# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2015

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_amv228
_database_code_depnum_ccdc_archive 'CCDC 1001617'
_audit_update_record             
;
2015-09-14 deposited with the CCDC.
2015-09-23 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C13 H9 N3 O3 S2'
_chemical_formula_weight         319.35

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   P21/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                   18.882(2)
_cell_length_b                   3.9209(5)
_cell_length_c                   20.007(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 107.813(13)
_cell_angle_gamma                90.00
_cell_volume                     1410.2(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    295(2)
_cell_measurement_reflns_used    2513
_cell_measurement_theta_min      3.56
_cell_measurement_theta_max      25.10

_exptl_crystal_description       Block
_exptl_crystal_colour            Yellow
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.23
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.504
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             656
_exptl_absorpt_coefficient_mu    0.390
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  0.8853
_exptl_absorpt_correction_T_max  0.9156
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      295(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  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0
_diffrn_reflns_number            5032
_diffrn_reflns_av_R_equivalents  0.0307
_diffrn_reflns_av_sigmaI/netI    0.0433
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         3.56
_diffrn_reflns_theta_max         25.10
_reflns_number_total             2513
_reflns_number_gt                2013
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_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)+(0.1129P)²+0.4012P] 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         2513
_refine_ls_number_parameters     191
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0554
_refine_ls_R_factor_gt           0.0406
_refine_ls_wR_factor_ref         0.1409
_refine_ls_wR_factor_gt          0.1192
_refine_ls_goodness_of_fit_ref   0.854
_refine_ls_restrained_S_all      0.854
_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
N2 N 1.08597(16) 0.2838(9) 0.40724(12) 0.0685(9) Uani 1 1 d . . .
H2A H 1.1280 0.3677 0.4071 0.082 Uiso 1 1 calc R . .
H2B H 1.0787 0.2305 0.4463 0.082 Uiso 1 1 calc R . .
C13 C 0.79275(17) -0.0364(8) 0.15822(15) 0.0524(8) Uani 1 1 d . . .
H13A H 0.7934 0.2010 0.1467 0.079 Uiso 1 1 calc R . .
H13B H 0.7429 -0.1221 0.1403 0.079 Uiso 1 1 calc R . .
H13C H 0.8246 -0.1609 0.1376 0.079 Uiso 1 1 calc R . .
N3 N 0.9168(2) -0.0912(11) 0.44477(16) 0.0913(13) Uani 1 1 d . . .
S1 S 0.95606(3) 0.21961(16) 0.21465(3) 0.0326(2) Uani 1 1 d . . .
S2 S 0.82502(4) -0.08688(17) 0.25148(4) 0.0395(2) Uani 1 1 d . . .
C3 C 1.17819(14) 0.3762(7) 0.18384(14) 0.0373(6) Uani 1 1 d . . .
H3 H 1.2153 0.2709 0.2196 0.045 Uiso 1 1 calc R . .
O3 O 1.16362(12) 0.4685(7) 0.31855(10) 0.0595(6) Uani 1 1 d . . .
C10 C 0.96015(15) 0.1031(7) 0.34158(14) 0.0403(6) Uani 1 1 d . . .
C11 C 0.91391(14) 0.0762(6) 0.27371(13) 0.0330(6) Uani 1 1 d . . .
C4 C 1.11214(13) 0.4713(6) 0.19595(13) 0.0319(6) Uani 1 1 d . . .
C5 C 1.05629(14) 0.6214(6) 0.14176(13) 0.0341(6) Uani 1 1 d . . .
H5 H 1.0113 0.6791 0.1487 0.041 Uiso 1 1 calc R . .
C1 C 1.13387(15) 0.5910(7) 0.06869(13) 0.0371(6) Uani 1 1 d . . .
C7 C 1.10645(14) 0.4210(7) 0.26860(13) 0.0381(6) Uani 1 1 d . . .
C6 C 1.06721(15) 0.6854(7) 0.07772(14) 0.0391(6) Uani 1 1 d . . .
H6 H 1.0304 0.7897 0.0416 0.047 Uiso 1 1 calc R . .
N1 N 1.14639(16) 0.6701(8) 0.00110(14) 0.0598(7) Uani 1 1 d . . .
O1 O 1.2028(2) 0.5676(9) -0.00852(16) 0.1043(11) Uani 1 1 d . . .
C2 C 1.18983(15) 0.4342(7) 0.12042(14) 0.0400(6) Uani 1 1 d . . .
H2 H 1.2340 0.3698 0.1126 0.048 Uiso 1 1 calc R . .
C9 C 1.03200(16) 0.2362(7) 0.34679(14) 0.0414(7) Uani 1 1 d . . .
C12 C 0.93710(18) -0.0033(9) 0.39961(15) 0.0566(9) Uani 1 1 d . . .
C8 C 1.03877(14) 0.3152(7) 0.28081(12) 0.0360(6) Uani 1 1 d . . .
O2 O 1.09935(15) 0.8391(9) -0.04145(12) 0.0880(9) 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
N2 0.0559(17) 0.119(3) 0.0293(12) 0.0074(14) 0.0110(11) -0.0322(17)
C13 0.0502(18) 0.0643(19) 0.0435(16) -0.0003(15) 0.0155(13) -0.0066(15)
N3 0.085(2) 0.149(4) 0.0473(17) 0.014(2) 0.0320(16) -0.037(2)
S1 0.0312(4) 0.0389(4) 0.0309(4) 0.0017(3) 0.0143(3) -0.0024(3)
S2 0.0331(4) 0.0438(4) 0.0468(4) 0.0034(3) 0.0200(3) -0.0026(3)
C3 0.0287(13) 0.0436(15) 0.0377(14) 0.0023(12) 0.0076(10) -0.0017(11)
O3 0.0435(12) 0.1010(18) 0.0323(10) 0.0008(11) 0.0090(9) -0.0261(12)
C10 0.0417(15) 0.0467(16) 0.0381(14) 0.0035(12) 0.0203(11) -0.0068(12)
C11 0.0352(13) 0.0295(12) 0.0402(14) 0.0015(11) 0.0203(11) 0.0002(10)
C4 0.0313(13) 0.0321(12) 0.0336(13) -0.0004(10) 0.0118(10) -0.0072(10)
C5 0.0300(13) 0.0360(14) 0.0396(14) 0.0031(11) 0.0159(11) 0.0032(11)
C1 0.0423(15) 0.0428(14) 0.0294(13) -0.0011(11) 0.0155(11) -0.0062(12)
C7 0.0368(15) 0.0485(16) 0.0302(13) 0.0023(12) 0.0121(11) -0.0077(12)
C6 0.0376(14) 0.0418(14) 0.0367(14) 0.0095(12) 0.0097(11) -0.0008(12)
N1 0.0585(17) 0.0865(19) 0.0418(14) 0.0038(15) 0.0260(13) -0.0111(16)
O1 0.108(2) 0.157(3) 0.0750(18) 0.026(2) 0.0684(18) 0.033(2)
C2 0.0313(14) 0.0497(16) 0.0426(15) -0.0028(12) 0.0168(11) 0.0001(12)
C9 0.0426(15) 0.0490(16) 0.0349(14) 0.0021(12) 0.0153(12) -0.0090(12)
C12 0.0499(18) 0.084(2) 0.0399(17) 0.0037(16) 0.0204(14) -0.0163(17)
C8 0.0353(14) 0.0440(14) 0.0301(13) 0.0008(11) 0.0122(11) -0.0051(11)
O2 0.0742(18) 0.146(3) 0.0427(13) 0.0343(16) 0.0159(12) 0.0021(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
N2 C9 1.335(4) . ?
N2 H2A 0.8600 . ?
N2 H2B 0.8600 . ?
C13 S2 1.788(3) . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
N3 C12 1.138(4) . ?
S1 C11 1.709(2) . ?
S1 C8 1.751(3) . ?
S2 C11 1.723(3) . ?
C3 C2 1.371(4) . ?
C3 C4 1.392(4) . ?
C3 H3 0.9300 . ?
O3 C7 1.240(3) . ?
C10 C11 1.375(4) . ?
C10 C12 1.422(4) . ?
C10 C9 1.427(4) . ?
C4 C5 1.391(4) . ?
C4 C7 1.503(3) . ?
C5 C6 1.382(3) . ?
C5 H5 0.9300 . ?
C1 C6 1.376(4) . ?
C1 C2 1.377(4) . ?
C1 N1 1.475(3) . ?
C7 C8 1.434(4) . ?
C6 H6 0.9300 . ?
N1 O1 1.207(4) . ?
N1 O2 1.221(4) . ?
C2 H2 0.9300 . ?
C9 C8 1.399(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
C9 N2 H2A 120.0 . . ?
C9 N2 H2B 120.0 . . ?
H2A N2 H2B 120.0 . . ?
S2 C13 H13A 109.5 . . ?
S2 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
S2 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C11 S1 C8 92.52(12) . . ?
C11 S2 C13 102.86(13) . . ?
C2 C3 C4 121.5(2) . . ?
C2 C3 H3 119.3 . . ?
C4 C3 H3 119.3 . . ?
C11 C10 C12 121.6(3) . . ?
C11 C10 C9 113.7(2) . . ?
C12 C10 C9 124.7(3) . . ?
C10 C11 S1 111.59(19) . . ?
C10 C11 S2 123.9(2) . . ?
S1 C11 S2 124.52(16) . . ?
C5 C4 C3 118.9(2) . . ?
C5 C4 C7 123.2(2) . . ?
C3 C4 C7 117.8(2) . . ?
C6 C5 C4 120.5(2) . . ?
C6 C5 H5 119.8 . . ?
C4 C5 H5 119.8 . . ?
C6 C1 C2 122.9(2) . . ?
C6 C1 N1 118.3(2) . . ?
C2 C1 N1 118.8(2) . . ?
O3 C7 C8 120.5(2) . . ?
O3 C7 C4 117.2(2) . . ?
C8 C7 C4 122.3(2) . . ?
C1 C6 C5 118.4(2) . . ?
C1 C6 H6 120.8 . . ?
C5 C6 H6 120.8 . . ?
O1 N1 O2 124.0(3) . . ?
O1 N1 C1 118.2(3) . . ?
O2 N1 C1 117.8(3) . . ?
C3 C2 C1 117.8(2) . . ?
C3 C2 H2 121.1 . . ?
C1 C2 H2 121.1 . . ?
N2 C9 C8 124.0(2) . . ?
N2 C9 C10 124.2(2) . . ?
C8 C9 C10 111.8(2) . . ?
N3 C12 C10 178.1(3) . . ?
C9 C8 C7 124.6(2) . . ?
C9 C8 S1 110.37(19) . . ?
C7 C8 S1 124.63(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
C12 C10 C11 S1 -179.5(2) . . . . ?
C9 C10 C11 S1 -1.2(3) . . . . ?
C12 C10 C11 S2 -0.3(4) . . . . ?
C9 C10 C11 S2 178.13(19) . . . . ?
C8 S1 C11 C10 0.8(2) . . . . ?
C8 S1 C11 S2 -178.48(17) . . . . ?
C13 S2 C11 C10 177.4(2) . . . . ?
C13 S2 C11 S1 -3.4(2) . . . . ?
C2 C3 C4 C5 1.5(4) . . . . ?
C2 C3 C4 C7 -175.6(2) . . . . ?
C3 C4 C5 C6 -2.2(4) . . . . ?
C7 C4 C5 C6 174.8(2) . . . . ?
C5 C4 C7 O3 -141.1(3) . . . . ?
C3 C4 C7 O3 35.8(4) . . . . ?
C5 C4 C7 C8 40.2(4) . . . . ?
C3 C4 C7 C8 -142.8(3) . . . . ?
C2 C1 C6 C5 0.4(4) . . . . ?
N1 C1 C6 C5 -178.0(2) . . . . ?
C4 C5 C6 C1 1.3(4) . . . . ?
C6 C1 N1 O1 -175.2(3) . . . . ?
C2 C1 N1 O1 6.3(4) . . . . ?
C6 C1 N1 O2 5.6(4) . . . . ?
C2 C1 N1 O2 -172.8(3) . . . . ?
C4 C3 C2 C1 0.1(4) . . . . ?
C6 C1 C2 C3 -1.1(4) . . . . ?
N1 C1 C2 C3 177.3(3) . . . . ?
C11 C10 C9 N2 -179.8(3) . . . . ?
C12 C10 C9 N2 -1.5(5) . . . . ?
C11 C10 C9 C8 1.0(4) . . . . ?
C12 C10 C9 C8 179.3(3) . . . . ?
C11 C10 C12 N3 1(13) . . . . ?
C9 C10 C12 N3 -177(100) . . . . ?
N2 C9 C8 C7 7.3(5) . . . . ?
C10 C9 C8 C7 -173.5(3) . . . . ?
N2 C9 C8 S1 -179.6(3) . . . . ?
C10 C9 C8 S1 -0.3(3) . . . . ?
O3 C7 C8 C9 -4.4(5) . . . . ?
C4 C7 C8 C9 174.2(2) . . . . ?
O3 C7 C8 S1 -176.6(2) . . . . ?
C4 C7 C8 S1 2.0(4) . . . . ?
C11 S1 C8 C9 -0.3(2) . . . . ?
C11 S1 C8 C7 172.9(3) . . . . ?

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        25.10
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.259
_refine_diff_density_min         -0.320
_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_a
_database_code_depnum_ccdc_archive 'CCDC 1015213'
_audit_update_record             
;
2015-09-14 deposited with the CCDC.
2015-09-23 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C8 H8 N2 O S2'
_chemical_formula_sum            'C8 H8 N2 O S2'
_chemical_formula_weight         212.28

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   'C 2/c'
_symmetry_space_group_name_Hall  '-C 2yc'

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

_cell_length_a                   15.8510(16)
_cell_length_b                   10.6692(5)
_cell_length_c                   13.4352(12)
_cell_angle_alpha                90.00
_cell_angle_beta                 124.182(9)
_cell_angle_gamma                90.00
_cell_volume                     1879.6(3)
_cell_formula_units_Z            8
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    2230
_cell_measurement_theta_min      3.1070
_cell_measurement_theta_max      27.5070

_exptl_crystal_description       prism
_exptl_crystal_colour            'light brown'
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.500
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             880
_exptl_absorpt_coefficient_mu    0.525
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_correction_T_min  0.852
_exptl_absorpt_correction_T_max  0.923
_exptl_absorpt_process_details   'CrysAlis PRO (Agilent, 2014)'

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'SuperNova (Mo) X-ray Source'
_diffrn_radiation_monochromator  Mirror
_diffrn_measurement_device_type  
'Agilent Technologies SuperNova Dual diffractometer with Atlas detector'
_diffrn_detector_area_resol_mean 10.4041
_diffrn_measurement_method       'ω scan'
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0
_diffrn_reflns_number            5465
_diffrn_reflns_av_R_equivalents  0.0279
_diffrn_reflns_av_sigmaI/netI    0.0343
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         3.11
_diffrn_reflns_theta_max         27.61
_reflns_number_total             2177
_reflns_number_gt                1829
_reflns_threshold_expression     I>2σ(I)

_computing_data_collection       'CrysAlis PRO (Agilent, 2014)'
_computing_cell_refinement       'CrysAlis PRO (Agilent, 2014)'
_computing_data_reduction        'CrysAlis PRO (Agilent, 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'X-Seed (Barbour, 2001)'
_computing_publication_material  'publCIF (Westrip, 2010)'

_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)+(0.0486P)²+1.5430P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2177
_refine_ls_number_parameters     150
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0421
_refine_ls_R_factor_gt           0.0319
_refine_ls_wR_factor_ref         0.0887
_refine_ls_wR_factor_gt          0.0800
_refine_ls_goodness_of_fit_ref   0.998
_refine_ls_restrained_S_all      0.998
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.001

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 0.40261(3) 0.87905(4) 0.56405(4) 0.01430(13) Uani 1 1 d . . .
S2 S 0.43670(3) 0.61411(4) 0.51222(4) 0.01752(13) Uani 1 1 d . . .
O1 O 0.29973(10) 1.04634(11) 0.73607(11) 0.0214(3) Uani 1 1 d . . .
N1 N 0.29416(11) 0.78234(15) 0.75308(13) 0.0165(3) Uani 1 1 d . . .
H1 H 0.2731(18) 0.851(2) 0.767(2) 0.039(7) Uiso 1 1 d . . .
H2 H 0.2729(16) 0.711(2) 0.7594(19) 0.027(6) Uiso 1 1 d . . .
N2 N 0.34392(12) 0.45488(14) 0.68415(13) 0.0217(3) Uani 1 1 d . . .
C1 C 0.35482(16) 1.13776(17) 0.61915(18) 0.0229(4) Uani 1 1 d . . .
H1A H 0.3460(17) 1.217(2) 0.648(2) 0.041(6) Uiso 1 1 d . . .
H1B H 0.427(2) 1.131(2) 0.645(2) 0.049(7) Uiso 1 1 d . . .
H1C H 0.3098(18) 1.136(2) 0.534(2) 0.038(6) Uiso 1 1 d . . .
C2 C 0.33298(12) 1.02924(15) 0.67309(14) 0.0156(3) Uani 1 1 d . . .
C3 C 0.35167(13) 0.90487(15) 0.64857(14) 0.0144(3) Uani 1 1 d . . .
C4 C 0.33275(12) 0.79188(14) 0.68618(14) 0.0130(3) Uani 1 1 d . . .
C5 C 0.36071(12) 0.68689(15) 0.64439(14) 0.0138(3) Uani 1 1 d . . .
C6 C 0.39926(12) 0.72009(15) 0.57745(14) 0.0138(3) Uani 1 1 d . . .
C7 C 0.35114(12) 0.55850(15) 0.66731(14) 0.0148(3) Uani 1 1 d . . .
C8 C 0.48477(14) 0.71646(17) 0.44850(16) 0.0192(4) Uani 1 1 d . . .
H8A H 0.4995(16) 0.664(2) 0.3996(19) 0.034(6) Uiso 1 1 d . . .
H8B H 0.4319(16) 0.7740(19) 0.3932(19) 0.027(5) Uiso 1 1 d . . .
H8C H 0.5441(17) 0.759(2) 0.514(2) 0.035(6) Uiso 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 0.0172(2) 0.0106(2) 0.0182(2) 0.00026(14) 0.01190(18) -0.00038(15)
S2 0.0238(2) 0.0125(2) 0.0231(2) 0.00152(15) 0.0173(2) 0.00343(16)
O1 0.0313(7) 0.0137(6) 0.0268(6) -0.0025(5) 0.0211(6) 0.0006(5)
N1 0.0227(8) 0.0112(7) 0.0202(7) -0.0004(6) 0.0148(6) -0.0004(6)
N2 0.0303(8) 0.0139(7) 0.0239(7) 0.0008(6) 0.0170(7) 0.0019(7)
C1 0.0359(11) 0.0111(8) 0.0267(10) -0.0012(7) 0.0205(9) -0.0017(8)
C2 0.0170(8) 0.0115(8) 0.0169(8) -0.0016(6) 0.0086(6) -0.0021(6)
C3 0.0166(8) 0.0121(7) 0.0158(8) -0.0008(6) 0.0099(7) -0.0006(6)
C4 0.0121(7) 0.0111(7) 0.0127(7) -0.0008(6) 0.0049(6) 0.0004(6)
C5 0.0141(8) 0.0112(7) 0.0145(7) 0.0004(6) 0.0072(6) -0.0004(6)
C6 0.0132(8) 0.0127(7) 0.0144(7) 0.0005(6) 0.0071(6) 0.0014(6)
C7 0.0171(8) 0.0136(8) 0.0148(7) -0.0004(6) 0.0097(6) 0.0020(7)
C8 0.0231(9) 0.0189(8) 0.0223(9) 0.0011(7) 0.0169(8) 0.0004(8)

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 C6 1.7094(17) . ?
S1 C3 1.7458(17) . ?
S2 C6 1.7271(16) . ?
S2 C8 1.7997(18) . ?
O1 C2 1.236(2) . ?
N1 C4 1.345(2) . ?
N1 H1 0.87(3) . ?
N1 H2 0.86(2) . ?
N2 C7 1.147(2) . ?
C1 C2 1.506(2) . ?
C1 H1A 0.97(2) . ?
C1 H1B 1.00(3) . ?
C1 H1C 0.95(2) . ?
C2 C3 1.438(2) . ?
C3 C4 1.403(2) . ?
C4 C5 1.430(2) . ?
C5 C6 1.388(2) . ?
C5 C7 1.431(2) . ?
C8 H8A 0.98(2) . ?
C8 H8B 0.96(2) . ?
C8 H8C 0.97(2) . ?

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
C6 S1 C3 92.00(8) . . ?
C6 S2 C8 101.66(8) . . ?
C4 N1 H1 116.9(16) . . ?
C4 N1 H2 119.1(15) . . ?
H1 N1 H2 121(2) . . ?
C2 C1 H1A 110.3(14) . . ?
C2 C1 H1B 108.1(14) . . ?
H1A C1 H1B 109(2) . . ?
C2 C1 H1C 110.1(14) . . ?
H1A C1 H1C 108.6(19) . . ?
H1B C1 H1C 111(2) . . ?
O1 C2 C3 121.01(15) . . ?
O1 C2 C1 121.17(15) . . ?
C3 C2 C1 117.82(15) . . ?
C4 C3 C2 126.67(15) . . ?
C4 C3 S1 111.67(12) . . ?
C2 C3 S1 121.66(12) . . ?
N1 C4 C3 125.10(15) . . ?
N1 C4 C5 124.08(15) . . ?
C3 C4 C5 110.82(15) . . ?
C6 C5 C7 121.50(15) . . ?
C6 C5 C4 113.63(14) . . ?
C7 C5 C4 124.87(15) . . ?
C5 C6 S1 111.88(12) . . ?
C5 C6 S2 124.31(13) . . ?
S1 C6 S2 123.80(10) . . ?
N2 C7 C5 178.68(18) . . ?
S2 C8 H8A 107.3(13) . . ?
S2 C8 H8B 109.6(13) . . ?
H8A C8 H8B 105.9(17) . . ?
S2 C8 H8C 107.9(13) . . ?
H8A C8 H8C 113.7(18) . . ?
H8B C8 H8C 112.2(18) . . ?

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
O1 C2 C3 C4 2.4(3) . . . . ?
C1 C2 C3 C4 -177.38(16) . . . . ?
O1 C2 C3 S1 -177.82(13) . . . . ?
C1 C2 C3 S1 2.4(2) . . . . ?
C6 S1 C3 C4 0.05(13) . . . . ?
C6 S1 C3 C2 -179.78(14) . . . . ?
C2 C3 C4 N1 -0.5(3) . . . . ?
S1 C3 C4 N1 179.63(13) . . . . ?
C2 C3 C4 C5 179.82(15) . . . . ?
S1 C3 C4 C5 0.00(18) . . . . ?
N1 C4 C5 C6 -179.70(15) . . . . ?
C3 C4 C5 C6 -0.1(2) . . . . ?
N1 C4 C5 C7 0.3(3) . . . . ?
C3 C4 C5 C7 179.93(15) . . . . ?
C7 C5 C6 S1 -179.89(12) . . . . ?
C4 C5 C6 S1 0.11(18) . . . . ?
C7 C5 C6 S2 1.5(2) . . . . ?
C4 C5 C6 S2 -178.46(11) . . . . ?
C3 S1 C6 C5 -0.09(13) . . . . ?
C3 S1 C6 S2 178.49(11) . . . . ?
C8 S2 C6 C5 -176.77(14) . . . . ?
C8 S2 C6 S1 4.83(13) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1 O1 0.87(3) 2.21(2) 2.831(2) 128(2) .
N1 H2 O1 0.86(2) 2.12(2) 2.970(2) 172(2) 4_546

_diffrn_measured_fraction_theta_max 0.995
_diffrn_reflns_theta_full        27.61
_diffrn_measured_fraction_theta_full 0.995
_refine_diff_density_max         0.345
_refine_diff_density_min         -0.268
_refine_diff_density_rms         0.064

#===============================================================================
####################################################################### 
# 
# 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_added_by_encifer
_database_code_depnum_ccdc_archive 'CCDC 1061750'
_audit_update_record             
;
2015-09-14 deposited with the CCDC.
2015-09-23 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 H12 N4 S3'
_chemical_formula_weight         272.44

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           Orthorhombic
_symmetry_space_group_name_H-M   Pnma

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

_cell_length_a                   15.5299(17)
_cell_length_b                   7.0738(14)
_cell_length_c                   12.0531(17)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1324.1(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    4774
_cell_measurement_theta_min      2.62
_cell_measurement_theta_max      27.00

_exptl_crystal_description       Plate
_exptl_crystal_colour            Yellow
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.07
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.367
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             568
_exptl_absorpt_coefficient_mu    0.539
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_correction_T_min  0.9354
_exptl_absorpt_correction_T_max  0.9801
_exptl_absorpt_process_details   'shape of crystal determined optically'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'STOE IPDS 2T'
_diffrn_measurement_method       'rotation method'
_diffrn_detector_area_resol_mean '0.15 mm'
_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            4774
_diffrn_reflns_av_R_equivalents  0.0764
_diffrn_reflns_av_unetI/netI     0.0644
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.62
_diffrn_reflns_theta_max         26.99
_reflns_number_total             1553
_reflns_number_gt                990
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'X-Area 1.31 (Stoe & Cie GmbH, 2005)'
_computing_cell_refinement       'X-Area 1.31 (Stoe & Cie GmbH, 2005)'
_computing_data_reduction        'X-Area 1.31 (Stoe & Cie GmbH, 2005)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX (Farrugia, 1999)'

_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)+(0.0498P)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         1553
_refine_ls_number_parameters     99
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1010
_refine_ls_R_factor_gt           0.0542
_refine_ls_wR_factor_ref         0.1106
_refine_ls_wR_factor_gt          0.0981
_refine_ls_goodness_of_fit_ref   1.000
_refine_ls_restrained_S_all      1.000
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C -0.0754(3) 0.2500 0.0491(4) 0.0859(18) Uani 1 2 d S . .
H1C H -0.0153 0.2769 0.0390 0.103 Uiso 0.50 1 calc PR . .
H1B H -0.1091 0.3449 0.0123 0.103 Uiso 0.50 1 calc PR . .
H1A H -0.0884 0.1282 0.0182 0.103 Uiso 0.50 1 calc PR . .
C2 C -0.2116(3) 0.2500 0.1948(3) 0.0507(11) Uani 1 2 d S . .
C3 C -0.3528(3) 0.2500 0.1421(3) 0.0532(11) Uani 1 2 d S . .
H3A H -0.3824 0.1383 0.1152 0.064 Uiso 0.50 1 calc PR . .
H3B H -0.3824 0.3617 0.1152 0.064 Uiso 0.50 1 calc PR . .
C4 C -0.3469(3) 0.2500 0.2692(3) 0.0581(12) Uani 1 2 d S . .
H4A H -0.3737 0.3618 0.3005 0.070 Uiso 0.50 1 calc PR . .
H4B H -0.3737 0.1382 0.3005 0.070 Uiso 0.50 1 calc PR . .
C5 C 0.0506(3) 0.2500 -0.3463(4) 0.0711(14) Uani 1 2 d S . .
H5C H 0.0957 0.2088 -0.2976 0.085 Uiso 0.50 1 calc PR . .
H5B H 0.0629 0.3755 -0.3721 0.085 Uiso 0.50 1 calc PR . .
H5A H 0.0469 0.1657 -0.4085 0.085 Uiso 0.50 1 calc PR . .
C6 C -0.1285(3) 0.2500 -0.3778(3) 0.0411(10) Uani 1 2 d S . .
C7 C -0.2127(2) 0.2500 -0.3360(3) 0.0424(9) Uani 1 2 d S . .
C8 C -0.2288(3) 0.2500 -0.2207(3) 0.0505(10) Uani 1 2 d S . .
C9 C -0.2852(3) 0.2500 -0.4085(3) 0.0496(10) Uani 1 2 d S . .
N1 N -0.2628(2) 0.2500 0.1085(3) 0.0563(10) Uani 1 2 d S . .
H1D H -0.2454 0.2500 0.0407 0.068 Uiso 1 2 calc SR . .
N2 N -0.2549(2) 0.2500 0.2881(3) 0.0618(11) Uani 1 2 d S . .
H2A H -0.2314 0.2500 0.3527 0.074 Uiso 1 2 calc SR . .
N3 N -0.3444(3) 0.2500 -0.4641(3) 0.0758(13) Uani 1 2 d S . .
N4 N -0.2400(3) 0.2500 -0.1278(3) 0.0755(13) Uani 1 2 d S . .
S1 S -0.10023(8) 0.2500 0.19381(11) 0.0790(5) Uani 1 2 d S . .
S2 S -0.04938(7) 0.2500 -0.27328(9) 0.0531(3) Uani 1 2 d S . .
S3 S -0.10345(8) 0.2500 -0.51243(8) 0.0560(3) Uani 1 2 d S . .

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
C1 0.058(3) 0.145(5) 0.055(3) 0.000 0.009(3) 0.000
C2 0.064(3) 0.053(3) 0.0348(19) 0.000 -0.002(2) 0.000
C3 0.065(3) 0.051(3) 0.044(2) 0.000 -0.011(2) 0.000
C4 0.065(3) 0.065(3) 0.044(2) 0.000 0.005(2) 0.000
C5 0.045(3) 0.106(4) 0.063(3) 0.000 0.008(2) 0.000
C6 0.043(2) 0.042(2) 0.038(2) 0.000 -0.0002(16) 0.000
C7 0.040(2) 0.055(2) 0.0322(18) 0.000 -0.0021(17) 0.000
C8 0.038(2) 0.074(3) 0.039(2) 0.000 -0.0013(18) 0.000
C9 0.044(3) 0.071(3) 0.034(2) 0.000 0.0060(19) 0.000
N1 0.061(2) 0.079(3) 0.0299(17) 0.000 -0.0010(17) 0.000
N2 0.064(3) 0.091(3) 0.0301(19) 0.000 -0.0024(17) 0.000
N3 0.049(2) 0.128(4) 0.050(2) 0.000 -0.012(2) 0.000
N4 0.049(2) 0.140(4) 0.037(2) 0.000 0.0017(17) 0.000
S1 0.0606(8) 0.1259(13) 0.0505(7) 0.000 -0.0078(6) 0.000
S2 0.0403(6) 0.0791(8) 0.0399(5) 0.000 -0.0034(5) 0.000
S3 0.0570(7) 0.0781(8) 0.0329(5) 0.000 0.0048(5) 0.000

_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 S1 1.786(5) . ?
C1 H1C 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1A 0.9600 . ?
C2 N1 1.309(5) . ?
C2 N2 1.310(5) . ?
C2 S1 1.729(5) . ?
C3 N1 1.456(6) . ?
C3 C4 1.534(5) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C4 N2 1.447(6) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C5 S2 1.785(5) . ?
C5 H5C 0.9600 . ?
C5 H5B 0.9600 . ?
C5 H5A 0.9600 . ?
C6 C7 1.401(5) . ?
C6 S3 1.668(4) . ?
C6 S2 1.761(4) . ?
C7 C8 1.412(5) . ?
C7 C9 1.425(6) . ?
C8 N4 1.133(5) . ?
C9 N3 1.138(5) . ?
N1 H1D 0.8600 . ?
N2 H2A 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
S1 C1 H1C 109.5 . . ?
S1 C1 H1B 109.5 . . ?
H1C C1 H1B 109.5 . . ?
S1 C1 H1A 109.5 . . ?
H1C C1 H1A 109.5 . . ?
H1B C1 H1A 109.5 . . ?
N1 C2 N2 111.7(4) . . ?
N1 C2 S1 127.0(3) . . ?
N2 C2 S1 121.3(3) . . ?
N1 C3 C4 102.8(3) . . ?
N1 C3 H3A 111.2 . . ?
C4 C3 H3A 111.2 . . ?
N1 C3 H3B 111.2 . . ?
C4 C3 H3B 111.2 . . ?
H3A C3 H3B 109.1 . . ?
N2 C4 C3 102.5(3) . . ?
N2 C4 H4A 111.3 . . ?
C3 C4 H4A 111.3 . . ?
N2 C4 H4B 111.3 . . ?
C3 C4 H4B 111.3 . . ?
H4A C4 H4B 109.2 . . ?
S2 C5 H5C 109.5 . . ?
S2 C5 H5B 109.5 . . ?
H5C C5 H5B 109.5 . . ?
S2 C5 H5A 109.5 . . ?
H5C C5 H5A 109.5 . . ?
H5B C5 H5A 109.5 . . ?
C7 C6 S3 124.6(3) . . ?
C7 C6 S2 113.2(3) . . ?
S3 C6 S2 122.2(2) . . ?
C6 C7 C8 121.4(3) . . ?
C6 C7 C9 121.1(3) . . ?
C8 C7 C9 117.6(3) . . ?
N4 C8 C7 178.5(5) . . ?
N3 C9 C7 178.3(4) . . ?
C2 N1 C3 111.2(3) . . ?
C2 N1 H1D 124.4 . . ?
C3 N1 H1D 124.4 . . ?
C2 N2 C4 111.8(3) . . ?
C2 N2 H2A 124.1 . . ?
C4 N2 H2A 124.1 . . ?
C2 S1 C1 102.9(2) . . ?
C6 S2 C5 104.7(2) . . ?

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
N1 C3 C4 N2 0.0 . . . . ?
S3 C6 C7 C8 180.0 . . . . ?
S2 C6 C7 C8 0.0 . . . . ?
S3 C6 C7 C9 0.0 . . . . ?
S2 C6 C7 C9 180.0 . . . . ?
N2 C2 N1 C3 0.0 . . . . ?
S1 C2 N1 C3 180.0 . . . . ?
C4 C3 N1 C2 0.0 . . . . ?
N1 C2 N2 C4 0.0 . . . . ?
S1 C2 N2 C4 180.0 . . . . ?
C3 C4 N2 C2 0.0 . . . . ?
N1 C2 S1 C1 0.0 . . . . ?
N2 C2 S1 C1 180.0 . . . . ?
C7 C6 S2 C5 180.0 . . . . ?
S3 C6 S2 C5 0.0 . . . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        26.99
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.260
_refine_diff_density_min         -0.252
_refine_diff_density_rms         0.048
