d . . . . .
C3 C 0.5016(5) 0.1857(3) -0.1526(4) 0.0418(12) Uani 1 1 d . . . . .
H3A H 0.4148 0.2332 -0.1394 0.050 Uiso 1 1 calc R U . . .
H3B H 0.5766 0.1942 -0.0736 0.050 Uiso 1 1 calc R U . . .
C5 C 0.1150(5) 0.2227(4) 0.1714(4) 0.0426(12) Uani 1 1 d . . . . .
C7 C -0.0690(5) 0.0687(3) 0.2929(5) 0.0599(15) Uani 1 1 d . . . . .
H7A H -0.1739 0.0518 0.2543 0.072 Uiso 1 1 calc R U . . .
H7B H -0.0486 0.0241 0.3733 0.072 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
O1A C1 1.209(10) . ?
S1A C1 1.638(10) . ?
O1B C5 1.227(10) . ?
S1B C5 1.629(9) . ?
C4 O3 1.207(4) . ?
C4 N1 1.365(5) . ?
C4 C3 1.472(5) . ?
O4 C8 1.209(4) . ?
N1 C1 1.366(5) . ?
N1 H1 0.8600 . ?
O5 C6 1.215(5) . ?
N3 C5 1.356(5) . ?
N3 C6 1.355(5) . ?
N3 H3 0.8600 . ?
N4 C8 1.351(5) . ?
N4 C5 1.367(4) . ?
N4 H4 0.8600 . ?
O2 C2 1.206(4) . ?
C2 N2 1.359(5) . ?
C2 C3 1.494(5) . ?
C6 C7 1.471(5) . ?
N2 C1 1.362(4) . ?
N2 H2 0.8600 . ?
C8 C7 1.470(6) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C7 H7A 0.9700 . ?
C7 H7B 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
O3 C4 N1 121.3(4) . . ?
O3 C4 C3 124.0(4) . . ?
N1 C4 C3 114.7(3) . . ?
C1 N1 C4 127.1(3) . . ?
C1 N1 H1 116.5 . . ?
C4 N1 H1 116.5 . . ?
C5 N3 C6 126.2(4) . . ?
C5 N3 H3 116.9 . . ?
C6 N3 H3 116.9 . . ?
C8 N4 C5 125.8(4) . . ?
C8 N4 H4 117.1 . . ?
C5 N4 H4 117.1 . . ?
O2 C2 N2 120.9(4) . . ?
O2 C2 C3 123.6(4) . . ?
N2 C2 C3 115.4(3) . . ?
O5 C6 N3 121.6(4) . . ?
O5 C6 C7 122.4(4) . . ?
N3 C6 C7 116.0(4) . . ?
C2 N2 C1 126.3(4) . . ?
C2 N2 H2 116.8 . . ?
C1 N2 H2 116.8 . . ?
O4 C8 N4 120.6(4) . . ?
O4 C8 C7 123.1(4) . . ?
N4 C8 C7 116.3(4) . . ?
O1A C1 N1 123.1(7) . . ?
O1A C1 N2 121.3(7) . . ?
N1 C1 N2 115.5(4) . . ?
O1A C1 S1A 0.6(10) . . ?
N1 C1 S1A 122.5(5) . . ?
N2 C1 S1A 121.9(5) . . ?
C4 C3 C2 116.5(3) . . ?
C4 C3 H3A 108.2 . . ?
C2 C3 H3A 108.2 . . ?
C4 C3 H3B 108.2 . . ?
C2 C3 H3B 108.2 . . ?
H3A C3 H3B 107.3 . . ?
O1B C5 N3 122.3(6) . . ?
O1B C5 N4 120.9(7) . . ?
N3 C5 N4 116.7(4) . . ?
O1B C5 S1B 7.2(10) . . ?
N3 C5 S1B 121.1(5) . . ?
N4 C5 S1B 122.1(5) . . ?
C8 C7 C6 118.3(4) . . ?
C8 C7 H7A 107.7 . . ?
C6 C7 H7A 107.7 . . ?
C8 C7 H7B 107.7 . . ?
C6 C7 H7B 107.7 . . ?
H7A C7 H7B 107.1 . . ?

_refine_diff_density_max         0.275
_refine_diff_density_min         -0.273
_refine_diff_density_rms         0.061



####################################################################### 
# 
# 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 1498574'
_audit_update_record             
;
2016-08-10 deposited with the CCDC.
2016-09-02 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         ?
_chemical_formula_sum            'C8 H8 N4 O5.20 S0.80'
_chemical_formula_weight         269.03

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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

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

_cell_length_a                   8.4662(13)
_cell_length_b                   12.9681(12)
_cell_length_c                   9.6819(11)
_cell_angle_alpha                90
_cell_angle_beta                 92.490(14)
_cell_angle_gamma                90
_cell_volume                     1062.0(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    613
_cell_measurement_theta_min      3.6150
_cell_measurement_theta_max      22.6320

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.10
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.06
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.683
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             554
_exptl_absorpt_coefficient_mu    0.290
_exptl_absorpt_correction_T_min  0.83046
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35h (release 09-02-2015 CrysAlis171 .NET)
(compiled Feb  9 2015,16:26:32)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_special_details           
;
 ?  
;

_diffrn_ambient_temperature      295(2)
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            Sapphire3
_diffrn_detector_area_resol_mean 16.1340
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            4603
_diffrn_reflns_av_sigmaI/netI    0.0989
_diffrn_reflns_av_R_equivalents  0.0479
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         3.268
_diffrn_reflns_theta_max         29.353
_diffrn_reflns_theta_full        26.315
_diffrn_measured_fraction_theta_max 0.834
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.833
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.833
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             2431
_reflns_number_gt                962
_reflns_threshold_expression     'I > 2σ(I)'
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35h (release 09-02-2015 CrysAlis171 .NET)
(compiled Feb  9 2015,16:26:32)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35h (release 09-02-2015 CrysAlis171 .NET)
(compiled Feb  9 2015,16:26:32)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35h (release 09-02-2015 CrysAlis171 .NET)
(compiled Feb  9 2015,16:26:32)
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2005)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_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 > 2σ(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     
'w=1/[σ²(Fo²)+(0.1126P)²] 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         2431
_refine_ls_number_parameters     181
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.2337
_refine_ls_R_factor_gt           0.1059
_refine_ls_wR_factor_ref         0.2839
_refine_ls_wR_factor_gt          0.2172
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_restrained_S_all      1.021
_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
O1A O 0.166(2) 0.5277(11) 0.0980(19) 0.089(6) Uani 0.6 1 d . . P A 1
S1A S 0.1844(11) 0.5562(6) 0.0708(9) 0.0423(15) Uani 0.4 1 d . . P A 1
O1B O -0.306(3) 0.2157(13) 0.627(2) 0.099(7) Uani 0.6 1 d . . P B 2
S1B S -0.2877(12) 0.1898(6) 0.5967(9) 0.0509(17) Uani 0.4 1 d . . P B 2
O3 O 0.1014(5) 0.1956(3) 0.1846(4) 0.0520(13) Uani 1 1 d . . . . .
N1 N 0.1384(5) 0.3644(3) 0.1451(5) 0.0396(13) Uani 1 1 d . . . . .
H1 H 0.1997 0.3490 0.0797 0.048 Uiso 1 1 calc R U . . .
C2 C 0.0831(7) 0.2851(4) 0.2191(6) 0.0381(15) Uani 1 1 d . . . . .
O5 O -0.4310(6) 0.5464(3) 0.6495(5) 0.0585(14) Uani 1 1 d . . . . .
O4 O -0.6525(5) 0.2960(4) 0.9388(5) 0.0617(14) Uani 1 1 d . . . . .
O2 O -0.1616(5) 0.4498(3) 0.4286(4) 0.0565(13) Uani 1 1 d . . . . .
C3 C -0.0629(7) 0.4217(4) 0.3519(6) 0.0397(15) Uani 1 1 d . . . . .
N3 N -0.3761(6) 0.3773(4) 0.6323(5) 0.0479(15) Uani 1 1 d . . . . .
H3 H -0.3154 0.3904 0.5655 0.057 Uiso 1 1 calc R U . . .
N2 N 0.0057(5) 0.4900(3) 0.2647(5) 0.0418(13) Uani 1 1 d . . . . .
H2 H -0.0173 0.5541 0.2747 0.050 Uiso 1 1 calc R U . . .
N4 N -0.4857(6) 0.2553(3) 0.7762(5) 0.0484(14) Uani 1 1 d . . . . .
H4 H -0.4935 0.1917 0.8000 0.058 Uiso 1 1 calc R U . . .
C1 C 0.1074(7) 0.4662(4) 0.1631(6) 0.0383(15) Uani 1 1 d . . . . .
C4 C 0.0025(7) 0.3144(4) 0.3473(6) 0.0432(16) Uani 1 1 d . . . . .
H4A H 0.0772 0.3058 0.4253 0.052 Uiso 1 1 calc R U . . .
H4B H -0.0835 0.2663 0.3597 0.052 Uiso 1 1 calc R U . . .
C6 C -0.4534(7) 0.4590(4) 0.6876(7) 0.0450(16) Uani 1 1 d . . . . .
C8 C -0.5741(7) 0.3247(5) 0.8451(6) 0.0449(16) Uani 1 1 d . . . . .
C5 C -0.3859(7) 0.2773(5) 0.6729(6) 0.0415(16) Uani 1 1 d . . . . .
C7 C -0.5704(8) 0.4317(5) 0.7934(7) 0.058(2) Uani 1 1 d . . . . .
H7A H -0.5511 0.4767 0.8724 0.069 Uiso 1 1 calc R U . . .
H7B H -0.6750 0.4480 0.7547 0.069 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
O1A C1 1.142(13) . ?
S1A C1 1.623(8) . ?
O1B C5 1.149(14) . ?
S1B C5 1.605(9) . ?
O3 C2 1.219(6) . ?
N1 C2 1.349(6) . ?
N1 C1 1.358(7) . ?
N1 H1 0.8600 . ?
C2 C4 1.492(7) . ?
O5 C6 1.208(7) . ?
O4 C8 1.206(6) . ?
O2 C3 1.199(6) . ?
C3 N2 1.369(6) . ?
C3 C4 1.499(8) . ?
N3 C5 1.358(7) . ?
N3 C6 1.367(7) . ?
N3 H3 0.8600 . ?
N2 C1 1.371(6) . ?
N2 H2 0.8600 . ?
N4 C8 1.363(7) . ?
N4 C5 1.368(7) . ?
N4 H4 0.8600 . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C6 C7 1.498(8) . ?
C8 C7 1.476(8) . ?
C7 H7A 0.9700 . ?
C7 H7B 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
C2 N1 C1 126.8(5) . . ?
C2 N1 H1 116.6 . . ?
C1 N1 H1 116.6 . . ?
O3 C2 N1 122.0(5) . . ?
O3 C2 C4 122.6(5) . . ?
N1 C2 C4 115.4(5) . . ?
O2 C3 N2 120.7(5) . . ?
O2 C3 C4 124.6(5) . . ?
N2 C3 C4 114.5(5) . . ?
C5 N3 C6 126.2(5) . . ?
C5 N3 H3 116.9 . . ?
C6 N3 H3 116.9 . . ?
C3 N2 C1 126.4(5) . . ?
C3 N2 H2 116.8 . . ?
C1 N2 H2 116.8 . . ?
C8 N4 C5 126.2(5) . . ?
C8 N4 H4 116.9 . . ?
C5 N4 H4 116.9 . . ?
O1A C1 N1 121.2(10) . . ?
O1A C1 N2 122.6(11) . . ?
N1 C1 N2 116.2(5) . . ?
O1A C1 S1A 2.1(12) . . ?
N1 C1 S1A 122.9(5) . . ?
N2 C1 S1A 120.8(5) . . ?
C2 C4 C3 116.3(5) . . ?
C2 C4 H4A 108.2 . . ?
C3 C4 H4A 108.2 . . ?
C2 C4 H4B 108.2 . . ?
C3 C4 H4B 108.2 . . ?
H4A C4 H4B 107.4 . . ?
O5 C6 N3 121.5(5) . . ?
O5 C6 C7 123.2(5) . . ?
N3 C6 C7 115.2(5) . . ?
O4 C8 N4 119.8(6) . . ?
O4 C8 C7 124.4(6) . . ?
N4 C8 C7 115.7(5) . . ?
O1B C5 N3 120.5(11) . . ?
O1B C5 N4 122.0(11) . . ?
N3 C5 N4 117.3(5) . . ?
O1B C5 S1B 5.8(15) . . ?
N3 C5 S1B 120.2(5) . . ?
N4 C5 S1B 122.5(5) . . ?
C8 C7 C6 118.6(5) . . ?
C8 C7 H7A 107.7 . . ?
C6 C7 H7A 107.7 . . ?
C8 C7 H7B 107.7 . . ?
C6 C7 H7B 107.7 . . ?
H7A C7 H7B 107.1 . . ?

_refine_diff_density_max         0.569
_refine_diff_density_min         -0.306
_refine_diff_density_rms         0.129



